JP2014164208A - Optical material and use of the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide optical material excellent in visibility or the like at night, and to provide use of the optical material.SOLUTION: Optical material comprises a fluorescent substance having excitation wavelength at 280 to 600 nm, and fluorescent wavelength at 450 to 750 nm, and maximum fluorescent wavelength at 500 to 600 nm.

Description

  The present invention relates to an optical material and use thereof.

  When walking at night or when driving at night or when driving a vehicle, it is difficult to distinguish objects such as obstacles due to darkness or diffuse reflection, and considerable caution is required.

  Patent Document 1 describes a clear vision device using a combination of a polarizing filter and a colored sheet. This document describes that night visibility during rain can be improved.

  Patent Document 2 describes an illuminated spectacle frame in which illumination is attached to an spectacle frame. The document describes that the visibility of an object at night or in a dark place can be improved by illuminating the front of the eyes with illumination.

JP-A-6-72151 JP 2004-163839 A

  However, since the clear vision device described in Patent Document 1 uses a combination of a polarizing sheet that absorbs incident light and a dye, there is a problem that it looks dark. This is an unavoidable problem in terms of the mechanism of action even when a yellow pigment is used.

  The eyeglass frame described in Patent Document 2 has a lighting device composed of a battery and a lamp on the frame, and becomes heavy. Therefore, when used for a long time, there is a problem that the feeling of use such as feeling fatigue is bad. It was.

The present invention can be described below.
[1] An optical material comprising a phosphor having an excitation wavelength of 280 to 600 nm, a fluorescence wavelength of 450 to 750 nm, and a maximum fluorescence wavelength of 500 to 600 nm.
[2] The optical material according to [1], wherein the phosphor comprises rubrene and / or rhodamines.
[3] A lens base material, and a film layer and a coating layer laminated as necessary,
The optical material according to [1] or [2], wherein the phosphor is included in at least one of the lens substrate, the film layer, and the coating layer.
[4] A phosphor in which at least one of the lens substrate and the film layer has an excitation wavelength of 280 to 600 nm, a fluorescence wavelength of 450 to 750 nm, and a maximum fluorescence wavelength of 500 to 600 nm, and an optical material The optical material according to [3], which is obtained from a composition for optical materials, comprising a resin or a resin monomer.
[5] The optical material according to [4], wherein the resin for optical material or the resin obtained from the resin monomer is polyurethane, polythiourethane, polysulfide, polycarbonate, poly (meth) acrylate, or polyolefin.
[6] A plastic spectacle lens made of the optical material according to any one of [1] to [5].
[7] A composition for optical materials, comprising a phosphor having an excitation wavelength of 280 to 600 nm, a fluorescence wavelength of 450 to 750 nm, and a maximum fluorescence wavelength of 500 to 600 nm, and a resin or resin monomer for optical materials. .
[8] The composition for optical materials according to [7], wherein the phosphor comprises rubrene and / or rhodamines.
[9] The optical material according to [7] or [8], wherein the resin for optical material or the resin obtained from the resin monomer is polyurethane, polythiourethane, polysulfide, polycarbonate, poly (meth) acrylate, or polyolefin. Composition.
[10] A molded article comprising the composition according to any one of [7] to [9].
[11] A molded article comprising a phosphor having an excitation wavelength of 280 to 600 nm, a fluorescence wavelength of 450 to 750 nm, and a maximum fluorescence wavelength of 500 to 600 nm, and a resin for optical materials.
[12] An optical material comprising the molded article according to [10] or [11].
[13] A plastic spectacle lens provided with a lens substrate made of the molded article according to [10] or [11].
[14] A film comprising the molded article according to [10] or [11].
[15] A plastic spectacle lens comprising a layer made of the film according to [14] on at least one of the surfaces of the lens substrate.
[16] A plastic spectacle lens provided with a lens base layer on both sides of the film according to [14].

  According to the optical material of the present invention, it is excellent in visibility of an object at night regardless of the presence or absence of rainfall, and can be suitably used particularly as a plastic spectacle lens.

The optical material of the present invention includes a phosphor having an excitation wavelength at 280 to 600 nm, a fluorescence wavelength at 450 to 750 nm, and a maximum fluorescence wavelength at 500 to 600 nm.
Hereinafter, embodiments of the present invention will be specifically described.
In the present embodiment, an embodiment in which an optical material is prepared using a composition for optical material containing a phosphor will be described.

The composition for an optical material of the present embodiment has a phosphor having an excitation wavelength of 280 to 600 nm, a fluorescence wavelength of 450 to 750 nm, and a maximum fluorescence wavelength of 500 to 600 nm, a resin for optical material or a resin monomer, Containing.
Details will be described below.

[Phosphor]
The phosphor used in this embodiment has an excitation wavelength in the wavelength region of 280 to 600 nm. Further, the absorbed light fluoresces in a wavelength region of 450 to 750 nm, and has a maximum fluorescence wavelength of 500 to 600 nm. The phosphor comprises a fluorescent material. The phosphor may be the fluorescent substance itself, a mixture of the fluorescent substance with another substance, or a substance obtained by attaching the fluorescent substance to another particulate substance. The particulate material is not particularly limited, but may be a particulate organic polymer such as polyurethane resin, latex resin, polyolefin resin, polyester resin, or particulate inorganic material such as alumina, silica, glass, zirconia. May be.

The fluorescent substance is not particularly limited as long as it is a dye satisfying the above-mentioned fluorescence characteristics, but from the viewpoint of the sharpness of fluorescence emission, rubrene and rhodamines can be used, and they can also be used in combination.
Rubrene has an excitation wavelength in the wavelength region of 280 to 580 nm. Further, the absorbed light fluoresces in a wavelength region of 505 to 720 nm, and has a maximum fluorescence wavelength of 540 to 580 nm.
Rhodamines have an excitation wavelength in the wavelength region of 420 to 580 nm. Further, the absorbed light fluoresces in a wavelength region of 490 to 680 nm, and has a maximum fluorescence wavelength of 530 to 570 nm.
Many types of rhodamines are known, such as rhodamine B, rhodamine 6G, rhodamine 123, and the like, depending on the side chain, but all can be used as long as they have the wavelength characteristics of the present invention.

  The phosphor can be contained in a lens substrate or an optical film described later. Further, it may be contained in the coating layer.

[Resin or resin monomer for optical materials]
In the present embodiment, the optical material resin or the optical material resin obtained from the resin monomer is not particularly limited as long as it is a transparent resin. As the transparent resin, polyurethane, polythiourethane, polysulfide, polycarbonate, poly (meth) acrylate, polyolefin, cyclic polyolefin, polyallyl, polyurethane urea, polyene-polythiol polymer, ring-opening metathesis polymer, polyester, epoxy resin are preferably used. be able to. These materials are highly transparent materials and can be suitably used for optical material applications. In addition, these materials may be individual or these composite materials may be sufficient.

