JPWO2020218614A1 - Optical materials, polymerizable compositions for optical materials, plastic lenses, eyewear, infrared sensors and infrared cameras - Google Patents

Abstract

CIE1976 (L *, a *, b) containing at least one resin selected from the group consisting of polycarbonate resin, (thio) urethane resin and episulfide resin, and a near-infrared absorber, and measured at a thickness of 2 mm. *) An optical material in which a * is -30 or more and 0 or less and L * is 80 or more in the color space.

Description

The present disclosure relates to optical materials containing near infrared absorbers, polymerizable compositions for optical materials, plastic lenses, eyewear, infrared sensors and infrared cameras.

Conventionally, lenses that cut a specific wavelength range have been developed.

Patent Document 1 describes a near-infrared ray cut having a near-infrared reflective 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.

Patent Documents 3 to 7 disclose a resin composition containing a predetermined phthalocyanine dye and a resin. Patent Document 7 describes that a lens for protective eyeglasses can be obtained from the resin composition.
Patent Document 8 and Patent Document 9 disclose a far-infrared cut lens composed of a phthalocyanine dye 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. 2017-529415 Patent Document 9: Japanese Patent Application Laid-Open No. 2018-528829

However, in the conventional technique described in the patent document, there is room for improvement in the following points.

Although 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.

Therefore, when we proceeded with the study of optical materials in which a near-infrared absorber was added to the resin, the near-infrared absorber did not dissolve in the resin, and 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, the near-infrared ray cutting effect and the designability have a trade-off relationship.

An object to be solved by one embodiment of the present disclosure is to provide an optical material having a high near-infrared cut rate and excellent design.

As a result of diligent studies, the present inventors have made 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. We have found that it is possible to achieve both, and completed the invention of the present disclosure.
That is, the present disclosure can be shown below.

<1> CIE1976 (L *, a) containing at least one resin selected from the group consisting of polycarbonate resin, (thio) urethane resin, and episulfide resin, and a near-infrared absorber, and measured at a thickness of 2 mm. *, B *) An optical material in which a * is -30 or more and 0 or less and L * is 80 or more in the color space.
<2> The optical material according to <1>, wherein 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.
<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.
<6> 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 optical material according to any one of <1> to <5>, which has a minimum value of less than 50% spectral transmittance within at least one range of a wavelength region of about 1100 nm.
<7> The optical material according to any one of <1> to <6>, wherein the near-infrared absorber contains a phthalocyanine compound.
<8> 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 absorption coefficient (ml / g · cm) of (the point showing the maximum absorption 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. Moreover, 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 is in 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).

(In the general formula (I), 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 each independently represent a hydrogen atom or a halogen atom. 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.)

In the general formula (II), R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are linear or branched alkyl groups, alkoxyalkyl groups or dialkylaminoalkyl groups. Shown, X ₁ , X ₂ , X ₃ , X ₄ , X ₅ , X ₆ , X ₇ , X ₈ indicate a sulfur atom or> NR ₉ , and X ₁ = ( _{either X 3} or X ₄ ). = (One of X ₅ and X ₆ ) = (one of X ₇ and X ₈ ) = sulfur atom and X ₂ = ( _{the other of X 3} and X ₄ ) = (X ₅ and X) _{The other of 6} ) = (the other of X ₇ and X ₈ ) => NR _9. R ₉ represents a hydrogen atom or an alkyl group, and M is two hydrogen atoms, a divalent metal or a trivalent. Or a tetravalent metal derivative.)

(In the general formula (III), R _{1 to} R ₄ each independently represent an alkyl group or an alkoxyalkyl group, and X is a phenylthio group or a substituent which may have a halogen atom, an alkylthio group or a substituent. It indicates a naphthylthio group which may be possessed, and M indicates two hydrogen atoms, a divalent metal or a derivative of a trivalent or tetravalent metal.)
<10> 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.
<11> The optical material according to <10>, wherein the phthalocyanine compound contains a compound represented by the general formula (I).
<12> 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, and the near-infrared absorber is (2) within the range of the wavelength region of 825 nm to 875 nm in the spectral transmittance curve. The optical material according to <9>, which has a minimum value of less than 50% spectral transmittance.
<13> The optical material according to <12>, wherein the phthalocyanine compound contains a compound represented by the general formula (II).
<14> 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 within the range of the wavelength region of 1000 nm to 1100 nm in (3) 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).
<16> The optical material according to any one of <1> to <15>, which contains the near-infrared absorber at 3 ppm or more and 80 ppm or less.
<17> The optical material according to any one of <1> to <16>, wherein the near-infrared absorber contains a plurality of phthalocyanine compounds having different structures in combination.
<18> The (thio) urethane resin is composed of at least one of a constituent unit derived from a polyisocyanate compound, a constituent unit derived from a polythiol compound, and a constituent 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, and the like. 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 include 4-mercaptomethyl-1,8-dimercapto-3,6-dithiane octane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiandecan, 4,7-. Dimercaptomethyl-1,11-dimercapto-3,6,9-trithiandecan, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithianeundecane, pentaerythritol tetrakis (3- Mercaptopropionate), bis (mercaptoethyl) sulfide, pentaerythritol tetrakis (2-mercaptoacetate), 2,5-bis (mercaptomethyl) -1,4-dithiane, 1,1,3,3-tetrakis (mercapto) Methylthio) Propane, at least one selected from 4,6-bis (mercaptomethylthio) -1,3-dithiane, and 2- (2,2-bis (mercaptomethylthio) ethyl) -1,3-dithiane.
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.
<19> The episulfide resin is composed of a constituent unit derived from an episulfide compound, or a constituent unit derived from an episulfide compound and a constituent unit derived from a polythiol compound.
The episulfide compounds include bis (2,3-epithiopropyl) sulfide, bis (2,3-epiothiopropyl) disulfide, bis (1,2-epithioethyl) sulfide, bis (1,2-epithioethyl) 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. The optical material according to any one of <1> to <17>, which is at least one selected from −cyclohexanediol and 1,4-cyclohexanediol.
<20> A polymerizable composition used for producing the optical material according to any one of <1> to <19>.
A polymerizable compound composed 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.
At least one range of (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) a wavelength region of 1000 nm to 1100 nm in the spectral transmittance curve. A near-infrared absorber having a minimum spectral transmittance of less than 50%,
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.
<22> 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 absorption coefficient (ml / g · cm) of (the point showing the maximum absorption 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. Moreover, 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> The polymerizable composition for an optical material according to <21> or <22>, wherein the phthalocyanine compound contains at least one compound represented by the general formulas (I) to (III).

(In the general formula (I), 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 each independently represent a hydrogen atom or a halogen atom. 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.)

In the general formula (II), R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are linear or branched alkyl groups, alkoxyalkyl groups or dialkylaminoalkyl groups. Shown, X ₁ , X ₂ , X ₃ , X ₄ , X ₅ , X ₆ , X ₇ and X ₈ indicate sulfur atom or -NR ₉ and X ₁ = ( _{either X 3} or X ₄ ). = (One of X ₅ and X ₆ ) = (one of X ₇ and X ₈ ) = sulfur atom and X ₂ = ( _{the other of X 3} and X ₄ ) = (X ₅ and X) _{The other of 6} ) = (the other of X ₇ and X ₈ ) = -NR _9. R ₉ represents a hydrogen atom or an alkyl group, and M is two hydrogen atoms, a divalent metal or a trivalent. Or a tetravalent metal derivative.)

