TWI770058B - Dye compound - Google Patents

Abstract

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

The present invention is a compound represented by the general formula (1).

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

In the general formula (2), R ¹ represents a hydrogen atom or the like, and R ² represents a hydrogen atom, a cyano group or the like. R ³ represents a hydrogen atom or the like. R ⁴⁰² to R ⁴⁰⁵ are the same or different, and represent a hydrogen atom, an alkyl group, or the like.

Description

pigment compounds

The present invention relates to a compound and the like which can be used as a pigment.

Ultraviolet rays or blue light have strong energy, and may damage the retina and cause eye diseases. Therefore, a compound that can be used as an ultraviolet absorber, a blue light cut-off colorant, or the like has been sought. As an ultraviolet absorber, it is proposed to use a methine type compound instead of a benzophenone type or a benzotriazole type ultraviolet absorber, for example (Patent Documents 1 and 2).

[Patent Document 1] Japanese Patent Laid-Open No. 2009-067973

[Patent Document 2] Japanese Patent Laid-Open No. 2011-184414

Since the absorbance of the conventional methine-based compound is low in the vicinity of the visible light region, it is necessary to increase the amount of addition in order to reduce blue light. Therefore, there is a need for improvement in the shape or absorbance of the absorption spectrum.

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

As a result of diligent studies to solve the above-mentioned problems, the present inventors found that a compound having a nitrogen-containing aromatic ring and an electron-withdrawing group and having a methine structure represented by the following general formula (1) has an absorption maximum around 400 nm , and the absorbance near 400nm is high. Based on this knowledge, the inventors of the present invention conducted repeated studies and completed the present invention.

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

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

(In the general formula (2), R ¹ represents a hydrogen atom, an alkyl group which may have a substituent or an aryl group which may have a substituent; R ² represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic ring-containing group base, -C(O)-R ⁷ or -SO ₂ -R ⁸ ; R ⁷ represents hydroxyl or -OR ⁷¹ , R ⁸ represents halogen atom, hydroxyl, -OR ⁸¹ , -NR ⁸² R ⁸³ or -R ⁸⁴ ; R ⁷¹ and R ⁸¹ to R ⁸⁴ are the same or different, and represent a hydrogen atom, an alkyl group that may have a substituent or an aryl group that may have a substituent; R ³ represents a hydrogen atom, a halogen atom, a cyano group, an alkane that may have a substituent R ⁴⁰² and R ⁴⁰³ are the same or different, and represent a hydrogen atom, a halogen atom, an alkyl group that may have a substituent, an aryl group that may have a substituent, -NR ⁴⁰⁶ R ⁴⁰⁷ , -OR ⁴⁰⁸ , cyano group, -C(O)R ⁴⁰⁹ , -OC(O)R ⁴¹⁰ or -C(O)OR ⁴¹¹ , R ⁴⁰⁴ to R ⁴¹¹ are the same or different, and represent a hydrogen atom, an alkyl group which may have a substituent or Aryl which may have a substituent; a nitrogen-containing heterocycle of 4-8 members which may have a substituent may also be formed by the nitrogen atom bounded by R ⁴⁰⁴ and R ⁴⁰⁵ and R ⁴⁰⁴ and R ⁴⁰⁵ ))

In the present invention, m in the above general formula (1) is preferably 1 or 2.

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

(In the general formula (3), R ^1a represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms that may have a substituent, or an aryl group that may have a substituent group having 6 to 20 carbon atoms, and R ^2a represents a hydrogen atom, a cyano group , nitro, trifluoromethyl, heterocyclic group, -C(O)-R ^7a or -SO ₂ -R ^8a ; R ^7a represents hydroxyl or -OR ^71a , R ^8a represents halogen atom, hydroxyl, -OR ^81a , -NR ^82a R ^83a or -R ^84a ; R ^71a and R ^81a to R ^84a are the same or different, and represent a hydrogen atom, an alkyl group with 1 to 20 carbon atoms that may have a substituent, or a carbon number 6 that may have a substituent group Aryl group of ~20; R ^3a represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group with 1 to 20 carbon atoms which may have a substituent or an aryl group with 6 to 20 carbon atoms that may have a substituent; R ^402a represents hydrogen Atom, halogen atom, alkyl group with 1 to 20 carbon atoms which may have a substituent, aryl group with 6 to 20 carbon atoms which may have a substituent, -NR ^406a R ^407a , -OR ^408a , cyano group, -C(O ) R ^409a , -OC(O)R ^410a or -C(O)OR ^411a , R ^404a ～R ^411a are the same or different, and represent a hydrogen atom, an alkyl group with 1 to 20 carbon atoms that may have a substituent or a substituent The aryl group of the carbon number of the base is 6~20; it can also form a nitrogen-containing heterocyclic ring with 4~8 members that can have substituents by the nitrogen atoms bonded by R ^404a and R ^405a and R ^404a and R ^405a ; R ⁴¹³ represents hydrogen Atom, an optionally substituted alkyl group with 1 to 20 carbon atoms, an optionally substituted aryl group with 6 to 20 carbon atoms, or a group represented by the following general formula (4);

(In the general formula (4), Q ² represents a divalent hydrocarbon group with 1 to 20 carbon atoms which may have a substituent, * represents a bonding site with the general formula (3); R ^1b represents a hydrogen atom, which may have a substituent Alkyl with 1 to 20 carbon atoms or aryl group with 6 to 20 carbon atoms that may have substituents, R ^2b represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a group containing a heterocyclic ring, -C(O )-R ^7b or -SO ₂ -R ^8b ; R ^7b represents a hydroxyl group or -OR ^71b , R ^8b represents a halogen atom, a hydroxyl group, -OR ^81b , -NR ^82b R ^83b or -R ^84b ; R ^71b and R ^81b ～R ^84b are the same or different, and represent a hydrogen atom, an alkyl group with a carbon number of 1 to 20 that may have a substituent or an aryl group with a carbon number of 6 to 20 that may have a substituent; R ^3b represents a hydrogen atom, a halogen atom, a cyano group, C 1-20 alkyl group with substituent or aryl group with carbon number 6-20 which may have substituent; R ^402b represents hydrogen atom, halogen atom, alkyl group with 1-20 carbon number which may have substituent, Aryl with 6 to 20 carbon atoms, -NR ^406b R ^407b , -OR ^408b , cyano group, -C(O)R ^409b , -OC(O)R ^410b or -C(O)OR ^411b , R ^404b ~ R ^411b are the same or different, and represent a hydrogen atom, an alkyl group with a carbon number of 1 to 20 that can have a substituent or an aryl group with a carbon number of 6 to 20 that can have a substituent; R ^404b and R ^405b and The nitrogen atoms that R ^404b and R ^405b are bonded to form a nitrogen-containing heterocycle of 4 to 8 members which may have substituents))

In one aspect of the present invention, preferably, the above R ⁴¹³ is a group represented by the above general formula (4).

The compound represented by the above general formula (1) is also preferably a compound represented by the following general formula (5).

(In the general formula (5), R ^2c represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a group containing a heterocyclic ring, -C(O)-R ^7c or -SO ₂ -R ^8c ; R ^7c represents Hydroxyl or -OR ^71c , R ^8c represents a halogen atom, hydroxyl, -OR ^81c , -NR ^82c R ^83c or -R ^84c ; R ^71c and R ^81c to R ^84c are the same or different, represent a hydrogen atom, a carbon that may have a substituent Alkyl with 1 to 20 carbon atoms or aryl group with 6 to 20 carbon atoms that may have substituents; R ^3c represents hydrogen atom, halogen atom, cyano group, alkyl group with 1 to 20 carbon atoms that may have substituents or may have The aryl group with 6~20 carbon atoms of the substituent; R ^402c and R ^403c are the same or different, and represent a hydrogen atom, a halogen atom, an alkyl group with a carbon number of 1~20 that may have a substituent, and a carbon number 6 that may have a substituent Aryl group of ~20, -NR ^406c R ^407c , -OR ^408c , cyano group, -C(O)R ^409c , -OC(O)R ^410c or -C(O)OR ^411c , R ^404c ~R ^411c are the same or Differently, it represents a hydrogen atom, an alkyl group with a carbon number of 1 to 20 that may have a substituent, or an ^aryl group with a ^{carbon number} of ⁶ to 20 that may have a substituent. The nitrogen atom forms a nitrogen-containing heterocyclic ring with 4 to 8 members that may have a substituent; R ⁵⁰¹ represents a hydrogen atom, an alkyl group with a carbon number of 1 to 20 that may have a substituent, and an alkyl group with a carbon number of 6 to 20 that may have a substituent. An aryl group or a group represented by the following general formula (6);

(In the general formula (6), Q ³ represents a divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, * represents a bonding site with the general formula (5); R ^2d represents a hydrogen atom, a cyano group, a nitro group , trifluoromethyl, group containing a heterocyclic ring, -C(O)-R ^7d or -SO ₂ -R ^8d ; R ^7d represents hydroxyl or -OR ^71d ; R ^8d represents halogen atom, hydroxyl, -OR ^81d , - NR ^82d R ^83d or -R ^84d ; R ^71d and R ^81d to R ^84d are the same or different, and represent a hydrogen atom, an alkyl group with 1 to 20 carbon atoms that may have a substituent, or an alkyl group with 6 to 20 carbon atoms that may have a substituent Aryl; R ^3d represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group with 1 to 20 carbon atoms that may have a substituent or an aryl group with 6 to 20 carbon atoms that may have a substituent; R ^402d and R ^403d are the same or Different, it represents a hydrogen atom, a halogen atom, an alkyl group with 1 to 20 carbon atoms that may have a substituent, an aryl group with 6 to 20 carbon atoms that may have a substituent, -NR ^406d R ^407d , -OR ^408d , cyano group, -C(O)R ^409d , -OC(O)R ^410d or -C(O)OR ^411d , R ^404d to R ^411d are the same or different, and represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms that may have a substituent Or an aryl group with a carbon number of 6 to 20 that may have a substituent; a nitrogen-containing heterocyclic ring with 4 to 8 members that may have a substituent can also be formed from the nitrogen atoms bound by R ^404d and R ^405d and R ^404d and R ^405d ) )

In one aspect of the present invention, the above-mentioned R ⁵⁰¹ is preferably a group represented by the above-mentioned general formula (6).

