JP2020007383A - Resin composition and molding - Google Patents

Abstract

To provide a resin composition that effectively prevents glare when used for optics and can improve contrast.SOLUTION: A resin composition contains (A) a thermoplastic resin or thermosetting resin, and (B) a coumarin compound, as an organic dye, represented by formula (1). [In formula (1), R-Reach represent H, halogen, an alkyl group, an aralkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylcarbonyl group, an arylcarbonyl group, and an amino group. Adjacent ones of R-Rmay be coupled to form an aliphatic ring, an aromatic ring or a heterocycle].SELECTED DRAWING: None

Description

  The present invention relates to a resin composition used for an optical material and a molded product obtained by molding the same. More specifically, a resin composition which can be used for an anti-glare optical article, has a low coloring effect, and has a high effect of cutting a wavelength that causes glare of external light or a light source, and a molded article obtained by molding the same. In particular, the present invention relates to a resin composition for an optical material and an optical product. Further, the present invention relates to the above-mentioned molded article which is also used for improving the life of an image display device such as a liquid crystal display device or an organic EL display and improving contrast in a bright room.

  It is known to provide a so-called anti-glare function to, for example, an eyeglass lens in order to reduce glare of sun rays and headlights of automobiles, and related discomfort and blurring of contrast, and visual fatigue. ing. In this technique, a wavelength band in which glare is easily perceived is selectively cut as much as possible, and a technique of blending a rare earth metal compound such as a neodymium compound into an eyeglass lens is disclosed in Patent Document 1 and the like. The neodymium compound has a sharp absorption around 570 to 590 nm, and can selectively absorb light of 550 to 610 nm, which has high human visibility and is easy to feel glare. Inorganic rare earth metal compounds such as neodymium compounds can be easily blended into glass lenses, but in recent years plastics that have become widely used as materials for spectacle lenses are difficult to disperse and blend with uniform transparent resin for lenses. It is difficult to get.

It is also being considered to mix specific organic rare earth metal complexes with plastic lens materials, but the selection of compounds is limited and limited to expensive compounds, resulting in insufficient solubility and dispersibility in resins. Still remain.
Patent Documents 2 to 4 disclose a technique in which a tetraazaporphyrin compound is contained in a plastic spectacle lens in place of a neodymium compound to cut off light near 580 nm to 590 nm to provide antiglare property and visibility. ing.
However, in order to prevent glare such as sunlight, it is not sufficient to simply cut light of 550 to 600 nm. In addition, it is necessary to cut off light having a shorter wavelength, particularly light in a blue to purple region of 450 nm or less, which causes glare and causes flickering and blurring of the visual field, and is harmful to the eyes. In addition, elderly people and cataract patients tend to have white turbidity in the crystalline lens of their eyes, and light having a wavelength of 450 nm or less is easily scattered.

  In recent years, with the increase in efficiency and price reduction of blue LED elements, lighting by LED light sources, displays for liquid crystal televisions and personal computers using LED light sources as backlights, portable electronic devices, and LED light sources have been used. Car lights and the like are increasing. These lights contain more blue components than conventional light sources, resulting in more glare.

Patent Documents 5 and 6 disclose spectacle lenses using a yellow dye or an orange dye as a blue light absorber. Patent Document 7 discloses that a yellow dye, an orange dye, or the like is applied as a blue light absorber to an antiglare optical article.
However, these anti-glare optical articles are colored yellow or orange, and the effect of preventing glare is not necessarily sufficient for spectacle lenses using the same.

In recent years, flat displays using a liquid crystal element, an organic EL element, and the like have been widely used. As an optical filter for improving the life of various display devices such as organic EL displays and liquid crystal displays, improving contrast, and cutting blue light of LED backlight displays, it has excellent long-wavelength UV cut ability, visible light transparency, and light resistance. There is a need for excellence. An optical filter having an absorption maximum in a wavelength region of 380 to 420 nm, a wavelength region of 480 nm to 520 nm, and a wavelength region of 585 nm to 620 nm is disclosed as an optical filter for improving the contrast of an image display device in a bright room. (Patent Document 8). The optical filter containing the dye described therein has problems in visible transparency and light resistance.
Patent Document 9 discloses an optical filter containing a specific squarylium compound. However, this optical filter has a problem in light resistance, and further improvement in visible light transparency is required.

JP 2000-75128 A JP 2008-134618 A JP 2011-145341 A JP 2011-175176 A JP-A-6-324293 JP-A-9-43550 JP 2001-356212 A JP 2008-203436 A JP 2009-139911 A

An object of the present invention is to provide a resin composition and a molded article having excellent antiglare performance and less coloring. More specifically, a resin composition that efficiently cuts blue light in the vicinity of 380 nm to 450 nm, prevents glare and glare, enhances contrast, and has almost no coloration, is excellent in product appearance, and has a wide application range. An object of the present invention is to provide a molded antiglare optical article such as a spectacle lens, a sun visor, a helmet shield, an antiglare coat for an information device display device, or an antiglare film.
Another object of the present invention is to provide an optical filter which is excellent in contrast enhancement and transparency of visible light and is stable to light.

The present inventors have studied the above problems, and found that this can be solved by including a coumarin compound having a specific structure in a thermoplastic resin or a thermosetting resin, and have completed the present invention. .
That is, the present invention
(I) a resin composition comprising (A) a thermoplastic resin or a thermosetting resin, and (B) at least a coumarin-based compound represented by the following general formula (1) as an organic dye;
[In the formula (1), R _{1 to} R ₉ are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group. Represents a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, an alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group, a substituted or unsubstituted amino group, ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , R ₇ and R ₈ , R ₈ and R ₉ are bonded to form an aliphatic ring or an aromatic ring Alternatively, a heterocyclic ring may be formed. ]
(Ii) In the general formula (1), R _{1 to} R ₉ each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, a trifluoromethyl group, a perfluoroalkyl group having 2 to 12 carbon atoms. A resin composition of (i), which is an alkoxy group having 1 to 12 carbon atoms or an alkoxyalkyl group having 2 to 16 carbon atoms, an alkylamino group having 1 to 8 carbon atoms, and a dialkylamino group having 2 to 16 carbon atoms in total;
(Iii) The thermoplastic resin is at least one selected from a polycarbonate resin, a polyamide resin, an acrylic resin, and a polyester resin, and the thermosetting resin is at least one selected from a polyurethane resin, a polythiourethane resin, and an allyl diglycol carbonate resin. Any one of (i) to (ii) a resin composition,
(Iv) a molded article obtained by molding the resin composition according to any one of (i) to (iii);
(V) the molded article of (iv), which is an optical article for antiglare;
(Vi) a molded product of (iv), which is an optical filter;
(Vii) a molded article of (iv), which is a sun visor;
(Viii) a molded article of (iv), which is a shield for a helmet,
(Ix) The molded article according to (iv), which is an antiglare coat for a display device of an information device or an antiglare film for a display device of an information device.

The resin composition of the present invention can efficiently cut blue light in the vicinity of 380 nm to 450 nm, prevent glare and glare, improve contrast, and increase visible transmittance.
Further, since there is almost no coloring, a molded article obtained by molding this is very suitable for an anti-glare optical article such as an eyeglass lens, a sun visor, a shield for a helmet, an anti-glare coat for an information device display device, or an anti-glare film. It is also useful for improving the life of image display devices such as liquid crystal display devices and organic EL displays, and for improving contrast in bright rooms. The resin composition of the present invention containing the coumarin-based compound represented by the general formula (1) as an organic dye has lower coloring than the case where a compound having another structure is used.
In addition, the resin composition of the present invention has high transparency because the pigment is well dissolved in the resin, and therefore transmits visible light other than unnecessary light well, and has a small decrease in light transmittance. Further, the resin composition of the present invention is useful because it has high light resistance and little deterioration of the dye in the resin.

9 is a transmission spectrum of a resin composition according to Example 7 of the present invention. 9 is a transmission spectrum of a resin composition according to Example 8 of the present invention. 15 is a transmission spectrum of the optical filter according to Example 9 of the present invention. 13 is a transmission spectrum of the optical filter according to Example 10 of the present invention.

Hereinafter, the present invention will be described in detail.
The resin composition of the present invention is characterized by containing (A) a thermoplastic resin or a thermosetting resin and (B) at least a coumarin compound having a specific structure as an organic dye.
First, the organic dye (B) will be described below.

[Coumarin compounds]
The coumarin compound having a specific structure according to the resin composition of the present invention is represented by the following general formula (1).
[In the formula (1), R _{1 to} R ₉ are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group. A substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, an alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group, an alkylamino group, a dialkylamino group, a substituted or unsubstituted Represents a substituted arylamino group, wherein R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , R ₇ and R ₈ , R ₈ and R ₉ They may combine to form an aliphatic ring, an aromatic ring or a heterocyclic ring. ]

Specific examples of R _{1 to} R ₉ will be described below.
Examples of the case where R _{1 to} R ₉ are a halogen atom include a chlorine atom, a fluorine atom, a bromine atom and an iodine atom, and a chlorine atom and a fluorine atom are preferred.

As those in which R _{1 to} R ₉ are a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms is preferable, and a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms is more preferable. preferable.