(In the general formula (III), R _{1 to} R ₄ each independently represent an alkyl group or an alkoxyalkyl group, and X is a phenylthio group or a substituent which may have a halogen atom, an alkylthio group or a substituent. It indicates a naphthylthio group which may be possessed, and M indicates two hydrogen atoms, a divalent metal or a derivative of a trivalent or tetravalent metal.)
<24> A polymerizable composition used for producing an optical material having 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, wherein the near-infrared absorber is (1). ) 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 700 nm to 750 nm in the spectral transmittance curve.
<25> The polymerizable composition for an optical material according to <24>, wherein the phthalocyanine compound contains a compound represented by the general formula (I).
<26> A polymerizable composition used for producing an optical material having 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, wherein the near-infrared absorber is (2) spectroscopic. 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.
<27> The polymerizable composition for an optical material according to <26>, wherein the phthalocyanine compound contains a compound represented by the general formula (II).
<28> A polymerizable composition used for producing an optical material having 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, wherein the near-infrared absorber is (3) spectroscopic. 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.
<32> 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) ) At least one selected from cyclohexane, isophorone diisocyanate, 1,6-hexamethylene diisocyanate, and 1,5-pentamethylene diisocyanate.
The polythiol compounds include 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiandecan, 4,7-. Dimercaptomethyl-1,11-dimercapto-3,6,9-trithiandecan, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithianeundecane, pentaerythritol tetrakis (3- Mercaptopropionate), bis (mercaptoethyl) sulfide, pentaerythritol tetrakis (2-mercaptoacetate), 2,5-bis (mercaptomethyl) -1,4-dithiane, 1,1,3,3-tetrakis (mercapto) Methylthio) Propane, at least one selected from 4,6-bis (mercaptomethylthio) -1,3-dithiane, and 2- (2,2-bis (mercaptomethylthio) ethyl) -1,3-dithiane.
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.
<33> The episulfide compound is bis (2,3-epithiopropyl) sulfide, bis (2,3-epiothiopropyl) disulfide, bis (1,2-epithioethyl) sulfide, bis (1,2-epioethyl). The polymerizable composition for an optical material according to any one of <20> to <31>, which is at least one selected from disulfide and bis (2,3-epithiopropylthio) methane.
<34> A plastic lens made of the optical material according to any one of <1> to <19>.
<35> Eyewear provided with the plastic lens according to <34>.
<36> An infrared sensor or an infrared camera provided with the plastic lens according to <34>.

According to the present disclosure, it is possible to provide an optical material having a high near-infrared cut rate and 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.

In the present disclosure, 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.
In the present disclosure, 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.
In the numerical range described stepwise in the present disclosure, 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 the numerical range described in another stepwise description. .. Further, in the numerical range described in the present disclosure, the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
Hereinafter, embodiments of the present disclosure will be specifically described.

≪Optical material≫
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. (L *, a *, b *) In the color space, a * is -30 or more and 0 or less, and 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.

In this embodiment, 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. By setting * in the above range, it is possible to achieve both a high near-infrared cut rate and designability.

From the viewpoint of the effect of the present invention, the optical material of the present embodiment has 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 700 nm to 750 nm at a thickness of 2 mm: 0.05% or more and 70% or less, preferably 3% or more and 50% or less, still more preferably 5% or more and 40% or less. Transmittance: 4% or more and 70% or less, preferably 6% or more and 50% or less, more preferably 8% or more and 40% or less. 6% or more and 50% or less, more preferably 8% or more and 40% or less

Since the optical material of the present embodiment suppresses turbidity and coloring and is excellent in design, 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.

[Near infrared absorber]
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.

As 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.
In order to realize a high cut rate in a wide near-infrared region, the near-infrared absorber having the characteristics (1) to (3) can be used in combination, and 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 absorption coefficient (ml / g · cm) of the point indicating the absorption 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 1/2 of the absorbance of (Pmax) of the peak (P) is 130 nm or less, and the peak width at 2/3 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 the phthalocyanine compound includes at least one compound represented by the general formulas (I) to (III). Is preferable.

In the general formula (I), 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.

Specific examples of 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 include 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.}
The _{substituted or unsubstituted alkoxy group having a total carbon number of 3 to 18 in R 1} and R ₂ may have, for example, a substituent, 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.
Examples of the substituent 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.

Specific examples of preferable phthalocyanine dyes are described in, for example, JP-A-3-62878, JP-A-3-141582, and JP-A-3-215466. Particularly preferred is a compound represented by the chemical formula (I-1) described later.

In general formula (II), 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. , X ₁ , X ₂ , X ₃ , X ₄ , X ₅ , X ₆ , X ₇ and X ₈ indicate sulfur atom or -NR ₉ and X ₁ = ( _{either X 3} or X ₄ ) = (One of X ₅ and X ₆ ) = (one of X ₇ and X ₈ ) = sulfur atom and X ₂ = ( _{the other of X 3} and X ₄ ) = (X ₅ and X ₆₎ the other) = (the other _{X 7} and _{X 8)} =
-NR ₉ R ₉ represents a hydrogen atom or an alkyl group, and M represents two hydrogen atoms, a divalent metal or a trivalent or tetravalent metal derivative.

In the phthalocyanine compound represented by the general formula (II), when R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are alkyl groups, the present invention is not particularly limited. However, 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 from the viewpoint of availability and the like. 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 and 2-ethylhexyl group can be mentioned.

When R _{1 to} R ₈ are alkoxyalkyl groups, those having 3 to 6 carbon atoms are preferable. Examples thereof include a methoxyethyl group, a methoxypropyl group, a methoxybutyl group, an ethoxyethyl group, an ethoxypropyl group, an ethoxybutyl group, an n-propoxyethyl group and an iso-propoxyethyl group.
When R _{1 to} R ₈ are dialkylaminoalkyl groups, those having 3 to 12 carbon atoms are preferable, and a group represented by the general formula (II-a) is particularly preferable.

In formula (II-a), R ₁₂ represents an alkylene group having 1 to 4 carbon atoms, and R ₁₃ and R ₁₄ individually represent an alkyl group having 1 to 4 carbon atoms. ) Examples are 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.

Regarding the types of substituents _{of R 1 to} R ₈ in the present embodiment _{, R 1} = (one of R ₃ and R ₄ ) = (one of R ₅ and R ₆ ) = (R ₇ and R _8). Of any one of them), and R ₂ = ( _{the other of R 3} and R ₄ ) = (the other of R ₅ and R ₆ ) = (the other of R ₇ and R ₈ ) is particularly preferable. .. Further, it is also preferable that all of _{R 1 to} R _{8 have the same substituent.}

When R ₉ is an alkyl group, one having 1 to 6 carbon atoms is preferable. Examples thereof include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group and an n-hexyl group.