  The polyurethane is obtained from a polyisocyanate compound and a polyol compound, which are resin monomers. Polythiourethane is obtained from a polyisocyanate compound and a polythiol compound. The composition for optical materials can contain a resin monomer constituting these resins.

Examples of the polyisocyanate compound include hexamethylene diisocyanate, 2,2,4-trimethylhexane diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, lysine diisocyanatomethyl ester, lysine triisocyanate, m-xylylene diisocyanate, α, α, α ', α'-tetramethylxylylene diisocyanate, bis (isocyanatomethyl) naphthalene, mesityrylene triisocyanate, bis (isocyanatomethyl) sulfide, bis (isocyanatoethyl) sulfide, bis (isocyanatomethyl) Disulfide, bis (isocyanatoethylthio) disulfide, bis (isocyanatomethylthio) methane, bis (isocyanatoethylthio) methane, bis (isocyanatoethylthio) ethane, bis ( Aliphatic polyisocyanate compounds such Socia diisocyanate methyl thio) ethane;
Isophorone diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane isocyanate, 2,5-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, 2 , 6-Bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, 3,8-bis (isocyanatomethyl) tricyclodecane, 3,9-bis (isocyanatomethyl) tricyclodecane, 4 , 8-bis (isocyanatomethyl) tricyclodecane, 4,9-bis (isocyanatomethyl) tricyclodecane, and other alicyclic polyisocyanate compounds;
Aromatic polyisocyanate compounds such as diphenyl sulfide-4,4-diisocyanate;
2,5-diisocyanatothiophene, 2,5-bis (isocyanatomethyl) thiophene, 2,5-diisocyanatotetrahydrothiophene, 2,5-bis (isocyanatomethyl) tetrahydrothiophene, 3,4-bis ( Isocyanatomethyl) tetrahydrothiophene, 2,5-diisocyanato-1,4-dithiane, 2,5-bis (isocyanatomethyl) -1,4-dithiane, 4,5-diisocyanato-1,3-dithiolane, 4, Examples include heterocyclic polyisocyanate compounds such as 5-bis (isocyanatomethyl) -1,3-dithiolane.

  The polyol compound is one or more aliphatic or alicyclic alcohols, and specifically includes linear or branched aliphatic alcohols, alicyclic alcohols, these alcohols and ethylene oxide, propylene oxide, ε- Examples include alcohol to which caprolactone is added.

  Examples of linear or branched aliphatic alcohols include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,3-propanediol, 2,2-dimethyl-1,3- Propanediol, 2,2-diethyl-1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 3-methyl-1,3-butanediol, , 2-pentanediol, 1,3-pentanediol, 1,5-pentanediol, 2,4-pentanediol, 2-methyl-2,4-pentanediol, 3-methyl-1,5-pentanediol, 1 , 6-hexanediol, 2,5-hexanediol, glycerol, diglycerol, poly Examples include reglycerol, trimethylolpropane, pentaerythritol, di (trimethylolpropane) and the like.

  Examples of the alicyclic alcohol include 1,2-cyclopentanediol, 1,3-cyclopentanediol, 3-methyl-1,2-cyclopentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, , 4-cyclohexanediol, 4,4′-bicyclohexanol, 1,4-cyclohexanedimethanol and the like.

  Compounds obtained by adding these alcohols to ethylene oxide, propylene oxide, and ε-caprolactone may also be used. For example, ethylene oxide adduct of glycerol, ethylene oxide adduct of trimethylolpropane, ethylene oxide adduct of pentaerythritol, propylene oxide adduct of glycerol, propylene oxide adduct of trimethylolpropane, propylene oxide adduct of pentaerythritol, Examples include caprolactone-modified glycerol, caprolactone-modified trimethylolpropane, and caprolactone-modified pentaerythritol.

Polythiol compounds include methanedithiol, 1,2-ethanedithiol, 1,2,3-propanetrithiol, 1,2-cyclohexanedithiol, bis (2-mercaptoethyl) ether, tetrakis (mercaptomethyl) methane, and diethylene glycol bis. (2-mercaptoacetate), diethylene glycol bis (3-mercaptopropionate), ethylene glycol bis (2-mercaptoacetate), ethylene glycol bis (3-mercaptopropionate), trimethylolpropane tris (2-mercaptoacetate) , Trimethylolpropane tris (3-mercaptopropionate), trimethylolethane tris (2-mercaptoacetate), trimethylolethanetris (3-mercaptopropionate), pentaerythro Ritoletetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate), bis (mercaptomethyl) sulfide, bis (mercaptomethyl) disulfide, bis (mercaptoethyl) sulfide, bis (mercaptoethyl) disulfide, Bis (mercaptopropyl) sulfide, bis (mercaptomethylthio) methane, bis (2-mercaptoethylthio) methane, bis (3-mercaptopropylthio) methane, 1,2-bis (mercaptomethylthio) ethane, 1,2-bis (2-mercaptoethylthio) ethane, 1,2-bis (3-mercaptopropylthio) ethane, 1,2,3-tris (mercaptomethylthio) propane, 1,2,3-tris (2-mercaptoethylthio) Propane, 1,2,3-tri (3-mercaptopropylthio) propane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, tetrakis ( Mercaptomethylthiomethyl) methane, tetrakis (2-mercaptoethylthiomethyl) methane, tetrakis (3-mercaptopropylthiomethyl) methane, bis (2,3-dimercaptopropyl) sulfide, 2,5-dimercaptomethyl-1, 4-dithiane, 2,5-dimercapto-1,4-dithiane, 2,5-dimercaptomethyl-2,5-dimethyl-1,4-dithia And esters of thioglycolic acid and mercaptopropionic acid, hydroxymethyl sulfide bis (2-mercaptoacetate), hydroxymethyl sulfide bis (3-mercaptopropionate), hydroxyethyl sulfide bis (2-mercaptoacetate), hydroxy Ethyl sulfide bis (3-mercaptopropionate), hydroxymethyl disulfide bis (2-mercaptoacetate), hydroxymethyl disulfide bis (3-mercaptopropionate), hydroxyethyl disulfide bis (2-mercaptoacetate), hydroxyethyl disulfide Bis (3-mercaptopropinate), 2-mercaptoethyl ether bis (2-mercaptoacetate), 2-mercaptoethyl ether bis (3-merca Topropionate), thiodiglycolic acid bis (2-mercaptoethyl ester), thiodipropionic acid bis (2-mercaptoethyl ester), dithiodiglycolic acid bis (2-mercaptoethyl ester), dithiodipropionic acid bis (2- Mercaptoethyl ester), 1,1,3,3-tetrakis (mercaptomethylthio) propane, 1,1,2,2-tetrakis (mercaptomethylthio) ethane, 4,6-bis (mercaptomethylthio) -1,3-dithiane , Aliphatic polythiol compounds such as tris (mercaptomethylthio) methane and tris (mercaptoethylthio) methane;
1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis (mercaptomethyl) benzene, 1,3-bis (mercaptomethyl) benzene, 1,4- Bis (mercaptomethyl) benzene, 1,2-bis (mercaptoethyl) benzene, 1,3-bis (mercaptoethyl) benzene, 1,4-bis (mercaptoethyl) benzene, 1,3,5-trimercaptobenzene, 1,3,5-tris (mercaptomethyl) benzene, 1,3,5-tris (mercaptomethyleneoxy) benzene, 1,3,5-tris (mercaptoethyleneoxy) benzene, 2,5-toluenedithiol, 3, Aromatic polythiol compounds such as 4-toluenedithiol, 1,5-naphthalenedithiol, 2,6-naphthalenedithiol;
2-methylamino-4,6-dithiol-sym-triazine, 3,4-thiophenedithiol, bismuthiol, 4,6-bis (mercaptomethylthio) -1,3-dithiane, 2- (2,2-bis (mercapto) And heterocyclic polythiol compounds such as methylthio) ethyl) -1,3-dithietane.

