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WO2013168565A1 - Composition de résine et article moulé - Google Patents

Composition de résine et article moulé Download PDF

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Publication number
WO2013168565A1
WO2013168565A1 PCT/JP2013/061990 JP2013061990W WO2013168565A1 WO 2013168565 A1 WO2013168565 A1 WO 2013168565A1 JP 2013061990 W JP2013061990 W JP 2013061990W WO 2013168565 A1 WO2013168565 A1 WO 2013168565A1
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Prior art keywords
group
substituted
unsubstituted
carbon atoms
compound
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PCT/JP2013/061990
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English (en)
Japanese (ja)
Inventor
尊道 尼子
健一郎 堀内
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Yamamoto Chemicals Inc
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Yamamoto Chemicals Inc
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Priority to JP2014514666A priority Critical patent/JP6117192B2/ja
Publication of WO2013168565A1 publication Critical patent/WO2013168565A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments

Definitions

  • the present invention relates to a resin composition used for an optical material and a molded body formed by molding the resin composition. More specifically, the present invention relates to a resin composition that is less colored and has a high effect of cutting wavelengths that cause glare and adverse effects on the human body, and a molded body formed by molding the resin composition, particularly a resin composition for optical materials and an optical article. Moreover, this invention relates to the adhesive containing the said resin composition, and the optical article containing this.
  • a neodymium compound has a sharp absorption in the vicinity of 570 to 590 nm, and has a feature that it can selectively absorb light of 550 to 610 nm, which is highly visible to humans and easily feels dazzling.
  • inorganic rare earth metal compounds such as neodymium compounds are easily compounded into glass lenses, but in recent years plastics are mainly used as a material for eyeglass lenses, and inorganic rare earth metal compounds are uniformly transparent lenses. There is a problem that it cannot be dispersed and mixed in the resin.
  • Patent Documents 2 to 4 disclose a technique in which a tetraazaporphyrin compound is contained in a plastic spectacle lens instead of a neodymium compound to cut light in the vicinity of 580 nm to 590 nm, thereby providing antiglare property and visibility. ing.
  • a tetraazaporphyrin compound is contained in a plastic spectacle lens instead of a neodymium compound to cut light in the vicinity of 580 nm to 590 nm, thereby providing antiglare property and visibility.
  • a tetraazaporphyrin compound is contained in a plastic spectacle lens instead of a neodymium compound to cut light in the vicinity of 580 nm to 590 nm, thereby providing antiglare property and visibility.
  • a tetraazaporphyrin compound is contained in a plastic spectacle lens instead of a neodymium compound to cut light in the vicinity of 580 nm to 590 nm
  • Patent Document 5 discloses a spectacle lens that uses a yellow dye or an orange dye as a blue light absorber.
  • Patent Document 6 discloses a spectacle lens using a yellow dye or an orange dye as a blue light absorber and a squarylium compound as an organic dye having a maximum absorption value near 555 nm, which is the central wavelength of the standard relative luminous sensitivity curve.
  • Patent Document 7 discloses an antiglare optical article using a yellow dye or an orange dye as a blue light absorber and a squarylium compound as an organic dye having a maximum absorption value in a wavelength range of 550 to 600 nm.
  • Patent Documents 10 to 12 disclose the use of a wavelength selection layer or a color correction film containing a tetraazaporphyrin compound in order to improve the color reproducibility of a liquid crystal display using an LED light source as a backlight.
  • the blue light emitted from the LED light source is also efficiently cut, which not only prevents glare and adverse effects on the human body, but also suppresses color change caused by external light such as unnecessary light emission and illumination, and the filter itself
  • An optical filter with almost no coloring is not known.
  • the subject of this invention is providing the resin composition and molded object which are excellent in anti-glare performance and unnecessary light cut performance, and are little coloring. More specifically, it effectively cuts blue light in the vicinity of 380 nm to 460 nm and light with high human visibility near 580 nm to 590 nm, prevents glare and glare, increases contrast, and has little coloration, so the appearance of the product
  • An optical article such as a spectacle lens, a sun visor, a helmet shield, a display device coat, a display mounting optical filter, or a spectacle lens mounting optical filter formed by molding a resin composition having an excellent application range. Is to provide.
  • the subject of the present invention is a resin composition capable of preventing adverse effects on the human body due to display or illumination using an LED light source, automobile light, etc., by efficiently cutting blue light contained in a large amount in the LED light source, It is in providing a molded object and an optical article.
  • the other subject of this invention is providing the adhesive which contains the said resin composition, and the optical article containing this.
  • the present invention (I) (A) a resin, (B) a tetraazaporphyrin compound (B-1) represented by the following general formula (1) as an organic dye, and a maximum absorption between wavelengths of 380 to 470 nm in a toluene solution And a ratio (A1 / A2) of the absorbance (A1) at the maximum absorption wavelength between 520 to 800 nm and the absorbance (A2) at the maximum absorption wavelength between 380 to 470 nm is less than 0.1 ( B-2) at least, and a resin composition, [In formula (1), R 1 to R 8 are each independently a hydrogen atom, halogen atom, cyano group, nitro group, alkyl group, alkenyl group, halogenoalkyl group, alkoxy group, halogenoalkoxy group, alkylthio group, alkoxy group.
  • M represents two hydrogen atoms, two monovalent
  • Z 1 to Z 9 are each independently a hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, mercapto group, carboxyl group, alkyl group, alkenyl group, halogenoalkyl group, alkoxy group, Halogenoalkoxy group, alkylthio group, alkoxyalkyl group, alkoxyalkoxyalkyl group, halogenoalkoxyalkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted aralkyl group, substituted or unsubstituted amino group, substituted or unsubstituted Amide group, substituted or unsubstituted acyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted aryloxyal
  • X 1 to X 8 are each independently a hydrogen atom, a halogen atom, an alkyl group, a halogenoalkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, a substituted or unsubstituted aryl group, a substituted or An unsubstituted aralkyl group or a substituted or unsubstituted arylthio group is shown.
  • at least one of X 1 to X 8 is necessarily a substituted or unsubstituted arylthio group.
  • R 1 to R 8 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an alkyl group having 1 to 12 carbon atoms.
  • Halogenoalkyl group alkoxy group having 1 to 12 carbon atoms, halogenoalkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, alkoxyalkyl group having 2 to 16 carbon atoms, halogenoalkoxy having 2 to 16 carbon atoms
  • Y 1 to Y 11 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an alkyl group having 1 to 12 carbon atoms.
  • Halogenoalkyl group alkoxy group having 1 to 12 carbon atoms, halogenoalkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, alkoxyalkyl group having 2 to 16 carbon atoms, alkoxyalkoxy having 3 to 20 carbon atoms Alkyl group, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted amino group having 1 to 18 carbon atoms, substituted or unsubstituted amide group having 1 to 18 carbon atoms, 7 to 20 carbon atoms Substituted or unsubstituted aralkyl groups, substituted or unsubstituted aryloxy groups having 6 to 18 carbon atoms, substituted or unsubstituted aryloxyalkyl groups having 7 to 20 carbon atoms, Any of (iii) to (vi) is an alkyloxycarbonyl group having 2 to 13 prime atoms
  • Z 1 to Z 9 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an alkyl group having 1 to 12 carbon atoms.
  • Halogenoalkyl group alkoxy group having 1 to 12 carbon atoms, halogenoalkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, alkoxyalkyl group having 2 to 16 carbon atoms, alkoxyalkoxy having 3 to 20 carbon atoms Alkyl group, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted amino group having 1 to 18 carbon atoms, substituted or unsubstituted amide group having 1 to 18 carbon atoms, 7 to 20 carbon atoms Substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted aryloxyalkyl group having 7 to 20 carbon atoms, carbon Alkyloxycarbonyl group having 2 to 13, a substituted or unsubstituted aryloxycarbon
  • X 1 to X 8 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, a halogenoalkyl group having 1 to 12 carbon atoms, or 1 to 12 carbon atoms.
  • An alkoxy group having 1 to 12 carbon atoms, an alkoxyalkyl group having 2 to 16 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms, and at least one of X 1 to X 8 must be carbon (V) to (viii) any one of the resin compositions, which is a substituted or unsubstituted arylthio group of formula 6-18,
  • thermoplastic resin is at least one selected from a polycarbonate resin, a polyamide resin, an acrylic resin, and a polyester resin
  • thermosetting resin is at least selected from a polyurethane resin, a polythiourethane resin, and an allyl diglycol carbonate resin.
  • the resin composition of the present invention can efficiently cut blue light in the vicinity of 380 nm to 460 nm and light having high human visibility near 580 nm to 590 nm, prevent glare and glare, and increase contrast. Moreover, the blue light contained abundantly in the LED light source can be efficiently cut to prevent adverse effects on the human body caused by a display or illumination using the LED light source, a car light, or the like. Furthermore, since there is almost no coloring, the molded product obtained by molding this is for anti-glare such as spectacle lens, sun visor, helmet shield, display device coat, display mounting optical filter, spectacle lens mounting optical filter, etc. It is very useful for optical articles, optical articles for reducing short wavelength light, and optical filters.
  • the resin composition of the present invention is particularly low in color and is almost colorless.
  • the resin composition of the present invention has high transparency because the dye is well dissolved in the resin. Therefore, visible light other than unnecessary light is transmitted well, and the decrease in light transmittance is small.
  • the resin composition of the present invention has high light resistance and little deterioration of the pigment in the resin, the optical fastness of a product using the resin composition is excellent.
  • 2 is a transmission spectrum of a resin composition according to Example 1-14 of the present invention.
  • 2 is a transmission spectrum of a resin composition according to Example 1-15 of the present invention.
  • 2 is a transmission spectrum of a resin composition according to Example 1-16 of the present invention. It is a transmission spectrum of the resin composition which concerns on Example 1-17 of this invention.
  • 2 is a transmission spectrum of a resin composition according to Example 1-18 of the present invention.
  • 2 is a transmission spectrum of a resin composition according to Example 1-19 of the present invention.
  • It is a transmission spectrum of the optical filter which concerns on Example 1-28 of this invention.
  • It is a transmission spectrum of the optical filter which concerns on Example 1-31 of this invention.
  • It is a transmission spectrum of the optical filter which concerns on Example 1-33 of this invention.
  • Example 37 is a schematic cross-sectional view of an optical filter according to Example 1-37 of the present invention. It is a transmission spectrum of the resin composition which concerns on Example 2-12 of this invention. It is a transmission spectrum of the resin composition which concerns on Example 2-13 of this invention. It is a transmission spectrum of the resin composition which concerns on Example 2-14 of this invention. It is a transmission spectrum of the resin composition which concerns on Example 2-15 of this invention. It is a transmission spectrum of the resin composition which concerns on Example 3-11 of this invention. It is a transmission spectrum of the optical filter which concerns on Example 3-32 of this invention.
  • the resin composition of the present invention comprises at least (A) a resin and (B) an organic dye.
  • the organic dye contains at least a tetraazaporphyrin-based compound (B-1) represented by the following general formula (1) and a compound (B-2) having specific light absorption characteristics.
  • B-1 a tetraazaporphyrin-based compound represented by the following general formula (1)
  • B-2 a compound having specific light absorption characteristics.
  • Compound (B-1) The tetraazaporphyrin-based compound (B-1) according to the resin composition of the present invention is represented by the following general formula (1).
  • R 1 to R 8 are each independently a hydrogen atom, halogen atom, cyano group, nitro group, alkyl group, alkenyl group, halogenoalkyl group, alkoxy group, halogenoalkoxy group, alkylthio group, alkoxy group.
  • M represents two hydrogen atoms, two monovalent
  • a halogen atom a cyano group, a nitro group, a hydroxyl group, a mercapto group, a carboxyl group, an alkyl group, an alkenyl group, a halogeno
  • R 1 to R 8 are preferably each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an alkyl group having 1 to 12 carbon atoms.
  • Halogenoalkyl group alkoxy group having 1 to 12 carbon atoms, halogenoalkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, alkoxyalkyl group having 2 to 16 carbon atoms, halogenoalkoxy having 2 to 16 carbon atoms
  • R 1 to R 8 are more preferably each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, An alkoxy group having 1 to 8 carbon atoms, a halogenoalkoxy group having 1 to 8 carbon atoms, an alkylthio group having 1 to 8 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, a halogenoalkoxyalkyl group having 2 to 12 carbon atoms, carbon A substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted amino group having 1 to 14 carbon atoms,
  • M is more preferably Cu, Pt, Pd, Ni or VO.
  • R 1 to R 8 Specific examples of R 1 to R 8 will be described below. Examples of those in which R 1 to R 8 are halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, a fluorine atom, a chlorine atom, and a bromine atom are preferable, and a chlorine atom is particularly preferable.
  • R 1 to R 8 are alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl.
