JP6545746B2 - Dye compound - Google Patents

Description

The present invention relates to a compound etc. which can be used as a dye.

Ultraviolet light and blue light have strong energy and may damage the retina and cause eye disease. Therefore, compounds that can be used as ultraviolet light absorbers, colorants for blue light cutting, and the like are required. As a UV absorber, for example, using a methine compound in place of a benzophenone type or a benzotriazole type UV absorber has been proposed (Patent Documents 1 and 2).

JP, 2009-067973, A JP, 2011-184414, A

Since the conventional methine compound has a low absorbance near the visible light region, it has been necessary to increase the addition amount to reduce blue light. For this reason, improvement in the absorption spectrum shape and the absorbance has been required.

The main object of the present invention is to provide a compound having a high absorbance around 400 nm.

The inventors of the present invention conducted intensive studies to solve the above problems, and as a result, a compound having a methine structure having a nitrogen-containing aromatic ring and an electron-withdrawing group represented by the following general formula (1) has a wavelength of about 400 nm. It was found to have an absorption maximum and to have a high absorbance around 400 nm. Based on this finding, the present inventors have conducted further studies to complete the present invention.

That is, the compound of the present invention is characterized by being represented by the following general formula (1).

(In the general formula (1), m represents an integer of 1 to 6,
Q ¹ represents a hydrogen atom when m is 1 and a divalent to hexavalent linking group when m is 2 to 6,
D ¹ represents a group in which one hydrogen atom is removed from the compound represented by the following general formula (2), and when m is 2 to 6, a plurality of D ¹ may be all the same or different It may be

(In the general formula (2), R ¹ represents a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, —O—C (O) H, —C (O) —R ⁷ or —SO ₂ — represents R ^{8, R 2} is a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic ring-containing group, -O-C (O) H , -C (O) -R 7 or -SO ₂ - or represents R ^8, or, ^{R 2} represents -C (O) -R ^9, and ^{R 1,} with the ^{R 2,} with the carbon atom ^{to which R 1} and ^{R 2} are attached, a substituent R ⁷ represents a hydrogen atom, a halogen atom, -NR ⁷² R ⁷³ or -R ⁷⁴ , and R ⁸ represents a halogen atom, a hydroxy group,- oR ^81, represents ^-NR 82 ^{R 83} or ^{-R 84, R 9} represents a hydrogen atom, a halogen atom, hydroxy ^group, -OR 91, -NR ^{9 .R 72 ~R 74, R 81 ~R} 84 and ^R 91 ^{to R 94} representing a R ⁹³ or ^{-R 94} are the same or different, a hydrogen atom, an optionally substituted alkyl group or a substituted group And an aryl group which may have
R ³ represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group which may have a substituent, or an aryl group which may have a substituent.
R ⁴⁰² and R ⁴⁰³ are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, -NR ⁴⁰⁶ R ⁴⁰⁷ , -OR ^408, a cyano ^{group, -C (O) R 409,} -O-C (O) R 410 or -C ^{(O) oR 411,}
R ^{404 to} R ⁴¹¹ are the same or different and each represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent. R ⁴⁰⁴ , R ^405, and the nitrogen atom to which R ⁴⁰⁴ and R ⁴⁰⁵ are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent. )))

In the present invention, m in the above general formula (1) is preferably 1 or 2.
The compound represented by the above general formula (1) is preferably a compound represented by the following general formula (3).

(In the general formula (3), R ^1a represents a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, —O—C (O) H, —C (O) —R ^7a or —SO ₂ — It represents R ^{8a, R 2a} is a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic ring-containing group, -O-C (O) H , -C (O) -R 7a or -SO ₂ - or represents R ^{8a, or, R 2a} represents a -C (O) ^{-R 9a,} with a ^{R 1a,} and ^{R 2a,} with the carbon atom ^{to which R 1a} and ^{R 2a} are bonded, substituted R ^7a represents a hydrogen atom, a halogen atom, -NR ^72a R ^73a or -R ^74a , and R ^8a represents a halogen atom, a hydroxy group,- oR ^81a, represents ^-NR 82a ^{R 83a} or ^{-R 84a, R 9a} is a hydrogen atom, halogen Atom, hydroxy ^{group, .R} 72a ^{to R} 74a representing the -OR ^91a, -NR ^{92a R 93a} or ^{-R 94a, R} 81a ^{~R 84a} and ^R 91a ^{to R 94a} are the same or different, a hydrogen atom, a substituent Or an alkyl group having 1 to 20 carbon atoms which may have 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms which may have a substituent.
R ^3a represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent .
R ^402a is a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, -NR ^406a R ^407a , -OR ^408a , cyano group, -C (O) R ^409a , ^-OC (O) R ^410a or -C (O) OR ^411a , wherein R ^{404a to} R ^411a are the same or different and hydrogen; This represents an atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. R ^{404 a} , R ^{405 a,} and the nitrogen atom to which R ^{404 a} and R ^{405 a} are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent.
R ⁴¹³ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, or This represents a group represented by formula (4).

(In the general formula (4), Q ² represents a divalent hydrocarbon group having 1 to 20 carbon atoms that may have a substituent, and * represents a bonding site to the general formula (3).
R ^1b represents a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, -O-C (O) H, -C (O) -R ^7b or -SO ₂ -R ^8b , and R ^2b represents Or a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, -O-C (O) H, -C (O) -R ^7b or -SO ₂ -R ^8b , or R 2 ^b represents —C (O) —R ^{9 b} , and R 4 ^b , R 2 ^b, and a carbon atom to which R 1 ^b and R 2 ^b are bonded may have a substituent and may be 4 to 8 members Form a heterocycle of R ^7b represents a hydrogen atom, a halogen atom, -NR ^72b R ^73b or -R ^74b , R ^8b represents a halogen atom, a hydroxy group, -OR ^81b , -NR ^82b R ^83b or -R ^84b , R ^9b Represents a hydrogen atom, a halogen atom, a hydroxy group, -OR ^91b , -NR ^92b R ^93b or -R ^94b . ^{R 72b ~R 74b, R 81b ~R} 84b and ^R 91b ^{to R 94b} are the same or different, a hydrogen atom, have an alkyl group or a substituent of carbon atoms which may 20 have a substituent Represents an optionally substituted aryl group having 6 to 20 carbon atoms.
R ^3b represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent .
R ^402b is a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, -NR ^406b R ^{407 b} , -OR ^{408 b} , cyano group, -C (O) R ^{409 b} , -O-C (O) R ^{410 b} or -C (O) OR ^{411 b} , and R ^{404 b to} R ^{411 b} are the same or different and hydrogen; This represents an atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. R ^{404 b} , R ^{405 b,} and the nitrogen atom to which R ^{404 b} and R ^{405 b} are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent. )))

In one aspect of the present invention, the R ⁴¹³ is preferably a group represented by the general formula (4).
In one aspect of the present invention, a substituent is a carbon atom to which R ^2a is —C (O) —R ^9a , and R ^1a , R ^2a , and R ^1a and R ^2a are bonded to each other. It is preferable to form the 4-8 membered heterocyclic ring which may have.

It is also preferable that the compound represented by the said General formula (1) is a compound represented by following General formula (5).

(In the general formula (5), R ^2c represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, —O—C (O) H, —C (O) —R ^7c or — ^{.R 7c} representing the SO ₂ -R ^8c is hydrogen atom, a halogen ^atom, an -NR ^{72c R 73c} or ^{-R 74c, R 8c} represents a halogen atom, hydroxy ^group, -OR ^81c, -NR ^{82c R 83c} or ^{-R 84c .R} 72c ^{~R 74c} and ^R 81c represents a ^{to R 84c} are the same or different, a hydrogen atom, have an alkyl group or a substituent of carbon atoms which may 20 have a substituent Represents an optionally substituted aryl group having 6 to 20 carbon atoms.
R ^3c represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent .
R ^402c and R ^403c are the same or different and each is a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 to 20 carbon atoms which may have a substituent aryl ^group, -NR ^406c R ^407c, represent ^{-OR 408 c,} a cyano ^group, -C (O) R ^409c, a -O-C ^{(O) R 410c} or ^{-C (O) oR 411c, R} 404c ~R 411c The same or different and each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. And R ^404c, and ^{R 405c, R 404c} and ^{R 405c} together with the nitrogen to atom to which they are attached, may form a nitrogen-containing heterocycle 4-8 membered which may have a substituent.
R ⁵⁰¹ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, or the following general formula (6) Represents a group represented by).
Y ^1c represents —NR ^{502 c} —, and R ^{502 c} represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 to 20 carbon atoms which may have a substituent Represents an aryl group of

(In the general formula (6), Q ³ represents a divalent hydrocarbon group having 1 to 20 carbon atoms that may have a substituent, and * represents a bonding site to the general formula (5).
Y ^1d represents —NR ^{502 d} —, and R ^{502 d} represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 to 20 carbon atoms which may have a substituent Represents an aryl group of
R ^2d represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, -O-C (O) H, -C (O) -R ^7d or -SO ₂ -R ^8d . R ^7d represents a hydrogen atom, a halogen atom, -NR ^72d R ^73d or -R ^74d , and R ^8d represents a halogen atom, a hydroxy group, -OR ^81d , -NR ^82d R ^83d or -R ^84d . R ^{72 d to} R ^{74 d} and R ^{81 d to} R ^{84 d} are the same or different and each is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or a carbon number which may have a substituent 6-20 aryl groups are represented.
R ^3d represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent .
R ^402d and ^{R 403d} are the same or different, a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms that may have a substituent group, carbon atoms which may have a substituent having 6 to 20 aryl ^group, -NR ^406d R ^407d, represents ^{-OR 408d,} a cyano ^group, -C (O) R ^409d, a -O-C ^{(O) R 410d} or ^{-C (O) oR 411d, R} 404d ~R 411d The same or different and each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. R ^{404 d} , R ^{405 d,} and the nitrogen atom to which R ^{404 d} and R ^{405 d} are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent. )))
In one aspect of the present invention, the R ⁵⁰¹ is preferably a group represented by the general formula (6).

It is also preferable that the compound represented by the said General formula (1) is a compound represented by following General formula (7).

(In the general formula (7), ^{Q 4} is, -SO ₂ - represents a divalent hydrocarbon group or carbon atoms which may 20 have a substituent.
R ^1e represents a hetero ring-containing group, —C (O) —R 7 ^e or —SO ₂ —R ^{8 e} , and R ^{2 e} is a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a hetero ring-containing group, -O-C (O) H, -C (O) -R ^7e or -SO ₂ -R ^8e . R ^7e represents a hydrogen atom, a halogen ^atom, an -NR ^{72e R 73e,} or ^{-R 74e, R 8e} represents a halogen atom, hydroxy ^group, -OR ^81e, a -NR ^{82e R 83e,} or ^{-R 84e.} R ^72e to R ^74e and ^R 81e ^{to R 84e,} which may be the same or different, a hydrogen atom carbon atoms, which may have an alkyl group or a substituent having 1 to 20 carbon atoms that may have a substituent 6-20 aryl groups are represented.
R ^3e represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent .
R ^{402 e} and R ^{403 e} are the same or different and each is a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 to 20 carbon atoms which may have a substituent aryl ^group, -NR ^406e R ^407e, represent ^{-OR 408e,} a cyano ^group, -C (O) R ^409e, a -O-C ^{(O) R 410e} or ^{-C (O) oR 411e, R} 404e ~R 411e The same or different and each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. And R ^404e, and ^{R 405e, R 404e} and ^{R 405e} with the nitrogen atom to which they are attached, may form a nitrogen-containing heterocycle 4-8 membered which may have a substituent. )
In one aspect of the present invention, Q ⁴ is preferably -SO _2- .

The dye composition of the present invention is characterized by containing the compound of the present invention.
The optical filter of the present invention is characterized by containing the compound of the present invention.
As the above-mentioned optical filter, a color filter is preferred.
The blue light shielding material of the present invention is characterized by containing the compound of the present invention.
The ultraviolet absorber of the present invention is characterized by containing the compound of the present invention.

According to the present invention, a compound having a high absorbance near 400 nm can be provided. The compound of the present invention can be suitably used as a pigment or the like for an optical filter such as a color filter of a liquid crystal display.

The compound of the present invention is a compound represented by the above general formula (1). In the present specification, the compound represented by the above general formula (1) is also referred to as a compound (1). The same applies to compounds of other formula numbers. For example, the compound represented by General Formula (2) is also referred to as Compound (2).

