WO2022114064A1 - Matériau optique, lentille et lunettes - Google Patents

Matériau optique, lentille et lunettes Download PDF

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WO2022114064A1
WO2022114064A1 PCT/JP2021/043217 JP2021043217W WO2022114064A1 WO 2022114064 A1 WO2022114064 A1 WO 2022114064A1 JP 2021043217 W JP2021043217 W JP 2021043217W WO 2022114064 A1 WO2022114064 A1 WO 2022114064A1
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Prior art keywords
maximum absorption
absorption wavelength
optical material
composition
group
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PCT/JP2021/043217
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English (en)
Japanese (ja)
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愛美 竹中
伸雄 河戸
泰三 西本
大貴 伊藤
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三井化学株式会社
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Priority to JP2022565409A priority Critical patent/JPWO2022114064A1/ja
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/11—Anti-reflection coatings
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/10—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses

Definitions

  • This disclosure relates to optical materials, lenses and eyewear.
  • optical material for example, an optical material containing a polymer and an organic dye is widely known.
  • Patent Document 1 discloses an organic glass material containing a specific wavelength absorbing dye such as a tetraazaporphyrin-based metal complex compound having an absorption peak wavelength of 595 nm or 760 nm, and an ultraviolet absorber.
  • a specific wavelength absorbing dye such as a tetraazaporphyrin-based metal complex compound having an absorption peak wavelength of 595 nm or 760 nm, and an ultraviolet absorber.
  • Patent Document 1 Japanese Unexamined Patent Publication No. 2013-238634
  • Patent Document 1 does not specify the color difference between red and green of the optical material, and it may be difficult to clearly recognize the red and green of the object when visually recognizing the object through the optical material.
  • One embodiment of the present disclosure has been made in view of the above, and provides an optical material capable of clearly recognizing the red color and green color of an object, and a lens and eyewear containing the optical material. The purpose.
  • ⁇ E * RG represents the color difference between red and green of the optical material obtained by using the formula (2)
  • ⁇ E * RG (w0) is 2- (2).
  • thiol composition 1 containing mercaptopropionate
  • thiol composition 2 containing 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, wherein the 2- (2'-hydroxy-5'- The content of t-octylphenyl) benzotriazole is 1.5% by mass, the mass ratio of the thiol composition 2 to the thiol composition 1 is 1.07, and the thiol composition with respect to the isocyanate group contained in the isocyanate composition.
  • the above formula (2) can be obtained by using a D65 light source. Represents the color difference between red and green obtained by using.
  • ⁇ 2> The optical material according to ⁇ 1>, wherein in the spectrum measured according to CIE1976, (B) the maximum absorption wavelength b exists in the range of 400 nm to 520 nm.
  • ⁇ 3> The optical material according to ⁇ 2>, wherein the ratio of the integrated value of the peak of the maximum absorption wavelength b to the integrated value of the peak of the maximum absorption wavelength a is 1.00 to 2.50.
  • ⁇ 4> The optical material according to ⁇ 2> or ⁇ 3>, wherein the difference between the maximum absorption wavelength a and the maximum absorption wavelength b is 130 nm to 200 nm.
  • ⁇ 5> The optical material according to any one of ⁇ 1> to ⁇ 4>, wherein the half width of the absorption peak of the maximum absorption wavelength a is 10 nm to 70 nm.
  • ⁇ 6> Contains a first dye having a maximum absorption wavelength in the range of 560 nm to 610 nm.
  • the blue light absorption rate of 380 nm to 500 nm in the spectrum measured according to EN ISO12312-1: 2013 is 15% to 50% ⁇ 1> to ⁇ 6>.
  • the optical material according to any one of. ⁇ 8> Described in any one of ⁇ 1> to ⁇ 7> in which (a * 2 + b * 2 ) 1/2 is 10 or less in the CIE1976 (L *, a *, b *) color system.
  • Optical material Optical material.
  • ⁇ C * RB The color difference parameter ⁇ C * RB of the CIE1976 (L *, a *, b *) color system obtained from the above equation (2) and the following equation (3) by using the D65 light source is 0 or more and 7
  • ⁇ C * RB ⁇ E * RB - ⁇ E * RB (w0) ⁇ ⁇ ⁇ (3)
  • ⁇ E * RB represents the color difference between red and blue of the optical material obtained by using the formula (2)
  • ⁇ E * RB (w0) is 2- (2 (w0).
  • the content of -t-octylphenyl) benzotriazole is 1.5% by mass, the mass ratio of the thiol composition 2 to the thiol composition 1 is 1.07, and the thiol composition with respect to the isocyanate group contained in the isocyanate composition.
  • a comparative optical material obtained by heat-curing a curable composition having a total molar ratio of thiol groups contained in the product 1 and the thiol composition 2 of 0.86 is described in the above formula (2) by using a D65 light source.
  • the optics according to any one of ⁇ 1> to ⁇ 9> which comprises at least one polymer selected from the group consisting of polyurethane, polythiourethane, polysulfide, polycarbonate, and poly (meth) acrylate. material.
  • the lens according to ⁇ 11> for use in a spectacle lens.
  • An eyewear that may include at least two optical members, an optical member on the objective side and an optical member on the opposite eye side facing the optical member on the objective side.
  • an optical material capable of clearly recognizing red and green of an object, and a lens and eyewear containing the optical material.
  • the amount of each component of the composition means the total amount of the plurality of substances present in the composition when a plurality of substances corresponding to each component are present in the layer, unless otherwise specified.
  • the combination of preferred embodiments is a more preferred embodiment.
  • ppm parts per million means ppm on a mass basis.
  • the present disclosure includes a first embodiment and a second embodiment.
  • first embodiment and the second embodiment will be described in detail.
  • the optical material of the first embodiment contains one or more dyes, has a maximum absorption wavelength a in the range of (A) 560 nm to 610 nm in a spectrum measured according to CIE1976, and uses a D65 light source. Therefore, the color difference parameter ⁇ C * RG of the CIE1976 (L *, a *, b *) color system obtained from the following equations (1) and (2) is 0 or more and 10 or less.
  • ⁇ C * RG ⁇ E * RG ⁇ E * RG (w0) ⁇ ⁇ ⁇ (1)
  • ⁇ E * ( ⁇ L * 2 + ⁇ a * 2 + ⁇ b * 2 ) 1/2 ...
  • ⁇ E * RG represents the color difference between red and green of the optical material obtained by using the formula (2)
  • ⁇ E * RG (w0) is 2- (2).
  • thiol composition 1 containing mercaptopropionate
  • thiol composition 2 containing 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, wherein the 2- (2'-hydroxy-5'- The content of t-octylphenyl) benzotriazole is 1.5% by mass, the mass ratio of the thiol composition 2 to the thiol composition 1 is 1.07, and the thiol composition with respect to the isocyanate group contained in the isocyanate composition.
  • the above formula (2) can be obtained by using a D65 light source. Represents the color difference between red and green obtained by using.
  • the red color and the green color of the object can be clearly recognized.
  • the reason for this is presumed as follows.
  • the maximum absorption wavelength a exists in the range of 560 nm to 610 nm, the light whose wavelength range is located between the red light and the green light is easily absorbed by the optical material.
  • the transmittance of light whose wavelength range is located between the red light and the green light in the optical material is lowered, and it becomes easy to clearly recognize the red and green of the object.
  • ⁇ C * RG when ⁇ C * RG is 0 or more, the color difference between red and green is larger than a certain level with respect to the comparative optical material. Since it can be clearly recognized and ⁇ C * RG is 10 or less, the color difference between red and green does not become too large, and as a result, the brightness is impaired when the object is visually recognized through the optical material. Red and green can be clearly recognized without any problem.
  • the color difference parameter ⁇ C * RG of the CIE1976 (L *, a *, b *) color system is preferably 2 or more and 10 or less from the viewpoint of making it easier to recognize the red color and green color of the object more clearly. It is more preferably 3 or more and 9 or less, further preferably 3.5 or more and 9 or less, particularly preferably 3.7 or more and 8.5 or less, and further preferably 4 or more and 8 or less. preferable.
  • the optical material of the first embodiment is a CIE1976 (L *, a *, b *) color difference parameter ⁇ C * R obtained from the above formula (2) and the following formula (3) by using a D65 light source.
  • -B is preferably 0 or more and 7 or less.
  • ⁇ C * RB ⁇ E * RB - ⁇ E * RB (w0) ⁇ ⁇ ⁇ (3)
  • ⁇ E * RB represents the color difference between red and blue of the optical material obtained by using the formula (2)
  • ⁇ E * RB (w0) is 2- (2 (w0).
  • the content of -t-octylphenyl) benzotriazole is 1.5% by mass, the mass ratio of the thiol composition 2 to the thiol composition 1 is 1.07, and the thiol composition with respect to the isocyanate group contained in the isocyanate composition.
  • a comparative optical material obtained by heat-curing a curable composition having a total molar ratio of thiol groups contained in the product 1 and the thiol composition 2 of 0.86 is described in the above formula (2) by using a D65 light source. Represents the color difference between red and blue obtained using.
  • the color difference parameter ⁇ C * RB of the CIE1976 (L *, a *, b *) color system is 0 or more and 7 or less, the object is subjected to the optical material.
  • the red and blue colors of the object can be clearly recognized when visually recognized.
  • the color difference parameter ⁇ C * RB of the CIE1976 (L *, a *, b *) color system shall be 0.5 or more and 7 or less from the viewpoint of making it easier to recognize the red and blue of the object more clearly. It is preferable, and it is more preferable that it is 1 or more and 6 or less.
  • ⁇ C * RG and ⁇ C * RB can be measured by the methods described in Examples described later.
  • the optical material of the first embodiment for example, the type, amount, combination, etc. of the dye contained in the optical material, the type, amount, combination, etc. of the additive such as the ultraviolet absorber contained in the optical material as needed, the optical
  • the above -mentioned ⁇ C * RG and ⁇ C * RB can be adjusted by appropriately adjusting the type, amount, combination, etc. of the polymer contained in the material as needed.
  • the thickness of the optical material of the first embodiment is not particularly limited, and may be, for example, 0.5 mm to 10 mm, 1 mm to 5 mm, or 1.5 mm to 3 mm. As an example, the thickness of the optical material of the first embodiment may be 2 mm. In the first embodiment, the thickness of the optical material means the maximum thickness.
  • the maximum absorption wavelength a is present in the range of 560 nm to 610 nm, preferably the maximum absorption wavelength a is present in the range of 570 nm to 600 nm, and more preferably within the range of 570 nm to 590 nm.
  • the maximum absorption wavelength a is present in the range of 570 nm to 600 nm, absorption of light between red light or green light necessary for visually recognizing an object tends to be suppressed.
  • only one maximum absorption wavelength a may be present in the range of 560 nm to 610 nm, or two or more of them may be present.
  • the half width of the absorption peak of the maximum absorption wavelength a is preferably 10 nm to 70 nm, more preferably 15 nm to 50 nm, and further preferably 20 nm to 40 nm.