  In this embodiment, polyurethane and polythiourethane may or may not use a polymerization catalyst. Moreover, you may use arbitrary additives, such as an internal mold release agent and a bluing agent. When the UV absorber is added in a large amount, the fluorescent performance of the fluorescent material is impaired. Therefore, when used, it is preferable to add the minimum necessary amount while confirming the fluorescent performance.

  The polysulfide can be obtained by a method by ring-opening polymerization of a polyepithio compound or a polythietane compound, which is a resin monomer. The composition for optical materials can contain a resin monomer constituting these resins.

Polyepithio compounds include bis (1,2-epithioethyl) sulfide, bis (1,2-epithioethyl) disulfide, bis (epithioethylthio) methane, bis (epithioethylthio) benzene, bis [4- (epithio Epithioethylthio compounds such as ethylthio) phenyl] sulfide, bis [4- (epithioethylthio) phenyl] methane;
Bis (2,3-epithiopropyl) sulfide, bis (2,3-epithiopropyl) disulfide, bis (2,3-epithiopropylthio) methane, 1,2-bis (2,3-epithiopropyl) Thio) ethane, 1,2-bis (2,3-epithiopropylthio) propane, 1,3-bis (2,3-epithiopropylthio) propane, 1,3-bis (2,3-epithio) Propylthio) -2-methylpropane, 1,4-bis (2,3-epithiopropylthio) butane, 1,4-bis (2,3-epithiopropylthio) -2-methylbutane, 1,3- Bis (2,3-epithiopropylthio) butane, 1,5-bis (2,3-epithiopropylthio) pentane, 1,5-bis (2,3-epithiopropylthio) -2-methylpentane 1,5-bis (2, -Epithiopropylthio) -3-thiapentane, 1,6-bis (2,3-epithiopropylthio) hexane, 1,6-bis (2,3-epithiopropylthio) -2-methylhexane, , 8-bis (2,3-epithiopropylthio) -3,6-dithiaoctane, 1,2,3-tris (2,3-epithiopropylthio) propane, 2,2-bis (2,3- Epithiopropylthio) -1,3-bis (2,3-epithiopropylthiomethyl) propane, 2,2-bis (2,3-epithiopropylthiomethyl) -1- (2,3-epithio Propylthio) butane, 1,5-bis (2,3-epithiopropylthio) -2- (2,3-epithiopropylthiomethyl) -3-thiapentane, 1,5-bis (2,3-epi Thiopropylthio) -2,4-bis ( , 3-epithiopropylthiomethyl) -3-thiapentane, 1- (2,3-epithiopropylthio) -2,2-bis (2,3-epithiopropylthiomethyl) -4-thiahexane, 1, 5,6-Tris (2,3-epithiopropylthio) -4- (2,3-epithiopropylthiomethyl) -3-thiahexane, 1,8-bis (2,3-epithiopropylthio)- 4- (2,3-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (2,3-epithiopropylthio) -4,5-bis (2,3-epithiopropylthio) Methyl) -3,6-dithiaoctane, 1,8-bis (2,3-epithiopropylthio) -4,4-bis (2,3-epithiopropylthiomethyl) -3,6-dithiaoctane, 1, 8-bis (2,3-epithiop Lopyrthio) -2,5-bis (2,3-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (2,3-epithiopropylthio) -2,4,5-tris ( 2,3-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,1,1-tris [[2- (2,3-epithiopropylthio) ethyl] thiomethyl] -2- (2,3- Epithiopropylthio) ethane, 1,1,2,2-tetrakis [[2- (2,3-epithiopropylthio) ethyl] thiomethyl] ethane, 1,11-bis (2,3-epithiopropylthio) ) -4,8-bis (2,3-epithiopropylthiomethyl) -3,6,9-trithiaundecane, 1,11-bis (2,3-epithiopropylthio) -4,7-bis (2,3-epithiopropylthiomethyl) 3,6,9-trithiaundecane, 1,11-bis (2,3-epithiopropylthio) -5,7-bis (2,3-epithiopropylthiomethyl) -3,6,9-tri Chain aliphatic 2,3-epithiopropylthio compounds such as thiaundecane;
1,3-bis (2,3-epithiopropylthio) cyclohexane, 1,4-bis (2,3-epithiopropylthio) cyclohexane, 1,3-bis (2,3-epithiopropylthiomethyl) Cyclohexane, 1,4-bis (2,3-epithiopropylthiomethyl) cyclohexane, 2,5-bis (2,3-epithiopropylthiomethyl) -1,4-dithiane, 2,5-bis [[ 2- (2,3-epithiopropylthio) ethyl] thiomethyl] -1,4-dithiane, 2,5-bis (2,3-epithiopropylthiomethyl) -2,5-dimethyl-1,4- Cycloaliphatic 2,3-epithiopropylthio compounds such as dithiane;
1,2-bis (2,3-epithiopropylthio) benzene, 1,3-bis (2,3-epithiopropylthio) benzene, 1,4-bis (2,3-epithiopropylthio) benzene 1,2-bis (2,3-epithiopropylthiomethyl) benzene, 1,3-bis (2,3-epithiopropylthiomethyl) benzene, 1,4-bis (2,3-epithiopropyl) Thiomethyl) benzene, bis [4- (2,3-epithiopropylthio) phenyl] methane, 2,2-bis [4- (2,3-epithiopropylthio) phenyl] propane, bis [4- ( 2,3-epithiopropylthio) phenyl] sulfide, bis [4- (2,3-epithiopropylthio) phenyl] sulfone, 4,4′-bis (2,3-epithiopropylthio) biphenyl, etc. Aromatic 2 , 3-epithiopropylthio compound;
Bis (2,3-epithiopropyl) ether, bis (2,3-epithiopropyloxy) methane, 1,2-bis (2,3-epithiopropyloxy) ethane, 1,2-bis (2, 3-epithiopropyloxy) propane, 1,3-bis (2,3-epithiopropyloxy) propane, 1,3-bis (2,3-epithiopropyloxy) -2-methylpropane, 1,4 -Bis (2,3-epithiopropyloxy) butane, 1,4-bis (2,3-epithiopropyloxy) -2-methylbutane, 1,3-bis (2,3-epithiopropyloxy) butane 1,5-bis (2,3-epithiopropyloxy) pentane, 1,5-bis (2,3-epithiopropyloxy) -2-methylpentane, 1,5-bis (2,3-epi Thiopropyloxy) 3-thiapentane, 1,6-bis (2,3-epithiopropyloxy) hexane, 1,6-bis (2,3-epithiopropyloxy) -2-methylhexane, 1,8-bis (2, 3-epithiopropyloxy) -3,6-dithiaoctane, 1,2,3-tris (2,3-epithiopropyloxy) propane, 2,2-bis (2,3-epithiopropyloxy) -1 , 3-bis (2,3-epithiopropyloxymethyl) propane, 2,2-bis (2,3-epithiopropyloxymethyl) -1- (2,3-epithiopropyloxy) butane, 1, 5-bis (2,3-epithiopropyloxy) -2- (2,3-epithiopropyloxymethyl) -3-thiapentane, 1,5-bis (2,3-epithiopropyloxy) -2, 4-bis (2, -Epithiopropyloxymethyl) -3-thiapentane, 1- (2,3-epithiopropyloxy) -2,2-bis (2,3-epithiopropyloxymethyl) -4-thiahexane, 1,5, 6-Tris (2,3-epithiopropyloxy) -4- (2,3-epithiopropyloxymethyl) -3-thiahexane, 1,8-bis (2,3-epithiopropyloxy) -4- (2,3-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (2,3-epithiopropyloxy) -4,5-bis (2,3-epithiopropyloxymethyl) 3,6-dithiaoctane, 1,8-bis (2,3-epithiopropyloxy) -4,4-bis (2,3-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8- Screw( 2,3-epithiopropyloxy) -2,5-bis (2,3-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (2,3-epithiopropyloxy) -2 , 4,5-tris (2,3-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,1,1-tris [[2- (2,3-epithiopropyloxy) ethyl] thiomethyl]- 2- (2,3-epithiopropyloxy) ethane, 1,1,2,2-tetrakis [[2- (2,3-epithiopropyloxy) ethyl] thiomethyl] ethane, 1,11-bis (2 , 3-epithiopropyloxy) -4,8-bis (2,3-epithiopropyloxymethyl) -3,6,9-trithiaundecane, 1,11-bis (2,3-epithiopropyloxy) ) -4,7-Bis 2,3-epithiopropyloxymethyl) -3,6,9-trithiaundecane, 1,11-bis (2,3-epithiopropyloxy) -5,7-bis (2,3-epithiopropyl) Chain aliphatic 2,3-epithiopropyloxy compounds such as oxymethyl) -3,6,9-trithiaundecane;
1,3-bis (2,3-epithiopropyloxy) cyclohexane, 1,4-bis (2,3-epithiopropyloxy) cyclohexane, 1,3-bis (2,3-epithiopropyloxymethyl) Cyclohexane, 1,4-bis (2,3-epithiopropyloxymethyl) cyclohexane, 2,5-bis (2,3-epithiopropyloxymethyl) -1,4-dithiane, 2,5-bis [[ 2- (2,3-epithiopropyloxy) ethyl] thiomethyl] -1,4-dithiane, 2,5-bis (2,3-epithiopropyloxymethyl) -2,5-dimethyl-1,4- A cycloaliphatic 2,3-epithiopropyloxy compound such as dithiane; and
1,2-bis (2,3-epithiopropyloxy) benzene, 1,3-bis (2,3-epithiopropyloxy) benzene, 1,4-bis (2,3-epithiopropyloxy) benzene 1,2-bis (2,3-epithiopropyloxymethyl) benzene, 1,3-bis (2,3-epithiopropyloxymethyl) benzene, 1,4-bis (2,3-epithiopropyl) Oxymethyl) benzene, bis [4- (2,3-epithiopropyloxy) phenyl] methane, 2,2-bis [4- (2,3-epithiopropyloxy) phenyl] propane, bis [4- ( 2,3-epithiopropyloxy) phenyl] sulfide, bis [4- (2,3-epithiopropyloxy) phenyl] sulfone, 4,4′-bis (2,3-epithiopropyloxy) bi Examples include aromatic 2,3-epithiopropyloxy compounds such as phenyl.