Cu, Zn, Fe, Co, Ni, Ru, Pb, Rh, Pd, Pt, Mn, Sn or Pb are preferable as M being a divalent metal, and 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. In particular, Cu, Ni, Co, FeCl, Zn, VO, Pd or MnOH are preferable.
Specific examples of the phthalocyanine dye represented by the general formula (II) are described in Table 1 of JP-A-8-60008. Particularly preferred is a compound represented by the chemical formula (II-1) described later.

In the general formula (III), R _{1 to} R ₄ independently represent an alkyl group or an alkoxyalkyl group, and 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.

When 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 and 2-ethylhexyl group can be mentioned.

When R _{1 to} R ₄ are alkoxyalkyl groups, those having a total carbon number of 2 to 6 are preferable.
Examples thereof include a methoxyethyl group, a methoxypropyl group, a methoxybutyl group, an ethoxyethyl group, an ethoxypropyl group, an ethoxybutyl group, an n-propoxyethyl group and an 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 such as a chlorine atom, a bromine atom, or a bromine atom. A fluorine atom is preferable, and a chlorine atom is particularly preferable.

When 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.

When 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. Examples include good amino groups, halogen atoms and the like.

Specific examples of the 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. Thio group, p-tert-butylphenylthio group, pn-octylphenylthio group, p-methoxyphenylthio group, p-ethoxyphenylthio group, pn-propoxyphenylthio group, p-iso-propoxyphenyl Thio group, pn-butoxyphenylthio group, p-iso-butoxyphenylthio group, p-sec-butoxyphenylthio group, pn-pentoxyphenylthio group, pn-octylphenylthio group, 2 , 4-Dimethylphenylthio group, p-dimethylaminophenylthio group, p-diethylaminophenylthio group, p-di-n-butylaminophenylthio group, p-chlorophenylthio group, p-bromophenylthio group, p- Fluorophenylthio group, 2,4-dichlorophenylthio group and the like can be mentioned.

In particular, 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.

When 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. In particular, a naphthylthio group and a naphthylthio group having an alkyl group having 1 to 4 carbon atoms are preferable.

As the divalent metal, Cu, Zn, Fe, Co, Ni, Ru, Pb, Rh, Pd, Pt, Mn or Sn are preferable, and the derivative of the trivalent or tetravalent metal is preferable. As, 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. As 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 preferred is a compound represented by the chemical formula (III-1) described later.

From the viewpoint of the effect of the present invention, 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 or more. 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. This makes it possible to efficiently cut near infrared rays in a wide area.

From the viewpoint of the effect in the present disclosure, 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 effect in the present disclosure.

~ Aspect A ~
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.

(Near infrared absorber)
As 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 the above is preferable.
By using a near-infrared absorber satisfying (1), it becomes easy to set the spectral transmittance at a wavelength of 700 nm to 750 nm at a thickness of 2 mm within the above range.

Examples of the near-infrared absorber satisfying (1) include the compound represented by the above-mentioned general formula (I).

~ Aspect B ~
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 range of 825 nm to 875 nm in the spectral transmittance curve. A near-infrared absorber having the above 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).

~ Aspect C ~
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 range of 1000 nm to 1100 nm in the spectral transmittance curve. A near-infrared absorber having the above 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).

<Resin>
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.

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.

Examples of the polycarbonate resin include 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, and 1 , 1-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane polycarbonate resin, 9,9-bis (4-hydroxyphenyl) fluorene polycarbonate resin, 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.

Examples of 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. 2-Bis (4-hydroxyphenyl) octane, 2,2-bis (4-hydroxyphenyl) phenylmethane, 2,2-bis (4-hydroxy-3-methylphenyl) propane, 2,2-bis (4-) Hydroxy-3-3rd butylphenyl) propane, 1,1-bis (4-hydroxy-3-3rd butylphenyl) propane, 2,2-bis (4-hydroxy-3-bromophenyl) propane, 2,2 -Bis (4-hydroxy-3,5-dibromophenyl) propane, (hydroxyaryl) alkanes such as 2,2-bis (4-hydroxy-3,5-dichlorophenyl) propane, 1,1-bis (4) -Hydroxyphenyl) cyclopentane, (hydroxyaryl) cycloalkanes such as 1,1-bis (4-hydroxyphenyl) cyclohexane, 4,4'-dihydroxydiphenyl ether, 4,4'-dihydroxy-3,3'- Dihydroxydiaryl ethers such as dimethyldiphenyl ethers, dihydroxydiarylsulfides such as 4,4'-dihydroxydiphenylsulfide, 4,4'-dihydroxydiphenyl sulfoxide, 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfoxide Examples thereof include dihydroxydiaryl sulfoxides such as 4,4'-dihydroxydiphenyl sulfone, and dihydroxydiaryl sulfone such as 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfone.
These may be used alone or selected from two or more types.

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 1000 to 100,000, preferably 1000 to 4000,000.

The dihydroxydiaryl compounds may be used in combination with a phenol compound having a valence of 3 or more as shown below. Examples of the trivalent or higher phenol include fluoroglucosine, 1,3,5-tri- (4-hydroxyphenyl) -benzol, 1,1,1-tri- (4-hydroxyphenyl) -ethane and the like.
As the polycarbonate resin, a commercially available product may be used, for example, Panlite (manufactured by Teijin Limited), Upiron (manufactured by Mitsubishi Engineering Plastics Co., Ltd.), Novalex (manufactured by Mitsubishi Engineering Plastics Co., Ltd.), SD. Examples include Polycarbonate (manufactured by Sumitomo Polycarbonate Co., Ltd.).

The (thio) urethane resin is composed of at least one of a constituent unit derived from a polyisocyanate compound, a constituent unit derived from a polythiol compound, and a constituent 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.
These compounds will be described in detail in the section of Polymerizable Compositions for Optical Materials below.

<Polymerizable composition for optical materials>
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. Alternatively, 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 in the spectral transmittance curve, (2) a wavelength region of 825 nm to 875 nm in 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 the wavelength region of 1000 nm to 1100 nm in the spectral transmittance curve.

The above-mentioned near-infrared absorber 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.

As described above, preferred embodiments of the optical material of the present embodiment include embodiments A to C described above from the viewpoint of the effects in the present disclosure.
As 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.

As 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.

As the polymerizable composition used for producing the optical material according to the aspect C, it is preferable to use the near-infrared absorber described in the section of the aspect C.

(Polyisocyanate compound)
Examples of the polyisocyanate compound include an aliphatic isocyanate compound, an alicyclic isocyanate compound, an aromatic isocyanate compound, a heterocyclic isocyanate compound, an aromatic aliphatic isocyanate compound and the like, 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 / 0555540.

In the present embodiment, from the viewpoint of the effect in the present disclosure, 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, isophorone diisocyanate, 1,6-hexamethylene diisocyanate, and 1,5-pentamethylene diisocyanate, preferably at least one selected.
2,5-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, 2,6-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, m-xylylene diisocyanate, And at least one selected from 1,3-bis (isocyanatomethyl) cyclohexane is more preferred.

