JP7540625B2 - Optical materials, polymerizable compositions for optical materials, plastic lenses, eyewear and optical sensors - Google Patents

Description

This disclosure relates to optical materials, polymerizable compositions for optical materials, plastic lenses, eyewear, and optical sensors.

Lenses that cut out specific wavelength ranges have been developed in the past.

For example, Patent Document 1 discloses a near-infrared cut filter having a near-infrared reflective film formed by alternately laminating two dielectric layers with different refractive indices on at least one surface of a transparent substrate containing a cyclic olefin resin and a glass filler.

Patent Document 2 discloses a near-infrared cut filter that provides a predetermined transmittance for light in multiple 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.

Patent documents 3 to 7 disclose resin compositions containing a specific phthalocyanine dye and a resin. Patent document 7 describes that a lens for safety glasses can be obtained from the resin composition.
Patent Documents 8 and 9 disclose far-infrared cut lenses made of a phthalocyanine dye and a urethane resin or a polythiourethane resin.

JP 2009-258362 A JP 2011-100084 A Japanese Patent Application Publication No. 11-48612 JP 2000-313788 A JP 2006-282646 A International Publication No. 2014/208484 Japanese Patent Application Publication No. 8-60008 Special table 2017-529415 publication Special table 2018-529829 publication

The near-infrared cut filters of Patent Documents 1 and 2 can cut near-infrared rays, but the filters can become cloudy and lose transparency.

Therefore, when the inventors investigated optical materials in which a near-infrared absorbent was added to a resin, they found that the near-infrared absorbent did not dissolve in the resin, that when the content of the near-infrared absorbent was increased, the optical material became cloudy and the transparency decreased, and that coloring deteriorated the color (design).
Thus, in optical materials using a near-infrared absorbing agent, there is a trade-off between the near-infrared blocking effect and design properties.

The problem that one embodiment of the present disclosure aims to solve is to provide an optical material, a polymerizable composition for optical materials, a plastic lens, eyewear, and an optical sensor that have a high near-infrared cut rate and excellent design properties.

<1> An optical material comprising at least one resin selected from the group consisting of polycarbonate resins, (thio)urethane resins, and episulfide resins, and at least one near-infrared absorbing agent selected from the group consisting of a compound represented by the following formula (I), a compound represented by the following formula (II), and a compound represented by the following formula (III), in which a* is -0.8 or more and 10 or less, and L* is 70 or more in the CIE1976 (L*, a*, b*) color space when measured at a thickness of 2 mm.

In formula (I), R ₁ and R ₂ each independently represent an alkyl group which may be substituted, and M represents a divalent metal atom, a trivalent or tetravalent substituted metal, or an oxymetal.

In formula (II), _R1 and _R2 each independently represent an optionally substituted alkyl group, _R3 represents a nitro group or a group represented by _NR4R5 , which may be _the same or different from each other, and _R4 and _R5 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkylsulfonyl group or an optionally substituted arylsulfonyl group.

In formula (III), _R1 and _R2 each independently represent an optionally substituted alkyl group, _R3 and _R4 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkylsulfonyl group, or an optionally substituted arylsulfonyl group, and M represents a divalent metal atom, a trivalent or tetravalent substituted metal, or an oxymetal.
<2> The optical material according to <1>, having a transmittance of 80% or less at a maximum absorption wavelength.
<3> The optical material according to <1> or <2>, which has a minimum value of a transmittance curve in a wavelength range of 800 nm to 950 nm at a thickness of 2 mm, and the minimum value is 0.05% or more and 80% or less.
<4> The optical material according to any one of <1> to <3>, which has a luminous transmittance of 70% or more at a thickness of 2 mm.
<5> The optical material according to any one of <1> to <4>, wherein the near-infrared absorbent has a peak between 840 nm and 930 nm in a visible light absorption spectrum measured in a 3 ppm to 5 ppm toluene solution, the peak has an extinction coefficient of 1.10 x 10 ⁵ ml/g cm or more at an apex of the peak, the peak has a peak width of 1/4 of the absorbance at the apex of the peak of 100 nm or less, the peak width of 1/2 of the absorbance at the apex of the peak of 55 nm or less, and the peak width of 2/3 of the absorbance at the apex of the peak of 40 nm or less.
<6> The optical material according to any one of <1> to <5>, comprising the near infrared absorbing agent in an amount of 3 ppm by mass or more and 90 ppm by mass or less.
<7> The optical material according to any one of <1> to <6>, wherein the near infrared absorbing agent comprises two or more compounds.
<8> The (thio)urethane resin comprises a structural unit derived from a polyisocyanate compound and at least one of a structural unit derived from a polythiol compound and a structural unit derived from a polyol compound, and the polyisocyanate compound is selected from the group consisting of 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, 1,2-diisocyanate, 1,4-diisocyanate, 1,5-diisocyanate, 1,6-diisocyanate, 1,7-diisocyanate, 1,8-diisocyanate, 1,9-diisocyanate, 1,1-diisocyanate, 1,2-diisocyanate, 1,3 ... and the polythiol compound is at least one selected from the group consisting of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 5 ... pentaerythritol tetrakis(3-mercaptopropionate), bis(mercaptoethyl)sulfide, pentaerythritol tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl)-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)propane). The optical material according to any one of <1> to <7>, wherein the polyol compound is at least one selected from the group consisting of ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1,3-propanediol, 1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, and 1,4-cyclohexanediol.
<9> The episulfide resin is composed of a constituent unit derived from an episulfide compound, or composed of a constituent unit derived from an episulfide compound and a constituent unit derived from a polythiol compound,
The episulfide compound is at least one selected from the group consisting of bis(2,3-epithiopropyl)sulfide, bis(2,3-epithiopropyl)disulfide, bis(1,2-epithioethyl)sulfide, bis(1,2-epithioethyl)disulfide, and bis(2,3-epithiopropylthio)methane, and the polythiol compound is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8- The optical material according to any one of <1> to <7>, which is at least one selected from the group consisting of dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis(3-mercaptopropionate), bis(mercaptoethyl)sulfide, pentaerythritol tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl)-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane.
<10> A polymerizable composition for an optical material, comprising at least one of a polycarbonate resin and a polymerizable compound, and at least one near-infrared absorbent selected from the group consisting of a compound represented by the following formula (I), a compound represented by the following formula (II), and a compound represented by the following formula (III), wherein the polymerizable compound includes at least one selected from the group consisting of a combination of a polyisocyanate compound, and at least one of a polythiol compound and a polyol compound, an episulfide compound, and a combination of an episulfide compound and a polythiol compound.

In formula (I), R ₁ and R ₂ each independently represent an alkyl group which may be substituted, and M represents a divalent metal atom, a trivalent or tetravalent substituted metal, or an oxymetal.

In formula (II), _R1 and _R2 each independently represent an optionally substituted alkyl group, _R3 represents a nitro group or a group represented by _NR4R5 , which may be _the same or different from each other, and _R4 and _R5 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkylsulfonyl group or an optionally substituted arylsulfonyl group.

In formula (III), _R1 and _R2 each independently represent an optionally substituted alkyl group, _R3 and _R4 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkylsulfonyl group, or an optionally substituted arylsulfonyl group, and M represents a divalent metal atom, a trivalent or tetravalent substituted metal, or an oxymetal.
<11> The polyisocyanate compound is, for example, 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, isophorone diisocyanate, the polythiol compound is at least one selected from the group consisting of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8 ... mercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis(3-mercaptopropionate), bis(mercaptoethyl)sulfide, pentaerythritol tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl)-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithiane. The polymerizable composition for an optical material according to <10>, wherein the polyol compound is at least one selected from the group consisting of ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1,3-propanediol, 1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, and 1,4-cyclohexanediol.
<12> The polymerizable composition for an optical material according to <10> or <11>, containing the near infrared absorbing agent in an amount of 3 ppm by mass or more and 90 ppm by mass or less.
<13> The polymerizable composition for an optical material according to any one of <10> to <12>, wherein the near-infrared absorbent comprises two or more compounds.
<14> The polymerizable composition for an optical material according to any one of <10> to <13>, wherein the episulfide compound is at least one selected from the group consisting of bis(2,3-epithiopropyl)sulfide, bis(2,3-epithiopropyl)disulfide, bis(1,2-epithioethyl)sulfide, bis(1,2-epithioethyl)disulfide, and bis(2,3-epithiopropylthio)methane.
<15> A plastic lens comprising the optical material according to any one of <1> to <9>.
<16> Eyewear comprising the plastic lens according to <15>.
<17> An optical sensor comprising the plastic lens according to <15>.

