TW201943697A - Compound, light absorber, composition, and optical filter - Google Patents

Abstract

A compound of a specific structure represented by general formula (A), said compound having an indole ring and a cyanoethenyl structure. (In the formula, Ar is an indole ring, R1 represents a cyano group, -COOR, or the like, each R independently represents a hydrogen atom, C1-40 alkyl group, C6-30 aryl group, C7-30 arylalkyl group, or the like, R2 represents a hydrogen atom, C1-40 alkyl group, or the like, n represents an integer of 1-10, and X represents an n-valent group.).

Description

Compound, light absorber, composition and optical filter

The present invention relates to a compound having excellent light absorptivity near 400 nm.

Compounds with strong absorption of specific light are used as CD-R (Compact Disc-Recordable), DVD-R (Digital Versatile Disc-Recordable), DVD + R ( Digital Versatile Disc + Recordable, a recording layer for optical recording media such as blue laser recording discs, or liquid crystal display (LCD), plasma display panel (PDP), electroluminescent display ( ELD), cathode tube display device (CRT), fluorescent display tube, field emission display and other image display device optical elements.

Optical for image display devices such as liquid crystal display (LCD), plasma display panel (PDP), electroluminescence display (ELD), cathode tube display (CRT), fluorescent display tube, field emission display, etc. In the filter, various compounds that absorb light having a wavelength of 300 to 1100 nm are used as light absorbers.

For example, Patent Document 1 reports a filter for an organic EL (Electroluminescence) display element, which contains an ultraviolet absorber and blocks light from 200 nm to 410 nm.
[Prior technical literature]
[Patent Literature]

Patent Document 1: Japanese Patent Laid-Open No. 2004-102223

However, the ultraviolet absorbent described in Patent Document 1 may have insufficient absorption of light near 400 nm. As a result, the filter described in Patent Document 1, for example, has a problem that the degradation of the organic EL display element cannot be sufficiently suppressed in some cases.

The present invention has been made in view of the above problems, and a main object thereof is to provide a compound having excellent absorption of light near 400 nm.

The present inventors conducted diligent research in order to solve the above-mentioned problems, and as a result, they found that a compound having a specific structure of an indole ring and a cyanovinyl structure can efficiently absorb light around 400 nm, thereby completing the present invention.

That is, this invention is a compound represented by the following general formula (A) (henceforth a compound A).

[Chemical 1]

(Wherein Ar is an indole ring,
R ¹ represents cyano, -COOR, -OCOR, -CONHR, -NHCOR, -COONHR, -NHCOOR, -COR, -SO ₂ R, -SOR, -SO ₂ NRR ', halogen atom, nitro or phosphino ,
R and R 'each independently represent a hydrogen atom, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or an impurity containing 2 to 20 carbon atoms Ring base,
R ² represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or 2 carbon atoms ~ 20 containing heterocyclic group,
The alkyl, aryl, aralkyl, and heterocyclic group-containing methylene groups represented by R and R 'and R ² may be substituted with a carbon-carbon double bond, -O-, -S-, -CO- , -O-CO-, -CO-O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-,- O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NR ''-,> P = O, -SS-, -SO ₂ -or whatever In combination, R '' represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,
The hydrogen atom in the alkyl group, aryl group, aralkyl group and heterocyclic group represented by R and R ′ and R ² may be substituted with ethylenically unsaturated group, halogen atom, fluorenyl group, fluorenyloxy group, and substituted amine Sulfoamino, sulfoamido, sulfoamido, carboxyl, cyano, sulfo, hydroxy, nitro, mercapto, amidoimino, carbamate, sulfoamido, phosphonic acid, phosphate, and carboxy , Sulfo, phosphonic and phosphate salts,
n represents an integer from 1 to 10,
X represents n-valent basis)

Since the compound A of the present invention has the above-mentioned specific structure, it has excellent light absorptivity near 400 nm.

The compound A is preferably a compound represented by the following general formula (A1), (A2), or (A3). The reason for this is that the light absorption around 400 nm is more excellent.

[Chemical 2]

^{(Wherein, R 1, R 2, R} , R ', n and X in the general formula (A), the ^{R 1, R 2, R,} R', and n and X,
R ³ and R ⁴ represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or carbon Heterocyclic group containing 2 to 20 atoms,
R ⁵ and R ⁵⁵ each independently represent a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a carbon atom, respectively Heterocyclic group containing 2 to 20,
The alkyl, aryl, aralkyl, and methylene groups in the heterocyclic group represented by R ³ and R ⁴ and R ⁵ and R ⁵⁵ may be substituted with a carbon-carbon double bond, -O-, -S- , -CO-, -O-CO-, -CO-O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO- O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NR ''-,> P = O, -SS-, -SO _2- Or a combination thereof, R '' represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,
The hydrogen atoms in the alkyl group, aryl group, aralkyl group and heterocyclic group represented by R ³ and R ⁴ and R ⁵ and R ⁵⁵ may be substituted with ethylenically unsaturated groups, halogen atoms, fluorenyl groups, and fluorenyl oxides. Group, substituted amino group, sulfoamido group, sulfoamido group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, mercapto group, fluorenimine group, carbamate group, sulfonamido group, phosphonic acid group, phosphoric acid And carboxyl, sulfo, phosphonic and phosphate salts,
5a represents an integer from 0 to 4,
55a represents an integer from 0 to 3)

The 10% weight reduction temperature of the aforementioned compound A at normal pressure is preferably 250 ° C or higher. The reason for this is that the above-mentioned compound A is a compound having low volatility.

The above-mentioned n is preferably an integer of 2-10. The reason for this is that the above-mentioned compound A is a compound having excellent light absorptivity and low volatility around 400 nm.

The X is preferably an aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a methylene group in these groups is substituted by -O-, -S-, -CO- , -COO-, -OCO-. The reason for this is that the above-mentioned compound A is a compound having excellent light absorptivity and low volatility around 400 nm.

Preferably, at least one of R ³ , R ⁴ , R ⁵ and R ⁵⁵ is an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms. Or a hydrogen atom in a heterocyclic group having 2 to 20 carbon atoms is substituted with an ethylenically unsaturated group, or an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a carbon atom An aralkyl group having 7 to 30 or a methylene group in a heterocyclic group having 2 to 20 carbon atoms is substituted with a carbon-carbon double bond group. The reason for this is that the above-mentioned compound A is a compound having low volatility.

The compound A is preferably one that satisfies the following (1) or (2).
(1) is a compound represented by the general formula (A1), n is an integer of 2 or 3, X is an aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or the The methylene group in the isopropyl group is substituted with a -O-, -S-, -CO-, -COO-, -OCO- group.
(2) is a compound represented by the above general formula (A3), and n is 1, and R ⁴ is an alkyl group having 1 to 10 carbon atoms or one hydrogen atom in these groups is substituted with an ethylenically unsaturated group The methylene group in the alkyl group or the alkyl group having 1 to 40 carbon atoms is substituted with -COO- or -OCO-, and the hydrogen atom in the group is substituted with an ethylenically unsaturated group.
The reason is that the above-mentioned compound A is a compound having excellent light absorptivity and low volatility around 400 nm.

The maximum absorption wavelength of the compound A in a range of 250 nm to 600 nm is preferably 350 nm to 420 nm. The reason for this is that the above-mentioned compound A is more excellent in light absorption in the vicinity of 400 nm.

The present invention provides a light absorber, which comprises the above-mentioned compound A. By including the above-mentioned compound A, the light absorber becomes more excellent in the absorbance of light in the vicinity of 400 nm.

The present invention provides a composition comprising the above-mentioned compound A and a resin. By including the above-mentioned compound A, the composition becomes a more excellent absorber of light in the vicinity of 400 nm.

The present invention provides an optical filter having a light absorbing layer containing the compound A described above. When the light absorbing layer contains the compound A, the optical filter becomes more excellent in light absorption around 400 nm.

The invention relates to a compound, a light absorber, a composition and an optical filter.
Hereinafter, the compound, the light absorber, the composition, and the optical filter of the present invention will be described in detail.

A. Compound First, the compound of the present invention will be described.
The compound of the present invention is characterized by being represented by the general formula (A).

Since the compound of the present invention has the above-mentioned specific structure, that is, a structure in which a cyanovinyl group (-CR ² = C (CN) R ¹ ) is bonded to an indole ring, it has excellent light absorptivity near 400 nm. The reason why the light absorption near 400 nm is excellent due to the above-mentioned specific structure is not clear, but it is estimated as follows.

The indole ring has a maximum absorption wavelength from 250 nm to 300 nm if it is a separate component. By introducing a cyanovinyl group therein, the conjugated system becomes long, and a long wavelength shift of the maximum absorption wavelength occurs. As a result, light in the vicinity of 400 nm can be absorbed. Moreover, as said compound A, a dicyanovinyl group can be used as a cyanovinyl group. As a result, it is easy for the compound A to show a steep absorption peak near 400 nm, especially from 350 nm to 420 nm. In this case, it is considered that the compound A is excellent in light absorption around 400 nm by having the specific structure described above.

The optical filter containing the compound A is capable of stably absorbing specific light due to the characteristics of the compound A as described above. Therefore, when the optical filter is used together with an organic electroluminescence element, for example, it is possible to effectively suppress deterioration of the organic EL element.

Hereinafter, the compound of this invention is demonstrated in detail.
The compound of the present invention is represented by the general formula (A), and a cyanovinyl group (-CR ² = C (CN) R ¹ ) and an n-valent group X are directly bonded to the indole ring Ar. The bonding position is not limited as long as it is a position where the cyanovinyl group can be bonded, and it is preferably the third position of the indole ring represented by "**" in the following formula (a1). The reason for this is that by being the bonding position, the above-mentioned compound A becomes an excellent absorber of light around 400 nm. The reason is that the above compound A becomes an easy synthesizer.

[Chemical 3]

The aforementioned indole ring Ar is directly bonded to a cyanovinyl group and an n-valent group X, but hydrogen atoms other than the sites to which these groups are bonded may be substituted with a substituent.

In the case where n is 2 or more, the number of types of the bonding positions with the n-valent group X may be two or more, but one is preferable. The reason is that the above-mentioned compound A becomes an easy synthesizer. The above-mentioned compound A has two or more types of bonding positions with the n-valent group X, which means that, for example, when n is 2, the divalent group X and an indole ring Ar are in the first position. It is bonded to the position of the second position and is bonded to the position of the second indole ring Ar at the second position. The type of the bonding position between the compound A and the n-valent group X is one, which means that, for example, when n is 2, the divalent group X and the two indole rings Ar are respectively Bonded at the first position.

