KR20180123620A - Dye compound - Google Patents

Abstract

The objective of the present invention is to provide a compound having high absorbance around 400 nm. The present invention relates to a compound represented by chemical formula (1). In chemical 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 coupling group when m is 2 to 6; and D^1 represents a group in which one hydrogen atom is removed from a compound represented by chemical formula (2), wherein a plurality of D^1s all may be identical or different when m is 2 to 6. In chemical formula (2), R^1 represents a cyano group; R^2 represents a hydrogen atom, a cyano group, or others; R^3 represents a hydrogen atom, or others; and R^402 to R^405 are identical or different, and represent a hydrogen atom, an alkyl group, or others.

Description

Dye compound {DYE COMPOUND}

The present invention relates to compounds usable as coloring matters and the like.

Ultraviolet rays and blue light have strong energy, and damage to the retina may cause eye diseases. For this reason, a compound usable as an ultraviolet absorbing agent, a coloring material for a blue light cut, or the like is required. As an ultraviolet absorber, for example, it has been proposed to use a methine compound instead of a benzophenone or benzotriazole ultraviolet absorber (Patent Documents 1 and 2).

Japanese Laid-Open Patent Publication No. 2009-067973 Japanese Laid-Open Patent Publication No. 2011-184414

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

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

Means for Solving the Problem As a result of intensive studies to solve the above problems, the present inventors have found that a compound having a methine structure having a nitrogen-containing aromatic ring and an electron-attracting group represented by the following general formula (1) has an absorption maximum near 400 nm, It was found that the absorbance in the vicinity of 400 nm was high. The present inventors have conducted further research based on this finding and accomplished the present invention.

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

[Chemical 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 represents a linking group having a valency of 2 to 6 when m is 2 to 6,

D ¹ represents a group in which one hydrogen atom is separated from the compound represented by the following general formula (2), and when m is 2 to 6, plural D ^{1 s} may be the same or different.

(2)

(O) H, -C (O) -R ⁷ or -SO ₂ -R ⁸ (wherein R ¹ represents a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, R ² represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ⁷ or -SO ₂ -R ⁸ Or R ² represents -C (O) -R ⁹ , and R ¹ , R ² , and a carbon atom to which R ¹ and R ² are bonded may form a heterocyclic ring of 4 to 8 atoms which may have a substituent is formed. R ⁷ is a hydrogen atom, a halogen atom, -NR ⁷² R ⁷³ or -R ^74, R ⁸ is a halogen atom, a hydroxyl group, -OR ^81, -NR ⁸² R ⁸³ or -R ⁸⁴ represents a, R ⁹ is a hydrogen atom, a halogen atom, a hydroxyl group, -OR ^91, represents an -NR ⁹² R ⁹³ or ^{-R 94. R 72 ~ R 74} , R 81 ~ R 84 and R ⁹¹ ~ R ⁹⁴ Are the same or different and each represents a hydrogen atom, an alkyl group which may have a substituent, Aryl represents a group which may optionally 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 ) R ⁴⁰⁹ , -OC (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. And R ^404, R ⁴⁰⁵ and, R ⁴⁰⁴ and also 4 to 8 atoms which may have a nitrogen atom, R ⁴⁰⁵ is, substituents which are bonded to form a nitrogen heterocyclic ring.))

In the present invention, it is preferable that m in the general formula (1) is 1 or 2.

The compound represented by the above general formula (1) is preferably a compound represented by the following general formula (3).

(3)

(Wherein R ^1a represents a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ^7a or -SO ₂ -R ^8a R ^2a represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ^7a or -SO ₂ -R ^8a Or 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 may form a heterocyclic ring of 4 to 8 atoms which may have a substituent It is formed. R ^7a is a hydrogen atom, a halogen atom, -NR ^72a R ^73a or -R ^74a, R ^8a is a halogen atom, a hydroxyl group, -OR ^81a, -NR ^82a R ^83a -R ^84a or It represents a, R ^9a is a hydrogen atom, a halogen atom, a hydroxyl group, -OR ^91a, -NR ^92a R ^93a represents a or ^{-R 94a. R 72a ~ R 74a} , R 81a ~ R 84a and R ^91a R ^94a ~ Are the same or different and each represents a hydrogen atom or a substituent An alkyl group having 1 to 20 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 represents 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 , (O) R ^409a , -OC (O) R ^410a or -C (O) OR ^411a , and R ^404a to R ^411a are the same or different and each represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms Or an aryl group having 6 to 20 carbon atoms which may have a substituent. And R ^404a, R ^405a, and also 4 to 8 atoms which may optionally R ^404a and R ^405a has a nitrogen atom, and the substituent are bonded to form a nitrogen heterocyclic ring.

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 a group represented by the following formula (4).

[Chemical Formula 4]

(In the general formula (4), Q ² represents a divalent hydrocarbon group of 1 to 20 carbon atoms which may have a substituent, and * represents a bonding site with the general formula (3).

R ^1b is a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic ring-containing group, -OC (O) H, -C (O) -R ^7b represents or -SO ₂ -R ^8b, R ^2b is hydrogen -C (O) -R ^7b or -SO ₂ -R ^8b , or R ^2b represents -C (O) -R ^7b , (O) -R ^9b , and R ^1b , R ^2b and R ^1b and R ^2b are bonded to form a heterocyclic ring of 4 to 8 atoms which may have a substituent. R ^7b represents a hydrogen atom, a halogen atom, -NR ^72b R ^73b or -R ^74b , R ^8b represents a halogen atom, a hydroxyl group, -OR ^81b , -NR ^82b R ^83b or -R ^84b , R ^9b represents a hydrogen atom, a halogen atom, a hydroxyl group, -OR ^91b , -NR ^92b R ^93b or -R ^94b . R ^72b to R ^74b , R ^81b to R ^84b and R ^91b to R ^94b are the same or different and each represents 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 Lt; / RTI >

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 and may have a substituent.

R ^402b represents 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 ^407b , -OR ^408b , a cyano group, (O) R ^409b , -OC (O) R ^410b or -C (O) OR ^411b , and R ^404b to R ^411b are the same or different and each represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms Or an aryl group having 6 to 20 carbon atoms which may have a substituent. And R ^404b, and R ^405b, R ^404b and R ^405b are also coupled to form a nitrogen-containing heterocyclic ring of 4-8 atoms which may have a nitrogen atom, the substituents in.))

In one embodiment of the present invention, it is preferable that R ⁴¹³ is a group represented by the general formula (4).

In one embodiment of the present invention, R ^2a is -C (O) -R ^9a , and R ^1a , R ^2a , and R 4a, which are carbon atoms bonded to R ^1a and R ^2a , To form a heterocyclic ring of 8 to 8 atoms.

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

[Chemical Formula 5]

(5), R ^2c represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ^7c or -SO ₂ which represents the -R ^8c R ^7c is, represents a hydrogen atom, a halogen atom, -NR ^72c R ^73c or -R ^74c, R ^8c is a halogen atom, a hydroxyl group, -OR ^81c, -NR ^82c R ^83c or - It represents an R ^84c. R ^72c ~ R ^74c and R ^81c ~ R ^84c is the same or different, a hydrogen atom, which may have an alkyl group or a substituent having 1 to 20 carbon atoms which may be substituted 6-20 aryl groups of .

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 and may have a substituent.

R ^402c and R ^403c are the same or different and each represents 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 ^406c R ^407c , oR ^408c, a cyano ^{group, -C (O) R 409c,} -OC (O) R 410c , or represents a -C (O) oR ^{411c, 404c} R ~ R ^411c, the same or different, a hydrogen atom, a substituent An optionally substituted alkyl group having 1 to 20 carbon atoms or an optionally substituted aryl group having 6 to 20 carbon atoms. R ^404c , R ^405c , a nitrogen atom bonded to R ^404c and R ^405c , or a nitrogen-containing heterocycle having 4 to 8 atoms which may have a substituent.

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 a group represented by the following formula (6).

Y ^1c represents -NR ^502c -, R ^502c represents 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.

[Chemical Formula 6]

(In the general formula (6), Q ³ represents a divalent hydrocarbon group of 1 to 20 carbon atoms which may have a substituent, and * represents a bonding site with the general formula (5).

Y ^1d represents -NR ^502d - and R ^502d represents 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 ^2d represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic-containing group, -OC (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 hydroxyl group, -OR ^81d , -NR ^82d R ^83d or -R ^84d . R ^72d to R ^74d and R ^81d to R ^84d are the same or different and each represents 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 ^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 and may have a substituent.

R ^402d and R ^403d, the same or different, a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, having from 6 to 20 carbon atoms which may have a substituent, an aryl group, and -NR R ^{406d 407d,} - OR ^408d , cyano group, -C (O) R ^409d , -OC (O) R ^410d or -C (O) OR ^411d , and R ^404d to R ^411d are the same or different and each represents a hydrogen atom or a substituent An optionally substituted alkyl group having 1 to 20 carbon atoms or an optionally substituted aryl group having 6 to 20 carbon atoms. And R ^{404d, 405d} and the R, R ^404d and R ^405d is also bonded to form a nitrogen-containing heterocyclic ring of 4-8 atoms which may have a nitrogen atom, the substituents in.))

In one embodiment of the present invention, it is preferable that R ⁵⁰¹ is a group represented by the above general formula (6).

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

(7)

(In the general formula (7), Q ⁴ represents -SO ₂ - or a divalent hydrocarbon group of 1 to 20 carbon atoms which may have a substituent.