The invention disclosed herein can provide optical materials, polymerizable compositions for optical materials, plastic lenses, eyewear, and optical sensors that have a high near-infrared cut rate and excellent design properties.

1 is a graph showing transmittance curves of the flat lenses obtained in Examples 1 to 5. 1 is a graph showing transmittance curves of the flat lenses obtained in Examples 6 to 10. 1 is a graph showing transmittance curves of the flat lenses obtained in Examples 11 to 15. 1 is a graph showing transmittance curves of the flat lenses obtained in Examples 16 to 20. 1 is a graph showing transmittance curves of the flat lenses obtained in Examples 21 to 25. 1 is a graph showing transmittance curves of the flat lenses obtained in Examples 26 to 30. 1 is a graph showing a transmittance curve of a flat lens obtained in Example 31.

In the present disclosure, a numerical range indicated using "to" means a range that includes the numerical values before and after "to" as the minimum and maximum values, respectively.
In the numerical ranges described in the present disclosure, the upper or lower limit value described in a certain numerical range may be replaced with the upper or lower limit value of another numerical range described in the present disclosure. In addition, in the numerical ranges described in the present disclosure, the upper or lower limit value described in a certain numerical range may be replaced with a value shown in the examples.
In the present disclosure, a combination of two or more preferred aspects is a more preferred aspect.
In the present disclosure, when there are multiple substances corresponding to each component, the amount of each component means the total amount of multiple substances, unless otherwise specified.
In this disclosure, "(thio)urethane" means urethane or thiourethane.

<Optical materials>
The optical material of the present disclosure comprises at least one resin selected from the group consisting of a polycarbonate resin, a (thio)urethane resin, and an episulfide resin, and at least one near-infrared absorbent selected from the group consisting of a compound represented by the following formula (I), a compound represented by the following formula (II), and a compound represented by the following formula (III), and has a* of -0.8 or more and 10 or less, and L* of 70 or more in the CIE1976 (L*, a*, b*) color space when measured at a thickness of 2 mm.

In formula (I), R ₁ and R ₂ each independently represent an optionally substituted alkyl group, and M represents a divalent metal atom, a trivalent or tetravalent substituted metal, or an oxymetal.

In formula (II), _R1 and _R2 each independently represent an optionally substituted alkyl group, _R3 represents a nitro group or a group represented by _NR4R5 , which may be _the same or different from each other, and _R4 and _R5 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkylsulfonyl group or an optionally substituted arylsulfonyl group.

In formula (III), _R1 and _R2 each independently represent an optionally substituted alkyl group, _R3 and _R4 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkylsulfonyl group, or an optionally substituted arylsulfonyl group, and M represents a divalent metal atom, a trivalent or tetravalent substituted metal, or an oxymetal.

As a result of intensive research, the inventors of the present disclosure have discovered that by incorporating at least one near-infrared absorbing agent selected from the group consisting of compounds represented by formulas (I) to (III) and a specified resin, and by setting L* and a* within specific ranges in the CIE1976 color space, it is possible to achieve both a high near-infrared blocking rate and designability, and have completed the invention of the present disclosure.

Near-infrared light (light in the near-infrared region, with wavelengths in the 700-2,500 nm range) is strongly absorbed by water (water has a high near-infrared absorption coefficient), and because the lens of the eye is approximately 70% water, it has been suggested that near-infrared light may have adverse effects, such as raising the temperature of the eye.
Use of the optical material of the present disclosure is expected to inhibit the progression of cataracts, which are caused by ultraviolet light, high-energy visible light, and the like passing through the eye lens heated by near-infrared light, for example.

<CIE1976 (L*, a*, b*) color space>
The optical material of the present disclosure has, in the CIE1976 (L*, a*, b*) color space, a* is -0.8 or more and 10 or less, and L* is 70 or more, when measured at a thickness of 2 mm. .
In the optical material of the present disclosure, from the viewpoint of improving color and design, a* is -0.7 or more in the CIE1976 (L*, a*, b*) color space measured at a thickness of 2 mm. It is preferably 8 or less, and more preferably from −0.5 to 7.
In addition, from the viewpoint of improving the design by improving the color tone, the optical material of the present disclosure has an L* of 80 or more in the CIE 1976 (L*, a*, b*) color space measured at a thickness of 2 mm. It is preferable that the molecular weight is 85 or more, more preferable that the molecular weight is 88 or more.
In the optical material of the present disclosure, from the viewpoint of improving design by improving color, b* is -5 or more and 20 or less in the CIE1976 (L*, a*, b*) color space measured at a thickness of 2 mm. It is preferable that the ratio is from −2 to 15, and more preferable that the ratio is from −2 to 15.
The CIE1976 (L*, a*, b*) color space can be measured using a spectrophotometer (for example, CM-5 manufactured by Konica Minolta).

From the viewpoint of improving design by improving color, the optical material of the present disclosure preferably has a yellowness index (YI) measured at a thickness of 2 mm of −15 or more and 32 or less, and more preferably −10 or more and 25 or less.
The yellowness index (YI) can be measured using a spectrophotometer (for example, CM-5 manufactured by Konica Minolta).

The optical material of the present disclosure preferably has a transmittance of 80% or less at the maximum absorption wavelength (i.e., λmax).
The optical material of the present disclosure can achieve a high near-infrared cut rate while maintaining excellent design properties. The transmittance at λmax can be used as an index of the degree of the near-infrared cut rate. That is, the lower the transmittance at λmax, the higher the near-infrared cut rate.
The optical material of the present disclosure can achieve a transmittance of 80% or less at λmax while maintaining excellent design properties.
From the same viewpoint as above, the optical material of the present disclosure more preferably has a transmittance at λmax of 74% or less, and further preferably has a transmittance of 65% or less.

From the viewpoint of the effects of the present invention, it is preferable that the optical material of the present disclosure has at least one of the light transmittance at wavelengths of 720 nm to 800 nm and the light transmittance at wavelengths of 840 nm to 950 nm at a thickness of 2 mm satisfy the following range.

In the optical material of the present disclosure, the light transmittance at a wavelength of 720 nm to 800 nm at a thickness of 2 mm may be 20% or more and 80% or less, preferably 30% or more and 80% or less, and more preferably 40% or more and 75% or less.
In the optical material of the present disclosure, the light transmittance at a wavelength of 840 nm to 950 nm at a thickness of 2 mm may be 0.05% or more and 80% or less, preferably 5% or more and 65% or less, and more preferably 10% or more and 55% or less.
The optical material of the present disclosure has, at a thickness of 2 mm, a minimum value of the transmittance curve within a wavelength region of 800 nm to 950 nm, and the minimum value is preferably 0.05% or more and 80% or less, more preferably 0.05% or more and 75% or less, and even more preferably 0.05% or more and 73% or less.

The optical material of the present disclosure preferably has a total light transmittance of 70% or more at a thickness of 2 mm. The optical material of the present disclosure has excellent designability with suppressed turbidity and coloring, and therefore it is possible to make the total light transmittance at a thickness of 2 mm 70% or more.
In addition, the optical material of the present disclosure preferably has a luminous transmittance of 70% or more at a thickness of 2 mm. Since the optical material of the present disclosure has excellent design properties with suppressed turbidity and coloring, it is possible to make the luminous transmittance at a thickness of 2 mm 70% or more.
The optical material of the present disclosure more preferably has a luminous transmittance of 75% or more at a thickness of 2 mm.

<Near infrared absorbing agent>
The optical material of the present disclosure contains at least one near infrared absorbent selected from the group consisting of a compound represented by formula (I), a compound represented by formula (II), and a compound represented by formula (III).
This makes it possible to improve the near-infrared cut rate of the optical material.

In formula (I), R ₁ and R ₂ each independently represent an alkyl group which may be substituted, and M represents a divalent metal atom, a trivalent or tetravalent substituted metal, or an oxymetal.
In this disclosure, oxymetal refers to oxymetals other than trivalent or tetravalent substituted metals.

