Compositions and their cured products, molded products, display devices, and solid-state image sensors

Abstract

To provide a composition capable of producing a cured product that exhibits a high refractive index and high transparency. [Solution] A composition is provided comprising a compound (A) having a thiirane group or a thietan group and a resin (B). The resin (B) comprises a resin (B1) containing structural units derived from an unsaturated compound having a carbazole ring.

Description

[Technical Field]

[0001] The present invention relates to compositions and their cured products, molded products, display devices, and solid-state image sensors. [Background technology]

[0002] High refractive index materials are in demand in the field of optical instruments. Lenses can be obtained from high refractive index materials, and lenses can be used to control the optical path within optical instruments. Lenses are used in solid-state image sensors to improve the light collection efficiency to each photoelectric conversion element, and in display devices to improve the light extraction efficiency from pixels. Conventionally, compositions containing a compound having a thiirane group or a thiethane group and an alkali-soluble resin are known as high refractive index materials (for example, Patent Document 1). [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2024-035818 [Overview of the project] [Problems that the invention aims to solve]

[0004] However, cured products obtained from conventional compositions may not be sufficiently transparent.

[0005] Therefore, the main objective of the present invention is to provide a composition that can produce a cured product exhibiting a high refractive index and high transparency. [Means for solving the problem]

[0006] The present invention provides the compositions described in [1] to [7], the molded article described in [8], the cured article described in [9], the display device described in

[10] , and the solid-state image sensor described in

[11] . [1] Compound (A) having a thiirane group or a thiethane group, Resin (B) and contain a composition, wherein the resin (B) contains a resin (B1) including a structural unit derived from an unsaturated compound having a carbazole ring. [2] The composition according to [1], wherein the resin (B1) further contains a structural unit derived from an unsaturated compound having a cyclic ether structure with 2 to 4 carbon atoms. [3] The composition according to [1] or [2], wherein the resin (B1) further contains a structural unit derived from a (meth) acrylate having a tertiary alkyl group. [4] The composition according to any one of [1] to [3], further containing an alicyclic epoxy compound (C) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized. [5] The composition according to any one of [1] to [4], further containing an acid (D). [6] The composition according to any one of [1] to [5], further containing an acid generator (E). [7] The composition according to any one of [1] to [6], wherein the compound (A) contains a compound represented by formula (II). [Chemical formula] [In formula (II), L 1x , 1x , , 1x , , 1x , , , , , , 2x , 1x , 1x , , 1x , , 1x , , , , represents a single bond or a divalent group, and two Ls 1x may be the same or different. A 1x represents an oxygen atom or a sulfur atom, and two As 1x may be the same or different. However, at least one of the two As 1x is a sulfur atom. mx represents 0 or 1, and two mx may be the same or different. nx represents an integer from 0 to 6. R 1x represents a monovalent substituent, and when there are a plurality of Rs 1x the plurality of Rs 1x may be the same or different. R 2xR represents a hydrogen atom or a monovalent substituent, and there are two R 2x They may be the same or different. A molded article obtained by curing any of the compositions described in [8], [1], to [7]. A cured product of any of the compositions described in [9], [1], to [7]. A display device containing the cured product described in

[10] [9]. A solid-state image sensor comprising the cured material described in

[11] [9]. [Effects of the Invention]

[0007] The present invention provides a composition capable of producing a cured product exhibiting a high refractive index and high transparency. Compositions according to several embodiments tend to be excellent in terms of adhesion, film-forming properties, and resistance to yellowing. Furthermore, the present invention provides a molded product obtained by curing such a composition, a cured product of such a composition, a display device containing the cured product, and a solid-state image sensor containing the cured product. [Modes for carrying out the invention]

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

[0009] In this specification, numerical ranges indicated using "~" represent a range that includes the numbers before and after "~" as the minimum and maximum values, respectively. In numerical ranges described in stages within this specification, the upper or lower limit of one numerical range may be replaced with the upper or lower limit of another numerical range described in stages. Furthermore, in numerical ranges described within this specification, the upper or lower limit of that numerical range may be replaced with the values ​​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)acryloyloxy group and (meth)acrylic acid ester.

[0011] In this specification, unless otherwise specified, the materials exemplified below may be used individually or in combination of two or more, to the extent that the conditions are met. The content of each component refers to the total amount of multiple substances corresponding to each component, unless otherwise specified.

[0012] <Composition> The composition of one embodiment contains a compound (A) having a thiirane group or a thietan group (hereinafter sometimes referred to as "component (A)") and a resin (B) (hereinafter sometimes referred to as "component (B)"). The composition of this embodiment may further contain an alicyclic epoxy compound (C) (hereinafter sometimes referred to as "component (C)") having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized, an acid (D) (hereinafter sometimes referred to as "component (D)"), an acid generator (E) (hereinafter sometimes referred to as "component (E)"), etc. According to the composition of this embodiment, it is possible to provide a cured product that exhibits a high refractive index and also high transparency. The composition of this embodiment also tends to be excellent in terms of adhesion, film-forming ability, and resistance to yellowing.

[0013] (A) Component: Compound having a thiirane group or a thietan group (A) The composition of this embodiment contains component (A). Component (A) may be a curable compound. By containing component (A) in the composition, component (A) itself can polymerize to produce a cured product exhibiting a high refractive index.

[0014] Component (A) can be used without particular limitations as long as it is a compound having at least one thiirane group or thiethane group. Component (A) may be, for example, a compound having at least one group represented by formula (II-a), and preferably a compound having at least one group represented by formula (II-b).

[0015] [ka]

[0016] In formula (II-a), mx represents either 0 or 1. R 2x represents a hydrogen atom or a monovalent substituent. * indicates the connection position.

[0017] [ka]

[0018] In formula (II-b), L 1x This represents a single bond or a divalent group. mx represents either 0 or 1. R 2x represents a hydrogen atom or a monovalent substituent. * indicates the connection position.

[0019] L 1x Examples of divalent groups represented by include divalent aliphatic chain hydrocarbon groups which may have substituents; divalent alicyclic hydrocarbon groups which may have substituents; divalent aromatic hydrocarbon groups which may have substituents; and divalent groups which are combinations of these (e.g., aralkylene groups). The methylene group (-CH2-) included in the divalent group is -O-, -S-, -NR A -(R A represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. It may be substituted with -CO- or -SO2-.

[0020] Examples of divalent aliphatic chain hydrocarbon groups include saturated or unsaturated aliphatic chain hydrocarbon groups. More specifically, examples include methylene group, ethylene group, propanediyl group, butanediyl group, pentanediyl group, hexanediyl group, heptanediyl group, octanediyl group, nonanediyl group, decanediyl group, undecanediyl group, dodecanediyl group, tridecanediyl group, tetradecanediyl group, pentadecanediyl group, hexadecanediyl group, heptadecanediyl group, octadecanediyl group, nonadecanediyl group, eicosanediyl group, and other alkanediyl groups. Divalent aliphatic chain hydrocarbon groups may be linear or branched. The number of carbon atoms in a divalent aliphatic chain hydrocarbon group is usually 1 to 20, preferably 1 to 10, more preferably 1 to 6, even more preferably 1 to 4, and particularly preferably 1 or 2.

[0021] Examples of substituents that a divalent aliphatic chain hydrocarbon group may have include halogen atoms such as fluorine, chlorine, bromine, and iodine; hydroxyl groups; amino groups; acetyl groups; and cyano groups.

[0022] Examples of divalent alicyclic hydrocarbon groups include saturated or unsaturated alicyclic hydrocarbon groups. More specifically, monocyclic alicyclic hydrocarbon groups such as cyclopropanediyl, cyclobutanediyl, cyclopentanediyl, cyclohexanediyl, cyclooctanediyl, cyclononanediyl, and cyclodecanediyl groups; and polycyclic alicyclic hydrocarbon groups such as bicyclo[1.1.0]butanediyl, tricyclo[2.2.1.0]heptanediyl, bicyclo[3.2.1]octanediyl, bicyclo[2.2.2]octanediyl, adamantanediyl, bicyclo[4.3.2]undecanediyl, and tricyclo[5.3.1.1]dodecanediyl groups. The number of carbon atoms in a 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.

[0023] Examples of substituents that a 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 groups; halogen atoms such as fluorine, chlorine, bromine, and iodine atoms; hydroxyl groups; amino groups; acetyl groups; and cyano groups.

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

[0025] Examples of substituents that a 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 groups; halogen atoms such as fluorine, chlorine, bromine, and iodine atoms; hydroxyl groups; amino groups; acetyl groups; and cyano groups.

[0026] R 2xThe monovalent substituents represented by include, for example, monovalent hydrocarbon groups such as optionally substituted monovalent aliphatic chain hydrocarbon groups, optionally substituted monovalent alicyclic hydrocarbon groups, optionally substituted monovalent aromatic hydrocarbon groups, and monovalent groups consisting of combinations thereof (e.g., aralkyl groups); hydroxyl groups; and groups substituted with one or two alkyl groups having 1 to 6 carbon atoms, such as amino groups, monomethylamino groups, monoethylamino groups, dimethylamino groups, diethylamino groups, and methylethylamino groups. Possible amino groups include: aliphatic heterocyclic groups with 4 to 20 carbon atoms such as pyrrolidinyl group, pyrrolidinyl 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, or heterocyclic groups with 3 to 20 carbon atoms such as aromatic heterocyclic groups; halogen atoms; nitro group; cyano group; carboxyl group; sulfo group; thiol group; formyl group; -SF3 group; and -SF5 group. Methylene groups (-CH2-) included in monovalent substituents are -O-, -S-, and -NR. B -(R B The ∫ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. It may be substituted with -CO- or -SO2-. Examples of groups in which the methylene group (-CH2-) in a monovalent substituent is substituted with -O- include alkoxy groups having 1 to 12 carbon atoms such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy groups; and alkoxyalkyl groups such as methoxymethyl, ethoxymethyl, and methoxyethyl groups.

