Compositions and optical materials and lenses using the same

Abstract

A composition is provided that yields an optical material with high refractive index and excellent hue. One composition comprises the following formula (1): [wherein, Ar represents an aromatic ring, m represents an integer from 2 to 8, n represents an integer from 0 to 6, and m+n is the number of carbon atoms constituting the aromatic ring or less, R...] 1 The compounds (a) and polythiols shown are represented independently by alkylthio, epoxyalkylthio, thiol, halogen, hydroxyl, dialkylthiocarbamoyl, or dialkylcarbamoylthio.

Description

Technical Field

[0001] This invention relates to compositions and optical materials and lenses using the same. Background Technology

[0002] Optical materials, especially those used in eyeglass lenses, require optical properties such as heat resistance, low specific gravity, high transparency, low yellowness, high refractive index, and high Abbe number. In recent years, there has been a demand for further high-performance optical materials, particularly those with high refractive index and high Abbe number.

[0003] Polymerizable compositions for optical materials using cyclic sulfide compounds have attracted considerable attention as materials for achieving high refractive indices and high Abbe numbers. For example, Patent Document 1 discloses an invention relating to a polymerizable composition containing a thioepoxy compound having one or more intramolecular disulfide bonds, wherein the curing resin has a refractive index (nd) of 1.71 or higher. It is stated that, in this case, bis(2,3-cyclothiopropyl) disulfide is most preferably the thioepoxy compound having one or more intramolecular disulfide bonds.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: Japanese Patent Application Publication No. 2002-194083 Summary of the Invention

[0007] The problem the invention aims to solve

[0008] According to the polymerizable composition described in Patent Document 1, optical materials with high refractive index can be obtained. However, optical materials with even higher refractive indices are needed. Furthermore, it has been found that sometimes, the higher the refractive index of an optical material, the lower its hue. Therefore, the present invention provides a composition that yields optical materials with both high refractive index and excellent hue.

[0009] Solution for solving the problem

[0010] The inventors conducted in-depth research to solve the aforementioned technical problems. They discovered that by combining cyclic sulfur compounds and polythiol compounds with aromatic skeletons, the above-mentioned technical problems could be solved, thus completing the present invention. For example, the present invention is as follows.

[0011] [1] A composition comprising a compound (a) of formula (1) and a polythiol (b).

[0012]

[0013] In the above formula,

[0014] Ar represents the aromatic ring.

[0015] m represents an integer from 2 to 8.

[0016] n represents an integer from 0 to 6.

[0017] Where m+n represents the number of carbons forming the aromatic ring or less.

[0018] R 1 Each of these groups independently represents an alkylthio group, an epoxy alkylthio group, a thiol group, a halogen group, a hydroxyl group, a dialkylthiocarbamoyl group, or a dialkylcarbamoylthio group.

[0019] [2] According to the composition described in [1] above, Ar is an aromatic ring composed of carbon and hydrogen.

[0020] [3] The composition according to [1] or [2] above, wherein m is 2 or 3.

[0021] [4] The composition according to any one of [1] to [3] above, wherein m+n is 2 to 6.

[0022] [5] The composition according to any one of [1] to [4] above, wherein the content of said compound (a) is 5 to 95% by mass relative to the total mass of the composition.

[0023] [6] The composition according to any one of [1] to [5] above, wherein the polythiol (b) comprises selected from 1,2,6,7-tetramercapto-4-thiaheptan, methanedithiol, (mercaptomethyldithio)methanethiol, bis(2-mercaptoethyl) sulfide, 2,5-bis(mercaptomethyl)-1,4-dithiane, 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, 4,8-dimercaptomethyl-1,11-dimercaptopropane. At least one of the following groups: 3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 1,1,3,3-tetra(mercaptomethylthio)propane, pentaerythritol, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, and thiacyclopropanemethanethiol.

[0024] [7] The composition according to any one of [1] to [6] above further comprises the compound (c) shown in formula (2).

[0025]

[0026] In the above formula,

[0027] p represents an integer from 0 to 4.

[0028] q represents an integer from 0 to 2.

[0029] [8] The composition according to any one of [1] to [7] above further comprises sulfur.

[0030] [9] The composition according to any one of [1] to [8] above further comprises a prepolymerization catalyst.

[0031]

[10] According to the composition described above [9], wherein the prepolymer catalyst comprises at least one selected from the group consisting of 2-mercapto-1-methylimidazole, 2-methyl-N-imidazole and 1,2,2,6,6-pentamethylpiperidin methacrylate.

[0032]

[11] A precured material, which is formed by prepolymerizing the composition described in any one of [1] to

[10] above.

[0033]

[12] An optical material which is formed by curing the composition of any one of [1] to

[10] above or the precured material described in

[11] above.

[0034]

[13] An optical lens comprising the optical material described in

[12] above.

[0035] The effects of the invention

[0036] According to the present invention, it is possible to provide compositions that yield optical materials with high refractive index and excellent hue. Detailed Implementation

[0037] The present invention will now be described in detail with reference to embodiments and examples. However, the present invention is not limited to the embodiments and examples shown below, and can be implemented by any modifications without departing from the spirit of the present invention.

[0038] <Composition>

[0039] The composition of the present invention comprises compound (a) of formula (1) and polythiol (b). In addition, it may further comprise compound (c) of formula (2), sulfur, polymerizable compound, prepolymerization catalyst, polymerization catalyst, polymerization modifier, additives, etc.

[0040] The composition, by including compound (a) of formula (1), i.e., a cyclic sulfur compound having an aromatic skeleton, can achieve a high refractive index in the resulting cured material (optical material). Furthermore, by including polythiol (b), the composition can improve the hue of the resulting cured material (optical material). By combining these components, both the refractive index and hue of the resulting cured material (optical material) can be improved. Therefore, the composition is preferably a composition for optical materials.

[0041] [Compound(a)]

[0042] Compound (a) is represented by the following formula (1).

[0043]

[0044] Ar represents an aromatic ring. Examples of aromatic rings include aromatic rings composed of carbon and hydrogen, and aromatic heterocycles (aromatic rings containing heteroatoms). It should be noted that Ar has 2 or more carbon atoms, preferably 2 to 18, more preferably 2 to 12, and even more preferably 3 to 6. Furthermore, Ar is preferably a 5-membered ring or a 6-membered ring, more preferably a 6-membered ring.