In formula (I), examples of the optionally substituted alkyl group for R ₁ and R ₂ include linear or branched alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a n-pentyl group, an isopentyl group, a neopentyl group, a n-hexyl group, an isohexyl group, a sec-hexyl group, a n-heptyl group, an isoheptyl group, a sec-heptyl group, a n-octyl group, and a 2-ethylhexyl group;
halogenoalkyl groups such as a chloroethyl group, a bromoethyl group, or a trifluoromethyl group;
alkoxyalkyl groups such as a methoxymethyl group, a methoxyethyl group, an ethoxyethyl group, a propoxyethyl group, and a butoxyethyl group;
hydroxyalkyl groups such as a hydroxyethyl group and a hydroxypropyl group;
hydroxypolyether groups such as a hydroxyethoxyethyl group and a hydroxyethoxyethoxyethyl group;
Examples include alkoxy polyether groups such as a methoxyethoxyethyl group, an ethoxyethoxyethyl group, a propoxyethoxyethyl group, and a butoxyethoxyethyl group; and the like.

In formula (I), examples of divalent metal atoms for M include Cu(II), Zn(II), Fe(II), Co(II), Ni(II), Ru(II), Rh(II), Pd(II), Pt(II), Mn(II), Mg(II), Ti(II), Be(II), Ca(II), Ba(II), Cd(II), Hg(II), Pb(II), Sn(II), etc.

In the formula (I), examples of the trivalent substituted metal which is monosubstituted for M include Al-Cl, Al-Br, Al-F, Al-I, Ga-Cl, Ga-F, Ga-I, Ga-Br, In-Cl, In-Br, In-I, In-F, Tl-Cl, Tl-Br, Tl-I, Tl-F, Al-C ₆ H ₅ , Al-C ₆ H ₄ (CH ₃ ), In-C ₆ H ₅ , In-C ₆ H ₄ (CH ₃ ), In-C ₆ H ₅ , Mn(OH), Mn(OC ₆ H ₅ ), Mn[OSi(CH ₃ ) ₃ ], Fe-Cl, Ru-Cl, and the like.

In the formula (I), examples of the tetravalent metals which are disubstituted for M include _CrCl2 , _SiCl2 , SiBr2, _SiF2 , SiI2, ZrCl2 _, GeCl2 _{, GeBr2 , GeI2 ,} GeF2 _{, SnCl2} , _SnBr2 , _SnF2 , _TiCl2 , _TiBr2 , _TiF2 , Si(OH) ₂ , Ge(OH) ₂ , Zr(OH) _{2, Mn(OH)2} , Sn(OH) ₂ , TiR, CrR, SiR, SnR, GeR ( _R represents an alkyl group, a phenyl group, a naphthyl group, or a derivative thereof), Si(OR') ₂ , Sn(OR') ₂ , and Ge(OR') _2. Examples include Ti(OR') ₂ , Cr(OR') ₂ (wherein R' represents an alkyl group, a phenyl group, a naphthyl group, a trialkylsilyl group, a dialkylalkoxysilyl group, or a derivative thereof), Sn(SR") ₂ , and Ge(SR") ₂ (wherein R" represents an alkyl group, a phenyl group, a naphthyl group, or a derivative thereof).

In formula (I), examples of oxymetals include VO, MnO, TiO, etc.

Among the above, M is preferably Co, Ni, Cu, Zn, Pd, AlCl, InCl, TiO, and VO, and more preferably Cu.

In the compound represented by formula (I) of the present disclosure, R ₁ and R ₂ are preferably a linear or branched unsubstituted alkyl group, and R ₃ is preferably a nitro group. In addition to the above, M is more preferably Cu.

The compounds of formula (I) of the present disclosure can be prepared using known methods.
An example of the known method is the method described in JP-A-11-152416.

In formula (II), _R1 and _R2 each independently represent an optionally substituted alkyl group, _R3 represents a nitro group or a group represented by _NR4R5 , which may be _the same or different from each other, and _R4 and _R5 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkylsulfonyl group or an optionally substituted arylsulfonyl group.

In formula (II), examples of the optionally substituted alkyl group in _R1 and _R2 include the same specific examples as those given as the optionally substituted alkyl group in _R1 and _R2 in formula (I) above.

In formula (II), examples of the optionally substituted alkyl group in R ₄ and R ₅ include alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, an n-octyl group, and a 2-ethylhexyl group;
halogenoalkyl groups such as a chloroethyl group;
Examples include alkoxyalkyl groups such as a methoxymethyl group, a methoxyethyl group, an ethoxyethyl group, a propoxyethyl group, and a butoxyethyl group; and the like.

In formula (II), examples of the aryl group which may be substituted include a phenyl group, a naphthyl group, a 4-methylphenyl group, a 4-ethylphenyl group, a 4-propylphenyl group, a 4-tert-butylphenyl group, a 4-methoxyphenyl group, a 4-ethoxyphenyl group, a 4-chlorophenyl group, a 4-bromophenyl group, a 2-methylphenyl group, a 2-ethylphenyl group, a 2-propylphenyl group, a 2-t-butylphenyl group, a 2-methoxyphenyl group, a 2-ethoxyphenylthio group, a 2-hydroxyphenylthio group, a 2-chlorophenyl group, and a 2-bromophenyl group.

In formula (II), examples of the optionally substituted alkylcarbonyl group include alkylcarbonyl groups such as an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovaleryl group, a trimethylacetyl group, a hexanoyl group, a tert-butylacetyl group, a heptanoyl group, an octanoyl group, and a 2-ethylhexanoyl group;
halogenoalkylcarbonyl groups such as a cyclopentanecarbonyl group, a 6-chlorohexanoyl group, a 6-bromohexanoyl group, a trifluoroacetyl group, a pentafluoropropionyl group, or a perfluorooctanoyl group;
methoxyacetyl group and other alkoxyalkylcarbonyl groups; and the like.

In formula (II), examples of the optionally substituted arylcarbonyl group include benzoyl, o-chlorobenzoyl, m-chlorobenzoyl, p-chlorobenzoyl, o-fluorobenzoyl, m-fluorobenzoyl, p-fluorobenzoyl, o-acetylbenzoyl, m-acetylbenzoyl, p-acetylbenzoyl, o-methoxybenzoyl, m-methoxybenzoyl, p-methoxybenzoyl, o-methylbenzoyl, m-methylbenzoyl, p-methylbenzoyl, o-trifluoromethylbenzoyl, p-trifluoromethylbenzoyl, pentafluorobenzoyl, and 4-(trifluoromethyl)benzoyl groups.

In formula (II), examples of the alkylsulfonyl group which may be substituted include alkylsulfonyl groups such as methanesulfonyl group, ethanesulfonyl group, propanesulfonyl group, butanesulfonyl group, heptanesulfonyl group, and hexanesulfonyl group, halogenoalkylsulfonyl groups such as 2-chloroethanesulfonyl group, 2,2,2-trifluoroethanesulfonyl group, and trifluoromethanesulfonyl group, and benzylsulfonyl group.

In formula (II), examples of the optionally substituted arylsulfonyl group include a benzenesulfonyl group, an o-chlorobenzenesulfonyl group, a m-chlorobenzenesulfonyl group, a p-chlorobenzenesulfonyl group, an o-fluorobenzenesulfonyl group, a m-fluorobenzenesulfonyl group, a p-fluorobenzenesulfonyl group, a pentafluorobenzenesulfonyl group, an o-methoxybenzenesulfonyl group, a m-methoxybenzenesulfonyl group, a p-methoxybenzenesulfonyl group, an o-methylbenzenesulfonyl group, a m-methylbenzenesulfonyl group, a p-methylbenzenesulfonyl group, a 2-mesitylenesulfonyl group, a 4-tert-butylbenzenesulfonyl group, and an N-acetylsulfanilyl group.

In the compound represented by formula (II) in the present disclosure, R ₁ and R ₂ are preferably a linear or branched unsubstituted alkyl group, and R ₃ is preferably a nitro group.

The compound represented by formula (II) of the present disclosure can be produced using a known method. An example of the known method is the method described in JP-A-2000-86919.

In formula (III), _R1 and _R2 each independently represent an optionally substituted alkyl group, _R3 and _R4 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkylsulfonyl group, or an optionally substituted arylsulfonyl group, and M represents a divalent metal atom, a trivalent or tetravalent substituted metal, or an oxymetal.

In formula (III), examples of the optionally substituted alkyl group in _R1 and _R2 include the same specific examples as those given as the optionally substituted alkyl group in _R1 and _R2 in formula (I) above.

In formula (III), examples of the optionally substituted alkyl group in _R3 and _R4 include the same specific examples as those exemplified as the optionally substituted alkyl group in _R1 and _R2 in formula (I) above.

In formula (III), examples of the optionally substituted aryl group, the optionally substituted alkylcarbonyl group, the optionally substituted arylcarbonyl group, the optionally substituted alkylsulfonyl group and the optionally substituted arylsulfonyl group in _R3 and _R4 include the same specific examples as those given as the optionally substituted aryl group, the optionally substituted alkylcarbonyl group, the optionally substituted arylcarbonyl group, the optionally substituted alkylsulfonyl group and the optionally substituted arylsulfonyl group in formula (II) above.

