JP7659249B2 - Compound - Google Patents

Description

The present invention relates to a compound that can be used as an ultraviolet absorber, an optical filter containing the compound, and an ultraviolet absorber.

Ultraviolet rays have strong energy and can, for example, damage the retina and cause eye diseases. Ultraviolet rays are also known to damage the skin. For this reason, compounds that can be used as ultraviolet absorbents are in demand. Patent Document 1 describes an ethylene compound that shows an absorption peak in the ultraviolet to purple region.

JP 2019-14707 A

Optical filters are used to cut light of specific wavelengths from light emitted from lighting devices, display devices, etc., and from natural light. Optical filters and various instruments and devices using them may be used in high-temperature environments. In addition, in the manufacture of optical filters, etc., kneading at high temperatures and heat treatment may be performed. For this reason, the development of an ultraviolet absorber with good heat resistance is desired. In addition, when an ultraviolet absorber is mixed into an optical filter, etc., an ultraviolet absorber with low absorption in the visible light region is desired to suppress coloring. In addition, if the ultraviolet absorber has low ultraviolet absorbance, it is necessary to add a large amount to effectively reduce ultraviolet light, so a compound with high absorbance in the ultraviolet region is desired. The compound of Patent Document 1 shows an absorption peak in the ultraviolet to purple region, but there is room for improvement to more efficiently absorb light in the ultraviolet region and to absorb less in the visible light region.

The present invention aims to provide a compound that has good heat resistance, efficiently absorbs ultraviolet light, particularly light in the wavelength range of 370 to 380 nm, and has low absorption in the visible light range.

The present inventors conducted extensive research to solve the above problems and discovered that the compound represented by the following general formula (1) has good heat resistance, has an absorption maximum in the wavelength region of 370 to 380 nm, and has high absorbance, making it possible to efficiently absorb light of this wavelength, while also exhibiting low absorption in the visible light region.

That is, the compound of the present invention is a compound represented by the following general formula (1):

In general formula (1), R ^1a and R ^2a each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent;
R ^3a represents a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, the alkyl group in which one or more of -CH ₂ - constituting the alkyl group are substituted with at least one selected from the group consisting of an unsaturated bond, -O-, -S-, -CO-, -CO ₂ -, -OCO-, -NR ^6a -, -CONR ^6a -, -NR ^6a CO- and an arylene group, or a group represented by general formula (2),
R ^4a represents a nitro group, a cyano group, a trifluoromethyl group, a -COR ^7a group, a -CO ₂ R ^7a group, a -CONR ^7a R ^7aa group or a -SO ₂ R ^7a group;
R ^5a represents a cyclic alkyl group which may have a substituent or a group represented by general formula (3),
R ^6a represents a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent;
R ^7a and R ^7aa each independently represent a hydrogen atom, an optionally substituted linear, branched or cyclic alkyl group, or an optionally substituted aryl group.

(In general formula (2), L ^1a represents a group in which one hydrogen atom has been removed from a linear, branched or cyclic alkyl group which may have a substituent, or a group in which one or more of the -CH ₂ - constituting the alkyl group in the alkyl group are substituted with at least one selected from the group consisting of an unsaturated bond, -O-, -S-, -CO-, -CO ₂ -, -OCO-, -NR ^6b -, -CONR ^6b -, -NR ^6b CO- and an arylene group, and one hydrogen atom has been removed from the group; R ^6b represents a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent;
T ^1a represents a group represented by general formula (4).
* indicates the bonding site with the nitrogen atom in general formula (1).

In general formula (4), R ^1b and R ^2b each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent;
R ^4b represents a nitro group, a cyano group, a trifluoromethyl group, a -COR ^7b group, a -CO ₂ R ^7b group, a -CONR ^7b R ^7bb group or a -SO ₂ R ^7b group;
R ^5b represents a cyclic alkyl group which may have a substituent;
R ^7b and R ^7bb each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent.
* indicates the bonding site with L ^1a in general formula (2).

(In general formula (3), L ^2a represents a group in which one hydrogen atom has been eliminated from a cyclic alkyl group which may have a substituent, or a group in which one or more of the -CH ₂ - constituting the alkyl group in the cyclic alkyl group are substituted with at least one selected from the group consisting of an unsaturated bond, -O-, -S-, -CO-, -CO ₂ -, -OCO-, -NR ^6c , -CONR ^6c -, -NR ^6c CO- and an arylene group, and one hydrogen atom has been eliminated from the group; R ^6c represents a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent;
^T2a represents a hydrogen atom or a group represented by formula (5).
* indicates the bonding site with the oxygen atom in general formula (1).

In general formula (5), R ^1c and R ^2c each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent;
R ^3c represents a linear, branched or cyclic alkyl group which may have a substituent, or the alkyl group in which one or more of -CH ₂ - constituting the alkyl group are substituted with at least one selected from the group consisting of an unsaturated bond, -O-, -S-, -CO-, -CO ₂ -, -OCO-, -NR ^6d -, -CONR ^{6d -} , -NR ^6d CO- and an arylene group;
R ^4c represents a nitro group, a cyano group, a trifluoromethyl group, a -COR ^7c group, a -CO ₂ R ^7c group, a -CONR ^7c R ^7cc group, or a SO ₂ R ^7c group;
R ^6d represents a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent;
R ^7c and R ^7cc each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent.
* indicates the bonding site with ^L2a in general formula (3).

In the present invention, it is preferable that R ^4a in general formula (1) represents a cyano group.
In the present invention, it is preferred that R ^1a and R ^2a in general formula (1) each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms, R ^5a represents a cyclohexyl group which may have a substituent, a norbornyl group which may have a substituent, an adamantyl group which may have a substituent, or a group represented by general formula (3), L ^2a in general formula (3) represents a group in which one hydrogen atom has been eliminated from a cyclic alkyl group which may have a substituent, T ^2a represents a group represented by general formula (5), and R ^1c and R ^2c in general formula (5) each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms, R ^4c represents a cyano group, and R ^3c represents a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms.

The optical filter of the present invention is characterized by containing the compound of the present invention.
The ultraviolet absorbent of the present invention is characterized by containing the compound of the present invention.

The present invention provides a compound that has good heat resistance, efficiently absorbs ultraviolet light, particularly light in the wavelength range of 370 to 380 nm, and has low absorption in the visible light range. The compound of the present invention can be suitably used as an ultraviolet absorber, etc.