(Polythiol compound)
The polythiol compound is a compound having two or more mercapto groups, and examples thereof include the compounds exemplified in WO2016 / 125736.
In the present embodiment, from the viewpoint of the effect in the present disclosure, the polythiol compound is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiane octane, 5,7-dimercaptomethyl-1,11-dimercapto-3. , 6,9-Trithiandecan, 4,7-Dimercaptomethyl-1,11-Dimercapto-3,6,9-Trithiandecan, 4,8-Dimercaptomethyl-1,11-Dimercapto-3,6 , 9-Trithiane decane, 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-It is preferably at least one selected from the group consisting of dithiane.
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 at least one selected from the group consisting of pentaerythritol tetrakis (2-mercaptoacetate).

The polyol compound is one or more aliphatic or alicyclic alcohols, specifically, linear or branched aliphatic alcohols, alicyclic alcohols, these alcohols and ethylene oxide, propylene oxide, ε. -Alcohol to which caprolactone is added can be mentioned, and specifically, the compound 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 of the episulfide compound include an epithioethylthio compound, a chain aliphatic 2,3-epiothiopropylthio compound, a cyclic aliphatic 2,3-epithiopropylthio compound, and an aromatic 2,3-epiothiol compound. Examples thereof include propylthio compounds, chain aliphatic 2,3-epithiopropyloxy compounds, cyclic aliphatic 2,3-epiopropyloxy compounds, aromatic 2,3-epiopropyloxy compounds, and the like. It is used by one kind or a mixture of two or more kinds. Examples of these episulfide compounds include the compounds exemplified in WO2015 / 137401.
The episulfide compound is preferably bis (2,3-epithiopropyl) sulfide, bis (2,3-epiothiopropyl) disulfide, bis (1,2-epithioethyl) sulfide, bis (1,2-epithioethyl) disulfide. , And at least one selected from the group consisting of bis (2,3-epithiopropylthio) methane.

Examples of the additive include a polymerization catalyst, an internal mold release agent, a brewing agent, an ultraviolet absorber, and the like. In the present embodiment, when polyurethane and polythiourethane are obtained, a polymerization catalyst 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 phosphoric acid monoester and 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 range in the visible light region and having a function of adjusting the hue of an optical material made of a resin. More specifically, the bluing agent contains a substance showing a blue color to a purple color.

The UV absorbers used include 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-4-acryloyloxybenzophenone, 2-hydroxy-4-acryloyloxy-5-tert-butylbenzophenone, 2-hydroxy-. 4-Acryloyloxy-2', 4'-Benzophenone-based ultraviolet absorbers such as 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 (2,4dimethylphenyl) -1,3,5-triazine, 2- [4- [ (2-Hydroxy-3- (2'-ethyl) hexyl) Oxy] -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2,4- Bis (2-hydroxy-4-butyloxyphenyl) -6- (2,4-bis-butyloxyphenyl) -1,3,5-triazine, 2- (2-hydroxy-4- [1-octyloxycarbonyl) Ethoxy] phenyl) -4,6-bis (4-phenylphenyl) -1,3,5-triazine and other triazine-based UV absorbers,

2- (2H-benzotriazole-2-yl) -4-methylphenol, 2- (2H-benzotriazole-2-yl) -4-tert-octylphenol, 2- (2H-benzotriazole-2-yl)- 4,6-bis (1-methyl-1-phenylethyl) phenol, 2- (2H-benzotriazole-2-yl) -4,6-di-tert-pentylphenol, 2- (5-chloro-2H-) Benzotriazole-2-yl) -4-methyl-6-tert-butylphenol, 2- (5-chloro-2H-benzotriazole-2-yl) -2,4-tert-butylphenol, 2,2'-methylenebis [ Examples thereof include benzotriazole-based ultraviolet absorbers such as 6- (2H-benzotriazole-2-yl) -4- (1,1,3,3-tetramethylbutyl) phenol], and 2- (2H) is preferable. -Benzotriazole-2-yl) -4-tert-octylphenol and 2- (5-chloro-2H-benzotriazole-2-yl) -4-methyl-6-tert-butylphenol benzotriazole-based ultraviolet absorbers are mentioned. Be done. These UV absorbers can be used alone or in combination of two or more.
The composition for optical materials 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 uniformly mixed, and a known method can be used.

[Optical material]
The 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, wrenchular lenses, contact lenses, infrared sensor lenses, infrared camera lenses, sunglasses and fashion lenses. Various 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 glass, a motorcycle helmet, a transparent substrate, and the like. The optical material of the present embodiment may contain an ultraviolet absorber. As the optical material, 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.
Hereinafter, a plastic lens, which is a preferred embodiment of the optical material, will be described in detail.

[Plastic lens]
Examples of the plastic lens include the following configurations.
(A) A plastic lens provided with 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 provided with a film or coating layer made of the composition for optical materials 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 materials of the present embodiment. However, a plastic lens in which (excluding the lens base material obtained from the composition for optical materials of the present embodiment) is laminated, these plastic lenses can be preferably used in the present embodiment.
Hereinafter, each embodiment will be described.

(Embodiment a)
The method for producing a plastic lens including the lens substrate made of the composition for 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 is used for the optical material of the present embodiment, which comprises a near-infrared absorber and a monomer of these resins (resin monomer for an optical material). The composition can be used.

Specifically, the composition for an optical material is injected into the cavity of the molding mold held by a gasket, tape or the like. At this time, depending on the physical characteristics required for the obtained plastic lens, it is often preferable to perform defoaming treatment under reduced pressure, filtration treatment such as pressurization and reduced pressure, and the like, if necessary.

Then, after the composition is injected, the lens casting mold is heated by a predetermined temperature program in a heatable device such as in an oven or in water to cure and mold. The resin molded product may be subjected to a treatment such as annealing, if necessary.

In the present embodiment, when molding the resin, in addition to the above-mentioned "arbitrary additive", a chain extender, a cross-linking agent, a light stabilizer, and an antioxidant, as in the case of a known molding method depending on the purpose. , Oil-soluble dyes, fillers, adhesion improvers and the like may be added.

Further, the plastic lens in the present embodiment may have various coating layers on the lens base material made of the composition for optical materials of the present embodiment according to the purpose and use thereof. 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.

(Embodiment b)
The plastic lens of the present embodiment may be provided with a film or layer made of the composition for optical materials of the present embodiment on at least one surface of the surface of the lens substrate. 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.

As a method for manufacturing a plastic lens in the present embodiment, for example, (b-1) 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) In a cavity of a molding mold held by a gasket or tape as described later, one of the molds is a film or a sheet made of the composition for an optical material of the present embodiment. 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 materials 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 method for the plastic lens 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).

Further, the plastic lens in the present embodiment may have various coating layers on a lens base material or a "film or layer" made of a composition for an optical material, depending on the purpose and use thereof. Similar to the plastic lens in embodiment a, the coating layer may contain a near infrared absorber.