The compound A is more specifically a compound represented by the general formula (A1), (A2), or (A3) (hereinafter, sometimes referred to as a compound A1, a compound A2, and a compound A3). Among them, the compound A is more preferably a compound A1. The reason is that the compound A1 is excellent in the absorbance of light near 400 nm because the bonding position with the n-valent group X is the first position of the indole ring Ar. The reason is that the compound A1 is easy to synthesize.

The compound A2 is an example in which the bonding position with the n-valent group X is the position at the second position of the indole ring Ar, and the compound A3 is the example with the bonding position in the n-valent group X at positions 4 to 7. In addition, the compounds A1 to A3 are examples in which the type of the bonding position to the n-valent group X is one.

Examples of the alkyl group having 1 to 40 carbon atoms represented by R, R ', R ² , R ³ , R ⁴ , R ⁵ and R ⁵⁵ include methyl, ethyl, propyl, isopropyl, and butyl , Second butyl, third butyl, isobutyl, pentyl, isopentyl, third pentyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl , Heptyl, 2-heptyl, 3-heptyl, isoheptyl, third heptyl, 1-octyl, isooctyl, third octyl, adamantyl and the like.

Examples of the aryl group having 6 to 30 carbon atoms represented by R, R ′, R ² , R ³ , R ⁴ , R ⁵ and R ⁵⁵ include a phenyl group, a naphthyl group and an anthryl group.

Examples of the aralkyl group having 7 to 30 carbon atoms represented by R, R ′, R ² , R ³ , R ⁴ , R ⁵ and R ⁵⁵ include benzyl, fluorenyl, indenyl and 9-fluorenylmethyl Base etc.

Examples of the heterocyclic group having 2 to 20 carbon atoms represented by R, R ', R ² , R ³ , R ⁴ , R ⁵ and R ⁵⁵ include pyridyl, pyrimidinyl, daphthyl, piperidinyl, Pyranyl, pyrazolyl, triyl, pyrrolyl, quinolinyl, isoquinolinyl, imidazolyl, benzimidazolyl, triazolyl, furyl, furanyl, benzofuran , Thienyl, thiophenyl, benzothienyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl Base, indolyl, 2-pyrrolidinone-1-yl, 2-piperidone-1-yl, 2,4-dioxyimidazol-3-yl, and 2,4-dioxyoxazolidine -3-yl, etc.

Examples of the halogen atom represented by R ² , R ³ , R ⁴ , R ^5, and R ⁵⁵ include fluorine, chlorine, bromine, and iodine.

R, R ', R ² , R ³ , R ⁴ , R ⁵ and R ⁵⁵ represented by the alkyl, aryl, aralkyl and heterocyclic methylene groups may be substituted with carbon-carbon double bonds , -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO- S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NR ''-,> P = O, -SS-, -SO ₂ -or a combination of these.

That is, R, R ', R ² , R ³ , R ⁴ , R ⁵ and R ⁵⁵ may be an alkyl group, an aryl group, an aralkyl group, and a methylene group in a heterocyclic group is substituted with a carbon-carbon double bond , -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO- S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NR ''-,> P = O, -SS-, -SO ₂ -or a combination thereof.

The above-mentioned "R" represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. Examples of the alkyl group having 1 to 8 carbon atoms include those satisfying a specific number of carbon atoms among those exemplified by R ² and the like.
Specific examples of the carbon-carbon double bond include -CH = CH-, -C (CH ₃ ) = CH-, -C (CH ₃ ) = C (CH ₃ )-, and the like.

R, R ', R ² , R ³ , R ⁴ , R ⁵ and R ⁵⁵ represent alkyl, aryl, aralkyl and heterocyclic group-containing methylene groups by the above-mentioned carbon-carbon double bonds, etc. The number of substitutions is not limited to one, and may be two or more.

In the present invention, regarding the number of carbon atoms of the group, when the methylene group in the group is substituted with the above carbon-carbon double bond, etc., the number of carbon atoms of the substituted group is specified. For example, in the present specification, when a methylene group in an alkyl group having 1 to 40 carbon atoms is replaced with the above carbon-carbon double bond, etc., the "carbon number 1 to 40" means that the methylene group is replaced by The number of carbon atoms after substitution does not refer to the number of carbon atoms before the methylene group is substituted. Therefore, for example, as in R ¹ of the compound (41) described below, the number of carbon atoms in a group in which one methylene group in a propyl group is substituted with -CO-O- is three.

The alkyl group, aryl group, aralkyl group, and heterocyclic group represented by R, R ′, R ² , R ³ , R ⁴ , R ^5, and R ⁵⁵ may have a substituent. The compound A includes those having no substituent and those having a substituent unless otherwise specified.

The hydrogen atom in the alkyl group, aryl group, aralkyl group and heterocyclic group represented by R, R ', R ² , R ³ , R ⁴ , R ⁵ and R ⁵⁵ may be substituted with vinyl, allyl , Ethylenically unsaturated groups such as propylene, methacryl and methacryl; halogen atoms such as fluorine, chlorine, bromine, and iodine; ethenyl, 2-chloroethyl, propyl, octyl, acryl, and acryl Propylene amidino, phenylcarbonyl (benzylidene), phthalofluorenyl, 4-trifluoromethylbenzyl, trimethylethylamyl, o-hydroxybenzyl, oxalyl, stearyl Fluorenyl groups such as fluorenyl, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, n-octadecyloxycarbonyl, and carbamoyl; fluorenyl groups such as ethanyloxy and benzyloxy ; Amino, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecylamino, aniline, Chlorophenylamine, toluidine, methoxyaniline, N-methyl-aniline, diphenylamino, naphthylamine, 2-pyridylamino, methoxycarbonylamino, phenoxy Carbonylamino, ethylamino, benzamidoamino, methylamido Group, trimethylethylamino, laurylamino, aminomethylamino, N, N-dimethylaminocarbonylamino, N, N-diethylaminocarbonylamino, Phenylcarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, tert-butoxycarbonylamino, n-octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino , Phenoxycarbonylamino, sulfamoylamino, N, N-dimethylaminosulfoamidoamino, methylsulfoamidoamino, butylsulfoamidoamine, and phenylsulfoamido Substituted amino groups such as sulfonylamino groups; sulfonamido, sulfofluorenyl, carboxyl, cyano, sulfo, hydroxyl, nitro, thiol, fluorenimine, carbamoyl, sulfonamido, phosphonic acid groups , Phosphate, and salts of carboxyl, sulfo, phosphonic and phosphate groups.

That is, R, R ', R ² , R ³ , R ⁴ , R ⁵ and R ⁵⁵ may be an alkyl group, an aryl group, an aralkyl group, and a hydrogen atom in a heterocyclic group may be substituted with an ethylenically unsaturated group, Halogen atom, fluorenyl, fluorenyloxy, substituted amino, sulfonamido, sulfonamido, carboxyl, cyano, sulfo, hydroxyl, nitro, mercapto, fluorenimine, carbamoyl, sulfamo Amino, phosphonic, phosphoric, or carboxy, sulfo, phosphonic, or phosphate salts.

The number of the alkyl group, aryl group, aralkyl group, and heterocyclic group-containing hydrogen atom substituted with a substituent group represented by R, R ', R ² , R ³ , R ⁴ , R ⁵ and R ⁵⁵ is not limited to 1 It can also be 2 or more.

In the present invention, regarding the number of carbon atoms of a radical, when a hydrogen atom in the radical is substituted with a substituent, the number of carbon atoms of the radical after the substitution is specified. For example, in the case where the hydrogen atom of the alkyl group having 1 to 40 carbon atoms is substituted, the carbon number 1 to 40 refers to the number of carbon atoms after the hydrogen atom is substituted, not the carbon atom before the hydrogen atom is substituted. number. Therefore, for example, as in R ⁴ of the compound (40) described below, the number of carbon atoms in a group in which one hydrogen atom at the terminal of the propyl group is substituted with -CH = CH _{2 is} five. The number of carbon atoms of R ⁴ in the compound (103) and the compound (104) described below is 13 and 17, respectively.

The above R ¹ represents cyano, -COOR, -OCOR, -CONHR, -NHCOR, -COONHR, -NHCOOR, -COR, -SO ₂ R, -SOR, -SO ₂ NRR ', halogen atom, nitro or phosphine Among the fluorenyl groups, cyano and -COOR are preferred, and cyano is particularly preferred. The reason for this is that, with the above-mentioned R ^{1 being} such a group, the above-mentioned compound A becomes an excellent absorber of light around 400 nm. Furthermore, the reason is that the above-mentioned compound A is excellent in the balance of light absorption, low volatility, and ease of synthesis in the vicinity of 400 nm.

The above-mentioned R and R 'independently represent a hydrogen atom, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or 2 to 20 carbon atoms, respectively. Those having a heterocyclic group are preferably an alkyl group having 1 to 40 carbon atoms and an aralkyl group having 7 to 30 carbon atoms. Among them, an alkyl group having 1 to 40 carbon atoms is preferred, and a carbon number is particularly preferred. The alkyl group having 1 to 10 is particularly preferably an alkyl group having 1 to 5 carbon atoms such as methyl, ethyl, and propyl. The reason for this is that by using R and R ′ as these groups, the compound A is excellent in light absorption around 400 nm. The reason is that the above compound A becomes an easy synthesizer. Furthermore, the reason is that the above-mentioned compound A is excellent in the balance of light absorption, low volatility, and ease of synthesis in the vicinity of 400 nm.

The above-mentioned R and R ′ are each preferably an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms and 2 to 20 carbon atoms. A hydrogen atom in a heterocyclic group is substituted with an ethylenically unsaturated group, or an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or The methylene group in the heterocyclic group having 2 to 20 carbon atoms is substituted with a carbon-carbon double bond group. Among them, it is preferable that a hydrogen atom in an alkyl group having 1 to 40 carbon atoms is substituted with an ethylenically unsaturated group, or a methylene group in the alkyl group having 1 to 40 carbon atoms is substituted with carbon- The carbon double bond group is particularly preferably a group in which a hydrogen atom in an alkyl group having 1 to 10 carbon atoms is replaced with an ethylenically unsaturated group, or a methylene group in the alkyl group having 1 to 10 carbon atoms is substituted. Substituted by a carbon-carbon double bond. Among them, it is particularly preferred that a hydrogen atom in an alkyl group having 3 to 7 carbon atoms is replaced with an ethylenically unsaturated group, or a methylene group in the above alkyl group having 3 to 7 carbon atoms is replaced with a carbon-carbon The base of double bonds. The reason for this is that, when R and the like are the above-mentioned groups, the above-mentioned compound A becomes a compound having low volatility. The reason is that the above compound A becomes an easy synthesizer.

The R ² is a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a carbon atom. The heterocyclic group containing 2 to 20 is preferably a hydrogen atom, a cyano group, or an alkyl group having 1 to 40 carbon atoms, and among these, a hydrogen atom is preferred. The reason is that, with the above R ^{2 being} such a group, the above-mentioned compound A becomes an excellent absorber of light around 400 nm. The reason is that the above compound A becomes an easy synthesizer.