  Examples of unsubstituted alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl Group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, n-octyl group, 1- Examples thereof include a linear or branched unsubstituted alkyl group such as a methylheptyl group and a 2-ethylhexyl group.

  Examples of the substituted alkyl group include, for example, methoxymethyl group, ethoxymethyl group, n-butoxymethyl group, n-hexyloxymethyl group, (2-ethylbutyloxy) methyl group, and 2- (4′-pentenyloxy) An alkyl group having an alkyloxy group or an alkenyloxy group such as an ethyl group, for example, an alkyl group having an aralkyloxy group such as a benzyloxymethyl group or a 2- (benzyloxymethoxy) ethyl group, a phenyloxymethyl group, Alkyl groups having an aryloxy group such as -chlorophenyloxymethyl group and 4- (2'-phenyloxyethoxy) butyl group; for example, thioalkyl groups such as n-butylthiomethyl group and 2-n-octylthioethyl group; Alkyl groups having, for example, fluoromethyl group, trifluoromethyl group, Oroechiru group, 4-fluoro-cyclohexyl group, dichloromethyl group, 4-chloro cyclohexyl group include alkyl groups having a halogen atom such as 7-chloro-heptyl group.

As R _{1 to} R ₉ being a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkyl group having 7 to 25 carbon atoms is preferable, and a substituted or unsubstituted aralkyl group having 7 to 19 carbon atoms is more preferable. preferable.
Examples of the substituted or unsubstituted aralkyl group include a benzyl group, an α-methylbenzyl group, a phenethyl group, an α-methylphenethyl group, an α, α-dimethylbenzyl group, an α, α-dimethylphenethyl group, and a 4-methylphenethyl group. Aryl groups such as unsubstituted or alkyl-containing aralkyl groups such as a 4-methylbenzyl group and 4-isopropylbenzyl group; for example, 4-benzylbenzyl group, 4-phenethylbenzyl group and 4-phenylbenzyl group Group or aralkyl group having an aralkyl group, for example, 4-methoxybenzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl Group, 4-vinyloxymethylbenzyl group, 4-benzyloxybenzyl group, 4- Aralkyl group having a substituent group, such as E phenethyl oxy benzyl group. For example, an aralkyl group having a hydroxyl group such as a 4-hydroxybenzyl group and a 4-hydroxy-3-methoxybenzyl group, for example, a halogen atom such as a 4-fluorobenzyl group, a 3-chlorobenzyl group, and a 3,4-dichlorobenzyl group And further include, for example, a 2-furfuryl group, a diphenylmethyl group, a 1-naphthylmethyl group, and a 2-naphthylmethyl group.

Examples of the substituted or unsubstituted aryl group in which R _{1 to} R ₉ are a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-anthracenyl group, a 1-phenanthryl group, a 2-phenanthryl group, and a 3-phenanthryl group , A 1-pyrenyl group, a 2-pyrenyl group, a 2-perylenyl group, a 3-perylenyl group, a 2-fluoranthenyl group, a 3-fluoranthenyl group, a 7-fluoranthenyl group, an 8-fluoranthenyl group and the like. An unsubstituted aryl group, for example, a 1-methyl-2-pyrenyl group, a 2-methylphenyl group, a 4-ethylphenyl group, a 4- (4′-tert-butylcyclohexyl) phenyl group, a 3-cyclohexylphenyl group, -Cyclohexylphenyl group, 4-ethyl-1-naphthyl group, 6-n-butyl-2-naphthyl group, 2,4-dimethylphenyl group, etc. Aryl group having a phenyl group, for example, 4-methoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group, 3-isopropoxyphenyl group, 2-isopropoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-methyl-5-methoxyphenyl group, 2 Aryl group having an alkoxy group such as -phenyloxyphenyl group or aryloxy group, 4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 2,6-diphenylphenyl group, 4- (2 ′ -Naphthyl) phenyl group, 2-phenyl-1-naphthyl group, 1-phenyl-2-naphth Aryl group having an aryl group such as 7-phenyl-1-pyrenyl group, for example, 4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 4-bromophenyl Group, 2-chloro-5-methylphenyl group, 2-chloro-6-methylphenyl group, 2-methyl-3-chlorophenyl group, 2-methoxy-4-fluorophenyl group, 2-fluoro-4-methoxyphenyl group Aryl group having a halogen atom, such as 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 3,5-bistrifluoromethylphenyl group, 4-perfluoroethylphenyl Group, 4-methylthiophenyl group, 4-ethylthiophenyl group, 4-cyanophenyl group, 3-cy And an anophenyl group.

As those in which R _{1 to} R ₉ are a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms is preferable, and a substituted or unsubstituted alkoxy group having 1 to 8 carbon atoms is more preferable. preferable.
Examples of unsubstituted alkoxy groups include, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, tert-butyloxy, sec-butyloxy, n-pentyloxy Group, isopentyloxy group, n-hexyloxy group, 2-methylpentyloxy group, 1,1-dimethylbutyloxy group, 1,2,2-trimethylpropyloxy group, 2-ethylbutyloxy group, 1.3 -Dimethylhexyloxy group, cyclohexyloxy group, methylcyclopentyloxy group, n-heptyloxy group, n-heptyloxy group, n-octyloxy group, 3,5,5-trimethylhexyloxy group, n-decyloxy group, n -Undecyloxy group, n-dodecyloxy group, 1-adamantyloxy group, n-pe Linear such Tadeshiruokishi group include unsubstituted alkoxy group branched or cyclic.

  Examples of the substituted alkoxy group include, for example, methoxymethoxy group, ethoxymethoxy group, n-propyloxymethoxy group, n-butyloxymethoxy group, isobutyloxymethoxy group, tert-butyloxymethoxy group, n-pentyloxymethoxy group , 2-methoxyethoxy group, 2-ethoxyethoxy group, 2-n-propyloxyethoxy group, 2-isopropyloxyethoxy group, 2-n-butyloxyethoxy group, 2-isobutyloxyethoxy group, 2-tert-butyl Oxyethoxy group, 2-sec-butyloxyethoxy group, 2-n-pentyloxyethoxy group, 2-isopentyloxyethoxy group, 2-tert-pentyloxyethoxy group, 2-sec-pentyloxyethoxy group, 2- Cyclopentyloxyethoxy group, 2-n-hexyloxyethoxy 1, 2- (4-ethylcyclohexyloxy) ethoxy, 2-n-nonyloxyethoxy, 2- (3,5,5-trimethylhexyloxy) ethoxy, 2-n-decyloxyethoxy, 2 -N-dodecyloxyethoxy group, 3-methoxypropyloxy group, 3-ethoxypropyloxy group, 3- (n-propyloxy) propyloxy group, 2-isopentyloxypropyloxy group, 2-methoxybutyloxy group, Alkoxy such as 4-ethoxybutyloxy group, 4- (n-propyloxy) butyloxy group, 4-isopropyloxybutyloxy group, 5-methoxypentyloxy group, 5-ethoxymethoxy group, and 6-n-propylhexyloxy group An alkoxy group substituted with a group;

Methoxymethoxymethoxy group, ethoxymethoxymethoxy group, propyloxymethoxymethoxy group, butyloxymethoxymethoxy group, methoxyethoxymethoxy group, ethoxyethoxymethoxy group, propyloxyethoxymethoxy group, methoxymethoxyethoxy group, ethoxymethoxyethoxy group, propyloxy Methoxyethoxy, butyloxymethoxyethoxy, propyloxyethoxyethoxy, butyloxyethoxyethoxy, propyloxybutyloxyethoxy, methoxymethoxypropyloxy, ethoxymethoxypropyloxy, butyloxymethoxypropyloxy, methoxymethoxy Butyloxy group, ethoxymethoxybutyloxy group, butyloxymethoxybutyloxy group, ethoxyethoxybutyl Alkoxy group, (4 Echirushikuro hexyloxy) ethoxyethoxy group, [4- (3,5,5-trimethyl hexyloxy) butyloxy] alkoxy group substituted with an alkoxyalkoxy group such as ethoxy group;

An alkoxy group substituted by an alkoxycarbonyl group such as methoxycarbonylmethoxy group, ethoxycarbonylmethoxy group, n-propyloxycarbonylmethoxy group, isopropyloxycarbonylmethoxy group, (4′-ethylcyclohexyloxy) carbonylmethoxy group, methoxycarbonylethoxy An ethoxy group substituted with an alkoxycarbonyl group such as a group, an ethoxycarbonylethoxy group, an n-propyloxycarbonylethoxy group, or an ethoxycarbonylpropyloxy group;

Methylaminomethoxy group, 2-methylaminoethoxy group, 2- (2-methylaminoethoxy) ethoxy group, 4-methylaminobutyloxy group, 1-methylaminopropan-2-yloxy group, 3-methylaminopropyloxy group 2-methylamino-2-methylpropyloxy group, 2-ethylaminoethoxy group, 2- (2-ethylaminoethoxy) ethoxy group, 3-ethylaminopropyloxy group, 1-ethylaminopropyloxy group, 2- An alkoxy group substituted with an alkylamino group such as an isopropylaminoethoxy group, a 2- (n-butylamino) ethoxy group, a 3- (n-hexylamino) propyloxy group, or a 4- (cyclohexylamino) butyloxy group;

