WO2020218614A1 - Matériau optique, composition polymérisable pour matériau optique, lentille en plastique, lunettes, capteur infrarouge et caméra infrarouge - Google Patents

Matériau optique, composition polymérisable pour matériau optique, lentille en plastique, lunettes, capteur infrarouge et caméra infrarouge Download PDF

Info

Publication number
WO2020218614A1
WO2020218614A1 PCT/JP2020/018016 JP2020018016W WO2020218614A1 WO 2020218614 A1 WO2020218614 A1 WO 2020218614A1 JP 2020018016 W JP2020018016 W JP 2020018016W WO 2020218614 A1 WO2020218614 A1 WO 2020218614A1
Authority
WO
WIPO (PCT)
Prior art keywords
optical material
bis
material according
group
spectral transmittance
Prior art date
Application number
PCT/JP2020/018016
Other languages
English (en)
Japanese (ja)
Inventor
勇輔 松井
伸介 伊藤
戸谷　由之
浩之 佐々木
Original Assignee
三井化学株式会社
山本化成株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 三井化学株式会社, 山本化成株式会社 filed Critical 三井化学株式会社
Priority to CN202080029166.XA priority Critical patent/CN113711113B/zh
Priority to KR1020217033867A priority patent/KR20210144775A/ko
Priority to JP2021516329A priority patent/JP7254167B2/ja
Publication of WO2020218614A1 publication Critical patent/WO2020218614A1/fr

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • 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
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • 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
    • 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
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/58—Epoxy resins
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • 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
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/06—Polythioethers from cyclic thioethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/45—Heterocyclic compounds having sulfur in the ring
    • C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C08L81/02—Polythioethers; Polythioether-ethers
    • 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
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/208—Filters for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation
    • 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
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • 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