The pigment composition of the present invention is characterized by containing the compound of the present invention.

The blue light shielding molded body 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 around 400 nm can be provided. The compound of the present invention can be suitably used as a dye or the like for a blue light shielding molded body or the like.

The compound of the present invention is a compound represented by the above-mentioned general formula (1). In this specification, the compound represented by the said general formula (1) is also called compound (1). The same applies to compounds numbered by other formulae. For example, the compound represented by general formula (2) is also referred to as compound (2).

When there is geometric isomerism in the compound (1) of the present invention, the present invention includes any one of the geometric isomers. In addition, when there is one or more asymmetric carbon atoms in the compound (1) of the present invention, the present invention includes compounds in which each asymmetric carbon atom is arranged in R, compounds in which it is arranged in S, and any combination thereof. any of the compounds. In addition, any of these racemic compounds, racemic mixtures, single enantiomers, and diastereomer mixtures are included in the present invention.

In the above general formula (1), m represents an integer of 1 to 6. When m is 2 to 6, since the heat resistance of the compound (1) is improved, it is preferable. In one aspect of the present invention, m is preferably 1 or 2, more preferably 2.

When m is 1, Q ¹ represents a hydrogen atom, and when m is 2 to 6, it represents a 2- to 6-valent linking group.

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

Examples of the 2- to 6-valent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent include a linear, branched or cyclic 2-6 valent alkyl group having 1 to 20 carbon atoms which may have a substituent; A 2- to 6-valent extended aryl group with 6 to 20 carbon atoms in the substituent. Q ¹ is preferably a hydrogen atom or a divalent linking group.

The divalent linking group is preferably a divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, -SO ₂ - and the like, and more preferably a divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. The divalent hydrocarbon group with 1 to 20 carbon atoms which may have a substituent is preferably a linear, branched or cyclic divalent alkyl group with 1 to 20 carbon atoms which may have a substituent, and a 6~20 carbon group which may have a substituent 20 of the 2-valent aryl extended.

The linear, branched or cyclic divalent alkyl group with 1 to 20 carbon atoms can also be a divalent alkyl group in which an oxygen atom, a sulfur atom or an aryl extended group which may have a substituent is inserted between carbon-carbon, preferably It is a linear divalent alkyl group with 1 to 20 carbon atoms represented by -(CH ₂ ) _k1 -(k1 represents an integer of 1 to 20), for example, methylene group, ethylidene group, propylidene group, ethylene group Butyl, pentyl, hexyl, heptyl, octyl, decyl, etc. Moreover, a divalent alkyl group substituted with one or more halogen atoms is also preferable, and examples thereof include bis(trifluoromethyl)methylene and the like. The carbon number of the linear divalent alkyl group is more preferably 2 to 10 (k1 in the above formula is 2 to 10), more preferably 4 to 8 (k1 in the above formula is 4 to 8).

As the divalent aryl extended 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.

In the above general formula (20), X independently represents 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, and s represents an integer of 0 to 4. . The 2-position bond of the benzene ring can be any of o-, m-, and p-alignments. Moreover, it is preferable that a benzene ring does not have a substituent (s=0).

In the general formula (1), D ¹ represents a group from which one hydrogen atom is removed from the compound (2). The group from which one hydrogen atom is removed from the compound (2) may also be referred to as a group from which one hydrogen atom is removed from the compound (2). The compound (2) contains a nitrogen-containing aromatic ring and an electron-withdrawing group, and contains a methine structure that can become a dye. Since the compound (1) contains such a methine structure, it can be used as a dye compound. When m is 2 to 6, the plurality of D ¹ may all be the same or different. In one aspect, it is preferred that the plurality of D ^1s are all the same.

In the general formula (1), the compound (1) in which m is 1 is the compound (2). The compound (1) in which m is 1 is also referred to as a monomer compound. The compound (1) in which m is 2 to 6 is a compound having a 2 to 6-mer structure in which 2 to 6 groups from which a hydrogen atom is removed from the compound (2) are connected by a linking group (Q ¹ ). The compound (1) in which m is 2 to 6 may also be referred to as a 2 to 6 polymer compound.

D ¹ is preferably a group from which one hydrogen atom is removed from R ¹ , R ⁴⁰³ or R ⁴⁰⁴ of compound (2) (in the case where R ¹ is a hydrogen atom, the group from which R ¹ is removed), more preferably It is a base for removing 1 hydrogen atom from R ¹ or R ⁴⁰³ . In other words, in the general formula (1), Q ¹ is preferably bonded to a part of R ¹ , R ⁴⁰³ or R ⁴⁰⁴ in the general formula (2), more preferably a part of R ¹ or R ⁴⁰³ .

In the general formula (2), R ¹ represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group. As an alkyl group which may have a substituent, the alkyl group of C1-C20 which may have a substituent is mentioned. As an aryl group which may have a substituent, the C6-C20 aryl group which may have a substituent is mentioned. -C(O)-OR ¹ in the general formula (2) is an electron-withdrawing group. R ¹ is preferably an optionally substituted alkyl group having 1 to 20 carbon atoms or an optionally substituted aryl group having 6 to 20 carbon atoms, more preferably an optionally substituted alkyl group having 1 to 20 carbon atoms.

R ² represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group (CF ₃ group), a group containing a heterocyclic ring, -C(O)-R ⁷ or -SO ₂ -R ⁸ . R ⁷ represents a hydroxyl group or -OR ⁷¹ , and R ⁸ represents a halogen atom, a hydroxyl group, -OR ⁸¹ , -NR ⁸² R ⁸³ or -R ⁸⁴ . R ⁷¹ and R ⁸¹ to R ⁸⁴ are the same or different, and represent a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group.

環、吡

環、咪唑環、苯并咪唑環、三

環、三唑環、四唑環等含氮雜環；呋喃環、苯并呋喃環等含氧雜環；噻吩環、苯并噻吩環等含硫雜環；

唑環、苯并

唑環等含有氧原子及氮原子之雜環；噻唑環、苯并噻唑環、噻二唑環等含硫雜環等；該等環亦可進而與其他碳環(例 如苯環)或雜環(例如吡啶環)形成縮合環，較佳為

唑環、苯并

唑環。 Examples of the group containing a heterocyclic ring in R ² include pyrrole ring, pyridine ring, quinoline ring, pyrimidine ring, pyridine ring, and pyridine ring.

Cyclo, pyridine

ring, imidazole ring, benzimidazole ring, three

Nitrogen-containing heterocycles such as ring, triazole ring and tetrazole ring; oxygen-containing heterocycles such as furan ring and benzofuran ring; sulfur-containing heterocycles such as thiophene ring and benzothiophene ring;

azole ring, benzo

Heterocycles containing oxygen atoms and nitrogen atoms such as azole rings; sulfur-containing heterocycles such as thiazole rings, benzothiazole rings, thiadiazole rings, etc.; these rings can also be further combined with other carbon rings (such as benzene rings) or heterocycles (such as a pyridine ring) to form a condensed ring, preferably

azole ring, benzo

azole ring.

唑環或

唑環之氮與氧之間的碳(2位)脫去氫原子之基(亦可稱為去掉氫原子之基)，更佳為自苯并

唑環之氮與氧之間的碳(2位)脫去氫原子之基。 In one aspect of the present invention, as the group containing a heterocyclic ring in R ² , it is preferably from benzo

azole ring or

The carbon (2-position) between the nitrogen and oxygen of the azole ring is a base from which a hydrogen atom is removed (also called a base from which a hydrogen atom is removed), more preferably from benzo

The carbon (2-position) between the nitrogen and oxygen of the azole ring removes the hydrogen atom.

唑環或

唑環中脫去氫原子之基，於Q¹與D¹於化合物(2)之R²之部位鍵結之情形時，R²較佳為以苯并

唑環或

唑環之氮與氧之間的碳(2位)以外之碳原子與Q¹鍵結。 Also, for example, in the general formula (1), m is 2 to 6, and R ² is from benzo

azole ring or

In the base of dehydrogen atom in the azole ring, when Q ¹ and D ¹ are bonded at the position of R ² of compound (2), R ² is preferably benzo

azole ring or

A carbon atom other than the carbon (2-position) between nitrogen and oxygen of the azole ring is bonded to Q ¹ .