When geometrical isomerism exists in the compound (1) of the present invention, the present invention includes any of its geometrical isomers. When one or more asymmetric carbon atoms are present in the compound (1) of the present invention, the present invention provides compounds wherein each asymmetric carbon atom is in the R configuration, compounds in the S configuration, and compounds of any combination thereof Includes any of Also, their racemates, racemic mixtures, single enantiomers and diastereomeric mixtures are all included in the present invention.

In the above general formula (1), m represents an integer of 1 to 6. Since the heat resistance of a compound (1) improves that m is 2-6, it is preferable. In one aspect of the present invention, m is preferably 1 or 2, more preferably 2.

Q ¹ represents a hydrogen atom when m is 1 and a divalent to hexavalent linking group when m is 2 to 6.
Examples of the di- to hexa-valent linking group include, for example, a divalent to hexa-valent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, -SO _2- and the like.
As a C1-C20 2 to 6-valent hydrocarbon group which may have a substituent, a linear, branched or cyclic 2 to 6 carbon atom having 1 to 20 carbons which may have a substituent And alkyl groups having 6 to 20 carbon atoms which may have a substituent and a divalent to hexavalent arylene group. Q ¹ is preferably a hydrogen atom or a divalent linking group.

As the divalent linking group, a divalent hydrocarbon group having 1 to 20 carbon atoms that may have a substituent, -SO 2 _- and the like are preferable. The C1-C20 divalent hydrocarbon group which may have a substituent is preferably a linear, branched or cyclic divalent C1-C20 group which may have a substituent. Or an alkyl group having 6 to 20 carbon atoms which may have a substituent.
The linear, branched or cyclic divalent alkyl group having 1 to 20 carbon atoms is a divalent alkyl in which an oxygen atom, a sulfur atom or an arylene group which may have a substituent may be inserted between carbon and carbon It may be a group, preferably a linear divalent alkyl group having 1 to 20 carbon atoms, represented _by- (CH ₂ ) _k1- (where k 1 represents an integer of 1 to 20) For example, methylene group, ethylene group, propylene group, butylene group, pentylene group, hexylene group, heptylene group, octylene group, decylene group and the like can be mentioned. Moreover, it is also preferable that it is a bivalent alkyl group substituted by one or more halogen atoms, for example, a bis trifluoromethyl methylene group etc. are mentioned. The carbon number of the linear divalent alkyl group is preferably 2 to 10 (k1 in the above formula is 2 to 10), and more preferably 4 to 8 (k1 in the above formula is 4 to 8).

As a C6-C20 bivalent arylene group which may have a substituent, the group represented by following General formula (20) is preferable, for example.

In the above general formula (20), X independently represents a halogen atom, a nitro group, a hydroxy group, a sulfo group, an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms, and s is 0 Represents an integer of ~ 4. The two bonds in the benzene ring may be either o-, m- or p-oriented. In addition, it is preferable that the benzene ring has no substituent (s = 0).

In general formula (1), D ¹ represents a group in which one hydrogen atom is removed from compound (2). A group in which one hydrogen atom is removed from compound (2) can also be said to be a group in which one hydrogen atom is removed from compound (2). The compound (2) contains a nitrogen-containing aromatic ring and an electron-withdrawing group, and contains a methine structure which can be a dye. The compound (1) can be used as a dye compound because it contains such methine structure. When m is 2 to 6, the plurality of D ¹ may be all the same or different. In one aspect, it is preferable that all of the plurality of D ¹ be the same.
The compound (1) in which m is 1 in the general formula (1) is a compound (2). The compound (1) in which m is 1 is also referred to as a monomeric compound. The compound (1) in which m is 2 to 6 is a compound having a 2- to 6-mer structure in which a group in which a hydrogen atom is removed from the compound (2) is linked 2 to 6 depending on the linking group (Q ¹ ). The compound (1) in which m is 2 to 6 can also be referred to as a 2 to 6-mer compound.
D ¹ is preferably a group in which one hydrogen atom is removed from R ¹ , R ⁴⁰³ or R ⁴⁰⁴ in the compound (2), and a group in which one hydrogen atom is removed from R ¹ or R ⁴⁰³ Is more preferred. In other words, in the general formula (1), Q ¹ is preferably bonded to the portion of R ¹ , R ⁴⁰³ or R ^{404 in} the general formula (2), and is bonded to the portion of R ¹ or R ⁴⁰³ Is more preferable.

In the general formula (2), R ¹ represents a cyano group, a nitro group, a trifluoromethyl group (CF ₃ group), a heterocycle-containing group, —O—C (O) H, —C (O) —R ⁷ or It represents a -SO ₂ -R ^8. A cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -O-C (O) H, -C (O) -R ⁷ and -SO ₂ -R ⁸ are all electron withdrawing groups. is there.
Does R ² represent a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -O-C (O) H, -C (O) -R ⁷ or -SO ₂ -R ⁸ ? Or R ² represents —C (O) —R ⁹ . In the general formula (2), when ^{R 2} represents -C (O) -R ⁹ includes a ^{R 1,} and ^{R 2,} with the carbon atom ^{to which R 1} and ^{R 2} are attached, a substituent It forms a 4- to 8-membered heterocyclic ring which may be possessed. -C (O) -R ⁹ is an electron withdrawing group.
R ⁷ represents a hydrogen atom, a halogen atom, -NR ⁷² R ⁷³ or -R ⁷⁴ , R ⁸ represents a halogen atom, a hydroxy group, -OR ⁸¹ , -NR ⁸² R ⁸³ or -R ⁸⁴ , R ⁹ It represents a hydrogen atom, a halogen atom, hydroxy ^group, an -OR ^{91, -NR} 92 ^{R 93,} or ^{-R 94.} R ^{72 to} R ⁷⁴ , R ^{81 to} R ⁸⁴ and R ^{91 to} R ⁹⁴ are the same or different and each represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent Represents
R ¹ and R ² may be the same or different.

As a heterocycle-containing group in R ¹ and R ² , nitrogen-containing heterocycles such as pyrrole ring, pyridine ring, quinoline ring, pyrimidine ring, pyridazine ring, pyrazine ring, pyrazine ring, imidazole ring, benzimidazole ring, triazine ring, triazole ring and tetrazole ring Rings; Oxygen-containing heterocycles such as furan ring and benzofuran ring; Sulfur-containing heterocycles such as thiophene ring and benzothiophene ring; Heterocycles containing an oxygen atom and nitrogen atom such as oxazole ring and benzoxazole ring; Thiazole ring, benzothiazole And sulfur-containing heterocyclic rings such as thiadiazole rings, etc., and these rings may further form a condensed ring with another carbon ring (for example, a benzene ring) or a heterocyclic ring (for example, a pyridine ring), Oxazole ring and benzoxazole ring are preferred.

In one embodiment of the present invention, as a heterocycle-containing group in R ¹ and R ^2, a group in which a hydrogen atom is removed from carbon (2-position) between nitrogen and oxygen of benzoxazole ring or oxazole ring (excluding hydrogen atom Is preferable, and more preferable is a group in which a hydrogen atom is removed from carbon (2-position) between nitrogen and oxygen of benzoxazole ring.
Also, for example, in the general formula (1), m is 2 to 6, R ¹ is a group in which a hydrogen atom is removed from a benzoxazole ring or an oxazole ring, and Q ¹ and D ¹ are compounds (2) When R ¹ is bonded at R ¹ , it is preferable that R ¹ is bonded to Q ¹ at a carbon atom other than carbon (position 2) between nitrogen and oxygen in the benzoxazole ring or oxazole ring.
R ¹ is preferably a cyano group, a heterocycle-containing group, —O—C (O) H or —C (O) —R ⁷ . R ² is preferably a cyano group, a heterocycle-containing group, —O—C (O) H or —C (O) —R ⁷ , or R ² is —C (O) —R ⁹ is there.

R ⁷² , R ⁷³ and R ⁷⁴ , R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ , and an alkyl group which may have a substituent in R ⁹¹ , R ⁹² , R ⁹³ and R ⁹⁴ , a substituent C1-C20 alkyl group which may have is mentioned. As a C1-C20 alkyl group which may have a substituent, the C1-C20 linear, branched or cyclic alkyl group which may have a substituent mentioned later is mentioned. In one aspect of the present invention, the alkyl group having 1 to 20 carbon atoms which may have a substituent is preferably a linear, branched or cyclic alkyl group having 4 to 20 carbon atoms, and has 4 carbon atoms The above branched or cyclic sterically bulky alkyl group is preferable, more preferably a cyclic alkyl group having 6 to 20 carbon atoms, and particularly preferably having a linear or branched alkyl group as a substituent It may be a cyclic alkyl group. Examples of the alkyl group having 1 to 20 carbon atoms as R ^{72 to} R ⁷⁴ and R ^{81 to} R ⁸⁴ and R ^{91 to} R ⁹⁴ include, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n- Butyl group, i-butyl group, t-butyl group, n-hexyl group, cyclohexyl group, n-octyl group, 2-ethylhexyl group, 4-t-butylcyclohexyl group, 2,6-di-t-butyl-4 -Methylcyclohexyl and the like are preferable, and t-butyl, cyclohexyl, 4-t-butylcyclohexyl, 2,6-di-t-butyl-4-methylcyclohexyl and the like are more preferable, and 4-t-butylcyclohexyl is more preferable. And 2,6-di-t-butyl-4-methylcyclohexyl and the like are more preferable.
R ⁷² , R ⁷³ and R ⁷⁴ , R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ , and an aryl group which may have a substituent in R ⁹¹ , R ⁹² , R ⁹³ and R ⁹⁴ , a substituent And an aryl group having 6 to 20 carbon atoms which may have one of the following. Examples of the aryl group having 6 to 20 carbon atoms which may have a substituent include aryl groups having 6 to 20 carbon atoms which may have a substituent described later, and for example, it is substituted with an alkyl group Preferred is a phenyl group (eg, phenyl group, 3-methylphenyl group, 2,6-dimethylphenyl group etc.) and the like.
R ⁸¹ and R ⁹¹ are the same or different and, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl, n-hexyl, cyclohexyl, n-octyl, 2-ethylhexyl, 4-tert-butylcyclohexyl, 2,6-di-tert-butyl-4-methylcyclohexyl and the like are preferable, 4-t-butylcyclohexyl, 2,6-di-t-butyl-4-methylcyclohexyl and the like are more preferable. R ⁷² , R ⁸² and R ⁹² are the same or different, preferably a hydrogen atom. R ⁷³ , R ⁸³ and R ⁹³ are the same or different and are preferably a hydrogen atom, a phenyl group, a 3-methylphenyl group or a 2,6-dimethylphenyl group. R ⁷⁴ , R ⁸⁴ and R ⁹⁴ are the same or different and are preferably a methyl group, an ethyl group, a t-butyl group, a cyclohexyl group, a phenyl group, a naphthyl group or the like.

When R ² is —C (O) —R ⁹ , R ⁴ , R ² and the carbon atom to which R ¹ and R ² are bonded may have a substituent It forms an 8-membered heterocyclic ring.
The 4- to 8-membered heterocyclic ring formed by R ¹ , R ² and a carbon atom to which R ¹ and R ² are bonded is at least one selected from a nitrogen atom, an oxygen atom and a sulfur atom And 4 to 8 membered heterocyclic rings containing the hetero atom of The heterocycle may be an aromatic heterocycle or a nonaromatic heterocycle. Examples of the 4- to 8-membered heterocyclic ring include pyrazolone ring, isoxazolone ring, oxindole ring, barbituric ring, thiobarbital ring, rhodanine ring, pyridone ring, 2,4-oxazolidinedione ring, 2-thio- 2,4-oxazolidinedione ring, 2,5-thiazolidinedione ring, 2-thio-2,5-thiazolidinedione ring, thiazolidone ring, 4-thiazolone ring, 2,4-imidazolinion ring (hydantoin ring), 2- Thiohydantoin ring, 5-imidazolone ring, succinimide ring, 1,3-dioxane-4,6-dione ring and the like can be mentioned. Preferably, it is a heterocycle containing at least one hetero atom selected from 5 or 6 membered nitrogen atom, oxygen atom and sulfur atom, more preferably a heterocycle containing 5 or 6 membered nitrogen atom and oxygen atom And pyrazolone ring, barbituric ring, 2,4-oxazolidinedione ring and the like.
The substituent in the 4-8 membered heterocyclic ring which may have a substituent is not particularly limited, and, for example, it has a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, and a substituent. The C6-C20 aryl group which may be contained, a carboxy group, an alkoxycarbonyl group etc. are mentioned. As an aryl group having a substituent, nitrophenyl group, cyanophenyl group, hydroxyphenyl group, methylphenyl group, dimethylphenyl group, trimethylphenyl group, fluorophenyl group, chlorophenyl group, dichlorophenyl group, bromophenyl group, methoxyphenyl group, A phenyl group having a substituent such as ethoxyphenyl group, trifluoromethylphenyl group, N, N-dimethylaminophenyl group, and the like can be mentioned. Preferably, the substituent is a non-substituted alkyl group, a halogenated alkyl group, a carboxy group-substituted alkyl group, an aralkyl group, an aryl group which may have a substituent (preferably a phenyl group, a methylphenyl group, dimethylphenyl) Group, trimethylphenyl group and the like).

