Episulfide compound, resin composition containing same, and optical material formed through polymerization and curing of said resin composition

Abstract

The present invention provides an episulfide compound represented by formula (1). (R1 and R2 each independently represent a group selected from the group consisting of a hydrogen atom, a phenyl group, a naphthyl group, alkyl groups, and halogen atoms. n and m each independently represent an integer of 0-5.)　In particular, a mode in which R1 and R2 each represent a group selected from the group consisting of a hydrogen atom, a phenyl group, and a naphthyl group, and n and m each represent 1 is preferable.

Description

Episulfide compounds, resin compositions containing the same, and optical materials obtained by polymerizing and curing the resin composition. 【0001】 The present invention relates to an episulfide compound, a resin composition containing the same, and an optical material obtained by polymerizing and curing the resin composition. 【0002】 Conventionally, curable compositions that can be cured into any shape have been used in a wide range of industrial fields, including electrical and electronic equipment, office automation equipment, heavy electrical machinery, precision machinery, and automobiles. In particular, resin materials are lightweight, tough, and easy to process, and have been widely used in various optical components, especially lenses, in recent years. Furthermore, in recent years, optical devices such as cameras mounted on mobile products such as mobile phones, smartphones, tablet terminals, and mobile computers have become dramatically smaller, lighter, and more high-performance. Accordingly, there is a growing demand for smaller, lighter, and thinner lenses used in these optical devices. 【0003】 When cured materials obtained by curing a curable composition are used in optical components, various properties are required depending on the application. For example, when the cured material is used in an optical lens, in addition to having the desired refractive index and Abbe number, heat resistance, transparency, low water absorption, chemical resistance, low birefringence, and moisture resistance may also be required depending on the application of the optical lens. Furthermore, it may be required that the curable composition has a viscosity suitable for molding. Much research has been conducted to develop curable compositions with excellent properties in these areas. In recent years, due to the technological advancements described above, there is a particular demand for curable compositions that can produce optical components with high refractive indices. For example, in the case of optical lenses, a high refractive index allows lens elements with the same refractive index to be realized on surfaces with less curvature, thereby reducing the amount of aberration that occurs on these surfaces. As a result, it becomes possible to reduce the number of lenses, reduce the eccentricity sensitivity of the lenses, and make the lenses thinner and lighter. In addition, resin compositions with low curing shrinkage rates are sometimes required in order to transfer the lens shape with high precision during lens molding. 【0004】The epoxy resin described in Patent Document 1 is excellent in that it has a low curing shrinkage rate, but it has the problem that its refractive index is about 1.6 and the curable composition has high viscosity. On the other hand, the episulfide described in Patent Document 2 has a refractive index of 1.7 or higher and low viscosity, but it has the problem that it has a high curing shrinkage rate. 【0005】 Patent No. 6700369 Patent No. 4639418 【0006】 The present invention aims to provide a resin composition with a low curing shrinkage rate, a high refractive index, and relatively low viscosity, as well as an optical material obtained by polymerizing and curing the same. 【0007】 The present inventors have diligently studied to solve the above problems and have found that the above problems can be solved by the present invention described below. That is, the present invention is as follows: <1> An episulfide compound represented by the following formula (1). (R １ and R ２ Each independently represents a group selected from the group consisting of a hydrogen atom, a phenyl group, a naphthyl group, an alkyl group, and a halogen atom. n and m each independently represent an integer from 0 to 5.) <2> The episulfide compound described in <1> above, wherein formula (1) is the following formula (2). (R １ , R ２ , n and m are equivalent to those in equation (1).) <3> R １ and R ２ The episulfide compound described in <1> or <2> above, wherein n represents a group selected from the group consisting of a hydrogen atom, a phenyl group, and a naphthyl group, and n and m represent 1. <4> A resin composition containing the episulfide compound described in any of <1> to <3> above. <5> An optical material obtained by polymerizing and curing the resin composition described in <4> above. <6> An optical lens containing the optical material described in <5> above. <7> An epoxy compound represented by the following formula (3). <8> A resin composition containing the epoxy compound described in <7> above. <9> An optical material obtained by polymerizing and curing the resin composition described in <8> above. <10> An optical lens including the optical material described in <9> above. 【0008】 According to the present invention, it is possible to provide a resin composition having a low curing shrinkage rate, a high refractive index, and a relatively low viscosity, and an optical material obtained by polymerizing and curing the resin composition. 【0009】 Figure 1 is a chart of the H-NMR spectrum of the epoxy compound obtained in Example 1. １ Figure 2 is a chart of the H-NMR spectrum of the episulfide compound obtained in Example 2. １ Figure 3 is a chart of the H-NMR spectrum of the episulfide compound obtained in Example 3. １ Figure 4 is a chart of the H-NMR spectrum of the episulfide compound obtained in Example 4. １ Figure 5 is a chart of the H-NMR spectrum of the episulfide compound obtained in Example 5. １ Figure 6 is a chart of the H-NMR spectrum of the episulfide compound obtained in Comparative Example 1. １ Figure 6 is a chart of the H-NMR spectrum of the episulfide compound obtained in Comparative Example 1. 