[0045] There are no particular limitations on the aromatic rings composed of carbon and hydrogen mentioned above, and examples include benzene rings, naphthalene rings, fluorene rings, anthracene rings, and phenanthrene rings. Among them, benzene rings are preferred as aromatic rings composed of carbon and hydrogen.

[0046] The aforementioned aromatic heterocycles are not particularly limited, and examples include furan rings, pyran rings, pyrrole rings, imidazole rings, pyrazole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, triazole rings, thiadiazole rings, pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, triazine rings, indole rings, isoindole rings, indazole rings, quinoline rings, isoquinoline rings, phthalazine rings, phenanthridine rings, and acridine rings. Preferably, the aromatic heterocycle is a furan ring, pyran ring, pyrrole ring, imidazole ring, pyrazole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, triazole ring, thiadiazole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, or triazine ring; more preferably, a triazine ring or a thiadiazole ring; and even more preferably, a thiadiazole ring.

[0047] In the above, Ar is preferably an aromatic ring composed of carbon and hydrogen, and more preferably a benzene ring.

[0048] m represents an integer from 2 to 8. From the viewpoint of hue and ease of composition, it is preferably 2, 3 or 6, more preferably 2 or 3, and even more preferably 3.

[0049] n represents an integer from 0 to 6, preferably from 0 to 2, more preferably 0 or 1, and even more preferably 0.

[0050] m+n is the number of carbons constituting the aromatic ring or less, preferably 2 to 6, more preferably 3 to 6, even more preferably 2 to 3, and particularly preferably 3. It should be noted that "the number of carbons constituting the aromatic ring or less" means no more than the number of carbons present in an aromatic ring. For example, in the case of a benzene ring, which is an aromatic ring composed of carbon and hydrogen, the number of carbons constituting the ring is 6, therefore m+n is 6 or less. Furthermore, in the case of a thiadiazole ring, which is an aromatic heterocyclic ring, the number of carbons constituting the ring is 2, therefore m+n is 2 or less.

[0051] R 1Each can be independently represented as alkylthio, epoxyalkylthio, thiol, halogen, hydroxyl, dialkylthiocarbamoyl, or dialkylcarbamoylthio.

[0052] There are no particular limitations on the aforementioned alkylthio groups, and examples include methylthio, ethylthio, propylthio, butylthio, isobutylthio, sec-butylthio, tert-butylthio, pentylthio, hexylthio, etc.

[0053] As for the aforementioned alkyl thio group, there are no particular limitations; β-epoxypropyl thio group can be listed as an example.

[0054] There are no particular limitations on the aforementioned halogen groups, and examples include fluorine (-F), chlorine (-Cl), bromine (-Br), and iodine (-I).

[0055] There are no particular limitations on the aforementioned dialkylthiocarbamoyl group; examples include dimethylthiocarbamoyl, diethylthiocarbamoyl, and ethylmethylthiocarbamoyl.

[0056] In another embodiment, compound (a) is represented by the following formula (1').

[0057]

[0058] In formula (1'), m represents an integer from 2 to 6. From the viewpoint of hue and ease of synthesis, it is preferably 2, 3 or 6, more preferably 2 or 3, and even more preferably 3.

[0059] In formula (1'), n represents an integer from 0 to 4, preferably from 0 to 2, more preferably 0 or 1, and even more preferably 0.

[0060] In formula (1'), m+n is 6 or less (m+n≤6), preferably 2 to 6, more preferably 3 to 6, and even more preferably 3.

[0061] In equation (1'), R 1 Same as equation (1) above.

[0062] As specific examples of compound (a), there are no particular limitations, and examples include bis(cyclic sulfide) compounds such as 1,3-bis(β-cyclic thiopropylthio)benzene and 1,4-bis(β-cyclic thiopropylthio)benzene; tri(cyclic sulfide) compounds such as 1,3,5-tris(β-cyclic thiopropylthio)benzene, 1,2,4-tris(β-cyclic thiopropylthio)benzene, and 1,2,5-tris(β-cyclic thiopropylthio)benzene; alkylthio-substituted bis(cyclic sulfide) compounds such as 1-methyl-3,5-bis(β-cyclic thiopropylthio)benzene, 1-methyl-2,4-bis(β-cyclic thiopropylthio)benzene, 1-methyl-2,5-bis(β-cyclic thiopropylthio)benzene, 1-ethyl-3,5-bis(β-cyclic thiopropylthio)benzene, and 1-tert-butylthio-3,5-bis(β-cyclic thiopropylthio)benzene. Sulfur compounds; epoxide thiolated di(cyclic sulfur) compounds such as 1-(β-epoxypropylthio)-3,5-bis(β-cyclic thiopropylthio)benzene, 1-(β-epoxypropylthio)-2,4-bis(β-cyclic thiopropylthio)benzene, 1-(β-epoxypropylthio)-2,5-bis(β-cyclic thiopropylthio)benzene; thiol-substituted di(cyclic sulfur) compounds such as 1-mercapto-3,5-bis(β-cyclic thiopropylthio)benzene, 1-mercapto-2,4-bis(β-cyclic thiopropylthio)benzene, 1-mercapto-2,5-bis(β-cyclic thiopropylthio)benzene; 1-fluoro-3,5-bis(β-cyclic thiopropylthio)benzene, 1-chloro-3,5-bis(β-cyclic thiopropylthio)benzene, 1-bromo-3,5-bis(β-cyclic thiopropylthio)benzene, Halogen-substituted bis(cyclic sulfur) compounds such as 1-chloro-2,4-bis(β-cyclothiopropylthio)benzene and 1-chloro-2,5-bis(β-cyclothiopropylthio)benzene; hydroxy-substituted bis(cyclic sulfur) compounds such as 1-hydroxy-3,5-bis(β-cyclothiopropylthio)benzene, 1-hydroxy-2,4-bis(β-cyclothiopropylthio)benzene and 1-hydroxy-2,5-bis(β-cyclothiopropylthio)benzene; 1-dimethylthiocarbamoyl-3,5-bis(β-cyclothiopropylthio)benzene, 1-diethylthiocarbamoyl-3,5-bis(β-cyclothiopropylthio)benzene, 1-diethylthiocarbamoyl-2,4-bis(β-cyclothiopropylthio)benzene, 1-diethylthiocarbamoyl-2,5-bis(β-cyclothiopropylthio)benzene Dialkyl thiocarbamoyl-substituted bis(cyclic sulfide) compounds such as benzene; 1-dimethylcarbamoylthio-3,5-bis(β-cyclothiopropylthio)benzene, 1-diethylcarbamoylthio-3,5-bis(β-cyclothiopropylthio)benzene, 1-dimethylcarbamoylthio-2,4-bis(β-cyclothiopropylthio)benzene, 1-dimethylcarbamoylthio-2,5-bis(β-cyclothiopropylthio)benzene and other dialkylcarbamoylthio-substituted bis(cyclic sulfide) compounds; 2,5-bis(β-cyclothiopropylthio)-1,3,4-thiadiazole, 3,4-bis(β-cyclothiopropylthio)-1,2,5-thiadiazole, 2,4,6-tris(β-cyclothiopropylthio)-1,3,5-triazine and other heterocyclic compounds.Preferably, the following are selected: 1,3-bis(β-cyclothiopropylthio)benzene, 1,4-bis(β-cyclothiopropylthio)benzene, 1,3,5-tris(β-cyclothiopropylthio)benzene, 1-alkylthio-3,5-bis(β-cyclothiopropylthio)benzene, 1-epoxyalkylthio-3,5-bis(β-cyclothiopropylthio)benzene, 1-thio-3,5-bis(β-cyclothiopropylthio)benzene, 1-halo-3,5-bis(β-cyclothiopropylthio)benzene, 1-hydroxy-3,5-bis(β-cyclothiopropylthio)benzene, 1-dialkylthiocarbamoyl-3,5-bis(β-cyclothiopropylthio)benzene, and 1-alkylcarbamoylthio-3,5-bis(β-cyclothiopropylthio)benzene. The compounds are 2,5-bis(β-cyclothiopropylthio)-1,3,4-thiadiazole, 3,4-bis(β-cyclothiopropylthio)-1,2,5-thiadiazole, and 2,4,6-tris(β-cyclothiopropylthio)-1,3,5-triazine, more preferably 1,3-bis(β-cyclothiopropylthio)benzene, 1,4-bis(β-cyclothiopropylthio)benzene, 1,3,5-tris(β-cyclothiopropylthio)benzene, 2,5-bis(β-cyclothiopropylthio)-1,3,4-thiadiazole, and 2,4,6-tris(β-cyclothiopropylthio)-1,3,5-triazine. From the viewpoint of further increasing the refractive index, 1,3,5-tris(β-cyclothiopropylthio)benzene is even more preferred. It should be noted that the above compound (a) can be used alone or in combination of two or more.