In general formula (2), R ³ represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group which may have a substituent, or an aryl group which may have a substituent.
R ⁴⁰² and R ⁴⁰³ are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, -NR ⁴⁰⁶ R ⁴⁰⁷ , -OR ^408, a cyano ^group, -C (O) R ^409, represents an -O-C ^{(O) R 410} or -C ^{(O) oR 411.}
R ^{404 to} R ⁴¹¹ are the same or different and each represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent. R ⁴⁰⁴ , R ^405, and the nitrogen atom to which R ⁴⁰⁴ and R ⁴⁰⁵ are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent.

As an alkyl group in R ^{< 3 >} , R ^<402> and R ^<403> , a C1-C20 linear, branched or cyclic alkyl group is mentioned, for example. Specifically, as a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec- Butyl group, t-butyl group, n-pentyl group, 2-methylbutyl group, 1-methylbutyl group, neo-pentyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, cyclopentyl group, n-hexyl Group, 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3,3-dimethylbutyl group, 2,3-dimethylbutyl group, 1,3-dimethylbutyl group, 2,2-dimethylbutyl group, 1,2-dimethylbutyl group, 1,1-dimethylbutyl group, 2-ethylbutyl group, 1-ethylbutyl group, 1,1,2-trimethylbutyl group 1-ethyl-2-methylpropyl group, cyclohexyl group, n-heptyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 2,4-dimethylpentyl group , N-octyl group, 2-ethylhexyl group, 2,5-dimethylhexyl group, 2,4-dimethylhexyl group, 2,2,4-trimethylpentyl group, t-octyl group, n-nonyl group, 3,5 3,5-trimethylhexyl group, n-decyl group, 4-ethyloctyl group, 4-ethyl-4,5-dimethylhexyl group, 4-t-butylcyclohexyl group, n-undecyl group, n-dodecyl group, 1, 3,5,7-Tetramethyloctyl group, 4-butyloctyl group, 6,6-diethyloctyl group, n-tridecyl group, 6-methyl-4-butyloctyl group, n- Tradecyl, n-pentadecyl, 3,5-dimethylheptadecyl, 2,6-dimethylheptadecyl, 2,4-dimethylheptadecyl, 2,2,5,5-tetramethylhexyl, 1- Examples thereof include a cyclopentyl-2,2-dimethylpropyl group, a 1-cyclohexyl-2,2-dimethylpropyl group, a 2,6-di-t-butyl-4-methylcyclohexyl group, an n-octadecyl group and the like.

The substituent in the alkyl group which may have a substituent is not particularly limited, and is a monocyclic or polycyclic aromatic ring group having 6 to 10 carbon atoms (phenyl group, naphthyl group, etc.), 1 to 8 carbon atoms Linear, branched or cyclic alkoxy group, amino group, mono- or di-alkylamino group (alkyl carbon number is 1 to 8), halogen atom, cyano group, hydroxy group, nitro group, carboxy group, carbon number 1 To 8 alkoxycarbonyl groups, acyl groups having 2 to 10 carbon atoms (eg, acetyl group, propionyl group, butyryl group, valeryl group, pivaloyl group, acryloyl group, methacryloyl group, benzoyl group, toluoyl group, cinnamoyl group, anisoyl group , Naphthoyl group, etc., an acyloxy group having 2 to 10 carbon atoms, and the like.

As an aryl group in R ^{< 3 >} , R ^<402> and R ^<403 >, a C6-C20 monocyclic or polycyclic aromatic ring group is mentioned. Specific examples of the monocyclic or polycyclic aromatic ring group having 6 to 20 carbon atoms include a monocyclic aromatic hydrocarbon group such as a phenyl group; naphthyl group, anthracenyl group, naphthacenyl group, pentacenyl group, phenanthrenyl group, Polycyclic aromatic hydrocarbon groups such as pyrenyl group can be mentioned.
The substituent in the aryl group which may have a substituent is not particularly limited. For example, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an amino group, Mono- or di-alkylamino group (alkyl carbon number is 1 to 8), halogen atom, cyano group, hydroxy group, nitro group, halogenated hydrocarbon group having 1 to 8 carbon atoms, carboxy group, 1 to 5 carbon atoms 8 alkoxycarbonyl group etc. are mentioned. Preferably, it is a C1-C8 linear, branched or cyclic alkyl group. For example, to cite one example of phenyl group and naphthyl group having a substituent, nitrophenyl group, cyanophenyl group, hydroxyphenyl group, methylphenyl group, dimethylphenyl group, trimethylphenyl group, fluorophenyl group, chlorophenyl group, dichlorophenyl group , Bromophenyl group, methoxyphenyl group, ethoxyphenyl group, trifluoromethylphenyl group, N, N-dimethylaminophenyl group, nitronaphthyl group, cyanonaphthyl group, hydroxynaphthyl group, methylnaphthyl group, fluoronaphthyl group, chloronaphthyl group Groups, bromonaphthyl group, trifluoromethylnaphthyl group and the like.

In the general formula (2), the 4- to 8-membered nitrogen-containing heterocyclic ring formed by R ⁴⁰⁴ , R ⁴⁰⁵ and the nitrogen atom to which R ⁴⁰⁴ and R ⁴⁰⁵ are bonded is a nitrogen-containing nitrogen atom containing an oxygen atom It may be a heterocycle. Examples of the nitrogen-containing heterocyclic ring include non-aromatic nitrogen-containing heterocyclic rings. Examples of the 4- to 8-membered nitrogen-containing heterocyclic ring include non-aromatic nitrogen-containing heterocyclic rings such as pyrrolidine ring, piperidine ring, piperazine ring and morpholine ring.
The substituent in the 4-8 membered nitrogen-containing heterocyclic ring which may have a substituent is not particularly limited, and, for example, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, 1 to 8 carbon atoms Alkoxy group, amino group, mono- or di-alkylamino group (alkyl carbon number is 1 to 8), halogen atom, cyano group, hydroxy group, nitro group, halogenated hydrocarbon group having 1 to 8 carbon atoms, A carboxy group, a C1-C8 alkoxycarbonyl group, etc. are mentioned. Preferably, it is a C1-C8 linear, branched or cyclic alkyl group.

When rings, such as an alkyl group, an aryl group, a nitrogen-containing heterocyclic ring, and a heterocyclic ring, have a substituent, when there are two or more substituents, each substituent may be the same or different.

The preferable aspect of each group in General formula (2) is demonstrated.
R ³ is preferably a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or a cyano group, and more preferably a hydrogen atom or a carbon number 1 which may have a substituent. It is an alkyl group of 5 to 5, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and particularly preferably a hydrogen atom.

R ⁴⁰² is preferably a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, or an alkoxy group, More preferably, it is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms which may have a substituent, still more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group It is.

R ⁴⁰³ is preferably -OR ⁴⁰⁸ . R ⁴⁰⁸ is preferably a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent; The C1-C20 alkyl group which may have is more preferable. R ⁴⁰⁸ is more preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms which may have a substituent, still more preferably an alkyl group having 1 to 3 carbon atoms, and particularly preferably an ethyl group. It is.
In one aspect of the present invention, it is preferable that at least one of R ⁴⁰² and R ⁴⁰³ is a substituent other than a hydrogen atom, and R ⁴⁰² and R ⁴⁰³ are the same or different and are a substituent other than a hydrogen atom It is more preferable that

R ⁴⁰⁴ and R ⁴⁰⁵ are the same or different, preferably an alkyl group having 1 to 20 carbon atoms which may have a substituent or an aryl group having 6 to 20 carbon atoms which may have a substituent And more preferably an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, still more preferably an alkyl group having 1 to 10 carbon atoms, and particularly preferably a methyl group, an ethyl group, or n- Propyl and n-butyl.
^R406 , ^R407 , ^R408 , ^R409 , ^R410 and ^R411 are the same or different, and preferably have an alkyl group having 1 to 20 carbon atoms which may have a substituent or a substituent It is a C6-C20 aryl group which may be.

As a compound in which m is 1 or 2 in the general formula (1), a compound represented by the above general formula (3) (compound (3)), a compound represented by the general formula (5) (compound (5)) The compound (compound (7)) etc. which are represented by General formula (7) etc. are preferable.

In one aspect of the present invention, compound (3) is preferred as compound (1). The compound (3) is preferable because it is excellent in light resistance.
In the general formula (3), R ^1a represents a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -O-C (O) H, -C (O) -R ^7a or -SO ₂ -R Represents ^8a .
^Does R ^2a represent a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, -O-C (O) H, -C (O) -R ^7a or -SO ₂ -R ^8a ? Or R ^2a represents —C (O) —R ^9a . When R ^2a represents -C (O) -R ^9a , R ^1a , R ^2a, and a carbon atom to which R ^1a and R ^2a are bonded may have a substituent 4 Form an 8-membered heterocyclic ring.
R ^7a represents a hydrogen atom, a halogen atom, -NR ^72a R ^73a or -R ^74a , R ^8a represents a halogen atom, a hydroxy group, -OR ^81a , -NR ^82a R ^83a or -R ^84a , R ^9a And represents a hydrogen atom, a halogen atom, a hydroxy group, -OR ^91a , -NR ^92a R ^93a or -R ^94a . R ^{72 a to} R ^{74 a} , R ^{81 a to} R ^{84 a} and R ^{91 a to} R ^{94 a} are the same or different and each has a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or a substituent Represents an optionally substituted aryl group having 6 to 20 carbon atoms. R ^1a and R ^2a may be the same or different.
R ^1a is preferably a cyano group, a heterocycle-containing group, —O—C (O) H, or —C (O) —R ^7a . R ^2a is preferably a cyano group, a heterocycle-containing group, —O—C (O) H or —C (O) —R ^7a , or R ^2a is —C (O) —R ^9a is there. In a preferred embodiment of the optionally substituted 4-8 membered heterocyclic ring in R ^1a and R ^2a, R ¹ , R ² , R ¹ and R ² in general formula (1) are combined And the preferred embodiment of the 4-8 membered heterocyclic ring formed by the carbon atom.
Preferred embodiments of R ^72a , R ^73a and R ^74a , R ^81a , R ^82a , R ^83a and R ^84a , and R ^91a , R ^92a , R ^93a and R ^94a are the above-mentioned R ⁷² , R ⁷³ and R ⁷⁴ , Preferred embodiments are the same as the preferred embodiments of R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ , and R ⁹¹ , R ⁹² , R ⁹³ and R ⁹⁴ , respectively.

In the general formula (3), R ^3a is a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 carbon atoms which may have a substituent And an aryl group of -20.
R ^402a is a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, -NR ^406a R ^407a , -OR ^408a , cyano group, -C (O) R ^409a , ^-OC (O) R ^410a or -C (O) OR ^411a , wherein R ^{404a to} R ^411a are the same or different and hydrogen; This represents an atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. R ^{404 a} , R ^{405 a,} and the nitrogen atom to which R ^{404 a} and R ^{405 a} are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent.
Preferred embodiments of R ^3a , R ^402a , R ^404a , R ^405a , R ^406a , R ^407a , R ^408a , R ^409a , R ^409a , R ^410a and R ^411a are the same as described above for R ³ , R ⁴⁰² , R ⁴⁰⁴ , R ⁴⁰⁵ , R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ are respectively the same as the preferred embodiments.