  • the above-mentioned half-price width is 10 nm or more, light located between red light and green light tends to be absorbed in a wide wavelength range, and when the above-mentioned half-price width is 100 nm or less, it is a target. There is a tendency to suppress the absorption of light between the red light and the green light necessary for visually recognizing an object.
  • the full width at half maximum is the full width at half maximum, and is formed by a straight line parallel to the horizontal axis and an absorption peak drawn by 1/2 of the absorption coefficient value ( ⁇ g) at the maximum absorption wavelength in the absorption spectrum. It is expressed as the distance (nm) between two intersections.
  • the optical material of the first embodiment preferably has a maximum absorption wavelength b in the range of (B) 400 nm to 520 nm in the spectrum measured according to CIE1976.
  • the optical material of the first embodiment has a natural color tone in which blue color is suppressed.
  • only one maximum absorption wavelength b may be present in the range of 400 nm to 520 nm, or two or more maximum absorption wavelengths b may be present.
  • the maximum absorption wavelength b is preferably in the range of 430 nm to 490 nm, and more preferably in the range of 440 nm to 480 nm.
  • the transmittance at the maximum absorption wavelength b is preferably 3% to 60%, more preferably 10% to 55%, and even more preferably 15% to 50%.
  • the half width of the peak of the maximum absorption wavelength b is preferably 20 nm to 100 nm, more preferably 30 nm to 90 nm, and even more preferably 40 nm to 80 nm.
  • the half width of the peak of the maximum absorption wavelength b is 20 nm or more, light in the complementary color region of 560 nm to 610 nm can be effectively absorbed.
  • the half width of the peak of the maximum absorption wavelength b is 100 nm or less, it is possible to suppress the absorption of light other than the light in the complementary color region and the deterioration of the visibility of the object.
  • the transmittance at the maximum absorption wavelength b is 3% to 60%, and the half width of the peak of the maximum absorption wavelength b is 20 nm to 100 nm.
  • the difference between the maximum absorption wavelength a and the maximum absorption wavelength b is preferably 100 nm or more from the viewpoint that the maximum absorption wavelength b is the wavelength of the complementary color region of the maximum absorption wavelength a. It is more preferably 130 nm or more.
  • the difference between the maximum absorption wavelength a and the maximum absorption wavelength b is preferably 200 nm or less from the viewpoint that the maximum absorption wavelength b is the wavelength in the complementary color region of the maximum absorption wavelength a. It is more preferably 180 nm or less, and further preferably 160 nm or less.
  • the difference between the maximum absorption wavelength a and the maximum absorption wavelength b may be 130 nm to 200 nm.
  • the optical material of the first embodiment preferably has (a * 2 + b * 2 ) 1/2 of 10 or less, and preferably 9 or less. Is more preferable, and 8 or less is further preferable.
  • the optical material of the first embodiment preferably has b * of -10 to +10, more preferably -9 to +9, and-. It is more preferably 8 to +8.
  • the ratio of the integrated value of the peak of the maximum absorption wavelength b to the integrated value of the peak of the maximum absorption wavelength a is preferably 1.00 to 2.50.
  • the ratio of the integrated value of the peak of the maximum absorption wavelength b to the integrated value of the peak of the maximum absorption wavelength a is more preferably 1.10 to 2.20, and 1.20 to 2.00. It is more preferably 1.30 to 1.80, and particularly preferably 1.30 to 1.80.
  • the integrated value of the absorptivity at 560 nm to 610 nm may be 1800% to 2800%, preferably 2000% to 2500%.
  • the integrated value of the absorptivity at 400 nm to 520 nm may be 2800% to 4800%, preferably 3000% to 4500%.
  • the optical material of the first embodiment preferably contains a first dye having a maximum absorption wavelength in the range of 560 nm to 610 nm.
  • the first dye may be one kind alone or two or more kinds.
  • the first dye preferably contains a tetraazaporphyrin-based metal complex compound.
  • the tetraazaporphyrin-based metal complex compound is not particularly limited as long as it is a metal complex compound having a tetraazaporphyrin skeleton and a metal atom, and for example, a compound represented by the following general formula (1) is preferable.
  • a 1 to A 8 are independently hydrogen atom, halogen atom, nitro group, cyano group, hydroxy group, amino group, carboxyl group, sulfonic acid group, and linear chain having 1 to 20 carbon atoms.
  • Branched or cyclic alkyl group straight chain with 2 to 20 carbon atoms, branched or cyclic alkenyl group, straight chain with 2 to 20 carbon atoms, branched or cyclic alkynyl group, alkoxy group with 1 to 20 carbon atoms, carbon Aryloxy group with 6 to 20 carbon atoms, monoalkylamino group with 1 to 20 carbon atoms, dialkylamino group with 2 to 20 carbon atoms, dialkylamino group with 7 to 20 carbon atoms, aralkyl group with 7 to 20 carbon atoms, carbon It represents an aryl group having 6 to 20 carbon atoms, a heteroaryl group, an alkylthio group having 6 to 20 carbon atoms, or an arylthio group having 6 to 20 carbon atoms.
  • a 1 and A 2 , A 3 and A 4 , A 5 and A 6 , and A 7 and A 8 may independently form a ring excluding an aromatic ring.
  • 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.
  • Examples of the halogen atom in A 1 to A 8 include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, preferably a fluorine atom, a chlorine atom or a bromine atom, and more preferably a fluorine atom or a bromine atom.
  • Examples of the linear, branched or cyclic alkenyl group in A 1 to A 8 include a vinyl group, a 1-methylvinyl group, a propenyl group, a 2-butenyl group, a 2-pentenyl group and the like.
  • the linear, branched or cyclic alkynyl groups in A1 to A8 include ethynyl group, propynyl group, butynyl group, 1,3-butadiynyl group, 2-pentynyl group, 2,4-pentadiynyl group and 2-hexynyl group. , 3,3-Dimethyl-1-butynyl group, 3-heptynyl group, 4-octynyl group and the like.
  • M is preferably a divalent metal atom, and more preferably divalent copper.
  • the tetraazaporphyrin-based metal complex compound include a tetra-t-butyl-tetraazaporphyrin-copper complex represented by the following formula (1a).
  • Examples of commercially available products of the tetra-t-butyl-tetraazaporphyrin-copper complex include PD-311S (manufactured by Yamamoto Chemicals, Inc.).
  • Cu represents divalent copper
  • t—C 4 H 9 represents a tertiary butyl group
  • one of A 1 and A 2 one of A 3 and A 4 , A 5 and A 6
  • one of A 7 and A 8 is t-C 4 H 9 .
  • the content of the first dye is preferably 5 ppm to 18 ppm, more preferably 8 ppm to 15 ppm.
  • the first dye may be read as a tetraazaporphyrin-based metal complex compound.
  • the optical material of the first embodiment preferably satisfies at least one of the following (a) and (b), and more preferably satisfies both of the following (a) and (b).
  • (A) It has one or more maximum absorption wavelengths in the range of 400 nm or more and less than 500 nm.
  • (B) When the thickness of the optical material is 2 mm, the light transmittance at a wavelength of 380 nm or less is 20% or less.
  • the optical material When the optical material satisfies the above (a), the amount of stimulation of photoreceptor cells having photoresponsiveness to green light can be reduced, and red can be recognized more clearly. Further, it has an excellent blue light absorption rate, and can suppress adverse effects such as eye strain even when the screen of a personal computer or the like is viewed for a long time through the optical material of the first embodiment.
  • the optical material When the optical material satisfies the above (b), the transmission of ultraviolet light can be suppressed.
  • the light transmittance at a wavelength of 380 nm or less is preferably 10% or less, and more preferably 5% or less. Further, the above-mentioned "380 nm or less” is preferably read as "400 nm or less", and more preferably read as "420 nm or less”.
  • the light transmittance may be measured using an optical material having a thickness other than 2 mm, and the measured value may be converted into the light transmittance of the optical material when the thickness is 2 mm.
  • the light transmittance at a wavelength of 280 nm or more may be 20% or less, 10% or less, or 5% or less. good.
  • the blue light absorption rate of 380 nm to 500 nm in the spectrum measured according to EN ISO12312-1: 2013 is 15% to 50%. It is more preferably 20% to 50%, and even more preferably 30% to 50%.
  • the blue light absorption rate is 15% or more, the blue light is suitably cut and there is a tendency that adverse effects such as eye strain can be suppressed.
  • the blue light absorption rate is 50% or less, the visibility of blue color can be maintained, the visual transmittance does not decrease too much, and the darkening of the visual field can be suppressed.
  • the optical material of the first embodiment preferably contains at least one of a porphyrin-based compound and a merocyanine-based compound, and more preferably contains a porphyrin-based compound.
  • a porphyrin-based compound, a merocyanine-based compound, or the like When the optical material contains a porphyrin-based compound, a merocyanine-based compound, or the like, light having a wavelength in the range of 400 nm or more and less than 500 nm is suitably absorbed.
  • the porphyrin-based compound, the merocyanine-based compound, and the like may be independently used alone or in combination of two or more.
  • the porphyrin-based compound can be a second dye contained in the optical material of the first embodiment.
  • the spectacle lens of the present disclosure preferably contains a second dye having a maximum absorption wavelength in the range of 400 nm to 520 nm.
  • the second dye may be one kind alone or two or more kinds.
  • the second dye preferably contains at least one of a porphyrin-based compound and a merocyanine-based compound, and more preferably contains a porphyrin-based compound. Since the second dye contains a porphyrin-based compound, a merocyanine-based compound, or the like, it preferably absorbs light having a wavelength in the range of 400 nm or more and less than 500 nm.
  • the porphyrin-based compound preferably contains a compound represented by the following general formula (2).
  • X 1 to X 8 are independently hydrogen atom, halogen atom, nitro group, cyano group, hydroxy group, amino group, carboxyl group, sulfonic acid group, and linear chain having 1 to 20 carbon atoms.
  • Branched or cyclic alkyl group straight chain with 2 to 20 carbon atoms, branched or cyclic alkenyl group, straight chain with 2 to 20 carbon atoms, branched or cyclic alkynyl group, alkoxy group with 1 to 20 carbon atoms, carbon Aryloxy group with 6 to 20 carbon atoms, monoalkylamino group with 1 to 20 carbon atoms, dialkylamino group with 2 to 20 carbon atoms, dialkylamino group with 7 to 20 carbon atoms, aralkyl group with 7 to 20 carbon atoms, carbon It represents an aryl group having 6 to 20 carbon atoms, a heteroaryl group, an alkylthio group having 6 to 20 carbon atoms, or an arylthio group having 6 to 20 carbon atoms.
  • R 1 to R 4 independently represent a hydrogen atom or a linear or branched alkyl group
  • M is a two hydrogen atom, a divalent metal atom, a trivalent substituted metal atom, or a tetravalent substitution.
  • At least one of X 1 to X 8 is preferably a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a linear chain having 2 to 20 carbon atoms, a branched or branched. It is preferably a cyclic alkenyl group or a linear, branched or cyclic alkynyl group having 2 to 20 carbon atoms.