The compound of the present invention is a compound represented by the following general formula (1). The compound represented by the following general formula (1) is also referred to as compound (1) in this specification.

(In general formula (1), R ^1a and R ^2a each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent; R ^3a represents a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, a group in which one or more of -CH ₂ - constituting the alkyl group are substituted with at least one selected from the group consisting of an unsaturated bond, -O-, -S-, -CO-, -CO ₂ -, -OCO-, -NR ^6a -, -CONR ^6a -, -NR ^6a CO- and an arylene group, or a group represented by general formula (2); R ^4a represents a nitro group, a cyano group, a trifluoromethyl group, a -COR ^7a group, a -CO ₂ R ^7a group, a -CONR ^7a R ^7aa group or a -SO ₂ R ^7a group; R ^{R 5a} represents a cyclic alkyl group which may have a substituent or a group represented by general formula (3); R ^6a represents a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent; and R ^7a and R ^7aa each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent.

(In general formula (2), L ^1a represents a group in which one hydrogen atom has been removed from a linear, branched or cyclic alkyl group which may have a substituent, or a group in which one hydrogen atom has been removed from a group in which one or more of the -CH ₂ - constituting the alkyl group in the alkyl group are substituted with at least one selected from the group consisting of an unsaturated bond, -O-, -S-, -CO-, -CO ₂ -, -OCO-, -NR ^6b -, -CONR ^6b -, -NR ^6b CO- and an arylene group; R ^6b represents a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent; T ^1a represents a group represented by general formula (4). * represents a bonding site with the nitrogen atom in general formula (1).)

(In general formula (4), R ^1b and R ^2b each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent; R ^4b represents a nitro group, a cyano group, a trifluoromethyl group, a -COR ^7b group, a -CO ₂ R ^7b group, a -CONR ^7b R ^7bb group, or a -SO ₂ R ^7b group; R ^5b represents a cyclic alkyl group which may have a substituent; R ^7b and R ^7bb each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent. * represents a bonding site with L ^1a in general formula (2).)

(In general formula (3), L ^2a represents a group in which one hydrogen atom has been eliminated from a cyclic alkyl group which may have a substituent, or a group in which one or more of the -CH ₂ - constituting the alkyl group in the cyclic alkyl group are substituted with at least one selected from the group consisting of an unsaturated bond, -O-, -S-, -CO-, -CO ₂ -, -OCO-, -NR ^6c , -CONR ^6c -, -NR ^6c CO- and an arylene group and one hydrogen atom has been eliminated from the group; R ^6c represents a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent; T ^2a represents a hydrogen atom or a group represented by general formula (5). * represents a bonding site with the oxygen atom in general formula (1).)

(In general formula (5), R ^1c and R ^2c each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent; R ^3c represents a linear, branched or cyclic alkyl group which may have a substituent, or the alkyl group in which one or more of -CH ₂ - constituting the alkyl group are substituted with at least one selected from the group consisting of an unsaturated bond, -O-, -S-, -CO-, -CO ₂ -, -OCO-, -NR ^6d -, -CONR ^6d -, -NR ^6d CO- and an arylene group; R ^4c represents a nitro group, a cyano group, a trifluoromethyl group, a -COR ^7c group, a -CO ₂ R ^7c group, a -CONR ^7c R ^7cc group or a SO ₂ R ^7c group; R ^6d represents a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent, and R ^7c and R ^7cc each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or an aryl group which may have a substituent. * represents the bonding site with L ^2a in general formula (3).

In the present invention, examples of the linear, branched or cyclic alkyl group which may have a substituent include linear, branched or cyclic alkyl groups which may have a substituent and have 1 to 20 carbon atoms. In this specification, the number of carbon atoms of a group which may have a substituent refers to the number of carbon atoms of the entire group including the substituent.
Examples of the linear, branched or cyclic alkyl group include linear alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, and an n-pentadecyl group;
Isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-methylbutyl group, 1-methylbutyl group, neopentyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3,3-dimethylbutyl group, 2,3-dimethylbutyl group, 1,3-dimethylbutyl group, 2,2-dimethylbutyl group, 1,2-dimethylbutyl group, 1,1-dimethylbutyl group, 3-ethylbutyl group, 2-ethylbutyl group, 1-ethylbutyl group, 1,1,2-trimethylpropyl group, 1-ethyl-2-methylpropyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group branched-chain alkyl groups such as 1-ethylpentyl group, 2,4-dimethylpentyl group, 2-ethylhexyl group, 2,5-dimethylhexyl group, 2,5,5-trimethylpentyl group, 2,4-dimethylhexyl group, 2,2,4-trimethylpentyl group, 1,1-dimethylhexyl group, 1,1,3,3-tetramethylbutyl group, 3,5,5-trimethylhexyl group, 4-ethyloctyl group, 4-ethyl-4,5-dimethylhexyl group, 1,3,5,7-tetramethyloctyl group, 4-butyloctyl group, 6,6-diethyloctyl group, 6-methyl-4-butyloctyl group, 3,5-dimethylheptadecyl group, 2,6-dimethylheptadecyl group, 2,4-dimethylheptadecyl group, and 2,2,5,5-tetramethylhexyl group;
Examples of the cyclic alkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a norbornyl group, and an adamantyl group.

The substituent in the linear, branched or cyclic alkyl group which may have a substituent is not particularly limited, and examples thereof include a monocyclic or polycyclic aromatic ring group having 6 to 10 carbon atoms (e.g., a phenyl group, a naphthyl group, etc.), a linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms, an amino group, a mono- or di-alkylamino group (the alkyl group has 1 to 8 carbon atoms), a halogen atom, a cyano group, a hydroxy group, a nitro group, a carboxy group, an alkoxycarbonyl group having 1 to 8 carbon atoms, an acyl group having 2 to 10 carbon atoms (e.g., 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, anisoyl group, a naphthoyl group, etc.), an acyloxy group having 2 to 10 carbon atoms, and an alkenyl group having 2 to 10 carbon atoms (e.g., a vinyl group, a 1-propenyl group, an allyl group, a butenyl group, a styryl group, etc.).
Examples of the substituent in the cyclic alkyl group which may have a substituent include linear or branched alkyl groups having 1 to 10 carbon atoms (e.g., methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, 2-methylbutyl group, 1-methylbutyl group, neopentyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, etc.).
When the alkyl group has two or more substituents, the respective substituents may be the same or different.