In the general formula (3), R ⁴¹³ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. Or a group represented by the above general formula (4). R ⁴¹³ is preferably an alkyl group having 1 to 5 carbon atoms which may have a substituent or a group represented by the general formula (4), and more preferably an alkyl group having 1 to 3 carbon atoms or It is a group represented by the general formula (4), more preferably an ethyl group or a group represented by the above general formula (4). In one aspect of the present invention, R ⁴¹³ is preferably a group represented by General Formula (4).

In General Formula (4), Q ² represents a C 1 to C 20 divalent hydrocarbon group which may have a substituent, and * represents a bonding site to General Formula (3). In the general formula (4), Q ² is bonded to the general formula (3). The C 1 to C 20 divalent hydrocarbon group which may have a substituent in Q ² and the preferable embodiment thereof are the C 1 to 20 carbon optionally having a substituent in Q ¹ described above It is the same as the divalent hydrocarbon group and its preferred embodiment.

In the general formula (4), R ^1b is a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, -O-C (O) H, -C (O) -R ^7b or -SO ₂ -R Represents ^8b .
^Does R ^2b represent a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, -O-C (O) H, -C (O) -R ^7b or -SO ₂ -R ^8b ? Or R ^2b represents —C (O) —R ^9b . When R ^2b represents -C (O) -R ^9b , R ^1b , R ^2b, and a carbon atom to which R ^1b and R ^2b are bonded may have a substituent 4 Form an 8-membered heterocyclic ring.
R ^7b represents a hydrogen atom, a halogen atom, -NR ^72b R ^73b or -R ^74b , R ^8b represents a halogen atom, a hydroxy group, -OR ^81b , -NR ^82b R ^83b or -R ^84b , R ^9b Represents a hydrogen atom, a halogen atom, a hydroxy group, -OR ^91b , -NR ^92b R ^93b or -R ^94b . ^{R 72b ~R 74b, R 81b ~R} 84b and ^R 91b ^{to R 94b} are the same or different, a hydrogen atom, have an alkyl group or a substituent of carbon atoms which may 20 have a substituent Represents an optionally substituted aryl group having 6 to 20 carbon atoms.
R ^1b is preferably a cyano group, a heterocycle-containing group, —O—C (O) H, or —C (O) —R ^7b . R ^2b is preferably a cyano group, a heterocycle-containing group, —O—C (O) H or —C (O) —R ^7b , or R ^2b is —C (O) —R ^9b is there. In a preferred embodiment of the optionally substituted 4-8 membered heterocyclic ring at R ^1b and R ^2b, R ¹ , R ² , R ¹ and R ² in general formula (1) are combined And the preferred embodiment of the 4-8 membered heterocyclic ring formed by the carbon atom. R ^1b and R ^2b may be the same or different.
Preferred embodiments of R ^72b , R ^73b and R ^74b , R ^81b , R ^82b , R ^83b and R ^84b , and R ^91b , R ^92b , R ^93b and R ^94b are the above-mentioned R ⁷² , R ⁷³ and R ⁷⁴ , Preferred embodiments are the same as the preferred embodiments of R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ , and R ⁹¹ , R ⁹² , R ⁹³ and R ⁹⁴ , respectively.

In the general formula (4), R ^3b is a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 carbon atoms which may have a substituent And an aryl group of -20.
R ^402b is a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, -NR ^406b R ^{407 b} , -OR ^{408 b} , cyano group, -C (O) R ^{409 b} , -O-C (O) R ^{410 b} or -C (O) OR ^{411 b} , and R ^{404 b to} R ^{411 b} are the same or different and hydrogen; This represents an atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. R ^{404 b} , R ^{405 b,} and the nitrogen atom to which R ^{404 b} and R ^{405 b} are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent.
Preferred embodiments of R ^3b , R ^402b , R ^404b , R ^405a , R ^406b , R ^407b , R ^408b , R ^409b , R ^410b and R ^411b are the same as described above for R ³ , R ⁴⁰² , R ⁴⁰⁴ , R ⁴⁰⁵ , R ⁴⁰⁶ and R ^406. , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ are respectively the same as the preferred embodiments.

In one aspect, in general formula (3), R ^2a represents —C (O) —R ^9a , and R ^1a , R ^2a, and a carbon atom to which R ^1a and R ^2a are bonded, It is also preferable to form a 4- to 8-membered heterocyclic ring which may have a substituent. The 4- to 8-membered heterocyclic ring includes a 4- to 8-membered heterocyclic ring containing at least one hetero atom selected from a nitrogen atom, an oxygen atom and a sulfur atom, and may optionally have a substituent Preferred embodiments of the 8-membered heterocyclic ring are the same as preferred embodiments of the 4- to 8-membered heterocyclic ring formed by R ¹ , R ² and the carbon atom to which R ¹ and R ² are bonded. .

As the compound (1), the compound (5) is also preferred.
In the general formula (5), R ^2c represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -O-C (O) H, -C (O) -R ^7c or -SO _2- R ^8c is represented. R ^7c represents a hydrogen atom, a halogen atom, -NR ^72c R ^73c or -R ^74c , and R ^8c represents a halogen atom, a hydroxy group, -OR ^81c , -NR ^82c R ^83c or -R ^84c . R ^{72 c to} R ^{74 c} and R ^{81 c} to R ^{84 c} are the same or different and each is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or the carbon number which may have a substituent 6-20 aryl groups are represented. R ^2c is preferably a cyano group, a heterocyclic group or -C (O) -R ^7c , and more preferably a cyano group, -C (O) -NR ^72c R ^73c . Preferred embodiments of R ^72c , R ^73c and R ^74c , and R ^81c , R ^82c , R ^83c and R ^84c are the above-mentioned R ⁷² , R ⁷³ and R ⁷⁴ , and R ⁸¹ , R ⁸² , R ⁸³ and R Each of them is the same as the ⁸⁴ preferred embodiments.

In the general formula (5), R ^3c is a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 carbon atoms which may have a substituent And an aryl group of -20.
R ^402c and R ^403c are the same or different and each is a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 to 20 carbon atoms which may have a substituent aryl ^group, -NR ^406c R ^407c, represent ^{-OR 408 c,} a cyano ^group, -C (O) R ^409c, a -O-C ^{(O) R 410c} or ^{-C (O) oR 411c, R} 404c ~R 411c The same or different and each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. And R ^404c, and ^{R 405c, R 404c} and ^{R 405c} together with the nitrogen to atom to which they are attached, may form a nitrogen-containing heterocycle 4-8 membered which may have a substituent.
Preferred embodiments of R ^3c , R ^402c , R ^403c , R ^404c , R ^405c , R ^406c , R ^407c , R ^408c , R ^409c , R ^410c and R ^411c are the same as described above for R ³ , R ⁴⁰² , R ⁴⁰³ and R ⁴⁰⁴ , R ⁴⁰⁵ , R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ are respectively the same as the preferable embodiments.

In the general formula (5), R ⁵⁰¹ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, Or, it represents a group represented by the above general formula (6). R ⁵⁰¹ is preferably an alkyl group having 1 to 20 carbon atoms which may have a substituent (eg, methyl group, ethyl group, t-butyl group, cyclohexyl group, 4-t-butylcyclohexyl group, 2, 6-di-t-butyl-4-methylcyclohexyl and the like), an aryl group having 6 to 20 carbon atoms which may have a substituent (eg, phenyl group, methylphenyl group, dimethylphenyl group, trimethylphenyl group) And the like, or a group represented by the above general formula (6). In one aspect of the present invention, R ⁵⁰¹ is preferably a group represented by the above general formula (6).

In the general formula (5), Y ^1c represents -NR ^502c- , and R ^502c has a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or a substituent It also represents an aryl group having 6 to 20 carbon atoms. Y ^1c is preferably -NH-.

In the general formula (6), Q ³ represents a divalent hydrocarbon group having 1 to 20 carbon atoms that may have a substituent, and * represents a bonding site to the general formula (5). In the general formula (6), Q ³ is bonded to the general formula (5). The C 1 to C 20 divalent hydrocarbon group which may have a substituent in Q ³ and the preferable embodiments thereof are the C 1 to 20 carbon optionally having a substituent in Q ¹ described above It is the same as the divalent hydrocarbon group and its preferred embodiment. In one aspect, Q ³ is more preferably a divalent aryl group represented by the above general formula (20) and s is 0.

In the general formula (6), Y ^1d represents —NR ^{502 d} —, and R ^{502 d} has a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or a substituent It also represents an aryl group having 6 to 20 carbon atoms. Preferred embodiments of Y ^1d are the same as the preferred embodiments of Y ^1c described above.

In the general formula (6), R ^2d represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -O-C (O) H, -C (O) -R ^7d or -SO _2- R ^8d is represented. R ^7d represents a hydrogen atom, a halogen atom, -NR ^72d R ^73d or -R ^74d , and R ^8d represents a halogen atom, a hydroxy group, -OR ^81d , -NR ^82d R ^83d or -R ^84d . R ^{72 d to} R ^{74 d} and R ^{81 d to} R ^{84 d} are the same or different and each is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or a carbon number which may have a substituent 6-20 aryl groups are represented.
R ^2d is preferably a cyano group, a heterocyclic group, -O-C (O) H or -C (O) -R ^7d , and a cyano group, -C (O) -NR ^72d R ^73d is more preferable . Preferred embodiments of R ^72d , R ^73d and R ^74d and R ^81d , R ^82d , R ^83d and R ^84d are the same as described above for R ⁷² , R ⁷³ and R ⁷⁴ , and R ⁸¹ , R ⁸² , R ⁸³ and R Each of them is the same as the ⁸⁴ preferred embodiments.

R ^3d represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent .
R ^402d and ^{R 403d} are the same or different, a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms that may have a substituent group, carbon atoms which may have a substituent having 6 to 20 aryl ^group, -NR ^406d R ^407d, represents ^{-OR 408d,} a cyano ^group, -C (O) R ^409d, a -O-C ^{(O) R 410d} or ^{-C (O) oR 411d, R} 404d ~R 411d The same or different and each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. R ^{404 d} , R ^{405 d,} and the nitrogen atom to which R ^{404 d} and R ^{405 d} are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent.
Preferred embodiments of R ^3d , R ^402d , R ^403d , R ^404d , R ^405d , R ^406d , R ^407d , R ^408d , R ^409d , R ^410d and R ^411d are the same as described above for R ³ , R ⁴⁰² , R ⁴⁰³ and R ⁴⁰⁴ , R ⁴⁰⁵ , R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ are respectively the same as the preferable embodiments.

In one aspect of the present invention, it is also preferable that the compound (1) is a compound (7).
In general formula (7), Q ⁴ represents —SO ₂ — or a divalent C 1-20 hydrocarbon group which may have a substituent. The C 1 to C 20 divalent hydrocarbon group which may have a substituent in Q ⁴ and the preferable embodiment thereof are the C 1 to 20 carbon optionally having a substituent in Q ¹ described above It is the same as the divalent hydrocarbon group and its preferred embodiment. In one aspect of the present invention, Q ⁴ is preferably a bistrifluoromethylmethylene group or -SO _2- , and more preferably -SO _2- .

In the general formula (7), R ^1e represents a heterocycle-containing group, —C (O) —R ^7e or —SO ₂ —R ^8e , and R ^2e is a hydrogen atom, a cyano group, a nitro group, trifluoromethyl And a heterocycle-containing group, -O-C (O) H, -C (O) -R ^7e or -SO ₂ -R ^8e . R ^7e represents a hydrogen atom, a halogen ^atom, an -NR ^{72e R 73e,} or ^{-R 74e, R 8e} represents a halogen atom, hydroxy ^group, -OR ^81e, a -NR ^{82e R 83e,} or ^{-R 84e.} R ^72e to R ^74e and ^R 81e ^{to R 84e,} which may be the same or different, a hydrogen atom carbon atoms, which may have an alkyl group or a substituent having 1 to 20 carbon atoms that may have a substituent 6-20 aryl groups are represented. R ^1e and R ^2e may be the same or different.
R ^1e and R ^2e are preferably the same or different and are a cyano group, a heterocycle-containing group, —O—C (O) H, or —C (O) —R ^7e . R ^{72e, R 73e} and ^{R 74e and,} R ^81e R ^82e, a preferred embodiment of ^{R 83e} and ^{R 84e} is, ^{R 72, R 73} and ^{R 74} mentioned above, as well ^as the R ^81, R ^{82, R 83} and ^{R 84} Each of them is the same as the preferred embodiment.