【0010】Embodiments of the present invention will be described in detail below. The inventors have found that a resin composition containing the episulfide compound represented by formula (1) above, and a cured product obtained by curing the same, have particularly desirable physical properties for optical materials. It has been found that, with the episulfide compound represented by formula (1) above, a resin composition and its cured product can be obtained that have suitable solubility, viscosity, refractive index, and curing shrinkage rate compared to conventionally used low molecular weight episulfide compounds and episulfide compounds having a fluorene skeleton. Generally, a high refractive index of an optical material allows lens elements with the same refractive index to be realized on a surface with less curvature, thereby reducing the amount of aberration that occurs on this surface. As a result, it becomes possible to reduce the number of lenses, reduce the eccentricity sensitivity of the lenses, and reduce the thickness of the lenses to make them lighter. Furthermore, because the resin composition has an appropriate viscosity and a low curing shrinkage rate, it has excellent moldability, making it possible to manufacture small and more complex shaped components. Furthermore, while compounds with such properties generally have a large molecular weight and low solubility, the episulfide compound represented by formula (1) has high solubility, and does not cause problems such as precipitation or clouding of the resin composition. Thus, the resin composition according to the embodiment of the present invention can be said to have a good balance of desirable properties for optical materials. 【0011】 The episulfide compound of the present invention is represented by the following formula (1). In equation (1) above, R １ and R ２ Each of these independently represents a group selected from the group consisting of a hydrogen atom, a phenyl group, a naphthyl group, an alkyl group, and a halogen atom. Preferably, R １ and R ２ n represents a group selected from the group consisting of a hydrogen atom, a phenyl group, and a naphthyl group. In formula (1) above, n and m each independently represent an integer from 0 to 5. Preferably, n and m represent 1. 【0012】 A preferred embodiment of the present invention is an episulfide compound represented by the following formula (2). In equation (2) above, R １ , R ２n and m are equivalent to those in equation (1) above. 【0013】 The episulfide compounds of the present invention are synthesized by reacting an aromatic diol compound with an epihalohydrin, such as epichlorohydrin, in the presence of an alkali to produce an epoxy compound represented by the following formula (4). (R １ and R ２ Each of these independently represents a group selected from the group consisting of a hydrogen atom, a phenyl group, a naphthyl group, an alkyl group, and a halogen atom. Each of n and m independently represents an integer from 0 to 5.) The epoxy compound can then be produced by reacting it with a thiatting agent such as a thiocyanate, thiourea, triphenylphosphine sulfide, or 3-methylbenzothiazole-2-thion, preferably with a thiocyanate or thiourea. 【0014】 Among these, the epoxy compound represented by formula (3) below is one of the preferred embodiments. 【0015】 In the method for producing the epoxy compound represented by formula (4) above, the preferred epihalohydrin compound is epichlorohydrin. Furthermore, while stoichiometrically, twice the molar amount of the aromatic diol compound is used for the epihalohydrin compound, less or more may be used if the purity of the product, reaction rate, and economic efficiency are important. Preferably, 2 to 20 times the molar amount is used for the reaction. The reaction may be carried out without a solvent or in a solvent, but when a solvent is used, it is desirable to use one in which the aromatic diol compound is soluble. Specific examples include alcohols, ethyl compounds, aromatic hydrocarbons, halogenated hydrocarbons, etc. The reaction proceeds readily in the presence of a base in amounts greater than or equal to the stoichiometric amount. That is, it can proceed in the presence of at least twice the molar amount of the aromatic diol compound. 【0016】Examples of bases include pyridine, triethylamine, tertiary amines such as diazabicycloundecene, and hydroxides of alkali or alkaline earth metals. Preferably, alkali or alkaline earth metal hydroxides are preferred, and more preferably, sodium hydroxide, potassium hydroxide, etc. 【0017】 The reaction temperature is usually carried out at -10 to 100°C, but preferably at 20 to 70°C. The reaction time can be any time required for the reaction to be completed under the above conditions, but usually 10 hours or less is appropriate. 【0018】 In a method for producing an episulfide compound represented by formula (1) from an epoxy compound represented by formula (4) above, when a thiocyanate is used as a thiatting agent, preferred thiocyanates are salts of amines, alkalis, or alkaline earth metals, and more preferably potassium thiocyanate and sodium thiocyanate. It is also preferable to use thiourea as a thiatting agent. Stoichiometrically, 2 times the molar amount of the epoxy compound represented by formula (4) above is used for thiourea or thiocyanate, but if the purity of the product, reaction rate, economy, etc. are important, less or more than this amount may be used. Preferably, 2 to 10 times the molar amount, more preferably 2 to 5 times the molar amount, is used for the reaction. 【0019】 The reaction may be carried out either without a solvent or in a solvent, but when a solvent is used, it is desirable to use one that is soluble in thiocyanates, thiourea, or epoxy compounds represented by formula (4) above. Specific examples include water, alcohols such as methanol, ethanol, and isopropanol; ethers such as diethyl ether, tetrahydrofuran, and dioxane; hydroxyethers such as methyl cellsolve, ethyl cellsolve, and butyl cellsolve; aromatic hydrocarbons such as benzene, toluene, and xylene; and halogenated hydrocarbons such as dichloroethane, chloroform, and chlorobenzene. The combined use of these, for example, combinations of ethers, hydroxyethers, halogenated hydrocarbons, or aromatic hydrocarbons with alcohols, is effective. 