[0027] Examples of monovalent aliphatic hydrocarbon groups include saturated or unsaturated aliphatic hydrocarbon groups. More specifically, examples include alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and eicosyl groups. Monovalent aliphatic hydrocarbon groups may be linear or branched. The number of carbon atoms in a monovalent aliphatic hydrocarbon group is usually 1 to 20, preferably 1 to 10, more preferably 1 to 8, even more preferably 1 to 6, particularly preferably 1 to 4, and most preferably 1 or 2.

[0028] Examples of substituents that a monovalent aliphatic chain hydrocarbon group may have include halogen atoms such as fluorine, chlorine, bromine, and iodine; hydroxyl groups; amino groups; acetyl groups; and cyano groups.

[0029] Examples of monovalent alicyclic hydrocarbon groups include saturated or unsaturated alicyclic hydrocarbon groups. More specifically, these include monocyclic alicyclic hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclononyl, and cyclodecyl groups; 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 groups. The number of carbon atoms in a 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.

[0030] Examples of substituents that a 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 groups; halogen atoms such as fluorine, chlorine, bromine, and iodine atoms; hydroxyl groups; amino groups; acetyl groups; and cyano groups.

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

[0032] Examples of substituents that a 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 groups; halogen atoms such as fluorine, chlorine, bromine, and iodine atoms; hydroxyl groups; amino groups; acetyl groups; and cyano groups.

[0033] mx represents either 0 or 1. When mx is 0, it represents a three-membered ring structure that is a thiirane group, and when mx is 1, it represents a four-membered ring structure that is a thietan group. mx is preferably 0.

[0034] Component (A) is preferably a compound containing an aromatic ring from the viewpoint of a high refractive index of the cured product. Examples of aromatic rings include aromatic hydrocarbon rings such as benzene rings, naphthalene rings, and anthracene rings; and aromatic heterocycles such as furan, pyrrole, benzofuran, thiophene, benzothiophene, indole, pyridine, quinoline, isoquinoline, pyridazine, pyrimidine, and triazine. The aromatic ring is preferably a benzene ring or a naphthalene ring, more preferably a naphthalene ring.

[0035] Component (A) preferably includes a compound represented by formula (II) from the viewpoint of a high refractive index of the cured product.

[0036] [ka]

[0037] In formula (II), L 1x represents a single bond or a divalent group, and there are two L 1x They may be the same or different. A 1x represents an oxygen atom or a sulfur atom, and there are two A 1x They may be the same or different. However, if there are two A 1x At least one of them is a sulfur atom. mx represents either 0 or 1, and the two mx values ​​may be the same or different. nx represents an integer between 0 and 6. R 1x represents a monovalent substituent, R 1x If there are multiple R 1x They may be the same or different. R 2x R represents a hydrogen atom or a monovalent substituent, and there are two R 2x They may be the same or different.

[0038] In the compound represented by formula (II), the two groups represented by formula (II-c) may be bonded to any position between positions 1 and 8 of the naphthalene ring. The group represented by formula (II-c) on the naphthalene ring may be bonded to any two positions between positions 1 and 4 (or between positions 5 and 8), or to any one position between positions 1 and 4 (or between positions 5 and 8) and any one position between positions 5 and 8 (or between positions 1 and 4). Preferably, the group represented by formula (II-c) on the naphthalene ring is bonded to any one position between positions 1 and 4 (or between positions 5 and 8) and any one position between positions 5 and 8 (or between positions 1 and 4).

[0039] [ka]

[0040] In formula (II-c), L 1x , A 1x , mx, and R 2x The above has the same meaning as above, and * indicates the joining position.

[0041] R is a compound represented by formula (II) with one or more components. 1x If it has a monovalent substituent represented by R 1x The monovalent substituent represented by may be bonded to any position from 1 to 8 of the naphthalene ring, excluding the bonded position of the group represented by formula (II-c).

[0042] L 1x represents a single bond or a divalent group, and there are two L 1x L may be the same or different, or it may be the same. In the compound represented by formula (II), there are two L 1x Preferably, at least one of the groups is an alkanediyl group, and 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 particularly preferably 1 or 2.

[0043] A 1x represents an oxygen atom or a sulfur atom, and there are two A 1x They may be the same or different. However, if there are two A 1x At least one of them is a sulfur atom. In the compound represented by formula (II), two A 1x Preferably, both are sulfur atoms. 1x As the number of sulfur atoms increases, it tends to be possible to obtain cured products that exhibit a higher refractive index and have superior solvent resistance.

[0044] mx represents either 0 or 1, and the two mx values ​​may be the same, different, or the same. In the compound represented by formula (II), the two mx values ​​are preferably both 0.

[0045] nx represents an integer from 0 to 6. Preferably, nx is an integer from 0 to 3, more preferably from 0 to 2, even more preferably 0 or 1, and particularly preferably 0.

[0046] R 1x represents a monovalent substituent, R 1x If there are multiple R 1x They may be the same or different, or they may be the same. 1x As a monovalent substituent represented by , R 2x Examples of monovalent substituents similar to those represented by can be given.

[0047] R 2x R represents a hydrogen atom or a monovalent substituent, and there are two R 2x They may be the same or different, or they may be the same. In the compound represented by formula (II), there are two R 2x Preferably, it is 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.

[0048] (A) Examples of component (compound represented by formula (II)) include compounds represented by formula (II-A), formula (II-B), formula (II-C), formula (II-D), formula (II-E), and formula (II-F). L in formulas (II-A), (II-B), (II-C), (II-D), (II-E), and (II-F) 1x , A 1x ,mx,nx,R 1x , and R 2x This expresses the same meaning as above.

[0049] [ka]

[0050] In equations (II-A), (II-B), (II-C), (II-D), (II-E), and (II-F), there are two L 1x Preferably, at least one of the groups is an alkanediyl group, and 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 particularly preferably 1 or 2.

[0051] In formulas (II-A), (II-B), (II-C), (II-D), (II-E), and (II-F), the two mx values ​​are each independently 0 or 1, preferably 0.

[0052] In equations (II-A), (II-B), (II-C), (II-D), (II-E), and (II-F), nx is independently an integer from 0 to 6, preferably an integer from 0 to 3, more preferably an integer from 0 to 2, even more preferably 0 or 1, and particularly preferably 0.

[0053] In equations (II-A), (II-B), (II-C), (II-D), (II-E), and (II-F), there are two A 1x Each of these is independently either an oxygen atom or a sulfur atom. However, there are two A 1x At least one of them is a sulfur atom. 1x Preferably, both are sulfur atoms.

[0054] In equations (II-A), (II-B), (II-C), (II-D), (II-E), and (II-F), there are two R 2xEach of these 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. 2x They are preferably the same.

[0055] The following are specific examples of component (A) (compounds represented by formula (II)), but are not limited to these.

[0056] [ka]

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] [ka]

[0062] [ka]

[0063] [ka]

[0064] [ka]

[0065] [ka]

[0066] [ka]

[0067] [ka]

[0068] [ka]

[0069] [ka]

[0070] [ka]

[0071] [ka]

[0072] The molecular weight of component (A) (the compound represented by formula (II)) is preferably 2000 or less, more preferably 1000 or less, and even 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 even more preferably 150 or more, from the viewpoint of volatility.

[0073] (A) The compound represented by formula (II) as a component can be obtained by synthesizing the compound represented by formula (II-1) and reacting the compound represented by formula (II-1) with a sulfidating agent.

[0074] [ka]

[0075] In formula (II-1), L 1x ,mx,nx,R 1x , and R 2x This has the same meaning as (Equation (I)) above.

[0076] The compound represented by formula (II-1) can be obtained, for example, by a method that includes a step of reacting the compound represented by formula (II-1a) with the compound represented by formula (II-1b).

[0077] [ka]

[0078] In equation (II-1a), nx and R 1x This expresses the same meaning as above.

[0079] [ka]

[0080] In formula (II-1b), L 1x , mx, and R 2x This has the same meaning as above, X 1X represents a leaving group.

[0081] The reaction between the compound represented by formula (II-1a) and the compound represented by formula (II-1b) can be carried out, for example, in the presence of a base. Examples of bases 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, and cesium bicarbonate; metal alkoxides such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, sodium isopropoxide, potassium isopropoxide, sodium t-butoxide, and potassium t-butoxide; and organic bases such as ammonia, methylamine, dimethylamine, trimethylamine, triethylamine, diisopropylethylamine, triisopropylamine, DBU (diazabicycloundecene), DB1BCO (1,4-diazabicyclo[2.2.2]octane), pyridine, 2,6-dimethylpyridine, 2,6-di-t-butylpyridine, dimethylaminopyridine, triphenylphosphine, tetramethylammonium bromide, and tetramethylammonium chloride. The amount of base used may be, for example, 0.0001 to 10 moles, preferably 0.001 to 5 moles, more preferably 0.01 to 4 moles, and even more preferably 0.1 to 3 moles, per mole of the compound represented by formula (II-1a).