R ^1e represents a heterocyclic group, -C (O) -R ^7e or -SO ₂ -R ^8e , and R ^2e represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, -OC (O) H, -C (O) -R ^7e or -SO ₂ -R ^8e . R ^7e represents a hydrogen atom, a halogen atom, -NR ^72e R ^73e or -R ^74e , and R ^8e represents a halogen atom, a hydroxyl group, -OR ^81e , -NR ^82e R ^83e or -R ^84e . R ^72e to R ^74e and R ^81e to R ^84e are the same or different and each represents 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 ^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 and may have a substituent.

R ^402e and R ^403e are the same or different and each represents 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 ^406e R ^407e , oR ^408e, a cyano ^{group, -C (O) R 409e,} -OC (O) R 410e or represents a ^{-C (O) oR 411e, R} 404e ~ R 411e is the same or different, a hydrogen atom, a substituent An optionally substituted alkyl group having 1 to 20 carbon atoms or an optionally substituted aryl group having 6 to 20 carbon atoms. R ^404e, and R ^405e, and also of 4-8 atoms which may optionally R ^404e and R ^405e has a nitrogen atom, and the substituent are bonded to form a nitrogen heterocyclic ring.)

In one embodiment of the present invention, it is preferable that Q ⁴ is -SO ₂ -.

The colorant 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 optical filter, a color filter is preferable.

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 in the vicinity of 400 nm can be provided. The compound of the present invention can be preferably used as a coloring matter 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). The compound represented by the above general formula (1) is also referred to as the compound (1) in the present specification. The same applies to the compounds of other formula numbers. For example, the compound represented by formula (2) is also referred to as compound (2).

When geometric identity exists in the compound (1) of the present invention, the present invention encompasses all of the geometric isomers thereof. In the case where at least one asymmetric carbon atom is present in the compound (1) of the present invention, the present invention includes both compounds in which the asymmetric carbon atoms are in the R configuration, compounds in the S configuration, and any combination thereof. Also, the racemic compounds, racemic mixtures, single enantiomers, diastereomer mixtures thereof are all included in the present invention.

In the general formula (1), m represents an integer of 1 to 6. When m is 2 to 6, the heat resistance of the compound (1) is improved, which 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 represents a linking group of 2 to 6 when m is 2 to 6.

Examples of the linking group having 2 to 6 carbon atoms include a hydrocarbon group of 2 to 6 carbon atoms having 1 to 20 carbon atoms which may have a substituent, -SO ₂ -, and the like.

A 2 to 6-membered hydrocarbon group having 1 to 20 carbon atoms which may have a substituent and is preferably a linear, branched or cyclic 2- to 6-membered alkyl group having 1 to 20 carbon atoms and may have a substituent, And an arylene group having 2 to 6 carbon atoms. 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 which may have a substituent, -SO ₂ -, and the like are preferable. The divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent is preferably a linear, branched or cyclic divalent alkyl group having 1 to 20 carbon atoms which may have a substituent, an optionally substituted divalent alkyl group having 6 to 20 carbon atoms ≪ / RTI >

The straight, branched or cyclic divalent alkyl group having 1 to 20 carbon atoms may be a divalent alkyl group having an oxygen atom, a sulfur atom or an arylene group inserted thereinto, which may have a substituent, and is preferably - ( CH ₂ ) _k 1 - (k 1 is an integer of 1 to 20), and examples thereof include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group , A hexylene group, a heptylene group, an octylene group, and a decylene group. Further, it is also preferably a divalent alkyl group substituted with at least one halogen atom, and examples thereof include a bistrifluoromethylmethylene group and the like. The number of carbon atoms 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 the divalent arylene group having 6 to 20 carbon atoms which may have a substituent, for example, a group represented by the following general formula (20) is preferable.

[Chemical Formula 8]

X is independently a halogen atom, a nitro group, a hydroxyl group, a sulfo group, an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms, s is an integer of 0 to 4 . The bonding of two points of the benzene ring may be either o-, m- or p- orientation. It is also preferable that the benzene ring has no substituent (s = 0).

In the general formula (1), D ¹ represents a group in which one hydrogen atom has been removed from the compound (2). The group in which one hydrogen atom is removed from the compound (2) may be a group obtained by removing one hydrogen atom from the compound (2). The compound (2) contains a nitrogen-containing aromatic ring and an electron-attracting group, and contains a methine structure which can be a pigment. The compound (1) contains such a methine structure and can be used as a dye compound. When m is 2 to 6, plural D ^{1 s} may be the same or different. In an embodiment, it is preferable that all of the plurality of D ¹ are the same.

In the general formula (1), the compound (1) wherein m is 1 is the compound (2). The compound (1) wherein m is 1 is also referred to as a monomer compound. The compound (1) wherein m is 2 to 6 is a compound having a 2- to 6-mer structure in which two or more groups in which a hydrogen atom has been removed from the compound (2) by a linking group (Q ¹ ) The compound (1) wherein m is 2 to 6 may 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 of the compound (2), more preferably a group in which one hydrogen atom is removed from R ¹ or R ⁴⁰³ . In other words, in the general formula (1), Q ¹ is preferably bonded to the R ¹ , R ⁴⁰³ or R ⁴⁰⁴ moiety in the general formula (2), and it is preferable that Q ¹ is bonded to the R ¹ or R ⁴⁰³ moiety Is more preferable.

In the general formula (2), R ¹ is a cyano group, a nitro group, a trifluoromethyl group (CF ₃ group), a heterocyclic ring-containing group, -OC (O) H, -C (O) -R 7 or -SO _2- R ⁸ . A cyano group, a nitro group, a trifluoromethyl group, a heterocyclic-containing group, -OC (O) H, -C (O) -R ⁷ and -SO ₂ -R ⁸ are both electron-attracting groups.

R ² represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ⁷ or -SO ₂ -R ⁸ , R ² represents -C (O) -R ⁹ . In the general formula (2), when R ² represents -C (O) -R ⁹ , R ¹ , R ² , and a carbon atom bonded to R ¹ and R ² , To form a heterocyclic ring of 8 atoms. -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 hydroxyl group, -OR ⁸¹ , -NR ⁸² R ⁸³ or -R ⁸⁴ , R ⁹ represents a hydrogen atom, a halogen atom, a hydroxyl group, -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.

R ¹ and R ² may be the same or different.

Examples of the heterocyclic ring-containing group in R ¹ and R ² include a pyrrole ring, pyridine ring, quinoline ring, pyrimidine ring, pyridazine ring, pyrazine ring, imidazole ring, , A nitrogen-containing heterocycle such as a tetrazole ring; Oxygen-containing heterocycle such as furan ring, benzofuran ring and the like; Thiophene ring, benzothiophene ring and the like; A heterocyclic ring containing an oxygen atom and a nitrogen atom such as an oxazole ring and a benzooxazole ring; A thiadiazole ring, a benzothiazole ring, a thiadiazole ring and the like, and these rings may further be substituted with another carbon ring (for example, a benzene ring) or a heterocyclic ring (for example, a pyridine ring ) And a condensed ring may be formed, and an oxazole ring or a benzoxazole ring is preferable.

In one embodiment of the present invention, as the heterocyclic-containing group in R ¹ and R ² , a group in which a hydrogen atom is removed from a carbon (2-position) between nitrogen and oxygen in a benzoxazole ring or an oxazole ring , And more preferably a group in which a hydrogen atom is separated from carbon (2-position) between nitrogen and oxygen in the benzoxazole ring.

For example, when m is 2 to 6 in the general formula (1), 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 groups in which the compound (2) for bonded at the site of R ^1, R ¹ is preferably bonded and benzoxazole ring or oxazole carbon atoms other than carbon in Q ¹ (second position) between the nitrogen and oxygen in the ring.

R ¹ is preferably a cyano group, a heterocyclic-containing group, -OC (O) H, or -C (O) -R ⁷ .

R ² is preferably a cyano group, a heterocyclic containing group, -OC (O) H or -C (O) -R ⁷ , or R ² is -C (O) -R ⁹ .

R ⁷² , R ⁷³ and R ⁷⁴ , R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ , and R ⁹¹ , R ⁹² , R ⁹³ and R ⁹⁴ , which may have a substituent, An alkyl group having 1 to 20 carbon atoms. Examples of the alkyl group having 1 to 20 carbon atoms which may have a substituent include a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms which may have a substituent described below. In one embodiment 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 may be a branched or cyclic three- Is preferably a bulky alkyl group, more preferably a cyclic alkyl group having 6 to 20 carbon atoms, and particularly preferably a cyclic alkyl group which may have a linear or branched alkyl group as a substituent. Examples of the alkyl group having 1 to 20 carbon atoms in R ⁷² to R ⁷⁴ , R ⁸¹ to R ⁸⁴ , and R ⁹¹ to R ⁹⁴ include methyl group, ethyl group, n-propyl group, i-propyl group, butyl group, n-hexyl group, cyclohexyl group, n-octyl group, 2-ethylhexyl group, 4-t- butylcyclohexyl group, 2,6- 4-methylcyclohexyl and the like are preferable, and a t-butyl group, a cyclohexyl group, a 4-t-butylcyclohexyl group and a 2,6-di-t- 4-t-butylcyclohexyl group, 2,6-di-t-butyl-4-methylcyclohexyl group and the like. R ⁷² , R ⁷³ and R ⁷⁴ , R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ , and R ⁹¹ , R ⁹² , R ⁹³ and R ⁹⁴ , which may have a substituent, And an aryl group having 6 to 20 carbon atoms. Examples of the aryl group having 6 to 20 carbon atoms which may have a substituent include an aryl group having 6 to 20 carbon atoms which may have a substituent, which will be described later. Examples of the aryl group include a phenyl group (for example, Methylphenyl group, 2,6-dimethylphenyl group, etc.) and the like are preferable.