[0063] The content of compound (a) relative to the total mass of the composition is preferably 0.1 to 99.5% by mass, more preferably 5 to 95% by mass, even more preferably 10 to 95% by mass, and particularly preferably 10 to 85% by mass. When the content of compound (a) is within the above range, a sufficient color-enhancing effect can be obtained. It should be noted that, in one embodiment, from the viewpoint of improving color tone, the content of compound (a) relative to the total mass of the composition is preferably 0.1 to 60% by mass, more preferably 1 to 55% by mass, and even more preferably 3 to 30% by mass.

[0064] [Polythiols(b)]

[0065] Polythiols (b) are compounds having two or more thiol groups (-SH) in one molecule. In this case, substances belonging to compound (a) (cyclic sulfur compounds with an aromatic skeleton) are not included in polythiols (b).

[0066] As for polythiols (b), there are no particular limitations, but from the viewpoint of high color improvement effect, 1,2,6,7-tetramercapto-4-thiaheptane, methanedithiol, (mercaptomethyldithio)methanethiol, bis(2-mercaptoethyl) sulfide, 2,5-bis(mercaptomethyl)-1,4-dithiaane, 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane are preferred. Undecane, 1,1,3,3-tetra(mercaptomethylthio)propane, pentaerythritol, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, and thiacyclopropane methanethiol, more preferably bis(2-mercaptoethyl) sulfide, 1,2,6,7-tetramercapto-4-thiaheptane, methanedithiol, (mercaptomethyldithio)methanethiol, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and even more preferably bis(2-mercaptoethyl) sulfide, 1,2,6,7-tetramercapto-4-thiaheptane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane. It should be noted that the above polythiols (b) can be used alone or in combination of two or more.

[0067] The content of polythiol (b) relative to the total mass of the composition is preferably 0.1 to 30% by mass, more preferably 0.1 to 20% by mass, even more preferably 0.5 to 20% by mass, and particularly preferably 1 to 15% by mass. When the content of polythiol (b) is within the above range, the balance between color stabilization and heat resistance is improved, and therefore preferred. It should be noted that, in one embodiment, from the viewpoint of improving color hue, the content of compound (b) relative to the total mass of the composition is preferably 2 to 30% by mass, more preferably 4 to 30% by mass, and even more preferably 7.5 to 25% by mass.

[0068] [Compound (c)]

[0069] In one embodiment, the composition may further comprise compound (c). Compound (c) is represented by the following formula (2). Compound (c) can copolymerize with compound (a), and by using it with compound (a), it has the effect of improving curing reactivity.

[0070]

[0071] p represents an integer from 0 to 4, preferably from 0 to 2, and more preferably 0 or 1.

[0072] q represents an integer from 0 to 2, preferably from 0 to 2, and more preferably 0 or 1.

[0073] As specific examples of compound (c), there are no particular limitations, and bis(β-cyclothiopropyl) sulfide and bis(β-cyclothiopropyl) disulfide can be listed. Among them, bis(β-cyclothiopropyl) sulfide is preferred. The above compound (c) can be used alone or in combination of two or more. It should be noted that bis(β-cyclothiopropyl) sulfide is equivalent to the compound in formula (2) above where p = q = 0, and bis(β-cyclothiopropyl) disulfide is equivalent to the compound in formula (2) above where p = 0 and q = 1.

[0074] The content of compound (c) relative to the total mass of the composition is 0 to 70% by mass, preferably 1 to 60% by mass, and more preferably 1 to 50% by mass. When the content of compound (c) is within the above range, the curing reactivity can be improved while ensuring heat resistance, and is therefore preferred.

[0075] [sulfur]

[0076] In one embodiment, the composition may further contain sulfur. By containing sulfur, the refractive index of the resulting optical material can be increased.

[0077] There are no particular restrictions on the shape of sulfur; it can be any shape. Specific forms include micronized sulfur, colloidal sulfur, precipitated sulfur, crystalline sulfur, and sublimed sulfur. Among these, micronized sulfur is preferred from the viewpoint of dissolution rate.

