TW201406844A - Resin composition anf formed body thereof - Google Patents

Abstract

This invention provides an resin composition, which would nearly not be colored and shows excellent antiglare and blocking properties for undesired light when applying on optical articles, to avoid dazzlement, glare and damages to eyes. The resin composition at least contains (A) a resin, and (B) an organic pigment including a tetraazaporphyrin compound represented by the following general formula (1) (B-1) and a compound (B-2), the compound (B-2) is a compound having a maximum absorption within the wavelength of 380 to 470 nm in the toluene solution, wherein the ratio (A1/A2) of the absorbancy (A1) of the largest absorption wavelength within 520 to 800nm to the absorbancy (A2) of the largest absorption wavelength within 380 to 470nm is less than 0.1. [wherein, R1 to R8 each independently represents a hydrogen atom or a predetermined substitutent; the adjacent groups selected from R1 to R8 combine to each other, and may form a substituted or unsubstituted five or more-menbered ring with substuted carbon atoms; however, not all of R1 to R8 form the ring; M represents two hydrogen atoms, two monovalent metal atoms, a divalent metal atom, a substituted trivalent metal atom, a substituted tetravalent metal atom or an oxided metal atom.]

Description

Resin composition and formed body

The present invention relates to a resin composition usable for an optical material and a molded body obtained by molding the same. More specifically, it is a resin composition having a high effect of wavelength blocking which causes little glare and causes adverse effects on the human body, and a molded body obtained by molding the same, especially related to optics. A resin composition for materials and an optical article.

Furthermore, the present invention relates to an adhesive containing the resin composition, and an optical article comprising the composition.

To reduce the glare of sunlight or car headlights A so-called anti-glare function such as an eyeglass lens is known, for example, in an unpleasant feeling or a contrasting unsatisfactory feeling, visual fatigue, and the like. The purpose of this is to selectively block a wavelength band in which glare is easily observed, and Patent Document 1 discloses a technique in which a spectacle lens contains a rare earth metal compound such as a ruthenium compound.

The ruthenium compound has a characteristic of having a sharp absorption near 570 to 590 nm, and selectively absorbing light of 550 to 610 nm which is highly glare-insensitive and which is pleasing to the eye.

However, although inorganic rare earth metal compounds such as ruthenium compounds are easily adjusted In the case of a glass lens, in recent years, the material trend of the spectacle lens is mainly the use of plastic, and there is a problem that the inorganic rare earth metal compound cannot be uniformly dispersed and mixed in the lens resin.

Although it has also been explored to make certain organic rare earth metals The problem of blending materials in plastic lens materials is limited by the fact that the choice of compounds can only be limited to high-priced compounds, and there are still problems such as insufficient solubility or decomposition of the resin.

Patent Document 2 to Patent Document 4 disclose that the plastic lens contains tetraazaporporin instead of the ruthenium compound to block light in the vicinity of 580 to 590 nm, thereby providing antiglare property and visibility. However, to prevent dazzlement such as sunlight, it is only insufficient to block light of 550 to 600 nm. In addition, light of shorter wavelengths, especially blue to purple areas below 460 nm, causes glare (glare). The reason is not only causing flicker and blurring of the horizon, but also harmful to the eyes. Furthermore, elderly people or cataract patients are more likely to have a more glare-like sensation of light in this wavelength range because of the whitening of the crystals of the eye and the opacity of light at wavelengths below 460 nm.

In addition, recently, with the increase in efficiency and price of blue LED elements, the display of liquid crystal displays or personal computers used for illumination of LED light sources, LED light sources used for backlights, and portable electronic devices have been used. LED light source for car lights, etc. These light sources contain more blue components than previous light sources, resulting in more glare than ever before.

And, this blue light, in addition to the visual vertigo problem, Recently, it is also suspected of its impact on the human body.

For example, there is a possibility that the cornea, the omentum or the lens of the eye is injured and becomes a cause of cataract, and the physiological influence on the secretion of melatonin becomes a possibility of disturbing the cause of rhythm in the body, and the possibility of physiological damage to the skin. The accusation, such as an ophthalmology or psychiatric physician, also began to verify the impact on the eyes or the human body. Patent Document 5 discloses an eyeglass lens using a yellow dye or an orange dye as a blue light absorber.

Further, Patent Document 6 discloses the use of a yellow dye or an orange dye as a blue light absorber, and a squarylium compound as an organic dye having a maximum absorption value around 555 nm of a standard wavelength of the visual acuity curve. Spectacle lenses. Patent Document 7 discloses an anti-glare optical article using a yellow dye or an orange dye as a blue light absorber and a squaraine compound as an organic dye having a maximum absorption value in a wavelength range of 550 to 600 nm.

However, such spectacle lenses or anti-glare optical articles When the dye concentration is increased to improve the antiglare effect, the yellowish color is thicker and the visible light transmittance is lowered. On the other hand, Patent Documents 8 and 9 disclose that it is possible to suppress the unnecessary light emission of a display such as a plasma display or a liquid crystal display, or to change the color of the screen due to external light such as illumination, and it is possible to use a tetraazaporphyrin. Optical filter for the compound. Further, Patent Documents 10 to 12 disclose that a wavelength selective layer or a color correction film containing a porphyrazine compound is used to improve the color reproducibility of a liquid crystal display using an LED light source as a backlight.

However, it is still unknown that not only the blue light emitted by the LED light source can be effectively blocked, but also comprehensively preventing vertigo or adverse effects on the human body, and suppressing the change in color tone caused by unnecessary external light such as illumination or illumination, and The filter lens itself has almost no colored optical lenses.

[Previous Technical Literature] [Patent Literature]

Patent Document 1: Japanese Laid-Open Patent Publication No. 2000-75128

Patent Document 2: Japanese Laid-Open Patent Publication No. 2008-134618

Patent Document 3: Japanese Laid-Open Patent Publication No. 2011-145341

Patent Document 4: Japanese Laid-Open Patent Publication No. 2011-175176

Patent Document 5: Japanese Laid-Open Patent Publication No. Hei 6-324293

Patent Document 6: Japanese Patent Laid-Open No. Hei 9-43550

Patent Document 7: Japanese Laid-Open Patent Publication No. 2001-356212

Patent Document 8: Japanese Patent Laid-Open Publication No. 2002-40233

Patent Document 9: International Patent Publication No. WO2009/031406

Patent Document 10: Japanese Laid-Open Patent Publication No. 2011-221456

Patent Document 11: Japanese Patent Laid-Open Publication No. 2012-27298

Patent Document 12: Japanese Laid-Open Patent Publication No. 2012-84512

An object of the present invention is to provide a resin composition and a molded article thereof which are excellent in antiglare performance and ability to block unnecessary light, and have less coloration. More specifically, to effectively block humans near 580 nm to 590 nm High-visibility light, glare-proof or glare-proof, contrast-free, and almost non-colored products, providing a resin composition with excellent appearance and wide application range, and thus formed spectacle lenses and sun visors (sun visor) ), optical cover such as a mask for a helmet, a cover for a display device, an optical filter for display assembly, or an optical filter for eyeglass lens assembly.

Further, an object of the present invention is to provide a resin composition, a molded body, and an optical article, which can prevent a blue light that is mostly contained in an LED light source from being effectively blocked, and can prevent a display or an illumination lamp or an automobile lamp that uses an LED light source. Waiting for adverse effects on the human body. Further, another object of the present invention is to provide an adhesive containing the above resin composition, and an optical article containing the adhesive.

As a result of the investigation of the above problems, the present inventors have found that by including a resin composition having a specific structure of a porphyrazine compound and a compound having a specific absorption property in a resin, the problem can be solved. invention.

That is, the present invention relates to (i) a resin composition containing at least (A) a resin and (B) an organic dye, and (B) an organic dye comprising a tetra nitrogen represented by the following formula (1) a heteroporphyrin compound (B-1) having a maximum absorption between 380 and 470 nm in a toluene solution, and a compound (B-2) having a maximum absorption between 520 and 800 nm The ratio of the absorbance (A1) of the maximum absorption wavelength to the absorbance (A2) of the maximum absorption wavelength between 380 and 470 nm (A1/A2) is less than 0.1, [In the formula (1), R ₁ to R ₈ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group, an alkenyl group, an alkyl halide group, an alkoxy group, a halogenated alkoxy group, or an alkylthio group. , alkoxyalkyl, alkoxyalkoxyalkyl, halogenated alkoxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, substituted or unsubstituted Amine, substituted or unsubstituted fluorenyl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryloxyalkyl, substituted or unsubstituted aralkyl An oxy group, a substituted or unsubstituted aralkyloxyalkyl group, or a substituted or unsubstituted arylthio group, and mutually adjacent groups selected from R ₁ to R ₈ may be bonded to each other, and A substituted or unsubstituted 5-membered ring or more is formed together with the substituted carbon atom, but not all of R ₁ to R ₈ form a ring.

M represents two hydrogen atoms, two monovalent metal atoms, a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom or an oxidized metal atom. ]

(ii) The resin composition of (i), wherein the compound (B-2) is at least one compound selected from the group consisting of an azo compound, a quinophthalone compound, and a quinone compound; The resin composition of (ii), wherein the azo compound is represented by the following formula (2): [In the formula (2), Y ₁ to Y ₁₁ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a decyl group, a carboxyl group, an alkyl group, an alkenyl group, an alkyl halide group, an alkoxy group, or a halogenated alkoxy group. Alkyl, alkylthio, alkoxyalkyl, alkoxyalkoxyalkyl, halogenated alkoxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, Substituted or unsubstituted amino, substituted or unsubstituted guanylamino, substituted or unsubstituted fluorenyl, substituted or unsubstituted aryloxy, substituted or unsubstituted Aryloxyalkyl, substituted or unsubstituted aralkyloxy, substituted or unsubstituted aralkyloxyalkyl, alkyloxycarbonyl, substituted or unsubstituted aryl An oxycarbonyl group, or a substituted or unsubstituted arylthio group. ]

(iv) The resin composition according to (ii) or (iii), wherein the quinophthalone compound is represented by the following formula (3): [In the formula (3), each of Z ₁ to Z ₉ independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a carboxyl group, an alkyl group, an alkenyl group, an alkyl halide group, an alkoxy group, or an alkyl halide. Oxyl, alkylthio, alkoxyalkyl, alkoxyalkoxyalkyl, halogenated alkoxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl , substituted or unsubstituted amino, substituted or unsubstituted guanylamino, substituted or unsubstituted fluorenyl, substituted or unsubstituted aryloxy, substituted or unsubstituted Aryloxyalkyl, substituted or unsubstituted aralkyloxy, substituted or unsubstituted aralkyloxyalkyl, alkyloxycarbonyl, substituted or unsubstituted aryl a oxycarbonyl group, or a substituted or unsubstituted arylthio group, and the mutually adjacent groups selected from Z ₆ to Z ₉ may be bonded to each other to form a substituted or unsubstituted group together with the substituted carbon atom. Replace the ring with a 5 member ring or more. ]

(v) The resin composition according to any one of (ii) to (iv), wherein the lanthanoid compound is represented by the following formula (4): [In the formula (4), X ₁ to X ₈ each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkyl halide group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, a substituted or unsubstituted group. An aryl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl thio group. However, at least one of X ₁ to X ₈ must be a substituted or unsubstituted arylthio group. ]

(vi) The resin composition according to any one of (i) to (v), wherein R ₁ to R ₈ in the formula (1) each independently represent a hydrogen atom, a halogen atom, and a carbon number of 1 to 12. An alkyl group, an alkenyl group having 2 to 6 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, and an alkyl group having 1 to 12 carbon atoms a thiol group, an alkoxyalkyl group having 2 to 16 carbon atoms, a halogenated alkoxyalkyl group having 2 to 16 carbon atoms, an alkoxyalkoxyalkyl group having 3 to 20 carbon atoms, and a carbon number of 6 to 18 a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group having 1 to 18 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, and a carbon number of 6 to 18 a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxyalkyl group having 7 to 20 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms, M is Cu, Zn, Fe, Co, Ni, Pd, Mn, Mg, Mn(OH), Mn(OH) ₂ , VO or TiO; (vii) as in any one of (iii) to (vi) resin composition, wherein the general formula Y (2) ₁ to Y ₁₁ each independently represent a hydrogen atom, a halogen atom, an alkyl group of 1 to carbon atoms, alkenyl having 2 to 12 6, a halogenated alkyl group of 1 to 12, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, an alkoxy group having 2 to 16 carbon atoms An alkyl group, an alkoxyalkoxyalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted amino group having 1 to 18 carbon atoms, a substituted or unsubstituted guanamine group having 1 to 18 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms a substituted or unsubstituted aryloxyalkyl group having 7 to 20 carbon atoms, an alkyloxycarbonyl group having 2 to 13 carbon atoms, or a substituted or unsubstituted aryloxy group having 7 to 19 carbon atoms a carbonyl group, a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms; (viii) a resin composition according to any one of (iv) to (vii), wherein, in the formula (3) Z ₁ to Z ₉ each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, and an alkyl group having 1 to 12 carbon atoms. An oxy group, a halogenated alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, and an alkoxy group having 2 to 16 carbon atoms Alkoxy group, alkoxyalkoxyalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted amino group having 1 to 18 carbon atoms a substituted or unsubstituted guanamine group having 1 to 18 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms An oxy group, a substituted or unsubstituted aryloxyalkyl group having 7 to 20 carbon atoms, an alkyloxycarbonyl group having 2 to 13 carbon atoms, a substituted or unsubstituted aryl group having 7 to 19 carbon atoms An oxycarbonyl group, a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms, or a mutually adjacent group selected from Z6 to Z9 may be bonded to each other to form a substituted or substituted carbon atom together (1) The resin composition according to any one of (v) to (viii), wherein X ₁ to X ₈ in the formula (4) each independently represent a hydrogen atom. a halogen atom, an alkyl group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, and 2 to 16 carbon atoms. Alkoxyalkyl group, substituted or unsubstituted carbon number 6 to 18 Thio group, and at least one of X ₁ to X ₈ must be a carbon number of 6 to 18 by the substituted or unsubstituted arylthio group; any one of (x) as (i) to (ix) in a resin composition, wherein the resin is a thermoplastic resin or a thermosetting resin; (xi) a resin composition according to (x), wherein the thermoplastic resin is selected from the group consisting of polycarbonate resins and polyamide resins. At least one resin of an acrylic resin and a polyester resin, and the thermosetting resin is at least one resin selected from the group consisting of a polyurethane resin, a polythiamine resin, and allyl diglycol carbonate.

(xii) A molded body obtained by molding the resin composition in any one of (i) to (xi).

(xiii) The molded article of (xii), wherein the molded article is an optical article for preventing glare, or an optical article for reducing short-wavelength light or an optical filter.

(xiv) The molded article of (xii) or (xiii), wherein the molded body is an eyeglass lens, a sun visor, a mask for a helmet, a cover for a display device, an optical filter for display assembly, or an optical for assembling an eyeglass lens Filter.

(xv) An adhesive comprising the resin composition of any one of (i) to (ix).

(xvi) An optical article for antiglare, an optical article for reducing short-wavelength light, or an optical filter, which is an adhesive containing (xv).

The resin composition of the present invention can efficiently block blue light in the vicinity of 380 nm to 460 nm and light having high human visual sensitivity in the vicinity of 580 nm to 590 nm, thereby preventing glare or glare and improving contrast.

Furthermore, by blocking the blue light mostly contained in the LED light source, it is possible to prevent adverse effects on the human body such as a display or illumination using an LED light source, a lamp of a car, and the like.

Further, since the resin composition has almost no coloration, the molded article obtained by molding the resin composition is very suitable for use in an eyeglass lens, a sun visor, a mask for a helmet, a cover for a display device, and an optical microscope for display assembly. Anti-glare optical articles such as optical lenses for lens and eyeglass lens assembly, optical articles for short wavelengths, and optical filters. The resin composition of the present invention has a particularly low coloring and is almost colorless.

Further, since the resin composition of the present invention has a high transparency because the dye is well dissolved in the resin, the visible light rays other than unnecessary light are transmitted well, and the light transmittance is rarely lowered.

Further, in the resin composition of the present invention, since the dye deterioration in the resin having high light resistance is small, the product using the resin composition is excellent in optical fastness.

191‧‧‧ functional transparent layer (G) hard coating

192‧‧‧Transparent adhesive layer (H)

193‧‧‧Transparent support (F)

194‧‧‧Transparent adhesive layer (H)

D‧‧‧ The porphyrazine compound (B-1) represented by the formula (1) and the azo compound represented by the formula (2) (dissolved in the resin)

Fig. 1 is a transmission spectrum of a resin composition according to Examples 1 to 14 of the present invention.

Fig. 2 is a transmission spectrum of a resin composition according to Examples 1 to 15 of the present invention.

Fig. 3 is a transmission spectrum of a resin composition according to Examples 1 to 16 of the present invention.

Fig. 4 is a transmission spectrum of a resin composition related to Example 1-17 of the present invention.

Fig. 5 is a transmission spectrum of a resin composition according to Examples 1 to 18 of the present invention.

Fig. 6 is a transmission spectrum of the resin composition of Examples 1 to 19 of the present invention.

Figure 7 is a transmission of the optical filter of the embodiment 1-28 of the present invention. spectrum.

Fig. 8 is a transmission spectrum of an optical filter relating to Examples 1-31 of the present invention.

Figure 9 is a transmission spectrum of an optical filter related to Examples 1-33 of the present invention.

Figure 10 is a transmission spectrum of an optical filter of Examples 1-37 of the present invention.

Fig. 11 is a transmission spectrum of a resin composition relating to Examples 2 to 12 of the present invention.

Fig. 12 is a transmission spectrum of the resin composition of Examples 2 to 13 of the present invention.

Fig. 13 is a transmission spectrum of the resin composition of Examples 2 to 14 of the present invention.

Fig. 14 is a transmission spectrum of the resin composition of Examples 2 to 15 of the present invention.

Fig. 15 is a transmission spectrum of a resin composition relating to Examples 3 to 11 of the present invention.

Figure 16 is a transmission spectrum of an optical filter of Example 3-32 of the present invention.

Hereinafter, the present invention will be described in detail.

The resin composition of the present invention is at least formed of (A) a resin and (B) an organic dye. First, (B) an organic pigment will be described. (B) The organic dye contains at least a tetraazaporphyrin compound (B-1) represented by the following formula (1) and has specific Compound (B-2) having a light absorbing property.

[Compound (B-1)]

The porphyrazine compound (B-1) related to the resin composition of the present invention can be represented by the following formula (1).

[In the formula (1), R ₁ to R ₈ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group, an alkenyl group, an alkyl halide group, an alkoxy group, a halogenated alkoxy group, or an alkylthio group. , alkoxyalkyl, alkoxyalkoxyalkyl, halogenated alkoxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, substituted or unsubstituted Amine, substituted or unsubstituted fluorenyl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryloxyalkyl, substituted or unsubstituted aralkyl An oxy group, a substituted or unsubstituted aralkyloxyalkyl group, or a substituted or unsubstituted arylthio group, and mutually adjacent groups selected from R ₁ to R ₈ may be bonded to each other, and A substituted or unsubstituted 5-membered ring or more is formed together with the substituted carbon atom, but not all of R ₁ to R ₈ form a ring.

M represents two hydrogen atoms, two monovalent metal atoms, a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxidized metal atom. ]

Here, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxyalkyl group, a substituted or unsubstituted aralkyloxy group, a substituted or unsubstituted aralkyloxyalkyl group, a substituted or unsubstituted arylthio group, selected from R ₁ to R ₈ adjacent to each other The substituents may be bonded to each other, and the substituted substituent may be substituted with a substituted or unsubstituted 5-membered or more ring, and each of the substituents may be a halogen atom, a cyano group, a nitro group or a hydroxyl group. Mercapto, carboxyl, alkyl, alkenyl, halogenated alkyl, alkoxy, halogenated alkoxy, alkylthio, alkoxyalkyl, amine, alkylamino, dialkylamino; substituted Or a substituent of the unsubstituted amino group, the substituted or unsubstituted fluorenyl group, each of which may be exemplified by an alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group. .

R ₁ to R ₈ in the formula (1) are preferably each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an alkyl halide having 1 to 12 carbon atoms. Alkoxy group having 1 to 12 carbon atoms, halogenated alkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, alkoxyalkyl group having 2 to 16 carbon atoms, carbon number 3 to Alkoxyalkoxyalkyl group of 20, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted amine group having 1 to 18 carbon atoms, and carbon number 7 to 20 a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms, a substituted or unsubstituted aryloxyalkyl group having 7 to 20 carbon atoms, or a carbon A substituted or unsubstituted arylthio group of from 6 to 18.

M is preferably Cu, Zn, Fe, Co, Ni, Pt, Pd, Mn, Mg, Mn(OH), Mn(OH) ₂ , VO or TiO.

R ₁ to R ₈ in the formula (1) are more preferably each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, and a carbon number. Alkoxy group of 1 to 8, alkoxyalkyl group having 1 to 8 carbon atoms, alkylthio group having 1 to 8 carbon atoms, alkoxyalkyl group having 2 to 12 carbon atoms, halogenated alkane having 2 to 12 carbon atoms An oxyalkyl group, a finely substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted amino group having 1 to 14 carbon atoms, a substituted or unsubstituted carbon number of 7 to 18. An aralkyl group, a substituted or unsubstituted aryloxy group having 6 to 14 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 14 carbon atoms.

Further, M is more preferably Cu, Pt, Pd, Ni or VO.

Specific examples of R ₁ to R ₈ are as follows.

When R ₁ to R ₈ are a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like may be mentioned, and a fluorine atom, a chlorine atom or a bromine atom is preferred, and a chlorine atom is particularly preferred.

When R ₁ to R ₈ are an alkyl group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a neopentyl group are exemplified. , third amyl, 1,2-dimethylpropyl, 1-methylbutyl, 2-methylbutyl, n-hexyl, 2-methylpentyl, 4-methylpentyl, 4-methyl Benzyl-2-pentyl, 1,2-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 3-methylhexyl, 5-methylhexyl, 2,4-Dimethylpentyl, cyclohexylmethyl, n-octyl, trioctyl, 2-ethylhexyl, 2-propylpentyl, 2,5-dimethylhexyl, 2,5, 5-trimethylhexyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, 4-ethyl octyl Base, n-undecyl, 1-methylindolyl, n-dodecyl, 1,3,5,7-tetramethyloctyl, n-tridecyl, 1-hexylheptyl, positive fifteen Alkyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-icosyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, Cycloheptyl, cyclooctyl, etc.; preferably methyl, ethyl, n-propyl, isopropyl, n-butyl Base, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, 1,2-dimethylpropyl, 1-methylbutyl, n-hexyl, 1,2-dimethyl Butyl, 2-ethylbutyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, 4-ethyloctyl, n-undecyl, n-dodecyl; more preferably Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, 1,2-dimethylbutyl, 2- Ethyl butyl, n-heptyl, n-octyl.

When R ₁ to R ₈ are alkenyl groups, examples thereof include a vinyl group, a propenyl group, a 1-butenyl group, an isobutenyl group, a 1-pentenyl group, a 2-pentenyl group, and a 2-methyl-1-butenyl group. 1-hexenyl or the like is preferably a vinyl group, a propenyl group or a 1-butenyl group, more preferably a vinyl group or a propenyl group.

When R ₁ to R ₈ are a halogenated alkyl group, the alkyl group in which the above-mentioned R ₁ to R ₈ is an alkyl group is substituted with a chlorine atom or a fluorine atom, for example, a fluoromethyl group or a trifluoromethyl group, 2-fluoroethyl, perfluoroethyl, 3-fluoropropyl, 1,1-dihydro-perfluoro-n-propyl, 2-hydro-perfluoro-2-propyl, 4-fluoroisobutyl, 1 ,1-dihydro-perfluoro-n-butyl, perfluoro-n-pentyl, 2,2-bis(trifluoromethyl)propyl, 6-fluorohexyl, perfluoro-n-hexyl, 4-fluorocyclohexyl, 8 -Fluoxinyl, 1,1-dihydro-perfluoro-n-octyl, 1,1-dihydro-perfluoro-n-decyl, 1,1-dihydro-perfluoro-n-dodecyl, 1,1- Dihydro-perfluoro-n-hexadecyl, chloromethyl, dichloromethyl, trichloromethyl, 2-chloroethyl, 2,2,2-trichloroethyl, 3-chloropropyl, perfluoro N-butyl, 5-chloropentyl, 7-chloroheptyl, etc., preferably fluoromethyl, trifluoromethyl, 2-fluoroethyl, perfluoroethyl, 3-fluoropropyl, 1,1- Dihydro-perfluoro-n-propyl, 4-fluoroisobutyl, perfluoro-n-pentyl, 2,2-bis(trifluoromethyl)propyl, 6-fluorohexyl, 4-fluorocyclohexyl, 8-fluoro Octyl, 1,1-dihydro-perfluoro-n-octyl, chloromethyl, dichloromethyl, trichloromethyl, 2-chloroethyl, 2,2,2-trichloro , 3-chloropropyl, perfluoro-n-butyl, 5-chloropentyl, 7-chloroheptyl, more preferably fluoromethyl, trifluoromethyl, 2-fluoroethyl, perfluoroethyl, 3 - fluoropropyl, 4-fluoroisobutyl, chloromethyl, dichloromethyl, trichloromethyl, 2-chloroethyl, 2,2,2-trichloroethyl, 3-chloropropyl.