As the polythietane compound, a metal-containing thietane compound or a non-metallic thietane compound can be used.
These polythietane compounds contain one or more thietanyl groups in the molecule as disclosed in WO2005-95490 and JP2003-327583. Preferably, it is a compound containing at least two thietanyl groups. For example, sulfide-type thietane compounds such as bisthietanyl sulfide, bis (3-thietanylthio) disulfide, bis (3-thietanylthio) methane, 3-(((3′-thietanylthio) methylthio) methylthio) thietane: bis (3-thietanyl And polysulfide-type thietane compounds such as disulfide, bis (3-thietanyl) trisulfide, bis (3-thietanyl) tetrasulfide, and bis (3-thietanyl) pentasulfide.

  Polycarbonate can be obtained by the reaction of alcohol and phosgene, the method of reacting alcohol and chloroformate, or the ester exchange reaction of a carbonic acid diester compound, but generally available commercially available polycarbonate resins are used. It is also possible. As a commercial product, Panlite series manufactured by Teijin Chemicals Ltd. can be used. The composition for optical material of the present embodiment can contain polycarbonate as a resin for optical material.

Poly (meth) acrylates include ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, hexylene glycol di (meth) acrylate, Poly (meth) acrylates of alkane polyols such as trimethylopropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate,
Diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, dibutylene glycol di (meth) acrylate, Polyoxyalkane polyol poly (meth) acrylates such as dipentaerythritol hexa (meth) acrylate,
Etc.
The composition for optical materials of this embodiment can contain poly (meth) acrylate as a resin for optical materials.

  The polyolefin is produced by polymerizing at least one olefin selected from α-olefins in the presence of a known olefin polymerization catalyst such as a Ziegler-Natta catalyst, a metallocene catalyst, or a so-called postmetallocene catalyst. The α-olefin monomer may be a single component or a composite component may be copolymerized.

The polymerization reaction of olefin in the production of polyolefin can be performed by a liquid phase polymerization method such as solution polymerization, suspension polymerization, bulk polymerization method, gas phase polymerization method, and other known polymerization methods. Preferably, for the production of polyolefin, liquid phase polymerization methods such as solution polymerization and suspension polymerization (slurry polymerization) are used, and more preferably suspension polymerization (slurry polymerization) method is used. Known conditions can be applied to the polymerization temperature and pressure conditions.
The composition for optical materials of this embodiment can contain polyolefin as a resin for optical materials.