[0078] The particle size (diameter) of sulfur is preferably less than 10 mesh (1.70 mm opening), more preferably less than 30 mesh (500 μm opening), and even more preferably less than 60 mesh (250 μm opening). Sulfur is more easily soluble when the particle size is less than 10 mesh, which is therefore preferred.

[0079] The purity of sulfur is not particularly limited, but is preferably 98% or higher, more preferably 99.0% or higher, even more preferably 99.5% or higher, and particularly preferably 99.9% or higher. A sulfur purity of 98% or higher further improves the color tone of the resulting optical material, and is therefore preferred.

[0080] The sulfur content relative to the total mass of the composition is preferably 0 to 20% by mass, more preferably 0.1 to 18% by mass, and even more preferably 1 to 15% by mass. When the sulfur content is within the above range, the balance between the refractive index enhancement effect and solubility is excellent, and therefore preferred.

[0081] [Polymerizing compounds]

[0082] In one embodiment, the composition may further comprise a polymerizable compound. By comprising a polymerizable compound, the physical properties of the optical material can be adjusted. It should be noted that a "polymerizable compound" refers to a compound that can copolymerize with compound (a).

[0083] There are no particular restrictions on the polymerizable compounds mentioned above, as long as they can copolymerize with compound (a). Examples include cyclic sulfur compounds, vinyl compounds, methacrylamide compounds, acryloyl compounds, and allyl compounds, excluding compounds (a) and (c). These compounds can be used alone or in combination of two or more.

[0084] There are no particular limitations on the amount of polymeric compound added, as long as it does not impede the effect of the present invention. For example, it is preferably 0 to 30% by mass, more preferably 1 to 30% by mass, and even more preferably 1 to 20% by mass, relative to the total mass of the composition.

[0085] [Prepolymerization catalyst]

[0086] In one embodiment, the composition may further comprise a prepolymerization catalyst. By comprising a prepolymerization catalyst, the precured product described later can be suitably manufactured.

[0087] There are no particular limitations on the prepolymerization catalysts, and examples include imidazoles, phosphines, thioureas, quaternary ammonium salts, quaternary phosphonium salts, tertiary sulfonium salts, secondary iodonium salts, and hindered amines. Among these, imidazoles and hindered amines are preferred from the viewpoint of good compatibility with the composition.

[0088] As for the aforementioned imidazoles, there are no particular restrictions, and examples include N-benzylimidazole, 4-methylimidazole, 4-ethylimidazole, 1-phenylimidazole, 2-methyl-N-methylimidazole, etc.

[0089] There are no particular limitations on the hindered amines mentioned above, and examples include 1,2,2,6,6-pentamethylpiperidin methacrylate, 1,2,2,6,6-pentamethylpiperidin acrylate, and 1,2,2,6,6-pentamethylpiperidin 4-vinylbenzoic acid.

[0090] The prepolymerization catalyst preferably comprises at least one selected from the group consisting of 2-mercapto-1-methylimidazolium, 2-methyl-N-imidazolium, and 1,2,2,6,6-pentamethylpiperidinium methacrylate. It should be noted that the above-mentioned prepolymerization catalyst can be used alone or in combination of two or more.

[0091] The amount of prepolymer catalyst added varies depending on the composition, mixing ratio, and polymerization curing method, and therefore cannot be generalized. However, generally, it is preferably 0.0001% to 10% by mass, more preferably 0.003% to 3.0% by mass, relative to 100% by mass of the total of compound (a), polythiol (b), compound (c), and sulfur. When the amount of prepolymer catalyst added is 0.0001% by mass or more, the prepolymerization reaction can proceed appropriately, which is preferred. On the other hand, when the amount of prepolymer catalyst added is 10% by mass or less, the oxidation resistance is improved, which is also preferred.

[0092] [Polymerization catalyst]

[0093] In one embodiment, the composition may further comprise a polymerization catalyst. By comprising a polymerization catalyst, the composition can be suitably polymerized to produce an optical material.

[0094] There are no particular limitations on polymerization catalysts, and examples include amines, phosphines, quaternary ammonium salts, quaternary phosphonium salts, tertiary sulfonium salts, secondary iodonium salts, inorganic acids, Lewis acids, organic acids, silicic acids, tetrafluoroborates, peroxides, azo compounds, condensates of aldehydes and ammonia compounds, guanidines, thioureas, thiazoles, sulfenamides, thiurams, dithiocarbamates, xanthates, and acidic phosphates. Among these, amines, phosphines, quaternary ammonium salts, and quaternary phosphonium salts are preferred. It should be noted that these polymerization catalysts can be used alone or in combination of two or more.

[0095] The amount of polymerization catalyst added is preferably 0.0001 to 10% by mass relative to the total mass of the composition, more preferably 0.01 to 3% by mass.

[0096] [Polymerization modifier]

[0097] In one embodiment, the composition may further comprise a polymerization modifier.

[0098] There are no particular limitations on the polymerization modifiers, and halides from groups 13 to 16 of the long-period periodic table can be listed. Among them, halides of silicon, germanium, tin, and antimony are preferred, and chlorides of germanium, tin, and antimony having alkyl groups are more preferred. These polymerization modifiers can be used alone or in combination of two or more.

[0099] The amount of polymerization modifier added relative to the total mass of the composition is preferably 0.0001 to 5.0% by mass, more preferably 0.01 to 2% by mass.

[0100] [additive]

[0101] In one embodiment, the composition may further include additives. There are no particular limitations on the additives, and examples include antioxidants, bluing agents, UV absorbers, deodorizers, adhesion improvers, release agents, and free radical polymerization initiators. These additives may be used alone or in combination of two or more.

[0102] The content of the additive relative to the total mass of the composition is preferably 0 to 10% by mass, more preferably 0.5 to 10% by mass.

[0103] [Composition of the composition]

[0104] In one embodiment, the composition has the following composition. That is, the composition comprises, relative to the total amount of the composition:

[0105] Compound (a): 5-95% by mass, preferably 10-95% by mass;

[0106] Polythiols (b): 0.1–30% by mass, preferably 0.5–20% by mass;

[0107] Compound (c): 0–85% by mass, preferably 0–80% by mass;

[0108] Sulfur: 0–20% by mass, preferably 0–15% by mass;

[0109] Prepolymerization catalyst: 0-5% by mass, preferably 0-3% by mass;

[0110] Polymerization catalyst: 0-5% by mass, preferably 0.0001-3% by mass; and

[0111] Polymerization modifier: 0-5% by mass, preferably 0.0001-3% by mass.