  • halogen atom in X1 to X8 examples include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, preferably a fluorine atom, a chlorine atom or a bromine atom, and more preferably a fluorine atom or a bromine atom.
  • R 1 to R 4 are independently hydrogen atoms or linear or branched alkyl groups having 1 to 8 carbon atoms.
  • M is preferably Cu, Zn, Fe, Co, Ni, Pt, Pd, Mn, Mg, Mn (OH), Mn (OH) 2 , VO, or TiO, and more preferably Ni, Pd or VO.
  • the preferred configuration of the cyclic alkynyl group is the same as A 1 to A 8 in the above-mentioned general formula (1).
  • the linear or branched alkyl group having 1 to 8 carbon atoms in R 1 to R 4 includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, and n.
  • -Pentyl group isopentyl group, neopentyl group, tert-pentyl group, 1,2-dimethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, n-hexyl group, 2-methylpentyl group, 4-methylpentyl group, 4-Methyl-2-pentyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, n-heptyl group, 3-methylhexyl group, 5-methylhexyl group, 2,4 -Includes dimethylpentyl group, n-octyl group, tert-octyl group, 2-ethylhexyl group, 2-propylpentyl group, 2,5-dimethylhexyl group and the like.
  • methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, 1,2-dimethylpropyl group, 1-Methylbutyl group, n-hexyl group, 1,2-dimethylbutyl group, 2-ethylbutyl group, n-heptyl group, n-octyl group or 2-ethylhexyl group are preferable, and methyl group, ethyl group and n-propyl group are preferable.
  • n-octyl group is more preferred.
  • the porphyrin-based compound that can be used as the optical material of the first embodiment can be produced with reference to a method known per se. For example, it can be produced by the method described in Inorganic Chem. 991, 30, 239-245 (Inorgan. Chem. 991, 30, 239-245). Further, as the compound represented by the general formula (2), for example, a pyrrole compound and an aldehyde compound were used to obtain a compound synthesized by a dehydration condensation reaction with an acid catalyst and a Rosemund reaction through an oxidation reaction with an oxidizing agent. Later, the compound can be produced by reacting the compound with a metal or a metal salt (for example, an acetylacetone complex or a metal acetate) in a solvent.
  • a metal or a metal salt for example, an acetylacetone complex or a metal acetate
  • Examples of the pyrrole compound include compounds represented by the general formulas (B-1) to (B-4), and examples of the aldehyde compound include general formulas (C-1) to (C-4). Examples include the represented compounds.
  • Examples of the acid catalyst include propionic acid, borontrifluoride-ethyl ether complex, trifluoroacetic acid and the like, and examples of the oxidizing agent include 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and the like. ..
  • X1 to X8 and R1 to R4 in the general formula (B- 1 ) to the general formula (B-4) and the general formula (C-1) to the general formula (C- 4 ) are the general formula (2). It is the same as X 1 to X 8 and R 1 to R 4 in.
  • the compound represented by the general formula (2) may be one kind or a mixture consisting of two or more kinds of isomers.
  • the content of the porphyrin-based compound is preferably 1.5 ppm to 16 ppm, more preferably 2 ppm to 12 ppm.
  • the content of the merocyanine-based compound is preferably 1.5 ppm to 14 ppm, more preferably 2 ppm to 12 ppm.
  • UVY-0026 manufactured by Yamamoto Kasei Co., Ltd.
  • UVY-1023 manufactured by Yamamoto Kasei Co., Ltd.
  • FDB-001 manufactured by Yamada Chemical Co., Ltd.
  • ABS 430 Longottica
  • the optical material of the first embodiment preferably contains a polymer.
  • a polymer such as a commercially available product may be used, or a monomer, a polymer obtained from the monomer or the like may be used.
  • the polymer can be used without particular limitation, and is preferably a transparent polymer.
  • the polymer and the monomer for obtaining the polymer will be described.
  • the polymer is not particularly limited, and for example, polyurethane, polythiourethane, polysulfide, polycarbonate, poly (meth) acrylate, polyolefin, cyclic polyolefin, polyallyl, polyurethane urea, polyene-polythiol polymer, ring-opened metasessis polymer, and the like.
  • examples thereof include polyester and epoxy resin.
  • One type of polymer may be used, or two or more types may be used in combination.
  • the optical material preferably contains at least one polymer selected from the group consisting of polyurethane, polythiourethane, polysulfide, polycarbonate, and poly (meth) acrylate, and more preferably contains polythiourethane. These polymers are highly transparent materials and can be suitably used for optical material applications.
  • Polyurethane contains a structural unit derived from a polyisocyanate compound and a structural unit derived from a polyol compound.
  • Polythiourethane contains a structural unit derived from a polyisocyanate compound and a structural unit derived from a polythiol compound.
  • polyisocyanate compound examples include 1,6-hexamethylene diisocyanate, 1,5-pentamethylene diisocyanate, 2,2,4-trimethylhexanediisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, and lysine diisocyanatomethyl ester.
  • Lysine triisocyanate m-xylylene diisocyanate, ⁇ , ⁇ , ⁇ ', ⁇ '-tetramethylxylylene diisocyanate, bis (isocyanatomethyl) naphthalin, mesitylylene triisocyanate, bis (isocyanatomethyl) sulfide, bis ( Isocyanatoethyl) sulfide, bis (isocyanatomethyl) disulfide, bis (isocyanatoethyl) disulfide, bis (isocyanatomethylthio) methane, bis (isocyanatoethylthio) methane, bis (isocyanatoethylthio) methane, bis (isocyanatoethylthio) ethane, bis (isocyanatoethylthio) An aliphatic polyisocyanate compound such as isocyanatomethylthio) ethane; isophor
  • Dicyclohexyldimethylmethaneisocyanate 2,5-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, 2,6-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, 3,8-bis (isocyanatomethyl) tricyclodecane, 3,9-bis (isocyanatomethyl) tricyclodecane, 4,8-bis (isocyanatomethyl) tricyclodecane, 4,9-bis (isocyanato) Alicyclic polyisocyanate compounds such as methyl) tricyclodecane; naphthalene diisocyanate, m-phenylenedi isocyanate, p-phenylenedi isocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, biphenyldiisocyanate, diphenylmethane-2, Aromatic polyisocyanate compounds such as
  • the polyol compound is one or more aliphatic or alicyclic alcohols, specifically, linear or branched aliphatic alcohols, alicyclic alcohols, these alcohols and ethylene oxide, propylene oxide, ⁇ -. Examples thereof include alcohols to which caprolactone is added, and at least one selected from these can be used.
  • ethylene glycol diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,3-propanediol, 2,2-dimethyl-1,3- Propylene diol, 2,2-diethyl-1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 3-methyl-1,3-butanjiol, 1 , 2-Pentinediol, 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, diglycerol
  • Examples of the alicyclic alcohol include 1,2-cyclopentanediol, 1,3-cyclopentanediol, 3-methyl-1,2-cyclopentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, and 1, , 4-Cyclohexanediol, 4,4'-bicyclohexanol, 1,4-Cyclohexanedimethanol and the like, and at least one selected from these can be used.
  • a compound to which these alcohols, ethylene oxide, propylene oxide, and ⁇ -caprolactone are added may be used.
  • an ethylene oxide adduct of glycerol, an ethylene oxide adduct of trimethylolpropane, an ethylene oxide adduct of pentaerythritol, a propylene oxide adduct of glycerol, a propylene oxide adduct of trimethylolpropane, a propylene oxide adduct of pentaerythritol examples thereof include caprolactone-modified glycerol, caprolactone-modified trimethylolpropane, caprolactone-modified pentaerythritol and the like, and at least one selected from these can be used.
  • polythiol compound examples include methanedithiol, 1,2-ethanedithiol, 1,2,3-propanetrithiol, 1,2-cyclohexanedithiol, bis (2-mercaptoethyl) ether, tetrakis (mercaptomethyl) methane, and diethylene glycol bis.
  • Aromatic polythiol compounds 2-methylamino-4,6-dithio Ru-sym-triazine, 3,4-thiophenethiol, bismuthiol, 2,5-bis (mercaptomethyl) -1,4-dithiane, 4,6-bis (mercaptomethylthio) -1,3-dithiane, 2- ( Heterocyclic polythiol compounds such as 2,2-bis (mercaptomethylthio) ethyl) -1,3-dithietane can be mentioned, and at least one selected from these can be used.
  • Polysulfide can be obtained by a method of ring-opening polymerization of a monomer such as a polyepithio compound or a polythietan compound.
  • the composition for optical materials can contain monomers constituting these polymers.
  • the polyepithio compound can be used without particular limitation, and for example, the compound described in Japanese Patent No. 6216383 can be used.
  • the polythietan compound a metal-containing thietan compound or a non-metal thietan compound can be used. Specifically, for example, those described in Japanese Patent No. 6216383 can be used.
  • Polycarbonate can be obtained by a reaction of alcohol with phosgene, a method of reacting alcohol with chlorohomet, or a transesterification reaction of a carbonic acid diester compound, but a generally available commercially available polycarbonate resin is used. It is also possible. As a commercially available product, a panlight series manufactured by Teijin Chemicals Ltd. or the like can be used.
  • the composition for an optical material of the first embodiment can contain polycarbonate as a resin material.
  • the poly (meth) acrylate can be used without particular limitation, and for example, the one described in Japanese Patent No. 6216383 can be used.
  • the polyolefin can be used without particular limitation, and for example, the specific examples described in Japanese Patent No. 6216383, the polymerization reaction of cyclic polyolefins and olefins, and the method for producing polyolefins can be used.
  • Polyallyl is 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.
  • allyl group-containing monomer allyl diglycol carbonate and diallyl phthalate are generally commercially available, and these can be preferably used.
  • Polyurethane urea is a reaction product of a polyurethane prepolymer and a diamine curing agent, and is a trademark TRIVEX of PPG Industries, Inc. A typical example is the one sold by. Polyurethane urea is a highly transparent material and can be suitably used.
  • the polyene-polythiol polymer is an addition polymerization composed 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, and high by ethylene chain polymerization. It is a molecular product.
  • polyene compound in the polyene-polythiol polymer for example, the one described in Japanese Patent No. 6216383 can be used.
  • the ring-opening metathesis polymer is a polymer obtained by ring-opening polymerization of cyclic olefins using a catalyst.
  • cyclic olefins that can be subjected to ring-opening polymerization, for example, those described in Japanese Patent No. 6216383 can be used.
  • Polyester is condensation polymerized in the presence of known polyester production catalysts such as Lewis acid catalysts typified by antimony and germanium compounds, organic acids and inorganic acids. Specifically, one or more selected from polyvalent carboxylic acids containing dicarboxylic acids and ester-forming derivatives thereof, and one or more selected from polyhydric alcohols containing glycols. Alternatively, it refers to a hydroxycarboxylic acid and an ester-forming derivative thereof, or a cyclic ester.