  • the present disclosure relates to optical materials containing near-infrared absorbers, polymerizable compositions for optical materials, plastic lenses, eyewear, infrared sensors and infrared cameras.
  • Patent Document 1 describes a near-infrared ray cut having a near-infrared ray reflecting film formed by alternately laminating two dielectric layers having different refractive indexes on at least one surface of a transparent substrate containing a cyclic olefin resin and a glass filler. The filter is disclosed.
  • Patent Document 2 discloses a near-infrared cut filter having a predetermined transmittance of light in a plurality of wavelength ranges. It is described that this near-infrared cut filter contains a transparent resin such as a cyclic olefin resin and a near-infrared absorber such as a phthalocyanine compound.
  • a transparent resin such as a cyclic olefin resin
  • a near-infrared absorber such as a phthalocyanine compound.
  • Patent Documents 3 to 7 disclose resin compositions and the like containing a predetermined phthalocyanine pigment and a resin. Patent Document 7 describes that a lens for protective goggles can be obtained from the resin composition. Patent Document 8 and Patent Document 9 disclose a far-infrared cut lens composed of a phthalocyanine pigment and a urethane resin or a polythiourethane resin.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 2009-258362
  • Patent Document 2 Japanese Patent Application Laid-Open No. 2011-100084
  • Patent Document 3 Japanese Patent Application Laid-Open No. 11-48612
  • Patent Document 4 Japanese Patent Application Laid-Open No. 2000-313788
  • Patent Document 5 Japanese Patent Application Laid-Open No. 2006-228646
  • Patent Document 6 International Publication No. 2014/208484
  • Patent Document 7 Japanese Patent Application Laid-Open No. 8-60008
  • Patent Document 8 Japanese Patent Application Laid-Open No. 2017-528415
  • Patent Document 9 Japanese Patent Application Laid-Open No. 2018-528829
  • the near-infrared ray cut filter described in Patent Document 1 and Patent Document 2 can cut near infrared ray, the filter may become turbid and the transparency may be lowered.
  • the near-infrared absorber did not dissolve in the resin, or when the amount added was increased, the optical material became turbid and the transparency decreased. Or, there was a tendency for the color (design) to deteriorate due to coloring. As described above, in the optical material using the near-infrared absorber, there was a trade-off relationship between the near-infrared ray cutting effect and the design.
  • the problem to be solved by one embodiment of the present disclosure is to provide an optical material having a high near-infrared ray cut rate and excellent design.
  • the present inventors have set a high near-infrared cut rate and design by containing a near-infrared absorber and a predetermined resin and setting L * and a * in a specific range in the CIE1976 color space.
  • the invention of the present disclosure has been completed by finding that it is possible to achieve both. That is, the present disclosure can be shown below.
  • ⁇ 3> The optical material according to ⁇ 1>, wherein the spectral transmittance at a wavelength of 825 nm to 875 nm at a thickness of 2 mm is 4% or more and 70% or less.
  • ⁇ 4> The optical material according to ⁇ 1>, wherein the spectral transmittance at a wavelength of 1000 nm to 1100 nm at a thickness of 2 mm is 4% or more and 70% or less.
  • ⁇ 5> The optical material according to any one of ⁇ 1> to ⁇ 4>, which has a visual transmittance of 70% or more at a thickness of 2 mm.
  • the near-infrared absorber has (1) a wavelength region of 700 nm to 750 nm in the spectral transmittance curve, (2) a wavelength region of 825 nm to 875 nm in the spectral transmittance curve, and (3) 1000 nm in the spectral transmittance curve.
  • the phthalocyanine compound has a main absorption peak (P) between 700 nm and 1100 nm in a visible light absorption spectral spectrum measured with a toluene solution, and the peak peak (Pmax: in the peak) of the peak (P).
  • the extinction coefficient (ml / g ⁇ cm) of (the point showing the maximum extinction coefficient) is 30,000 or more, and the peak width at the absorbance of 1/4 of the absorbance of (Pmax) of the peak (P) is 360 nm or less.
  • the peak width at half the absorbance of (Pmax) of the peak (P) is 130 nm or less, and the peak width at two-thirds of the absorbance of (Pmax) of the peak (P) is 90 nm.
  • the optical material according to ⁇ 7> which has the following range. ⁇ 9> The optical material according to ⁇ 7> or ⁇ 8>, wherein the phthalocyanine compound contains at least one compound represented by the general formulas (I) to (III).
  • R 1 and R 2 each independently represent a substituted or unsubstituted alkoxy group having a total carbon number of 3 to 18, and an alkylene group not bonded to an oxygen atom is an oxygen atom.
  • R 3 and R 4 independently represent a hydrogen atom or a halogen atom, respectively.
  • M represents two hydrogen atoms, a divalent metal, an oxide or a halide of a metal. However, R 1 and R 2 and R 3 and R 4 may be interchanged.
  • R 9 represents a hydrogen atom or an alkyl group
  • M is two hydrogen atoms, a divalent metal or a trivalent. Or a tetravalent metal derivative.
  • R 1 to R 4 independently represent an alkyl group or an alkoxyalkyl group
  • X is a phenylthio group or a substituent which may have a halogen atom, an alkylthio group or a substituent.
  • the spectral transmittance at a wavelength of 700 nm to 750 nm at a thickness of 2 mm is 0.05% or more and 70% or less, and the near-infrared absorber is (1) in the range of the wavelength region of 700 nm to 750 nm in the spectral transmittance curve.
  • the optical material according to ⁇ 9> which has a minimum value of less than 50% spectral transmittance.
  • the spectral transmittance at a wavelength of 1000 nm to 1100 nm at a thickness of 2 mm is 4% or more and 70% or less, and the near-infrared absorber is (3) within the range of the wavelength region of 1000 nm to 1100 nm in the spectral transmittance curve.
  • the optical material according to ⁇ 9> which has a minimum value of less than 50% spectral transmittance.
  • ⁇ 15> The optical material according to ⁇ 14>, wherein the phthalocyanine compound contains a compound represented by the general formula (III).
  • the (thio) urethane resin is composed of at least one of a constitutional unit derived from a polyisocyanate compound, a constitutional unit derived from a polythiol compound, and a constitutional unit derived from a polyol compound.
  • the polyisocyanate compound is 2,5-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, 2,6-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, m-xylylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, dicyclohexylmethane diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, 1,4-bis (isocyanatomethyl) cyclohexane, At least one selected from isophorone diisocyanate, 1,6-hexamethylene diisocyanate, and 1,5-pentamethylene diisocyanate.
  • the polythiol compounds are 4-mercaptomethyl-1,8-dimercapto-3,6-dithiane octane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithianecan, 4,7-.
  • the polyol compound is ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1,3-propanediol, 1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, 1,3.
  • the optical material according to any one of ⁇ 1> to ⁇ 17>, which is at least one selected from -cyclohexanediol and 1,4-cyclohexanediol.
  • the episulfide resin is composed of a structural unit derived from an episulfide compound, or a structural unit derived from an episulfide compound and a structural unit derived from a polythiol compound.
  • the episulfide compounds include bis (2,3-epiopropyl) sulfide, bis (2,3-epiothiopropyl) disulfide, bis (1,2-epioethyl) sulfide, bis (1,2-epiothiolethyl) disulfide, and , Bis (2,3-epithiopropylthio) is at least one selected from methane,
  • the polyol compound is ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1,3-propanediol, 1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, 1,3.
  • optical material according to any one of ⁇ 1> to ⁇ 17> which is at least one selected from -cyclohexanediol and 1,4-cyclohexanediol.
  • a polymerizable compound consisting of a combination of a polyisocyanate compound and at least one of a polythiol compound and a polyol compound, an episulfide compound, or a combination of an episulfide compound and a polythiol compound.
  • a polymerizable composition for an optical material containing. ⁇ 21> The polymerizable composition for an optical material according to ⁇ 20>, wherein the near-infrared absorber contains a phthalocyanine compound.
  • the phthalocyanine compound has a main absorption peak (P) between 700 nm and 1100 nm in a visible light absorption spectral spectrum measured with a toluene solution, and the peak peak (Pmax: in the peak) of the peak (P).
  • the extinction coefficient (ml / g ⁇ cm) of (the point showing the maximum extinction coefficient) is 30,000 or more, and the peak width at the absorbance of 1/4 of the absorbance of (Pmax) of the peak (P) is 360 nm or less.
  • the peak width at half the absorbance of (Pmax) of the peak (P) is 130 nm or less, and the peak width at two-thirds of the absorbance of (Pmax) of the peak (P) is 90 nm.
  • the polymerizable composition for an optical material according to ⁇ 21> which has the following range. ⁇ 23>
  • R 1 and R 2 each independently represent a substituted or unsubstituted alkoxy group having a total carbon number of 3 to 18, and an alkylene group not bonded to an oxygen atom is an oxygen atom.
  • R 3 and R 4 independently represent a hydrogen atom or a halogen atom, respectively.
  • M represents two hydrogen atoms, a divalent metal, an oxide or a halide of a metal. However, R 1 and R 2 and R 3 and R 4 may be interchanged.
  • R 9 represents a hydrogen atom or an alkyl group
  • M is two hydrogen atoms, a divalent metal or a trivalent. Or a tetravalent metal derivative.
  • R 1 to R 4 independently represent an alkyl group or an alkoxyalkyl group
  • X is a phenylthio group or a substituent which may have a halogen atom, an alkylthio group or a substituent.
  • the polymerizable composition for an optical material according to ⁇ 23> which has a minimum value of less than 50% spectral transmittance in the wavelength region of 825 nm to 875 nm in the transmittance curve.
  • the polymerizable composition for an optical material according to ⁇ 23> which has a minimum value of less than 50% spectral transmittance in the wavelength region of 1000 nm to 1100 nm in the transmittance curve.
  • ⁇ 29> The polymerizable composition for an optical material according to ⁇ 28>, wherein the phthalocyanine compound contains a compound represented by the general formula (III).
  • ⁇ 30> The polymerizable composition for an optical material according to any one of ⁇ 20> to ⁇ 29>, which contains the near-infrared absorber at 3 ppm or more and 80 ppm or less.