[0082] Furthermore, two or more bases may be used in combination. When used in combination, it is preferable to use a combination of a carbonate such as sodium carbonate, potassium carbonate, lithium carbonate, or cesium carbonate, or a bicarbonate such as sodium bicarbonate, potassium bicarbonate, lithium bicarbonate, or cesium bicarbonate, and a metal hydroxide such as sodium hydroxide, potassium hydroxide, lithium hydroxide, or cesium hydroxide, or a metal alkoxide such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, sodium isopropoxide, potassium isopropoxide, sodium t-butoxide, or potassium t-butoxide, and it is more preferable to use a combination of a bicarbonate and a metal hydroxide. When used in combination, the two types may be added simultaneously or in stages.

[0083] In the compound represented by formula (II-1b), X 1X Examples of leaving groups represented by formula (II-1b) 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. Specific examples of compounds represented by formula (II-1b) include epihalohydrin compounds (L 1x It is a methylene group, and mx is 0, R 2x Examples include compounds in which (I) is a hydrogen atom and X is a halogen atom. The amount of compound represented by formula (II-1b) used may be, for example, 0.01 to 20 moles, preferably 0.5 to 15 moles, per mole of the compound represented by formula (II-1a). In this step, the reaction may be carried out using two or more compounds represented by formula (II-1b).

[0084] The reaction between the compound represented by formula (II-1a) and the compound represented by formula (II-1b) is preferably carried out in a solvent. Examples of solvents include water, ketones, aromatic hydrocarbons, halogenated aromatic hydrocarbons, aliphatic hydrocarbons, halogenated aliphatic hydrocarbons, ethers, alcohols, glimes, esters, aliphatic nitriles, sulfoxides, and amides. The following are examples of solvents:

[0085] 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. Aliphatic halogenated 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.

[0086] The reaction temperature between the compound represented by formula (II-1a) and the compound represented by formula (II-1b) 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.

[0087] In this way, the compound represented by formula (II-1) can be obtained. When the obtained compound represented by formula (II-1) is used in the synthesis of the compound represented by formula (II), the compound represented by formula (II-1) may be used after isolation, or it may be used as is without isolation.

[0088] The compound represented by formula (II) can be obtained, for example, by a method that includes a step of reacting the compound represented by formula (II-1) with a sulfurizing agent.

[0089] The reaction between the compound represented by formula (II-1) and a sulfurizing agent is a reaction in which the oxygen atom of the epoxy ring or oxetanyl ring of the compound represented by formula (II-1) is replaced with a sulfur atom using the sulfurizing agent, thereby forming a thiirane ring (episulfide ring) or thietane ring. Examples of sulfurizing agents include thiourea, methylthiourea, dimethylthiourea, trimethylthiourea, tetramethylthiourea, tetraethylthiourea, ethylenethiourea, phenylthiourea, diphenylthiourea, tolylthiourea, ditolylthiourea, sodium thiocyanate, potassium thiocyanate, etc. The amount of sulfurizing agent used can be arbitrarily adjusted according to the oxygen atom to be substituted. The amount of sulfurizing agent used is, for example, 0.01 to 20 moles, preferably 0.5 to 10 moles, per mole of the compound represented by formula (II-1). Furthermore, by adjusting the amount of sulfurizing agent used, the reaction temperature, the reaction time, etc., it is possible to replace both oxygen atoms in the compound represented by formula (II-1) with sulfur atoms, or to replace one of the oxygen atoms in the compound represented by formula (II-1) with a sulfur atom.

[0090] The reaction between the compound represented by formula (II-1) and the sulfiding agent is preferably carried out in a solvent. Examples of solvents include those similar to those exemplified in the reaction between the compound represented by formula (II-1a) and the compound represented by formula (II-1b). The reaction between the compound represented by formula (II-1) and the sulfiding agent may take place at, for example, -80 to 200°C, preferably -40 to 100°C, more preferably -20 to 80°C, and even more preferably -5 to 60°C.

[0091] A polymerization inhibitor may be added to the reaction system to suppress the polymerization of the compound represented by formula (II) that is produced. Examples of polymerization inhibitors include acids and acid anhydrides. 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, pyroaric acid, phosphoric acid, phosphorous acid, hypophosphorous acid, phosphorus oxychloride, phosphorus oxybromide, phosphorus sulfide, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, hydrogen cyanide, chromic acid, anhydrous nitric acid, anhydrous sulfuric acid, boron oxide, arsenic acid pentoxide, phosphorus pentoxide, anhydrous chromic acid, silica, alumina, aluminum chloride, zinc chloride, lithium hydrogen phosphate, sodium hydrogen phosphate, potassium hydrogen phosphate, cesium hydrogen phosphate, lithium dihydrogen phosphate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, cesium dihydrogen phosphate, etc. Organic carboxylic acids such as formic acid, acetic acid, peracetic acid, thioacetic acid, oxalic acid, tartaric acid, propionic acid, butyric acid, succinic acid, valeric acid, caproic acid, caprylic acid, naphthenic acid, methyl mercaptopropionate, malonic acid, glutaric acid, adipic acid, cyclohexanecarboxylic acid, thiodipropionic acid, dithiodipropionic acid acetic acid, maleic acid, benzoic acid, phenylacetic acid, o-toluic acid, m-toluic acid, p-toluic acid, salicylic acid, 2-methoxybenzoic acid, 3-methoxybenzoic acid, benzoylbenzoic acid, phthalic acid, isophthalic acid, terephthalic acid, salicylic acid, benzyl 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, and other organic carboxylic acids; Phosphates such as mono, di, and trimethyl phosphates, mono, di, and triethyl phosphates, mono, di, and triisobutyl phosphates, mono, di, and tributyl phosphates, mono, di, and trilauryl phosphates, and phosphites in which the phosphate portion thereof has been converted to a phosphite; Organophosphorus compounds such as dialkyldithiophosphates, exemplified by dimethyldithiophosphate; 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, hydroxyphenylacetic acid amide, hydroxyphenylacetic acid methyl, 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; 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, metanylic acid, sulfanilic acid, 4B-acid, diaminostilbenesulfonic acid, biphenylsulfonic acid, α-naphthalenesulfonic acid, β-naphthalenesulfonic acid, peric acid, laurentic acid, phenylJ acid, etc. These are some examples.

[0092] The amount of polymerization inhibitor used may be, for example, 0.0001 to 1.0 mole per mole of the compound represented by formula (II), preferably 0.001 to 0.5 moles, more preferably 0.01 to 0.25 moles, and even more preferably 0.05 to 0.15 moles. Among these, the polymerization inhibitor is preferably acetic acid, acetic anhydride, maleic acid, maleic anhydride, phosphoric acid, alkali metal hydrogen phosphate, or alkali metal dihydrogen phosphate.

[0093] The long-term stability of the compound represented by formula (II) obtained by washing the reaction product solution with an acidic aqueous solution can be improved. Specific examples of acids used in the acidic aqueous solution include those exemplified above as polymerization inhibitors. These acids may be used alone or in mixtures of two or more. The acidic aqueous solution generally tends to exhibit its effect at pH 6 or below, but the most effective range is pH 3 or below. The acids used in the acidic aqueous solution are preferably aqueous solutions of hydrogen chloride (hydrochloric acid), sulfuric acid, phosphoric acid, and / or maleic acid.

[0094] Furthermore, hydrogen sulfide adsorbents can be used to improve the stability of the compound represented by formula (II). Examples of hydrogen sulfide adsorbents include iron(III) hydroxide, zinc oxide, KNK-301 (zinc oxide-based adsorbent, manufactured by Kureha Oil & Fat Industry Co., Ltd.), Nionon 202A (iron oxide-based adsorbent, manufactured by Ibuki Shoji Co., Ltd.), and Limonic (iron hydroxide-based, manufactured by Nippon Limonite Co., Ltd.). The hydrogen sulfide adsorbent may be added during the reaction or added during the purification process after the reaction.

[0095] The content of the compound represented by formula (II) may be, for example, 50% by mass or more, 70% by mass or more, or 90% by mass or more, or 100% by mass, based on the total amount of component (A).

[0096] The content of component (A) may be, for example, 30 to 95% by mass, based on the total amount of solids in the composition, in order to easily obtain the effects of the present invention. The content of component (A) is preferably 40% by mass or more, more preferably 50% by mass or more, even more preferably 60% by mass or more, preferably 90% by mass or less, more preferably 87% by mass or less, and even more preferably 85% by mass or less, based on the total amount of solids in the composition.

[0097] The total amount of solids in a composition refers to the sum of the components contained in the composition, excluding the solvent. The content of each component in the solids of a composition can be measured using known analytical methods such as liquid chromatography and gas chromatography. The content of each component in the solids of a composition may also be calculated from the formulation at the time of composition preparation.

[0098] (B) Component: Resin (B) The composition of this embodiment contains resin (B). Resin (B) contains resin (B1) which includes structural units derived from an unsaturated compound having a carbazole ring. By containing component (B) which includes resin (B1), the composition can provide a cured product that exhibits high transparency.

