Quinophthalone compound, resin composition, and molding

Abstract

To provide: a quinophthalone compound that effectively reduces glare and dazzling and has excellent contrast and visible light transmittance; a resin composition containing the compound; and a molding obtained from the composition.SOLUTION: A compound is represented by a formula (1), where at least one of R1 to R10 is a group represented by a formula (1-i).SELECTED DRAWING: Figure 4

Description

[Technical field]

[0001] The present invention relates to a quinophthalone compound, a resin composition, and a molded article. [Background technology]

[0002] In order to reduce the glare of sunlight and automobile headlights and the associated discomfort, blurred contrast, visual fatigue, etc., it is known to impart a so-called anti-glare function to, for example, eyeglass lenses. This is aimed at selectively cutting out the wavelength range in which glare is easily felt, and a technology for incorporating rare earth metal compounds such as neodymium compounds into eyeglass lenses is disclosed in Patent Document 1 and the like. Neodymium compounds have a sharp absorption in the vicinity of 570 to 590 nm, and are characterized by being able to selectively absorb light in the 550 to 610 nm range, which has high human visual sensitivity and is easily glare-sensitive.

[0003] However, although inorganic rare earth metal compounds such as neodymium compounds can be easily blended into glass lenses, in recent years plastics have come to be primarily used as the material for eyeglass lenses, and there is a problem in that inorganic rare earth metal compounds cannot be uniformly and transparently dispersed and mixed into lens resins.

[0004] The incorporation of specific organic rare earth metal complexes into plastic lens materials has also been considered, but problems remain, such as the limited choice of compounds being restricted to expensive compounds, and insufficient solubility and dispersibility in resin.

[0005] Patent Documents 2 to 4 disclose techniques in which a tetraazaporphyrin compound is incorporated into a plastic eyeglass lens instead of a neodymium compound to cut out light in the range of 580 nm to 590 nm and provide anti-glare properties and improved visibility.

[0006] However, to prevent glare from sunlight, it is not enough to only cut light of 550 to 600 nm, and it is also necessary to cut light of shorter wavelengths, particularly light in the blue to purple region of 450 nm or less. This short-wavelength light not only causes glare, flickering and blurring of vision, but is also harmful to the eyes. In addition, elderly people and cataract patients have cloudy lenses, which tend to scatter light of wavelengths of 450 nm or less, and therefore feel strong glare from light in this wavelength region.

[0007] Recently, with the increasing efficiency and price reduction of blue LED elements, there has been an increase in lighting with LED light sources, LCD TVs and personal computer displays that use LED light sources for backlighting, portable electronic devices, and automobile lights that use LED light sources, etc. These lights contain more blue components than conventional light sources, and as a result, there are more opportunities than before to feel glare.

[0008] Patent Documents 5 and 6 disclose spectacle lenses that use a yellow dye or an orange dye as a blue light absorbing agent. Patent Document 7 discloses the application of a yellow dye or an orange dye as a blue light absorbing agent to an anti-glare optical article. However, these anti-glare optical articles are colored yellow or orange, and eyeglass lenses using these articles do not necessarily have a sufficient effect of preventing glare.

[0009] In recent years, flat displays using liquid crystal elements and organic EL elements have become widespread. Optical filters for improving the life span and contrast of various display devices such as organic EL displays and liquid crystal displays, and for cutting blue light in LED backlight displays are required to have excellent long-wavelength ultraviolet blocking ability, visible light transparency, and light resistance. Optical filters that improve the contrast of image display devices in bright rooms have been disclosed that have absorption maxima in the wavelength ranges of 380 to 420 nm, 480 to 520 nm, and 585 to 620 nm (Patent Document 8). Optical filters containing the dyes described therein have problems with visible transparency and light resistance.

[0010] Patent Document 9 discloses an optical filter containing a specific squarylium compound. However, this optical filter has a problem in terms of light resistance, and further improvement in visible light transparency is required.

[0011] Patent Document 10 discloses a crude resin for cutting blue light containing a specific quinophthalone compound. However, it is not necessarily superior to conventional resin materials using a yellow pigment reactive dye in terms of the cut rate for 400 to 500 nm light and the transmittance for 510 to 580 nm light, and further improvements are required.

[0012] Patent Document 11 discloses an antiglare optical article having a filter function that can reduce the glare of headlights of oncoming vehicles and ensure sufficient visibility at night. A quinophthalone compound is used as a blue light absorbing material, but improvement in resin compatibility is required.

[0013] Patent Document 12 describes coumarin derivatives, silole derivatives, and fluorene as dyes that selectively absorb blue light (e.g., wavelengths of 400 nm to 600 nm) among the photoelectric conversion elements used in image sensors, but there is a demand for improvement in light absorption efficiency. [Prior art documents] [Patent documents]

[0014] [Patent Document 1] JP 2000-75128 A [Patent Document 2] JP 2008-134618 A [Patent Document 3] JP 2011-145341 A [Patent Document 4] JP 2011-175176 A [Patent Document 5] Japanese Patent Application Publication No. 6-324293 [Patent Document 6] Japanese Patent Application Publication No. 9-43550 [Patent Document 7] JP 2001-356212 A [Patent Document 8] JP 2008-203436 A [Patent Document 9] JP 2009-139911 A [Patent Document 10] Patent No. 6204726 [Patent Document 11] JP 2003-149605 A [Patent Document 12] International Publication No. 2017 / 010398 Summary of the Invention [Problem to be solved by the invention]

[0015] The object of the present invention is to provide a molded article having excellent antiglare performance and little coloring by using a novel compound or a resin composition containing the compound. More specifically, the object of the present invention is to provide an antiglare optical article that efficiently cuts blue light in the range of about 380 nm to 450 nm, suppresses glare and glare, enhances contrast, and has almost no coloring, resulting in excellent product appearance. A further object of the present invention is to provide an optical filter which has improved contrast, is excellent in visible light transparency, and is stable to light. [Means for solving the problem]

[0016] As a result of investigations into the above problems, the present inventors have found that these problems can be solved by using a quinophthalone compound having a specific structure, and have thus completed the present invention. That is, the present invention can be shown as follows.

[0017] [1] A quinophthalone compound represented by general formula (1). [ka] (In formula (1), R1~R 10 each independently represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a sulfone group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a mercapto group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, a carboxylate group, a sulfonate group, or a group represented by the following general formula (1-i): R1~R 10 At least one of the above is a group represented by the following general formula (1-i). R1 and R2, R2 and R 3、 R3 and R4, R4 and R5, R5 and R6, R7 and R8, R8 and R9, R9 and R 10 may be bonded to form an aliphatic ring, an aromatic ring or a heterocyclic ring. [ka] In formula (1-i), n is an integer of 1 to 3, Y represents a single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted alkynylene group, a substituted or unsubstituted arylene group, an oxygen atom, a sulfur atom, a carbonyl group, a sulfonyl group, a substituted or unsubstituted imino group, or a divalent to tetravalent sulfur atom-containing hydrocarbon group; R 11 ~R 14 each independently represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a sulfone group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a mercapto group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, a carboxylate group, or a sulfonate group; R 11 and R 12 , R 12 and R 13、 R 13 and R 14 may be bonded to form an aliphatic ring, an aromatic ring, or a heterocyclic ring. [2] In general formula (1), R1 to R 10 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 8 carbon atoms, a substituted or unsubstituted amino group having 1 to 16 carbon atoms, a mercapto group, a substituted or unsubstituted alkylthio group having 1 to 8 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 12 carbon atoms, or a group represented by general formula (1-i), and R1 to R 10 At least one of the groups is a group represented by the following general formula (1-i): In general formula (1-i), R 11 ~R 14are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 8 carbon atoms, a substituted or unsubstituted amino group having 1 to 16 carbon atoms, a mercapto group, a substituted or unsubstituted alkylthio group having 1 to 8 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 12 carbon atoms. [3] The quinophthalone compound according to [1] or [2], wherein in general formula (1-i), n is an integer of 1 to 3, and Y is a single bond. [4] The quinophthalone compound according to any one of [1] to [3], wherein in general formula (1-i), n is an integer of 1 to 3, and Y is a substituted or unsubstituted alkylene group having 1 to 12 carbon atoms, an oxygen atom, a sulfur atom, a substituted or unsubstituted imino group having 1 to 12 carbon atoms, or a divalent to tetravalent sulfur atom-containing hydrocarbon group. [5] The quinophthalone compound according to any one of [1] to [4], which has a maximum wavelength of 440 to 470 nm. [6] (A) a thermoplastic or thermosetting resin; (B) one or more quinophthalone compounds represented by general formula (1) according to any one of [1] to [5]; A resin composition comprising: [7] The resin composition according to [6], wherein the thermoplastic resin is at least one selected from a polycarbonate resin, a polyamide resin, an acrylic resin, and a polyester resin, and the thermosetting resin is at least one selected from a polyurethane resin, a polythiourethane resin, and an allyl diglycol carbonate resin. [8] A molded article obtained by molding the resin composition according to [6] or [7]. [9] The molded article according to [8], which is an anti-glare optical article.

[10] A molded product of [8] which is an optical filter.

[11] A sun visor, the molding of [8].

[12] A molded product of [8], which is a helmet shield.

[13] The molded article according to [8], which is an antiglare coating for a display device of an information device or an antiglare film for a display device of an information device. Effect of the Invention

[0018] The quinophthalone compound of the present invention efficiently blocks blue light in the range of about 380 nm to 450 nm, suppresses glare and dazzling, and is excellent in improving contrast and in visible light transmittance. Furthermore, since the quinophthalone compound of the present invention is almost free from coloration and exhibits little decrease in light transmittance, a molded article obtained by molding a composition containing the compound is also useful for improving the life of image display devices and improving contrast in bright rooms. [Brief description of the drawings]

[0019] [Figure 1] 1 is a transmission spectrum of the compound produced in Example 1. [Diagram 2] 1 is a transmission spectrum of the compound produced in Example 2. [Diagram 3] 1 is a transmission spectrum of the compound produced in Example 3. [Figure 4] 1 shows the HOMO values ​​of Examples 1 to 3 and a conventional quinophthalone dye (Comparative Example 1). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0020] Hereinafter, the embodiments of the present invention will be described in detail. For example, "1 to 10" means "1 or more" to "10 or less" unless otherwise specified.

[0021] [Quinophthalone compounds] The quinophthalone compound of the present embodiment is represented by the following general formula (1).

[0022] [ka]

[0023] In formula (1), R1~R 10each independently represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a sulfone group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a mercapto group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, a carboxylate group, a sulfonate group, or a group represented by the following general formula (1-i): R1~R 10 At least one of the above is a group represented by the following general formula (1-i). R1 and R2, R2 and R 3、 R3 and R4, R4 and R5, R5 and R6, R7 and R8, R8 and R9, R9 and R 10 may be bonded to form an aliphatic ring, an aromatic ring or a heterocyclic ring.

[0024] [ka]

[0025] In formula (1-i), n is an integer of 1 to 3, Y represents a single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted alkynylene group, a substituted or unsubstituted arylene group, an oxygen atom, a sulfur atom, a carbonyl group, a sulfonyl group, a substituted or unsubstituted imino group, or a divalent to tetravalent hydrocarbon group containing a sulfur atom.

[0026] R 11 ~R 14each independently represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a sulfone group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a mercapto group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, a carboxylate group, or a sulfonate group; R 11 and R 12 , R 12 and R 13、 R 13 and R 14 may be bonded to form an aliphatic ring, an aromatic ring or a heterocyclic ring.

[0027] R to R in general formula (1) 10 Preferred groups for are as follows: In the present embodiment, R1 to R 10 each independently represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a sulfone group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 24 carbon atoms, mercapto group, a substituted or unsubstituted alkylthio group having 1 to 18 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 24 carbon atoms, an amino group, a substituted amino group having 1 to 24 carbon atoms, a substituted or unsubstituted alkylcarbonyl group having 2 to 13 carbon atoms, a substituted or unsubstituted arylcarbonyl group having 7 to 25 carbon atoms, a substituted or unsubstituted aminocarbonyl group having 1 to 12 carbon atoms, a carboxylate group, a sulfonate group, or a group represented by the above general formula (1-i) is preferred, and R1 to R 10 At least one of the above is a group represented by general formula (1-i).