  • ⁇ 31> The polymerizable composition for an optical material according to any one of ⁇ 20> to ⁇ 30>, wherein the near-infrared absorber contains a plurality of phthalocyanine compounds having different structures in combination.
  • the polyisocyanate compound is 2,5-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, 2,6-bis (isocyanatomethyl) bicyclo- [2.2.1].
  • the polythiol compounds are 4-mercaptomethyl-1,8-dimercapto-3,6-dithiane octane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithianecan, 4,7-.
  • the polyol compound is ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1,3-propanediol, 1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, 1,3.
  • the polymerizable composition for an optical material according to any one of ⁇ 20> to ⁇ 31>, which is at least one selected from -cyclohexanediol and 1,4-cyclohexanediol.
  • the episulfide compound includes bis (2,3-epiopropyl) sulfide, bis (2,3-epiopropyl) disulfide, bis (1,2-epioethyl) sulfide, and bis (1,2-epioethyl).
  • Eyewear provided with the plastic lens according to ⁇ 34>.
  • ⁇ 36> An infrared sensor or an infrared camera including the plastic lens according to ⁇ 34>.
  • an optical material having a high near-infrared ray cut rate and also having excellent design.
  • the spectral transmittance curve of the flat plate lens obtained in Example 3 is shown.
  • the spectral transmittance curve of the flat plate lens obtained in Example 10 is shown.
  • the spectral transmittance curve of the flat plate lens obtained in Example 13 is shown.
  • the spectral transmittance curve of the flat plate lens obtained in Example 16 is shown.
  • the spectral transmittance curve of the flat plate lens obtained in Example 22 is shown.
  • the spectral transmittance curve of the flat plate lens obtained in Example 24 is shown.
  • the spectral transmittance curve of the flat plate lens obtained in Comparative Example 8 is shown.
  • the spectral transmittance curve of the flat plate lens obtained in Example 26 is shown.
  • the spectral transmittance curve of the flat plate lens obtained in Example 30 is shown.
  • the spectral transmittance curve of the flat plate lens obtained in Example 32 is shown.
  • the spectral transmittance curve of the flat plate lens obtained in Example 35 is shown.
  • the spectral transmittance curve of the flat plate lens obtained in Example 41 is shown.
  • the spectral transmittance curve of the flat plate lens obtained in Example 43 is shown.
  • the numerical range represented by using "-" means a range including the numerical values before and after "-" as the lower limit value and the upper limit value.
  • the amount of each component in the composition is the total amount of the plurality of substances present in the composition unless otherwise specified, when a plurality of substances corresponding to each component are present in the composition. means.
  • the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of another numerical range described stepwise. ..
  • the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
  • the optical material of the present embodiment contains at least one resin selected from the group consisting of polycarbonate resin, (thio) urethane resin, and episulfide resin, and a near-infrared absorber, and is measured at a thickness of 2 mm in CIE1976.
  • a * is -30 or more and 0 or less
  • L * is 80 or more.
  • the optical material of the present embodiment has a * of -30 or more and 0 or less, L * of 80 or more, preferably a * of-in the CIE1976 (L *, a *, b *) color space measured at a thickness of 2 mm. 20 or more and 0 or less, L * is 82 or more, more preferably a * is -15 or more and 0 or less, L * is 85 or more, particularly preferably a * is -10 or more and 0 or less, and L * is 88 or more.
  • a near-infrared absorber and a resin which is at least one selected from the group consisting of a polycarbonate resin, a (thio) urethane resin and an episulfide resin are contained, and L *, a in the CIE1976 color space.
  • the optical material of the present embodiment has at least one of a spectral transmittance of 700 nm to 750 nm at a thickness of 2 mm, a spectral transmittance of 825 nm to 875 nm, and a spectral transmittance of 1000 nm to 1100 nm. It is preferable that one satisfies the following range.
  • Spectral transmittance at a wavelength of 1000 nm to 1100 nm at a thickness of 2 mm 4% or more and 70% or less, preferably 6% or more and 50% or less, more preferably 8% or more and 40% or less
  • the total light transmittance at a thickness of 2 mm can be 70% or more, and the visual transmittance is 70% or more. It can be preferably 75% or more.
  • the structure of the near-infrared absorber in the present embodiment is not particularly limited as long as the effect in the present disclosure can be obtained, and the near-infrared absorber can be selected and used from conventionally known near-infrared absorbers.
  • the near-infrared absorber in the present embodiment for example, in order to realize a high near-infrared cut rate, (1) a minimum spectral transmittance of less than 50% within the wavelength range of 700 nm to 750 nm in the spectral transmittance curve. Those having a value, (2) having a minimum value of less than 50% spectral transmittance within the wavelength range of 825 nm to 875 nm in the spectral transmittance curve, and (3) having a wavelength of 1000 nm to 1100 nm in the spectral transmittance curve. Those having a minimum value of less than 50% spectral transmittance can be used within at least one range of the region.
  • the near-infrared absorber having the characteristics (1) to (3) can be used in combination.
  • the near-infrared absorber is not particularly limited. It preferably contains a phthalocyanine compound.
  • the phthalocyanine compound has a main absorption peak (P) between 700 nm and 1100 nm in the visible light absorption spectral spectrum measured with a toluene solution, and the peak peak (Pmax: maximum among the peaks) of the peak (P).
  • the extinction coefficient (ml / g ⁇ cm) of the point indicating the extinction coefficient) is 30,000 or more, the peak width at the absorbance of 1/4 of the absorbance of (Pmax) of the peak (P) is 360 nm or less, and the above.
  • the peak width at half the absorbance of (Pmax) of the peak (P) is 130 nm or less, and the peak width at two-thirds of the absorbance of (Pmax) of the peak (P) is 90 nm or less.
  • Compounds in the range can be used.
  • the visible light absorption spectroscopic spectrum is measured using a toluene solution at an optical path length of 10 mm.
  • the concentration of the toluene solution may be appropriately adjusted, and may be, for example, 3.3 mass ppm to 36.5 mass ppm.
  • the extinction coefficient (ml / g ⁇ cm) of the peak apex (Pmax: the point showing the maximum extinction coefficient in the peak) of the peak (P) is preferably 50,000 or more, and more preferably 70,000 or more.
  • Examples of the phthalocyanine compound include compounds represented by the general formulas (I) to (III), and at least one compound represented by the general formulas (I) to (III) is contained. Is preferable.
  • R 1 and R 2 each independently represent a substituted or unsubstituted alkoxy group having a total carbon number of 3 to 18, and an alkylene group not bonded to an oxygen atom becomes an oxygen atom. It may be replaced.
  • R 3 and R 4 independently represent a hydrogen atom or a halogen atom, respectively.
  • M represents two hydrogen atoms, a divalent metal, a metal oxide or a halide. However, R 1 and R 2 and R 3 and R 4 may be interchanged.
  • M in the phthalocyanine dye represented by the general formula (I) include divalent metals such as Cu, Pd, Ni, Mg, Zn, Pb and Cd, metal oxides such as VO and AlCl and the like. Examples of metal halides and the like.
  • the substituted or unsubstituted alkoxy group having a total carbon number of 3 to 18 in R 1 and R 2 may be linear, branched, or cyclic.
  • Examples of the substituted or unsubstituted alkoxy group having a total carbon number of 3 to 18 in R 1 and R 2 may have a substituent, such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and the like.
  • substituent such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and the like.
  • Examples thereof include a pentyloxy group, an allyloxy group, a cyclohexyloxy group, a benzyloxy group, a phenoxy group, a naphthyloxy group and the like.
  • substituents examples include a hydroxy group, a carboxy group, a nitrile group, a formyl group, an amino group, a nitro group, a halogen group, a sulfo group, an alkoxy group, a benzoyl group, a thiol group, an aryl group, an ester group, an amide group and an alkyl group.
  • the group etc. can be mentioned.
  • preferable phthalocyanine dyes are described in, for example, JP-A-3-62878, JP-A-3-141582, and JP-A-3-215466. Particularly preferably, it is a compound represented by the chemical formula (I-1) described later.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 represent linear or branched alkyl groups, alkoxyalkyl groups or dialkylaminoalkyl groups.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are alkyl groups
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are alkyl groups
  • R 5 , R 6 , R 7 and R 8 are alkyl groups
  • R 5 , R 6 , R 7 and R 8 are alkyl groups
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are alkyl groups
  • R 5 , R 6 , R 7 and R 8 are alkyl groups
  • Examples are methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-heptyl group, isoheptyl group, sec. -Heptyl group, n-octyl group, 2-ethylhexyl group and the like.
  • R 1 to R 8 are alkoxyalkyl groups, those having 3 to 6 carbon atoms are preferable. Examples thereof include methoxyethyl group, methoxypropyl group, methoxybutyl group, ethoxyethyl group, ethoxypropyl group, ethoxybutyl group, n-propoxyethyl group and iso-propoxyethyl group.
  • R 1 to R 8 are dialkylaminoalkyl groups, those having 3 to 12 carbon atoms are preferable, and the group represented by the general formula (II-a) is particularly preferable.
  • R 12 represents an alkylene group having 1 to 4 carbon atoms
  • R 13 and R 14 individually represent an alkyl group having 1 to 4 carbon atoms.
  • Examples include dimethylaminoethyl group, dimethylaminopropyl group, dimethylaminobutyl group, diethylaminoethyl group, diethylaminopropyl group, diethylaminobutyl group, dipropylaminoethyl group, dipropylaminopropyl group, dipropylaminobutyl group, dibutyl.
  • Examples thereof include an aminoethyl group, a dibutylaminopropyl group and a dibutylaminobutyl group.
  • R 9 is an alkyl group
  • those having 1 to 6 carbon atoms are preferable. Examples include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group and an n-hexyl group.
  • M being a divalent metal
  • the trivalent or tetravalent metal derivative is preferable.
  • AlCl, AlOH, InCl, FeCl, MnOH, SiCl 2 , SnCl 2 , GeCl 2 , Si (OH) 2 , Sn (OH) 2 , Ge (OH) 2 , VO or TiO are preferable.
  • Cu, Ni, Co, FeCl, Zn, VO, Pd or MnOH are preferable.
  • Specific examples of the phthalocyanine pigment represented by the general formula (II) are described in Table 1 of JP-A-8-60008. Particularly preferably, it is a compound represented by the chemical formula (II-1) described later.