Dimethylaminomethoxy group, 2-dimethylaminoethoxy group, 2- (2-dimethylaminoethoxy) ethoxy group, 4-dimethylaminobutyloxy group, 1-dimethylaminopropan-2-yloxy group, 3-dimethylaminopropyloxy group , 2-dimethylamino-2-methylpropyloxy group, 2-diethylaminoethoxy group, 2- (2-diethylaminoethoxy) ethoxy group, 3-diethylaminopropyloxy group, 1-diethylaminopropyloxy group, 2-diisopropylaminoethoxy group An alkoxy group substituted with a dialkylamino group such as, 2- (di-n-butylamino) ethoxy group, 2-piperidylethoxy group, 3- (di-n-hexylamino) propyloxy group;

Alkoxy substituted with an alkylaminoalkoxy group such as a methylaminomethoxymethoxy group, a methylaminoethoxyethoxy group, a methylaminoethoxypropyloxy group, an ethylaminoethoxypropyloxy group, or a 4- (2′-isobutylaminopropyloxy) butyloxy group Group;

Alkoxy groups substituted by dialkylaminoalkoxy groups such as dimethylaminomethoxymethoxy group, dimethylaminoethoxyethoxy group, dimethylaminoethoxypropyloxy group, diethylaminoethoxypropyloxy group, and 4- (2'-diisobutylaminopropyloxy) butyloxy group ;

Methylthiomethoxy group, 2-methylthioethoxy group, 2-ethylthioethoxy group, 2-n-propylthioethoxy group, 2-isopropylthioethoxy group, 2-n-butylthioethoxy group, 2-isobutylthioethoxy group, ( An alkoxy group substituted with an alkylthio group such as a 3,5,5-trimethylhexylthio) hexyloxy group;

2-N-morpholinylethoxy group, 2-N-pyridylethoxy group, 2-N-pyrrolylethoxy group, 2- (2-furyl) ethoxy group, 2- (1-indolyl) ethoxy group, 2- ( Complexes such as 3-thienyl) ethoxy group, 3-N-morpholinylpropyloxy group, 3-N-pyridylpropyloxy group, 3-N-pyrrolylpropyloxy group, and 3- (1-indolyl) propyloxy group An alkoxy group substituted with a ring group;

As R _{1 to} R ₉ being a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group having 6 to 24 carbon atoms is preferable, and a substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms is preferable. Groups are more preferred.

  The substituted or unsubstituted aryloxy group also includes a heteroaryloxy group, and includes a phenyloxy group, a 2-methylphenyloxy group, a 4-methylphenyloxy group, a 4-ethylphenyloxy group, a 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 , 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, 3-methoxyphenyloxy group, 3-ethoxyphenyloxy group, 4-n-propoxyphenyloxy group, 4-n-butoxyphenyloxy group, 4-n-pentyloxy Phenyloxy group, 4-cyclohexyloxyphenyloxy group, 4-n-octyloxyphenyloxy group, 4-n-decyloxyphenyloxy group, 4-n-dodecyloxyphenyloxy group, 4-n-hexadecyloxyphenyl Oxy group, 2,3-dimethoxyphenyloxy group, 2,5-dimethoxyphenyloxy group, 3,5-dimethoxyphenyloxy group, 2-methoxy-4-methylphenyloxy group, 3-methoxy-4-methylphenyloxy Group, 3-methyl-4-methoxyphenyloxy group, 2-fluoro Phenyloxy group, 4-fluorophenyloxy group, 3-chlorophenyloxy group, 4-bromophenyloxy group, 3-trifluoromethylphenyloxy group, 3,5-difluorophenyloxy group, 3,4-dichlorophenyloxy group, 2 -Methyl-4-chlorophenyloxy group, 3-chloro-4-methylphenyloxy group, 3-methoxy-4-fluorophenyloxy group, 3-fluoro-4-methoxyphenyloxy group, 4-phenylphenyloxy group, -Phenylphenyloxy group, 4- (4'-methylphenyl) phenyloxy group, 4- (4'-methoxyphenyl) phenyloxy group, 1-naphthyloxy group, 4-methyl-1-naphthyloxy group, 6- n-butyl-2-naphthyloxy group, 7-ethoxy-2-naphthyloxy group, 2-thio Niruokishi group, 2-pyridyloxy group, 4-pyridyloxy group.

As R _{1 to} R ₉ being a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkylthio group having 1 to 18 carbon atoms is preferable, and a substituted or unsubstituted alkylthio group having 1 to 8 carbon atoms is more preferable. preferable.
Examples of unsubstituted alkylthio groups include, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, Isopentylthio, n-hexylthio, 2-methylpentylthio, 1,1-dimethylbutylthio, 1,2,2-trimethylpropylthio, 2-ethylbutylthio, 1,3-dimethylhexyl Thio group, cyclohexylthio group, methylcyclopentylthio group, n-heptylthio group, n-heptylthio group, n-octylthio group, 3,5,5-trimethylhexylthio group, n-decylthio group, n-undecylthio group, a straight-chain, branched or cyclic radical such as n-dodecylthio, 1-adamantylthio, n-pentadecylthio, etc. Alkylthio groups of the conversion.

  Examples of the substituted alkylthio group include, for example, methoxymethylthio, ethoxymethylthio, n-propyloxymethylthio, n-butyloxymethylthio, isobutyloxymethylthio, tert-butyloxymethylthio, n-pentyloxymethylthio 2-methoxyethylthio group, 2-ethoxyethylthio group, 2-n-propyloxyethylthio group, 2-isopropyloxyethylthio group, 2-n-butyloxyethylthio group, 2-isobutyloxyethylthio group A 2-tert-butyloxyethylthio group, a 2-sec-butyloxyethylthio group, a 2-n-pentyloxyethylthio group, a 2-isopentyloxyethylthio group, a 2-sec-pentyloxyethylthio group, 2-n-hexyloxyethylthio group, 2- (4-ethylcyclohexyl) (Siloxy) ethylthio, 2-n-nonyloxyethylthio, 2- (3,5,5-trimethylhexyloxy) ethylthio, 2-n-decyloxyethylthio, 2-n-dodecyloxyethylthio , 3-methoxypropylthio, 3-ethoxypropylthio, 3- (n-propylthio) propylthio, 2-isopentyloxypropylthio, 2-methoxybutylthio, 4-ethoxybutylthio, 4- an alkylthio group substituted with an alkoxy group such as a (n-propyloxy) butylthio group, a 5-methoxypentylthio group, a 5-ethoxypentylthio group, a 6-n-propyloxyhexylthio group;

Methoxymethoxymethylthio, ethoxymethoxymethylthio, propyloxymethoxymethylthio, butyloxymethoxymethylthio, ethoxyethoxymethylthio, propyloxyethoxymethylthio, methoxymethoxyethylthio, ethoxymethoxyethylthio, propyloxymethoxyethylthio Group, butyloxymethoxyethylthio group, propyloxyethoxyethylthio group, butyloxyethoxyethylthio group, propyloxybutyloxyethylthio group, methoxymethoxypropylthio group, ethoxymethoxypropylthio group, butyloxymethoxypropylthio group, Butyloxymethoxybutylthio group, ethoxyethoxybutylthio group, cyclohexyloxyethoxyethylthio group, [4- (3,5,5-tri Ethylhexyl oxy) butyloxy] alkylthio group substituted with an alkoxyalkoxy group such as an ethylthio group;
With an alkoxycarbonyl group such as a methoxycarbonylmethylthio group, an ethoxycarbonylmethylthio group, an n-propyloxycarbonylmethylthio group, a methoxycarbonylethylthio group, an ethoxycarbonylethylthio group, an n-propyloxycarbonylethylthio group, an ethoxycarbonylpropylthio group, etc. Substituted alkylthio group;
Methylaminomethylthio group, 2-methylaminoethylthio group, 2- (2-methylaminoethoxy) ethylthio group, 4-methylaminobutylthio group, 1-methylaminopropan-2-yloxy group, 3-methylaminopropylthio Group, 2-ethylaminoethylthio group, 2- (2-ethylaminoethoxy) ethylthio group, 3-ethylaminopropylthio group, 1-ethylaminopropylthio group, 2-isopropylaminoethylthio group, 2- (n An alkylthio group substituted with an alkylamino group such as -butylamino) ethylthio group, 3- (n-hexylamino) propylthio group, 4- (cyclohexylamino) butylthio group;
Dimethylaminomethylthio, 2-dimethylaminoethylthio, 4-dimethylaminobutylthio, 1-dimethylaminopropan-2-ylthio, 3-dimethylaminopropylthio, 2-diethylaminoethylthio, 3-diethylamino Dialkylamino groups such as propylthio group, 2-diisopropylaminoethylthio group, 2- (di-n-butylamino) ethylthio group, 2-piperidylethylthio group and 3- (di-n-hexylamino) propylthio group; A substituted alkylthio group;
Methylthiomethylthio, 2-methylthioethylthio, 2-ethylthioethylthio, 2-n-propylthioethylthio, 2-isopropylthioethylthio, 2-n-butylthioethylthio, 2-isobutyl An alkylthio group substituted with an alkylthio group such as a thioethylthio group or a (3,5,5-trimethylhexylthio) hexylthio group;
2-N-morpholinylethylthio group, 2-N-pyridylethylthio group, 2-N-pyrrolylethylthio group, 2- (2-furyl) ethylthio group, 2- (1-indolyl) ethylthio group, 2- (3-thienyl) ethylthio group, 3-N-morpholinylpropylthio group, 3-N-pyridylpropylthio group, 3-N-pyrrolylpropylthio group, 3- (1-indolyl) propylthio group, etc. And an alkylthio group substituted with a heterocyclic group.