The above R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an aromatic group having 7 to 30 carbon atoms. The alkyl group or the heterocyclic group containing 2 to 20 carbon atoms is preferably a hydrogen atom or an alkyl group having 1 to 40 carbon atoms. The reason is that the above-mentioned compound A is excellent in light absorptivity near 400 nm. The reason is that the above-mentioned compound A is a compound having low volatility, and further, it is easy to synthesize.
In the present invention, when R ³ is a group without a polymerizable group described below, a hydrogen atom, an alkyl group having 1 to 40 carbon atoms, or an aryl group having 6 to 30 carbon atoms is preferred, Among them, a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 15 carbon atoms is preferred, and a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or 6 to 12 carbon atoms is particularly preferred. Of aryl. The reason is that the above-mentioned compound A is excellent in light absorptivity near 400 nm. The reason is that the above-mentioned compound A is a compound having low volatility, and further, it is easy to synthesize. In addition, from the viewpoint of achieving an excellent balance of the light absorptivity, low volatility, and ease of synthesis in the vicinity of 400 nm, R ³ is preferably a hydrogen atom.
In addition, in the present invention, when R ⁴ is a group having no polymerizable group described below, an alkyl group having 1 to 40 carbon atoms is preferred, and among them, 1 to 20 carbon atoms are preferred. The alkyl group is particularly preferably an alkyl group having 1 to 5 carbon atoms. The reason is that, with the R ⁴ being the above-mentioned group, the compound A is excellent in a balance of light absorption, low volatility, and ease of synthesis in the vicinity of 400 nm.

The R ⁵ and R ⁵⁵ each independently represent a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or The heterocyclic group containing 2 to 20 carbon atoms is preferably a hydrogen atom and an alkyl group having 1 to 40 carbon atoms, and particularly preferably a hydrogen atom. The reason is that it is excellent in the balance of light absorption, low volatility, and ease of synthesis in the vicinity of 400 nm. When plural R ⁵ and R ⁵⁵ are present, they may be the same or different.

The reason is that, with the above-mentioned R ³ , R ⁴ , R ⁵ and R ⁵⁵ as these groups, the above-mentioned compound A becomes an excellent absorber of light near 400 nm. The reason is that the above compound A becomes an easy synthesizer. Furthermore, the reason is that the above-mentioned compound A is a compound having low volatility.

The compound A is preferably one in which at least one of R ³ , R ⁴ , R ^5, and R ⁵⁵ is a polymerizable group. Thereby, the said compound A becomes a compound with low volatility. More specifically, the reason is that the aforementioned compound A can be polymerized by, for example, polymerizing the compounds A with each other, and can be polymerized by polymerizing with a polymerizable compound such as an acrylate monomer. As a result, the volatility is relatively low. Low compounds. The polymerizable group may be any polymer that can be polymerized by polymerizing the polymerizable groups with each other, and examples thereof include a radical polymerizable group, a cation polymerizable group, and an anionic polymerizable group.
In the present invention, it is preferred that only one of R ³ , R ⁴ , R ^5, and R ⁵⁵ be a polymerizable group, and among them, only R ⁴ has a polymerizable group. The reason is that the above-mentioned compound A is excellent in the balance of light absorption, low volatility, and ease of synthesis in the vicinity of 400 nm.

Examples of the radically polymerizable group include a (meth) acrylfluorenyl group and an ethylenically unsaturated group such as a vinyl group. Moreover, as said radically polymerizable group, you may use the said carbon-carbon double bond which substituted methylene. Examples of the cationically polymerizable group include an epoxy group, an oxetanyl group, and a vinyl ether group. Examples of the anionic polymerizable group include an epoxy group and a lactone group. As said polymerizable group, a radically polymerizable group, such as an ethylenically unsaturated group and a carbon-carbon double bond, is preferable. The reason is that the above-mentioned compound A is easily made into a compound having low volatility.

The compound A is more specifically preferably such that at least one of R ³ , R ⁴ , R ^5, and R ⁵⁵ is an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, and carbon number. Aryl groups of 7 to 30 or heterocyclic groups containing 2 to 20 carbon atoms, alkyl groups of 1 to 40 carbon atoms, aryl groups of 6 to 30 carbon atoms, and aralkyl groups of 7 to 30 carbon atoms Group or a hydrogen atom in a heterocyclic group containing 2 to 20 carbon atoms is substituted with an ethylenically unsaturated group, or the alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, An aralkyl group having 7 to 30 carbon atoms or a methylene group in a heterocyclic group having 2 to 20 carbon atoms is substituted with a carbon-carbon double bond group. Among them, the above-mentioned R ³ , R ⁴ , At least one of R ⁵ and R ⁵⁵ is an alkyl group having 1 to 40 carbon atoms, or a hydrogen atom in an alkyl group having 1 to 40 carbon atoms is substituted with an ethylenically unsaturated group, or 1 carbon atom The methylene group in the alkyl group of ～ 40 is substituted with a carbon-carbon double bond group, and it is particularly preferred that R ⁴ is a hydrogen group in the alkyl group having 1 to 40 carbon atoms, or a hydrogen group in the alkyl group having 1 to 40 carbon atoms. Atoms substituted with ethylenically unsaturated groups, or 1 carbon atom The alkyl group in the 40-substituted methylene group is a carbon - carbon double bond group, wherein R ⁴ is particularly preferably an alkyl group having 1 to 10 carbon atoms, the carbon atoms or an alkyl group of 1 to 10 in the hydrogen A group in which an atom is substituted with an ethylenically unsaturated group, or a methylene group in an alkyl group having 1 to 10 carbon atoms is replaced with a carbon-carbon double bond group, preferably R ⁴ is 3 to 10 carbon atoms An alkyl group, or a hydrogen atom in an alkyl group having 3 to 10 carbon atoms is substituted with an ethylenically unsaturated group, or a methylene group in an alkyl group having 3 to 10 carbon atoms is substituted It is the base of carbon-carbon double bond. The reason for this is that the above compound A is a compound having a lower volatility when the above R ³ and the like are the above-mentioned groups. The reason is that the above compound A becomes an easy synthesizer.

In the present invention, a hydrogen atom in which R ⁴ is an alkyl group having 1 to 40 carbon atoms, or an alkyl group having 1 to 40 carbon atoms is substituted with an ethylenically unsaturated group, or a carbon number of 1 to When the methylene group in the alkyl group of 40 is substituted with a carbon-carbon double bond group, as R ⁴ , it is also preferable that two or more hydrogen atoms in the alkyl group having 1 to 40 carbon atoms are substituted with A group having two or more methylene groups in the ethylenically unsaturated group or the alkyl group having 1 to 40 carbon atoms is substituted with a carbon-carbon double bond group. Among them, it is preferable that two or more hydrogen atoms in an alkyl group having 5 to 25 carbon atoms be substituted with an ethylenically unsaturated group or two or more methylene groups in an alkyl group having 5 to 25 carbon atoms. A group substituted with a carbon-carbon double bond, particularly preferably a group in which 2 to 5 hydrogen atoms in an alkyl group having 8 to 22 carbon atoms are replaced with an ethylenically unsaturated group, or an alkyl group having 8 to 22 carbon atoms 2 to 5 methylene groups in an alkyl group are substituted with a carbon-carbon double bond group, particularly preferably 2 to 4 hydrogen atoms in an alkyl group with 10 to 20 carbon atoms are substituted with an ethylenically unsaturated group A group having 2 to 4 methylene groups or an alkyl group having 10 to 20 carbon atoms is substituted with a carbon-carbon double bond group. The reason is that, with the R ⁴ being the above-mentioned group, the compound A is excellent in a balance of light absorption, low volatility, and ease of synthesis in the vicinity of 400 nm.

In addition, in the case where R ⁴ is an alkyl group having 1 to 40 carbon atoms, two or more hydrogen atoms are substituted with an ethylenically unsaturated group, or two or more sub groups in the alkyl group having 1 to 40 carbon atoms. When a methyl group is substituted with a carbon-carbon double bond group, it is preferred that the methylene groups in these groups are independently substituted with a -COO- or -OCO- group. The reason is that, with the R ⁴ being the above-mentioned group, the compound A is excellent in a balance of light absorption, low volatility, and ease of synthesis in the vicinity of 400 nm.

The carbon number of the methylene group in the above-mentioned alkyl group having 1 to 40 carbon atoms is replaced by a carbon-carbon double bond refers to the number of carbon atoms after the methylene group is replaced with a carbon-carbon double bond, and does not refer to the methylene group. The number of carbon atoms before the methyl group was replaced with a carbon-carbon double bond. The same applies to the case where the methylene group in the other group is substituted.
In addition, the number of carbon atoms of the hydrogen atom substituted by a substituent in the alkyl group having 1 to 40 carbon atoms refers to the number of carbon atoms after the hydrogen atom is substituted with the substituent, and does not mean that the hydrogen atom is substituted before the substituent. Of carbon atoms. The same applies to the case where a hydrogen atom in another group is substituted.

The aforementioned n is an integer of 1 to 10, preferably an integer of 2 to 10, of which an integer of 2 to 6 is preferred, and an integer of 2 to 4 is particularly preferred. The reason for this is that when n is in the above range, the compound A is a compound having excellent light absorptivity and low volatility around 400 nm.

The above 5a represents an integer of 0 to 4, preferably an integer of 0 or 1.
The above 55a represents an integer of 0 to 3, preferably an integer of 0 or 1.
The reason is that when 5a and 55a are in the above range, the above-mentioned compound A becomes an excellent absorber of light near 400 nm. The reason is that the above compound A becomes an easy synthesizer.

The compound A represented by the general formula (A) has a structure in which an n-valent group represented by X is bonded to n specific structures including an indole ring Ar and a cyanovinyl structure. The n specific structures may be the same or different from each other.

The X represents an n-valent group.
Specific examples of the X include a direct bond, a hydrogen atom, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a group represented by the following (II-a) or (II-b), and> C = O ,> NR ⁵³ , -OR ⁵³ , -SR ⁵³ , -NR ⁵³ R ⁵⁴ or an aliphatic hydrocarbon group having 1 to 120 carbon atoms having the same number of valence as n, and an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms Or a heterocyclic group containing 2 to 35 carbon atoms.