[0099] The resin (B1) contains structural units derived from an unsaturated compound having a carbazole ring (hereinafter sometimes referred to as "structural unit (B1a)"). The resin (B1) may further contain structural units derived from an unsaturated compound having a cyclic ether structure with 2 to 4 carbon atoms (hereinafter sometimes referred to as "structural unit (B1b)"). The resin (B1) may further contain structural units derived from a (meth)acrylate having a tertiary alkyl group (hereinafter sometimes referred to as "structural unit (B1c)"). The resin (B1) may further contain structural units other than structural unit (B1a), structural unit (B1b), and structural unit (B1c) (hereinafter sometimes referred to as "structural unit (B1d)").

[0100] • Structural unit (B1a) Structural unit (B1a) is a structural unit derived from an unsaturated compound having a carbazole ring. The carbazole ring may have substituents. Examples of substituents include R 2xExamples of monovalent substituents similar to those represented by can be cited. Structural unit (B1a) can be obtained by polymerization using an unsaturated compound having a carbazole ring as a monomer. Structural unit (B1a) can also be obtained by reacting another structural unit (B1a') with a compound having a carbazole ring which may have substituents (B1a''). The inclusion of structural unit (B1a) in the resin (B1) can increase the refractive index of the resulting cured product.

[0101] The unsaturated compound that gives structural unit (B1a) is preferably a compound represented by formula (III).

[0102] [ka]

[0103] In formula (III), R 1 represents a hydrogen atom, a methyl group, or a hydroxymethyl group. R 2 ~R 9 Each of these independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with an alkoxy group or an aryl group. X represents a single bond, an alkanediyl group with one or more carbon atoms, or a group represented by formula (V).

[0104] [ka]

[0105] In formula (V), l represents an integer greater than or equal to 0, and m represents an integer greater than or equal to 1. The base represented by formula (V) may be linear or branched.

[0106] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine.

[0107] Examples of alkyl groups having 1 to 20 carbon atoms include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and eicosyl groups; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and 2-ethylhexyl groups; and alicyclic alkyl groups such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl groups.

[0108] Examples of alkyl groups in which a hydrogen atom is substituted with an alkoxy group (i.e., alkoxyalkyl groups) include methoxymethyl, ethoxymethyl, and methoxyethyl groups.

[0109] Examples of alkyl groups in which a hydrogen atom is substituted with an aryl group (i.e., aralkyl groups) include the benzyl group, (2-methylphenyl)methyl group, (3-methylphenyl)methyl group, (4-methylphenyl)methyl group, (2,4-dimethylphenyl)methyl group, (ethylphenyl)methyl group, and naphthylmethyl group.

[0110] Examples of aryl groups having 6 to 20 carbon atoms include phenyl, naphthyl, anthracenyl, biphenyl, and triphenyl groups (o-terphenyl, m-terphenyl, and p-terphenyl groups).

[0111] Examples of alkanediyl groups with one or more carbon atoms include methanediyl (methylene) group, ethanediyl (ethylene) group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, and hexane-1,6-diyl group.

[0112] Examples of compounds represented by formula (III) include 9-vinylcarbazole, 9-allylcarbazole, 9-(meth)acryloylcarbazole, 2-(9-carbazolyl)ethyl (meth)acrylate, 2-(9-carbazolyl)ethoxyethyl (meth)acrylate, 2-(9-carbazolyl)-2-methylethyl (meth)acrylate, and 2-(9-carbazolyl)-1-methylethyl (meth)acrylate. Among these, the compound represented by formula (III) is preferably 9-vinylcarbazole, 9-allylcarbazole, or 2-(9-carbazolyl)ethyl (meth)acrylate.

[0113] • Structural unit (B1b) Structural unit (B1b) is a structural unit derived from an unsaturated compound having a cyclic ether structure with 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring). The cyclic ether structure may have substituents. Examples of substituents include R 2x Examples of monovalent substituents similar to those represented by can be cited. By further containing structural units (B1b) in resin (B1), it is expected that the resin will react with component (A), improving compatibility with component (A), further enhancing transparency, and also further enhancing solvent resistance. Structural units (B1b) can be obtained by polymerization using an unsaturated compound having a cyclic ether structure with 2 to 4 carbon atoms as a monomer. Structural units (B1b) can also be obtained by reacting other structural units (B1b') with a compound (B1b'') having a cyclic ether structure with 2 to 4 carbon atoms.

[0114] Examples of unsaturated compounds that provide structural unit (B1b) include monomers having an oxiranil group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (B1b1)"), monomers having an oxetanil group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (B1b2)"), and monomers having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (B1b3)"). Monomer (B1b1) is preferably a monomer having an oxiranil group and a (meth)acryloyloxy group. Monomer (B1b2) is preferably a monomer having an oxetanil group and a (meth)acryloyloxy group. Monomer (B1b3) is preferably a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group.

[0115] Monomer (B1b1) may include, for example, a monomer having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "monomer (B1b1-1)"), or a monomer having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "monomer (B1b1-2)"). The monomer that provides the structural unit (B1b) is preferably monomer (B1b1) in that it can provide higher reliability, such as solvent resistance, of the resulting cured product, and more preferably monomer (B1b1-2) in that it provides excellent storage stability of the composition.

[0116] The monomers (B1b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, α-methyl-o-vinylbenzylglycidyl ether, α-methyl-m-vinylbenzylglycidyl ether, α-methyl-p-vinylbenzylglycidyl ether, and 2,3-bis(glycidyl Examples include tris(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0117] Examples of monomers (B1b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celoxide 2000 (manufactured by Daicel Corporation)), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400 (manufactured by Daicel Corporation)), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100 (manufactured by Daicel Corporation)), compounds represented by formula (VI), compounds represented by formula (VII), and others.

[0118] [ka]

[0119] In equations (VI) and (VII), R b1 and R b2 This represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group. X b1 and Xb2 This is a single bond, *-R b3 -, *-R b3 -O-, *-R b3 -S-, or *-R b3 Represents -NH- R b3 This represents an alkanediyl group with 1 to 6 carbon atoms. * indicates the bonding position with O.

[0120] Examples of alkyl groups having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group.

[0121] Examples of alkyl groups in which a hydrogen atom is substituted with a hydroxyl group include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, and 4-hydroxybutyl group.

[0122] R b1 and R b2 Preferably, this is a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, or a 2-hydroxyethyl group, more preferably a hydrogen atom or a methyl group.

[0123] Examples of alkanediyl groups having 1 to 6 carbon atoms include methanediyl (methylene) group, ethanediyl (ethylene) group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, and hexane-1,6-diyl group.

[0124] X b1 and X b2 Preferably, it is a single bond, a methylene group, an ethylene group, *-CH2-O-, or *-CH2CH2-O-, more preferably a single bond or *-CH2CH2-O-. * represents the bond position with O.

[0125] Compounds represented by formula (VI) include those represented by formulas (VI-1) to (VI-15). The compounds represented by formula (VI) are preferably those represented by formulas (VI-1), (VI-3), (VI-5), (VI-7), (VI-9), or (VI-11) to (VI-15), and more preferably those represented by formulas (VI-1), (VI-7), (VI-9), or (VI-15).

[0126] [ka]

[0127] [ka]

[0128] Compounds represented by formula (VII) include those represented by formulas (VII-1) to (VII-15). Preferably, compounds represented by formula (VII) are those represented by formulas (VII-1), (VII-3), (VII-5), (VII-7), (VII-9), or (VII-11) to (VII-15), and more preferably, those represented by formulas (VII-1), (VII-7), (VII-9), or (VII-15).

[0129] [ka]

[0130] [ka]

[0131] The compound represented by formula (VI) and the compound represented by formula (VII) may be used individually or in combination of two or more. When used in combination, their content (compound represented by formula (VI):compound represented by formula (VII)) is preferably 5:95 to 95:5, more preferably 20:80 to 80:20 on a molar basis. An example of a commercially available mixture containing the compound represented by formula (VI-1) and the compound represented by formula (VII-1) in a molar ratio of 50:50 is E-DCPA (trade name, manufactured by Daicel Corporation).

[0132] Examples of monomers (B1b2) include 3-methyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-acryloyloxymethyl oxetane, 3-ethyl-3-methacryloyloxymethyl oxetane, 3-ethyl-3-acryloyloxymethyl oxetane, 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, and 3-ethyl-3-acryloyloxyethyl oxetane.

[0133] Examples of monomers (B1b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofurfuryl methacrylate.

[0134] The structural unit (B1b) is preferably a structural unit derived from monomer (B1b1-2), and more preferably a structural unit represented by formula (B1b-1) and / or formula (B1b-2), in terms of excellent transparency and solvent resistance of the resulting cured product. The structural unit represented by formula (B1b-1) is derived from the compound represented by formula (VI), and the structural unit represented by formula (B1b-2) is derived from the compound represented by formula (VII).

[0135] [ka]

[0136] In formula (B1b-1) and formula (B1b-2), R b1 and R b2 each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X b1 and X b2 each represents a single bond, *-R b3 -, *-R b3 -O-, *-R b3 -S-, or *-R b3 -NH-. R b3 represents an alkanediyl group having 1 to 6 carbon atoms. * represents the bonding position with O.

[0137] · Structural unit (B1c) The structural unit (B1c) is a structural unit derived from a (meth)acrylate having a tertiary alkyl group. The (meth)acrylate having a tertiary alkyl group means a (meth)acrylate having an alkyl group in which the carbon atom bonded to the oxygen atom of the (meth)acryloyloxy group is a tertiary carbon atom. The tertiary alkyl group may have a substituent. Examples of the substituent include the same ones as the monovalent substituents represented by R 2x . By the resin (B1) further containing the structural unit (B1b), the solubility is further improved, and an improvement in transparency can also be expected.