(Embodiment c)
In the plastic lens of the present embodiment, a lens base material (excluding the lens base material obtained from the optical material composition of the present embodiment) is laminated on both sides of a film made of the optical material composition of the present embodiment. You may.

As a method for manufacturing a plastic lens in the present embodiment, for example, (c-1) a method of manufacturing 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 molded 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 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 the method of the plastic lens (b-1) in the embodiment b. Things can be used.
A known method can be used as a method of bonding the film or sheet made of the composition for optical materials of the present embodiment on the surface of the lens base material.
The method (c-2) can be specifically carried out as follows.

In the space of the lens casting mold used in the method for manufacturing a plastic lens in the embodiment a, 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.

Next, in the space of the lens casting mold, 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.

Then, after the composition is injected, the lens casting mold is heated by a predetermined temperature program in a heatable device such as in an oven or in water to cure and mold. The resin molded product may be subjected to a treatment such as annealing, if necessary.

Further, 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 may contain a near infrared absorber.

[Plastic spectacle lens]
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.

Specific examples of the coating layer include a primer layer, a hard coat layer, an antireflection layer, an anti-fog coat layer, an anti-contamination 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 layers. When the coating layers are applied to both surfaces, the same coating layer may be applied to each surface, or different coating layers may be applied to each surface.

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 an 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 temperature. For the layer to be coated by coating, various leveling agents for the purpose of improving the coatability may be used.

The primer layer is usually formed between the hard coat layer described later and the lens. 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, or polyvinyl acetal as the 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. When the 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 a primer layer. When it is carried out by a dry method, it is formed by a known dry method such as a CVD method or a vacuum vapor deposition method. When forming the primer layer, 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. ..

In addition to the above components, 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. Examples of the curing method include heat curing and a curing method by irradiation with energy rays such as ultraviolet rays and visible light. In order to suppress the occurrence of interference fringes, 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 hardcourt layer as needed. The antireflection layer includes an inorganic type and an organic type. In the case of the inorganic type, _{an inorganic oxide such as SiO 2} or TiO ₂ is used, and a vacuum vapor deposition method, a sputtering method, an ion plating method, an ion beam assist method, or a CVD method is used. It is formed by a dry method such as. In the case of an organic system, it is formed by a wet method using a composition containing an organosilicon compound and silica-based fine particles having internal cavities.

The antireflection layer has a single layer and a multilayer, and when used as a single layer, it is preferable that the refractive index is at least 0.1 or more lower than the refractive index of the hard coat layer. In order to effectively exhibit the antireflection function, it is preferable to use a multilayer antireflection film, in which case the low refractive index film and the high refractive index film are alternately laminated. In this case as well, 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 such as ZnO, TiO ₂ , CeO ₂ , Sb ₂ O ₅ , SnO ₂ , ZrO ₂ , and Ta ₂ O _5, and examples of the low-refractive index film include SiO _{2 film.} ..

An anti-fog layer, an anti-contamination layer, and a water-repellent layer may be formed on the anti-reflection layer, if necessary. The method for forming the anti-fog layer, the anti-fouling 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, and known anti-fog treatment is performed. Methods, antifouling treatment methods, water repellent treatment methods, materials can be used. For example, in the anti-fog treatment method and the anti-fouling treatment method, a method of covering the surface with a surfactant, 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 superhydrophobic treatment to prevent the adhesion of water droplets, and the like. Further, as a water-repellent treatment method, 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 the water-repellent treatment layer to form a water-repellent treatment layer. And so on.

Although the embodiments of the present disclosure have been described above, these are examples of the present disclosure, and various configurations other than the above can be adopted as long as the effects in the present disclosure are not impaired.

Hereinafter, the present disclosure will be described in more detail by way of examples, but the present disclosure is not limited thereto. The evaluation methods and materials used in the examples of the present disclosure are as follows.

[Measurement method of spectral transmittance and visual transmittance]
A Shimadzu spectrophotometer UV-1800 manufactured by Shimadzu Corporation was used as a measuring device, and the ultraviolet-visible light spectrum was measured using a flat plate lens with a thickness of 2 mm to obtain a spectral transmittance curve. The visual transmittance was calculated based on the obtained spectral transmittance.

[Measurement method of L *, a *, b *]
Using a spectrophotometer (CM-5 manufactured by Konica Minolta), under the following measurement conditions, L *, a *, in the CIE1976 (L *, a *, b *) color system of a 2 mm thick flat plate lens. b * was measured.
~Measurement condition~
Light source: C Light source Measurement method: Transmission measurement Measurement area: Circular viewing angle with a diameter of 30 mm: 2 ° field of view

[YI measurement method]
YI was measured with a 2 mm thick flat lens with a spectrophotometer CM-5 manufactured by Konica Minolta.

[Measurement method of haze and total light transmittance]
The haze and total light transmittance of a 2 mm thick flat lens were measured with a HazeMeter NDH2000 manufactured by Nippon Denshoku Kogyo Co., Ltd.

In the examples, the near-infrared absorber shown below was used.

化学式（Ｉ−１）で表される近赤外線吸収剤Ａの３．７質量ｐｐｍのトルエン溶液で、光路長１０ｍｍにて、測定された可視光吸収分光スペクトルにおいて、７２０ｎｍに主吸収ピーク（Ｐ）を有し、上記ピーク（Ｐ）のピーク頂点（Ｐｍａｘ：ピーク中で最大吸光係数を示す点）の吸光係数（ｍｌ／ｇ・ｃｍ）が１．５７×１０^５であり、上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の１／４の吸光度におけるピーク幅が４３ｎｍであり、かつ上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の１／２の吸光度におけるピーク幅が２８ｎｍであり、かつ上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の２／３の吸光度におけるピーク幅が２０ｎｍであった。・ Near infrared absorber A

The main absorption peak (P) at 720 nm in the visible light absorption spectroscopic spectrum measured with a toluene solution of 3.7 mass ppm of the near-infrared absorber A represented by the chemical formula (I-1) at an optical path length of 10 mm. has a peak apex of the peak (P): 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.

化学式（ＩＩ−１）で表される近赤外線吸収剤Ｂの５．２質量ｐｐｍのトルエン溶液で、光路長１０ｍｍにて、測定された可視光吸収分光スペクトルにおいて、８３０ｎｍに主吸収ピーク（Ｐ）を有し、上記ピーク（Ｐ）のピーク頂点（Ｐｍａｘ：ピーク中で最大吸光係数を示す点）の吸光係数（ｍｌ／ｇ・ｃｍ）が１．１１×１０^５であり、上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の１／４の吸光度におけるピーク幅が８０ｎｍであり、かつ上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の１／２の吸光度におけるピーク幅が４７ｎｍであり、かつ上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の２／３の吸光度におけるピーク幅が３５ｎｍであった。・ Near infrared absorber B

The main absorption peak (P) at 830 nm in the visible light absorption spectroscopic spectrum measured with a 5.2 mass ppm toluene solution of the near-infrared absorber B represented by the chemical formula (II-1) at an optical path length of 10 mm. has a peak apex of the peak (P): 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) is (Pmax). The peak width at the absorbance of 2/3 of the absorbance of (Pmax) of P) was 35 nm.