When R ₁ to R ₈ are alkoxy groups, a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, a second butoxy group, a n-pentyloxy group, and a cyclopentyl group are exemplified. Alkoxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, cyclohexyloxy, n-heptyloxy, n-octyloxy, 2-B Hexyloxy, n-decyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy , n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, n-tricosyloxy, n-tetracosyloxy, etc., preferably methoxy , ethoxy, n-propoxy, isopropoxy, n-butoxy, second butoxy, n-pentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2 -ethylbutyloxy, cyclohexyloxy, n-heptyloxy, n-octyloxy, 2-ethylhexyloxy, n-dodecyloxy, more preferably methoxy, ethoxy Base, n-propoxy, isopropoxy, n-butoxy, second butoxy, n-pentyloxy, n-hexyloxy, 2-ethylbutyl Group, a cyclohexyl group, a n-heptyl group, n-octyl group.

When R ₁ to R ₈ are a halogenated alkoxy group, the above-mentioned alkyl group in which R ₁ to R ₈ are alkoxy groups is substituted with a chlorine atom or a fluorine atom, for example, a fluoromethoxy group, Fluoromethoxy, 2-fluoroethoxy, perfluoroethoxy, 3-fluoropropoxy, 1,1-dihydro-perfluoro-n-propyloxy, 4-fluoroisobutyloxy, 1 , 1-dihydro-perfluoro-n-butyloxy, perfluoro-n-pentyloxy, 2,2-bis(trifluoromethyl)propyloxy, 6-fluorohexyloxy, perfluoro-n-hexyl Oxyl, 4-fluorocyclohexyloxy, 8-fluorooctyloxy, chloromethoxy, dichloromethoxy, trichloromethoxy, 2-chloroethoxy, 2,2,2-trichloro Ethoxy, 3-chloropropyloxy, perfluoro-n-butoxy, 5-chloropentyloxy, 7-chloroheptyloxy, etc., preferably fluoromethoxy, trifluoromethoxy , 2-fluoroethoxy, perfluoroethoxy, 3-fluoropropyloxy, 1,1-dihydro-perfluoro-n-propyloxy, 4-fluoroisobutyloxy, perfluoro-n-pentyl Alkoxy, 2,2-bis(trifluoromethyl)propyloxy, 6-fluorohexyloxy, 4-fluorocyclohexyloxy, 8-fluorooctyloxy, 1,1-dihydro- Perfluoro-n-octyloxy, chloromethoxy, dichloromethoxy, trichloro Base, 2-chloroethoxy, 2,2,2-trichloroethoxy, 3-chloropropyloxy, perfluoro-n-butyloxy, 5-chloropentyloxy, 7-chloroheptyl More preferably, fluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, perfluoroethoxy, 3-fluoropropyloxy, 4-fluoroisobutyloxy, chloromethoxy Base, dichloromethoxy, trichloromethoxy, 2-chloroethoxy, 2,2,2-trichloroethoxy, 3-chloropropyloxy.

When R ₁ to R ₈ are an alkylthio group, a methylthio group, an ethylthio group, a n-propylthio group, an isopropylthio group, an n-butylthio group, a second butylthio group, and a positive one are exemplified. Amylthio, cyclopentylthio, n-hexylthio, 3,3-dimethylbutylthio, 2-ethylbutylthio, cyclohexylthio, n-heptylthio, n-octyl Thiothio group, 2-ethylhexylthio group, n-decylthio group, n-undecylthio group, n-dodecylthio group, n-tridecylthio group, n-tetradecylthio group, N-pentadecylthio, n-hexadecylthio, n-heptadecylthio, n-octadecylthio, n-tricosylthio, n-tetradecylthio, etc. Preferred is methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, t-butylthio, n-pentylthio, n-hexylthio, 3,3-Dimethylbutylthio, 2-ethylbutylthio, cyclohexylthio, n-heptylthio, n-octylthio, 2-ethylhexylthio, n-dodecane Thiyl group, more preferably methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, second Group, n-pentyl group, n-hexyl group, 2-ethylbutyl group, a cyclohexyl group, a n-heptyl group, n-octyl group.

When R ₁ to R ₈ are alkoxyalkyl groups, a methoxymethyl group, an ethoxymethyl group, a n-butoxymethyl group, a n-pentyloxymethyl group, a n-hexyloxymethyl group, ( 2-ethylbutyloxy)methyl, n-heptyloxymethyl, n-octyloxymethyl, n-dodecyloxymethyl, 2-methoxyethyl, 2-ethoxy Ethyl ethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-n-hexyloxyethyl, 2-n-heptyloxyethyl, 2-n-octyloxyethyl , 2-n-dodecyloxyethyl, 2-n-tetradecyloxyethyl, 2-cyclohexyloxyethyl, 2-methoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3-isopropoxypropyl, 3-n-butoxypropyl, 3-n-pentyloxypropyl, 3-(2'-ethylbutoxy)propyl , 3-n-octyloxypropyl, 3-n-decyloxypropyl, 3-cyclohexyloxypropyl, 4-methoxybutyl, 4-ethoxybutyl, 4-n-propyl Oxybutyl, 4-isopropoxybutyl, 4-n-butoxybutyl, 4-n-octyloxybutyl, 4-n-decyloxybutyl, 4-n-dodecyl Oxybutyl, 5-methoxypentyl, 5-ethoxypentyl, 5-n-pentyloxy Pentyl, 6-methoxyhexyl, 6-ethoxyhexyl, 6-n-butyloxypentyl, 6-n-hexyloxypentyl, 6-n-decyloxypentyl, 4-methoxy Cyclohexyl, 7-ethoxybutyl, 8-methoxyoctyl, 9-methoxyindenyl, 10-methoxyindenyl, 10-n-butoxydecyl, 12-methoxy Dodecyl, 12-isopropoxydodecyl, tetrahydrofuranyl, etc., preferably methoxymethyl, ethoxymethyl, n-butoxymethyl, n-pentyloxymethyl, N-hexyloxymethyl, n-octyloxymethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2 - n-hexyloxyethyl, 2-n-octyloxyethyl, 2-cyclohexyloxyethyl, 2-methoxypropyl, 3-methoxypropyl, 3-ethoxypropyl , 3-isopropoxypropyl, 3-n-butoxypropyl, 3-n-pentyloxypropyl, 3-(2'-ethylbutoxy)propyl, 3-cyclohexyloxy Propyl, 4-methoxybutyl, 4-ethoxybutyl, 4-n-propoxybutyl, 4-n-butoxybutyl, 4-n-octyloxybutyl, 5-methyl Oxypentyl, 5-ethoxypentyl, 5-n-pentyloxypentyl , 6-ethoxyhexyl, 6-n-butoxyhexyl, 4-methoxycyclohexyl, 7-ethoxybutyl, 8-methoxyoctyl, 10-methoxyindenyl, 10- a n-butoxycarbonyl group, a 12-methoxydodecyl group, a tetrahydrofuranyl group, more preferably a methoxymethyl group, an ethoxymethyl group, a n-butoxymethyl group, a 2-methoxyethyl group, 2-ethoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-n-hexyloxyethyl, 2-n-octyloxyethyl, 2-methoxy Propyl, 3-methoxypropyl, 3-ethoxypropyl, 3-n-butoxypropyl, 3-n-pentyloxypropyl, 3-cyclohexyloxypropyl, 4-methyl Oxybutyl, 4-ethoxybutyl, 4-n-propoxybutyl, 4-n-butoxybutyl, 4-n-octyloxybutyl, 4-n-decyloxybutyl , 5-methoxypentyl, 5-ethoxypentyl, 6-ethoxyhexyl, 6-n-butoxyhexyl, 4-methoxycyclohexyl, 7-ethoxybutyl, 8- Methoxyoctyl.

When R ₁ to R ₈ are alkoxyalkoxyalkyl groups, (2-methoxyethoxy)methyl, (2-ethoxyethoxy)methyl, (2-n-butyl) Oxyethoxy)methyl, (3-methoxypropyloxy)methyl, (3-ethoxypropyloxy)methyl, (3-n-pentyloxypropoxy)methyl , (6-methoxyhexyloxy)methyl, (10-ethoxydecyloxy)methyl, 2-(2-methoxyethoxy)ethyl, 2-(2-ethyl Oxyethoxyethyl)ethyl, 2-(3-ethoxypropyloxy)ethyl, 2-(4-ethoxybutyloxy)ethyl, 2-(4-butyloxy Butyloxy)ethyl, 2-(5-methyloxypentyloxy)ethyl, 3-(1-methoxyethoxy)propyl, 3-(2-ethoxyethoxy) Propyl, 3-(3-methoxypropyloxy)propyl, 3-(3-propyloxypropyloxy)propyl, 3-(4-ethoxybutyloxy )propyl, 3-(4-butyloxybutyloxy)propyl, 3-(5-methyloxypentyloxy)propyl, 4-(2-methoxyethoxy) Butyl, 4-(2-ethoxyethoxy)butyl, 4-(3-ethoxypropyloxy)butyl, 4-(4-butyloxybutyloxy)butyl , 2-(5-methyloxypentyloxy)butyl, 5-(2-methoxyethoxy) Pentyl, 5-(2-ethoxyethoxy)pentyl, 5-(3-ethoxypropyloxy)pentyl, 5-(4-butyloxybutyloxy)pentyl , 5-(5-pentyloxypentyloxy)pentyl, 6-(2-methoxyethoxy)hexyl, 6-(2-ethoxyethoxy)hexyl, 6-(6 -butyloxybutyloxy)hexyl, 8-(2-ethoxyethoxy)octyl, etc., preferably (2-methoxyethoxy)methyl, (2-ethoxyl) Ethoxy)methyl, (2-n-butyloxyethoxy)methyl, (3-methoxypropyloxy)methyl, (3-ethoxypropyloxy)methyl, 2-(2-methoxyethoxy)ethyl, 2-(2-ethoxyethoxy)ethyl, 2-(3-ethoxypropyloxy)ethyl, 2-(4 -ethoxybutyloxy)ethyl, 2-(4-butyloxybutyloxy)ethyl, 2-(5-methyloxypentyloxy)ethyl, 3-(1 -methoxyethoxy)propyl, 3-(2-ethoxyethoxy)propyl, 3-(3-methoxypropyloxy)propyl, 3-(3-propyloxy Propyloxy)propyl, 3-(4-ethoxybutyloxy)propyl, 4-(2-methoxyethoxy)butyl, 4-(2-ethoxyethoxy) Butyl, 4-(3-ethoxypropyloxy)butyl, 4-(4-butyloxybutyloxy) , 5-(2-methoxyethoxy)pentyl, 5-(2-ethoxyethoxy)pentyl, 5-(3-ethoxypropyloxy)pentyl, 5- (4-Butoxybutyloxy)pentyl, 6-(2-methoxyethoxy)hexyl, 6-(2-ethoxyethoxy)hexyl, 8-(2-ethoxylated) Ethyl ethoxy) octyl, more preferably (2-methoxyethoxy)methyl, (2-ethoxyethoxy)methyl, (3-methoxypropyloxy)methyl ,(3-ethoxypropyloxy)methyl, 2-(2-methoxyethoxy)ethyl, 2-(2-ethoxyethoxy)ethyl, 2-(3- Ethoxypropyloxy)ethyl, 2-(4-ethoxybutyloxy)ethyl, 3-(1-methoxyethoxy)propyl, 3-(2-ethoxyl) Ethoxy)propyl, 3-(3-methoxypropyloxy)propyl, 3-(3-propyloxypropyloxy)propyl, 4-(2-methoxyethoxy) Butyl, 4-(2-ethoxyethoxy)butyl, 4-(3-ethoxypropyloxy)butyl, 5-(2-ethoxyethoxy)pentyl 5-(3-ethoxypropyloxy)pentyl.

When R ₁ to R ₈ are a halogenated alkoxyalkyl group, the alkoxyalkyl group substituted by a chlorine atom or a fluorine atom in the case where the above R ₁ to R ₈ are alkoxyalkyl groups may, for example, be mentioned, for example. Fluoromethyloxymethyl, trifluoromethyloxymethyl, 2-fluoroethyloxymethyl, perfluoroethyloxymethyl, 3-fluoro-n-propyloxymethyl, 1,1 -dihydro-perfluoroethyloxymethyl, 1,1-dihydro-perfluoro-n-propyloxymethyl, 1,1-dihydro-perfluoro-n-butyloxymethyl, 1,1 - dihydro-perfluoro-n-tetradecyloxymethyl, fluoromethyloxyethyl, trifluoromethyloxyethyl, 2-fluoroethyloxyethyl, perfluoroethyloxy , 2-(8-fluoro-n-octyloxy)ethyl, 2-(6-fluoro-n-hexyloxy)ethyl, fluoromethyloxypropyl, trifluoromethyloxypropyl, 2-fluoroethyloxypropyl, perfluoroethyloxypropyl, 3-(1,1-dihydro-perfluoroethyloxy)propyl, 4-(perfluoro-n-hexyloxy)butyl Base, 6-(2-chloroethyloxy)hexyl, etc., preferably fluoromethyloxymethyl, trifluoromethyloxymethyl, 2-fluoroethyloxymethyl, perfluoroethyl Oxymethyl, 3-fluoro-n-propyloxymethyl, 1,1-dihydro- Perfluoroethyloxymethyl, 1,1-dihydro-perfluoro-n-butyloxymethyl, fluoromethyloxyethyl, trifluoromethyloxyethyl, 2-fluoroethyloxy Ethyl, perfluoroethyloxyethyl, 2-(6-fluoro-n-hexyloxy)ethyl, fluoromethyloxypropyl, trifluoromethyloxypropyl, 2-fluoroethyloxy a propyl group, a perfluoroethyloxypropyl group, a 4-(perfluoro-n-hexyloxy)butyl group, a 6-(2-chloroethyloxy)hexyl group, more preferably a fluoromethyloxymethyl group, Trifluoromethyloxymethyl, 2-fluoroethyloxymethyl, perfluoroethyloxymethyl, 3-fluoro-n-propyloxymethyl, 1,1-dihydro-perfluoroethyl Oxymethyl, fluoromethyloxyethyl, trifluoromethyloxyethyl, 2-fluoroethyloxyethyl, perfluoroethyloxyethyl, fluoromethyloxypropyl, three Fluoromethyloxypropyl, perfluoroethyloxypropyl, 4-(perfluoro-n-hexyloxy)butyl.

When R ₁ to R ₈ are a substituted or unsubstituted aryl group, they may contain a heteroaryl group, and examples thereof include a phenyl group, a 2-methylphenyl group, a 4-methylphenyl group, and a 3-ethylphenyl group. 4-n-propylphenyl, 4-n-butylphenyl, 4-isobutylphenyl, 4-tert-butylphenyl, 4-n-pentylphenyl, 4-tripentylphenyl, 4-n-hexylphenyl, 4-cyclohexylphenyl, 4-n-octylphenyl, 4-n-decylphenyl, 4-n-decylphenyl, 4-n-dodecylphenyl, 4- N-tetradecylphenyl, 4-n-octadecylphenyl, 2,5-dimethylphenyl, 3,4-dimethylphenyl, 3,4,5-trimethylphenyl, 5-hydroindenyl, 1,2,3,4-tetrahydro-6-naphthyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-ethoxyphenyl, 4 - n-propoxyphenyl, 4-isopropoxyphenyl, 4-n-butoxyphenyl, 4-n-pentyloxyphenyl, 4-cyclohexyloxyphenyl, 4-n-heptyl Oxyphenyl, 4-n-octyloxyphenyl, 4-n-decyloxyphenyl, 4-n-undecyloxyphenyl, 4-n-tetradecyloxyphenyl, 4 - n-hexadecyloxyphenyl, 2,3-dimethoxyphenyl, 2,4-dimethoxyphenyl, 3,5-diethoxyphenyl, 2- Oxy-4-methylphenyl, 2-methyl-4-methoxyphenyl, 2-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 4-bromophenyl, 4-tri Fluoromethylphenyl, 3-trifluoromethylphenyl, 2,4-difluorophenyl, 2,4-dichlorophenyl, 2-methyl-4-chlorophenyl, 2-chloro-4- Methoxyphenyl, 3-fluoro-4-methoxyphenyl, 2-phenylphenyl, 3,5-diphenylphenyl, 1-naphthyl, 2-naphthyl, 4-methyl- 1-naphthyl, 4-ethoxy-1-naphthyl, 6-n-butyl-2-naphthyl, 2-furyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 4-amine Phenylphenyl, 3-aminophenyl, 2-aminophenyl, 2-(N-n-butylamino)phenyl, 4-(N,N-dimethylamino)phenyl, 4- (N-cyclohexyl-N-methylamino)phenyl, 4-(N,N-diethylamino)-1-naphthyl, 4-pyrrolylphenyl, 4-piperidylphenyl, 4-morphinylphenyl, 4-pyrrolyl-1-naphthyl, 4-(N-methyl-N-phenylamino)phenyl, 4-[N,N-bis(4'-methyl) Phenyl)amino]phenyl, 4-[N,N-bis(4'-ethoxyphenyl)amino]phenyl, 4-[N,N-bis(4'-n-hexyloxybenzene) Amino]phenyl, 4-[N-phenyl-N-(1'-naphthyl)amino]phenyl, 4-(N-morphine Phenylzinyl) phenyl or the like, preferably phenyl, 2-methylphenyl, 4-methylphenyl, 3-ethylphenyl, 4-n-propylphenyl, 4-n-butylbenzene , 4-n-pentylphenyl, 4-tripentylphenyl, 4-n-hexylphenyl, 4-cyclohexylphenyl, 4-n-octylphenyl, 4-n-decylphenyl, 4 - n-dodecylphenyl, 4-n-octadecylphenyl, 2,5-dimethylphenyl, 3,4-dimethylphenyl, 3,4,5-trimethylphenyl , 2-methoxyphenyl, 3-methoxyphenyl, 4-ethoxyphenyl, 4-n-propoxyphenyl, 4-isopropoxyphenyl, 4-n-butoxybenzene Base, 4-n-pentyloxyphenyl, 4-n-octyloxyphenyl, 2,3-dimethoxyphenyl, 2,4-dimethoxyphenyl, 3,5-diethyl Oxyphenyl, 2-methoxy-4-methylphenyl, 2-methyl-4-methoxyphenyl, 2-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 4 -Bromophenyl, 4-trifluoromethylphenyl, 3-trifluoromethylphenyl, 2,4-difluorophenyl, 2,4-dichlorophenyl, 2-methyl-4-chlorobenzene , 2-chloro-4-methoxyphenyl, 3,5-diphenylphenyl, 1-naphthyl, 2-naphthyl, 4-methyl-1-naphthyl, 4-ethoxy- 1-naphthyl, 2-furyl, 2-pyridyl 3-pyridyl, 4-pyridyl, 4-aminophenyl, 3-aminophenyl, 2-aminophenyl, 4-(N,N-dimethylamino)phenyl, 4-( N-cyclohexyl-N-methylamino)phenyl, 4-(N,N-diethylamino)-1-naphthyl, 4-pyrrolylphenyl, 4-(N-methyl-N -phenylamino)phenyl, 4-[N,N-bis(4'-ethoxyphenyl)amino]phenyl, more preferably phenyl, 2-methylphenyl, 4-methyl Phenyl, 3-ethylphenyl, 4-n-propylphenyl, 4-n-butylphenyl, 4-n-pentylphenyl, 4-n-octylphenyl, 2,5-dimethylbenzene , 3,4-dimethylphenyl, 3,4,5-trimethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-ethoxyphenyl, 4- Isopropoxyphenyl, 4-n-butoxyphenyl, 4-n-octyloxyphenyl, 2,3-dimethoxyphenyl, 2,4-dimethoxyphenyl, 3, 5-diethoxyphenyl, 2-methoxy-4-methylphenyl, 2-methyl-4-methoxyphenyl, 2-fluorophenyl, 4-fluorophenyl, 2-chloro Phenyl, 4-bromophenyl, 4-trifluoromethylphenyl, 3-trifluoromethylphenyl, 2,4-difluorophenyl, 2,4-dichlorophenyl, 2-methyl- 4-chlorophenyl, 2-chloro-4-methoxyphenyl, 1-naphthyl, 2-naphthyl, 4-methyl-1-naphthyl 4-ethoxy-1-naphthyl, 2-furyl, 4-aminophenyl, 3-aminophenyl, 2-aminophenyl, 4-(N,N-dimethylamino) Phenyl.

When R ₁ to R ₈ are a substituted or unsubstituted aralkyl group, a benzyl group, an α-methylbenzyl group, an α,α-dimethylbenzyl group, or an α-phenylbenzyl group may be mentioned. , phenethyl, α-methylphenethyl, α,α-dimethylphenethyl, 4-methylphenethyl, 4-methylbenzyl, 2-methylbenzyl, 4- Ethylbenzyl, 4-isopropylbenzyl, 4-t-butylbenzyl, 4-tripentylbenzyl, 4-cyclohexylbenzyl, 4-n-octylbenzene Base, 4-vinylbenzyl, 4-phenylbenzyl, 4-(4'-tert-butylphenyl)benzyl, 4-methoxybenzyl, 3-methoxybenzene Methyl, 2-ethoxybenzyl, 4-n-butoxybenzyl, 3,4-dimethoxybenzyl, 4-fluorobenzyl, 2-fluorobenzyl, 4- Chlorobenzyl, 2-chlorobenzyl, 2-furyl, 1-naphthylmethyl, 4-diethylaminobenzyl, etc., preferably benzyl, α-methylbenzyl , α,α-dimethylbenzyl, phenethyl, α-methylphenethyl, 4-methylphenethyl, 4-methylbenzyl, 2-methylbenzyl, 4- Ethylbenzyl, 4-isopropylbenzyl, 4-t-butylbenzyl, 4-n-octylbenzyl, 4-benzene Benzyl, 4-methoxybenzyl, 2-ethoxybenzyl, 4-n-butoxybenzyl, 4-fluorobenzyl, 2-fluorobenzyl, 4-chlorobenzene Methyl, 2-chlorobenzyl, 2-furyl, 1-naphthylmethyl, 4-diethylaminobenzyl, more preferably benzyl, α,α-dimethylbenzyl , phenethyl, 4-methylphenethyl, 4-methylbenzyl, 4-ethylbenzyl, 4-isopropylbenzyl, 4-tert-butylbenzyl, 4- n-Octylbenzyl, 4-phenylbenzyl, 4-methoxybenzyl, 2-ethoxybenzyl, 4-n-butoxybenzyl, 4-chlorobenzyl, 2-Chlorobenzyl, 2-furyl, 4-diethylaminobenzyl.

When R ₁ to R ₈ are a substituted or unsubstituted amino group, an amine group, an N-methylamino group, an N-ethylamino group, an N-n-propylamino group, and an N-n-butylamine are mentioned. , N-cyclohexylamino, N-n-octylamino, N-benzylamino, N-phenylamino, N-(3-methylphenyl)amino, N-(4- Methoxyphenyl)amino, N-(3-fluorophenyl)amine, N-(4-chlorophenyl)amine, N-(2-naphthyl)amine, N,N-dimethyl Amino, N,N-diethylamino, N,N-di-n-propylamino, N,N-di-n-butylamino, N,N-di-n-octylamino, N,N - Di-n-decylamino, N-methyl-N-ethylamino, N-ethyl-N-ethylamino, N-ethyl-N-n-butylamino, N-methyl- N-phenylamino, N-n-butyl-N-phenylamino, N-benzyl-N-phenylamino, N,N-diphenylamino, N,N-di(3 -Methylphenyl)amino, N,N-bis(4-ethylphenyl)amino, N,N-bis(4-tert-butylphenyl)amine, N,N-di (4 -Methoxyphenyl)amino, N,N-bis(4-ethoxyphenyl)amine, N,N-bis(4-n-hexyloxyphenyl)amine, N,N-di (2-Naphthyl)amino, N-phenyl-N-(4-methylphenyl)amino, N-phenyl-N-(4-methoxyphenyl)amino, N-phenyl - N-(4-n-hexyloxyphenyl)amino, N-phenyl-N-(1-naphthyl)amine, N-phenyl-N-(2-naphthyl)amine, N-benzene ke-N-(4-phenylphenyl)amine, N-morphine N-thiophene Phenothyzinyl or the like, preferably an amine group, an N-methylamino group, an N-ethylamino group, an N-n-propylamino group, an N-n-butylamino group, an N-n-octylamino group, N-benzylamino, N-phenylamino, N-(4-methoxyphenyl)amine, N-(3-fluorophenyl)amine, N-(4-chlorophenyl) Amine, N,N-dimethylamino, N,N-diethylamino, N,N-di-n-propylamino, N,N-di-n-butylamino, N,N- n-Octylamino, N-methyl-N-ethylamino, N-ethyl-N-n-butylamino, N-methyl-N-phenylamino, N,N-diphenyl Amino, N,N-bis(3-methylphenyl)amino, N,N-bis(4-methoxyphenyl)amine, N-phenyl-N-(4-methylphenyl Amino group, more preferably amine group, N-methylamino group, N-ethylamino group, N-n-propylamino group, N-n-butylamino group, N-n-octylamino group, N- Phenylamino, N,N-dimethylamino, N,N-diethylamino, N,N-di-n-propylamino, N,N-di-n-butylamino, N,N - Di-n-octylamino group, N-methyl-N-ethylamino group, N-ethyl-N-n-butylamino group, N-methyl-N-phenylamino group, N,N-di Phenylamino, N,N-bis(3-methylphenyl)amino, N,N-bis(4-methoxyphenyl)amine.