【0020】Furthermore, adding acids and acid anhydrides to the reaction solution as polymerization inhibitors is an effective way to improve reaction performance. Specific examples of acids and acid anhydrides include nitric acid, hydrochloric acid, sulfuric acid, fuming sulfuric acid, boric acid, arsenic acid, phosphoric acid, hydrocyanic acid, acetic acid, peracetic acid, thioacetic acid, oxalic acid, tartaric acid, propionic acid, butyric acid, succinic acid, maleic acid, benzoic acid, nitric anhydride, sulfuric acid anhydride, boron oxide, arsenic pentoxide, phosphorus pentoxide, chromic anhydride, acetic anhydride, propionic anhydride, butyric anhydride, succinic anhydride, maleic anhydride, benzoic anhydride, phthalic anhydride, silica gel, silica alumina, aluminum chloride, etc., and it is also possible to use some of these in combination. The amount added is usually 0.001 to 10% by mass relative to the total volume of the reaction solution. 【0021】 The reaction temperature is usually 0 to 100°C, but preferably 20 to 70°C. The reaction time can be any time required for the reaction to be completed under the above conditions, but usually 1 to 50 hours is appropriate, and 5 to 30 hours is more preferable. The stability of the resulting compound can be improved by washing the reaction product with an acidic aqueous solution. Specific examples of acids that can be used in the acidic aqueous solution include nitric acid, hydrochloric acid, sulfuric acid, boric acid, arsenic acid, phosphoric acid, hydrogen cyanide, acetic acid, peracetic acid, thioacetic acid, oxalic acid, tartaric acid, succinic acid, maleic acid, etc. These can be used individually or in mixtures of two or more. The aqueous solutions of these acids are usually effective at a pH of 6 or below, but more effective at a pH of 3 or below. 【0022】The episulfide compound of the present invention or a resin composition containing the episulfide compound can be subjected to thermal polymerization in or out of the presence of a curing catalyst to produce cured products such as optical materials. A preferred method is one using a curing catalyst, and suitable curing catalysts include amines, phosphines, mineral acids, Lewis acids, organic acids, silicic acids, tetrafluoroboric acid, and the like. Specific examples include: (1) Ethylamine, n-propylamine, sec-propylamine, n-butylamine, sec-butylamine, i-butylamine, t-butylamine, pentylamine, hexylamine, heptylamine, octylamine, decylamine, laurylamine, mystyrylamine, 1,2-dimethylhexylamine, 3-pentylamine, 2-ethylhexylamine, allylamine, aminoethanol, 1-aminopropanol, 2-aminopropanol, aminobutanol, aminopentanol, aminohexanol, 3-ethoxypropylamine, 3-propoxypropylamine, 3-isopropoxypropylamine, 3-butoxypropylamine, 3-isobutoxypropylamine, 3-(2-ethylhexyloxy)propylamine, aminocyclopentane, aminocyclohexane, aminonorbornene, aminomethylcyclohexane, aminobenzene, benzylamine, phenethylamine Primary amines such as α-phenylethylamine, naphthylamine, furfurylamine; ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,2-diaminobutane, 1,3-diaminobutane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, dimethylaminopropylamine, diethylaminopropylamine, bis-(3-aminopropyl) ether, 1,2-bis-(3-aminopropoxy)ethane, 1,3-bis-(3-aminopropoxy)-2,2'-dimethylpropane, aminoethylethanolamine, 1,2-, 1,3- or 1,4-bisaminocyclohexane, 1,3- or 1,4-bisaminomethylcyclohexane, 1,3- or 1,4-bisaminoethylcyclohexane, 1,3- or 1,4-bisaminopropylcyclohexane, hydrogenated 4,4'-diaminodiphenylmethane, 2- or 4-aminopiperidine, 2- or 4-aminomethylpiperidine, 2- or 4-aminoethylpiperidine, N-aminoethylpiperidine, N-aminopropylpiperidine, N-aminoethylmorpholine, N-aminopropylmorpholine, isophoronediamine, menthanediamine, 1,4-bisaminopropylpiperazine, o-, m-, or p-phenylenediamine, 2,4- or 2,6-toylenediamine, 2,4-toluenediamine, m-amino Benzylamine, 4-chloro-o-phenylenediamine, tetrachloro-p-xylylenediamine, 4-methoxy-6-methyl-m-phenylenediamine, m- or p-xylylenediamine, 1,5- or 2,6-naphthalenediamine, benzidine, 4,4'-bis(o-toluidine), dianisidine, 4,4'-diaminodiphenylmethane, 2,2-(4,4'-diaminodiphenyl)propane, 4,4'-diaminodiphenyl ether, 4,4'-thiodianiline, 4,4'-diaminodiphenyl Sulfone, 4,4'-diaminoditolylsulfone, methylenebis(o-chloroaniline), 3,9-bis(3-aminopropyl)2,4,8,10-tetraoxaspiro[5,5]undecane, diethylenetriamine, iminobispropylamine, methyliminobispropylamine, bis(hexamethylene)triamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, N-aminoethylpiperazine, N-aminopropylpiperazine, 1,4-bis(aminoethylpiperazine) Primary polyamines such as 1,4-bis(aminopropylpiperazine), 2,6-diaminopyridine, bis(3,4-diaminophenyl)sulfone; diethylamine, dipropylamine, di-n-butylamine, di-sec-butylamine, diisobutylamine, di-n-pentylamine, di-3-pentylamine, dihexylamine, octylamine, di(2-ethylhexyl)amine, methylhexylamine, diallylamine, pyrrolidine, piperidine, 2-,3-,4-picoline, 2,4-,2,6-,3,Secondary amines such as 5-lupetidine, diphenylamine, N-methylaniline, N-ethylaniline, dibenzylamine, methylbenzylamine, dinaphthylamine, pyrrole, indoline, indole, and morpholine; N,N'-dimethylethylenediamine, N,N'-dimethyl-1,2-diaminopropane, N,N'-dimethyl-1,3-diaminopropane, N,N'-dimethyl-1,2-diaminobutane, N,N'-dimethyl-1,3-diaminobutane, N,N'-dimethyl-1,4-diaminobutane, and N,N'-dimethyl-1,5-diaminopene. Tan, N,N'-dimethyl-1,6-diaminohexane, N,N'-dimethyl-1,7-diaminoheptane, N,N'-diethylethylenediamine, N,N'-diethyl-1,2-diaminopropane, N,N'-diethyl-1,3-diaminopropane, N,N'-diethyl-1,2-diaminobutane, N,N'-diethyl-1,3-diaminobutane, N,N'-diethyl-1,4-diaminobutane, N,N'-diethyl-1,6-diaminohexane, piperazine, 2-methylpiperazine, 2,5-or 2,6-dimethylpiperazine, homopiperazine Secondary polyamines such as 1,1-di-(4-piperidyl)methane, 1,2-di-(4-piperidyl)ethane, 1,3-di-(4-piperidyl)propane, 1,4-di-(4-piperidyl)butane, tetramethylguanidine, etc.; trimethylamine, triethylamine, tri-n-propylamine, tri-iso-propylamine, tri-1,2-dimethylpropylamine, tri-3-methoxypropylamine, tri-n-butylamine, tri-iso-butylamine, tri-sec-butylamine, tri-pentylamine, tri-3-pentylamine, L-n-hexylamine, tri-n-octylamine, tri-2-ethylhexylamine, tri-dodecylamine, tri-laurylamine, tricyclohexylamine, N,N-dimethylhexylamine, N-methyldihexylamine, N,N-dimethylcyclohexylamine, N-methyldicyclohexylamine, triethanolamine, tribenzylamine, N,N-dimethylbenzylamine, diethylbenzylamine, triphenylamine, N,N-dimethylamino-p-cresol, N,N-dimethylaminomethylphenol, 2-(N,N-dimethylaminomethyl)phenol, N,N-dimethylaniline, N,N-diethylaniline, pyridine, quinoline, N-methylmorpholine, N-methylpiperidine, tertiary amines such as 2-(2-dimethylaminoethoxy)-4-methyl-1,3,2-dioxabornane; tetramethylethylenediamine, pyrazine, N,N'-dimethylpiperazine, N,N'-bis((2-hydroxy)propyl)piperazine, hexamethylenetetramine, N,N,N', Tertiary