  The cyclic polyolefin is produced by polymerizing at least one cyclic olefin selected from cyclic olefins in the presence of a known olefin polymerization catalyst. The cyclic olefin monomer may be a single component or a composite component may be copolymerized. As a cyclic polyolefin, trademark Apel manufactured by Mitsui Chemicals, Inc. has high transparency and can be suitably used.

  Polyallyl is produced by polymerizing at least one allyl group-containing monomer selected from allyl group-containing monomers in the presence of a known radical-generating polymerization catalyst. As the allyl group-containing monomer, allyl diglycol carbonate and diallyl phthalate are generally commercially available, and these can be suitably used.

  Polyurethane urea is a reaction product formed from a polyurethane prepolymer and a diamine curing agent, and is registered under the trademark TRIVEX under the name PPG Industries, Inc. A typical example is the one sold by Polyurethane polyurea is a highly transparent material and can be suitably used.

  The polyene-polythiol polymer is a polymer produced by addition polymerization consisting of a polyene compound having two or more ethylenic functional groups in one molecule and a polythiol compound having two or more thiol groups in one molecule and ethylene chain polymerization. It is a molecular product.

  Examples of the polyene compound in the polyene-polythiol polymer include allyl alcohol derivatives, esters of (meth) acrylic acid and polyhydric alcohol, urethane acrylate, and divinylbenzene. These 1 type (s) or 2 or more types can be used. Examples of allyl alcohol derivatives include triallyl isocyanurate, triallyl cyanurate, diallyl maleate, diallyl fumarate, diallyl adipate, diallyl phthalate, triallyl trimellitate, tetraallyl pyromellitate, glyceryl diallyl ether, trimethylolpropane diallyl Examples include ether, pentaerythritol diallyl ether, and sorbitol diallyl ether. Among the esters of (meth) acrylic acid and polyhydric alcohols, polyhydric alcohols include ethylene glycol, propylene glycol, 1,4-butanediol, 1,6-hexanediol, glycerin, trimethylolpropane, penta Examples include erythritol and sorbitol.

  The ring-opening metathesis polymer is a polymer obtained by ring-opening polymerization of cyclic olefins using a catalyst. Cyclic olefins that can be subjected to ring-opening polymerization are not particularly limited as long as they are olefins having a cyclic structure, but are usually monocyclic cycloalkenes having 3 to 40 carbon atoms, monocyclic cycloalkadienes. , Polycyclic cycloalkenes, and polycyclic cycloalkadienes. Specific examples of monocyclic cycloalkenes include, for example, cyclobutene, cyclopentene, cyclohexene, cyclooctene and the like. Specific examples of the monocyclic cycloalkadiene include, for example, cyclobutadiene, 1,3-cyclopentadiene, 1,3-cyclohexadiene, 1,4-cyclohexadiene, 1,5-cyclooctadiene, and the like. . Examples of the polycyclic cycloalkenes include norbornene and tetracyclo [6.2.1.1/3, 6.0 / 2.7] dodeca-4ene. Examples of the polycyclic cycloalkadiene include norbornadiene and dicyclopentadiene. These may be substituted with oxygen, sulfur, halogen or the like. Further, it may be used after hydrogenation. For example, JSR ARTON (trademark) can be cited as a suitable example.

  The polyester is subjected to condensation polymerization in the presence of a Lewis acid catalyst typified by antimony or a germanium compound, or a known polyester production catalyst such as an organic acid or an inorganic acid. Specifically, one or two or more selected from polycarboxylic acids including dicarboxylic acids and ester-forming derivatives thereof and one or two or more selected from polyhydric alcohols including glycols, or hydroxy Those consisting of carboxylic acids and their ester-forming derivatives, or those consisting of cyclic esters.

  Dicarboxylic acids include succinic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, dodecanedicarboxylic acid, tetradecanedicarboxylic acid, hexadecanedicarboxylic acid, 1,3 -Cyclobutanedicarboxylic acid, 1,3-cyclopentanedicarboxylic acid, 1,2-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, 2,5-norbornanedicarboxylic acid, dimer acid, etc. Saturated aliphatic dicarboxylic acids exemplified, or ester-forming derivatives thereof, unsaturated aliphatic dicarboxylic acids exemplified by fumaric acid, maleic acid, itaconic acid, etc., or ester-forming derivatives thereof, orthophthalic acid, isophthalic acid, terephthalic acid Acid, 5- (alkali metal) Rufoisophthalic acid, diphenic acid, 1,3-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid, 1,5-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, 4, 4 ′ -Biphenyldicarboxylic acid, 4,4'-biphenylsulfone dicarboxylic acid, 4,4'-biphenyl ether dicarboxylic acid, 1,2-bis (phenoxy) ethane-p, p'-dicarboxylic acid, pamoic acid, anthracene dicarboxylic acid, etc. And aromatic dicarboxylic acids exemplified in (1) or ester-forming derivatives thereof. Of these dicarboxylic acids, terephthalic acid and naphthalenedicarboxylic acid, particularly 2,6-naphthalenedicarboxylic acid, are preferable from the viewpoint of the physical properties of the resulting polyester, and other dicarboxylic acids are used as constituents as necessary. As polyvalent carboxylic acids other than these dicarboxylic acids, ethanetricarboxylic acid, propanetricarboxylic acid, butanetetracarboxylic acid, pyromellitic acid, trimellitic acid, trimesic acid, 3, 4, 3 ', 4'-biphenyltetracarboxylic acid, And ester-forming derivatives thereof.

As glycols, ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, diethylene glycol, triethylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 2,3-butylene glycol, 1,4 -Butylene glycol, 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanediol, 1,2-cyclohexanedi Methanol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, 1,4-cyclohexanediethanol, 1,10-decamethylene glycol, 1,12-dodecanediol, polyethylene glycol, polytrimethylene glycol, polytetra Michile Aliphatic glycols such as glycol, hydroquinone, 4,4′-dihydroxybisphenol, 1,4-bis (β-hydroxyethoxy) benzene, 1,4-bis (β-hydroxyethoxyphenyl) sulfone, bis ( p-hydroxyphenyl) ether, bis (p-hydroxyphenyl) sulfone, bis (p-hydroxyphenyl) methane, 1,2-bis (p-hydroxyphenyl) ethane, bisphenol A, bisphenol C, 2,5-naphthalenediol And aromatic glycols exemplified by glycols obtained by adding ethylene oxide to these glycols.
Of these glycols, ethylene glycol, 1,3-propylene glycol, 1,4-butylene glycol, and 1,4-cyclohexanedimethanol are preferred. Examples of polyhydric alcohols other than these glycols include trimethylolmethane, trimethylolethane, trimethylolpropane, pentaerythritol, glycerol, hexanetriol and the like.