  • R 1 to R 4 independently represent an alkyl group or an alkoxyalkyl group
  • X has a halogen atom, an alkylthio group, and a phenylthio group or a substituent which may have a substituent. It represents a optionally naphthylthio group, where M represents two hydrogen atoms, a divalent metal or a derivative of a trivalent or tetravalent metal.
  • R 1 to R 4 are alkyl groups
  • a linear or branched alkyl group having 1 to 12 carbon atoms is preferable, and a linear or branched alkyl group having 1 to 8 carbon atoms is particularly preferable.
  • Examples are methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-heptyl group, isoheptyl group, sec. -Heptyl group, n-octyl group, 2-ethylhexyl group and the like.
  • R 1 to R 4 are alkoxyalkyl groups, those having a total carbon number of 2 to 6 are preferable. Examples thereof include methoxyethyl group, methoxypropyl group, methoxybutyl group, ethoxyethyl group, ethoxypropyl group, ethoxybutyl group, n-propoxyethyl group and iso-propoxyethyl group.
  • X is a halogen atom, an alkylthio group, a phenylthio group which may have a substituent or a naphthylthio group which may have a substituent, and X is a halogen atom as a chlorine atom, a bromine atom, or a bromine atom.
  • a fluorine atom is preferable, and a chlorine atom is particularly preferable.
  • X is an alkylthio group
  • an alkylthio group having 1 to 12 carbon atoms is preferable. Specific examples include methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, sec-butylthio group, tert-butylthio group, n-pentylthio group, isopentylthio group, neopentylthio group, n.
  • -Hexylthio group isohexylthio group, sec-hexylthio group, cyclohexylthio group, n-heptylthio group, isoheptylthio group, sec-heptylthio group, n-octylthio group, 2-ethylhexylthio group, n-nonylthio group, n-decylthio Examples include a group, an n-undecylthio group, an n-dodecylthio group and the like.
  • X is a phenylthio group which may have a substituent
  • such a substituent may be substituted with an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkyl group.
  • Good amino groups, halogen atoms and the like can be mentioned.
  • phenylthio group which may have such a substituent include a phenylthio group, a p-methylphenylthio group, a p-ethylphenylthio group, a pn-butylphenylthio group and a pn-propylphenyl.
  • a phenylthio group an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a dialkylamino group having 1 to 8 carbon atoms or a phenylthio group having a halogen atom as a substituent is preferable.
  • X is a naphthylthio group which may have a substituent
  • examples of such a substituent include an alkyl group having 1 to 4 carbon atoms, a halogen atom and the like.
  • Specific examples of the naphthylthio group which may have such a substituent include a naphthylthio group, a methylnaphthylthio group, an n-propylnaphthylthio group, an iso-propylnaphthylthio group, an n-butylnaphthylthio group and a tert-.
  • Examples thereof include a butylnaphthylthio group, a chloronaphthylthio group, a bromonaphthylthio group, a fluoronaphthylthio group and the like.
  • a naphthylthio group and a naphthylthio group having an alkyl group having 1 to 4 carbon atoms are preferable.
  • M is divalent
  • Cu, Zn, Fe, Co, Ni, Ru, Pb, Rh, Pd, Pt, Mn or Sn are preferable, and those which are derivatives of trivalent or tetravalent metals.
  • AlCl, AlOH, InCl, FeCl, MnOH, SiCl 2 , SnCl 2 , GeCl 2 , Si (OH) 2 , Sn (OH) 2 , Ge (OH) 2 , VO or TiO are preferable.
  • M Cu, Ni, Co, FeCl, Zn, VO, Pd or MnOH is particularly preferable.
  • Specific examples of the phthalocyanine dye represented by the general formula (III) are described in Table 1 of JP-A-2000-313788. Particularly preferably, it is a compound represented by the chemical formula (III-1) described later.
  • the phthalocyanine compounds represented by the general formulas (I) to (III) preferably have a weight average molecular weight of 900 or more and 5000 or less, excluding the central metal M, of 1200 or more and 2000. The following is more preferable.
  • the near-infrared absorber in the present embodiment preferably contains a plurality of phthalocyanine compounds having different structures in combination. As a result, near infrared rays can be efficiently cut in a wide area.
  • the optical material of the present embodiment may contain the near-infrared absorber at 3 ppm or more and 80 ppm or less, preferably 5 ppm or more and 65 ppm or less, and more preferably 10 ppm or more and 50 ppm or less.
  • Preferred embodiments of the optical material of the present embodiment include the following embodiments A to C from the viewpoint of the effects in the present disclosure.
  • the optical material according to the aspect A has a spectral transmittance of 0.05% or more and 70% or less at a wavelength of 700 nm to 750 nm at a thickness of 2 mm.
  • the spectral transmittance of the wavelength of 700 nm to 750 nm at a thickness of 2 mm in the aspect A is preferably 3% or more and 50% or less, and more preferably 5% or more and 40% or less.
  • the near-infrared absorber in aspect A for example, in order to realize a high near-infrared cut rate, (1) a minimum value of less than 50% spectral transmittance within the wavelength region of 700 nm to 750 nm in the spectral transmittance curve.
  • a near-infrared absorber having is preferable.
  • Examples of the near-infrared absorber satisfying (1) include the compound represented by the above-mentioned general formula (I).
  • the optical material according to the aspect B has a spectral transmittance of 4% or more and 70% or less at a wavelength of 825 nm to 875 nm at a thickness of 2 mm.
  • the spectral transmittance of the wavelength of 825 nm to 875 nm at a thickness of 2 mm in the aspect B is preferably 6% or more and 50% or less, and more preferably 8% or more and 40% or less.
  • near-infrared absorber As the near-infrared absorber in aspect B, for example, in order to realize a high near-infrared cut rate, (2) a minimum value of less than 50% spectral transmittance within the wavelength region of 825 nm to 875 nm in the spectral transmittance curve. A near-infrared absorber having is also preferable. By using a near-infrared absorber satisfying (2), it becomes easy to set the spectral transmittance at a wavelength of 825 nm to 875 nm at a thickness of 2 mm within the above range.
  • Examples of the near-infrared absorber satisfying (2) include the compound represented by the above-mentioned general formula (II).
  • the optical material according to the aspect C has a spectral transmittance of 4% or more and 70% or less at a wavelength of 1000 nm to 1100 nm at a thickness of 2 mm.
  • the spectral transmittance of the wavelength of 1000 nm to 1100 nm at a thickness of 2 mm in the aspect C is preferably 6% or more and 50% or less, and more preferably 8% or more and 40% or less.
  • near-infrared absorber As the near-infrared absorber in aspect C, for example, in order to realize a high near-infrared cut rate, (3) a minimum value of less than 0% spectral transmittance within the wavelength region of 1000 nm to 1100 nm in the spectral transmittance curve. A near-infrared absorber having is also preferable. By using a near-infrared absorber satisfying (3), it becomes easy to set the spectral transmittance at a wavelength of 1000 nm to 1100 nm at a thickness of 2 mm within the above range.
  • Examples of the near-infrared absorber satisfying (3) include the compound represented by the above-mentioned general formula (III).
  • the optical material of the present embodiment includes at least one resin selected from the group consisting of polycarbonate resin, (thio) urethane resin and episulfide resin.
  • the polycarbonate resin may be produced by a phosgene method in which dihydroxydiaryl compounds are reacted with phosgene, a transesterification method in which dihydroxydiaryl compounds are reacted with carbonic acid esters such as diphenyl carbonate, and the like.
  • polycarbonate resin examples include a polycarbonate resin produced from 2,2-bis (4-hydroxyphenyl) propane (also called bisphenol A), a polycarbonate resin produced from 1,1-bis (4-hydroxyphenyl) cyclohexane, and 1 , 1-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane, polycarbonate resin, 9,9-bis (4-hydroxyphenyl) fluorene, 9,9-bis [4- (2-Hydroxyethyloxy) phenyl]
  • a polycarbonate resin produced from fluorene, a copolymerized polycarbonate resin produced from a mixture of dihydroxydiaryl compounds may be used, and a mixture of the above-mentioned polycarbonate resins may be used. There may be.
  • dihydroxydiaryl compounds include bis (4-hydroxyphenyl) methane, 1,1-bis (4-hydroxyphenyl) ethane, 2,2-bis (4-hydroxyphenyl) butane, and 2, in addition to bisphenol A.
  • the dihydroxydiaryl compounds may be used in combination with piperazine, dipiperidyl hydroquinone, resorcin, 4,4'-dihydroxydiphenyl and the like.
  • the viscosity average molecular weight of the polycarbonate resin is usually 10,000 to 100,000, preferably 10,000 to 400,000.
  • a phenol compound having a valence of 3 or more as shown below may be used in combination.
  • the trivalent or higher-valent phenol include fluoroglucin, 1,3,5-tri- (4-hydroxyphenyl) -benzol, 1,1,1-tri- (4-hydroxyphenyl) -ethane and the like.
  • the polycarbonate resin a commercially available product may be used, for example, Panlite (manufactured by Teijin Co., Ltd.), Upiron (manufactured by Mitsubishi Engineering Plastics Co., Ltd.), Novarex (manufactured by Mitsubishi Engineering Plastics Co., Ltd.), SD. Polycarbonate (manufactured by Sumitomo Polycarbonate Co., Ltd.) and the like can be mentioned.
  • the (thio) urethane resin is composed of at least one of a constitutional unit derived from a polyisocyanate compound, a constitutional unit derived from a polythiol compound, and a constitutional unit derived from a polyol compound.
  • the episulfide resin is composed of a structural unit derived from an episulfide compound, a structural unit derived from an episulfide compound, and a structural unit derived from a polythiol compound.
  • the polymerizable composition for an optical material of the present embodiment is a polymerizable composition used for producing the optical material of the present disclosure, and is a combination of a polyisocyanate compound and at least one of a polythiol compound and a polyol compound, an episulfide compound, and the like.
  • a polymerizable compound composed of a combination of an episulfide compound and a polythiol compound (1) a wavelength region of 700 nm to 750 nm on the spectral transmittance curve, (2) a wavelength region of 825 nm to 875 nm on the spectral transmittance curve, and (3).
  • a near-infrared absorber having a minimum value of less than 50% spectral transmittance is included in at least one range of a wavelength region of 1000 nm to 1100 nm in the spectral transmittance curve.
  • the above-mentioned one can be used, and is contained in the polymerizable composition in an amount of 3 ppm or more and 80 ppm or less, preferably 5 ppm or more and 65 ppm or less, and more preferably 10 ppm or more and 50 ppm or less.