In the compound represented by formula (III) in the present disclosure, R ₁ and R ₂ are preferably linear or branched unsubstituted alkyl groups, and R ₃ and R ₄ are preferably hydrogen atoms or linear or branched unsubstituted alkyl groups. In addition to the above, M is more preferably Cu.

In formula (III), specific examples of the divalent metal atom, the monosubstituted trivalent substituted metal, the disubstituted tetravalent substituted metal, and the oxymetal are the same as the specific examples of the divalent metal atom, the monosubstituted trivalent substituted metal, the disubstituted tetravalent substituted metal, and the oxymetal in formula (I) described above.
Preferable specific examples of M in formula (III) include the same as the preferable specific examples of M in formula (I).

The compound represented by formula (III) of the present disclosure can be produced using a known method. An example of the known method is the method described in JP-A-11-152414.

As the near-infrared absorbent in the present disclosure, for example, in order to realize a high near-infrared cut rate, (1) a near-infrared absorbent having a minimum value of a spectral transmittance curve with a transmittance of less than 50% within a wavelength range of 720 nm to 800 nm, or (2) a near-infrared absorbent having a minimum value of a spectral transmittance curve with a transmittance of less than 50% within a wavelength range of 800 nm to 950 nm can be used.
In order to realize a high cut rate in a wide near-infrared region, near-infrared absorbents having the above properties (1) and (2) can be used in combination.

As the near-infrared absorbent, a compound can be used which has a peak between 840 nm and 930 nm in a visible light absorption spectrum measured in a 3 ppm to 5 ppm by mass toluene solution, the absorption coefficient of the peak apex (also referred to as Pmax) being 1.10 × 10 ⁵ ml/g cm or more, the peak width at ¼ of the absorbance of the peak at Pmax being 100 nm or less, the peak width at ½ of the absorbance of the peak at Pmax being 55 nm or less, and the peak width at ⅔ of the absorbance of the peak at Pmax being 40 nm or less.
It should be noted that Pmax refers to the point in the peak that exhibits the maximum extinction coefficient.

The near-infrared absorbent in the present disclosure may include isomeric compounds having different substitution positions of the substituents, compounds having different types of substituents produced as by-products in the synthesis, etc.

[0043] In the near-infrared absorbent according to the present disclosure, from the viewpoint of obtaining an optical material having a high near-infrared cut rate and excellent designability, the mass average molecular weight excluding the central metal M of the compound represented by formula (I) is preferably 900 or more and 5000 or less, and more preferably 1200 or more and 2000 or less.
From the same viewpoint as above, the mass average molecular weight of the compound represented by formula (II) is preferably 900 or more and 5000 or less, and more preferably 1200 or more and 2000 or less. From the same viewpoint as above, the mass average molecular weight excluding the central metal M of the compound represented by formula (III) is preferably 900 or more and 5000 or less, and more preferably 1200 or more and 2000 or less.

The near-infrared absorbing agent in the present disclosure is preferably a combination of a plurality of compounds having different structures, that is, the near-infrared absorbing agent in the present disclosure is preferably composed of two or more types of compounds.
This allows near-infrared rays to be efficiently blocked over a wide area.

From the viewpoint of obtaining an optical material having a high near-infrared cut rate and excellent designability, the optical material of the present disclosure preferably contains 3 ppm by mass or more and 90 ppm by mass or less of a near-infrared absorbent, more preferably 5 ppm by mass or more and 65 ppm by mass or less, and even more preferably 10 ppm by mass or more and 50 ppm by mass or less.
In the present disclosure, the content of the near-infrared absorbent refers to the content of the near-infrared absorbent relative to the total mass of the optical material of the present disclosure.

<Resin>
The optical material of the present disclosure contains at least one resin selected from the group consisting of polycarbonate resins, (thio)urethane resins, and episulfide resins.

Polycarbonate resins may be produced by the phosgene method, in which dihydroxydiaryl compounds are reacted with phosgene, or the ester exchange method, in which dihydroxydiaryl compounds are reacted with carbonates such as diphenyl carbonate.

The polycarbonate resin may be a polycarbonate resin made from 2,2-bis(4-hydroxyphenyl)propane (also called bisphenol A), a polycarbonate resin made from 1,1-bis(4-hydroxyphenyl)cyclohexane, a polycarbonate resin made from 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, a polycarbonate resin made from 9,9-bis(4-hydroxyphenyl)fluorene, a polycarbonate resin made from 9,9-bis[4-(2-hydroxyethyloxy)phenyl]fluorene, a copolymer polycarbonate resin made from a mixture of dihydroxydiaryl compounds, or a mixture of the polycarbonate resins listed above.

Examples of dihydroxydiaryl compounds include, in addition to bisphenol A, (hydroxyaryl)aryl compounds such as bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)octane, 2,2-bis(4-hydroxyphenyl)phenylmethane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 2,2-bis(4-hydroxy-3-tert-butylphenyl)propane, 1,1-bis(4-hydroxy-3-tert-butylphenyl)propane, 2,2-bis(4-hydroxy-3-bromophenyl)propane, 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane, and 2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane. dihydroxydiaryl ethers such as 4,4'-dihydroxydiphenyl ether and 4,4'-dihydroxy-3,3'-dimethyldiphenyl ether; dihydroxydiaryl sulfides such as 4,4'-dihydroxydiphenyl sulfoxide and 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfoxide; and dihydroxydiaryl sulfones such as 4,4'-dihydroxydiphenyl sulfone and 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfone.
These may be used alone or in combination of two or more.

The dihydroxydiaryl compounds may be used in combination with piperazine, dipiperidylhydroquinone, resorcinol, 4,4'-dihydroxydiphenyl, and the like.
The viscosity average molecular weight of the polycarbonate resin is usually 10,000 to 100,000, and preferably 10,000 to 400,000.

The dihydroxydiaryl compounds may be used in combination with trivalent or higher phenolic compounds such as those shown below. Examples of trivalent or higher phenolic compounds include phloroglucin, 1,3,5-tri-(4-hydroxyphenyl)-benzene, and 1,1,1-tri-(4-hydroxyphenyl)-ethane.
In addition, commercially available products may be used as the polycarbonate resin, and examples thereof include Panlite (manufactured by Teijin Limited), Iupilon (manufactured by Mitsubishi Engineering Plastics Corporation), Novarex (manufactured by Mitsubishi Engineering Plastics Corporation), and SD Polyca (manufactured by Sumitomo Polycarbonate Co., Ltd.).

The (thio)urethane resin preferably comprises a constituent unit derived from a polyisocyanate compound, and at least one of a constituent unit derived from a polythiol compound and a constituent unit derived from a polyol compound.
The episulfide resin preferably comprises a constituent unit derived from an episulfide compound, or comprises a constituent unit derived from an episulfide compound and a constituent unit derived from a polythiol compound.

Methods for producing the above-mentioned (thio)urethane resin and episulfide resin include methods using the above-mentioned polyisocyanate compounds, polythiol compounds, polyol compounds, and episulfide compounds. Each of the above compounds will be described in detail in the section on polymerizable compositions for optical materials below.

≪Polymerizable composition for optical materials≫
The polymerizable composition for an optical material of the present disclosure includes at least one of a polycarbonate resin and a polymerizable compound, a compound represented by formula (I), a compound represented by formula (II), and a compound represented by formula (III). and a near-infrared absorbing agent which is at least one selected from the group consisting of compounds represented by the formula: and a combination of an episulfide compound and a polythiol compound.
As the polycarbonate resin and the near infrared absorbing agent, specific examples can be mentioned similar to the specific examples of the polycarbonate resin and the near infrared absorbing agent mentioned above.

The polymerizable composition for optical materials of the present disclosure preferably contains 3 ppm by mass or more and 90 ppm by mass or less of the near-infrared absorbent, more preferably 5 ppm by mass or more and 65 ppm by mass or less, and even more preferably 10 ppm by mass or more and 50 ppm by mass or less.

<Polymerizable Compound>
The polymerizable compound in the polymerizable composition for an optical material of the present disclosure includes at least one selected from the group consisting of (1) a combination of a polyisocyanate compound and at least one of a polythiol compound and a polyol compound, (2) an episulfide compound, or (3) a combination of an episulfide compound and a polythiol compound.