When R ₁ to R ₈ are a substituted or unsubstituted fluorenyl group, a fluorenyl group, an ethyl fluorenyl group, a propyl fluorenyl group, a n-propylcarbonyl group, a n-butylcarbonyl group, an isobutylcarbonyl group, and a t-butyl group are exemplified. Carbonyl, n-pentylcarbonyl, isopentylcarbonyl, 2-methylbutylcarbonyl, acryloyl, benzhydryl, 4-methylbenzhydryl, 2,4-dimethylbenzimidyl, 3-chlorobenzhydryl, 4-dimethylaminobenzimidyl, 2-methoxybenzimidyl, 3-butoxy-2-naphthylmethyl, cinnamoyl, etc. Preferred is indenyl, ethyl hydrazino, propyl fluorenyl, n-propylcarbonyl, n-butylcarbonyl, isobutylcarbonyl, n-pentylcarbonyl, isopentylcarbonyl, acrylonitrile, benzhydryl, 4-methylbenzhydryl, 2,4-dimethylbenzimidyl, 3-chlorobenzhydryl, 4-dimethylaminobenzimidyl, 2-methoxybenzimidyl Cinnamonyl, more preferably methyl, ethyl, propyl, n-propylcarbonyl, benzhydryl, 4-methylbenzhydryl, 2,4-dimethylbenzimidyl , 3-chlorobenzhydryl, 4-dimethylaminobenzimidyl, cinnamyl.

When R ₁ to R ₈ are a substituted or unsubstituted aryloxy group, a phenyloxy group, a 2-methylphenyloxy group, a 4-methylphenyloxy group, a 4-ethylphenyl group are exemplified. Oxyl, 4-isopropylphenyloxy, 4-isobutylphenyloxy, 4-n-pentylphenyloxy, 4-tripentylphenyloxy, 4-cyclohexylphenyl Oxy, 4-n-octylphenyloxy, 4-n-decylphenyloxy, 4-n-dodecylphenyloxy, 4-n-hexadecylphenyloxy, 2,3 - dimethylphenyloxy, 2,5-dimethylphenyloxy, 3,4-dimethylphenyloxy, 3,4,5-trimethylphenyloxy, 5-hydrogen Mercaptooxy, 1,2,3,4-tetrahydro-6-naphthyloxy, 3-methoxyphenyloxy, 3-ethoxyphenyloxy, 4-n-propoxybenzene Alkoxy, 4-n-butoxyphenyloxy, 4-n-pentyloxyphenyloxy, 4-cyclohexyloxyphenyloxy, 4-n-octyloxyphenyloxy, 4-n-decyloxyphenyloxy, 4-n-dodecyloxyphenyloxy, 4-n-hexadecyloxyphenyloxy, 2,3-dimethoxyphenyl Oxyl, 2,5-dimethoxyphenyloxy, 3,5-dimethoxyphenyloxy, 2-methoxy-4-methylphenyl , 3-methoxy-4-methylphenyloxy, 3-methyl-4-methoxyphenyloxy, 2-fluorophenyloxy, 4-fluorophenyloxy, 3- Chlorophenyloxy, 4-bromophenyloxy, 3-trifluoromethylphenyloxy, 3,5-difluorophenyloxy, 3,4-dichlorophenyloxy, 2-methyl 4-chlorophenyloxy, 3-chloro-4-methylphenyloxy, 3-methoxy-4-fluorophenyloxy, 3-fluoro-4-methoxyphenyloxy , 4-phenylphenyloxy, 3-phenylphenyloxy, 4-(4'-methylphenyl)phenyloxy, 4-(4'-methoxyphenyl)phenyloxy , 1-naphthyloxy, 4-methyl-1-naphthyloxy, 6-n-butyl-2-naphthyloxy, 7-ethoxy-2-naphthyloxy, 2-thiophene Alkoxy, 2-pyridyloxy, 4-pyridyloxy, etc., preferably phenyloxy, 2-methylphenyloxy, 4-methylphenyloxy, 4-ethylbenzene Alkoxy, 4-isopropylphenyloxy, 4-isobutylphenyloxy, 4-n-pentylphenyloxy, 4-n-octylphenyloxy, 4-n-dodecane Phenyloxy, 2,3-dimethylphenyloxy, 2,5-dimethylphenyloxy, 3,4,5-trimethylphenyloxy, 1,2,3, 4-tetrahydro-6-naphthyloxy, 3-methoxy Alkoxy, 3-ethoxyphenyloxy, 4-n-propoxyphenyloxy, 4-n-butoxyphenyloxy, 2,3-dimethoxyphenyloxy, 3 , 5-dimethoxyphenyloxy, 2-methoxy-4-methylphenyloxy, 4-fluorophenyloxy, 3-chlorophenyloxy, 4-bromophenyloxy , 3-trifluoromethylphenyloxy, 3,4-difluorophenyloxy, 3-chloro-4-methylphenyloxy, 1-naphthyloxy, 4-methyl-1- Naphthyloxy, particularly preferably phenyloxy, 2-methylphenyloxy, 4-methylphenyloxy, 4-ethylphenyloxy, 4-isopropylphenyloxy, 4-isobutylphenyloxy, 2,3-dimethylphenyloxy, 2,5-dimethylphenyloxy, 3,4,5-trimethylphenyloxy, 3- Methoxyphenyloxy, 3-ethoxyphenyloxy, 4-n-propoxyphenyloxy, 4-n-butoxyphenyloxy, 2,3-dimethoxyphenyl Oxyl, 3,5-dimethoxyphenyloxy, 2-methoxy-4-methylphenyloxy, 4-fluorophenyloxy, 3-chlorophenyloxy, 4-bromo Phenyloxy, 3-trifluoromethylphenyloxy, 3,4-difluorophenyloxy, 1-naphthyloxy, 4-methyl-1-naphthyloxy.

When R ₁ to R ₈ are a substituted or unsubstituted aryloxyalkyl group, for example, phenyloxymethyl, 4-methylphenyloxymethyl, 4-ethylphenyloxy is exemplified. Methyl, 4-n-butylphenyloxymethyl, 4-n-hexylphenyloxymethyl, 4-n-decylphenyloxymethyl, 4-methoxyphenyloxymethyl , 4-butoxyphenyloxymethyl, 4-n-pentyloxyphenyloxymethyl, 4-fluorophenyloxymethyl, 2-fluorophenyloxymethyl, 3,4 -difluorophenyloxymethyl, 4-chlorophenyloxymethyl, 4-phenylphenyloxymethyl, 2-naphthyloxymethyl, 1-phenyloxyethyl, 2 -(4'-methylphenyloxy)ethyl, 2-(4'-ethylphenyloxy)ethyl, 2-(4'-methoxyphenyloxy)ethyl, 2- (4'-n-butoxyphenyloxy)ethyl, 2-(4'-fluorophenyloxy)ethyl, 2-(3'-chlorophenyloxy)ethyl, 2-(1 '-Naphthyloxy)ethyl, 2-phenyloxypropyl, 3-phenyloxypropyl, 3-(4'-methylphenyloxy)propyl, 4-phenyloxy Butyl, 4-(2'-ethylphenyloxy)butyl, 4-phenyloxypentyl, 5-(4'-tert-butylphenyloxy)pentyl, 6-phenyl Oxyhexyl, 8-phenyloxyoctyl, 10-(3'-methylphenyloxy)indolyl, etc., preferably phenyloxymethyl, 4-methylphenyloxymethyl, 4-ethyl Phenyloxymethyl, 4-n-butylphenyloxymethyl, 4-n-hexylphenyloxymethyl, 4-n-nonylphenyloxymethyl, 4-methoxyphenyl Oxymethyl, 4-butoxyphenyloxymethyl, 4-fluorophenyloxymethyl, 3,4-difluorophenyloxymethyl, 4-chlorophenyloxymethyl, 2-naphthyloxymethyl, 1-phenyloxyethyl, 2-(4'-methylphenyloxy)ethyl, 2-(4'-ethylphenyloxy)ethyl, 2-(4'-methoxyphenyloxy)ethyl, 2-(4'-n-butoxyphenyloxy)ethyl, 2-(4'-fluorophenyloxy)ethyl, 2-(3'-Chlorophenyloxy)ethyl, 2-(1'-naphthyloxy)ethyl, 3-phenyloxypropyl, 3-(4'-methylphenyloxy , propyl, 4-phenyloxybutyl, 4-phenyloxypentyl, 6-phenyloxyhexyl, 8-phenyloxyoctyl, more preferably phenyloxymethyl, 4 -methylphenyloxymethyl, 4-ethylphenyloxymethyl, 4-n-butylphenyloxymethyl, 4-methoxyphenyloxymethyl, 4-butoxy Phenyloxy , 4-chlorophenyloxymethyl, 2-naphthyloxymethyl, 1-phenyloxyethyl, 2-(4'-methylphenyloxy)ethyl, 2-(4 '-Ethylphenyloxy)ethyl, 2-(4'-methoxyphenyloxy)ethyl, 2-(3'-chlorophenyloxy)ethyl, 2-(1'- Naphthyloxy)ethyl, 3-phenyloxypropyl, 3-(4'-methylphenyloxy)propyl, 4-phenyloxybutyl, 4-phenyloxypentyl .

When R ₁ to R ₈ are a substituted or unsubstituted aralkyloxy group, a benzyloxy group, an α-methylbenzyloxy group, an α-ethylbenzyloxy group, α, Α-dimethylbenzyloxy, α-phenylbenzyloxy, α,α-diphenylbenzyloxy, phenethyloxy, α-methylphenethyloxy, --methylphenethyloxy, α,α-dimethylphenethyloxy, 4-methylphenethyloxy, 4-methylbenzyloxy, 2-methylbenzyl Oxyl, 4-ethylbenzyloxy, 2-ethylbenzyloxy, 4-tert-butylbenzyloxy, 2-tert-butylbenzyloxy, 4-positive Pentylbenzyloxy, 4-cyclohexylbenzyloxy, 4-n-octylbenzyloxy, 4-phenylbenzyloxy, 4-(4'-methylphenyl) Benzyloxy, 4-(4'-tert-butylphenyl)benzyloxy, 4-methoxybenzyloxy, 2-ethoxybenzyloxy, 4-正Heptyloxybenzyloxy, 3,4-dimethoxybenzyloxy, 4-fluorobenzyloxy, 3-chlorobenzyloxy, 3,4-dichlorobenzene a methoxy group, a 2-furyloxy group, a 2-naphthylmethyloxy group, etc., preferably a benzyloxy group, Α-methylbenzyloxy, α-ethylbenzyloxy, α,α-dimethylbenzyloxy, phenethyloxy, α-methylphenethyloxy, β -methylphenethyloxy, α,α-dimethylphenethyloxy, 4-methylphenethyloxy, 4-methylbenzyloxy, 2-methylbenzyloxy Base, 4-ethylbenzyloxy, 2-ethylbenzyloxy, 4-t-butylbenzyloxy, 4-n-pentylbenzyloxy, 2-ethoxy Benzyloxy, 3,4-dimethoxybenzyloxy, 4-fluorobenzyloxy, 3-chlorobenzyloxy, 3,4-dichlorobenzyloxy, 2-furyloxy, 2-naphthylmethyloxy, more preferably benzyloxy, α-methylbenzyloxy, α-ethylbenzyloxy, α,α-di Methylbenzyloxy, phenethyloxy, α-methylphenethyloxy, β-methylphenethyloxy, α,α-dimethylphenethyloxy, 4-methyl Benzomethyloxy, 2-methylbenzyloxy, 4-ethylbenzyloxy, 2-ethylbenzyloxy, 2-ethoxybenzyloxy, 3, 4-dimethoxybenzyloxy, 3-chlorobenzyloxy, 3,4-dichlorobenzyloxy 2-furyl group, 2-naphthylmethyl group.

When R ₁ to R ₈ are a substituted or unsubstituted aralkyloxyalkyl group, a benzyloxymethyl group, a phenethyloxymethyl group, a 4-methylbenzyloxymethyl group may be mentioned. , 4-n-propylbenzyloxymethyl, 4-n-octylbenzyloxymethyl, 4-methoxybenzyloxymethyl, 4-n-butoxybenzyl Oxymethyl, 4-fluorobenzyloxymethyl, 3-fluorobenzyloxymethyl, 4-chlorobenzyloxymethyl, 2-benzyloxyethyl, 2- Phenylethyloxyethyl, 2-(4'-methylbenzyloxy)ethyl, 2-(4'-fluorobenzyloxy)ethyl, 2-(4'-chlorobenzyl Ethyloxy)ethyl, 3-(4'-methoxybenzyloxy)propyl, 4-benzyloxybutyl, 4-(4'-phenylbenzyloxy)butyl a group, a 6-benzyloxyhexyl group, etc., preferably a benzyloxymethyl group, a phenethyloxymethyl group, a 4-methylbenzyloxymethyl group, a 4-n-propyl benzoyl group Hydroxymethyl, 4-methoxybenzyloxymethyl, 4-n-butoxybenzyloxymethyl, 3-fluorobenzyloxymethyl, 4-chlorobenzyl Oxymethyl, 2-benzyloxyethyl, 2-phenylethyloxyethyl, 3-(4'-methoxybenzene Methoxy)propyl, 4-benzyloxybutyl, 4-(4'-phenylbenzyloxy)butyl, preferably benzyloxymethyl, phenethyloxy Methyl, 4-methylbenzyloxymethyl, 4-methoxybenzyloxymethyl, 4-n-butoxybenzyloxymethyl, 3-fluorobenzyloxy Methyl, 4-chlorobenzyloxymethyl, 2-benzyloxyethyl, 2-phenylethyloxyethyl, 3-(4'-methoxybenzyloxy)propane Base, 4-benzyloxybutyl.

When R ₁ to R ₈ are a substituted or unsubstituted arylthio group, they also contain a heteroarylthio group, and examples thereof include a phenylthio group, a 2-methylphenylthio group, and a 4-methylphenyl sulfide. , 3-ethylphenylthio, 4-n-propylphenylthio, 4-n-butylphenylthio, 4-isobutylphenylthio, 4-tert-butylphenylsulfide , 4-n-pentylphenylthio, 4-n-hexylphenylthio, 4-cyclohexylphenylthio, 4-n-octylphenylthio, 4-n-dodecylphenylsulfide Base, 4-n-octadecylphenylthio, 2,5-dimethylphenylthio, 3,4-dimethylphenylthio, 5-hydrodecylthio, 1,2, 3,4-tetrahydro-6-naphthylthio, 2-methoxyphenylthio, 3-methoxyphenylthio, 4-ethoxyphenylthio, 4-n-propoxy Phenylthio, 2,4-dimethoxyphenylthio, 3,5-diethoxyphenylthio, 2-methoxy-4-methylphenylthio, 2-methyl 4-methoxyphenylthio, 2-fluorophenylthio, 4-fluorophenylthio, 2-chlorophenylthio, 4-bromophenylthio, 4-trifluorophenyl Thio, 3-trifluorophenylthio, 2,4-difluorophenylthio, 2,4-dichlorophenylthio, 2-chloro-4-methoxy Thiothio, 2-naphthylthio, 4-methyl-1-naphthylthio, 4-ethoxy-1-naphthylthio, 2-pyridylthio, 4-aminophenylsulfide , 4-(N,N-dimethylamino)phenylthio, 4-(N,N-diethylamino)naphthylthio, 4-[N,N-di(4'- Methylphenyl)amino]phenylthio, 4-(N-morphine Phenylthio group or the like, preferably phenylthio, 2-methylphenylthio, 4-methylphenylthio, 3-ethylphenylthio, 4-n-propylphenyl Sulfuryl, 4-n-butylphenylthio, 2,5-dimethylphenylthio, 3,4-dimethylphenylthio, 1,2,3,4-tetrahydro-6- Naphthylthio, 2-methoxyphenylthio, 4-ethoxyphenylthio, 2,4-dimethoxyphenylthio, 3,5-diethoxyphenylthio , 2-methoxy-4-methylphenylthio, 2-fluorophenylthio, 2-chlorophenylthio, 4-trifluoromethylphenylthio, 2,4-difluorobenzene Thiothio, 2,4-dichlorophenylthio, 2-chloro-4-methoxyphenylthio, 2-naphthylthio, 4-methyl-1-naphthylthio, 2- Pyridylthio, 4-(N,N-dimethylamino)phenylthio, 4-(N,N-diethylamino)naphthylthio, more preferably phenylthio, 2 -methylphenylthio, 4-methylphenylthio, 3-ethylphenylthio, 2,5-dimethylphenylthio, 3,4-dimethylphenylthio, 2-methoxyphenylthio, 4-ethoxyphenylthio, 2,4-dimethoxyphenylthio, 2-methoxy-4-methylphenylthio, 2- Chlorophenylthio, 4-trifluoromethylbenzene Thio, 2,4-dichlorophenyl group, a 2-chloro-4-methoxyphenyl group, 2-naphthyl group.

a group selected from R ₁ to R ₈ adjacent to each other, and a substituted or unsubstituted 5 membered ring or more together with a substituted carbon atom, an unsubstituted benzene ring or a naphthalene ring, and It preferably has a halogen atom, a cyano group, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkylthio group having 1 to 8 carbon atoms, and carbon. Alkoxyalkyl group of 2 to 12, substituted or unsubstituted aryl group having 6 to 12 carbon atoms, substituted or unsubstituted amine group, substituted or unsubstituted carbon number 7 to 16. An aralkyl group, a substituted or unsubstituted aryloxy group having 6 to 12 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 12 carbon atoms as a substituent of a benzene ring or a naphthalene ring, For example, a benzene ring or a naphthalene ring; having a chlorine atom, a fluorine atom, a bromine atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, and a n-pentyl group; , n-hexyl, 1,2-dimethylbutyl, n-octyl, 2-ethylhexyl, vinyl, propenyl, 1-butenyl, methoxy, ethoxy, n-propoxy, iso Propyloxy, n-butoxy, second butoxy, Pentyloxy, 2-ethylbutyloxy, n-octyloxy, methylthio, ethylthio, n-propylthio, n-butylthio, second butylthio, n-pentyl Thio, n-octylthio, phenyl, 2-methylphenyl, 2-methoxyphenyl, 2-chlorophenyl, 1-naphthyl, 2-pyridyl, methoxymethyl, B Oxymethyl, n-butoxymethyl, benzyl, phenethyl, amine, N-ethylamino, N,N-dimethylamino, N,N-diethylamino, a benzene ring or a naphthalene ring having a N,N-di-n-butylamino group, a benzyloxy group or a phenylthio group as a substituent; preferably a benzene ring; having a chlorine atom, a fluorine atom, a bromine atom, a methyl group, Ethyl, n-propyl, isopropyl, n-butyl, n-octyl, 2-ethylhexyl, vinyl, propenyl, methoxy, ethoxy, n-propoxy, isopropoxy, positive Butoxy, methylthio, ethylthio, n-propylthio, n-butylthio, phenyl, 2-methylphenyl, 2-methoxyphenyl, 2-chlorophenyl, Methoxymethyl, ethoxymethyl, n-butoxymethyl, benzyl, amine, N,N-dimethylamino, N,N-diethylamino, N,N- Erzheng Ding a benzene ring having an amine group, a benzyloxy group or a phenylthio group as a substituent, more preferably a benzene ring; having a chlorine atom, a fluorine atom, a bromine atom, a methyl group, an ethyl group, an n-butyl group, a vinyl group, and a propylene group. Base, methoxy, ethoxy, methylthio, ethylthio, n-butylthio, phenyl, 2-methylphenyl, 2-methoxyphenyl, methoxymethyl, a benzene ring having an ethoxymethyl group, a benzyl group, an amine group, an N,N-dimethylamino group, an N,N-diethylamino group, a benzyloxy group, or a phenylthio group as a substituent.

Further, the tetraazaporphyrin compound of the formula (1) may be substituted by the substitution positions of each of R ₁ and R ₂ , R ₃ and R ₄ , R ₅ and R ₆ , and R ₇ and R ₈ . a positional isomer, and a bonding site of a pyrrole ring of each of R ₁ and R ₂ , R ₃ and R ₄ , R ₅ and R ₆ , and R ₇ and R _{8 in} the tetraazaporphyrin ring structure There are isomers. Mixtures of these various positional isomers are often obtained by conventional methods. The absorption characteristics of the individual excipients of each isomer are more sharp, and even a mixture can be used undoubtedly in the resin composition of the present invention.

Specific examples of the porphyrazine compound (B-1) related to the resin composition of the present invention are shown in Table 1 below, but are not limited thereto. Since each specific example compound also contains a positional isomer of each substituent, a substituent is represented by a combination of R ₁ and R ₂ , R ₃ and R ₄ , R ₅ and R ₆ , and R ₇ and R ₈ . Further, isomers relating to the bonding position of the pyrrole ring in the combined tetraazaporphyrin structure are also within the scope of the present invention.

The porphyrazine compound (B-1) related to the resin composition of the present invention can be produced by a known method.

For example, Japanese Laid-Open Patent Publication No. H11-35837, Japanese Patent Application Laid-Open No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. It is produced by the method described in JP-A-2007-186708. For example, one or two or more kinds of maleonitrile derivatives of the following formula (A) or a 2,5-diimidopyrrole derivative of the following formula (B) may be used. Manufactured by heating.

(In the formula, Ra and Rb represent the same as those of R ₁ to R _{8 of the} formula (2).)

[Compound (B-2)]

The resin composition of the present invention contains the compound (B-2) contained together with the porphyrazine compound (B-1) represented by the formula (1) at a wavelength of 380 to 470 nm in a toluene solution. The ratio (A1/A2) of the absorbance (A1) having the maximum absorption and the maximum absorption wavelength between 520 and 800 nm and the maximum absorption wavelength between 380 and 470 nm (A1/A2) is less than 0.1.

Further, in the present specification, "the absorption in the toluene solution having a maximum absorption wavelength between 380 and 470 nm, and the absorption at the maximum absorption wavelength between 520 and 800 nm (A1) and the maximum absorption wavelength between 380 and 470 nm. The ratio (A1/A2) of the absorbance (A2) is less than 0.1" and is collectively referred to as "the absorption characteristic specified in the present invention". Further, in the present specification, the absorption of the compound (B-2) The value obtained by using a U-3500 self-recording spectrophotometer manufactured by Hitachi, Ltd. as a measuring instrument, and measuring a wavelength of 350 to 900 nm in a toluene solution having a concentration of 0.01 g/L in a light path length of 10 mm is The horizontal axis represents the value of the vertical axis when the absorption spectrum is plotted as the wavelength (nm).

In detail, the compound (B2) is measured using a toluene solution. When the absorption spectrum is fixed, among the visible light regions of about 380 to 800 nm, the absorbance value (A2) of the maximum absorption wavelength in a specific wavelength region of 380 to 470 nm and the absorbance at the maximum absorption wavelength of a specific wavelength region of 520 to 800 nm are obtained. The numerical value (A1) is a compound in which the ratio (A1) to (A2) (A1/A2) is less than 0.1. Further, even if a peak of a clear absorption wavelength is not recognized in a specific wavelength region of 520 to 800 nm, the maximum value of the absorbance which can be confirmed in this range is (A1).

The ratio (A1/A2) of (A1) to (A2) in the compound (B-2) is preferably less than 0.09, more preferably less than 0.08. When a compound having a ratio (A1) to (A2) (A1/A2) of 0.1 or more is used in the resin composition of the present invention, there is a possibility that the color of the resin composition is increased and the visible light transmittance is lowered. .

Further, the preferred embodiment of the compound (B-2) is not particularly limited as long as it has the absorption characteristics specified in the present invention and has a yellow hue, but it is more preferable to have the absorption characteristics specified in the present invention. And when the absorption spectrum is measured using a toluene solution, a compound having a yellow hue of a peak which does not recognize the absorption wavelength in a specific wavelength range of 471 to 519 nm is more preferably used for measuring an absorption spectrum using a toluene solution. 380 A compound having a maximum absorption wavelength to a specific wavelength region of 470 nm and a yellow hue of a peak of an absorption wavelength that is not recognized in a specific wavelength region of 471 to 800 nm.

In particular, the compound which satisfies the absorption property specified in the present invention is preferably at least one selected from the group consisting of an azo compound having a specific structure, a quinophthalone compound having a specific structure, and a specific lanthanoid compound. .

Hereinafter, preferred embodiments will be described in detail.

[Azo compound]

The azo compound is not particularly limited as long as it has the absorption property specified in the present invention, but is preferably a compound represented by the following formula (2).

