Optical material and spectacle lens

Abstract

An optical material containing: an organic dye (A) containing a porphyrin compound (a) represented by formula (A1); an organic dye (B) containing a porphyrin compound (b) represented by formula (B1); and a resin. In formula (A1), M represents cobalt or vanadium oxide, R1 represents a chlorine atom or a bromine atom, n represents 1 or 2, and R2 represents a phenyl group or a phenyl group substituted with an aromatic group or an aliphatic group having 1-7 carbon atoms. In formula (B1), M represents a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a metal hydroxide atom, or a metal oxide atom, and R3 and R4 each represent a hydrogen atom, a halogen atom, an aliphatic group having 3-10 carbon atoms, or an aromatic group which may contain a halogen atom. # imgabs0 #

Description

Technical Field

[0001] The present disclosure relates to optical materials and eyeglass lenses. Background Art

[0002] In recent years, optical materials are used in various applications. As optical materials, for example, optical materials containing polymers and organic pigments are widely known. As optical materials, specifically, filters, lenses, etc. can be cited.

[0003] Among them, plastic lenses are lighter and less likely to break than inorganic lenses, and therefore have rapidly become popular as optical materials for eyeglass lenses, camera lenses, and the like in recent years.

[0004] For example, Patent Document 1 describes a filter, in which, in the transmission spectrum of the filter, the minimum value of the transmittance in the wavelength range of 550 nm to 650 nm is 20% to 60%, and is included in the range of 570 nm to 620 nm. The filter contains one or more absorption pigments, and the absorption pigments are tetraazaporphyrin pigments whose central metal is nickel or cobalt and whose substituents are fluorobenzoic acid.

[0005] For example, Japanese Patent Document 2 describes an optical component having the following transmission spectrum characteristics: it includes a local maximum in a wavelength range greater than 315 nm and less than 400 nm, and a local minimum in a wavelength range greater than 380 nm and less than 500 nm, and the wavelength of the local maximum is shorter than the wavelength of the local minimum.

[0006] For example, Japanese Patent Document 3 describes an optical material that satisfies the following (1) to (3) in a transmittance curve when measured at a thickness of 2 mm and is CIE 1976 (L ＊ , a ＊ , b ＊ ) hue in color space, a ＊ is above -4 and below 1, b ＊ is greater than -1 and less than 11. (1) The transmittance curve has a maximum transmittance T1 in the wavelength range of 400nm to 445nm, and the maximum T1 is greater than 65%. (2) The transmittance curve has a minimum transmittance T2 in the wavelength range of 445nm to 485nm, and the minimum T2 is greater than 60% and less than 90%. (3) The minimum transmittance in the wavelength range of 650nm to 800nm ​​is greater than 75%, and the average transmittance in the wavelength range of 650nm to 800nm ​​is greater than 80%.

[0007] Patent Document 1: Japanese Patent Application Publication No. 2021-162625

[0008] Patent Document 2: International Publication No. 2017-090128

[0009] Patent Document 3: International Publication No. 2021-024962 Summary of the invention

[0010] Problems to be solved by the invention

[0011] As the optical material, for example, a spectacle lens can be cited. As the spectacle lens, a spectacle lens having a blue light blocking capability is known.

[0012] The blue light blocking capability of eyeglass lenses having a blue light blocking capability may decrease over time after manufacture.

[0013] Additionally, the appearance of eyeglass lenses with blue light blocking capabilities sometimes has an unnatural color tint.

[0014] An embodiment of the present disclosure has been devised in view of the above circumstances to provide an optical material and an eyeglass lens that can suppress a decrease in blue light blocking capability for a long period of time and have a natural color tone in appearance.

[0015] Means for solving problems

[0016] Means for solving the above-mentioned problems include the following.

[0017] <1> An optical material comprising: an organic dye A containing a porphyrin compound a represented by the following formula (A1); an organic dye B containing a porphyrin compound b represented by the following formula (B1); and a resin.

[0018] [Chemical formula 1]

[0019]

[0020] In formula (A1), M represents cobalt or vanadium oxide, R 1 represents a chlorine atom or a bromine atom, n represents 1 or 2, R 2 It represents a phenyl group, or a phenyl group substituted with an aromatic group or an aliphatic group having 1 to 7 carbon atoms.

[0021] [Chemical formula 2]

[0022]

[0023] In formula (B1), M represents a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a hydroxide metal atom or an oxide metal atom, and R 3 and R 4 Each represents a hydrogen atom, a halogen atom, an aliphatic group having 3 to 10 carbon atoms, or an aromatic group which may contain a halogen atom.

[0024] <2> The optical material according to <1>, wherein in the formula (B1), M is cobalt or vanadium oxide.

[0025] <3> The optical material according to <1> or <2>, wherein the porphyrin-based compound a is a compound represented by the following formula (A2).

[0026] [Chemical formula 3]

[0027]

[0028] In formula (A2), M represents cobalt or vanadium oxide.

[0029] <4> The optical material according to any one of <1> to <3>, wherein the porphyrin-based compound b is a compound represented by the following formula (B2), the following formula (B3), or the following formula (B4).

[0030] [Chemical formula 4]

[0031]

[0032] In formula (B2), M represents a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a hydroxide metal atom or an oxide metal atom.

[0033] [Chemical formula 5]

[0034]

[0035] In formula (B3), M represents a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a hydroxide metal atom or an oxide metal atom.

[0036] [Chemical formula 6]

[0037]

[0038] In formula (B4), M represents a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a hydroxide metal atom, or an oxide metal atom.

[0039] <5> The optical material according to any one of <1> to <4>, wherein a ratio of a content of the organic dye B to a content of the organic dye A is 0.5 to 5.0.

[0040] <6> An optical material as described in any one of <1> to <5>, wherein, in a spectral spectrum, when the maximum absorption wavelength in the wavelength range of 440nm to 500nm is set as the maximum absorption wavelength a, and the maximum absorption wavelength in the wavelength range of 550nm to 600nm is set as the maximum absorption wavelength b, the value obtained by subtracting the maximum absorption wavelength a from the maximum absorption wavelength b is 100nm to 160nm.

[0041] <7> The optical material according to any one of <1> to <6>, wherein in the spectral spectrum, the maximum absorption wavelength in the wavelength range of 440 nm to 500 nm is set as the maximum absorption wavelength a, the maximum absorption wavelength in the wavelength range of 550 nm to 600 nm is set as the maximum absorption wavelength b, the transmittance at the maximum absorption wavelength a when the thickness is 2 mm is set as transmittance T1, and the transmittance at the maximum absorption wavelength b when the thickness is 2 mm is set as transmittance T2,

[0042] The transmittance T1 is within the range of 65%T to 85%T, and the transmittance T2 is within the range of 65%T to 85%T.

[0043] <8> The optical material according to any one of <1> to <7>, wherein in the spectral spectrum, when the maximum absorption wavelength in the wavelength range of 440 nm to 500 nm is defined as the maximum absorption wavelength a and the transmittance at the maximum absorption wavelength a when the thickness is 2 mm is defined as the transmittance T1,

[0044] The absolute value of the difference in transmittance T1 before and after the weather resistance test described below, namely ΔT1, is 1.0%T or less.

[0045] <Weather resistance test>

[0046] The test sample with a thickness of 2 mm formed of the above optical material was subjected to temperature of 50°C, humidity of 40% RH, and illumination of 60 W / m 2 , and irradiation time of 150 hours, irradiated with a xenon lamp.

[0047] <9> The optical material according to any one of <1> to <7>, wherein in the spectral spectrum, the maximum absorption wavelength in the wavelength range of 440 nm to 500 nm is set as the maximum absorption wavelength a, the maximum absorption wavelength in the wavelength range of 550 nm to 600 nm is set as the maximum absorption wavelength b, the transmittance at the maximum absorption wavelength a when the thickness is 2 mm is set as transmittance T1, and the transmittance at the maximum absorption wavelength b when the thickness is 2 mm is set as transmittance T2,

[0048] The total of the absolute value ΔT1 of the difference in transmittance T1 before and after the weathering test described below and the absolute value ΔT2 of the difference in transmittance T2 before and after the weathering test described below is 3.0%T or less.

[0049] <Weather resistance test>

[0050] The test sample with a thickness of 2 mm formed of the above optical material was subjected to temperature of 50°C, humidity of 40% RH, and illumination of 60 W / m 2 , and irradiation time of 150 hours, irradiated with a xenon lamp.

[0051] <10> The optical material according to any one of <1> to <9>, which has a visible light transmittance of 80%T or more.

[0052] <11> The optical material according to any one of <1> to <10>, wherein the chroma C ＊ It is 0.01~4.0.

[0053] <12> The optical material according to any one of <1> to <11>, wherein the resin comprises polythiourethane or polysulfide.

[0054] <13> A spectacle lens comprising the optical material according to any one of <1> to <12>.

[0055] Effects of the Invention

[0056] According to one embodiment of the present disclosure, an optical material and eyeglass lens can be provided that can suppress the reduction of blue light interception capability for a long period of time and have a natural color tone in appearance. BRIEF DESCRIPTION OF THE DRAWINGS

[0057] [ Figure 1 ] is the spectral spectrum of the lens in which the content of the pigment (1-A) in Comparative Example 3 was changed to 10 ppm before and after 300 hours in the weather resistance test.