In the present invention, examples of the aryl group which may have a substituent include an aryl group having 6 to 20 carbon atoms which may have a substituent. The aryl group is not particularly limited, and examples thereof include monocyclic aromatic hydrocarbon groups such as a phenyl group, and polycyclic aromatic hydrocarbon groups such as a naphthyl group, anthracenyl group, naphthacenyl group, pentacenyl group, phenanthrenyl group, and pyrenyl group.
The substituent in the aryl group which may have a substituent is not particularly limited, and examples thereof include 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 mono- or di-alkylamino group (wherein the alkyl group has 1 to 8 carbon atoms), a halogen atom, a cyano group, a hydroxy group, a nitro group, a halogenated hydrocarbon group having 1 to 8 carbon atoms, a carboxy group, an alkoxycarbonyl group having 1 to 8 carbon atoms, etc. A linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, or a halogen atom is preferred.
As the aryl group having 6 to 20 carbon atoms which may have a substituent, for example, a phenyl group which may be substituted with an alkyl group (for example, a phenyl group, a 3-methylphenyl group, a 2,6-dimethylphenyl group, etc.) is preferable.
When the aryl group has two or more substituents, the respective substituents may be the same or different.

In general formula (1), R ^1a and R ^2a each independently represent preferably a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms, more preferably a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, further preferably a hydrogen atom, a methyl group, or an ethyl group, and particularly preferably a methyl group.

R ^3a is preferably a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms which may have a substituent, or a group represented by the general formula (2).
As the linear, branched or cyclic alkyl group having 1 to 8 carbon atoms which may have a substituent in R ^3a , a linear or branched alkyl group having 1 to 8 carbon atoms which may have a substituent is preferable, a methyl group or an ethyl group which may have a substituent is more preferable, a methyl group, an ethyl group, a phenylmethyl group or a phenylethyl group is further preferable, and a methyl group or a phenylmethyl group is particularly preferable. R ^6a preferably represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent.

In general formula (2), L ^1a preferably represents a group in which one hydrogen atom has been removed from a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms which may have a substituent, or a group in which one hydrogen atom has been removed from a group in which one or more of the -CH ₂ - constituting the alkyl group are substituted with at least one selected from the group consisting of an unsaturated bond, -O-, -S-, _-CO- , -CO ² -, -OCO-, -NR ^6b -, -CONR 6b -, -NR ^6b CO- and an arylene group. R ^6b preferably represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent. L ^1a is more preferably a group in which one hydrogen atom has been eliminated from a linear or branched alkyl group having 1 to 10 carbon atoms (preferably 1 to 8 carbon atoms), and even more preferably a group in which one hydrogen atom has been eliminated from a linear alkyl group having 1 to 10 carbon atoms.

In the group represented by general formula (4), R ^1b and R ^2b each independently represent preferably a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms, more preferably a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, further preferably a hydrogen atom, a methyl group, or an ethyl group, and particularly preferably a methyl group.
It is preferable that R ^7b and R ^7bb each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or an optionally substituted aryl group having 6 to 20 carbon atoms.
In the group represented by formula (4), R ^4b preferably represents a cyano group.

In the group represented by general formula (4), R ^5b is preferably a cyclic alkyl group having 6 to 20 carbon atoms which may have a substituent, more preferably a cyclohexyl group which may have a substituent, a norbornyl group which may have a substituent, an adamantyl group which may have a substituent, or the like, and even more preferably a cyclohexyl group, a 4-tert-butylcyclohexyl group, a 2,6-di-tert-butyl-4-methylcyclohexyl group, or the like.

In one embodiment, an example of the group represented by general formula (4) includes a group represented by the following formula (4-1) or formula (4-2). In formulas (4-1) and (4-2), * indicates a bonding site with L ^1a in general formula (2). In one embodiment, the group represented by general formula (4) is preferably a group represented by the following formula (4-1) or a group represented by the following formula (4-2).

In general formula (1), R ^4a preferably represents a cyano group. ^{R 7a} and R ^7aa each preferably represent, independently, a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or an optionally substituted aryl group having 6 to 20 carbon atoms.

In general formula (1), the optionally substituted cyclic alkyl group for R ^5a is preferably a optionally substituted cyclic alkyl group having 6 to 20 carbon atoms, and more preferably a cyclohexyl group optionally having a substituent, a norbornyl group optionally having a substituent, or an adamantyl group optionally having a substituent.
In one embodiment, R ^5a preferably represents a cyclohexyl group which may have a substituent, a norbornyl group which may have a substituent, an adamantyl group which may have a substituent, or a group represented by general formula (3). The cyclic alkyl group which may have a substituent in R ^5a is more preferably a cyclohexyl group, a 4-tert-butylcyclohexyl group, a 2,6-di-tert-butyl-4-methylcyclohexyl group, a 1- or 2-adamantyl group, or an isobornyl group.

In the general formula (3), it is preferable that L ^2a represents a group in which one hydrogen atom has been eliminated from a cyclic alkyl group which may have a substituent. In one embodiment, it is preferable that T ^2a is a hydrogen atom. The cyclic alkyl group which may have a substituent in L ^2a is more preferably a cyclopentyl group which may have a substituent, a cyclohexyl group which may have a substituent, a cycloheptyl group which may have a substituent, or a cyclooctyl group which may have a substituent, and more preferably a cyclohexyl group, a 4-tert-butylcyclohexyl group, or a 2,6-di-tert-butyl-4-methylcyclohexyl group. It is preferable that R ^6c represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aryl group having 6 to 20 carbon atoms which may have a substituent.

In general formula (5), R ^1c and R ^2c each independently represent preferably a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms, more preferably a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, further preferably a hydrogen atom, a methyl group, or an ethyl group, and particularly preferably a methyl group.
R ^3c preferably represents a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms, more preferably a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, and even more preferably a methyl group or an ethyl group. R ^4c preferably represents a cyano group. R ^6d preferably represents a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms.

In one embodiment, the group represented by formula (5) is preferably a group represented by the following formula (5-1): In formula (5-1), * indicates the bonding site with L ^2a in formula (3).