[In the formula (2), Y ₁ to Y ₁₁ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a decyl group, a carboxyl group, an alkyl group, an alkenyl group, an alkyl halide group, an alkoxy group, or a halogenated alkoxy group. Alkyl, alkylthio, alkoxyalkyl, alkoxyalkoxyalkyl, halogenated alkoxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, Substituted or unsubstituted amino, substituted or unsubstituted guanylamino, substituted or unsubstituted fluorenyl, substituted or unsubstituted aryloxy, substituted or unsubstituted Aryloxyalkyl, substituted or unsubstituted aralkyloxy, substituted or unsubstituted aralkyloxyalkyl, alkyloxycarbonyl, substituted or unsubstituted aryl An oxycarbonyl group, or a substituted or unsubstituted arylthio group. ]

Here, Y ₁ to Y ₁₁ are a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group. Alkoxyalkyl, substituted or unsubstituted aralkyloxy, substituted or unsubstituted aralkyloxyalkyl, substituted or unsubstituted aryloxycarbonyl, substituted or The unsubstituted arylthio group is a substituent at the time of substitution, and each of them may be a halogen atom, a cyano group, a nitro group, a hydroxyl group, a decyl group, a carboxyl group, an alkyl group, an alkenyl group, an alkyl halide group, an alkoxy group or a halogenated alkoxy group. a group, an alkylthio group, an alkoxyalkyl group, an amine group, an alkylamino group, a dialkylamino group.

Y ₁ to Y ₁₁ are a substituted or unsubstituted amino group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group is a substituted group, and each may be an alkyl group, Substituted or unsubstituted aryl, substituted or unsubstituted aralkyl.

Y ₁ to Y ₁₁ in the formula (2) are preferably a halogenated alkyl group each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, a carbon number of 2 to 6 alkenyl groups, and a carbon number of 1 to 12. Alkoxy group having 1 to 12 carbon atoms, halogenated alkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, alkoxyalkyl group having 2 to 16 carbon atoms, and carbon number 3 to 20 Alkoxyalkoxyalkyl group, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted amino group having 1 to 18 carbon atoms, substituted with 1 to 18 carbon atoms Or unsubstituted amidino group, substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms, carbon number 7 to 20 a substituted or unsubstituted aryloxyalkyl group, a substituted or unsubstituted alkyloxycarbonyl group having 2 to 13 carbon atoms, a substituted or unsubstituted aryloxy group having 7 to 19 carbon atoms A carbonyl group, a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms.

Further, Y ₁ to Y _{11 are more} preferably independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 8 carbon atoms, a carbon number of 2 to 4 alkenyl groups, and an alkyl group having 1 to 8 carbon atoms. An oxy group, a halogenated alkoxy group having 1 to 8 carbon atoms, an alkylthio group having 1 to 8 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, a halogenated alkoxyalkyl group having 2 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted amino group having 1 to 14 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 18 carbon atoms, carbon A substituted or unsubstituted aryloxy group of 6 to 14 or a substituted or unsubstituted arylthio group having 6 to 14 carbon atoms.

Specific examples of Y ₁ to Y ₁₁ will be described below.

Y ₁ to Y ₁₁ are a halogen atom, an alkyl group, an alkenyl group, an alkyl halide group, an alkoxy group, a halogenated alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkoxyalkoxyalkyl group, or an alkyl halide. Oxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl, substituted or unsubstituted amino, substituted or unsubstituted fluorenyl, substituted or not Specific when substituted aryloxy, substituted or unsubstituted aryloxyalkyl, substituted or unsubstituted aralkyloxy, or substituted or unsubstituted arylthio In the case of the porphyrazine compound of the above formula (1), the substituents of R ₁ to R _{8 of} the above formula (1) are the same as those exemplified.

When Y ₁ to Y ₁₁ are a substituted or unsubstituted guanylamino group, an anthranyl group, an N-methyl decylamino group, an N-ethyl decylamino group, and an N-positive group are mentioned. Propyl amidino, N-n-butyl decylamino, N-cyclohexyl decylamino, N-n-octyl decylamino, N-benzylmethylguanamine, N-phenyldecylamine, N -(3-methylphenyl)nonylamino, N-(4-methoxyphenyl)nonylamino, N-(3-fluorophenyl)decylamino, N-(4-chlorophenyl) Amidino, N-(2-naphthyl)nonylamino, N,N-dimethylammonium, N,N-diethylguanamine, N,N-di-n-propylammonium, N,N-di-n-butylammonium, N,N-di-n-octylphosphonium, N,N-di-n-decylamino, N-methyl-N-ethylguanamine, N -ethyl-N-n-butylamylamine, N-methyl-N-phenyldecylamino, N-n-butyl-N-phenyldecylamino, N-benzyl-N-phenyl Amidino, N,N-diphenylguanamine, N,N-bis(3-methylphenyl)decylamine, N,N-bis(4-ethylphenyl)decylamine, N , N-bis(4-t-butylphenyl)nonylamino, N,N-bis(4-methoxyphenyl)nonylamino, N,N-bis(4-ethoxyphenyl) Amidino, N,N-bis(4-n-hexyloxyphenyl)nonylamino, N,N-di(2 -naphthyl)nonylamino, N-phenyl-N-(4-methylphenyl)nonylamino, N-phenyl-N-(4-methylphenyl)nonylamino, N-phenyl -N-(4-n-hexyloxyphenyl)nonylamino, N-phenyl-N-(1-naphthyl)nonylamino, N-phenyl-N-(2-naphthyl)nonylamino , N-phenyl-N-(4-phenylphenyl)nonylamino, etc., preferably decylamino, N-methylnonylamino, N-ethylguanamine, N-n-propylhydrazine Amine, N-n-butylamylamine, N-n-octyldecylamine, N-benzylmethylguanamine, N-phenyldecylamine, N-(4-methoxyphenyl)fluorene Amine, N-(3-fluorophenyl)decylamino, N-(4-chlorophenyl)decylamine, N,N-dimethylamidoamine, N,N-diethylguanamine , N,N-di-n-propylammonium, N,N-di-n-butylammonium, N,N-di-n-octylphosphonium, N-methyl-N-ethylantimony, N-ethyl-N-n-butylammonium, N-methyl-N-phenylnonylamino, N,N-diphenylnonylamino, N,N-bis(3-methylphenyl An amidino group, an N,N-bis(4-methoxyphenyl)nonylamino group, an N-phenyl-N-(4-phenylphenyl)phosphonium group, more preferably an amidino group, N -methyl decylamino, N-ethyl decylamino, N-n-propyl decylamino, N-n-butyl decylamino, N-n-octyl decylamine , N-phenylguanamine, N,N-dimethylamidino, N,N-diethylguanamine, N,N-di-n-propylammonium, N,N-di-n-butyl Amino group, N,N-di-n-octyl decylamino group, N-methyl-N-ethyl decylamino group, N-ethyl-N-n-butyl decylamino group, N-methyl-N -Phenylguanamine, N,N-diphenyldecylamino, N,N-bis(3-methylphenyl)decylamino, N,N-bis(4-methoxyphenyl)fluorene Amine.

When Y ₁ to Y ₁₁ are an alkyloxycarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group, an isopropoxycarbonyl group, a n-butoxycarbonyl group, a second butoxycarbonyl group, N-pentyloxycarbonyl, cyclopentyloxycarbonyl, n-hexyloxycarbonyl, 3,3-dimethylbutyloxycarbonyl, 2-ethylbutyloxycarbonyl, cyclohexyloxycarbonyl, positive Heptyloxycarbonyl, n-octyloxycarbonyl, 2-ethylhexyloxycarbonyl, n-decyloxycarbonyl, n-undecyloxycarbonyl, n-dodecyloxycarbonyl, n-tride Alkyloxycarbonyl, n-tetradecyloxycarbonyl, n-pentadecyloxycarbonyl, n-hexadecyloxycarbonyl, n-heptadecyloxycarbonyl, n-octadecyloxycarbonyl , n-tricosyloxycarbonyl, n-tetracosyloxycarbonyl, etc., preferably methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxy Carbonyl group, second butoxycarbonyl group, n-pentyloxycarbonyl group, n-hexyloxycarbonyl group, 3,3-dimethylbutyloxycarbonyl group, 2-ethylbutyloxycarbonyl group, cyclohexyloxy group carbonyl , n-heptyloxycarbonyl, n-octyloxycarbonyl, 2-ethylhexyloxycarbonyl, n-dodecyloxycarbonyl, more preferably methoxycarbonyl, ethoxycarbonyl, n-propoxy Carbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, second butoxycarbonyl group, n-pentyloxycarbonyl group, n-hexyloxycarbonyl group, 2-ethylbutyloxycarbonyl group, cyclohexyloxycarbonyl group, n-Heptyloxycarbonyl, n-octyloxycarbonyl.

When Y ₁ to Y ₁₁ are a substituted or unsubstituted aryloxycarbonyl group, a phenyloxycarbonyl group, a 2-methylphenyloxycarbonyl group, a 4-methylphenyloxycarbonyl group, and a 4- Ethyl phenyloxycarbonyl, 4-isopropylphenyloxycarbonyl, 4-isobutylphenyloxycarbonyl, 4-n-pentylphenyloxycarbonyl, 4-tripentylphenyloxy Carbocarbonyl, 4-cyclohexylphenyloxycarbonyl, 4-n-octylphenyloxycarbonyl, 4-n-decylphenyloxycarbonyl, 4-n-dodecylphenyloxycarbonyl, 4- N-hexadecylphenyloxycarbonyl, 2,3-dimethylphenyloxycarbonyl, 2,5-dimethylphenyloxycarbonyl, 3,4-dimethylphenyloxycarbonyl, 3,4,5-trimethylphenyloxycarbonyl, 5-hydrodecyloxycarbonyl, 1,2,3,4-tetrahydro-6-naphthyloxycarbonyl, 3-methoxyphenyl Oxycarbonyl, 3-ethoxyphenyloxycarbonyl, 4-n-propoxyphenyloxycarbonyl, 4-n-butoxyphenyloxycarbonyl, 4-n-pentyloxyphenyloxy Carbonyl, 4-cyclohexyloxyphenyloxycarbonyl, 4-n-octyloxyphenyloxycarbonyl, 4-n-decyloxyphenyloxycarbonyl, 4-n-dodecyloxybenzene Oxycarbonyl, 4-n-hexadecyloxyphenyloxycarbonyl, 2,3-dimethoxyphenyloxycarbonyl, 2,5-dimethoxyphenyloxycarbonyl, 3,5 -dimethoxyphenyloxycarbonyl, 2-methoxy-4-methylphenyloxycarbonyl, 3-methoxy-4-methylphenyloxycarbonyl, 3-methyl-4- Methoxyphenyloxycarbonyl, 2-fluorophenyloxycarbonyl, 4-fluorophenyloxycarbonyl, 3-chlorophenyloxycarbonyl, 4-bromophenyloxycarbonyl, 3-trifluoromethyl Phenyloxycarbonyl, 3,5-difluorophenyloxycarbonyl, 3,4-dichlorophenyloxycarbonyl, 2-methyl-4-chlorophenyloxycarbonyl, 3-chloro-4 -methylphenyloxycarbonyl, 3-methoxy-4-fluorophenyloxycarbonyl, 3-fluoro-4-methoxyphenyloxycarbonyl, 4-phenylphenyloxycarbonyl, 3-phenylphenyloxycarbonyl, 4-(4'-methylphenyl)phenyloxycarbonyl, 4-(4'-methoxyphenyl)phenyloxycarbonyl, 1-naphthyloxy Carbocarbonyl, 4-methyl-1-naphthyloxycarbonyl, 6-n-butyl-2-naphthyloxycarbonyl, 7-ethoxy-2-naphthyloxycarbonyl, 2-thienyloxy a carbonyl group, a 2-pyridyloxycarbonyl group, a 4-pyridyloxycarbonyl group or the like, preferably Phenyloxycarbonyl, 2-methylphenyloxycarbonyl, 4-methylphenyloxycarbonyl, 4-ethylphenyloxycarbonyl, 4-isopropylphenyloxycarbonyl, 4-iso Butylphenyloxycarbonyl, 4-n-pentylphenyloxycarbonyl, 4-n-octylphenyloxycarbonyl, 4-n-dodecylphenyloxycarbonyl, 2,3-dimethyl Phenyloxycarbonyl, 2,5-dimethylphenyloxycarbonyl, 3,4,5-trimethylphenyloxycarbonyl, 1,2,3,4-tetrahydro-6-naphthyloxy Carbocarbonyl, 3-methoxyphenyloxycarbonyl, 3-ethoxyphenyloxycarbonyl, 4-n-propoxyphenyloxycarbonyl, 4-n-butoxyphenyloxycarbonyl, 2 , 3-dimethoxyphenyloxycarbonyl, 3,5-dimethoxyphenyloxycarbonyl, 2-methoxy-4-methylphenyloxycarbonyl, 4-fluorophenyloxy Carbonyl, 3-chlorophenyloxycarbonyl, 4-bromophenyloxycarbonyl, 3-trifluoromethylphenyloxycarbonyl, 3,4-dichlorophenyloxycarbonyl, 3-chloro-4- Methylphenyloxycarbonyl, 1-naphthyloxycarbonyl, 4-methyl-1-naphthyloxycarbonyl, more preferably phenyloxycarbonyl, 2-methylphenyloxycarbonyl, 4- Methylphenyloxycarbonyl, 4-ethylbenzene Oxycarbonyl, 4-isopropylphenyloxycarbonyl, 4-isobutylphenyloxycarbonyl, 2,3-dimethylphenyloxycarbonyl, 2,5-dimethylphenyloxy Carbonyl, 3,4,5-trimethylphenyloxycarbonyl, 3-methoxyphenyloxycarbonyl, 3-ethoxyphenyloxycarbonyl, 4-n-propoxyphenyloxycarbonyl 4-n-Butoxyphenyloxycarbonyl, 2,3-dimethoxyphenyloxycarbonyl, 3,5-dimethoxyphenyloxycarbonyl, 2-methoxy-4-methyl Phenyloxycarbonyl, 4-fluorophenyloxycarbonyl, 3-chlorophenyloxycarbonyl, 4-bromophenyloxycarbonyl, 3-trifluoromethylphenyloxycarbonyl, 3,4- Dichlorophenyloxycarbonyl, 1-naphthyloxycarbonyl, 4-methyl-1-naphthyloxycarbonyl.

Although specific examples of the azo compound of the formula (2) are listed in the following Table (2), it is not limited to these ranges.

Further, the azo compound of the formula (2) has a tautomer of the following formula (2'), and these isomers represent the same compound as the formula (2), and the same is also indicated in the present invention. effect.

[wherein, Y ₁ to Y ₁₁ represent the same as Y ₁ to Y _{11 of the} general formula (2). ]

The azo compound of the formula (2) can be produced by a known method.

For example, it can be produced by the method described in Chem. Pharm. Bull. 35 (4) 1360 to 1371 (1987) and the like.

For example, a nitrosourea derivative of the following formula (C) can be produced by reacting a pyrazole derivative of the following formula (D) with carbon tetrachloride.

[wherein, Y ₁ to Y ₁₁ represent the same as Y ₁ to Y _{11 of the} general formula (2). ]

[Quinone compound]

The quinacridone compound is not particularly limited as long as it has a property specified in the present invention, but is preferably a compound represented by the following formula (3).

[In the formula (3), Z ₁ to Z ₉ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a decyl group, a carboxyl group, an alkyl group, an alkenyl group, an alkyl halide group, an alkoxy group, or an alkyl halide. Oxyl, alkylthio, alkoxyalkyl, alkoxyalkoxyalkyl, halogenated alkoxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl , substituted or unsubstituted amino, substituted or unsubstituted guanylamino, substituted or unsubstituted fluorenyl, substituted or unsubstituted aryloxy, substituted or unsubstituted Aryloxyalkyl, substituted or unsubstituted aralkyloxy, substituted or unsubstituted aralkyloxyalkyl, alkyloxycarbonyl, substituted or unsubstituted aryl a oxycarbonyl group, or a substituted or unsubstituted arylthio group, and the mutually adjacent groups selected from Z ₆ to Z ₉ may be bonded to each other to form a substituted or unsubstituted group together with the substituted carbon atom. Replace the ring with a 5 member ring or more. ]

Here, Z ₁ to Z ₉ are a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group. Alkoxyalkyl, substituted or unsubstituted aralkyloxy, substituted or unsubstituted aralkyloxyalkyl, substituted or unsubstituted aryloxycarbonyl, substituted or The unsubstituted arylthio group, the mutually adjacent groups selected from Z ₆ to Z ₉ may be bonded to each other, and the substituted or unsubstituted 5 membered ring or more together with the substituted carbon atom is a ring The substituents at the time of substitution may each be a halogen atom, a cyano group, a nitro group, a hydroxyl group, a decyl group, a carboxyl group, an alkyl group, an alkenyl group, a halogenated alkyl group, an alkoxy group, a halogenated alkoxy group, an alkylthio group, an alkoxy group. An alkyl group, an amine group, an alkylamino group, a dialkylamino group.

Z ₁ to Z ₉ are a substituted or unsubstituted amino group, a substituted or unsubstituted amidino group, a substituted or unsubstituted fluorenyl group is a substituted substituent, and each may be an alkyl group, Substituted or unsubstituted aryl, substituted or unsubstituted aralkyl.

Z ₁ to Z ₉ in the formula (3) are preferably a halogenated alkyl group each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, a carbon number of 2 to 6 alkenyl groups, and a carbon number of 1 to 12. Alkoxy group having 1 to 12 carbon atoms, halogenated alkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, alkoxyalkyl group having 2 to 16 carbon atoms, and carbon number 3 to 20 Alkoxyalkoxyalkyl group, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted amino group having 1 to 18 carbon atoms, substituted with 1 to 18 carbon atoms Or unsubstituted amidino group, substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms, carbon number 7 to 20 a substituted or unsubstituted aryloxyalkyl group, an alkyloxycarbonyl group having 2 to 13 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 7 to 19 carbon atoms, and a carbon number of 6 to 18 The substituted or unsubstituted arylthio group, or the mutually adjacent groups selected from Z ₆ to Z ₉ may be bonded to each other, and form a substituted or unsubstituted 5-membered ring together with the substituted carbon atom. The above substituted or unsubstituted benzene or naphthalene ring.

More preferably, Z ₁ to Z ₉ are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 8 carbon atoms, a carbon number of 2 to 4 alkenyl groups, and an alkoxy group having 1 to 8 carbon atoms. a group, an alkylthio group having 1 to 8 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted carbon number of 1 to 14 or Unsubstituted amino group, substituted or unsubstituted guanylamino group having 1 to 14 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 18 carbon atoms, substituted with 6 to 14 carbon atoms or Unsubstituted aryloxy group, substituted or unsubstituted alkyloxycarbonyl group having 2 to 9 carbon atoms, substituted or unsubstituted aryloxycarbonyl group having 7 to 15 carbon atoms, carbon number 6 A substituted or unsubstituted arylthio group to 14.

Specific examples of Z ₁ to Z ₉ will be described below.

Z ₁ to Z ₉ are a halogen atom, an alkyl group, an alkenyl group, an alkyl halide group, an alkoxy group, a halogenated alkoxy group, an alkylthio group, an alkoxyalkyl group, an alkoxyalkoxyalkyl group, or an alkyl halide. Oxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl, substituted or unsubstituted amino, substituted or unsubstituted fluorenyl, substituted or not Substituted aryloxy, substituted or unsubstituted aryloxyalkyl, substituted or unsubstituted aralkyloxy, substituted or unsubstituted aralkyloxyalkyl, In a specific example of the substituted or unsubstituted arylthio group, preferred examples of the arsenazo compound of the above formula (1) include R ₁ to R ₈ each having such a substituent. The example given is the same.

When Z ₁ to Z ₉ are a substituted or unsubstituted amidino group, an alkyloxycarbonyl group, a substituted or unsubstituted aryloxycarbonyl group, a tetraaza complex with the above formula (1) may be mentioned. The examples of Y ₁ to Y _{11 of} the porphyrin compound are the same as those exemplified for the substituents.

Specific examples of the quinophthalone compound of the formula (3) are shown in Table 3 below, but are not limited to these ranges.

[table 3]

Further, the quinophthalone compound of the formula (3) has a tautomer of the following formula (3'), and these isomers represent the same compound as the formula (3), and also represent the same in the present invention. Effect.

[wherein, Z ₁ to Z ₉ represent the same as Z ₁ to Z _{9 of the} formula (3). ]

The quinophthalone compound of the formula (3) can be produced by a known method.

For example, Japanese Patent Publication No. Sho. No. Sho. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. It is produced by the method described in JP-A-2008-45130.

One of them is produced by subjecting a hydroquinaldine derivative of the following formula (E) to a phthalic anhydride derivative of the following formula (F) by heat condensation reaction.

[wherein, Z ₁ to Z ₉ represent the same as Z ₁ to Z _{9 of the} formula (3). ]

[蒽醌系化合物]

The oxime compound is not particularly limited as long as it has a absorbing property specified in the present invention, but is preferably represented by the following formula (4). compound of.

[In the formula (4), X ₁ to X ₈ each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkyl halide group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, a substituted or unsubstituted group. An aryl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl thio group. However, at least one of X ₁ to X ₈ must be a substituted or unsubstituted arylthio group. ]

Here, preferably, X ₁ to X ₈ are a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, and a substituted or unsubstituted arylthio group is a substituted group. The group may be a halogen atom, an alkyl group, an alkenyl group, a halogenated alkyl group, an alkoxy group or an alkylthio group.

X ₁ to X ₈ in the formula (4) are preferably each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, and an alkyl group having 1 to 12 carbon atoms. An oxy group, an alkylthio group having 1 to 12 carbon atoms, an alkoxyalkyl group having 2 to 16 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms, and X ₁ to X ₈ At least one of them must be a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms.

More preferably, X ₁ to X _{8 are} each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, and an alkyl group having 1 to 8 carbon atoms. a thio group, a substituted or unsubstituted phenylthio group having 6 to 12 carbon atoms, and at least one of X ₁ to X ₈ must be a substituted or unsubstituted arylthio group having 6 to 12 carbon atoms. .

Specific examples of X ₁ to X ₈ will be described below.

X ₁ to X ₈ are a halogen atom, an alkyl group, an alkenyl group, an alkyl halide group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, a substituted or unsubstituted aryl group, substituted or unsubstituted Specific examples of the aralkyl group or the substituted or unsubstituted arylthio group include R ₁ to R ₈ each of which is a tetraazaporphyrin compound of the above formula (1). The same examples are given for the substituents.

Although specific examples of the oxime compound of the formula (4) are shown in Table 4 below, it is not limited to these ranges.

[Table 4]

Although a part of the lanthanoid compound of the formula (4) (Solvent yellow 163, Solvent yellow 167, etc.) can be obtained from the market, it can also be produced by a known method.

One of them is produced by reacting an anthracene derivative having a halogen atom with a benzene sulfide derivative.

[Other organic pigments]

In the resin composition of the present invention, in order to prevent unnecessary light or to adjust the coloring matter, in the range which does not impair the effects of the present invention, other organic dyes may be used in combination.

For example, a porphyrin compound represented by the following formula (5) can be used in combination to block light in the vicinity of 480 to 490 nm.

[wherein, L ₁ to L ₈ each independently represent a halogen atom, a vinyl group or a vinyl group having an alkyl group having 1 to 12 carbon atoms as a substituent, and Q represents a divalent metal atom or an oxidized metal atom. ]

L ₁ to L _{8 are} preferably a bromine atom, a vinyl group having a third butyl group, that is, 3,3-dimethyl-1-butyl group; and Q is preferably Ni, VO or Cu.

Further, a yellow pigment such as KAYA Set Yellow A to G or an orange pigment such as PS Orange GG may be used in combination.

Other organic pigments that can be used in combination are desirably compatible with the resin.

[(A) Resin]

Next, the resin (A) will be described below.

The resin used in the resin composition of the present invention is preferably a thermoplastic resin or a thermosetting resin, or may be an adhesive resin or a transparent resin.

Examples of the thermoplastic resin include polycarbonate resin, polyamide resin, polyester resin, acrylic resin, polyurethane resin, polystyrene resin, acrylonitrile, styrene resin, norbornene resin, cellulose resin, and the like. It is preferably at least one selected from the group consisting of a polycarbonate resin, a polyamide resin, an acrylic resin, and a polyester resin.

The polycarbonate resin is mainly a phosgene method in which a dihydroxydiaryl compound reacts with phosgene or a transesterification reaction in which a dihydroxydiaryl compound and a carbonate such as diphenyl carbonate are reacted. The obtained polymer is a representative resin, and a polycarbonate resin produced from 2,2-bis(4-hydroxyphenyl)propane (bisphenol A) can be cited.

The above dihydroxydiaryl compounds, in addition to bisphenol A In addition, there may be mentioned, for example, 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-hydroxyl 3-tert-butylphenyl)propane, 2,2-bis(4-hydroxy-3-bromophenyl)propane, 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane (hydroxyaryl)alkanes of 2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane; such as 1,1-bis(4-hydroxyphenyl)cyclopentane, 1,1 -(Hydroxyaryl)cycloalkanes of bis(4-hydroxyphenyl)cyclohexane; such as 4,4'-dihydroxydiphenyl ether, 4,4'-dihydroxy-3,3'-dimethyl Dihydroxydiaryl ethers of diphenyl ethers; dihydroxydiaryl sulfides such as 4,4'-dihydroxydiphenyl sulfide; such as 4,4'-dihydroxydiphenylarylene a dihydroxydiarylhydrazone of 4,4'-dihydroxy-3,3'-dimethyldiphenylarylene; such as 4,4'-dihydroxydiphenylanthracene, 4,4'- Dihydroxydiaryl fluorenes of dihydroxy-3,3'-dimethyldiphenyl hydrazine and the like.