(Polyisocyanate Compound)
The polyisocyanate compound may be an aliphatic isocyanate compound, an alicyclic isocyanate compound, an aromatic isocyanate compound, a heterocyclic isocyanate compound, an aromatic aliphatic isocyanate compound, or the like, and may be used alone or in combination of two or more. These isocyanate compounds may include dimers, trimers, and prepolymers. Examples of these isocyanate compounds include the compounds exemplified in WO2011/055540.

In the present disclosure, from the viewpoint of improving the solubility of the near-infrared absorbent in the resin, the polyisocyanate compound is preferably at least one selected from the group consisting of 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, isophorone diisocyanate, 1,6-hexamethylene diisocyanate, and 1,5-pentamethylene diisocyanate,
More preferably, it is at least one selected from the group consisting of 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, m-xylylene diisocyanate, and 1,3-bis(isocyanatomethyl)cyclohexane;
More preferably, it is at least one selected from the group consisting of 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane.

(Polythiol Compound)
The polythiol compound is a compound having two or more mercapto groups, and examples of the compounds exemplified in WO2016/125736 can be mentioned.
In the present disclosure, from the viewpoint of improving the solubility of a near-infrared absorbent in a resin, the polythiol compound is, for example, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetraacetate, It is preferable that the tetrakis(3-mercaptopropionate), bis(mercaptoethyl)sulfide, pentaerythritol tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl)-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane are at least one selected from the group consisting of tetrakis(3-mercaptopropionate), bis(mercaptoethyl)sulfide, pentaerythritol tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl)-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane.
More preferably, it is at least one selected from the group consisting of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis(3-mercaptopropionate), and pentaerythritol tetrakis(2-mercaptoacetate).

Furthermore, in the case where the polymerizable compound includes a combination of a polyisocyanate compound and a polythiol compound among the above (1), from the viewpoint of improving the solubility of the near infrared absorber in the resin, it is further preferable that the polyisocyanate compound is at least one selected from the group consisting of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritol tetrakis(3-mercaptopropionate), and pentaerythritol tetrakis(2-mercaptoacetate).
Furthermore, in the case where the polymerizable compound contains a combination of the episulfide compound and the polythiol compound, which is the above (3), from the viewpoint of improving the solubility of the near infrared absorber in the resin, it is more preferable that the polyisocyanate compound is at least one selected from the group consisting of 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane.

(Polyol Compound)
The polyol compound is one or more aliphatic or alicyclic alcohols. Specific examples of the polyol compound include linear or branched aliphatic alcohols, alicyclic alcohols, and alcohols obtained by adding these alcohols to ethylene oxide, propylene oxide, or ε-caprolactone. Specific examples of the polyol compound that can be used include the compounds exemplified in WO2016/125736.

The polyol compound is preferably at least one selected from the group consisting of ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1,3-propanediol, 1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, and 1,4-cyclohexanediol.

(Episulfide Compounds)
Examples of the episulfide compound include epithioethylthio compounds, linear aliphatic 2,3-epithiopropylthio compounds, cyclic aliphatic 2,3-epithiopropylthio compounds, aromatic 2,3-epithiopropylthio compounds, linear aliphatic 2,3-epithiopropyloxy compounds, cyclic aliphatic 2,3-epithiopropyloxy compounds, aromatic 2,3-epithiopropyloxy compounds, etc., and these are used alone or in combination of two or more. Examples of these episulfide compounds include the compounds exemplified in WO2015/137401.

From the viewpoint of improving the solubility of the near-infrared absorber in the resin, the episulfide compound is preferably at least one selected from the group consisting of bis(2,3-epithiopropyl) sulfide, bis(2,3-epithiopropyl) disulfide, bis(1,2-epithioethyl) sulfide, bis(1,2-epithioethyl) disulfide, and bis(2,3-epithiopropylthio)methane, and more preferably bis(2,3-epithiopropyl) disulfide.

(Optional Additives)
Optional additives may include polymerization catalysts, internal mold release agents, bluing agents, ultraviolet absorbers, etc. In the present disclosure, the polyurethanes and polythiourethanes may or may not be prepared using a polymerization catalyst.

An example of an internal mold release agent is an acidic phosphate ester. Examples of acidic phosphate esters include monoester phosphate esters and diester phosphate esters, each of which can be used alone or in combination of two or more types. An example of a bluing agent is one that has an absorption band in the orange to yellow wavelength range of the visible light region and has the function of adjusting the hue of the optical material made of resin. More specifically, the bluing agent includes a substance that exhibits a blue to purple color.

Examples of the ultraviolet absorber to be used include benzophenone-based ultraviolet absorbers such as 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-acryloyloxybenzophenone, 2-hydroxy-4-acryloyloxy-5-tert-butylbenzophenone, and 2-hydroxy-4-acryloyloxy-2',4'-dichlorobenzophenone;

2-[4-[(2-hydroxy-3-dodecyloxypropyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 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]- Triazine-based ultraviolet absorbers such as 2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-butyloxyphenyl)-6-(2,4-bis-butyloxyphenyl)-1,3,5-triazine, and 2-(2-hydroxy-4-[1-octyloxycarbonylethoxy]phenyl)-4,6-bis(4-phenylphenyl)-1,3,5-triazine;

2-(2H-benzotriazol-2-yl)-4-methylphenol, 2-(2H-benzotriazol-2-yl)-4-tert-octylphenol, 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol, 2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenol, 2-(5-chloro-2H-benzotriazol-2-yl)-4-methyl-6-tert-butylphenol, 2-(5-chloro-2H-benzotriazol-2-yl)-4-methyl-6-tert-butylphenol, Examples of the benzotriazole-based ultraviolet absorbers include 2-(2H-benzotriazol-2-yl)-4-tert-octylphenol and 2-(5-chloro-2H-benzotriazol-2-yl)-4-methyl-6-tert-butylphenol. These ultraviolet absorbers can be used alone or in combination of two or more.
The composition for optical materials can be obtained by mixing the above-mentioned components by a predetermined method.
The mixing order and method of the components in the composition are not particularly limited as long as the components can be mixed uniformly, and any known method can be used.

<Applications of optical materials>
The optical material of the present disclosure can be obtained by polymerizing and curing the composition for optical materials of the present disclosure.
Examples of applications of the optical material include plastic eyeglass lenses, goggles, eyeglass lenses for vision correction, lenses for imaging devices, Fresnel lenses for liquid crystal projectors, lenticular lenses, contact lenses, lenses for optical sensors (e.g., lenses for infrared sensors), lenses for infrared cameras, various plastic lenses such as eyewear such as sunglasses and fashion lenses, sealing materials for light-emitting diodes (LEDs), optical waveguides, optical adhesives used for bonding optical lenses and optical waveguides, near-infrared absorbing films used for optical lenses, transparent coatings used for liquid crystal display device members (substrates, light guide plates, films, sheets, etc.) or windshields of automobiles and motorcycle helmets, transparent substrates, etc. The optical material of the present disclosure may contain an ultraviolet absorbing agent. Examples of optical materials include plastic lenses, lenses for optical sensors (e.g., lenses for infrared sensors), lenses for infrared cameras, eyewear, and near-infrared absorbing films used for these optical lenses, etc.
Among the above, as applications of the optical material, a plastic lens including the optical material of the present disclosure is preferable, eyewear including the above-mentioned plastic lens and a lens for an optical sensor including the above-mentioned plastic lens are more preferable, and an infrared sensor including the above-mentioned plastic lens is even more preferable.
A plastic lens, which is a preferred embodiment of the optical material, will be described in detail below.

(Plastic lenses)
The plastic lens in the present disclosure may be a plastic lens including the optical material of the present disclosure.
The plastic lens may have the following structure:
(a) a plastic lens comprising a lens substrate made of the composition for optical materials of the present disclosure; (b) a plastic lens comprising a film or coating layer made of the composition for optical materials of the present disclosure on at least one surface of a lens substrate (excluding lens substrates obtained from the composition for optical materials of the present disclosure); (c) a plastic lens in which a lens substrate (excluding lens substrates obtained from the composition for optical materials of the present disclosure) is laminated on both surfaces of a film made of the composition for optical materials of the present disclosure. These plastic lenses can be preferably used in the present disclosure.
Each embodiment will be described below.

[Embodiment A]
The method for producing a plastic lens having a lens substrate made of the composition for optical materials of the present disclosure is not particularly limited, but a preferred production method is cast polymerization using a lens casting mold. The lens substrate can be composed of a polyurethane resin, a polythiourethane resin, or an episulfide resin, and the composition for optical materials of the present disclosure containing a near-infrared absorbing agent and a monomer of these resins (resin monomer for optical materials) can be used.