  • Lewis acid catalysts typified by antimony and germanium compounds
  • organic acids and inorganic acids Specifically, one or more selected from polyvalent carboxylic acids containing dicarboxylic acids and ester-forming derivatives thereof, and one or more selected from polyhydric alcohols containing glycols. Alternatively, it refers to a hydroxycarboxylic acid and an ester-forming derivative thereof, or a cyclic ester.
  • dicarboxylic acid and glycol for example, those described in Japanese Patent No. 6216383 can be used.
  • polyester for example, the polyester described in Japanese Patent No. 6216383 can be used.
  • the epoxy resin is a polymer obtained by ring-opening polymerization of an epoxy compound, and as the epoxy compound, for example, the one described in Japanese Patent No. 6216383 can be used.
  • the optical material of the first embodiment may contain an additive as a component other than the above.
  • the additive include a polymerization catalyst, an internal mold release agent, a dye, and an ultraviolet absorber.
  • a polymerization catalyst may or may not be used.
  • the internal mold release agent include acidic phosphoric acid esters.
  • the acidic phosphoric acid ester include a phosphoric acid monoester and a phosphoric acid diester, which can be used alone or in combination of two or more.
  • ultraviolet absorber examples include 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-acryloyloxybenzophenone, 2-hydroxy-4-acryloyloxy-5-tert-butylbenzophenone, and 2-hydroxy-4-.
  • Abenzophenone-based ultraviolet absorbers such as acryloyloxy-2', 4'-dichlorobenzophenone, 2- [4-[(2-hydroxy-3-dodecyloxypropyl) oxy] -2-hydroxyphenyl] 4,6-bis ( 2,4-dimethylphenyl) -1,3,5-triazine, 2- [4- (2-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-bis-butyloxyphenyl) -1,3, Triazine-based
  • a commercially available product may be used as the ultraviolet absorber.
  • Examples of the commercially available product include Tinuvin 326 (manufactured by BASF Japan Ltd.) and Viosorb 583 (manufactured by Kyodo Yakuhin Co., Ltd.).
  • the optical material of the first embodiment may contain a color tone adjusting agent.
  • the content of the color tone adjusting agent may be 3 ppm to 50 ppm or 5 ppm to 40 ppm.
  • Examples of the color tone adjusting agent include those having an absorption band in the wavelength range from orange to yellow in the visible light region and having a function of adjusting the hue of an optical material containing a polymer.
  • Examples of the color tone adjusting agent include a bluing agent.
  • Examples of the bluing agent include those having an absorption band in the orange to yellow wavelength range in the visible light region and having a function of adjusting the hue of an optical material made of a resin material.
  • the bluing agent may contain a substance exhibiting blue to purple.
  • the optical material of the first embodiment preferably has a visual transmittance of 65% or more, more preferably 68% or more, and further preferably 70% or more.
  • the visual transmittance can be measured using a spectrocolorimeter (for example, CM-5 manufactured by Konica Minolta) and an optical material having a thickness of 2 mm.
  • the optical material can be produced, for example, by using the composition for an optical material described below.
  • the composition for an optical material contains (A) a first dye having a maximum absorption wavelength a in the range of 560 nm to 610 nm in a spectrum measured according to CIE1976, and the composition for an optical material is cured.
  • the obtained optical material has the CIE1976 (L *, a *, b *) color difference parameter ⁇ C * RG obtained from the above equations (1) and (2) by using the D65 light source. Satisfy 0 or more and 10 or less.
  • composition for an optical material may contain the above-mentioned polymer or the above-mentioned monomer, may contain the above-mentioned porphyrin compound which can be the second dye, and may contain an additive such as an ultraviolet absorber. May be good.
  • the content of the dye is preferably 0.0001 part by mass to 0.008 part by mass, and more preferably 0.0001 part by mass to 0.006 part by mass with respect to 100 parts by mass of the total of the above-mentioned polymer and the above-mentioned monomer. , 0.0002 part by mass to 0.004 part by mass is more preferable.
  • the content of the dye means the total content of all the dyes contained in the composition for optical materials.
  • the composition for an optical material can be obtained by mixing the above components by a predetermined method.
  • the mixing order, mixing method, etc. of each component in the composition are not particularly limited, and a known method can be used.
  • a known method for example, there is a method of preparing a masterbatch containing a predetermined amount of additives, dispersing the masterbatch in a solvent, and dissolving the masterbatch.
  • a polyurethane resin there is a method of dispersing an additive in a polyisocyanate compound and dissolving it to prepare a masterbatch.
  • optical material of the first embodiment examples include an optical material made of a base material, an optical material made of a base material and a coating layer, and the like.
  • base material examples include a lens base material.
  • the coating layer examples include a primer layer, a hard coat layer, an antireflection layer, an anti-fog coating layer, an anti-contamination layer, and a water-repellent layer.
  • a primer layer a hard coat layer
  • an antireflection layer an anti-fog coating layer
  • an anti-contamination layer an anti-contamination layer
  • a water-repellent layer a coating layer that covers the coating layer.
  • Each of these coating layers can be used alone, or a plurality of coating layers can be used in layers. When the coating layers are applied to both surfaces, the same coating layer may be applied to each surface, or different coating layers may be applied to each surface.
  • a molded product for example, a lens substrate
  • a composition for an optical material containing no dye is prepared using a composition for an optical material containing no dye, and then the molded product is immersed in a dispersion obtained by dispersing the dye in water or a solvent.
  • the dye may be impregnated into the molded body, and the molded body impregnated with the dye may be dried.
  • An optical material can be prepared using the molded body thus obtained.
  • the porphyrin-based compound can be impregnated into the optical material.
  • a spectacle lens including a lens base material and a coating layer laminated as needed can be immersed in a dispersion liquid containing a dye to impregnate the lens with the dye.
  • the impregnation amount of the dye may be adjusted to a desired impregnation amount depending on the concentration of the dye in the dispersion liquid, the temperature of the dispersion liquid, the time for immersing the molded product, the optical material, and the like. The higher the concentration, the higher the temperature, and the longer the immersion time, the higher the impregnation amount.
  • the immersion may be repeated a plurality of times under the condition that the impregnation amount is small.
  • a composition for an optical material containing a dye may be used as a coating material to form a dye-containing coating layer on an optical material such as a plastic lens.
  • An optical material having such a structure can be suitably used as a lens, preferably a spectacle lens.
  • the first embodiment is not limited to the above-described embodiment, and various embodiments can be taken as long as the effects of the present invention are not impaired.
  • Lenses such as spectacle lenses, goggles, spectacle lenses for vision correction, lenses for imaging devices, frennel lenses for liquid crystal projectors, wrenchular lenses, contact lenses, lenses for wearable devices; Encapsulant for light emitting diode (LED); Optical waveguide; Optical lens; Optical adhesive used for joining optical waveguides, etc .; Antireflection film used for optical lenses, etc .; Liquid crystal display device member (substrate, light guide plate, film, sheet) Transparent coating used for (etc.); Windshield used for car front glass, motorcycle helmet, etc .; Transparent substrate; Cover for lighting equipment, film to be attached to the irradiation surface of lighting equipment, etc.; And so on. Since the optical material of the first embodiment can contain an ultraviolet absorber, a lens is preferable among the above.
  • the lens of the first embodiment includes the optical material of the first embodiment described above.
  • the lens of the first embodiment may be a lens having a lens base material made of an optical material, or may have a coating layer on one side or both sides of the lens base material.
  • the lens of the first embodiment may be any of the various lenses exemplified in the above-mentioned use of the optical material.
  • the coating layer include a primer layer, a hard coat layer, an antireflection layer, an anti-fog coat layer, an anti-staining layer, and a water-repellent layer.
  • a primer layer a hard coat layer
  • an antireflection layer an anti-fog coat layer
  • an anti-staining layer an anti-staining layer
  • a water-repellent layer a coating layer that covers the coating layer.
  • Each of these coating layers can be used alone, or a plurality of coating layers can be used in layers. When the coating layers are applied to both surfaces, the same coating layer may be applied to each surface, or different coating layers may be applied to each surface.
  • These coating layers provide the performance of dyes, infrared absorbers, light stabilizers, antioxidants, dyes, pigments, photochromic dyes, photochromic pigments, antistatic agents, and other lenses used in the first embodiment. It may contain a known additive or the like for enhancing.
  • various leveling agents for the purpose of improving the coatability may be used.
  • the primer layer is usually formed between the hard coat layer described later and the lens substrate.
  • the primer layer is a coating layer for the purpose of improving the adhesion between the hard coat layer formed on the primer layer and the lens base material, and it is also possible to improve the impact resistance in some cases.
  • the primer layer may be a primer layer having high adhesion to the obtained lens substrate.
  • a primer composition containing a urethane resin, an epoxy resin, a polyester resin, a melamine resin, or a polyvinyl acetal as a main component may be used. It is used to form a primer layer.
  • a solvent that does not affect the lens substrate may be used or may not be used for the purpose of adjusting the viscosity of the composition.
  • the primer layer can be formed by either the coating method or the dry method.
  • the coating method is used, the primer layer is formed by applying the primer composition to the lens substrate by a known coating method such as spin coating or dip coating and then solidifying the primer composition.
  • a dry method it is formed by a known dry method such as a CVD method or a vacuum vapor deposition method.
  • the surface of the lens substrate may be subjected to pretreatment such as alkali treatment, plasma treatment, or ultraviolet treatment, if necessary, for the purpose of improving adhesion.
  • the hard coat layer is a coating layer for the purpose of imparting functions such as scratch resistance, abrasion resistance, moisture resistance, temperature water resistance, heat resistance, and weather resistance to the lens surface.
  • an organic silicon compound having curability and an element selected from the element group of Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In and Ti are used for the formation of the hard coat layer.
  • a hard coat composition containing one or more of the oxide fine particles contained therein may be used.
  • a composite oxide containing a curable organic silicon compound and two or more elements selected from the element group of Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In and Ti A hard coat composition containing one or more of the fine particles of the above may be used.
  • the hard coat composition comprises amines, amino acids, metal acetylacetonate complexes, organic acid metal salts, perchloric acids, perchloric acid salts, acids, metal chlorides and polyfunctional epoxy compounds. It is preferred to include at least one selected from the group.
  • the hard coat composition may or may not contain a solvent that does not affect the lens substrate.
  • the hard coat layer is usually formed by applying a hard coat composition by a known coating method such as spin coating or dip coating and then curing it.
  • a hard coat composition by a known coating method such as spin coating or dip coating and then curing it.
  • the curing method include irradiation with energy rays such as ultraviolet rays and visible light, and heat curing.
  • the refractive index of the hard coat layer is preferably in the range of ⁇ 0.1 in the difference in refractive index from the lens substrate.
  • the antireflection layer includes an inorganic type and an organic type.
  • the inorganic antireflection layer is formed by a dry method such as a vacuum vapor deposition method, a sputtering method, an ion plating method, an ion beam assist method, and a CVD method using an inorganic oxide such as SiO 2 or TiO 2 .
  • the organic antireflection layer is formed by a wet process using a composition containing an organosilicon compound and silica-based fine particles having internal cavities. The antireflection layer may be formed on the hard coat layer, if necessary.