[0058] [ Figure 2 ] are spectral spectra of the lens in which the content of the pigment (3-A) in Comparative Example 4 was changed to 10 ppm before the test, after 150 hours, and after 300 hours in the weather resistance test. DETAILED DESCRIPTION

[0059] Hereinafter, the contents of the present disclosure will be described in detail.

[0060] Although the description of the constituent elements described below may be made based on representative embodiments of the present disclosure, the present disclosure is not limited to such embodiments.

[0061] In the present disclosure, “to” indicating a numerical range is used to mean that the numerical values ​​described before and after it are included as the lower limit and the upper limit.

[0062] In the numerical range recorded in stages in this disclosure, the upper limit or lower limit recorded in one numerical range can be replaced by the upper limit or lower limit of the numerical range recorded in other stages. In addition, in the numerical range recorded in this disclosure, the upper limit or lower limit of its numerical range can be replaced by the value shown in the embodiment.

[0063] In the present disclosure, compounds not explicitly described as substituted or unsubstituted may have any substituent within a range that does not impair the effects of the present disclosure.

[0064] In the present disclosure, when a plurality of substances belonging to each component are present in a layer, the amount of each component of the composition refers to the total amount of the plurality of substances present in the composition unless otherwise specified.

[0065] It should be noted that in the present disclosure, a combination of preferred embodiments is a more preferred embodiment.

[0066] In the present disclosure, ppm (parts per million) refers to ppm based on mass.

[0067] <<Optical Materials>>

[0068] The optical material of the present disclosure comprises: an organic pigment A containing a porphyrin compound a represented by the following formula (A1); an organic pigment B containing a porphyrin compound b represented by the following formula (B1); and a resin.

[0069] The optical material of the present disclosure can suppress the reduction of the blue light interception capability for a long period of time by including the above-mentioned structure, and has a natural color tone in appearance.

[0070] In the present disclosure, the natural color tone refers to a gray tone with suppressed chroma.

[0071] The blue light blocking capability of eyeglass lenses having a blue light blocking capability may decrease over time after manufacture.

[0072] The reason why the optical material of the present disclosure can suppress the reduction of the blue light intercepting ability over a long period of time is considered to be due to its excellent weather resistance.

[0073] <Organic pigment A>

[0074] The organic dye A contains a porphyrin compound a represented by the following formula (A1).

[0075] The organic dye A preferably has a maximum absorption wavelength within a wavelength range of 440 nm to 500 nm.

[0076] The wavelength of maximum absorption can be the minimum value of transmittance.

[0077] [Chemical formula 7]

[0078]

[0079] In formula (A1), M represents cobalt or vanadium oxide, R 1 represents a chlorine atom or a bromine atom, n represents 1 or 2, R 2 It represents a phenyl group, or a phenyl group substituted with an aromatic group or an aliphatic group having 1 to 7 carbon atoms.

[0080] The multiple R in formula (A1) 1 It can be the same or different.

[0081] The multiple R in formula (A1) 2 It can be the same or different.

[0082] R 1 Preferably it represents a bromine atom.

[0083] R 2 Preferably it represents phenyl.

[0084] R 2 In the aliphatic group having 1 to 7 carbon atoms, there can be mentioned a linear, branched or cyclic alkyl group having 1 to 7 carbon atoms, a linear, branched or cyclic alkenyl group, a linear, branched or cyclic alkynyl group, and the like.

[0085] Examples of the linear, branched or cyclic alkyl group having 1 to 7 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1,2-dimethylpropyl, 1-methylbutyl, 2-methylbutyl, n-hexyl, 2-methylpentyl, 4-methylpentyl, 4-methyl-2-pentyl, 1,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 3-methylhexyl, 5-methylhexyl and 2,4-dimethylpentyl.

[0086] Examples of the linear, branched or cyclic alkenyl group having 1 to 7 carbon atoms include vinyl, 1-methylvinyl, propenyl, 2-butenyl and 2-pentenyl.

[0087] Examples of the linear, branched or cyclic alkynyl group having 1 to 7 carbon atoms include ethynyl, propynyl, butynyl, 1,3-butadienyl, 2-pentynyl, 2,4-pentadienyl, 2-hexynyl, 3,3-dimethyl-1-butynyl and 3-heptynyl.

[0088] R 2 In the above, examples of the aromatic group include substituted or unsubstituted phenyl and the like.

[0089] As described above, the porphyrin compound a has cobalt or vanadium oxide as the central metal. This is particularly helpful in improving weather resistance. As a result, it also helps to suppress the reduction of blue light interception ability.

[0090] The reason why the central metal of the porphyrin compound a, cobalt or vanadium oxide, helps to suppress the decrease in blue light interception capability is unclear, but it is speculated that it is due to the following factors: the electronic state of the complex (pigment) can be stabilized by using cobalt or vanadium oxide as the central metal.

[0091] In addition, from the viewpoint of weather resistance, it is considered that the porphyrin compound a absorbs wavelengths on the shorter wavelength side compared with the porphyrin compound b, and therefore contributes more.

[0092] In the optical material of the present disclosure, the porphyrin-based compound a is preferably a compound represented by the following formula (A2).

[0093] [Chemical formula 8]

[0094]

[0095] In formula (A2), M represents cobalt or vanadium oxide.

[0096] The content of the organic dye A is preferably 0.5 ppm to 10.0 ppm.

[0097] By setting the content of the organic dye A to 0.5 ppm or more, the blue light intercepting capability can be maintained more favorably.

[0098] The organic pigment A easily absorbs light of higher energy (ie, shorter wavelength) than the organic pigment B. Therefore, the lower limit of the content of the organic pigment A is helpful for maintaining the blue light interception capability well.

[0099] From the above viewpoints, the content of the organic dye A is more preferably 1.0 ppm or more, and further preferably 1.5 ppm or more.

[0100] By setting the content of the organic dye A to 10.0 ppm or less, the appearance has a more natural color.

[0101] From the above viewpoints, the content of the organic dye A is more preferably 8.0 ppm or less, and even more preferably 5.0 ppm or less.

[0102] <Organic pigment B>

[0103] The organic dye B contains a porphyrin compound b represented by the following formula (B1).

[0104] The organic dye B preferably has a maximum absorption wavelength within a wavelength range of 550 nm to 600 nm.

[0105] [Chemical formula 9]

[0106]

[0107] In formula (B1), M represents a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a hydroxide metal atom or an oxide metal atom, and R 3 and R 4 Each represents a hydrogen atom, a halogen atom, an aliphatic group having 3 to 10 carbon atoms, or an aromatic group which may contain a halogen atom.

[0108] M is preferably copper, palladium, cobalt or vanadium oxide, more preferably cobalt or vanadium oxide.

[0109] R 3 and R 4 In the above, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, and a fluorine atom is preferred.

[0110] Examples of the aliphatic group having 3 to 10 carbon atoms include linear, branched or cyclic alkyl groups, linear, branched or cyclic alkenyl groups, and linear, branched or cyclic alkynyl groups.

[0111] Examples of the linear, branched or cyclic alkyl group which is an aliphatic group having 3 to 10 carbon atoms include n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1,2-dimethylpropyl, 1-methylbutyl, 2-methylbutyl, n-hexyl, 2-methylpentyl, 4-methylpentyl, 4-methyl-2-pentyl, 1,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 3-methylhexyl, 5-methylhexyl and 2,4-dimethylpentyl.

[0112] Examples of the linear, branched or cyclic alkenyl group, which is an aliphatic group having 3 to 10 carbon atoms, include 1-methylvinyl, propenyl, 2-butenyl and 2-pentenyl.

[0113] Examples of the linear, branched or cyclic alkynyl group which is an aliphatic group having 3 to 10 carbon atoms include propynyl, butynyl, 1,3-butadienyl, 2-pentynyl, 2,4-pentadienyl, 2-hexynyl, 3,3-dimethyl-1-butynyl and 3-heptynyl.

[0114] In the aromatic group which may contain a halogen atom, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, and fluorine is preferred.

[0115] Among the aromatic groups which may contain a halogen atom, examples of the aromatic group include substituted or unsubstituted phenyl groups.

[0116] In the optical material of the present disclosure, the porphyrin compound b is preferably a compound represented by the following formula (B2), the following formula (B3), or the following formula (B4).

[0117] [Chemical formula 10]

[0118]

[0119] In formula (B2), M represents a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a hydroxide metal atom or an oxide metal atom.

[0120] [Chemical formula 11]

[0121]

[0122] In formula (B3), M represents a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a hydroxide metal atom or an oxide metal atom.

[0123] [Chemical formula 12]

[0124]

[0125] In formula (B4), M represents a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a hydroxide metal atom, or an oxide metal atom.

[0126] In formula (B2) to formula (B4), specific examples, preferred embodiments, etc. of M are the same as the specific examples, preferred embodiments, etc. of M in formula (B1).