  • R 1 to R 8 are alkenyl groups such as vinyl, propenyl, 1-butenyl, isobutenyl, 1-pentenyl, 2-pentenyl, 2-methyl-1-butenyl, 1-hexenyl
  • a vinyl group, a propenyl group, and a 1-butenyl group are preferable, and a vinyl group and a propenyl group are more preferable.
  • R 1 to R 8 are halogenoalkyl groups
  • R 1 to R 8 are alkyl groups in which an alkyl group is substituted with a chlorine atom or a fluorine atom.
  • R 1 to R 8 are alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, n-pentyloxy group, cyclopentyloxy group, n -Hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n- Undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy Group, n-tricosyloxy
  • a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, sec -Butoxy group, n-pentyloxy group, n-hexyloxy group, 2-ethylbutyloxy group, cyclohexyloxy group, n-heptyloxy group, and n-octyloxy group are more preferable.
  • R 1 to R 8 are halogenoalkoxy groups
  • R 1 to R 8 are halogenoalkoxy groups
  • R 1 to R 8 are halogenoalkoxy groups
  • R 1 to R 8 are halogenoalkoxy groups
  • Fluoromethoxy group trifluoromethoxy group, 2-fluoroethoxy group, perfluoroethoxy group, 3-fluoropropyloxy group, 4-fluoroisobutyloxy group, chloromethoxy group, dichloromethoxy group, trichloromethoxy group, 2-chloro An ethoxy group, 2,2,2-trichloroethoxy group, and 3-chloropropyloxy group are more preferable.
  • R 1 to R 8 are alkylthio groups such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, n-pentylthio, cyclopentylthio, n- Hexylthio group, 3,3-dimethylbutylthio group, 2-ethylbutylthio group, cyclohexylthio group, n-heptylthio group, n-octylthio group, 2-ethylhexylthio group, n-nonylthio group, n-undecylthio group, n -Dodecylthio group, n-tridecylthio group, n-tetradecylthio group, n-pentadecylthio group, n-hexadecylthio group, n
  • Isopropylthio group, n-butylthio group, sec-butylthio group, n-pentylthio group, n-hexylthio group, 3,3-dimethylbutylthio group, 2-ethylbutylthio group, cyclohexylthio group, n-heptylthio group, n -Octylthio group, 2-ethylhexylthio group, n-dodecylthio group are preferred, methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, sec-butylthio group, n-pentylthio group, n-hexylthio group Group, 2-ethylbutylthio group, cyclohexylthio group, n-heptylthio group, and n-o
  • R 1 to R 8 are alkoxyalkyl groups such as methoxymethyl group, ethoxymethyl group, n-butoxymethyl group, n-pentyloxymethyl group, n-hexyloxymethyl group, (2-ethylbutyloxy) Methyl group, n-heptyloxymethyl group, n-octyloxymethyl group, n-dodecyloxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-isopropoxyethyl group, 2-n-butoxyethyl group 2-n-hexyloxyethyl group, 2-n-heptyloxyethyl group, 2-n-octyloxyethyl group, 2-n-dodecyloxyethyl group, 2-n-tetradecyloxyethyl group, 2-cyclohexyl Oxyethyl, 2-methoxypropyl, 3-methoxyprop
  • R 1 to R 8 are alkoxyalkoxyalkyl groups such as (2-methoxyethoxy) methyl group, (2-ethoxyethoxy) methyl group, (2-n-butyloxyethoxy) methyl group, (3-methoxy) Propyloxy) methyl group, (3-ethoxypropyloxy) methyl group, (3-n-pentyloxypropyloxy) methyl group, (6-methoxyhexyloxy) methyl group, (10-ethoxydecyloxy) methyl group, 2 -(2-methoxyethoxy) ethyl group, 2- (2-ethoxyethoxy) ethyl group, 2- (3-ethoxypropyloxy) ethyl group, 2- (4-ethoxybutyloxy) ethyl group, 2- (4- Butyloxybutyloxy) ethyl group, 2- (5-methyloxypentyloxy) ethyl group, 3- (1-methoxyeth
  • R 1 to R 8 are halogenoalkoxyalkyl groups
  • R 1 to R 8 are alkoxyalkyl groups substituted with chlorine atoms or fluorine atoms.
  • fluoromethyloxymethyl Group trifluoromethyloxymethyl group, 2-fluoroethyloxymethyl group, perfluoroethyloxymethyl group, 3-fluoro-n-propyloxymethyl group, 1,1-dihydro-perfluoroethyloxymethyl group, 1, 1-dihydro-perfluoro-n-propyloxymethyl group, 1,1-dihydro-perfluoro-n-butyloxymethyl group, 1,1-dihydro-perfluoro-n-tetradecyloxymethyl group, fluoromethyloxy Ethyl group, trifluoromethyloxyethyl group, 2-fluoroethyl Xylethyl group, perfluoroethyloxyethyl group,
  • R 1 to R 8 are a substituted or unsubstituted aryl group includes a heteroaryl group, such as a phenyl group, 2-methylphenyl group, 4-methylphenyl group, 3-ethylphenyl group, 4-n -Propylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-tert-butylphenyl group, 4-n-pentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group 4-cyclohexylphenyl group, 4-n-octylphenyl group, 4-n-nonylphenyl group, 4-n-decylphenyl group, 4-n-dodecylphenyl group, 4-n-tetradecylphenyl group, 4- n-octadecylphenyl group, 2,5-dimethylphenyl group, 3,
  • R 1 to R 8 are substituted or unsubstituted aralkyl groups such as benzyl group, ⁇ -methylbenzyl group, ⁇ , ⁇ -dimethylbenzyl group, ⁇ -phenylbenzyl group, phenethyl group, ⁇ -methylphenethyl group , ⁇ , ⁇ -dimethylphenethyl group, 4-methylphenethyl group, 4-methylbenzyl group, 2-methylbenzyl group, 4-ethylbenzyl group, 4-isopropylbenzyl group, 4-tert-butylbenzyl group, 4-tert -Pentylbenzyl group, 4-cyclohexylbenzyl group, 4-n-octylbenzyl group, 4-ethenylbenzyl group, 4-phenylbenzyl group, 4- (4'-tert-butylphenyl) benzyl group, 4-methoxybenzyl Group, 3-methoxybenzyl group, 2-e
  • R 1 to R 8 are substituted or unsubstituted amino groups such as amino group, N-methylamino group, N-ethylamino group, Nn-propylamino group, Nn-butylamino group, N-cyclohexylamino group, Nn-octylamino group, N-benzylamino group, N-phenylamino group, N- (3-methylphenyl) amino group, N- (4-methoxyphenyl) amino group, N- (3-fluorophenyl) amino group, N- (4-chlorophenyl) amino group, N- (2-naphthyl) amino group, N, N-dimethylamino group, N, N-diethylamino group, N, N-di- n-propylamino group, N, N-di-n-butylamino group, N, N-di-n-octylamino group, N, N-di-n
  • R 1 to R 8 are substituted or unsubstituted acyl groups such as formyl group, acetyl group, propanoyl group, n-propylcarbonyl group, n-butylcarbonyl group, isobutylcarbonyl group, tert-butylcarbonyl group, n-pentylcarbonyl group, isopentylcarbonyl group, 2-methylbutylcarbonyl group, propenoyl group, benzoyl group, 4-methylbenzoyl group, 2,4-dimethylbenzoyl group, 3-chlorobenzoyl group, 4-dimethylaminobenzoyl group , 2-methoxybenzoyl group, 3-butoxy-2-naphthoyl group, cinnamoyl group, etc., including formyl group, acetyl group, propanoyl group, n-propylcarbonyl group, n-butylcarbonyl group, iso
  • R 1 to R 8 are substituted or unsubstituted aryloxy groups such as phenyloxy group, 2-methylphenyloxy group, 4-methylphenyloxy group, 4-ethylphenyloxy group, 4-isopropylphenyloxy Group, 4-isobutylphenyloxy group, 4-n-pentylphenyloxy group, 4-tert-pentylphenyloxy group, 4-cyclohexylphenyloxy group, 4-n-octylphenyloxy group, 4-n-decylphenyloxy group Group, 4-n-dodecylphenyloxy group, 4-n-hexadecylphenyloxy group, 2,3-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3, 4,5-trimethylphenyloxy group, 5-indanyloxy group, 1,2,3,4 Tetrahydro-6-naphthyloxy group
  • R 1 to R 8 are substituted or unsubstituted aryloxyalkyl groups
  • aryloxyalkyl groups include, for example, phenyloxymethyl group, 4-methylphenyloxymethyl group, 4-ethylphenyloxymethyl group, 4-n-butylphenyl Oxymethyl group, 4-n-hexylphenyloxymethyl group, 4-n-decylphenyloxymethyl group, 4-methoxyphenyloxymethyl group, 4-butoxyphenyloxymethyl group, 4-n-pentyloxyphenyloxymethyl group 4-fluorophenyloxymethyl group, 2-fluorophenyloxymethyl group, 3,4-difluorophenyloxymethyl group, 4-chlorophenyloxymethyl group, 4-phenylphenyloxymethyl group, 2-naphthyloxymethyl group, 1 -Phenyloxyethyl group, 2- (4'-methyl) Ruphenyloxy) ethyl group, 2- (4′-eth
  • Enyloxymethyl group 4-methylphenyloxymethyl group, 4-ethylphenyloxymethyl group, 4-n-butylphenyloxymethyl group, 4-n-hexylphenyloxymethyl group, 4-n-decylphenyloxymethyl group 4-methoxyphenyloxymethyl group, 4-butoxyphenyloxymethyl group, 4-fluorophenyloxymethyl group, 3,4-difluorophenyloxymethyl group, 4-chlorophenyloxymethyl group, 2-naphthyloxymethyl group, 1 -Phenyloxyethyl group, 2- (4'-methylphenyloxy) ethyl group, 2- (4'-ethylphenyloxy) ethyl group, 2- (4'-methoxyphenyloxy) ethyl group, 2- (4 ' -N-butoxyphenyloxy) ethyl group, 2- (4'-fluorophenyloxy) ethyl 2- (3′-chlorophen
  • R 1 to R 8 are substituted or unsubstituted aralkyloxy groups such as benzyloxy group, ⁇ -methylbenzyloxy group, ⁇ -ethylbenzyloxy group, ⁇ , ⁇ -dimethylbenzyloxy group, ⁇ -phenyl Benzyloxy group, ⁇ , ⁇ -diphenylbenzyloxy group, phenethyloxy group, ⁇ -methylphenethyloxy group, ⁇ -methylphenethyloxy group, ⁇ , ⁇ -dimethylphenethyloxy group, 4-methylphenethyloxy group, 4-methyl Benzyloxy group, 2-methylbenzyloxy group, 4-ethylbenzyloxy group, 2-ethylbenzyloxy group, 4-tert-butylbenzyloxy group, 2-tert-butylbenzyloxy group, 4-n-pentylbenzyloxy Group, 4-cyclohexylbenzyloxy group, 4-n-oc
  • R 1 to R 8 are substituted or unsubstituted aralkyloxyalkyl groups such as benzyloxymethyl group, phenethyloxymethyl group, 4-methylbenzyloxymethyl group, 4-n-propylbenzyloxymethyl group, 4 -N-octylbenzyloxymethyl group, 4-methoxybenzyloxymethyl group, 4-n-butoxybenzyloxymethyl group, 4-fluorobenzyloxymethyl group, 3-fluorobenzyloxymethyl group, 4-chlorobenzyloxymethyl group 2-benzyloxyethyl group, 2-phenethyloxyethyl group, 2- (4′-methylbenzyloxy) ethyl group, 2- (4′-fluorobenzyloxy) ethyl group, 2- (4′-chlorobenzyloxy) ) Ethyl group, 3- (4′-methoxybenzyloxy) propyl group, 4-base Benzyloxybutyl group, 4- (4′-pheny
  • R 1 to R 8 are substituted or unsubstituted arylthio groups, including heteroarylthio groups, including phenylthio groups, 2-methylphenylthio groups, 4-methylphenylthio groups, 3-ethylphenylthio groups.
  • Examples of the substituted or unsubstituted 5-membered ring or more formed by bonding adjacent groups selected from R 1 to R 8 together with a substituted carbon atom include an unsubstituted benzene ring or naphthalene ring , A halogen atom, a cyano group, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkylthio group having 1 to 8 carbon atoms, 2 carbon atoms An alkoxyalkyl group having 12 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted aralkyl group having 7 to 16 carbon atoms, and 6 to 12 carbon atoms A benzene ring or naphthalene ring having a substitute
  • Examples include benzene ring, naphthalene ring; chlorine, fluorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n- Pentyl group, n-hexyl group, 1,2-dimethylbutyl group, n-octyl group, 2-ethylhexyl group, vinyl group, propenyl group, 1-butenyl group, methoxy group, ethoxy group, n-propoxy group, isopropoxy group Group, n-butoxy group, sec-butoxy group, n-pentyloxy group, 2-ethylbutyloxy group, n-octyloxy group, methylthio group, ethylthio group, n-propylthio group, n-butylthio group, sec-butylthio group Group, n-p
  • the substitution positions of the substituents R 1 and R 2 , R 3 and R 4 , R 5 and R 6 , R 7 and R 8 are individually switched.