In the general formula (7), R ^3e is a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 carbon atoms which may have a substituent And an aryl group of -20. R ^{402 e} and R ^{403 e} are the same or different and each is a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 to 20 carbon atoms which may have a substituent aryl ^group, -NR ^406e R ^407e, represent ^{-OR 408e,} a cyano ^group, -C (O) R ^409e, a -O-C ^{(O) R 410e} or ^{-C (O) oR 411e, R} 404e ~R 411e The same or different and each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. And R ^404e, and ^{R 405e, R 404e} and ^{R 405e} with the nitrogen atom to which they are attached, may form a nitrogen-containing heterocycle 4-8 membered which may have a substituent.
^{R 3e, R 402e, R 403e} , R 404e, R 405e, R 406e, R 407e, R 408e, R 409e, preferred embodiments of ^{R 410e} and ^{R 411e may, R} 3, ^{R 402} described ^{above, R 403,} R ⁴⁰⁴ , R ⁴⁰⁵ , R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ are respectively the same as the preferable embodiments.

Compound ^(3), when ^{R 413} is a group represented by the general formula (4) has the general formula (1) ^{Q 1} is ^{Q 2} (carbon atoms which may have a substituent 1 to 20 in A compound represented by formula (3), and a group represented by the general formula (3) and a group represented by the general formula (4) according to Q ^2: is there. The group represented by the general formula (3) and the group represented by the general formula (4) contain a methine structure, and both have a structure to be a pigment. Since the molecular weight is increased due to the dimer structure of the structure to be such a dye, the compound becomes difficult to sublime, and a dye compound having excellent heat resistance is obtained. The compound (3) in which R ⁴¹³ is a group represented by general formula (4) is a compound represented by the following general formula (3-1).

In the above formula (3-1), R ^1a , R ^2a , R ^3a , R ^402a , R ^404a and R ^405a , and Q ² , R ^1b , R ^2b , R ^3b , R ^402b , R ^404b and R ^405b are , And the same as the above.

Compound ^(5), when ^{R 501} is a group represented by the general formula (6) has the general formula (1) ^{Q 1} is ^{Q 3} (carbon atoms which may have a substituent 1 to 20 in Compounds having a dimer structure in which the group represented by the general formula (5) and the group represented by the general formula (6) are linked on both sides by Q ³ ; is there. The group represented by the general formula (5) and the structure represented by the general formula (6) include a methine structure and are structures to be dyes. Since the molecular weight is increased due to the dimer structure of the structure to be such a dye, the compound becomes difficult to sublime, and a dye compound having excellent heat resistance is obtained.
The compound (5) in which R ⁵⁰¹ is a group represented by general formula (6) is a compound represented by the following general formula (5-1).

In the above general formula (5-1), R ^2c , R ^3c , R ^402c , R ^403c , R ^404c , R ^405c and Y ^1c , and Q ³ , R ^2d , R ^3d , R ^402d , R ^403d , R ^404d , R ^{405 d} and Y ^{1 d} are as defined above.

Examples of preferred embodiments of the compound (1) of the present invention include the compounds A1 to A6, the compounds B1 to B4, the compound D1 and the compound E1 prepared in the examples. Among them, compounds A1 to A6 are preferable because of high light resistance. Compounds A1 to A5, compounds B2 and B4, and compound D1 are preferable from the viewpoint of high heat resistance. Compounds A2 to A4 and A6 and compound B4 are preferred in that they have high solubility in organic solvents.
The compounds A1 to A6 and the compound E1 are examples of the compound (3), the compounds B1 to B4 are an example of the compound (5), and the compound D1 is an example of the compound (7). The compound B4 can be said to be an example of the compound (3).

The method for producing the compound (1) of the present invention is not particularly limited, and can be produced, for example, by the following method. The method for producing the compound of the present invention will be described below with reference to an example of the synthesis method, but the method for producing the compound (1) of the present invention is not limited to the following method. Moreover, when performing the below-mentioned reaction, about functional groups other than the said site | part, you may protect beforehand with a suitable protective group as needed, and you may deprotect this at an appropriate stage.

In one embodiment of the present invention, when the compound represented by the general formula (1) is a compound represented by the following general formula (11) (compound (11)), for example, the compound is synthesized by the following method Can. The compound (11) is an example of the compound (1) of the present invention, and is a compound (dimeric compound) in which m is 2 in the general formula (1). The compound (11) can be said to be an example of a compound in which in the compound (3), R ⁴¹³ is a group represented by the general formula (4). In the following, compound (M21) is subjected to dehydration condensation reaction with compound (M4) to obtain compound (11).

In the above reaction formula, Q ^f represents a divalent linking group. R ^{402f, R 404f} and ^{R 405 f} as well as a preferred embodiment thereof are respectively ^{R 402, R 404} and ^{R 405} and their preferred embodiments as described above the same. The divalent linking group in Q ^f is the same as the divalent linking group in Q ¹ . Q ^f is preferably a divalent ^C 1-20 hydrocarbon group which may have a substituent. R ^1f , R ^2f and their preferred embodiments are the same as R ¹ and R ² described above and their preferred embodiments, respectively.
Wavy line

Represents a single bond, and the configuration of the double bond to which it is attached is, independently, E configuration or Z configuration or a mixture thereof. The same applies to the following.

The compound (M4) can be obtained, for example, by reacting a compound (M1) represented by the following general formula (M1) with a dihalogenated alkyl compound to alkoxylate the hydroxy group of the compound (M1). The compound (M1) can be obtained according to the method described in the Journal of the Chemical Society 1957, 4845.

In the above general formula (M1), R ^402f , R ^404f and R ^405f are as ^defined above.
The compound (11) can also be obtained by dimerization of the compound (M1) and the compound (M21) by dehydration after condensation of the compound (M1) and the compound (M21).

When the compound represented by General formula (1) is a compound (compound (12)) represented by following General formula (12), it can synthesize | combine, for example by the following methods. The compound (12) is an example of the compound (1) of the present invention, and is a dimer compound. The compound (12) can be said to be an example of a compound in which R ⁵⁰¹ is a group represented by general formula (6) in the compound (5). Below, a compound (12) is obtained by dehydrating-condensing a compound (M22) with a compound (M2-1).

In the above reaction formulae, R ^2g is a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, -O-C (O) H, -C (O) -R ^7g or -SO _2- R ^8g is represented. R ^7g represents a hydrogen atom, a halogen atom, -NR ^72g R ^73g or -R ^74g , and R ^8g represents a halogen atom, a hydroxy group, -OR ^81g , -NR ^82g R ^83g or -R ^84g . R ^2g is preferably a cyano group, a heterocycle-containing group, or -C (O) -R ^7g described above. R ^71g , R ^81g , R ^82g , R ^83g and R ^84g and their preferred embodiments are the same as the above-mentioned R ⁷¹ , R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ and their preferred embodiments, respectively. W ^g represents -C (O) -NH-Q ^g -NH-C (O)-, and the divalent linking group in Q ^g is the same as the divalent linking group in Q ¹ . Q ^g represents a divalent linking group. Q ^g is preferably a C 1 to C 20 divalent hydrocarbon group which may have a substituent. ^{R 402g,} R 403g, R ^404g and ^{R 405 g} and a preferred embodiment thereof is ^R 402 described ^above, R ^{403, R 404} and ^{R 405} and each and these preferred embodiments the same.
The compound (M2-1) and the compound (M2-2) described later can be obtained, for example, by alkoxylating the hydroxy group of the compound (M1).
The compound (12) can also be obtained by dehydrating condensation of the compound (M21) and the compound (M2-1) and then linking with R 1 ^f to dimerize as W ^g .

When the compound represented by General Formula (1) is a compound (Compound (13)) represented by the following General Formula (13), for example, it can be synthesized by the following method. The compound (13) is an example of the compound (1) of the present invention, and the monomer compound (m in the general formula (1) is 1). In the compound (3), in the compound (3), R ⁴¹³ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 to 20 carbon atoms which may have a substituent. It is also an example of a compound representing an aryl group of In the following, compound (M2) is subjected to dehydration condensation reaction with compound (M23) to obtain compound (13).

In the above reaction ^scheme , R ^402h , R ^403h , R ^404h and R ^405h and their preferred embodiments are the same as the above-described R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ and their preferred embodiments, respectively. R ^1h , R ^2h and their preferred embodiments are the same as R ¹ and R ² described above and their preferred embodiments, respectively.

The isolation and purification of each product in the above production method can be carried out by appropriately combining methods used in ordinary organic synthesis, such as filtration, extraction, washing, drying, concentration, crystallization, various chromatographies, etc. . In addition, intermediates can be subjected to the next reaction without particular purification.

The compound (1) of the present invention usually has an absorption maximum wavelength at 360 to 430 nm. If it has an absorption maximum wavelength in 360-430 nm, ultraviolet light and blue light can be selectively absorbed. The compound (1) of the present invention preferably has an absorption maximum wavelength at 370 to 430 nm. In addition, the compound (1) of the present invention preferably has a gram absorption coefficient of 400 nm of 30 or more. The absorption maximum wavelength and the gram absorption coefficient can be measured by the methods described in the examples.

The compound (1) of the present invention is preferably a compound that dissolves in the following organic solvent.
Examples of the organic solvent include aromatic hydrocarbons (eg, toluene, xylene etc.), ketones (methyl ethyl ketone, acetone, cyclohexanone, 2-heptanone, 3-heptanone etc.), ethers (eg propylene glycol monomethyl ether acetate) , Methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether etc., esters (eg methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl lactate, ethyl acetate, butyl acetate, methyl 3-methoxypropionate) And the like, and mixed solvents of two or more thereof.
The compound (1) is preferably dissolved in at least one of the organic solvents in an amount of 0.1% by mass or more, for example, 0.1% by mass or more and 50% by mass or less, preferably 1% by mass or more It is more preferable to dissolve 40% by mass or less, and it is further preferable to dissolve 3% by mass to 30% by mass. More preferably, the solubility in an organic solvent at 20 ° C. is in such a range. When the solubility in an organic solvent is in such a range, the compound (1) of the present invention is preferable, for example, when it is used for the production of an optical filter such as a color filter, and the like.

It is preferable that the thermal decomposition temperature of the compound (1) of this invention is 200 degreeC or more, 210 degreeC or more is more preferable, for example, it is preferable that it is 250-400 degreeC. The thermal decomposition temperature can be measured by a thermogravimetric apparatus.

The compound (1) of the present invention usually has an absorption maximum wavelength at 360 to 430 nm, and can effectively absorb light of this wavelength. The compound (1) of the present invention can effectively absorb light around 400 nm. In one aspect, the compound (1) of the present invention can improve heat resistance when it is a 2- to 6-mer compound (m is 2 to 6 in the general formula (1)). In a preferred embodiment of the present invention, the compound (1) of the present invention is excellent in solubility in an organic solvent. Therefore, the compound (1) of the present invention is suitably used, for example, as a dye for an optical filter such as a color filter, a color conversion filter, or a light absorption filter. The compound (1) of the present invention is also suitably used as a blue light shielding material, an ultraviolet light absorber, a recording material of a recording medium, and the like.

The compound (1) of the present invention can be made into a dye composition, for example, by mixing it with a resin or the like. The dye composition is suitably used as a coloring composition.
The above-mentioned resin is not particularly limited, and a thermoplastic resin, a photocurable resin, a thermosetting resin and the like may be appropriately selected depending on the application of the coloring composition and the like. For example, acrylic resin, polycarbonate resin, polystyrene resin, low density polyethylene resin, polypropylene resin, polyurethane resin, polyamide resin, polyacetal resin, polyphenylene sulfide resin, polyethylene terephthalate resin, polybutylene terephthalate resin, polycycloolefin resin, polysulfone resin, poly Resins, such as ether sulfone resin, a fluorine resin, a silicone resin, a polyester resin, an epoxy resin, a phenol resin, a melamine resin, are mentioned. These may be used alone or in combination of two or more.

The compounding amount of the compound (1) in the dye composition is, for example, preferably 0.001 to 50% by mass, and 0.01 to 40% by mass of the compound (1) based on the total solid content of the dye composition. It is more preferable that

The dye composition may contain an optional component other than the compound (1) of the present invention and the resin, depending on the use and the like. Examples of optional components include antioxidants, antifoaming agents, other dyes (dyes, pigments, etc.), infrared absorbers, polymerizable monomers, polymerization initiators, sensitizers and the like. Moreover, you may also contain ultraviolet absorbers other than a compound (1).
The method for producing the dye composition is not particularly limited, and for example, the compound (1) of the present invention and the resin, and optionally blended optional components may be mixed.