In this specification, the wavy lines in general formulas (1), (4), (5), etc.

indicates that the configuration of a single bond about the double bond to which it is attached is E or Z, or a mixture of both.

As an example of a preferred embodiment of the compound of the present invention, there is a compound in which, in the general formula (1), R ¹ and R ² are methyl groups, R ³ is a methyl group, a phenylmethyl group, a group represented by the above formula (4-1) or a group represented by the formula (4-2), R ⁴ is a cyano group, and R ⁵ is a cyclohexyl group, a 4-tert-butylcyclohexyl group, a 2,6-di-tert-butyl-4-methylcyclohexyl group, a 1- or 2-adamantyl group, an isobornyl group, or a group represented by the above formula (5-1). Examples of such compounds include compounds (1-1) to (1-10) described in the examples. Among them, a compound in which R ³ is a methyl group or a group represented by the above formula (4-2) and R ⁵ is a 2,6-di-tert-butyl-4-methylcyclohexyl group is more preferred because of its excellent heat resistance and light resistance.

When the compound of the present invention has geometric isomerism, the present invention includes all of the geometric isomers. In addition, when the compound of the present invention has one or more asymmetric carbon atoms, the present invention includes compounds in which each asymmetric carbon atom has the R configuration, the S configuration, and any combination thereof. In addition, the present invention includes all of the racemic compounds, racemic mixtures, single enantiomers, and diastereomeric mixtures thereof.

The method for producing the compound of the present invention will be described below with an example of a synthesis method, but the method for producing the compound of the present invention is not limited to the method described below. In addition, when carrying out the reaction described below, functional groups other than the relevant site may be protected in advance with an appropriate protecting group as necessary, and the functional groups may be deprotected at an appropriate stage.

The method for producing the compound represented by general formula (1) is not particularly limited, and the compound can be obtained by a method utilizing a well-known general method. For example, compound (1) can be synthesized from a compound represented by general formula (6a) (compound (6a)) and a compound represented by general formula (7a) (compound (7a)) by the reaction shown below.

In the above formula, R ^1a , R ^2a , R ^3a , R ^4a and R ^5a and preferred embodiments thereof are the same as those in the general formula (1). ^Xa represents a monovalent anion. N(Ac)Ph represents an acetanilide group. The same applies below.

The compound represented by the general formula (1) in which R ^3a is a group represented by the general formula (2) can be synthesized from the compound represented by the general formula (6b) (compound (6b)), compound (7a) and compound represented by the general formula (7b) (compound (7b)) by the reaction shown below. The compound represented by the following general formula (1b) is a compound represented by the general formula (1) in which R ^3a is a group represented by the general formula (2).

In the above formula, R ^1a , R ^2a , R ^4a and R ^5a and preferred embodiments thereof are the same as those in formula (1). ^{L 1a} and preferred embodiments thereof are the same as those in formula (2). R ^1b , R ^2b , R ^4b and R ^5b and preferred embodiments thereof are the same as those in formula (4).
^Xa and ^Xb each independently represent a monovalent anion.

A compound in which R ^5a in general formula (1) is a group represented by general formula (3) (a compound represented by general formula (1c) below) can be synthesized from compound (6a), a compound represented by general formula (6c) (compound (6c)), and a compound represented by general formula (7c) (compound (7c)) by, for example, the reaction shown below. The compound represented by general formula (1c) below is an example of a compound in which R ^5a in general formula (1) is a group represented by general formula (3).

In the above formula, R ^1a , R ^2a , R ^3a and R ^4a and preferred embodiments thereof are the same as those in formula (1). L ^2a and preferred embodiments thereof are the same as those in formula (3). R ^1c , R ^2c , R ^3c and R ^4c and preferred embodiments thereof are the same as those in formula (5).
^Xa and ^Xc each independently represent a monovalent anion.

Examples of the monovalent anion in X ^a , X ^b and X ^c include halide ions such as a fluoride ion, a chloride ion, a bromide ion and an iodide ion; a tosylate ion; and the like.

The above compounds (6a), (6b) and (6c) can be obtained by reacting an alkyl halide with 2,4,4-trialkyloxazoline to form an alkylated compound, and then reacting the resulting compound with diphenylformamidine. Compounds (7a) and (7b) can be obtained, for example, by the method described in US Pat. No. 6,271,410 B1. Compound (7c) can be obtained, for example, by the method described in Macromolecules, 1992, 25 (22), pp. 6055-6058.

The conditions for reacting the compounds (6a) and (7a), the conditions for reacting the compounds (6b), (7a) and (7b), and the conditions for reacting the compounds (6a), (6c) and (7c) are not particularly limited. The reaction is usually carried out in a solvent in the presence of a base. The base is not particularly limited, and examples thereof include inorganic bases such as alkali metal carbonates such as sodium carbonate and potassium carbonate; and organic bases such as triethylamine, diisopropylethylamine, and DBU (diazabicycloundecene).
The solvent is not particularly limited as long as it is inert to the reaction, and examples thereof include methanol, ethanol, propanol, butanol, pentanol, hexanol, acetone, toluene, xylene, dimethylformamide, N-methylmorpholine, dimethylsulfoxide, dimethylacetamide, pyridine, and tetrahydrofuran.
The reaction temperature may be from 5 to 100° C., and preferably from 10 to 50° C. The reaction time may be from 0.5 to 48 hours, and preferably from 1 to 24 hours.

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

The compounds of the present invention usually have a maximum absorption wavelength (λmax) of 370 to 380 nm. This allows them to effectively absorb ultraviolet light. The maximum absorption wavelength of the compounds of the present invention can be determined, for example, as the wavelength of the maximum absorption peak obtained by measuring the absorption spectrum of a chloroform solution of the compound using a UV-visible spectrophotometer. The compounds of the present invention preferably have a maximum absorption wavelength of 375 to 380 nm.

The compound of the present invention preferably has a gram absorption coefficient of 100 or more, more preferably 120 or more, at the absorption maximum wavelength when measured in a chloroform solution. If the gram absorption coefficient at the absorption maximum wavelength is 100 or more, light of a wavelength near the absorption maximum wavelength can be absorbed more effectively. The gram absorption coefficient can be determined by the method described in the Examples.