  • the bonding position of the pyrrole ring having each pair of R 1 and R 2 , R 3 and R 4 , R 5 and R 6 , R 7 and R 8 in the tetraazaporphyrin ring structure Isomers exist. In many cases, it is obtained as a mixture of these respective positional isomers according to the usual production method.
  • each isomer isolate has sharper absorption characteristics, but even a mixture can be used in the resin composition of the present invention without problems.
  • Specific examples of the tetraazaporphyrin-based compound (B-1) according to the resin composition of the present invention are shown in Table 1 below, but are not limited to these ranges. Since each specific example compound also includes positional isomers of each substituent, R 1 and R 2 , R 3 and R 4 , A combination of R 5 and R 6 , R 7 and R 8 represents a substituent. Also, isomers of these combinations with respect to the bonding position of the pyrrole ring in the tetraazaporphyrin ring structure are within the scope of the present invention.
  • the tetraazaporphyrin-based compound (B-1) according to the resin composition of the present invention can be produced according to a known method.
  • It can be produced with reference to the method described in the publication.
  • it can be produced by heating one or more of a maleonitrile derivative of the following general formula (A) or a 2,5-diiminopyrrole derivative of the following general formula (B).
  • Ra and Rb are the same as R 1 to R 8 in the general formula (2).
  • Compound (B-2) The compound (B-2) contained together with the tetraazaporphyrin-based compound (B-1) represented by the general formula (1) in the resin composition of the present invention has a maximum absorption in the toluene solution at a wavelength of 380 to 470 nm.
  • the ratio (A1 / A2) of the absorbance (A1) at the maximum absorption wavelength between 520 and 800 nm and the absorbance (A2) at the maximum absorption wavelength between 380 and 470 nm is less than 0.1.
  • the toluene solution has a maximum absorption between wavelengths 380 to 470 nm, and the absorbance (A1) at the maximum absorption wavelength between 520 to 800 nm and the maximum absorption wavelength between 380 to 470 nm.
  • the fact that the ratio (A1 / A2) of the absorbance (A2) is less than 0.1 is generally expressed as “absorption characteristics defined in the present invention”.
  • the absorbance of the compound (B-2) is determined by using a toluene solution having a concentration of 0.01 g / L and using a U-3500 self-recording spectrophotometer manufactured by Hitachi, Ltd. as a measuring instrument. This is a numerical value obtained when a wavelength region of 350 to 900 nm is measured at 10 mm, and is a numerical value on the vertical axis when the absorption spectrum is graphed with the horizontal axis as the wavelength (nm).
  • the compound (B-2) has an absorbance at a maximum absorption wavelength in a specific wavelength region of 380 to 470 nm in a visible light region of about 380 to 800 nm when an absorption spectrum is measured using a toluene solution.
  • the numerical value (A1) of the absorbance at the maximum absorption wavelength in the specific wavelength region of 520 to 800 nm, and the ratio (A1 / A2) of (A1) and (A2) is less than 0.1 Is a compound. Even when no clear absorption wavelength peak is observed in the specific wavelength region of 520 to 800 nm, the maximum value of absorbance that can be confirmed in this range is defined as (A1).
  • the ratio (A1 / A2) of (A1) to (A2) is preferably less than 0.09, more preferably less than 0.08.
  • the resin composition becomes deeply colored or the visible light transmittance decreases.
  • the preferred form of the compound (B-2) is not particularly limited as long as it has the absorption characteristics defined in the present invention and has a yellow hue, but more preferably, the absorption defined in the present invention.
  • a compound having a yellow hue in which no absorption wavelength peak is observed in a specific wavelength region of 471 to 519 nm when an absorption spectrum is measured using a toluene solution When an absorption spectrum is measured using a toluene solution, a yellow color having a maximum absorption wavelength in a specific wavelength region of 380 to 470 nm and no absorption wavelength peak in a specific wavelength region of 471 to 800 nm is observed. It is a compound which has the following hue.
  • the compound satisfying the absorption characteristics defined in the present invention is particularly preferably at least one selected from an azo compound having a specific structure, a quinophthalone compound having a specific structure, and a specific anthraquinone compound.
  • Y 1 to Y 11 are each independently a hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, mercapto group, carboxyl group, alkyl group, alkenyl group, halogenoalkyl group, alkoxy group, Halogenoalkoxy group, alkylthio group, alkoxyalkyl group, alkoxyalkoxyalkyl group, halogenoalkoxyalkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted aralkyl group, substituted or unsubstituted amino group, substituted or unsubstituted Amido group, substituted or unsubstituted acyl group, substituted or unsubstituted aryloxy group, substituted or unsubsub
  • Y 1 to Y 11 are substituted or unsubstituted aryl groups, substituted or unsubstituted aralkyl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted aryloxyalkyl groups, substituted or unsubstituted aralkyls.
  • Substituents in the case of an oxy group, a substituted or unsubstituted aralkyloxyalkyl group, a substituted or unsubstituted aryloxycarbonyl group, and a substituted or unsubstituted arylthio group include a halogen atom, a cyano group, a nitro group, and a hydroxyl group, respectively.
  • Mercapto group carboxyl group, alkyl group, alkenyl group, halogenoalkyl group, alkoxy group, halogenoalkoxy group, alkylthio group, alkoxyalkyl group, amino group, alkylamino group, and dialkylamino group.
  • Y 1 to Y 11 are a substituted or unsubstituted amino group, a substituted or unsubstituted amide group, or a substituted or unsubstituted acyl group is substituted, the substituent is an alkyl group, substituted or unsubstituted aryl, respectively.
  • Y 1 to Y 11 are preferably each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an alkyl group having 1 to 12 carbon atoms.
  • Halogenoalkyl group alkoxy group having 1 to 12 carbon atoms, halogenoalkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, alkoxyalkyl group having 2 to 16 carbon atoms, alkoxyalkoxy having 3 to 20 carbon atoms Alkyl group, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted amino group having 1 to 18 carbon atoms, substituted or unsubstituted amide group having 1 to 18 carbon atoms, 7 to 20 carbon atoms Substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted aryloxyalkyl group having 7 to 20 carbon atoms Group, an alkyloxycarbonyl group, a substituted or unsubstituted aryloxycarbonyl
  • Y 1 to Y 11 are more preferably each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, or 1 to 8 carbon atoms.
  • Y 1 to Y 11 are a halogen atom, alkyl group, alkenyl group, halogenoalkyl group, alkoxy group, halogenoalkoxy group, alkylthio group, alkoxyalkyl group, alkoxyalkoxyalkyl group, halogenoalkoxyalkyl group, substituted or unsubstituted aryl group Substituted or unsubstituted aralkyl group, substituted or unsubstituted amino group, substituted or unsubstituted acyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted aryloxyalkyl group, substituted or unsubstituted aralkyl Specific examples and preferred examples in the case of an oxy group, a substituted or unsubstituted aralkyloxyalkyl group, or a substituted or unsubstituted aralkyl
  • Y 1 to Y 11 are substituted, substituted or unsubstituted amide groups such as amide group, N-methylamide group, N-ethylamide group, Nn-propylamide group, Nn-butylamide group, N -Cyclohexylamide group, Nn-octylamide group, N-benzylamide group, N-phenylamide group, N- (3-methylphenyl) amide group, N- (4-methoxyphenyl) amide group, N- ( 3-fluorophenyl) amide group, N- (4-chlorophenyl) amide group, N- (2-naphthyl) amide group, N, N-dimethylamide group, N, N-diethylamide group, N, N-di-n -Propylamide group, N, N-di-n-butylamide group, N, N-di-n-octylamide group, N, N-di-n
  • Y 1 to Y 11 are alkyloxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, sec-butoxycarbonyl group, n-pentyl.
  • Y 1 to Y 11 being a substituted or unsubstituted aryloxycarbonyl group, a phenyloxycarbonyl group, a 2-methylphenyloxycarbonyl group, a 4-methylphenyloxycarbonyl group, a 4-ethylphenyloxycarbonyl group, 4-isopropylphenyloxycarbonyl group, 4-isobutylphenyloxycarbonyl group, 4-n-pentylphenyloxycarbonyl group, 4-tert-pentylphenyloxycarbonyl group, 4-cyclohexylphenyloxycarbonyl group, 4-n-octylphenyl Oxycarbonyl group, 4-n-decylphenyloxycarbonyl group, 4-n-dodecylphenyloxycarbonyl group, 4-n-hexadecylphenyloxycarbonyl group, 2,3-dimethylphenyloxycarbonyl Group, 2,5-dimethylphen
  • the azo compound of the general formula (2) has a tautomer such as the following general formula (2 ′), which represents the same compound as the general formula (2) and is the same in the present invention. Show the effect.
  • Y 1 ⁇ Y 11 have the same meanings as Y 1 ⁇ Y 11 in the general formula (2).
  • the azo compound of the general formula (2) can be produced by a known method. For example, Chem. Pharm. Bull. 35 (4) 1360-1371 (1987) and the like. As an example, it can be produced by reacting a nitrosurea derivative of the following general formula (C) with a pyrazole derivative of the following general formula (D) in carbon tetrachloride.
  • Y 1 ⁇ Y 11 have the same meanings as Y 1 ⁇ Y 11 in the general formula (2).
  • Z 1 to Z 9 are each independently a hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, mercapto group, carboxyl group, alkyl group, alkenyl group, halogenoalkyl group, alkoxy group, Halogenoalkoxy group, alkylthio group, alkoxyalkyl group, alkoxyalkoxyalkyl group, halogenoalkoxyalkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted aralkyl group, substituted or unsubstituted amino group, substituted or unsubstituted Amide group, substituted or unsubstituted acyl group, substituted or unsubstituted aryloxy group, substitute
  • Z 1 to Z 9 are substituted or unsubstituted aryl groups, substituted or unsubstituted aralkyl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted aryloxyalkyl groups, substituted or unsubstituted aralkyls. Adjacent groups selected from an oxy group, a substituted or unsubstituted aralkyloxyalkyl group, a substituted or unsubstituted aryloxycarbonyl group, a substituted or unsubstituted arylthio group, and Z 1 to Z 9 are bonded to each other and substituted.
  • Substituents in the case where a substituted or unsubstituted 5-membered ring or more formed with carbon atoms are substituted are each a halogen atom, cyano group, nitro group, hydroxyl group, mercapto group, carboxyl group, alkyl group, Alkenyl group, halogenoalkyl group, alkoxy group, halogenoalkoxy group, Kiruchio group, an alkoxyalkyl group, an amino group, an alkylamino group, dialkylamino group.
  • Z 1 to Z 9 are a substituted or unsubstituted amino group, a substituted or unsubstituted amide group, or a substituted or unsubstituted acyl group is substituted, the substituent is an alkyl group, substituted or unsubstituted aryl, respectively. Group, substituted or unsubstituted aralkyl group.
  • Z 1 to Z 9 are preferably each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an alkyl group having 1 to 12 carbon atoms.
  • Halogenoalkyl group alkoxy group having 1 to 12 carbon atoms, halogenoalkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, alkoxyalkyl group having 2 to 16 carbon atoms, alkoxyalkoxy having 3 to 20 carbon atoms Alkyl group, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted amino group having 1 to 18 carbon atoms, substituted or unsubstituted amide group having 1 to 18 carbon atoms, 7 to 20 carbon atoms Substituted or unsubstituted aralkyl group, substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms, substituted or unsubstituted aryloxyalkyl having 7 to 20 carbon atoms Selected, an alkyloxycarbonyl group having 2 to 13 carbon atoms, a substituted or unsubstitute
  • Z 1 to Z 9 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, or 1 to An alkoxy group having 8 to 8 carbon atoms, an alkylthio group having 1 to 8 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, and a substituted or unsubstituted amino group having 1 to 14 carbon atoms A substituted or unsubstituted amide group having 1 to 14 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 18 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 carbon atoms, 2 carbon atoms An alkyloxycarbonyl group having 9 to 9,
  • Z 1 to Z 9 are a halogen atom, alkyl group, alkenyl group, halogenoalkyl group, alkoxy group, halogenoalkoxy group, alkylthio group, alkoxyalkyl group, alkoxyalkoxyalkyl group, halogenoalkoxyalkyl group, substituted or unsubstituted aryl group Substituted or unsubstituted aralkyl group, substituted or unsubstituted amino group, substituted or unsubstituted acyl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted aryloxyalkyl group, substituted or unsubstituted aralkyl Specific examples and preferred examples in the case of an oxy group, a substituted or unsubstituted aralkyloxyalkyl group, or a substituted or unsubstituted aryl
  • Z 1 to Z 9 are a substituted, substituted or unsubstituted amide group, alkyloxycarbonyl group, substituted or unsubstituted aryloxycarbonyl group.