化学式（ＩＩＩ−１）で表される近赤外線吸収剤Ｃの８．０質量ｐｐｍのトルエン溶液で、光路長１０ｍｍにて、測定された可視光吸収分光スペクトルにおいて、１００５ｎｍに主吸収ピーク（Ｐ）を有し、上記ピーク（Ｐ）のピーク頂点（Ｐｍａｘ：ピーク中で最大吸光係数を示す点）の吸光係数（ｍｌ／ｇ・ｃｍ）が７．２２×１０^４であり、上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の１／４の吸光度におけるピーク幅が２５０ｎｍであり、かつ上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の１／２の吸光度におけるピーク幅が１１２ｎｍであり、かつ上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の２／３の吸光度におけるピーク幅が８１ｎｍであった。・ Near infrared absorber C

The main absorption peak (P) at 1005 nm in the visible light absorption spectroscopic spectrum measured with a toluene solution of 8.0 mass ppm of the near-infrared absorber C represented by the chemical formula (III-1) at an optical path length of 10 mm. has a peak apex of the peak (P): 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 the absorbance of 1/4 of the absorbance of (Pmax) is 250 nm, and the peak width at the absorbance of 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.

近赤外線吸収剤Ｄの３．３質量ｐｐｍのトルエン溶液で、光路長１０ｍｍにて、測定された可視光吸収分光スペクトルにおいて、７８０ｎｍに主吸収ピーク（Ｐ）を有し、上記ピーク（Ｐ）のピーク頂点（Ｐｍａｘ：ピーク中で最大吸光係数を示す点）の吸光係数（ｍｌ／ｇ・ｃｍ）が１．７５×１０^５であり、上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の１／４の吸光度におけるピーク幅が３７ｎｍであり、かつ上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の１／２の吸光度におけるピーク幅が２４ｎｍであり、かつ上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の２／３の吸光度におけるピーク幅が１７ｎｍであった。・ Near infrared absorber D

A 3.3 mass ppm toluene solution of the near-infrared absorber D, having a main absorption peak (P) at 780 nm in the visible light absorption spectral spectrum measured at an optical path length of 10 mm, of the above peak (P). 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 in the absorbance of the above peak (P) is 37 nm, and the peak width in the absorbance of 1/2 of the absorbance of the peak (P) (Pmax) is 24 nm, and the absorbance of the peak (P) (Pmax) is 2. The peak width at the absorbance of / 3 was 17 nm.

近赤外線吸収剤Ｅの３６．５質量ｐｐｍのトルエン溶液で、光路長１０ｍｍにて、測定された可視光吸収分光スペクトルにおいて、９３５ｎｍに主吸収ピーク（Ｐ）を有し、上記ピーク（Ｐ）のピーク頂点（Ｐｍａｘ：ピーク中で最大吸光係数を示す点）の吸光係数（ｍｌ／ｇ・ｃｍ）が１．５８×１０^４であり、かつ上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の１／２の吸光度におけるピーク幅が３７９ｎｍであり、かつ上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の２／３の吸光度におけるピーク幅が２５２ｎｍであった。なお、上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の１／４の吸光度におけるピーク幅は、上記ピーク（Ｐ）の（Ｐｍａｘ）の吸光度の１／４となる値が存在しなかったことから測定することができなかった。・ 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 has a main absorption peak (P) of 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). I couldn't.

[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 preparation, and the mixture 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 μm PTFE filter, and then poured 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. After cooling to room temperature, 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 characteristics of the flattened lens subjected to this annealing treatment were measured. The results are shown in Table 1.

[Examples 2 to 7]
A flat plate 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 characteristics 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 plate 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 thereof was the amount shown in Table 1. Table 1 shows the measurement results of the physical characteristics 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 plate 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 thereof was the amount shown in Table 1. Table 1 shows the measurement results of the physical characteristics of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 13 is shown in FIG.

[Comparative Example 3]
The near-infrared absorber A was changed to the near-infrared absorber D, and the mixture was stirred at 25 ° C. for 1 hour in the same manner as in Example 1 except that the addition amount was 0.00165 parts by weight. However, the near-infrared absorber D did not dissolve.

[Comparative Example 4]
The near-infrared absorber A was changed to the near-infrared absorber E, and the mixture was stirred at 25 ° C. for 1 hour in the same manner as in Example 1 except that the amount added was 0.01825 parts by weight. However, the near-infrared absorber E did not dissolve.

[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 (isosianatomethyl) ) Vicyclo- [2.2.1] -heptane and 2,6-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane in an amount of 50.6 parts by weight, 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. Then, 25.5 parts by weight of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and 23.9 parts by weight of pentaerythritol tetrakis (3-mercaptopropionate) were added to this preparation solution. This was stirred at 25 ° C. for 30 minutes to obtain a uniform solution. This solution was defoamed at 400 Pa for 1 hour, filtered through a 1 μm PTFE filter, and then poured 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. After cooling to room temperature, 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 characteristics of the flattened lens subjected to this annealing treatment were measured. The results are shown in Table 2.

[Examples 15 to 20]
A flat plate 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 characteristics 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 plate 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 thereof was the amount shown in Table 2. Table 2 shows the measurement results of the physical characteristics 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 plate 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 thereof was the amount shown in Table 2. Table 2 shows the measurement results of the physical characteristics of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 24 is shown in FIG.

[Comparative Example 7]
The near-infrared absorber A was changed to the near-infrared absorber D, and the mixture was stirred at 25 ° C. for 1 hour in the same manner as in Example 14 except that the amount added was 0.00165 parts by weight. However, the near-infrared absorber D did not dissolve.

[Comparative Example 8]
A flat plate 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 thereof was the amount shown in Table 2. Table 2 shows the measurement results of the physical characteristics 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. A mixture of 9-trichiaundecane and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane was charged in 49.3 parts by weight, and the mixture was stirred at 25 ° C. for 30 minutes. , A uniform solution. This solution was defoamed at 400 Pa for 1 hour, filtered through a 1 μm PTFE filter, and then poured 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. After cooling to room temperature, 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 characteristics of the flattened lens subjected to this annealing treatment were measured. The results are shown in Table 3.

[Examples 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 characteristics of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 26 is shown in FIG.

[Examples 29 to 30, Comparative Example 9]
A flat plate 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 thereof was the amount shown in Table 3. Table 3 shows the measurement results of the physical characteristics 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 plate 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 thereof was the amount shown in Table 3. Table 3 shows the measurement results of the physical characteristics of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 32 is shown in FIG.

[Comparative Example 11]
The near-infrared absorber A was changed to the near-infrared absorber D, and the mixture was stirred at 25 ° C. for 1 hour in the same manner as in Example 25 except that the addition amount was 0.00165 parts by weight. However, the near-infrared absorber D did not dissolve.

[Comparative Example 12]
The near-infrared absorber A was changed to the near-infrared absorber E, and the mixture was stirred at 25 ° C. for 30 minutes in the same manner as in Example 25 except that the amount added was 0.01825 parts by weight. However, the near-infrared absorber E did not dissolve.