The compound of the present invention preferably has a half-width of less than 20 nm.
In this specification, the half-width is a value indicating the steepness of the absorption spectrum represented by the following formula.
Half width = λ _1/2 - λ _max
In the above formula, λ _max represents the maximum absorption wavelength in the range of 350 to 800 nm in a chloroform solution, and λ _1/2 represents the wavelength at which the absorbance at that wavelength is half that at λ _max and λ _1/2 >λ _max .
The smaller the half-width, the steeper the absorption spectrum becomes on the visible light side, and coloring can be suppressed.
When the half-width is less than 20 nm, light having a wavelength near the maximum absorption wavelength can be selectively absorbed. Also, since the absorption in the visible light region is small, coloration can be effectively suppressed. The compound of the present invention more preferably has a half-width of 17 nm or less, even more preferably 15 nm or less, and particularly preferably less than 15 nm.
The half-width can be determined, for example, from the maximum absorption peak obtained by measuring the absorption spectrum of a chloroform solution of the compound using an ultraviolet-visible spectrophotometer.

The compound of the present invention is preferably a compound that is soluble in an organic solvent.
Examples of the organic solvent include aromatic hydrocarbons (e.g., toluene, xylene, etc.), ketones (methyl ethyl ketone, acetone, cyclohexanone, 2-heptanone, 3-heptanone, etc.), ethers (e.g., propylene glycol monomethyl ether acetate, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether, etc.), esters (e.g., methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl lactate, ethyl acetate, butyl acetate, methyl 3-methoxypropionate, etc.), and mixed solvents of two or more of these.
The compound of the present invention is preferably dissolved in at least one of the organic solvents at 0.1% by weight or more, for example, preferably dissolved at 0.1% by weight or more and 50% by weight or less, more preferably dissolved at 1% by weight or more and 40% by weight or less, and even more preferably dissolved at 3% by weight or more and 30% by weight or less. More preferably, the solubility in the organic solvent at 20° C. is in such a range. When the solubility in the organic solvent is in such a range, the compound of the present invention is preferably used for, for example, the production of an optical filter, because the manufacturability is good.

The compound of the present invention has good heat resistance. The compound of the present invention preferably has a thermal decomposition temperature of 205°C or higher, more preferably 210°C or higher, for example, 250 to 400°C. The thermal decomposition temperature can be measured using a thermogravimetric measuring device.

The compound of the present invention has an absorption wavelength of 370 to 380 nm, can efficiently absorb light of this wavelength, and has good heat resistance. Therefore, the compound of the present invention is suitable for use in, for example, optical filters. Only one type of compound of the present invention may be used, or two or more types may be used. For example, when the compound of the present invention is used in an optical filter, ultraviolet rays can be selectively and effectively reduced.

The compound of the present invention can be made into a resin composition, for example, by mixing with a resin.
The resin is not particularly limited, and may be appropriately selected from thermoplastic resins, photocurable resins, thermosetting resins, etc., depending on the application of the resin composition. For example, acrylic resins, polycarbonate resins, polystyrene resins, low-density polyethylene resins, polypropylene resins, polyurethane resins, polyamide resins, polyacetal resins, polyphenylene sulfide resins, polyethylene terephthalate resins, polybutylene terephthalate resins, polycycloolefin resins, polysulfone resins, polyethersulfone resins, fluororesins, silicone resins, polyester resins, epoxy resins, phenolic resins, melamine resins, and other resins. These may be used alone or in combination of two or more.

The amount of the compound of the present invention in the resin composition is, for example, preferably 0.001 to 50% by weight, and more preferably 0.01 to 40% by weight, of the total solid content of the resin composition.

The resin composition may contain optional components other than the compound of the present invention and the resin, depending on the application, etc. Examples of optional components include antioxidants, defoamers, colorants (dyes, pigments, etc.), infrared absorbers, polymerizable monomers, polymerization initiators, sensitizers, etc. In addition, the resin composition may contain an ultraviolet absorber other than the compound of the present invention.
The method for producing the resin composition is not particularly limited, and for example, the compound of the present invention and the resin, as well as any optional components that are added as desired, may be mixed together.
The compound of the present invention and a resin composition containing the compound of the present invention are suitably used for producing an optical filter, for example. The optical filter containing the compound of the present invention also constitutes the present invention.

The optical filter may contain the compound of the present invention, and the configuration of the optical filter is not particularly limited. For example, like conventional optical filters, the optical filter may have at least a support, and may have various functional layers such as an adhesive layer, an optical functional layer, an anti-reflection layer, and a hard coat layer, as necessary. In the optical filter, the compound of the present invention may be contained in either the support or the various functional layers, and is preferably contained in the support or the optical functional layer, for example. The size and shape of the optical filter are not particularly limited, and may be appropriately selected depending on the application, etc.

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

The method for producing an optical filter is not particularly limited. For example, a method for forming an optical functional layer containing the compound of the present invention on a support includes dissolving or dispersing the compound of the present invention and a binder resin in a solvent, and then forming a coating film on the support by a coating method such as dip coating, air knife coating, curtain coating, roller coating, wire bar coating, gravure coating, spin coating, or extrusion coating. The above-mentioned solvent is not particularly limited, and an organic solvent, etc. can be used.

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

The optical filters can be suitably used as, for example, ultraviolet shielding filters, color filters, color conversion filters, light absorption filters, and other optical filters in liquid crystal displays, organic electroluminescence displays, imaging devices, lighting equipment, window glass, and other insect repellent materials (to prevent the arrival of phototactic flying insects).

The compound of the present invention and the resin composition containing the compound of the present invention are also suitable for use in the manufacture of, for example, ultraviolet shielding materials, ultraviolet absorbers, recording materials, and cosmetics. The ultraviolet absorbers containing the compound of the present invention are also part of the present invention.
The ultraviolet shielding material, ultraviolet absorbing agent, recording material, and cosmetic are not particularly limited as long as they contain the compound of the present invention. The compound of the present invention may be used alone or in combination of two or more kinds.
The ultraviolet shielding material is not particularly limited, and examples thereof include ultraviolet cut films; ultraviolet shielding lenses such as ultraviolet cut eyeglass lenses or contact lenses. As a method for producing a lens, which is an example of an ultraviolet shielding material, various methods can be adopted, such as a method of kneading the compound of the present invention into a transparent resin and molding it by injection molding, compression molding, extrusion molding, etc., or a method of forming an optical functional layer containing the compound of the present invention on the above-mentioned support. The ultraviolet absorber can be used in various materials such as glass, plastic, fiber, paper, paint, ink, and cosmetics. The ultraviolet absorber can be used by mixing it with various materials, and may be dispersed or dissolved in the materials. In addition, the ultraviolet absorber may be chemically or physically supported on various materials.
Recording materials containing the compounds of the present invention include optical disks and the like.