[0028] R1~R 10 are each independently preferably a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 19 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 8 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms, a mercapto group, a substituted or unsubstituted alkylthio group having 1 to 8 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms, an amino group, a substituted amino group having 1 to 16 carbon atoms, or a group represented by the above general formula (1-i), 10 At least one of the above is a group represented by general formula (1-i).

[0029] R1~R 10 are each independently preferably a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 8 carbon atoms, a substituted or unsubstituted amino group having 1 to 16 carbon atoms, a mercapto group, a substituted or unsubstituted alkylthio group having 1 to 8 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 12 carbon atoms, or a group represented by general formula (1-i), 10 At least one of the above is a group represented by general formula (1-i).

[0030] R in general formula (1-i) 11 ~R 14 Preferred groups for are as follows: R in general formula (1-i) 11 ~R 14each independently represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a sulfone group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, Preferred are aryloxy groups, mercapto groups, substituted or unsubstituted alkylthio groups having 1 to 18 carbon atoms, substituted or unsubstituted arylthio groups having 6 to 24 carbon atoms, substituted amino groups having 1 to 24 carbon atoms, substituted or unsubstituted alkylcarbonyl groups having 2 to 13 carbon atoms, substituted or unsubstituted arylcarbonyl groups having 7 to 25 carbon atoms, substituted or unsubstituted aminocarbonyl groups having 1 to 12 carbon atoms, carboxylate groups, and sulfonate groups.

[0031] R 11 ~R 14 are each independently preferably a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 19 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 8 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms, a mercapto group, a substituted or unsubstituted alkylthio group having 1 to 8 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms, an amino group, or a substituted amino group having 1 to 16 carbon atoms.

[0032] R 11 ~R 14 are particularly preferably each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 8 carbon atoms, a substituted or unsubstituted amino group having 1 to 16 carbon atoms, a mercapto group, a substituted or unsubstituted alkylthio group having 1 to 8 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 12 carbon atoms.

[0033] R1~R 14 Examples of these substituents, as described in, are shown below. Examples of the halogen atom include a chlorine atom, a fluorine atom, a bromine atom, and an iodine atom. Examples of unsubstituted alkyl groups include linear or branched unsubstituted alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, 1-methylheptyl, and 2-ethylhexyl.

[0034] Examples of the substituted alkyl group include alkyl groups having an alkoxy group, such as a methoxymethyl group, an ethoxymethyl group, an n-butoxymethyl group, an n-hexyloxymethyl group, and a (2-ethylbutyloxy)methyl group; an alkyl group having an alkoxyalkoxy group, such as a methoxymethoxymethyl group or an ethoxyethoxymethyl group; Alkyl groups having an alkenyloxy group, such as a 2-(4'-pentenyloxy)ethyl group; an alkyl group having an aralkyloxy group, such as a benzyloxymethyl group or a 2-(benzyloxymethoxy)ethyl group; Alkyl groups having an aryl group, such as a phenylmethyl group, a phenylethyl group, or a naphthylmethyl group; an alkyl group having a heteroaryl group, such as a furanylmethyl group, a thienylmethyl group, or a pyridylmethyl group; an alkyl group having an aryloxy group, such as a phenyloxymethyl group, a 4-chlorophenyloxymethyl group, or a 4-(2'-phenyloxyethoxy)butyl group; Alkyl groups having an alkylthio group, such as an n-butylthiomethyl group or a 2-n-octylthioethyl group; Examples of the alkyl group include alkyl groups having a halogen atom, such as a fluoromethyl group, a trifluoromethyl group, a perfluoroethyl group, a 4-fluorocyclohexyl group, a dichloromethyl group, a 4-chlorocyclohexyl group, and a 7-chloroheptyl group.

[0035] Examples of substituted or unsubstituted alkenyl groups include vinyl, propenyl, 1-butenyl, isobutenyl, 1-pentenyl, 2-pentenyl, 2-methyl-1-butenyl, 2-cyclopentenyl, 1-vinylhexyl, styryl, styrylmethyl, and 2-styrylethyl groups.

[0036] Examples of the substituted or unsubstituted alkynyl group include an acetylenyl group, a propynyl group, a 1-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 2-methyl-1-pentynyl group, and a phenylacetylenyl group.

[0037] Examples of the substituted or unsubstituted aralkyl group include unsubstituted or alkyl group-containing aralkyl groups such as benzyl group, α-methylbenzyl group, phenethyl group, α-methylphenethyl group, α,α-dimethylbenzyl group, α,α-dimethylphenethyl group, 4-methylphenethyl group, 4-methylbenzyl group, and 4-isopropylbenzyl group; aralkyl groups having an aryl group or an aralkyl group, such as a 4-benzylbenzyl group, a 4-phenethylbenzyl group, or a 4-phenylbenzyl group; aralkyl groups having a substituted oxy group, such as a 4-methoxybenzyl group, a 4-n-tetradecyloxybenzyl group, a 4-n-heptadecyloxybenzyl group, a 3,4-dimethoxybenzyl group, a 4-methoxymethylbenzyl group, a 4-vinyloxymethylbenzyl group, a 4-benzyloxybenzyl group, or a 4-phenethyloxybenzyl group; Aralkyl groups having a hydroxyl group, such as a 4-hydroxybenzyl group and a 4-hydroxy-3-methoxybenzyl group; Aralkyl groups having a halogen atom, such as a 4-fluorobenzyl group, a 3-chlorobenzyl group, or a 3,4-dichlorobenzyl group; Examples include a 2-furfuryl group, a diphenylmethyl group, a 1-naphthylmethyl group, and a 2-naphthylmethyl group.

[0038] Examples of the substituted or unsubstituted aryl group include unsubstituted aryl groups such as a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-anthracenyl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 1-pyrenyl group, a 2-pyrenyl group, a 2-perylenyl group, a 3-perylenyl group, a 2-fluoranthenyl group, a 3-fluoranthenyl group, a 7-fluoranthenyl group, and an 8-fluoranthenyl group; aryl groups having an alkyl group, such as a 1-methyl-2-pyrenyl group, a 2-methylphenyl group, a 4-ethylphenyl group, a 4-(4'-tert-butylcyclohexyl)phenyl group, a 3-cyclohexylphenyl group, a 2-cyclohexylphenyl group, a 4-ethyl-1-naphthyl group, a 6-n-butyl-2-naphthyl group, or a 2,4-dimethylphenyl group; aryl groups having an alkoxy group or an aryloxy group, such as a 4-methoxyphenyl group, a 3-ethoxyphenyl group, a 2-ethoxyphenyl group, a 4-n-propoxyphenyl group, a 3-n-propoxyphenyl group, a 4-isopropoxyphenyl group, a 3-isopropoxyphenyl group, a 2-isopropoxyphenyl group, a 2-sec-butoxyphenyl group, a 4-n-pentyloxyphenyl group, a 4-isopentyloxyphenyl group, a 2-methyl-5-methoxyphenyl group, or a 2-phenyloxyphenyl group; Aryl groups having an aryl group, such as a 4-phenylphenyl group, a 3-phenylphenyl group, a 2-phenylphenyl group, a 2,6-diphenylphenyl group, a 4-(2'-naphthyl)phenyl group, a 2-phenyl-1-naphthyl group, a 1-phenyl-2-naphthyl group, or a 7-phenyl-1-pyrenyl group; Aryl groups having a halogen atom, such as a 4-fluorophenyl group, a 3-fluorophenyl group, a 2-fluorophenyl group, a 4-chlorophenyl group, a 4-bromophenyl group, a 2-chloro-5-methylphenyl group, a 2-chloro-6-methylphenyl group, a 2-methyl-3-chlorophenyl group, a 2-methoxy-4-fluorophenyl group, or a 2-fluoro-4-methoxyphenyl group; Examples of such groups include a 2-trifluoromethylphenyl group, a 3-trifluoromethylphenyl group, a 4-trifluoromethylphenyl group, a 3,5-bistrifluoromethylphenyl group, a 4-perfluoroethylphenyl group, a 4-methylthiophenyl group, a 4-ethylthiophenyl group, a 4-cyanophenyl group, and a 3-cyanophenyl group.

[0039] The substituted or unsubstituted alkoxy group is preferably a substituted or unsubstituted alkoxy group having 1 to 18 carbon atoms, and more preferably a substituted or unsubstituted alkoxy group having 1 to 8 carbon atoms.

[0040] Examples of unsubstituted alkoxy groups include linear, branched or cyclic unsubstituted alkoxy groups such as methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, tert-butyloxy, sec-butyloxy, n-pentyloxy, isopentyloxy, n-hexyloxy, 2-methylpentyloxy, 1,1-dimethylbutyloxy, 1,2,2-trimethylpropyloxy, 2-ethylbutyloxy, 1,3-dimethylhexyloxy, cyclohexyloxy, methylcyclopentyloxy, n-heptyloxy, n-heptyloxy, n-octyloxy, 3,5,5-trimethylhexyloxy, n-decyloxy, n-undecyloxy, n-dodecyloxy, 1-adamantyloxy and n-pentadecyloxy.

[0041] Examples of the substituted alkoxy group include a methoxymethoxy group, an ethoxymethoxy group, an n-propyloxymethoxy group, an n-butyloxymethoxy group, an isobutyloxymethoxy group, a tert-butyloxymethoxy group, an n-pentyloxymethoxy group, a 2-methoxyethoxy group, a 2-ethoxyethoxy group, a 2-n-propyloxyethoxy group, a 2-isopropyloxyethoxy group, a 2-n-butyloxyethoxy group, a 2-isobutyloxyethoxy group, a 2-tert-butyloxyethoxy group, a 2-sec-butyloxyethoxy group, a 2-n-pentyloxyethoxy group, a 2-isopentyloxyethoxy group, a 2-tert-pentyloxyethoxy group, a 2-sec-pentyloxyethoxy group, a 2-cyclopentyloxyethoxy group, and alkoxy groups having an alkoxy group such as an alkoxy group, a 2-n-hexyloxyethoxy group, a 2-(4-ethylcyclohexyloxy)ethoxy group, a 2-n-nonyloxyethoxy group, a 2-(3,5,5-trimethylhexyloxy)ethoxy group, a 2-n-decyloxyethoxy group, a 2-n-dodecyloxyethoxy group, a 3-methoxypropyloxy group, a 3-ethoxypropyloxy group, a 3-(n-propyloxy)propyloxy group, a 2-isopentyloxypropyloxy group, a 2-methoxybutyloxy group, a 4-ethoxybutyloxy group, a 4-(n-propyloxy)butyloxy group, a 4-isopropyloxybutyloxy group, a 5-methoxypentyloxy group, a 5-ethoxymethoxy group, or a 6-n-propyloxyhexyloxy group; alkoxy groups having an alkoxyalkoxy group such as a methoxymethoxymethoxy group, an ethoxymethoxymethoxy group, a propyloxymethoxymethoxy group, a butyloxymethoxymethoxy group, a methoxyethoxymethoxy group, an ethoxyethoxymethoxy group, a propyloxyethoxymethoxy group, a methoxymethoxyethoxy group, an ethoxymethoxyethoxy group, a propyloxymethoxyethoxy group, a butyloxymethoxyethoxy group, a propyloxyethoxyethoxy group, a butyloxyethoxyethoxy group, a propyloxybutyloxyethoxy group, a methoxymethoxypropyloxy group, an ethoxymethoxypropyloxy group, a butyloxymethoxypropyloxy group, a methoxymethoxybutyloxy group, an ethoxymethoxybutyloxy group, a butyloxymethoxybutyloxy group, an ethoxyethoxybutyloxy group, a (4-ethylcyclohexyloxy)ethoxyethoxy group, or a [4-(3,5,5-trimethylhexyloxy)butyloxy]ethoxy group; alkoxy groups having an alkoxycarbonyl group, such as a methoxycarbonylmethoxy group, an ethoxycarbonylmethoxy group, an n-propyloxycarbonylmethoxy group, an isopropyloxycarbonylmethoxy group, or a (4'-ethylcyclohexyloxy)carbonylmethoxy group; alkoxy groups having an alkoxycarbonyl group, such as a methoxycarbonylethoxy group, an ethoxycarbonylethoxy group, an n-propyloxycarbonylethoxy group, or an ethoxycarbonylpropyloxy group; alkoxy groups having an alkylamino group, such as a methylaminomethoxy group, a 2-methylaminoethoxy group, a 2-(2-methylaminoethoxy)ethoxy group, a 4-methylaminobutyloxy group, a 1-methylaminopropan-2-yloxy group, a 3-methylaminopropyloxy group, a 2-methylamino-2-methylpropyloxy group, a 2-ethylaminoethoxy group, a 2-(2-ethylaminoethoxy)ethoxy group, a 3-ethylaminopropyloxy group, a 1-ethylaminopropyloxy group, a 2-isopropylaminoethoxy group, a 2-(n-butylamino)ethoxy group, a 3-(n-hexylamino)propyloxy group, or a 4-(cyclohexylamino)butyloxy group; alkoxy groups having a dialkylamino group, such as a dimethylaminomethoxy group, a 2-dimethylaminoethoxy group, a 2-(2-dimethylaminoethoxy)ethoxy group, a 4-dimethylaminobutyloxy group, a 1-dimethylaminopropan-2-yloxy group, a 3-dimethylaminopropyloxy group, a 2-dimethylamino-2-methylpropyloxy group, a 2-diethylaminoethoxy group, a 2-(2-diethylaminoethoxy)ethoxy group, a 3-diethylaminopropyloxy group, a 1-diethylaminopropyloxy group, a 2-diisopropylaminoethoxy group, a 2-(di-n-butylamino)ethoxy group, a 2-piperidylethoxy group, or a 3-(di-n-hexylamino)propyloxy group; alkoxy groups having an alkylaminoalkoxy group, such as a methylaminomethoxymethoxy group, a methylaminoethoxyethoxy group, a methylaminoethoxypropyloxy group, an ethylaminoethoxypropyloxy group, or a 4-(2'-isobutylaminopropyloxy)butyloxy group; alkoxy groups having a dialkylaminoalkoxy group, such as a dimethylaminomethoxymethoxy group, a dimethylaminoethoxyethoxy group, a dimethylaminoethoxypropyloxy group, a diethylaminoethoxypropyloxy group, or a 4-(2'-diisobutylaminopropyloxy)butyloxy group; alkoxy groups having an alkylthio group, such as a methylthiomethoxy group, a 2-methylthioethoxy group, a 2-ethylthioethoxy group, a 2-n-propylthioethoxy group, a 2-isopropylthioethoxy group, a 2-n-butylthioethoxy group, a 2-isobutylthioethoxy group, or a (3,5,5-trimethylhexylthio)hexyloxy group; Examples of the alkoxy group having a heterocyclic group include a 2-N-morpholinyl ethoxy group, a 2-N-pyridyl ethoxy group, a 2-N-pyrrolyl ethoxy group, a 2-(2-furyl)ethoxy group, a 2-(1-indolyl)ethoxy group, a 2-(3-thienyl)ethoxy group, a 3-N-morpholinyl propyloxy group, a 3-N-pyridyl propyloxy group, a 3-N-pyrrolyl propyloxy group, and a 3-(1-indolyl)propyloxy group.