[0112] <Method for manufacturing the composition>

[0113] The above composition can be manufactured using known methods without particular limitations. Specifically, it can be manufactured by mixing compound (a), polythiol (b), and, if necessary, compound (c), sulfur, etc.

[0114] <Pre-cured material>

[0115] According to one aspect of the present invention, a pre-cured material can be provided. The aforementioned pre-cured material is formed by prepolymerizing the above-described composition. From these viewpoints, it is preferred to produce a pre-cured material because it reduces the rate of viscosity increase, improves the transparency of optical materials, and facilitates handling. It should be noted that, in this specification, "pre-cured material" refers to a liquid with a viscosity of 5000 mps or less, including polymers, partial polymers, oligomers, etc., formed by polymerization of at least one of compound (a), polythiol (b), compound (c), sulfur, and polymerizable compounds. It should also be noted that, in this specification, "viscosity" is a value measured by the following method.

[0116] [Viscosity Measurement Methods]

[0117] The viscosity of the pre-cured material at 30°C was measured using a cone-plate viscometer DV2THACP (Brookfield AMETEK).

[0118] <Pre-cured material manufacturing method>

[0119] According to one aspect of the present invention, a method for manufacturing a pre-cured material can be provided. The aforementioned method for manufacturing a pre-cured material includes a prepolymerization step of prepolymerizing the composition.

[0120] [Prepolymerization process]

[0121] The prepolymerization process is the process of prepolymerizing the composition.

[0122] The composition described above can be used. Preferably, the aforementioned composition contains a prepolymerization catalyst.

[0123] From the viewpoint that the polymerization process described later is preferably performed after prepolymerization, the prepolymerization process is preferably performed by injecting the material into a mold or similar mold. At this time, from the viewpoint of improving the quality of the optical material, it is preferable to remove impurities by filtering with a filter or similar device with a pore size of approximately 0.1 to 5 μm before injection molding.

[0124] The aforementioned prepolymerization temperature is preferably -10 to 160°C, more preferably 0 to 100°C, and even more preferably 20 to 80°C.

[0125] The prepolymerization time is preferably 0.1 to 480 minutes, more preferably 0.1 to 420 minutes, and even more preferably 0.1 to 360 minutes.

[0126] In one embodiment, the prepolymerization is preferably carried out at -10 to 160°C for 0.1 to 480 minutes, more preferably at 0 to 100°C for 0.1 to 420 minutes, and even more preferably at 20 to 80°C for 0.1 to 360 minutes.

[0127] Prepolymerization can be carried out under normal pressure, under pressure, or under reduced pressure. When prepolymerization is carried out under reduced pressure, the reaction typically proceeds more gently compared to when it is carried out at normal pressure, as hydrogen sulfide, which promotes the reaction, can be removed. It should be noted that when carried out at normal pressure, it can be conducted in the atmosphere or in a non-reactive gas.

[0128] In the prepolymerization process, it is preferable to detect the degree of progress of the prepolymerization reaction. There are no particular limitations on the aforementioned detection methods; examples include liquid chromatography, viscosity measurement, specific gravity measurement, and refractive index measurement. Among these, refractive index measurement is preferred due to its simplicity. It should be noted that these detection methods can be used individually or in combination of two or more.

[0129] It is preferable to detect the progress of the prepolymerization reaction online. In particular, when prepolymerization is carried out under pressure or depressurization, online detection eliminates the need to depressurize or depressurize to obtain a sample for testing, which is even more preferable. During online detection, for example, when measuring the refractive index, by immersing the detection section of the refractometer in the composition before prepolymerization and the prepolymerization reaction solution, the increase in refractive index accompanying the reaction can be detected, thus controlling the progress of the reaction. It should be noted that when using a detection method that measures the change in refractive index or other measured values ​​due to temperature, it is preferable to perform a multiple regression analysis on the measurement temperature, refractive index, and refractive index at a reference temperature to predetermine the relationship between the temperature of the detection section and the refractive index. Specifically, it is preferable to use a refractometer with a temperature correction function that can automatically convert the refractive index to a reference temperature. Examples of online refractometers include those using a light-emitting diode as a light source and a CCD unit to identify the angle of light reflected from a prism.

[0130] <Optical Materials>

[0131] According to one aspect of the present invention, an optical material can be provided. The aforementioned optical material is obtained by curing the aforementioned composition or the aforementioned pre-cured material. That is, the optical material is a cured product of the aforementioned composition or pre-cured material.

[0132] The optical materials used in this method have high refractive index and excellent color tone.

[0133] Specifically, the refractive index of the optical material is preferably 1.70 or higher, more preferably 1.72 or higher, even more preferably 1.73 or higher, and particularly preferably 1.75 or higher. That is, the refractive index of the optical material obtained from the above composition is preferably 1.70 or higher, more preferably 1.72 or higher, even more preferably 1.73 or higher, and particularly preferably 1.75 or higher. It should be noted that the value of "refractive index" was determined by the method described in the examples.

[0134] Furthermore, regarding the hue of the optical material, the YI value is preferably 5 or less, more preferably 4 or less, even more preferably 3 or less, and particularly preferably 2 or less. That is, the YI value of the optical material obtained from the above composition is preferably 5 or less, more preferably 4 or less, even more preferably 3 or less, and particularly preferably 2 or less. It should be noted that in this specification, the "YI value" is determined by the method described in the examples.

[0135] The optical materials produced by this method have high refractive index and excellent color tone, so various comonomers can be blended in the composition and their blending amount can be increased, thereby enabling the design of optical materials with a wide range of physical properties.

[0136] <Methods for Manufacturing Optical Materials>

[0137] According to one aspect of the present invention, a method for manufacturing an optical material can be provided. The aforementioned manufacturing method includes a polymerization step of polymerizing the aforementioned composition or the aforementioned pre-cured material.

[0138] [Polymerization Process]

[0139] The polymerization process is the process of polymerizing the above composition or the above pre-cured material.

[0140] The polymerization process is typically carried out by injecting the composition or pre-cured material into a mold such as a casting mold, allowing it to polymerize. When using a composition, from the viewpoint of improving the quality of optical materials, it is preferable to remove impurities by filtering with a filter or the like with a pore size of about 0.1 to 5 μm before injection molding.

[0141] In one embodiment, the polymerization process includes: a process of heating to a polymerization temperature, a process of maintaining the polymerization temperature, and a process of cooling down.