[0127] The content of the organic dye B is preferably 1.0 ppm to 20.0 ppm.

[0128] When the content of the organic dye B is 1.0 ppm or more, the lens has a natural color.

[0129] From the above viewpoints, the content of the organic dye B is more preferably 2.0 ppm or more, and further preferably 5.0 ppm or more.

[0130] By setting the content of the organic dye B to 20.0 ppm or less, the color of the film is natural, and a high visible light transmittance can be maintained, so that the film is bright and easy to observe.

[0131] From the above viewpoints, the content of the organic dye B is more preferably 15.0 ppm or less, further preferably 10.0 ppm or less, and particularly preferably 8.0 ppm or less.

[0132] The total content of the organic dye A and the organic dye B is preferably 1.0 ppm to 100.0 ppm.

[0133] By setting the total content of the organic dye A and the organic dye B to 1.0 ppm or more, the blue light blocking capability can be maintained more favorably.

[0134] From the above viewpoints, the total content of the organic dye A and the organic dye B is more preferably 3.0 ppm or more, further preferably 5.0 ppm or more, and particularly preferably 7.0 ppm or more.

[0135] By setting the total content of the organic dye A and the organic dye B to 100.0 ppm or less, the appearance has a more natural color.

[0136] From the above viewpoints, the total content of the organic dye A and the organic dye B is more preferably 50.0 ppm or less, further preferably 30.0 ppm or less, and particularly preferably 15.0 ppm or less.

[0137] The ratio of the content of the organic dye B to the content of the organic dye A (organic dye B / organic dye A) is preferably 0.5 to 5.0.

[0138] As described above, organic pigment A easily absorbs light of higher energy (i.e., short wavelength) compared to organic pigment B. Therefore, from the viewpoint of maintaining good blue light interception capability, it is not necessary to include a large amount of organic pigment A. For example, organic pigment B / organic pigment A is more preferably 1.0 to 4.5, further preferably 1.5 to 4.0, and particularly preferably 2.0 to 3.0.

[0139] In addition, the content of the organic dye A is preferably smaller than the content of the organic dye B.

[0140] <Resin>

[0141] The optical material of the present disclosure includes a resin.

[0142] In the present disclosure, the resin may be a commercially available resin or a resin obtained from a monomer.

[0143] In the present disclosure, the resin may be used without particular limitation, but a transparent resin is preferred.

[0144] Hereinafter, the resin and the monomers used to obtain the resin will be described.

[0145] The resin is not particularly limited, and examples thereof include polyurethane, polythiourethane, polysulfide, polycarbonate, poly(meth)acrylate, polyolefin, cyclic polyolefin, polyallyl, polyurethaneurea, polyene-polythiol polymer, ring-opening metathesis polymer, polyester, and epoxy resin.

[0146] Among the above, the resin preferably contains polythiourethane or polysulfide.

[0147] The resin may be used alone or in combination of two or more.

[0148] The optical material preferably includes at least one selected from the group consisting of polyurethane, polythiourethane, polysulfide, polycarbonate, and poly(meth)acrylate, and more preferably includes polythiourethane. These resins are highly transparent materials and can be suitably used for optical material applications.

[0149] Polyurethane contains structural units derived from polyisocyanate compounds and structural units derived from polyol compounds. Polythiourethane contains structural units derived from polyisocyanate compounds and structural units derived from polythiol compounds.

[0150] Examples of the polyisocyanate compound include hexamethylene diisocyanate, 1,5-pentamethylene diisocyanate, 2,2,4-trimethyl-1,6-hexamethylene diisocyanate, 2,4,4-trimethyl-1,6-hexamethylene diisocyanate, lysine methyl diisocyanate, lysine triisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, α,α,α',α'-tetramethylxylylene diisocyanate, bis(isocyanate methyl)naphthalene, mesitylene triisocyanate, bis(isocyanate methyl)sulfide, bis(isocyanate ethyl)sulfide, bis(isocyanate methyl)disulfide, bis(isocyanate ethyl)disulfide aliphatic polyisocyanate compounds such as ether, bis(isocyanate methylthio)methane, bis(isocyanate ethylthio)methane, bis(isocyanate ethylthio)ethane, bis(isocyanate methylthio)ethane; isophorone diisocyanate, 1,3-bis(isocyanate methyl)cyclohexane, 1,4-bis(isocyanate methyl)cyclohexane, dicyclohexylmethane diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane diisocyanate, 2,5-bis(isocyanate methyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanate methyl)bicyclo-[2.2.1]-heptane , 3,8-bis(isocyanate methyl)tricyclodecane, 3,9-bis(isocyanate methyl)tricyclodecane, 4,8-bis(isocyanate methyl)tricyclodecane, 4,9-bis(isocyanate methyl)tricyclodecane and other alicyclic polyisocyanate compounds; naphthalene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, biphenyl diisocyanate, diphenylmethane-2,2'-diisocyanate, diphenylmethane-2,4'-diisocyanate, diphenylmethane-4,4'-diisocyanate, benzene triisocyanate, diphenyl sulfide-4,4-diisocyanate, etc. Aromatic polyisocyanate compounds; heterocyclic polyisocyanate compounds such as 2,5-diisocyanate thiophene, 2,5-bis(isocyanate methyl) thiophene, 2,5-diisocyanate tetrahydrothiophene, 2,5-bis(isocyanate methyl) tetrahydrothiophene, 3,4-bis(isocyanate methyl) tetrahydrothiophene, 2,5-diisocyanate-1,4-dithiolane, 2,5-bis(isocyanate methyl)-1,4-dithiolane, 4,5-diisocyanate-1,3-dithiolane, and 4,5-bis(isocyanate methyl)-1,3-dithiolane, etc., and at least one selected from them can be used.

[0151] The polyol compound is one or more aliphatic or alicyclic alcohols, and specifically includes linear or branched aliphatic alcohols, alicyclic alcohols, and alcohols obtained by adding ethylene oxide, propylene oxide, or ε-caprolactone to these alcohols, and at least one selected from these can be used.

[0152] Examples of the linear or branched aliphatic alcohol include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,3-propylene glycol, 2,2-dimethyl-1,3-propylene glycol, 2,2-diethyl-1,3-propylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, 3-methyl-1,3-butylene glycol, 1,2-pentanediol, 1,3-pentanediol, 1,5-pentanediol, 2,4-pentanediol, 2-methyl-2,4-pentanediol, 3-methyl-1,5-pentanediol, 1,6-hexanediol, 2,5-hexanediol, glycerol, dipropylene glycol, polyglycerol, trimethylolpropane, pentaerythritol, and di(trimethylolpropane).

[0153] Examples of the alicyclic alcohol include 1,2-cyclopentanediol, 1,3-cyclopentanediol, 3-methyl-1,2-cyclopentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanediol, 4,4′-bicyclohexanol, and 1,4-cyclohexanedimethanol. At least one selected from these can be used.

[0154] Compounds obtained by adding ethylene oxide, propylene oxide, or ε-caprolactone to these alcohols may also be used. For example, ethylene oxide adducts of glycerol, ethylene oxide adducts of trimethylolpropane, ethylene oxide adducts of pentaerythritol, propylene oxide adducts of glycerol, propylene oxide adducts of trimethylolpropane, propylene oxide adducts of pentaerythritol, caprolactone-modified glycerol, caprolactone-modified trimethylolpropane, caprolactone-modified pentaerythritol, and at least one selected from these may be used.