The compound (1) of the present invention, and the dye for an optical filter and the dye composition containing the compound (1) of the present invention are suitably used, for example, in the production of an optical filter.

The optical filter may be any one containing the compound (1) of the present invention, and the configuration of the optical filter is not particularly limited. For example, as in the prior art, it has at least a support, and if necessary, it can have various functional layers such as an adhesive layer, an optical functional layer, an antireflective layer, a hard coat layer and the like. In the optical filter, the compound (1) of the present invention may be contained in any of the support and various functional layers, and for example, is preferably contained in the support or the optical functional layer. Further, the size and shape of the optical filter are not particularly limited, and may be appropriately selected according to the application and the like.

The configurations of the support and the various functional layers are also not particularly limited. For example, the support is usually formed using a transparent resin. As transparent resin, for example, cyclic olefin resin, aromatic polyether resin, polyimide resin, fluorene polycarbonate resin, fluorene polyester resin, polycarbonate resin, polyamide (aramid) resin, polyarylate resin, polysulfone Resin, polyether sulfone resin, polyparaphenylene resin, polyamideimide resin, polyethylene naphthalate (PEN) resin, fluorinated aromatic polymer resin, (modified) acrylic resin, epoxy resin etc. It can be mentioned.

The manufacturing method of the optical filter is not particularly limited. For example, as a method of forming an optical functional layer containing the compound (1) of the present invention on a support, the compound (1) of the present invention and a binder resin are dissolved or dispersed in a solvent, Examples include a method of forming a coating on a support by a coating method such as air knife coating, curtain coating, roller coating, wire bar coating, gravure coating, spin coating and extrusion coating. Although it does not restrict | limit especially as said solvent, The organic solvent etc. which were mentioned above are mentioned.

Moreover, as a method for producing an optical functional layer or a support comprising the compound (1) of the present invention, the compound (1) of the present invention, a photocurable resin and / or a thermosetting resin, and a photopolymerization initiator and / or After mixing with a thermal polymerization initiator, a cured film may be formed by light irradiation and / or heat treatment, and this may be used as an optical functional layer or a support.

The optical filter is, for example, an optical filter such as a color filter, a color conversion filter, a light absorption filter, a liquid crystal display, an organic EL display, an imaging device, an insect repellent such as a lighting tool or window glass ) It can be suitably used for materials and the like.

The dye composition containing the compound (1) of the present invention and the compound (1) of the present invention is also suitably used, for example, in the production of blue light shielding materials, ultraviolet light absorbers, recording materials and cosmetics.
Also included in the present invention are blue light shielding materials, ultraviolet light absorbers, recording materials and cosmetics containing the compound (1) of the present invention. The blue light shielding material, the ultraviolet light absorber, the recording material, and the cosmetic may be any one containing the compound (1), and the configuration thereof is not particularly limited.
The blue light shielding material is not particularly limited, and examples thereof include blue light cut films; blue light blocking lenses such as lenses for blue light cutting glasses or contact lenses. As a method of producing a lens which is an example of a blue light shielding material, for example, a method of kneading the compound (1) of the present invention in a transparent resin and molding it by injection molding, compression molding, extrusion molding etc. Various methods such as a method of forming an optical functional layer containing the compound (1) of the present invention on a support described later can be adopted. The UV absorber can be used for various materials such as glass, plastic, fiber, paper, paint, ink, cosmetics and the like. The UV absorber can be used as a mixture with various materials, and may be dispersed or dissolved in the material. In addition, the UV absorber may be supported chemically or physically on various materials.
Examples of the recording material containing the compound (1) of the present invention include an optical disc and the like.

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

The equipment and measurement conditions used when measuring the physical property of the compound obtained below are as follows.
(GC-MS)
Gas chromatograph mass spectrometer GCMS-QP2010 Plus (EI method) manufactured by Shimadzu Corporation
(LC / MS)
Shimadzu Corporation high performance liquid chromatograph mass spectrometer LCMS-2010 EV (ESI method)

<Production Example 1>
Compound A6 represented by the following formula was synthesized. The reaction formula is shown below.

(Synthesis of Compound IM2)
In the synthesis of 2-dimethylamino-4-hydroxy-6-methylpyrimidine described in Journal of American Chemical Society 1954, 76, 1879 in a 1 L four-necked flask provided with a condenser and a thermometer, N, N-dimethyl A compound IM1 was obtained in the same manner except that guanidine sulfate was replaced with 1,1-dibutylguanidine hydrochloride obtained in the same manner as the method described in BE639386. Compound IM1 was used for formylation by Reimer-Tiemann reaction according to a procedure similar to the method described in Journal of the Chemical Society 1957, 4845 to give compound IM2 (18.4 g, yield 69%) The
GC-MS: m / z = 265 ([M] ⁺ )

(Synthesis of Compound IM3)
Compound IM2 (15.8 g), ethyl iodide (manufactured by Tokyo Chemical Industry Co., Ltd.) (14 g), potassium carbonate (14 g), dimethylformamide (DMF) in a 100 mL four-necked flask provided with a condenser and a thermometer The mixture of (60 mL) was stirred at 70 ° C. for 3 hours and allowed to cool to room temperature. The reaction was poured into water (300 mL) and extracted with toluene (300 mL). The organic layer was concentrated under reduced pressure to give compound IM3 (17.3 g, yield 99%).
GC-MS: m / z = 293 ([M] ⁺ )

(Synthesis of Compound A6)
Compound IM3 (2.2 g), malononitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.5 g), piperidine (0.03 g), ethanol (6 mL) in a 25 mL four-necked flask provided with a condenser and a thermometer The mixture was stirred at 75 ° C. for 1 hour. The mixture was allowed to cool to room temperature, and the precipitated crystals were collected by filtration. The obtained crystals were washed with ethanol to give compound A6 (1.4 g, yield 67%).
LC-MS: m / z = 342 ([M + H] ⁺ )

<Production Example 2>
Compounds A1 to A4 represented by the following formulas were synthesized. The compound A1 is a compound in which k in the following is 4. The compound A2 is a compound in which k in the following formula is 5. The compound A3 is a compound in which k in the following formula is 6. The compound A4 is a compound in which k in the following formula is 8.

The reaction formula is shown below. The k and corresponding compounds in the formula are shown in Table 1.

(Synthesis of Compound IM4)
Compound IM2 (2.7 g), 1,4-diiodobutane (manufactured by Tokyo Chemical Industry Co., Ltd.) (1.5 g), potassium carbonate (1.7 g) in a 50 mL four-necked flask provided with a condenser and a thermometer The mixture was charged with DMF (20 mL) and stirred at 80 ° C. for 2.5 hours. The reaction solution was drained into water, and the precipitated crystals were collected by filtration. The crystals were washed with methanol to give compound IM4 (2.6 g, yield 89%).

(Synthesis of Compound A1)
Compound IM4 (2.3 g), malononitrile (0.64 g), piperidine (0.17 g), ethanol (10 mL) are charged into a 25 mL four-necked flask equipped with a condenser and a thermometer, and heated at 70 ° C. Stir for 5 hours. The reaction solution was allowed to cool to room temperature and then the crystals were filtered off. The crystals were washed with isopropyl alcohol (IPA) to give compound A1 (1.4 g, yield 56%).
LC-MS: m / z = 681 ([M + H] ⁺ )

(Synthesis of Compound IM5)
Compound IM5 was obtained by a similar procedure except that 1,4-diiodobutane in synthesis of compound IM4 was replaced with 1,5-dibromopentane (manufactured by Tokyo Chemical Industry Co., Ltd.) (yield 71%).

(Synthesis of Compound A2)
Compound A2 was obtained by the same procedure except that the compound IM4 in the synthesis of the compound A1 was replaced with the compound IM5 (yield: 67%).
LC-MS: m / z = 695 ([M + H] ⁺ )

(Synthesis of Compound IM6)
Compound IM6 was obtained (yield 82%) by the same procedure except that 1,4-diiodobutane in the synthesis of compound IM4 was replaced with 1,6-dibromohexane (manufactured by Tokyo Chemical Industry Co., Ltd.).

(Synthesis of Compound A3)
A compound A3 was obtained by the same procedure except that the compound IM4 in the synthesis of the compound A1 was replaced with the compound IM6 (yield 90%).
LC-MS: m / z = 709 ([M + H] ⁺ )

(Synthesis of Compound IM7)
Compound IM7 was obtained (yield 84%) by the same procedure except that 1,4-diiodobutane in the synthesis of compound IM4 was replaced with 1,8-diiodooctane (manufactured by Tokyo Chemical Industry Co., Ltd.).

(Synthesis of Compound A4)
Compound A4 was obtained by the same procedure except that the compound IM4 in the synthesis of the compound A1 was replaced with the compound IM7 (yield 40%).
LC-MS: m / z = 737 ([M + H] ⁺ )

<Production Example 3>
The compound A5 represented by the following formula was synthesized. The reaction formula is shown below.

(Synthesis of Compound IM8)
Compound IM2 (2.7 g), α, α'-dibromo-p-xylene (manufactured by Tokyo Chemical Industry Co., Ltd.) (1.3 g), potassium carbonate in a 50 mL four-necked flask provided with a condenser and a thermometer (1.5 g), DMF (20 mL) was charged and stirred at 60 ° C. for 90 minutes. The mixture was poured into water (60 mL), and the precipitated crystals were collected by filtration and washed with water. The obtained crude crystals were washed with methanol to give compound IM8 (2.8 g, yield 89%).
LC-MS: m / z = 633 ([M + H] ⁺ )

(Synthesis of Compound A5)
Compound IM8 (2.7 g), malononitrile (0.62 g), piperidine (0.08 g), ethanol (18 mL), DMF (4 mL) are charged into a 50 mL four-necked flask equipped with a condenser and a thermometer. Stir at 4 ° C for 4 hours. The reaction solution was allowed to cool to room temperature, and the precipitated crystals were collected by filtration. The crystals were washed with methanol to give compound A5 (2.57 g, yield 82%).

Production Example 4
The compound B4 represented by the following formula was synthesized. The reaction formula is shown below.

(Synthesis of Compound B4)
Compound IM3 (1.5 g), 2-cyanoacetanilide (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.82 g), pyrimidine (0.05 g), toluene in a 25 mL four-necked flask provided with a condenser and a thermometer (5 mL) and n-butanol (5 mL) were added and stirred at 95 ° C. for 4.5 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to give a crude product, which was washed with ethanol to give compound B4 (1.1 g, yield 49%).
LC-MS: m / z = 436 ([M + H] ⁺ )

<Production Example 5>
The compound B1-the compound B3 represented by a following formula were synthesize | combined.

The reaction formula is shown below. The positions of substituents on the benzene ring in the formula and the corresponding compounds are shown in Table 2.

(Synthesis of Compound IM9)
In a 500 mL four-necked flask provided with a condenser and a thermometer, cyanoacetic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) (10.2 g), o-phenylenediamine (manufactured by Tokyo Chemical Industry Co., Ltd.) (6.5 g), 4-dimethylaminopyridine (made by Tokyo Chemical Industry Co., Ltd.) (4.9 g), ginger sulfonic acid (made by Tokyo Chemical Industry Co., Ltd.) (3.1 g), chloroform (160 mL) are mixed, 1-ethyl- A mixed solution of 3- (3-dimethylaminopropyl) carbodiimide (EDC) (manufactured by Tokyo Chemical Industry Co., Ltd.) (25.3 g) and chloroform (80 mL) was dropped. After stirring at room temperature for 2 hours, the reaction mixture was concentrated, and the obtained crude product was washed with methanol to give compound IM9 (5.9 g, yield 41%).

(Synthesis of Compound B1)
Compound IM3 (1.2 g), compound IM9 (0.49 g), piperidine (0.04 g), toluene (5 mL), n-butanol (5 mL) in a 25 mL four-necked flask equipped with a condenser and a thermometer Were stirred at 95.degree. C. for 16.5 hours. The reaction mixture was concentrated under reduced pressure, and silica gel column chromatography was performed to obtain Compound B1 (0.25 g, yield 16%).
LC-MS: m / z = 793 ([M + H] ⁺ )

(Synthesis of Compound IM10)
Compound IM10 was obtained by the same procedure except that o-phenylenediamine in the synthesis of compound IM9 was replaced with p-phenylenediamine (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (yield: 59%).