polyamines such as N'-tetramethyl-1,3-butanamine, 2-dimethylamino-2-hydroxypropane, diethylaminoethanol, N,N,N-tris(3-dimethylaminopropyl)amine, 2,4,6-tris(N,N-dimethylaminomethyl)phenol, heptamethylisobiguanide; imidazole, N-methylimidazole, 2-methylimidazole, 4-methylimidazole, N-ethylimidazole, 2-ethylimidazole, 4 -Ethylimidazole, N-butylimidazole, 2-butylimidazole, N-undecylimidazole, 2-undecylimidazole, N-phenylimidazole, 2-phenylimidazole, N-benzylimidazole, 2-benzylimidazole, 1-benzyl-2-methylimidazole, N-(2'-cyanoethyl)-2-methylimidazole, N-(2'-cyanoethyl)-2-undecylimidazole, N-(2'-cyanoethyl)-2-fe Various imidazoles such as nilimidazole, 3,3-bis-(2-ethyl-4-methylimidazolyl)methane, adducts of alkylimidazole and isocyanuric acid, and condensates of alkylimidazole and formaldehyde; amidines such as 1,8-diazabicyclo(5,4,0)undecene-7, 1,5-diazabicyclo(4,3,0)nonene-5,6-dibutylamino-1,8-diazabicyclo(5,4,0)undecene-7; and amine compounds represented above. 【0023】(2) Quaternary ammonium salts of the amines in (1) with halogens, mineral acids, Lewis acids, organic acids, silicic acid, tetrafluoroboric acid, etc. (3) Complexes of the amines in (1) with borane and boron trifluoride. (4) Phosphines such as trimethylphosphine, triethylphosphine, tri-isopropylphosphine, tri-n-butylphosphine, tri-n-cyclohexylphosphine, tri-n-octylphosphine, tricyclohexylphosphine, triphenylphosphine, trybenzylphosphine, tris(2-methylphenyl)phosphine, tris(3-methylphenyl)phosphine, tris(4-methylphenyl)phosphine, tris(diethylamino)phosphine, dimethylphenylphosphine, diethylphenylphosphine, dicyclohexylphenylphosphine, diethylphenylphosphine, dicyclohexylphenylphosphine, ethyldiphenylphosphine, diphenylcyclohexylphosphine, chlorodiphenylphosphine, etc. (5) Mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and carbonic acid, and their semi-esters. (6) Lewis acids, represented by boron trifluoride and boron trifluoride etherate. (7) Organic acids, represented by carboxylic acids, and their semi-esters. (8) Silicic acid, tetrafluoroboric acid, etc. 【0024】 Among these, those preferred for their low discoloration of the cured product are primary monoamines, secondary monoamines, tertiary monoamines, tertiary polyamines, imidazoles, amidines, quaternary ammonium salts, and phosphines. More preferred are secondary monoamines, tertiary monoamines, tertiary polyamines, imidazoles, amidines, quaternary ammonium salts, and phosphines having one or less groups that can react with an episulfide group. These may be used individually or in combination of two or more types. 【0025】The curing catalyst described above is typically used in an amount of 0.0001 to 1.0 mole per mole of episulfide compound, preferably 0.0001 to 0.5 moles, more preferably 0.0001 to less than 0.1 moles, and most preferably 0.0001 to 0.05 moles. If the amount of curing catalyst is greater than this, the refractive index and heat resistance of the cured product will decrease, and discoloration may occur. If the amount is less than this, curing may not be sufficient, resulting in insufficient heat resistance. 【0026】 Furthermore, the episulfide compounds of the present invention can also be used to produce optical materials by curing polymerization with compounds having two or more functional groups that can react with an episulfide group, compounds having one or more of these functional groups and one or more other homopolymerizable functional groups, or compounds having one functional group that can react with an episulfide group and can also be homopolymerized. Examples of compounds having two or more functional groups that can react with an episulfide group include epoxy compounds, known episulfide compounds, polycarboxylic acids, polycarboxylic acid anhydrides, mercaptocarboxylic acids, polymercaptans, mercapto alcohols, mercaptophenols, polyphenols, amines, amides, and the like. On the other hand, examples of compounds having one or more functional groups that can react with an episulfide group and one or more other homopolymerizable functional groups include epoxy compounds having unsaturated groups such as vinyl, aromatic vinyl, methacrylic, acrylic, and allyl, episulfide compounds, carboxylic acids, carboxylic acid anhydrides, mercaptocarboxylic acids, mercaptans, phenols, amines, and amides. Specific examples of compounds having two or more functional groups that can react with an episulfide group are shown below. 【0027】Specific examples of epoxy compounds include phenolic epoxy compounds produced by the condensation of polyhydric phenolic compounds such as hydroquinone, catechol, resorcinol, bisphenol A, bisphenol F, bisphenol sulfone, bisphenol ether, bisphenol sulfide, halogenated bisphenol A, and novolac resins with epihalohydrins; ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 1,3-propane Alcohol-based epoxy compounds produced by the condensation of polyhydric alcohol compounds such as benzoyl diol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, glycerin, trimethylolpropane trimethacrylate, pentaerythritol, 1,3- and 1,4-cyclohexanediol, 1,3- and 1,4-cyclohexanedimethanol, hydrogenated bisphenol A, bisphenol A ethylene oxide adduct, and bisphenol A propylene oxide adduct with epihalohydrins; adipic acid, sebatic acid, dodecandyl Glycidyl ester epoxy compounds produced by the condensation of polycarboxylic acid compounds such as carboxylic acids, dimer acids, phthalic acids, iso, terephthalic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, hexahydrophthalic acid, hetic acid, nadic acid, maleic acid, succinic acid, fumaric acid, trimellitic acid, benzenetetracarboxylic acid, benzophenonetetracarboxylic acid, naphthalenedicarboxylic acid, and diphenyldicarboxylic acid with epihalohydrins; ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,2-diaminobutane, 1,3-diaminobutane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, bis-(3-aminopropyl)ether, 1,2-bis-(3-aminopropoxy)ethane, 1,3-bis-(3-aminopropoxy)-2,2'-dimethylpropane, 1,2-, 1,3- or 1,4-bisaminocyclohexane, 1,3- or 1,4-bisaminomethylcyclohexane, 1,3- or 1,4-bisaminoethylcyclohexane, 1,3- or 1,4-Bisaminopropylcyclohexane, hydrogenated 4,4'-diaminodiphenylmethane, isophoronediamine, 1,4-bisaminopropylpiperazine, m- or p-phenylenediamine, 2,4- or 2,6-tolylenediamine, m- or p-xylylenediamine, 1,5- or 2,6-naphthalenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl ether, primary diamines such as 