  As the polyester, polyethylene terephthalate, polybutylene terephthalate, polypropylene terephthalate, poly (1,4-cyclohexanedimethylene terephthalate), polyethylene naphthalate, polybutylene naphthalate, polypropylene naphthalate and copolymers thereof are preferable.

The epoxy resin is a resin obtained by ring-opening polymerization of an epoxy compound, and the epoxy compound is a phenol obtained by a condensation reaction between a polyhydric phenol compound such as bisphenol A glycidyl ether or bisphenol F glycidyl ether and an epihalohydrin compound. Epoxy compounds;
An alcohol-based epoxy compound obtained by condensation of a polyhydric alcohol compound such as hydrogenated bisphenol A glycidyl ether, hydrogenated bisphenol F glycidyl ether or cyclohexanedimethanol with an epihalohydrin compound;
Glycidyl ester epoxy obtained by condensation of a polyvalent organic acid compound such as 3,4-epoxycyclohexylmethyl-3 ′, 4′-epoxycyclohexanecarboxylate or 1,2-hexahydrophthalic acid diglycidyl ester with an epihalohydrin compound Compound;
Examples thereof include amine-based epoxy compounds obtained by condensation of primary and secondary amine compounds and epihalohydrin compounds. In addition, aliphatic polyhydric epoxy compounds such as vinylcyclohexene diepoxide such as 4-vinyl-1-cyclohexane diepoxide can be used.

<Composition for optical material>
The composition for optical materials of this embodiment contains a phosphor and a resin for optical materials or a resin monomer. Further, as other components, a resin modifier or the like may be included. The composition for optical materials can be obtained by mixing these components by a predetermined method.
In the optical material composition of the present embodiment, from the viewpoint of the above effects, the phosphor is used in an amount of 0.00001 to 1 part by weight, preferably 0.0001 to 100 parts by weight of the optical material resin or resin monomer. It can be included in an amount of 0.1 parts by weight.
In order to contain a phosphor in a resin molded body, a method for mixing and polymerizing a composition for an optical material containing a phosphor and a resin monomer for an optical material, and an optical material containing a phosphor and an optical material resin are used. It can be performed by a method of curing the composition.

<Application>
The molded body of this embodiment includes a phosphor and a resin for optical materials, and can be used as an optical material. Optical materials include plastic eyeglass lenses, goggles, eyesight correction eyeglass lenses, imaging equipment lenses, liquid crystal projector Fresnel lenses, lenticular lenses, contact lenses and other plastic lenses, light emitting diode (LED) encapsulants, light Waveguide, optical lens, optical adhesive used for bonding optical waveguide, antireflection film used for optical lens, etc., transparent coating or transparent substrate used for liquid crystal display device members (substrate, light guide plate, film, sheet, etc.) Can be mentioned. The said molded object can be obtained from the composition for optical materials of this embodiment. In addition, the optical material of this embodiment does not contain an ultraviolet absorber.

  When a dark place is observed at night through the plastic spectacle lens of this embodiment made of a phosphor and a resin for optical materials, visibility is improved regardless of whether there is rainfall or not, and a good field of view can be obtained. Nighttime street lights and vehicle headlights contain a lot of highly diffusible short-wavelength visible light, and the object that is illuminated is flickering, making it difficult to see. Since the plastic spectacle lens absorbs short-wavelength visible light by a phosphor and emits light having a wavelength with high visibility, it can obtain a high brightness image while suppressing flickering.

  The optical material of the present embodiment can be suitably used as a plastic lens including a lens substrate, and a film layer and a coating layer that are laminated as necessary. The phosphor described above may be included in either the lens base material or the film layer, and the phosphor may be included in the coating layer. From the viewpoint of the above effects, the phosphor can be included in an amount of 0.00001 to 1 part by weight, preferably 0.0001 to 0.1 part by weight, with respect to 100 parts by weight of the optical material.

Examples of the plastic lens of the present embodiment include the following configurations.
Plastic lens A: A lens substrate made of a composition for optical materials is provided.
Plastic lens B: A film or a layer made of the composition for optical material is provided on at least one surface of the surface of the lens substrate (excluding the lens substrate obtained from the composition for optical material).
Plastic lens C: A lens base material (excluding a lens base material obtained from the optical material composition) is laminated on both surfaces of the film made of the optical material composition.
The optical material can be suitably used for a plastic spectacle lens.

(Plastic lens A)
Although the method of manufacturing the plastic lens A provided with the lens base material which consists of a composition for optical materials is not specifically limited, Cast polymerization using the lens casting mold is mentioned as a preferable manufacturing method. The lens substrate can be composed of polyurethane, polythiourethane, polysulfide, poly (meth) acrylate, or the like, and includes a phosphor and a monomer for these resins (resin monomer for optical material). Can be used.

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

  After the composition is injected, the lens casting mold is heated and molded by a predetermined temperature program in a heatable apparatus such as an oven or water. The resin molded body may be subjected to a treatment such as annealing as necessary.

In the present embodiment, when molding the resin, in addition to the above “other components”, a chain extender, a crosslinking agent, a light stabilizer, an antioxidant, Various additives such as bluing agents, oil-soluble dyes, fillers, and adhesion improvers may be added.
In addition, the plastic lens A in the present embodiment may have various coating layers on a lens substrate made of the composition for optical materials according to the purpose and application. The coating layer can include a phosphor. The coating layer containing the phosphor can be prepared using a coating material (composition) containing the phosphor, or the dispersion obtained by dispersing the phosphor in water or a solvent after forming the coating layer. It can be prepared by immersing a plastic lens with a coating layer in the liquid and impregnating the phosphor in the coating layer.

(Plastic lens B)
The plastic lens B in the present embodiment includes a film or layer made of the composition for optical materials on at least one surface of the lens substrate surface. The lens substrate is not formed from the composition for optical materials of the present embodiment.
As a manufacturing method of the plastic lens B, (1) a method of manufacturing a lens substrate, and then bonding a film or sheet made of the composition for optical material on at least one surface of the lens substrate, (2) A film or sheet made of the composition for optical materials is placed along one inner wall of the mold in the cavity of the molding mold held by a gasket or tape as described later, and then the polymerizable composition is placed in the cavity. Examples thereof include a method of injecting and curing.

The film or sheet made of the composition for optical material used in the method (1) is not particularly limited, but pellets of the composition for optical material obtained by melt kneading, impregnation, etc. are conventionally known in various ways. Specifically, for example, an injection molding method, a profile extrusion molding method, a pipe molding method, a tube molding method, a heterogeneous molded article coating method, an injection blow molding method, a direct blow molding method, a T-die sheet or film molding method, It can be obtained by a molding method such as an inflation film molding method or a press molding method. The resulting film or sheet comprises polycarbonate, polyolefin, or the like.
The lens substrate can be obtained from a known optical resin, and examples of the optical resin include (thio) urethane and polysulfide.
A known method can be used as a method of bonding a film or sheet made of the composition for optical materials onto the surface of the lens substrate.