[0142] The aforementioned polymerization can be carried out in multiple stages. That is, there can be two or more steps in maintaining the polymerization temperature. In one embodiment, the polymerization step includes: a step of heating to a first polymerization temperature, a step of maintaining the first polymerization temperature, a step of heating to a second polymerization temperature, a step of maintaining the second polymerization temperature, and a step of cooling. In this case, the first polymerization temperature is lower than the second polymerization temperature. In another embodiment, the polymerization step includes: a step of heating to a first polymerization temperature, a step of maintaining the first polymerization temperature, a step of cooling to a second polymerization temperature, a step of maintaining the second polymerization temperature, and a step of cooling. In this case, the first polymerization temperature is higher than the second polymerization temperature.

[0143] The heating rate for the heating process is preferably 0.1℃ to 100℃ / h. Similarly, the cooling rate for the cooling process is preferably 0.1℃ to 100℃ / h.

[0144] The polymerization temperature is usually -10℃ to 140℃, preferably 0 to 140℃.

[0145] The polymerization time is typically 1 to 100 hours, preferably 1 to 72 hours. It should be noted that "polymerization time" in this specification refers to the time including the heating and cooling processes.

[0146] It should be noted that after polymerization, the resulting optical material is preferably annealed. Annealing can prevent or suppress deformation of the optical material. The annealing temperature is preferably 50–150°C. Furthermore, the annealing time is preferably 10 minutes to 5 hours.

[0147] The resulting optical materials can be subjected to surface treatments such as dyeing, hard coating, impact-resistant coating, anti-reflection, and anti-fogging as needed.

[0148] <Applications of Optical Materials>

[0149] The aforementioned optical materials are useful not only in optical components, mechanical parts, electrical / electronic parts, automotive parts, civil engineering materials, and molding materials, but also in various applications such as coatings and adhesives. Specifically, these optical materials are preferably used in lenses such as eyeglass lenses, (digital) camera lenses, beam focusing lenses, and light-diffusing lenses; LED sealing materials; optical adhesives; light propagation bonding materials; optical fibers; prisms; filters; diffraction gratings; surface glass; and transparent and protective glass for display devices. They are also used in display device applications such as substrates for display elements (LCDs, OLEDs, PDPs), substrates for color filters, substrates for touch panels, information recording substrates, display backlights, light guides, display protective films, anti-reflective films, and anti-fog films. The aforementioned optical materials are particularly preferred for applications such as optical lenses, prisms, optical fibers, information recording substrates, and filters, and more preferably for optical lenses. In one embodiment, an optical lens comprising the aforementioned optical materials is provided.

[0150] The optical lenses obtained from the compositions of this invention exhibit excellent stability, hue, and transparency, making them highly useful in fields such as telescopes, bifocal glasses, and television projectors, where expensive high-refractive-index glass lenses have historically been used. Preferably, they are used in the form of aspherical lenses, depending on the requirements.

[0151] Example

[0152] The present invention will now be described in detail with reference to specific embodiments. However, the implementation methods may be modified as appropriate as long as the effects of the present invention can be achieved.

[0153] The following methods are used to analyze and evaluate optical materials.

[0154] Refractive index of optical materials

[0155] The refractive index of optical materials at 25°C was measured using a KPR-2000 digital precision refractometer (manufactured by Shimadzu Corporation) for e-rays (546.1 nm).

[0156] [Tone Evaluation of Optical Materials]

[0157] The YI value of a 2.6 mm thick optical material was measured using a CM-5 spectrophotometer (KONICAMINOLTA JAPAN, INC.) at 25 °C.

[0158] [Synthetic Example 1: Synthesis of 1,3,5-trimercaptobenzene (hereinafter referred to as TMB)]

[0159]

[0160] The synthesis was performed according to Beilstein Journal of Organic Chemistry, 8, 461-471, No. 53; 2012. Details are as follows.

[0161] Specifically, a four-necked flask equipped with a thermometer and a dropping funnel was purged with nitrogen. Then, 400 g of N-methylpyrrolidone and 82.7 g (2067 mmol) of sodium hydroxide were added, and the mixture was stirred at 5 °C. Next, 186.4 g (2067 mmol) of tert-butylthiol was added dropwise, and the mixture was stirred at 5 °C for 3 hours. Then, 50.0 g (275.56 mmol) of 1,3,5-trichlorobenzene was added, the temperature was raised to 120 °C, and the mixture was stirred for 24 hours. The reaction mixture was then cooled to 25 °C, 400 g of toluene was added, and the mixture was washed three times with 400 g of water. The solvent was removed by distillation, yielding 45.3 g (132.3 mmol) of crude 1,3,5-tris(tert-butylthio)benzene (TTBB).

[0162] 45.3 g (132.3 mmol) of the crude TTBB product was placed in a three-necked flask equipped with a thermometer, and the reaction vessel was purged with nitrogen. Then, 436 g of toluene was added, and the mixture was stirred at 20 °C. Next, 19.4 g (145.4 mmol) of aluminum chloride was added, and the mixture was stirred for 3 hours. 225 g of 20% sulfuric acid was added, and the toluene layer was washed three times with water. The solvent was removed by distillation, yielding 16.1 g (92.4 mmol) of crude TMB product.

[0163] The crude TMB product was purified by silica gel column chromatography, yielding a fraction of TMB1 (100% purity) (TMB fraction 1) and two fractions containing TMB2 and TMB3 (TMB fractions 2 and 3). The results are shown in Table 1 below.

[0164] [Synthesis Example 2: Synthesis of TMB]

[0165]

[0166] The synthesis was performed with reference to Bulletin de la Societe Chimique de France, (2), 302-8; 1987. Details are as follows.

[0167] Specifically, 30.0 g (238 mmol) of phloroglucinol and 375 g of N,N-dimethylformamide were added to a three-necked flask equipped with a thermometer. The reaction mixture was then cooled to 5 °C, and 133.4 g (1189 mmol) of 1,4-diazabicyclo[2.2.2]octane and 147.0 g (1189 mmol) of dimethylthiocarbamoyl chloride were added, followed by stirring for 24 hours. Next, 300 g of chloroform was added, and the mixture was washed three times with 300 g of 10% NaOH aqueous solution. The solvent was removed by distillation, yielding 73.8 g (190 mmol) of crude 1,3,5-tris(dimethylthiocarbamoyl)benzene.