  • the antireflection layer may be a multilayer or a single layer. From the viewpoint of effectively exhibiting the antireflection function, the antireflection layer is preferably multi-layered, and in that case, the low refractive index layer and the high refractive index layer are preferably laminated alternately. Further, the difference in refractive index between the low refractive index layer and the high refractive index layer is preferably 0.1 or more.
  • the high refractive index layer include layers such as ZnO, TiO 2 , CeO 2 , Sb2O 5 , SnO 2 , ZrO 2 , and Ta 2 O 5
  • examples of the low refractive index layer include layers such as SiO 2 . When used in a single layer, it is preferable that the refractive index is at least 0.1 or more lower than the refractive index of the hard coat layer.
  • An anti-fog coat layer, an anti-contamination layer, a water-repellent layer, etc. may be formed on the anti-reflection layer, if necessary.
  • the method for forming the anti-fog layer, the anti-contamination layer, the water-repellent layer and the like is not particularly limited, and conventionally known methods can be applied.
  • the wearable device of the first embodiment includes a lens for use in the wearable device.
  • the wearable device of the first embodiment may be, for example, a wearable device used for a computer game or the like, a wearable device that realizes virtual reality (VR: Virtual Reality), augmented reality (AR), or the like.
  • VR Virtual Reality
  • AR augmented reality
  • the wearable device provided with the lens of the first embodiment can clearly recognize the red and green of an object even when used in a computer game or the like in which an image is processed at high speed, for example. It is also suitable for electronic competitions by computer games such as e-sports.
  • the eyewear of the first embodiment is eyewear that may include at least two optical members, an optical member on the objective side and an optical member on the opposite eye side facing the optical member on the objective side.
  • the maximum absorption wavelength a exists in the range of 560 nm to 610 nm, and the maximum absorption wavelength a exists.
  • the maximum absorption wavelength b exists in the range of 400 nm to 520 nm, and the maximum absorption wavelength b exists.
  • the ratio of the integrated value of the peak of the maximum absorption wavelength b to the integrated value of the peak of the maximum absorption wavelength a is 1.00 to 2.50.
  • the eyewear of the first embodiment has a natural color tone in which blue is suppressed, and the red and green of the object can be clearly recognized.
  • the optical material of the first embodiment can be used as an optical member in the eyewear of the first embodiment.
  • the preferred embodiment of the optical material of the first embodiment can be used as a preferred embodiment of the optical member in the eyewear of the first embodiment.
  • the range of the color difference parameter of the CIE1976 (L *, a *, b *) color system obtained from the above equations (1), (2), (3) and the like is also the eye of the first embodiment. It can be applied to optical members in clothing.
  • the eyewear of the first embodiment may include at least two optical members, an optical member on the objective side and an optical member on the eye-to-eye side facing the optical member on the objective side.
  • the eyewear of the first embodiment is the above-mentioned in the spectrum measured according to CIE1976 between the outermost surface of the objective side of the optical member on the objective side and the outermost surface of the eyepiece side of the optical member on the opposite eye side.
  • the limitation is particularly limited. do not have.
  • Eyewear that includes at least two optical members, an optical member on the objective side and an optical member on the opposite eye side facing the optical member on the objective side, includes, for example, clip-on type eyeglasses, eyeglasses provided with overglasses, and the like. Can be mentioned.
  • the eyewear of the first embodiment may include one optical member.
  • Examples of eyewear including one optical member include eyeglasses having a dyed lens.
  • optical member examples include a lens, a filter, goggles, a mirror, a visor for a helmet, an LED (light emitting dimension) screen, a computer screen, a windshield, and the like.
  • the spectacle lens of the second embodiment includes a functional layer, and the functional layer has a maximum absorption wavelength a in the range of (A) 560 nm to 610 nm in a spectrum measured according to CIE1976, and (B).
  • the maximum absorption wavelength b exists in the range of 400 nm to 520 nm, and the ratio of the integrated value of the peak of the maximum absorption wavelength b to the integrated value of the peak of the maximum absorption wavelength a is 1.00 to 2.50.
  • the red color and the green color of the object can be clearly recognized.
  • the reason for this is presumed as follows. First, since the maximum absorption wavelength exists in the range of 560 nm to 610 nm, the light whose wavelength range is located between the red light and the green light is easily absorbed by the spectacle lens. As a result, the transmittance of light whose wavelength range is located between the red light and the green light is reduced by the spectacle lens, and it becomes easy to clearly recognize the red and green of the object.
  • the transmittance of light in the blue region that is, wavelength 400 nm to 520 nm
  • the transmittance of light in the blue region can be reduced by the presence of the maximum absorption wavelength b in the range of 400 nm to 520 nm.
  • the ratio of the integrated value of the peak of the maximum absorption wavelength b to the integrated value of the peak of the maximum absorption wavelength a is 1.00 to 2.50.
  • the spectacle lens of the second embodiment including each of the above configurations has a natural color tone in which blue is suppressed, and the red and green of the object can be clearly recognized.
  • the spectacle lens of the second embodiment includes a functional layer, and the functional layer has a maximum absorption wavelength a in the range of (A) 560 nm to 610 nm in a spectrum measured according to CIE1976, and (B) 400 nm.
  • the maximum absorption wavelength b exists in the range of about 520 nm, and the ratio of the integrated value of the peak of the maximum absorption wavelength b to the integrated value of the peak of the maximum absorption wavelength a is 1.00 to 2.50.
  • only one maximum absorption wavelength a may be present in the range of 560 nm to 610 nm, or two or more of them may be present.
  • only one maximum absorption wavelength b may be present in the range of 400 nm to 520 nm, or two or more of them may be present.
  • the functional layer has a maximum absorption wavelength a in the range of (A) 560 nm to 610 nm. This makes it possible to clearly recognize the red color and green color of the object. From the above viewpoint, the maximum absorption wavelength a is preferably in the range of 570 nm to 600 nm, and more preferably in the range of 580 nm to 595 nm.
  • the transmittance at the maximum absorption wavelength a is preferably 5% to 50%, more preferably 10% to 40%, and even more preferably 20% to 40%.
  • the half width of the peak of the maximum absorption wavelength a is preferably 10 nm to 70 nm, more preferably 10 nm to 50 nm, and even more preferably 20 nm to 40 nm. Since the half width of the peak of the maximum absorption wavelength a is 10 nm or more, the light located between the red light and the green light tends to be absorbed in a wide wavelength range. When the half width of the peak of the maximum absorption wavelength a is 70 nm or less, the absorption of light between the red light or the green light necessary for visually recognizing the object tends to be suppressed.
  • the full width at half maximum is the full width at half maximum, and the straight line parallel to the horizontal axis and the absorption peak drawn by 1/2 of the absorption coefficient value ( ⁇ g) at the maximum absorption wavelength in the absorption spectrum. It is expressed as the distance (nm) between the two intersections formed by.
  • the functional layer has a maximum absorption wavelength b in the range of (B) 400 nm to 520 nm.
  • the spectacle lens of the second embodiment has a natural color tone in which blue color is suppressed.
  • the maximum absorption wavelength b is preferably in the range of 430 nm to 490 nm, and more preferably in the range of 440 nm to 480 nm.
  • the transmittance at the maximum absorption wavelength b is preferably 3% to 60%, more preferably 10% to 55%, and even more preferably 15% to 50%.
  • the half width of the peak of the maximum absorption wavelength b is preferably 20 nm to 100 nm, more preferably 30 nm to 90 nm, and even more preferably 40 nm to 80 nm.
  • the half width of the peak of the maximum absorption wavelength b is 20 nm or more, light in the complementary color region of 560 nm to 610 nm can be effectively absorbed.
  • the half width of the peak of the maximum absorption wavelength b is 100 nm or less, it is possible to suppress the absorption of light other than the light in the complementary color region and the deterioration of the visibility of the object.
  • the transmittance at the maximum absorption wavelength b is 3% to 60%, and the half width of the peak of the maximum absorption wavelength b is 20 nm to 100 nm.
  • the difference between the maximum absorption wavelength a and the maximum absorption wavelength b is preferably 100 nm to 200 nm, preferably 100 nm to 180 nm, from the viewpoint that the maximum absorption wavelength b is the wavelength of the complementary color region of the maximum absorption wavelength a. It is more preferably present, and even more preferably 100 nm to 160 nm.
  • (a * 2 + b * 2 ) 1/2 is preferably 10 or less, and 9 or less. Is more preferable, and 8 or less is further preferable.
  • b * is preferably -10 to +10, more preferably -9 to +9, and-. It is more preferably 8 to +8.
  • the ratio of the integrated value of the peak of the maximum absorption wavelength b to the integrated value of the peak of the maximum absorption wavelength a is 1.00 to 2.50.
  • the ratio of the integrated value of the peak of the maximum absorption wavelength b to the integrated value of the peak of the maximum absorption wavelength a is preferably 1.10 to 2.20, preferably 1.20 to 2.00. It is more preferably 1.30 to 1.80, and even more preferably 1.30 to 1.80.
  • the integrated value of the absorptivity at 560 nm to 610 nm may be 1800% to 2800%, preferably 2000% to 2500%.
  • the integrated value of the absorptivity at 400 nm to 520 nm may be 2800% to 4800%, preferably 3000% to 4500%.
  • the color difference parameter ⁇ C * RG of the CIE1976 (L *, a *, b *) color system obtained by the following formula (1) is 0 or more and 10 or less.
  • ⁇ C * RG ⁇ E * RG ⁇ E * RG (w0) ⁇ ⁇ ⁇ (1)
  • ⁇ E * ( ⁇ L * 2 + ⁇ a * 2 + ⁇ b * 2 ) 1/2 ... (2)
  • ⁇ E * RG represents the color difference between red and green obtained by the formula (2) for the spectacle lens using the D65 light source.
  • ⁇ E * RG (w0) is 2- (2'-hydroxy-5'-t-octylphenyl) benzotriazole, 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1]. ] From an isocyanate composition containing heptane, a thiol composition containing pentaerythritol tetrakis (3-mercaptopropionate), and a thiol composition 2 containing 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane.
  • the content of the 2- (2'-hydroxy-5'-t-octylphenyl) benzotriazole is 1.5% by mass, and the mass ratio of the thiol composition 2 to the thiol composition 1 is 1.07.
  • the color difference between red and green obtained by the formula (2) using a D65 light source is represented.
  • ⁇ L * represents the difference in brightness
  • ⁇ a represents the difference in chromaticity in the red-green direction
  • ⁇ b represents the difference in chromaticity in the blue-yellow direction.
  • the color difference between red and green with respect to the comparative optical material becomes larger than a certain level. Can be clearly recognized.
  • ⁇ C * RG is 10 or less, the color difference between red and green does not become too large, and as a result, the brightness is not impaired when the object is visually recognized through the spectacle lens. You can clearly recognize the green color.