These compounds can be used singly or in combination of two or more. In addition to this, piperidine, dipyridinium hydroquinone, resorcin, 4,4'-dihydroxydiphenyl or the like may be used in combination. Further, the polycarbonate resin has a viscosity average molecular weight of usually 10,000 to 100,000, preferably 10,000 to 400,000.

Further, a dihydroxyaryl compound as described above and a trivalent or higher phenol compound as shown below may be used in combination. Examples of the phenol compound having a valence of 3 or more include fluorophlool, 1,3,5-tris-(4-hydroxyphenyl)benzene, and 1,1-tris-(4-hydroxyphenyl)ethane. Wait.

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. The aliphatic group herein also contains an alicyclic aliphatic group. The above resin having a structure of a dehydration polycondensate of a diamine compound and a dicarboxylic acid compound does not limit a tree which must be obtained by a dehydration polycondensation reaction. The fat may be obtained, for example, by ring-opening polymerization of one or two or more kinds of indoleamine compounds.

Examples of the above diamine compound include hexamethylenediamine and m-diamine. Toluene diamine, bis(4-aminocyclohexyl)methane, bis(4-amino-3-methylcyclohexyl)methane, trimethylhexamethylenediamine, bis(aminomethyl)norbornane, double (Aminomethyl) tetrahydrodicyclopentadiene or the like can be used alone or in combination of two or more kinds.

Examples of the above dicarboxylic acid compound include adipic acid, dodecanedicarboxylic acid, isodecanoic acid, phthalic acid, bis(hydroxycarbonylmethyl)norbornane, and bis(hydroxycarbonylmethyl)tetrahydrogen. For the cyclopentadiene or the like, one or two or more kinds of the dicarboxylic acid compounds can be used.

In terms of transparency, a non-crystalline polyamine resin, which is generally referred to as a transparent nylon, may be exemplified by GriLamid TR-55, GriLamid TR-90, GriLamid TR-XE3805 of EMS, or Trogamid of Huls. (transliteration) CX-7323 and so on.

The acrylic resin is a monomer mainly composed of an alkyl methacrylate, and may be a single polymer of an alkyl methacrylate or a copolymer of two or more kinds of alkyl methacrylates, or may be methacrylic acid. A copolymer of 50% by weight or more of the alkyl ester and 50% by weight or less of the monomer other than the alkyl methacrylate. The alkyl methacrylate can usually be used in an alkyl group having a carbon number of from 1 to 4, and among them, methyl methacrylate is preferably used.

Furthermore, monomers other than alkyl methacrylate, although It may be a monofunctional monomer having one polymerizable carbon-carbon double bond in the molecule, or may be a polyfunctional single having two or more polymerizable carbon-carbon double bonds in the molecule. Body, but it is especially preferred to use a monofunctional monomer. As examples thereof, an alkyl acrylate such as methyl acrylate or ethyl acrylate, a styrene monomer such as styrene or alkyl styrene, an unsaturated nitrile such as acrylonitrile or methacrylonitrile, and the like can be given.

In particular, the monomer is preferably a polymer formed substantially only of an alkyl methacrylate, and a representative polymer is a polymethyl methacrylate resin (PMMA).

The polymethyl methacrylate resin is commercially available as MX150, which is commercially available, and Eposter-MA from Japan Catalyst, and MBX series, which is manufactured by Sekisui Chemicals Co., Ltd.

Representative examples of the polyester resin include a homopolyester having a poly C _2-4 alkyl phthalate or a poly C _2-4 alkyl phthalic acid methyl ester, and a C _2-4 alkyl aryl ester. a unit (C _2-4 alkyl phthalic acid methyl ester and/or C _2-4 alkyl phthalic acid methyl ester unit) as a main component of a copolyester or the like, but also contains a polyarylate resin, and An individual or a copolymer of an aliphatic polyester such as an aliphatic dicarboxylic acid such as an acid or a caprolactone such as ε-caprolactam.

Contained in the copolyester constituting units based poly aryl C _2-4 alkyl ester, C _2-4 alkoxy part of poly-diols of C _2-4 alkanediols, polyethylene glycols C _6-10 alkyl , alicyclic diol (cyclohexane diol, hydrogenated bisphenol A, etc.), diol having an aromatic ring (9,9-bis(4-(2-hydroxyethoxy))phenyl group having a fluorenone side chain a copolyester substituted with hydrazine, bisphenol A, bisphenol A-alkylene oxide adduct, etc., a part of the aromatic dicarboxylic acid is asymmetric aromatic such as phthalic acid or isophthalic acid a substituted copolyester such as an aliphatic C _6-12 dicarboxylic acid such as dicarboxylic acid or adipic acid.

The polyester resin is preferably polyethylene terephthalate (PET), polytrimethylene terephthalate (PTT), polybutylene terephthalate (PBT), or the like. Polyethylene naphthalate (PEN) and the like. Further, the amorphous copolyester such as a C _2-4 alkyl arylate-based polyester is also excellent in workability. In particular, PET is preferred because it can be produced in a large amount, excellent in heat resistance, strength, and the like.

Examples of the thermosetting resin include a mixture of an allyl glycol carbonate monomer, a diallyl phthalate monomer, an isocyanate compound, a polyhydric alcohol, a polythiol, and the like, and a corrective lens such as an acrylic monomer. a cured product of a monomer to be used in the production, but preferably a polyurethane resin obtained by polymerization of an isocyanate compound and a polyhydric alcohol, a polythiourethane resin obtained by polymerizing an isocyanate compound and a polythiol, and At least one of a hardened propylene glycol carbonate resin of an allyl glycol carbonate monomer.

The polyurethane resin is a resin containing a block type polyisocyanate and a polyol as a main component, and the block type polyisocyanate may, for example, be hexamethylene diisocyanate, xylene diisocyanate, tetramethyl xylene diisocyanate, 4, 4 '-Dicyclohexylmethane diisocyanate, isodecyl ketone diisocyanate, hydrogenated xylene diisocyanate, each molecular-bonded addition, isocyanurate or allophanate, etc. A polymer of a malonic acid block or the like; and a polyhydric alcohol, a polyester having a hydroxyl group, a polyether, a polycarbonate, a polyacrylate, a polycaprolactone, or the like can be given.

The polythiamine resin is exemplified by a polythiourethane resin produced from p-xylene diisocyanate and pentaerythritol tetrakis(3-mercaptopropionate).

The allyl glycol carbonate resin is preferably polydiethylene glycol bisallyl carbonate, and examples thereof include CR-39 resin (or may be referred to as ADC resin).

Further, among the acrylic resins, the glass transition temperature is low, For example, a polymethyl (meth) acrylate-based resin having a glass transition temperature of less than 0 ° C, preferably -20 ° C or less is used as an adhesive, an adhesive, etc., and can be widely used, for example, in the layers of optical filters for thin displays. , or the optical filter and the display screen.

The poly(methyl) methacrylate-based resin to be used as the adhesive is preferably a resin having 50% by weight or more of a methyl (meth) propylene monomer acid methyl ester having an alkyl group having 1 to 14 carbon atoms as a monomer.

(meth)acrylic acid having an alkyl group having 1 to 14 carbon atoms Examples of the esters include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, and n-octyl (meth)acrylate. Ester, isooctyl (meth)acrylate, benzyl (meth)acrylate, dicyclopentenyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenolic oxy (meth)acrylate Diethylene glycol ester and the like. In particular, when an alkyl acrylate having an alkyl group having 4 to 8 carbon atoms is used, the adhesion and flexibility of the obtained adhesive can be improved.

Examples of other copolymerizable monomers include (meth) Hydroxyethyl acrylate, hydroxypropyl (meth) acrylate, methoxyethyl (meth) acrylate, ethoxyethyl (meth) acrylate, (meth) acrylate, etc. Ethyl ethoxylates; styrene monomers represented by α-methylstyrene, vinyl toluene, styrene, etc.; ethylene represented by methyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, etc. An ether monomer; a fumaric acid, a monoalkyl ester of fumaric acid, a dialkyl ester of fumaric acid; a monoalkyl ester of maleic acid or maleic acid; Dialkyl ester of maleic acid, itaconic acid, monoalkyl ester of itaconic acid, itaconic acid Dialkyl ester, (meth)acrylonitrile, vinyl chloride, vinylidene chloride, vinyl acetate, ketene, vinyl pyridine, vinyl carbazole, and the like.

Further, when a monomer having a carboxyl group or a monomer having a hydroxyl group is copolymerized, crosslinking can be carried out using an isocyanate crosslinking agent or the like. As the curing agent for the acrylic pressure-sensitive adhesive, an isocyanate-based curing agent, an epoxy-based curing agent, a metal chelating curing agent, or the like can be used.

Further, in addition to the acrylic resin, for example, a silicone resin, an amine ester resin, a polyvinyl butyral resin, an ethyl acetate-vinyl acetate resin, a polyvinyl ether, a saturated polyester, or the like may be used. Melamine resin and the like.

[Resin composition]

The resin composition of the present invention is characterized in that it contains at least (A) a resin and (B) an organic dye, and (B) is a tetraazaporphyrin compound (B-1) having the following formula (1) and The compound (B-2) having the absorption property specified in the present invention is obtained.

The amount of the (A) resin and the (B) organic dye in the resin composition of the present invention may vary depending on the use or the thickness of the resin molded body, but it is within the limit of light transmittance and transparency. The concentration may be, and the visible light transmittance in the thickness direction of the molded body is usually 12 to 99%, preferably 20 to 90%. For example, in the spectacle lens having a thickness of 2.15 mm, the amount of the organic dye used is 0.001% by weight to 0.1% by weight based on the polycarbonate resin as long as it can be mixed with the polycarbonate resin. Generally, as long as the thickness of the molded body is from 0.1 mm to 20 mm, the amount of the organic dye used relative to the thermoplastic resin or the thermosetting resin is from 0.0001% by weight to 0.2% by weight. This is the same as when the resin composition is an adhesive.

The ratio of use of the porphyrazine compound (B-1) of the formula (1) to the compound (B-2) having the absorption property specified in the present invention is based on the total amount of the organic dye, and the resin composition In the case of a medical opaque eyeglass or a filter for an LED light source, for example, in the case of a cataract patient, the ratio of the compound (B-2) having the absorption property specified in the present invention is high. However, in order to reduce the coloration of the resin composition, the tetraazaporphyrin compound (B-1): the ratio (weight ratio) of the compound (B-2) having an absorption property specified in the present invention is preferably 90. : 10 to 10:90, more preferably 80:20 to 20:80.

In the resin composition of the present invention, in addition to the resin and the organic dye, other components such as an ultraviolet absorber, an infrared absorber, various resin additives, and the like may be blended as needed. Various resin additives include phenolic antioxidants, release agents, dyes, phosphorus-based heat stabilizers, weathering improvers, antistatic agents, antifogging agents, anti-caking agents, anti-caking agents, flame retardants, and fluids. Sex modifiers, plasticizers, dispersants, antibacterial agents, and the like.

The method for producing the resin composition of the present invention will be described below.

The resin composition of the present invention can be obtained by mixing a resin and an organic dye, and it is desirable to make the resin and the organic dye compatible even in a molded article, an adhesive, an optical article, or an optical lens containing the composition.

When the resin of the resin composition is a thermoplastic resin, a powder or a granular material of the organic dye and the thermoplastic resin is mixed with various mixers such as a tumbler or a Henschel mixer to obtain a resin composition. Banbury mixer, heating roller, Brabender A resin composition in which an organic dye and a thermoplastic resin are uniform can be produced by melt-kneading a well-known melt kneader such as a uniaxial kneading extruder, a two-axis kneading extruder, or a kneading machine.

Further, the thermoplastic resin and the organic dye are dissolved and mixed in a soluble organic solvent, and then removed by an organic solvent. The organic solvent which can be used at this time may, for example, be hexane, heptane, acetone, methyl ethyl ketone, benzene, toluene, dichloromethane, chloroform or the like, but is not chemically reactive with respect to the above resin composition. And a moderately low boiling point, that is, no particular limitation.

Further, after the organic dye is dissolved in a solvent, the organic dye can be produced by being brought into contact with the resin or the resin molded body to diffuse and penetrate the resin, and the obtained resin composition is also within the scope of the present invention. . The organic solvent which can dissolve the organic dye is not particularly limited, but must be a solvent which does not deteriorate the thermoplastic resin. Usually, liquid ketones or alcohols are often used. The concentration of the solution may be any concentration in accordance with the purpose, but is in the range of 0.01% to 30%. Although the conditions of the diffusion may vary depending on the type of the organic dye, the solvent, the thermoplastic resin, etc., it is usually 25 ° C to 200 ° C under normal pressure or pressure for several minutes to 5 hours.

Further, the organic dye may be mixed in the raw material monomer of the thermoplastic resin by the above method, and then polymerized. In the production method, the resin described in the resin composition described below is a thermosetting resin.

When the resin of the resin composition is a thermosetting resin, the organic dye may be dissolved in a resin after being dissolved in a solvent, or the organic dye may be diffused into the resin, or the organic dye may be mixed in the heat. A method of polymerizing a raw material monomer of a curable resin, but a method of using the latter is often used. The latter method will be described below.

a raw material sheet in which an organic pigment is mixed in a thermosetting resin In the step of the body, a method of preparing a monomer mixture, mixing a monomer mixture and other additives by mixing the monomer with the monomer of the monomer group constituting the monomer mixture according to the mixing target of the organic coloring matter After the mixture is formed, a catalyst is added, or a monomer mixture, a catalyst, and other additives are mixed into a mixture.

The monomer used in the polymerization hardening and components other than the organic dye include a polymerization catalyst and other additives.

Examples of the polymerization catalyst include organic peroxides, and examples thereof include compounds such as dimercapto peroxide, peroxydicarbonate, peroxyester, peroxyacetal, dialkyl peroxide, and hydrogen peroxide.

Other additives, such as dibutyltin dichloride a reaction initiator, a chain extender, a crosslinking agent, a filler, etc. of an internal release agent such as a catalyst, an ultraviolet absorber, an acid phosphate, or the like, a photostabilizer, an antioxidant, a radical reaction initiator, and the like, and A well-known resin modifier may be added as needed, and examples thereof include olefins containing a hydroxy compound, a thiol compound, an epoxy compound, an episulfide compound, an organic acid and an acid anhydride thereof, and a (meth) acrylate compound. Compounds, etc.

When the organic dye is mixed with the thermosetting resin raw material monomer, the organic dye may be directly mixed, or the organic dye may be dissolved in a low boiling organic solvent in advance, and the organic solvent solution may be mixed in the raw material monomer. Thereafter, the organic solvent is removed by evaporation under heating and/or reduced pressure. this The organic solvent to be used may, for example, be hexane, heptane, acetone, methyl ethyl ketone, benzene, toluene, dichloromethane, chloroform or the like, but has no chemical reaction activity to the raw material monomer, and is moderately low. The solvent of the boiling point is not particularly limited.

At the time of mixing, it is equivalent to organic pigments deemed necessary The amount of the concentration may be such that the amount of the resin composition contained in the resin composition may be mixed. Further, the masterbatch containing the organic dye may be prepared at a higher concentration than the target concentration in any one of the raw material monomers. Batch), and if necessary, add other ingredients to be blended, and dilute to produce a resin composition of the desired concentration. In addition, when the organic dye is dissolved, it may be heated in a range that does not hinder the implementation from the viewpoints of deterioration of the resin composition or the usable time.

The polymerization hardening conditions in the injection molding method of the molded body described later will be described.

When the resin composition is an adhesive, the method is based on the case where the resin of the molded body is a thermoplastic resin. However, since the resin tends to have fluidity at normal temperature, it is required for the solid resin. Processing varies.

[formed body]

Hereinafter, the molded body 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.

The form of the molded body may be an optical article formed of a resin composition, or an optical article partially containing a resin composition, or an intermediate material produced by an optical article such as a powder or a bead state.

As an embodiment to be described later, the optical article can be exemplified by an eyeglass lens, a sun visor, a mask for a helmet, a cover for an display device or an anti-glare film, and a display assembly. Various optical filters such as optical filters for mounting optical filters or spectacle lenses, anti-glare optical articles such as masks for illumination devices, and optical articles for short-wavelength light are used.

In the present invention, an optical article partially containing a resin composition is an optical article in a state in which it is applied or attached to the surface of each element or film of the optical article or the surface of each layer.

Although the molding method may vary depending on the type of the product or the resin to be used, when a resin composition of a thermoplastic resin is used, for example, a compression molding method, a transfer molding method, an extrusion molding method, an injection molding method, or the like can be used. When forming a resin composition of a thermosetting resin, for example, an injection polymerization method can be used.

The injection polymerization method will be described below.

The resin composition is injected into a mold for injection molding, and is placed therein, and then the mold for injection molding is heated in a heating device such as a furnace or water at a set temperature for several hours to several tens of hours. The temperature and time of the polymerization hardening may vary depending on the composition of the mixture, the type of the catalyst, the shape of the mold, and the like, but it is about 1 to 100 hours at a temperature of -50 to 200 °C. Usually, it starts from a temperature in the range of 5 ° C to 40 ° C, and then slowly rises to a range of 80 ° C to 130 ° C, and is usually heated at this temperature for 1 hour to 4 hours.

After the hardening is completed, the self-injection type mold is taken out, and the desired molded body can be obtained.

[adhesive]

The resin composition of the present invention is also very useful as an adhesive used in optical articles.

The adhesive can be used by bonding a substrate, a transparent support, a functional transparent layer or the like in an optical article, or by bonding a transparent support to any layer formed of an optical article such as a functional transparent layer. And it has the function of following with anti-glare and blocking unnecessary light.

The resin used in the adhesive is as described in the above-mentioned "resin". In addition, the composition ratio of the resin and the organic dye is also as described in the item of the "resin composition".

The adhesive may be in the form of a sheet or a liquid. When a sheet-shaped pressure-sensitive adhesive is used as the pressure-sensitive adhesive, the sheet-like adhesive is applied or after the application of the adhesive, and the pressure is applied to the adhesive. When a liquid adhesive is used as the adhesive, after application and bonding, it is bonded by a ripening treatment at room temperature or under heating or by irradiation with ultraviolet rays.

[Anti-glare optical articles]

The molded article and the adhesive of the resin composition of the present invention are very useful for an optical article for antiglare.

Examples of the optical article for anti-glare include a spectacle lens, a sun visor, a mask for a helmet, a film for an automobile or an airplane windshield, a cover for an automobile headlight, a goggle for skiing, and a display device for an information device having a display device. An anti-glare cover or an anti-glare film, a filter for LED illumination, a film for a building glazing, or the like, but not limited to use for anti-glare, contrast, or purpose for ensuring natural color tone.

The method for producing an optical article for antiglare can vary depending on the form of the article or the type of the resin, and the above-described method for producing a molded article can be applied.

In addition, it can also be equipped with anti-glare optical articles. Any one or more functions of reflective function, hard coating function (abrasion resistance), antistatic function, antifouling function, gas barrier function, and UV resistance function.

[Reduce short wavelength]

The molded article and the adhesive of the resin composition of the present invention are also very useful for reducing optical articles for short wavelengths.

In the optical article for short-wavelength reduction, the above-described form of the anti-glare optical article can be reused. However, even if the eye is not consciously glare, it can be used for the purpose of protecting the eye from the influence of short wavelength.

In particular, it can be applied to items for the purpose of protecting the eyes, such as illumination using LEDs, display devices, signal cameras or headlights, and illumination.

For example, spectacle lenses, sun visors, masks for hard hats, films for automobiles, films for car headlights, anti-glare covers for anti-glare devices, anti-glare films, LED lighting shields, contact lenses (intraocular lenses) )Wait.

[Optical filter]

Examples of the optical article using the molded article and/or the adhesive of the resin composition of the present invention include the above-described optical filter.

The molded article and the adhesive of the resin composition of the present invention have an optical filter function even if it is a monomer. For example, an anti-glare film or the like may have an optical filter depending on the use, and may be applied to a plurality of layers. Optical filter for display assembly, optical filter for eyeglass lens assembly.

A representative article of such an optical filter is formed of a single layer or a plurality of layers of a transparent support, a transparent adhesive layer, a functional transparent layer, or the like. The at least one layer or element of the optical filter contains the porphyrazine compound (B-1) represented by the formula (1) and a compound having the absorption characteristics specified in the present invention. (B-2).

The transparent support may be an inorganic material such as transparent glass or a transparent resin, but in terms of production efficiency, it is preferably a transparent resin, and the thickness of the transparent support is preferably from 10 μm to 10 mm, more preferably from 20 μm to 5 mm.

The functional transparent layer is equipped with an optical filter setting method or required function, and has anti-reflection function, anti-glare function, anti-reflection anti-glare function, hard film coating function (wearing function), anti-static function, anti-proof Any one or more of the dirt function, the gas barrier function, the electromagnetic wave shielding function, the blocking infrared function, the blocking ultraviolet function, the polarizing function, and the coloring function.

The transparent adhesive layer is a layer containing the aforementioned adhesive.

Although an embodiment of such an optical filter is not particularly limited, it can be used particularly as a filter for display assembly or an optical filter for spectacle lens assembly.

The display assembly filter can be embedded in various displays such as a plasma display, a liquid crystal display, an organic electroluminescent display, a FED (Field Emission Display), a CRT (Cathode Ray Tube), or the like. The assembly of the space.

In such a filter for display assembly, a known form, configuration, element, and manufacturing method of the filter for a display can be applied.

Further, the optical filter for attaching the spectacle lens can be attached to the surface or the inner surface of the general-purpose spectacle lens, or can be used in any form such as a filter at a position separated from the lens.

Specifically, for example, the following forms: (a) a film-like filter attached to the surface or the inner surface of the spectacle lens; (b) a film-like filter used in a state of being sandwiched inside the spectacle lens; (c) a filter formed by laminating a resin layer on the spectacle lens; (d) by being on the surface or inside the spectacle lens (a) a tetraazaporphyrin compound (B-1) represented by the formula (1) and a compound having the absorption property specified in the present invention (B) are coated with a resin coating agent to form a coating layer as a coating layer; -2) a filter formed by dissolving the solution in contact with the resin of the spectacle lens or the resin of the spectacle lens to diffuse and penetrate, and (f) setting the space in front of the spectacle lens from the lens. Filter.

[Examples]

The present invention will be more specifically described by the following examples, but the present invention is not limited to the following examples.

[Example 1-1]

1,000 parts by weight of a polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering Plastics Co., Ltd.), and 0.001 to 0.0068 parts by weight of a specific example compound of the porphyrazine compound (B-1), as having the present invention Specific examples of the compound (B-2) having a predetermined absorption characteristic: 0.008 parts by weight of an azo compound of the compound 2-4 (A1/A2=0.03), which was mixed by a rolling machine for 20 minutes, and then set at a drum by a uniaxial extruder. The pellet was pelletized by melting and kneading at 260 ° C and a screw rotation number of 56 rpm.

[Example 1-2]

In addition to the specific example compound 1-11 of the tetraazaporphyrin compound (B-1), 0.0058 parts by weight and as the absorption specified in the present invention The pellets were produced in the same manner as in Example 1-1 except that 0.006 parts by weight of the azo compound of the compound 2-2 (A1/A2 = 0.02) of the compound (B-2).

[Example 1-3]

In addition to 0.0208 parts by weight of the specific compound 1-12 as the tetraazaporphyrin compound (B-1) and the specific compound 2-5 (the compound (B-2) having the absorption property specified in the present invention) The pellets were produced in the same manner as in Example 1-1, except that 0.012 parts by weight of the azo compound of A1/A2 = 0.02).

[Example 1-4]

In addition to the specific example compound 1-18 of the porphyrazine compound (B-1), 0.0065 parts by weight and the specific compound 2-12 (the compound (B-2) having the absorption property specified in the present invention) The same procedure as in Example 1-1 was carried out, except that 0.008 parts by weight of the azo compound of A1/A2 = 0.05), to prepare pellets.

[Example 1-5]

In addition to the specific example compound 1-1-5 used as the tetraazaporphyrin compound (B-1), 0.0104 parts by weight and the specific compound 2-17 (the compound (B-2) having the absorption property specified in the present invention) The pellets were produced in the same manner as in Example 1-1 except that 0.012 parts by weight of the azo compound of A1/A2 = 0.06) was used.

[Example 1-6]

In addition to the specific example compound 1-58 0.0087 parts by weight as the tetraazaporphyrin compound (B-1), and as having the absorption specified in the present invention The pellets were produced in the same manner as in Example 1-1 except that 0.010 parts by weight of the azo compound of the compound 2-20 (A1/A2 = 0.03) of the compound (B-2).

[Examples 1-7]

In addition to the use of the specific example compound 1-60 as a tetraazaporphyrin compound (B-1), 0.0067 parts by weight and the specific compound 2-29 as a compound (B-2) having the absorption property specified in the present invention ( The same procedure as in Example 1-1 was carried out except that 0.008 parts by weight of the azo compound of A1/A2 = 0.04) was used to produce pellets.