R ⁸¹ and R ⁹¹ are the same or different and are, for example, a methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s- Butyl group, a pentyl group, an n-hexyl group, a cyclohexyl group, an n-octyl group, a 2-ethylhexyl group, a 4-t- butylcyclohexyl group, a 2,6- More preferred are 4-t-butylcyclohexyl group, 2,6-di-t-butyl-4-methylcyclohexyl group and the like. R ⁷² , R ⁸² and R ⁹² are the same or different and preferably a hydrogen atom. R ⁷³ , R ⁸³ and R ⁹³ are the same or different and 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 preferably represent a methyl group, an ethyl group, a t-butyl group, a cyclohexyl group, a phenyl group or a naphthyl group.

When R ² is -C (O) -R ⁹ , R ¹ , R ² and a carbon atom bonded to R ¹ and R ² form a heterocyclic ring of 4 to 8 atoms which may have a substituent have.

The heterocyclic group of 4 to 8 atoms formed by R ¹ , R ² and a carbon atom to which R ¹ and R ² are bonded is a heterocyclic group containing at least one hetero atom selected from a nitrogen atom, an oxygen atom and a sulfur atom A heterocyclic ring of 4 to 8 atoms. The heterocyclic ring may be an aromatic heterocyclic ring or a non-aromatic heterocyclic ring. Examples of the heterocyclic ring of 4 to 8 atoms include, for example, pyrazolone ring, isooxazolone ring, oxyindole ring, barbitur ring, thiobarbitur ring, rhodanine ring, pyridone ring, 2,4- 2-thio-2, 4-oxazolidinedione ring, 2,5-thiazolidinedione ring, 2-thio-2,5-thiazolidinedione ring, thiazolidinedione ring, Imidazoline ring, succinimide ring, 1,3-dioxane-4,6-dione ring (heterocyclic ring) And the like. Preferably a heterocyclic ring containing 5 or 6 atoms of at least one hetero atom selected from a nitrogen atom, an oxygen atom and a sulfur atom, more preferably a heterocyclic ring containing 5 or 6 nitrogen atoms and oxygen atoms, A pyrazolone ring, a barbitur ring, a 2,4-oxazolidinedione ring and the like.

The substituent in the 4- to 8-membered heterocyclic ring which may have a substituent is not particularly limited and includes, for example, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms described below, An aryl group having 6 to 20 carbon atoms, a carboxyl group, an alkoxycarbonyl group, and the like. Examples of the aryl group having a substituent include an aryl group having a substituent such as a nitrophenyl group, a cyanophenyl group, a hydroxyphenyl group, a methylphenyl group, a dimethylphenyl group, a trimethylphenyl group, a fluorophenyl group, a chlorophenyl group, a dichlorophenyl group, a bromophenyl group, a methoxyphenyl group, A phenyl group having a substituent such as a fluoromethylphenyl group or an N, N-dimethylaminophenyl group. Preferably, the substituent is an unsubstituted alkyl group, a halogenated alkyl group, a carboxyl-substituted alkyl group, an aralkyl group, or an aryl group which may have a substituent (preferably a phenyl group, a methylphenyl group, a dimethylphenyl group or a trimethylphenyl group).

In the 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, R ⁴⁰⁹ , -OC (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 , a nitrogen atom bonded to R ⁴⁰⁴ and R ⁴⁰⁵ , or a nitrogen-containing heterocycle having 4 to 8 atoms which may have a substituent.

Examples of the alkyl group for R ³ , R ⁴⁰² and R ⁴⁰³ include linear, branched or cyclic alkyl groups of 1 to 20 carbon atoms. Specific examples of the linear, branched or cyclic alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec- Propyl group, n-butyl group, n-pentyl group, 2-methylbutyl group, 1-methylbutyl group, neo- Dimethylbutyl group, 2,3-dimethylbutyl group, 2, 3-dimethylbutyl group, 3-methylbutyl group, 2-methylbutyl group, Dimethylbutyl group, 1,1-dimethylbutyl group, 2-ethylbutyl group, 1-ethylbutyl group, 1,1,2-trimethylbutyl group, 1-ethyl- Methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 2,4-dimethylpentyl group, n-octyl group, Dimethylhexyl group, 2,4-dimethylhexyl group, 2,2,4-trimethylpentyl group, t-octyl group, n-nonyl group, 3,5,5-trimethylhexyl group N-decyl, 4-ethyl N-heptyl group, n-octyl group, n-heptyl group, 4-ethyl-4,5-dimethylhexyl group, N-pentyldecyl group, 3, 5-dimethylheptadecyl group, 2, 3-dimethylheptadecyl group, Dimethylheptadecyl group, 2,4-dimethylheptadecyl group, 2,2,5,5-tetramethylhexyl group, 1-cyclopentyl-2,2-dimethylpropyl group, 1-cyclohexyl- -Dimethylpropyl group, 2,6-di-t-butyl-4-methylcyclohexyl group, and n-octadecyl group.

The substituent on the alkyl group which may have a substituent is not particularly limited and includes a monocyclic or polycyclic aromatic ring group having 6 to 10 carbon atoms (phenyl group, naphthyl group, etc.), a linear, branched or cyclic A halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, An acyl group (for example, an acetyl group, a propionyl group, a butyryl group, a valeryl group, a pivaloyl group, an acryloyl group, a methacryloyl group, a benzoyl group, a toluoyl group, a cinnamoyl group, Diaryl, etc.) and an acyloxy group having 2 to 10 carbon atoms.

Examples of the aryl group for R ³ , R ⁴⁰² and R ⁴⁰³ include a monocyclic or polycyclic aromatic ring group having 6 to 20 carbon atoms. As the aromatic ring group of a monocyclic or polycyclic ring having 6 to 20 carbon atoms, there may be mentioned a monocyclic aromatic hydrocarbon group such as a phenyl group; A naphthyl group, an anthracenyl group, a naphthacenyl group, a pentacenyl group, a phenanthrenyl group, and a pyrenyl group.

The substituent in the aryl group which may have a substituent is not particularly limited and includes, 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, A halogen atom, a cyano group, a hydroxyl group, a nitro group, a halogenated hydrocarbon group having 1 to 8 carbon atoms, a carboxyl group, and an alkoxycarbonyl group having 1 to 8 carbon atoms. It is preferably a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms. For example, examples of the phenyl group and naphthyl group having a substituent include a nitrophenyl group, a cyanophenyl group, a hydroxyphenyl group, a methylphenyl group, a dimethylphenyl group, a trimethylphenyl group, a fluorophenyl group, a chlorophenyl group, a dichlorophenyl group, A substituted or unsubstituted phenyl group such as a methoxyphenyl group, an ethoxyphenyl group, a trifluoromethylphenyl group, an N, N-dimethylaminophenyl group, a nitronaphthyl group, a cyanonaphthyl group, a hydroxynaphthyl group, a methylnaphthyl group, a fluoronaphthyl group, A monopropyl group, a trifluoromethylnaphthyl group, and the like.

In the formula (2), R ⁴⁰⁴ and, R ⁴⁰⁵ and, R ⁴⁰⁴ and R ⁴⁰⁵ is a nitrogen-containing heterocyclic ring of 4-8 atoms, which is bonded to the nitrogen to form atoms, which is, also containing an oxygen atom of nitrogen heterocyclic . As the nitrogen-containing heterocyclic ring, there may be mentioned a non-aromatic nitrogen-containing heterocyclic ring. Examples of the nitrogen-containing heterocyclic ring of 4 to 8 atoms include non-aromatic nitrogen-containing heterocycles such as pyrrolidine ring, piperidine ring, piperazine ring and morpholine ring.

The substituent in the nitrogen-containing heterocycle having 4 to 8 atoms which may have a substituent is not particularly limited and includes, for example, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms , A halogen atom, a cyano group, a hydroxyl group, a nitro group, a halogenated hydrocarbon group having 1 to 8 carbon atoms, a carboxyl group, an alkoxy group having 1 to 8 carbon atoms Carbonyl group and the like. It is preferably a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms.

When a ring such as an alkyl group, an aryl group, a nitrogen-containing heterocycle, a heterocyclic ring, etc. has a substituent, when two or more substituents are present, the respective substituents may be the same or different.

Preferred embodiments of each group in the general formula (2) will be described.

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

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, more preferably an alkyl group having 1 to 20 carbon atoms which may have a substituent Do. More preferably, R ⁴⁰⁸ is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms which may have a substituent, more preferably an alkyl group having 1 to 3 carbon atoms, and particularly preferably an ethyl group.

In one embodiment of the present invention, at least one of R ⁴⁰² and R ⁴⁰³ is preferably a substituent other than a hydrogen atom, and R ⁴⁰² and R ⁴⁰³ are the same or different and more preferably a substituent other than a hydrogen atom.

R ⁴⁰⁴ and R ⁴⁰⁵ are the same or different, and are 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, more preferably an alkyl group having 1 to 10 carbon atoms Or an aryl group having 6 to 10 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and particularly preferably a methyl group, ethyl group, n-propyl group or n-butyl group.

R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ are the same or different and are 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 to be.

The compound represented by the general formula (3) (compound (3)), the compound represented by the general formula (5) (compound (5)), the compound represented by the general formula (3) 7) (compound (7)) and the like are preferable.

In one embodiment of the present invention, compound (3) is preferable as compound (1). The compound (3) is preferable because it has excellent light resistance.

In formula (3), R ^1a represents a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ^7a or -SO ₂ -R ^8a .

R ^2a represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ^7a or -SO ₂ -R ^8a , R ^2a represents -C (O) -R ^9a . When R ^2a represents -C (O) -R ^9a , R ^1a , R ^2a , and a carbon atom bonded to R ^1a and R ^2a form a heterocyclic ring of 4 to 8 atoms which may have a substituent .