  • the color difference parameter ⁇ C * RG of the CIE1976 (L *, a *, b *) color system is preferably 3 or more and 9 or less from the viewpoint of making it easier to recognize the red color and green color of the object more clearly. , 3.5 or more and 9 or less, more preferably 3.7 or more and 8.5 or less, and particularly preferably 4 or more and 8 or less.
  • ⁇ C * RG can be measured by the method described in Examples described later.
  • the type, amount, combination, etc. of the dye contained in the spectacle lens for example, the type, amount, combination, etc. of the additive such as the ultraviolet absorber contained in the spectacle lens as needed, the spectacles.
  • the above -mentioned ⁇ C * RG can be adjusted by appropriately adjusting the type, amount, combination, etc. of the polymer contained in the lens as needed.
  • the thickness of the spectacle lens of the second embodiment is not particularly limited, and may be, for example, 0.5 mm to 10 mm, 1 mm to 5 mm, or 1.5 mm to 3 mm. As an example, the thickness of the spectacle lens of the second embodiment may be 2 mm. In the second embodiment, the thickness of the spectacle lens means the maximum thickness.
  • the spectacle lens of the second embodiment preferably contains a first dye having a maximum absorption wavelength in the range of 560 nm to 610 nm.
  • the first dye may be one kind alone or two or more kinds.
  • the details of the specific embodiment, the preferred embodiment, the preferred content, etc. of the first dye in the second embodiment are the same as the details of the specific embodiment, the preferred embodiment, the preferred content, etc. of the first dye in the first embodiment. Is.
  • the spectacle lens of the second embodiment preferably contains a second dye having a maximum absorption wavelength in the range of 400 nm to 520 nm.
  • the second dye may be one kind alone or two or more kinds.
  • the details of the specific embodiment, the preferred embodiment, the preferred content, etc. of the second dye in the second embodiment are the same as the details of the specific embodiment, the preferred embodiment, the preferred content, etc. of the second dye in the first embodiment. Is.
  • the functional layer in the second embodiment preferably contains a polymer.
  • the details of the specific embodiment, the preferred embodiment, the preferred content, etc. of the polymer in the second embodiment are the same as the details of the specific embodiment, the preferred embodiment, the preferred content, etc. of the polymer in the first embodiment.
  • the spectacle lens of the second embodiment may contain an additive as an ingredient other than the above.
  • the additive include a polymerization catalyst, an internal mold release agent, a dye, and an ultraviolet absorber.
  • a polymerization catalyst may or may not be used. Details of specific embodiments, preferred embodiments, preferred contents and the like of the additives such as the polymerization catalyst, the internal release agent, the dye and the ultraviolet absorber in the second embodiment are described in detail in the polymerization catalyst and the internal release form in the first embodiment. It is the same as the details of the specific embodiment, the preferable embodiment, the preferable content and the like of each additive such as an agent, a dye and an ultraviolet absorber.
  • the spectacle lens of the second embodiment may contain a color tone adjusting agent, but does not necessarily have to contain the color tone adjusting agent. As described above, the spectacle lens of the second embodiment has a natural color tone in which blue color is suppressed even if the color tone adjusting agent is not contained. Therefore, it is not necessary to include a color tone adjusting agent.
  • the color tone adjusting agent one having an absorption band in the wavelength range from orange to yellow in the visible light region and having a function of adjusting the hue of a spectacle lens containing a polymer may be used.
  • a bluing agent may be used.
  • the brewing agent an agent having an absorption band in the wavelength range from orange to yellow in the visible light region and having a function of adjusting the hue of a spectacle lens made of a resin material may be used.
  • the bluing agent may contain a substance exhibiting blue to purple.
  • the spectacle lens of the second embodiment has a natural color tone in which blue color is suppressed even if it does not contain a color tone adjusting agent, but may contain a color tone adjusting agent.
  • the content of the color tone adjusting agent may be relatively small.
  • the content of the color tone adjusting agent may be 5 ppm or less, or may be 3 ppm or less.
  • the lower limit of the content of the color tone adjusting agent in the spectacle lens of the second embodiment is not particularly limited.
  • the content of the color tone adjusting agent may be 0 ppm or more, or may be more than 0 ppm.
  • the spectacle lens of the second embodiment preferably has a visual transmittance of 65% or more, more preferably 68% or more, and further preferably 70% or more.
  • the visual transmittance can be measured using a spectrocolorimeter (for example, CM-5 manufactured by Konica Minolta) and a spectacle lens having a thickness of 2 mm.
  • the spectacle lens can be manufactured, for example, by using the composition for spectacle lens described below.
  • the composition for a spectacle lens has a first dye having a maximum absorption wavelength a in the range of 560 nm to 610 nm in the spectrum measured according to CIE1976, and a composition in the range of 400 nm to 520 nm in the spectrum measured according to CIE1976.
  • the ratio of the integrated value of the peak of the maximum absorption wavelength b to the integrated value of the peak of the maximum absorption wavelength a is 1.00 to 2.50, including the second dye having the maximum absorption wavelength b inside. ..
  • composition for a spectacle lens may contain the above-mentioned polymer or the above-mentioned monomer, or may contain an additive such as an ultraviolet absorber.
  • the preferred content of the dye in the second embodiment is the same as the preferred content of the dye in the first embodiment.
  • the details of the method for producing the composition for spectacle lenses such as the mixing method in the second embodiment are the same as the details of the method for producing the composition for spectacle lenses such as the mixing method in the first embodiment.
  • Examples of the spectacle lens of the second embodiment include a spectacle lens composed of a functional layer, a spectacle lens composed of a functional layer and a coating layer, and the like.
  • the spectacle lens of the second embodiment further includes an antireflection layer on the surface.
  • the details of the specific embodiment, the preferred embodiment, the manufacturing method and the like of the antireflection layer in the second embodiment are the same as the details of the specific aspect, the preferable mode, the manufacturing method and the like of the antireflection layer in the first embodiment.
  • the primer layer is usually formed between the hard coat layer and the lens substrate.
  • the details of the specific aspect, the preferable aspect, the manufacturing method and the like of the primer layer in the second embodiment are the same as the details of the specific aspect, the preferable aspect, the manufacturing method and the like of the primer layer in the first embodiment.
  • the hard coat layer is a coating layer for the purpose of imparting functions such as scratch resistance, abrasion resistance, moisture resistance, temperature water resistance, heat resistance, and weather resistance to the lens surface.
  • the details of the specific aspect, the preferable aspect, the manufacturing method and the like of the hard coat layer in the second embodiment are the same as the details of the specific aspect, the preferable aspect, the manufacturing method and the like of the hard coat layer in the first embodiment.
  • the eyewear of the second embodiment is eyewear that may include at least two optical members, an optical member on the objective side and an optical member on the opposite eye side facing the optical member on the objective side.
  • the maximum absorption wavelength a exists in the range of 560 nm to 610 nm, and the maximum absorption wavelength a exists.
  • the maximum absorption wavelength b exists in the range of 400 nm to 520 nm, and the maximum absorption wavelength b exists.
  • the ratio of the integrated value of the peak of the maximum absorption wavelength b to the integrated value of the peak of the maximum absorption wavelength a is 1.00 to 2.50.
  • the details of the specific aspects, preferred embodiments, etc. of the eyewear in the second embodiment are the same as the details of the specific embodiments, preferred embodiments, etc. of the eyewear in the first embodiment.
  • the second embodiment includes the following aspects.
  • the functional layer has a maximum absorption wavelength a in the range of (A) 560 nm to 610 nm and (B) 400 nm to 520 nm in the spectrum measured according to CIE1976.
  • a spectacle lens in which the maximum absorption wavelength b exists within the range, and the ratio of the integrated value of the peak of the maximum absorption wavelength b to the integrated value of the peak of the maximum absorption wavelength a is 1.00 to 2.50.
  • ⁇ 2-3> Described in ⁇ 2-1> or ⁇ 2-2> in which (a * 2 + b * 2 ) 1/2 is 10 or less in the CIE1976 (L *, a *, b *) color system. Glasses lens.
  • the color difference parameter ⁇ C * RG of the CIE1976 (L *, a *, b *) color system obtained by the following equation (1) is 0 or more and 10 or less ⁇ 2-1> to ⁇ 2.
  • ⁇ C * RG ⁇ E * RG ⁇ E * RG (w0) ⁇ ⁇ ⁇ (1)
  • ⁇ E * ( ⁇ L * 2 + ⁇ a * 2 + ⁇ b * 2 ) 1/2 ...
  • ⁇ E * RG represents the color difference between red and green obtained by the formula (2) for the spectacle lens using the D65 light source.
  • ⁇ E * RG (w0) is 2- (2'-hydroxy-5'-t-octylphenyl) benzotriazole, 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1]. ] From an isocyanate composition containing heptane, a thiol composition containing pentaerythritol tetrakis (3-mercaptopropionate), and a thiol composition 2 containing 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane.
  • the content of the 2- (2'-hydroxy-5'-t-octylphenyl) benzotriazole is 1.5% by mass, and the mass ratio of the thiol composition 2 to the thiol composition 1 is 1.07.
  • the color difference between red and green obtained by the formula (2) using a D65 light source is represented.
  • ⁇ L * represents the difference in brightness
  • ⁇ a * represents the difference in chromaticity in the red-green direction
  • ⁇ b * represents the difference in chromaticity in the blue-yellow direction.
  • ⁇ 2-5> The spectacle lens according to any one of ⁇ 2-1> to ⁇ 2-4>, wherein the maximum absorption wavelength b is 430 nm to 490 nm.
  • the transmittance at the maximum absorption wavelength b is 3% to 60%
  • the half width of the peak of the maximum absorption wavelength b is 20 nm to 100 nm.
  • the transmittance at the maximum absorption wavelength a is 5% to 50%, and the half width of the peak of the maximum absorption wavelength a is 10 nm to 70 nm.
  • the functional layer contains at least one polymer selected from the group consisting of polyurethane, polythiourethane, polysulfide, polycarbonate, and poly (meth) acrylate ⁇ 2-1> to ⁇ 2-.
  • ⁇ 2-9> The spectacle lens according to any one of ⁇ 2-1> to ⁇ 2-8>, further comprising an antireflection layer on the surface.
  • An eyewear that may include at least two optical members, an optical member on the objective side and an optical member on the opposite eye side facing the optical member on the objective side.
  • the maximum absorption wavelength a exists in the range of 560 nm to 610 nm, and the maximum absorption wavelength a exists.
  • the maximum absorption wavelength b exists in the range of 400 nm to 520 nm, and the maximum absorption wavelength b exists. Eyewear in which the ratio of the integrated value of the peak of the maximum absorption wavelength b to the integrated value of the peak of the maximum absorption wavelength a is 1.00 to 2.50.
  • Example 1 (Making a lens) 0.020 g of dimethyltin (II) dichloride, 0.10 g of internal mold release agent for MR (manufactured by Mitsui Chemicals, Inc.), Biosorb 583 (manufactured by Kyodo Yakuhin Co., Ltd., UV absorber, 2- () in a sufficiently dried flask. 2'-Hydroxy-5'-t-octylphenyl) benzotriazole) 1.50 g, 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1] heptane-containing composition 46.8 g Was charged to prepare a mixed solution (1).