[0138] Examples of (meth)acrylates that provide the structural unit (B1c) include tert-butyl (meth)acrylate, tert-amyl (meth)acrylate, 1-methylcyclopentyl (meth)acrylate, 1-ethylcyclopentyl (meth)acrylate, 1-isopropylcyclopentyl (meth)acrylate, 1-ethylcyclohexyl (meth)acrylate, mevalonate lactone (meth)acrylate, 1-adamantyl (meth)acrylic acid, and (meth)acrylic acid. Examples include 2-cyclohexylpropane-2-yl, 2-methyladamantan-2-yl (meth)acrylate, 2-(meth)acryloyloxy-2-methyladamantan, 3-hydroxy-1-(meth)acryloyloxyadamantan, 2-ethyl-2-(meth)acryloyloxyadamantan, 2-isopropyl-2-(meth)acryloyloxyadamantan, and 2-[(3r,5r,7r)-adamantan-1-yl]propane-2-yl (meth)acrylate.

[0139] Other examples of (meth)acrylates that provide the structural unit (B1c) include, for example, (meth)acrylates having the group shown below. Note that * indicates the bond position with the oxygen atom of the (meth)acrylate (the oxygen atom of the (meth)acryloyl group that constitutes the (meth)acrylate).

[0140] [ka]

[0141] • Structural unit (B1d) Structural unit (B1d) is a structural unit other than structural unit (B1a), structural unit (B1b), and structural unit (B1c). Examples of structural unit (B1d) include structural units derived from compounds selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as "structural unit (B1d1)"). Examples of compounds selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides include, Unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; Bicyclounsaturated compounds containing carboxyl groups, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hepto-2-ene anhydride; unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Examples include unsaturated acrylates that contain both a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid.

[0142] Examples of structural units other than structural unit (B1d1) (hereinafter sometimes referred to as "structural unit (B1d2)") include, Methyl (meth)acrylate, sec-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6] Decane-8-yl (meth)acrylate (In the relevant technical field, it is sometimes commonly called "dicyclopentanyl (meth)acrylate". It is also sometimes called "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 2,6 (Meth)acrylic acid esters such as decen-8-yl (meth)acrylate (sometimes referred to as "dicyclopentenyl (meth)acrylate" in the relevant technical field), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; Diethyl maleate, diethyl fumarate, diethyl itaconate, and other dicarboxylic acid diesters; Bicyclounsaturated compounds such as bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, and 5,6-dihydroxybicyclo[2.2.1]hept-2-ene; Dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, and N-succinimidyl-4-maleimide butyrate; Structural units derived from styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-methoxystyrene, (meth)acrylonitrile, vinyl chloride, vinylidene chloride, (meth)acrylamide, vinyl acetate, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene are examples.

[0143] • Content of each structural unit In resin (B1), the content of each structural unit is, relative to the total structural units that make up resin (B1), Structural unit (B1a): 25-95 mol%, Structural unit (B1b): 1-30 mol%, Structural unit (B1c): 0.1-10 mol%, The structural unit (B1d) is preferably 0 to 40 mol%, Structural unit (B1a): 35-90 mol%, Structural unit (B1b): 1-20 mol%, Structural unit (B1c): 0.1-5 mol%, Structural unit (B1d): More preferably 0-30 mol%, Structural unit (B1a): 45-90 mol%, Structural unit (B1b): 1-15 mol%, Structural unit (B1c): 0.1-3 mol%, It is more preferable that the structural unit (B1d) is 0 to 10 mol%, Structural unit (B1a): 60-90 mol%, Structural unit (B1b): 1-10 mol%, Structural unit (B1c): 0.1-3 mol%, It is particularly preferable that the structural unit (B1d) is 0 to 10 mol%.

[0144] When the content of structural units constituting the resin (B1) falls within the above range, the resulting cured product tends to exhibit even greater transparency, film-forming properties, and solvent resistance.

[0145] Resin (B1) can be manufactured, for example, by referring to the method described in the literature "Experimental Methods for Polymer Synthesis" (by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, March 1, 1972) and the cited literature.

[0146] Specifically, one method involves placing monomers such as compounds that provide structural units (B1a), polymerization initiators, and solvents into a reaction vessel, creating a deoxygenated atmosphere by, for example, replacing oxygen with nitrogen, and heating and maintaining the temperature while stirring. The polymerization initiators and solvents are not particularly limited and can be those commonly used in the field. Examples of polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.). The solvent is not particularly limited as long as it dissolves each monomer, and examples include solvents used in the composition, as described later.

[0147] In preparing the composition, the resin solution obtained by the reaction may be used as is, a concentrated or diluted solution may be used, or a solid (powder) precipitated by methods such as reprecipitation may be used. In particular, by using the solvent used in the composition as the solvent used in polymerization, the solution after the reaction can be used directly in the production of the composition, thereby simplifying the production process of the composition.

[0148] The weight-average molecular weight (Mw) of resin (B1) in terms of polystyrene is preferably 1,000 to 100,000, more preferably 3,000 to 70,000, even more preferably 5,000 to 50,000, and particularly preferably 7,000 to 30,000. When the weight-average molecular weight (Mw) of resin (B1) is within the above range, the composition tends to have good coatability, transparency, and film-forming properties.

[0149] The degree of dispersion of resin (B1) [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] is preferably 1.1 to 6.0, more preferably 1.2 to 4.0. When the degree of dispersion is within the above range, the solvent resistance of the resulting cured product tends to be improved.

[0150] When the resin (B1) contains structural units (B1d1), its acid value is preferably 30 to 180 mg-KOH / g, more preferably 40 to 150 mg-KOH / g, and even more preferably 50 to 135 mg-KOH / g or less. Here, the acid value is measured as the amount of potassium hydroxide (mg) required to neutralize 1 g of resin, and can be determined by titration with an aqueous potassium hydroxide solution. When the acid value of the resin (B1) is within the above range, the adhesion of the resulting cured product to the substrate tends to improve.

[0151] The content of resin (B1) is preferably 60 to 100% by mass, more preferably 70 to 100% by mass, even more preferably 80 to 100% by mass, and particularly preferably 90 to 100% by mass, based on the total amount of resin (B). When the content of resin (B1) is within the above range, the resulting cured product tends to have better transparency. The content of resin (B1) may be 100% by mass, based on the total amount of resin (B).

[0152] Component (B) may include resins other than resin (B1), i.e., resin (B2) that does not contain structural units derived from unsaturated compounds having a carbazole ring. Resin (B2) is not particularly limited as long as it does not contain structural units derived from unsaturated compounds having a carbazole ring. Examples of resin (B2) include thermoplastic resins and curable resins. The curable resin may be a photocurable resin that hardens by irradiation with active energy rays, or a thermosetting resin that hardens by heat.

[0153] Examples of thermoplastic resins include olefin resins such as polyethylene resin, polypropylene resin, and polycycloolefin resin; (meth)acrylic resins such as poly(meth)acrylic acid ester resins; 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; and polyphenylene sulfide resin. One or more of these resins may be used as a polymer blend or polymer alloy.

[0154] Examples of curable resins include resins having photopolymerizable groups or thermopolymerizable groups. More specifically, examples include (meth)acrylic resins, epoxy resins, melamine resins, unsaturated polyester resins, phenolic resins, urea resins, alkyd resins, and polyimide resins.

[0155] Other examples of resin (B2) include alkali-soluble resins. The inclusion of an alkali-soluble resin in the composition can impart developability to the cured product of the composition. An alkali-soluble resin refers to a resin that is soluble in an alkaline aqueous solution. Specifically, examples include resins having carboxyl groups and / or phenolic hydroxyl groups.

[0156] The acid value of the alkali-soluble resin is preferably 10 to 170 mg KOH / g, more preferably 20 to 150 mg KOH / g, and even more preferably 30 to 140 mg KOH / g, from the viewpoint of improving the developability and solvent resistance of the cured product of the composition.

[0157] Another example of resin (B2) is high refractive index resin. High refractive index resin refers to resin whose refractive index at a wavelength of 550 nm is 1.60 or higher.

[0158] The weight-average molecular weight (Mw) of resin (B2), measured by gel permeation chromatography (GPC) on a standard polystyrene basis, may be, for example, 5 to 2 million, preferably 10 to 1 million, and more preferably 15 to 750,000. The Mw of resin (B2) can be adjusted by appropriately combining reaction conditions such as the selection of raw materials used, the preparation method, the reaction temperature, and the reaction time.

[0159] The content of resin (B2) is preferably 0 to 40% by mass, more preferably 0 to 30% by mass, even more preferably 0 to 20% by mass, and particularly preferably 0 to 10% by mass, based on the total amount of resin (B). The content of resin (B2) may be 0% by mass, based on the total amount of resin (B).

[0160] The content of resin (B) may be, for example, 1 to 50% by mass, based on the total amount of solids in the composition. When the content of resin (B) is within the above range, the resulting cured film tends to have excellent transparency, as well as excellent adhesion to the substrate and solvent resistance. The content of resin (B) is preferably 3% by mass or more, more preferably 5% by mass or more, even more preferably 7.5% by mass or more, particularly preferably 10% by mass or more, preferably 40% by mass or less, more preferably 35% by mass or less, even more preferably 30% by mass or less, and particularly preferably 25% by mass or less, based on the total amount of solids in the composition.