Examples of the optionally substituted alkyl group among R ¹ , R ⁷¹ , R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ include optionally substituted alkyl groups having 1 to 20 carbon atoms. Examples of the alkyl group having 1 to 20 carbon atoms which may have a substituent include the following linear, branched or cyclic alkyl groups having 1 to 20 carbon atoms which may have a substituent. In one aspect of the present invention, the alkyl group with 1 to 20 carbon atoms that may have a substituent is preferably a straight-chain, branched or cyclic alkyl group with 4 to 20 carbon atoms, preferably 4 or more carbon atoms. The branched or cyclic sterically bulky alkyl group is more preferably a cyclic alkyl group having 6 to 20 carbon atoms, and particularly preferably a cyclic alkyl group which may have a straight-chain or branched alkyl group as a substituent. As the alkyl group having 1 to 20 carbon atoms in R ¹ , R ⁷¹ , R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ , for example, methyl, ethyl, n-propyl, isopropyl, n-butyl are preferred , isobutyl, tert-butyl, n-hexyl, cyclohexyl, n-octyl, 2-ethylhexyl, 4-tert-butylcyclohexyl, 2,6-di-tert-butyl-4-methyl Cyclohexyl, etc., more preferably tert-butyl, cyclohexyl, 4-tert-butylcyclohexyl, 2,6-di-tert-butyl-4-methylcyclohexyl, etc., more preferably 4-tert-butylcyclohexyl Tributylcyclohexyl, 2,6-di-tert-butyl-4-methylcyclohexyl, etc.

Among R ¹ , R ⁷¹ , R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ , the optionally substituted aryl group includes an optionally substituted 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 the following aryl groups having 6 to 20 carbon atoms which may have a substituent, for example, preferably a phenyl group which may be substituted with an alkyl group (for example, phenyl, 3-methylphenyl, 2,6-dimethylphenyl, etc.) and the like.

R ¹ is preferably n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclohexyl, n-octyl, 2-ethylhexyl, 4-tert-butyl ring Hexyl, 2,6-di-tert-butyl-4-methylcyclohexyl, etc., more preferably 4-tert-butylcyclohexyl, 2,6-di-tert-butyl-4-methylcyclohexyl Wait.

R ² is preferably a cyano group, a nitro group, a trifluoromethyl group, a group containing a heterocyclic ring, -C(O)-R ⁷ or -SO ₂ -R ⁸ , more preferably a cyano group, a group containing a heterocyclic ring or -C(O)-R ⁷ , more preferably cyano or -C(O)-OR ⁷¹ .

R ⁷¹ and R ⁸¹ are the same or different, for example, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl cyclohexyl, cyclohexyl, n-octyl, 2-ethylhexyl, 4-tert-butylcyclohexyl, 2,6-di-tert-butyl-4-methylcyclohexyl, etc., more preferably 4-tertiary Butylcyclohexyl, 2,6-di-tert-butyl-4-methylcyclohexyl, etc. R ⁸² is preferably a hydrogen atom. R ⁸³ is preferably a hydrogen atom, phenyl, 3-methylphenyl or 2,6-dimethylphenyl. R ⁸⁴ is preferably methyl, ethyl, tert-butyl, cyclohexyl, phenyl, naphthyl and the like.

In the general formula (2), R ³ represents a hydrogen atom, a halogen atom, a cyano group, an optionally substituted alkyl group, or an optionally substituted aryl group.

R ⁴⁰² and R ⁴⁰³ are the same or different, and represent a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, -NR ⁴⁰⁶ R ⁴⁰⁷ , -OR ⁴⁰⁸ , a cyano group, -C(O) R ⁴⁰⁹ , -OC(O)R ⁴¹⁰ or -C(O)OR ⁴¹¹ .

R ⁴⁰⁴ to R ⁴¹¹ are the same or different and represent a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent. A nitrogen-containing heterocycle of 4 to 8 members which may have a substituent can also be formed from the nitrogen atom to which R ⁴⁰⁴ and R ⁴⁰⁵ are bonded to R ⁴⁰⁴ and R ⁴⁰⁵ .

Examples of the alkyl group among R ³ , R ⁴⁰² and R ⁴⁰³ include linear, branched, or cyclic alkyl groups having 1 to 20 carbon atoms. Specific examples of linear, branched or cyclic alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and sec-butyl. , tert-butyl, n-pentyl, 2-methylbutyl, 1-methylbutyl, neopentyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, cyclopentyl base, n-hexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3,3-dimethylbutyl, 2,3-dimethyl Butyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 1,2-dimethylbutyl, 1,1-dimethylbutyl, 2-ethylbutyl, 1-ethylbutyl, 1,1,2-trimethylbutyl, 1-ethyl-2-methylpropyl, cyclohexyl, n-heptyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 2,4-dimethylpentyl, n-octyl, 2-ethylhexyl, 2,5-dimethylhexyl, 2,4-dimethylhexyl, 2,2,4-trimethylpentyl, tert-octyl, n-nonyl, 3,5,5-trimethylhexyl, n-decyl, 4-ethyloctyl, 4-ethyl-4, 5-dimethylhexyl, 4-tert-butylcyclohexyl, n-undecyl, n-dodecyl, 1,3,5,7-tetramethyloctyl, 4-butyloctyl, 6 ,6-Diethyloctyl, n-tridecyl, 6-methyl-4-butyloctyl, n-tetradecyl, n-pentadecyl, 3,5-dimethylheptadecyl , 2,6-dimethylheptadecyl, 2,4-dimethylheptadecyl, 2,2,5,5-tetramethylhexyl, 1-cyclopentyl-2,2-dimethyl propylpropyl, 1-cyclohexyl-2,2-dimethylpropyl, 2,6-di-tert-butyl-4-methylcyclohexyl, n-octadecyl, etc.

The substituents in the alkyl group which may have a substituent are not particularly limited, and examples include monocyclic or polycyclic aromatic ring groups (phenyl, naphthyl, etc.) with 6 to 10 carbon atoms, and straight chain with 1 to 8 carbon atoms. , branched or cyclic alkoxy group, amine group, mono- or di-alkylamine group (the carbon number of the alkyl group is 1~8), halogen atom, cyano group, hydroxyl group, nitro group, carboxyl group, carbon number 1 ~8 alkoxycarbonyl group, carbon number 2~10 acyl group (such as acetyl group, propionyl group, butyryl group, pentamyl group, trimethylacetyl group, acrylyl group, methacrylyl group, benzene carboxyl, tolyl carboxyl, cinnamonyl, methoxybenzyl, naphthyl, etc.), carbon number 2-10 carboxyloxy, etc.

Examples of the aryl group in R ³ , R ⁴⁰² and R ⁴⁰³ include monocyclic or polycyclic aromatic ring groups having 6 to 20 carbon atoms. Specific examples of the monocyclic or polycyclic aromatic ring group having 6 to 20 carbon atoms include monocyclic aromatic hydrocarbon groups such as phenyl; naphthyl, anthracenyl, and naphthacenyl , Polycyclic aromatic hydrocarbon groups such as pentacenyl, phenanthrenyl, and pyrene.

The substituents in the optionally substituted aryl group are not particularly limited, for example, linear, branched or cyclic alkyl groups with 1 to 8 carbon atoms, alkoxy groups with 1 to 8 carbon atoms, amine groups, mono- - or di-alkylamino group (the carbon number of the alkyl group is 1~8), halogen atom, cyano group, hydroxyl group, nitro group, halogenated hydrocarbon group with 1~8 carbon number, carboxyl group, alkoxy group with 1~8 carbon number carbonyl, etc. It is preferably a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms. For example, nitrophenyl, cyanophenyl, hydroxyphenyl, methylphenyl, dimethylphenyl, trimethylphenyl, fluorine, etc. Phenyl, chlorophenyl, dichlorophenyl, bromophenyl, methoxyphenyl, ethoxyphenyl, trifluoromethylphenyl, N,N-dimethylaminophenyl, nitronaphthalene Naphthyl, cyano naphthyl, hydroxynaphthyl, methyl naphthyl, fluoronaphthyl, chloronaphthyl, bromonaphthyl, trifluoromethyl naphthyl and the like.

環、嗎福啉環等非芳香族性含氮雜環。 In the general formula (2), the 4- to 8-membered nitrogen-containing heterocycle formed by R ⁴⁰⁴ and R ⁴⁰⁵ and the nitrogen atom to which R ⁴⁰⁴ and R ⁴⁰⁵ are bonded may also be a nitrogen-containing heterocycle containing an oxygen atom. As the nitrogen-containing heterocyclic ring, a non-aromatic nitrogen-containing heterocyclic ring is exemplified. As the nitrogen-containing heterocyclic ring having 4 to 8 members, for example, a pyrrolidine ring, a piperidine ring, a piperidine ring, a

Non-aromatic nitrogen-containing heterocycles such as ring, morpholine ring, etc.