  • preferred embodiments of the optical material of the present embodiment include aspects A to C described above from the viewpoint of the effects in the present disclosure.
  • the polymerizable composition used for producing the optical material according to the aspect A it is preferable to use the near-infrared absorber described in the section of the aspect A.
  • the polymerizable composition used for producing the optical material according to the aspect B it is preferable to use the near-infrared absorber described in the section of the aspect B.
  • the polymerizable composition used for producing the optical material according to Aspect C it is preferable to use the near-infrared absorber described in the section of Aspect C.
  • polyisocyanate compound examples include an aliphatic isocyanate compound, an alicyclic isocyanate compound, an aromatic isocyanate compound, a heterocyclic isocyanate compound, and an aromatic aliphatic isocyanate compound, and one or a mixture of two or more thereof is used.
  • These isocyanate compounds may include dimers, trimers and prepolymers. Examples of these isocyanate compounds include the compounds exemplified in WO2011 / 055540.
  • the polyisocyanate compound is 2,5-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, 2,6-bis (isocyanatomethyl).
  • the polythiol compound is a compound having two or more mercapto groups, and examples thereof include the compounds exemplified in WO2016 / 125736.
  • the polythiol compound is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiane octane, 5,7-dimercaptomethyl-1,11-dimercapto-3.
  • the polyol compound is one or more aliphatic or alicyclic alcohols, and specifically, linear or branched aliphatic alcohols, alicyclic alcohols, these alcohols and ethylene oxide, propylene oxide, ⁇ . -Alcohols to which caprolactone is added can be mentioned, and specifically, the compounds exemplified in WO2016 / 125736 can be used.
  • the polyol compound is preferably ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1,3-propanediol, 1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, and the like. It is at least one selected from the group consisting of 1,3-cyclohexanediol and 1,4-cyclohexanediol.
  • episulfide compound examples include an epithioethylthio compound, a chain aliphatic 2,3-epithiopropylthio compound, a cyclic aliphatic 2,3-epiopropylthio compound, and an aromatic 2,3-epithio.
  • examples thereof include propylthio compounds, chain aliphatic 2,3-epiopropyloxy compounds, cyclic aliphatic 2,3-epiopropyloxy compounds, and aromatic 2,3-epiopropyloxy compounds. It is used alone or in combination of two or more.
  • these episulfide compounds include the compounds exemplified in WO2015 / 137401.
  • the episulfide compound is preferably bis (2,3-epiopropyl) sulfide, bis (2,3-epiothiopropyl) disulfide, bis (1,2-epioethyl) sulfide, bis (1,2-epioethyl) disulfide. , And at least one selected from the group consisting of bis (2,3-epithiopropylthio) methane.
  • the additive examples include a polymerization catalyst, an internal mold release agent, a bluing agent, an ultraviolet absorber, and the like.
  • a polymerization catalyst when obtaining polyurethane and polythiourethane, may or may not be used.
  • Examples of the internal mold release agent include acidic phosphoric acid esters.
  • Examples of 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.
  • Examples of the bluing agent include those having an absorption band in the orange to yellow wavelength region of the visible light region and having a function of adjusting the hue of an optical material made of resin. More specifically, the bluing agent contains a substance showing a blue to purple color.
  • the ultraviolet absorbers used include 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-acryloyloxybenzophenone, 2-hydroxy-4-acryloyloxy-5-tert-butylbenzophenone, 2-hydroxy-.
  • Benzophenone-based UV absorbers such as 4-acryloyloxy-2', 4'-dichlorobenzophenone,
  • the composition for an optical material can be obtained by mixing the above components by a predetermined method.
  • the mixing order and mixing method of each component in the composition are not particularly limited as long as each component can be mixed uniformly, and a known method can be used.
  • optical material of the present embodiment can be obtained by polymerizing and curing the composition for an optical material of the present embodiment.
  • Optical materials include plastic spectacle lenses, goggles, vision correction spectacle lenses, imaging device lenses, LCD projector frennel lenses, lenticular lenses, contact lenses, infrared sensor lenses, infrared camera lenses, sunglasses and fashion lenses.
  • plastic lenses such as eyewear, encapsulants for light emitting diodes (LEDs), optical waveguides, optical adhesives used for joining optical lenses and optical waveguides, near-infrared absorbing films used for optical lenses, liquid crystal display device members ( Examples include a transparent coating used for a substrate, a light guide plate, a film, a sheet, etc., a windshield of a car front lens, a motorcycle helmet, a transparent substrate, and the like.
  • the optical material of the present embodiment may contain an ultraviolet absorber.
  • a plastic lens, a lens for an infrared sensor, a lens for an infrared camera, eyewear, a near-infrared absorbing film used for these optical lenses and the like are preferable.
  • a plastic lens which is a preferred embodiment of the optical material, will be described in detail.
  • plastic lens examples include the following configurations.
  • a plastic lens including a lens base material made of the composition for optical material of the present embodiment (b) A lens base material (excluding the lens base material obtained from the composition for optical material of this embodiment) surface.
  • a plastic lens having a film or coating layer made of the composition for optical material of the present embodiment on at least one surface (c) A lens base material (c) on both sides of a film made of the composition for optical material of the present embodiment.
  • a plastic lens on which (excluding the lens base material obtained from the composition for an optical material of the present embodiment) is laminated these plastic lenses can be preferably used in the present embodiment.
  • each embodiment will be described.
  • the method for producing a plastic lens including the lens base material composed of the composition for an optical material of the present embodiment is not particularly limited, but a preferred production method includes casting polymerization using a lens casting mold.
  • the lens base material can be composed of a polyurethane resin, a polythiourethane resin, or an episulfide resin, and contains a near-infrared absorber and a monomer of these resins (resin monomer for an optical material) for the optical material of the present embodiment.
  • the composition can be used.
  • the composition for optical material is injected into the cavity of the molding mold held by a gasket or tape or the like.
  • defoaming treatment under reduced pressure, filtration treatment such as pressurization and reduced pressure, and the like, if necessary.
  • the lens casting mold is heated in a heatable device such as in an oven or water with a predetermined temperature program to cure and mold.
  • the resin molded product may be subjected to a treatment such as annealing, if necessary.
  • a chain extender in addition to the above-mentioned "arbitrary additive", a chain extender, a cross-linking agent, a light stabilizer, an antioxidant, as in a known molding method depending on the purpose.
  • Oil-soluble dyes, fillers, adhesion improvers and the like may be added.
  • the plastic lens in the present embodiment may have various coating layers on a lens base material made of the composition for an optical material of the present embodiment according to its purpose and application.
  • the coating layer can contain a near infrared absorber.
  • the coating layer containing the near-infrared absorber can be prepared by using a coating material (composition) containing the near-infrared absorber, or after forming the coating layer, the near-infrared absorber is dispersed in water or a solvent. It can be prepared by immersing a plastic lens with a coating layer in the dispersion liquid thus obtained and impregnating the coating layer with a near-infrared absorber.
  • the plastic lens of the present embodiment may include a film or layer of the composition for optical materials of the present embodiment on at least one surface of the lens base material surface.
  • the lens base material does not have to be formed from the composition for optical materials of the present embodiment, and various lens base materials can be used.
  • a lens base material is manufactured, and then the composition for an optical material of the present embodiment is formed on at least one surface of the lens base material.
  • a method of laminating a film or a sheet, (b-2) One of the molds of the film or sheet made of the composition for optical material of the present embodiment in the cavity of the molding mold held by a gasket or tape as described later.
  • a method of arranging the composition along the inner wall of the lens and then injecting the composition for an optical material into the cavity and curing the composition can be mentioned.
  • the film or sheet made of the composition for optical materials of the present embodiment used in the method (b-1) is not particularly limited and can be obtained by a known molding method.
  • the lens base material can be obtained from a known optical resin, and various optical resins can be used.
  • a known method can be used as a method of bonding the film or sheet made of the composition for optical material of the present embodiment on the surface of the lens base material.
  • the casting polymerization in the method (b-2) can be carried out in the same manner as the plastic lens method in the embodiment a, and the composition used for the casting polymerization is a composition containing a resin monomer for an optical material ( (Does not contain near-infrared absorber).
  • the plastic lens in the present embodiment may have various coating layers on a lens base material made of a composition for an optical material or on a "film or layer" according to its purpose and application. Similar to the plastic lens in embodiment a, the coating layer can contain a near infrared absorber.
  • a lens base material (excluding the lens base material obtained from the composition for the optical material of the present embodiment) is laminated on both sides of the film made of the composition for the optical material of the present embodiment. You may.