The following examples are provided to more specifically explain the present invention, but the present invention is not limited to these examples.

The following instruments were used to measure the physical properties of the compounds obtained.
(LC/MS)
Shimadzu Corporation High Performance Liquid Chromatograph Mass Spectrometer LCMS-2010EV (ESI method)
(NMR)
Nuclear magnetic resonance apparatus JNM-ECZ400S manufactured by JEOL Ltd.

Example 1
Synthesis of intermediate (6-1) 2,4,4-trimethyloxazoline (Tokyo Chemical Industry Co., Ltd., 70.8 g), methyl iodide (118 g), and tetrahydrofuran (THF) (80 ml) were placed in a 300 mL reaction flask and stirred for 15 hours. The crystals precipitated from the reaction solution were collected by filtration. The crystals were dried at 50° C. to obtain 126 g of 2,3,4,4-tetramethyloxazolinium iodide.
2,3,4,4-Tetramethyloxazolinium iodide (5.0 g), N,N'-diphenylformamidine (Tokyo Chemical Industry Co., Ltd., 4.0 g), and acetic anhydride (20 mL) were mixed in a 50 mL reaction flask and stirred at 95 to 100°C for 6.5 hours. After the reaction, crystals were precipitated using ethyl acetate and collected by filtration to obtain 3.0 g of a compound represented by the following formula (6-1) (intermediate (6-1)). In the formula, N(Ac)Ph represents an acetanilide group. The same applies below.

Synthesis of Intermediate (7-1) A compound represented by the following formula (7-1) (intermediate (7-1)) was synthesized by the method described in JP-A-2000-310841. In the formula, t-Bu represents a tert-butyl group. The same applies below.

Synthesis of Compound (1-1) In a 50 mL reaction flask, triethylamine (1.0 g) was added dropwise to a mixture of intermediate (6-1) (3.0 g), intermediate (7-1) (2.2 g), and N,N-dimethylformamide (DMF) (15 mL) at about 25° C. After stirring at room temperature for 19 hours, the mixture was poured into water and stirred for a while, and the precipitated crystals were collected by filtration. The crystals were washed with isopropyl alcohol (IPA), and the obtained crystals were dried at 80° C. to obtain 2.1 g of compound (1-1).
MS: m/z=431 [M+H] ^+
1 H-NMR (400 MHz, CDCl ₃ ): δ8.24 (d, 1H), 5.73 (s, 1H), 4.93 (d, 1H), 4.18 (s, 2H), 2.85 (s, 3H), 1.64 (s, 1H) ), 1.56 (d, 2H), 1.41 (t, 2H), 1.33 (s, 6H), 1.13 (d, 2H), 1.02 (d, 3H), 0.87 (s, 18H)

Example 2
Synthesis of Intermediate (6-2) A mixture of N-benzyl-2,4,4-trimethyloxazolinium bromide (7.2 g) obtained by the method described in JP-A-07-126314, N,N'-diphenylformamidine (Tokyo Chemical Industry Co., Ltd., 5.0 g), and IPA (25 mL) was reacted in a 100 mL recovery flask at 80°C for 4.5 hours and concentrated under reduced pressure to obtain an oily product.
In a 50 mL recovery flask, a mixture of the above oil (8.5 g) and acetic anhydride (22 mL) was reacted at 90 to 95° C. for 5.5 hours, and concentrated under reduced pressure to obtain 5.8 g of a compound represented by the following formula (6-2) (intermediate (6-2)).

Synthesis of Compound (1-2) Compound (1-2) was obtained in the same manner as in the synthesis of compound (1-1) in Example 1, except that intermediate (6-1) in the synthesis of compound (1-1) in Example 1 was changed to intermediate (6-2).
MS: m/z=507 [M+H] ⁺

Example 3
Synthesis of Intermediate (7-2) A compound represented by the following formula (7-2) (intermediate (7-2)) was obtained in the same manner as described in US Pat. No. 6,271,410 B1.

Synthesis of Compound (1-3) Compound (1-3) was obtained in the same manner as in the synthesis of compound (1-1) in Example 1, except that intermediate (7-1) in the synthesis of compound (1-1) in Example 1 was changed to intermediate (7-2).
MS: m/z=361 [M+H] ⁺

Example 4
Synthesis of Intermediate (7-3) A compound represented by the following formula (7-3) (intermediate (7-3)) was obtained by the method described in US Pat. No. 6,271,410 B1.

Synthesis of Compound (1-4) Compound (1-4) was obtained in the same manner as in the synthesis of compound (1-1) in Example 1, except that intermediate (7-1) in the synthesis of compound (1-1) in Example 1 was changed to intermediate (7-3).
MS: m/z=305 [M+H] ⁺

Example 5
Synthesis of Intermediate (7-4) A compound represented by the following formula (7-4) (intermediate (7-4)) was obtained in the same manner as described in US Pat. No. 6,271,410 B1.

Synthesis of Compound (1-5) Compound (1-5) was obtained in the same manner as in the synthesis of compound (1-1) in Example 1, except that intermediate (7-1) in the synthesis of compound (1-1) in Example 1 was changed to intermediate (7-4).
MS: m/z=357 [M+H] ^+
1H -NMR (400MHz, CDCl ₃ ): δ8.14 (d, 1H), 4.89 (d, 1H), 4.18 (s, 2H), 2.83 (s, 3H), 2.17 (s, 9H), 1.69-1.61 (m, 6H), 1.33 (s, 6H)

Example 6
Synthesis of Intermediate (7-5) A compound represented by the following formula (7-5) (intermediate (7-5)) was obtained in the same manner as described in US Pat. No. 6,271,410 B1.

Synthesis of Compound (1-6) Compound (1-6) was obtained in the same manner as in the synthesis of compound (1-1) in Example 1, except that intermediate (7-1) in the synthesis of compound (1-1) in Example 1 was changed to intermediate (7-5).
MS: m/z=357 [M+H] ⁺

Example 7
Synthesis of Intermediate (7-6) A compound represented by the following formula (7-6) (intermediate (7-6)) was synthesized in the same manner as described in Macromolecules, 1992, 25(22), pp. 6055-6058.