As R _{1 to} R ₉ being a substituted or unsubstituted arylthio group, a substituted or unsubstituted arylthio group having 6 to 24 carbon atoms is preferable, and a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms is more preferable. preferable.
The substituted or unsubstituted arylthio group also includes a heteroarylthio group, and includes a phenylthio group, a 2-methylphenylthio group, a 4-methylphenylthio group, a 3-ethylphenylthio group, and a 4-n-propylphenylthio group. , 4-n-butylphenylthio, 4-isobutylphenylthio, 4-tert-butylphenylthio, 4-n-pentylphenylthio, 4-n-hexylphenylthio, 4-cyclohexylphenylthio , 4-n-octylphenylthio, 4-n-dodecylphenylthio, 4-n-octadecylphenylthio, 2,5-dimethylphenylthio, 3,4-dimethylphenylthio, 5-indanylthio 1,2,3,4-tetrahydro-6-naphthylthio group, 2-methoxyphenylthio group, 3-methoxyphenyl Nilthio group, 4-ethoxyphenylthio group, 4-n-propoxyphenylthio group, 2,4-dimethoxyphenylthio group, 3,5-diethoxyphenylthio group, 2-methoxy-4-methylphenylthio group, 2 -Methyl-4-methoxyphenylthio group, 2-fluorophenylthio group, 4-fluorophenylthio group, 2-chlorophenylthio group, 4-bromophenylthio group, 4-trifluoromethylphenylthio group, 3-trifluoro Methylphenylthio, 2,4-difluorophenylthio, 2,4-dichlorophenylthio, 2-chloro-4-methoxyphenylthio, 2-naphthylthio, 4-methyl-1-naphthylthio, 4-ethoxy -1-naphthylthio group, 2-pyridylthio group, 4-aminophenylthio group, 4- (N, N-dimethyla No) phenylthio group, 4- (N, N-diethylamino) -1-naphthylthio group, 4- [N, N-di (4'-methylphenyl) amino] phenylthio group, 4- (N-phenoxadiyl) phenylthio And the like.

As R _{1 to} R ₉ being a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted alkylcarbonyl group having a total of 2 to 13 carbon atoms is preferable, and a substituted or unsubstituted alkylcarbonyl group having a total of 2 to 9 carbon atoms is preferable. Alkylcarbonyl groups are more preferred.
Examples of the substituted or unsubstituted alkylcarbonyl group include formyl group, acetyl group, propionyl group, butyryl group, valeryl group, iso-valeryl group, sec-valeryl group, trimethylacetyl group, hexanoyl group, t-butylacetyl group, and heptanoyl. Group, octanoyl group, 2-ethylhexanoyl group, nonanoyl group, decanoyl group, undecanoyl group, lauroyl group, tridecanoyl group, tetradecanoyl group, pentadecanoyl group, hexadecanoyl group, heptadecanoyl group, octadecanoyl group, Oleoyl, cyclopentanecarbonyl, cyclohexanecarbonyl, 6-chlorohexanoyl, 6-bromohexanoyl, trifluoroacetyl, pentafluoropropionyl, perfluorooctanoyl, 2,2,4, 4, , 5,7,7,7- nonafluoro-3,6-oxa heptanoyl group, methoxyacetyl group, 3,6-oxa heptanoyl group, cinnamoyl group and the like.
As R _{1 to} R ₉ being a substituted or unsubstituted arylcarbonyl group, a substituted or unsubstituted arylcarbonyl group having a total of 7 to 25 carbon atoms is preferable, and a substituted or unsubstituted arylcarbonyl group having a total of 7 to 19 carbon atoms is preferable. An arylcarbonyl group is more preferred.

As the substituted or unsubstituted arylcarbonyl group, a benzoyl group, a 2-methylbenzoyl group, a 3-methylbenzoyl group, a 4-methylbenzoyl group, a 4-ethylbenzoyl group, a 4-n-propylbenzoyl group, a 4-tert- Butylbenzoyl group, 2,4-dimethylbenzoyl group, 2,4,6-trimethylbenzoyl group, 2,4,5-trimethylbenzoyl group, 4-ethylbenzoyl group, 4-isopropylbenzoyl group, 4-n-butylbenzoyl Group, 4-isobutylbenzoyl group, 4-sec-butylbenzoyl group, 4-tert-butylbenzoyl group, 4-n-pentylbenzoyl group, 4-isopentylbenzoyl group, 4-neopentibenzoyl group, 4-isohexyl Benzoyl group, 4-cyclohexylbenzoyl group, 4-octylbenzoyl group, 4-cyano Benzoyl group, 4-nitrobenzoyl group, 4-trifluoromethylbenzoyl group, 3-bromobenzoyl group, 2-fluorobenzoyl group, 4-chlorobenzoyl group, 2,6-dichlorobenzoyl group, 2,4-difluorobenzoyl A naphthylcarbonyl-1-yl group and a naphthylcarbonyl-2-yl group.
As R _{1 to} R ₉ being a substituted or unsubstituted amino group, an amino group or a substituted amino group having a total of 1 to 24 carbon atoms is preferable, and a dialkylamino group having a total of 2 to 16 carbon atoms is more preferable.
As the substituent of the substituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group are preferable.
Examples include methylamino, ethylamino, propylamino, butylamino, pentylamino, hexylamino, heptylamino, octylamino, 2-ethylhexylamino, cyclohexylamino, 3,5 Monoalkylamino groups such as, 5-trimethylhexylamino group, nonylamino group, decylamino group;
Dimethylamino group, diethylamino group, methylethylamino group, di-n-propylamino group, di-n-butylamino group, di-n-pentylamino group, N-methyl-N-ethylamino group, N-ethyl- Dialkylamino groups such as N-isopropylamino group, N-ethyl-N-cyclohexylamino group, N-methyl-Nn-octylamino group;
N-methyl-N-phenylamino group, N-ethyl-N-phenylamino group, N-ethyl-N- (2,4-dimethylphenyl) amino group, Nn-propyl-N- (2-ethoxyphenyl A) an amino group, an N-methyl-N- (3-chlorophenyl) amino group, a diphenylamino group, a di- (p-tolyl) amino group, an N-methyl-N- (2-naphthyl) amino group or the like; An amino group having;
Benzylamino group, phenethylamino group, 3-phenylpropylamino group, 4-ethylbenzylamino group, 4-isopropylbenzylamino group, dibenzylamino group, diphenethylamino group, bis (4-ethylbenzyl) amino group, bis An amino group having an aralkyl group such as (4-isopropylbenzyl) amino group, N-ethyl-N-benzylamino group, N-methyl-N-phenethylamino group; and the like.

  Specific examples of the coumarin-based compound of the general formula (1) contained in the resin composition of the present invention are shown in Table 1 below, but are not limited to these ranges.

The coumarin compound of the general formula (1) contained in the resin composition of the present invention is known and can be produced by a known method.
For example, it can be produced by the method described in JP-A-8-28326.
As an example, it can be produced by reacting a coumarin carboxylic acid derivative of the following general formula (2) with an aniline derivative of the following general formula (3) in toluene in the presence of thionyl chloride and pyridine.
[Wherein, R _{1 to} R ₉ are the same as R _{1 to} R _{9 in} formula (1). ]

[Thermoplastic resin or thermosetting resin]
Next, the thermoplastic resin or thermosetting resin (A) will be described below.
The resin used in the resin composition of the present invention may be either a thermoplastic resin or a thermosetting resin, but is preferably a transparent resin.

Examples of the thermoplastic resin include a polycarbonate resin, a polyamide resin, a polyester resin, an acrylic resin, a polyurethane resin, a polystyrene resin, an acrylonitrile / styrene resin, a norbornene resin, and a cellulosic resin.A polycarbonate resin, a polyamide resin, an acrylic resin and It is preferably at least one selected from polyester resins.
The polycarbonate resin is a polymer obtained mainly by a phosgene method of reacting a dihydroxydiaryl compound with phosgene, or a transesterification method of reacting a dihydroxydiaryl compound with a carbonic acid ester such as diphenyl carbonate. And a polycarbonate resin produced from 2,2-bis (4-hydroxyphenyl) propane (bisphenol A).
Examples of the dihydroxydiaryl compounds include bisphenol A, 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-dichlorophenyl) ) (Hydroxyaryl) alkanes such as propane, (hydroxyaryl) cycloalkanes such as 1,1-bis (4-hydroxyphenyl) cyclopentane, 1,1-bis (4-hydroxyphenyl) cyclohexane, Dihydroxydiaryl ethers such as 4,4'-dihydroxydiphenyl ether, 4,4'-dihydroxy-3,3'-dimethyldiphenyl ether, dihydroxydiaryl sulfides such as 4,4'-dihydroxydiphenyl sulfide, 4,4'- Dihydroxydiarylsulfoxides such as dihydroxydiphenylsulfoxide and 4,4′-dihydroxy-3,3′-dimethyldiphenylsulfoxide, 4,4′-dihydroxydiphenylsulfone, and 4,4′-dihydroxy-3,3′-dimethyldioxide Such as dihydroxy diaryl sulfones such as Enirusuruhon thereof.
These are used alone or selected from two or more types. In addition to these, it may be used in combination with piperazine, dipiperidyl hydroquinone, resorcin, 4,4'-dihydroxydiphenyl and the like. The viscosity average molecular weight of the polycarbonate resin is usually 10,000 to 100,000, preferably 10,000 to 400,000.