[0168] 73.8 g of the crude 1,3,5-tris(dimethylcarbamoyl)benzene was placed in a three-necked flask equipped with a thermometer and stirred at 240 °C for 7 hours. Then, it was cooled to 25 °C to obtain 73.8 g (190 mmol) of crude 1,3,5-tris(dimethylcarbamoyl)thiobenzene.

[0169] 73.8 g of the crude 1,3,5-tris(dimethylcarbamoylthio)benzene was placed in a three-necked flask equipped with a thermometer. Next, 826 g of diethylene glycol, 89.1 g of water, and 53.4 g (952 mmol) of potassium hydroxide were added, and the mixture was stirred at 95 °C for 10 hours. Then, the mixture was cooled to 25 °C, and 370 g of 20% sulfuric acid and 740 g of chloroform were added. The organic layer was washed three times with water, and the solvent was removed by distillation, yielding 15.9 g (91 mmol) of crude TMB product.

[0170] The crude TMB product was purified by silica gel column chromatography, yielding a fraction of TMB1 (100% purity) (TMB fraction 4) and three fractions containing TMB4, TMB5, and TMB6 (TMB fractions 5–7). The results are shown in Table 1 below.

[0171]

[0172] [Table 1]

[0173]

[0174] [Synthetic Example 3: Synthesis of Cyclic Sulfur Compounds]

[0175] 15.0 g (86.1 mmol) of TMB fraction 1 was added to a four-necked flask equipped with a thermometer and a dropping funnel, and the reaction vessel was purged with nitrogen. Then, a solution obtained by dissolving 0.72 g of 24% sodium hydroxide aqueous solution in 59.4 g of methanol and 65.0 g of toluene were added to the same reaction vessel, and the mixture was stirred while cooling to 5 °C. Next, 24.7 g (266.8 mmol) of epichlorohydrin was added dropwise while stirring, maintaining the liquid temperature between 5 and 15 °C. After the addition was complete, the mixture was stirred at 5 °C for 3 hours to obtain 1,3,5-tris(3-chloro-2-hydroxypropylthio)benzene.

[0176] Next, while maintaining the liquid temperature at 5–15°C, 64.6 g (387.3 mmol) of a 24% sodium hydroxide aqueous solution was added dropwise. After the addition was complete, the liquid temperature was maintained at 15°C, and the mixture was allowed to mature for 17 hours. The organic layer was washed three times with 150 g of water, and the solvent was removed by distillation, yielding 29.0 g of 1,3,5-tris(β-epoxypropylthio)benzene (overall yield 98%).

[0177] To the obtained 29.0 g (84.7 mol) of 1,3,5-tris(β-(epoxypropylthio)benzene), 145 mL of toluene, 145 mL of methanol, 1.56 g (15.2 mmol) of acetic anhydride, and 38.7 g (508.0 mmol) of thiourea were added, and the mixture was stirred at 20°C for 24 hours. 145 g of 20% sulfuric acid was added, and the toluene layer was washed three times with water. The solvent was removed by distillation, yielding 23.1 g of 1,3,5- Crude tri(β-(cyclothiopropylthio)benzene) (hereinafter referred to as compound 1) was obtained. The crude product was purified by silica gel column chromatography, thereby obtaining a fraction (a-1) of 100% purity of compound 1 and two fractions (a-2 and a-3) containing compound 2 (1-mercapto-3,5-bis(β-(cyclothiopropylthio)benzene) and compound 3 (1-(ββ-epoxypropylthio)-3,5-bis(β-(cyclothiopropylthio)benzene). The results are shown in Table 2 below.

[0178] [Synthetic Example 4: Synthesis of Cyclic Sulfur Compounds]

[0179] TMB fraction 2 was used instead of TMB fraction 1, and the crude product of compound 1 was obtained using the same method as in Synthesis Example 3. The crude product was purified by silica gel column chromatography to obtain a fraction (a-1) of 100% purity of compound 1 and a fraction (a-4) containing compound 4 (1-chloro-3,5-bis(β-cyclothiopropylthio)benzene). The results are shown in Table 2 below.

[0180] [Synthetic Example 5: Synthesis of Cyclic Sulfides]

[0181] TMB fraction 3 was used instead of TMB fraction 1, and the crude product of compound 1 was obtained using the same method as in Synthesis Example 3. The crude product was purified by silica gel column chromatography to obtain a fraction (a-1) of 100% purity of compound 1 and a fraction (a-5) containing compound 5 (1-tert-butylthio-3,5-bis(β-cyclothiopropylthio)benzene). The results are shown in Table 2 below.

[0182] [Synthetic Example 6: Synthesis of Cyclic Sulfides]

[0183] TMB fraction 5 was used instead of TMB fraction 1, and the crude product of compound 1 was obtained using the same method as in Synthesis Example 3. The crude product was purified by silica gel column chromatography to obtain a fraction (a-1) of 100% purity of compound 1 and a fraction (a-6) containing compound 6 (1-hydroxy-3,5-bis(β-cyclothiopropylthio)benzene). The results are shown in Table 2 below.

[0184] [Synthetic Example 7: Synthesis of Cyclosulfide Compounds]

[0185] The crude product of compound 1 was obtained by replacing TMB fraction 1 with TMB fraction 6, otherwise using the same method as in Synthesis Example 3. The crude product was purified by silica gel column chromatography to obtain a fraction (a-1) of 100% purity of compound 1 and a fraction (a-7) containing compound 7 (1-dimethylthiocarbamoyl-3,5-bis(β-cyclothiopropylthio)benzene). The results are shown in Table 2 below.

[0186] [Synthetic Example 8: Synthesis of Cyclic Sulfur Compounds]

[0187] The crude product of compound 1 was obtained by replacing TMB fraction 1 with TMB fraction 7, otherwise using the same method as in Synthesis Example 3. The crude product was purified by silica gel column chromatography to obtain a fraction (a-1) of 100% purity of compound 1 and a fraction (a-8) containing compound 8 (1-dimethylcarbamoylthio-3,5-bis(β-cyclothiopropylthio)benzene). The results are shown in Table 2 below.

[0188] [Synthetic Example 9: Synthesis of Cyclic Sulfides]

[0189] Using 1,3-dimercaptobenzene (manufactured by Tokyo Chemical Industry Co., Ltd.) instead of TMB fraction 1, the crude product of compound 9 (1,3-bis(β-cyclothiopropylthio)benzene) was obtained by the same method as in Synthesis Example 3. The crude product was purified by silica gel column chromatography to obtain fractions (a-9) of 100% purity of compound 9. The results are shown in Table 2 below.