[0161] (C) Component: Alicyclic epoxy compound having a structure in which alicyclic unsaturated hydrocarbons are epoxidized (C) The composition of this embodiment may further contain component (C). Component (C) may be a curable compound. The composition tends to have better resistance to yellowing of the cured product when it contains component (C).

[0162] Component (C) can be used without particular limitations as long as it is a compound having at least one structure in which an alicyclic unsaturated hydrocarbon is epoxidized. Examples of alicyclic unsaturated hydrocarbons include hydrocarbons having a cyclopentene skeleton and hydrocarbons having a cyclohexene skeleton. The alicyclic unsaturated hydrocarbon may be a monocyclic compound or a condensed polycyclic compound. Component (C) is preferably a compound having at least two (2 or more) structures in which an alicyclic unsaturated hydrocarbon is epoxidized in one molecule. The number of structures in which an alicyclic unsaturated hydrocarbon is epoxidized in one molecule is preferably eight or less (8 or less), more preferably six or less (6 or less), and even more preferably four or less (4 or less).

[0163] Specific examples of component (C) include, for example, Celoxide 2021P, Celoxide 8010, Celoxide 2081, Celoxide 2000, Epolid GT401, Cyclomer M100 (all manufactured by Daicel Corporation), Epocalic THI-DE, Epocalic DE-102, and Epocalic DE-103 (all manufactured by ENEOS Corporation). Among these, component (C) is preferably a compound having at least two structures in which alicyclic unsaturated hydrocarbons are epoxidized in one molecule, such as Celoxide 2021P, Celoxide 8010, Celoxide 2081, Epolid GT401, Epocalic THI-DE, Epocalic DE-102, or Epocalic DE-103.

[0164] The molecular weight of component (C) is preferably 3000 or less, more preferably 2000 or less, even more preferably 1000 or less, and particularly preferably 500 or less. The molecular weight of component (C) is preferably 50 or more, more preferably 100 or more, and even more preferably 150 or more.

[0165] The content of component (C) may be, for example, 0.1 to 20% by mass, based on the total amount of solids in the composition. The content of component (C) is preferably 0.3% by mass or more, more preferably 0.5% by mass or more, even more preferably 1% by mass or more, particularly preferably 2% by mass or more, preferably 15% by mass or less, more preferably 7% by mass or less, and even more preferably 5% by mass or less, based on the total amount of solids in the composition.

[0166] (D) Component: Acid (D) The composition may further contain component (D). Component (D) may be a component that acts as a polymerization inhibitor. Component (D) may be added during the preparation of the composition or after the production of component (A). By containing component (D) in the composition, unintended polymerization of component (A) is suppressed, thereby improving the storage stability of the composition.

[0167] Component (D) can be exemplified by an acid similar to a polymerization inhibitor added to the reaction system to suppress the polymerization of the compound represented by formula (II) that is produced. Component (D) is preferably an organic carboxylic acid, more preferably an organic carboxylic acid having 10 or fewer carbon atoms, and even more preferably formic acid or acetic acid.

[0168] From the viewpoint of improving the storage stability of the composition, the content of component (D) is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, even more preferably 0.5 parts 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, even more preferably 25 parts by mass or less, particularly preferably 10 parts by mass or less, and most preferably 5 parts by mass or less.

[0169] (E) Ingredient: Acid generator (E) The composition of this embodiment may further contain component (E). Component (E) is a compound that generates a substance (acid) that initiates cationic polymerization upon at least one of heat and / or active energy ray irradiation, thereby promoting the cationic polymerization of components (A), (B), and (C). Compounds that generate acid upon heat are called thermal acid generators. Compounds that generate acid upon irradiation with active energy rays are called photoacid generators. Some thermal acid generators also generate a substance (acid) that initiates cationic polymerization upon irradiation with active energy rays. Some photoacid generators also generate a substance (acid) that initiates cationic polymerization upon heat. Component (E) is either a thermal acid generator or a photoacid generator, and is preferably a thermal acid generator.

[0170] Examples of component (E) include aromatic diazonium salts, aromatic sulfonium salts, aliphatic sulfonium salts, aromatic iodonium salts, pyridinium salts, and cyclopentadienyl iron(II) complexes. When component (E) is an onium salt, the counter anion can be hexafluoroantimonate, hexafluorophosphate, or P(F) x (Rf) 6-x - Examples include (Rf represents a perfluoroalkyl group, and x represents an integer from 1 to 5), tetrafluoroborate, and tetrakis(pentafluorophenyl)borate. Depending on their structure, these can be subjected to at least one of thermal and active energy ray irradiation to initiate cationic polymerization.

[0171] (E)Specific examples of component include the TA-100 series, IK-1 series (both manufactured by Sunapro Co., Ltd.), SunAid SI series (manufactured by Sanshin Chemical Industry Co., Ltd.), and K-PURE CXC series (manufactured by King Industries).

[0172] The content of component (E) is preferably 0.1 part by mass or more, more preferably 0.25 part by mass or more, still more preferably 0.5 part by mass or more, particularly preferably 1 part by mass or more, from the viewpoint of enhancing curability and / or heat resistance, with respect to 100 parts by mass of the total amount of component (A), component (B), component (C), and curable compounds other than component (A), component (B), and component (C). From the viewpoint of improving physical properties such as the mechanical properties of the cured product, it is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, still more preferably 4 parts by mass or less, particularly preferably 3 parts by mass or less.

[0173] Solvent The composition may contain one or more solvents. The solvent is preferably one that can dissolve or disperse component (A), and more preferably one that can further dissolve or disperse other components in addition to component (A). Examples of the solvent include, for example, the solvents (organic solvents) exemplified by the reaction of the compound represented by formula (II-1a) and the compound represented by formula (II-1b), 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.

[0174] 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.

[0175] As ether solvents, 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, anisole, phenethole, methylanisole, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dipropyl ether, ethylene glycol dibutyl ether, ethylene glycol ethyl methyl ether, ethylene glycol methylpropyl ether, ethylene glycol butyl methyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene Dipropyl glycol ether, propylene glycol dibutyl ether, propylene glycol ethyl methyl ether, propylene glycol methyl propyl ether, propylene glycol butyl methyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, diethylene glycol ethyl methyl ether, diethylene glycol methyl propyl ether, diethylene glycol butyl methyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, dipropylene glycol dipropyl ether, dipropylene glycol dibutyl ether, dipropylene glycol ethyl methyl ether, dipropylene glycol methyl ether, dipropylene glycol butyl methyl ether, triethylene glycol dimethyl ether, triethylene glycol diethyl ether, triethylene glycol dipropyl ether, triethylene glycol dibutyl ether, triethylene glycol ethyl methyl ether,Triethylene glycol methyl propyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tripropylene glycol diethyl ether, tripropylene glycol dipropyl ether, tripropylene glycol dibutyl ether, tripropylene glycol ethyl methyl ether, tripropylene glycol methyl propyl ether, tripropylene glycol butyl methyl ether, tetraethylene glycol dimethyl ether, tetraethylene glycol diethyl ether, tetraethylene glycol dipropyl ether, tetraethylene glycol dibutyl ether, tetraethylene glycol ethyl methyl ether, tetraethylene glycol methyl propyl ether, tetraethylene glycol butyl methyl ether, etc. may be mentioned.

[0176] Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, etc.

[0177] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0178] Examples of alcoholic solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0179] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0180] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0181] If the composition contains a solvent, the solvent content is preferably 60 parts by mass or more, more preferably 80 parts by mass or more, preferably 1000 parts by mass or less, and more preferably 500 parts by mass or less, based on 100 parts by mass of the total solid content of the composition. If 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.

[0182] Other components included in the composition include, for example, curable compounds other than components (A), (B), and (C), additives, etc. Examples of additives include inorganic particles, fillers, polymerization initiators, sensitizers, leveling agents, stabilizers, surfactants, antistatic agents, lubricants, antifouling agents, UV absorbers, antioxidants, dispersants, etc.

[0183] (Curable compounds other than components (A), (B), and (C)) The composition may contain one or more curable compounds other than components (A), (B), and (C). By including curable compounds other than components (A), (B), and (C) in the composition, the viscosity or curability of the composition can be adjusted, and the mechanical and / or optical properties of the resulting cured product and the molded product containing it can be adjusted.

[0184] Examples of curable compounds other than component (A) include epoxy compounds other than components (A), (B), and (C), oxetane compounds other than components (A) and (B), hydroxy compounds, vinyl ether compounds, allyl compounds, thiol compounds, polyphenol compounds, iso(thio)cyanate compounds, acid anhydrides, and the like.

[0185] If the composition contains curable compounds other than components (A), (B), and (C), the content of curable compounds other than components (A), (B), and (C) is preferably 1% by mass or more, more preferably 2% by mass or more, preferably 30% by mass or less, and more preferably 20% by mass or less, based on the total amount of solids in the composition.

[0186] <Cured products and molded products> The cured product of one embodiment is a cured product of the composition. The molded product of one embodiment is made by curing the composition and includes the cured product of the composition. Because the composition has excellent film-forming properties, adhesion, curability, etc., it can be suitably used as a curable material for making a cured product or a molded product containing the cured product. The cured product can preferably be obtained by curing component (A) in the composition by heat. The shape of the molded product containing the cured product is not particularly limited and may include film-like, plate-like, lens-like, powder-like, granular, non-spherical particulate, crushed particulate, porous, continuous mass, fibrous, tubular, hollow fiber-like, etc., and may be any shape depending on the intended use of the molded product.