  • Y 1 to Z of the azo compound of the general formula (2) Examples similar to those given when Y 11 is each of these substituents are included.
  • Specific examples of the quinophthalone compound of the general formula (3) are shown in Table 3 below, but are not limited to these ranges.
  • the quinophthalone compound of the general formula (3) has a tautomer such as the following general formula (3 ′), which represents the same compound as the general formula (3) and is the same in the present invention. Show the effect. [Wherein Z 1 to Z 9 are the same as those in the general formula (3). ]
  • the quinophthalone compound of the general formula (3) can be produced by a known method. For example, JP-B-48-20476, JP-A-58-93778, JP-A-63-49705, JP-A-5-39269, JP-A-2006-16479, JP-A-2008-45130. It can be produced with reference to the method described in the publication.
  • the anthraquinone compound is not particularly limited as long as it has the absorption characteristics defined in the present invention, but is preferably a compound represented by the following general formula (4).
  • X 1 to X 8 are each independently a hydrogen atom, a halogen atom, an alkyl group, a halogenoalkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, a substituted or unsubstituted aryl group, a substituted or An unsubstituted aralkyl group or a substituted or unsubstituted arylthio group is shown.
  • X 1 to X 8 is necessarily a substituted or unsubstituted arylthio group.
  • the substituent is a halogen atom, an alkyl group, an alkenyl group, or a halogenoalkyl group, respectively.
  • An alkoxy group and an alkylthio group are preferable.
  • X 1 to X 8 are preferably each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, a halogenoalkyl group having 1 to 12 carbon atoms, or 1 to 12 carbon atoms.
  • X 1 to X 8 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or 1 to An alkylthio group having 8 carbon atoms, a substituted or unsubstituted phenylthio group having 6 to 12 carbon atoms, and at least one of X 1 to X 8 is necessarily a substituted or unsubstituted phenylthio group having 6 to 12 carbon atoms.
  • X 1 to X 8 are a halogen atom, an alkyl group, a halogenoalkyl group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted arylthio group
  • a substituted or unsubstituted aryl group a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted arylthio group
  • Specific examples and preferred examples in the case of the above are the same examples as those given when R 1 to R 8 of the tetraazaporphyrin-based compound of the general formula (1) are each these substituents. .
  • Specific examples of the anthraquinone compound of the general formula (4) are shown in Table 4 below, but are not limited to these ranges.
  • a part of the anthraquinone compound of the general formula (4) is commercially available as Solvent yellow 163, Solvent yellow 167, etc., but can also be produced by a known method. As an example, it can be produced by reacting an anthraquinone derivative having a halogen atom with a benzenethiol derivative.
  • ком ⁇ онент organic dyes In the resin composition of the present invention, other organic dyes can be used in combination for the purpose of cutting unnecessary light, adjusting the color tone, and the like within a range not impeding the effects of the present invention.
  • a porphyrin compound of the following general formula (5) can be used in combination in order to cut light in the vicinity of 480 to 490 nm.
  • L 1 to L 8 each independently represents a halogen atom, an ethynyl group or an ethynyl group having a C 1-12 alkyl group as a substituent, and Q represents a divalent metal atom or a metal oxide atom.
  • L 1 to L 8 are preferably a bromine atom, an ethynyl group having a tert-butyl group, that is, a 3,3-dimethyl-1-butyne group, and Q is preferably Ni, VO or Cu.
  • a yellow pigment such as Kayaset Yellow AG or an orange pigment such as PS Orange GG may be used in combination.
  • Such other organic pigments that can be used in combination are desirably compatible with the resin.
  • the resin used in the resin composition of the present invention is preferably a thermoplastic resin or a thermosetting resin, and may be an adhesive-like resin, but is preferably a transparent resin.
  • the thermoplastic resin include polycarbonate resin, polyamide resin, polyester resin, acrylic resin, polyurethane resin, polystyrene resin, acrylonitrile / styrene resin, norbornene resin, and cellulose resin. It is preferably at least one selected from polyester resins.
  • Polycarbonate resin is a polymer that is obtained mainly by the phosgene method in which dihydroxydiaryl compounds and phosgene are reacted, or the ester exchange method in which dihydroxydiaryl compounds and carbonic esters such as diphenyl carbonate are reacted. And a polycarbonate resin produced from 2,2-bis (4-hydroxyphenyl) propane (bisphenol A).
  • dihydroxydiaryl compounds examples include bisphenol 4-, bis (4-hydroxyphenyl) methane, 1,1-bis (4-hydroxyphenyl) ethane, 2,2-bis (4-hydroxyphenyl) butane, 2 , 2-bis (4-hydroxyphenyl) octane, 2,2-bis (4-hydroxyphenyl) phenylmethane, 2,2-bis (4-hydroxy-3-methylphenyl) propane, 2,2-bis (4 -Hydroxy-3-tert-butylphenyl) propane, 1,1-bis (4-hydroxy-3-tert-butylphenyl) propane, 2,2-bis (4-hydroxy-3-bromophenyl) propane, 2, 2-bis (4-hydroxy-3,5-dibromophenyl) propane, 2,2-bis (4-hydroxy-3,5-dichloropheny ) (Hydroxyaryl) alkanes such as propane, (hydroxyaryl) cycloalkanes such as 1,1-bis (4-hydroxyphenyl) cyclo
  • the viscosity average molecular weight of the polycarbonate resin is usually 10,000 to 100,000, preferably 10,000 to 400,000.
  • dihydroxy aryl compound and the trivalent or more phenol compound as shown below. Examples of the trivalent or higher phenol include phloroglucin, 1,3,5-tri- (4-hydroxyphenyl) -benzol, 1,1,1-tri- (4-hydroxyphenyl) -ethane, and the like.
  • the polyamide resin is a resin having a dehydration polycondensate structure of a diamine compound containing an aromatic or aliphatic group and a dicarboxylic acid compound containing an aromatic or aliphatic group.
  • the aliphatic group also includes an alicyclic aliphatic group.
  • the resin having the structure of the dehydration polycondensate of the diamine compounds and dicarboxylic acid compounds is not necessarily limited to those obtained from the dehydration polycondensation reaction. For example, ring opening of one or more lactam compounds It can also be obtained from polymerization or the like.
  • diamine compounds examples include hexamethylenediamine, m-xylylenediamine, bis (4-aminocyclohexyl) methane, bis (4-amino-3-methylcyclohexyl) methane, trimethylhexamethylenediamine, and bis (aminomethyl) norbornane.
  • Bis (aminomethyl) tetrahydrodicyclopentadiene and the like, and one or more of these diamine compounds can be selected and used.
  • dicarboxylic acid compounds examples include adipic acid, dodecanedicarboxylic acid, isophthalic acid, terephthalic acid, bis (hydroxycarbonylmethyl) norbornane, bis (hydroxycarbonylmethyl) tetrahydrodicyclopentadiene, and the like. 1 type or 2 types or more can be selected and used.
  • an amorphous polyamide resin is preferable from the viewpoint of transparency, and is generally referred to as transparent nylon.
  • Emamide's Grillamide TR-55, Grillamide TR-90, Grillamide TR-XE3805, or Hulus's Trogamide CX -7233 etc. can be illustrated.
  • the monomer may be a polymer mainly composed of alkyl methacrylate, which may be a homopolymer of alkyl methacrylate or a copolymer using two or more kinds of alkyl methacrylate, It may be a copolymer of 50% by weight or more of alkyl acid and 50% by weight or less of monomers other than alkyl methacrylate.
  • alkyl methacrylate those having 1 to 4 carbon atoms of the alkyl group are usually used, and methyl methacrylate is preferably used.
  • the monomer other than alkyl methacrylate may be a monofunctional monomer having one polymerizable carbon-carbon double bond in the molecule, or two or more polymerizable carbons in the molecule.
  • -A polyfunctional monomer having a carbon double bond may be used, but a monofunctional monomer is particularly preferably used.
  • alkyl acrylates such as methyl acrylate and ethyl acrylate
  • styrene monomers such as styrene and alkyl styrene
  • unsaturated nitriles such as acrylonitrile and methacrylonitrile.
  • a polymer in which the monomer is substantially composed only of alkyl methacrylate is preferable, and a typical example is polymethyl methacrylate resin (PMMA).
  • PMMA polymethyl methacrylate resin
  • Many commercially available polymethyl methacrylate resins are available, such as MX150 manufactured by Soken Chemical Co., Ltd., Eposta MA manufactured by Nippon Shokubai, and MBX series manufactured by Sekisui Plastics.
  • polyester resin examples include homopolyesters such as poly C 2-4 alkylene terephthalate and poly C 2-4 alkylene naphthalate, C 2-4 alkylene arylate units (C 2-4 alkylene terephthalate and / or C 2- Copolyesters containing 4 alkylene naphthalate units) as the main component, polyarylate resins, aliphatic polyesters using aliphatic dicarboxylic acids such as adipic acid, and lactones such as ⁇ -caprolactone alone or in combination Mergers are also included.
  • homopolyesters such as poly C 2-4 alkylene terephthalate and poly C 2-4 alkylene naphthalate
  • C 2-4 alkylene arylate units C 2-4 alkylene terephthalate and / or C 2- Copolyesters containing 4 alkylene naphthalate units
  • polyarylate resins aliphatic polyesters using aliphatic dicarboxylic acids such as adipic acid
  • copolyesters poly C 2-4 among constituent units of alkylene arylate, C 2-4 part of the alkylene glycol, polyoxy C 2-4 alkylene glycols, C 6-10 alkylene glycol, alicyclic diols (cyclohexane Dimethanol, hydrogenated bisphenol A and the like, diols having aromatic rings (9,9-bis (4- (2-hydroxyethoxy) phenyl) fluorene having a fluorenone side chain, bisphenol A, bisphenol A-alkylene oxide adducts, etc.
  • copolyesters substituted with asymmetric aromatic dicarboxylic acids such as phthalic acid and isophthalic acid
  • copolyesters substituted with aliphatic C 6-12 dicarboxylic acids such as adipic acid It is.
  • polyester resin polyethylene terephthalate (PET), polytrimethylene terephthalate (PTT), polybutylene terephthalate (PBT), polyethylene naphthalate (PEN) and the like are preferable in terms of high transparency.
  • Amorphous copolyesters such as C 2-4 alkylene arylate copolyesters are also preferred because of their excellent processability.
  • PET is preferable because it is produced in large quantities and is excellent in heat resistance, strength, and the like.
  • thermosetting resins include allyl diglycol carbonate monomers, diallyl phthalate monomers, mixtures of isocyanate compounds and polyols and polythiols, and cured products of monomers used in the manufacture of correction lenses such as acrylic monomers.
  • the polyurethane resin is mainly composed of a block type polyisocyanate and a polyol.
  • Examples of the block type polyisocyanate include hexamethylene diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, Examples include adducts obtained by bonding several molecules of isophorone diisocyanate and hydrogenated xylylene diisocyanate, and isocyanurate and allophanate blocked with acetoacetic acid and malonic acid. Examples include ether, polycarbonate, polyacrylate, polycaptolactone, and the like.
  • a typical example of the polythiourethane resin is a polythiourethane resin produced from metaxylylene diisocyanate and pentaerythritol tetrakis (3-mercaptopropionate).
  • the allyl diglycol carbonate resin polydiethylene glycol bisallyl carbonate is preferable, and examples thereof include CR-39 resin (also referred to as ADC resin).
  • the acrylic resins a poly (meth) acrylic ester resin having a low glass transition temperature, for example, a glass transition temperature of less than 0 ° C., preferably ⁇ 20 ° C. or less is used as an adhesive, an adhesive, and the like.
  • the poly (meth) acrylic acid ester resin used as the pressure-sensitive adhesive is preferably one using 50% by weight or more of (meth) acrylic acid ester having an alkyl group having 1 to 14 carbon atoms as a monomer.
  • Examples of (meth) acrylic acid esters having an alkyl group having 1 to 14 carbon atoms include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n -Octyl (meth) acrylate, i-octyl (meth) acrylate, benzyl (meth) acrylate, dicyclopentenyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate and the like.
  • an acrylic acid alkyl ester having 4 to 8 carbon atoms in the alkyl group is used, the adhesive strength and flexibility of the obtained adhesive are improved.
  • copolymerizable monomers include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, methoxyethyl (meth) acrylate, ethoxyethyl (meth) acrylate, ethoxyethoxyethyl (meth) acrylate, etc.