The R ⁵³ and R ⁵⁴ each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic group containing 2 to 35 carbon atoms. The methylene groups in the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group and the heterocyclic group represented by the above X, R ⁵³ and R ⁵⁴ may be substituted with -O-, -S-, -CO-, -O-CO -, -CO-O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S -, -CO-NH-, -NH-CO-, -NH-CO-O-, -NH-CO-O-, -NR ^' -, -SS-, -SO _2- , nitrogen atom or the like combination. The number of substituted methylene groups is not limited to one, and may be two or more.
That is, the above-mentioned X, R ⁵³ and R ⁵⁴ may be one of an aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms or a heterocyclic group containing 2 to 35 carbon atoms. Methyl is substituted with -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -O-CO-O-, -S-CO- , -CO-S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NH-CO-O- , -NR ^' -, -SS-, -SO _2- , a nitrogen atom, or a combination thereof.
The aromatic ring or heterocyclic ring may be condensed with another ring.

When X is a nitrogen atom, a phosphorus atom, or a bonding group represented by the following (II-a) or (II-b), n is 3, and X is a direct bond, an oxygen atom or a sulfur atom, and> C = O, -NH-CO-, -CO-NH-, or> NR ⁵³ , n is 2, and when X is -OR ⁵³ , -SR ^53, or -NR ⁵³ R ⁵⁴ , n is 1, X may also form a ring with a benzene ring.

[Chemical 4]

(* Means that the * part is bonded to the adjacent base)

Regarding the aliphatic hydrocarbon group having 1 to 120 carbon atoms having the same number of valences as represented by X in the above X, the monovalent ones include methyl, ethyl, propyl, isopropyl, and cyclopropyl. , Butyl, second butyl, third butyl, isobutyl, pentyl, isopentyl, third pentyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, bicyclohexyl , 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, third heptyl, n-octyl, isooctyl, third octyl, 2-ethylhexyl, nonyl Alkyl groups such as alkyl, isononyl and decyl; methoxy, ethoxy, propoxy, isopropoxy, butoxy, second butoxy, third butoxy, isobutoxy, Pentyloxy, isopentyloxy, third pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, third heptyloxy, n-octyloxy, isooctyloxy, Alkoxy groups such as trioctyloxy, 2-ethylhexyloxy, nonyloxy and decyloxy; methylthio, ethylthio, propylthio, isopropylthio, butylthio, second butylthio Base, third butylthio, isobutylthio, pentylthio, isopentylthio, third pentylthio Alkyl sulfides such as hexylthio, cyclohexylthio, heptylthio, isoheptylthio, third heptylthio, n-octylthio, isooctylthio, third octylthio and 2-ethylhexylthio Vinyl; 1-methylvinyl, 2-methylvinyl, 2-propenyl, 1-methyl-3-propenyl, 3-butenyl, 1-methyl-3-butenyl , Isobutenyl, 3-pentenyl, 4-hexenyl, cyclohexenyl, dicyclohexenyl, heptenyl, octenyl, decenyl, pentadecenyl, eicosenyl And alkenyl groups such as behenyl alkenyl; and groups in which a hydrogen atom of these groups is substituted with a substituent described below.

Regarding the aliphatic hydrocarbon group having 1 to 120 carbon atoms having the same number of valences as represented by X in the above-mentioned X, as the divalent group, a group obtained by removing one hydrogen atom from the above-mentioned monovalent aliphatic hydrocarbon group, Specific examples include: alkylene groups such as methylene, ethylene, propyl, butyl, and butyldiyl; the methylene in the alkylene is substituted with -O-, -S -, -CO-O-, -O-CO-; residues of glycol groups such as ethylene glycol, propylene glycol, butanediol, pentanediol, and hexanediol; ethylenedithiol, propylene glycol Residues of dithiol groups such as thiol, butanethiol, glutar dithiol, hexamethylene dithiol, and the hydrogen atom of these groups are substituted with the substituents described below.

Regarding the aliphatic hydrocarbon group having 1 to 120 carbon atoms having the same number of valences as represented by X in the above X, as the trivalent group, a group obtained by removing two hydrogen atoms from the above monovalent aliphatic hydrocarbon group may be mentioned. For example, an oxyalkylene group such as propylidene group and 1,1,3-butylidene propylidene group; and a group in which a hydrogen atom of these groups is substituted with a substituent described below, and the like are mentioned.
The trivalent group is not limited to a group obtained by removing three hydrogen atoms from one carbon atom in an aliphatic hydrocarbon such as propane and butane, as in the case of an alkylene group, and may include two carbon atoms in an aliphatic hydrocarbon. A group obtained by removing three hydrogen atoms in total, and a group obtained by removing one hydrogen atom from each of three different carbon atoms in the aliphatic hydrocarbon.

Regarding the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms having the same number of valences as represented by X in the above X, examples of the monovalent group include benzyl, phenethyl, benzyl, and trityl. Aryl groups such as phenyl, styryl, and cinnamyl; aryl groups such as phenyl and naphthyl; aryloxy groups such as phenoxy and naphthyloxy; arylthio groups such as phenylthio and naphthylthio: and such groups A hydrogen atom is substituted with a substituent described below, and the like.

Regarding the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms having the same number of valences as represented by X in the above X, as the divalent group, arylene groups such as phenylene and naphthyl; catechol groups Residues of bifunctional phenol groups such as bisphenol and bisphenol; 2,4,8,10-tetraoxaspiro [5,5] undecyl; sequential alkylene, alkylene, and alkylene bonds A base formed by combining an alkylene group and an alkylene group; and a base in which a hydrogen atom of these groups is replaced with a substituent described below.
Examples of the alkylene group include the same as the alkylene group represented by X.

Regarding the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms having the same number of valences as that represented by X described above, examples of the trivalent group include phenyl-1,3,5-trimethylene and the group A hydrogen atom is substituted with a substituent described below, and the like.

As for the heterocyclic group containing 2 to 35 carbon atoms having the same number of valences as represented by X in the above X, those in which n is monovalent include pyridyl, pyrimidinyl, daphthyl, piperidinyl, Pyranyl, pyrazolyl, triyl, pyrrolyl, quinolinyl, isoquinolinyl, imidazolyl, benzimidazolyl, triazolyl, furyl, furanyl, benzofuran , Thienyl, thiophenyl, benzothienyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl , Indolyl, 2-pyrrolidone-1-yl, 2-piperidone-1-yl, 2,4-dioxyimidazol-3-yl, 2,4-dioxyoxazolidine- 3-yl, benzotriazolyl, and the like in which a hydrogen atom of these groups is substituted with a substituent described below.

Regarding the heterocyclic group having 2 to 35 carbon atoms having the same number of valences as represented by X in the above X, those in which n is divalent include a pyridine ring, a pyrimidine ring, a piperidine ring, a piperidine ring, The trivalent, furan ring, thiophene ring, and indole ring are divalent groups, and those groups in which a hydrogen atom is substituted with a substituent described below, and the like.

Regarding the heterocyclic group containing 2 to 35 carbon atoms having the same number of valences as represented by X in the above X, as n is a trivalent group, a trivalent group having an isotricyanate ring and The trivalent radical of the ring and the hydrogen atom of these radicals are substituted with a substituent described below, and the like.

Examples of the aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by R ⁵³ and R ⁵⁴ include those in which the aliphatic hydrocarbon group represented by X or the hydrogen atom of the aliphatic hydrocarbon group is substituted with a substituent described below. The number of carbon atoms in the group is 1 to 35.

Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms or the heterocyclic group containing 2 to 35 carbon atoms represented by R ⁵³ and R ⁵⁴ include the aromatic ring containing 6 to 35 carbon atoms represented by X described above. A hydrocarbon group or a heterocyclic group containing 2 to 35 carbon atoms or a hydrogen atom of such a group is substituted with a substituent described below.

Each functional group such as an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group and a heterocyclic group represented by X, R ⁵³ , R ⁵⁴ and the like may have a substituent. Examples of such a substituent substituted for a hydrogen atom such as an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group, and a heterocyclic group include the same substituents as those substituted for a hydrogen atom such as an alkyl group represented by R ² and the like. The compound A of the present invention includes those having no substituent and those having a substituent unless otherwise specified.

As said X, when n is 2, the group represented by the following general formula (1) is mentioned.
As said X, when n is 3, the group represented by following General formula (2) is mentioned.
As said X, when n is 4, the group represented by the following general formula (3) is mentioned.
As said X, when n is 5, the group represented by the following general formula (4) is mentioned.
As said X, when n is 6, the group represented by the following general formula (5) is mentioned.

[Chemical 5]

(In the above general formula (1), Y ¹ represents -CR ⁵⁵ R ^56- , -NR ^57- , a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, and a divalent aromatic group containing 6 to 35 carbon atoms. A cyclic hydrocarbon group, a divalent heterocyclic group containing 2 to 35 carbon atoms, or any of the groups (1-1) to (1-3) below,
R ⁵⁵ and R ⁵⁶ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms,
Z ¹ and Z ² independently represent a direct bond, -O-, -S-,> CO, -CO-O-, -O-CO-, -SO _2- , -SS-, -SO-,> NR ⁵⁷ Or ＞ PR ⁵⁸
R ⁵⁷ and R ⁵⁸ represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a heterocyclic group containing 2 to 35 carbon atoms,
The aliphatic hydrocarbon group represented by the above Y ¹ , R ⁵⁵ , R ^56, and R ⁵⁷ , the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, and the methylene group in the heterocyclic group containing 2 to 35 carbon atoms can also be replaced by Substituted with -O-, -S-, -CO-, -COO-, -OCO-, or -NH- or a combination of these,
(* Means that the * part is bonded to the adjacent base)

[Chemical 6]

(In the above formula, R ⁵⁹ represents a hydrogen atom, a phenyl group which may have a substituent, or a cycloalkyl group having 3 to 10 carbon atoms which may have a substituent.
R ⁶⁰ represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group or halogen atom having 2 to 10 carbon atoms, and the alkyl group, alkoxy group, and alkenyl group may have a substituent. base,
c1 represents an integer from 0 to 5,
(* Means that the * part is bonded to the adjacent base)

[Chemical 7]

(* Means that the * part is bonded to the adjacent base)

[Chemical 8]

(In the above formula, R ⁶¹ and R ⁶² each independently represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, and 6 to 20 carbon atoms. An arylthio group, an arylalkenyl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, a heterocyclic group or halogen atom having 2 to 20 carbon atoms,
The methylene group in the alkyl group and the aralkyl group represented by the above R ⁶¹ and R ⁶² may be substituted with a carbon-carbon double bond, -O- or -S-,
R ⁶¹ can also form a ring with each other by using adjacent R ⁶¹ ,
c2 represents a number from 0 to 4,
c3 represents a number from 0 to 8,
c4 is a number from 0 to 4,
c5 is a number from 0 to 4,
The total number of c4 and c5 is 2 to 4,
(* Means that the * part is bonded to the adjacent base)

[Chemical 9]