Specifically, the optical material composition is injected into the cavity of a mold held by a gasket or tape, etc. At this time, depending on the physical properties required for the resulting plastic lens, it is often preferable to perform a degassing process under reduced pressure, or a filtration process using pressure or reduced pressure, etc., as necessary.

After the composition is injected, the lens casting mold is heated in a heating device such as an oven or underwater according to a predetermined temperature program to harden and mold the resin. The resin molded body may be annealed or otherwise treated as necessary.

In the present disclosure, when molding the resin, in addition to the above-mentioned "optional additives," various additives such as chain extenders, crosslinking agents, light stabilizers, antioxidants, oil-soluble dyes, fillers, and adhesion improvers may be added in the same manner as known molding methods depending on the purpose.

The plastic lens of the present disclosure may have various coating layers on a lens substrate made of the composition for optical materials of the present disclosure according to its purpose and use. The coating layer may contain a near-infrared absorbing agent. The coating layer containing the near-infrared absorbing agent can be prepared using a coating material (composition) containing the near-infrared absorbing agent, or it can be prepared by forming a coating layer and then immersing a plastic lens with the coating layer in a dispersion obtained by dispersing the near-infrared absorbing agent in water or a solvent to impregnate the near-infrared absorbing agent into the coating layer.

[Embodiment B]
The plastic lens of the present disclosure may have a film or layer made of the composition for optical materials of the present disclosure on at least one surface of a lens substrate. The lens substrate does not have to be one formed from the composition for optical materials of the present disclosure, and various lens substrates can be used.

Examples of methods for producing plastic lenses in the present disclosure include (b-1) a method of producing a lens substrate, and then laminating a film or sheet made of the optical material composition of the present disclosure onto at least one surface of the lens substrate, and (b-2) a method of placing a film or sheet made of the optical material composition of the present disclosure along one inner wall of a mold cavity held by a gasket or tape as described below, and then injecting the optical material composition into the cavity and curing it.

The film or sheet made of the composition for optical materials of the present disclosure, which is used in the above method (b-1), is not particularly limited and can be obtained by a known molding method.
The lens substrate can be made of a known optical resin, and various optical resins can be used.
A film or sheet made of the composition for optical materials of the present disclosure can be attached to the surface of a lens substrate by a known method.

The cast polymerization in the above method (b-2) can be carried out in the same manner as the method for the plastic lens in embodiment a, and the composition used in the cast polymerization can be a composition containing a resin monomer for optical materials (not containing a near-infrared absorbing agent).

In addition, the plastic lens of the present disclosure may have various coating layers on the lens substrate or "film or layer" made of the composition for optical materials according to its purpose and use. As with the plastic lens of embodiment a, the coating layer may contain a near-infrared absorbing agent.

[Embodiment C]
In the plastic lens of the present disclosure, a lens substrate (excluding a lens substrate obtained from the composition for optical materials of the present disclosure) may be laminated on both sides of a film made of the composition for optical materials of the present disclosure.

Examples of methods for producing plastic lenses in the present disclosure include (c-1) a method in which a lens substrate is produced and then laminated onto both sides of a film or sheet made of the composition for optical materials of the present disclosure, and (c-2) a method in which a film or sheet made of the composition for optical materials of the present disclosure is placed in a cavity of a molding mold held by a gasket or tape or the like, while being spaced apart from the inner wall of the mold, and then the composition for optical materials is injected into the cavity and cured.

The film or sheet made of the composition for optical materials of the present disclosure and the lens substrate used in the above method (c-1) can be the same as those used in the method (b-1) for the plastic lens in embodiment b.
A film or sheet made of the composition for optical materials of the present disclosure can be attached to the surface of a lens substrate by a known method.
Specifically, the above method (c-2) can be carried out as follows.

A film or sheet made of the optical material composition of the present disclosure is placed in the space of the lens casting mold used in the plastic lens manufacturing method in embodiment a, so that both sides of the film or sheet are parallel to the opposing inner surface of the front mold.

Next, in the space of the lens casting mold, a composition containing a resin monomer for optical materials (not containing a near-infrared absorbing agent) is injected into the two gaps between the mold and the polarizing film using a specified injection means.

After the composition is injected, the lens casting mold is heated in a heating device such as an oven or underwater according to a predetermined temperature program to harden and mold the resin. The resin molded body may be annealed or otherwise treated as necessary.

In addition, the plastic lens of the present disclosure may have various coating layers on the lens substrate depending on the purpose and application. As with the plastic lens of embodiment a, the coating layer may contain a near-infrared absorbing agent.

[Plastic eyeglass lenses]
The plastic lens of the present disclosure can be used to obtain a plastic eyeglass lens. If necessary, a coating layer may be applied to one or both sides of the lens.

Specific examples of coating layers include a primer layer, a hard coat layer, an anti-reflection layer, an anti-fogging coat layer, an anti-fouling layer, and a water-repellent layer. Each of these coating layers can be used alone or in a multi-layer configuration. When coating layers are applied to both sides, the same coating layer or different coating layers can be applied to each side.

Each of these coating layers may contain near-infrared absorbents used in the present disclosure, infrared absorbents for protecting the eyes from infrared rays, light stabilizers and antioxidants for improving the weather resistance of the lens, dyes and pigments for enhancing the fashionability of the lens, photochromic dyes and photochromic pigments, antistatic agents, and other known additives for improving lens performance. For layers that are coated by application, various leveling agents may be used to improve application properties.

The primer layer is usually formed between the hard coat layer described below and the lens. The primer layer is a coating layer intended to improve adhesion between the hard coat layer formed thereon and the lens, and in some cases can also improve impact resistance. Any material can be used for the primer layer as long as it has high adhesion to the resulting lens, but primer compositions mainly made of urethane resin, epoxy resin, polyester resin, melamine resin, polyvinyl acetal, etc. are usually used. The primer composition may contain an appropriate solvent that does not affect the lens in order to adjust 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. When a coating method is used, the primer composition is applied to the lens by a known coating method such as spin coating or dip coating, and then solidified to form the primer layer. When a dry method is used, the primer layer is formed by a known dry method such as a CVD method or a vacuum deposition method. When forming the primer layer, the surface of the lens may be pretreated, as necessary, with an alkali treatment, a plasma treatment, an ultraviolet treatment, or the like, in order to improve adhesion.
The hard coat layer is a coating layer intended to impart functions such as scratch resistance, abrasion resistance, moisture resistance, warm water resistance, heat resistance, and weather resistance to the lens surface.

The hard coat layer generally uses a hard coat composition containing at least one of a curable organosilicon compound and one or more oxide fine particles of an element selected from the group consisting of Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In, and Ti, and one or more fine particles composed of a composite oxide of two or more elements selected from this group.

In addition to the above components, the hard coat composition preferably contains at least one of amines, amino acids, metal acetylacetonate complexes, organic acid metal salts, perchloric acids, salts of perchloric acids, acids, metal chlorides, and polyfunctional epoxy compounds. The hard coat composition may be used in an appropriate solvent that does not affect the lens, or may be used without a solvent.

The hard coat layer is usually formed by applying a hard coat composition by a known application method such as spin coating or dip coating, and then curing the applied composition. Examples of the curing method include heat curing and curing by irradiation with energy rays such as ultraviolet rays or visible light. In order to suppress the occurrence of interference fringes, it is preferable that the difference in refractive index between the hard coat layer and the lens is within ±0.1.

The anti-reflection layer is usually formed on the hard coat layer as required. Anti-reflection layers are classified into inorganic and organic types. In the case of inorganic types, inorganic oxides such as SiO ₂ and TiO ₂ are used and the layers are formed by dry methods such as vacuum deposition, sputtering, ion plating, ion beam assisted, and CVD. In the case of organic types, the layers are formed by wet methods using a composition containing an organosilicon compound and silica-based fine particles having internal cavities.

The antireflection layer may be a single layer or a multilayer, and when used as a single layer, the refractive index is preferably at least 0.1 lower than that of the hard coat layer. To effectively exhibit the antireflection function, it is preferable to use a multilayer antireflection film, and in this case, a low refractive index film and a high refractive index film are alternately laminated. In this case, the refractive index difference between the low refractive index film and the high refractive index film is preferably 0.1 or more. As the high refractive index film, there are films such as ZnO, TiO ₂ , CeO ₂ , Sb ₂ O ₅ , SnO ₂ , ZrO ₂ , Ta ₂ O ₅ , and as the low refractive index film, there are films such as SiO ₂ film.