  • (Meth) acrylates styrene monomers represented by ⁇ -methyl styrene, vinyl toluene, styrene, etc .; vinyl ether monomers represented by methyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, etc .; fumaric acid, fumaric acid Monoalkyl ester of acid, dialkyl ester of fumaric acid; maleic acid, monoalkyl ester of maleic acid, dialkyl ester of maleic acid, itaconic acid, monoalkyl ester of itaconic acid, dialkyl ester of itaconic acid, Meth) acrylonitrile, vinyl chloride, vinylidene chloride, vinyl acetate, vinyl ketones, vinyl pyridine, and vinyl carbazole.
  • crosslinking can be performed using an isocyanate-based crosslinking agent or the like.
  • an isocyanate curing agent an epoxy curing agent, a metal chelate curing agent, or the like is used.
  • the adhesive in addition to the acrylic resin, for example, a silicone resin, a urethane resin, a polyvinyl butyral resin, an ethylene-vinyl acetate resin, a polyvinyl ether, a saturated polyester, a melamine resin, and the like are also used.
  • the resin composition of the present invention comprises (A) a resin, (B) a tetraazaporphyrin-based compound (B-1) represented by the following general formula (1) as an organic dye, and absorption characteristics defined in the present invention. And a compound (B-2) having at least The blending amount of the (A) resin and the (B) organic dye in the resin composition of the present invention varies depending on the use and the thickness of the resin molded body, but if the concentration is within the limits where the translucency and transparency are not lost.
  • the visible light transmittance is usually adjusted to 12 to 99%, preferably 20 to 90% with respect to the thickness direction of the molded body.
  • the amount of the organic dye used is 0.001% to 0.1% by weight with respect to the polycarbonate resin.
  • the amount of the organic dye used is 0.0001 to 0.2% by weight based on the thermoplastic resin or the thermosetting resin. This is the same when the resin composition is an adhesive.
  • the ratio of the tetraazaporphyrin compound (B-1) of the general formula (1) and the compound (B-2) having the absorption characteristics defined in the present invention to the total amount of the organic dye depends on the use of the resin composition.
  • the ratio of the compound (B-2) having the absorption characteristics defined in the present invention increases.
  • the ratio of the tetraazaporphyrin-based compound (B-1) to the compound (B-2) having the absorption characteristics defined in the present invention is 90:10 to The ratio is preferably 10:90, more preferably 80:20 to 20:80.
  • other components such as an ultraviolet absorber, an infrared absorber, various resin additives, and the like can be blended in the resin composition of the present invention as necessary.
  • Various resin additives include phenolic antioxidants, mold release agents, dyes and pigments, phosphorus heat stabilizers, weather resistance improvers, antistatic agents, antifogging agents, lubricants / antiblocking agents, flame retardants, fluidity Examples include improvers, plasticizers, dispersants, antibacterial agents and the like.
  • the manufacturing method of the resin composition of this invention is demonstrated below.
  • the resin composition of the present invention is obtained by mixing a resin and an organic dye, and the resin and the organic dye may be in a compatible state even in a molded article, an adhesive, an optical article, or an optical filter containing the resin composition. desirable.
  • the resin of the resin composition is a thermoplastic resin
  • the resin composition can be obtained by mixing the organic dye and the thermoplastic resin powder or pellets using various mixers such as a tumbler or a Henschel mixer.
  • melt-kneaded in a known melt kneader such as a Banbury mixer, heating roll, Brabender, single-screw kneading extruder, twin-screw kneading extruder, kneader, etc.
  • a known melt kneader such as a Banbury mixer, heating roll, Brabender, single-screw kneading extruder, twin-screw kneading extruder, kneader, etc.
  • a known melt kneader such as a Banbury mixer, heating roll, Brabender, single-screw kneading extruder, twin-screw kneading extruder, kneader, etc.
  • it can also manufacture by removing an organic solvent after melt
  • organic solvent used in this case examples include hexane, heptane, acetone, methyl ethyl ketone, benzene, toluene, dichloromethane, chloroform, etc., but are chemically inert to the resin composition and have a moderately low boiling point. If it is a thing, it will not specifically limit. It is also possible to produce an organic dye by dissolving the organic dye in a solvent and then bringing the resin or resin molded body into contact with the organic dye to diffuse and penetrate into the resin. The resin composition thus obtained is also the present invention. Is within the scope of rights.
  • the organic solvent for dissolving the organic dye is not particularly limited, but should not decompose the organic dye or alter the thermoplastic resin.
  • liquid ketones and alcohols are often used.
  • concentration of the solution is arbitrary depending on the purpose, but usually about 0.01% to 30% is a good range.
  • the diffusion conditions vary depending on the type of organic dye, solvent, thermoplastic resin, etc., but are usually 25 ° C. to 200 ° C. and several minutes to 5 hours under normal pressure or pressure.
  • polymerize this. This manufacturing method will be described collectively in the case where the resin of the following resin composition is a thermosetting resin.
  • the resin of the resin composition is a thermosetting resin
  • the resin or resin molded body is brought into contact to diffuse and infiltrate the organic dye into the resin, or the thermosetting resin
  • an organic dye is mixed with a raw material monomer and then polymerized, but the latter is often used. The latter method will be described below.
  • a method of making the monomer mixture after mixing with any of the monomer groups constituting the monomer mixture, the monomer mixture and other additions There are a method of adding a catalyst after mixing with a mixture of agents, a method of mixing with a mixture of monomer mixture, catalyst, and other additives.
  • Components other than monomers and organic dyes used for polymerization and curing include polymerization catalysts and other additives.
  • the polymerization catalyst an organic peroxide is known, and examples thereof include diacyl peroxide, peroxydicarbonate, peroxyester, peroxyketal, dialkyl peroxide, and hydroperoxide.
  • additives include catalysts such as dibutyltin dichloride, UV absorbers, internal mold release agents such as acidic phosphate esters, light stabilizers, antioxidants, reaction initiators such as radical initiators, chain extenders ,
  • a known resin modifier such as a hydroxy compound, a thiol compound, an epoxy compound, an episulfide compound, an organic acid and its anhydride, and a (meth) acrylate compound. Olefin compounds containing etc. are mentioned.
  • the organic dye may be mixed directly, or the organic dye is dissolved in a low boiling point organic solvent in advance and this organic solvent solution is mixed with the raw material monomer.
  • the organic solvent may be removed by evaporation under conditions such as heating and / or reduced pressure.
  • the organic solvent used in this case include hexane, heptane, acetone, methyl ethyl ketone, benzene, toluene, dichloromethane, chloroform, etc., but are chemically inert to the raw material monomers and have a moderately low boiling point. If it is, it will not specifically limit.
  • the resin composition may be mixed so that the amount corresponding to the organic dye concentration required for the resin composition is contained in the resin composition.
  • a master batch containing an organic dye at a concentration may be prepared, and another component to be blended may be added and diluted as necessary to produce a resin composition having a target concentration. Further, in dissolving the organic dye, it can be heated within a range where there is no problem in terms of deterioration of the resin composition and pot life.
  • the conditions for the polymerization and curing will be described in the cast polymerization method of the molded article described later.
  • the production method in the case where the resin composition is an adhesive is the same as the case where the resin of the molded body is a thermoplastic resin, but since the resin often has fluidity at room temperature, the case of a solid resin accordingly Handling is different.
  • the molded body of the present invention is formed by molding the resin composition of the present invention.
  • the form of the molded body may be an optical article made of a resin composition, an optical article partially containing the resin composition, or an intermediate material for manufacturing an optical article such as a powder or a pellet.
  • Optical articles include spectacle lenses, sun visors, helmet shields, display device coats or anti-glare films, various optical filters such as display mounting optical filters and spectacle lens mounting optical filters, and lighting equipment as described later. Examples thereof include an antiglare optical article such as a cover and an optical article for reducing short wavelength light.
  • the optical article partially containing the resin composition is a state in which it is contained inside various members or films of the optical article, and a state in which the surface of each member or each layer is coated or pasted.
  • the molding method varies depending on the type of product and resin used, but in the case of a resin composition using a thermoplastic resin, for example, molding by compression molding, transfer molding, extrusion molding, injection molding, etc., thermosetting
  • a resin composition using a conductive resin for example, a cast polymerization method is used. The cast polymerization method will be described below.
  • the resin composition is poured into the casting mold and incorporated therein, and then the casting mold is heated in a heatable apparatus such as an oven or in water for several hours to several tens of hours with a predetermined temperature program.
  • the temperature and time for polymerization and curing vary depending on the composition of the mixture, the type of catalyst, the shape of the mold, etc., but are approximately -50 to 200 ° C. and 1 to 100 hours. In general, it is common to start at a temperature in the range of 5 ° C. to 40 ° C., then gradually raise the temperature to a range of 80 ° C. to 130 ° C. and heat at that temperature for 1 to 4 hours. After completion of the curing and molding, the target molded product can be obtained by taking it out from the casting mold.
  • the resin composition of the present invention is also very useful as an adhesive used for optical articles.
  • Such an adhesive is used in optical articles for laminating a substrate and a transparent support, a functional transparent layer, etc., or for laminating any layer that forms an optical article, such as a transparent support and a functional transparent layer. It combines the functions of adhesion, anti-glare and unnecessary light cut.
  • the resin used for the pressure-sensitive adhesive is as described in the above section [Resin].
  • the composition ratio of the resin and the organic pigment is as described in the above section [Resin composition].
  • the pressure-sensitive adhesive may be in the form of a sheet or liquid.
  • the sheet-like adhesive When a sheet-like pressure-sensitive adhesive is used as the adhesive, the sheet-like adhesive is pasted or after the adhesive is applied, it is bonded by pressure bonding. In the case of using a liquid adhesive as the pressure-sensitive adhesive, it is cured and bonded by aging treatment at room temperature or under heating, or by irradiating ultraviolet rays after application and bonding.
  • Anti-glare optical article The molded article and pressure-sensitive adhesive of the resin composition of the present invention are very useful for optical articles for antiglare.
  • Anti-glare optical articles include spectacle lenses, sun visors, helmet shields, films for windshields for automobiles and airplanes, automobile headlight covers, ski goggles, and anti-glare for display devices of information equipment having display devices. Examples thereof include a coat or an antiglare film, a filter for LED lighting, and a film for building window glass. However, it can be used for any purpose for preventing glare and ensuring contrast and natural color tone.
  • the manufacturing method of the antiglare optical article differs depending on the form of the article and the type of resin, and the above-described manufacturing method of the molded body can be applied.
  • an antireflection function a hard coat function (friction resistance function), an antistatic function, an antifouling function, a gas barrier function, and an ultraviolet cut function A function may be provided.
  • optical article for reducing short wavelength light The molded article and pressure-sensitive adhesive of the resin composition of the present invention are also very useful for optical articles for reducing short wavelength light. Many optical articles for reducing short-wavelength light overlap those of the above-described anti-glare optical article, but protect the eyes from the effects of short-wavelength light even when the eye is not aware of glare. Can be used for the intended purpose. It is particularly suitable for articles intended to protect the eyes from illumination using LED, display devices, traffic lights, headlights, illumination, and the like. For example, spectacle lenses, sun visors, helmet shields, automobile glass films, automobile headlight covers, antiglare coatings or antiglare films for display devices, LED illumination covers, intraocular lenses, and the like.
  • optical filter examples of the optical article using the molded article and / or the pressure-sensitive adhesive of the resin composition of the present invention include the optical filters as described above.
  • an anti-glare film or the like is an optical filter depending on the use situation, but a display mounting optical system comprising a plurality of layers. It is also preferably used for filters and optical filters for wearing spectacle lenses.
  • Such an optical filter is typically composed of a single layer or a plurality of layers or members such as a transparent support, a transparent adhesive layer, and a functional transparent layer.
  • At least one layer or member of the optical filter contains a tetraazaporphyrin-based compound (B-1) represented by the general formula (1) and a compound (B-2) having an absorption characteristic defined in the present invention.
  • a transparent support an inorganic material such as transparent glass or a transparent resin is used, but a transparent resin is preferable from the viewpoint of production efficiency.
  • the thickness of the transparent support is preferably 10 ⁇ m to 10 mm, and more preferably 20 ⁇ m to 5 mm.
  • the functional transparent layer has an anti-reflective function, anti-glare function, anti-reflective function, anti-glare function, hard coat function (anti-friction function), anti-static function, anti-stain function, depending on the installation method and required functions of the optical filter.
  • a transparent adhesion layer is a layer containing an above-described adhesive.
  • the embodiment of such an optical filter is not limited, but can be used publicly as a display mounting filter or a spectacle lens mounting optical filter.
  • the display mounting filter can be mounted on various displays such as a plasma display, a liquid crystal display, an organic electroluminescence display, an FED (Field Emission Display), a CRT (Cathode Ray Tube) or the like with a space therebetween.