The substituents in the nitrogen-containing heterocyclic ring with 4 to 8 members which may have substituents are not particularly limited, for example, straight-chain, branched or cyclic alkyl groups with 1 to 8 carbon atoms, and alkanes with 1 to 8 carbon atoms are exemplified. Oxygen group, amino group, mono- or di-alkylamine group (the carbon number of the alkyl group is 1~8), halogen atom, cyano group, hydroxyl group, nitro group, halogenated hydrocarbon group with carbon number 1~8, carboxyl group, carbon group Alkoxycarbonyl groups from 1 to 8, etc. 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, and a heterocycle has a substituent, when there are two or more substituents, each substituent may be the same or different.

The preferred aspect of each group in the general formula (2) will be further described.

R ³ is preferably a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or a cyano group that may have a substituent, more preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms that may have a substituent group, and more preferably hydrogen atom or an alkyl group having 1 to 3 carbon atoms, particularly preferably a hydrogen atom.

R ⁴⁰² is preferably a hydrogen atom, an alkyl group with a carbon number of 1 to 20 that may have a substituent, an aryl group or an alkoxy group with a carbon number of 6 to 20 that may have a substituent, more preferably a carbon number that may have a substituent 1~20 alkyl. More preferably, it is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms which may have 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 with 1 to 20 carbon atoms that may have a substituent, or an aryl group with 6 to 20 carbon atoms that may have a substituent, more preferably a hydrogen atom or an alkyl group with 1 to 20 carbon atoms that may have a substituent An alkyl group of ~5 is more preferably an alkyl group having 1 to 3 carbon atoms, and an ethyl group is particularly preferred.

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

R ⁴⁰⁴ and R ⁴⁰⁵ are the same or different, preferably an alkyl group having 1 to 20 carbon atoms which may have a substituent or an aryl group having 6 to 20 carbon atoms that may have a substituent, more preferably an alkane having 1 to 10 carbon atoms group or an aryl group having 6 to 10 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, particularly preferably a methyl group, an ethyl group, an n-propyl group, and an n-butyl group.

R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ are the same or different, preferably an alkyl group with 1 to 20 carbon atoms which may have a substituent or an aryl group with 6 to 20 carbon atoms which may have a substituent base.

As the compound in which m is 1 or 2 in the general formula (1), the compound represented by the above-mentioned general formula (3) (compound (3)), the compound represented by the general formula (5) (compound (5)), and the like are preferable.

In one aspect of the present invention, the compound (1) is preferably the compound (3). Compound (3) is preferable because it is excellent in light resistance.

In the general formula (3), R ^1a represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms that may have a substituent, or an aryl group that may have a substituent group having 6 to 20 carbon atoms, and R ^2a represents a hydrogen atom, a cyano group, Nitro, trifluoromethyl, heterocycle-containing group, -C(O)-R ^7a or -SO ₂ -R ^8a . R ^7a represents a hydroxyl group or -OR ^71a , and R ^8a represents a halogen atom, a hydroxyl group, -OR ^81a , -NR ^82a R ^83a or -R ^84a . R ^71a and R ^81a to R ^84a are the same or different, and represent a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 20 carbon atoms.

The preferred aspect of R ^1a is the same as the preferred aspect of R ¹ described above.

R ^2a is preferably a cyano group, a heterocyclic-containing group or -C(O)-R ^7a , more preferably a cyano group or -C(O)-OR ^71a . Preferred embodiments of R ^71a , R ^81a , R ^82a , R ^83a and R ^84a are the same as the preferred embodiments of R ⁷¹ , R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ described above, respectively.

In the general formula (3), R ^3a represents a hydrogen atom, a halogen atom, a cyano group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 20 carbon atoms.

R ^402a represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted aryl group having 6 to 20 carbon atoms, -NR ^406a R ^407a , -OR ^408a , cyano, -C(O)R ^409a , -OC(O)R ^410a or -C(O)OR ^411a , R ^404a to R ^411a are the same or different, and represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms that may have a substituent Or an aryl group having 6 to 20 carbon atoms which may have a substituent. A nitrogen-containing heterocycle of 4 to 8 members which may have a substituent may also be formed from the nitrogen atom to which R ^404a and R ^405a and R ^404a and R ^405a are bonded.

Preferred embodiments of R ^3a , R ^402a , R ^404a , R ^405a , R ^406a , R ^407a , R ^408a , R ^409a , R ^410a and R ^411a are the same as those of the above R ³ , R ⁴⁰² , R ⁴⁰⁴ , R ⁴⁰⁵ , R ⁴⁰⁶ The preferred aspects of R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R4 ¹¹ are respectively the same.

In the general formula (3), R ⁴¹³ represents a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted aryl group having 6 to 20 carbon atoms, or the above general formula (4). foundation. R ⁴¹³ is preferably an alkyl group having 1 to 5 carbon atoms or a group represented by the general formula (4) that may have a substituent, more preferably an alkyl group having 1 to 3 carbon atoms or a group represented by the general formula (4), and further Preferably, it is an ethyl group or a group represented by the above-mentioned general formula (4). In one aspect 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 having 1 to 20 carbon atoms which may have a substituent, and * represents a bonding site to the general formula (3). In the general formula (4), Q ² is bonded to the general formula (3). The divalent hydrocarbon group with 1 to 20 carbon atoms that may have a substituent in Q ² and its preferred embodiments and the divalent hydrocarbon group with 1 to 20 carbon atoms that can have a substituent in the above-mentioned Q ¹ and its preferred embodiments same.

In the general formula (4), R ^1b represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms that may have a substituent, or an aryl group that may have a substituent group having 6 to 20 carbon atoms, and R ^2b represents a hydrogen atom, a cyano group, Nitro, trifluoromethyl, heterocyclic group, -C(O)-R ^7b or -SO ₂ -R ^8b ; R ^7b represents hydroxyl or -OR ^71b , R ^8b represents halogen atom, hydroxyl, -OR ^81b , -NR ^82b R ^83b or -R ^84b ; R ^71b and R ^81b ～R ^84b are the same or different, and represent a hydrogen atom, an alkyl group with a carbon number of 1 to 20 that may have a substituent or an alkyl group with a carbon number of 6 to 20 that may have a substituent Aryl of 20.

The preferred aspect of R ^1b is the same as the preferred aspect of R ¹ described above.

R ^2b is preferably a cyano group, a heterocyclic-containing group or -C(O)-R ^7b , more preferably a cyano group or -C(O)-OR ^71b . Preferred embodiments of R ^71b , R ^81b , R ^82b , R ^83b and R ^84b are the same as the preferred embodiments of R ⁷¹ , R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ described above, respectively.

In the general formula (4), R ^3b represents a hydrogen atom, a halogen atom, a cyano group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 20 carbon atoms.

R ^402b represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted aryl group having 6 to 20 carbon atoms, -NR ^406b R ^407b , -OR ^408b , cyano, -C(O)R ^409b , -OC(O)R ^410b or -C(O)OR ^411b , R ^404b to R ^411b are the same or different, and represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms that may have a substituent Or an aryl group having 6 to 20 carbon atoms which may have a substituent. A nitrogen-containing heterocycle of 4 to 8 members which may have a substituent may also be formed from the nitrogen atom to which R ^404b and R ^405b and R ^404b and R ^405b are bonded.

Preferred embodiments of R ^3b , R ^402b , R ^404b , R ^405a , R ^406b , R ^407b , R ^408b , R ^409b , R ^410b and R ^411b are the same as the above-mentioned R ³ , R ⁴⁰² , R ⁴⁰⁴ , R ⁴⁰⁵ , R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ have the same preferred aspects, respectively.

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

In the general formula (5), R ^2c represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a group containing a heterocyclic ring, -C(O)-R ^7c or -SO ₂ -R ^8c . R ^7c represents a hydroxyl group or -OR ^71c , and R ^8c represents a halogen atom, a hydroxyl group, -OR ^81c , -NR ^82c R ^83c or -R ^84c . R ^71c and R ^81c to R ^84c are the same or different, and represent a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 20 carbon atoms. R ^2c is preferably a cyano group, a heterocyclic ring-containing group or -C(O)-R ^7c , more preferably a cyano group or -C(O)-OR ^71c .

Preferred embodiments of R ^71c , R ^81c , R ^82c , R ^83c and R ^84c are the same as the preferred embodiments of R ⁷¹ , R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ described above, respectively.

In the general formula (5), R ^3c represents a hydrogen atom, a halogen atom, a cyano group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 20 carbon atoms.

R ^402c and R ^403c are the same or different, and represent a hydrogen atom, a halogen atom, an alkyl group with 1 to 20 carbon atoms that may have a substituent, an aryl group with 6 to 20 carbon atoms that may have a substituent, -NR ^406c R ^407c , -OR ^408c , cyano group, -C(O)R ^409c , -OC(O)R ^410c or -C(O)OR ^411c , R ^404c ~ R ^411c are the same or different, and represent a hydrogen atom and a carbon that may have 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. A nitrogen-containing heterocycle of 4 to 8 members which may have a substituent may also be formed from the nitrogen atom to which R ^404c and R ^405c and R ^404c and R ^405c are bonded.

Preferred embodiments of R ^3c , R ^402c , R ^403c , R ^404c , R ^405c , R ^406c , R ^407c , R ^408c , R ^409c , R ^410c and R ^411c are the same as the above-mentioned R ³ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ The preferred embodiments of R ⁴⁰⁵ , R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ are respectively the same.