  • a method for producing a plastic lens in the present embodiment for example, (c-1) a method of producing a lens base material and laminating it on both sides of a film or a sheet made of the composition for an optical material of the present embodiment, (c). -2) In the cavity of the molding mold held by a gasket or tape, the film or sheet made of the composition for optical material of the present embodiment is placed in a state of being separated from the inner wall of the mold, and then the optical material is placed in the cavity. Examples thereof include a method of injecting a composition for a material and curing it.
  • the film or sheet made of the composition for optical material of the present embodiment and the lens base material used in the method (c-1) are the same as those of the method (b-1) of the plastic lens in the embodiment b.
  • a known method can be used as a method of bonding the film or sheet made of the composition for optical material of the present embodiment on the surface of the lens base material.
  • the method (c-2) can be specifically carried out as follows.
  • a film or a sheet made of the composition for an optical material of the present embodiment is placed on the inner surface of the mold on the front side where both sides face each other. Install so that it is parallel to.
  • a composition containing a resin monomer for an optical material (not containing a near-infrared absorber) in two gaps between the mold and the polarizing film by a predetermined injection means. Inject.
  • the lens casting mold is heated in a heatable device such as in an oven or water with a predetermined temperature program to cure and mold.
  • the resin molded product may be subjected to a treatment such as annealing, if necessary.
  • the plastic lens in the present embodiment may have various coating layers on the lens base material according to its purpose and application. Similar to the plastic lens in embodiment a, the coating layer can contain a near infrared absorber.
  • a plastic spectacle lens can be obtained by using the plastic lens of the present embodiment. If necessary, a coating layer may be applied to one side or both sides.
  • the coating layer include a primer layer, a hard coat layer, an antireflection layer, an antifogging coat layer, an antifouling layer, and a water repellent layer.
  • Each of these coating layers can be used alone, or a plurality of coating layers can be used in multiple 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.
  • Each of these coating layers is a near-infrared absorber used in the present embodiment, an infrared absorber for the purpose of protecting the eyes from infrared rays, a light stabilizer or antioxidant for the purpose of improving the weather resistance of the lens, and fashionability of the lens.
  • Dyes and pigments, photochromic dyes and photochromic pigments, antistatic agents, and other known additives for enhancing the performance of lenses may be used in combination for the purpose of enhancing the lens performance.
  • various leveling agents for the purpose of improving coatability may be used.
  • the primer layer is usually formed between the hard coat layer and the lens, which will be described later.
  • 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, and it is also possible to improve the impact resistance in some cases.
  • Any material can be used for the primer layer as long as it has high adhesion to the obtained lens, but usually, a primer containing urethane resin, epoxy resin, polyester resin, melamine resin, and polyvinyl acetal as main components. Compositions and the like are used.
  • the primer composition may use an appropriate solvent that does not affect the lens for the purpose of adjusting the viscosity of the composition. Of course, it may be used without a solvent.
  • the primer layer can be formed by either a coating method or a dry method.
  • the coating method the primer layer is formed by applying the primer composition to the lens by a known coating method such as spin coating or dip coating and then solidifying the lens.
  • the 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 may be subjected to pretreatment such as alkali treatment, plasma treatment, and 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.
  • the hard coat layer is generally 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.
  • a hard coat composition containing one or more of the oxide fine particles of the above and at least one of the fine particles composed of a composite oxide of two or more elements selected from these element groups is used. ..
  • the hard coat composition includes at least amines, amino acids, metal acetylacetonate complexes, organic acid metal salts, perchloric acids, perchloric acid salts, acids, metal chlorides and polyfunctional epoxy compounds. It is preferable to include any of them.
  • a suitable solvent that does not affect the lens may be used for the hard coat composition, or a solvent-free solvent may be used.
  • 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 known coating method such as spin coating or dip coating
  • the curing method include heat curing and a curing method by irradiation with energy rays such as ultraviolet rays and visible light.
  • 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.
  • the antireflection layer is usually formed on the hard coat layer as needed.
  • inorganic layers inorganic oxides such as SiO 2 and TiO 2 are used, and vacuum deposition method, sputtering method, ion plating method, ion beam assist method, and CVD method are used. It is formed by a dry method such as.
  • an organic system it is formed by a wet process using a composition containing an organosilicon compound and silica-based fine particles having internal cavities.
  • the antireflection layer has a single layer and a plurality of layers, and when used as a single layer, the refractive index is preferably at least 0.1 or more lower than the refractive index of the hard coat layer.
  • a multilayer antireflection film is preferable, and in that case, a low refractive index film and a high refractive index film are alternately laminated.
  • the difference in refractive index between the low refractive index film and the high refractive index film is preferably 0.1 or more.
  • Examples of the high-refractive index film include films of ZnO, TiO 2 , CeO 2 , Sb 2 O 5 , SnO 2 , ZrO 2 , Ta 2 O 5, and the like, and examples of the low-refractive index film include SiO 2 film. ..
  • An antifogging layer, an antifouling layer, and a water repellent layer may be formed on the antireflection layer, if necessary.
  • the method for forming the antifogging layer, the antifouling layer, and the water repellent layer is not particularly limited as long as it does not adversely affect the antireflection function, and the treatment method, treatment material, and the like are not particularly limited. Methods, antifouling treatment methods, water repellent treatment methods, materials can be used.
  • a method of covering the surface with a surfactant for example, a method of adding a hydrophilic film to the surface to make it water-absorbent, and a method of covering the surface with fine irregularities to improve water absorption.
  • a method of making water absorbent by utilizing photocatalytic activity a method of applying a super-water repellent treatment to prevent the adhesion of water droplets, and the like.
  • a method of forming a water repellent treatment layer by vapor deposition or sputtering of a fluorine-containing silane compound or the like, or a method of dissolving a fluorine-containing silane compound in a solvent and then coating it to form a water repellent treatment layer a method of forming a water repellent treatment layer by vapor deposition or sputtering of a fluorine-containing silane compound or the like, or a method of dissolving a fluorine-containing silane compound in a solvent and then coating it to form a water repellent treatment layer. And so on.
  • YI measurement method YI was measured with a 2 mm thick flat lens with a spectrophotometer CM-5 manufactured by Konica Minolta.
  • the near-infrared absorber shown below was used.
  • extinction coefficient (Pmax point indicating the maximum extinction coefficient in the peak) (ml / g ⁇ cm) is 1.57 ⁇ 10 5
  • the peak (P) The peak width at the absorbance of 1/4 of the absorbance of (Pmax) is 43 nm, and the peak width at the absorbance of 1/2 of the absorbance of (Pmax) of the peak (P) is 28 nm, and the peak (Pmax) The peak width at the absorbance of 2/3 of the absorbance of (Pmax) of P) was 20 nm.
  • extinction coefficient (Pmax point indicating the maximum extinction coefficient in the peak) (ml / g ⁇ cm) is 1.11 ⁇ 10 5
  • the peak (P) The peak width at the absorbance of 1/4 of the absorbance of (Pmax) is 80 nm, and the peak width at the absorbance of 1/2 of the absorbance of (Pmax) of the peak (P) is 47 nm, and the peak (Pmax) The peak width at the absorbance of 2/3 of the absorbance of (Pmax) of P) was 35 nm.
  • extinction coefficient (Pmax point indicating the maximum extinction coefficient in the peak) (ml / g ⁇ cm) is 7.22 ⁇ 10 4
  • the peak (P) The peak width at 1/4 of the absorbance of (Pmax) is 250 nm, and the peak width at 1/2 of the absorbance of (Pmax) of the peak (P) is 112 nm, and the peak (Pmax) The peak width at the absorbance of 2/3 of the absorbance of (Pmax) of P) was 81 nm.
  • peak apex a extinction coefficient (ml / g ⁇ cm) is 1.75 ⁇ 10 5 of (Pmax maximum point which shows the extinction coefficient in the peak), 1/4 of the absorbance at the peak of the (P) (Pmax)
  • the peak width at the absorbance of (Pmax) is 37 nm
  • the peak width at the absorbance of 1/2 of the absorbance at (Pmax) of the peak (P) is 24 nm
  • the absorbance at (Pmax) of the peak (P) is 2.
  • the peak width at the absorbance of / 3 was 17 nm.
  • ⁇ Near infrared absorber E It has a main absorption peak (P) at 935 nm in the visible light absorption spectral spectrum measured with a toluene solution of 36.5 mass ppm of the near-infrared absorber E at an optical path length of 10 mm, and the above peak (P) peak apex: extinction coefficient (Pmax point indicating the maximum extinction coefficient in the peak) (ml / g ⁇ cm) is 1.58 ⁇ 10 4, and the peak of the (P) of the absorbance (Pmax) 1 /
  • the peak width at the absorbance of 2 was 379 nm, and the peak width at the absorbance of 2/3 of the (Pmax) absorbance of the peak (P) was 252 nm.
  • the peak width at 1/4 of the absorbance of (Pmax) of the peak (P) was measured because there was no value that was 1/4 of the absorbance of (Pmax) of the peak (P).
  • Example 1 0.015 parts by weight of dibutyltin (II) dichloride, 0.1 parts by weight of internal mold release agent for MR manufactured by Mitsui Chemicals, 0.15 parts by weight of ultraviolet absorber Tinuvin 329, 52 parts by weight of m-xylylene diisocyanate. , 0.00042 part by weight of the near-infrared absorber A was charged to prepare a mixed solution. The mixed solution was stirred at 25 ° C. for 1 hour to completely dissolve. Then, 48 parts by weight of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane was added to this mixture, and this was stirred at 25 ° C. for 30 minutes to prepare a uniform solution.