  Further, the above dihydroxyaryl compound may be used in combination with a trivalent or higher 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 structure of a dehydration polycondensate of a diamine compound containing an aromatic or aliphatic group and a dicarboxylic acid compound containing an aromatic or aliphatic group. Here, the aliphatic group includes an alicyclic aliphatic group. The resin having the structure of the dehydration polycondensate of the diamine compound and the dicarboxylic acid compound is not necessarily limited to the resin obtained from the dehydration polycondensation reaction. For example, ring-opening of one or more lactam compounds It can also be obtained from polymerization and the like.

Examples of the diamine compounds include hexamethylenediamine, m-xylylenediamine, bis (4-aminocyclohexyl) methane, bis (4-amino-3-methylcyclohexyl) methane, trimethylhexamethylenediamine, bis (aminomethyl) norbornane , Bis (aminomethyl) tetrahydrodicyclopentadiene and the like, and one or more of these diamine compounds can be selected and used.
Examples of the dicarboxylic acid compounds include adipic acid, dodecanedicarboxylic acid, isophthalic acid, terephthalic acid, bis (hydroxycarbonylmethyl) norbornane, bis (hydroxycarbonylmethyl) tetrahydrodicyclopentadiene, and the like. And one or more of them can be selected and used.
Amorphous polyamide resins are particularly preferred from the viewpoint of transparency, and are generally referred to as transparent nylons. For example, Glylamide TR-55, Glylamide TR-90, Glylamide TR-XE3805 by Ems, or Trogamide CX by Huls -7323 and the like.

The acrylic resin is a polymer mainly composed of alkyl methacrylate, and may be a homopolymer of alkyl methacrylate or a copolymer using two or more kinds of alkyl methacrylates, or may be a 50% by weight alkyl methacrylate. % Or less and 50% by weight or less of a monomer other than alkyl methacrylate. As the alkyl methacrylate, those having an alkyl group of 1 to 4 carbon atoms are usually used, and among them, methyl methacrylate is preferably used.
In addition, the monomer other than the alkyl methacrylate may be a monofunctional monomer having one polymerizable carbon-carbon double bond in the molecule, or two or more polymerizable carbon atoms in the molecule. Although a polyfunctional monomer having a carbon double bond may be used, a monofunctional monomer is particularly preferably used. Examples thereof include alkyl acrylates such as methyl acrylate and ethyl acrylate, styrene monomers such as styrene and alkyl styrene, and unsaturated nitriles such as acrylonitrile and methacrylonitrile.

As the acrylic resin, the monomer is a polymer consisting essentially of only alkyl methacrylate, or the alkyl methacrylate accounts for, for example, 70% by weight or more, preferably 90% by weight or more of the monomer composition, It is preferably a copolymer of substantially only a monomer selected from an alkyl acrylate, a styrene monomer and an unsaturated nitrile. In particular, a polymer in which the monomer substantially consists only of alkyl methacrylate is most preferable, and a typical example is polymethyl methacrylate resin (PMMA). Many commercially available polymethyl methacrylate resins are available such as Soken Chemical MX150, Nippon Shokubai Eposter MA and Sekisui Plastics MBX Series.
Further, among acrylic resins, a glass transition temperature is low, for example, a glass transition temperature is less than 0 ℃, preferably -20 ℃ or less poly (meth) acrylate resin is used as an adhesive, an adhesive, etc. For example, it is widely used for laminating each layer of an optical filter for a thin display or bonding an optical filter to a display screen.
A resin composition containing the quinophthalone-based compound and the tetraazaporphyrin-based compound as the organic dye in the adhesive of the poly (meth) acrylate-based resin is also within the scope of the present invention.

As the poly (meth) acrylate-based resin used as the pressure-sensitive adhesive, a resin obtained by using 50% by weight or more of a (meth) acrylate having an alkyl group having 1 to 14 carbon atoms as a monomer is preferable.
Examples of the (meth) acrylate 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.
Other examples of copolymerizable monomers include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, methoxyethyl (meth) acrylate, ethoxyethyl (meth) acrylate, and ethoxyethoxyethyl (meth) acrylate. (Meth) acrylates; styrene monomers represented by α-methylstyrene, vinyltoluene, styrene, etc .; vinyl ether monomers represented by methylvinylether, ethylvinylether, isobutylvinylether, etc .; fumaric acid, fumaric acid Monoalkyl esters of acids, dialkyl esters of fumaric acid; maleic acid, monoalkyl esters of maleic acid, dialkyl esters of maleic acid, itaconic acid, monoalkyl esters of itaconic acid, dialkyl esters of itaconic acid, (T) Acrylonitrile, vinyl chloride, vinylidene chloride, vinyl acetate, vinyl ketone, vinyl pyridine, vinyl carbazole and the like.

As the polyester resin, typically, a homopolyester such as poly _C2-4 alkylene terephthalate or poly _C2-4 alkylene naphthalate, a _C2-4 alkylene arylate unit ( _C2-4 alkylene terephthalate and / or _{C2- A} copolyester containing ₄ alkylene naphthalate units as a main component. Examples thereof include polyarylate resins, aliphatic polyesters using aliphatic dicarboxylic acids such as adipic acid, and lactones such as ε-caprolactone alone or in combination. Coalescing is also included.
As the copolyester, a part of the C _2-4 alkylene glycol among the constituent units of the poly C _2-4 alkylene arylate may be replaced with a polyoxy C _2-4 alkylene glycol, a C _6-10 alkylene glycol, an alicyclic diol (cyclohexane Dimethanol, hydrogenated bisphenol A, etc., diol having an aromatic ring (9,9-bis (4- (2-hydroxyethoxy) phenyl) fluorene having a fluorenone side chain), bisphenol A, bisphenol A-alkylene oxide adduct, etc. ), And copolyesters in which part of an aromatic dicarboxylic acid is substituted with an asymmetric aromatic dicarboxylic acid such as phthalic acid or isophthalic acid, or an aliphatic C _6-12 dicarboxylic acid such as adipic acid. It is.
As the polyester resin, polyethylene terephthalate (PET), polytrimethylene terephthalate (PTT), polybutylene terephthalate (PBT), polyethylene naphthalate (PEN), and the like are preferable in terms of high transparency and the like. Also, non-crystalline copolyesters such as _C2-4 alkylene arylate copolyesters are preferable because of their excellent workability. In particular, PET is preferable because it is produced in large quantities and has excellent heat resistance, strength, and the like.

  Examples of the thermosetting resin include allyl diglycol carbonate monomer, diallyl phthalate monomer, a mixture of an isocyanate compound and a polyol or polythiol, and a cured product of a monomer used in the production of a corrective lens such as an acrylic monomer. It is selected from a polyurethane resin obtained by a polymerization reaction of an isocyanate compound and a polyol, a polythiourethane resin obtained by polymerizing an isocyanate compound and a polythiol compound, and an allyl diglycol carbonate resin which is a cured allyl diglycol carbonate monomer. Preferably, at least one kind is used.

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, tetramethyl xylylene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, Isophorone diisocyanate, an adduct in which several molecules of each of hydrogenated xylylene diisocyanate are bonded, isocyanurate or allophanate, etc. blocked with acetoacetic acid or malonic acid, and the like.Polyols include hydroxyl-containing polyesters, poly Ether, polycarbonate, polyacrylate, polycaptolactone and the like can be mentioned.
Representative examples of the polythiourethane resin include a polythiourethane resin produced from meta-xylylene diisocyanate and pentaerythritol tetrakis (3-mercaptopropionate).

  As the allyl diglycol carbonate resin, polydiethylene glycol bisallyl carbonate is preferable, and examples thereof include CR-39 resin (also referred to as ADC resin).

[Resin composition]
The resin composition of the present invention comprises (A) a thermoplastic resin or a thermosetting resin (both are also simply referred to as a resin) and (B) a coumarin compound represented by the general formula (1) as an organic dye. , At least.
The compounding amount of the resin and the organic dye in the resin composition of the present invention varies depending on the application and the thickness of the resin molded product. It is adjusted so that the visible light transmittance is 12 to 99%, preferably 20 to 90% in the thickness direction. For example, when mixing with a polycarbonate resin using a 2.15 mm thick spectacle lens, the amount of the organic dye used is 0.001% by weight to 0.1% by weight based on the polycarbonate resin. Generally, when the thickness of the molded body is 0.1 mm to 20 mm, the amount of the organic dye used is 0.0001 to 2% by weight based on the thermoplastic resin or the thermosetting resin.
In addition to the resin and the organic dye, known ultraviolet absorbers, infrared absorbers, and various resin additives can be added to the resin composition of the present invention, if necessary. Various resin additives include phenolic antioxidants, release agents, dyes and pigments, phosphorus heat stabilizers, weather resistance improvers, antistatic agents, antifogging agents, lubricants / antiblocking agents, flame retardants, fluidity Examples include an improver, a plasticizer, a dispersant, and a germicide.