In the general formula (5), R ⁵⁰¹ represents a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted aryl group having 6 to 20 carbon atoms, or a group represented by the above general formula (6) . R ⁵⁰¹ is preferably an alkyl group having 1 to 20 carbon atoms (such as methyl, ethyl, tert-butyl, cyclohexyl, 4-tert-butylcyclohexyl, 2,6-di- tributyl-4-methylcyclohexyl, etc.), aryl groups with 6 to 20 carbon atoms that may have substituents (such as phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, etc.), or a group represented by the above general formula (6). In one aspect of the present invention, R ⁵⁰¹ is preferably a group represented by the aforementioned general formula (6).

In the general formula (6), Q ³ represents a divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and * represents a bonding site to the general formula (5). In the general formula (6), Q ³ is bonded to the general formula (5). The divalent hydrocarbon group with 1 to 20 carbon atoms that may have a substituent in Q ³ and its preferred embodiments and the divalent hydrocarbon group with 1 to 20 carbon atoms that can have a substituent in the above-mentioned Q ¹ and its preferred embodiments same. In one aspect, Q ³ is more preferably a divalent aryl group represented by the above general formula (20) and s is 0.

In the general formula (6), R ^2d represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a group containing a heterocyclic ring, -C(O)-R ^7d or -SO ₂ -R ^8d . R ^7d represents a hydroxyl group or -OR ^71d , and R ^8d represents a halogen atom, a hydroxyl group, -OR ^81d , -NR ^82d R ^83d or -R ^84d . R ^71d and R ^81d to R ^84d are the same or different, and represent a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 20 carbon atoms.

R ^2d is preferably a cyano group, a heterocyclic-containing group or -C(O)-R ^7d , more preferably a cyano group or -C(O)-OR ^71d . Preferred embodiments of R ^71d , R ^81d , R ^82d , R ^83d and R ^84d are the same as the preferred embodiments of R ⁷¹ , R ⁸¹ , R ⁸² , R ⁸³ and R ⁸⁴ described above, respectively.

R ^3d represents a hydrogen atom, a halogen atom, a cyano group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 20 carbon atoms.

R ^402d and R ^403d are the same or different, and represent a hydrogen atom, a halogen atom, an alkyl group with 1 to 20 carbon atoms that may have a substituent, an aryl group with 6 to 20 carbon atoms that may have a substituent, -NR ^406d R ^407d , -OR ^408d , cyano group, -C(O)R ^409d , -OC(O)R ^410d or -C(O)OR ^411d , R ^404d to R ^411d are the same or different, and represent a hydrogen atom and a carbon that may have 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. A 4- to 8-membered nitrogen-containing heterocycle which may have a substituent can also be formed from the nitrogen atom to which R ^404d and R ^405d are bonded to R ^404d and R ^405d .

Preferred embodiments of R ^3d , R ^402d , R ^403d , R ^404d , R ^405d , R ^406d , R ^407d , R ^408d , R ^409d , R ^410d and R ^411d are the same as the above-mentioned R ³ , R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ The preferred embodiments of R ⁴⁰⁵ , R ⁴⁰⁶ , R ⁴⁰⁷ , R ⁴⁰⁸ , R ⁴⁰⁹ , R ⁴¹⁰ and R ⁴¹¹ are respectively the same.

In the compound (3), when R ⁴¹³ is a group represented by the general formula (4), in the general formula (1) Q ¹ is Q ² (a divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent) , and the group represented by the general formula (3) and the group represented by the general formula (4) are connected to the compound of the dimer structure on both sides through the Q ² . The group represented by the general formula (3) and the group represented by the general formula (4) include a methine structure, and both are structures that become a dye. Since the structure which becomes the dye becomes a dimer structure and the molecular weight increases, the compound is not easily sublimated, and it becomes a dye compound excellent in heat resistance. The compound (3) in which R ⁴¹³ is a group represented by the general formula (4) is a compound represented by the following general formula (3-1).

In the above formula (3-1), R ^1a , R ^2a , R ^3a , R ^402a , R ^404a and R ^405a , and Q ² , R ^1b , R ^2b , R ^3b , R ^402b , R ^404b and R ^405b are respectively The above has the same meaning.

In the compound (5), when R ⁵⁰¹ is a group represented by the general formula (6), in the general formula (1) Q ¹ is Q ³ (a divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent) , and the group represented by the general formula (5) and the group represented by the general formula (6) are connected to the compound of the dimer structure on both sides through the Q ³ . The group represented by the general formula (5) and the structure represented by the general formula (6) include a methine structure, and become a structure of a dye. Since the structure which becomes the dye becomes a dimer structure and the molecular weight increases, the compound is not easily sublimated, and it becomes a dye compound excellent in heat resistance.

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

In the above general formula (5-1), R ^2c , R ^3c , R ^402c , R ^403c , R ^404c and R ^405c , and Q ³ , R ^2d , R ^3d , R ^402d , R ^403d , R ^404d and R ^405d and The above has the same meaning.

As an example of a preferable aspect of the compound (1) of this invention, the compound C1-C5 etc. which were produced in an Example are mentioned, for example. Among them, compounds C1, C2, and C5 are preferred in terms of high light resistance. In terms of high heat resistance, compounds C1 to C3 are preferred. Compounds C1 to C5 are preferred in terms of high solubility in organic solvents. Compounds C1 to C5 are examples of compounds (3).

The manufacturing method of the compound (1) of this invention is not specifically limited, For example, it can manufacture by the following method. The production method of the compound of the present invention will be described below with an example of a synthesis method, but the production method of the compound (1) of the present invention is not limited to the following method. In addition, when the following reaction is carried out, functional groups other than the site may be protected by an appropriate protecting group in advance, and deprotected at an appropriate stage.

As an aspect of the present invention, when the compound represented by the general formula (1) is a compound represented by the following general formula (11) (compound (11)), 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 (dimer compound) in which m is 2 in the general formula (1). The compound (11) can also be described as an example of the compound in which R ⁴¹³ is a group represented by the general formula (4) in the compound (3). Hereinafter, compound (11) is obtained by subjecting compound (M21) to a dehydration condensation reaction with compound (M4).

In the above reaction formula, Q ^f represents a divalent linking group. Preferred aspects of R ^1f , R ^2f and these are the same as the preferred aspects of R ¹ , R ² and these described above, respectively. R ^402f , R ^404f and R ^405f and preferred aspects of these are the same as the above-mentioned R ⁴⁰² , R ⁴⁰⁴ and R ⁴⁰⁵ and preferred aspects of these, respectively. The 2-valent linking group in Q ^f is the same as the 2-valent linking group in Q ¹ . Q ^f is preferably a divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

The wavy line is a single bond, and indicates that the steric configuration relative to the double bond to which it is bonded is independently an E configuration or a Z configuration or a mixture of these. The following is also the same.

The compound (M4) can be obtained, for example, by reacting a dihalogenated alkyl compound with a compound (M1) represented by the following general formula (M1) 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.

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

Moreover, the compound (11) can also be obtained by carrying out the dehydration condensation of the compound (M1) and the compound (M21), followed by dimerization by alkoxylation.

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

In the above reaction formula, R ^2g and its preferred aspects are the same as the above-mentioned R ^2c and their preferred aspects, respectively. W ^g represents -C(O)-OQ ^g -OC(O)-, and Q ^g represents a divalent linking group. The divalent linking group in Q ^g is the same as the divalent linking group in Q ¹ . Q ^g is preferably a divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. R ^402g , R ^403g , R ^404g and R ^405g and preferred aspects of these are the same as the above-mentioned R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ and preferred aspects of these, respectively.

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

Moreover, the compound (12) can also be obtained by ^dehydrating and condensing the above-mentioned compound (M21) and the compound ( ^M2-1 ).

When the compound represented by the general formula (1) is a compound represented by the following general formula (13) (compound (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 is a monomer compound (m in the general formula (1) is 1). Compound (13) is also an example of a compound in which R ⁴¹³ in compound (3) represents a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 20 carbon atoms. Hereinafter, compound (13) is obtained by subjecting compound (M23) to a dehydration condensation reaction with compound (M2-2).

In the above formula, R ^402h , R ^403h , R ^404h and R ^405h and their preferred embodiments are the same as the above-mentioned R ⁴⁰² , R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ and their preferred embodiments, respectively. Preferred aspects of R ^1h , R ^2h and these are the same as the preferred aspects of R ¹ , R ² and these described above, respectively.

The isolation or purification of each product in the above-mentioned production method can be carried out by appropriately combining methods used in ordinary organic synthesis, such as filtration, extraction, washing, drying, concentration, crystallization, and various types of chromatography. In addition, the intermediate product may be used for the subsequent reaction without being particularly purified.

The compound (1) of the present invention usually has a maximum absorption wavelength at 360 to 430 nm. If it has a maximum absorption wavelength at 360~430nm, it can selectively absorb ultraviolet and blue light. The compound (1) of the present invention preferably has a maximum absorption wavelength at 370 to 420 nm, and more preferably has a maximum absorption wavelength at 380 to 400 nm. In addition, the compound (1) of the present invention also preferably has a gram absorption coefficient at 400 nm of 30 or more. The maximum absorption wavelength and the gram absorption coefficient can be measured by the methods described in the examples.