R ^7a represents a hydrogen atom, a halogen atom, -NR ^72a R ^73a or -R ^74a , R ^8a represents a halogen atom, a hydroxyl group, -OR ^81a , -NR ^82a R ^83a or -R ^84a , R ^9a represents a hydrogen atom, a halogen atom, a hydroxyl group, -OR ^91a , -NR ^92a R ^93a or -R ^94a . R ^72a to R ^74a , R ^81a to R ^84a and R ^91a to R ^94a are the same or different and each represents 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, . R ^1a and R ^2a may be the same or different.

R ^1a is preferably a cyano group, a heterocyclic-containing group, -OC (O) H, or -C (O) -R ^7a . R ^2a is preferably a cyano group, a heterocyclic containing group, -OC (O) H or -C (O) -R ^7a , or R ^2a is -C (O) -R ^9a . A preferable embodiment of the heterocyclic ring of 4 to 8 atoms which may have a substituent in R ^1a and R ^2a is a compound wherein R ¹ , R ² and R ¹ and R ² in the general formula (1) are bonded Is the same as the preferred embodiment of the 4- to 8-membered heterocyclic ring formed by a 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 same as R ⁷² , R ⁷³ and R ⁷⁴ , 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 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 represents 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 , (O) R ^409a , -OC (O) R ^410a or -C (O) OR ^411a , R ^404a to R ^411a are the same or different and each 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. And R ^404a, R ^405a, and also 4 to 8 atoms which may optionally R ^404a and R ^405a has a nitrogen atom, and the substituent are bonded to form a nitrogen heterocyclic ring.

^{R 3a, R 402a, R 404a} , R 405a, R 406a, R 407a, R 408a, R 409a, R a preferred embodiment of the ^410a and R ^411a, the above-mentioned R ^3, R ^402, R ^404, R ^405, R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ , respectively.

In the general formula (3), R ⁴¹³ represents 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, Lt; / RTI > R ⁴¹³ is preferably an alkyl group having 1 to 5 carbon atoms which may have a substituent or a group represented by the formula (4), more preferably an alkyl group having 1 to 3 carbon atoms or a group represented by the formula (4) , More preferably an ethyl group or a group represented by the general formula (4). In one embodiment of the present invention, R ⁴¹³ is preferably a group represented by the general formula (4).

In the general formula (4), Q ² represents a divalent hydrocarbon group of 1 to 20 carbon atoms which may have a substituent, and * represents a bonding site with the general formula (3). In the general formula (4), Q ² is bonded to the general formula (3). The divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent in Q ² and a preferable embodiment thereof are the divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent in the above-mentioned Q ¹ , .

R ^1b represents a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ^7b or -SO ₂ -R ^8b in the general formula .

R ^2b represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ^7b or -SO ₂ -R ^8b , R ^2b represents -C (O) -R ^9b . When R ^2b represents -C (O) -R ^9b , R ^1b , R ^2b and a carbon atom bonded to R ^1b and R ^2b form a heterocyclic ring of 4 to 8 atoms which may have a substituent .

R ^7b represents a hydrogen atom, a halogen atom, -NR ^72b R ^73b or -R ^74b , R ^8b represents a halogen atom, a hydroxyl group, -OR ^81b , -NR ^82b R ^83b or -R ^84b , R ^9b represents a hydrogen atom, a halogen atom, a hydroxyl group, -OR ^91b , -NR ^92b R ^93b or -R ^94b . R ^72b to R ^74b , R ^81b to R ^84b and R ^91b to R ^94b are the same or different and each represents 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, . R ^1b is preferably a cyano group, a heterocyclic-containing group, -OC (O) H, or -C (O) -R ^7b . R ^2b is preferably a cyano group, a heterocyclic group, -OC (O) H or -C (O) -R ^7b , or R ^2b is -C (O) -R ^9b . A preferable embodiment of the heterocyclic ring of 4 to 8 atoms which may have a substituent in R ^1b and R ^2b is that in which R ¹ , R ² and R ¹ and R ² in the general formula (1) are bonded Is the same as the preferred embodiment of the 4- to 8-membered heterocyclic ring formed by a 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 same as R ⁷² , R ⁷³ and R ⁷⁴ , 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 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 represents 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 ^407b , -OR ^408b , a cyano group, (O) R ^409b , -OC (O) R ^410b or -C (O) OR ^411b , R ^404b to R ^4111b are the same or different and each 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. R ^404b and R ^405b, and a box of four to eight atoms which may optionally R ^404b and R ^405b has a nitrogen atom, and the substituent are bonded to form a nitrogen heterocyclic ring.

^{R 3b, R 402b, R 404b} , R 405a, R 406b, R 407b, R 408b, R 409b, R a preferred embodiment of ^410b and R ^411b, the above-mentioned R ^3, R ^402, R ^404, R ^405, R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ , respectively.

In the general formula (3), R ^2a represents -C (O) -R ^9a , and R ^1a , R ^2a , and R ^1a and R ^2a are bonded to each other to form a substituent Which may form a heterocyclic ring of 4 to 8 atoms. The heterocyclic ring of 4 to 8 atoms may be 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 be a 4- to 8-membered the heterocyclic ring the preferred embodiment is the same as the preferred embodiment of R ¹ and, R ² and, R ¹ and R ² heterocyclic ring of 4-8 atoms, which is formed of carbon atoms, which is bonded.

As the compound (1), the compound (5) is also preferable.

R ^2c represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ^7c or -SO ₂ - R ^8c . R ^7c represents a hydrogen atom, a halogen atom, -NR ^72c R ^73c or -R ^74c , and R ^8c represents a halogen atom, a hydroxyl group, -OR ^81c , -NR ^82c R ^83c or -R ^84c . R ^72c to R ^74c and R ^81c to R ^84c are the same or different and each represents 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 and may have a substituent. R ^2c is preferably a cyano group, a heterocyclic group or -C (O) -R ^7c , 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 same as R ⁷² , R ⁷³ and R ⁷⁴ described above and R ⁸¹ , R ⁸² , R ⁸³ and R ^84c Respectively.

In the general formula (5), 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 represents 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 and may have a substituent, -NR ^406c R ^407c , -OR ^408c, a cyano ^{group, -C (O) R 409c,} -OC (O) R 410c , or represents a -C (O) oR ^{411c, 404c} R ~ R ^411c is which may have the same or different, a hydrogen atom, a substituent An alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms and may have a substituent. R ^404c , R ^405c , a nitrogen atom bonded to R ^404c and R ^405c , or a nitrogen-containing heterocycle having 4 to 8 atoms which may have a substituent.

^{R 3c, R 402c, R 403c} , R 404c, R 405c, R 406c, R 407c, R 408c, R 409c, R a preferred embodiment of ^410c and R ^411c, the above-mentioned R ^3, R ^402, R ^403, R ⁴⁰⁴ , R ⁴⁰⁵ , R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ , respectively.

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 a group represented by the general formula (6) . R ⁵⁰¹ is preferably an alkyl group having 1 to 20 carbon atoms which may have a substituent (for example, a methyl group, an ethyl group, a t-butyl group, a cyclohexyl group, a 4-t-butylcyclohexyl group, methylphenyl group, dimethylphenyl group, trimethylphenyl group and the like) or an aryl group having 6 to 20 carbon atoms (for example, a phenyl group, a methylphenyl group, a dimethylphenyl group or a trimethylphenyl group) ). In one embodiment 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 represents 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. Y ^1c is preferably -NH-.

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

In formula (6), Y ^1d represents -NR ^502d -, R ^502d represents 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. A preferred embodiment of Y ^1d is the same as the preferred embodiment of Y ^1c described above.

R ^2d represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (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 hydroxyl group, -OR ^81d , -NR ^82d R ^83d or -R ^84d . R ^72d to R ^74d and R ^81d to R ^84d are the same or different and each represents 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 and may have a substituent.

R ^2d is preferably a cyano group, a heterocyclic group, -OC (O) H or -C (O) -R ^7d , more preferably a cyano group, -C (O) -NR ^72d R ^73d . Preferred embodiments of R ^72d , R ^73d and R ^74d and R ^81d , R ^82d , R ^83d and R ^84d are the same as R ⁷² , R ⁷³ and R ⁷⁴ described above and R ⁸¹ , R ⁸² , R ⁸³ and R ^84d Respectively.

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 and may have a substituent.

R ^402d and R ^403d are the same or different and each represents 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 ^406d R ^407d , -OR ^408d, a cyano ^{group, -C (O) R 409d,} -OC (O) R 410d , or represents a -C (O) oR ^{411d, 404d} R ~ R ^411d is which may have the same or different, a hydrogen atom, a substituent An alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms and may have a substituent. R ^404d , R ^405d , a nitrogen atom bonded to R ^404d and R ^405d , or a nitrogen-containing heterocycle having 4 to 8 atoms which may have a substituent.

^{R 3d, R 402d, R 403d} , R 404d, R 405d, R 406d, R 407d, R 408d, R 409d, R a preferred embodiment of ^410d and R ^411d, the above-mentioned R ^3, R ^402, R ^403, R ⁴⁰⁴ , R ⁴⁰⁵ , R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ , respectively.

In one embodiment of the present invention, it is also preferable that the compound (1) is the compound (7).

In the general formula (7), Q ⁴ represents -SO ₂ - or a divalent hydrocarbon group of 1 to 20 carbon atoms which may have a substituent. The divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent in Q ⁴ and a preferable embodiment thereof are the divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent in the above-mentioned Q ¹ , . In one embodiment of the present invention, Q ⁴ is preferably a bistrifluoromethylmethylene group or -SO ₂ -, more preferably -SO ₂ -.