[0042] The substituted or unsubstituted aryloxy group also includes a heteroaryloxy group, and is preferably a phenyloxy group, a 2-methylphenyloxy group, a 4-methylphenyloxy group, a 4-ethylphenyloxy group, a 4-isopropylphenyloxy group, a 4-isobutylphenyloxy group, a 4-n-pentylphenyloxy group, a 4-tert-pentylphenyloxy group, a 4-cyclohexylphenyloxy group, a 4-n-octylphenyloxy group, a 4-n-decylphenyloxy group, a 4-n-dodecylphenyloxy group, a 4-n-hexadecylphenyloxy group, a 2,3-dimethylphenyloxy group, a 2,5-dimethylphenyloxy group, a 3,4-dimethylphenyloxy group, a 3,4,5-trimethylphenyloxy group, a 5-indanyloxy group, a 1,2,3,4-tetrahydro-6-naphthyloxy group, a 3-methoxyphenyloxy group, a 3-ethoxyphenyloxy group, a 2-methoxy ... nyloxy group, 4-n-propoxyphenyloxy group, 4-n-butoxyphenyloxy group, 4-n-pentyloxyphenyloxy group, 4-cyclohexyloxyphenyloxy group, 4-n-octyloxyphenyloxy group, 4-n-decyloxyphenyloxy group, 4-n-dodecyloxyphenyloxy group, 4-n-hexadecyloxyphenyloxy group, 2,3-dimethoxyphenyloxy group, 2,5-dimethoxyphenyloxy group, 3,5-dimethoxyphenyloxy group, 2-methoxy-4-methylphenyloxy group, 3-methoxy-4-methylphenyloxy group, 3-methyl-4-methoxyphenyloxy group, 2-fluorophenyloxy group, 4-fluorophenyloxy group, 3-chlorophenyloxy group, 4-bromophenyloxy group, 3-trifluoromethylphenyloxy group, 3,5-difluorophenyloxy group, 3,Examples of the aryloxy group include a 4-dichlorophenyloxy group, a 2-methyl-4-chlorophenyloxy group, a 3-chloro-4-methylphenyloxy group, a 3-methoxy-4-fluorophenyloxy group, a 3-fluoro-4-methoxyphenyloxy group, a 4-phenylphenyloxy group, a 3-phenylphenyloxy group, a 4-(4'-methylphenyl)phenyloxy group, a 4-(4'-methoxyphenyl)phenyloxy group, a 1-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 6-n-butyl-2-naphthyloxy group, a 7-ethoxy-2-naphthyloxy group, a 2-thienyloxy group, a 2-pyridyloxy group, and a 4-pyridyloxy group.

[0043] Examples of unsubstituted alkylthio groups include linear, branched, or cyclic unsubstituted alkylthio groups such as a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, a tert-butylthio group, a sec-butylthio group, an n-pentylthio group, an isopentylthio group, an n-hexylthio group, a 2-methylpentylthio group, a 1,1-dimethylbutylthio group, a 1,2,2-trimethylpropylthio group, a 2-ethylbutylthio group, a 1,3-dimethylhexylthio group, a cyclohexylthio group, a methylcyclopentylthio group, an n-heptylthio group, an n-heptylthio group, an n-octylthio group, a 3,5,5-trimethylhexylthio group, an n-decylthio group, an n-undecylthio group, an n-dodecylthio group, a 1-adamantylthio group, or an n-pentadecylthio group.

[0044] Examples of the substituted alkylthio group include a methoxymethylthio group, an ethoxymethylthio group, an n-propyloxymethylthio group, an n-butyloxymethylthio group, an isobutyloxymethylthio group, a tert-butyloxymethylthio group, an n-pentyloxymethylthio group, a 2-methoxyethylthio group, a 2-ethoxyethylthio group, a 2-n-propyloxyethylthio group, a 2-isopropyloxyethylthio group, a 2-n-butyloxyethylthio group, a 2-isobutyloxyethylthio group, a 2-tert-butyloxyethylthio group, a 2-sec-butyloxyethylthio group, a 2-n-pentyloxyethylthio group, a 2-isopentyloxyethylthio group, a 2-sec-pentyloxyethylthio group, an alkylthio group having an alkoxy group, such as a 2-n-hexyloxyethylthio group, a 2-(4-ethylcyclohexyloxy)ethylthio group, a 2-n-nonyloxyethylthio group, a 2-(3,5,5-trimethylhexyloxy)ethylthio group, a 2-n-decyloxyethylthio group, a 2-n-dodecyloxyethylthio group, a 3-methoxypropylthio group, a 3-ethoxypropylthio group, a 3-(n-propylthio)propylthio group, a 2-isopentyloxypropylthio group, a 2-methoxybutylthio group, a 4-ethoxybutylthio group, a 4-(n-propyloxy)butylthio group, a 5-methoxypentylthio group, a 5-ethoxypentylthio group, or a 6-n-propyloxyhexylthio group; alkylthio groups having an alkoxyalkoxy group, such as a methoxymethoxymethylthio group, an ethoxymethoxymethylthio group, a propyloxymethoxymethylthio group, a butyloxymethoxymethylthio group, an ethoxyethoxymethylthio group, a propyloxyethoxymethylthio group, a methoxymethoxyethylthio group, an ethoxymethoxyethylthio group, a propyloxymethoxyethylthio group, a butyloxymethoxyethylthio group, a propyloxyethoxyethylthio group, a butyloxyethoxyethylthio group, a propyloxybutyloxyethylthio group, a methoxymethoxypropylthio group, an ethoxymethoxypropylthio group, a butyloxymethoxypropylthio group, a butyloxymethoxybutylthio group, an ethoxyethoxybutylthio group, a cyclohexyloxyethoxyethylthio group, or a [4-(3,5,5-trimethylhexyloxy)butyloxy]ethylthio group; an alkoxycarbonyl group, such as a methoxycarbonylmethylthio group, an ethoxycarbonylmethylthio group, an n-propyloxycarbonylmethylthio group, a methoxycarbonylethylthio group, an ethoxycarbonylethylthio group, an n-propyloxycarbonylethylthio group, or an ethoxycarbonylpropylthio group; alkylthio groups having an alkylamino group, such as a methylaminomethylthio group, a 2-methylaminoethylthio group, a 2-(2-methylaminoethoxy)ethylthio group, a 4-methylaminobutylthio group, a 1-methylaminopropan-2-yloxy group, a 3-methylaminopropylthio group, a 2-ethylaminoethylthio group, a 2-(2-ethylaminoethoxy)ethylthio group, a 3-ethylaminopropylthio group, a 1-ethylaminopropylthio group, a 2-isopropylaminoethylthio group, a 2-(n-butylamino)ethylthio group, a 3-(n-hexylamino)propylthio group, or a 4-(cyclohexylamino)butylthio group; alkylthio groups having a dialkylamino group, such as a dimethylaminomethylthio group, a 2-dimethylaminoethylthio group, a 4-dimethylaminobutylthio group, a 1-dimethylaminopropan-2-ylthio group, a 3-dimethylaminopropylthio group, a 2-diethylaminoethylthio group, a 3-diethylaminopropylthio group, a 2-diisopropylaminoethylthio group, a 2-(di-n-butylamino)ethylthio group, a 2-piperidylethylthio group, or a 3-(di-n-hexylamino)propylthio group; an alkylthio group having an alkylthio group, such as a methylthiomethylthio group, a 2-methylthioethylthio group, a 2-ethylthioethylthio group, a 2-n-propylthioethylthio group, a 2-isopropylthioethylthio group, a 2-n-butylthioethylthio group, a 2-isobutylthioethylthio group, or a (3,5,5-trimethylhexylthio)hexylthio group; Examples of such alkylthio groups include alkylthio groups having a heterocyclic group, such as a 2-N-morpholinylethylthio group, a 2-N-pyridylethylthio group, a 2-N-pyrrolylethylthio group, a 2-(2-furyl)ethylthio group, a 2-(1-indolyl)ethylthio group, a 2-(3-thienyl)ethylthio group, a 3-N-morpholinylpropylthio group, a 3-N-pyridylpropylthio group, a 3-N-pyrrolylpropylthio group, and a 3-(1-indolyl)propylthio group.

[0045] The substituted or unsubstituted arylthio group also includes a heteroarylthio group, and examples thereof include a phenylthio group, a 2-methylphenylthio group, a 4-methylphenylthio group, a 3-ethylphenylthio group, a 4-n-propylphenylthio group, a 4-isopropylphenylthio group, a 4-n-butylphenylthio group, a 4-isobutylphenylthio group, a 4-tert-butylphenylthio group, a 4-n-pentylphenylthio group, a 4-n-hexylphenylthio group, a 4-cyclohexylphenylthio group, a 4-n-octylphenylthio group, a 4-n-dodecylphenylthio group, a 4-n-octadecylphenylthio group, a 2,5-dimethylphenylthio group, a 3,4-dimethylphenylthio group, a 5-indanylthio group, a 1,2,3,4-tetrahydro-6-naphthylthio group, a 2-methoxyphenylthio group, a 3-methoxyphenylthio group, a 4-ethoxyphenylthio group, a 4-n-propoxyphenylthio group, a 2,4 -dimethoxyphenylthio group, 3,5-diethoxyphenylthio group, 2-methoxy-4-methylphenylthio group, 2-methyl-4-methoxyphenylthio group, 2-fluorophenylthio group, 4-fluorophenylthio group, 2-chlorophenylthio group, 4-bromophenylthio group, 4-trifluoromethylphenylthio group, 3-trifluoromethylphenylthio group, 2,4-difluorophenylthio group, 2,4-dichlorophenylthio group, 2-chloro-4-methoxyphenylthio group, 2-naphthylthio group, 4-methyl-1-naphthylthio group, 4-ethoxy-1-naphthylthio group, 2-pyridylthio group, 4-aminophenylthio group, 4-(N,N-dimethylamino)phenylthio group, 4-(N,N-diethylamino)-1-naphthylthio group, 4-[N,N-di(4'-methylphenyl)amino]phenylthio group, and 4-(N-phenoxadiyl)phenylthio group.