[0155] Examples of the polythiol compound include methanedithiol, 1,2-ethanedithiol, 1,2,3-propanetrithiol, 1,2-cyclohexanedithiol, bis(2-mercaptoethyl)ether, tetrakis(mercaptomethyl)methane, diethylene glycol bis(2-mercaptoacetate), diethylene glycol bis(3-mercaptopropionate), ethylene glycol bis(2-mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate), trimethylolethane tris(2-mercaptoacetate), trimethylolethane tris(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), bis(mercaptomethyl)sulfide, and bis(mercaptomethyl)disulfide. 、bis(mercaptoethyl) sulfide, bis(mercaptoethyl) disulfide, bis(mercaptopropyl) sulfide, bis(mercaptomethylthio)methane, bis(2-mercaptoethylthio)methane, bis(3-mercaptopropylthio)methane, 1,2-bis(mercaptomethylthio)ethane, 1,2-bis(2-mercaptoethylthio)ethane, 1,2-bis(3-mercaptopropylthio)ethane, 1,2,3-tris(mercaptomethylthio)propane, 1,2,3-tris(2-mercaptoethylthio)propane, 1,2,3-tris(3-mercaptopropylthio)propane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11 -dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, tetrakis(mercaptomethylthiomethyl)methane, tetrakis(2-mercaptoethylthiomethyl)methane, tetrakis(3-mercaptopropylthiomethyl)methane, bis(2,3-dimercaptopropyl)sulfide, 2,5-dimercaptomethyl-1,4-dithiacyclohexane, 2,5-dimercapto-1,4-dithiacyclohexane, 2,5-dimercaptomethyl-2,5-dimethyl-1,4-dithiacyclohexane, and their thioglycolates and thiopropionates, hydroxymethyl sulfide bis(2-thioglycolate), hydroxymethyl sulfide bis(3-thiopropionate), hydroxyethyl sulfide bis(2-thioglycolate), Hydroxyethyl sulfide bis(3-mercaptopropionate), hydroxymethyl disulfide bis(2-mercaptoacetate), hydroxymethyl disulfide bis(3-mercaptopropionate), hydroxyethyl disulfide bis(2-mercaptoacetate), hydroxyethyl disulfide bis(3-mercaptopropionate), 2-mercaptoethyl ether bis(2-mercaptoacetate), 2-mercaptoethyl ether bis(3-mercaptopropionate), thiodiacetic acid bis(2-mercaptoethyl ester), thiodipropionic acid bis(2-mercaptoethyl ester), dithiodiacetic acid bis(2-mercaptoethyl ester), dithiodipropionic acid bis(2-mercaptoethyl ester), 1,1,3,3-tetrakis(mercaptomethylthio)propane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 4,6-bis(mercaptomethylthio)-1,aliphatic polythiol compounds such as 3-dithiocyclohexane, tris(mercaptomethylthio)methane, and tris(mercaptoethylthio)methane; 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis(mercaptomethyl)benzene, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 1,2-bis(mercaptoethyl)benzene, 1,3-bis(mercaptoethyl)benzene, 1,4-bis(mercaptoethyl)benzene, 1,3,5-trimercaptobenzene, 1,3,5-tris(mercaptomethyl)benzene, 1,3,5-tris(mercaptomethyleneoxy)benzene, 1,3,5 -Aromatic polythiol compounds such as tris(mercaptoethyleneoxy)benzene, 2,5-toluenedithiol, 3,4-toluenedithiol, 1,5-naphthalenedithiol, and 2,6-naphthalenedithiol; heterocyclic polythiol compounds such as 2-methylamino-4,6-dithiol-s-triazine, 3,4-thiophenedithiol, bismuth reagent, 2,5-bis(mercaptomethyl)-1,4-dithiohexane, 4,6-bis(mercaptomethylthio)-1,3-dithiohexane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithiohexane, etc., and at least one selected from them can be used. ,

[0156] The polysulfide can be obtained by a method based on the ring-opening polymerization of a polyepisulfide, a polythietane compound, or the like as a monomer. The optical material composition may contain monomers constituting these resins.

[0157] As the polyepisulfide, any one can be used without particular limitation, and for example, those described in Japanese Patent No. 6216383 can be used.

[0158] As the polythietane compound, a metal-containing thietane compound or a non-metal thietane compound can be used. Specifically, for example, a compound described in Japanese Patent No. 6216383 can be used.

[0159] Polycarbonate can be obtained by reacting alcohol with phosgene, or by reacting alcohol with chloroformate, or by transesterification of carbonic acid diester compound, or commonly available commercial polycarbonate resin can be used. As commercial products, Panlite series manufactured by Teijin Chemicals Co., Ltd. can be used. The optical material composition of the present disclosure may include polycarbonate as a resin material.

[0160] As the poly(meth)acrylate, any one can be used without particular limitation, and for example, those described in Japanese Patent No. 6216383 can be used.

[0161] As the polyolefin, any polyolefin can be used without particular limitation, and for example, specific examples described in Japanese Patent No. 6216383, cyclic polyolefins, olefin polymerization reactions, and methods for producing polyolefins can be used.

[0162] The polyallyl group can be produced by polymerizing at least one allyl group-containing monomer selected from allyl group-containing monomers in the presence of a known radical-generating polymerization catalyst.

[0163] As the allyl group-containing monomer, allyl diglycol carbonate and diallyl phthalate are generally commercially available, and these can be preferably used.

[0164] Polyurethane urea is a reaction product obtained from a polyurethane prepolymer and a diamine curing agent, and polyurethane urea sold under the trademark TRIVEX by PPG Industries, Inc. is a representative example. Polyurethane urea is a highly transparent material and can be preferably used.

[0165] The polyene-polythiol polymer is a resin product formed by addition polymerization and vinyl chain polymerization of a polyene compound having two or more ethylenic functional groups in one molecule and a polythiol compound having two or more thiol groups in one molecule.

[0166] As the polyene compound in the polyene-polythiol polymer, for example, those described in Japanese Patent No. 6216383 can be used.

[0167] The ring-opening metathesis polymer is a resin obtained by ring-opening polymerization of cyclic olefins using a catalyst. As the cyclic olefins that can be ring-opening polymerized, for example, those described in Japanese Patent No. 6216383 can be used.

[0168] Polyesters can be polycondensed in the presence of known polyester production catalysts such as Lewis acid catalysts represented by antimony and germanium compounds, organic acids, and inorganic acids. Specifically, it refers to a substance formed from one or more kinds of polycarboxylic acids including dicarboxylic acids and their ester-forming derivatives and one or more kinds of polyols including diols, or a substance formed from hydroxycarboxylic acids and their ester-forming derivatives, or a substance formed from cyclic esters.

[0169] As the dicarboxylic acid and the diol, for example, those described in Japanese Patent No. 6216383 can be used.

[0170] As the polyester, for example, those described in Japanese Patent No. 6216383 can be used.

[0171] The epoxy resin is a resin obtained by ring-opening polymerization of an epoxy compound, and as the epoxy compound, for example, those described in Japanese Patent No. 6216383 can be used.

[0172] (additive)

[0173] The optical material of the present disclosure may contain additives as other components than those described above.

[0174] Examples of the additives include polymerization catalysts, internal mold release agents, dyes, ultraviolet absorbers, etc. In the present disclosure, a polymerization catalyst may or may not be used when obtaining polyurethane and polythiourethane.

[0175] As an internal release agent, an acidic phosphate ester can be mentioned. As an acidic phosphate ester, a phosphoric acid monoester and a phosphoric acid diester can be mentioned, each of which can be used alone or mixed with two or more. For example, the internal release agent exemplified in WO2021 / 132559 can be used.

[0176] Examples of the ultraviolet absorber include benzophenone-based ultraviolet absorbers such as 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-acryloyloxybenzophenone, 2-hydroxy-4-acryloyloxy-5-tert-butylbenzophenone, and 2-hydroxy-4-acryloyloxy-2',4'-dichlorobenzophenone; 2-[4-[(2-hydroxy-3-dodecyloxypropyl)oxy]-2-hydroxyphenyl]4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine; and 2-[4-[(2-hydroxy-3-dodecyloxypropyl)oxy]-2-hydroxyphenyl]4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine. -hydroxy-3-tridecyloxypropyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[4-[(2-hydroxy-3-(2'-ethyl)hexyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-butyloxyphenyl)-6-(2,4-bisbutyloxyphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-[1-octyloxy triazine-based ultraviolet absorbers such as [[(4-(((((((((((((((((((((((((- ...-((-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(-(- Benzotriazole-based ultraviolet absorbers such as 2-(2H-benzotriazole-2-yl)-4-tert-octylphenol and 2-(5-chloro-2H-benzotriazole-2-yl)-4-methyl-6-tert-butylphenol can be used. These ultraviolet absorbers can be used alone or in combination of two or more.

[0177] A commercially available product may be used as the ultraviolet absorber. Examples of the commercially available product include Tinuvin 326 (manufactured by BASF Japan Co., Ltd.) and Viosorb 583 (manufactured by Kyodo Pharmaceutical Co., Ltd.).

[0178] The optical material of the present disclosure may contain a color tone adjuster. When the optical material contains a color tone adjuster, the content of the color tone adjuster may be 3 ppm to 50 ppm, or 5 ppm to 40 ppm.

[0179] As a color tone adjusting agent, there can be mentioned substances having an absorption band in the wavelength region of orange to yellow in the visible light region and having a function of adjusting the hue of an optical material containing a resin. As a color tone adjusting agent, there can be mentioned a bluing agent. As a bluing agent, there can be mentioned substances having an absorption band in the wavelength region of orange to yellow in the visible light region and having a function of adjusting the hue of an optical material formed of a resin material. The bluing agent may include substances that display blue to purple.

[0180] (Visible light transmittance)

[0181] From the viewpoint of visibility, the visible light transmittance of the optical material of the present disclosure is preferably 75%T or more, more preferably 78%T or more, and even more preferably 80%T or more.

[0182] The visible light transmittance can be measured using a spectrophotometer (for example, CM-5 manufactured by Konica Minolta) in accordance with ISO 8980-3 using an optical material having a thickness of 2 mm.

[0183] (Preferred spectral characteristics)

[0184] Preferred spectral characteristics of the optical material of the present disclosure are shown below.

[0185] The following preferred spectral characteristics are in the spectroscopic spectrum,

[0186] The maximum absorption wavelength in the wavelength range of 440 nm to 500 nm is defined as the maximum absorption wavelength a.

[0187] The maximum absorption wavelength in the wavelength range of 550nm to 600nm is defined as the maximum absorption wavelength b.

[0188] The transmittance at the maximum absorption wavelength a when the thickness is 2 mm is defined as transmittance T1.