Synthesis of Compound (1-7) Compound (1-7) was obtained in the same manner as in the synthesis of compound (1-1) in Example 1, except that intermediate (7-1) in the synthesis of compound (1-1) in Example 1 was changed to intermediate (7-6).
MS: m/z=525 [M+H] ⁺

Example 8
Synthesis of Intermediate (7-7) A compound represented by the following formula (7-7) (intermediate (7-7)) was obtained in the same manner as described in US Pat. No. 6,271,410 B1.

Synthesis of Compound (1-8) Compound (1-8) was obtained in the same manner as in the synthesis of compound (1-1) in Example 1, except that intermediate (7-1) in the synthesis of compound (1-1) in Example 1 was changed to intermediate (7-7).
MS: m/z=359 [M+H] ⁺

<Example 9>
Synthesis of intermediate (6-3) A mixture of 2,4,4-trimethyloxazoline (Tokyo Chemical Industry Co., Ltd., 3.4 g), 1,6-diiodohexane (Tokyo Chemical Industry Co., Ltd., 3.4 g), and acetonitrile (10 mL) in a 25 mL reaction flask was reacted at about 75° C. for 18.5 hours and then at about 90° C. for 2.5 hours. The crystals were collected by filtration and washed with ethyl acetate to obtain 4.8 g of the intermediate as crystals.
A mixture of the above crystals (4.8 g), N,N'-diphenylformamidine (3.5 g), and acetonitrile (20 mL) was placed in a 50 mL reaction flask and reacted for 15 hours at about 75° C. The precipitated crystals were collected by filtration to obtain 3.9 g of an intermediate product as crystals.
The above crystals (3.9 g) and acetic anhydride (20 mL) were placed in a 50 mL recovery flask and stirred for 2 hours at about 130° C. After the reaction, the crystals were precipitated with ethyl acetate and collected by filtration to obtain 4.2 g of a compound represented by the following formula (6-3) (intermediate (6-3)).

Synthesis of Compound (1-9) In a 50 mL reaction flask, intermediate (6-3) (3.0 g), intermediate (7-3) (1.3 g), and DMF (13 mL) were placed, and a mixture of triethylamine (0.80 g) and DMF (2 mL) was added dropwise at about 20° C. The mixture was stirred at room temperature for 14 hours, and the reaction solution was poured into water. The precipitated crystals were collected by filtration and washed with methanol to obtain 1.2 g of compound (1-9).
MS: m/z=663 [M+H] ⁺

Example 10
Synthesis of Compound (1-10) Compound (1-10) was obtained in the same manner as in the synthesis of compound (1-9) in Example 9, except that intermediate (7-3) in the synthesis of compound (1-9) in Example 9 was changed to intermediate (7-1).
MS: m/z=916 [M+H] ^+
1 H-NMR (400 MHz, CDCl ₃ ): δ8.22 (d, 2H), 5.73 (s, 2H), 4.90 (d, 2H), 4.17 (s, 4H), 3.20 (t, 4H), 1.72-1.40 (m, 8H), 1.6 0 (s, 2H), 1.56 (d, 4H), 1.50-40 (m, 4H), 1.35 (s, 12H), 1.12 (d, 4H), 1.01 (d, 6H), 0.88 (s, 36H)

<Comparative Example 1>
Synthesis of Compound (1'-1) Compound (1'-1) was obtained in the same manner as in the synthesis of compound (1-1) in Example 1, except that intermediate (7-1) in the synthesis of compound (1-1) in Example 1 was changed to ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.).

<Comparative Example 2>
Synthesis of Compound (1'-2) Compound (1'-2) was obtained in the same manner as in the synthesis of compound (1-1) in Example 1, except that intermediate (7-1) in the synthesis of compound (1-1) in Example 1 was changed to tert-butyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.).

<Comparative Example 3>
Synthesis of Compound (1'-3) Compound (1'-3) was obtained by the method described in WO2019/004046.

The compounds (1-1) to (1-10) obtained in Examples 1 to 10 are compounds represented by the following general formula (11), in which ^R3 and ^R5 are each a group shown in Table 1. In the following formula, Me represents a methyl group.

Compounds (1'-1) to (1'-2) obtained in Comparative Examples 1 to 3 are compounds represented by the above general formula (11), in which ^R3 and ^R5 are groups shown in Table 2. Compound (1'-3) is a compound having a structure shown in Table 2.

The following evaluations were carried out on the compounds obtained in the Examples and Comparative Examples. The results are shown in Tables 1 and 2.

<Absorption wavelength measurement test>
For each compound obtained in the Examples and Comparative Examples, the absorption spectrum in chloroform was measured, and the maximum absorption wavelength (λmax) in the wavelength range of 300 to 800 nm, the half-width, and the gram absorption coefficient at the maximum absorption wavelength were determined.
Measuring equipment: JASCO Corporation, UV-visible spectrophotometer V-560

The half-width is a value indicating the steepness of the absorption spectrum represented by the following formula (I).
Half width = λ _1/2 - λ _max (I)
In the above formula, λ _max represents the maximum absorption wavelength in the range of 350 to 800 nm, and λ _1/2 represents the wavelength at which the absorbance at that wavelength is half that at λ _max and λ _1/2 > λ _max . The half width was evaluated according to the following criteria.
A: Half-value width is less than 15 B: Half-value width is 15 or more and less than 20 C: Half-value width is 20 or more

The gram absorption coefficient was evaluated according to the following criteria.
A: Gram absorptivity coefficient is greater than 120 B: Gram absorptivity coefficient is greater than 90 and is 120 or less C: Gram absorptivity coefficient is 90 or less

<Heat resistance test>
For the compounds obtained in the Examples and Comparative Examples, the weight loss due to thermal decomposition was measured under the following measurement conditions using a thermogravimetric analyzer TGA-50 manufactured by Shimadzu Corporation, and the temperature at which a weight loss of 1% of the initial weight was observed was defined as the decomposition onset temperature.
(Measurement conditions)
The measurement was performed under the conditions of a sample weight of 10 mg, a temperature rise rate of 10° C./min (maximum temperature reached: 500° C.), in a nitrogen atmosphere, and a flow rate of 20 mL/min.
The heat resistance was evaluated based on the decomposition starting temperature according to the following criteria.
A: Decomposition starting temperature is higher than 240°C. B: Decomposition starting temperature is higher than 200°C and 240°C or lower C: Decomposition starting temperature is 200°C or lower