[0046] The substituent of the substituted amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group. Examples of the substituted amino group include monoalkylamino groups such as methylamino group, ethylamino group, propylamino group, butylamino group, pentylamino group, hexylamino group, heptylamino group, octylamino group, 2-ethylhexylamino group, cyclohexylamino group, 3,5,5-trimethylhexylamino group, nonylamino group, and decylamino group; dialkylamino groups such as a dimethylamino group, a diethylamino group, a methylethylamino group, a di-n-propylamino group, a di-n-butylamino group, a di-n-pentylamino group, an N-methyl-N-ethylamino group, an N-ethyl-N-isopropylamino group, an N-ethyl-N-cyclohexylamino group, or an N-methyl-N-octylamino group; amino groups having an aryl group, such as a phenylamino group, an N-methyl-N-phenylamino group, an N-ethyl-N-phenylamino group, an N-ethyl-N-(2,4-dimethylphenyl)amino group, an Nn-propyl-N-(2-ethoxyphenyl)amino group, an N-methyl-N-(3-chlorophenyl)amino group, a diphenylamino group, a di-(p-tolyl)amino group, or an N-methyl-N-(2-naphthyl)amino group; Examples of the amino group include amino groups having an aralkyl group, such as a benzylamino group, a phenethylamino group, a 3-phenylpropylamino group, a 4-ethylbenzylamino group, a 4-isopropylbenzylamino group, a dibenzylamino group, a diphenethylamino group, a bis(4-ethylbenzyl)amino group, a bis(4-isopropylbenzyl)amino group, an N-ethyl-N-benzylamino group, and an N-methyl-N-phenethylamino group.

[0047] Examples of the substituted or unsubstituted alkylcarbonyl group include an acetyl group, a propionyl group, a butyryl group, a valeryl group, an iso-valeryl group, a sec-valeryl group, a trimethylacetyl group, a hexanoyl group, a t-butylacetyl group, a heptanoyl group, an octanoyl group, a 2-ethylhexanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, a lauroyl group, a tridecanoyl group, a tetradecanoyl group, a pentadecanoyl group, a hexadecanoyl group, a heptanoyl group, a hex ... Examples of such groups include a tadecanoyl group, an octadecanoyl group, an oleyl group, a cyclopentanecarbonyl group, a cyclohexanecarbonyl group, a 6-chlorohexanoyl group, a 6-bromohexanoyl group, a trifluoroacetyl group, a pentafluoropropionyl group, a perfluorooctanoyl group, a 2,2,4,4,5,5,7,7,7-nonafluoro-3,6-dioxaheptanoyl group, a methoxyacetyl group, a 3,6-dioxaheptanoyl group, and a cinnamoyl group.

[0048] Examples of the substituted or unsubstituted arylcarbonyl group include a benzoyl group, a 2-methylbenzoyl group, a 3-methylbenzoyl group, a 4-methylbenzoyl group, a 4-ethylbenzoyl group, a 4-n-propylbenzoyl group, a 4-tert-butylbenzoyl group, a 2,4-dimethylbenzoyl group, a 2,4,6-trimethylbenzoyl group, a 2,4,5-trimethylbenzoyl group, a 4-ethylbenzoyl group, a 4-isopropylbenzoyl group, a 4-n-butylbenzoyl group, a 4-isobutylbenzoyl group, a 4-sec-butylbenzoyl group, a 4-tert-butylbenzoyl group, Examples of the benzoyl group include a benzoyl group, a 4-n-pentylbenzoyl group, a 4-isopentylbenzoyl group, a 4-neopentylbenzoyl group, a 4-isohexylbenzoyl group, a 4-cyclohexylbenzoyl group, a 4-octylbenzoyl group, a 4-cyanobenzoyl group, a 4-nitrobenzoyl group, a 4-trifluoromethylbenzoyl group, a 3-bromobenzoyl group, a 2-fluorobenzoyl group, a 4-chlorobenzoyl group, a 2,6-dichlorobenzoyl group, a 2,4-difluorobenzoyl group, a naphthylcarbonyl-1-yl group, and a naphthylcarbonyl-2-yl group.

[0049] Examples of the substituted or unsubstituted aminocarbonyl group include an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, an n-butylaminocarbonyl group, a sec-butylaminocarbonyl group, a tert-butylaminocarbonyl group, a dimethylaminocarbonyl group, a diethylaminocarbonyl group, a di-n-butylaminocarbonyl group, a di-sec-butylaminocarbonyl group, and a di-tert-butylaminocarbonyl group.

[0050] A carboxylate group can be represented by the formula: ROC(=O)-*, where R is a hydrocarbon group and * represents a bond. Examples of the carboxylate group include a methyl carboxylate group, an ethyl carboxylate group, an n-propyl carboxylate group, an isopropyl ester group, an n-butyl carboxylate group, a tert-butyl carboxylate group, an n-pentyl carboxylate group, an isopentyl carboxylate group, a cyclohexyl carboxylate group, an n-octyl carboxylate group, a trifluoropropyl carboxylate group, a benzyl carboxylate group, a phenyl carboxylate group, and a toluyl carboxylate group.

[0051] The sulfonate group can be represented by the formula ROS(=O)2-*, where R is a hydrocarbon group and * represents a bond. Examples of the sulfonate ester group include a methyl sulfonate group, an ethyl sulfonate group, an n-propyl sulfonate group, an isopropyl ester sulfonate group, an n-butyl sulfonate group, a tert-butyl sulfonate group, an n-pentyl sulfonate group, an isopentyl sulfonate group, a cyclohexyl sulfonate group, an n-octyl sulfonate group, a trifluoropropyl sulfonate group, a benzyl sulfonate group, a phenyl sulfonate group, and a toluyl sulfonate group.

[0052] R1 and R2, R2 and R 3、R3 and R4, R4 and R5, R5 and R6, R7 and R8, R8 and R9, R9 and R 10 may be bonded to form a ring structure. The ring structure is each of R to R 10 forms a ring structure including the carbon atom to which it is attached. The ring structure formed may be an aliphatic ring, an aromatic ring or a heterocyclic ring. Specific examples of the aliphatic ring include a cyclopentane ring, a cyclohexane ring, a cyclohexene ring, a cycloheptane ring, a cyclooctane ring, and a cyclodecane ring. Specific examples of the aromatic ring include a benzene ring and a naphthalene ring. Specific examples of the heterocycle include a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a pyrrole ring, and a silole ring. The aliphatic ring, aromatic ring or hetero ring formed may have a substituent. Examples of the substituent include a halogen atom, a carboxyl group, a cyano group, a nitro group, a hydroxyl group, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, or Examples of the alkyl group include an aryl group which may be substituted with a halogen atom, a carboxyl group, a cyano group, a nitro group, a hydroxyl group, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, and a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms.

[0053] In the present embodiment, Y in general formula (1-i) is as follows. Y represents a single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted alkynylene group, a substituted or unsubstituted arylene group, an oxygen atom, a sulfur atom, a carbonyl group, a sulfonyl group, a substituted or unsubstituted imino group, or a divalent to tetravalent hydrocarbon group containing a sulfur atom.

[0054] Y is preferably a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, an oxygen atom, a sulfur atom, a carbonyl group, a sulfonyl group, a substituted or unsubstituted imino group having 1 to 25 carbon atoms, or a divalent to tetravalent hydrocarbon group containing a sulfur atom.

[0055] Y is more preferably a single bond, a substituted or unsubstituted alkylene group having 1 to 12 carbon atoms, a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, an oxygen atom, a sulfur atom, a carbonyl group, a sulfonyl group, a substituted or unsubstituted imino group having 1 to 12 carbon atoms, or a divalent to tetravalent hydrocarbon group containing a sulfur atom. Examples of these substituents are shown below.

[0056] Examples of unsubstituted alkylene groups include linear or branched unsubstituted alkylene groups such as methylene, ethylene, n-propylene, isopropylene, n-butylene, isobutylene, sec-butylene, tert-butylene, n-pentylene, isopentylene, neopentylene, tert-pentylene, n-hexylene, 1-methylpentylene, 4-methyl-2-pentylene, 2-ethylbutylene, n-heptylene, 1-methylhexylene, n-octylene, 1-methylheptylene, and 2-ethylhexylene.

[0057] Examples of the substituted alkylene group include alkylene groups having an alkyloxy group, such as a methoxymethylene group, an ethoxymethylene group, an n-butoxymethylene group, an n-hexyloxymethylene group, and a (2-ethylbutyloxy)methylene group; Alkylene groups having an alkenyloxy group, such as a 2-(4'-pentenyloxy)ethylene group; an alkylene group having an aralkyloxy group, such as a benzyloxymethylene group or a 2-(benzyloxymethoxy)ethylene group; Alkylene groups having an aryloxy group, such as a phenyloxymethylene group, a 4-chlorophenyloxymethylene group, or a 4-(2'-phenyloxyethoxy)butylene group; Alkylene groups having an alkylthio group, such as an n-butylthiomethylene group or a 2-n-octylthioethylene group; Examples of the alkylene group include alkylene groups having a halogen atom, such as a fluoromethylene group, a trifluoromethylene group, a perfluoroethylene group, a 4-fluorocyclohexylene group, a dichloromethylene group, a 4-chlorocyclohexylene group, and a 7-chloroheptylene group.

[0058] Examples of substituted or unsubstituted alkenylene groups include a vinylene group, a propenylene group, a 1-butenylene group, an isobutenylene group, a 1-pentenylene group, a 2-pentenylene group, a 2-methyl-1-butenylene group, a 2-cyclopentenylene group, a 1-vinylhexylene group, a styrylene group, a styrylmethylene group, and a 2-styrylethylene group.

[0059] Examples of the substituted or unsubstituted alkynylene group include an acetylenylene group, a propynylene group, a 1-butynylene group, a 1-pentynylene group, a 2-pentynylene group, a 2-methyl-1-pentynylene group, and a phenylacetylenylene group.

[0060] Examples of the substituted or unsubstituted arylene group include unsubstituted arylene groups such as a phenylene group, a 1-naphthylene group, a 2-naphthylene group, a 2-anthracenylene group, a 1-phenanthrylene group, a 2-phenanthrylene group, a 3-phenanthrylene group, a 1-pyrenylene group, a 2-pyrenylene group, a 2-perylenylene group, a 3-perylenylene group, a 2-fluoranthenylene group, a 3-fluoranthenylene group, a 7-fluoranthenylene group, and an 8-fluoranthenylene group; arylene groups having an alkyl group, such as a 1-methyl-2-pyrenylene group, a 2-methylphenylene group, a 4-ethylphenylene group, a 4-(4'-tert-butylcyclohexyl)phenylene group, a 3-cyclohexylphenylene group, a 2-cyclohexylphenylene group, a 4-ethyl-1-naphthylene group, a 6-n-butyl-2-naphthylene group, or a 2,4-dimethylphenylene group; arylene groups having an alkoxy group or an aryloxy group, such as a 4-methoxyphenylene group, a 3-ethoxyphenylene group, a 2-ethoxyphenylene group, a 4-n-propoxyphenylene group, a 3-n-propoxyphenylene group, a 4-isopropoxyphenylene group, a 3-isopropoxyphenylene group, a 2-isopropoxyphenylene group, a 2-sec-butoxyphenylene group, a 4-n-pentyloxyphenylene group, a 4-isopentyloxyphenylene group, a 2-methyl-5-methoxyphenylene group, or a 2-phenyloxyphenylene group; arylene groups having an aryl group, such as a 4-phenylphenylene group, a 3-phenylphenylene group, a 2-phenylphenylene group, a 2,6-diphenylphenylene group, a 4-(2'-naphthyl)phenylene group, a 2-phenyl-1-naphthylene group, a 1-phenyl-2-naphthylene group, or a 7-phenyl-1-pyrenylene group; arylene groups having a halogen atom, such as a 4-fluorophenylene group, a 3-fluorophenylene group, a 2-fluorophenylene group, a 4-chlorophenylene group, a 4-bromophenylene group, a 2-chloro-5-methylphenylene group, a 2-chloro-6-methylphenylene group, a 2-methyl-3-chlorophenylene group, a 2-methoxy-4-fluorophenylene group, or a 2-fluoro-4-methoxyphenylene group; Examples of such groups include a 2-trifluoromethylphenylene group, a 3-trifluoromethylphenylene group, a 4-trifluoromethylphenylene group, a 3,5-bistrifluoromethylphenylene group, a 4-perfluoroethylphenylene group, a 4-methylthiophenylene group, a 4-ethylthiophenylene group, a 4-cyanophenylene group, and a 3-cyanophenylene group.