  • known display filter modes, configurations, components, and manufacturing methods can be applied.
  • the spectacle lens mounting optical filter can be used in any manner, such as being attached to the front or back surface of a general spectacle lens, or a filter mounted at a position spatially separated from the lens.
  • Example 1-9 Polyamide resin (Ms Chemie Japan product: Grilamid TR90) 1000 parts by weight, tetraazaporphyrin-based compound (B-1) as a specific example compound 1-10, 0.00525 parts by weight, having the absorption characteristics defined in the present invention
  • Example 1-11 1000 parts by weight of polymethyl methacrylate resin (Asahi Kasei Co., Ltd .: 80N) and 0.0065 parts by weight of specific example compound 1-10 as a tetraazaporphyrin-based compound (B-1), having the absorption characteristics defined in the present invention
  • Example 1-14 Using the pellets produced in Example 1-1 as a raw material, an injection molding machine was used to form a flat plate resin having an outer diameter of 150 mm ⁇ 300 mm and a thickness of 2 mm under conditions of a cylinder temperature of 260 ° C., a mold temperature of 80 ° C., and a molding cycle of 60 seconds. The composition was molded. When the transmission spectrum of this resin composition was measured, the spectrum shown in FIG. 1 was obtained. This resin composition was almost colorless.
  • Example 1-15 A flat resin composition was molded in the same manner as in Example 1-14, except that the pellets produced in Example 1-2 were used as raw materials. When the transmission spectrum of this resin composition was measured, the spectrum shown in FIG. 2 was obtained. This resin composition was almost colorless.
  • Example 1-16 A flat resin composition was molded in the same manner as in Example 1-14, except that the pellets produced in Example 1-8 were used as raw materials. When the transmission spectrum of this resin composition was measured, the spectrum shown in FIG. 3 was obtained. This resin composition was almost colorless.
  • Example 1-17 A flat resin composition was molded in the same manner as in Example 1-14, except that the pellets produced in Example 1-11 were used as raw materials. When the transmission spectrum of this resin composition was measured, the spectrum shown in FIG. 4 was obtained. This resin composition was almost colorless.
  • Example 1-18 A flat resin composition was molded in the same manner as in Example 1-14, except that the pellets produced in Example 1-12 were used as raw materials.
  • Example 1-19 A flat resin composition was molded in the same manner as in Example 1-14, except that the pellets produced in Example 1-13 were used as raw materials. When the transmission spectrum of this resin composition was measured, the spectrum shown in FIG. 6 was obtained. This resin composition was almost colorless.
  • the obtained prepolymer was a colorless transparent liquid, and had an NCO content of 9.9%, a viscosity of 8600 mPa ⁇ s / 30 ° C., and 750 mPa ⁇ s / 60 ° C.
  • After heating 1000 parts by weight of the resulting prepolymer to 70 ° C. 0.0075 parts by weight of the specific example compound 1-10 as the tetraazaporphyrin-based compound (B-1) and the absorption characteristics defined in the present invention
  • the mixture was defoamed and mixed with 314 parts by weight of 4,4′-methylene-bis (2-chloroaniline) melted at 120 ° C.
  • This mixture was poured into a mold preheated at 100 ° C. and heat-cured at 100 ° C. for 24 hours to produce a spectacle lens having a lens thickness of about 2.6 mm.
  • the obtained lens was almost colorless. Further, when observing through the glasses equipped with this lens, the glare was rarely felt even when used for a long time under fine weather. In addition, the lines of tree twigs and the contrast of red, yellow and green looked very clear.
  • Example 1-21 Manufacture of spectacle lenses
  • the pellets produced in Example 1-1 were used as raw materials, melted at 250 ° C., and molded by an injection molding machine using a predetermined mold to obtain a plastic lens having an outer diameter of 75 mm ⁇ and a center thickness of 2 mm.
  • the obtained lens was almost colorless. Further, when observing through the glasses equipped with this lens, the glare was rarely felt even when used for a long time under fine weather. In addition, the lines of tree twigs and the contrast of red, yellow and green looked very clear.
  • Example 1-22 Manufacture of spectacle lenses A plastic lens having an outer diameter of 75 mm ⁇ and a center thickness of 2 mm was obtained in the same manner as in Example 1-21 except that the pellets produced in Example 1-11 were used as raw materials. The obtained lens was almost colorless. Further, when observing through the glasses equipped with this lens, the glare was rarely felt even when used for a long time under fine weather. In addition, the lines of tree twigs and the contrast of red, yellow and green looked very clear.
  • Example 1-23 Manufacture of spectacle lenses A plastic lens having an outer diameter of 75 mm ⁇ and a center thickness of 2 mm was obtained in the same manner as in Example 1-21 except that the pellets produced in Example 1-8 were used as raw materials. The obtained lens was almost colorless. Further, when observing through the glasses equipped with this lens, the glare was rarely felt even when used for a long time under fine weather. In addition, the lines of tree twigs and the contrast of red, yellow and green looked very clear.
  • Example 1-24 Production of automobile sun visor
  • a flat plate having an outer diameter of 150 mm ⁇ 300 mm and a thickness of 2 mm manufactured in Example 1-14 is integrally attached to a normal sun visor body used in an automobile via a hinge portion of a flexible resin.
  • the glare was not felt so much.
  • the transmitted color tone is almost colorless, it is not difficult to distinguish blue (green), yellow, and red used for the signal as compared with daytime. Further, even when this antiglare sun visor was used, the light transmittance did not decrease so much.
  • Example 1-25 Manufacture of helmet shield A flat plate having an outer shape of 150 mm ⁇ 300 mm and a thickness of 2 mm manufactured in Example 1-17 was cut into the shape of a motorcycle helmet shield and placed in a heating furnace and heated to 160 ° C. The heated flat plate was put into a mold, and a curved surface molded product having a curvature radius of about 120 mm was taken out from the mold after cooling to obtain a helmet shield.
  • this shield to a helmet and using it for daytime and nighttime driving, there was little feeling of glare in driving under fine weather, and the light transmittance was not so lowered even during nighttime driving. Moreover, blue (green), yellow, and red of the signal could be clearly confirmed.
  • Example 1-26 Production of optical filter
  • 300 parts by weight of methyl ethyl ketone, 100 parts by weight of a polymethyl methacrylate resin (Asahi Kasei Co., Ltd .: 80N), 0.09 part by weight of a specific compound 1-11 as a tetraazaporphyrin-based compound (B-1), 0.045 parts by weight of the azo compound of the specific example compound 2-4 (A1 / A2 0.03) was dissolved as the compound (B-2) having the prescribed absorption characteristics to prepare a coating solution.
  • This coating solution was applied to a surface of a polyethylene terephthalate (PET) sheet having a thickness of about 200 ⁇ m with a Mayer bar so that the film thickness after drying was about 10 ⁇ m and dried.
  • PET polyethylene terephthalate
  • This anti-glare-coated PET sheet was placed in front of a personal computer display screen of an LED backlight to obtain an optical filter for a display device.
  • the pellets were mixed and extruded in a twin screw extruder to produce a film (sheet) having a thickness of about 200 ⁇ m.
  • the temperature in the extrusion zone and the melting line was 275 ° C. at maximum, and the temperature of the cooling roll was 30 ° C.
  • the obtained film was cut and attached as a display device optical film on the display surface of a portable information device (smartphone) using an acrylic adhesive.
  • This pressure-sensitive adhesive composition was applied on a polyethylene terephthalate film (manufactured by Teijin DuPont Films, Inc., thickness 75 ⁇ m) using a bar coater so as to have a dry film thickness of 25 ⁇ m, and dried at 90 ° C. for 2 minutes.
  • An optical filter was produced by laminating a release film having a silicone release layer on the coated surface. This optical filter was colorless. The transmission spectrum of this optical filter is shown in FIG.
  • This optical filter was affixed to the front surface of a liquid crystal television (AQUAL SLC-16K5, manufactured by Sharp Corporation) using a white LED as a backlight unit to obtain an optical filter for a display device.
  • the optical filter manufactured above was affixed to the outer surface of a non-colored spectacle lens made of polythiourethane resin and having a center thickness of about 2 mm to obtain an optical filter for spectacle lenses.
  • a non-colored spectacle lens made of polythiourethane resin and having a center thickness of about 2 mm to obtain an optical filter for spectacle lenses.
  • Example 1-29 Production of optical filter As the tetraazaporphyrin-based compound (B-1), 0.0058 parts by weight of the specific example compound 1-11 and a compound having the absorption characteristics defined in the present invention (B-2)
  • the obtained optical filter was colorless.
  • the same operation as in Example 1-28 was performed except that this optical filter was used, and the optical filter was attached to the front surface of the liquid crystal television to obtain an optical filter for a display device. As a result of observing the screen of the liquid crystal television through this optical filter, the same effect as in Example 1-28 was obtained.
  • the obtained optical filter was colorless.
  • This optical filter was affixed to the liquid crystal display surface of a smartphone-type mobile phone terminal (iPhone 3GS 16GB SoftBank) to obtain an optical filter for a display device.
  • An optical filter was produced in the same manner as in Example 1-28 except that parts by weight were used. This optical filter was colorless. The transmission spectrum of this optical filter is shown in FIG.
  • Example 1-28 The same operation as in Example 1-28 was performed except that this optical filter was used, and the optical filter was attached to the front surface of the liquid crystal television to obtain an optical filter for a display device. As a result of observing the screen of the liquid crystal television through this optical filter, the same effect as in Example 1-28 was obtained.
  • the pellets were mixed and extruded in a twin screw extruder to produce a film (sheet) having a thickness of about 200 ⁇ m.
  • the temperature in the extrusion zone and the melting line was 275 ° C. at maximum, and the temperature of the cooling roll was 30 ° C. Thereafter, this film was stretched biaxially to produce a film having a thickness of 100 ⁇ m.
  • methyl ethyl ketone 80 parts by weight of methyl ethyl ketone, 30 parts by weight of acrylic pressure-sensitive adhesive PX4-IR-PT-076 (manufactured by Nippon Shokubai, solid content concentration 37.5%), isocyanate-based curing agent (L-55E, manufactured by Nippon Polyurethane Industry) 0 0.057 parts by weight and 0.0057 parts by weight of a curing accelerator (dibutyltin dilaurate manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred with a homogenizer at 10000 rpm for 10 minutes to obtain an adhesive composition having a solid content concentration of about 10%. .
  • the pressure-sensitive adhesive composition was prepared by using a bar coater to form a dry film thickness of 25 ⁇ m on the polymethyl methacrylate resin film prepared in advance and containing (B) specific compound 1-11 and specific compound 2-4 as organic dyes. And then dried.
  • An optical filter was produced by laminating a release film having a silicone release layer on the coated surface. This optical filter was colorless. The transmission spectrum of this optical filter is shown in FIG.
  • the obtained optical filter was colorless.
  • This optical filter was affixed to the outer surface of an uncolored spectacle lens made of polythiourethane resin and having a center thickness of about 2 mm in the same manner as in Example 1-28 to obtain an optical filter for spectacle lenses. As a result of wearing the glasses equipped with this lens indoors and outdoors, the same effect as in Example 1-28 was obtained.
  • a smartphone type mobile phone terminal iPhone 3GS 16GB SoftBank
  • the pellets were mixed and extruded in a twin screw extruder to produce a film (sheet) having a thickness of about 200 ⁇ m.
  • the temperature in the extrusion zone and the melting line was 275 ° C. at maximum, and the temperature of the cooling roll was 30 ° C. Thereafter, this film was stretched biaxially to produce a film having a thickness of 100 ⁇ m.
  • methyl ethyl ketone 80 parts by weight of methyl ethyl ketone, 30 parts by weight of acrylic pressure-sensitive adhesive PX4-IR-PT-076 (manufactured by Nippon Shokubai, solid content concentration 37.5%), isocyanate-based curing agent (L-55E, manufactured by Nippon Polyurethane Industry) 0 0.057 parts by weight and 0.0057 parts by weight of a curing accelerator (dibutyltin dilaurate manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred with a homogenizer at 10000 rpm for 10 minutes to obtain an adhesive composition having a solid content concentration of about 10%. .
  • the pressure-sensitive adhesive composition was prepared by using a bar coater on the surface of the polymethyl methacrylate resin film prepared in advance and containing (B) specific compound 1-13 and specific compound 2-9 as organic dyes. It was applied and dried. A release film having a silicone release layer formed thereon was bonded to the coated surface. Next, the adhesive composition was applied and dried on the back surface of the obtained film in the same manner, and a release film was bonded to the coated surface. The release film on one side of the obtained film is peeled off and bonded to a polycarbonate hard coat film (MGP fill sheet Iupilon sheet MR58, thickness 0.5 mm) to produce an optical filter with a hard coat film. did. The obtained optical filter was colorless.