The casting polymerization in the method (2) can be performed in the same manner as in the plastic lens A method. As the composition used for the casting polymerization, a composition containing a resin monomer for an optical material (not including a phosphor) is used. ).
In addition, the plastic lens B in the present embodiment may have various coating layers on the lens base material or “film or layer” made of the composition for optical materials in accordance with the purpose and application. Similar to the plastic lens A, the coating layer can contain a phosphor.

(Plastic lens C)
In the plastic lens C in the present embodiment, a lens base material (excluding a lens base material obtained from the optical material composition) is laminated on both surfaces of a film made of the optical material composition.
As a manufacturing method of the plastic lens C, (1) a method of manufacturing a lens base material and pasting it onto both surfaces of a film or sheet made of the composition for optical materials, and (2) a molding mold held by a gasket or a tape or the like. In this cavity, a film or sheet made of the composition for optical material is disposed in a state of being separated from the inner wall of the mold, and then a polymerizable composition is injected into the cavity and cured.

  As the film or sheet and the lens base material made of the composition for optical materials used in the method (1), those similar to the method (1) for the plastic lens B can be used. A known method can be used as a method of bonding a film or sheet made of the composition for optical materials onto the surface of the lens substrate.

The method (2) can be specifically performed as follows.
In the space of the lens casting mold used in the method of manufacturing the plastic lens A, a film or sheet made of the composition for optical material is placed so that both surfaces thereof are parallel to the front mold inner surface facing each other. To do.
Next, in the space of the lens casting mold, the composition containing the resin monomer for the optical material (not including the phosphor) is injected into the two gaps between the mold and the polarizing film by a predetermined injection means. To do.

After the composition is injected, the lens casting mold is heated and molded by a predetermined temperature program in a heatable apparatus such as an oven or water. The resin molded body may be subjected to a treatment such as annealing as necessary.
Further, the plastic lens C in the present embodiment may have various coating layers on the lens substrate in accordance with the purpose and application. Similar to the plastic lens A, the coating layer can contain a phosphor.

[Plastic eyeglass lenses]
A plastic spectacle lens can be obtained using the plastic lens of the present embodiment. If necessary, a coating layer may be provided on one side or both sides.

  Specific examples of the coating layer include a primer layer, a hard coat layer, an antireflection layer, an antifogging coat layer, a stainproof layer, and a water repellent layer. Each of these coating layers can be used alone, or a plurality of coating layers can be used in multiple layers. When a coating layer is applied to both sides, a similar coating layer or a different coating layer may be applied to each surface.

  These coating layers are the phosphor used in this embodiment, an infrared absorber for the purpose of protecting the eyes from infrared rays, a light stabilizer and an antioxidant for the purpose of improving the weather resistance of the lens, and the fashionability of the lens. For the purpose, dyes and pigments, photochromic dyes and photochromic pigments, antistatic agents, and other known additives for enhancing the performance of the lens may be used in combination. For the layer to be coated by coating, various leveling agents for the purpose of improving coating properties may be used.

  The primer layer is usually formed between a hard coat layer described later and the lens. The primer layer is a coating layer for the purpose of improving the adhesion between the hard coat layer formed thereon and the lens, and in some cases, the impact resistance can also be improved. Any material can be used for the primer layer as long as it has high adhesion to the obtained lens, but usually a primer mainly composed of urethane resin, epoxy resin, polyester resin, melamine resin, or polyvinyl acetal. A composition or the like is used. The primer composition may use an appropriate solvent that does not affect the lens for the purpose of adjusting the viscosity of the composition. Of course, you may use it without a solvent.

The primer layer can be formed by either a coating method or a dry method. In the case of using the coating method, the primer layer is formed by solidifying after applying the primer composition to the lens by a known coating method such as spin coating or dip coating. When performing by a dry method, it forms by well-known dry methods, such as CVD method and a vacuum evaporation method. When forming the primer layer, the surface of the lens may be subjected to a pretreatment such as an alkali treatment, a plasma treatment, or an ultraviolet treatment as necessary for the purpose of improving adhesion.
The hard coat layer is a coating layer for the purpose of imparting functions such as scratch resistance, abrasion resistance, moisture resistance, warm water resistance, heat resistance, and weather resistance to the lens surface.

  The hard coat layer is generally composed of an organic silicon compound having a curing property and an element selected from the element group of Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In, and Ti. A hard coat composition containing at least one kind of fine particles composed of one or more kinds of oxide fine particles and / or a composite oxide of two or more elements selected from these element groups is used.

  In addition to the above components, the hard coat composition includes at least amines, amino acids, metal acetylacetonate complexes, organic acid metal salts, perchloric acids, perchloric acid salts, acids, metal chlorides and polyfunctional epoxy compounds. It is preferable to include any of them. A suitable solvent that does not affect the lens may be used for the hard coat composition, or it may be used without a solvent.

  The hard coat layer is usually formed by applying a hard coat composition by a known application method such as spin coating or dip coating, followed by curing. Examples of the curing method include thermal curing, a curing method by irradiation with energy rays such as ultraviolet rays and visible rays, and the like. In order to suppress the occurrence of interference fringes, the refractive index of the hard coat layer is preferably in the range of ± 0.1 in the difference in refractive index from the lens.

The antireflection layer is usually formed on the hard coat layer as necessary. There are inorganic and organic antireflection layers. In the case of inorganic systems, inorganic oxides such as SiO ₂ and TiO ₂ are used, and vacuum deposition, sputtering, ion plating, ion beam assist, and CVD are used. It is formed by the dry method. In the case of an organic type, it is formed by a wet method using a composition containing an organosilicon compound and silica-based fine particles having internal cavities.

The antireflection layer has a single layer and a multilayer, and when used in a single layer, the refractive index is preferably at least 0.1 lower than the refractive index of the hard coat layer. In order to effectively exhibit the antireflection function, a multilayer antireflection film is preferably used. In that case, a low refractive index film and a high refractive index film are alternately laminated. Also in this case, the refractive index difference between the low refractive index film and the high refractive index film is preferably 0.1 or more. Examples of the high refractive index film include ZnO, TiO ₂ , CeO ₂ , Sb ₂ O ₅ , SnO ₂ , ZrO ₂ , and Ta ₂ O _5, and examples of the low refractive index film include an SiO ₂ film. .