In formula (7), R ^1e represents a heterocyclic group, -C (O) -R ^7e or -SO ₂ -R ^8e , and R ^2e represents a hydrogen atom, a cyano group, a nitro group, A methyl group, a heterocyclic group, -OC (O) H, -C (O) -R ^7e or -SO ₂ -R ^8e . R ^7e represents a hydrogen atom, a halogen atom, -NR ^72e R ^73e or -R ^74e , and R ^8e represents a halogen atom, a hydroxyl group, -OR ^81e , -NR ^82e R ^83e or -R ^84e . R ^72e to R ^74e and R ^81e to R ^84e are the same or different and each represents 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 ^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 heterocyclic-containing group, -OC (O) H, or -C (O) -R ^7e . Preferred embodiments of R ^72e , R ^73e and R ^74e and R ^81e , R ^82e , R ^83e and R ^84e are the same as R ⁷² , R ⁷³ and R ⁷⁴ described above and R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ Respectively.

In the general formula (7), 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 ^402e and R ^403e are the same or different and each represents 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 ^406e R ^407e , -OR ^408e, a cyano ^{group, -C (O) R 409e,} -OC (O) R 410e or represents a ^{-C (O) oR 411e, R} 404e ~ R 411e is which may have the same or different, a hydrogen atom, a substituent An alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms and may have a substituent. R ^404e , R ^405e , a nitrogen atom bonded to R ^404e and R ^405e , or a nitrogen-containing heterocycle having 4 to 8 atoms which may have a substituent.

^{R 3e, R 402e, R 403e} , R 404e, R 405e, R 406e, R 407e, R 408e, R 409e, R a preferred embodiment of ^410e and R ^411e, the above-mentioned R ^3, R ^402, R ^403, R ⁴⁰⁴ , R ⁴⁰⁵ , R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ , respectively.

When R ⁴¹³ is a group represented by the general formula (4), Q ¹ in the general formula (1) is Q ² (a divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent) Is a compound having a dimer structure in which a group represented by the general formula (3) and a group represented by the general formula (4) are connected to each other by Q ² . The group represented by the general formula (3) and the group represented by the general formula (4) each have a structure containing a methine structure, and all of which are pigments. Since the structure of such a pigment is a dimer structure, the molecular weight is increased, so that the compound does not sublimate well and becomes a dye compound having excellent heat resistance. The compound (3) wherein R ⁴¹³ is a group represented by the general formula (4) is a compound represented by the following general formula (3-1).

[Chemical Formula 9]

In the 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, Are the same as above.

When R ⁵⁰¹ is a group represented by the general formula (6), the compound (5) is a compound wherein Q ¹ in the general formula (1) is Q ³ (a divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent) Is a compound having a dimer structure in which a group represented by the general formula (5) and a group represented by the general formula (6) are connected to each other by Q ³ . The group represented by the general formula (5) and the structure represented by the general formula (6) are structures containing a methine structure and becoming a pigment. Since the structure of such a pigment is a dimer structure, the molecular weight is increased, so that the compound does not sublimate well and becomes a dye compound having excellent heat resistance.

The compound (5) wherein R ⁵⁰¹ is a group represented by the general formula (6) is a compound represented by the following general formula (5-1).

[Chemical formula 10]

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 ^405d and Y ^1d have the same meanings as defined above.

Examples of preferred embodiments of the compound (1) of the present invention include, for example, the compounds A1 to A6, B1 to B4, D1 and E1 prepared in the examples. Among them, the compounds A1 to A6 are preferable from the viewpoint of high light resistance. From the viewpoint of high heat resistance, the compounds A1 to A5, the compounds B2 and B4, and the compound D1 are preferable. Compounds A2 to A4, A6 and B4 are preferable in view of high solubility in an organic solvent.

The compounds A1 to A6 and E1 are examples of the compound (3), the compounds B1 to B4 are examples of the compound (5), and the compound D1 is an example of the compound (7). The compound B4 may be referred to as an example of the compound (3).

The method for producing the compound (1) of the present invention is not particularly limited, and for example, it can be produced 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. When a reaction to be described later is carried out, the functional groups other than the site may be protected by an appropriate protecting group in advance and deprotected in an appropriate step, if necessary.

In one embodiment of the present invention, when the compound represented by the general formula (1) is a compound (compound (11)) represented by the following general formula (11), it can be synthesized, for example, by the following method. 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) may also be referred to as an example of a compound in which R ⁴¹³ is a group represented by the general formula (4) in the compound (3). In the following, compound (11) is obtained by subjecting compound (M4) to dehydration condensation reaction with compound (M21).

(11)

In the above formulas, Q ^f represents a divalent linking group. R ^402f , R ^404f and R ^405f, and preferred embodiments thereof are the same as R ⁴⁰² , R ⁴⁰⁴ and R ⁴⁰⁵ described above and preferred embodiments thereof, respectively. The divalent linking group in Q ^f is the same as the divalent linking group in Q ¹ . Q ^f is preferably a divalent hydrocarbon group of 1 to 20 carbon atoms which may have a substituent. R ^1f and R ^2f and preferred embodiments thereof are the same as R ¹ and R ² described above and preferred embodiments thereof.

Dashed line

[Chemical Formula 12]

Represents a single bond, and the stereochemical configuration for the double bond to which it is bonded is each independently an E configuration, a Z configuration, or a mixture thereof. The same goes for the following.

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

[Chemical Formula 13]

In the general formula (M1), R ^402f , R ^404f and R ^405f have the same meanings as defined above.

The compound (11) can also be obtained by subjecting the compound (M1) and the compound (M21) to dehydration condensation and then quantifying the compound (M1) by alkoxylation.

When the compound represented by the general formula (1) is a compound (compound (12)) represented by the following general formula (12), it can be synthesized, for example, by the following method. The compound (12) is an example of the compound (1) of the present invention and is a dimer compound. The compound (12) may also be referred to as an example of a compound in which R ⁵⁰¹ in the compound (5) is a group represented by the general formula (6). In the following, a compound (12) is obtained by subjecting a compound (M2-1) to a dehydration condensation reaction with a compound (M22).

[Chemical Formula 14]

R ^2g represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ^7g or -SO ₂ -R ^8g . R ^7g represents a hydrogen atom, a halogen atom, -NR ^72g R ^73g or -R ^74g , and R ^8g represents a halogen atom, a hydroxyl group, -OR ^81g , -NR ^82g R ^83g or -R ^84g . R ^2g is preferably the above-mentioned cyano group, heterocyclic-containing group, or -C (O) -R ^7g . R ^71g , R ^81g , R ^82g , R ^83g and R ^84g and preferred embodiments thereof are the same as R ⁷¹ , R ⁸¹ , R ⁸² , R ⁸³ and R ^{84 described above} and preferred embodiments thereof. 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 divalent hydrocarbon group of 1 to 20 carbon atoms which may have a substituent. R ^{402g, 403g} R, R and R ^{404g 405g} and their preferred embodiments, the above-mentioned R ^402, R ^403, R ⁴⁰⁴ and R ⁴⁰⁵ and those of the preferred embodiment and is the same, respectively.

The compound (M2-1) and the compound (M2-2) described later can be obtained, for example, by alkoxylating the hydroxyl group of the compound (M1).

The compound (12) can also be obtained by dehydration condensation of the compound (M21) and the compound (M2-1), followed by coupling with R ^1f to obtain W ^g .

When the compound represented by the general formula (1) is a compound (compound (13)) represented by the following general formula (13), it can be synthesized, for example, 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). The compound (13) is also an example of the compound (3) in which R ⁴¹³ represents 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. In the following, a compound (13) is obtained by subjecting a compound (M2-2) to a dehydration condensation reaction with a compound (M23).

[Chemical Formula 15]

In the above formulas, R ^402h , R ^403h , R ^404h and R ^405h and preferred embodiments thereof are the same as R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ described above and preferred embodiments thereof, respectively. R ^1h , R ^2h and preferred embodiments thereof are the same as R ¹ and R ² described above and preferred embodiments thereof, respectively.

The isolation and purification of each product in the above production method can be carried out by appropriately combining the methods used in conventional organic synthesis, for example, filtration, extraction, washing, drying, concentration, crystallization, and various chromatographies have. In the case of intermediates, it is also possible to provide the following reaction without special 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 at 360 to 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. It is also preferable that the compound (1) of the present invention has a gram extinction coefficient of 400 nm or more. The absorption maximum wavelength and the gram extinction coefficient can be measured by the method described in the Examples.

The compound (1) of the present invention is preferably a compound dissolved in the following organic solvent.

Examples of the organic solvent include aromatic hydrocarbons such as toluene and xylene, ketones such as methyl ethyl ketone, acetone, cyclohexanone, 2-heptanone and 3-heptanone, (For example, propylene glycol monomethyl ether acetate, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether and the like), esters (for example, methyl 3-ethoxypropionate, Ethyl propionate, ethyl lactate, ethyl acetate, butyl acetate, methyl 3-methoxypropionate), and a mixed solvent of two or more of these.

The compound (1) is preferably dissolved in an amount of 0.1 mass% or more, for example, 0.1 mass% or more and 50 mass% or less, and more preferably 1 mass% or more and 40 mass By mass or less, more preferably 3% by mass or more and 30% by mass or less. More preferably, the solubility in an organic solvent at 20 占 폚 is in this range. When the solubility in an organic solvent is within this range, it is preferable that the compound (1) of the present invention is used because it has good manufacturability when used in the production of optical filters such as color filters.

The compound (1) of the present invention preferably has a thermal decomposition temperature of 200 ° C or higher, more preferably 210 ° C or higher, for example, 250-400 ° C. The thermal decomposition temperature can be measured by a thermogravimetric analyzer.