[0189] Spectral characteristics when the transmittance at the maximum absorption wavelength b when the thickness is 2 mm is defined as transmittance T2.

[0190] The above-mentioned spectral spectrum is measured using a test sample having a thickness of 2 mm formed of the optical material of the present disclosure and a spectrophotometer (for example, UV-1800 ultraviolet visible spectrophotometer, manufactured by Shimadzu Corporation).

[0191] The value obtained by subtracting the maximum absorption wavelength a from the maximum absorption wavelength b (ie, the difference [maximum absorption wavelength b-maximum absorption wavelength a]) is preferably 100 nm to 160 nm, more preferably 100 nm to 140 nm.

[0192] When the difference [maximum absorption wavelength b−maximum absorption wavelength a] is 100 nm to 160 nm, the effect of giving the appearance a natural color is more excellent.

[0193] The transmittance T1 is preferably in the range of 60%T to 95%T, and more preferably in the range of 65%T to 85%T.

[0194] When the transmittance T1 is within the range of 60%T to 95%T, the effect of having a natural color tone in the appearance is more excellent.

[0195] The transmittance T2 is preferably in the range of 60%T to 95%T, and more preferably in the range of 65%T to 85%T.

[0196] When the transmittance T2 is within the range of 60%T to 95%T, the effect of having a natural color tone in the appearance is more excellent.

[0197] (Weather resistance test)

[0198] In the optical material of the present disclosure, the absolute value ΔT1 of the difference between the transmittance T1 before and after the weather resistance test described below is preferably 2.5%T or less, more preferably 2.0%T or less, and further preferably 1.0%T or less.

[0199] When ΔT1 is 2.5%T or less, the effect of being able to suppress the reduction in the blue light blocking capability for a long period of time is more excellent.

[0200] Here, the light resistance test is conducted on a test sample having a thickness of 2 mm formed of the optical material of the present disclosure at a temperature of 50° C., a humidity of 40% RH, and an illumination of 60 W / m 2 , and the irradiation time is 150 hours under the conditions of xenon lamp irradiation test.

[0201] Irradiation with a xenon lamp is performed, for example, using a weather resistance acceleration tester (for example, Xenon Weather Meter NX75, manufactured by Suga Test Instruments Co., Ltd.).

[0202] As for the optical material of the present disclosure, the sum of the absolute value of the difference between the transmittance T1 before and after the weather resistance test, i.e., ΔT1, and the absolute value of the difference between the transmittance T2 before and after the weather resistance test, i.e., ΔT2 (i.e., ΔT1+ΔT2) is preferably less than 6.0%T, and more preferably less than 3.0%T.

[0203] When ΔT1+ΔT2 is 6.0%T or less, weather resistance over a long period of time is more excellent.

[0204] (Chroma ＊ )

[0205] The chromaticity C of the optical material of the present disclosure ＊ It is preferably 4.0 or less.

[0206] By making the chroma C ＊ The optical material has an excellent appearance when the value is 4.0 or less.

[0207] Chroma C ＊ It is more preferably 3.5 or less, further preferably 2.5 or less, and particularly preferably 1.5 or less.

[0208] As chroma C ＊ There is no particular limit on the lower limit of chroma C. ＊ It may be greater than 0, and may be greater than 0.01.

[0209] Chroma C ＊ For example, it is preferably 0.01 to 4.0.

[0210] Chroma C ＊ The determination method is as follows.

[0211] Using an optical material with a thickness of 2 mm, L was measured using a spectrophotometer CM-5 (manufactured by Konica Minolta, Inc.) under the conditions of light source C and a viewing angle of 2°. ＊ a ＊ b ＊ a in color space (CIE 1976) ＊ , b ＊ Calculate the chroma C using the following formula ＊ .

[0212] [Mathematical formula 1]

[0213]

[0214] <Composition for optical material>

[0215] The optical material can be produced using, for example, the optical material composition described below.

[0216] The optical material composition may include, for example: an organic dye A containing the porphyrin compound a represented by the above formula (A1); an organic dye B containing the porphyrin compound b represented by the above formula (B1); and the above monomer.

[0217] The monomer is a monomer that can produce the above-mentioned resin by curing.

[0218] In the present disclosure, the composition for an optical material can be obtained by mixing the above-mentioned components by a predetermined method.

[0219] The mixing order and mixing method of the components in the composition are not particularly limited and can be carried out by known methods. As known methods, for example, there are methods of preparing a masterbatch containing a predetermined amount of additives, dispersing the masterbatch in a solvent and dissolving it, etc. For example, in the case of a polyurethane resin, there are methods of preparing a masterbatch by dispersing additives in a polyisocyanate compound and dissolving it, etc.

[0220] <Optical material method>

[0221] Examples of the optical material aspect of the present disclosure include an optical material consisting of a substrate, an optical material consisting of a substrate and a coating layer, and the like.

[0222] As said base material, a lens base material is mentioned, for example.

[0223] As the coating layer, for example, a primer layer, a hard coating layer, an antireflection layer, an antifogging coating layer, an anti-pollution layer, a waterproof layer, etc. can be cited. These coating layers can be used alone, or multiple coating layers can be multilayered and used. When the coating layers are applied to both sides, the same coating layer can be applied to each side, or different coating layers can be applied.

[0224] For example, a molded body (e.g., a lens substrate) can be prepared using a composition for an optical material that does not contain a pigment, and then the pigment is dispersed in water or a solvent, and the molded body is immersed in the obtained dispersion, so that the pigment is impregnated in the molded body, and the molded body impregnated with the pigment is dried. The molded body obtained in the above manner can be used to prepare an optical material.

[0225] Alternatively, the porphyrin compound may be impregnated into the optical material after the optical material is prepared. Alternatively, a spectacle lens having a lens substrate and a coating layer laminated as required may be immersed in a dispersion containing a pigment to impregnate the lens with the pigment.

[0226] The impregnation amount of the pigment can be adjusted to the desired impregnation amount by the concentration of the pigment in the dispersion, the temperature of the dispersion, the molded body, the time of dipping the optical material, etc. The higher the concentration, the higher the temperature, and the longer the dipping time, the more the impregnation amount increases. In the case of more precisely adjusting the impregnation amount, it can be implemented by repeatedly dipping under the condition of less impregnation amount.

[0227] Alternatively, a coating layer containing a pigment may be formed on an optical material such as a plastic lens by using a composition for an optical material containing a pigment as a coating material.

[0228] An optical material having such a structure can be suitably used as a lens, preferably a spectacle lens.

[0229] It should be noted that the present disclosure is not limited to the above-described embodiments, and various forms can be adopted within a range that does not impair the effects of the present invention.

[0230] <Applications of optical materials>

[0231] Examples of uses of the optical material of the present disclosure include:

[0232] Eyeglass lenses, goggles, eyeglass lenses for vision correction, lenses for camera equipment, Fresnel lenses for LCD projectors, biconvex lenses, contact lenses, lenses for wearable devices, etc.

[0233] Sealing materials for light emitting diodes (LEDs);

[0234] Optical waveguides;

[0235] Optical lenses;

[0236] Optical adhesives used in joining optical waveguides, etc.

[0237] Anti-reflection films used in optical lenses, etc.

[0238] Transparent coatings used in liquid crystal display device components (substrates, light guide plates, films, sheets, etc.);

[0239] Windshields used in car windshields, motorcycle helmets, etc.

[0240] Transparent substrate;

[0241] A film attached to a cover of a lighting fixture, an irradiation surface of a lighting fixture, etc. (i.e., a film serving as an optical material (e.g., a filter));

[0242] Films that are attached to windows (i.e., films that act as optical materials such as filters);

[0243] Films attached to lenses (i.e., films that act as optical materials such as filters);

[0244] etc.

[0245] (lens)

[0246] The lens of the present disclosure is a lens using the optical material of the present disclosure.

[0247] That is, the lens of the present disclosure includes the optical material of the present disclosure. The lens of the present disclosure may be a lens having a lens substrate formed of an optical material, and may have a coating layer on one or both surfaces of the lens substrate.

[0248] The lens of the present disclosure may be any of the various lenses exemplified in the aforementioned uses of the optical material, and is preferably a spectacle lens.

[0249] As the coating layer, specifically, a primer layer, a hard coating layer, an antireflection layer, an antifogging coating layer, an anti-pollution layer, a waterproof layer, etc. can be cited. These coating layers can be used alone, or multiple coating layers can be multilayered and used. When the coating layers are applied to both sides, the same coating layer can be applied to each side, or different coating layers can be applied.

[0250] These coating layers may contain pigments, infrared absorbers, light stabilizers, antioxidants, etc., dyes, pigments, etc., photochromic dyes, photochromic pigments, etc., antistatic agents, and other known additives for improving the performance of the lens, etc. used in the present disclosure.

[0251] For the layer applied by coating, various leveling agents may be used for the purpose of improving coating properties.