On the anti-reflection layer, an anti-fog layer, an anti-pollution layer, or a water-repellent layer may be formed as necessary. As a method for forming the anti-fog layer, the anti-pollution layer, or the water-repellent layer, there are no particular limitations on the treatment method, treatment material, etc., and known anti-fog treatment methods, anti-pollution treatment methods, and water-repellent treatment methods and materials can be used as long as they do not adversely affect the anti-reflection function. For example, anti-fog treatment methods and anti-pollution treatment methods include a method of covering the surface with a surfactant, a method of adding a hydrophilic film to the surface to make it water-absorbent, a method of covering the surface with fine irregularities to increase water absorbency, a method of making it water-absorbent by utilizing photocatalytic activity, and a method of applying a super-water-repellent treatment to prevent adhesion of water droplets. In addition, water-repellent treatment methods include a method of forming a water-repellent treatment layer by vapor deposition or sputtering a fluorine-containing silane compound, etc., and a method of dissolving a fluorine-containing silane compound in a solvent and then coating it to form a water-repellent treatment layer.

The above describes embodiments of the present disclosure, but these are merely examples of the present disclosure, and various configurations other than those described above can be adopted as long as they do not impair the effects of the present disclosure.

The invention of this disclosure will be explained in more detail below using examples, but this disclosure is not limited to these. The evaluation methods and materials used in the examples of this disclosure are as follows.

[Method of measuring transmittance and luminous transmittance]
The measurement equipment used was a Shimadzu UV-1800 spectrophotometer manufactured by Shimadzu Corporation, and the ultraviolet-visible light spectrum was measured using a 2 mm thick flat lens to obtain a transmittance curve. The luminous transmittance was calculated based on the obtained light transmittance.
When the luminous transmittance of a flat lens is 75% or more, this means that the flat lens can ensure visibility when, for example, driving a car at night.
Moreover, the lower the transmittance at λmax, the higher the infrared blocking rate.

[Method of measuring L*, a*, b*]
Using a spectrophotometer (CM-5 manufactured by Konica Minolta), L*, a*, and b* in the CIE1976 (L*, a*, b*) color system of a 2 mm thick flat lens were measured.
[Method of measuring YI]
The YI of a 2 mm thick flat lens was measured using a spectrophotometer CM-5 manufactured by Konica Minolta.

[Method for measuring total light transmittance]
The total light transmittance of the 2 mm thick flat lens was measured using a HazeMeter NDH2000 manufactured by Nippon Denshoku Industries Co., Ltd.

In the examples, the following near-infrared absorbents were used:

Near infrared absorbing agent A

In a visible light absorption spectrum measured on a 4.7 ppm by mass toluene solution of the near infrared absorber A represented by chemical formula (I-1), the near infrared absorber A had a peak at 858 nm, and the absorption coefficient of the peak apex (Pmax: a point showing the maximum absorption coefficient in the peak) was 1.22 × 10 ⁵ ml/g cm, the peak width at ¼ of the absorbance at Pmax of the peak was 69.5 nm, the peak width at ½ of the absorbance at Pmax of the peak was 42.5 nm, and the peak width at ⅔ of the absorbance at Pmax of the peak was 31.5 nm.

Near infrared absorbing agent B

In a visible light absorption spectrum measured on a 3.1 ppm by mass toluene solution of the near infrared absorber B represented by chemical formula (II-1), the near infrared absorber B had a peak at 873.5 nm, and the absorption coefficient of the peak apex (Pmax: a point showing the maximum absorption coefficient in the peak) was 1.86 × 10 ⁵ ml/g cm, the peak width at ¼ of the absorbance at Pmax of the peak was 62.5 nm, the peak width at ½ of the absorbance at Pmax of the peak was 40.5 nm, and the peak width at ⅔ of the absorbance at Pmax of the peak was 30.5 nm.

Near infrared absorbing agent C

In a visible light absorption spectrum measured on a 3.6 ppm by mass toluene solution of the near infrared absorber C represented by chemical formula (III-1), the near infrared absorber C had a peak at 913.5 nm, and the absorption coefficient of the peak apex (Pmax: a point showing the maximum absorption coefficient in the peak) was 1.61 × 10 ⁵ ml/g cm, the peak width at ¼ of the absorbance at Pmax of the peak was 71.5 nm, the peak width at ½ of the absorbance at Pmax of the peak was 43.5 nm, and the peak width at ⅔ of the absorbance at Pmax of the peak was 30.5 nm.

Near infrared absorbing agent D

In a visible light absorption spectrum measured on a 3.3 ppm by mass toluene solution of the near infrared absorber D represented by the above formula, the near infrared absorber D had a peak at 780 nm, and the absorption coefficient of the peak apex (Pmax: a point showing the maximum absorption coefficient in the peak) was 1.75×10 ⁵ ml/g cm, the peak width at ¼ of the absorbance of the peak at Pmax was 36 nm, the peak width at ½ of the absorbance of the peak at Pmax was 24 nm, and the peak width at ⅔ of the absorbance of the peak at Pmax was 17 nm.

Near infrared absorbing agent E

In the visible light absorption spectrum measured with a 36.5 mass ppm toluene solution of the near infrared absorber E represented by the above formula, there was a peak at 935 nm, the absorption coefficient at Pmax of the peak was 1.58 x 10 ⁴ ml/g cm, the peak width at 1/2 the absorbance at Pmax of the peak was 379 nm, and the peak width at 2/3 the absorbance at Pmax of the peak was 252 nm. Note that the peak width at 1/4 the absorbance at Pmax of the peak could not be measured because there was no value that was 1/4 of the absorbance at Pmax of the peak.

[Example 1]
A mixed solution was prepared by adding 0.035 parts by mass of dibutyltin (II) dichloride, 0.1 parts by mass of an internal release agent for MR manufactured by Mitsui Chemicals, 1.5 parts by mass of an ultraviolet absorber Tinuvin 329, 50.6 parts by mass of a mixture of 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, and an amount of near-infrared absorber A to be the amount shown in Table 1. The mixed solution was stirred at 25°C for 1 hour to completely dissolve. Thereafter, 25.5 parts by mass of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 23.9 parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) were added to the prepared solution, and the mixture was stirred at 25°C for 30 minutes to prepare a uniform solution. The solution was degassed at 400 Pa for 1 hour, filtered with a 1 μm PTFE filter, and then poured into a flat glass mold with a center thickness of 2 mm and a diameter of 77 mm. The glass mold was heated from 25° C. to 120° C. over 16 hours. The glass mold was cooled to room temperature and 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 annealed flat lens were measured, and the results are shown in Table 1.

[Examples 2 to 15]
A flat lens was obtained in the same manner as in Example 1, except that the type and content of the near-infrared absorbing agent were set to the types and contents shown in Table 1. The measurement results of the physical properties of the obtained flat lens are shown in Table 1.
Moreover, the transmittance curves of the flat lenses of Examples 1 to 5 are shown in Fig. 1. The transmittance curves of the flat lenses of Examples 6 to 10 are shown in Fig. 2. The transmittance curves of the flat lenses of Examples 11 to 15 are shown in Fig. 3.

[Comparative Example 1]
The mixture was stirred at 25° C. for 1 hour in the same manner as in Example 1, except that the near infrared absorbent A was changed to the near infrared absorbent D and the content of the near infrared absorbent D was set to an amount shown in Table 1. However, the near infrared absorbent D did not dissolve.

[Comparative Examples 2 to 7]
The mixture was stirred at 25° C. for 1 hour in the same manner as in Example 1, except that the near-infrared absorbent A was changed to the near-infrared absorbent E and the content of the near-infrared absorbent E was set to an amount shown in Table 1. The measurement results of the physical properties of the obtained flat lens are shown in Table 1.

[Example 16]
100 parts by mass of bis(2,3-epithiopropyl)disulfide, 1.1 parts by mass of Tinuvin PS (manufactured by BASF Japan Ltd.) as an ultraviolet absorber, 0.02 parts by mass of N,N-dimethylcyclohexylamine, 0.1 parts by mass of N,N-dicyclohexylmethylamine, 10 parts by mass of a mixture of 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and an amount of near-infrared absorber A such that the content would be the amount shown in Table 2 were charged, and the mixture was stirred at 20° C. for 15 minutes to prepare a homogeneous solution.
The solution was degassed at 400 Pa for 1 hour, filtered through a 1 μm PTFE filter, and then poured into a flat glass mold with a center thickness of 2 mm and a diameter of 77 mm. The glass mold was heated from 25° C. to 120° C. over 20 hours. The glass mold was cooled to room temperature and 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 annealed flat lens were measured, and the results are shown in Table 2.