2,2-(4,4'-diaminodiphenyl)propane, N,N'-dimethylethylenediamine, N,N'-dimethyl-1,2-diaminopropane, N,N'-dimethyl-1,3-diaminopropane, N,N'-dimethyl-1,2-diaminobutane, N,N'-dimethyl-1,3-diaminobutane, N,N'-dimethyl-1,4 -diaminobutane, N,N'-dimethyl-1,5-diaminopentane, N,N'-dimethyl-1,6-diaminohexane, N,N'-dimethyl-1,7-diaminoheptane, N,N'-diethylethylenediamine, N,N'-diethyl-1,2-diaminopropane, N,N'-diethyl-1,3-diaminopropane, N,N'-diethyl-1,2-diaminobutane, N,N'-di Ethyl-1,3-diaminobutane, N,N'-diethyl-1,4-diaminobutane, N,N'-diethyl-1,6-diaminohexane, piperazine, 2-methylpiperazine, 2,5-or 2,6-dimethylpiperazine, homopiperazine, 1,1-di-(4-piperidyl)methane, 1,2-di-(4-piperidyl)ethane, 1,3-di-(4-piperidyl)propane, 1,Amine epoxy compounds produced by the condensation of secondary diamines such as 4-di-(4-piperidyl)-butane and epihalohydrin; alicyclic epoxy compounds such as 3,4-epoxycyclohexyl-3,4-epoxycyclohexanecarboxylate, vinylcyclohexanedioxide, 2-(3,4-epoxycyclohexyl)-5,5-spiro-3,4-epoxycyclohexane-metha-dioxide, bis(3,4-epoxycyclohexyl) adipate; epoxy compounds produced by the epoxidation of unsaturated compounds such as cyclopentadiene epoxide, epoxidized soybean oil, epoxidized polybutadiene, vinylcyclohexene epoxide; urethane-based epoxy compounds produced from the above-mentioned polyhydric alcohols, phenolic compounds, diisocyanates, glycidol, etc. can be mentioned. 【0028】 Specific examples of known episulfide compounds include episulfide compounds obtained by episulfidizing part or all of the epoxy groups of the above epoxy compounds. 【0029】 Specific examples of polyvalent carboxylic acids, polyvalent carboxylic acid anhydrides, polyphenols, amines, etc. include those described above as raw materials to react with epihalohydrin, which were explained in the section of the above epoxy compounds. 【0030】Polymercaptans specifically include linear dimercaptan compounds such as 1,2-dimercaptoethane, 1,3-dimercaptopropane, 1,4-dimercaptobutane, 1,6-dimercaptohexane, di(2-mercaptoethyl) sulfide, and 1,2-[bis(2-mercaptoethylthio)]ethane; branched aliphatic polymercaptan compounds such as 2-mercaptomethyl-1,3-dimercaptopropane, 2-mercaptomethyl-1,4-dimercaptobutane, 2-(2-mercaptoethylthio)-1,3-dimercaptopropane, 1,2-bis[(2-mercaptoethylthio)]-3-mercaptopropane, 1,1,1-tris(mercaptomethyl)propane, and tetrakismercaptomethylmethane; ethylene glycol dithioglycolate, ethylene glycol dithiopropionate, and 1,4-butane Examples include ester-containing aliphatic polymer mercaptan compounds such as diol dithioglycolate, 1,4-butanediol dithiopropionate, trimethylolpropanetris (β-thioglycolate), trimethylolpropanetris (β-thiopropionate), pentaerythritol tetrakis (β-thioglycolate), and pentaerythritol tetrakis (β-thiopropionate); and aliphatic cyclic dimercaptan compounds such as 1,4-dimercaptocyclohexane, 1,3-dimercaptocyclohexane, 1,4-dimercaptomethylcyclohexane, 1,3-dimercaptomethylcyclohexane, 2,5-dimercaptomethyl-1,4-dithiane, 2,5-dimercaptoethyl-1,4-dithiane, 2,5-dimercaptomethyl-1-thiane, and 2,5-dimercaptoethyl-1-thiane. 【0031】Also, representative specific examples of compounds having one or more functional groups capable of reacting with an episulfide group and one or more other monomers-polymerizable functional groups are shown below. Examples of epoxy compounds having an unsaturated group include vinylphenyl glycidyl ether, vinylbenzyl glycidyl ether, glycidyl methacrylate, glycidyl acrylate, allyl glycidyl ether, and the like. Examples of episulfide compounds having an unsaturated group include compounds obtained by episulfiding the epoxy groups of the above epoxy compounds having an unsaturated group, for example, vinylphenyl thioglycidyl ether, vinylbenzyl thioglycidyl ether, thioglycidyl methacrylate, thioglycidyl acrylate, allyl thioglycidyl ether, and the like. 【0032】 Examples of carboxylic acid compounds having an unsaturated group include α,β-unsaturated carboxylic acids such as acrylic acid, methacrylic acid, maleic acid, maleic anhydride, fumaric acid, and the like. Also, examples of amides having an unsaturated group include amides of the above α,β-unsaturated carboxylic acids. 【0033】 Also, preferable specific examples of compounds having one functional group capable of reacting with an episulfide group and also capable of monomer polymerization include compounds having one epoxy group or one episulfide group. More specifically, monoepoxy compounds such as ethylene oxide and propylene oxide, glycidyl esters of monocarboxylic acids such as acetic acid, propionic acid, and benzoic acid, glycidyl ethers such as methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, and butyl glycidyl ether, or monoepisulfide compounds such as ethylene sulfide and propylene sulfide, thioglycidyl esters having a structure derived from the above monocarboxylic acids and thioglycidol (1,2-epithio-3-hydroxypropane), and thioglycidyl ethers such as methyl thioglycidyl ether (1,2-epithiopropyloxymethane), ethyl thioglycidyl ether, propyl thioglycidyl ether, and butyl thioglycidyl ether. Among these, more preferable are compounds having one episulfide group. 【0034】 Compounds having two or more functional groups that can react with an episulfide group, compounds having one or more of these functional groups and one or more other homopolymerizable functional groups, and compounds having one functional group that can react with an episulfide group and is homopolymerizable can be produced by curative polymerization in the presence of a curative polymerization catalyst. Examples of curative catalysts include the aforementioned amines, phosphines, acids, etc. Specific examples of those used here are also mentioned above. 【0035】Furthermore, when using compounds containing unsaturated groups, it is preferable to use a radical polymerization initiator as a polymerization accelerator. A radical polymerization initiator can be any agent that generates radicals by heating or by ultraviolet light or electron beams, such as cumyl peroxyneodecanoate, diisopropyl peroxydicarbonate, diallyl peroxydicarbonate, di-n-propyl peroxydicarbonate, dimyristil peroxydicarbonate, cumyl peroxyneohexanoate, ter-hexyl peroxyneodecanoate, ter-butyl peroxyneodecanoate, ter-hexyl peroxyneohexanoate, ter-butyl peroxyneohexanoate, 2,4-dichlorobenzoyl peroxide, benzoyl peroxide, dicumyl peroxide, diter-butyl peroxide, and other peroxides; cumene hydroperoxide, ter-butyl hydroperoxide Examples of known thermal polymerization catalysts include hydroperoxides such as phosphates; azo compounds such as 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2-cyclopropylpropionitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonnitrile), 1-[(1-cyano-1-methylethyl)azo]formamide, 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile, 2,2'-azobis(2-methylpropane), and 2,2'-azobis(2,4,4-trimethylpentane); and known photopolymerization catalysts such as benzophenone, benzoin, and benzoin methyl ether. 