[0187] The method for obtaining a molded product from the composition is not particularly limited and includes methods such as forming a film on a substrate and then molding it by etching, injection molding, and casting polymerization.

[0188] In the casting polymerization method, for example, the composition is injected into a molding mold, degassing is performed as needed, and then the mixture is cured by heating in an oven, and the resulting molded product is removed. The removed molded product can also be further cured by irradiation with active energy rays.

[0189] When forming a film as a molded product on a substrate, a composition is applied to the substrate, dried as necessary to form a coating film (coating layer), and the molded product, which is a cured film (cured layer), is obtained by curing the coating film (coating layer). The molded product may be a patterned cured film (cured layer). A patterned cured film can be obtained by patterning using methods such as photolithography, inkjet printing, or other printing methods. The patterning method may be, for example, photolithography. Photolithography is a method in which a composition is applied to a substrate, dried as necessary to form a coating film (coating layer), the coating film (coating layer) is exposed through a photomask, and the coating film (coating layer) after exposure is developed.

[0190] Examples of substrates include glass plates such as quartz glass, borosilicate glass, aluminasilate glass, soda-lime glass with a silica-coated surface, and alkali-free glass; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon; and substrates on which thin films of aluminum, silver, or silver / copper / palladium alloy are formed. Methods for coating the composition onto the substrate include spin coating, slit coating, and slit-and-spin coating.

[0191] The light source used for exposure is preferably a light source that generates light with a wavelength of 250 to 450 nm. For example, from light with wavelengths in this range, light around 436 nm, 408 nm, or 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, halogen lamps, etc.

[0192] After pattern exposure, the exposed coating film (coating layer) may be heated (pre-development baked) before development.

[0193] Examples of developing solutions include aqueous solutions and solvents containing alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide. As solvents, for example, solvents (organic solvents) exemplified by the reaction between the compound represented by formula (II-1a) and the compound represented by formula (II-1b), or the solvents mentioned above, can be used. The developing solution may also contain surfactants. Developing methods include the paddle method, dipping method, and spray method. Further heating (post-baking) may be performed on the patterned cured film (cured layer) obtained by development.

[0194] Since the cured product or molded product containing the same is formed from a composition, it can exhibit a high refractive index, and its refractive index can be controlled to a desired value by adjusting the composition of the composition, etc. The refractive index of the cured product or molded product containing the same at a wavelength of 550 nm may be 1.65 or higher, 1.68 or higher, 1.70 or higher, 1.72 or higher, 1.74 or higher, 1.75 or higher, or 1.76 or higher. The refractive index of the cured product or molded product containing the same at a wavelength of 550 nm may be, for example, 2.00 or lower, or 1.90 or lower.

[0195] The refractive index at 550 nm of a cured product or a molded product containing it can be measured, for example, by the following method. First, a coating film is formed on a silicon wafer, and the coating film is cured to obtain a silicon wafer with the cured film formed on it. Next, the Δψ spectrum in the range of 400 nm to 800 nm is measured on the silicon wafer with the cured film using an ellipsometer (JAWoollam, "M-2000"), and the Δψ spectrum is analyzed using the accompanying analysis software to determine the refractive index dispersion from 400 nm to 800 nm. The Cauchy model is applied as the analysis model. The refractive index at 550 nm is determined from the determined refractive index dispersion. This allows the refractive index at 550 nm of the cured product or a molded product containing it to be determined.

[0196] <Usage> Examples of 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 food, chemicals, pharmaceuticals, etc.; bottles, boxes, blisters, cups, for special packaging, compact disc coats, industrial and agricultural sheets or film materials; fading preventives 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 fibers for sportswear, stockings, hats, etc.; household interior items 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.; display boards, indicators, etc. and their surface coating materials; substrates used in optical devices, etc.; optical waveguides; holograms; LED encapsulation materials, etc.

[0197] The molded product is suitably used as a lens, an optical component used in optical instruments. Examples of optical instruments include solid-state image sensors and display devices. In solid-state image sensors, lenses are used to improve the light-gathering efficiency to each photoelectric conversion element. In display devices, lenses are used to improve the light extraction efficiency from pixels. The lenses may also be microlenses. Examples of display devices include liquid crystal displays and organic light-emitting diode (EL) displays.

[0198] Inorganic compounds such as zirconium oxide and titanium oxide are conventionally known as high refractive index materials. However, when manufacturing molded products containing high refractive index materials made of inorganic compounds, molding can be difficult, such as difficulty in etching, and contamination problems can arise from the scattering of the high refractive index material during molding. These problems can be solved by using the high refractive index material of this embodiment, which is an organic compound.

[0199] The cured product of the composition of this embodiment can be suitably used as a main-chain severing type positive resist. In forming a resist pattern using the cured product of the composition of this embodiment, irradiation with ionizing radiation (e.g., electron beam, KrF laser, ArF laser, EUV laser, etc.) severs the main chains of polymers such as component (A) and component (B) that constitute the cured product in the irradiated area of ​​the resist film, resulting in a reduction in molecular weight. As a result, a difference in solubility in the developer occurs between the exposed and unexposed areas, and a resist pattern is formed. The resist pattern using the cured product of the composition of this embodiment can be applied when forming resist patterns in the manufacture of printed circuit boards such as build-up substrates, semiconductors, photomasks, molds, etc. [Examples]

[0200] The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to these examples. In the following, unless otherwise specified, "parts" means "parts by mass".

[0201] In the following examples, "room temperature" means 18-24°C.

[0202] [Synthesis Example 1] <Synthesis of compound (A-1)> Synthesis of compound (A-1a) [ka]

[0203] A four-necked flask equipped with a Liebig condenser and thermometer was placed under a nitrogen atmosphere. 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 dissolved completely. These were then added dropwise to the four-necked 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 the compound represented by formula (A-1a) (compound (A-1a)).

[0204] 1 1H-NMR analysis and LC-MS measurements were performed to confirm the formation of compound (A-1a). 1 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

[0205] Synthesis of compound (A-1) [ka]

[0206] A four-necked flask equipped with a Liebig condenser and thermometer was placed under a nitrogen atmosphere. Three parts of compound (A-1a), 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 compound (compound (A-1)) represented by formula (A-1).

[0207] 1 1H-NMR analysis and LC-MS measurements were performed to confirm the formation of compound (A-1). 1 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

[0208] [Synthesis Example 2-1] <Synthesis of resin (B1-1)> A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen. 287 parts of propylene glycol monomethyl ether acetate were added and heated to 80°C while stirring. Then, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6A mixture of 30 parts of decane-9-yl acrylate (with a molar ratio of 1:1), 15 parts of acrylic acid, 252 parts of 9-vinylcarbazole, 3 parts of tert-butyl acrylate, and 273 parts of cyclopentanone was added dropwise over 4 hours. Meanwhile, a mixture of 15 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 120 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition was complete, 5 parts of 2,2-azobisisobutyronitrile were added, and the mixture was held at 85°C for 5 hours, then cooled to room temperature to obtain a copolymer (resin (B1-1)) with a B-type viscosity (23°C) of 36 mPas and a solid content of 30.5%. The weight-average molecular weight Mw of the resulting resin (B1-1) was 9.5 × 10⁻⁶. 3 The variance was 2.58.

[0209] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the obtained resin were measured using the GPC method under the following conditions. Equipment: HLC-8120GPC (manufactured by Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: THF (tetrahydrofuran) Flow rate: 1.0mL / min Test liquid solid content concentration: 0.001~0.01% by mass Injection volume: 50μL Detector: RI Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight-average molecular weight to the number-average molecular weight (Mw / Mn) obtained above in polystyrene terms was defined as the degree of dispersion.

[0210] [Synthesis Example 2-2] <Synthesis of resin (B1-2)> A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen. 296 parts of propylene glycol monomethyl ether acetate were added and heated to 85°C while stirring. Then, 3,4-epoxytricyclo[5.2.1.02,6 ] Decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixture of 30 parts of decane-9-yl acrylate (with a molar ratio of 1:1), 15 parts of acrylic acid, 252 parts of 9-vinylcarbazole, 3 parts of tert-butyl acrylate, and 278 parts of cyclopentanone was added dropwise over 5 hours. Meanwhile, a mixture of 1.5 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 120 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the dropwise addition was complete, 2.5 parts of azobisisobutyronitrile was added, and the mixture was maintained at the same temperature for 5 hours. After cooling to room temperature, a copolymer (resin (B1-2)) with a B-type viscosity (23°C) of 104 mPas and a solid content of 32.5% was obtained. The weight-average molecular weight Mw of the resulting resin (B1-2) was 1.80 × 10⁻⁶ 4 The variance was 3.40.

[0211] [Synthesis Example 2-3] <Synthesis of resins (B1-3)> A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen. 290 parts of propylene glycol monomethyl ether acetate were added and heated to 85°C while stirring. Then, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixed solution of 24.5 parts of decane-9-yl acrylate (with a molar ratio of 1:1), 33.5 parts of acrylic acid, 202 parts of 9-vinylcarbazole, and 210 parts of cyclopentanone was added dropwise over 5 hours. Meanwhile, a mixed solution of 40 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 200 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the addition was complete, the mixture was held at the same temperature for 3 hours and then cooled to room temperature to obtain a copolymer (resin (B1-3)) with a B-type viscosity (23°C) of 27 mPas and a solid content of 29.4%. The weight-average molecular weight Mw of the resulting resin (B1-3) was 7.9 × 10⁻⁶. 3 The variance was 2.05.