  • This solution was defoamed at 400 Pa for 1 hour, filtered through a 1 ⁇ m PTFE filter, and then injected into a flat glass mold having a center thickness of 2 mm and a diameter of 77 mm.
  • the temperature of this glass mold was raised from 25 ° C. to 120 ° C. over 16 hours.
  • the lens was removed from the glass mold to obtain a flat lens.
  • the obtained flat lens was further annealed at 120 ° C. for 2 hours.
  • the physical properties of the flattened lens subjected to this annealing treatment were measured. The results are shown in Table 1.
  • Example 2 to 7 A flat lens was obtained in the same manner as in Example 1 except that the amount of the near-infrared absorber A added was the amount shown in Table 1. Table 1 shows the measurement results of the physical properties of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 3 is shown in FIG.
  • Examples 8 to 10, Comparative Example 1 A flat lens was obtained in the same manner as in Example 1 except that the near-infrared absorber A was changed to the near-infrared absorber B and the amount added was the amount shown in Table 1.
  • Table 1 shows the measurement results of the physical properties of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 10 is shown in FIG.
  • Examples 11 to 13, Comparative Example 2 A flat lens was obtained in the same manner as in Example 1 except that the near-infrared absorber A was changed to the near-infrared absorber C and the amount added was the amount shown in Table 1.
  • Table 1 shows the measurement results of the physical properties of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 13 is shown in FIG.
  • Example 14 0.035 parts by weight of dibutyltin (II) dichloride, 0.1 parts by weight of internal mold release agent for MR manufactured by Mitsui Chemicals, 1.5 parts by weight of ultraviolet absorber Tinuvin 329, 2,5-bis (isocyanatomethyl) ) 50.6 parts by weight of a mixture of bicyclo- [2.2.1] -heptane and 2,6-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, near-infrared absorber A A mixed solution was prepared by charging 0.00042 parts by weight. The mixed solution was stirred at 25 ° C. for 1 hour to completely dissolve.
  • the lens was removed from the glass mold to obtain a flat lens.
  • the obtained flat lens was further annealed at 120 ° C. for 2 hours.
  • the physical properties of the flattened lens subjected to this annealing treatment were measured. The results are shown in Table 2.
  • Example 15 to 20 A flat lens was obtained in the same manner as in Example 14 except that the amount of the near-infrared absorber A added was the amount shown in Table 2.
  • Table 2 shows the measurement results of the physical properties of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 16 is shown in FIG.
  • Examples 21 to 22, Comparative Example 5 A flat lens was obtained in the same manner as in Example 14 except that the near-infrared absorber A was changed to the near-infrared absorber B and the amount added was the amount shown in Table 2.
  • Table 2 shows the measurement results of the physical properties of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 22 is shown in FIG.
  • Examples 23 to 24, Comparative Example 6 A flat lens was obtained in the same manner as in Example 14 except that the near-infrared absorber A was changed to the near-infrared absorber C and the amount added was the amount shown in Table 2.
  • Table 2 shows the measurement results of the physical properties of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 24 is shown in FIG.
  • Example 8 A flat lens was obtained in the same manner as in Example 14 except that the near-infrared absorber A was changed to the near-infrared absorber E and the amount added was the amount shown in Table 2.
  • Table 2 shows the measurement results of the physical properties of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Comparative Example 8 is shown in FIG.
  • Example 25 0.008 parts by weight of dimethyl tin (II) dichloride, 0.1 parts by weight of Mitsui Chemicals' MR internal mold release agent, 0.6 parts by weight of ultraviolet absorbers Tinuvin 329 and Seesorb 709, respectively, m-xylylene diisocyanate 50.7 parts by weight and 0.00042 part by weight of the near-infrared absorber A were charged to prepare a mixed solution. The mixed solution was stirred at 25 ° C. for 1 hour to completely dissolve. Then, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane and 4,7-dimercaptomethyl-1,11-dimercapto-3,6 were added to this mixture.
  • Example 26 to 28 A flat lens was obtained in the same manner as in Example 25 except that the amount of the near-infrared absorber A added was the amount shown in Table 3. Table 3 shows the measurement results of the physical properties of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 26 is shown in FIG.
  • Example 29 to 30, Comparative Example 9 A flat lens was obtained in the same manner as in Example 25 except that the near-infrared absorber A was changed to the near-infrared absorber B and the amount added was the amount shown in Table 3.
  • Table 3 shows the measurement results of the physical properties of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 30 is shown in FIG.
  • Examples 31 to 32, Comparative Example 10 A flat lens was obtained in the same manner as in Example 25 except that the near-infrared absorber A was changed to the near-infrared absorber C and the amount added was the amount shown in Table 3.
  • Table 3 shows the measurement results of the physical properties of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 32 is shown in FIG.
  • Example 33 0.012 parts by weight of N, N-dimethylcyclohexylamine, 0.092 parts by weight of N, N-dicyclohexylmethylamine, 1 part by weight of the ultraviolet absorber nitrogenPS, 90 parts by weight of bis (2,3-epithiopropyl) disulfide.
  • This mixed solution was defoamed at 400 Pa for 1 hour, filtered through a 1 ⁇ m PTFE filter, and then injected into a flat glass mold having a center thickness of 2 mm and a diameter of 77 mm.
  • the temperature of this glass mold was raised from 25 ° C. to 120 ° C. over 20 hours.
  • the lens was removed from the glass mold to obtain a flat lens.
  • the obtained flat lens was further annealed at 120 ° C. for 2 hours.
  • the physical properties of the flattened lens subjected to this annealing treatment were measured. The results are shown in Table 4.
  • Examples 34 to 39 A flat lens was obtained in the same manner as in Example 33 except that the amount of the near-infrared absorber A added was the amount shown in Table 4. Table 4 shows the measurement results of the physical properties of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 35 is shown in FIG.
  • Examples 40 to 41, Comparative Example 13 A flat lens was obtained in the same manner as in Example 33 except that the near-infrared absorber A was changed to the near-infrared absorber B and the amount added was the amount shown in Table 4.
  • Table 4 shows the measurement results of the physical properties of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 41 is shown in FIG.
  • Examples 42 to 43, Comparative Example 14 A flat lens was obtained in the same manner as in Example 33 except that the near-infrared absorber A was changed to the near-infrared absorber C and the amount added was the amount shown in Table 4.
  • Table 4 shows the measurement results of the physical properties of the obtained flat lens. Further, the spectral transmittance curve of the flat lens of Example 43 is shown in FIG.
  • Example 44 0.452 parts by weight of dimethyltin (II) dichloride, 0.18 parts by weight of JP-506H manufactured by Johoku Chemical Industry Co., Ltd., 1 part by weight of the ultraviolet absorber Tinuvin329, and 48 parts by weight of 1,3-bis (isocyanismethyl) cyclohexane.
  • a mixed solution was prepared by charging 0.00184 parts by weight of the near-infrared absorber A. The mixed solution was stirred at 25 ° C. for 1 hour to completely dissolve.
  • the lens was removed from the glass mold to obtain a flat lens.
  • the obtained flat lens was further annealed at 120 ° C. for 2 hours.
  • the physical properties of the flattened lens subjected to this annealing treatment were measured. The results are shown in Table 5.
  • Example 45 A flat lens was obtained in the same manner as in Example 44 except that the near-infrared absorber A was changed to the near-infrared absorber B and the amount added was 0.0026 parts by weight. Table 5 shows the measurement results of the physical properties of the obtained flat lens.
  • Example 46 A flat lens was obtained in the same manner as in Example 44 except that the near-infrared absorber A was changed to the near-infrared absorber C and the amount added was 0.00399 parts by weight. Table 5 shows the measurement results of the physical properties of the obtained flat lens.
  • Example 18 A flat lens was obtained in the same manner as in Example 44 except that the near-infrared absorber A was changed to the near-infrared absorber E and the amount added was 0.01825 parts by weight. Table 5 shows the measurement results of the physical properties of the obtained flat lens.
  • Example 101 and Example 102 Polycarbonate resin (Panlite L-1225WP manufactured by Teijin Co., Ltd.) and the near-infrared absorber shown in Table 6 are mixed by a tumbler at an amount such that the content of the near-infrared absorber is the content shown in Table 6.
  • pellets (resin composition) were prepared by melting and kneading with a single-screw extruder under the conditions of a cylinder set temperature of 280 ° C. and a screw rotation speed of 56 rpm (revolutions per minute).
  • a flat lens having an outer diameter of 150 mm ⁇ 300 mm and a thickness of 2 mm was molded by an injection molding machine under the conditions of a cylinder temperature of 280 ° C., a mold temperature of 80 ° C., and a molding cycle of 60 seconds.
  • Table 6 shows the measurement results of the physical properties of the obtained flat lens.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Ophthalmology & Optometry (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Optical Filters (AREA)
  • Eyeglasses (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne un matériau optique contenant une résine qui représente au moins un type sélectionné dans le groupe constitué par une résine polycarbonate, une résine (thio)uréthane et une résine épisulfure, et un absorbant proche infrarouge. Selon l'invention, dans un espace colorimétrique CIE 1976 (L*, a*, b*) lorsqu'il est mesuré à une épaisseur de 2 mm, a* représente 30-0 compris et L* est supérieur ou égal à 80.
PCT/JP2020/018016 2019-04-26 2020-04-27 Matériau optique, composition polymérisable pour matériau optique, lentille en plastique, lunettes, capteur infrarouge et caméra infrarouge WO2020218614A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN202080029166.XA CN113711113B (zh) 2019-04-26 2020-04-27 光学材料、光学材料用聚合性组合物、塑料透镜、护目镜、红外线传感器及红外线照相机
KR1020217033867A KR20210144775A (ko) 2019-04-26 2020-04-27 광학 재료, 광학 재료용 중합성 조성물, 플라스틱 렌즈, 아이웨어, 적외선 센서 및 적외선 카메라
JP2021516329A JP7254167B2 (ja) 2019-04-26 2020-04-27 光学材料、光学材料用重合性組成物、プラスチックレンズ、アイウェア、赤外線センサー及び赤外線カメラ