(In the above general formula (2), Y ¹¹ represents a trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms, an alicyclic hydrocarbon group having 3 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or Heterocyclic group containing 2 to 35 carbon atoms,
Z ¹ , Z ² and Z ³ each independently represent a group in the same range as the group represented by Z ¹ to Z ² in the general formula (1),
The aliphatic hydrocarbon group represented by the above Y ¹¹ , the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, and the heterocyclic group-containing methylene group having 2 to 35 carbon atoms may be substituted with a carbon-carbon double bond, -O -, -CO-, -O-CO-, -CO-O- or -SO _2- )

[Chemical 10]

(In the general formula (3), Y ¹² represents a carbon atom, a tetravalent carbon atom having 1 to 35 carbon atoms, a tetravalent carbon atom having 6 to 35 carbon atoms, or an aromatic ring-containing hydrocarbon group, or a tetravalent carbon atom. Heterocyclic group containing 2 to 35,
The aliphatic hydrocarbon group represented by the above Y ¹² , the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms or the heterocyclic group-containing methylene group having 2 to 35 carbon atoms may be substituted with -COO-, -O-, -OCO-, -NHCO-, -NH- or -CONH-,
Z ¹ to Z ⁴ are each independently a base in the same range as the base represented by Z ¹ to Z ² in the general formula (1))

[Chemical 11]

(In the above general formula (4), Y ¹³ represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, a pentavalent carbon atom having 6 to 30 aromatic ring-containing hydrocarbon groups, or a pentavalent carbon atom having 2 to 30 Heterocyclic group,
The aliphatic hydrocarbon group represented by the above Y ¹³ , the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms or the heterocyclic group-containing methylene group having 2 to 35 carbon atoms may be substituted with -COO-, -O-, -OCO-, -NHCO-, -NH- or -CONH-,
Z ¹ to Z ⁵ are each independently a base in the same range as the base represented by Z ¹ to Z ² in the general formula (1))

[Chemical 12]

(In the general formula (5), Y ¹⁴ represents a hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, a hexavalent aromatic ring group having 6 to 35 carbon atoms, or a hexavalent carbon atom having 2 to 35 Heterocyclic group,
The aliphatic hydrocarbon group represented by the above Y ¹⁴ , the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms or the heterocyclic group-containing methylene group having 2 to 35 carbon atoms may be substituted with -COO-, -O-, -OCO-, -NHCO-, -NH- or -CONH-,
Z ¹ to Z ⁶ are each independently a group in the same range as the group represented by Z ¹ to Z ² in the general formula (1))

Among the divalent aliphatic hydrocarbon groups having 1 to 35 carbon atoms represented by Y ^{1 in} the group represented by the general formula (1), specific examples of the divalent aliphatic hydrocarbon groups represented by X are listed. Examples of the carbon number group include methane, ethane, propane, isopropane, butane, second butane, third butane, isobutane, hexane, 2-methylhexane, and 3-methyl. Hexane, heptane, 2-methylheptane, 3-methylheptane, isoheptane, third heptane, 1-methyloctane, isooctane, third octane, cyclopropane, cyclobutane Hydrogen atoms of aliphatic hydrocarbons such as alkane, cyclopentane, cyclohexane, cycloheptane, 2,4-dimethylcyclobutane, 4-methylcyclohexane are substituted with Z ¹ and Z ² 2-valent base. The methylene group in these groups may be substituted with -O-, -S-, -CO-, -COO-, -OCO-, -NH- or a combination of these groups.

Examples of the divalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms having a divalent number represented by Y ^{1 in} the group represented by the general formula (1) include a divalent aromatic ring-containing hydrocarbon group represented by the above X. For example, Examples include divalent groups in which a hydrogen atom containing an aromatic cyclic hydrocarbon such as benzene, naphthalene, and biphenyl is substituted with Z ¹ and Z ² .

Examples of the divalent heterocyclic group having 2 to 35 carbon atoms represented by Y ^{1 in} the group represented by the general formula (1) include a divalent heterocyclic group having a divalent number represented by X. For example, List piperidine, piperidine, pyrimidine, da, tri, hexahydrotri, furan, tetrahydrofuran, pyrene, A bivalent group in which a hydrogen atom of a heterocyclic compound such as thiophene, tetrahydrothiophene (thiolane) is substituted with Z ¹ and Z ² .

Among the groups represented by the general formula (1), the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group and the heterocyclic group-containing hydrogen atom represented by Y ¹ may be substituted with a halogen atom, a cyano group, a nitro group, or a carbon atom number. 1 to 8 alkoxy groups. Examples of such a substituent substituted for a hydrogen atom such as an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group, and a heterocyclic group include the same substituents as those substituted for a hydrogen atom such as an alkyl group represented by R ² and the like. Each of the functional groups such as the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group, and the heterocyclic group may have a substituent. Unless otherwise specified, they are unsubstituted or substituted without a substituent.

Examples of the alkyl group having 1 to 8 carbon atoms represented by R ⁵⁵ and R ⁵⁶ among the groups represented by the general formula (1) include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, Second butyl, third butyl, isobutyl, pentyl, isopentyl, third pentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2 -Heptyl, 3-heptyl, isoheptyl, third heptyl, 1-octyl, isooctyl, third octyl, etc.

Examples of the aryl group having 6 to 20 carbon atoms represented by R ⁵⁵ and R ⁵⁶ among the groups represented by the general formula (1) include a phenyl group, a naphthyl group, a 2-methylphenyl group, and a 3-methyl group. Phenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, 4 -Third butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4- (2-ethylhexyl) phenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-di-tertiary-butylphenyl, 2,5-di-tertiary-butylphenyl, 2,6-di-tertiary-butylphenyl, 2,4-di-tertiary-pentylbenzene Group, 2,5-di-third-pentylphenyl, 2,4,5-trimethylphenyl and the like.

Examples of the aralkyl group having 7 to 20 carbon atoms represented by R ⁵⁵ and R ⁵⁶ in the group represented by the general formula (1) include a benzyl group, a phenethyl group, and a 2-phenylpropane-2-yl group. , Diphenylmethyl, triphenylmethyl, styryl, phenallyl and the like.

Among the groups represented by the general formula (1), R ⁵⁷ and R ⁵⁸ represent aliphatic hydrocarbon groups having 1 to 35 carbon atoms, aromatic ring hydrocarbon groups having 6 to 35 carbon atoms, or 2 to 35 carbon atoms. The heterocyclic group may be the same as those exemplified as R ⁵³ and R ⁵⁴ .

Examples of the cycloalkyl group having 3 to 10 carbon atoms represented by R ⁵⁹ among the groups represented by the general formula (1-1) include cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, and cyclo An octyl group and the like are substituted with a hydrogen atom of an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms.

Examples of the alkyl group having 1 to 10 carbon atoms represented by R ⁶⁰ among the groups represented by the general formula (1-1) include carbon atoms among those exemplified as the alkyl group represented by R ² and the like. For 1 to 10.

As the alkoxy group having 1 to 10 carbon atoms represented by R ^{60 in} the group represented by the above-mentioned general formula (1-1), the above-mentioned terminal of the group exemplified as the alkyl group represented by R ² and the like can be used. Among those in which methylene is substituted with -O-, the number of carbon atoms is 1 to 10. Examples of the alkoxy group include a methoxy group, an ethoxy group, and an isopropoxy group.

Examples of the alkenyl group having 2 to 10 carbon atoms represented by R ⁶⁰ among the groups represented by the general formula (1-1) include vinyl, allyl, 1-propenyl, isopropenyl, 2- Butenyl, 1,3-butadienyl, 2-pentenyl, and 2-octenyl.

The hydrogen atom of the alkyl group, alkoxy group, and alkenyl group represented by R ⁶⁰ may be substituted with a halogen atom, and the substitution position is not limited. Examples of the halogen atom include those exemplified above as R ² and the like.

Among the groups represented by the general formula (1-3), R ⁶¹ and R ⁶² represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and an alkyl group having 7 to 20 carbon atoms. Examples of the aralkyl group and the halogen atom include those satisfying a specific number of carbon atoms among those exemplified as R ² described above.

Examples of the aryloxy group having 6 to 20 carbon atoms represented by R ⁶¹ and R ⁶² in the group represented by the general formula (1-3) include a phenoxy group, a naphthyloxy group, and 2-methylbenzene. Oxy, 3-methylphenoxy, 4-methylphenoxy, 4-vinylphenoxy, 3-isopropylphenoxy, 4-isopropylphenoxy, 4-butylbenzene Oxy, 4-tert-butylphenoxy, 4-hexylphenoxy, 4-cyclohexylphenoxy, 4-octylphenoxy, 4- (2-ethylhexyl) phenoxy, 2 , 3-dimethylphenoxy, 2,4-dimethylphenoxy, 2,5-dimethylphenoxy, 2,6-dimethylphenoxy, 3,4-dimethyl Phenoxy, 3,5-dimethylphenoxy, 2,4-di-third-butylphenoxy, 2,5-di-third-butylphenoxy, 2,6-di-th Tributylphenoxy, 2,4-di-tertiarypentylphenoxy, 2,5-tertiarypentylphenoxy, 4-cyclohexylphenoxy, 2,4,5-trimethyl A phenoxy group and a ferrocenyloxy group and a group in which a hydrogen atom is substituted with a halogen atom.

Examples of the arylthio group having 6 to 20 carbon atoms represented by R ⁶¹ and R ⁶² in the group represented by the general formula (1-3) include a carbon atom having 6 to 20 carbon atoms which may be substituted with a halogen atom. The oxygen atom of the aryloxy group is substituted by a sulfur atom.

Examples of the arylalkenyl group having 8 to 20 carbon atoms represented by R ⁶¹ and R ⁶² in the group represented by the general formula (1-3) include 6 to 6 carbon atoms which may be substituted with a halogen atom. The oxygen atom of the aryloxy group of 20 is substituted with vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 2-octyl Alkenyl and other alkenyl groups.

Examples of the heterocyclic group having 2 to 20 carbon atoms represented by R ⁶¹ and R ⁶² in the group represented by the general formula (1-3) include pyridyl, pyridyl, piperidinyl, piperidinyl, Pyrimidinyl, daphyl, triyl, hexahydrotriyl, furyl, tetrahydrofuryl, fluorenyl, Group, thienyl group, thiofuranyl group, and a group obtained by substituting a hydrogen atom of these groups with a halogen atom, and the like.

Each functional group such as an aryloxy group, an arylthio group, an arylalkenyl group, and a heterocyclic group-containing group represented by R ⁶¹ and R ⁶² in the group represented by the general formula (1-3) may have a substituent, as long as Unless otherwise specified, they are unsubstituted or substituted. Examples of the substituent that replaces a hydrogen atom such as an aryloxy group, an arylthio group, an arylalkenyl group, and a heterocyclic group include the same substituents as those substituted with a hydrogen atom such as an alkyl group represented by R ² and the like. base.