[Examples 1-8]

Specific Example Compound 2-13 (Compound Example 1-11, which is a specific compound of the tetraazaporphyrin compound (B-1), is used as the compound (B-2) having the absorption property specified in the present invention. The same operation as in Example 1-1 was carried out except that 0.006 part by weight of the azo compound of A1/A2 = 0.02) and 0.001 part by weight of the quinophthalone compound of the specific example compound 3-21 (A1/A2 = 0.01) were used. Globules.

[Examples 1-9]

1,000 parts by weight of a polyamidamine resin (GriLamid TR90, manufactured by EMS Chem Japan Co., Ltd.), and 0.001,500,525 parts by weight of a specific example compound of the porphyrazine compound (B-1), as defined in the present invention Specific Example Compound Absorbing Compound (B-2) 0.0035 parts by weight of the azo compound of Compound 2-7 (A1/A2=0.04), which was mixed by a rolling machine for 20 minutes, and then set by a uniaxial extruder at a temperature of 260 ° C. Under the condition of a screw rotation number of 56 rpm, it was melted and kneaded to be granulated.

[Example 1-10]

In addition to the specific example compound 1-10 0.0067 parts by weight as the tetraazaporphyrin compound (B-1) and the specific example compound 2-4 as the compound (B-2) having the absorption property specified in the present invention ( The pellets were produced in the same manner as in Example 1-9 except that 0.008 parts by weight of the azo compound of A1/A2 = 0.03) was used.

[Examples 1-11]

1,000 parts by weight of a polymethyl methacrylate resin (80N manufactured by Asahi Kasei Co., Ltd.), and 0.001 to 0.0065 parts by weight of a specific example compound of the porphyrazine compound (B-1), as defined in the present invention Specific Example Compound Absorption Compound (B-2): 0.008 parts by weight of an azo compound of Compound 2-4 (A1/A2=0.03), which was mixed by a rolling machine for 20 minutes, and then set at a temperature of 260 ° C by a uniaxial extruder. Under the condition of a screw rotation number of 56 rpm, it was melted and kneaded to be granulated.

[Examples 1-12]

In addition to the specific example compound 1-13 0.009 parts by weight as the tetraazaporphyrin compound (B-1) and the specific example compound 2-9 (the compound (B-2) having the absorption property specified in the present invention) ( The pellets were produced in the same manner as in Example 1-11 except that 0.009 parts by weight of the azo compound of A1/A2 = 0.05) was used.

[Examples 1-13]

In addition to the specific example compound 1-11 as a tetraazaporphyrin compound (B-1), 0.0045 parts by weight and the specific compound 2-2 as a compound (B-2) having the absorption property specified in the present invention ( A1/A2=0.07) The pellets were produced in the same manner as in Example 1-11 except that 0.0035 parts by weight of the nitrogen compound was used, and 0.001 parts by weight of the following compound (5-1) was used.

[Examples 1-14]

The pellets produced in Example 1-1 were used as a raw material, and were molded into a shape of 150 mm × 300 mm and a thickness of 2 mm under the conditions of a drum setting temperature of 260 ° C, a mold temperature of 80 ° C, and a molding cycle of 60 seconds. The resin composition of the flat plate. When the transmission spectrum of the resin composition was measured, the spectrum shown in Fig. 1 was obtained. This resin composition is almost colorless.

[Examples 1-15]

The same procedure as in Example 1-14 was carried out except that the pellets produced in Example 1-2 were used as a raw material, and formed into a resin composition of a flat plate. When the transmission spectrum of the resin composition was measured, the spectrum shown in Fig. 2 was obtained. This resin composition is almost colorless.

[Examples 1-16]

The same procedure as in Example 1-14 was carried out except that the pellets produced in Examples 1 to 8 were used as a raw material, and formed into a resin composition of a flat plate. When the transmission spectrum of the resin composition was measured, the spectrum shown in Fig. 3 was obtained. This resin composition is almost colorless.

[Examples 1-17]

The same procedure as in Example 1-14 was carried out, except that the pellets produced in Examples 1 to 11 were used as a raw material, and formed into a resin composition of a flat plate. When the transmission spectrum of the resin composition was measured, the spectrum shown in Fig. 4 was obtained. This resin composition is almost colorless.

[Examples 1-18]

The same procedure as in Example 1-14 was carried out except that the pellets produced in Examples 1 to 12 were used as a raw material, and formed into a resin composition of a flat plate. When the transmission spectrum of this resin composition was measured, the spectrum shown in Fig. 5 was obtained. This resin composition is almost colorless.

[Examples 1-19]

The same procedure as in Example 1-14 was carried out except that the pellets produced in Example 1-13 were used as a raw material, and formed into a resin composition of a flat plate. When the transmission spectrum of this resin composition was measured, the spectrum shown in Fig. 6 was obtained. This resin composition is almost colorless.

[Examples 1-20] Manufacture of spectacle lenses

In a 2 L separation flask equipped with a thermometer, a stirrer, and a nitrogen-sealed tube, 1,000 parts by weight of polyoxybutylene glycol (PGT-1000N, manufactured by Hodogaya Chemical Co., Ltd.) having an average molecular weight of 1,014 was added, and heated while stirring in a nitrogen stream. Dehydrated under reduced pressure of 100 to 110 ° C / 3 to 5 mmHg for 1 hour. After the completion of the dehydration, 850 parts by weight of 4,4'-methylene-bis(cyclohexyl isocyanate) (Desmodur W) was added, and the reaction was carried out at 120 to 130 ° C for 2 hours. Prepolymer. The obtained prepolymer was a colorless transparent liquid having an NCO content of 9.9%, a viscosity of 8,600 mPa·s/30 ° C, and a temperature of 750 mPa·s/60 °C.

After heating 1,000 parts by weight of the obtained prepolymer to 70 ° C, a specific example compound 1-10 0.0075 parts by weight as a tetraazaporphyrin compound (B-1) is added and as having the absorption characteristics specified in the present invention. Specific compound 2-4 (A1/A2 = 0.03) of the compound (B-2): 0.005 parts by weight of an azo compound, which was mixed. Next, it was mixed with 314 parts by weight of 4,4'-methylene-bis(2-chlorinated aniline) melted at 120 ° C for de-aerating.

This mixture was poured into a mold which had been preheated at 100 ° C, and heat-hardened at 100 ° C for 24 hours to obtain a lens for spectacles having a lens thickness of about 2.6 mm.

The resulting lens is almost colorless. Furthermore, in the observation of the glasses in which the lenses are assembled, there is little glare even when used for a long time on a sunny day. Moreover, the contrast of the branches of the trees or the contrast of red, yellow and green can be seen at a glance.

[Examples 1-21] Manufacture of spectacle lenses

The pellets produced in Example 1-1 were used as raw materials, melted at 250 ° C, and molded by an injection molding machine using a set metal mold to obtain an outer diameter of 75 mm. Plastic lens with a center thickness of 2mm.

The resulting lens is almost colorless. Furthermore, in the observation of the glasses in which the lenses are assembled, there is little glare even when used for a long time on a sunny day. And, for the twigs of trees, red, yellow, green The comparison can be seen at a glance.

[Examples 1-22] Manufacture of spectacle lenses

Except that the pellets produced in Examples 1 to 11 were used as the raw materials, the same operations as in Example 1-21 were carried out to obtain an outer diameter of 75 mm. Plastic lens with a center thickness of 2mm.

The resulting lens is almost colorless. Furthermore, in the observation of the glasses in which the lenses are assembled, there is little glare even when used for a long time on a sunny day. Moreover, the contrast of the branches of the trees or the contrast of red, yellow and green can be seen at a glance.

[Examples 1-23] Manufacture of spectacle lenses

Except that the pellets produced in Examples 1-8 were used as the raw materials, the same operations as in Example 1-21 were carried out to obtain an outer diameter of 75 mm. Plastic lens with a center thickness of 2mm.

The resulting lens is almost colorless. Furthermore, in the observation of the glasses in which the lenses are assembled, there is little glare even when used for a long time on a sunny day. Moreover, the contrast of the branches of the trees or the contrast of red, yellow and green can be seen at a glance.

[Embodiment 1-24] Manufacturing of a sun visor for automobiles

The flat plate having an outer shape of 150 mm × 300 mm and a thickness of 2 mm manufactured in Example 1-14 was integrally attached to a sun visor body which is generally used in automobiles through a hinge portion of a flexible resin to obtain an anti-glare shade. board.

In the state of hanging the sun visor, it is not very dazzling when observing the opposite car equipped with the light. Furthermore, since the transmitted color is almost colorless, even in the daytime, the blue (green), yellow, and red colors used in the signal. Identification will not be difficult. Furthermore, even with this anti-glare sun visor, the light transmittance is not so lowered.

[Embodiment 1-25] Manufacturing of a mask for a helmet

The flat plate having a shape of 150 mm × 300 mm and a thickness of 2 mm manufactured in Example 1-17 was cut into a shape of a helmet cap of a locomotive, and placed in a heating furnace and heated to 160 ° C. The heated flat plate was placed in a molding die to prepare a spherical molded product having a radius of curvature of about 120 mm, and after cooling, it was taken out from the forming die to obtain a mask for a helmet.

This mask is attached to the helmet, and when it is used during the day and night, it is rarely dazzled during traveling on a clear day, and the transmittance of the light is reduced even during nighttime driving. Furthermore, blue (green), yellow, and red can be clearly identified.

[Examples 1-26] Fabrication of Optical Filters

100 parts by weight of polymethyl methacrylate resin (manufactured by Asahi Kasei Co., Ltd.: 80N) was dissolved in 300 parts by weight of methyl ethyl ketone, and specific examples of the compound of the tetraazaporphyrin compound (B-1) were 1-11 0.09. 0.045 parts by weight of the azo compound of the specific example compound 2-4 (A1/A2=0.03) which is a compound (B-2) having the absorption property specified in the present invention, as a coating liquid. This coating liquid was applied on the surface of polyethylene terephthalate (PET) having a thickness of about 200 μm with a Meyer rod, and the film thickness after drying was 10 μm, and dried.

The PET plate with the anti-glare cover is placed on the display screen of the personal computer for the LED backlight, and is used as an optical filter for the display device. Observe the picture under various conditions such as text display, image display, and animation display As a result, not only the glare and the glare are lowered before the setting, but also the fatigue of the eyes is reduced, the contrast of the image is improved, and the outline is clearly seen, and the color tone is not changed.

[Example 1-27] Fabrication of Optical Filters

1,000 parts by weight of a polymethyl methacrylate resin (manufactured by Asahi Kasei Co., Ltd.: 80N), and 0.077 parts by weight of a specific example compound 1-11 as a tetraazaporphyrin compound (B-1), and having the absorption specified in the present invention Specific compound (B-2): 0.055 parts by weight of an azo compound of compound 2-4 (A1/A2=0.03), which was mixed by a rolling machine for 20 minutes, and then set at a temperature of 260 ° C by a uniaxial extruder at a drum. Under the condition of a screw rotation number of 56 rpm, it was melted and kneaded to be pelletized.

The pellets were mixed and extruded in a two-axis extruder to obtain a film (plate) having a thickness of about 200 μm. The temperature in the extruding zone and the melting line is at most 275 ° C, and the temperature of the cooling axis is 30 ° C.

The obtained film was cut out as an optical film of a display device, and attached to the surface of a portable data device (Smartphone) using an acrylic adhesive. The results of observing the display surface under various conditions such as text display and image display not only reduce the glare and glare before the attachment, but also reduce the fatigue of the eyes. The contrast of the image is improved and the outline is clearly seen. Variety.

[Example 1-28] Fabrication of Optical Filters

1-10 0.008 parts by weight of a specific example compound of the tetraazaporphyrin compound (B-1) and a specific example compound 2-4 (A1) as the compound (B-2) having the absorption property specified in the present invention. /A2=0.03) 0.012 parts by weight of the compound was dissolved in 80 parts by weight of methyl ethyl ketone.

30 parts by weight of an acrylic pressure-sensitive adhesive PX4-IR-PT-076 (manufactured by Nippon Shokubai Co., Ltd., solid content: 37.5%) and an isocyanate-based curing agent (L-55E manufactured by Nippon Polyurethane Co., Ltd.) were added in an amount of 0.057 parts by weight. 0.0057 parts by weight of a hardening accelerator (dibutyltin dilaurate manufactured by Tokyo Chemical Industry Co., Ltd.) was stirred at a homogenizer at 10,000 rpm for 10 minutes to obtain an adhesive composition having a solid content concentration of about 10%.

The adhesive composition was applied onto a polyethylene terephthalate (PET) film (manufactured by Teijin DuPont Film Co., Ltd., thickness: 75 μm) by a bar coater, and the film thickness after drying was 25 μm. It was dried at 90 ° C for 2 minutes. The release film on which the hafnium release layer was formed was bonded to the coated surface to prepare an optical filter. This optical filter is colorless. The transmission spectrum of this optical filter is shown in Fig. 7.

This optical filter was attached to a front side of a liquid crystal television (AQUOSLC-16K5 manufactured by Sharp Co., Ltd.) using a white LED as a backlight unit, and used as an optical filter for a liquid crystal display device. Observing the result of the TV screen through the optical filter, the contrast of the image is improved, the outline is clearly seen, and the color tone is not changed. Furthermore, when compared with before attaching an optical filter, the degree of eye fatigue and blurring during long-term appreciation is greatly reduced.

Further, the optical filter manufactured as described above was attached to the outside of a colorless spectacle lens having a center thickness of about 2 mm made of a polythiline resin to form an optical filter for an eyeglass lens. As a result of the use of the lens in which the lens is mounted, the inside and outside of the house are used, and there is little glare in the long-term use under the LED lighting indoors or outdoors. And, for the line of twigs of trees The contrast of bars or red, yellow and green can be seen at a glance.

[Example 1-29] Fabrication of Optical Filters

In addition to the specific example compound 1-11 of the tetraazaporphyrin compound (B-1), 0.0058 parts by weight and the specific compound 2-2 (the compound (B-2) having the absorption property specified in the present invention) ( An optical filter was produced in the same manner as in Example 1-28 except that 0.006 part by weight of the azo compound of A1/A2 = 0.02) was used. The resulting optical filter is colorless.

Except that this optical filter was used, the same operation as in Example 1-28 was carried out, and an optical filter was attached to the front surface of the liquid crystal television to form an optical filter for a display device. The same effect as in Example 1-28 was obtained as a result of observing the screen of the display through the optical filter.

[Example 1-30] Fabrication of Optical Filters

In addition to 0.01 parts by weight of the specific compound 1-12 as the tetraazaporphyrin compound (B-1) and the specific example compound 2-5 (the compound (B-2) having the absorption property specified in the present invention) An optical filter was produced in the same manner as in Example 1-28 except that 0.012 parts by weight of the azo compound of A1/A2 = 0.02). The resulting optical filter is colorless.

This optical filter is attached to the outside of the liquid crystal display surface of the smart phone terminal (iPhone 3GS 16GB SoftBank) to form an optical filter for the display device. As a result of observing the screen of the display through the optical filter, the contrast of the image or the text is improved, the outline is clearly seen, and the color tone is not changed. Furthermore, the degree of eye fatigue and blurring during long-term use is greatly reduced as compared with before the attachment of the optical filter.

[Example 1-31] Fabrication of Optical Filters

In addition to the specific example compound 1-11 of the tetraazaporphyrin compound (B-1), 0.007 parts by weight, as a specific example compound 2-13 (the compound (B-2) having the absorption property specified in the present invention) ( The same operation as in Example 1-28 was carried out, except that 0.007 part by weight of the azo compound of A1/A2 = 0.02) and 0.002 part by weight of the quinophthalone compound of the specific example compound 3-21 (A1/A2 = 0.01), Make an optical filter. The transmission spectrum of this optical filter is shown in Fig. 8.

Using this optical filter, the same operation as in Example 1-28 was carried out, and an optical filter was attached to the front surface of the liquid crystal television to form an optical filter for a display device. The same effect as in Example 1-28 was obtained as a result of observing the screen of the display through an optical filter.

[Examples 1-32] Fabrication of Optical Filters

In addition to the specific example compound 1-18 as a tetraazaporphyrin compound (B-1), 0.007 parts by weight and a specific example compound 2-12 as a compound (B-2) having an absorption property specified in the present invention ( An optical filter was produced in the same manner as in Example 1-28 except that 0.01 parts by weight of the azo compound of A1/A2 = 0.05) was used. The resulting optical filter is colorless.

[Examples 1-33] Fabrication of Optical Filters

1,000 parts by weight of a polymethyl methacrylate resin (manufactured by Asahi Kasei Co., Ltd.: 80N), and a specific example compound of the porphyrazine compound (B-1), from 1 to 10 parts by weight, and having the absorption specified in the present invention Specific compound (B-2): 0.01 parts by weight of an azo compound of compound 2-4 (A1/A2=0.03), which was mixed by a rolling machine for 20 minutes, and then set at a temperature of 260 ° C by a uniaxial extruder at a drum. Melting, screw rotation number of 56 rpm Mix and granulate.

The pellets were mixed and extruded in a two-axis extruder to obtain a film (plate) having a thickness of about 200 μm. The temperature in the extruding zone and the melting line was at most 275 ° C, and the temperature of the chill roll was 30 ° C. Then, the film was extended in the two-axis direction to prepare a film having a thickness of 100 μm.

On the other hand, 80 parts by weight of methyl ethyl ketone and 30 parts by weight of an acrylic pressure-sensitive adhesive PX4-IR-PT-076 (manufactured by Nippon Shokubai Co., Ltd., solid content: 37.5%) and an isocyanate-based curing agent (manufactured by Nippon Polyurethane Co., Ltd.) L-55E) 0.057 parts by weight, a hardening accelerator (dibutyltin dilaurate, manufactured by Tokyo Chemical Industry Co., Ltd.), 0.0057 parts by weight, and stirred at a homogenizer at 10,000 rpm for 10 minutes to obtain an adhesive composition having a solid content concentration of about 10%.

This adhesive composition was applied onto a polymethyl methacrylate film containing the specific example compound 1-11 as the (B) organic dye and the specific compound 2-4 by a bar coater, and dried. The film thickness was 25 μm and it was dried. The release film on which the hafnium release layer was formed was bonded to the coated surface to prepare an optical filter. This optical filter is colorless. The transmission spectrum of this optical filter is as shown in Fig. 9.

[Example 1-34] Fabrication of Optical Filters

In addition to the specific example compound 1-13 0.009 parts by weight as the tetraazaporphyrin compound (B-1) and the specific example compound 2-9 (the compound (B-2) having the absorption property specified in the present invention) ( An optical filter was produced in the same manner as in Example 1-33 except that 0.009 parts by weight of the azo compound of A1/A2 = 0.05). The resulting optical filter is colorless.

This optical filter was attached to the same polysulfide ester as in Examples 1-28. The outer surface of the colorless spectacle lens having a center thickness of about 2 mm was made into a spectacle lens optical filter.

The same effect as in Example 1-28 was obtained as a result of the use of the lens in which the lens was assembled and carried out in and out of the house.

[Examples 1-35] Fabrication of Optical Filters

In addition to the specific example compound 1-11 as a tetraazaporphyrin compound (B-1), 0.0045 parts by weight and the specific compound 2-2 as a compound (B-2) having the absorption property specified in the present invention ( The optical filter was prepared by the same operation as in Example 1-33 except that 0.0035 parts by weight of the azo compound of A1/A2 = 0.07) was used, and 0.001 parts by weight of the above compound (5-1) was used. The resulting optical filter is colorless.

This optical filter was attached to the outside of the liquid crystal display surface of the smart phone terminal (iPhone 3GS 16GB SoftBank) in the same manner as in Example 1-30 to form an optical filter for a display device. The same effect as in Example 1-30 was obtained as a result of observing the screen of the display through the optical filter.

[Examples 1-36] Fabrication of Optical Filters

1,000 parts by weight of a polymethyl methacrylate resin (manufactured by Asahi Kasei Co., Ltd.: 80N), and 1 to 13 0.009 parts by weight of a specific example compound of the porphyrazine compound (B-1), and having the absorption specified in the present invention Specific Example Compound (B-2), Compound 9-2 (A1/A2 = 0.05) of azo compound, 0.009 parts by weight, was mixed by a rolling machine for 20 minutes, and then set to a temperature of 260 ° C by a uniaxial extruder at a drum. Under the condition of a screw rotation number of 56 rpm, it was melted and kneaded to be pelletized.

The pellets are mixed and extruded in a two-axis extruder to obtain a thickness of approximately 200 μm film (plate). The temperature in the extruding zone and the melting line was at most 275 ° C, and the temperature of the chill roll was 30 ° C. Then, the film was extended in the two-axis direction to prepare a film having a thickness of 100 μm.

On the other hand, 80 parts by weight of methyl ethyl ketone and 30 parts by weight of an acrylic pressure-sensitive adhesive PX4-IR-PT-076 (manufactured by Nippon Shokubai Co., Ltd., solid content: 37.5%) and an isocyanate-based curing agent (manufactured by Nippon Polyurethane Co., Ltd.) L-55E) 0.057 parts by weight, a hardening accelerator (dibutyltin dilaurate, manufactured by Tokyo Chemical Industry Co., Ltd.), 0.0057 parts by weight, and stirred at a homogenizer at 10,000 rpm for 10 minutes to obtain an adhesive composition having a solid content concentration of about 10%.

This adhesive composition was applied onto a polymethyl methacrylate film containing the specific example compound 1-13 as the (B) organic dye and the specific example compound 2-9 by a bar coater, and dried. The film thickness was 25 μm and it was dried. The release film on which the hafnium release layer has been formed is bonded to the coated surface. Next, the adhesive composition was applied and dried on the inner surface of the obtained film by the same operation, and the release film was bonded to the coated surface.

The release film on the other side of the obtained film was peeled off and bonded to a polycarbonate hard coat film (Iupilon Sheet MR58 manufactured by MGC Filsheet, thickness: 0.5 mm) to prepare an optical filter to which a hard coat film was attached. The resulting optical filter is colorless.

The optical filter was attached to the liquid crystal display surface of the portable navigator device (Sanyo Electric Mechanism NV-LB51DT) to form an optical filter for the display device. Through the optical filter, the result of the display screen is observed, and the contrast of the image or the text is improved, the outline is clearly seen, and the color tone is not changed. Furthermore, when compared with before attaching the optical filter, when used for a long time The degree of eye fatigue and blurring is greatly reduced.

[Example 1-37] Fabrication of Optical Filters

Specific examples of the compound of the tetraazaporphyrin compound (B-1): 0.0067 parts by weight and the specific compound 2-29 (A1) which is the compound (B-2) having the absorption property specified in the present invention. 0.008 parts by weight of the azo compound of /A2 = 0.04 was dissolved in 80 parts by weight of methyl ethyl ketone. In this solution, 30 parts by weight of an acrylic adhesive PX4-IR-PT-076 (37.5% of a solid content of a Japanese catalyst), 0.057 parts by weight of an isocyanate-based curing agent (L-55E manufactured by Nippon Polyurethane Co., Ltd.), and hardening were added. 0.0057 parts by weight of an accelerator (dibutyltin dilaurate manufactured by Tokyo Chemical Industry Co., Ltd.) was stirred at a homogenizer at 10,000 rpm for 10 minutes to obtain an adhesive composition having a solid content concentration of about 10%.

The adhesive composition was applied to a polyethylene terephthalate (PET) film (manufactured by Teijin DuPont Film Co., Ltd., thickness: 75 μm) by a bar coater, and the film thickness after drying was 25 μm. It is dry. The release film on which the hafnium release layer has been formed is bonded to the coated surface.

On the other hand, the same operation as above was carried out except that the specific example compound 1-60 which is the organic dye (B) and the specific example compound 2-29 were not contained, and the adhesive composition containing no (B) organic pigment was obtained. Things. The adhesive composition was applied onto the other side of the polyethylene terephthalate film (the surface on which the dye-adhesive layer was not formed) by a bar coater, and the dried film thickness was 25 μm, and dried. . The release film having formed the hafnium release layer is bonded to the coated surface.

The obtained film is peeled off from the release film of the adhesive composition of the (B) organic dye, and is bonded to a polycarbonate hard coat film (MGC Filsheet) An Iupilon Sheet MR58 (0.5 mm thick) was fabricated as an optical filter to which a hard coating film was attached. The resulting optical filter is colorless. The mode structure diagram of this optical filter is as shown in Figure 10.

[Comparative Example 1-1] Production of spectacle lenses

1,000 parts by weight of a polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering Plastics Co., Ltd.) and 0.005 parts by weight of an azo compound of a specific example compound 2-4 (A1/A2=0.03) were mixed for 20 minutes in a rolling machine. The uniaxial extruder was spheroidized by melting and kneading under the conditions of a drum setting temperature of 260 ° C and a screw rotation number of 56 rpm.

Using the pellet as a raw material, an eyeglass lens was obtained in the same manner as in Example 1-21. The resulting lens has a yellow hue. Further, when the glasses are attached to the lens, the glare is less than that when the glasses are not used, but the glare is felt under certain conditions such as the sun in the daytime. Although the contrast of the blue (green), yellow, and red of the signal can be clearly confirmed, the hue changes.

[Comparative Example 1-2] Production of spectacle lenses

1,000 parts by weight of a polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering Plastics Co., Ltd.) and 0.005 parts by weight of a specific example compound 1-11 as a tetraazaporphyrin compound (B-1) were mixed by a rolling machine. After a minute, the uniaxial extruder was spheroidized by melting and kneading under the conditions of a drum setting temperature of 260 ° C and a screw rotation number of 56 rpm.