(Synthesis of Compound B2)
The compound B2 was obtained by the same procedure except that the compound IM9 in the synthesis of the compound B1 was replaced with the compound IM10 (yield: 61%).
LC-MS: m / z = 793 ([M + H] ⁺ )

(Synthesis of Compound IM11)
Compound IM11 was obtained by a similar procedure except that o-phenylenediamine in the synthesis of compound IM9 was replaced with m-phenylenediamine (manufactured by Tokyo Chemical Industry Co., Ltd.) (yield 41%).

(Synthesis of Compound B3)
Compound B3 was obtained by the same procedure except that the compound IM9 in the synthesis of the compound B1 was replaced with the compound IM11 (yield: 38%).
LC-MS: m / z = 793 ([M + H] ⁺ )

<Production Example 6>
The compound D1 represented by the following formula was synthesized. The reaction formula is shown below.

(Synthesis of Compound IM16)
Malononitrile (3.3 g), ethanol (5 g) and ethyl acetate (15 mL) were mixed in a 50 mL four-necked flask equipped with a condenser and a thermometer, and thionyl chloride (6 g) was dropped at 8 ° C. The reaction solution was stirred at room temperature for 20 hours, and then the precipitated crystals were collected by filtration. The residue was washed with ethyl acetate to give compound IM16 (6.4 g, yield 86%).

(Synthesis of Compound IM17)
In a 100 mL four-necked flask provided with a condenser and a thermometer, bis (3-amino-4-hydroxyphenyl) sulfone (manufactured by Tokyo Chemical Industry Co., Ltd.) (4.2 g) and methanol (30 mL) are mixed, Compound IM16 (5 g) was added at 5 ° C. or less, the temperature was gradually raised, and after stirring for 19 hours at 60 ° C., the mixture was allowed to cool to room temperature. The precipitated crystals were collected by filtration and washed with methanol and warm water to give compound IM17 (4.4 g, yield 77%).

(Synthesis of Compound D1)
Compound D1 was obtained by the same procedure except that the compound IM9 in the synthesis of the compound B1 was replaced with the compound IM17 (yield 74%).
LC-MS: m / z = 929 ([M + H] ⁺ )

Production Example 7
The compound E1 represented by the following formula was synthesized. The reaction formula is shown below.

(Synthesis of Compound E1)
Compound E1 is obtained by the same procedure as the synthesis of compound A6 except that malononitrile in the synthesis of compound A6 is replaced with compound IM15 obtained in the same manner as the method described in Tetrahedron 1999, 55 (1), 193-200. (Yield 14%).
LC-MS: m / z = 481 ([M + H] ⁺ )

<Comparative production example (comparative example compound)>

(Synthesis of Comparative Example Compound Z1)
Comparative example compound Z1 was obtained in the same manner as the method described in JP2011-184414A.
(Synthesis of Comparative Example Compound Z2)
Comparative example compound Z2 was obtained in the same manner as the method described in JP-A-2014-194508.

(Synthesis of Comparative Example Compound Z3)
Comparative example compound Z3 was obtained in the same manner as the method described in JP-A-2009-067973.
(Synthesis of Comparative Example Compound Z4)
A comparative example compound Z4 was obtained in the same manner as the method described in US2986528.

The following evaluation was performed about the compound obtained by each manufacture example. The results are shown in Table 3.
<Spectroscopic characteristic test>
The absorption spectrum of each compound in chloroform was measured, and the absorption maximum wavelength (λmax) and the gram absorption coefficient at 400 nm were measured and evaluated according to the following criteria.
Measuring instrument: UV-visible spectrophotometer V-560 manufactured by JASCO Corporation
A: Gram absorption coefficient 30 or more B: Gram absorption coefficient 20 or more, less than 30 C: Gram absorption coefficient 10 or more, less than 20 D: Gram absorption coefficient less than 10

<Light resistance test>
The light resistance test was done about the one part compound obtained by the manufacture example and the comparative manufacture example. 10 mg of each compound was melted in 5 mL of a polymethacrylate 8 wt% toluene solution, applied onto a glass substrate by spin coating, and dried to prepare a thin film having a thickness of 1.5 μm.
The thin film produced was continuously irradiated with light of a xenon lamp (142 klux) for 96 hours continuously, the transmittance of the thin film after irradiation was measured with a spectrophotometer before irradiation (0 hour), and the dye remained according to the following formula (1) The rate was measured.
Dye residual ratio (%) = {(1-T ₁ ) / (1-T ₀ )} × 100 (1)
[Wherein T ₀ is the transmittance before irradiation with the xenon lamp, T ₁ is the transmittance after irradiation with the xenon lamp, and T ₀ and T ₁ are 0 to ₁ . ]
The “transmittance” represents the transmittance at the absorption maximum wavelength of each compound, and the higher the dye residual rate, the more difficult the compound is to be decomposed by light and the higher the light resistance.
The light resistance was evaluated according to the following criteria.
A: Dye residual rate is 65% or more B: Dye residual rate is 40% or more and less than 65% C: Dye residual rate is 10% or more and less than 40% D: Dye residual rate is less than 10%

<Heat resistance>
For some compounds obtained in Production Examples and Comparative Production Examples, the weight loss due to thermal decomposition was measured under the following measurement conditions using a thermogravimetry apparatus TGA-50 manufactured by Shimadzu Corporation, and from the initial weight The temperature reduced by 1% was measured as the decomposition initiation temperature.
(Measurement condition)
The sample amount was 5 mg, the temperature rising rate was 10 ° C./min (the maximum temperature reached 400 ° C.), and the measurement was performed in a nitrogen atmosphere under a flow rate of 10 mL / min.
The heat resistance was evaluated from the decomposition initiation temperature according to the following criteria.
A: 250 ° C. or more B: 210 ° C. or more and less than 250 ° C. C: less than 210 ° C.

<Solubility test>
The solubility (% by weight) in toluene, methyl ethyl ketone (MEK) and propylene glycol monomethyl ether acetate (PGMEA) at 20 ° C. was measured by the following method for some of the compounds obtained in Production Examples and Comparative Production Examples.
Each compound was weighed in a glass test tube, the solvents were mixed, stirred at 20 ° C. for dissolution, the state of the solution was visually observed, and the soluble weight concentration was evaluated.
A: 3 wt% or more dissolved B: 1 wt% or more and less than 3 wt% dissolved C: less than 1 wt% dissolved

From the above results, it was found that the compounds A1 to A6, B1 to B4, D1 and E1 produced in the respective production examples have an absorption maximum wavelength near 400 nm and a high gram absorption coefficient at 400 nm. These compounds can effectively absorb light around 400 nm. Moreover, these compounds were also good in durability. For example, the compounds A2 to A4 produced in Production Example 2 are excellent in light resistance, solubility, and heat resistance, and are compounds which can be suitably applied as, for example, dyes for blue light shielding materials and optical filters. I understand. Comparative Example Compounds Z1 to Z2 and Z4 had an absorption maximum wavelength at 363 to 382 nm, but had a low gram absorption coefficient at 400 nm. The compounds of the present invention produced in each production example can absorb light near 400 nm more effectively than the comparative compounds Z1 to Z2 and Z4. The comparative example compound Z3 had insufficient durability.

Claims (11)

Compound represented by the following general formula (3).

(In the general formula (3), R ^1a represents a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, —O—C (O) H, —C (O) —R ^7a or —SO ₂ — It represents R ^{8a, R 2a} is a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic ring-containing group, -O-C (O) H , -C (O) -R 7a or -SO ₂ - or represents R ^{8a, or, R 2a} represents a -C (O) ^{-R 9a,} with a ^{R 1a,} and ^{R 2a,} with the carbon atom ^{to which R 1a} and ^{R 2a} are bonded, substituted R ^7a represents a hydrogen atom, a halogen atom, -NR ^72a R ^73a or -R ^74a , and R ^8a represents a halogen atom, a hydroxy group,- oR ^81a, represents ^-NR 82a ^{R 83a} or ^{-R 84a, R 9a} is a hydrogen atom, halogen Atom, hydroxy ^{group, .R} 72a ^{to R} 74a representing the -OR ^91a, -NR ^{92a R 93a} or ^{-R 94a, R} 81a ^{~R 84a} and ^R 91a ^{to R 94a} are the same or different, a hydrogen atom, a substituent Or an alkyl group having 1 to 20 carbon atoms which may have 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms which may have a substituent.
R ^3a represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent .
R ^402a is a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, -NR ^406a R ^407a , -OR ^408a , cyano group, -C (O) R ^409a , ^-OC (O) R ^410a or -C (O) OR ^411a , wherein R ^{404a to} R ^411a are the same or different and hydrogen; This represents an atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. R ^{404 a} , R ^{405 a,} and the nitrogen atom to which R ^{404 a} and R ^{405 a} are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent.
R ⁴¹³ represents a group represented by the following general formula (4).

(In the general formula (4), Q ² represents a divalent hydrocarbon group having 1 to 20 carbon atoms that may have a substituent, and * represents a bonding site to the general formula (3).
R ^1b represents a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, -O-C (O) H, -C (O) -R ^7b or -SO ₂ -R ^8b , and R ^2b represents Or a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, -O-C (O) H, -C (O) -R ^7b or -SO ₂ -R ^8b , or R 2 ^b represents —C (O) —R ^{9 b} , and R 4 ^b , R 2 ^b, and a carbon atom to which R 1 ^b and R 2 ^b are bonded may have a substituent and may be 4 to 8 members Form a heterocycle of R ^7b represents a hydrogen atom, a halogen atom, -NR ^72b R ^73b or -R ^74b , R ^8b represents a halogen atom, a hydroxy group, -OR ^81b , -NR ^82b R ^83b or -R ^84b , R ^9b Represents a hydrogen atom, a halogen atom, a hydroxy group, -OR ^91b , -NR ^92b R ^93b or -R ^94b . ^{R 72b ~R 74b, R 81b ~R} 84b and ^R 91b ^{to R 94b} are the same or different, a hydrogen atom, have an alkyl group or a substituent of carbon atoms which may 20 have a substituent Represents an optionally substituted aryl group having 6 to 20 carbon atoms.
R ^3b represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent .
R ^402b is a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, -NR ^406b R ^{407 b} , -OR ^{408 b} , cyano group, -C (O) R ^{409 b} , -O-C (O) R ^{410 b} or -C (O) OR ^{411 b} , and R ^{404 b to} R ^{411 b} are the same or different and hydrogen; This represents an atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. R ^{404 b} , R ^{405 b,} and the nitrogen atom to which R ^{404 b} and R ^{405 b} are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent. ))) Compound represented by the following general formula (3).

(In the general formula (3), R ^1a represents a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, —O—C (O) H, —C (O) —R ^7a or —SO ₂ — R ^8a is represented, R ^2a is —C (O) —R ^9a , and R ^1a , R ^2a, and a carbon atom to which R ^1a and R ^2a are bonded have a substituent .R ^7a forming the heterocyclic ring may also be 4-8 membered represents a hydrogen atom, a halogen ^atom, a -NR ^{72a R 73a} or ^{-R 74a, R 8a} represents a halogen atom, hydroxy ^{group, -OR 81a} And -NR ^82a R ^83a or -R ^84a , wherein R ^9a represents a hydrogen atom, a halogen atom, a hydroxy group, -OR ^91a , -NR ^92a R ^93a or -R ^94a R ^{72a to} R ^74a , R ^81a ~R ^84a and ^R 91a ^{~R 94a} , Identical or different, represent a hydrogen atom, having 1 to 20 carbon atoms that may have a substituent alkyl or optionally substituted aryl group having 6 to 20 carbon atoms.
R ^3a represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent .
R ^402a is a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, -NR ^406a R ^407a , -OR ^408a , cyano group, -C (O) R ^409a , ^-OC (O) R ^410a or -C (O) OR ^411a , wherein R ^{404a to} R ^411a are the same or different and hydrogen; This represents an atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. R ^{404 a} , R ^{405 a,} and the nitrogen atom to which R ^{404 a} and R ^{405 a} are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent.
R ⁴¹³ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, or This represents a group represented by formula (4).