  • MGP fill sheet Iupilon sheet MR58 thickness 0.5 mm
  • This optical filter was affixed to the liquid crystal display surface of a portable navigation device (Sanyo Electric NV-LB51DT) to obtain an optical filter for a display device.
  • a portable navigation device Sanyo Electric NV-LB51DT
  • the fine contrast of images and characters was improved, and it was clearly visible, while the color tone did not change.
  • the degree of eye fatigue and haze when using for a long time was greatly reduced compared to before applying the optical filter.
  • This pressure-sensitive adhesive composition was applied on a polyethylene terephthalate film (manufactured by Teijin DuPont Films Co., Ltd., thickness 75 ⁇ m) using a bar coater so as to have a dry film thickness of 25 ⁇ m and dried. A release film having a silicone release layer formed thereon was bonded to the coated surface.
  • a pressure-sensitive adhesive composition not containing (B) an organic dye was obtained by the same operation as above except that (B) no specific compound 1-60 and specific compound 2-29 were not used as the organic dye.
  • This pressure-sensitive adhesive composition was applied to the other surface of the polyethylene terephthalate film (the surface on which the dye-containing pressure-sensitive adhesive composition layer was not formed) using a bar coater so as to have a dry film thickness of 25 ⁇ m and dried. .
  • a release film having a silicone release layer formed thereon was bonded to the coated surface.
  • the release film on the surface of the adhesive composition containing no organic pigment (B) is peeled off and attached to a hard coat film made of polycarbonate (MGP fill sheet Iupilon sheet MR58, thickness 0.5 mm).
  • MGP fill sheet Iupilon sheet MR58 thickness 0.5 mm
  • an optical filter with a hard coat film was produced. The obtained optical filter was colorless.
  • a schematic structural view of this optical filter is shown in FIG.
  • This pressure-sensitive adhesive composition was applied on a polyethylene terephthalate film (manufactured by Teijin DuPont Films, Inc., thickness 75 ⁇ m) using a bar coater so as to have a dry film thickness of 25 ⁇ m, and dried at 90 ° C. for 2 minutes.
  • An optical filter was produced by laminating a release film having a silicone release layer on the coated surface. The obtained optical filter was tinged with blue. Next, this optical filter was attached to the front surface of a liquid crystal television (AQUAS LC-16K5 manufactured by Sharp Corporation) using a white LED as a backlight unit.
  • the optical filter obtained above was affixed to the outer surface of an uncolored spectacle lens made of polythiourethane resin and having a center thickness of about 2 mm to produce a spectacle lens with an optical film.
  • the optical filter obtained above was affixed to the outer surface of an uncolored spectacle lens made of polythiourethane resin and having a center thickness of about 2 mm to produce a spectacle lens with an optical film.
  • the glasses equipped with this lens indoors and outdoors, it was less likely to feel dazzling than when the glasses were not used, but sometimes it was dazzling under certain conditions such as in daylight.
  • the contrast of blue (green), yellow, and red in the signal could be clearly seen, but the color changed.
  • Example 2-9 Polyamide resin (produced by Emschemy Japan: Grilamid TR90) 1000 parts by weight and tetraazaporphyrin-based compound (B-1) as specific compound 1-13 by 0.00055 parts by weight, having the absorption characteristics defined in the present invention
  • Example 2-10 1000 parts by weight of polymethyl methacrylate (Asahi Kasei Co., Ltd .: 80N), 0.00045 parts by weight of the specific compound 1-11 as the tetraazaporphyrin-based compound (B-1), and a compound having absorption characteristics defined in the present invention
  • Example 2-12 The pellets produced in Example 2-1 were used as raw materials, and the resin was a flat plate having an outer shape of 150 mm ⁇ 300 mm and a thickness of 2 mm under the conditions of a cylinder temperature of 260 ° C., a mold temperature of 80 ° C., and a molding cycle of 60 seconds using an injection molding machine. The composition was molded. When the transmission spectrum of this resin composition was measured, the spectrum shown in FIG. 11 was obtained. This resin composition was almost colorless.
  • Example 2-13 A flat resin composition was molded in the same manner as in Example 2-12 except that the pellets produced in Example 2-8 were used as raw materials. When the transmission spectrum of this resin composition was measured, the spectrum shown in FIG. 12 was obtained. This resin composition was almost colorless.
  • Example 2-14 A flat resin composition was molded in the same manner as in Example 2-12, except that the pellets produced in Example 2-10 were used as raw materials. When the transmission spectrum of this resin composition was measured, the spectrum shown in FIG. 13 was obtained. This resin composition was almost colorless.
  • Example 2-15 A flat resin composition was molded in the same manner as in Example 2-12, except that the pellets produced in Example 2-11 were used as raw materials. When the transmission spectrum of this resin composition was measured, the spectrum shown in FIG. 14 was obtained. This resin composition was almost colorless.
  • Example 2-16 Manufacture of spectacle lenses A 2 L separable flask equipped with a thermometer, stirrer, and nitrogen seal tube was charged with polyoxytetramethylene glycol having an average molecular weight of 1014 (manufactured by Hodogaya Chemical Co., Ltd .: PTG-1000N) 1000 A part by weight was added, heated with stirring in a nitrogen stream, and dehydrated under reduced pressure of 100 to 110 ° C./3 to 5 mmHg for 1 hour.
  • PTG-1000N polyoxytetramethylene glycol having an average molecular weight of 1014 (manufactured by Hodogaya Chemical Co., Ltd .: PTG-1000N) 1000 A part by weight was added, heated with stirring in a nitrogen stream, and dehydrated under reduced pressure of 100 to 110 ° C./3 to 5 mmHg for 1 hour.
  • the obtained prepolymer was a colorless transparent liquid, and had an NCO content of 9.9%, a viscosity of 8600 mPa ⁇ s / 30 ° C., and 750 mPa ⁇ s / 60 ° C.
  • Example 2-17 Manufacture of spectacle lens
  • the pellets manufactured in Example 2-1 were used as raw materials, melted at 250 ° C., and molded by an injection molding machine using a predetermined mold, and had an outer diameter of 75 mm ⁇ and a center thickness.
  • a 2 mm plastic lens was obtained.
  • the obtained lens was almost colorless. Further, when observing through the glasses equipped with this lens, the glare was rarely felt even when used for a long time under fine weather. In addition, the lines of tree twigs and the contrast of red, yellow and green looked very clear.
  • Example 2-18 Manufacture of eyeglass lens A plastic lens having an outer diameter of 75 mm ⁇ and a center thickness of 2 mm was obtained by the same operation as in Example 2-17, except that the pellets manufactured in Example 2-9 were used as raw materials. Obtained. The obtained lens was almost colorless. Further, when observing through the glasses equipped with this lens, the glare was rarely felt even when used for a long time under fine weather. In addition, the lines of tree twigs and the contrast of red, yellow and green looked very clear.
  • Example 2-19 Manufacture of automobile sun visor
  • the flat plate of 150 mm x 300 mm and 2 mm thickness manufactured in Example 2-12 was used as a flexible resin hinge for a normal sun visor body used in automobiles.
  • the sun visor for anti-glare was obtained by attaching integrally through the part.
  • the anti-glare sun visor was lowered and an oncoming vehicle equipped with a discharge light was observed, the glare was not felt so much.
  • the transmitted color tone is almost colorless, it is not difficult to distinguish blue (green), yellow, and red used for the signal as compared with daytime. Further, even when this antiglare sun visor was used, the light transmittance was not greatly reduced.
  • Example 2-20 Manufacture of helmet shield
  • the flat plate of 150 mm x 300 mm and 2 mm thickness manufactured in Example 2-13 was cut into the shape of a motorcycle helmet shield and heated to 160 ° C in a heating furnace. did.
  • the heated flat plate was put into a mold, and a curved surface molded product having a curvature radius of about 120 mm was taken out from the mold after cooling to obtain a helmet shield.
  • a curved surface molded product having a curvature radius of about 120 mm was taken out from the mold after cooling to obtain a helmet shield.
  • blue (green), yellow, and red of the signal could be clearly confirmed.
  • This coating solution was applied to a surface of a polyethylene terephthalate (PET) sheet having a thickness of about 200 ⁇ m with a Mayer bar so that the film thickness after drying was about 10 ⁇ m and dried.
  • PET polyethylene terephthalate
  • This anti-glare coated PET sheet was placed in front of a personal computer display screen of an LED backlight, and the screen was observed under various conditions such as character display, image display, and video display. As a result, not only the glare and dazzling decreased from before the installation and the fatigue of the eyes was reduced, but also the contrast of the image and the like was improved and the color tone was not changed.
  • the pellets were mixed and extruded in a twin screw extruder to produce a film (sheet) having a thickness of about 200 ⁇ m.
  • the temperature in the extrusion zone and the melting line was 275 ° C. at maximum, and the temperature of the cooling roll was 30 ° C.
  • the obtained film was cut and affixed on the display surface of the portable information device using an acrylic adhesive.
  • This pressure-sensitive adhesive composition was applied on a polyethylene terephthalate film (manufactured by Teijin DuPont Films, Inc., thickness 75 ⁇ m) using a bar coater so as to have a dry film thickness of 25 ⁇ m, and dried at 90 ° C. for 2 minutes.
  • An optical filter was produced by laminating a release film having a silicone release layer on the coated surface. This optical filter was colorless. This optical filter was affixed to the front surface of a liquid crystal television (AQUAL SLC-16K5, manufactured by Sharp Corporation) using a white LED as a backlight unit to obtain an optical filter for a display device.
  • the optical filter manufactured above was affixed to the outer surface of a non-colored spectacle lens made of polythiourethane resin and having a center thickness of about 2 mm to obtain an optical filter for spectacle lenses.
  • a non-colored spectacle lens made of polythiourethane resin and having a center thickness of about 2 mm to obtain an optical filter for spectacle lenses.
  • Example 2-24 Production of optical filter As tetraazaporphyrin-based compound (B-1), 0.009 part by weight of specific example compound 1-12 and a compound (B-2) having an absorption characteristic defined in the present invention
  • This optical filter was colorless.
  • an optical filter was attached to the front surface of the liquid crystal television in the same manner as in Example 2-23 to obtain an optical filter for a display device. As a result of observing the screen of the liquid crystal television through this optical filter, the same effect as in Example 2-23 was obtained.
  • the pellets were mixed and extruded in a twin screw extruder to produce a film (sheet) having a thickness of about 200 ⁇ m.
  • the temperature in the extrusion zone and the melting line was 275 ° C. at maximum, and the temperature of the cooling roll was 30 ° C. Thereafter, this film was stretched biaxially to produce a film having a thickness of 100 ⁇ m.
  • methyl ethyl ketone 80 parts by weight of methyl ethyl ketone, 30 parts by weight of acrylic pressure-sensitive adhesive PX4-IR-PT-076 (manufactured by Nippon Shokubai, solid content concentration 37.5%), isocyanate-based curing agent (L-55E, manufactured by Nippon Polyurethane Industry) 0 0.057 parts by weight and 0.0057 parts by weight of a curing accelerator (dibutyltin dilaurate manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred with a homogenizer at 10000 rpm for 10 minutes to obtain an adhesive composition having a solid content concentration of about 10%. .
  • This pressure-sensitive adhesive composition was prepared by using a bar coater to add a dry film thickness of 25 ⁇ m to the polymethyl methacrylate resin film prepared in advance and containing (B) specific compound 1-11 and specific compound 3-21 as organic dyes. It was applied and dried.
  • An optical filter was produced by laminating a release film having a silicone release layer on the coated surface. This optical filter was colorless.
  • This optical filter was affixed to the liquid crystal display surface of a smartphone-type mobile phone terminal (iPhone 3GS 16GB SoftBank) to obtain an optical filter for a display device. As a result of observing the screen of the liquid crystal display through this optical filter, the fine contrast of images and characters was improved, and it was clearly visible, while the color tone did not change. In addition, the degree of eye fatigue and haze when using for a long time was greatly reduced compared to before applying the optical filter.
  • Example 3-1 1000 parts by weight of a polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering Plastics Co., Ltd.), 0.005 parts by weight of a specific compound 1-10 as a tetraazaporphyrin-based compound (B-1), and the absorption specified in the present invention
  • a polycarbonate resin H-3000FN manufactured by Mitsubishi Engineering Plastics Co., Ltd.
  • a specific compound 1-10 as a tetraazaporphyrin-based compound (B-1)
  • Example 3-11 Using the pellets produced in Example 3-1 as a raw material, a flat plate resin having an outer diameter of 150 mm ⁇ 300 mm and a thickness of 2 mm on an injection molding machine under conditions of a cylinder temperature of 260 ° C., a mold temperature of 80 ° C., and a molding cycle of 60 seconds. The composition was molded. When the transmission spectrum of this resin composition was measured, the spectrum shown in FIG. 15 was obtained. This resin composition was almost colorless. [Example 3-12] A flat resin composition was molded in the same manner as in Example 3-11 except that the pellets produced in Example 3-2 were used as raw materials. This resin composition was almost colorless.