[0252] The primer layer is usually formed between the hard coating layer described later and the lens substrate. The primer layer is a coating layer for the purpose of improving the adhesion of the hard coating layer formed thereon to the lens substrate, and according to the circumstances, the impact resistance can also be improved. For the primer layer, as long as the adhesion relative to the obtained lens substrate is high, for example, a primer composition with urethane resin, epoxy resin, polyester resin, melamine resin, and polyvinyl acetal as the main component can be used in the formation of the primer layer. In the preparation of the primer composition, a solvent that does not affect the lens substrate can be used for the purpose of adjusting the viscosity of the composition, or a solvent may not be used.

[0253] The primer layer can also be formed by any method of a coating method or a dry method. In the case of a coating method, the primer composition is applied to the lens substrate by a known coating method such as spin coating or dip coating, and then cured to form a primer layer. In the case of a dry method, the primer layer is formed by a known dry method such as a CVD method or a vacuum evaporation method. When forming the primer layer, the surface of the lens substrate may be subjected to a pre-treatment such as an alkali treatment, a plasma treatment, or an ultraviolet treatment, as required, in order to improve adhesion.

[0254] The hard coat layer is a coating layer for the purpose of imparting functions such as scratch resistance, abrasion resistance, moisture resistance, warm water resistance, heat resistance, and weather resistance to the lens surface.

[0255] In forming the hard coating layer, the following hard coating composition can be used, the hard coating composition comprising: a curable organosilicon compound; and one or more oxide microparticles containing an element selected from the element group consisting of Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In and Ti.

[0256] The following hard coating composition can also be used, which comprises: a curable organic silicon compound; and one or more microparticles of a composite oxide containing two or more elements selected from the element group of Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In and Ti.

[0257] The hard coating composition preferably contains at least one selected from the group consisting of amines, amino acids, metal acetylacetonate complexes, organic acid metal salts, perchloric acids, perchloric acid salts, acids, metal chlorides and polyfunctional epoxy compounds in addition to the above components.

[0258] The hard coating composition may contain a solvent that does not affect the lens substrate, or may not contain a solvent.

[0259] The hard coating layer is usually formed by applying the hard coating composition by a known coating method such as spin coating or dip coating, and then curing. As the curing method, energy ray irradiation such as ultraviolet rays and visible light, thermal curing, etc. can be cited. From the viewpoint of suppressing the generation of interference fringes, the difference between the refractive index of the hard coating layer and the refractive index of the lens substrate is preferably within the range of ±0.1.

[0260] The anti-reflection layer includes inorganic and organic ones.

[0261] For the inorganic anti-reflection layer, SiO 2 、TiO 2 Inorganic oxides such as titanium dioxide and titanium dioxide are formed by a dry method such as vacuum evaporation, sputtering, ion plating, ion beam assist, or CVD.

[0262] The organic antireflection layer is formed by a wet method using a composition containing an organic silicon compound and silica-based fine particles having internal voids.

[0263] An antireflection layer may be formed on the hard coat layer as needed.

[0264] The anti-reflection layer may be a multi-layer or a single-layer.

[0265] From the viewpoint of effectively exhibiting the antireflection function, the antireflection layer is preferably a multilayer, in which case, the low refractive index layer and the high refractive index layer are preferably alternately stacked. In addition, the refractive index difference between the low refractive index layer and the high refractive index layer is preferably 0.1 or more.

[0266] As the high refractive index layer, there are ZnO, TiO 2 、CeO 2 , Sb 2 O 5 SnO 2 、ZrO 2 、 2 O 5 As the low refractive index layer, SiO 2 Equal layers.

[0267] When used as a single layer, the refractive index is preferably lower than that of the hard coat layer by at least 0.1.

[0268] On the antireflection layer, an antifogging coating, an antifouling layer, a water-repellent layer, etc. may be formed as necessary. The method for forming the antifogging layer, the antifouling layer, the water-repellent layer, etc. is not particularly limited, and a conventionally known method may be applied.

[0269] Example

[0270] Hereinafter, the present disclosure will be described in more detail by way of examples, but the present disclosure is not limited to the following examples unless it exceeds the gist thereof. It should be noted that, unless otherwise specified, "parts" are based on mass.

[0271] (Preparation of porphyrin compounds)

[0272] (Synthesis Example 1: Preparation of (1-A))

[0273] 17.0 g of the compound represented by the following structural formula (1-a) was dissolved in 170 ml of N,N-dimethylformamide, and 35.8 g of bromine was added dropwise thereto at 10°C to 20°C. After stirring at room temperature for 4 hours, the mixture was discharged into 800 g of ice water and neutralized with an aqueous sodium hydroxide solution. The precipitate was filtered, washed with water, washed with methanol, and dried to obtain a compound represented by the following structural formula (1-A) (hereinafter also referred to as (1-A) compound).

[0274] [Chemical formula 13]

[0275]

[0276] (Synthesis Example 2: Preparation of (2-A))

[0277] The compound represented by structural formula (1-a) is changed to the compound represented by the following structural formula (2-a), and the solvent is changed from N,N-dimethylformamide to 1,2-dichlorobenzene. The same operation as (Synthesis Example 1) is carried out to obtain a compound represented by the following structural formula (2-A) (hereinafter also referred to as (2-A) compound).

[0278] [Chemical formula 14]

[0279]

[0280] (Synthesis Example 3: Preparation of (3-A))

[0281] 30.0 g of the compound represented by the following structural formula (3-a) was dispersed in 150 g of 1,1,2-trichloroethane and 60 g of water, and a solution containing 58.7 g of bromine and 60 g of 1,2,2-trichloroethane was added dropwise thereto at 50°C to 55°C. The mixture was stirred at 50°C to 55°C for 3 hours, and then cooled to room temperature. An aqueous sodium sulfite solution (4.2 g of sodium sulfite, 21 g of water) was added to the reaction solution, and the mixture was stirred at room temperature for 15 minutes. Next, an aqueous sodium hydroxide solution (16.2 g of sodium hydroxide, 162 g of water) was added, and the mixture was stirred at room temperature for 30 minutes. The precipitate was filtered, washed with water, cleaned with methanol, and dried to obtain 45.6 g of the compound represented by the following structural formula (3-A) (hereinafter also referred to as (3-A) compound).

[0282] [Chemical formula 15]

[0283]

[0284] (Synthesis Example 4: Preparation of (1-B2))

[0285] 18 g of 2-fluorobenzyl cyanide, 16.7 g of pivaloyl cyanide and 700 mL of dichloromethane were mixed and cooled to -10 ° C. Then, 82 g of titanium tetrachloride was added dropwise at this temperature over 70 minutes, and then 88 g of N-methylmorpholine was added dropwise over 2 hours, and stirred at room temperature for 15 hours. The reaction solution was discharged into water, chloroform was added and stirred, and then the insoluble components were filtered. The filtrate was washed with sodium bicarbonate aqueous solution and water in turn, and concentrated. The column purified product was dissolved in 400 mL of acetonitrile, stirred for 94 hours at room temperature while irradiating an ultraviolet fluorescent lamp, and separated and purified by silica gel column chromatography after concentration to obtain a compound represented by the following structural formula (1-b).

[0286] 2 g of the compound represented by the structural formula (1-b) was mixed with 20 mL of 1-pentanol and nitrogen substitution was performed. After adding 0.33 g of formamide and 0.38 g of vanadium (III) chloride, 0.83 g of potassium tert-butoxide was slowly added. Then, the reaction solution was heated to 105°C and stirred for 15 hours. After the stirring was completed, the reaction solution was cooled and discharged into 80 mL of methanol. 40 mL of ion exchange water was added dropwise thereto, and the precipitated crystals were separated by filtration and dried at 100°C. The obtained crystals were dissolved in toluene, activated clay and silica gel were added, stirred, the insoluble components were filtered out, and the filtrate was concentrated. The obtained solid component was washed with methanol and dried to obtain 0.91 g of the compound represented by the following structural formula (1-B2) (hereinafter also referred to as (1-B2) compound).

[0287] [Chemical formula 16]

[0288]

[0289] (Synthesis Example 5: Preparation of (2-B2))

[0290] The same operation as in (Synthesis Example 4) was carried out except that vanadium (III) chloride was replaced with anhydrous cobalt (II) chloride to obtain a compound represented by the following structural formula (2-B2) (hereinafter also referred to as (2-B2) compound).

[0291] [Chemical formula 17]

[0292]

[0293] (Synthesis Example 6: Preparation of (1-B4))

[0294] 1.57 g of vanadium (III) chloride and 5.38 g of the compound represented by the following structural formula (2-b) were added to 50 g of 1-pentanol, and 1.02 g of ammonia gas was introduced at 20°C over 1 hour. Ammonia gas was introduced into the reaction solution, and heat was generated during the introduction of ammonia. After stirring at 20°C to 30°C for 1 hour, the temperature was raised to 125°C. After the temperature was raised, stirring was continued at 125°C for 6 hours. Next, about 40 g of 1-pentanol was removed from the reaction mixture by distillation, and methanol water was added at a mass ratio of 1:1. The precipitated compound was filtered, recovered, and dried to obtain 5.00 g of the compound represented by the following structural formula (1-B4) (hereinafter also referred to as (1-B4) compound).