  • UVY-0026 manufactured by Yamamoto Chemicals, Inc., a porphyrin compound in which X1 to X8 are bromine atoms, R1 to R4 are hydrogen atoms, and M is Pd in the general formula (2)
  • PD -311S manufactured by Yamamoto Chemicals, Inc., tetra-t-butyl-tetraazaporphyrin-copper complex, compound represented by the above formula (1a)
  • PD -311S manufactured by Yamamoto Chemicals, Inc., tetra-t-butyl-tetraazaporphyrin-copper complex, compound represented by the above formula (1a)
  • PD -311S manufactured by Yamamoto Chemicals, Inc., tetra-t-butyl-tetraazaporphyrin-copper complex, compound represented by the above formula (1a)
  • This solution was defoamed at 400 Pa for 1 hour, filtered through a 1 ⁇ m PTFE (polytetrafluoroethylene) filter, and then injected into a 4C glass mold for planau having a center thickness of 2 mm and a diameter of 77 mm.
  • PTFE polytetrafluoroethylene
  • this glass mold was raised from 25 ° C to 120 ° C over 21 hours. Then, it was cooled to room temperature and the plano lens was removed from the glass mold. The obtained planau lens was further annealed at 120 ° C. for 2 hours. As a result, the lens of Example 1 was produced.
  • This solution was defoamed at 400 Pa for 1 hour, filtered through a 1 ⁇ m PTFE filter, and then poured into a 4C glass mold for planau having a center thickness of 2 mm and a diameter of 77 mm.
  • this glass mold was raised from 25 ° C to 120 ° C over 21 hours. Then, it was cooled to room temperature and the plano lens was removed from the glass mold. The obtained planau lens was further annealed at 120 ° C. for 2 hours. As a result, a standard lens was produced.
  • Examples 2 and 3 Same as Example 1 except that the content of UVY-0026 was changed as shown in Table 1 with respect to Example 1 or the content of each dye was changed as shown in Table 4 with respect to Example 1. I made a lens.
  • Example 4 In Example 1, instead of Viosorb 583 1.50 g, Tinuvin 326 (manufactured by BASF Japan Co., Ltd., UV absorber, 2- (2'-hydroxy-3'-tert-butyl-5'-methylphenyl) -5-chloro Performed in the same manner as in Example 1 except that 1.0 g of benzotriazole) was used, the masterbatch (1) in which UVY-0026 was dissolved was not used, and the content of PD-311S was changed as shown in Table 1. The lens of Example 4 was prepared.
  • Example 5 A lens was produced in the same manner as in Example 4 except that the content of PD-311S was changed as shown in Table 1 with respect to Example 4.
  • Example 7 In place of the master batch (1) in which UVY-0026 was dissolved in Example 1, UVY-1023 (manufactured by Yamamoto Chemicals, Inc., in general formula ( 2 ), X1 to X8 are 3,3-dimethyl- 1- . Composition 100 containing a butynyl group, a porphyrin compound in which R1 to R4 are hydrogen atoms and M is Pd), and 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1] heptane. Using the master batch (3) dissolved in 0.0 g, the lens of Example 7 was prepared in the same manner as in Example 1 except that the content of PD-311S was changed as shown in Table 1.
  • Example 8 The lens of Example 8 was produced in the same manner as in Example 7 except that the content of each dye was changed as shown in Table 1.
  • Example 9 In Example 9, the masterbatch (1) in which UVY-0026 was dissolved was not used for Example 1, and the content of PD-311S was changed as shown in Table 2 in the same manner as in Example 1. I made a lens.
  • Example 10 was similarly added to Example 1 except that a masterbatch (3) in which UVY-1023 was dissolved was additionally added and the content of each dye was changed as shown in Table 2. I made a lens.
  • Example 11 Instead of the masterbatch (1) in which UVY-0026 was dissolved with respect to Example 1, FDB-001 (copper porphyrin complex manufactured by Yamada Chemical Co., Ltd.) was used as 2,5 (6) -bis (isocyanatomethyl). -Same as Example 1 except that a masterbatch (4) dissolved in 100.0 g of a composition containing bicyclo [2.2.1] heptane was used and the content of each dye was changed as shown in Table 2. The lens of Example 11 was produced.
  • FDB-001 copper porphyrin complex manufactured by Yamada Chemical Co., Ltd.
  • Example 12 Instead of the masterbatch (4) in which FDB-001 was dissolved in Example 11, FDB-002 (vanadium porphyrin complex manufactured by Yamada Chemical Co., Ltd.) was used as 2,5 (6) -bis (isocyanatomethyl). -The lens of Example 12 was prepared in the same manner as in Example 11 except that the masterbatch (5) dissolved in 100.0 g of the composition containing bicyclo [2.2.1] heptane was used.
  • Example 13 Instead of the masterbatch (4) in which FDB-001 was dissolved in Example 11, FDB-003 (merocyanine dye manufactured by Yamada Chemical Co., Ltd.) was used in 2,5 (6) -bis (isocyanatomethyl)-. Using a masterbatch (6) dissolved in 100.0 g of a composition containing bicyclo [2.2.1] heptane, the same as in Example 11 except that the content of each dye was changed as shown in Table 2. The lens of Example 13 was produced.
  • Example 14 Instead of the masterbatch (4) in which FDB-001 was dissolved in Example 11, FDB-004 (oil-soluble dye manufactured by Yamada Chemical Co., Ltd.) was used as 2,5 (6) -bis (isocyanatomethyl). -The lens of Example 14 was prepared in the same manner as in Example 11 except that the masterbatch (7) dissolved in 100.0 g of the composition containing bicyclo [2.2.1] heptane was used.
  • Example 15 Instead of the masterbatch (4) in which FDB-001 was dissolved in Example 11, FDB-006 (merocyanine dye manufactured by Yamada Chemical Co., Ltd.) was used in 2,5 (6) -bis (isocyanatomethyl)-.
  • the lens of Example 15 was prepared in the same manner as in Example 11 except that the masterbatch (8) dissolved in 100.0 g of the composition containing bicyclo [2.2.1] heptane was used.
  • Example 16 instead of the masterbatch (4) in which FDB-001 was dissolved in Example 11, ABS 425 (manufactured by Luxottica) was used as 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1. ] The lens of Example 16 was prepared in the same manner as in Example 11 except that the masterbatch (9) dissolved in 100.0 g of the composition containing heptane was used.
  • Example 17 Instead of the masterbatch (4) in which FDB-001 was dissolved in Example 11, ABS 430 (manufactured by Luxottica) was used as 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1. ] The lens of Example 17 was prepared in the same manner as in Example 11 except that the masterbatch (10) dissolved in 100.0 g of the composition containing heptane was used.
  • Example 18 Instead of the masterbatch (4) in which FDB-001 was dissolved in Example 11, ABS 439 (manufactured by Luxottica) was used as 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1. ] The lens of Example 18 was prepared in the same manner as in Example 11 except that the masterbatch (11) dissolved in 100.0 g of the composition containing heptane was used.
  • Example 19 instead of the masterbatch (4) in which FDB-001 was dissolved in Example 11, ABS 462 (manufactured by Luxottica) was used as 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1. ] The lens of Example 19 was prepared in the same manner as in Example 11 except that the masterbatch (12) dissolved in 100.0 g of the composition containing heptane was used.
  • Example 20 Instead of the masterbatch (4) in which FDB-001 was dissolved in Example 11, ABS 473 (manufactured by Luxottica) was used as 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1. ] Using a masterbatch (13) dissolved in 100.0 g of a composition containing heptane, the lens of Example 20 was used in the same manner as in Example 11 except that the content of each dye was changed as shown in Table 3. Made.
  • Example 21 instead of the masterbatch (2) in which PD-311S was dissolved with respect to Example 1, ABS 574 (manufactured by Luxottica) was used as 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1]. ] Using a masterbatch (14) dissolved in 100.0 g of a composition containing heptane, the lens of Example 21 was used in the same manner as in Example 1 except that the content of each dye was changed as shown in Table 3. Made.
  • Example 22 ABS 584 (manufactured by Luxottica) was used in place of the masterbatch (14) in which ABS 574 was dissolved in Example 21.
  • the lens of Example 22 was prepared in the same manner as in Example 21 except that the masterbatch (15) dissolved in 100.0 g of the composition containing heptane was used.
  • Example 23 ABS 594 (manufactured by Luxottica) was used in place of the masterbatch (14) in which ABS 574 was dissolved in Example 21.
  • the lens of Example 23 was prepared in the same manner as in Example 21 except that the masterbatch (16) dissolved in 100.0 g of the composition containing heptane was used.
  • Example 1 The standard lens produced in Example 1 was used as the lens of Comparative Example 1.
  • Comparative Example 2 A lens of Comparative Example 2 was produced in the same manner as in Comparative Example 1 except that 1.0 g of Tinuvin 326 was used instead of Viosorb 583 1.50 g in Comparative Example 1.
  • Example 4 In Example 1, a masterbatch (3) in which UVY-1023 was dissolved was used instead of the masterbatch (1) in which UVY-0026 was dissolved, and a masterbatch (2) in which PD-311S was dissolved was used.
  • the lens of Comparative Example 4 was produced in the same manner as in Example 1 except that the dye content was not used and the dye content was changed as shown in Table 4.
  • Comparative Example 5 The lens of Comparative Example 5 was prepared in the same manner as in Example 1 except that the masterbatch (2) in which PD-311S was dissolved was not used in Example 1 and the dye content was changed as shown in Table 4. did.
  • CM-5 manufactured by Konica Minolta Co., Ltd.
  • Konica Minolta Co., Ltd. A spectrocolorimeter CM-5 (manufactured by Konica Minolta Co., Ltd.) was used as a measuring device.
  • One of the following Munsell color markers 1 to 3 is used under a D65 light source, and the lenses of the Examples and Comparative Examples having a thickness of 2 mm and the standard lens having a thickness of 2 mm are used as any of the above Munsell color markers. It was placed between the measuring unit.
  • Blue light cut rate 380 nm in a spectrum measured in accordance with EN ISO12312-1: 2013 using an ultraviolet-visible spectrophotometer UV-1800 (manufactured by Shimadzu Corporation) and lenses of each example and each comparative example having a thickness of 2 mm.
  • the blue light absorption rate of about 500 nm was determined.
  • the blue light cut rate was evaluated based on the following evaluation criteria. -Evaluation criteria- A: The blue light cut rate was 30% or more. B: The blue light cut rate was 20% or more and less than 30%. C: The blue light cut rate was 15% or more and less than 20%. D: The blue light cut rate was less than 15%.
  • the transmittance curve was measured using an ultraviolet-visible spectrophotometer UV-1800 (manufactured by Shimadzu Corporation) and the lenses of each example and each comparative example having a thickness of 2 mm, and at the maximum absorption wavelength and the maximum absorption wavelength.