In addition, the compound (1) of the present invention generally has good solubility in organic solvents.

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 (for example, toluene, xylene, etc.), ketones (methyl ethyl ketone, acetone, cyclohexanone, 2-heptanone, 3-heptanone, etc.), ethers (eg propylene glycol monomethyl ether acetate, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether, etc.), esters (eg 3-ethoxypropionic acid) methyl ester, ethyl 3-ethoxypropionate, ethyl lactate, ethyl acetate, butyl acetate, methyl 3-methoxypropionate, etc.) and a mixed solvent of two or more of these.

The compound (1) is preferably dissolved in at least one of the above-mentioned organic solvents by 0.1 mass % or more, for example, preferably 0.1 mass % or more and 50 mass % or less, more preferably 1 mass % or more and 40 mass % or less. , more preferably 3 mass % or more and 30 mass % or less are dissolved. More preferably, the solubility to an organic solvent at 20°C is in this range. When the solubility to an organic solvent is in such a range, when the compound (1) of the present invention is used for the production of, for example, a blue light shielding lens, the manufacturability is good, which is preferable.

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, preferably 250 to 400°C. The thermal decomposition temperature can be measured by a thermogravimetric measuring device.

The compound (1) of the present invention usually has a maximum absorption wavelength at 360-430 nm, and can effectively absorb light of this wavelength. The compound (1) of the present invention can effectively absorb light in the vicinity of 400 nm. As an aspect, if the compound (1) of the present invention is a 2-6 polymer compound (m is 2-6 in the general formula (1)), heat resistance can be improved. Moreover, in the preferable aspect of this invention, the compound (1) of this invention is excellent in the solubility to an organic solvent. Therefore, the compound (1) of the present invention can be suitably used, for example, for blue light shielding materials such as blue light shielding lenses; ultraviolet absorbers; recording materials for recording media, and the like. Moreover, the compound (1) of this invention can also be used suitably as a pigment|dye etc. for optical filters, such as a color filter and a color conversion filter.

The compound (1) of the present invention can be prepared as a pigment composition by, for example, mixing with a resin or the like. The coloring composition can be suitably used as the coloring composition.

The said resin is not specifically limited, What is necessary is just to select a thermoplastic resin, a photocurable resin, a thermosetting resin, etc. suitably according to the application etc. of a coloring composition. For example, acrylic resin, polycarbonate resin, polystyrene resin, low density polyethylene resin, polypropylene resin, polyurethane resin, polyamide resin, polyacetal resin, polyphenylene sulfide resin, polyterephthalic acid can be mentioned. Ethylene glycol resin, polybutylene terephthalate resin, polycyclic olefin resin, polysilicon resin, polyether resin, fluorine resin, polysiloxane resin, polyester resin, epoxy resin, phenol resin, melamine resin, etc. resin. Only one type of these may be used, or two or more types may be used in combination.

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

The coloring matter composition may contain optional components other than the compound (1) of the present invention and the resin according to the application and the like. Examples of optional components include antioxidants, antifoaming agents, other dyes (dyes, pigments, etc.), infrared absorbers, polymerizable monomers, polymerization initiators, sensitizers, and the like. Moreover, ultraviolet absorbers other than compound (1) may be contained.

The manufacturing method of a coloring matter composition is not specifically limited, For example, what is necessary is just to mix the compound (1) of this invention, resin, and the arbitrary components mixed as needed.

The compound (1) of the present invention and the pigment composition containing the compound (1) of the present invention can be suitably used for the production of, for example, blue light shielding materials, ultraviolet absorbers, recording materials, and cosmetics.

Blue light shielding materials, ultraviolet absorbers, recording materials, and cosmetics containing the compound (1) of the present invention are also included in the present invention. The blue light shielding material, the ultraviolet absorber, the recording material, and the cosmetic only need to contain the compound (1), and the composition thereof is not particularly limited.

The blue light blocking material is not particularly limited, and examples thereof include blue light blocking films, blue light blocking lenses such as lenses for blue light blocking glasses and contact lenses, and the like. These blue light shielding materials may be blue light shielding molded bodies formed by molding a material containing the compound (1) of the present invention.

As a method of manufacturing a lens as an example of a blue light shielding material, for example, the following method can be adopted: kneading the compound (1) of the present invention in a transparent resin, and performing injection molding, compression molding, extrusion molding, etc. Various methods, such as the method of shaping|molding, and the method of forming the optical function layer containing the compound (1) of this invention on the following support.

UV absorbers can be used in various materials such as glass, plastic, fiber, paper, paint, ink, cosmetics, etc. The ultraviolet absorber can be used in a mixture of various materials, can be dispersed in the material, and can also be dissolved in the material. In addition, the ultraviolet absorber may be chemically or physically supported on various materials.

An optical disc etc. are mentioned as a recording material containing the compound (1) of this invention.

The compound (1) of this invention, and the dye for optical filters containing the compound (1) of this invention, and a dye composition can be suitably used for manufacture of an optical filter, for example.

The optical filter should just contain the compound (1) of this invention, for example, it may have a support similarly to the conventional one, and may have an optical functional layer etc. as needed. In the optical filter, the compound (1) of the present invention is preferably contained in the support or the optical functional layer.

The structures of the support and the optical functional layer are also not particularly limited. For example, the support is usually formed using a transparent resin. Examples of transparent resins include cyclic olefin-based resins, aromatic polyether-based resins, polyimide-based resins, fluoride polycarbonate-based resins, fluoride-based polyester-based resins, polycarbonate-based resins, and polyamides. (polyarylate) resin, polyarylate resin, polyether resin, polyether resin, polyparaphenylene resin, polyamide imide resin, polyethylene naphthalate (PEN ) series resins, fluorinated aromatic polymer series resins, (modified) acrylic series resins, epoxy series resins, and the like.

The manufacturing method of an optical filter is not specifically limited. For example, as a method of forming an optically functional layer containing the compound (1) of the present invention on a support, a method of dissolving or dispersing the compound (1) of the present invention, a binder resin, etc. in a solvent, and then using It is supported by coating methods such as dip coating, air knife coating, curtain coating, roller coating, wire bar coating, gravure coating, spin coating, and extrusion coating. A coating film is formed on the body. It does not specifically limit as said solvent, The said organic solvent etc. are mentioned.

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

Optical filters can be suitably used as optical filters such as color filters, color conversion filters, etc., for insect repellants (suppression of phototropic flying insects) for imaging devices, lighting fixtures, window glass, and the like. ) materials, etc.

[Example]

Hereinafter, although the Example which demonstrates this invention more concretely is shown, this invention is not limited to these Examples.

Hereinafter, the apparatus and measurement conditions used for measuring the physical properties of the obtained compound are as follows.

(GC-MS)

Gas chromatography mass spectrometer GCMS-QP2010Plus (EI method) manufactured by Shimadzu Corporation

(LC/MS)

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

<Production Example 1>

Synthesis of Compound IM3, Compound IM5 and Compound IM6

Compound IM3 was synthesized by the following method. The reaction formula is shown below.

(Synthesis of compound IM2)

In a 1L four-necked flask with a condenser tube and a thermometer, in the synthesis of 2-dimethylamino-4-hydroxy-6-methylpyrimidine described in Journal of American Chemical Society 1954, 76, 1879, the Compound IM1 was obtained in the same manner, except that N,N-dimethylguanidine sulfate was replaced with 1,1-dibutylguanidine hydrochloride obtained in the same manner as the method described in BE639386. Using compound IM1, in the same order as the method described in Journal of the Chemical Society 1957, 4845, methylation was performed by Reimer-Tiemann reaction to obtain compound IM2 (18.4 g, yield 69 %).

GC-MS: m/z=265([M] ⁺ )

(Synthesis of compound IM3)

In a 100mL four-neck flask with a condenser tube and a thermometer, compound IM2 (15.8g), iodoethane (14g) (manufactured by Tokyo Chemical Industry Co., Ltd.), potassium carbonate (14g), dimethylformamide The mixture of (DMF) (60 mL) was stirred at 70° C. for 3 hours, and then left to cool to room temperature. The reaction liquid was drained into water (300 mL), and extracted with toluene (300 mL). Compound IM3 (17.3 g, 99% yield) was obtained by concentrating the organic layer under reduced pressure.

GC-MS: m/z=293([M] ⁺ )

Compound IM5 and compound IM6 were synthesized by the following method. The reaction formula is shown below. In the following formula, the compound in which p is 5 is compound IM5, and the compound in which p is 6 is compound IM6.

(Synthesis of compound IM5)

Compound IM2 (2.7g), 1,5-dibromopentane (1.1g) (manufactured by Tokyo Chemical Industry Co., Ltd.), potassium carbonate (1.7g), DMF (20 mL) and stirred at 80°C for 2.5 hours. The reaction solution was discharged into water, and the precipitated crystals were filtered and taken out. The crystals were washed with methanol to obtain 2.1 g of compound IM5 (yield: 71%).