The method for producing the resin composition of the present invention will be described below.
The resin composition of the present invention is obtained by mixing an organic dye and a thermoplastic resin or a thermosetting resin, and at least in a molded product obtained by molding this, the organic dye and the resin are in a compatible state. desirable.
When the resin of the resin composition is a thermoplastic resin, a resin composition is obtained by mixing the organic dye and the powder or pellets of the thermoplastic resin using various mixers such as a tumbler and a Henschel mixer. Is melt-kneaded with a known melt-kneader such as a Banbury mixer, a heating roll, a Brabender, a single-screw kneader-extruder, a twin-screw kneader-extruder, or a kneader, so that the organic pigment and the thermoplastic resin are uniformly mixed. Can be manufactured.
Alternatively, it can be produced by dissolving and mixing a thermoplastic resin and an organic dye in an organic solvent capable of dissolving the same, and then removing the organic solvent. As the organic solvent used at that time, hexane, heptane, acetone, methyl ethyl ketone, benzene, toluene, dichloromethane, chloroform and the like are mentioned, but are chemically inert to the resin composition, and have a moderately low boiling point It is not particularly limited as long as it is.
Further, after dissolving the organic dye in a solvent, the resin or the resin molded body may be brought into contact with the resin to diffuse and penetrate the organic dye into the resin, and thus the resin composition may be produced. Is within the scope of the rights. The organic solvent for dissolving the organic dye is not particularly limited, but must not decompose the organic dye or alter the thermoplastic resin. Usually, liquid ketones and alcohols are often used. The concentration of the solution is arbitrary according to the purpose, but is usually in a good range of about 0.01% to 30%. The diffusion conditions vary depending on the type of organic dye, solvent, thermoplastic resin and the like, but are usually 25 ° C. to 200 ° C. for several minutes to 5 hours under normal pressure or under pressure.

Further, an organic dye may be mixed with the raw material monomer of the thermoplastic resin by the above method and then polymerized. This production method will be described collectively in the case where the resin of the following resin composition is a thermosetting resin.
When the resin of the resin composition is a thermosetting resin, after dissolving the organic dye in a solvent, a method in which the organic dye is diffused into the resin by contacting the resin or a resin molded body, or a method of injecting the thermosetting resin. There is a method in which 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.
In the step of mixing an organic dye with a raw material monomer of a thermosetting resin, a method of forming a monomer mixture after mixing with any of a group of monomers constituting the monomer mixture depending on a mixing target of the organic dye, a monomer mixture and other additions There is a method of adding a catalyst after mixing with a mixture of agents, or a method of mixing with a mixture of a monomer mixture, a catalyst, and other additives.

Components other than monomers and organic dyes used for polymerization curing include polymerization catalysts and other additives.
As the polymerization catalyst, an organic peroxide is known, and examples thereof include compound systems such as diacyl peroxide, peroxydicarbonate, peroxyester, peroxyketal, dialkyl peroxide, and hydroperoxide.

  Other additives include catalysts such as dibutyltin dichloride, ultraviolet absorbers, internal release agents such as acidic phosphate esters, light stabilizers, antioxidants, reaction initiators such as radical reaction initiators, and chain extenders. , A crosslinking agent, a filler, and the like, and further added as necessary. Known resin modifiers 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 And the like.

When mixing the organic dye with the raw material monomer of the thermosetting resin, the organic dye may be directly mixed, or the organic dye may be dissolved in a low boiling point organic solvent in advance, and this organic solvent solution may be mixed with the raw material monomer. Thereafter, the organic solvent may be removed by evaporation under conditions such as heating and / or reduced pressure. Hexane, heptane, acetone, methyl ethyl ketone, benzene, toluene, dichloromethane, chloroform, etc. may be used as the organic solvent used at that time, but those which are chemically inert to the raw material monomers and have a moderately low boiling point If it is, there is no particular limitation.
In the mixing, the resin composition may be mixed so that an amount corresponding to the organic dye concentration required for the resin composition is contained in the resin composition, or one of the raw materials such as one monomer may have a higher concentration than the target concentration. A master batch containing an organic dye at a concentration may be prepared, and other components to be blended may be added and diluted as needed to produce a resin composition having a desired concentration. In dissolving the organic dye, it is also possible to heat the resin composition to such an extent that there is no problem in terms of deterioration of the resin composition, pot life and the like.

The conditions for the polymerization and curing will be described in the following cast polymerization method for molded articles.
[Molded body]
Hereinafter, the molded article of the present invention will be described.
The molded article of the present invention is obtained by molding the resin composition of the present invention.
As an embodiment of the molded article, an optical article made of a resin composition, an optical article partially containing the resin composition, or a powder or pellet state, a film, such as an intermediate material for producing an optical article, There may be.
Examples of the optical article include anti-glare optical articles such as spectacle lenses, sun visors, helmet shields, anti-glare coats or anti-glare films for display devices of information equipment, various filters, and covers for lighting equipment, as described below. it can. Further, examples thereof include an optical filter used for improving the life of an image display device such as a liquid crystal display device and an organic EL display, and improving contrast in a bright room.
In the present specification, the optical article partially containing the resin composition is a state in which the optical article is contained inside various members or films of the optical article, and is coated on or adhered to the surface of the member or each layer. It includes the state where it was set.

  The molding method varies depending on the product and the type of resin used, but in the case of a resin composition using a thermoplastic resin, for example, molding by a compression molding method, transfer molding method, extrusion molding method, injection molding method, etc., thermosetting In the case of a resin composition using a conductive resin, for example, a cast polymerization method is used.

The casting polymerization method will be described below.
The resin composition is poured into and built into the casting mold, and then the casting mold is heated in a heatable device such as an oven or water by a predetermined temperature program for several hours to several tens of hours. The polymerization curing temperature and time vary depending on the composition of the mixture, the type of catalyst, the shape of the mold, and the like, but are generally from -50 to 200C for 1 to 100 hours. Generally, it is common to start at a temperature in the range of 5 ° C. to 40 ° C., then gradually increase the temperature to a range of 80 ° C. to 130 ° C., and heat at that temperature for 1 hour to 4 hours. After the completion of the curing molding, the target molded product can be obtained by removing the molded product from the casting mold.
Further, there is a method in which a resin or a resin monomer and a coumarin-based compound are dispersed and dissolved in an organic solvent to produce a polymer molded body by a casting method.

[Optical article for anti-glare]
The molded article of the resin composition of the present invention is very useful as an anti-glare optical article.
Examples of anti-glare optical articles include spectacle lenses, sun visors, shields for helmets, windshield films for automobiles and airplanes, covers for automobile headlights, ski goggles, anti-glare coats or anti-glare films for display devices of information equipment And a filter for LED lighting, but can be used without limitation for the purpose of preventing glare and ensuring contrast and natural color tone.
The method for manufacturing the anti-glare optical article differs depending on the form of the article and the type of resin, and the above-described method for manufacturing a molded article can be applied.
In addition, depending on the functions required for the anti-glare optical article, one or more of an anti-reflection function, a hard coat function (anti-friction function), an anti-static function, an anti-fouling function, a gas barrier function, and an ultraviolet cut function are provided. A function may be provided.

[Optical filter]
The optical filter of the present invention preferably contains a coumarin compound represented by the general formula (1) in a substrate. In the present invention, being contained in a base material means being contained in the base material, applied to the surface of the base material, or sandwiched between the base materials.
Examples of the substrate include resin, glass and the like, and resin is preferable. As the resin, various forms such as an adhesive, a sheet, a film, a binder resin, and a molded body can be used. Also, a combination of a plurality of forms, such as having an adhesive on the sheet, may be used.
The thickness of the substrate is not particularly limited as long as it has a certain level of mechanical strength, but is usually 20 μm to 10 mm, preferably 20 μm to 1 mm, and more preferably 20 μm to 200 μm.

The method for producing the optical filter of the present invention using the coumarin-based compound of the general formula (1) is not limited, but (1) a method of including the compound in a transparent pressure-sensitive adhesive, and (2) a method of including the compound in a polymer molded article. And (3) a method of coating the surface of a polymer molding or glass.
(2) a method of incorporating the coumarin-based compound into a resin and a method of mixing the coumarin-based compound with a resin and heating the mixture; and (B) an organic solvent containing a resin or a resin monomer and a coumarin-based compound. Are dispersed and dissolved to produce a polymer molded body by a casting method.
The processing conditions vary depending on the coumarin compound and base polymer used, and the processing temperature and filming conditions are somewhat different.However, the coumarin compound is added to the base polymer powder or pellet, and heated to 150 to 350 ° C. and dissolved. And then forming the plate by molding. A method of forming a film with an extruder. A method in which a raw material is produced by an extruder, stretched uniaxially or biaxially by a factor of 2 to 5 at 30 to 120 ° C. to form a film having a thickness of 10 to 200 μm, or the like.
When kneading, an additive such as a plasticizer used for ordinary resin molding may be added. The amount of the coumarin-based compound to be added depends on the extinction coefficient, the thickness of the polymer molded article to be produced, the desired absorption intensity, the desired permeability / transmittance, etc., but is usually 1 ppm based on the weight of the base polymer molded article. -20 wt%, preferably 1 ppm-10 wt%, particularly preferably 1 ppm-5 wt%.