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2019-086155 2019-04-26
JP2019086155 2019-04-26

Publications (1)

Publication Number Publication Date
WO2020218614A1 true WO2020218614A1 (fr) 2020-10-29

Family

ID=72942577

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2020/018016 WO2020218614A1 (fr) 2019-04-26 2020-04-27 Matériau optique, composition polymérisable pour matériau optique, lentille en plastique, lunettes, capteur infrarouge et caméra infrarouge

Country Status (4)

Country Link
JP (1) JP7254167B2 (fr)
KR (1) KR20210144775A (fr)
CN (1) CN113711113B (fr)
WO (1) WO2020218614A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63270765A (ja) * 1986-12-26 1988-11-08 Mitsui Toatsu Chem Inc フタロシアニン化合物およびこれを含有する樹脂組成物
JPS6411153A (en) * 1987-07-03 1989-01-13 Mitsui Toatsu Chemicals Near infrared-absorbing polymer composition
JPH08176101A (ja) * 1994-12-19 1996-07-09 Yamamoto Chem Inc フタロニトリル化合物、その製造方法、このフタロニトリル化合物より得られるフタロシアニン化合物及びその用途
JP2004525802A (ja) * 2001-04-10 2004-08-26 バイエル アクチェンゲゼルシャフト 熱吸収性層系
JP2004529007A (ja) * 2001-04-10 2004-09-24 バイエル アクチェンゲゼルシャフト 熱吸収性コーティング系
WO2018082946A1 (fr) * 2016-11-04 2018-05-11 Essilor International Articles optiques de coupe de lumière proche infrarouge à faible couleur résiduelle

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3855067B2 (ja) 1999-04-28 2006-12-06 山本化成株式会社 半導体封止用エポキシ樹脂組成物
JP5288360B2 (ja) 2005-03-09 2013-09-11 山本化成株式会社 フタロシアニン化合物の製造方法及びこれより得られた該化合物の混合物
JP2009258362A (ja) * 2008-04-16 2009-11-05 Jsr Corp 近赤外線カットフィルター
JP5489669B2 (ja) 2008-11-28 2014-05-14 Ｊｓｒ株式会社 近赤外線カットフィルターおよび近赤外線カットフィルターを用いた装置
EP2866064B1 (fr) * 2012-06-26 2017-08-09 Mitsui Chemicals, Inc. Composition polymérisable pour matière optique, matière optique et lentille en matière plastique obtenue à partir de ladite composition
JP6026946B2 (ja) * 2013-04-19 2016-11-16 出光興産株式会社 ポリカーボネート系樹脂組成物及び成形体
JP6306003B2 (ja) 2013-06-27 2018-04-04 山本化成株式会社 テトラフェニルナフタロシアニン化合物、その製造方法および用途
KR101761828B1 (ko) 2014-07-14 2017-07-27 케이에스랩(주) 광학수지 조성물 및 이를 이용한 광학용 렌즈
CN107849207A (zh) 2015-07-13 2018-03-27 Ks试验研究株式会社 电磁波阻挡用光学组合物及利用所述光学组合物制造光学透镜的方法
JP6605039B2 (ja) * 2015-12-17 2019-11-13 富士フイルム株式会社 近赤外線吸収性組成物、膜、赤外線カットフィルタ、固体撮像素子、赤外線吸収剤および化合物
US10890699B2 (en) * 2016-09-07 2021-01-12 Largan Precision Co., Ltd. Optical image lens assembly, image capturing apparatus and electronic device
JP6983585B2 (ja) * 2017-09-05 2021-12-17 三菱瓦斯化学株式会社 調色シート

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63270765A (ja) * 1986-12-26 1988-11-08 Mitsui Toatsu Chem Inc フタロシアニン化合物およびこれを含有する樹脂組成物
JPS6411153A (en) * 1987-07-03 1989-01-13 Mitsui Toatsu Chemicals Near infrared-absorbing polymer composition
JPH08176101A (ja) * 1994-12-19 1996-07-09 Yamamoto Chem Inc フタロニトリル化合物、その製造方法、このフタロニトリル化合物より得られるフタロシアニン化合物及びその用途
JP2004525802A (ja) * 2001-04-10 2004-08-26 バイエル アクチェンゲゼルシャフト 熱吸収性層系
JP2004529007A (ja) * 2001-04-10 2004-09-24 バイエル アクチェンゲゼルシャフト 熱吸収性コーティング系
WO2018082946A1 (fr) * 2016-11-04 2018-05-11 Essilor International Articles optiques de coupe de lumière proche infrarouge à faible couleur résiduelle

Also Published As

Publication number Publication date
CN113711113B (zh) 2023-07-28
JP7254167B2 (ja) 2023-04-07
JPWO2020218614A1 (ja) 2021-12-09
CN113711113A (zh) 2021-11-26
KR20210144775A (ko) 2021-11-30

Similar Documents

Publication Publication Date Title
CN108026240B (zh) 光学材料用聚合性组合物、由该组合物得到的光学材料及塑料透镜
KR101849862B1 (ko) 광학 재료 및 그 용도
EP3103822B1 (fr) Composition polymérisable pour matériau optique et matériau optique et lentille en plastique obtenue à partir de ladite composition
JP6324973B2 (ja) 光学材料およびその用途
CN109716216B (zh) 光致变色透镜及聚合性组合物
WO2021024962A1 (fr) Matériau optique
CN113692550B (zh) 光学材料、光学材料用聚合性组合物、固化物、塑料透镜、光学材料的应用方法
WO2020218614A1 (fr) Matériau optique, composition polymérisable pour matériau optique, lentille en plastique, lunettes, capteur infrarouge et caméra infrarouge
WO2019131544A1 (fr) Composé à base d'indole, son procédé de production et son utilisation
JP7126383B2 (ja) 眼鏡用レンズ
JP2021107882A (ja) 光学材料、光学材料用重合性組成物、プラスチックレンズ、アイウェア及び光学センサー
WO2020218615A1 (fr) Matériau optique, composition polymérisable pour matériau optique, verre en matière plastique, lunettes, capteur infrarouge et caméra infrarouge
WO2022114064A1 (fr) Matériau optique, lentille et lunettes
WO2023229048A1 (fr) Matériau optique et verre de lunettes
JP2023161056A (ja) 光学材料用重合性組成物およびフォトクロミックレンズ

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20794753

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2021516329

Country of ref document: JP

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 20217033867

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 20794753

Country of ref document: EP

Kind code of ref document: A1