Using the pellet as a raw material, an eyeglass lens was obtained in the same manner as in Example 1-21. The resulting lens has a blue color. Furthermore, by observing the glasses equipped with this lens, although the eye is glare in the daytime sun, it is better than not using the eye. There are still few mirrors, but there is a glare in the light of a specific object such as an LED lamp or a display device, and the eyes feel tired. Although the contrast of the blue (green), yellow, and red of the signal can be clearly confirmed, the hue changes.

[Comparative Example 1-3] Fabrication of Optical Filters

0.02 parts by weight of a specific example compound 1-10 as a tetraazaporphyrin compound (B-1) was dissolved in 80 parts by weight of methyl ethyl ketone.

30 parts by weight of an acrylic pressure-sensitive adhesive PX4-IR-PT-076 (manufactured by Nippon Shokubai Co., Ltd., solid content: 37.5%) and an isocyanate-based curing agent (L-55E manufactured by Nippon Polyurethane Co., Ltd.) were added in an amount of 0.057 parts by weight. 0.0057 parts by weight of a hardening accelerator (dibutyltin dilaurate manufactured by Tokyo Chemical Industry Co., Ltd.) was stirred at a homogenizer at 10,000 rpm for 10 minutes to obtain an adhesive composition having a solid content concentration of about 10%.

The adhesive composition was applied to a polyethylene terephthalate film (manufactured by Teijin DuPont Film Co., Ltd., thickness: 75 μm) by a bar coater, and the film thickness after drying was 25 μm, and the film was dried at 90 ° C. Dry for 2 minutes. The release film on which the hafnium release layer was formed was bonded to the coated surface to prepare an optical filter. The resulting optical filter has a blue hue.

Next, this optical filter was attached to the front surface of a liquid crystal television (AQUOSLC-16K5 manufactured by Sharp Co., Ltd.) using a white LED in the backlight unit.

As a result of observing the television screen through the optical filter, although the glare is reduced as compared with the case where the optical filter is not used, the color reproducibility of the image is good, but the eyes are fatigued and the feeling is blurred during long-term appreciation.

Furthermore, the optical filter obtained above was attached to the outside of a colorless spectacle lens having a center thickness of about 2 mm made of polythiamine ester to form an attached optical lens. Spectacle lens for the filter.

As a result of the use of the lens in which the lens is attached and used inside and outside the house, although the glare is reduced compared to when the glasses are not used, there is a glare in the light of a specific object such as an LED lamp or a display device. Although the contrast of the blue (green), yellow, and red of the signal can be clearly confirmed, the hue changes.

[Comparative Example 1-4] Fabrication of Optical Filters

In addition to 0.02 parts by weight of the azo compound of the specific example compound 2-4 (A1/A2=0.03), 0.02 parts by weight of the specific example compound 1-10, which is a tetraazaporphyrin compound (B-1), is substituted. The rest was subjected to the same operation as in Comparative Example 1-3 to prepare an optical filter. The resulting optical filter has a yellow hue. Next, this optical filter was attached to the front surface of a liquid crystal television (AQUOSLC-16K5 manufactured by Sharp Co., Ltd.) using a white LED in the backlight unit.

As a result of observing the screen of the display through the optical filter, the glare and the feeling of fatigue of the eyes are reduced as compared with the case where the optical filter is not used, but the brightness of the bright image is high, and the glare is felt in a specific case. Furthermore, although the contrast of the images can be clearly confirmed, the hue changes.

Further, the optical filter obtained above was attached to the outside of a colorless spectacle lens having a center thickness of about 2 mm made of polythiamine ester to prepare an eyeglass lens with an optical filter.

As a result of the use of the lens in which the lens is mounted, the inside and the outside of the house are used, although the glare is reduced compared to when the glasses are not used, the glare is felt under certain conditions such as the sun in the daytime. Although the contrast of the blue (green), yellow, and red of the signal can be clearly confirmed, the hue changes. In addition, a substance such as paper which is originally white is regarded as yellow.

[Example 2-1]

1,000 parts by weight of a polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering Plastics Co., Ltd.), and 0.001 to 0.0055 parts by weight of a specific example compound of the porphyrazine compound (B-1), as in the present invention Specific compound of the compound (B-2) having a predetermined absorption property: 0.0035 parts by weight of a quinophthalone compound of 3-21 (A1/A2 = 0.01), which was mixed by a rolling machine for 20 minutes, and then set by a uniaxial extruder with a roller. The pellet was granulated by melting and kneading under the conditions of a temperature of 260 ° C and a screw rotation number of 56 rpm.

[Example 2-2]

In addition to the specific example compound 1-33 of the porphyrazine compound (B-1), 0.0055 parts by weight and the specific compound 3-40 (the compound (B-2) having the absorption property specified in the present invention) The same procedure as in Example 2-1 was carried out, except that 0.0045 parts by weight of the quinophthalone compound of A1/A2 = 0.02), to prepare pellets.

[Example 2-3]

In addition to 0.0060 parts by weight of the specific compound 1-12 as the tetraazaporphyrin compound (B-1) and the specific compound 3-24 (the compound (B-2) having the absorption property specified in the present invention) The same procedure as in Example 2-1 was carried out except that 0.0040 parts by weight of the quinophthalone compound of A1/A2 = 0.03) was used to produce pellets.

[Example 2-4]

In addition to the specific example compound 1-18 of the porphyrazine compound (B-1), 0.0066 parts by weight and the specific compound 3-10 (the compound (B-2) having the absorption property specified in the present invention) A1/A2=0.02) quinquin The pellets were produced in the same manner as in Example 2-1 except that the fluorenone compound was 0.0033 parts by weight.

[Example 2-5]

In addition to the specific example compound 1-53 used as the tetraazaporphyrin compound (B-1), 0.0075 parts by weight and the specific compound 3-28 as the compound (B-2) having the absorption property specified in the present invention ( The pellets were produced in the same manner as in Example 2-1 except that 0.0025 parts by weight of the quinophthalone compound of A1/A2 = 0.04) was used.

[Example 2-6]

In addition to the specific example compound 1-46 0.008 parts by weight as the tetraazaporphyrin compound (B-1) and the specific example compound 3-1 (the compound (B-2) having the absorption property specified in the present invention) The pellets were produced in the same manner as in Example 2-1 except that 0.001 part by weight of the quinophthalone compound of A1/A2 = 0.05) was used.

[Examples 2-7]

In addition to the specific example compound 1-57 0.0055 parts by weight as the tetraazaporphyrin compound (B-1) and the specific compound 3-3-4 (the compound (B-2) having the absorption property specified in the present invention ( The pellets were produced in the same manner as in Example 2-1 except that 0.0045 parts by weight of the quinophthalone compound of A1/A2 = 0.04) was used.

[Example 2-8]

In addition to the specific example compound 1-11 of the tetraazaporphyrin compound (B-1), 0.0065 parts by weight and the specific compound 3-21 which is the compound (B-2) having the absorption property specified in the present invention ( A1/A2=0.01) quinolin The pellet was produced in the same manner as in Example 2-1 except that the oxime compound was used in an amount of 0.0035 parts by weight, and 0.001 parts by weight of the above compound (5-1) was used.

[Embodiment 2-9]

1,000 parts by weight of a polyamidamine resin (Grilamid TR90, manufactured by EMS Chem Japan Co., Ltd.), and 0.00525 parts by weight of a specific example compound of the porphyrazine compound (B-1), as defined in the present invention Specific Example Compound 3-2 (A1/A2 = 0.01) of the quinone ketone compound having an absorption property of 0.0035 parts by weight, mixed by a rolling machine for 20 minutes, and then set to a temperature of 260 by a uniaxial extruder. Under the conditions of °C and screw rotation number of 56 rpm, it was melted and kneaded to pelletize it.

[Example 2-10]

1,000 parts by weight of polymethyl methacrylate (manufactured by Asahi Kasei Co., Ltd.: 80N), and 0.0045 parts by weight of a specific example compound 1-11 of the porphyrazine compound (B-1), as having the absorption specified in the present invention Specific Example Compound (B-2) Compound 0.0021 (A1/A2=0.01) quinacridone compound 0.0035 parts by weight, mixed in a rolling machine for 20 minutes, and then set at a drum temperature of 260 ° C using a uniaxial extruder. Under the condition of a screw rotation number of 56 rpm, it was melted and kneaded to be pelletized.

[Embodiment 2-11]

In addition to the specific example compound 1-13 0.0053 parts by weight of the tetraazaporphyrin compound (B-1), the specific compound 3-21 (the compound (B-2) having the absorption property specified in the present invention) Except for 0.0035 parts by weight of the quinophthalone compound of A1/A2=0.01), the others were carried out with Examples 2-10. The same operation produces pellets.

[Example 2-12]

The pellets produced in Example 2-1 were used as a raw material, and were formed into a flat plate having an outer shape of 150 mm × 300 mm and a thickness of 2 mm under the conditions of a drum temperature of 260 ° C, a mold temperature of 80 ° C, and a molding cycle of 60 seconds. The resin composition. When the transmission spectrum of this resin composition was measured, the spectrum shown in Fig. 11 was obtained. This resin composition is almost colorless.

[Example 2-13]

The same procedure as in Example 2-12 was carried out except that the pellets produced in Example 2-8 were used as a raw material, and the resin composition was formed into a flat plate. When the transmission spectrum of this resin composition was measured, the spectrum shown in Fig. 12 was obtained. This resin composition is almost colorless.

[Examples 2-14]

The same procedure as in Example 2-12 was carried out except that the pellets produced in Examples 2 to 10 were used as a raw material, and the resin composition was formed into a flat plate. When the transmission spectrum of this resin composition was measured, the spectrum shown in Fig. 13 was obtained. This resin composition is almost colorless.

[Embodiment 2-15]

The same procedure as in Example 2-12 was carried out except that the pellets produced in Examples 2 to 11 were used as a raw material, and the resin composition was formed into a flat plate. When the transmission spectrum of this resin composition was measured, the spectrum shown in Fig. 14 was obtained. This resin composition is almost colorless.

[Example 2-16] Manufacturing of spectacle lenses

2L split burner with thermometer, mixer, nitrogen sealed tube To the bottle, 1,000 parts by weight of polyoxybutylene glycol (PGT-1000N, manufactured by Hodogaya Chemical Co., Ltd.) having an average molecular weight of 1,014 was added, and while being stirred while stirring in a nitrogen stream, the pressure was reduced at 100 to 110 ° C / 3 to 5 mmHg. Dehydrated for 1 hour. After the completion of the dehydration, 850 parts by weight of 4,4'-methylene-bis(cyclohexyl isocyanate) (Desmodur W) was added, and the reaction was carried out at 120 to 130 ° C for 2 hours. Prepolymer. The obtained prepolymer was a colorless transparent liquid having an NCO content of 9.9%, a viscosity of 8600 mPa ‧ s / 30 ° C, and 750 mPa ‧ / 60 ° C.

After heating 1,000 parts by weight of the obtained prepolymer to 70 ° C, a specific example compound 1-10 0.0075 parts by weight as a tetraazaporphyrin compound (B-1) is added and as having the absorption characteristics specified in the present invention. Specific compound (B-2): 0.005 parts by weight of a quinophthalone compound of Compound 3-21 (A1/A2 = 0.01), which was mixed. Subsequently, it was degassed and mixed with 314 parts by weight of 4,4'-methylene-bis(2-chlorinated aniline) melted at 120 °C.

This mixture was poured into a model preheated at 100 ° C, and heat-hardened at 100 ° C for 24 hours to obtain a lens for spectacles having a lens thickness of about 2.6 mm.

The resulting lens is almost colorless. Furthermore, through the observation of the glasses in which the lenses are assembled, there is little glare even when used for a long time on a sunny day. Moreover, the contrast of the branches of the trees or the contrast of red, yellow and green can be seen at a glance.

[Example 2-17] Manufacture of spectacle lenses

The pellets produced in Example 2-1 were used as raw materials, melted at 250 ° C, and molded by an injection molding machine using a set metal mold to obtain an outer diameter of 75 mm. Plastic lens with a center thickness of 2mm.

The resulting lens is almost colorless. Furthermore, through the observation of the glasses in which the lenses are assembled, there is little glare even when used for a long time on a sunny day. Moreover, the contrast of the branches of the trees or the contrast of red, yellow and green can be seen at a glance.

[Example 2-18] Manufacture of spectacle lenses

Except that the pellets produced in Examples 2-9 were used as the raw materials, the same operations as in Examples 2-17 were carried out to obtain an outer diameter of 75 mm. Plastic lens with a center thickness of 2mm.

The resulting lens is almost colorless. Furthermore, through the observation of the glasses in which the lenses are assembled, there is little glare even when used for a long time on a sunny day. Moreover, the contrast of the branches of the trees or the contrast of red, yellow and green can be seen at a glance.

[Embodiment 2-19] Manufacturing of a sun visor for automobiles

The flat plate having an outer shape of 150 mm × 300 mm and a thickness of 2 mm manufactured in Example 2-12 is integrally attached to a sun visor body which is generally used in automobiles through a hinge portion of a flexible resin, and is provided with an anti-glare shade. board.

When the sun visor is hung, it is not glaring when observing the opposite vehicle with the light on. Furthermore, since the transmitted color tone is almost colorless, it is not difficult to recognize the blue (green), yellow, and red colors used in the signal even during the day. Furthermore, even if this anti-glare sun visor is used, the light transmittance is not greatly reduced.

[Embodiment 2-20] Manufacturing of a mask for a helmet

The flat plate of the outer shape 150mm×300mm and the thickness of 2mm manufactured in the embodiment 2-13 is cut into the shape of the helmet cap of the locomotive and placed in the heating furnace. Heat to 160 ° C. The heated flat plate was placed in a molding die to prepare a spherical molded product having a radius of curvature of about 120 mm, and after cooling, it was taken out from the forming die to obtain a mask for a helmet.

Attaching this mask to the helmet and using it during daytime and nighttime results in little glare during driving on a clear day, and the transparency of the light is greatly reduced even during nighttime driving. Furthermore, blue (green), yellow, and red can be clearly identified.

[Example 2-21] Manufacture of optical filter

In 3,000 parts by weight of methyl ethyl ketone, 1,000 parts by weight of polymethyl methacrylate resin (manufactured by Asahi Kasei Co., Ltd.: 80 N) was dissolved, and specific compound 1-11 0.009 as a tetraazaporphyrin compound (B-1) was dissolved. 0.0045 parts by weight of a quinophthalone compound which is a specific example compound 3-21 (A1/A2 = 0.01) which is a compound (B-2) having an absorption property specified in the present invention, is used as a coating liquid. This coating liquid was applied on the surface of polyethylene terephthalate (PET) having a thickness of about 200 μm with a Meyer rod, and the film thickness after drying was 10 μm, and dried.

The PET plate with the anti-glare cover is placed on the display screen of the personal computer for LED backlighting, and the screens under various conditions such as text display, video display, and animation display are observed. As a result, not only glare and glare are reduced before the setting, but also the fatigue of the eyes is reduced, the contrast of the images is improved and the outline is clearly seen, and the color tone is not changed.

[Example 2-22] Manufacture of optical filter

1,000 parts by weight of a polymethyl methacrylate resin (manufactured by Asahi Kasei Co., Ltd.: 80N), and a specific example compound 1-11 as a tetraazaporphyrin compound (B-1) 0.0077 parts by weight and 0.0055 parts by weight of a quinophthalone compound as a specific example compound 3-24 (A1/A2=0.03) having the absorption property specified in the present invention, after mixing for 20 minutes in a rolling machine The pellet was granulated by melting and kneading with a uniaxial extruder under the conditions of a drum setting temperature of 260 ° C and a screw rotation number of 56 rpm.

The pellets were mixed and extruded in a two-axis extruder to obtain a film (plate) having a thickness of about 200 μm. The temperature in the extruding zone and the melting line was at most 275 ° C, and the temperature of the chill roll was 30 ° C.

The obtained film was cut and attached to the surface of a portable data machine using an acrylic adhesive. The results of observing the display surface under various conditions such as text display and image display not only reduce the glare and glare before the attachment, but also reduce the fatigue of the eyes. The contrast of the image is improved and the outline is clearly seen. On the other hand, the color tone does not change. .

[Example 2-23] Fabrication of Optical Filters

1-10 0.008 parts by weight of a specific example compound of the tetraazaporphyrin compound (B-1) and a specific compound 3-21 (A1) which is a compound (B-2) having an absorption property specified in the present invention. 0.012 parts by weight of the quinophthalone compound of /A2 = 0.01) was dissolved in 80 parts by weight of methyl ethyl ketone.

30 parts by weight of an acrylic pressure-sensitive adhesive PX4-IR-PT-076 (manufactured by Nippon Shokubai Co., Ltd., solid content: 37.5%) and an isocyanate-based curing agent (L-55E manufactured by Nippon Polyurethane Co., Ltd.) were added in an amount of 0.057 parts by weight. 0.0057 parts by weight of a hardening accelerator (dibutyltin dilaurate manufactured by Tokyo Chemical Industry Co., Ltd.) was stirred at a homogenizer at 10,000 rpm for 10 minutes to obtain an adhesive composition having a solid content concentration of about 10%. Coating the adhesive composition on polyparaphenylene using a bar coater The ethylene dicarboxylate film (manufactured by Teijin DuPont Film Co., Ltd., thickness: 75 μm) was dried to a thickness of 25 μm, and dried at 90 ° C for 2 minutes. The release film on which the hafnium release layer was formed was bonded to the coated surface to prepare an optical filter. This optical filter is colorless.

This optical filter was attached to a front side of a liquid crystal television (AQUOSLC-16K5 manufactured by Sharp Co., Ltd.) using a white LED as a backlight unit, and used as an optical filter for a display device. As a result of observing the picture of the television through the optical filter, the contrast of the image is improved, the outline is clearly seen, and the hue does not change. Further, compared with before attaching the optical filter, the degree of eye fatigue and glare at the time of long-term appreciation is greatly reduced.

Further, the optical filter manufactured in the above was attached to the outside of the colorless spectacle lens having a center thickness of about 2 mm made of polythilyl ester to form an optical filter for the spectacle lens.

As a result of the use of the lens in which the lens is mounted, the inside and outside of the house are used, and there is little glare in the long-term use under the LED lighting indoors or outdoors. Moreover, the contrast of the branches of the trees or the contrast of red, yellow and green can be seen at a glance.

[Example 2-24] Manufacture of optical filter

In addition to the specific example compound 1-40 parts by weight of the compound as the tetraazaporphyrin compound (B-1) and the specific compound 3-40 (the compound (B-2) having the absorption property specified in the present invention) ( An optical filter was produced in the same manner as in Example 2-23 except that 0.011 part by weight of the quinophthalone compound of A1/A2 = 0.02) was used. The resulting optical filter is colorless.

Using this optical filter, the same operation as in Example 2-23 was carried out, An optical filter is attached to the front of the LCD TV to form an optical filter for the display device. The results of the screen of the liquid crystal television were observed through an optical filter, and the same effects as those of Example 2-23 were obtained.

[Example 2-25] Fabrication of Optical Filters

1,000 parts by weight of a polymethyl methacrylate resin (manufactured by Asahi Kasei Co., Ltd.: 80N), and a specific example compound of the porphyrazine compound (B-1), from 1 to 10 parts by weight, and having the absorption specified in the present invention Specific Example Compound (B-2) Compound No. 3-21 (A1/A2 = 0.01) 0.01 part by weight of a quinophthalone compound, which was mixed by a rolling machine for 20 minutes, and then set at a temperature of 260 ° C by a uniaxial extruder. Under the condition of a screw rotation number of 56 rpm, it was melted and kneaded to be pelletized.

The pellets were mixed and extruded in a two-axis extruder to obtain a film (plate) having a thickness of about 200 μm. The temperature in the extruding zone and the melting line was at most 275 ° C, and the temperature of the chill roll was 30 ° C. Then, the film was extended in the two-axis direction to prepare a film having a thickness of 100 μm.

On the other hand, 80 parts by weight of methyl ethyl ketone and 30 parts by weight of an acrylic pressure-sensitive adhesive PX4-IR-PT-076 (manufactured by Nippon Shokubai Co., Ltd., solid content: 37.5%) and an isocyanate-based curing agent (manufactured by Nippon Polyurethane Co., Ltd.) L-55E) 0.057 parts by weight, a hardening accelerator (dibutyltin dilaurate, manufactured by Tokyo Chemical Industry Co., Ltd.), 0.0057 parts by weight, and stirred at a homogenizer at 10,000 rpm for 10 minutes to obtain an adhesive composition having a solid content concentration of about 10%.

This adhesive composition was applied onto a polymethyl methacrylate film containing a specific example compound 1-11 as a (B) organic dye and a specific example compound 3-21 by a bar coater, and dried. The film thickness becomes 25 Μm and let it dry. The release film on which the hafnium release layer was formed was bonded to the coated surface to prepare an optical filter. This optical filter is colorless. The optical filter is attached to the outside of the liquid crystal display surface of the smart phone terminal (iPhone 3GS 16GB SoftBank) to form an optical filter for the display device. As a result of observing the screen of the display through the optical filter, the contrast of the image or the text is improved, the outline is clearly seen, and the color tone is not changed. Furthermore, the degree of eye fatigue and glare at the time of long-term use is greatly reduced when compared with before attaching an optical filter.

[Comparative Example 2-1] Production of spectacle lenses

1,000 parts by weight of a polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering Plastics Co., Ltd.), 0.005 parts by weight of a quinophthalone compound of a specific example compound 3-21 (A1/A2 = 0.01), and mixed by a rolling machine for 20 minutes. The pellet was granulated by melting and kneading with a uniaxial extruder under the conditions of a drum setting temperature of 260 ° C and a screw rotation number of 56 rpm.

Using the pellet as a raw material, an eyeglass lens was obtained in the same manner as in Example 2-17. The resulting lens has a yellow hue. Further, in the observation of the glasses in which the lens is attached, although the glare is less than that when the glasses are not used, there is a feeling of glare when the eyes are under special conditions such as the sun in the daytime. Although the contrast of the blue (green), yellow, and red of the signal can be clearly confirmed, the hue changes.

[Comparative Example 2-2] Production of spectacle lenses

1,000 parts by weight of a polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering Plastics Co., Ltd.) and 0.005 parts by weight of a specific example compound 1-11 as a tetraazaporphyrin compound (B-1) were mixed by a rolling machine. After a minute, extrude with a single axis The machine was granulated by melting and kneading under the conditions of a drum setting temperature of 260 ° C and a screw rotation number of 56 rpm.

Using the pellet as a raw material, an eyeglass lens was obtained in the same manner as in Example 2-17. The resulting lens has a blue hue. Furthermore, in the observation of the glasses in which the lens is assembled, although the glare is less in the sun during the day than when the glasses are not used, there is a glare in the light of a specific object such as an LED lamp or a display device, and the eyes feel. fatigue. Although the contrast of the blue (green), yellow, and red of the signal can be clearly confirmed, the hue changes.

[Example 3-1]

1,000 parts by weight of a polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering Plastics Co., Ltd.), and 0.001 to 0.005 parts by weight of a specific example compound of the porphyrazine compound (B-1), as in the present invention 0.02 parts by weight of a compound of the compound (B-2) having a predetermined absorption property, 4-1 (A1/A2 = 0.01), which was mixed in a rolling machine for 20 minutes, and then set by a uniaxial extruder with a roller. The pellet was granulated by melting and kneading under the conditions of a temperature of 260 ° C and a screw rotation number of 56 rpm.

[Example 3-2]

In addition to the specific example compound 1-11 of the tetraazaporphyrin compound (B-1), 0.0058 parts by weight and the specific compound 4-1 (as the compound (B-2) having the absorption property specified in the present invention) The same procedure as in Example 3-1 was carried out except that 0.02 parts by weight of the oxime compound of A1/A2 = 0.02) was carried out to prepare pellets.

[Example 3-3]

In addition to the specific characterization of the tetraazaporphyrin compound (B-1) In addition to 0.02 parts by weight of the oxime compound of the specific compound 4-24 (A1/A2=0.02) which is the compound (B-2) having the absorption property specified in the present invention, the compound 1-12 The same operation as in Example 3-1 was carried out to prepare pellets.

[Example 3-4]

In addition to the specific example compound 1-18 as a tetraazaporphyrin compound (B-1), 0.007 parts by weight and the specific compound 4-25 as a compound (B-2) having the absorption property specified in the present invention ( The same procedure as in Example 3-1 was carried out except that 0.02 parts by weight of the oxime compound of A1/A2 = 0.03) was carried out to prepare pellets.

[Example 3-5]

In addition to the specific example compound 1-10 0.0068 parts by weight as the tetraazaporphyrin compound (B-1) and the specific compound 4-41 (which is the compound (B-2) having the absorption property specified in the present invention ( A pellet was prepared in the same manner as in Example 3-1 except that 0.019 part by weight of the oxime compound of A1/A2 = 0.05) was used.