(In the general formula (4), Q ² represents a divalent hydrocarbon group having 1 to 20 carbon atoms that may have a substituent, and * represents a bonding site to the general formula (3).
R ^1b represents a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, -O-C (O) H, -C (O) -R ^7b or -SO ₂ -R ^8b , and R ^2b represents Or a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, -O-C (O) H, -C (O) -R ^7b or -SO ₂ -R ^8b , or R 2 ^b represents —C (O) —R ^{9 b} , and R 4 ^b , R 2 ^b, and a carbon atom to which R 1 ^b and R 2 ^b are bonded may have a substituent and may be 4 to 8 members Form a heterocycle of R ^7b represents a hydrogen atom, a halogen atom, -NR ^72b R ^73b or -R ^74b , R ^8b represents a halogen atom, a hydroxy group, -OR ^81b , -NR ^82b R ^83b or -R ^84b , R ^9b Represents a hydrogen atom, a halogen atom, a hydroxy group, -OR ^91b , -NR ^92b R ^93b or -R ^94b . ^{R 72b ~R 74b, R 81b ~R} 84b and ^R 91b ^{to R 94b} are the same or different, a hydrogen atom, have an alkyl group or a substituent of carbon atoms which may 20 have a substituent Represents an optionally substituted aryl group having 6 to 20 carbon atoms.
R ^3b represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent .
R ^402b is a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, -NR ^406b R ^{407 b} , -OR ^{408 b} , cyano group, -C (O) R ^{409 b} , -O-C (O) R ^{410 b} or -C (O) OR ^{411 b} , and R ^{404 b to} R ^{411 b} are the same or different and hydrogen; This represents an atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. R ^{404 b} , R ^{405 b,} and the nitrogen atom to which R ^{404 b} and R ^{405 b} are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent. ))) Compound represented by the following general formula (5).

(In the general formula (5), R ^2c represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, —O—C (O) H, —C (O) —R ^7c or — ^{.R 7c} representing the SO ₂ -R ^8c is hydrogen atom, a halogen ^atom, an -NR ^{72c R 73c} or ^{-R 74c, R 8c} represents a halogen atom, hydroxy ^group, -OR ^81c, -NR ^{82c R 83c} or ^{-R 84c .R} 72c ^{~R 74c} and ^R 81c represents a ^{to R 84c} are the same or different, a hydrogen atom, have an alkyl group or a substituent of carbon atoms which may 20 have a substituent Represents an optionally substituted aryl group having 6 to 20 carbon atoms.
R ^3c represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent .
R ^402c and R ^403c are the same or different and each is a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 to 20 carbon atoms which may have a substituent aryl ^group, -NR ^406c R ^407c, represent ^{-OR 408 c,} a cyano ^group, -C (O) R ^409c, a -O-C ^{(O) R 410c} or ^{-C (O) oR 411c, R} 404c ~R 411c The same or different and each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. And R ^404c, and ^{R 405c, R 404c} and ^{R 405c} together with the nitrogen to atom to which they are attached, may form a nitrogen-containing heterocycle 4-8 membered which may have a substituent.
R ⁵⁰¹ represents a group represented by the following general formula (6).
Y ^1c represents —NR ^{502 c} —, and R ^{502 c} represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 to 20 carbon atoms which may have a substituent Represents an aryl group of

(In the general formula (6), Q ³ represents a divalent hydrocarbon group having 1 to 20 carbon atoms that may have a substituent, and * represents a bonding site to the general formula (5).
Y ^1d represents —NR ^{502 d} —, and R ^{502 d} represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 to 20 carbon atoms which may have a substituent Represents an aryl group of
R ^2d represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, -O-C (O) H, -C (O) -R ^7d or -SO ₂ -R ^8d . R ^7d represents a hydrogen atom, a halogen atom, -NR ^72d R ^73d or -R ^74d , and R ^8d represents a halogen atom, a hydroxy group, -OR ^81d , -NR ^82d R ^83d or -R ^84d . R ^{72 d to} R ^{74 d} and R ^{81 d to} R ^{84 d} are the same or different and each is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or a carbon number which may have a substituent 6-20 aryl groups are represented.
R ^3d represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent .
R ^402d and ^{R 403d} are the same or different, a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms that may have a substituent group, carbon atoms which may have a substituent having 6 to 20 aryl ^group, -NR ^406d R ^407d, represents ^{-OR 408d,} a cyano ^group, -C (O) R ^409d, a -O-C ^{(O) R 410d} or ^{-C (O) oR 411d, R} 404d ~R 411d The same or different and each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. R ^{404 d} , R ^{405 d,} and the nitrogen atom to which R ^{404 d} and R ^{405 d} are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent. ))) Compound represented by the following general formula (7).

(In the general formula (7), ^{Q 4} is, -SO ₂ - represents a divalent hydrocarbon group or carbon atoms which may 20 have a substituent.
R ^1e represents a hetero ring-containing group, —C (O) —R 7 ^e or —SO ₂ —R ^{8 e} , and R ^{2 e} is a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a hetero ring-containing group, -O-C (O) H, -C (O) -R ^7e or -SO ₂ -R ^8e . R ^7e represents a hydrogen atom, a halogen ^atom, an -NR ^{72e R 73e,} or ^{-R 74e, R 8e} represents a halogen atom, hydroxy ^group, -OR ^81e, a -NR ^{82e R 83e,} or ^{-R 84e.} R ^72e to R ^74e and ^R 81e ^{to R 84e,} which may be the same or different, a hydrogen atom carbon atoms, which may have an alkyl group or a substituent having 1 to 20 carbon atoms that may have a substituent 6-20 aryl groups are represented.
R ^3e represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent .
R ^{402 e} and R ^{403 e} are the same or different and each is a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or 6 to 20 carbon atoms which may have a substituent aryl ^group, -NR ^406e R ^407e, represent ^{-OR 408e,} a cyano ^group, -C (O) R ^409e, a -O-C ^{(O) R 410e} or ^{-C (O) oR 411e, R} 404e ~R 411e The same or different and each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. And R ^404e, and ^{R 405e, R 404e} and ^{R 405e} with the nitrogen atom to which they are attached, may form a nitrogen-containing heterocycle 4-8 membered which may have a substituent. ) Wherein ^{Q 4} is, -SO ₂ - A compound according to claim 4. The compound according to any one of claims 1 to 5, which is a dye compound. A dye composition comprising the compound according to any one of claims 1 to 6 . An optical filter comprising a compound represented by the following general formula (1) .

(In the general formula (1), m represents an integer of 1 to 6,
Q ¹ represents a hydrogen atom when m is 1 and a divalent to hexavalent linking group when m is 2 to 6,
D ¹ represents a group in which one hydrogen atom is removed from the compound represented by the following general formula (2), and when m is 2 to 6, a plurality of D ¹ may be all the same or different It may be

(In the general formula (2), R ¹ represents a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, —O—C (O) H, —C (O) —R ⁷ or —SO ₂ — represents R ^{8, R 2} is a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic ring-containing group, -O-C (O) H , -C (O) -R 7 or -SO ₂ - or represents R ^8, or, ^{R 2} represents -C (O) -R ^9, and ^{R 1,} with the ^{R 2,} with the carbon atom ^{to which R 1} and ^{R 2} are attached, a substituent R ⁷ represents a hydrogen atom, a halogen atom, -NR ⁷² R ⁷³ or -R ⁷⁴ , and R ⁸ represents a halogen atom, a hydroxy group,- oR ^81, represents ^-NR 82 ^{R 83} or ^{-R 84, R 9} represents a hydrogen atom, a halogen atom, hydroxy ^group, -OR 91, -NR ^{9 .R 72 ~R 74, R 81 ~R} 84 and ^R 91 ^{to R 94} representing a R ⁹³ or ^{-R 94} are the same or different, a hydrogen atom, an optionally substituted alkyl group or a substituted group And an aryl group which may have
R ³ represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group which may have a substituent, or an aryl group which may have a substituent.
R ⁴⁰² and R ⁴⁰³ are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, -NR ⁴⁰⁶ R ⁴⁰⁷ , -OR ^408, a cyano ^{group, -C (O) R 409,} -O-C (O) R 410 or -C ^{(O) oR 411,}
R ^{404 to} R ⁴¹¹ are the same or different and each represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent. R ⁴⁰⁴ , R ^405, and the nitrogen atom to which R ⁴⁰⁴ and R ⁴⁰⁵ are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent. ))) The optical filter according to claim 8 , which is a color filter. A blue light shielding material comprising a compound represented by the following general formula (1) .

(In the general formula (1), m represents an integer of 1 to 6,
Q ¹ represents a hydrogen atom when m is 1 and a divalent to hexavalent linking group when m is 2 to 6,
D ¹ represents a group in which one hydrogen atom is removed from the compound represented by the following general formula (2), and when m is 2 to 6, a plurality of D ¹ may be all the same or different It may be

(In the general formula (2), R ¹ represents a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, —O—C (O) H, —C (O) —R ⁷ or —SO ₂ — represents R ^{8, R 2} is a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic ring-containing group, -O-C (O) H , -C (O) -R 7 or -SO ₂ - or represents R ^8, or, ^{R 2} represents -C (O) -R ^9, and ^{R 1,} with the ^{R 2,} with the carbon atom ^{to which R 1} and ^{R 2} are attached, a substituent R ⁷ represents a hydrogen atom, a halogen atom, -NR ⁷² R ⁷³ or -R ⁷⁴ , and R ⁸ represents a halogen atom, a hydroxy group,- oR ^81, represents ^-NR 82 ^{R 83} or ^{-R 84, R 9} represents a hydrogen atom, a halogen atom, hydroxy ^group, -OR 91, -NR ^{9 .R 72 ~R 74, R 81 ~R} 84 and ^R 91 ^{to R 94} representing a R ⁹³ or ^{-R 94} are the same or different, a hydrogen atom, an optionally substituted alkyl group or a substituted group And an aryl group which may have
R ³ represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group which may have a substituent, or an aryl group which may have a substituent.
R ⁴⁰² and R ⁴⁰³ are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, -NR ⁴⁰⁶ R ⁴⁰⁷ , -OR ^408, a cyano ^{group, -C (O) R 409,} -O-C (O) R 410 or -C ^{(O) oR 411,}
R ^{404 to} R ⁴¹¹ are the same or different and each represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent. R ⁴⁰⁴ , R ^405, and the nitrogen atom to which R ⁴⁰⁴ and R ⁴⁰⁵ are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent. ))) The ultraviolet absorber characterized by including the compound represented by following General formula (1) .

(In the general formula (1), m represents an integer of 1 to 6,
Q ¹ represents a hydrogen atom when m is 1 and a divalent to hexavalent linking group when m is 2 to 6,
D ¹ represents a group in which one hydrogen atom is removed from the compound represented by the following general formula (2), and when m is 2 to 6, a plurality of D ¹ may be all the same or different It may be

(In the general formula (2), R ¹ represents a cyano group, a nitro group, a trifluoromethyl group, a heterocycle-containing group, —O—C (O) H, —C (O) —R ⁷ or —SO ₂ — represents R ^{8, R 2} is a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic ring-containing group, -O-C (O) H , -C (O) -R 7 or -SO ₂ - or represents R ^8, or, ^{R 2} represents -C (O) -R ^9, and ^{R 1,} with the ^{R 2,} with the carbon atom ^{to which R 1} and ^{R 2} are attached, a substituent R ⁷ represents a hydrogen atom, a halogen atom, -NR ⁷² R ⁷³ or -R ⁷⁴ , and R ⁸ represents a halogen atom, a hydroxy group,- oR ^81, represents ^-NR 82 ^{R 83} or ^{-R 84, R 9} represents a hydrogen atom, a halogen atom, hydroxy ^group, -OR 91, -NR ^{9 .R 72 ~R 74, R 81 ~R} 84 and ^R 91 ^{to R 94} representing a R ⁹³ or ^{-R 94} are the same or different, a hydrogen atom, an optionally substituted alkyl group or a substituted group And an aryl group which may have
R ³ represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group which may have a substituent, or an aryl group which may have a substituent.
R ⁴⁰² and R ⁴⁰³ are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, -NR ⁴⁰⁶ R ⁴⁰⁷ , -OR ^408, a cyano ^{group, -C (O) R 409,} -O-C (O) R 410 or -C ^{(O) oR 411,}
R ^{404 to} R ⁴¹¹ are the same or different and each represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent. R ⁴⁰⁴ , R ^405, and the nitrogen atom to which R ⁴⁰⁴ and R ⁴⁰⁵ are bonded may form a 4- to 8-membered nitrogen-containing heterocyclic ring which may have a substituent. )))