  • Example 3-13 A flat resin composition was molded in the same manner as in Example 3-11 except that the pellets produced in Example 3-3 were used as raw materials. This resin composition was almost colorless.
  • Example 3-14 A flat resin composition was molded in the same manner as in Example 3-11 except that the pellets produced in Example 3-4 were used as raw materials. This resin composition was almost colorless.
  • Example 3-15 A flat resin composition was molded in the same manner as in Example 3-11 except that the pellets produced in Example 3-5 were used as raw materials. This resin composition was almost colorless.
  • Example 3-16 A flat resin composition was molded in the same manner as in Example 3-11 except that the pellets produced in Example 3-6 were used as raw materials. This resin composition was almost colorless.
  • Example 3-17 A flat resin composition was molded in the same manner as in Example 3-11 except that the pellets produced in Example 3-7 were used as raw materials. This resin composition was almost colorless.
  • Example 3-18 A flat resin composition was molded in the same manner as in Example 3-11 except that the pellets produced in Example 3-8 were used as raw materials. This resin composition was almost colorless.
  • Example 3-19 A flat resin composition was molded in the same manner as in Example 3-11 except that the pellets produced in Example 3-9 were used as raw materials. This resin composition was almost colorless.
  • the obtained prepolymer was a colorless transparent liquid, and had an NCO content of 9.9%, a viscosity of 8600 mPa ⁇ s / 30 ° C., and 750 mPa ⁇ s / 60 ° C.
  • After heating 1000 parts by weight of the obtained prepolymer to 70 ° C. 0.0075 parts by weight of the specific example compound 1-10 as the tetraazaporphyrin-based compound (B-1) and the absorption characteristics defined in the present invention are obtained.
  • the mixture was defoamed and mixed with 314 parts by weight of 4,4′-methylene-bis (2-chloroaniline) melted at 120 ° C.
  • This mixture was poured into a mold preheated at 100 ° C. and heat-cured at 100 ° C. for 24 hours to produce a spectacle lens having a lens thickness of about 2.6 mm.
  • the obtained lens was almost colorless. Further, when observing through the glasses equipped with this lens, the glare was rarely felt even when used for a long time under fine weather. In addition, the lines of tree twigs and the contrast of red, yellow and green looked very clear.
  • Example 3-21 Manufacture of spectacle lenses
  • the pellets produced in Example 3-1 were used as raw materials, melted at 250 ° C., and molded by an injection molding machine using a predetermined mold to obtain a plastic lens having an outer diameter of 75 mm ⁇ and a center thickness of 2 mm.
  • the obtained lens was almost colorless. Further, when observing through the glasses equipped with this lens, the glare was rarely felt even when used for a long time under fine weather. In addition, the lines of tree twigs and the contrast of red, yellow and green looked very clear.
  • Example 3-22 Manufacture of spectacle lenses A plastic lens having an outer diameter of 75 mm ⁇ and a center thickness of 2 mm was obtained in the same manner as in Example 3-21 except that the pellets produced in Example 3-3 were used as raw materials. The obtained lens was almost colorless. Further, in the observation through the glasses equipped with this lens, the same effect as in Example 3-21 was obtained.
  • Example 3-23 Manufacture of spectacle lenses A plastic lens having an outer diameter of 75 mm ⁇ and a center thickness of 2 mm was obtained in the same manner as in Example 3-21 except that the pellets produced in Example 3-5 were used as raw materials. The obtained lens was almost colorless. Further, in the observation through the glasses equipped with this lens, the same effect as in Example 3-21 was obtained.
  • Example 3-24 Manufacture of spectacle lenses A plastic lens having an outer diameter of 75 mm ⁇ and a center thickness of 2 mm was obtained in the same manner as in Example 3-21 except that the pellets produced in Example 3-6 were used as raw materials. The obtained lens was almost colorless. Further, in the observation through the glasses equipped with this lens, the same effect as in Example 3-21 was obtained.
  • Example 3-25 Manufacture of spectacle lenses A plastic lens having an outer diameter of 75 mm ⁇ and a center thickness of 2 mm was obtained in the same manner as in Example 3-21 except that the pellets produced in Example 3-7 were used as raw materials. The obtained lens was almost colorless. Further, in the observation through the glasses equipped with this lens, the same effect as in Example 3-21 was obtained.
  • Example 3-26 Manufacture of spectacle lenses A plastic lens having an outer diameter of 75 mm ⁇ and a center thickness of 2 mm was obtained in the same manner as in Example 3-21 except that the pellets produced in Example 3-9 were used as raw materials. The obtained lens was almost colorless. Further, in the observation through the glasses equipped with this lens, the same effect as in Example 3-21 was obtained.
  • Example 3-27 Manufacture of automobile sun visor A flat plate manufactured in Example 3-11 having an outer diameter of 150 mm x 300 mm and a thickness of 2 mm was applied to a normal sun visor body used in automobiles as a flexible resin.
  • the sun visor for anti-glare was obtained by attaching integrally through the hinge portion.
  • the anti-glare sun visor was lowered and an oncoming vehicle equipped with a discharge light was observed, the glare was not felt so much. Further, since the transmitted color tone is almost colorless, it is not difficult to distinguish blue (green), yellow, and red used for the signal as compared with daytime. Further, even when this antiglare sun visor was used, the light transmittance was not greatly reduced.
  • Example 3-28 Production of optical filter
  • This coating solution was applied to a surface of a polyethylene terephthalate (PET) sheet having a thickness of about 200 ⁇ m with a Mayer bar so that the film thickness after drying was about 10 ⁇ m and dried.
  • PET polyethylene terephthalate
  • This anti-glare-coated PET sheet was placed in front of a personal computer display screen of an LED backlight to obtain an optical filter for a display device.
  • the pellets were mixed and extruded in a twin screw extruder to produce a film (sheet) having a thickness of about 200 ⁇ m.
  • the temperature in the extrusion zone and the melting line was 275 ° C. at maximum, and the temperature of the cooling roll was 30 ° C.
  • the obtained film was cut and affixed on the display surface of the smartphone-type mobile phone terminal using an acrylic adhesive as a display device optical film.
  • This pressure-sensitive adhesive composition was applied on a polyethylene terephthalate film (manufactured by Teijin DuPont Films, Inc., thickness 75 ⁇ m) using a bar coater so as to have a dry film thickness of 25 ⁇ m, and dried at 90 ° C. for 2 minutes.
  • An optical filter was produced by laminating a release film having a silicone release layer on the coated surface. This optical filter was colorless. This optical filter was affixed to the front surface of a liquid crystal television (AQUAL SLC-16K5, manufactured by Sharp Corporation) using a white LED as a backlight unit to obtain an optical filter for a display device.
  • the optical filter manufactured above was affixed to the outer surface of a non-colored spectacle lens made of polythiourethane resin and having a center thickness of about 2 mm to obtain an optical filter for spectacle lenses.
  • a non-colored spectacle lens made of polythiourethane resin and having a center thickness of about 2 mm to obtain an optical filter for spectacle lenses.
  • Example 3-31 Production of optical filter As a tetraazaporphyrin-based compound (B-1), 0.0058 parts by weight of a specific example compound 1-12 and a compound (B-2) having absorption characteristics defined in the present invention
  • the obtained optical filter was colorless.
  • the same operation as in Example 3-30 was performed except that this optical filter was used, and the optical filter was attached to the front surface of the liquid crystal television to obtain an optical filter for a display device. As a result of observing the screen of the liquid crystal television through this optical filter, the same effect as in Example 3-30 was obtained.
  • the pellets were mixed and extruded in a twin screw extruder to produce a film (sheet) having a thickness of about 200 ⁇ m.
  • the temperature in the extrusion zone and the melting line was 275 ° C. at maximum, and the temperature of the cooling roll was 30 ° C. Thereafter, this film was stretched biaxially to produce a film having a thickness of 100 ⁇ m.
  • methyl ethyl ketone 80 parts by weight of methyl ethyl ketone, 30 parts by weight of acrylic pressure-sensitive adhesive PX4-IR-PT-076 (manufactured by Nippon Shokubai, solid content concentration 37.5%), isocyanate-based curing agent (L-55E, manufactured by Nippon Polyurethane Industry) 0 0.057 parts by weight and 0.0057 parts by weight of a curing accelerator (dibutyltin dilaurate manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred with a homogenizer at 10000 rpm for 10 minutes to obtain an adhesive composition having a solid content concentration of about 10%. .
  • the pressure-sensitive adhesive composition was prepared by using a bar coater to form a dry film thickness of 25 ⁇ m on the polymethyl methacrylate resin film prepared in advance and containing (B) the specific compound 1-10 and the specific compound 4-1 as the organic dye. And then dried.
  • An optical filter was produced by laminating a release film having a silicone release layer on the coated surface. This optical filter was colorless. The transmission spectrum of this optical filter is shown in FIG.
  • This optical filter was attached to the front surface of a liquid crystal television using a white LED as a backlight unit to obtain an optical filter for a display device. As a result of observing the screen of the liquid crystal television through this optical filter, the fine contrast of the image was improved and it was clearly visible, while the color tone did not change.
  • the degree of eye fatigue and haze when viewing for a long time was greatly reduced.
  • the resin composition of the present invention efficiently cuts blue light around 380 nm to 460 nm and light with high human visibility around 580 nm to 590 nm to prevent glare, glare, adverse effects on the eyes and human body, and contrast. Can be increased. Furthermore, there is almost no coloration, there is little decrease in light transmittance, and there is little deterioration of the pigment in the resin, so spectacle lenses, sun visors, helmet shields, coats for display devices, optical filters for mounting display, for mounting spectacle lenses It is very useful for a wide range of optical articles such as optical filters.
  • Hard coat film 192 Transparent adhesive layer (H) 193: Transparent support (F) 194: Transparent adhesive layer (H) D: Tetraazaporphyrin compound (B-1) represented by general formula (1) and azo compound represented by general formula (2) (dissolved in resin)

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  • Health & Medical Sciences (AREA)
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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Eyeglasses (AREA)
  • Optical Filters (AREA)
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WO2018143329A1 (fr) * 2017-02-03 2018-08-09 株式会社ニコン・エシロール Lentille de lunettes et procédé de fabrication de lentille de lunettes
JPWO2017090128A1 (ja) * 2015-11-25 2018-09-13 株式会社ジンズ 光学部材
JP2019120940A (ja) * 2017-12-27 2019-07-22 住友化学株式会社 粘着剤層付き光学フィルム及び表示装置
JP2020503537A (ja) * 2016-11-23 2020-01-30 エシロール アテルナジオナール 光劣化に耐性のある色素を含有する光学物品
JP2020034867A (ja) * 2018-08-31 2020-03-05 三井化学株式会社 硬化型封止材、硬化物および表示装置
JP2020041010A (ja) * 2018-09-06 2020-03-19 三井化学株式会社 透明シート、シートおよび施工方法
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TWI836438B (zh) * 2022-05-23 2024-03-21 晶碩光學股份有限公司 隱形眼鏡的包裝容器及其產品
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WO2017014272A1 (fr) * 2015-07-22 2017-01-26 Jsr株式会社 Filtre de correction de couleur et dispositif d'affichage dans lequel celui-ci est utilisé
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WO2018143329A1 (fr) * 2017-02-03 2018-08-09 株式会社ニコン・エシロール Lentille de lunettes et procédé de fabrication de lentille de lunettes
JP7022082B2 (ja) 2017-02-03 2022-02-17 株式会社ニコン・エシロール 眼鏡レンズ、及び眼鏡レンズの製造方法
JP2019120940A (ja) * 2017-12-27 2019-07-22 住友化学株式会社 粘着剤層付き光学フィルム及び表示装置
JP2020034867A (ja) * 2018-08-31 2020-03-05 三井化学株式会社 硬化型封止材、硬化物および表示装置
JP7182958B2 (ja) 2018-08-31 2022-12-05 三井化学株式会社 硬化型封止材、硬化物および表示装置
JP2020041010A (ja) * 2018-09-06 2020-03-19 三井化学株式会社 透明シート、シートおよび施工方法
JP7257120B2 (ja) 2018-09-06 2023-04-13 三井化学株式会社 透明シート、シートおよび施工方法
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CN113253486A (zh) * 2020-02-13 2021-08-13 亚立邦科技股份有限公司 抗眩光高对比的镜片组合
KR102603576B1 (ko) * 2022-11-01 2023-11-17 (주)대명솔루션 태양광등이 구비된 볼라드

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