Examples of the trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms represented by Y ^{11 in} the group represented by the general formula (2) include specific carbons among the trivalent aliphatic hydrocarbon groups represented by X described above. The atomic number group includes, for example, a trivalent group in which a hydrogen atom of the aliphatic hydrocarbon exemplified in the description of Y ¹ in the general formula (1) is substituted with Z ¹ , Z ^2, and Z ³ . The methylene groups in these groups may also be substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO _2- , -NH- or a combination thereof A base.

Examples of the trivalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y ^{11 in} the group represented by the general formula (2) include a trivalent aromatic ring-containing hydrocarbon group represented by the above X. For example, The trivalent group in which the hydrogen atom of the aromatic ring-containing hydrocarbon exemplified in the description of Y ¹ in the general formula (1) is substituted with Z ¹ , Z ² and Z ³ is listed.

Examples of the trivalent heterocyclic group having 2 to 35 carbon atoms represented by Y ^{11 in} the group represented by the general formula (2) include a trivalent heterocyclic group containing X represented by the above X. For example, The trivalent group in which the hydrogen atom of the heterocyclic compound exemplified in the description of Y ¹ in the general formula (1) is substituted with Z ¹ , Z ² and Z ³ is listed.

Examples of the tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y ^{12 in} the group represented by the general formula (3) include the removal of 3 hydrogens from the monovalent aliphatic hydrocarbon group represented by X. An atomic group may be, for example, a tetravalent group in which the hydrogen atom of the aliphatic hydrocarbon exemplified in the description of Y ¹ in the general formula (1) is substituted with Z ¹ , Z ² , Z ^3, and Z ⁴ base. The methylene group in these groups may be substituted with -O-, -S-, -CO-, -COO-, -OCO-, -NH- or a combination of these groups.

Examples of the tetravalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y ^{12 in} the group represented by the above general formula (3) include a monovalent aromatic ring-containing hydrocarbon group represented by X which is removed by 3 Examples of the group consisting of three hydrogen atoms include the aromatic ring-containing hydrogen atom exemplified in the description of Y ¹ in the general formula (1), which is substituted with Z ¹ , Z ² , Z ^3, and Z ⁴ . 4-valent base.

As the tetravalent heterocyclic group having 2 to 35 carbon atoms represented by Y ^{12 in} the group represented by the above general formula (3), a monovalent heterocyclic group containing 3 represented by X may be removed except for 3 Examples of the group consisting of three hydrogen atoms include those in which the hydrogen atom of the heterocyclic compound exemplified in the description of Y ¹ in the above general formula (1) is substituted with Z ¹ , Z ² , Z ³ and Z ⁴ 4-valent base.

Examples of the 5-valent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by Y ^{13 in} the group represented by the general formula (4) include the removal of 4 hydrogens from the monovalent aliphatic hydrocarbon group represented by X. Atom-based groups include, for example, those in which the hydrogen atom of the aliphatic hydrocarbon exemplified in the description of Y ¹ in the general formula (1) is substituted with Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ 5 valent base. The methylene groups in these groups may also be substituted with -O-, -S-, -CO-, -CO-O-, -O-CO-, -SO _2- , -NH- or a combination thereof A base.

Examples of the 5-valent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y ^{13 in} the group represented by the general formula (4) include the removal of 4 from the monovalent aromatic ring-containing hydrocarbon group represented by X described above. Examples of the group consisting of three hydrogen atoms include the aromatic ring-containing hydrogen atom exemplified in the description of Y ¹ in the general formula (1), which is substituted with Z ¹ , Z ² , Z ³ , Z ^4, and Z. ⁵ into a 5-valent base.

Examples of the 5-valent heterocyclic group having 2 to 35 carbon atoms represented by Y ^{13 in} the group represented by the above general formula (4) include the removal of 4 from the monovalent heterocyclic group containing X represented by the above X. Examples of the group consisting of three hydrogen atoms include the hydrogen atoms of the heterocyclic compound exemplified in the description of Y ¹ in the general formula (1), which are substituted with Z ¹ , Z ² , Z ³ , Z ^4, and Z. ⁵ into a 5-valent base.

Examples of the hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by Y ¹⁴ in the general formula (5) include those obtained by removing 5 hydrogen atoms from the monovalent aliphatic hydrocarbon group represented by X described above. For example, the hydrogen atom of the aliphatic hydrocarbon exemplified in the description of Y ¹ in the above general formula (1) may be substituted with Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ and Z ⁶ . 6-valent group, the methylene group in the group may also be substituted with -O-, -S-, -CO-, -COO-, -OCO-, -SO _2- , -NH- or a combination of these The base.

Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms having a valence of 6 to 35 represented by Y ¹⁴ in the general formula (5) include removal of 5 hydrogen atoms from the monovalent aromatic ring-containing hydrocarbon group represented by the above X For example, the aromatic ring-containing hydrogen atom exemplified in the description of Y ¹ in the above general formula (1) may be substituted with Z ¹ , Z ² , Z ³ , Z ⁴ , Z ^5, and Z ^6. Into a 6-valent base.

Examples of the hexavalent heterocyclic group containing 2 to 35 carbon atoms represented by Y ¹⁴ in the above general formula (5) include the removal of 5 hydrogen atoms from the monovalent heterocyclic group represented by X described above, and For example, the hydrogen atom of the heterocyclic-containing compound exemplified in the description of Y ¹ in the general formula (1) above may be substituted with Z ¹ , Z ² , Z ³ , Z ⁴ , Z ^5, and Z ^6. Into a 6-valent base.

The X is preferably an aliphatic hydrocarbon group having 1 to 120 carbon atoms, and among them, an aliphatic hydrocarbon group having 1 to 10 carbon atoms is preferred. The reason is that the above compound A becomes an easy synthesizer when X is the aforementioned group.

When n is 2 to 10, X is preferably an aliphatic hydrocarbon group having 1 to 120 carbon atoms, and particularly preferably an aliphatic hydrocarbon group having 1 to 10 carbon atoms. In addition, as the X, an aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a methylene group in these groups can be preferably substituted with -O-, -S. -, -CO-, -COO-, -OCO-. The reason is that, when X is the above-mentioned group, the compound A is excellent in light absorption around 400 nm. The reason is that the compound A is easy to be made into a compound with low volatility and is easy to synthesize.

When n is 2, the above-mentioned X is preferably a divalent aliphatic hydrocarbon group having 1 to 120 carbon atoms, particularly preferably a divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, and particularly preferably 2 Valent aliphatic hydrocarbon groups having 4 to 10 carbon atoms, of which hydrogen atoms in the base and unsubstituted methylene unsubstituted carbon atoms having 5 to 10 divalent aliphatic hydrocarbon groups (unsubstituted carbon) are particularly preferred. A bivalent aliphatic hydrocarbon group having 5 to 10 atoms). Among them, a hydrogen atom in a radical and a straight chain of methylene group which is unsubstituted are preferably a bivalent aliphatic hydrocarbon group having 5 to 10 carbon atoms (a straight chain and an unsubstituted carbon atom having 5 to 10 carbon atoms). Aliphatic hydrocarbon group), among which, a hydrogen atom in the group and an unsubstituted linear alkylene group having 5 to 10 carbon atoms (a straight chain and unsubstituted carbon atom having 5 to 10) 10 alkylene). The reason is that the above compound A becomes an easy synthesizer when X is the aforementioned group. The aliphatic hydrocarbon group may be linear or branched, but is preferably linear. The reason is that the above-mentioned compound A is excellent in light absorptivity near 400 nm. The reason is that the above compound A becomes an easy synthesizer. The reason is that the compound A is easily made into a compound having low volatility.

When n is 2, the X is also preferably a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms or a divalent methylene group in an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms. Substituted by -O-, -S-, -CO-, -COO-, -OCO-, among them, a divalent aliphatic hydrocarbon group having 3 to 20 carbon atoms or a divalent carbon atom is preferred. The methylene group in the aromatic ring-containing hydrocarbon group having a number of 8 to 20 is substituted by -O-, -S-, -CO-, -COO-, -OCO- 5 to 15 aliphatic hydrocarbon groups or divalent aromatic ring-containing hydrocarbon groups having 10 to 20 carbon atoms are substituted with -O-, -S-, -CO-, -COO-, -OCO- The formed group is particularly preferably a divalent aliphatic hydrocarbon group having 5 to 15 carbon atoms or a divalent aromatic ring-containing hydrocarbon group having 10 to 20 carbon atoms is substituted with -O-,- CO-, -COO-, -OCO-, especially preferred are those having 5 to 15 carbon atoms or those having 10 to 20 carbon atoms which are a combination of alkylene and alkylene The methylene group is substituted with -O-, -CO-, -COO-, -OCO-, and particularly preferred is a linear or branched alkylene having 5 to 15 carbon atoms. Or the methylene group in the above-mentioned alkylene group having 12 to 18 carbon atoms, an arylene group, and an alkylene group are sequentially substituted by -O-, -CO-, -COO-, -OCO -Creating the base.
The reason is that, when X is the above-mentioned group, the compound A is excellent in light absorption around 400 nm. The reason is that the above-mentioned compound A is easily made into a compound having low volatility and is easy to synthesize.

In the present invention, when n is 3, the X is preferably a trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms or a methylene group in the aliphatic hydrocarbon group is substituted with -O-, -S-, -CO-, -COO-, -OCO-, particularly preferably a trivalent aliphatic hydrocarbon group having 5 to 15 carbon atoms or a methylene group in the aliphatic hydrocarbon group is substituted by- O-, -S-, -CO-, -COO-, -OCO-, in which the methylene group in a trivalent aliphatic hydrocarbon group having 8 to 15 carbon atoms is more preferably substituted with -O -, -S-, -CO-, -COO-, -OCO-, in which the methylene group in a trivalent aliphatic hydrocarbon group having 8 to 15 carbon atoms is more preferably substituted with -O- , -CO-, -COO-, -OCO-. Among them, it is particularly preferable that the number of carbon atoms is 8 to 15, and each of the three carbon atoms in the aliphatic hydrocarbon is removed by one hydrogen atom. And a methylene group is substituted with -O-, -CO-, -COO-, -OCO-. The reason is that, when X is the above-mentioned group, the compound A is excellent in light absorption around 400 nm. The reason is that the above-mentioned compound A is easily made into a compound having low volatility and is easy to synthesize.

In the present invention, when n is 1, the X is a monovalent group. For example, when the compound A is represented by the general formula (A1), the X is preferably a hydrogen atom or a carbon atom. The alkyl group having a number of 1 to 40 is the same as a preferable group of R ^{4. When} the compound A is represented by the general formula (A2), the X is preferably an alkyl group having a hydrogen atom and 1 to 40 carbon atoms. Group or an aryl group having 6 to 30 carbon atoms, and the same group as the preferred group of R ^{3. When} the compound A is represented by the general formula (A3), X is preferably a hydrogen atom and a carbon number of 1 An alkyl group such as -40 is the same as a preferable group of R ⁵⁵ . The reason is that the above-mentioned compound A is excellent in light absorptivity near 400 nm. The reason is that the above-mentioned compound A is easily made into a compound having low volatility and is easy to synthesize.