[0061] The substituent of the substituted imino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group.

[0062] Examples of the substituted imino group include monoalkylimino groups such as a methylimino group, an ethylimino group, a propylimino group, a butylimino group, a pentylimino group, a hexylimino group, a heptylimino group, an octylimino group, a 2-ethylhexylimino group, a cyclohexylimino group, a 3,5,5-trimethylhexylimino group, a nonylimino group, and a decylimino group; dialkylimino groups such as a dimethylimino group, a diethylimino group, a methylethylimino group, a di-n-propylimino group, a di-n-butylimino group, a di-n-pentylimino group, an N-methyl-N-ethylimino group, an N-ethyl-N-isopropylimino group, an N-ethyl-N-cyclohexylimino group, or an N-methyl-Nn-octylimino group; imino groups having an aryl group, such as an N-methyl-N-phenylimino group, an N-ethyl-N-phenylimino group, an N-ethyl-N-(2,4-dimethylphenyl)imino group, an Nn-propyl-N-(2-ethoxyphenyl)imino group, an N-methyl-N-(3-chlorophenyl)imino group, a diphenylimino group, a di-(p-tolyl)imino group, or an N-methyl-N-(2-naphthyl)imino group; Examples of imino groups include imino groups having an aralkyl group, such as a benzylimino group, a phenethylimino group, a 3-phenylpropylimino group, a 4-ethylbenzylimino group, a 4-isopropylbenzylimino group, a dibenzylimino group, a diphenethylimino group, a bis(4-ethylbenzyl)imino group, a bis(4-isopropylbenzyl)imino group, an N-ethyl-N-benzylimino group, and an N-methyl-N-phenethylimino group.

[0063] Examples of the divalent to tetravalent sulfur atom-containing hydrocarbon group include groups represented by the following general formulas (a) to (c). [ka]

[0064] Q1 in the general formula (a) may be a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted alkynylene group, a substituted or unsubstituted arylene group, etc. Examples of these groups include the same groups as those described above. Q2 in general formula (b) may be a trivalent group derived from an aliphatic hydrocarbon compound, a trivalent group derived from an alicyclic hydrocarbon compound, a trivalent group derived from an aromatic hydrocarbon compound, etc. Q3 in general formula (c) may be a tetravalent group derived from an aliphatic hydrocarbon compound, a tetravalent group derived from an alicyclic hydrocarbon compound, a tetravalent group derived from an aromatic hydrocarbon compound, etc.

[0065] Examples of the aliphatic hydrocarbon compound include methane, ethane, propane, butane, pentane, hexane, octane, nonane, and decane. Examples of the alicyclic hydrocarbon compound include cyclopropane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, norbornene, methylcyclohexane, and norbornadiene. Examples of aromatic hydrocarbon compounds include monocyclic aromatic compounds such as benzene, toluene, xylene, mesitylene, cumene, butylbenzene, and styrene, and condensed polycyclic aromatic compounds having 3 to 6 rings such as naphthalene, phenanthrene, anthracene, and pyrene. * represents a bond.

[0066] n is an integer of 1 to 3, and is preferably 1 or 2.

[0067] R 11 and R 12 , R 12 and R 13、 R 13 and R 14 may be linked together to form a ring structure. The ring structure may be formed by combining each of R 11 ~R 14 can form a ring structure including the carbon atom to which it is attached. The ring structure formed may be an aliphatic ring, an aromatic ring, or a heterocyclic ring. The aliphatic ring, the aromatic ring, and the heterocyclic ring may be the same as those described above.

[0068] In general formula (1-i), preferred is (1) a combination in which n is an integer of 1 to 3 and Y is a single bond, or (2) a combination in which n is an integer of 1 to 3 and Y is a substituted or unsubstituted alkylene group having 1 to 12 carbon atoms, an oxygen atom, a sulfur atom, a substituted or unsubstituted imino group having 1 to 12 carbon atoms, or a divalent to tetravalent sulfur atom-containing hydrocarbon group.

[0069] The quinophthalone compound of the present embodiment preferably has a maximum absorption wavelength of 400 nm to 500 nm, and more preferably 440 nm to 470 nm.

[0070] The quinophthalone compound represented by the above general formula (1) has a tautomer shown in the following (2), which is also included in the present invention.

[0071] [ka]

[0072] Specific examples of the quinophthalone compound represented by the general formula (1) of this embodiment are shown in Table 1 below, but are not limited to these examples.

[0073] [Table 1]

[0074] [Table 2]

[0075] [Table 3]

[0076] [Table 4]

[0077] [Table 5]

[0078] [Table 6]

[0079] [Table 7]

[0080] [Table 8]

[0081] [Table 9]

[0082] [Table 10]

[0083] [Table 11]

[0084] [Method of producing quinophthalone compounds] The quinophthalone compound represented by formula (1) of the present embodiment may be produced by a known method. For example, it can be produced by the methods described in JP-A-05-039269, Med Chem Res (2011) 20:1638-1642, and the like.

[0085] The method for producing the quinophthalone compound of the present embodiment can be carried out, for example, as shown in the following reaction formula: A step a of reacting a compound (a) represented by the following formula (a) with a compound (b) represented by the following formula (b) to prepare a quinophthalone compound (c) represented by the following formula (c); Then, a step b of reacting the compound (c) with a chlorinating agent to prepare an acid chloride (d) represented by the following formula (d); and a step c of reacting the obtained acid chloride (d) with a compound (e) represented by the following formula (e) to prepare an amidated product (f) represented by the following formula (f), and further treating the amidated product (f) with a dehydrating agent to produce a quinophthalone compound of the formula (1). In addition, R1 to R2 in the following general formulas (a) to (f) 14 R1 to R in general formula (1) 14 is the same as:

[0086] [ka]

[0087] In step a, compound (a) is reacted with compound (b) in an organic solvent. Examples of the organic solvent include sulfolane, N-methyl-2-pyrrolidone, and 1,3-dimethyl-imidazolidinone. Step a can be carried out under atmospheric pressure at a reaction temperature of 170° C. to 200° C. for a reaction time of about 10 to 20 hours. The molar ratio (a / b) of compound (a) to compound (b) can be set to 0.5 to 1.0. By the step a, a quinophthalone compound (c) represented by formula (c) can be obtained. Specifically, the quinophthalone compound (c) is obtained as a reaction solution containing the quinophthalone compound (c), and can be purified by a known method.

[0088] In step b, a chlorinating agent and a quinophthalone compound (c) are reacted in an organic solvent to prepare an acid chloride (d) represented by formula (d). The organic solvent may be an organic solvent contained in a reaction solution containing the quinophthalone compound (c). When a purified quinophthalone compound (c) is used, it can be dissolved in an organic solvent such as toluene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, or 1,3-dimethyl-imidazolidinone and used in the reaction. Examples of the chlorinating agent include thionyl chloride, phosphorus oxychloride, and oxalyl chloride. The reaction in step b can be carried out in the presence of a catalyst, such as N,N-dimethylformamide. Step b can be carried out under atmospheric pressure, at a reaction temperature of 60° C. to 80° C., and for a reaction time of about 5 hours to 20 hours. The amount of the chlorinating agent added can be set to a molar ratio (chlorinating agent / c) to the quinophthalone compound (c) of 1.0 to 1.5.

[0089] In step c, an acid chloride (d) is reacted with a compound (e) in an organic solvent to prepare an amidated compound (f). The organic solvent may be the organic solvent contained in the reaction solution containing the acid chloride (d), or may be added separately. Step c can be carried out under atmospheric pressure, the reaction temperature is room temperature, and the reaction time is about 1 hour to 5 hours. The amount of the compound (e) added can be set to a molar ratio (e / d) of 1.0 to 1.5 relative to the acid chloride (d).

[0090] Next, the amidated product (f) is reacted with a dehydrating agent to produce the quinophthalone compound of formula (1). Examples of the dehydrating agent include acetic anhydride, concentrated sulfuric acid, and N,N-dicyclohexylcarbodiimide. The reaction can be carried out under atmospheric pressure at a reaction temperature of 50° C. to 130° C. for a reaction time of about 1 hour to 5 hours.

[0091] After the reaction in step c, known purification may be carried out as necessary to obtain the quinophthalone compound of formula (1).

[0092] [Resin composition] The resin composition of the present embodiment is (A) Thermoplastic resin or thermosetting resin (hereinafter, when referring to either alone or both, it will be referred to as resin for convenience) (B) one or more selected from the quinophthalone compounds represented by the general formula (1) (hereinafter, for convenience, referred to as quinophthalone compounds). The resin used in the resin composition of the present embodiment may be either a thermoplastic resin or a thermosetting resin, but is preferably a transparent resin.

[0093] Examples of the thermoplastic resin include polycarbonate resin, polyamide resin, polyester resin, acrylic resin, polystyrene resin, acrylonitrile-styrene resin, norbornene resin, and cellulose-based resin, and at least one selected from polycarbonate resin, polyamide resin, acrylic resin, and polyester resin is preferable.

[0094] Polycarbonate resins are polymers obtained mainly by the phosgene process, in which dihydroxydiaryl compounds are reacted with phosgene, or by the transesterification process, in which dihydroxydiaryl compounds are reacted with carbonates such as diphenyl carbonate. A representative example is polycarbonate resin made from 2,2-bis(4-hydroxyphenyl)propane (bisphenol A).

[0095] Examples of the dihydroxydiaryl compounds include, in addition to bisphenol A, (hydroxyaryl)aryls such as bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)octane, 2,2-bis(4-hydroxyphenyl)phenylmethane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 2,2-bis(4-hydroxy-3-tert-butylphenyl)propane, 1,1-bis(4-hydroxy-3-tert-butylphenyl)propane, 2,2-bis(4-hydroxy-3-bromophenyl)propane, 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane, and 2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane. Examples of the aryl sulfoxide include leucanes, (hydroxyaryl)cycloalkanes such as 1,1-bis(4-hydroxyphenyl)cyclopentane and 1,1-bis(4-hydroxyphenyl)cyclohexane, dihydroxydiaryl ethers such as 4,4'-dihydroxydiphenyl ether and 4,4'-dihydroxy-3,3'-dimethyldiphenyl ether, dihydroxydiaryl sulfides such as 4,4'-dihydroxydiphenyl sulfide, dihydroxydiaryl sulfoxides such as 4,4'-dihydroxydiphenyl sulfoxide and 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfoxide, and dihydroxydiaryl sulfones such as 4,4'-dihydroxydiphenyl sulfone and 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfone.

[0096] These may be used alone or in combination with two or more of them. In addition, piperazine, dipiperidylhydroquinone, resorcin, 4,4'-dihydroxydiphenyl, etc. may be used in combination. The viscosity average molecular weight of the polycarbonate resin is usually 10,000 to 100,000, preferably 10,000 to 400,000.

[0097] Furthermore, the above dihydroxyaryl compounds may be used in combination with the following trivalent or higher phenol compounds: Examples of trivalent or higher phenols include phloroglucin, 1,3,5-tri-(4-hydroxyphenyl)-benzene, and 1,1,1-tri-(4-hydroxyphenyl)-ethane.

[0098] The polyamide resin is a resin having a structure of a dehydration polycondensation product of diamine compounds containing aromatic or aliphatic groups and dicarboxylic acid compounds containing aromatic or aliphatic groups. Here, the aliphatic group includes an alicyclic aliphatic group. The resin having a structure of a dehydration polycondensation product of the diamine compounds and dicarboxylic acid compounds is not necessarily limited to those obtained by a dehydration polycondensation reaction, and can also be obtained, for example, by ring-opening polymerization of one or more lactam compounds.