[0295] [Chemical formula 18]

[0296]

[0297] (Synthesis Example 7: Preparation of (3-B4))

[0298] The same operation as in (Synthesis Example 6) was carried out except that vanadium (III) chloride was replaced with palladium (II) chloride to obtain a compound represented by the following structural formula (3-B4) (hereinafter also referred to as (3-B4) compound).

[0299] [Chemical formula 19]

[0300]

[0301] (Synthesis Example 8: Preparation of (4-B4))

[0302] The same operation as in (Synthesis Example 6) was carried out except that vanadium (III) chloride was replaced with anhydrous copper (II) chloride to obtain a compound represented by the following structural formula (4-B4) (hereinafter also referred to as (4-B4) compound).

[0303] [Chemical formula 20]

[0304]

[0305] (Examples 1 to 3, Examples 6 to 10, Comparative Examples 1 to 4, Comparative Example 6)

[0306] (Lens production)

[0307] The organic dye A (porphyrin dye) described in Tables 1 to 3 was used in the amounts described in Tables 1 to 3, the organic dye B (porphyrin dye) described in Tables 1 to 3 was used in the amounts described in Tables 1 to 3, 0.020 parts by mass of dibutyltin dichloride as a polymerization catalyst, 0.1 parts by mass of an internal mold release agent for MR (manufactured by Mitsui Chemicals, Inc.) as an internal mold release agent, 1.5 parts by mass of Viosorb 583 (manufactured by Kyodo Chemical Co., Ltd.) as an ultraviolet absorber, and 50.6 parts by mass of a composition containing 2,5-bis(isocyanatemethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatemethyl)bicyclo-[2.2.1]-heptane were stirred at 25° C. to completely dissolve the components.

[0308] Then, 25.5 parts by mass of a composition containing 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 23.9 parts by mass of a composition containing pentaerythritol tetrakis(3-mercaptopropionate) were added, and the mixture was stirred at 25° C. for 30 minutes to prepare a uniform solution.

[0309] The solution was degassed at 400 Pa for 1 hour, filtered through a 1 μm PTFE (polytetrafluoroethylene) filter, and then injected into a 4C flat glass mold with a center thickness of 2 mm and a diameter of 77 mm. The glass mold was heated from 25° C. to 120° C. over 16 hours.

[0310] Then, the plate lens was cooled to room temperature and released from the glass mold. The obtained plate lens was further annealed at 120° C. for 2 hours. Thus, a lens with a thickness of 2 mm was obtained.

[0311] It should be noted that in Comparative Examples 3, 4, and 6 in Table 3, “-” means that the corresponding organic pigment is not contained.

[0312] (Example 4)

[0313] The organic pigment A (porphyrin pigment) described in Table 1 is in the amount described in Table 1, the organic pigment B (porphyrin pigment) described in Table 1 is in the amount described in Table 1, 0.010 parts by mass of dibutyltin dichloride as a polymerization catalyst, 0.1 parts by mass of an internal mold release agent for MR (manufactured by Mitsui Chemicals, Inc.) as an internal mold release agent, 1.5 parts by mass of Viosorb583 (manufactured by Kyodo Pharmaceutical Co., Ltd.) as an ultraviolet absorber, and 52.0 parts by mass of a composition containing meta-xylylene diisocyanate were stirred at 25° C. to completely dissolve each component.

[0314] Then, 48.0 parts by mass of a composition containing 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane was added, and the mixture was stirred at 25° C. for 30 minutes to prepare a uniform solution.

[0315] The solution was degassed at 400 Pa for 1 hour, filtered through a 1 μm PTFE (polytetrafluoroethylene) filter, and then injected into a 4C flat glass mold with a center thickness of 2 mm and a diameter of 77 mm. The glass mold was heated from 25° C. to 120° C. over 16 hours.

[0316] Then, the plate lens was cooled to room temperature and released from the glass mold. The obtained plate lens was further annealed at 120° C. for 2 hours. Thus, a lens with a thickness of 2 mm was obtained.

[0317] (Example 5)

[0318] The organic pigment A (porphyrin pigment) described in Table 1 is in the amount described in Table 1, the organic pigment B (porphyrin pigment) described in Table 1 is in the amount described in Table 1, 0.008 parts by mass of dibutyltin dichloride as a polymerization catalyst, 0.1 parts by mass of an internal mold release agent for MR (manufactured by Mitsui Chemicals, Inc.) as an internal mold release agent, 1.5 parts by mass of Viosorb583 (manufactured by Kyodo Pharmaceutical Co., Ltd.) as an ultraviolet absorber, and 50.6 parts by mass of a composition containing meta-xylylene diisocyanate were stirred at 25° C. to completely dissolve the components.

[0319] Then, 49.4 parts by mass of a composition containing 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane was added, and stirred at 25° C. for 30 minutes to prepare a uniform solution.

[0320] The solution was degassed at 400 Pa for 1 hour, filtered through a 1 μm PTFE (polytetrafluoroethylene) filter, and then injected into a 4C flat glass mold with a center thickness of 2 mm and a diameter of 77 mm. The glass mold was heated from 25° C. to 120° C. over 16 hours.

[0321] Then, the plate lens was cooled to room temperature and released from the glass mold. The obtained plate lens was further annealed at 120° C. for 2 hours. Thus, a lens with a thickness of 2 mm was obtained.

[0322] (Comparative Example 5)

[0323] No (2-B2) was added as the organic dye B, but 0.00084 parts by mass of Plast Blue 8514 (manufactured by Arimoto Chemical Industry Co., Ltd.) and 0.00034 parts by mass of Plast Red 8320 (manufactured by Arimoto Chemical Industry Co., Ltd.) were added as bluing agents, and 0.95 parts by mass of Tinuvin 326 (manufactured by BASF Japan Co., Ltd.) was added as an ultraviolet absorber.

[0324] Except for the above changes, the same operation as in Example 1 was carried out to obtain a lens having a thickness of 2 mm.

[0325] <Evaluation>

[0326] The following evaluations were performed on the lenses having a thickness of 2 mm produced in the respective Examples and Comparative Examples.

[0327] The results are shown in Tables 1 to 3.

[0328] (Measurement of Maximum Absorption Wavelength a, Transmittance T1, Maximum Absorption Wavelength b, and Transmittance T2)

[0329] The spectral spectrum of each lens having a thickness of 2 mm produced in each Example and each Comparative Example was measured using a spectrophotometer (UV-1800 ultraviolet visible spectrophotometer, manufactured by Shimadzu Corporation).

[0330] Based on the obtained spectroscopic spectrum, the

[0331] The maximum absorption wavelength a, which is the maximum absorption wavelength in the wavelength range of 440 nm to 500 nm,

[0332] The maximum absorption wavelength b is the maximum absorption wavelength in the wavelength range of 550 nm to 600 nm.

[0333] The transmittance T1 is the transmittance at the maximum absorption wavelength a when the thickness is 2 mm, and the transmittance T2 is the transmittance at the maximum absorption wavelength b when the thickness is 2 mm.

[0334] (Visible light transmittance)

[0335] The visible light transmittance was calculated based on the measurement data of the above-mentioned spectral spectrum in accordance with ISO 8980-3.

[0336] (Initial blue light interception rate)

[0337] Based on the measurement data of the above spectral spectrum, the blue light absorption rate at 380 nm to 500 nm was obtained in accordance with EN ISO12312-1:2013.

[0338] (Chroma ＊ )

[0339] The chromaticity C of the 2 mm thick lens produced in each embodiment and each comparative example was measured by the above method. ＊ .

[0340] (Hue of the lens)

[0341] The hue of the lens having a thickness of 2 mm produced in each Example and each Comparative Example was evaluated by a panel of five people based on the following evaluation criteria.

[0342] 〔Benchmark〕

[0343] A: The color of the lens is gray, which is a natural hue.

[0344] B: Feel some color taste of yellow or blue.

[0345] C: The color is clearly yellow or blue, and has a strong color tone and is unnatural.

[0346] (Weather resistance test)

[0347] The lenses with a thickness of 2 mm produced in each embodiment and each comparative example were subjected to a weather resistance test (i.e., at a temperature of 50° C., a humidity of 40% RH, and an illumination of 60 W / m 2 , and irradiation time of 150 hours under the conditions of xenon lamp irradiation test).

[0348] The weather resistance test was performed using a weather resistance accelerated testing machine Xenon Weather Meter NX75 (manufactured by Suga Test Instruments Co., Ltd.).

[0349] The above-mentioned spectral spectrum was measured before and after the above-mentioned weather resistance test.

[0350] Based on the obtained spectroscopic spectrum, we can find

[0351] The absolute value of the difference between the transmittance T1 before and after the weathering test, ΔT1; the absolute value of the difference between the transmittance T2 before and after the weathering test, ΔT2; and the sum of ΔT1 and ΔT2 (ie, ΔT1+ΔT2).

[0352] ΔT1 and ΔT1+ΔT2 were evaluated according to the following evaluation criteria.

[0353] Regarding ΔT1, the level A is the most excellent in the effect of suppressing the reduction of the blue light blocking ability for a long period of time.

[0354] Regarding ΔT1+ΔT2, the most excellent grade in weather resistance over a long period of time is A.