Specific examples of the compound A include compounds represented by the following formulae (1) to (75).

[Chemical 13]

[Chemical 14]

[Chemical 15]

[Chemical 16]

[Chemical 17]

[Chemical 18]

[Chemical 19]

The compound of the present invention is preferably a compound represented by the above general formula (A1), and more preferably n is 2 or 3, X is an aliphatic hydrocarbon group having 1 to 35 carbon atoms, and 6 to 35 carbon atoms The aromatic ring-containing hydrocarbon group or the methylene group in these groups is substituted with -O-, -S-, -CO-, -COO-, -OCO-. The reason is that the above-mentioned compound A is more excellent in the balance of light absorption, low volatility, and ease of synthesis in the vicinity of 400 nm.

Among them, in the present invention, R ¹ in the general formula (A1) is preferably a cyano group or -COOR, and R is an alkyl group having 1 to 10 carbon atoms or an alkyl group having 1 to 10 carbon atoms. A hydrogen atom is substituted with an ethylenically unsaturated group, R ² is a hydrogen atom, R ³ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 15 carbon atoms, and X is An aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a methylene group in these groups is substituted with -O-, -S-, -CO-, -COO-, -OCO-, 5a is 0 and n is 2 or 3. The reason is that the above-mentioned compound A is more excellent in the balance of light absorption, low volatility, and ease of synthesis in the vicinity of 400 nm.

Further, in the compound represented by the general formula (A1), it is preferable that R ¹ in the formula is a cyano group or -COOR, and R is an alkyl group having 1 to 5 carbon atoms or an alkane having 1 to 5 carbon atoms. A group in which one hydrogen atom is substituted with an ethylenically unsaturated group, R ² is a hydrogen atom, R ³ is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an aromatic group having 6 to 12 carbon atoms X is an aliphatic hydrocarbon group having 5 to 10 carbon atoms, or an aliphatic hydrocarbon group having 5 to 15 carbon atoms or an aromatic ring-containing hydrocarbon group having 10 to 20 carbon atoms, and the methylene group in these groups is substituted Is a base of -COO- or -OCO-, 5a is 0, and n is 2 or 3. The reason is that the above-mentioned compound A is more excellent in the balance of light absorption, low volatility, and ease of synthesis in the vicinity of 400 nm.

The compound of the present invention is also preferably a compound represented by the general formula (A3). Among them, n is 1 and R ⁴ is preferably an alkyl group having 1 to 10 carbon atoms or a hydrogen atom in these groups. One of the groups is substituted with an ethylenically unsaturated group, or one or two or more of the methylene groups in the alkyl group having 1 to 40 carbon atoms are independently substituted with -COO- or -OCO- Compounds in which two or more hydrogen atoms in the group are substituted with an ethylenically unsaturated group, particularly preferably wherein R ¹ is a cyano group or -COOR, and R is an alkyl group or carbon atom having 1 to 10 carbon atoms One of the hydrogen atoms in the alkyl group of 1 to 10 is substituted with an ethylenically unsaturated group, R ² is a hydrogen atom, R ³ is a hydrogen atom, an alkyl group of 1 to 10 carbon atoms, or a carbon atom 6 to 15 aryl groups, R ⁴ is an alkyl group having 1 to 10 carbon atoms or one of the hydrogen atoms in these groups is substituted with an ethylenically unsaturated group or an alkyl group having 1 to 40 carbon atoms One or two or more of the methylene groups in the group are independently substituted with -COO- or -OCO- and two or more hydrogen atoms in the group are substituted with an ethylenically unsaturated group, and X is a hydrogen atom, 5a is 0 and n is 1 The reason is that the above-mentioned compound A is more excellent in the balance of light absorption, low volatility, and ease of synthesis in the vicinity of 400 nm.

Further, in the compound represented by the general formula (A3), it is preferable that R ¹ in the formula is a cyano group or -COOR, and R is an alkyl group having 1 to 5 carbon atoms or an alkane having 1 to 5 carbon atoms. One of the hydrogen atoms in the group is substituted with an ethylenically unsaturated group, R ² is a hydrogen atom, R ³ is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 6 to 12 carbon atoms Aryl, R ⁴ is an alkyl group having 1 to 5 carbon atoms, one of hydrogen atoms in an alkyl group having 3 to 10 carbon atoms is substituted with an ethylenically unsaturated group, or 5 to 25 carbon atoms One or two or more methylene groups in the alkyl group are independently substituted with -COO- or -OCO- and two or more hydrogen atoms in the group are substituted with an ethylenically unsaturated group, X is For a hydrogen atom, 5a is 0 and n is 1. The reason is that the above-mentioned compound A is more excellent in the balance of light absorption, low volatility, and ease of synthesis in the vicinity of 400 nm.

The manufacturing method of the said compound A is not specifically limited if it is a method which can obtain the compound A of a desired structure. Examples of the production method include a method of preparing a compound (compound (1)) having an aldehyde structure as described in Japanese Patent Application Laid-Open No. 11-246627, and adding a cyano-containing compound to Compound 1 for reaction. . Examples of the compound (1) include compounds having an indole-3-carbaldehyde structure. Examples of the cyano-containing compound include ethyl cyanoacetate and malononitrile.

The maximum absorption wavelength of the compound A is not limited as long as it can absorb light in the vicinity of 400 nm, and it can be set to 350 nm or more and 420 nm or less. The maximum absorption wavelength is preferably 360 nm or more and 420 nm or less, preferably 380 nm or more and 410 nm or less, preferably 390 nm or more and 410 nm or less, and more preferably 395 nm or more and 405 nm or less. The reason is that the above-mentioned compound A can effectively absorb light around 400 nm by the above-mentioned maximum absorption wavelength being within the above-mentioned range.

The maximum absorption wavelength can be obtained by measuring the absorbance in accordance with JIS K0115. The above-mentioned maximum absorption wavelength can be obtained, for example, by preparing Compound A dissolved in a solvent (chloroform) so as to have a concentration of 1.0 × 10 ^-5 mol / L as a sample for evaluation, and then evaluating A sample is filled in a quartz cell (optical path length 10 mm, thickness 1.25 mm), and the absorbance is measured using an absorbance photometer (for example, U-3900 (manufactured by Hitachi High-Tech Science). The maximum absorption wavelength can be above 250 nm The measurement was performed in a range of 600 nm or less.

The absorbance at 400 nm of the above-mentioned compound A can be appropriately set depending on the use of the above-mentioned compound A. For example, it is preferably 0.3 or more, of which 0.4 or more is preferable, and 0.5 or more is particularly preferable. The reason is that the above-mentioned compound A can efficiently absorb light around 400 nm. As a method for measuring the absorbance, the same method as that for measuring the maximum absorption wavelength can be used.

The absorbance at 450 nm of the compound A is not limited as long as it can absorb light in the vicinity of 400 nm, and may be set to 0.1 or less. Among them, 0.05 or less is preferred, and 0.01 or less is particularly preferred.

As the absorbance at 350 nm of the compound A, any material capable of absorbing light in the vicinity of 400 nm may be used, and may be set to 0.4 or less. Among them, 0.3 or less is preferred, and 0.2 or less is particularly preferred.

As the absorbance at 300 nm of the compound A, any material capable of absorbing light in the vicinity of 400 nm may be used, and it may be set to 0.3 or less. Among them, 0.1 or less is preferable, and 0.05 or less is particularly preferable.

The half-value width of the absorption peak including the maximum absorption wavelength of the compound A is not limited as long as it can absorb light around 400 nm. For example, it can be set to 100 nm or less. Among them, 80 nm or less is more preferable. It is 10 nm or more and 60 nm or less. The reason is that, as the half-value width is in the above range, the compound A can efficiently absorb light in the vicinity of 400 nm. As a method for measuring the absorption peak, the same method as that for measuring the maximum absorption wavelength can be used. The half-value width may be a width of a wavelength that becomes one half of the absorbance (maximum absorption peak) at the maximum absorption wavelength among the absorption peaks including the maximum absorption wavelength.

As the 10% weight reduction temperature of the above-mentioned compound A under normal pressure, there is no limitation as long as it has the required volatility, and it can be appropriately set depending on the application of the compound A, for example, preferably 250 ° C or higher. Above 300 ° C, particularly preferably above 350 ° C. The reason for this is that the above-mentioned compound A has a lower volatility. The upper limit of the 10% weight reduction temperature is not particularly limited because it is higher, and may be, for example, 450 ° C or lower.
Regarding the weight reduction temperature under normal pressure, a differential thermal-thermogravimetric simultaneous measurement device can be used for a sample of about 5 mg in a nitrogen atmosphere of 200 mL / min at an initial temperature of 30 ° C, an end temperature of 500 ° C, and a rate of 10 ° C. The heat reduction amount of the sample was measured when the temperature was raised, and the temperature at the time when the weight loss of the sample was 10% relative to the time point at 30 ° C was set as the 10% weight reduction temperature. The differential thermal-thermogravimetric simultaneous measurement device may be any device that can accurately measure the heat reduction amount. For example, a model manufactured by SII NanoTechnology: EXSTAR TG / DTA6200 can be used.

The absorbance maintenance rate of the above compound A can be appropriately set depending on the use of the compound A, and the higher the better, for example, it is preferably 60% or more, preferably 70% or more, of which 80% or more is particularly preferable More than 90. The reason is that the above-mentioned compound A is excellent in light resistance.
The following methods (1) to (3) can be used for the absorbance maintenance ratio.
(1) Compound A and thermoplastic polymethyl methacrylate (PMMA) are dissolved in dichloromethane and added to a petri dish to be dried, and the concentration of Compound A to be prepared as an evaluation sample is 3.8% by mass. PMMA film (100 μm).
(2) The sample for evaluation was irradiated with xenon light for 240 hours.
(3) For evaluation samples before and after irradiation with xenon light, the change in absorbance at the above-mentioned maximum absorption wavelength of Compound A was measured, and the absorbance maintenance ratio (absorbance after irradiation / absorbance before irradiation) was calculated.