[0099] Examples of the diamine compounds include hexamethylenediamine, m-xylylenediamine, bis(4-aminocyclohexyl)methane, bis(4-amino-3-methylcyclohexyl)methane, trimethylhexamethylenediamine, bis(aminomethyl)norbornane, and bis(aminomethyl)tetrahydrodicyclopentadiene. One or more of these diamine compounds can be selected and used.

[0100] Examples of the dicarboxylic acid compounds include adipic acid, dodecanedicarboxylic acid, isophthalic acid, terephthalic acid, bis(hydroxycarbonylmethyl)norbornane, and bis(hydroxycarbonylmethyl)tetrahydrodicyclopentadiene. One or more of these dicarboxylic acid compounds can be selected and used.

[0101] In particular, from the viewpoint of transparency, non-crystalline polyamide resins are preferred, which are generally referred to as transparent nylons, and examples thereof include Grilamid TR-55, Grilamid TR-90, and Grilamid TR-XE3805 manufactured by EMS Corporation, and Trogamid CX-7323 manufactured by Huels Corporation.

[0102] The acrylic resin is a polymer mainly composed of alkyl methacrylate, and may be a homopolymer of alkyl methacrylate, a copolymer using two or more kinds of alkyl methacrylate, or a copolymer of 50% by weight or more of alkyl methacrylate and 50% by weight or less of a monomer other than alkyl methacrylate. As the alkyl methacrylate, one having an alkyl group with 1 to 4 carbon atoms is usually used, and among them, methyl methacrylate is preferably used.

[0103] The monomer other than the alkyl methacrylate may be a monofunctional monomer having one polymerizable carbon-carbon double bond in the molecule, or a polyfunctional monomer having two or more polymerizable carbon-carbon double bonds in the molecule, but the monofunctional monomer is particularly preferably used. Examples of the monomer include alkyl acrylates such as methyl acrylate and ethyl acrylate, styrene-based monomers such as styrene and alkylstyrene, and unsaturated nitriles such as acrylonitrile and methacrylonitrile.

[0104] The acrylic resin is preferably a polymer whose monomer is substantially only alkyl methacrylate, or a copolymer in which alkyl methacrylate accounts for, for example, 70% by weight or more, preferably 90% by weight or more of the monomer composition, and which is substantially composed of only a monomer selected from alkyl acrylate, styrene monomer, and unsaturated nitrile. In particular, a polymer whose monomer is substantially only alkyl methacrylate is most preferable, and a representative example is polymethyl methacrylate resin (PMMA). Many commercially available polymethyl methacrylate resins are available, such as MX150 manufactured by Soken Chemical Industry Co., Ltd., Eposter MA manufactured by Nippon Shokubai Co., Ltd., and MBX series manufactured by Sekisui Chemical Co., Ltd.

[0105] Among acrylic resins, poly(meth)acrylic acid ester-based resins have a low glass transition temperature, for example, a glass transition temperature of less than 0°C, preferably less than -20°C, and are used as pressure sensitive adhesives, bonding agents, etc., and are widely used, for example, for bonding layers of optical filters for thin displays, or for bonding optical filters to display screens.

[0106] The poly(meth)acrylic ester resin used as the adhesive is preferably one containing 50% by weight or more of a (meth)acrylic ester having an alkyl group having 1 to 14 carbon atoms as a monomer.

[0107] Examples of (meth)acrylic acid esters having an alkyl group having 1 to 14 carbon atoms include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, i-octyl (meth)acrylate, benzyl (meth)acrylate, dicyclopentenyl (meth)acrylate, phenoxyethyl (meth)acrylate, and phenoxydiethylene glycol (meth)acrylate.

[0108] Other examples of copolymerizable monomers include (meth)acrylates such as hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, methoxyethyl (meth)acrylate, ethoxyethyl (meth)acrylate, and ethoxyethoxyethyl (meth)acrylate; Styrenic monomers such as α-methylstyrene, vinyltoluene, and styrene; Vinyl ether monomers such as methyl vinyl ether, ethyl vinyl ether, and isobutyl vinyl ether; Fumaric acid, monoalkyl esters of fumaric acid, dialkyl esters of fumaric acid; Examples of the alkyl group include maleic acid, monoalkyl esters of maleic acid, dialkyl esters of maleic acid, itaconic acid, monoalkyl esters of itaconic acid, dialkyl esters of itaconic acid, (meth)acrylonitrile, vinyl chloride, vinylidene chloride, vinyl acetate, vinyl ketone, vinylpyridine, and vinylcarbazole.

[0109] A typical example of polyester resin is PolyC. 2-4 Alkylene terephthalate and poly C 2-4Homopolyesters such as alkylene naphthalates, C 2-4 Alkylene arylate unit (C 2-4 Alkylene terephthalate and / or C 2-4 Examples of such polyesters include copolyesters containing alkylene naphthalate units as the main component, but also include polyarylate resins, aliphatic polyesters using aliphatic dicarboxylic acids such as adipic acid, and homopolymers or copolymers of lactones such as ε-caprolactone.

[0110] Copolyesters include polyC 2-4 Among the constituent units of alkylene arylate, C 2-4 Part of the alkylene glycol is replaced with polyoxy C 2-4 Alkylene glycol, C 6-10 Copolyesters in which some of the aromatic dicarboxylic acids have been substituted with unsymmetric aromatic dicarboxylic acids such as phthalic acid and isophthalic acid, and aliphatic C dicarboxylic acids such as adipic acid, etc. 6-12 Copolyesters substituted with dicarboxylic acids and the like are included.

[0111] As the polyester resin, polyethylene terephthalate (PET), polytrimethylene terephthalate (PTT), polybutylene terephthalate (PBT), polyethylene naphthalate (PEN), etc. are preferred because of their high transparency. 2-4 Amorphous copolyesters such as alkylene arylate copolyesters are also preferred because they have excellent processability. PET is particularly preferred because it is mass-produced and has excellent heat resistance, strength, etc.

[0112] Examples of thermosetting resins include allyl diglycol carbonate monomer, diallyl phthalate monomer, mixtures of isocyanate compounds with polyols or polythiols, and cured products of monomers used in the manufacture of corrective lenses, such as acrylic monomers. However, it is preferable to use at least one selected from polyurethane resins obtained by the polymerization reaction of isocyanate compounds with polyols, polythiourethane resins obtained by the polymerization of isocyanate compounds with polythiol compounds, and allyl diglycol carbonate resins obtained by the curing of allyl diglycol carbonate monomer.

[0113] The polyurethane resin is mainly composed of a blocked polyisocyanate and a polyol. Examples of the blocked polyisocyanate include adducts in which several molecules of hexamethylene diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, isophorone diisocyanate, and hydrogenated xylylene diisocyanate are bonded together, and isocyanurates and allophanates are blocked with acetoacetic acid or malonic acid. Examples of the polyol include polyesters, polyethers, polycarbonates, polyacrylates, and polycaprolactones having hydroxyl groups.

[0114] A representative example of the polythiourethane resin is a polythiourethane resin produced from metaxylylene diisocyanate and pentaerythritol tetrakis(3-mercaptopropionate).

[0115] The allyl diglycol carbonate resin is preferably polydiethylene glycol bisallyl carbonate, and an example thereof is CR-39 resin (also called ADC resin).

[0116] The blending amount of the resin and the quinophthalone compound in the resin composition of the present invention varies depending on the application and the thickness of the molded article, but it is sufficient that the concentration is within the limit where the light transmission and transparency are not lost, and is usually adjusted so that the visible light transmittance in the thickness direction of the molded article is 12 to 99%, preferably 20 to 90%. For example, if the quinophthalone compound is mixed with a polycarbonate resin in a 2.15 mm thick eyeglass lens, the amount of the quinophthalone compound used is 0.001 to 0.1% by weight relative to the resin (A). In general, if the thickness of the molded article is 0.1 mm to 20 mm, the amount of the quinophthalone compound used is 0.0001 to 2% by weight relative to the thermoplastic resin or thermosetting resin.

[0117] In addition to the resin and the quinophthalone compound, the resin composition of the present invention may contain known ultraviolet absorbers, infrared absorbers, various resin additives, and various dyes, as necessary. Examples of the various dyes include tetraazaporphyrin compounds, and examples of the various resin additives include phenolic antioxidants, release agents, dyes and pigments, phosphorus-based heat stabilizers, weather resistance improvers, antistatic agents, antifogging agents, lubricants / antiblocking agents, flame retardants, flow improvers, plasticizers, dispersants, and antibacterial agents.

[0118] The method for producing the resin composition of the present invention will be described below. The resin composition of the present invention is obtained by mixing a quinophthalone compound with a thermoplastic resin or a thermosetting resin, and it is desirable that the quinophthalone compound and the resin are in a compatible state at least in a molded article obtained by molding the composition.

[0119] When the resin of the resin composition is a thermoplastic resin, the quinophthalone compound and powder or pellets of the thermoplastic resin are mixed using various mixers such as a tumbler or a Henschel mixer to obtain a resin composition, which is then melt-kneaded using a known melt-kneader such as a Banbury mixer, a heating roll, a Brabender, a single-screw kneading extruder, a twin-screw kneading extruder, or a kneader to produce a resin composition containing the quinophthalone compound and the thermoplastic resin uniformly.

[0120] Alternatively, the thermoplastic resin and the quinophthalone compound can be dissolved and mixed in an organic solvent capable of dissolving them, and then the organic solvent can be removed to produce the resin composition. The organic solvent used in this case includes hexane, heptane, acetone, methyl ethyl ketone, benzene, toluene, dichloromethane, chloroform, etc., but is not particularly limited as long as it is chemically inactive with the resin composition and has an appropriately low boiling point.

[0121] It is also possible to produce the composition by dissolving the quinophthalone compound in a solvent, and then contacting the resin or polymer molded body to diffuse and penetrate the quinophthalone compound into the resin, and the resin composition thus obtained is also within the scope of the present invention. The organic solvent in which the quinophthalone compound is dissolved is not particularly limited, but it should not decompose the quinophthalone compound or alter the thermoplastic resin. Usually, liquid ketones or alcohols are often used. The concentration of the solution is arbitrary depending on the purpose, but usually, about 0.01% to 30% is in the good range. The diffusion conditions vary depending on the type of the quinophthalone compound, the solvent, the thermoplastic resin, etc., but are usually at normal pressure or under pressure, at 25°C to 200°C, for several minutes to 5 hours.

[0122] Furthermore, the quinophthalone compound may be mixed with the raw material monomer of the thermoplastic resin by the above-mentioned method, and then polymerized. This manufacturing method will be described below in the case where the resin of the resin composition is a thermosetting resin.

[0123] When the resin of the resin composition is a thermosetting resin, there are two methods: dissolving the quinophthalone compound in a solvent and then contacting the resin or a polymer molded product to cause the quinophthalone compound to diffuse and penetrate into the resin; or mixing the quinophthalone compound with the raw material monomer of the thermosetting resin and then polymerizing it, and the latter method is more commonly used. The latter method is described below.

[0124] In the step of mixing a quinophthalone compound with a raw material monomer for a thermosetting resin, depending on what the quinophthalone compound is to be mixed with, there may be used a method in which the quinophthalone compound is mixed with any one of the monomer groups constituting the monomer mixture and then used to prepare a monomer mixture, a method in which the quinophthalone compound is mixed with a mixture of the monomer mixture and other additives and then a catalyst is added, or a method in which the quinophthalone compound is mixed with a mixture of the monomer mixture, the catalyst, and other additives. Components other than the monomer and the quinophthalone compound used in polymerization curing include a polymerization catalyst and other additives.

[0125] Known examples of polymerization catalysts include organic peroxides, such as diacyl peroxides, peroxydicarbonates, peroxy esters, peroxy ketals, dialkyl peroxides, and hydroperoxides.

[0126] Other additives include catalysts such as dibutyltin dichloride, ultraviolet absorbers, internal release agents such as acidic phosphate esters, light stabilizers, antioxidants, reaction initiators such as radical reaction initiators, chain extenders, crosslinking agents, fillers, and the like. Further examples of the additives include known resin modifiers added as necessary, such as hydroxy compounds, thiol compounds, epoxy compounds, episulfide compounds, organic acids and their anhydrides, and olefin compounds including (meth)acrylate compounds.