[0212] [Synthesis Example 2-4] <Synthesis of resin (B2-1)> A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, dropping funnel, and stirrer to replace the atmosphere with nitrogen. 280 parts of propylene glycol monomethyl ether acetate were added and heated to 80°C while stirring. Then, 38 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixture of 289 parts of decane-9-yl acrylate (with a molar ratio of 1:1) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was complete, the mixture was held at 80°C for 4 hours, then cooled to room temperature to obtain a copolymer (resin (B2-1)) with a solid content of 35.1% and a viscosity of 125 mPas measured with a B-type viscometer (23°C). The weight-average molecular weight Mw of the resulting resin (B2-1) was 9.2 × 10⁻⁶. 3 The dispersion was 2.08, and the acid value on a solid content basis was 77 mg-KOH / g.

[0213] [Examples 1-6 and Comparative Example 1] <Preparation of Composition> The components shown in Table 1 were placed in flasks in the amounts (in parts by mass) shown in Table 1. Furthermore, 81 parts by mass of propylene glycol monomethyl ether acetate and 94 parts by mass of cyclopentanone were added as solvents, and the mixture was stirred to prepare the liquid compositions of Examples 1-6 and Comparative Example 1. The compositions of Examples 1-6 and Comparative Example 1 were visually transparent, confirming that the components were uniformly dissolved.

[0214] The details of the abbreviations for the ingredients shown in Table 1 are as follows: (A) Component: Compound having a thiirane group or a thietan group (A) ·(A-1): Compound (A-1) (B) Component: Resin (B) Resin (B1): Resin (B1) containing structural units derived from unsaturated compounds having a carbazole ring. ·(B1-1): Resin (B1-1) ·(B1-2): Resin (B1-2) ·(B1-3): Resin (B1-3) Resin (B2): Resin (B2) that does not contain structural units derived from unsaturated compounds having a carbazole ring. ·(B2-1): Resin (B2-1) (C) Component: Alicyclic epoxy compound having a structure in which alicyclic unsaturated hydrocarbons are epoxidized (C) • (C-1): Bifunctional alicyclic epoxy compound (Epocalic THI-DE (manufactured by ENEOS Corporation)) • (C-2): Bifunctional alicyclic epoxy compound (Celoxide 8010 (manufactured by Daicel Corporation)) • (C-3): Tetrafunctional alicyclic epoxy compound (Epolid GT401 (manufactured by Daicel Corporation)) (D) Component: Acid • (D-1): Formic acid (E) Ingredients: Acid generator • (E-1): Iodonium salt type acid generator (IK-1FG (SunApro Co., Ltd.))

[0215] <Evaluation Test> (1) Formation of a hardened film Approximately 5 mL of each composition from Examples 1-6 and Comparative Example 1 was dropped onto a 4-inch diameter silicon wafer (0.5 mm thick, manufactured by Rokko Electronics Co., Ltd.), and a coated film was formed by spin-coating using a spin coater (Mikasa Corporation, "MS-B100") at 1000 rpm for 20 seconds. The silicon wafer with the coated film was heated at 60°C for 2 minutes to remove the solvent. Next, the silicon wafer with the coated film was heated at 120°C for 10 minutes as a post-bake to obtain a silicon wafer with a cured film. The film thickness of the cured film on the silicon wafer was measured using a stylus-type film thickness gauge (Bruker, "DekTak XT"), and the film thickness was 1.5 μm in all cases.

[0216] (2) Refractive index For the silicon wafers with the cured film prepared in (1) above, the Δψ spectrum in the wavelength range from 400 nm to 800 nm was measured using an ellipsometer (JAWoolham, "M-2000"), and the refractive index dispersion in the wavelength range from 400 nm to 800 nm was determined by analyzing the Δψ spectrum with the accompanying analysis software. The Cauchy model was applied as the analysis model. The refractive index at a wavelength of 550 nm among the determined refractive index dispersions is shown in Table 2.

[0217] (3) Transparency Using the silicon wafers with the cured film formed as described in (1) above, the transparency (haze) of the composition (cured product) was evaluated according to the following evaluation criteria. Transparency was evaluated by measuring the haze of the silicon wafers with the cured film formed using a haze meter (Suga Test Instruments Co., Ltd., "HZ-2"). The light source specification selected for measurement was D65. The results are shown in Table 2. A result of 3 or higher indicates good transparency. 5. The haze was between 0% and less than 0.1%. 4. The haze level was between 0.1% and 0.2%. 3. The haze level was between 0.2% and less than 0.3%. 2: The haze was between 0.3% and 0.5%. 1: The haze level was 0.5% or higher.

[0218] (4) Film formability The silicon wafer with the coated film formed after the solvent was removed, as described in (1) above, was used as the sample. The coated film of the sample was observed, and the film-forming properties of the composition were evaluated according to the following evaluation criteria. The results are shown in Table 2. A perforation defect means that a hole of 1 mm or more in diameter is formed in the coated film, exposing the surface of the silicon wafer. A repellent defect means that although no exposed area is observed on the silicon wafer, the film thickness is partially thinned, mainly around environmental foreign matter, resulting in crater-like defects of less than 1 mm in diameter. A result of 3 or higher indicates good film-forming properties. 5: No holes or puncture defects were observed. 4: Two to five jack defects were observed. 3: Two to five perforated defects were observed. 2: Two to five perforation defects and fewer than five repellency defects were observed, and the coating turned white. 1: The coating film turned white after five or more perforation defects and five or more repellency defects were observed.

[0219] (5) Adhesion A silicon wafer with a cured film, prepared as described in (1) above, was used as the sample. The cured film of the sample was peeled off with a carving knife, partially exposing the silicon wafer surface. The exposed area was shaped like a cross. At this time, it was confirmed that the silicon wafer in the exposed area was not abraded. Next, air blowing was performed near the exposed area of ​​the silicon wafer, and the adhesion was evaluated by visually checking the condition of the sample before and after air blowing. Air blowing means blowing compressed air onto the sample surface. Air blowing was performed under the following conditions: pressure when closed 0.5 MPa, nozzle diameter 1 mm, angle between nozzle and sample 20°, distance between nozzle and sample 3 cm, and blowing time 5 seconds. The results are shown in Table 2. A result of 5 indicates good adhesion. 5: No changes were observed in the sample. 1: The cured film on the sample peeled off, and the exposed area expanded.

[0220] (6) Resistance to yellowing The yellowing resistance was evaluated for Examples 1-6 and Comparative Example 1. Using the silicon wafers with cured films prepared in (1) above, the yellowing resistance of the compositions (cured products) was evaluated according to the following evaluation criteria. Yellowing resistance was evaluated by placing the silicon wafers with cured films on a hot plate heated to 260°C for 5 minutes and calculating the change in transmittance of the cured film at a wavelength of 450 nm before and after heating (transmittance change = transmittance of the cured film before heating - transmittance of the cured film after heating). The results are shown in Table 2. If the result is 3 or higher, it can be said that the yellowing resistance is good. 5: The change in transmittance was between 0% and less than 5%. 4: The change in transmittance was between 5% and less than 10%. 3: The change in transmittance was between 10% and 12%. 2: The change in transmittance was between 12% and 15%. 1: The change in transmittance was 15% or more.

[0221] [Table 1]

[0222] [Table 2]

[0223] As shown in Table 2, the compositions of the examples exhibited a high refractive index and excellent transparency in the cured product. In contrast, the compositions of the comparative examples lacked sufficient refractive index and transparency. These results confirm that the compositions of the present invention can provide cured products that exhibit a high refractive index and high transparency.

Claims

1. Compound (A) having a thiirane group or a thiethane group, Resin (B) and It contains, A composition wherein the resin (B) comprises a resin (B1) containing structural units derived from an unsaturated compound having a carbazole ring.

2. The composition according to claim 1, wherein the resin (B1) further comprises structural units derived from an unsaturated compound having a cyclic ether structure with 2 to 4 carbon atoms.

3. The composition according to claim 1, wherein the resin (B1) further comprises structural units derived from a (meth)acrylate having a tertiary alkyl group.

4. The composition according to claim 1, further comprising an alicyclic epoxy compound (C) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized.

5. The composition according to claim 1, further containing acid (D).

6. The composition according to claim 1, further comprising an acid generator (E).

7. The composition according to claim 1, wherein the compound (A) comprises a compound represented by formula (II). 【Chemistry 1】 [In formula (II), L １ｘ represents a single bond or a divalent group, and there are two L １ｘ They may be the same or different. A １ｘ represents an oxygen atom or a sulfur atom, and there are two A １ｘ They may be the same or different. However, if there are two A １ｘ At least one of them is a sulfur atom. mx represents either 0 or 1, and the two mx values ​​may be the same or different. nx represents an integer between 0 and 6. R １ｘ represents a monovalent substituent, R １ｘ If there are multiple R １ｘ They may be the same or different. R ２ｘ represents a hydrogen atom or a monovalent substituent, and two R's ２ｘ may be the same or different.]

8. A molded article obtained by curing the composition according to any one of claims 1 to 7.

9. A cured product of the composition according to any one of claims 1 to 7.

10. A display device comprising the cured product described in claim 9.

11. A solid-state image sensor comprising the cured product described in claim 9.

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