(Synthesis of compound IM6)

In the synthesis of compound IM5, except that 1,5-dibromopentane was replaced with 1,6-dibromohexane (manufactured by Tokyo Chemical Industry Co., Ltd.), compound IM6 was obtained in the same procedure (yield: 82 %).

<Production Example 2>

Compounds C1~C5 were synthesized. Compound C1 is a compound represented by the following formula.

Compounds C2 to C4 are compounds represented by the following formulae. In compound C2, R in the following formula is 2,6-di-tert-butyl-4-methylcyclohexyl. Compound C3 is in the following formula where R is 4-tert-butylcyclohexyl. Compound C4 wherein R in the following formula is a tert-butyl group.

Compound C5 is a compound represented by the following formula.

Reaction formulas for obtaining compounds C1 to C4 are shown below. Table 1 shows p in the formula and the corresponding compound. The structures of compound IM12, compound IM13 and compound IM14 used in the synthesis are shown below.

(Synthesis of Compound C1)

In a 50 mL four-neck flask with a condenser and a thermometer, compound IM6 (2.0 g), compound IM12 (2.0 g) synthesized in the same manner as the method described in Japanese Patent Laid-Open No. 2000-310841, and piperidine (0.06 g) were prepared. g) and ethanol (13 mL) were mixed and stirred at 75°C for 18 hours. It was left to cool to room temperature, the precipitated crystals were filtered and taken out, and washed with ethanol to obtain compound C1 (3.5 g, yield 93%).

LC-MS: m/z=1164 ([M+H] ⁺ )

(Synthesis of Compound C2)

Compound C2 was obtained in the same order (yield 81%) except that compound IM6 in the synthesis of compound C1 was replaced with compound IM5.

LC-MS: m/z=1150 ([M+H] ⁺ )

(Synthesis of Compound C3)

Compound C3 was obtained in the same order (yield 61%) except that compound IM6 in the synthesis of compound C1 was replaced by compound IM5, and compound IM12 was replaced by compound IM13 obtained in the same manner as in the synthesis of compound IM12.

LC-MS: m/z=1010([M+H] ⁺ )

(Synthesis of compound C4)

Compound C4 was obtained in the same procedure (yield 80%) except that compound IM6 in the synthesis of compound C1 was replaced by compound IM5, and compound IM12 was replaced by compound IM14 (manufactured by Tokyo Chemical Industry Co., Ltd.).

LC-MS: m/z=846 ([M+H] ⁺ )

(Synthesis of compound C5)

In a 25 mL four-neck flask with a condenser and a thermometer, a mixture of compound IM3 (1.2 g), IM12 (1.5 g), piperidine (0.02 g) and ethanol (4 mL) was stirred at 75°C for 1 hour. It was left to cool to room temperature, and the precipitated crystals were filtered and taken out. The obtained crystals were washed with ethanol to obtain 1.9 g of compound C5 (yield 80%). The reaction formula is shown below.

LC-MS: m/z=569 ([M+H] ⁺ )

<Comparative Production Example (Comparative Example Compound)>

(Synthesis of Comparative Example Compound Z1)

Comparative Example Compound Z1 was obtained in the same manner as in the method described in Japanese Patent Laid-Open No. 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 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 Laid-Open No. 2009-067973.

(Synthesis of Comparative Example Compound Z4)

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

The following evaluations were performed on the compounds obtained in each production example. The results are shown in Table 2.

<Spectral characteristic test>

The absorption spectrum of each compound in chloroform was measured, the maximum absorption wavelength (λmax) and the gram absorption coefficient at 400 nm were measured, and evaluated by the following criteria.

Measuring machine: UV-Vis Spectrophotometer V-560 manufactured by Nippon Spectrum Corporation

A: The gram absorption coefficient is 30 or more

B: The gram absorption coefficient is 20 or more and less than 30

C: The gram absorption coefficient is 10 or more and less than 20

D: The gram absorption coefficient is less than 10

<Light fastness test>

A light resistance test was performed on some of the compounds obtained in the production examples and comparative production examples. 10 mg of each compound was melted in 5 mL of a polymethacrylate 8 wt % toluene solution, applied on a glass substrate by a spin coating method, and dried to prepare a thin film having a thickness of 1.5 μm.

The produced film was continuously irradiated with light of a xenon lamp (142klux) for 96 hours, and the transmittance of the film before irradiation (0 hours) and after irradiation was measured with a spectrophotometer, and the remaining pigment was measured according to the following formula (1). Rate.

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

[Wherein, T ₀ is the transmittance before xenon lamp irradiation, T ₁ is the transmittance after xenon lamp irradiation, T ₀ and T ₁ are 0~1]

Furthermore, the so-called "transmittance" refers to the transmittance at the maximum absorption wavelength of each compound. The higher the residual rate of the dye, the less likely the compound is to be decomposed by light, and the higher the light resistance.

The light resistance was evaluated according to the following criteria.

A: The residual rate of pigment is more than 65%

B: The residual rate of pigment is more than 40% and less than 65%

C: The residual rate of pigment is more than 10% and less than 40%

D: The residual rate of pigment is less than 10%

<heat resistance>

For some of the compounds obtained in the production examples and comparative production examples, the weight loss due to thermal decomposition was measured using a thermogravimetric measuring apparatus TGA-50 manufactured by Shimadzu Corporation under the following measurement conditions, and the weight loss from the initial weight was 1 The temperature at % was measured as the decomposition initiation temperature.

(measurement conditions)

The measurement was carried out under the conditions of a sample amount of 5 mg, a heating rate of 10° C./min (maximum temperature reached 400° C.), a nitrogen atmosphere, and a flow rate of 10 mL/min.

The heat resistance was evaluated by the following criteria based on the decomposition initiation temperature.

A: Above 250℃

B: Above 210°C and less than 250°C

C: less than 210℃

<Solubility Test>

For some of the compounds obtained in the production examples, the solubility (% by weight) of p-toluene, methyl ethyl ketone (MEK) and propylene glycol monomethyl ether acetate (PGMEA) at 20° C. was measured by the following method.

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

A: 3 wt% or more dissolved

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

C: Only less than 1 wt% dissolved

According to the above results, the compounds C1 to C5 produced in each production example have maximum absorption wavelengths near 400 nm, and high gram absorption coefficients at 400 nm. These compounds can effectively absorb light around 400 nm. Compounds C1-C5 have good solubility in organic solvents. Moreover, the durability of these compounds is also favorable. For example, it was found that compounds C1 to C2 are excellent in light resistance, solubility, and heat resistance, and can also be suitably used as compounds such as dyes for blue light shielding materials. Although the compounds Z1-Z2 and Z4 of the comparative examples have maximum absorption wavelengths at 363-382 nm, the gram absorption coefficients at 400 nm are relatively low. The compounds of the present invention produced in each production example can absorb light around 400 nm more effectively than the compounds Z1 to Z2 and Z4 of the comparative examples. The comparative example compound Z3 has insufficient durability.

Claims (6)

A compound represented by the following general formula (3),

(In the general formula (3), R ^1a represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms that may have a substituent, or an aryl group that may have a substituent group having 6 to 20 carbon atoms, and R ^2a represents a hydrogen atom, a cyano group , nitro, trifluoromethyl, heterocyclic group, -C(O)-R ^7a or -SO ₂ -R ^8a ; R ^7a represents hydroxyl or -OR ^71a , R ^8a represents halogen atom, hydroxyl, -OR ^81a , -NR ^82a R ^83a or -R ^84a ; R ^71a and R ^81a to R ^84a are the same or different, and represent a hydrogen atom, an alkyl group with 1 to 20 carbon atoms that may have a substituent, or a carbon number 6 that may have a substituent group Aryl group of ~20; R ^3a represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group with 1 to 20 carbon atoms which may have a substituent or an aryl group with 6 to 20 carbon atoms that may have a substituent; R ^402a represents hydrogen Atom, halogen atom, alkyl group with 1 to 20 carbon atoms which may have a substituent, aryl group with 6 to 20 carbon atoms which may have a substituent, -NR ^406a R ^407a , -OR ^408a , cyano group, -C(O ) R ^409a , -OC(O)R ^410a or -C(O)OR ^411a , R ^404a ～R ^411a are the same or different, and represent a hydrogen atom, an alkyl group with 1 to 20 carbon atoms that may have a substituent or a substituent The aryl group of the carbon number of the base is 6~20; it can also form a nitrogen-containing heterocyclic ring with 4~8 members that can have substituents by the nitrogen atoms bonded by R ^404a and R ^405a and R ^404a and R ^405a ; R ⁴¹³ represents the following The base represented by the general formula (4),