[0355] -ΔT1 Benchmarks-

[0356] A: ΔT1 is 1.0%T or less

[0357] B: ΔT1 exceeds 1.0%T and is 2.5%T or less

[0358] C: ΔT1 exceeds 2.5%T

[0359] -ΔT1+ΔT2 Benchmark-

[0360] A: ΔT1+ΔT2 is less than 3.0%T

[0361] B: ΔT1+ΔT2 exceeds 3.0%T and is 6.0%T or less

[0362] C: ΔT1+ΔT2 exceeds 6.0%T

[0363] The evaluation results of the lenses of the respective Examples and Comparative Examples are shown in Tables 1 to 3 below.

[0364] In addition, in Tables 1 to 3, "-" means that the component is not contained or the evaluation object does not exist. In Tables 1 to 3, the explanation of each component is as follows.

[0365] C1: 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane

[0366] C2: m-Xylylene diisocyanate

[0367] D1: Pentaerythritol tetrakis(3-mercaptopropionate)

[0368] D2: 4-Mercaptomethyl-1,8-dimercapto-3,6-dithiooctane

[0369] D3: 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane

[0370] [Table 1]

[0371]

[0372] [Table 2]

[0373]

[0374] [Table 3]

[0375]

[0376] As shown in Tables 1 to 3, the results of the weather resistance test were excellent for the examples using the optical material comprising the organic pigment A containing the porphyrin compound a represented by formula (A1), the organic pigment B containing the porphyrin compound b represented by formula (B1), and the resin. Therefore, it was possible to withstand long-term exposure (at least 50°C, 40%RH, 60W / m 2 The reduction of blue light interception capability is suppressed within 150 hours under the conditions of 150 hours. In addition, by limiting the central metal of the porphyrin compound b to cobalt or vanadium oxide, the weather resistance of the lens is improved.

[0377] In addition, chroma C ＊ The value of is small, and the hue evaluation of the lens is also excellent. Therefore, the appearance of the lens is gray and has a natural color.

[0378] On the other hand, the results of the weather resistance test were poor in Comparative Examples 1, 2 and 4 in which the central metal of the organic pigment A was not cobalt or vanadium oxide. Therefore, the effect of suppressing the reduction of the blue light interception ability over a long period of time (at least 150 hours) was poor.

[0379] In addition, the hue of the lens was different in Comparative Examples 3 to 5 which did not contain the organic dye B. Therefore, the appearance of the lens felt yellow or blue and did not have a natural color.

[0380] In addition, the hue of the lens was poor in Comparative Example 6 which did not contain the organic dye A. Therefore, the appearance of the lens felt yellow or blue, and did not have a natural color.

[0381] in addition, Figure 1 and Figure 2 The spectral spectra of the lens in which the content of the pigment (1-A) was changed to 10 ppm in Comparative Example 3 and the lens in which the content of the pigment (3-A) was changed to 10 ppm in Comparative Example 4 are shown. In the present disclosure, ppm is based on mass.

[0382] Figure 1 These are the spectral spectra of the lens in which the content of the dye (1-A) in Comparative Example 3 was changed to 10 ppm before the test and after 300 hours in the weather resistance test.

[0383] Figure 2 These are spectral spectra of the lens in which the content of the dye (3-A) in Comparative Example 4 was changed to 10 ppm before the test, after 150 hours, and after 300 hours in the weather resistance test.

[0384] The organic pigment A used in Comparative Example 3 belongs to the porphyrin compound a represented by formula (A1) in the present application. Figure 1As shown, the transmittance of the lens of Comparative Example 3 in the vicinity of 460 nm hardly changes even after 300 hours in the above-mentioned weather resistance test.

[0385] On the other hand, the organic dye A used in Comparative Example 4 has palladium as the central metal and does not belong to the porphyrin compound a represented by the formula (A1) in the present application.

[0386] like Figure 2 As shown, the transmittance of the lens of Comparative Example 4 in the weather resistance test above increased significantly at around 460 nm after 150 hours and 300 hours, that is, the blue light blocking capability decreased significantly.

[0387] It can be understood that the use of the porphyrin-based compound a represented by formula (A1) in the present application helps to suppress the reduction in the blue light interception ability.

[0388] The entire disclosure of Japanese Patent Application No. 2022-086829 filed on May 27, 2022 is incorporated into this specification by reference.

[0389] All documents, patent applications, and technical standards described in this specification are incorporated herein by reference to the same extent as if each document, patent application, and technical standard was specifically and individually described.

Claims

1. An optical material comprising: An organic pigment A containing a porphyrin compound a represented by the following formula (A1); An organic pigment B containing a porphyrin compound b represented by the following formula (B1); and Resin, [Chemical formula 1] In formula (A1), M represents cobalt or vanadium oxide, R1 represents a chlorine atom or a bromine atom, n represents 1 or 2, and R2 represents a phenyl group, or a phenyl group substituted with an aromatic group or an aliphatic group having 1 to 7 carbon atoms; [Chemical formula 2] In formula (B1), M represents a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a hydroxide metal atom or an oxide metal atom, and R3 and R4 each represent a hydrogen atom, a halogen atom, an aliphatic group having 3 to 10 carbon atoms, or an aromatic group which may contain a halogen atom.

2. The optical material according to claim 1, wherein In the formula (B1), M is cobalt or vanadium oxide.

3. The optical material according to claim 1, wherein The porphyrin compound a is a compound represented by the following formula (A2): [Chemical formula 3] In formula (A2), M represents cobalt or vanadium oxide.

4. The optical material according to claim 1, wherein The porphyrin compound b is a compound represented by the following formula (B2), the following formula (B3) or the following formula (B4), [Chemical formula 4] In formula (B2), M represents a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a hydroxide metal atom or an oxide metal atom; [Chemical formula 5] In formula (B3), M represents a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a hydroxide metal atom or an oxide metal atom; [Chemical formula 6] In formula (B4), M represents a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, a hydroxide metal atom, or an oxide metal atom.

5. The optical material according to claim 1, wherein The ratio of the content of the organic pigment B to the content of the organic pigment A is 0.5 to 5.

0.

6. The optical material according to claim 1, wherein In the spectral spectrum, when the maximum absorption wavelength in the wavelength range of 440 nm to 500 nm is defined as the maximum absorption wavelength a and the maximum absorption wavelength in the wavelength range of 550 nm to 600 nm is defined as the maximum absorption wavelength b, The value obtained by subtracting the maximum absorption wavelength a from the maximum absorption wavelength b is 100 nm to 160 nm.

7. The optical material according to claim 1, wherein In the spectral spectrum, when the maximum absorption wavelength in the wavelength range of 440nm to 500nm is set as the maximum absorption wavelength a, the maximum absorption wavelength in the wavelength range of 550nm to 600nm is set as the maximum absorption wavelength b, the transmittance at the maximum absorption wavelength a when the thickness is 2mm is set as the transmittance T1, and the transmittance at the maximum absorption wavelength b when the thickness is 2mm is set as the transmittance T2, The transmittance T1 is within the range of 65%T to 85%T, and the transmittance T2 is within the range of 65%T to 85%T.

8. The optical material according to claim 1, wherein In the spectral spectrum, when the maximum absorption wavelength in the wavelength range of 440 nm to 500 nm is defined as the maximum absorption wavelength a and the transmittance at the thickness of 2 mm at the maximum absorption wavelength a is defined as the transmittance T1, The absolute value of the difference in transmittance T1 before and after the weather resistance test described below, namely ΔT1, is 1.0%T or less. <Weather resistance test> A test sample with a thickness of 2 mm formed of the optical material was subjected to an experiment at a temperature of 50°C, a humidity of 40% RH, and an illumination of 60 W / m 2 , and irradiation time of 150 hours, irradiated with a xenon lamp.

9. The optical material according to claim 1, wherein In the spectral spectrum, when the maximum absorption wavelength in the wavelength range of 440nm to 500nm is set as the maximum absorption wavelength a, the maximum absorption wavelength in the wavelength range of 550nm to 600nm is set as the maximum absorption wavelength b, the transmittance at the maximum absorption wavelength a when the thickness is 2mm is set as the transmittance T1, and the transmittance at the maximum absorption wavelength b when the thickness is 2mm is set as the transmittance T2, The total of the absolute value of the difference between the transmittance T1 before and after the weathering test described below, ΔT1, and the absolute value of the difference between the transmittance T2 before and after the weathering test described below, ΔT2, is 3.0%T or less, <Weather resistance test> A test sample with a thickness of 2 mm formed of the optical material was subjected to an experiment at a temperature of 50°C, a humidity of 40% RH, and an illumination of 60 W / m 2 , and irradiation time of 150 hours, irradiated with a xenon lamp.

10. The optical material according to claim 1, which has a visible light transmittance of 80%T or more.

11. The optical material according to claim 1, wherein the chroma C ＊ It is 0.01~4.

0.

12. The optical material according to claim 1, wherein The resin comprises polythiourethane or polysulfide.

13. A spectacle lens comprising the optical material according to any one of claims 1 to 12.

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