[0127] When mixing the quinophthalone compound with the raw material monomer of the thermosetting resin, the quinophthalone compound may be mixed directly, or the quinophthalone compound may be dissolved in a low-boiling organic solvent in advance, and the organic solvent solution may be mixed with the raw material monomer, and then the organic solvent may be evaporated and removed under conditions of heating and / or reduced pressure, etc. Examples of the organic solvent used in this case include hexane, heptane, acetone, methyl ethyl ketone, benzene, toluene, dichloromethane, chloroform, etc., but there is no particular limitation as long as it is chemically inactive with the raw material monomer and has an appropriately low boiling point.

[0128] In mixing, the quinophthalone compound may be mixed in an amount corresponding to the concentration of the quinophthalone compound required for the resin composition, or a master batch may be prepared in which the quinophthalone compound is contained in one of the components, such as one of the raw material monomers, at a concentration higher than the desired concentration, and other components to be blended may be added as necessary to dilute the master batch to produce a resin composition of the desired concentration. In dissolving the quinophthalone compound, the resin composition may be heated within a range that does not cause practical problems in terms of deterioration of the resin composition, pot life, etc. The conditions for polymerization and curing will be explained in the cast polymerization method for molded articles described below.

[0129] [Molded body] The molded article of this embodiment will be described below. The molded article of the present embodiment is produced by molding the resin composition of the present embodiment. The molded article may be an optical article made of the resin composition, or an optical article partially containing the resin composition, or it may be an intermediate material for producing an optical article, such as a powder, pellet, or film.

[0130] As described below, examples of the optical article include anti-glare optical articles such as eyeglass lenses, sun visors, helmet shields, anti-glare coatings or anti-glare films for display devices of information devices, various filters, covers for lighting devices, etc. Further examples include optical filters used to improve the life of image display devices such as liquid crystal display devices and organic EL displays, and to improve contrast in bright rooms.

[0131] In this specification, an optical article partially containing the resin composition includes an optical article in which the resin composition is contained inside various members or films of the optical article, and an optical article in which the resin composition is coated or attached to the surface of a member or each layer.

[0132] The molding method varies depending on the product and the type of resin used. In the case of a resin composition using a thermoplastic resin, for example, compression molding, transfer molding, extrusion molding, injection molding, etc. are used, while in the case of a resin composition using a thermosetting resin, for example, cast polymerization is used. The cast polymerization method will be described below.

[0133] The resin composition is injected into a casting mold and then the casting mold is heated in a heating device such as an oven or underwater for several to several tens of hours according to a predetermined temperature program. The temperature and time of polymerization curing vary depending on the composition of the mixture, the type of catalyst, the shape of the mold, etc., but are generally about -50 to 200°C for 1 to 100 hours. Usually, the polymerization is started at a temperature in the range of 5°C to 40°C, and then the temperature is gradually increased to a range of 80°C to 130°C, and the mixture is generally heated at that temperature for 1 to 4 hours. After hardening and molding, the desired molded product can be obtained by removing it from the casting mold. Also, there is a method in which a resin or a resin monomer and a quinophthalone compound are dispersed or dissolved in an organic solvent, and a polymer molded article is produced by a casting method.

[0134] The molded article of the resin composition of this embodiment is extremely useful as an anti-glare optical article. Examples of anti-glare optical articles include eyeglass lenses, sun visors, helmet shields, films for automobile and airplane windshields, automobile headlight covers, ski goggles, anti-glare coatings or anti-glare films for display devices of information devices, and LED lighting filters, and the like, and the articles can be used without limitation for any application for the purpose of suppressing glare and ensuring contrast and natural color tones. The method for producing the antiglare optical article varies depending on the form of the article and the type of resin, and the above-mentioned methods for producing molded articles can be applied.

[0135] Depending on the functions required for the anti-glare optical article, one or more of the following functions may be provided: anti-reflection function, hard coat function (friction resistance function), antistatic function, anti-fouling function, gas barrier function, and ultraviolet ray blocking function.

[0136] Next, the optical filter will be described. The optical filter of the present invention preferably contains the quinophthalone compound represented by the general formula (1) in the substrate. In the present invention, "containing in the substrate" means that the compound is contained inside the substrate, that the compound is applied to the surface of the substrate, or that the compound is sandwiched between substrates.

[0137] Examples of the substrate include resin and glass, with resin being preferred. The resin may be in various forms, such as an adhesive, a sheet, a film, or a binder resin. A combination of a plurality of forms, such as a sheet having an adhesive, may also be used.

[0138] The thickness of the substrate is not particularly limited as long as it has a certain degree of mechanical strength, but is usually from 20 μm to 10 mm, preferably from 20 μm to 1 mm, and more preferably from 20 μm to 200 μm.

[0139] Methods for producing the optical filter of the present application using the quinophthalone compound represented by general formula (1) are not limited, but include (1) a method in which the compound is incorporated into a transparent adhesive, (2) a method in which the compound is incorporated into a polymer molded product, and (3) a method in which the compound is coated onto a polymer molded product or a glass surface.

[0140] Methods for incorporating the quinophthalone compound into the polymer molded article mentioned in (2) include a method in which the quinophthalone compound is kneaded into a resin and then heated and molded, and a method in which a polymer molded article is produced by a casting method in which a resin or a resin monomer and the quinophthalone compound are dispersed and dissolved in an organic solvent.

[0141] Processing conditions, such as processing temperature and film-forming conditions, vary slightly depending on the quinophthalone compound and base polymer used, but examples include a method in which a quinophthalone compound is added to a powder or pellet of a base polymer, heated to 150-350°C, dissolved, and then molded to produce a plate. A method in which a film is formed using an extruder. A method in which a raw roll is produced using an extruder, and stretched 2-5 times its original size uniaxially or biaxially at 30-120°C to produce a film with a thickness of 10-200 μm.

[0142] During kneading, additives such as plasticizers that are normally used in resin molding may be added. The amount of the quinophthalone compound added varies depending on the absorption coefficient, the thickness of the polymer molded product to be produced, the desired absorption intensity, the desired transparency and transmittance, etc., but is usually 1 ppm to 20 wt.%, preferably 1 ppm to 10 wt.%, and particularly preferably 1 ppm to 5 wt.%, based on the weight of the base polymer molded product.

[0143] In the casting method, a quinophthalone compound is added and dissolved in an organic solvent solution of resin or resin monomer, and if necessary a plasticizer, polymerization initiator, and antioxidant are added. The mixture is poured into a mold or drum with the required surface condition, and then the solvent is evaporated and dried, or polymerized, solvent is evaporated, and dried to produce a plate or film.

[0144] Examples of resins that can be used include aliphatic ester resins, acrylic resins, melamine resins, urethane resins, aromatic ester resins, polycarbonate resins, aliphatic polyolefin resins, aromatic polyolefin resins, polyvinyl resins, polyvinyl alcohol resins, polyvinyl-modified resins (PVA, EVA, etc.), and copolymer resin monomers thereof.

[0145] Examples of the solvent include halogen-based, alcohol-based, ketone-based, ester-based, aliphatic hydrocarbon-based, aromatic hydrocarbon-based, ether-based solvents, and mixtures thereof.

[0146] The concentration of the quinophthalone compound varies depending on the absorption coefficient of the dye, the thickness of the plate or film, the desired absorption intensity, and the desired transmission characteristics and transmittance, but is usually 1 ppm to 20% by weight based on the weight of the resin monomer. The resin concentration is 1 to 90% by weight based on the total paint.

[0147] Examples of the method of coating the polymer molded body or glass surface mentioned in (3) include a method of dissolving the quinophthalone compound in a binder resin and an organic solvent to form a coating, and a method of dispersing the quinophthalone compound finely ground (50 to 500 nm) in an uncolored acrylic emulsion paint to form an acrylic emulsion water-based paint. Examples of the binder resin include aliphatic ester resins, acrylic resins, melamine resins, urethane resins, aromatic ester resins, polycarbonate resins, aliphatic polyolefin resins, polyvinyl resins, polyvinyl alcohol resins, polyvinyl resins (PVA, EVA, etc.), or copolymer resins thereof. Examples of the solvent include halogen-based, alcohol-based, ketone-based, ester-based, aliphatic hydrocarbon, aromatic hydrocarbon, ether-based solvents, or mixtures thereof. The concentration of the quinophthalone compound varies depending on the absorption coefficient, coating thickness, desired absorption intensity, desired visible transmittance, etc., but is usually 0.1 ppm to 30% by weight based on the weight of the binder resin. The resin concentration is usually 1 to 50% by weight based on the total dye. In the case of acrylic emulsion-based water-based paint, it is obtained by dispersing finely ground (50 to 500 nm) pigment in uncolored acrylic emulsion paint in the same manner as above. Additives such as antioxidants that are used in normal paints may be added to the paint.

[0148] The method for coating the polymer molded article or glass surface can be appropriately selected from coating methods using a bar coater, blade coater, spin coater, reverse coater, die coater, spray, and the like.

[0149] The optical filter containing the quinophthalone compound of the general formula (1) of the present invention can be used for the purposes of extending the life of organic EL light-emitting devices, improving the contrast of liquid crystal displays, cutting blue light in LED liquid crystal displays, and improving the durability of near infrared absorption cut filters.

[0150] Although the embodiments of the present invention have been described above, these are merely examples of the present invention, and various configurations other than those described above can be adopted as long as they do not impair the effects of the present invention. EXAMPLES

[0151] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples.

[0152] Example 1: Preparation of specific compound (3-21) 8.54g of trimellitic anhydride was added to 41.8mL of dehydrated sulfolane and the temperature was raised to 180-185℃. 7.00g of 3-hydroxy-6-methoxyquinaldine-4-carboxylic acid was added in portions and the temperature was raised to 193-197℃, followed by stirring for 13 hours. After cooling the reaction solution to 60℃, 24.04g of methanol was added, and the solution was gradually cooled to 30℃. The solution was then filtered, washed with methanol, and dried to obtain 8.80g of intermediate (C). 7.00 g of intermediate (C) was placed in 53.2 mL of toluene and heated to 73-77°C. 0.17 g of N,N-dimethylformamide and 2.57 g of thionyl chloride were added dropwise to the toluene solution, and the mixture was stirred at 73-87°C for 20 hours. The remaining thionyl chloride was removed by distillation under reduced pressure, and the mixture was cooled to room temperature. Next, a solution of 3.17 g of anthranilic acid dissolved in 12.05 g of N,N-dimethylacetamide was added dropwise, and the mixture was stirred at room temperature for 6 hours. Further, 8.85 g of acetic anhydride was charged and the temperature was raised to 110° C. After stirring at 110-150° C. for 3 hours, the mixture was cooled to 60° C., and 8.3 g of methanol was added dropwise. After stirring at 60-65° C. for 30 minutes, the mixture was filtered, washed with methanol, and dried to obtain 5.64 g of the target product (3-21). [ka]

[0153] The resulting compound was confirmed to be the desired compound based on the following analytical results. ESI-Mass: 465(M+H) + , 463(MH) - The N,N-dimethylformamide solution of the compound thus obtained exhibited a maximum absorption at 451 nm, as shown in the transmission spectrum of Figure 1, and a gram absorption coefficient of 6.60 × 10 4 The concentration was mL / g cm. The Tg_DTA was measured and the Tg(-5wt%) was 419.3℃. The HOMO value was measured to be −5.650 eV and is shown in FIG.

[0154] In the examples, the maximum absorption wavelength and gram absorption coefficient of the quinophthalone compound were measured with a Shimadzu UV-1900i spectrophotometer manufactured by Shimadzu Corporation at an optical path length of 10 mm. Tg_DTA was measured using a Rigaku TheRmo Plus TG8120, and MS was measured using a Shimadzu LCMS-2020.

[0155] Example 2: Synthesis of specific compound (3-10) Example compound (3-10) (12.18 g) was obtained in the same manner as in Example 1, except that 15.0 g of the following compound (D) was used instead of 7.00 g of intermediate (C) in Example 1. [ka]

[0156] The resulting compound was confirmed to be the desired compound based on the following analytical results. ESI-Mass: 477(M+H) + , 475(MH) - The N,N-dimethylformamide solution of the compound thus obtained exhibited a maximum absorption at 448 nm, as shown in the transmission spectrum of Figure 2, and a gram absorption coefficient of 7.21 × 10 4 The concentration was mL / g cm. The Tg_DTA was measured and the Tg(-5wt%) was 425.7℃. The HOMO value was measured to be −5.722 eV and is shown in FIG.