(In the general formula (4), Q ² represents a divalent hydrocarbon group with 1 to 20 carbon atoms which may have a substituent, * represents a bonding site with the general formula (3); R ^1b represents a hydrogen atom, which may have a substituent Alkyl with 1 to 20 carbon atoms or aryl group with 6 to 20 carbon atoms that may have substituents, R ^2b represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a group containing a heterocyclic ring, -C(O )-R ^7b or -SO ₂ -R ^8b ; R ^7b represents a hydroxyl group or -OR ^71b , R ^8b represents a halogen atom, a hydroxyl group, -OR ^81b , -NR ^82b R ^83b or -R ^84b ; R ^71b and R ^81b ~R ^84b are the same or different, and represent a hydrogen atom, an alkyl group with a carbon number of 1 to 20 that may have a substituent or an aryl group with a carbon number of 6 to 20 that may have a substituent; R ^3b represents a hydrogen atom, a halogen atom, a cyano group, C 1-20 alkyl group with substituent or aryl group with carbon number 6-20 which may have substituent; R ^402b represents hydrogen atom, halogen atom, alkyl group with carbon number 1-20 which may have substituent, Aryl with 6-20 carbon atoms, -NR ^406b R ^407b , -OR ^408b , cyano group, -C(O)R ^409b , -OC(O)R ^410b or -C(O)OR ^411b , R ^404b ~ R ^411b are the same or different, and represent a hydrogen atom, an alkyl group with a carbon number of 1 to 20 that can have a substituent or an aryl group with a carbon number of 6 to 20 that can have a substituent; R ^404b and R ^405b can also be combined with The nitrogen atoms to which R ^404b and R ^405b are bonded form a 4- to 8-membered nitrogen-containing heterocycle which may have a substituent)). A compound represented by the following general formula (5),

(In the general formula (5), R ^2c represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a group containing a heterocyclic ring, -C(O)-R ^7c or -SO ₂ -R ^8c , and R ^7c represents Hydroxyl or -OR ^71c , R ^8c represents a halogen atom, hydroxyl, -OR ^81c , -NR ^82c R ^83c or -R ^84c , R ^71c and R ^81c to R ^84c are the same or different, represent a hydrogen atom, a carbon that may have a substituent Alkyl with 1 to 20 carbon atoms or aryl group with 6 to 20 carbon atoms that may have substituents; R ^3c represents hydrogen atom, halogen atom, cyano group, alkyl group with 1 to 20 carbon atoms that may have substituents or may have The aryl group with 6~20 carbon atoms of the substituent; R ^402c and R ^403c are the same or different, and represent a hydrogen atom, a halogen atom, an alkyl group with a carbon number of 1~20 that may have a substituent, and a carbon number 6 that may have a substituent Aryl group of ~20, -NR ^406c R ^407c , -OR ^408c , cyano group, -C(O)R ^409c , -OC(O)R ^410c or -C(O)OR ^411c , R ^404c ~R ^411c are the same or Different, represents a hydrogen atom, an alkyl group with a carbon number of 1 to 20 that may have a substituent, or an aryl group with a carbon number of 6 to 20 that may have a substituent; it can also be bonded by R ^404c and R ^405c and R ^404c and R ^405c The nitrogen atom of R ⁵⁰¹ represents a group represented by the following general formula (6),

(In the general formula (6), Q ³ represents a divalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, * represents a bonding site with the general formula (5); R ^2d represents a hydrogen atom, a cyano group, a nitro group , trifluoromethyl, group containing heterocyclic ring, -C(O)-R ^7d or -SO ₂ -R ^8d ; R ^7d represents hydroxyl or -OR ^71d , R ^8d represents halogen atom, hydroxyl, -OR ^81d , - NR ^82d R ^83d or -R ^84d ; R ^71d and R ^81d to R ^84d are the same or different, and represent a hydrogen atom, an alkyl group with 1 to 20 carbon atoms that may have a substituent, or a group of 6 to 20 carbon atoms that may have a substituent. Aryl; R ^3d represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group with 1 to 20 carbon atoms that may have a substituent or an aryl group with 6 to 20 carbon atoms that may have a substituent; R ^402d and R ^403d are the same or Different, it represents a hydrogen atom, a halogen atom, an alkyl group with 1 to 20 carbon atoms that may have a substituent, an aryl group with 6 to 20 carbon atoms that may have a substituent, -NR ^406d R ^407d , -OR ^408d , cyano group, -C(O)R ^409d , -OC(O)R ^410d or -C(O)OR ^411d , R ^404d to R ^411d are the same or different, and represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms that may have a substituent Or an aryl group with a carbon number of 6 to 20 that may have a substituent; a nitrogen-containing heterocyclic ring with 4 to 8 members that may have a substituent can also be formed from the nitrogen atoms bound by R ^404d and R ^405d and R ^404d and R ^405d ) ). The compound of claim 1 or 2, which is a pigment compound. A pigment composition comprising a compound represented by the following general formula (1),

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

(In the general formula (2), R ¹ represents a hydrogen atom, an alkyl group which may have a substituent or an aryl group which may have a substituent; R ² represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic ring-containing group the base, -C(O)-R ⁷ or -SO ₂ -R ⁸ ; R ⁷ represents hydroxyl or -OR ⁷¹ , R ⁸ represents halogen atom, hydroxyl, -OR ⁸¹ , -NR ⁸² R ⁸³ or -R ⁸⁴ ; R ⁷¹ and R ⁸¹ to R ⁸⁴ are the same or different, and represent a hydrogen atom, an alkyl group that may have a substituent or an aryl group that may have a substituent; R ³ represents a hydrogen atom, a halogen atom, a cyano group, an alkane that may have a substituent R ⁴⁰² and R ⁴⁰³ are the same or different, and represent a hydrogen atom, a halogen atom, an alkyl group that may have a substituent, an aryl group that may have a substituent, -NR ⁴⁰⁶ R ⁴⁰⁷ , -OR ⁴⁰⁸ , cyano group, -C(O)R ⁴⁰⁹ , -OC(O)R ⁴¹⁰ or -C(O)OR ⁴¹¹ , R ⁴⁰⁴ to R ⁴¹¹ are the same or different, and represent a hydrogen atom, an alkyl group which may have a substituent or An aryl group which may have a substituent; a nitrogen-containing heterocyclic ring with 4 to 8 members which may have a substituent may also be formed from the nitrogen atom to which R ⁴⁰⁴ and R ⁴⁰⁵ and R ⁴⁰⁴ and R ⁴⁰⁵ are bonded)). A blue light shielding molded body containing a compound represented by the following general formula (1),

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

(In the general formula (2), R ¹ represents a hydrogen atom, an alkyl group which may have a substituent or an aryl group which may have a substituent; R ² represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic ring-containing group the base, -C(O)-R ⁷ or -SO ₂ -R ⁸ ; R ⁷ represents hydroxyl or -OR ⁷¹ , R ⁸ represents halogen atom, hydroxyl, -OR ⁸¹ , -NR ⁸² R ⁸³ or -R ⁸⁴ ; R ⁷¹ and R ⁸¹ to R ⁸⁴ are the same or different, and represent a hydrogen atom, an alkyl group that may have a substituent or an aryl group that may have a substituent; R ³ represents a hydrogen atom, a halogen atom, a cyano group, an alkane that may have a substituent R ⁴⁰² and R ⁴⁰³ are the same or different, and represent a hydrogen atom, a halogen atom, an alkyl group that may have a substituent, an aryl group that may have a substituent, -NR ⁴⁰⁶ R ⁴⁰⁷ , -OR ⁴⁰⁸ , cyano group, -C(O)R ⁴⁰⁹ , -OC(O)R ⁴¹⁰ or -C(O)OR ⁴¹¹ , R ⁴⁰⁴ to R ⁴¹¹ are the same or different, and represent a hydrogen atom, an alkyl group which may have a substituent or An aryl group which may have a substituent; a nitrogen-containing heterocyclic ring with 4 to 8 members which may have a substituent may also be formed from the nitrogen atom to which R ⁴⁰⁴ and R ⁴⁰⁵ and R ⁴⁰⁴ and R ⁴⁰⁵ are bonded)). An ultraviolet absorber containing a compound represented by the following general formula (1),

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

(In the general formula (2), R ¹ represents a hydrogen atom, an alkyl group which may have a substituent or an aryl group which may have a substituent; R ² represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a heterocyclic ring-containing group the base, -C(O)-R ⁷ or -SO ₂ -R ⁸ ; R ⁷ represents hydroxyl or -OR ⁷¹ , R ⁸ represents halogen atom, hydroxyl, -OR ⁸¹ , -NR ⁸² R ⁸³ or -R ⁸⁴ ; R ⁷¹ and R ⁸¹ to R ⁸⁴ are the same or different, and represent a hydrogen atom, an alkyl group that may have a substituent or an aryl group that may have a substituent; R ³ represents a hydrogen atom, a halogen atom, a cyano group, an alkane that may have a substituent R ⁴⁰² and R ⁴⁰³ are the same or different, and represent a hydrogen atom, a halogen atom, an alkyl group that may have a substituent, an aryl group that may have a substituent, -NR ⁴⁰⁶ R ⁴⁰⁷ , -OR ⁴⁰⁸ , cyano group, -C(O)R ⁴⁰⁹ , -OC(O)R ⁴¹⁰ or -C(O)OR ⁴¹¹ , R ⁴⁰⁴ to R ⁴¹¹ are the same or different, and represent a hydrogen atom, an alkyl group which may have a substituent or An aryl group which may have a substituent; a nitrogen-containing heterocyclic ring with 4 to 8 members which may have a substituent may also be formed from the nitrogen atom to which R ⁴⁰⁴ and R ⁴⁰⁵ and R ⁴⁰⁴ and R ⁴⁰⁵ are bonded)).