[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 TinuvinPS, 90 parts by weight of bis (2,3-epithiopropyl) disulfide. .92 parts by weight, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane and 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-tri 9.08 parts by weight of a mixture of thiaundecane and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trichiaundecan, 0.00042 part by weight of near-infrared absorber A, and nitrogen. The mixture was mixed and dissolved by stirring at 25 ° C. for 30 minutes under an atmosphere.
This mixed solution was defoamed at 400 Pa for 1 hour, filtered through a 1 μm PTFE filter, and then poured into a glass mold for a flat plate 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. After cooling to room temperature, 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 characteristics of the flattened lens subjected to this annealing treatment were measured. The results are shown in Table 4.

[Examples 34 to 39]
A flat plate 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 characteristics of the obtained flat plate 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 plate 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 thereof was the amount shown in Table 4. Table 4 shows the measurement results of the physical characteristics of the obtained flat plate 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 plate 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 thereof was the amount shown in Table 4. Table 4 shows the measurement results of the physical characteristics of the obtained flat lens. Further, the spectral transmittance curve of the flat plate lens of Example 43 is shown in FIG.

[Comparative Example 15]
The near-infrared absorber A was changed to the near-infrared absorber D, and the mixture was stirred at 25 ° C. for 1 hour in the same manner as in Example 33 except that the addition amount was 0.00165 parts by weight. However, the near-infrared absorber D did not dissolve.

[Comparative Example 16]
The near-infrared absorber A was changed to the near-infrared absorber E, and the mixture was stirred at 25 ° C. for 1 hour in the same manner as in Example 33 except that the amount added was 0.01825 parts by weight. However, the near-infrared absorber E did not dissolve.

[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, 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. Then, 26.7 parts by weight of pentaerythritol tetrakis (2-mercaptoacetate) and 26.24 parts by weight of 2,5-bis (mercaptomethyl) -1,4-dithiane were added to this preparation solution, and 25 parts by weight was added. The mixture was stirred at ° C. for 30 minutes to obtain a uniform solution. This solution was defoamed at 400 Pa for 1 hour, filtered through a 1 μm PTFE filter, and then poured 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. After cooling to room temperature, 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 characteristics of the flattened lens subjected to this annealing treatment were measured. The results are shown in Table 5.

[Example 45]
A flat plate 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 characteristics of the obtained flat lens.

[Example 46]
A flat plate 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 characteristics of the obtained flat lens.

[Comparative Example 17]
The near-infrared absorber A was changed to the near-infrared absorber D, and the mixture was stirred at 25 ° C. for 1 hour in the same manner as in Example 44 except that the addition amount was 0.00165 parts by weight. However, the near-infrared absorber D did not dissolve.

[Comparative Example 18]
A flat plate 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 characteristics of the obtained flat lens.

[Example 101 and Example 102]
Polycarbonate resin (Panlite L-1225WP manufactured by Teijin Limited) and the near-infrared absorber shown in Table 6 are mixed by a tumbler in an amount such that the content of the near-infrared absorber is the content shown in Table 6. After partial mixing, 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).
Using the prepared pellets as a raw material, a flat plate 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 characteristics of the obtained flat lens.

The monomer types shown in Tables 1 to 5 are as follows.
a1: m-xylylene diisocyanate a2: 2,5-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane and 2,6-bis (isocyanatomethyl) bicyclo- [2.2.1] -Mixed with heptane a3: 1,3-bis (isocyanatomethyl) cyclohexane b1: 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane b2: pentaerythritol tetrakis (3-mercaptopropionate)
b3: 5,7-Dimercaptomethyl-1,11-Dimercapto-3,6,9-Trithiandecan and 4,7-Dimercaptomethyl-1,11-Dimercapto-3,6,9-Trithiandecan And 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane b4: pentaerythritol tetrakis (2-mercaptoacetate)
b5: 2,5-bis (mercaptomethyl) -1,4-dithian c1: bis (2,3-epithiopropyl) disulfide

The disclosure of Japanese Patent Application No. 2019-08615 filed on April 26, 2019 is incorporated herein by reference in its entirety.
All documents, patent applications, and technical standards described herein are to the same extent as if the individual documents, patent applications, and technical standards were specifically and individually stated to be incorporated by reference. Incorporated herein by reference.

Claims (36)

A resin that is at least one selected from the group consisting of polycarbonate resin, (thio) urethane resin, and episulfide resin, and
Near-infrared absorber and
Including
An optical material in which a * is -30 or more and 0 or less and L * is 80 or more in the CIE1976 (L *, a *, b *) color space measured at a thickness of 2 mm. The optical material according to claim 1, wherein 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. The optical material according to claim 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. The optical material according to claim 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. The optical material according to any one of claims 1 to 4, wherein the visual transmittance at a thickness of 2 mm is 70% or more. 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) a wavelength region of 1000 nm to 1100 nm in the spectral transmittance curve. The optical material according to any one of claims 1 to 5, which has a minimum value of less than 50% spectral transmittance within at least one range of the wavelength region. The optical material according to any one of claims 1 to 6, 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 the visible light absorption spectroscopic spectrum measured with a toluene solution, and the peak peak (Pmax: maximum absorbance in the peak) of the peak (P). The absorption coefficient (ml / g · cm) of the point indicating the 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 peak is The peak width in the absorbance of 1/2 of the absorbance of (Pmax) of (P) is 130 nm or less, and the peak width in the absorbance of 2/3 of the absorbance of (Pmax) of the peak (P) is in the range of 90 nm or less. The optical material according to claim 7. The optical material according to claim 7 or 8, wherein the phthalocyanine compound contains at least one compound represented by the general formulas (I) to (III).

(In the general formula (I), 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 each independently represent a hydrogen atom or a halogen atom. 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.)

In the general formula (II), R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are linear or branched alkyl groups, alkoxyalkyl groups or dialkylaminoalkyl groups. Shown, X ₁ , X ₂ , X ₃ , X ₄ , X ₅ , X ₆ , X ₇ , X ₈ indicate a sulfur atom or> NR ₉ , and X ₁ = ( _{either X 3} or X ₄ ). = (One of X ₅ and X ₆ ) = (one of X ₇ and X ₈ ) = sulfur atom and X ₂ = ( _{the other of X 3} and X ₄ ) = (X ₅ and X) _{The other of 6} ) = (the other of X ₇ and X ₈ ) => NR _9. R ₉ represents a hydrogen atom or an alkyl group, and M is two hydrogen atoms, a divalent metal or a trivalent. Or a tetravalent metal derivative.)