[Examples 17 to 30]
A flat lens was obtained in the same manner as in Example 16, except that the type and content of the near-infrared absorbing agent were set to the types and contents shown in Table 2. The measurement results of the physical properties of the obtained flat lens are shown in Table 2.
Moreover, the transmittance curves of the flat lenses of Examples 16 to 20 are shown in Fig. 4. The transmittance curves of the flat lenses of Examples 21 to 25 are shown in Fig. 5. The transmittance curves of the flat lenses of Examples 26 to 30 are shown in Fig. 6.

[Comparative Example 8]
The mixture was stirred at 25° C. for 1 hour in the same manner as in Example 16, except that the near infrared absorbent A was changed to the near infrared absorbent D and the content of the near infrared absorbent D was set to an amount shown in Table 2. However, the near infrared absorbent D did not dissolve.

[Comparative Example 9]
The mixture was stirred at 25° C. for 1 hour in the same manner as in Example 16, except that the near infrared absorbent A was changed to the near infrared absorbent E and the content of the near infrared absorbent E was set to an amount shown in Table 2. However, the near infrared absorbent E did not dissolve.

[Example 31]
A polycarbonate resin (Panlite L-1225WP manufactured by Teijin Limited) and near-infrared absorbent A were mixed in an amount such that the content of near-infrared absorbent A was 72 ppm by mass in a tumbler for 20 minutes, and then melted and kneaded in a single-screw extruder under conditions of a cylinder setting temperature of 280° C. and a screw rotation speed of 56 rpm (revolutions per minute) to prepare pellets (resin composition).
Using the prepared pellets as a raw material, a flat lens having an outer dimension of 150 mm×300 mm and a thickness of 2 mm was molded in 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. The measurement results of the physical properties of the obtained flat lens are shown in Table 2.
The transmittance curve of the flat lens of Example 31 is shown in FIG.

As shown in Table 1 or Table 2, the flat lenses in Examples 1 to 31 had low transmittance at λmax and excellent near-infrared cut rate. In addition, the flat lenses in Examples 1 to 31 had good evaluations of color and were excellent in design.
On the other hand, the flat lenses in Comparative Examples 2 and 3, which used a near-infrared absorbent E which does not correspond to any of the compounds represented by Formulae (I) to (III) in the present application, had high transmittance at λmax and poor near-infrared cut rate.
The flat lenses in Comparative Examples 4 to 7, which used a near-infrared absorbent E which does not correspond to any of the compounds represented by Formulae (I) to (III) in the present application, had low a* values in the CIE1976 (L*, a*, b*) color space and were inferior in color.
In Comparative Examples 1, 8 and 9, the near infrared absorbing agent was not dissolved, and therefore a flat lens could not be obtained.

Claims (14)

At least one resin selected from the group consisting of (thio)urethane resins and episulfide resins;
and a near infrared absorbing agent which is at least one selected from the group consisting of a compound represented by the following formula (I) and a compound represented by the following formula (II),
The near infrared absorbing agent is contained in an amount of 3 ppm by mass or more and 90 ppm by mass or less,
In the CIE 1976 (L*, a*, b*) color space when measured at a thickness of 2 mm, a* is greater than or equal to -0.8 and less than or equal to 10, and L* is greater than or equal to 85 ;
An optical material having a transmittance of 80% or less at the maximum absorption wavelength.


In formula (I), R ₁ and R ₂ each independently represent an alkyl group which may be substituted, and M represents a divalent metal atom, a trivalent or tetravalent substituted metal, or an oxymetal.


In formula (II), _R1 and _R2 each independently represent an optionally substituted alkyl group, _R3 represents a nitro group or a group represented by _NR4R5 , which may be _the same or different from each other, and _R4 and _R5 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkylsulfonyl group or an optionally substituted arylsulfonyl group. The optical material according to claim 1, which has a minimum value of the transmittance curve in the wavelength range of 800 nm to 950 nm at a thickness of 2 mm, and said minimum value is 0.05% or more and 80% or less. The optical material according to claim 1 or 2, which has a luminous transmittance of 70% or more at a thickness of 2 mm. The optical material according to any one of claims 1 to 3, wherein the near infrared absorber has a peak between 840 nm and 930 nm in a visible light absorption spectrum measured in a 3 ppm to 5 ppm by mass toluene solution, the extinction coefficient of the peak at an apex of the peak is 1.10 x 10 ⁵ ml/g cm or more, the peak width at 1/4 of the absorbance at the apex of the peak is 100 nm or less, the peak width at 1/2 of the absorbance at the apex of the peak is 55 nm or less, and the peak width at 2/3 of the absorbance at the apex of the peak is 40 nm or less. The optical material according to any one of claims 1 to 4, wherein the near-infrared absorbent is composed of two or more compounds. The (thio)urethane resin comprises a constituent unit derived from a polyisocyanate compound, and at least one of a constituent unit derived from a polythiol compound and a constituent unit derived from a polyol compound,
The polyisocyanate compound is at least one selected from the group consisting of 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, isophorone diisocyanate, 1,6-hexamethylene diisocyanate, and 1,5-pentamethylene diisocyanate;
The polythiol compound is, for example, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis(3-mercaptopropane), at least one selected from the group consisting of 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane;
The polyol compound is at least one selected from the group consisting of ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1,3-propanediol, 1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, and 1,4-cyclohexanediol. The optical material according to any one of claims 1 to 5. the episulfide resin is composed of a constituent unit derived from an episulfide compound, or composed of a constituent unit derived from an episulfide compound and a constituent unit derived from a polythiol compound,
the episulfide compound is at least one selected from the group consisting of bis(2,3-epithiopropyl)sulfide, bis(2,3-epithiopropyl)disulfide, bis(1,2-epithioethyl)sulfide, bis(1,2-epithioethyl)disulfide, and bis(2,3-epithiopropylthio)methane;
The polythiol compound is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis(3-mercaptopropionate), bis(mercaptomethyl)-1,11-dimercaptopropionate ... The optical material according to any one of claims 1 to 5, which is at least one selected from the group consisting of pentaerythritol tetrakis(2-mercaptoethyl) sulfide, pentaerythritol tetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl)-1,4-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane. A polymerizable compound,
and a near infrared absorbing agent which is at least one selected from the group consisting of a compound represented by the following formula (I) and a compound represented by the following formula (II),
The near infrared absorbing agent is contained in an amount of 3 ppm by mass or more and 90 ppm by mass or less,
The polymerizable compound is a polymerizable composition for an optical material, which includes at least one selected from the group consisting of a combination of a polyisocyanate compound and at least one of a polythiol compound and a polyol compound, an episulfide compound, and a combination of an episulfide compound and a polythiol compound.


In formula (I), R ₁ and R ₂ each independently represent an optionally substituted alkyl group, and M represents a divalent metal atom, a trivalent or tetravalent substituted metal, or an oxymetal.


In formula (II), _R1 and _R2 each independently represent an optionally substituted alkyl group, _R3 represents a nitro group or a group represented by _NR4R5 , which may be _the same or different from each other, and _R4 and _R5 each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkylsulfonyl group or an optionally substituted arylsulfonyl group. The polyisocyanate compound is at least one selected from the group consisting of 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, isophorone diisocyanate, 1,6-hexamethylene diisocyanate, and 1,5-pentamethylene diisocyanate;
The polythiol compound is, for example, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, pentaerythritol tetrakis(3-mercaptopropane), at least one selected from the group consisting of 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithiane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane;
The polymerizable composition for an optical material according to claim 8, wherein the polyol compound is at least one selected from the group consisting of ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1,3-propanediol, 1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, and 1,4-cyclohexanediol. The polymerizable composition for optical materials according to claim 8 or claim 9, wherein the near-infrared absorbent is composed of two or more compounds. The polymerizable composition for optical materials according to any one of claims 8 to 10, wherein the episulfide compound is at least one selected from the group consisting of bis(2,3-epithiopropyl)sulfide, bis(2,3-epithiopropyl)disulfide, bis(1,2-epithioethyl)sulfide, bis(1,2-epithioethyl)disulfide, and bis(2,3-epithiopropylthio)methane. A plastic lens comprising the optical material according to any one of claims 1 to 7. Eyewear comprising the plastic lens according to claim 12. An optical sensor comprising the plastic lens according to claim 12.