  On the antireflection film layer, an antifogging layer, an antifouling layer, and a water repellent layer may be formed as necessary. As a method for forming the antifogging layer, the antifouling layer, and the water repellent layer, as long as the antireflection function is not adversely affected, the processing method and processing materials are not particularly limited, and a known antifogging treatment is possible. Methods, antifouling treatment methods, water repellent treatment methods, and materials can be used. For example, in the antifogging treatment method and the antifouling treatment method, a method of covering the surface with a surfactant, a method of adding a hydrophilic film to the surface to make it water absorbent, a method of covering the surface with fine irregularities and increasing water absorption Examples thereof include a method of absorbing water by utilizing photocatalytic activity, and a method of preventing water droplet adhesion by applying a super water-repellent treatment. Further, in the water repellent treatment method, a method of forming a water repellent treatment layer by vapor deposition or sputtering of a fluorine-containing silane compound or the like, or a method of forming a water repellent treatment layer by coating after dissolving the fluorine-containing silane compound in a solvent Etc.

  The optical resin composition of the present embodiment can be bonded as a sheet or film to a windshield such as a helmet or a windshield such as a vehicle.

In addition, this invention is not limited to the above-mentioned embodiment, A various aspect can be taken in the range which does not impair the effect of this invention.
For example, an optical material can be obtained without using the “composition for an optical material containing a phosphor” in the above-described embodiment. If the phosphor is not included, the “composition for optical material” of the above-described embodiment can be used, and the same configuration can be adopted. This aspect will be described below. In addition, when it is the same as that of the above-mentioned embodiment, description is abbreviate | omitted suitably.

  The optical material in the said aspect can be used as a plastic lens provided with the lens base material, the film layer laminated | stacked as needed, and a coating layer. The phosphor may be contained in at least one of the lens substrate, the film layer, and the coating layer.

Specifically, a dispersion obtained by preparing a molded body (lens substrate or optical film) using a composition for optical materials that does not contain a phosphor, and then dispersing the phosphor in water or a solvent. The molded body is dipped in and the phosphor is impregnated in the molded body and dried. An optical material can be prepared using the molded body thus obtained.
In addition, after the optical material is prepared, the optical material can be impregnated with the phosphor. For example, a plastic spectacle lens including a lens substrate, and a film layer and a coating layer laminated as necessary can be immersed in a dispersion containing the phosphor to impregnate the phosphor.
The impregnation amount of the phosphor can be controlled to a desired impregnation amount by the concentration of the phosphor in the dispersion, the temperature of the dispersion, and the time during which the optical material resin composition is immersed. The higher the concentration, the higher the temperature, and the longer the immersion time, the greater the amount of impregnation. When it is desired to precisely control the amount of impregnation, it is carried out by repeating immersion several times under the condition that the amount of impregnation is small.

In addition, a phosphor-containing coating layer can be formed on an optical material such as a plastic lens using a coating material containing a phosphor.
The optical material having such a configuration can be suitably used as a plastic spectacle lens.

  EXAMPLES The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. The materials and evaluation methods used in the examples of the present invention are as follows.

Example 1
A well-dried flask was charged accurately with 0.042 g of dibutyltin (II) dichloride, 0.084 g of Stefan ZelecUN and 0.0028 g of rubrene, and 2,5 (6) -bis (isocyanatomethyl) -bicyclo [2, 2,1] Heptane (35.4 g) was charged and dissolved by stirring at 25 ° C. for 1 hour. Thereafter, 16.7 g of pentaerythritol tetrakis (3-mercaptopropionate) and 17.9 g of 1,2-bis [(2-mercaptoethyl) thio] -3-mercaptopropane were charged into this preparation solution, The preparation liquid which was stirred for 30 minutes was prepared.
The prepared solution was defoamed at 600 Pa for 1 hour, and then poured into a 6C glass plate for plano having a center thickness of 2 mm and a diameter of 80 mm.
The glass mold was gradually heated from 25 ° C. over 16 hours, raised to 120 ° C., and kept at 120 ° C. for 4 hours. After cooling to room temperature, it was removed from the glass mold to obtain a planar lens.
The lens was cut into an appropriate shape with an NIDEK edging machine, and a spectacle frame was attached to obtain sample glasses.

(Comparative Example 1)
A planar lens was prepared in the same manner as in Example 1 except that rubrene was not used, and sample glasses were obtained.

Evaluation of Sample Lens The sample lens created in the example and the comparative example was attached, and the visibility of the object at night was evaluated. Evaluation was performed by five people A to E, and evaluation was performed according to the following criteria on a day with rain and a day without rain. The results are shown in Table 1.
○: Visibility is improved as compared with observation with the naked eye.
(Triangle | delta): There is no change in visibility compared with observation with a naked eye.
X: The visibility is lower than that observed with the naked eye.

Claims (16)

  An optical material comprising a phosphor having an excitation wavelength of 280 to 600 nm, a fluorescence wavelength of 450 to 750 nm, and a maximum fluorescence wavelength of 500 to 600 nm.   The optical material according to claim 1, wherein the phosphor comprises rubrene and / or rhodamines. A lens substrate, and a film layer and a coating layer that are laminated as necessary,
The optical material according to claim 1, wherein the phosphor is included in at least one of the lens substrate, the film layer, and the coating layer.   At least one of the lens substrate and the film layer has a phosphor having an excitation wavelength of 280 to 600 nm, a fluorescence wavelength of 450 to 750 nm, and a maximum fluorescence wavelength of 500 to 600 nm, and a resin or resin for optical materials The optical material of Claim 3 obtained from the composition for optical materials containing a monomer.   The optical material according to claim 4, wherein the resin for optical material or the resin obtained from the resin monomer is polyurethane, polythiourethane, polysulfide, polycarbonate, poly (meth) acrylate, or polyolefin.   A plastic spectacle lens made of the optical material according to claim 1.   An optical material composition comprising a phosphor having an excitation wavelength of 280 to 600 nm, a fluorescence wavelength of 450 to 750 nm, and a maximum fluorescence wavelength of 500 to 600 nm, and a resin or resin monomer for optical materials.   The composition for optical materials according to claim 7, wherein the phosphor comprises rubrene and / or rhodamines.   The composition for optical materials according to claim 7 or 8, wherein the resin for optical materials or the resin obtained from the resin monomer is polyurethane, polythiourethane, polysulfide, polycarbonate, poly (meth) acrylate, or polyolefin.   The molded object which consists of a composition in any one of Claims 7 thru | or 9.   A molded article comprising a phosphor having an excitation wavelength of 280 to 600 nm, a fluorescence wavelength of 450 to 750 nm, and a maximum fluorescence wavelength of 500 to 600 nm, and a resin for optical materials.   The optical material which consists of a molded object of Claim 10 or 11.   A plastic spectacle lens comprising a lens substrate made of the molded article according to claim 10 or 11.   The film which consists of a molded object of Claim 10 or 11.   The plastic spectacle lens provided with the layer which consists of a film of Claim 14 on at least one of the lens base-material surface.   A plastic spectacle lens comprising lens substrate layers on both sides of the film of claim 14.