(In the general formula (III), R _{1 to} R ₄ each independently represent an alkyl group or an alkoxyalkyl group, and X is a phenylthio group or a substituent which may have a halogen atom, an alkylthio group or a substituent. It indicates a naphthylthio group which may be possessed, and M indicates two hydrogen atoms, a divalent metal or a derivative of a trivalent or tetravalent metal.) 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) spectroscopic within the wavelength region of 700 nm to 750 nm in the spectral transmittance curve. The optical material according to claim 9, which has a minimum value of less than 50% transmittance. The optical material according to claim 10, wherein the phthalocyanine compound contains a compound represented by the general formula (I). 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, and the near-infrared absorber has (2) a spectral transmittance within the wavelength range of 825 nm to 875 nm in the spectral transmittance curve. The optical material according to claim 9, which has a minimum value of less than 50%. The optical material according to claim 12, wherein the phthalocyanine compound contains a compound represented by the general formula (II). 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 has a spectral transmittance within the range of the wavelength region of 1000 nm to 1100 nm in (3) the spectral transmittance curve. The optical material according to claim 9, which has a minimum value of less than 50%. The optical material according to claim 14, wherein the phthalocyanine compound contains a compound represented by the general formula (III). The optical material according to any one of claims 1 to 15, which contains the near-infrared absorber in an amount of 3 ppm or more and 80 ppm or less. The optical material according to any one of claims 1 to 16, wherein the near-infrared absorber contains a plurality of phthalocyanine compounds having different structures in combination. The (thio) urethane resin is composed of at least one of a constituent unit derived from a polyisocyanate compound, a constituent unit derived from a polythiol compound, and a constituent 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, and the like. 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 include 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiandecan, 4,7-. Dimercaptomethyl-1,11-dimercapto-3,6,9-trithiandecan, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithianeundecane, pentaerythritol tetrakis (3- Mercaptopropionate), bis (mercaptoethyl) sulfide, pentaerythritol tetrakis (2-mercaptoacetate), 2,5-bis (mercaptomethyl) -1,4-dithiane, 1,1,3,3-tetrakis (mercapto) Methylthio) Propane, at least one selected from 4,6-bis (mercaptomethylthio) -1,3-dithiane, and 2- (2,2-bis (mercaptomethylthio) ethyl) -1,3-dithiane.
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 claims 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, a structural unit derived from an episulfide compound, and a structural unit derived from a polythiol compound.
The episulfide compounds include bis (2,3-epithiopropyl) sulfide, bis (2,3-epiothiopropyl) disulfide, bis (1,2-epithioethyl) sulfide, bis (1,2-epithioethyl) 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. The optical material according to any one of claims 1 to 17, which is at least one selected from −cyclohexanediol and 1,4-cyclohexanediol. A polymerizable composition used for producing the optical material according to any one of claims 1 to 19.
A polymerizable compound composed 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.
At least one range of (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) a wavelength region of 1000 nm to 1100 nm in the spectral transmittance curve. A near-infrared absorber having a minimum spectral transmittance of less than 50%,
A polymerizable composition for an optical material containing. The polymerizable composition for an optical material according to claim 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 the visible light absorption spectroscopic spectrum measured with a toluene solution, and the peak peak (Pmax: maximum absorbance in the peak) of the peak (P). The absorbance coefficient (ml / g · cm) of the point indicating the 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 peak is The peak width in the absorbance of 1/2 of the absorbance of (Pmax) of (P) is 130 nm or less, and the peak width in the absorbance of 2/3 of the absorbance of (Pmax) of the peak (P) is in the range of 90 nm or less. 21. The polymerizable composition for an optical material according to claim 21. The polymerizable composition for an optical material according to claim 21, wherein the phthalocyanine compound contains at least one compound represented by the general formulas (I) to (III).

(In the general formula (I), 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 each independently represent a hydrogen atom or a halogen atom. 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.)

In the general formula (II), R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are linear or branched alkyl groups, alkoxyalkyl groups or dialkylaminoalkyl groups. Shown, X ₁ , X ₂ , X ₃ , X ₄ , X ₅ , X ₆ , X ₇ , X ₈ indicate a sulfur atom or -NR ₉ , and X ₁ = ( _{either X 3} or X ₄ ). = (One of X ₅ and X ₆ ) = (one of X ₇ and X ₈ ) = sulfur atom and X ₂ = ( _{the other of X 3} and X ₄ ) = (X ₅ and X) _{The other of 6} ) = (the other of X ₇ and X ₈ ) = -NR _9. R ₉ represents a hydrogen atom or an alkyl group, and M is two hydrogen atoms, a divalent metal or a trivalent. Or a tetravalent metal derivative.)

(In the general formula (III), R _{1 to} R ₄ each independently represent an alkyl group or an alkoxyalkyl group, and X is a phenylthio group or a substituent which may have a halogen atom, an alkylthio group or a substituent. It indicates a naphthylthio group which may be possessed, and M indicates two hydrogen atoms, a divalent metal or a derivative of a trivalent or tetravalent metal.) A polymerizable composition used for producing an optical material having 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 polymerizable composition for an optical material according to claim 23, wherein the near-infrared absorber has (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. The polymerizable composition for an optical material according to claim 24, wherein the phthalocyanine compound contains a compound represented by the general formula (I). A polymerizable composition used for producing an optical material having 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 polymerizable composition for an optical material according to claim 23, wherein the near-infrared absorber has (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. The polymerizable composition for an optical material according to claim 26, wherein the phthalocyanine compound contains a compound represented by the general formula (II). A polymerizable composition used for producing an optical material having 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 polymerizable composition for an optical material according to claim 23, wherein the near-infrared absorber has (3) a minimum value of less than 50% spectral transmittance in the wavelength region of 1000 nm to 1100 nm in the spectral transmittance curve. The polymerizable composition for an optical material according to claim 28, wherein the phthalocyanine compound contains a compound represented by the general formula (III). The polymerizable composition for an optical material according to any one of claims 20 to 29, which comprises 3 ppm or more and 80 ppm or less of the near-infrared absorber. The polymerizable composition for an optical material according to any one of claims 20 to 30, wherein the near-infrared absorber contains a combination of a plurality of phthalocyanine compounds having different structures. The polyisocyanate compound is 2,5-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, 2,6-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, and the like. 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 include 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiandecan, 4,7-. Dimercaptomethyl-1,11-dimercapto-3,6,9-trithiandecan, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithianeundecane, pentaerythritol tetrakis (3- Mercaptopropionate), bis (mercaptoethyl) sulfide, pentaerythritol tetrakis (2-mercaptoacetate), 2,5-bis (mercaptomethyl) -1,4-dithiane, 1,1,3,3-tetrakis (mercapto) Methylthio) Propane, at least one selected from 4,6-bis (mercaptomethylthio) -1,3-dithiane, and 2- (2,2-bis (mercaptomethylthio) ethyl) -1,3-dithiane.
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 claims 20 to 31, which is at least one selected from -cyclohexanediol and 1,4-cyclohexanediol. The episulfide compounds include bis (2,3-epithiopropyl) sulfide, bis (2,3-epiothiopropyl) disulfide, bis (1,2-epithioethyl) sulfide, bis (1,2-epithioethyl) disulfide, and , The polymerizable composition for an optical material according to any one of claims 20 to 31, which is at least one selected from bis (2,3-epithiopropylthio) methane. A plastic lens made of the optical material according to any one of claims 1 to 19. Eyewear comprising the plastic lens according to claim 34. An infrared sensor or an infrared camera comprising the plastic lens according to claim 34.

Images