【0036】Among these, preferred are peroxides, hydroperoxides, and azo compounds; more preferred are peroxides and azo compounds; and most preferred are azo compounds such as 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2-cyclopropylpropionitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonitride), 1-[(1-cyano-1-methylethyl)azo]formamide, 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile, 2,2'-azobis(2-methylpropane), and 2,2'-azobis(2,4,4-trimethylpentane). Furthermore, all of these can be used in mixtures. The amount of radical polymerization initiator added varies depending on the composition and curing method, so it cannot be determined definitively, but it is usually in the range of 0.01% to 5.0% by mass, preferably 0.1% to 2.0% by mass, relative to the total amount of the composition. 【0037】 Furthermore, when polymerizing and curing the episulfide compound of the present invention or a resin composition containing the episulfide compound to obtain an optical material, it is certainly possible to further improve the practicality of the obtained optical material by adding known additives such as antioxidants and ultraviolet absorbers. It is also possible to improve the release properties of the obtained optical material from the mold by using or adding known external and / or internal release agents. Examples of internal release agents include fluorine-based nonionic surfactants, silicone-based nonionic surfactants, alkyl quaternary ammonium salts, phosphate esters, acidic phosphate esters, alkali metal salts of acidic phosphate esters, metal salts of higher fatty acids, higher fatty acid esters, paraffin, wax, higher aliphatic amides, higher aliphatic alcohols, polysiloxanes, aliphatic amine ethylene oxide adducts, and the like. 【0038】When polymerizing and curing the episulfide compound of the present invention or a resin composition containing the episulfide compound to obtain an optical material, if the raw material is an episulfide compound, and optionally a curing catalyst, and reactable with an unsaturated episulfide group such as glycidyl methacrylate or thioglycidyl methacrylate (glycidyl methacrylate with the epoxy group episulfide modified), then after mixing in additives such as a radical polymerization initiator, a radically polymerizable monomer, and a mold release agent, antioxidant, and ultraviolet absorber, the optical material such as a lens can be manufactured by polymerizing and curing as follows. That is, the mixed raw materials are poured into a glass or metal mold, the polymerization and curing reaction is advanced by heating, and then the material is removed from the mold to manufacture the product. 【0039】 The curing time is 0.1 to 100 hours, usually 1 to 48 hours, and the curing temperature is -10 to 160°C, usually -10 to 140°C. Furthermore, after curing is complete, annealing the material at a temperature of 50 to 150°C for about 10 minutes to 5 hours is a preferred treatment to remove distortion from the optical material of the present invention. Surface treatments such as hard coating, anti-reflective coating, and anti-fogging treatment can be performed as needed. The method for manufacturing the optical material of the present invention is described in more detail below. As described above, the main raw material and auxiliary raw materials can be mixed and then injected into a mold to cure. The main raw material is an episulfide compound, and optionally a compound having two or more functional groups that can react with an episulfide group, or a compound having one or more of these functional groups and one or more other homopolymerizable functional groups, and a compound having one functional group that can react with an episulfide group and is homopolymerizable. Furthermore, optional curing catalysts, radical polymerization initiators, release agents, stabilizers, etc., can all be mixed simultaneously under stirring in the same container, or each raw material can be added and mixed in stages, or several components can be mixed separately and then remixed in the same container. 【0040】When mixing, the set temperature and the time required should basically be such that each component is thoroughly mixed. However, excessive temperature and time are unsuitable as they can cause undesirable reactions between the raw materials and additives, increase viscosity, and make casting difficult. The mixing temperature should be in the range of -10°C to 100°C, with a preferred temperature range of -10°C to 50°C, and a more preferred range of -5°C to 30°C. The mixing time should be from 1 minute to 5 hours, preferably from 5 minutes to 2 hours, more preferably from 5 minutes to 30 minutes, and most preferably from 5 minutes to 15 minutes. Performing a degassing operation under reduced pressure before, during, or after mixing each raw material and additive is a preferred method in that it prevents the generation of bubbles during subsequent casting polymerization curing. The degree of reduced pressure at this time should be from 0.1 mmHg to 700 mmHg, but a preferred range of 10 mmHg to 300 mmHg. Furthermore, filtering and removing impurities using a microfilter or the like during injection into the mold is preferable in order to further improve the quality of the optical material of the present invention. 【0041】 The present invention will be described below with reference to examples, but the present invention is not limited in any way to the following examples. 【0042】(Example 1) 3.00 g (0.006 mol) of 2,2'-[(6,6'-diphenyl[1,1'-binaphthalene]-2,2'-diyl)bis(oxy)]di(ethane-1-ol), represented by the following structural formula, was charged into a 100 mL glass reaction vessel equipped with a stirrer, a condenser, and a thermometer, and the reaction vessel was purged with nitrogen at room temperature. 5.27 g (0.057 mol) of epichlorohydrin and 0.06 g (0.001 mol) of tetramethylammonium chloride were added. The temperature was then raised to 55°C, and 0.68 g (0.017 mol) of granular sodium hydroxide was added in installments over 15 minutes, and the mixture was stirred at the same temperature for 5 hours. 