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 near 400 nm. In one embodiment, the compound (1) of the present invention can improve the heat resistance when a 2- to 6-mer compound (m in the general formula (1) is 2 to 6). 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 preferably used as a coloring material for an optical filter such as a color filter, a color conversion filter, a light absorption filter and the like. The compound (1) of the present invention is also preferably used for a blue light shielding material, an ultraviolet absorber, and a recording material for a recording medium.

The compound (1) of the present invention can be made into a pigment composition by mixing with, for example, a resin or the like. The colorant composition is preferably used as a coloring composition.

The resin is not particularly limited, and a thermoplastic resin, a photo-curable resin, a thermosetting resin or the like may be appropriately selected depending on the use of the coloring composition and the like. Examples of the resin include 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 Resins such as a resin, a polycycloolefin resin, a polysulfone resin, a polyether sulfone resin, a fluororesin, a silicone resin, a polyester resin, an epoxy resin, a phenol resin and a melamine resin. These may be used alone or in combination of two or more.

The compounding amount of the compound (1) in the coloring matter composition is, for example, preferably 0.001 to 50 mass%, more preferably 0.01 to 40 mass%, relative to the total solid content of the coloring composition.

The colorant composition may contain an optional component other than the compound (1) of the present invention and the resin, depending on its use and the like. Examples of the optional components include antioxidants, antifoaming agents, other pigments (dyes, pigments, etc.), infrared absorbers, polymerizable monomers, polymerization initiators, sensitizers and the like. In addition, an ultraviolet absorber other than the compound (1) may be contained.

The method for producing the colorant composition is not particularly limited, and for example, the compound (1) of the present invention and the resin and optional components to be blended may be mixed.

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

The optical filter may be any as long as it contains the compound (1) of the present invention, and the constitution of the optical filter is not particularly limited. For example, it may have at least a support and, if necessary, various functional layers such as an adhesive layer, an optical functional layer, an antireflection layer, and a hard coat layer, as in the conventional case. In the optical filter, the compound (1) of the present invention may be contained in any one of the support and the various functional layers. For example, the compound (1) is preferably contained in the support or the optical functional layer. The size and shape of the optical filter are not particularly limited and may be appropriately selected depending on the use and the like.

The constitution of the support and various functional layers is also not particularly limited. For example, the support is usually formed using a transparent resin. Examples of the transparent resin include, for example, a cyclic olefin resin, an aromatic polyether resin, a polyimide resin, a fluorene polycarbonate resin, a fluorene polyester resin, a polycarbonate resin, a polyamide (aramid) (Denatured) acrylic resin, a polyarylate resin, a polyarylate resin, a polysulfone resin, a polyether sulfone resin, a polyparaphenylene resin, a polyamideimide resin, a polyethylene naphthalate resin, a fluorinated aromatic polymer resin, Resins, and epoxy resins.

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, a compound (1) of the present invention and a binder resin or the like are dissolved or dispersed in a solvent, A method of forming a coating film on a support by a coating method such as an air knife coating method, a curtain coating method, a roller coating method, a wire bar coating method, a gravure coating method, a spin coating method and an extrusion coating method. Examples of the solvent include, but are not limited to, the above-described organic solvents.

As the method for producing the optical functional layer or the support containing the compound (1) of the present invention, the compound (1) of the present invention is mixed with the photopolymerizable resin and / or the thermosetting resin and / or the photopolymerization initiator and / After that, 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 an optical filter such as a color filter, a color conversion filter, or a light absorption filter, and is used as an optical filter such as a liquid crystal display, an organic EL display, an imaging device, an insecticide Restraint) material) can be preferably used.

The colorant composition containing the compound (1) of the present invention and the compound (1) of the present invention is preferably used for producing, for example, a blue light shielding material, an ultraviolet absorber, a recording material and a cosmetic.

Also included in the present invention are a blue light shielding material, ultraviolet absorber, recording material, and cosmetics containing the compound (1) of the present invention. The blue light shielding material, ultraviolet ray absorbent, recording material, and cosmetics are not particularly limited as long as they contain the compound (1).

The blue light shielding material is not particularly limited, and for example, a blue light cut film; A blue light cut lens for blue light cut glasses or a blue light cut lens for contact lenses. Examples of the method for producing a lens which is an example of the blue light shielding material include a method of kneading the compound (1) of the present invention in a transparent resin, molding by injection molding, compression molding, extrusion molding, or the like, And a method of forming an optical functional layer containing the compound (1) of the present invention on a support. The ultraviolet absorber can be used for various materials such as glass, plastic, fiber, paper, paint, ink, and cosmetics. The ultraviolet absorber may be used in combination with various materials, and may be dispersed in the material or may be dissolved. The ultraviolet absorber may be chemically or physically supported on various materials.

Examples of the recording material containing the compound (1) of the present invention include optical disks and the like.

Example

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.

The equipment and measurement conditions used to measure the physical properties of the obtained compound are as follows.

(GC-MS)

Ltd. Shimadzu Works Manufacturing Gas Chromatograph Mass Spectrometer GCMS-QP2010Plus (EI method)

(LC / MS)

High-performance liquid chromatograph mass spectrometer LCMS-2010EV (ESI method) manufactured by Shimadzu Corporation

≪ Preparation Example 1 &

Compound A6 represented by the following formula was synthesized. The reaction formula is shown below.

[Chemical Formula 16]

[Chemical Formula 17]

(Synthesis of compound IM2)

Dimethylamino-4-hydroxy-6-methylpyrimidine described in Journal of American Chemical Society 1954, 76, 1879 was added to a 1 L four-necked flask equipped with a thermometer, Dimethylguanidine sulfate was replaced with 1,1-dibutylguanidine hydrochloride obtained in the same manner as in the method described in BE639386, to obtain the compound IM1. Compound IM2 (18.4 g, yield 69%) was obtained by formylation by the Reimer-Tiemann reaction in the same manner as described in Journal of the Chemical Society 1957, 4845 using compound IM1.

GC-MS: m / z = 265 ([M] ^< ⁺ &

(Synthesis of compound IM3)

(14 g), potassium carbonate (14 g) and dimethylformamide (DMF) (60 g) in a 100 ml four-necked flask equipped with a reflux condenser, Ml) was stirred at 70 占 폚 for 3 hours, and then cooled to room temperature. The reaction solution was poured into water (300 ml) and extracted with toluene (300 ml). The organic layer was concentrated under reduced pressure to obtain a compound IM3 (17.3 g, yield 99%).

GC-MS: m / z = 293 ([M] ^< ⁺ &

(Synthesis of Compound A6)

(2.2 g), malononitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.5 g), piperidine (0.03 g) and ethanol (6 ml) in a 25 ml four-necked flask equipped with a stirrer, And the mixture was stirred at 75 占 폚 for 1 hour. The mixture was cooled to room temperature, and the precipitated crystals were collected by filtration. The resulting crystals were washed with ethanol to obtain Compound A6 (1.4 g, yield 67%).

LC-MS: m / z = 342 ([M + H] <^+> )

&Lt; Preparation Example 2 &

Compounds A1 to A4 represented by the following formulas were synthesized. Compound A1 is a compound wherein k is 4 in the following. Compound A2 is a compound wherein k is 5 in the following formula. Compound A3 is a compound wherein k is 6 in the following formula. Compound A4 is a compound wherein k is 8 in the following formula.

[Chemical Formula 18]

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

[Chemical Formula 19]

(Synthesis of compound IM4)

(1.5 g), potassium carbonate (1.7 g) and DMF (20 g) were added to a 50 ml four-necked flask equipped with a stirrer, a condenser and a thermometer, Ml), and the mixture was stirred at 80 占 폚 for 2.5 hours. The reaction solution was poured into water, and the precipitated crystals were collected by filtration. The crystals were washed with methanol to obtain compound IM4 (2.6 g, yield 89%).

(Synthesis of Compound A1)

Compound IM4 (2.3 g), malononitrile (0.64 g), piperidine (0.17 g) and ethanol (10 ml) were charged into a 25 ml four-necked flask equipped with a stirrer, Lt; / RTI &gt; The reaction solution was cooled to room temperature, and the crystals were collected by filtration. This crystal was washed with isopropyl alcohol (IPA) to obtain Compound A1 (1.4 g, yield: 56%).

LC-MS: m / z = 681 ([M + H] <^+> )

(Synthesis of compound IM5)

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

(Synthesis of Compound A2)

Compound A2 was obtained (in a yield of 67%) in the same procedure, except that the compound IM4 in the synthesis of the compound A1 was replaced with the compound IM5.

LC-MS: m / z = 695 ([M + H] <^+> )

(Synthesis of compound IM6)

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

(Synthesis of Compound A3)

Compound A3 was obtained (yield: 90%) in the same manner as Compound IM4, except that the compound IM4 in the synthesis of Compound A1 was replaced with the compound IM6.

LC-MS: m / z = 709 ([M + H] <^+> )

(Synthesis of compound IM7)

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

(Synthesis of Compound A4)

Compound A4 was obtained (in a yield of 40%) in the same procedure, except that the compound IM4 in the synthesis of the compound A1 was replaced with the compound IM7.

LC-MS: m / z = 737 ([M + H] <^+> )

&Lt; Preparation Example 3 &

Compound A5 represented by the following formula was synthesized. The reaction formula is shown below.