[0190] [Synthetic Example 10: Synthesis of Cyclic Sulfur Compounds]

[0191] Bismuthiol (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of TMB fraction 1, and the crude product of compound 10 (2,5-bis(β-cyclothiopropylthio)-1,3,4-thiadiazole) was obtained using the same method as in Synthesis Example 3. The crude product was purified by silica gel column chromatography to obtain fractions (a-10) of compound 10 with a purity of 100%. The results are shown in Table 2 below.

[0192] [Synthetic Example 11: Synthesis of Cyclic Sulfur Compounds]

[0193] Thiocyanuric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of TMB fraction 1, and the crude product of compound 11 (2,4,6-tris(β-cyclothiopropylthio)-1,3,5-triazine) was obtained using the same method as in Synthesis Example 3. The crude product was purified by silica gel column chromatography to obtain a fraction (a-11) of 100% purity of compound 11. The results are shown in Table 2 below.

[0194] Compound 1: 1,3,5-Tris(β-cyclothiopropylthio)benzene

[0195] Compound 2: 1-Mercapto-3,5-bis(β-cyclothiopropylthio)benzene

[0196] Compound 3: 1-(β-epoxypropylthio)-3,5-bis(β-cyclothiopropylthio)benzene

[0197] Compound 4: 1-Chloro-3,5-bis(β-cyclothiopropylthio)benzene

[0198] Compound 5: 1-tert-butylthio-3,5-bis(β-cyclothiopropylthio)benzene

[0199] Compound 6: 1-Hydroxy-3,5-bis(β-cyclothiopropylthio)benzene

[0200] Compound 7: 1-Dimethylthiocarbamoyl-3,5-bis(β-cyclothiopropylthio)benzene

[0201] Compound 8: 1-Dimethylcarbamoylthio-3,5-bis(β-cyclothiopropylthio)benzene

[0202] Compound 9: 1,3-bis(β-cyclothiopropylthio)benzene

[0203] Compound 10: 2,5-bis(β-cyclothiopropylthio)-1,3,4-thiadiazole

[0204] Compound 11: 2,4,6-tris(β-cyclothiopropylthio)-1,3,5-triazine

[0205]

[0206] [Table 2]

[0207]

[0208] [raw material]

[0209] As polythiols (b), prepare the following compounds b-1 to b-3.

[0210] b-1: 1,2,6,7-Tetramercapto-4-thiaheptane

[0211] b-2: Bis(2-mercaptoethyl) sulfide

[0212] b-3: 4,8-Dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane

[0213]

[0214] In addition, as compound (c), the following compounds c-1 to c-2 are prepared.

[0215] c-1: Bis(β-cyclothiopropyl) sulfide

[0216] c-2: Bis(β-cyclothiopropyl)disulfide

[0217]

[0218] [Example 1]

[0219] The composition is prepared by mixing 80 parts by mass of fraction a-1, 20 parts by mass of compound b-1, 0.02 parts by mass of tetra-n-butylphosphine bromide as a polymerization catalyst, and 0.05 parts by mass of di-n-butyltin dichloride as a polymerization modifier, and simultaneously degassing under vacuum.

[0220] [Examples 2-18, Comparative Examples 1-3]

[0221] Except for the changes to the composition shown in Table 3, the composition was manufactured using the same method as in Example 1.

[0222] [evaluate]

[0223] The compositions prepared in Examples 1-18 and Comparative Examples 1-3 were heated at 30°C for 10 hours, then heated to 100°C over 10 hours, and finally heated at 100°C for 5 hours to polymerize and solidify. After natural cooling, they were annealed at 120°C for 30 minutes to produce optical materials.

[0224] The results of the evaluation of the refractive index and hue of the manufactured optical materials are shown in Table 3 below.

[0225] [Table 3]

[0226]

[0227] As can be seen from the results in Table 3, the cured products (optical materials) formed by curing the compositions of Examples 1 to 18 have high refractive index and excellent color tone.

[0228] On the other hand, Comparative Example 1 does not contain polythiols (b), resulting in an insufficient hue.

[0229] Furthermore, it is known that in Comparative Example 2, which involves the prior art using compound c-1 (bis(β-cyclothiopropyl) sulfide), the refractive index is insufficient.

[0230] Furthermore, it can be seen that when sulfur is added to Comparative Example 3 to increase the refractive index, the hue decreases.

Claims

1. A composition comprising a compound (a) of formula (1) and a polythiol (b), In the above formula, Ar represents the aromatic ring. m is 3. n represents an integer from 0 to 6. in, m+n is less than or equal to the number of carbons forming the aromatic ring. R 1 Each of these groups independently represents an alkylthio group, an epoxy alkylthio group, a thiol group, a halogen group, a hydroxyl group, a dialkylthiocarbamoyl group, or a dialkylcarbamoylthio group. The composition further comprises compound (c) of formula (2) below. In the above formula, p represents an integer from 0 to 4. q represents an integer from 0 to 2.

2. The composition according to claim 1, wherein, Ar is an aromatic ring composed of carbon and hydrogen.

3. The composition according to claim 1, wherein, m+n ranges from 3 to 6.

4. The composition according to claim 1, wherein, The content of compound (a) is 5-95% by mass relative to the total mass of the composition.

5. The composition according to any one of claims 1 to 4, wherein, The polythiol (b) comprises, selected from 1,2,6,7-tetramercapto-4-thiaheptane, methanedithiol, (mercaptomethyldithio)methanethiol, bis(2-mercaptoethyl) sulfide, 2,5-bis(mercaptomethyl)-1,4-dithiane, 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane. At least one of the following groups: 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 1,1,3,3-tetra(mercaptomethylthio)propane, pentaerythritol, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene and thiacyclopropanemethanethiol.

6. The composition according to any one of claims 1 to 4, further comprising sulfur.

7. The composition according to any one of claims 1 to 4, further comprising a prepolymerization catalyst.

8. The composition according to claim 7, wherein, The prepolymerization catalyst comprises at least one selected from the group consisting of 2-mercapto-1-methylimidazole, 2-methyl-N-imidazole and 1,2,2,6,6-pentamethylpiperidinium methacrylate.

9. A precured product formed by prepolymerizing the composition according to any one of claims 1 to 8.

10. An optical material formed by curing the composition of any one of claims 1 to 8 or the precured material of claim 9.

11. An optical lens comprising the optical material of claim 10.

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