[Examples 3-6]

1,000 parts by weight of a polyamidamine resin (GriLamid TR90, manufactured by EMS Chem Japan Co., Ltd.), and 0.0055 parts by weight of a specific compound of the porphyrazine compound (B-1), as specified in the present invention. Specific Example Compound Absorption Compound (B-2) Compound 4-1 (A1/A2 = 0.01) of an anthraquinone compound, 0.021 part by weight, was mixed by a rolling machine for 20 minutes, and then a uniaxial extruder was used to set a temperature of 260. Under the conditions of °C and screw rotation number of 56 rpm, the mixture was fused and kneaded to be pelletized.

[Examples 3-7]

In addition to the specific example compound 1-11 of the tetraazaporphyrin compound (B-1), 0.0067 parts by weight and the specific compound 4-24 as the compound (B-2) having the absorption property specified in the present invention ( The pellets were prepared in the same manner as in Example 3-6 except that the fluorene compound of A1/A2 = 0.02) was 0.0026 parts by weight.

[Examples 3-8]

In addition to the specific example compound 1-33 of the tetraazaporphyrin compound (B-1), 0.0067 parts by weight and the specific compound 4-30 as the compound (B-2) having the absorption property specified in the present invention ( A pellet was prepared in the same manner as in Example 3-6 except that the fluorene compound of A1/A2 = 0.02) was 0.0263 parts by weight.

[Examples 3-9]

1,000 parts by weight of a polymethyl methacrylate resin (manufactured by Asahi Kasei Co., Ltd.: 80N), and 0.001 0.0065 parts by weight of a specific example compound of the porphyrazine compound (B-1), and having the absorption specified in the present invention Specific Example Compound 4-1 (B-2) Compound 4-1 (A1/A2 = 0.01) of an anthraquinone compound of 0.021 part by weight, which was mixed by a rolling machine for 20 minutes, and then set at a drum temperature of 260 ° C by a uniaxial extruder. Under the condition of a screw rotation number of 56 rpm, it was melted and kneaded to be pelletized.

[Examples 3-10]

In addition to the specific example compound used as the tetraazaporphyrin compound (B-1), 1 to 13 0.009 parts by weight, and the specific example compound 4-44 (the compound (B-2) having the absorption property specified in the present invention) After A1/A2=0.03) The pellets were prepared in the same manner as in Example 3-9 except that the oxime compound was 0.036 parts by weight.

[Examples 3-11]

The pellets produced in Example 3-1 were used as a raw material, and were molded into a shape of 150 mm × 300 mm and a thickness of 2 mm under the conditions of a drum setting temperature of 260 ° C, a mold temperature of 80 ° C, and a molding cycle of 60 seconds. The resin composition of the flat plate. When the transmission spectrum of this resin composition was measured, the spectrum shown in Fig. 15 was obtained. This resin composition is almost colorless.

[Examples 3-12]

The same procedure as in Example 3-11 was carried out except that the pellets produced in Example 3-2 were used as a raw material, and formed into a resin composition of a flat plate. This resin composition is almost colorless.

[Examples 3-13]

The same procedure as in Example 3-11 was carried out except that the pellets produced in Example 3-3 were used as a raw material, and formed into a resin composition of a flat plate. This resin composition is almost colorless.

[Examples 3-14]

The same procedure as in Example 3-11 was carried out except that the pellets produced in Example 3-4 were used as a raw material, and formed into a resin composition of a flat plate. This resin composition is almost colorless.

[Examples 3-15]

The same procedure as in Example 3-11 was carried out except that the pellets produced in Example 3-5 were used as a raw material, and formed into a resin composition of a flat plate. This resin composition is almost colorless.

[Examples 3-16]

The same procedure as in Example 3-11 was carried out, except that the pellets produced in Example 3-6 were used as a raw material, and formed into a resin composition of a flat plate. This resin composition is almost colorless.

[Examples 3-17]

The same procedure as in Example 3-11 was carried out except that the pellets produced in Example 3-7 were used as a raw material, and formed into a resin composition of a flat plate. This resin composition is almost colorless.

[Examples 3-18]

The same procedure as in Example 3-11 was carried out except that the pellets produced in Examples 3 to 8 were used as a raw material, and formed into a resin composition of a flat plate. This resin composition is almost colorless.

[Examples 3-19]

The same procedure as in Example 3-11 was carried out except that the pellets produced in Examples 3 to 9 were used as a raw material, and formed into a resin composition of a flat plate. This resin composition is almost colorless.

[Examples 3-20] Manufacture of spectacle lenses

In a 2 L separation flask equipped with a thermometer, a stirrer, and a nitrogen-sealed tube, 1,000 parts by weight of polyoxybutylene glycol (PGT-1000N, manufactured by Hodogaya Chemical Co., Ltd.) having an average molecular weight of 1,014 was added, and heated while stirring in a nitrogen stream. Dehydrated under reduced pressure of 100 to 110 ° C / 3 to 5 mmHg for 1 hour. After the completion of the dehydration, 850 parts by weight of 4,4'-methylene-bis(cyclohexyl isocyanate) (Desmodur W) was added, and the reaction was carried out at 120 to 130 ° C for 2 hours. Prepolymer. Income The prepolymer was a colorless transparent liquid having an NCO content of 9.9%, a viscosity of 8600 mPa ‧ s / 30 ° C, and a temperature of 750 mPa ‧ / 60 ° C.

After heating 1,000 parts by weight of the obtained prepolymer to 70 ° C, a specific example compound 1-10 0.0075 parts by weight as a tetraazaporphyrin compound (B-1) is added and as having the absorption characteristics specified in the present invention. Specific compound 4-1 (A1/A2 = 0.01) of the compound (B-2): 0.025 parts by weight of an anthraquinone compound, which was mixed. Subsequently, it was degassed and mixed with 314 parts by weight of 4,4'-methylene-bis(2-chlorinated aniline) melted at 120 °C.

This mixture was poured into a model preheated at 100 ° C, and heat-hardened at 100 ° C for 24 hours to obtain a lens for spectacles having a lens thickness of about 2.6 mm.

The resulting lens is almost colorless. Furthermore, through the observation of the glasses in which the lenses are assembled, there is little glare even when used for a long time on a sunny day. Moreover, the contrast of the branches of the trees or the contrast of red, yellow and green can be seen at a glance.

[Example 3-21] Manufacture of spectacle lenses

The pellets produced in Example 3-1 were used as raw materials, melted at 250 ° C, and molded by an injection molding machine using a set metal mold to obtain an outer diameter of 75 mm. Plastic lens with a center thickness of 2mm.

The resulting lens is almost colorless. Furthermore, through the observation of the glasses in which the lenses are assembled, there is little glare even when used for a long time on a sunny day. Moreover, the contrast of the branches of the trees or the contrast of red, yellow and green can be seen at a glance.

[Example 3-22] Manufacturing of spectacle lenses

In addition to using the pellets produced in Example 3-3 as a raw material, The same operation as in Example 3-21 was carried out to obtain a plastic lens having an outer diameter of 75 mm φ and a center thickness of 2 mm.

The resulting lens is almost colorless. Further, the observation by the lens in which the lens was assembled was the same as that of Example 3-21.

[Examples 3-23] Manufacture of spectacle lenses

Except that the pellets produced in Examples 3-5 were used as the raw materials, the same operations as in Example 3-21 were carried out to obtain an outer diameter of 75 mm. Plastic lens with a center thickness of 2mm.

The resulting lens is almost colorless. Further, the observation by the lens in which the lens was assembled was the same as that of Example 3-21.

[Examples 3-24] Manufacture of spectacle lenses

Except that the pellets produced in Examples 3 to 6 were used as the raw materials, the same operations as in Example 3-21 were carried out to obtain an outer diameter of 75 mm. Plastic lens with a center thickness of 2mm.

The resulting lens is almost colorless. Further, the observation by the lens in which the lens was assembled was the same as that of Example 3-21.

[Example 3-25] Manufacturing of spectacle lenses

Except that the pellets produced in Examples 3-7 were used as the raw materials, the same operations as in Example 3-21 were carried out to obtain an outer diameter of 75 mm. Plastic lens with a center thickness of 2mm.

The resulting lens is almost colorless. Further, the observation by the lens in which the lens was assembled was the same as that of Example 3-21.

[Examples 3-26] Manufacture of spectacle lenses

Except that the pellets produced in Examples 3-9 were used as the raw materials, the same operations as in Example 3-21 were carried out to obtain an outer diameter of 75 mm. Plastic lens with a center thickness of 2mm.

The resulting lens is almost colorless. Further, the observation by the lens in which the lens was assembled was the same as that of Example 3-21.

[Embodiment 3-27] Manufacturing of a sun visor for automobiles

The flat plate having the outer shape of 150 mm × 300 mm and a thickness of 2 mm manufactured in Example 3-11 was integrally attached to the sun visor body which is generally used for automobiles through the hinge portion of the flexible resin, and the sunshade for anti-glare was obtained. board.

When the sun visor is hung, it is not glaring when observing the opposite vehicle with the light on. Furthermore, since the transmitted color tone is almost colorless, there is no difficulty in recognizing the blue (green), yellow, and red colors used in the signal during the day. Furthermore, even if this anti-glare sun visor is used, the light transmittance is not greatly reduced.

[Example 3-28] Fabrication of Optical Filters

100 parts by weight of polymethyl methacrylate resin (manufactured by Asahi Kasei Co., Ltd.: 80N) was dissolved in 300 parts by weight of methyl ethyl ketone, and specific examples of the compound of the tetraazaporphyrin compound (B-1) were 1-11 0.09. The weight fraction is 0.30 part by weight of the oxime compound of the specific example compound 4-24 (A1/A2 = 0.02) which is the compound (B-2) having the absorption property specified in the present invention, and is used as a coating liquid. This coating liquid was applied on the surface of a polyethylene terephthalate (PET) plate having a thickness of about 200 μm with a Meyer rod, and the film thickness after drying was 10 μm, and it was dried.

The PET plate with the anti-glare cover is placed on the display screen of the personal computer for the LED backlight, and is used as an optical filter for the display device. View The results of various screens such as text display, image display, and animation display, not only glare and glare are reduced before the setting, but also reduce the fatigue of the eyes. The contrast of the images is improved and the outline is clearly seen. No change.

[Example 3-29] Fabrication of Optical Filters

1,000 parts by weight of a polymethyl methacrylate resin (manufactured by Asahi Kasei Co., Ltd.: 80N), and 1-10 0.077 parts by weight of a specific example compound of the porphyrazine compound (B-1), and having the absorption specified in the present invention Specific Example Compound 4-1 (A-2/A2 = 0.01) 0.218 parts by weight of the oxime compound of the compound (B-2), which was mixed by a rolling machine for 20 minutes, and then set at a temperature of 260 ° C by a uniaxial extruder. Under the condition of a screw rotation number of 56 rpm, it was melted and kneaded to be granulated.

The pellets were mixed and extruded in a two-axis extruder to obtain a film (plate) having a thickness of about 200 μm. The temperature in the extruding zone and the melting line was at most 275 ° C, and the temperature of the chill roll was 30 ° C.

The obtained film was cut and attached as an optical filter to the surface of a portable smart phone terminal using an acrylic adhesive. The results of observing the display surface under various conditions such as text display and image display not only reduce the glare and glare before the attachment, but also reduce the fatigue of the eyes. The contrast of the image is improved and the outline is clearly seen. On the other hand, the color tone does not change. .

[Example 3-30] Fabrication of Optical Filters

Specific examples of the compound of the tetraazaporphyrin compound (B-1): 1 to 0.01 parts by weight, and specific examples of the compound (B-2) having the absorption property specified in the present invention, compound 4-24 (A1) /A2=0.01) The compound was 0.022 parts by weight dissolved in 80 parts by weight of methyl ethyl ketone.

30 parts by weight of an acrylic pressure-sensitive adhesive PX4-IR-PT-076 (manufactured by Nippon Shokubai Co., Ltd., solid content: 37.5%) and an isocyanate-based curing agent (L-55E manufactured by Nippon Polyurethane Co., Ltd.) were added in an amount of 0.057 parts by weight. 0.0057 parts by weight of a hardening accelerator (dibutyltin dilaurate manufactured by Tokyo Chemical Industry Co., Ltd.) was stirred at a homogenizer at 10,000 rpm for 10 minutes to obtain an adhesive composition having a solid content concentration of about 10%.

The adhesive composition was applied to a polyethylene terephthalate film (manufactured by Teijin DuPont Film Co., Ltd., thickness: 75 μm) by a bar coater, and the film thickness after drying was 25 μm, and the film was dried at 90 ° C. Dry for 2 minutes. The release film on which the hafnium release layer was formed was bonded to the coated surface to prepare an optical filter. This optical filter is colorless.

This optical filter was attached to a front side of a liquid crystal television (AQUOSLC-16K5 manufactured by Sharp Co., Ltd.) using a white LED as a backlight unit, and used as an optical filter for a display device. Observing the result of the TV screen through the optical filter, the contrast of the image is improved, the outline is clearly seen, and the color tone is not changed. Furthermore, when compared with before attaching an optical filter, the degree of eye fatigue and glare at the time of long-term appreciation is greatly reduced.

Further, the optical filter manufactured in the above was attached to the outside of the colorless spectacle lens having a center thickness of about 2 mm made of polythilyl ester to form an optical filter for the spectacle lens.

As a result of the use of the lens in which the lens is mounted, the inside and outside of the house are used, and there is little glare in the long-term use under the LED lighting indoors or outdoors. And, for the lines of the twigs of trees or red, The contrast between yellow and green can be seen at a glance.

[Example 3-31] Fabrication of Optical Filter

In addition to the specific example compound 1-12 of the tetraazaporphyrin compound (B-1), 0.0058 parts by weight and the specific compound 4-41 (as the compound (B-2) having the absorption property specified in the present invention) An optical filter was produced in the same manner as in Example 3-30 except that 0.196 parts by weight of the oxime compound of A1/A2 = 0.05). The resulting optical filter is colorless. The results of observing the liquid crystal television screen through the optical filter gave the same effects as those of Examples 2-23.

[Example 3-32] Fabrication of Optical Filter

1,000 parts by weight of a polymethyl methacrylate resin (manufactured by Asahi Kasei Co., Ltd.: 80N), and a specific example compound of the porphyrazine compound (B-1), from 1 to 10 parts by weight, and having the absorption specified in the present invention Specific Example Compound 4-1 (B-2) Compound 4-1 (A1/A2 = 0.01) of an anthraquinone compound of 0.021 part by weight, which was mixed by a rolling machine for 20 minutes, and then set at a drum temperature of 260 ° C by a uniaxial extruder. Under the condition of a screw rotation number of 56 rpm, it was melted and kneaded to be pelletized.

The pellets were mixed and extruded in a two-axis extruder to obtain a film (plate) having a thickness of about 200 μm. The temperature in the extruding zone and the melting line was at most 275 ° C, and the temperature of the chill roll was 30 ° C. Then, the film was extended in the two-axis direction to prepare a film having a thickness of 100 μm.

On the other hand, 80 parts by weight of methyl ethyl ketone and 30 parts by weight of an acrylic pressure-sensitive adhesive PX4-IR-PT-076 (manufactured by Nippon Shokubai Co., Ltd., solid content: 37.5%) and an isocyanate-based curing agent (manufactured by Nippon Polyurethane Co., Ltd.) L-55E) 0.057 weight 0.0057 parts by weight of a part by weight and a hardening accelerator (dibutyltin dilaurate manufactured by Tokyo Chemical Industry Co., Ltd.) was stirred at a homogenizer at 10,000 rpm for 10 minutes to obtain an adhesive composition having a solid content concentration of about 10%.

This adhesive composition was applied onto a polymethyl methacrylate film containing a specific example compound 1-10 as the (B) organic dye and a specific example compound 4-1 by a bar coater, and dried. The film thickness was 25 μm and it was dried. The release film on which the hafnium release layer was formed was bonded to the coated surface to prepare an optical filter. This optical filter is colorless. The transmission spectrum of this optical filter is as shown in Fig. 16.

This optical filter is attached to the front side of the liquid crystal television in which the backlight unit uses a white LED as an optical filter for a display device. Observing the result of the TV screen through the optical filter, the contrast of the image is improved, the outline is clearly seen, and the color tone is not changed. Furthermore, when compared with before attaching an optical filter, the degree of eye fatigue and glare at the time of long-term appreciation is greatly reduced.

[Possibility of application in industry]

The resin composition of the present invention can effectively block blue light in the vicinity of 380 nm to 460 nm and light having high visual acuity in the vicinity of 580 nm to 590 nm, thereby preventing glare or glare, adverse effects on the eyes or the human body, and The contrast is improved.

Moreover, since the resin composition is almost non-colored, the light transmittance is rarely lowered, and the deterioration of the pigment in the resin is small, it is very suitable for an eyeglass lens, a sun visor, a mask for a helmet, a cover for a display device, and a display assembly. Extensive light such as optical filters, optical filters for eyeglass lenses, etc. Learn about items.

Since the drawings in this case are only spectral map data, not the representative map of this case, there is no designated representative map in this case.

Claims (16)

A resin composition comprising at least (A) a resin and (B) an organic dye, and (B) an organic dye comprising a porphyrazine compound (B-1) represented by the following formula (1) and a compound (B) -2), the compound (B-2) has a maximum absorption between 380 and 470 nm in a toluene solution, and an absorbance (A1) at a maximum absorption wavelength between 520 and 800 nm and a maximum between 380 and 470 nm. The ratio of absorbance (A2) of the absorption wavelength (A1/A2) is less than 0.1, [In the formula (1), R ₁ to R ₈ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group, an alkenyl group, an alkyl halide group, an alkoxy group, a halogenated alkoxy group, or an alkylthio group. , alkoxyalkyl, alkoxyalkoxyalkyl, halogenated alkoxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, substituted or unsubstituted Amine, substituted or unsubstituted fluorenyl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryloxyalkyl, substituted or unsubstituted aralkyl An oxy group, a substituted or unsubstituted aralkyloxyalkyl group, a substituted or unsubstituted arylthio group, and mutually adjacent groups selected from R ₁ to R ₈ may be bonded to each other, and The substituted carbon atoms together form a substituted or unsubstituted ring of 5 membered or more rings, but not all of R ₁ to R ₈ form a ring; M represents 2 hydrogen atoms, 2 monovalent metal atoms, and 2 valence a metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom or an oxidized metal atom]. The resin composition according to the first aspect of the invention, wherein the compound (B-2) is at least one compound selected from the group consisting of an azo compound, a quinophthalone compound, and a quinone compound. The resin composition according to claim 2, wherein the azo compound is represented by the following formula (2): [In the formula (2), Y ₁ to Y ₁₁ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a carboxyl group, an alkyl group, an alkenyl group, an alkyl halide group, an alkoxy group, or an alkyl halide. Oxyl, alkylthio, alkoxyalkyl, alkoxyalkoxyalkyl, halogenated alkoxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl , substituted or unsubstituted amino, substituted or unsubstituted guanylamino, substituted or unsubstituted fluorenyl, substituted or unsubstituted aryloxy, substituted or unsubstituted Aryloxyalkyl, substituted or unsubstituted aralkyloxy, substituted or unsubstituted aralkyloxyalkyl, alkyloxycarbonyl, substituted or unsubstituted aryl Alkoxycarbonyl, or substituted or unsubstituted arylthio]. The resin composition according to claim 2, wherein the quinophthalone compound is represented by the following formula (3): [In the formula (3), Z ₁ to Z ₉ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a decyl group, a carboxyl group, an alkyl group, an alkenyl group, an alkyl halide group, an alkoxy group, or a halogenated alkoxy group. Alkyl, alkylthio, alkoxyalkyl, alkoxyalkoxyalkyl, halogenated alkoxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, Substituted or unsubstituted amino, substituted or unsubstituted guanylamino, substituted or unsubstituted fluorenyl, substituted or unsubstituted aryloxy, substituted or unsubstituted Aryloxyalkyl, substituted or unsubstituted aralkyloxy, substituted or unsubstituted aralkyloxyalkyl, alkyloxycarbonyl, substituted or unsubstituted aryl An oxycarbonyl group, or a substituted or unsubstituted arylthio group, and the mutually adjacent groups selected from Z ₆ to Z ₉ may be bonded to each other to form a substituted or unsubstituted group together with the substituted carbon atom. The ring of 5 members is above the ring]. The resin composition according to any one of claims 2 to 4, wherein the oxime compound is represented by the following formula (4): [In the formula (4), X ₁ to X ₈ each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkyl halide group, an alkoxy group, an alkylthio group, an alkoxyalkyl group, a substituted or unsubstituted group. An aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted arylthio group, but at least one of X ₁ to X ₈ must be a substituted or unsubstituted arylthio group. ]. The resin composition according to any one of the items 1 to 5, wherein R ₁ to R ₈ in the formula (1) each independently represent a hydrogen atom, a halogen atom, and a carbon number of 1 to 12. Alkyl group, alkenyl group having 2 to 6 carbon atoms, halogenated alkyl group having 1 to 12 carbon atoms, alkoxy group having 1 to 12 carbon atoms, halogenated alkoxy group having 1 to 12 carbon atoms, and carbon number 1 to 12 Alkylthio group, alkoxyalkyl group having 2 to 16 carbon atoms, halogenated alkoxyalkyl group having 2 to 16 carbon atoms, alkoxyalkoxyalkyl group having 3 to 20 carbon atoms, carbon number 6 to 18 Substituted or unsubstituted aryl, substituted or unsubstituted amino group having 1 to 18 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, carbon number 6 to 18 a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxyalkyl group having 7 to 20 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms M is Cu, Zn, Fe, Co, Ni, Pd, Mn, Mg, Mn(OH), Mn(OH) ₂ , VO or TiO. The resin composition according to any one of claims 3 to 6, wherein Y ₁ to Y ₁₁ in the formula (2) each independently represent a hydrogen atom, a halogen atom, and a carbon number of 1 to 12. Alkyl group, alkenyl group having 2 to 6 carbon atoms, halogenated alkyl group having 1 to 12 carbon atoms, alkoxy group having 1 to 12 carbon atoms, halogenated alkoxy group having 1 to 12 carbon atoms, and carbon number 1 to 12 Alkylthio group, alkoxyalkyl group having 2 to 16 carbon atoms, alkoxyalkoxyalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, carbon number a substituted or unsubstituted amino group of 1 to 18, a substituted or unsubstituted decylamino group having 1 to 18 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, and a carbon number a substituted or unsubstituted aryloxy group of 6 to 18, a substituted or unsubstituted aryloxyalkyl group having 7 to 20 carbon atoms, an alkyloxycarbonyl group having 2 to 13 carbon atoms, and a carbon number A substituted or unsubstituted aryloxycarbonyl group of 7 to 19, a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms. The resin composition according to any one of claims 4 to 7, wherein Z ₁ to Z ₉ in the formula (3) each independently represent a hydrogen atom, a halogen atom, and a carbon number of 1 to 12. Alkyl group, alkenyl group having 2 to 6 carbon atoms, halogenated alkyl group having 1 to 12 carbon atoms, alkoxy group having 1 to 12 carbon atoms, halogenated alkoxy group having 1 to 12 carbon atoms, and carbon number 1 to 12 Alkylthio group, alkoxyalkyl group having 2 to 16 carbon atoms, alkoxyalkoxyalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, carbon number a substituted or unsubstituted amino group of 1 to 18, a substituted or unsubstituted decylamino group having 1 to 18 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, and a carbon number a substituted or unsubstituted aryloxy group of 6 to 18, a substituted or unsubstituted aryloxyalkyl group having 7 to 20 carbon atoms, an alkyloxycarbonyl group having 2 to 13 carbon atoms, and a carbon number a substituted or unsubstituted aryloxycarbonyl group of 7 to 19, a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms, or a mutually adjacent group selected from Z ₆ to Z ₉ may be mutually Bonding, together with a substituted carbon atom, forming a substituted or unsubstituted a benzene ring or a naphthalene ring. The resin composition according to any one of the items 5 to 8, wherein X ₁ to X ₈ in the formula (4) each independently represent a hydrogen atom, a halogen atom, and a carbon number of 1 to 12. Alkyl group, halogenated alkoxy group having 1 to 12 carbon atoms, alkoxy group having 1 to 12 carbon atoms, alkylthio group having 1 to 12 carbon atoms, alkoxyalkyl group having 2 to 16 carbon atoms, carbon number A substituted or unsubstituted arylthio group of 6 to 18, and at least one of X ₁ to X ₈ must be a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms. The resin composition according to any one of claims 1 to 9, wherein the resin is a thermoplastic resin or a thermosetting resin. The resin composition according to claim 10, wherein the thermoplastic resin is at least one selected from the group consisting of a polycarbonate resin, a polyamide resin, an acrylic resin, and a polyester resin, and the thermosetting resin is At least one resin selected from the group consisting of a polyurethane resin, a polythiamine resin, and allyl diglycol carbonate. A molded body formed by molding the resin composition according to any one of the items 1 to 11. The molded article according to claim 12, wherein the molded article is an optical article for antiglare, and an optical article or light for reducing short-wavelength light Learn the filter. The molded body according to claim 12, wherein the molded body is an eyeglass lens, a sun visor, a mask for a helmet, a cover for a display device, an optical filter for display assembly, or an eyeglass lens assembly. Use an optical filter. An adhesive composition comprising the resin composition according to any one of claims 1 to 9. An optical article for preventing glare, an optical article for reducing short-wavelength light, or an optical filter, which is formed by the adhesive according to claim 15 of the patent application.