[Chemical Formula 20]

[Chemical Formula 21]

(Synthesis of compound IM8)

(1.3 g) and potassium carbonate (1.5 g) were added to a 50 ml four-necked flask equipped with a reflux condenser, a condenser tube and a thermometer, g) and DMF (20 ml), and the mixture was stirred at 60 캜 for 90 minutes. The solution was discharged into water (60 ml), and the precipitated crystals were filtered off and washed with water. The resulting crude crystals (crude crystals) were washed with methanol to obtain a 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) and DMF (4 ml) were charged into a 50 ml four-necked flask equipped with a thermometer and a cooling tube , And the mixture was stirred at 60 占 폚 for 4 hours. The reaction solution was cooled to room temperature, and the precipitated crystals were collected by filtration. The crystals were washed with methanol to obtain Compound A5 (2.57 g, yield 82%).

&Lt; Preparation Example 4 &

A compound B4 represented by the following formula was synthesized. The reaction formula is shown below.

[Chemical Formula 22]

(23)

(Synthesis of compound B4)

(1.5 g), 2-cyanoacetanilide (manufactured by Tokyo Chemical Industry Co., Ltd.) (0.82 g), pyrimidine (0.05 g) and toluene (5 mL) were placed in a 25 mL four-necked flask equipped with a stirrer, ) and n-butanol (5 ml), and the mixture was stirred at 95 캜 for 4.5 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure to obtain a crude product. The resulting crude product was washed with ethanol to obtain Compound B4 (1.1 g, yield 49%).

LC-MS: m / z = 436 ([M + H] <^+> )

&Lt; Production Example 5 &

Compounds B1 to B3 represented by the following formulas were synthesized.

&Lt; EMI ID =

(25)

(26)

The reaction formula is shown below. The compound corresponding to the position of the substituent of the benzene ring in the formula is shown in Table 2.

(27)

(Synthesis of compound IM9)

(10.2 g), o-phenylenediamine (manufactured by Tokyo Chemical Industry Co., Ltd.) (6.5 g) and 4-dimethyl (4-methylpyrrolidone) were added to a 500 ml four-necked flask equipped with a reflux condenser, Ethyl-3- (3-dimethylaminopropyl) aminopyridine (4.9 g), camphorsulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) (3.1 g) and chloroform (160 ml) A mixed solution of carbodiimide (EDC) (manufactured by Tokyo Chemical Industry Co., Ltd.) (25.3 g) and chloroform (80 ml) was added dropwise. After stirring at room temperature for 2 hours, the reaction solution was concentrated, and the obtained crude product was washed with methanol to obtain 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) and n-butanol (5 ml) were placed in a 25 ml four- And the mixture was stirred at 95 DEG C for 16.5 hours. The reaction solution was concentrated under reduced pressure, and then subjected to silica gel column chromatography to obtain Compound B1 (0.25 g, yield 16%).

LC-MS: m / z = 793 ([M + H] <^+> )

(Synthesis of compound IM10)

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

(Synthesis of Compound B2)

Compound B2 was obtained (yield: 61%) in the same procedure, except that the compound IM9 in the synthesis of the compound B1 was replaced with the compound IM10.

LC-MS: m / z = 793 ([M + H] <^+> )

(Synthesis of compound IM11)

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

(Synthesis of Compound B3)

Compound B3 was obtained (in a yield of 38%) in the same manner as Compound IM11, except that the compound IM9 in the synthesis of the compound B1 was replaced with the compound IM11.

LC-MS: m / z = 793 ([M + H] <^+> )

&Lt; Production Example 6 &

Compound D1 represented by the following formula was synthesized. The reaction formula is shown below.

(28)

[Chemical Formula 29]

(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 thermometer and a cooling tube and thionyl chloride (6 g) Respectively. The reaction solution was stirred at room temperature for 20 hours, and the precipitated crystals were collected by filtration. And washed with ethyl acetate to obtain compound IM16 (6.4 g, yield 86%).

(Synthesis of compound IM17)

Bis (3-amino-4-hydroxyphenyl) sulfone (manufactured by Tokyo Chemical Industry Co., Ltd.) (4.2 g) and methanol (30 ml) were mixed in a 100 ml four-necked flask equipped with a thermometer, Compound IM16 (5 g) was added thereto, the temperature was gradually raised, stirred at 60 DEG C for 19 hours, and then cooled to room temperature. The precipitated crystals were collected by filtration and washed with methanol and warm water to obtain compound IM17 (4.4 g, yield 77%).

(Synthesis of Compound D1)

Compound D1 was obtained (yield: 74%) in the same procedure, except that the compound IM9 in the synthesis of the compound B1 was replaced with the compound IM17.

LC-MS: m / z = 929 ([M + H] <^+> )

&Lt; Production Example 7 >

Compound E1 represented by the following formula was synthesized. The reaction formula is shown below.

(30)

(31)

(Synthesis of Compound E1)

Compound E1 was obtained in the same manner as in the synthesis of compound A6 except that malononitrile in the synthesis of compound A6 was replaced with compound IM15 obtained in the same manner as described in Tetrahedron 1999, 55 (1), 193-200 (Yield: 14%).

LC-MS: m / z = 481 ([M + H] <^+> )

Comparative Preparation Example (Comparative Example Compound)

(32)

(Synthesis of Comparative Example Compound Z1)

Comparative Example Compound Z1 was obtained in the same manner as in the method described in JP-A-2011-184414.

(Synthesis of Comparative Example Compound Z2)

Comparative Example Compound Z2 was obtained in the same manner as in the method described in Japanese Patent Application Laid-Open No. 2014-194508.

(Synthesis of Comparative Example Compound Z3)

Comparative Example Compound Z3 was obtained in the same manner as in the method described in Japanese Patent Application Laid-Open No. 2009-067973.

(Synthesis of Comparative Example Compound Z4)

In the same manner as in the method described in US2986528, Comparative Example Compound Z4 was obtained.

The following evaluations were carried out on the compounds obtained in each production example. The results are shown in Table 3.

&Lt; Spectral characteristics test &

The absorption spectrum of each compound in chloroform was measured, and the absorption maximum wavelength (? Max) and the gram extinction coefficient at 400 nm were measured and evaluated according to the following criteria.

Measuring instrument: Ultraviolet visible spectrophotometer V-560 manufactured by Nippon Bunko K.K.

A: a glass extinction coefficient of 30 or more

B: a gram absorptivity of 20 or more and less than 30

C: a gram absorptivity of 10 or more and less than 20

D: Gradient absorptivity less than 10

&Lt; Light resistance test &

For some of the compounds obtained in Production Examples and Comparative Production Examples, light resistance tests were carried out. 10 mg of each compound was melted in 5 ml of an 8 wt% toluene solution of polymethacrylate, spread on a glass substrate by a spin coating method, and dried to prepare a thin film having a thickness of 1.5 탆.

The prepared thin film was irradiated with light of a xenon lamp (142 klux) continuously for 96 hours, and the transmittance of the thin film after irradiation was measured by a spectrophotometer before irradiation (0 hour) Respectively.

(%) = {(1 - T ₁ ) / (1 - T ₀ )} × 100 (1)

Wherein T ₀ is a transmittance before irradiation with a xenon lamp, T ₁ is a transmittance after irradiation with a xenon lamp, and T ₀ and T ₁ are 0 to 1,

The term "transmittance" means the transmittance at the maximum absorption wavelength of each compound. The higher the residual dye ratio, the more the compound is not decomposed by light and the higher the light resistance.

The light resistance was evaluated according to the following criteria.

A: 65% or more residual pigment

B: residual pigment ratio of 40% or more and less than 65%

C: residual pigment percentage of 10% or more and less than 40%

D: Less than 10% residual pigment

<Heat resistance>

With respect to some of the compounds obtained in Production Examples and Comparative Production Examples, weight loss by thermal decomposition was measured under the following measurement conditions using a thermogravimetric analyzer TGA-50 (manufactured by Shimadzu Corporation) The reduced temperature was measured as the decomposition initiation temperature.

(Measuring conditions)

A sample amount of 5 mg, a temperature raising rate of 10 占 폚 / min (maximum arrival temperature: 400 占 폚), and a nitrogen flow rate of 10 ml / min.

The heat resistance was evaluated from the decomposition starting temperature by the following criteria.

A: 250 ° C or more

B: 210 DEG C or more and less than 250 DEG C

C: less than 210 캜

<Solubility test>

The solubility (% by weight) of toluene, methyl ethyl ketone (MEK) and propylene glycol monomethyl ether acetate (PGMEA) at 20 ° C for each of the compounds obtained in Production Examples and Comparative Production Examples was measured according to the following method .

Each compound was weighed into a glass test tube, mixed with the solvent, stirred and dissolved at 20 DEG C, and the state of the solution was observed visually to evaluate the soluble weight concentration.

A: 3 wt% or more dissolves

B: 1 wt% or more and less than 3 wt%

C: Less than 1 wt% soluble

From the above results, it was found that the compounds A1 to A6, B1 to B4, D1 and E1 prepared in each production example had a maximum absorption wavelength in the vicinity of 400 nm and a high gram extinction coefficient in 400 nm. These compounds are capable of effectively absorbing light in the vicinity of 400 nm. These compounds also had good durability. For example, the compounds A2 to A4 prepared in Production Example 2 are excellent in both light resistance, solubility and heat resistance, and are compounds that can be preferably applied as, for example, blue light shielding materials and optical dyes for optical filters Could know. Compounds Z1 to Z2 and Z4 of Comparative Examples have maximum absorption wavelengths at 363 to 382 nm, but have a low germicidal absorption coefficient at 400 nm. The compound of the present invention prepared in each production example can absorb light in the vicinity of 400 nm more effectively than the comparative compounds Z1 to Z2 and Z4. Comparative Example Compound Z3 was insufficient in durability.