50 g of ethyl acetate and 50 g of water were added to the resulting reaction mixture, and the aqueous layer was separated and removed. Next, the organic layer was washed several times with water, and the resulting extract was concentrated under reduced pressure. The extract was then purified by silica gel column (elution solvent: ethyl acetate:n-hexane = 1:1) to obtain 3.10 g of a colorless, viscous liquid (apparent yield 85%). NMR measurement identified the obtained product as an epoxy compound represented by the following structural formula. Epoxy compound obtained in Example 1 １ The H-NMR spectrum chart is shown in Figure 1. 2,2'-[(6,6'-diphenyl[1,1'-binaphthalene]-2,2'-diyl)bis(oxy)]di(ethane-1-ol) 【0043】(Example 2) In a 500 mL glass reaction vessel equipped with a stirrer and thermometer, 12.89 g (0.020 mol) of the epoxy compound obtained in Example 1, 29 g of tetrahydrofuran, and 26 g of methanol were charged and stirred at 25°C until dissolved. Then, 6.14 g (0.081 mol) of thiourea and 0.25 g (0.003 mol) of acetic anhydride were added and the mixture was stirred at 25°C for 23 hours. 100 g of 0.5 mol / L sulfuric acid was added to the resulting reaction mixture and stirred. Then, 100 g of ethyl acetate was added and the aqueous layer was separated and removed. Next, the organic layer was washed several times with water, and the extract obtained by concentrated under reduced pressure was purified by silica gel column (elution solvent: ethyl acetate:n-hexane = 1:3) to obtain 8.17 g of a colorless viscous liquid (apparent yield 60%). By NMR measurement, the obtained product was identified as an episulfide compound represented by the following structural formula. The episulfide compound obtained in Example 2 １ The H-NMR spectrum chart is shown in Figure 2. 【0044】 (Example 3) In a 500 mL glass reaction vessel equipped with a stirrer and thermometer, 20.00 g (0.041 mol) of the epoxy compound represented by the following structural formula, 59 g of tetrahydrofuran, and 53 g of methanol were charged and stirred at 25°C until dissolved. Then, 12.52 g (0.164 mol) of thiourea and 0.50 g (0.005 mol) of acetic anhydride were added and stirred at 25°C for 23 hours. 100 g of 0.5 mol / L sulfuric acid was added to the resulting reaction mixture and stirred. Then, 100 g of ethyl acetate was added and the aqueous layer was separated and removed. Next, the organic layer was washed several times with water, and the extract obtained by concentrated under reduced pressure was purified by silica gel column (elution solvent: ethyl acetate:n-hexane = 1:3) to obtain 15.80 g of a colorless viscous liquid (apparent yield 74%). By NMR measurement, the obtained product was identified as an episulfide compound represented by the following structural formula. The episulfide compound obtained in Example 3 １ The H-NMR spectrum chart is shown in Figure 3. 【0045】(Example 4) In a 500 mL glass reaction vessel equipped with a stirrer and thermometer, 10.00 g (0.014 mol) of the epoxy compound represented by the following structural formula, 190 g of tetrahydrofuran, and 112 g of methanol were charged and stirred at 25°C until dissolved. Then, 16.48 g (0.217 mol) of thiourea and 0.17 g (0.002 mol) of acetic anhydride were added and stirred at 25°C for 48 hours. 200 g of 0.5 mol / L sulfuric acid was added to the resulting reaction mixture and stirred. Then, 200 g of toluene was added and the aqueous layer was separated and removed. Next, the organic layer was washed several times with water, and the extract obtained by concentrated under reduced pressure was purified by silica gel column (elution solvent: ethyl acetate:n-hexane = 1:3) to obtain 5.22 g of a white solid (apparent yield 50%). By NMR measurement, the obtained product was identified as an episulfide compound represented by the following structural formula. The episulfide compound obtained in Example 4 １ The H-NMR spectrum chart is shown in Figure 4. 【0046】 (Example 5) In a 500 mL glass reaction vessel equipped with a stirrer and thermometer, 20.00 g (0.041 mol) of the epoxy compound represented by the following structural formula, 59 g of tetrahydrofuran, and 53 g of methanol were charged and stirred at 25°C until dissolved. Then, 12.52 g (0.164 mol) of thiourea and 0.50 g (0.005 mol) of acetic anhydride were added and stirred at 25°C for 23 hours. 100 g of 0.5 mol / L sulfuric acid was added to the resulting reaction mixture and stirred. Then, 200 g of toluene was added and the aqueous layer was separated and removed. Next, the organic layer was washed several times with water, and the extract obtained by concentrated under reduced pressure was purified by silica gel column (elution solvent: ethyl acetate:n-hexane = 1:20) to obtain 3.42 g of a colorless viscous liquid (apparent yield 26%). By NMR measurement, the obtained product was identified as an episulfide compound represented by the following structural formula. The episulfide compound obtained in Example 5 １ The H-NMR spectrum chart is shown in Figure 5. 【0047】(Comparative Example 1) In a 500 mL glass reaction vessel equipped with a stirrer and thermometer, 10.00 g (0.022 mol) of the epoxy compound represented by the following structural formula, 143 g of tetrahydrofuran, and 143 g of methanol were charged and stirred at 25°C until dissolved. Then, 13.69 g (0.086 mol) of thiourea and 0.26 g (0.003 mol) of acetic anhydride were added and stirred at 25°C for 23 hours. 100 g of 0.5 mol / L sulfuric acid was added to the resulting reaction mixture and stirred. Then, 100 g of ethyl acetate was added and the aqueous layer was separated and removed. Next, the organic layer was washed several times with water, and the extract obtained by concentrated under reduced pressure was purified by silica gel column (elution solvent: ethyl acetate:n-hexane = 1:3) to obtain 7.61 g of a white solid (apparent yield 71%). By NMR measurement, the obtained product was identified as an episulfide compound represented by the following structural formula. The episulfide compound obtained in Comparative Example 1 １ The H-NMR spectrum chart is shown in Figure 6. 