  • the transmittance, the visual transmittance according to ISO 8980-3: 2013, and the half-value range of the absorption peak at the maximum absorption wavelength a were determined.
  • the transmittance curves of the lenses of Examples 1 to 8 are shown in FIG. 1, the transmittance curves of the lenses of Examples 9 to 15 are shown in FIG. 2, and the transmittance curves of the lenses of Examples 16 to 23 are shown in FIG.
  • the transmittance curves of the lenses of Comparative Examples 1 to 6 are shown in FIG.
  • Tables 1 to 4 The evaluation results when the lenses of each example and each comparative example are used are shown in Tables 1 to 4 below.
  • "-" means that the corresponding component is not contained or the evaluation target does not exist, and the blank means that the evaluation has not been performed.
  • Tables 1 to 4 when two transmittances at the maximum absorption wavelength are described as in Example 1, the numerical value in the upper row is the maximum absorption wavelength on the short wavelength side (455 nm in Example 1). It is a numerical value of the transmittance, and the numerical value in the lower row is a numerical value of the transmittance at the maximum absorption wavelength (588 nm in Example 1) on the high wavelength side.
  • the lenses of Examples 1 to 23 had better evaluation of sharpness than the lenses of Comparative Examples 1 to 6.
  • Example 201 (Making a lens) 0.020 g of dimethyltin (II) dichloride, 0.10 g of internal mold release agent for MR (manufactured by Mitsui Chemicals, Inc.), Biosorb 583 (manufactured by Kyodo Yakuhin Co., Ltd., UV absorber, 2- () in a sufficiently dried flask. 2'-Hydroxy-5'-t-octylphenyl) benzotriazole) 1.50 g, 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1] heptane-containing composition 46.8 g Was charged to prepare a mixed solution (1).
  • UVY-0026 manufactured by Yamamoto Kasei Co., Ltd.
  • PD-311S manufactured by Yamamoto Kasei Co., Ltd.
  • a master batch (1) in which UVY-0026 was dissolved and a master batch (2) in which PD-311S were dissolved were prepared by dissolving them in 100.0 g of a composition containing heptane, respectively.
  • This solution was defoamed at 400 Pa for 1 hour, filtered through a 1 ⁇ m PTFE (polytetrafluoroethylene) filter, and then injected into a 4C glass mold for planau having a center thickness of 2 mm and a diameter of 77 mm.
  • PTFE polytetrafluoroethylene
  • this glass mold was raised from 25 ° C to 120 ° C over 21 hours. Then, it was cooled to room temperature and the plano lens was removed from the glass mold. The obtained planau lens was further annealed at 120 ° C. for 2 hours. As a result, the lens of Example 201 was produced.
  • This solution was defoamed at 400 Pa for 1 hour, filtered through a 1 ⁇ m PTFE filter, and then poured into a 4C glass mold for planau having a center thickness of 2 mm and a diameter of 77 mm.
  • this glass mold was raised from 25 ° C to 120 ° C over 21 hours. Then, it was cooled to room temperature and the plano lens was removed from the glass mold. The obtained planau lens was further annealed at 120 ° C. for 2 hours. As a result, a standard lens was produced.
  • Example 202 Instead of the masterbatch (1) in which UVY-0026 was dissolved, UVY-1023 (manufactured by Yamamoto Chemicals, Inc.) was used as 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1].
  • Example was carried out in the same manner as in Example 201 except that the masterbatch (3) dissolved in 100.0 g of the composition containing heptane was used and the content of each dye in the uniform solution was changed as shown in Table 5. 202 lenses were made.
  • Example 203 Instead of the masterbatch (1) in which UVY-0026 was dissolved, FDB-001 (manufactured by Yamada Chemical Co., Ltd.) was used as 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1].
  • Example was carried out in the same manner as in Example 201 except that the masterbatch (4) dissolved in 100.0 g of the composition containing heptane was used and the content of each dye in the uniform solution was changed as shown in Table 5. 203 lenses were made.
  • Example 204 Instead of the masterbatch (4) in which FDB-001 was dissolved, ABS 430 (manufactured by Luxottica) contained 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1] heptane. Using the masterbatch (5) dissolved in 100.0 g of the product, the lens of Example 204 was used in the same manner as in Example 203, except that the content of each dye in the uniform solution was changed as shown in Table 5. Made.
  • Example 205 Instead of the masterbatch (2) in which PD-311S was dissolved, ABS 574 (manufactured by Luxottica) was added to a composition containing 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1] heptane. Using the masterbatch (6) dissolved in 100.0 g of the product, the lens of Example 205 was used in the same manner as in Example 201 except that the content of each dye in the uniform solution was changed as shown in Table 5. Made.
  • Example 206 A composition containing 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1] heptane containing ABS 594 (manufactured by Luxottica) in place of the masterbatch (6) in which ABS 574 was dissolved. Using the masterbatch (7) dissolved in 100.0 g, the lens of Example 206 was prepared in the same manner as in Example 205 except that the content of each dye in the uniform solution was changed as shown in Table 5. did.
  • Comparative Example 201 instead of the masterbatch (2) in which PD-311S was dissolved, FDG-003 (Yamada Chemical Co., Ltd.) was used as 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2.2.1]. Comparative Example in the same manner as in Example 201 except that the masterbatch (8) dissolved in 100.0 g of the composition containing heptane was used and the content of each dye in the uniform solution was changed as shown in Table 5. 201 lenses were made.
  • Comparative Example 202 instead of using the masterbatch (2) in which PD-311S was dissolved, the above-mentioned masterbatch (3) in which UVY-1023 was dissolved was used instead of the masterbatch (1) in which UVY-0026 was dissolved.
  • the lens of Comparative Example 202 was produced in the same manner as in Example 201 except that the content of each dye in the uniform solution was changed as shown in Table 5.
  • ⁇ Evaluation ⁇ (Yellowness (YI value) Obtained by measuring at room temperature, viewing angle 2 °, and C light source three times by the transmission method according to ASM E313-73 using a spectrocolorimeter CM-5 manufactured by Konica Minolta, which has a pulse xenon lamp. It was calculated as the average value of the values obtained.
  • the measurement wavelength range is 360 nm to 740 nm.
  • CM-5 manufactured by Konica Minolta Co., Ltd.
  • Konica Minolta Co., Ltd. A spectrocolorimeter CM-5 (manufactured by Konica Minolta Co., Ltd.) was used as a measuring device.
  • One of the following Munsell color markers 1 to 3 is used under a D65 light source, and the lenses of the Examples and Comparative Examples having a thickness of 2 mm and the standard lens having a thickness of 2 mm are used as any of the above Munsell color markers. It was placed between the measuring unit.
  • the transmittance curve was measured using an ultraviolet visible spectrophotometer UV-1800 (manufactured by Shimadzu Corporation) and the lenses of each example and each comparative example having a thickness of 2 mm, and at the maximum absorption wavelength and the maximum absorption wavelength.
  • the transmittance, the visual transmittance according to ISO 8980-3: 2013, and the half-value range of the absorption peak having the maximum absorption wavelength in the range of 400 nm to 520 nm were determined.
  • the transmittance curves of the lenses of Examples 201 to 206 are shown in FIG. 5, and the transmittance curves of the lenses of Comparative Examples 201 to 202 are shown in FIG.
  • Table 5 shows the evaluation results when the lenses of each example and each comparative example were used.
  • "-" means that the corresponding component is not contained or the evaluation target does not exist.
  • Table 5 when two transmittances at the maximum absorption wavelength are described as in Example 201, the numerical value in the upper row is the transmittance at the maximum absorption wavelength on the short wavelength side (455 nm in Example 201). It is a numerical value, and the numerical value in the lower row is a numerical value of the transmittance at the maximum absorption wavelength (588 nm in Example 201) on the high wavelength side.
  • the functional layer includes the functional layer, and the functional layer has a maximum absorption wavelength a in the range of (A) 560 nm to 610 nm and (B) 400 nm to 520 nm in the spectrum measured according to CIE1976.
  • the example was excellent in the effect of having a natural color tone in which blue color was suppressed because the evaluation of the appearance was excellent.
  • Examples 201 and 203 using a spectacle lens in which the ratio of the integrated value of the peak of the maximum absorption wavelength b to the integrated value of the peak of the maximum absorption wavelength a is 1.4 to 2.5 is 1.4 to 2.5.
  • -Example 206 was superior in the effect of clearly recognizing the red color and green color of the object because it was superior in the evaluation of the degree of sharpness.
  • it since it is excellent in the evaluation of appearance, it is excellent in the effect of having a natural color tone in which blue color is suppressed.

Abstract

Un matériau optique selon la présente invention comprend au moins un type de pigment, et présente, dans un spectre mesuré selon la norme CIE 1976, (A) une longueur d'onde d'absorption maximale a dans la plage de 560 à 610 nm, et un paramètre de différence de couleur ΔC*R-G de 0 à 10, inclus, dans la CIE 1976 (L*a*b*) système de couleur, déterminé à partir des formules (1) et (2) ci-dessous et à l'aide d'une source de lumière D65. (1) ΔC*R-G=ΔE*R-G-ΔE*R-G(w0), (2) ΔE*=(ΔL*2+Δa*2+Δb*2)1/2
PCT/JP2021/043217 2020-11-30 2021-11-25 Matériau optique, lentille et lunettes WO2022114064A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008134618A (ja) * 2006-10-26 2008-06-12 Hopunikku Kenkyusho:Kk プラスチック眼鏡レンズ
JP2013109257A (ja) * 2011-11-24 2013-06-06 Talex Optical Co Ltd 防眩・高コントラスト性樹脂製レンズ
JP2017149820A (ja) * 2016-02-23 2017-08-31 三井化学株式会社 樹脂組成物およびその用途
JP2019066501A (ja) * 2016-02-23 2019-04-25 三井化学株式会社 光学材料用熱可塑性樹脂組成物およびその用途
WO2019138953A1 (fr) * 2018-01-09 2019-07-18 株式会社Adeka Composition, substance durcie, filtre optique, et procédé de fabrication d'une substance durcie
WO2020129930A1 (fr) * 2018-12-17 2020-06-25 株式会社トクヤマ Composition durcissable pour matériaux optiques et matériau optique

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008134618A (ja) * 2006-10-26 2008-06-12 Hopunikku Kenkyusho:Kk プラスチック眼鏡レンズ
JP2013109257A (ja) * 2011-11-24 2013-06-06 Talex Optical Co Ltd 防眩・高コントラスト性樹脂製レンズ
JP2017149820A (ja) * 2016-02-23 2017-08-31 三井化学株式会社 樹脂組成物およびその用途
JP2019066501A (ja) * 2016-02-23 2019-04-25 三井化学株式会社 光学材料用熱可塑性樹脂組成物およびその用途
WO2019138953A1 (fr) * 2018-01-09 2019-07-18 株式会社Adeka Composition, substance durcie, filtre optique, et procédé de fabrication d'une substance durcie
WO2020129930A1 (fr) * 2018-12-17 2020-06-25 株式会社トクヤマ Composition durcissable pour matériaux optiques et matériau optique

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