Claims (14)

A compound represented by the following general formula (1).
[Chemical 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 represents a linking group having a valency of 2 to 6 when m is 2 to 6,
D ¹ represents a group in which one hydrogen atom has been removed from the compound represented by the following general formula (2), and when m is 2 to 6, plural D ^{1 s} may be the same or different.
(2)

(O) H, -C (O) -R ⁷ or -SO ₂ -R ⁸ (wherein R ¹ represents a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, R ² represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ⁷ or -SO ₂ -R ⁸ Or R ² represents -C (O) -R ⁹ , and R ¹ , R ² , and a carbon atom to which R ¹ and R ² are bonded may form a heterocyclic ring of 4 to 8 atoms which may have a substituent is formed. R ⁷ is a hydrogen atom, a halogen atom, -NR ⁷² R ⁷³ or -R ^74, R ⁸ is a halogen atom, a hydroxyl group, -OR ^81, -NR ⁸² R ⁸³ or -R ⁸⁴ represents a, R ⁹ is a hydrogen atom, a halogen atom, a hydroxyl group, -OR ^91, represents an -NR ⁹² R ⁹³ or ^{-R 94. R 72 ~ R 74} , R 81 ~ R 84 and R ⁹¹ ~ R ⁹⁴ Are the same or different and each represents a hydrogen atom, an alkyl group which may have a substituent, Aryl represents a group which may optionally 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 ) R ⁴⁰⁹ , -OC (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. And R ^404, R ⁴⁰⁵ and, R ⁴⁰⁴ and also 4 to 8 atoms which may have a nitrogen atom, R ⁴⁰⁵ is, substituents which are bonded to form a nitrogen heterocyclic ring.)) The method according to claim 1,
Wherein m in the general formula (1) is 1 or 2. 3. The method according to claim 1 or 2,
Wherein the compound represented by the general formula (1) is a compound represented by the following general formula (3).
(3)

(Wherein R ^1a represents a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ^7a or -SO ₂ -R ^8a R ^2a represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ^7a or -SO ₂ -R ^8a Or 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 may form a heterocyclic ring having 4 to 8 atoms which may have a substituent a is formed. R ^7a is a hydrogen atom, a halogen atom, -NR ^72a R ^73a or -R ^74a, R ^8a is a halogen atom, a hydroxyl group, -OR ^81a, -NR ^82a R ^83a or -R It represents ^84a, R ^9a represents a hydrogen atom, a halogen atom, a hydroxyl group, -OR ^91a, -NR ^92a R ^93a or ^{-R 94a. R 72a ~ R 74a} , R 81a ~ R 84a and R ^91a ~ R ^94a are the same or different and each represents a hydrogen atom or a substituent An alkyl group having 1 to 20 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 represents 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 , (O) R ^409a , -OC (O) R ^410a or -C (O) OR ^411a , and R ^404a to R ^411a are the same or different and each represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms Or an aryl group having 6 to 20 carbon atoms which may have a substituent. And R ^404a, R ^405a, and also 4 to 8 atoms which may optionally R ^404a and R ^405a has a nitrogen atom, and the substituent are bonded to form a nitrogen heterocyclic ring.
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 a group represented by the following formula (4).
[Chemical Formula 4]

(In the general formula (4), Q ² represents a divalent hydrocarbon group of 1 to 20 carbon atoms which may have a substituent, and * represents a bonding site with the general formula (3).
R ^1b is a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic ring-containing group, -OC (O) H, -C (O) -R ^7b represents or -SO ₂ -R ^8b, R ^2b is hydrogen -C (O) -R ^7b or -SO ₂ -R ^8b , or R ^2b represents -C (O) -R ^7b , (O) -R ^9b , and R ^1b , R ^2b and R ^1b and R ^2b are bonded to form a heterocyclic ring of 4 to 8 atoms which may have a substituent. R ^7b represents a hydrogen atom, a halogen atom, -NR ^72b R ^73b or -R ^74b , R ^8b represents a halogen atom, a hydroxyl group, -OR ^81b , -NR ^82b R ^83b or -R ^84b , R ^9b represents a hydrogen atom, a halogen atom, a hydroxyl group, -OR ^91b , -NR ^92b R ^93b or -R ^94b . R ^72b to R ^74b , R ^81b to R ^84b and R ^91b to R ^94b are the same or different and each represents 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 Lt; / RTI &gt;
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 and may have a substituent.
R ^402b represents 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 ^407b , -OR ^408b , a cyano group, (O) R ^409b , -OC (O) R ^410b or -C (O) OR ^411b , and R ^404b to R ^411b are the same or different and each represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms Or an aryl group having 6 to 20 carbon atoms which may have a substituent. And R ^404b, and R ^405b, R ^404b and R ^405b are also coupled to form a nitrogen-containing heterocyclic ring of 4-8 atoms which may have a nitrogen atom, the substituents in.)) The method of claim 3,
^Wherein R ⁴¹³ is a group represented by the general formula (4). The method of claim 3,
Wherein R ^2a is -C (O) -R ^9a , and R ^1a , R ^2a , and R ^1a and R ^2a are bonded to form a heterocyclic ring of 4 to 8 atoms which may have a substituent , Compound. 3. The method according to claim 1 or 2,
Wherein the compound represented by the general formula (1) is a compound represented by the following general formula (5).
[Chemical Formula 5]

(5), R ^2c represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic group, -OC (O) H, -C (O) -R ^7c or -SO ₂ which represents the -R ^8c R ^7c is, represents a hydrogen atom, a halogen atom, -NR ^72c R ^73c or -R ^74c, R ^8c is a halogen atom, a hydroxyl group, -OR ^81c, -NR ^82c R ^83c or - It represents an R ^84c. R ^72c ~ R ^74c and R ^81c ~ R ^84c is the same or different, a hydrogen atom, which may have an alkyl group or a substituent having 1 to 20 carbon atoms which may be substituted 6-20 aryl groups of .
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 and may have a substituent.
R ^402c and R ^403c are the same or different and each represents 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 ^406c R ^407c , oR ^408c, a cyano ^{group, -C (O) R 409c,} -OC (O) R 410c , or represents a -C (O) oR ^{411c, 404c} R ~ R ^411c, the same or different, a hydrogen atom, a substituent An optionally substituted alkyl group having 1 to 20 carbon atoms or an optionally substituted aryl group having 6 to 20 carbon atoms. R ^404c , R ^405c , a nitrogen atom bonded to R ^404c and R ^405c , or a nitrogen-containing heterocycle having 4 to 8 atoms which may have a substituent.
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 a group represented by the following formula (6).
Y ^1c represents -NR ^502c -, R ^502c represents 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.
[Chemical Formula 6]

(In the general formula (6), Q ³ represents a divalent hydrocarbon group of 1 to 20 carbon atoms which may have a substituent, and * represents a bonding site with the general formula (5).
Y ^1d represents -NR ^502d - and R ^502d represents 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 ^2d represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic-containing group, -OC (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 hydroxyl group, -OR ^81d , -NR ^82d R ^83d or -R ^84d . R ^72d to R ^74d and R ^81d to R ^84d are the same or different and each represents 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 ^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 and may have a substituent.
R ^402d and R ^403d, the same or different, a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, having from 6 to 20 carbon atoms which may have a substituent, an aryl group, and -NR R ^{406d 407d,} - OR ^408d , cyano group, -C (O) R ^409d , -OC (O) R ^410d or -C (O) OR ^411d , and R ^404d to R ^411d are the same or different and each represents a hydrogen atom or a substituent An optionally substituted alkyl group having 1 to 20 carbon atoms or an optionally substituted aryl group having 6 to 20 carbon atoms. And R ^{404d, 405d} and the R, R ^404d and R ^405d is also bonded to form a nitrogen-containing heterocyclic ring of 4-8 atoms which may have a nitrogen atom, the substituents in.)) The method according to claim 6,
Wherein R &lt; ⁵⁰¹ &gt; is a group represented by the above general formula (6). 3. The method according to claim 1 or 2,
Wherein the compound represented by the general formula (1) is a compound represented by the following general formula (7).
(7)

(In the general formula (7), Q ⁴ represents -SO ₂ - or a divalent hydrocarbon group of 1 to 20 carbon atoms which may have a substituent.
R ^1e represents a heterocyclic group, -C (O) -R ^7e or -SO ₂ -R ^8e , and R ^2e represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, -OC (O) H, -C (O) -R ^7e or -SO ₂ -R ^8e . R ^7e represents a hydrogen atom, a halogen atom, -NR ^72e R ^73e or -R ^74e , and R ^8e represents a halogen atom, a hydroxyl group, -OR ^81e , -NR ^82e R ^83e or -R ^84e . R ^72e to R ^74e and R ^81e to R ^84e are the same or different and each represents 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 ^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 and may have a substituent.
R ^402e and R ^403e are the same or different and each represents 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 ^406e R ^407e , oR ^408e, a cyano ^{group, -C (O) R 409e,} -OC (O) R 410e or represents a ^{-C (O) oR 411e, R} 404e ~ R 411e is the same or different, a hydrogen atom, a substituent An optionally substituted alkyl group having 1 to 20 carbon atoms or an optionally substituted aryl group having 6 to 20 carbon atoms. R ^404e, and R ^405e, and also of 4-8 atoms which may optionally R ^404e and R ^405e has a nitrogen atom, and the substituent are bonded to form a nitrogen heterocyclic ring.) 9. The method of claim 8,
Wherein Q ^4, -SO ₂ - in the compounds. A colorant composition characterized by containing the compound according to any one of claims 1 to 9. An optical filter comprising the compound according to any one of claims 1 to 9. 12. The method of claim 11,
An optical filter, which is a color filter. A blue light shielding material characterized by containing a compound according to any one of claims 1 to 9. An ultraviolet absorber comprising a compound according to any one of claims 1 to 9.