In the casting method (B), a coumarin-based compound is added and dissolved in an organic solvent solution of a resin or a resin monomer, and if necessary, a plasticizer, a polymerization initiator, and an antioxidant are added, and the required surface state is adjusted. A plate or a film can be manufactured by pouring the mixture into a mold or a drum having the mixture and volatilizing and drying the solvent or polymerizing, volatilizing and drying the solvent.
As the resin used, an aliphatic ester resin, an acrylic resin, a melamine resin, a urethane resin, an aromatic ester resin, a polycarbonate resin, an aliphatic polyolefin resin, an aromatic polyolefin resin, a polyvinyl resin, a polyvinyl alcohol resin, Modified polyvinyl resins (PVA, EVA, etc.) or copolymerized resin monomers thereof are mentioned.

Examples of the solvent include halogen-based, alcohol-based, ketone-based, ester-based, aliphatic hydrocarbon-based, aromatic hydrocarbon-based, ether-based solvents, and mixtures thereof.
The concentration of the coumarin compound depends on the extinction coefficient of the dye, the thickness of the plate or film, the desired absorption intensity, the desired transmission characteristics and transmittance, but is usually 1 ppm to 20% by weight based on the weight of the resin monomer. is there. Further, the resin concentration is 1 to 90% by weight based on the whole paint.

As a method of coating the surface of the polymer molded article or glass mentioned in (3), a method of dissolving a coumarin-based compound in a binder resin and an organic solvent to apply the coumarin-based compound, or a method of applying the coumarin-based compound to an uncolored acrylic emulsion paint. There is a method of dispersing a finely pulverized (50 to 500 nm) material to obtain an acrylic emulsion-based aqueous coating.
Examples of the binder resin include aliphatic ester resins, acrylic resins, melamine resins, urethane resins, aromatic ester resins, polycarbonate resins, aliphatic polyolefin resins, polyvinyl resins, polyvinyl alcohol resins, and polyvinyl resins (PVA, EVA, etc.) or copolymer resins thereof.
Examples of the solvent include a halogen-based, alcohol-based, ketone-based, ester-based, aliphatic hydrocarbon, aromatic hydrocarbon, ether-based solvent, and a mixture thereof.

  The concentration of the coumarin compound varies depending on the extinction coefficient, the thickness of the coating, the desired absorption intensity, the desired visible transmittance, and the like, but is usually 0.1 ppm to 30% by weight based on the weight of the binder resin. The resin concentration is usually 1 to 50% by weight based on the entire dye. In the case of an acrylic emulsion-based water-based paint, similarly, a pigment obtained by finely pulverizing (50 to 500 nm) a pigment is dispersed in an uncolored acrylic emulsion paint. Additives such as antioxidants and the like used in ordinary paints may be added to the paint.

The method for coating the surface of the polymer molded article or glass can be appropriately selected from coating methods such as a bar coater, a blade coater, a spin coater, a reverse coater, a die coater, and a spray.
The optical filter containing the coumarin-based compound of the general formula (1) of the present invention has a longer life of the organic EL light emitting element, an improved contrast of a liquid crystal display, a blue light cut of an LED liquid crystal display, and a durability of a near-infrared ray absorption cut filter. Can be used for enhancement purposes.

Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited by the following examples.
[Synthesis Example 1] Production of Specific Example Compound (1) -1 i) Production of 7-methoxycoumarin-3-carboxylic acid 15.2 g of 2-hydroxy-4-methoxybenzaldehyde, 18.6 g of Meldrum's acid, and piperidine acetate 0 .36 g was stirred in 200 mL of ethanol under reflux for 4 hours.
After cooling, the precipitate was collected by filtration, washed with ethanol, and dried to obtain 19.4 g of a pale yellow powder.
The obtained compound was confirmed to be the target compound from the following analysis results.
-ESI-Mass: 221 (M + H) ⁺
Elemental analysis value: actual measurement value (C: 60.03%, H: 3.69%);
Theoretical value (C: 60.01%, H: 3.66%)
ii) Preparation of Specific Example Compound (1) -1 After stirring 11 g of 7-methoxycoumarin-3-carboxylic acid prepared in i) of Synthesis Example 1 in 100 mL of toluene at 75 ° C. for 30 minutes, 0.25 g of DMF was added. Thereafter, 7.27 g of thionyl chloride was added dropwise, and the mixture was stirred at 75 ° C for 6 hours. After the excess thionyl chloride was distilled off, 50 mL of toluene was added, and 4.43 g of pyridine and 9.1 g of 4-butoxyaniline were added dropwise at 75 ° C., and the mixture was reacted for 3.5 hours. The reaction mixture was washed with 300 mL of 1% sodium hydroxide solution, washed with hot water, toluene was distilled off, 200 mL of methanol was added to the residue, and the mixture was refluxed for 30 minutes.
After cooling, the precipitate was collected by filtration and dried to obtain 7.2 g of (Specific Example Compound (1) -1) having the following structural formula as a pale yellow powder.
The obtained compound was confirmed to be the target compound from the following analysis results.
・ ESI-Mass: 368 (M + H) ⁺
Elemental analysis value: actual measurement value (C: 68.68%, H: 5.80%, N: 3.78%);
Theoretical value (C: 68.65%, H: 5.76%, N: 3.81%)
The toluene solution of the compound thus obtained showed a maximum absorption at 356 nm, and the gram extinction coefficient was 6.83 × 10 ⁴ g / mL · cm.

Synthesis Example 2 Synthesis of Specific Example Compound (1) -31 i) Production of 7-diethylaminocoumarin-3-carboxylic acid Instead of 15.2 g of 2-hydroxy-4-methoxybenzaldehyde of i) of Synthesis Example 1, 4 -Light tan powder 16.2 was obtained in the same manner as in i) of Synthesis Example 1 except that 19.3 g of dimethylaminosalicylaldehyde was used.
The obtained compound was confirmed to be the target compound from the following analysis results.
-ESI-Mass: 262 (M + H) ⁺
Elemental analysis value: actual measurement value (C: 64.40%, H: 5.81%, N: 5.33%);
Theoretical value (C: 64.36%, H: 5.79%, N: 5.36%)
ii) Preparation of Specific Compound (1) -31 7-Diethylaminocoumarin-3-carboxylic acid prepared in i) of Synthesis Example 2 instead of 11 g of 7-methoxycoumarin-3-carboxylic acid in ii) of Synthesis Example 1 In the same manner as in Synthesis Example 1 ii) except that 10.45 g of the acid was used and 8.2 g of 4-butylaniline was used instead of 9.1 g of 4-butoxyaniline, the following structural formula (specific compound (1) ) -31)
12.9 g were obtained as a pale yellow powder.
-ESI-Mass: 393 (M + H) ⁺
Elemental analysis value: actual measurement value (C: 73.47%, H: 7.21%, N: 7.11%);
Theoretical value (C: 73.44%, H: 7.19%, N: 7.14%)
The toluene solution of the compound thus obtained showed a maximum absorption at 423.5 nm, and the gram extinction coefficient was 1.37 × 10 ⁵ g / mL · cm.

Synthesis Example 3 Preparation of Specific Compound (1) -57 i) Preparation of 5,6-benzocoumarin-3-carboxylic acid Instead of 15.2 g of 2-hydroxy-4-methoxybenzaldehyde of Synthesis Example 1 i) 23.1 g of a pale yellow powder was obtained in the same manner as in i) of Synthesis Example 1 except that 17.2 g of 2-hydroxynaphthaldehyde was used.
The obtained compound was confirmed to be the target compound from the following analysis results.
-ESI-Mass: 241 (M + H) ⁺
Elemental analysis value: actual measurement value (C: 70.03%, H: 3.40%);
Theoretical value (C: 70.00%, H: 3.36%)

ii) Preparation of Specific Example Compound (1) -57 In Example ii) of Synthesis Example 1, instead of 11 g of 7-methoxycoumarin-3-carboxylic acid, 5,6-benzocoumarin-3 prepared in i) of Synthesis Example 3 -In the same manner as in Synthesis Example 1 ii) except that 12 g of carboxylic acid was used and 8.2 g of 4-butylaniline was used instead of 9.1 g of 4-butoxyaniline, 1) -57) was obtained as a pale yellow powder.
・ ESI-Mass: 372 (M + H) ⁺
Elemental analysis value: actual measurement value (C: 77.63%, H: 5.73%, N: 3.75%);
Theoretical value (C: 77.61%, H: 5.70%, N: 3.77%)
The toluene solution of the compound thus obtained showed a maximum absorption at 381.5 nm, and the gram extinction coefficient was 5.9 × 10 ⁴ g / mL · cm.