【0048】 (Examples 6-9, Comparative Examples 2-4) A curable resin composition was obtained by mixing and stirring the components shown in Table 1 in predetermined ratios until uniform, and then evaporating and distilling off the solvent. The units of the components in Table 1 are expressed in parts by mass. The curable resin composition was sandwiched between two opposing glass plates separated by a 0.25 mm thick spacer, and cured by heating under the following conditions: heating from 30°C to 100°C in 10 hours, then heating from 100°C to 150°C in 1 hour, holding at 150°C for 1 hour, and then cooling from 150°C to 30°C in 1 hour. After that, the glass plates were removed to obtain a cured resin product. The physical properties of the obtained cured resin product were evaluated. 【0049】 <Temporal Stability of the Liquid> The prepared curable resin composition was stored at 25°C for one week, and the temporal stability of the liquid was evaluated by visual inspection to check for any changes in appearance such as crystal precipitation or solid sedimentation, according to the following criteria. Criteria for evaluating the temporal stability of the liquid ○: No change in appearance, and the liquid remained transparent. ×: Crystal precipitation or solid sedimentation was observed. 【0050】<Viscosity (mPa·s)> Measured at 23°C using an EMS viscometer (product name "EMS-1000S", manufactured by Kyoto Electronics Manufacturing Co., Ltd.). 【0051】 <Refractive Index, Abbe Number> The refractive index (nd) and Abbe number (νd) were measured using a refractometer (product name "KPR-3000", manufactured by Shimadzu Corporation). The measurement temperature was 25°C. 【0052】 <Curing Shrinkage Rate> The curing shrinkage rate was calculated using the following formula: Curing Shrinkage Rate (%) = (Specific Gravity of Cured Material - Specific Gravity of Monomer) ÷ Specific Gravity of Cured Material × 100 The specific gravity of the cured material was measured using an electronic hydrometer (product name "ELECTRONIC DENSIMETER ED-120T", manufactured by ALFA MiRAGE Co., Ltd.). The specific gravity of the monomer was measured using a density hydrometer (product name "DA-130N", manufactured by Kyoto Electronics Manufacturing Co., Ltd.). In both cases, the measurement temperature was 25°C. 【0053】 A1: Bis(2,3-epithiopropyl) sulfide B1: Episulfide compound obtained in Example 2 B2: Episulfide compound obtained in Example 3 B3: Episulfide compound obtained in Comparative Example 1 C1: Tetra-n-butylphosphonium bromide 【0054】 (Examples 10-14) When the physical properties of the epoxy compound (DPBN-EEP) obtained in Example 1 were investigated, it was found to be a liquid despite having a high refractive index of nd > 1.6. In this respect, the novel epoxy compound obtained in Example 1 is extremely useful, considering that the following compounds (BN-EEP, DNBN-EEP) are all solids. 【0055】Table 2 shows the results of measuring the physical properties of the epoxy compound (DPBN-EEP) obtained in Example 1, which was used to prepare the curable resin composition shown in Table 2. Specifically, the curable resin composition was obtained by mixing and stirring the components shown in Table 2 in a predetermined ratio until uniform, and then evaporating and distilling off the solvent. The units of the components in Table 2 are expressed in parts by mass. The curable resin composition was sandwiched between two opposing glass plates separated by a 0.25 mm thick spacer, and irradiated at 50 mW / cm using a UV-LED light irradiation device 365 (manufactured by Foseon Technology Japan Co., Ltd., peak wavelength 365 nm). ２ The resin was cured by repeating light irradiation for 10 minutes twice. Then, annealing was performed under the following conditions: heating from 30°C to 140°C in 1 hour, holding at 140°C for 4 hours, and then cooling from 140°C to 30°C in 1 hour. After that, the glass plate was removed to obtain the cured resin product. The physical properties of the obtained cured resin product were evaluated. 【0056】 <Temporal Stability of the Liquid> The prepared curable resin composition was stored at 25°C for one week, and the temporal stability of the liquid was evaluated by visual inspection to check for any changes in appearance such as crystal precipitation or solid sedimentation, according to the following criteria. Criteria for evaluating the temporal stability of the liquid ○: No change in appearance, and the liquid remained transparent. ×: Crystal precipitation or solid sedimentation was observed. 【0057】 <Viscosity (mPa·s)> Measured at 40°C using an EMS viscometer (product name "EMS-1000S", manufactured by Kyoto Electronics Manufacturing Co., Ltd.). 【0058】 <Refractive Index> The refractive index (nd) was measured using a refractometer (product name "KPR-3000", manufactured by Shimadzu Corporation). The measurement temperature was 25°C. - jER1750: Product name "jER1750", a bisphenol F type epoxy resin manufactured by Mitsubishi Chemical Corporation - KR-470: Product name "KR-470", a tetrafunctional oligomer containing alicyclic epoxy groups and cyclic siloxane manufactured by Shin-Etsu Chemical Co., Ltd. - X-40-2678: Product name "X-40-2678", a difunctional oligomer containing alicyclic epoxy groups and cyclic siloxane manufactured by Shin-Etsu Chemical Co., Ltd. - Celoxide 8010: Product name "Celoxide 8010", an alicyclic epoxy resin manufactured by Daicel Corporation - CPI-210S: Product name "CPI-210S", a photoacid generator manufactured by Sunapro Co., Ltd.

Claims

1. An episulfide compound represented by the following formula (1). (R １ and R ２ Each of these independently represents a group selected from the group consisting of a hydrogen atom, a phenyl group, a naphthyl group, an alkyl group, and a halogen atom. n and m each independently represent an integer from 0 to 5.

2. The episulfide compound according to claim 1, wherein the formula (1) is the following formula (2). (R １ , R ２ , n and m are as defined in formula (1).) 3. R １ and R ２ The episulfide compound according to claim 1, wherein n represents a group selected from the group consisting of a hydrogen atom, a phenyl group, and a naphthyl group, and n and m represent 1.

4. A resin composition containing the episulfide compound according to any one of claims 1 to 3.

5. An optical material obtained by polymerizing and curing the resin composition described in claim 4.

6. An optical lens comprising the optical material described in claim 5.

7. An epoxy compound represented by the following formula (3).

8. A resin composition containing the epoxy compound described in claim 7.

9. An optical material obtained by polymerizing and curing the resin composition described in claim 8.

10. An optical lens comprising the optical material described in claim 9.

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