<Light resistance test>
Some of the compounds obtained in the Examples and Comparative Examples were subjected to a light resistance test.
10 mg of each compound was dissolved in 5 mL of an 8 wt % polymethacrylate toluene solution, applied onto a glass substrate by spin coating, and dried to prepare a thin film with a thickness of 1.5 μm.
The prepared thin film was continuously irradiated with light from a xenon lamp (142 klux) for 24 hours, and the transmittance of the thin film before (0 hour) and after irradiation was measured with a spectrophotometer to determine the residual rate of the compound according to the following formula (II).
Compound residual rate (%) = {(1-T ₁ )/(1-T ₀ )}×100 (II)
[where _T0 is the transmittance before irradiation with the xenon lamp, _T1 is the transmittance after irradiation with the xenon lamp, and _T0 and _T1 are between 0 and 1.]
The term "transmittance" refers to the transmittance at the absorption maximum wavelength of each compound, and the higher the residual rate, the more difficult the compound is to be decomposed by light, and the higher the light resistance. The light resistance was evaluated according to the following criteria.
A: Residual compound rate is greater than 65%. B: Residual compound rate is greater than 50% and 65% or less. C: Residual compound rate is 50% or less.

In the substituents shown in Table 1, * indicates the bonding site with general formula (11). Me is a methyl group, Et is an ethyl group, Cy is a cyclohexyl group, t-Bu is a tert-butyl group, and Ph is a phenyl group.

The compounds (1-1) to (1-10) had good heat resistance. The compounds (1-1) to (1-10) had an absorption maximum wavelength at 370 to 380 nm, and the half width was less than 15 nm. The compounds (1-1) to (1-10) also had a gram absorption coefficient of 120 or more. These compounds have a narrow half width and a high gram absorption coefficient, and can selectively and effectively absorb light of 370 to 380 nm. In addition, since these compounds have a narrow half width, they have little absorption in the visible light region. The compounds (1-1) and (1-10) also had good light resistance. The compounds (1'-1) and (1'-2) of Comparative Examples 1 and 2 had inferior heat resistance compared to the compounds of the Examples. The compound (1'-3) of Comparative Example 3 had an absorption maximum at a wavelength longer than 380 nm. The compound (1'-3) of Comparative Example 3 had a wide half-value width and a small gram extinction coefficient.

Claims (5)

A compound represented by the following general formula (1):

In general formula (1), R ^1a and R ^2a each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms ;
R ^3a represents a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms which may have a phenyl group, or a group represented by general formula (2):
R ^4a represents a cyano group ;
R ^5a represents a cyclohexyl group, a norbornyl group or an adamantyl group which may have a linear or branched alkyl group having 1 to 10 carbon atoms , or a group represented by the general formula (3).

(In the general formula (2), L ^1a represents a group in which one hydrogen atom has been eliminated from a linear or branched alkyl group having 1 to 10 carbon atoms ,
T ^1a represents a group represented by general formula (4).
* indicates the bonding site with the nitrogen atom in general formula (1).

In the general formula (4), R ^1b and R ^2b each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms ;
R ^4b represents a cyano group ;
R ^5b represents a cyclohexyl group, a norbornyl group or an adamantyl group, which may have a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms .
* indicates the bonding site with L ^1a in general formula (2).

(In the general formula (3), L ^2a represents a group in which one hydrogen atom has been eliminated from a cyclohexyl group, a 4-tert-butylcyclohexyl group, or a 2,6-di-tert-butyl-4-methylcyclohexyl group ,
^T2a represents a group represented by formula (5) .
* indicates the bonding site with the oxygen atom in general formula (1).

In the general formula (5), R ^1c and R ^2c each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms .
R ^3c represents a linear or branched alkyl group having 1 to 8 carbon atoms ;
R ^4c represents a cyano group .
* indicates the bonding site with ^L2a in general formula (3). In general formula (1), R ^1a and R ^2a each independently represent a hydrogen atom , a methyl group, or an ethyl group ;
R3a represents a methyl group, an ethyl group, a phenylmethyl group, a phenylethyl group, ^or a group represented by general formula (2).
R ^5a represents a cyclohexyl group , a norbornyl group or an adamantyl group , each of which may have a methyl group or a tert-butyl group , or a group represented by general formula (3):
In formula (2), L ^1a represents a group in which one hydrogen atom has been eliminated from a linear or branched alkyl group having 1 to 8 carbon atoms;
In general formula (4), R ^1b and R ^2b each independently represent a hydrogen atom, a methyl group, or an ethyl group; R ^5b represents a cyclohexyl group, a norbornyl group, or an adamantyl group, which may have a methyl group or a tert-butyl group;
The compound according to claim 1 , wherein in general formula (5), R ^1c and R ^2c each independently represent a hydrogen atom, a methyl group, or an ethyl group , and R ^3c represents a linear or branched alkyl group having 1 to 6 carbon atoms. R in general formula (1) ^1a and R ^2a represents a methyl group,
R ^3a represents a methyl group, a phenylmethyl group, or a group represented by general formula (2),
R ^5a represents a cyclohexyl group, a 4-tert-butylcyclohexyl group, a 2,6-di-tert-butyl-4-methylcyclohexyl group, a 1- or 2-adamantyl group, an isobornyl group, or a group represented by general formula (3):
In the general formula (2), L ^1a represents a linear alkyl group having 1 to 8 carbon atoms from which one hydrogen atom has been eliminated,
In the general formula (4), R ^1b and R ^2b represents a methyl group, R ^5b represents a cyclohexyl group, a 4-tert-butylcyclohexyl group, or a 2,6-di-tert-butyl-4-methylcyclohexyl group,
In the general formula (5), R ^1c and R ^2c represents a methyl group, R ^3c 3. The compound according to claim 1 or 2, wherein represents a methyl group or an ethyl group. An optical filter comprising a compound according to any one of claims 1 to 3. An ultraviolet absorber comprising the compound according to any one of claims 1 to 3.