Synthesis Example 4 Specific Compound (1) -59
Synthesis Example 1 except that 12 g of 5,6-benzocoumarin-3-carboxylic acid prepared in i) of Synthesis Example 3 was used instead of 11 g of 7-methoxycoumarin-3-carboxylic acid in ii) of Synthesis Example 1. In the same manner as in ii), the following structural formula (specific compound (1) -57)
16.8 g were obtained as a pale yellow powder.
・ ESI-Mass: 388 (M + H) ⁺
Elemental analysis value: actual measurement value (C: 74.43%, H: 5.48%, N: 3.59%);
Theoretical value (C: 74.40%, H: 5.46%, N: 3.62%)
The toluene solution of the compound thus obtained showed a maximum absorption at 383 nm, and the gram extinction coefficient was 5.31 × 10 ⁴ g / mL · cm.

[Example 1]
After 1000 parts by weight of a polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering-Plastics Corporation) and 0.015 parts by weight of the coumarin-based compound (specific compound (1) -1) produced in Synthesis Example 1 were mixed by a tumbler for 20 minutes. The mixture was melted and kneaded by a single screw extruder under the conditions of a cylinder set temperature of 260 ° C. and a screw rotation speed of 56 rpm to form pellets.

[Example 2]
After mixing 1000 parts by weight of a polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering-Plastics Co., Ltd.) and 0.015 parts by weight of the coumarin-based compound (specific compound (1) -31) produced in Synthesis Example 2 for 20 minutes by a tumbler. The mixture was melted and kneaded by a single screw extruder under the conditions of a cylinder set temperature of 260 ° C. and a screw rotation speed of 56 rpm to form pellets.

[Example 3]
After 1000 parts by weight of a polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering-Plastics Corporation) and 0.015 parts by weight of the coumarin-based compound (specific compound (1) -57) produced in Synthesis Example 3 were mixed by a tumbler for 20 minutes. The mixture was melted and kneaded by a single screw extruder under the conditions of a cylinder set temperature of 260 ° C. and a screw rotation speed of 56 rpm to form pellets.

[Example 4]
1000 parts by weight of a polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering-Plastics Corporation) and 0.015 parts by weight of a coumarin-based compound (specific compound (1) -59) produced in Synthesis Example 4 were mixed by tumbling for 20 minutes. The mixture was melted and kneaded by a single screw extruder under the conditions of a cylinder set temperature of 260 ° C. and a screw rotation speed of 56 rpm to form pellets.

[Example 5]
After mixing 1000 parts by weight of a polyamide resin (manufactured by Ms. Chemie Japan: Grilamid TR90) and 0.01 part by weight of the specific compound (1) -1 by a tumbler for 20 minutes, the cylinder set temperature is 260 ° C. by a single screw extruder. The mixture was melted and kneaded under the conditions of a screw rotation number of 56 rpm to form pellets.

[Example 6]
After 1000 parts by weight of polymethyl methacrylate resin (manufactured by Asahi Kasei Corporation: 80 N) and 0.015 parts by weight of the specific compound (1) -31 were mixed by a tumbler for 20 minutes, the cylinder set temperature was 260 ° C. by a single screw extruder. The mixture was melted and kneaded under the conditions of a screw rotation number of 56 rpm to form pellets.

[Example 7]
Using the pellets produced in Example 1 as a raw material, a resin composition of 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. Was molded. When the transmission spectrum of this resin composition was measured, the spectrum shown in FIG. 1 was obtained.

Example 8
A flat plate resin composition was molded in the same manner as in Example 7, except that the pellets produced in Example 4 were used as raw materials. When the transmission spectrum of this resin composition was measured, the spectrum shown in FIG. 2 was obtained.

[Example 9]
400 parts by weight of a 7: 3 (mass ratio) mixed solution of cyclohexane and methylene chloride was mixed with 100 parts by weight of a cyclic olefin resin (APEL6015T, manufactured by Mitsui Chemicals, Inc.), and the coumarin compound produced in Synthesis Example 2 (specific examples (1 ) -31) By adding 0.1 part by weight, a solution having a resin concentration of 20% by mass was obtained.
Next, the obtained solution was cast on a smooth glass plate, dried at 40 ° C. for 4 hours and at 60 ° C. for 4 hours, and then peeled from the glass plate. The peeled coating film was further dried under reduced pressure at 100 ° C. for 8 hours to produce an optical filter having a thickness of 0.1 mm, a length of 60 mm and a width of 60 mm.
FIG. 3 shows a transmission spectrum diagram of the optical filter.

Example 10
An optical filter was obtained in the same manner as in Example 9 except that 0.1 part by weight of the coumarin-based compound (Specific Example (1) -57) synthesized in Synthesis Example 3 was used. FIG. 4 shows a transmission spectrum diagram of the optical filter.

[Example 11] Production of shield for helmet The flat plate of 150 mm x 300 mm and 2 mm in thickness produced in Example 7 was cut into a shape of a motorcycle helmet shield, placed in a heating furnace and heated to 160 ° C. The heated flat plate was placed in a molding die to form a curved molded product having a radius of curvature of about 120 mm. After cooling, the plate was taken out of the molding die to obtain a helmet shield.
This shield was attached to a helmet and used for daytime and nighttime running. As a result, glare was less likely to be felt in running under fine weather, and light transmittance was not significantly reduced during nighttime running. In addition, blue (green), yellow, and red of the signal were clearly confirmed.

[Example 12] Production of antiglare coat for display device of information equipment 300 parts by weight of methyl ethyl ketone, 100 parts by weight of polymethyl methacrylate resin (80N manufactured by Asahi Kasei Corporation) and coumarin-based compound produced in Synthesis Example 2 (specific examples ( 1) -31) 0.05 part by weight was dissolved to prepare a coating solution.
This coating solution was applied to the surface of a polyethylene terephthalate (PET) sheet having a thickness of about 200 μm using a Meyer bar so that the film thickness after drying was about 10 μm, and dried.
The PET sheet with the anti-glare coat was placed in front of a display screen for a personal computer with an LED backlight, and the screen was observed under various conditions such as character display, image display, and moving image display. As a result, not only the glare and glare were reduced than 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 image was clearly seen, while the color tone was not changed.

[Example 13] Production of antiglare film for display device of information equipment 1000 parts by weight of polymethyl methacrylate resin (manufactured by Asahi Kasei Corporation: 80N) and coumarin-based compound synthesized in Synthesis Example 3 (specific examples (1) -57) After 0.132 parts by weight was mixed by a tumbler for 20 minutes, the mixture was melted and kneaded by a single screw extruder under the conditions of a cylinder set temperature of 260 ° C. and a screw rotation speed of 56 rpm to be pelletized.
The pellets were mixed and extruded in a twin-screw extruder to produce a film (sheet) having a thickness of about 200 μm. The temperature in the extrusion zone and the melt line was up to 275 ° C, and the temperature of the chill roll was 30 ° C.
The obtained film was cut and attached on a display surface of a portable information device using an acrylic adhesive. As a result of observing the display surface under various conditions such as character display, image display, etc., not only the glare and glare was reduced than before pasting, the contrast of the image etc. was improved and it was clearly visible, while the color tone changed There was no.

  The resin composition of the present invention can efficiently cut blue light around 380 nm to 450 nm, prevent glare and glare, and enhance contrast. Furthermore, since there is almost no coloring, there is little decrease in light transmittance, and there is little deterioration of the pigment in the resin, the molded product obtained by molding this is used for spectacle lenses, sun visors, shields for helmets, display of information equipment It is very useful for optical articles such as anti-glare coats or anti-glare films for devices. It is also useful for improving the life of an image display device such as a liquid crystal display device and an organic EL display, and for improving contrast in a bright room.

Claims (9)

(A) a resin composition comprising at least a thermoplastic resin or a thermosetting resin, and (B) a coumarin-based compound represented by the following general formula (1) as an organic dye,
[In the formula (1), R _{1 to} R ₉ are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group. Represents a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, an alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group, a substituted or unsubstituted amino group, ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , R ₇ and R ₈ , R ₈ and R ₉ are bonded to form an aliphatic ring or an aromatic ring Alternatively, a heterocyclic ring may be formed. ] In the general formula (1), R _{1 to} R ₉ are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, a trifluoromethyl group, a perfluoroalkyl group having 2 to 12 carbon atoms, 3. The resin composition according to claim 2, which is an alkoxy group having 1 to 12 or an alkoxyalkyl group having 2 to 16 carbon atoms, an alkylamino group having 1 to 8 carbon atoms, or a dialkylamino group having 2 to 16 carbon atoms in total.   The thermoplastic resin is at least one selected from a polycarbonate resin, a polyamide resin, an acrylic resin, and a polyester resin, and the thermosetting resin is at least one selected from a polyurethane resin, a polythiourethane resin, and an allyl diglycol carbonate resin. The resin composition according to claim 1. A molded article obtained by molding the resin composition according to claim 1. The molded article according to claim 4, which is an anti-glare optical article. The molded article according to claim 4, which is an optical filter. The molded article according to claim 4, which is a sun visor. The molded article according to claim 4, which is a shield for a helmet. The molded article according to claim 4, which is an antiglare coat for a display device of an information device or an antiglare film for a display device of an information device.