[0157] (Example 3) Synthesis of specific compound (3-95) Example compound (3-95) (19.61 g) was obtained in the same manner as in Example 2, except that 10.36 g of 5-bromoanthranilic acid was used instead of 6.58 g of anthranilic acid. [ka]

[0158] The resulting compound was confirmed to be the desired compound based on the following analytical results. ESI-Mass: 556(M+H) + The N,N-dimethylformamide solution of the compound thus obtained exhibited a maximum absorption at 448 nm, as shown in the transmission spectrum of FIG. 3, and a gram absorption coefficient of 4.43×10 4 The concentration was mL / g cm. The Tg_DTA was measured and the Tg(-5wt%) was 399.8℃. The HOMO value was measured to be −5.783 eV and is shown in FIG.

[0159] Comparative Example 1: Synthesis of Comparative Compound [ka]

[0160] 22.80g of intermediate (D) was charged into 174mL of toluene and heated to 73-77℃. 0.54g of N,N-dimethylformamide and 8.10g of thionyl chloride were added dropwise to the toluene solution, and the mixture was stirred at 73-87℃ for 4 hours. The remaining thionyl chloride was removed by distillation under reduced pressure, and the mixture was cooled to room temperature. 5.40g of pyridine was then charged, and 8.10g of dibutylamine was added dropwise. After stirring at 75°C for 3 hours, the mixture was cooled to 60°C, separated, washed with water, crystallized, filtered and dried to obtain 24.6 g of the target product (comparative compound).

[0161] The resulting compound was confirmed to be the desired compound based on the following analytical results. ESI-Mass: 487(M+H) + The HOMO value was measured to be −5.422 eV and is shown in FIG. As shown in FIG. 4, compared with the quinophthalone compound of Comparative Example 1, the quinophthalone compounds of Examples 1 to 3 having a group of formula (1-i) had low HOMO values ​​and improved durability.

[0162] [Example 4] 1000 parts by weight of polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering Plastics Corporation) and 0.015 parts by weight of the quinophthalone compound produced in Example 1 (specific example compound 3-21) were mixed in a tumbler for 20 minutes, and then melted and kneaded in a single screw extruder under the conditions of a cylinder setting temperature of 260°C and a screw rotation speed of 56 rpm to form pellets.

[0163] [Example 5] 1000 parts by weight of polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering Plastics Corporation) and 0.015 parts by weight of the quinophthalone compound produced in Example 2 (specific example compound 3-10) were mixed in a tumbler for 20 minutes, and then melted and kneaded in a single-screw extruder under conditions of a cylinder setting temperature of 260°C and a screw rotation speed of 56 rpm to form pellets.

[0164] [Example 6] 1000 parts by weight of polycarbonate resin (H-3000FN manufactured by Mitsubishi Engineering Plastics Corporation) and 0.015 parts by weight of the quinophthalone compound produced in Example 3 (specific example compound 3-95) were mixed in a tumbler for 20 minutes, and then melted and kneaded in a single screw extruder under the conditions of a cylinder setting temperature of 260°C and a screw rotation speed of 56 rpm to form pellets.

[0165] [Example 7] 1000 parts by weight of polyamide resin (GRilamid TR90 manufactured by MSC Japan) and 0.01 parts by weight of specific example compound 3-21 were mixed in a tumbler for 20 minutes, and then melted and kneaded in a single screw extruder under the conditions of a cylinder setting temperature of 260°C and a screw rotation speed of 56 rpm to form pellets.

[0166] [Example 8] 1000 parts by weight of polyamide resin (GRilamid TR90 manufactured by M-Chemie Japan) and 0.01 parts by weight of specific example compound 3-10 were mixed in a tumbler for 20 minutes, and then melted and kneaded in a single screw extruder under the conditions of a cylinder setting temperature of 260°C and a screw rotation speed of 56 rpm to form pellets.

[0167] [Example 9] 1000 parts by weight of polymethyl methacrylate resin (Asahi Kasei Corporation: 80N) and 0.015 parts by weight of specific example compound 3-21 were mixed in a tumbler for 20 minutes, and then melted and kneaded in a single-screw extruder under conditions of a cylinder setting temperature of 260°C and a screw rotation speed of 56 rpm to form pellets.

[0168] [Example 10] Using the pellets produced in Example 4 as the raw material, a resin composition was molded into a flat plate having an outer dimension of 150 mm x 300 mm and a thickness of 2 mm in an injection molding machine under conditions of a cylinder temperature of 260°C, a mold temperature of 80°C, and a molding cycle of 60 seconds.

[0169] [Example 11] A flat resin composition was molded in the same manner as in Example 7, except that the pellets produced in Example 5 were used as the raw material.

[0170] [Example 12] A solution with a resin concentration of 20% by mass was obtained by adding 100 parts by mass of a cyclic olefin resin (APEL6015T, manufactured by Mitsui Chemicals, Inc.) and 0.1 parts by mass of the quinophthalone compound (specific example 3-21) produced in Example 1 to 400 parts by mass of a mixed solution of cyclohexane and methylene chloride at a ratio of 7:3 (mass ratio). The resulting solution was then cast onto a smooth glass plate, dried at 40° C. for 4 hours and at 60° C. for 4 hours, and then peeled off from the glass plate. The peeled coating film was further dried under reduced pressure at 100° C. for 8 hours to prepare an optical filter with a thickness of 0.1 mm, length of 60 mm, and width of 60 mm.

[0171] [Example 13] An optical filter was obtained in the same manner as in Example 9, except that 0.1 parts by weight of the quinophthalone compound (Specific Example 3-21) synthesized in Example 1 used in Example 12 was replaced with 0.1 parts by weight of the quinophthalone compound (Specific Example 3-10) synthesized in Example 2.

[0172] [Example 14] Manufacturing of helmet shield The flat plate produced in Example 10, having an outer dimension of 150 mm × 300 mm and a thickness of 2 mm, was cut into the shape of a motorcycle helmet shield and placed in a heating furnace and heated to 160° C. This heated flat plate was placed in a mold to form a curved molded product with a curvature radius of about 120 mm, and after cooling, it was removed from the mold to obtain a helmet shield. The shield was attached to a helmet and used during both daytime and nighttime rides. The results showed that there was little glare when riding on sunny days, and no significant decrease in light transmittance when riding at night. In addition, the blue (green), yellow, and red lights of traffic lights could be clearly seen.

[0173] [Example 15] Manufacture of anti-glare coating for display devices of information devices A coating liquid was prepared by dissolving 100 parts by weight of polymethyl methacrylate resin (80N manufactured by Asahi Kasei Corporation) and 0.05 parts by weight of the quinophthalone compound (specific example 3-21) produced in Example 1 in 300 parts by weight of methyl ethyl ketone. This coating solution was applied to the surface of a polyethylene terephthalate (PET) sheet having a thickness of about 200 μm using a Mayer bar, and then dried so that the film thickness after drying would be about 10 μm. This anti-glare coated PET sheet was placed in front of an LED-backlit computer display screen, and the screen was observed under various conditions, including displaying text, images, videos, etc. The results showed that not only was there less glare and less eye fatigue compared to before the sheet was installed, but the contrast of images was improved and they looked clearer, without any change in color tone.

[0174] [Example 16] Manufacture of anti-glare film for display devices of information devices 1,000 parts by weight of polymethyl methacrylate resin (Asahi Kasei Corporation: 80N) and 0.132 parts by weight of the quinophthalone compound (Specific Example 3-10) synthesized in Example 2 were mixed in a tumbler for 20 minutes, and then melted and kneaded in a single-screw extruder under conditions of a cylinder setting temperature of 260°C and a screw rotation speed of 56 rpm to form pellets. The pellets were mixed and extruded in a twin-screw extruder to produce a film (sheet) with a thickness of about 200 μm. The maximum temperature in the extrusion zone and melt line was 275°C, and the chill roll temperature was 30°C. The resulting film was cut and attached to the display surface of a portable information device using an acrylic adhesive. After observing the display surface under various conditions, such as displaying text and images, it was found that not only was there less glare and brightness than before application, but the contrast of images was improved and they looked clearer, while the color tone remained unchanged. [Industrial Applicability]

[0175] The resin composition containing the quinophthalone compound of the present invention can efficiently cut blue light of about 380 nm to 450 nm, suppress glare and glare, and increase contrast. Furthermore, since there is almost no coloring, there is little decrease in light transmittance, and there is little deterioration of the dye in the resin, the molded product obtained by molding this is very useful for optical articles such as eyeglass lenses, sun visors, helmet shields, and anti-glare coatings or anti-glare films for display devices of information devices. It is also useful for improving the life of image display devices such as liquid crystal display devices and organic EL displays, and improving contrast in bright rooms.

Claims

1. A quinophthalone compound represented by general formula (1): 【Chemical 1】 (In formula (1), R １ ~R １０ each independently represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a sulfone group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a mercapto group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, a carboxylic acid ester group, a sulfonic acid ester group, or a group represented by the following general formula (1-i): R １ ~R １０ At least one of the groups is a group represented by the following general formula (1-i): R １ and R ２ , R ２ and R ３、 R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ may be bonded to form an aliphatic ring, an aromatic ring or a heterocyclic ring. 【Chemistry 2】 (In formula (1-i), n is an integer of 1 to 3, Y represents a single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkenylene group, a substituted or unsubstituted alkynylene group, a substituted or unsubstituted arylene group, an oxygen atom, a sulfur atom, a carbonyl group, a sulfonyl group, a substituted or unsubstituted imino group, or a divalent to tetravalent sulfur atom-containing hydrocarbon group; R １１ ~R １４ each independently represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a sulfone group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a mercapto group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, a carboxylic acid ester group, or a sulfonic acid ester group; R １１ and R １２ , R １２ and R １３、 R １３ and R １４ may be bonded to form an aliphatic ring, an aromatic ring, or a heterocyclic ring.

2. In general formula (1), R １ ~R １０ are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 8 carbon atoms, a substituted or unsubstituted amino group having 1 to 16 carbon atoms, a mercapto group, a substituted or unsubstituted alkylthio group having 1 to 8 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 12 carbon atoms, or a group represented by general formula (1-i), and R １ ~R １０ at least one of is a group represented by general formula (1-i), In general formula (1-i), R １１ ~R １４ are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 8 carbon atoms, a substituted or unsubstituted amino group having 1 to 16 carbon atoms, a mercapto group, a substituted or unsubstituted alkylthio group having 1 to 8 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 12 carbon atoms.

3. 3. The quinophthalone compound according to claim 2, wherein in general formula (1-i), n is an integer of 1 to 3, and Y is a single bond.

4. The quinophthalone compound according to claim 2, wherein in general formula (1-i), n is an integer of 1 to 3, and Y is a substituted or unsubstituted alkylene group having 1 to 12 carbon atoms, an oxygen atom, a sulfur atom, a substituted or unsubstituted imino group having 1 to 12 carbon atoms, or a divalent, trivalent, or tetravalent sulfur atom-containing hydrocarbon group.

5. The quinophthalone compound according to claim 1, which has a maximum wavelength of 440 to 470 nm.

6. A quinophthalone compound according to claim 1, used as an additive for anti-glare optical articles.

7. (A) a thermoplastic resin or a thermosetting resin; (B) one or more quinophthalone compounds represented by general formula (1) according to any one of claims 1 to 6, A resin composition comprising:

8. The thermoplastic resin is at least one selected from a polycarbonate resin, a polyamide resin, an acrylic resin, and a polyester resin, and the thermosetting resin is at least one selected from a polyurethane resin, a polythiourethane resin, and an allyl diglycol carbonate resin. The resin composition according to claim 7.

9. A molded article obtained by molding the resin composition according to claim 7.

10. The molded article according to claim 9, which is an anti-glare optical article.

11. The molded article according to claim 9, which is an optical filter.

12. The molded article of claim 9, which is a sun visor.

13. The molded article of claim 9, which is a shield for a helmet.

14. The molded article according to claim 9, which is an antiglare coating or an antiglare film for a display device of an information device.

Images