For the irradiation of xenon light, for example, a xenon weather tester "ATLAS Weather-Ometer Ci4000" (manufactured by Toyo Seiki Seisakusho Co., Ltd.) can be used.
Examples of the irradiation conditions of xenon light include the following conditions.
Irradiance: 0.55 W / m ² (wavelength 340 nm)
Temperature in test tank: 62 ℃
Relative humidity in the test tank: 50%

As the above-mentioned compound A, it can be used as a light absorber that absorbs light near 400 nm. As a more specific application using such a light absorber, for example, a recording layer of an optical recording medium such as CD-R, DVD-R, DVD + R, or BD-R (Blu-ray Disc Recordable) And other optical recording materials, liquid crystal display devices (LCD), plasma display panels (PDP), electroluminescence displays (ELD), cathode tube display devices (CRT), fluorescent display tubes, field emission displays and other image display devices Optical filters, inks, coatings, coating agents, sealants, optical fibers, automotive interior and exterior materials used in various applications such as analysis equipment, semiconductor device manufacturing, astronomical observation, optical communication, eyeglass lenses, and windows , Building materials, etc.
Examples of the optical filter used in the liquid crystal display device (LCD) include a color filter and the like. Moreover, as an optical filter used for the said electroluminescent display, the use which prevents the light deterioration of a color filter and an organic electroluminescence element (organic EL element), etc. are mentioned.
Among the above applications, the above-mentioned optical filter is preferred, and among them, an optical filter used in an application for preventing light degradation of an organic EL element is preferred. The reason is that the organic EL element can be stably protected from light deterioration.

B. Light Absorbent Next, the light absorbent of the present invention will be described.
The light absorber of the present invention is characterized by including the above-mentioned compound A. By including the above-mentioned compound A, the above-mentioned light absorber becomes more excellent in light absorptivity in the vicinity of 400 nm.
Hereinafter, each component contained in the light absorber of this invention is demonstrated in detail.

Compound A
The content of the compound A is not particularly limited as long as it can provide a desired light absorbency to the light absorber. The content can be 100 parts by mass in 100 parts by mass of the light absorbent, that is, the light absorber can be the compound A. In addition, the above-mentioned content may include less than 100 parts by mass in 100 parts by mass of the light absorbent, that is, the light absorber may be a composition containing the above-mentioned compound A and other components. For example, it may be more than 10 parts by mass and 99 It is preferably 50 parts by mass or more and 95 parts by mass or less.
In this specification, when there is no special declaration, the content is a mass basis.

The type of the compound A contained in the light absorber may be only one kind, or two or more kinds. The above-mentioned types may be, for example, two or more and five or less. Examples of the light absorber containing the two types of the above-mentioned compound A include, for example, those containing the above-mentioned compound A1 and compound A2, those containing the compound A of n = 1 and compound A of the n = 2, and hydrogen atoms including a substituted indole ring. Compounds in which the substituent has a polymerizable group, compounds without a polymerizable group, and the like.

The above compound A can be the same as that described in the item "A. Compound", and therefore description thereof will be omitted.

2. Other Components The light absorber includes the compound A described above, but may include other components as necessary. Examples of such other components include those described in the items "2. Resin" and "3. Other components" in the "C. Composition" described below.

The shape of the light absorbing agent may be powder or granular.
In the case of a pellet, as the method for producing the light absorber, for example, the following method can be used: the compound A and the resin are mixed using an extruder or the like, and then molded into a pellet.

C. Composition Next, the composition of the present invention will be described.
The composition of the present invention is characterized by including the above-mentioned compound A and a resin. By including the above-mentioned compound A, the above-mentioned composition becomes a more excellent absorber of light in the vicinity of 400 nm.
Hereinafter, each component contained in the composition of this invention is demonstrated in detail.

Compound A
The content of the compound A is not particularly limited as long as it can provide a desired light absorption property to the composition. The content may be, for example, 0.05 parts by mass or more and 10 parts by mass or less with respect to 100 parts by mass of the solid component of the composition, and preferably 0.1 parts by mass or more and 5 parts by mass or less. The reason is that, when the content is in the above range, it is possible to efficiently give resin or the like the absorption energy of light in the vicinity of 400 nm. The so-called solid component refers to all components except for the solvent.

The kind of the compound A contained in the composition may be only one kind, or two or more kinds. The above-mentioned types may be, for example, two or more and five or less.

The above compound A can be the same as that described in the item "A. Compound", and therefore description thereof will be omitted.

2. Resin The compound A can stably hold the compound A by including the resin. As a result, the composition can easily form, for example, a film, a molded body, or the like containing the compound A. As such a resin, any compound can be used as long as it can stably hold Compound A, and examples thereof include a polymerizable compound having a polymerizable group and a polymer having no polymerizable group.

(1) Polymerizable compound The polymerizable compound has a polymerizable group. By polymerizing the polymerizable groups with each other, the molecular weight can be increased, and the compound A can be stably held. The polymerizable compound is different depending on the type of the polymerizable group, that is, the type of the polymerization reaction, and examples thereof include a radical polymerizable compound having a radical polymerizable group, a cationic polymerizable compound having a cation polymerizable group, and An anionic polymerizable compound and the like.

(1-1) Radical Polymerizable Compound A radical polymerizable compound is one having a radical polymerizable group.
The radical polymerizable group is not limited as long as it can be polymerized by a radical, and examples thereof include ethylenically unsaturated groups such as a (meth) acrylfluorenyl group and a vinyl group. The (meth) acrylfluorenyl group can be used including the meaning of acrylmethylene and methacrylmethyl.
The radical polymerizable compound may be one having one or more radical polymerizable groups, and a monofunctional compound having one radical polymerizable group or a polyfunctional compound having two or more radical polymerizable groups may be used.

As said radically polymerizable compound, the compound which has an acid value, the compound which does not have an acid value, etc. can be used. Examples of the compound having an acid value include a (meth) acrylate compound having a carboxyl group and the like such as (meth) acrylic acid. Examples of the compound having no acid value include (meth) acrylate compounds having no carboxyl group, such as epoxy acrylate resin and 2-hydroxyethyl (meth) acrylate.

The said radically polymerizable compound can be used individually or in mixture of 2 or more types. For example, the radically polymerizable compound may be a combination of a compound having an ethylenically unsaturated group and an acid value and a compound having an ethylenically unsaturated group and a non-acid value. Regarding the radically polymerizable compound, when two or more kinds are mixed and used, they may be copolymerized in advance to be used as a copolymer. Specific examples of such a radical polymerizable compound include the radical polymerizable compound described in Japanese Patent Laid-Open No. 2016-176009.

(1-2) Cationic polymerizable compound A cationically polymerizable compound is one having a cationic polymerizable group.
The cation polymerizable group is not limited as long as it can be polymerized by a cation, and examples thereof include an epoxy group, an oxetanyl group, and a vinyl ether group. Examples of the cationically polymerizable compound include a compound having a cyclic ether group such as an epoxy compound having an epoxy group and an oxetane compound having an oxetanyl group, and a vinyl ether having a vinyl ether group. Compounds etc.

The cationically polymerizable compound may be one having one or more cationically polymerizable groups, and a monofunctional compound having one cationically polymerizable group or a polyfunctional compound having two or more cationically polymerizable groups may be used. Specific examples of such a cationically polymerizable compound include a cationically polymerizable compound described in Japanese Patent Laid-Open No. 2016-176009.
Regarding the cationically polymerizable compound, when two or more kinds are mixed and used, these may be copolymerized in advance to be used as a copolymer.
The cationically polymerizable compound can be used together with a cationic initiator such as a photocationic initiator and a thermal cationic initiator.

(1-3) Anionic polymerizable compound The anionic polymerizable compound is an anionic polymerizable group.
The anionic polymerizable group may be any polymer that can be polymerized by an anion, and examples thereof include an epoxy group and a lactone group. Examples of the anionic polymerizable compound include an epoxy compound having an epoxy group, a lactone compound having a lactone group, and a compound having a (meth) acrylfluorenyl group.
The anionic polymerizable compound may be one having one or more anionic polymerizable groups, and a monofunctional compound having one of the polymerizable groups and a polyfunctional compound having two or more of the polymerizable groups may be used.
Examples of the lactone compound include β-propiolactone and ε-caprolactone.
As the epoxy compound, the epoxy compounds exemplified above as the cationically polymerizable compound can be used. As the compound having a (meth) acrylfluorenyl group, those exemplified as the radical polymerizable compound described above can be used.
Regarding an anionic polymerizable compound, when two or more kinds are mixed and used, they may be copolymerized in advance to be used as a copolymer.

(2) Polymer without polymerizable group The polymer described above does not have a polymerizable group.
As such a polymer, any polymer may be used as long as it includes a repeating structure, and examples thereof include a photosensitive resin having a photosensitive property and a non-photosensitive resin having no photosensitive property.

(2-1) Photosensitive resin The above-mentioned photosensitive resin is photosensitive, and examples thereof include use with an acid generator and cleavage of chemical bonds such as an ester group or an acetal group by the action of an acid. Positive resin that changes in the direction of increasing solubility in the developer. As the positive resin, for example, a resist matrix resin or a compound described in Japanese Patent Laid-Open No. 2016-89085 can be used.

(2-2) Non-photosensitive resin As the above-mentioned non-photosensitive resin, as long as it does not have photosensitivity, examples thereof include polycarbonate (PC), polyethylene terephthalate (PET), and polyethylene. Ether ether, polyvinyl butyral, polyvinyl pyrrolidone, polyvinyl alcohol, polyvinyl chloride, styrene-butadiene copolymer, polystyrene, polyphenylene ether, polyamine, polyamine Methacrylic resins such as imine, polyetherimide, norbornene-based resins, acrylic resins, polymethyl methacrylate, isobutylene maleic anhydride copolymer resins, and cyclic olefin-based thermoplastic resins. In addition, natural polymer materials such as gelatin, casein, starch, cellulose derivatives, and alginic acid can also be used. Furthermore, a polymer of the polymerizable compound may be used. That is, the said composition may be hardened | cured of the composition containing the said compound A and a polymerizable compound.

(2-3) Polymer The weight average molecular weight (Mw) of the polymer is appropriately set depending on the use of the composition and the like, and may be, for example, 1,500 or more, and 1,500 or more and 300,000 or less.
The weight average molecular weight Mw can be, for example, HLC-8120GPC manufactured by Tosoh Co., Ltd., the dissolution solvent is N-methylpyrrolidone to which 0.01 mol / liter lithium odor is added, and polystyrene for the calibration curve The standards are set to Mw377400, 210500, 96000, 50400, 20650, 10850, 5460, 2930, 1300, 580 (the above is the Easi PS-2 series manufactured by Polymer Laboratories) and Mw1090000 (manufactured by Tosoh). TSK-GEL ALPHA-M x 2 (manufactured by Tosoh) was measured and obtained. The measurement temperature can be set to 40 ° C, and the flow rate can be set to 1.0 mL / min.

(3) Other resins As the above resins, well-known adhesives such as silicon-based, urethane-based, acrylic-based adhesives, polyvinyl butyral adhesives, ethylene-vinyl acetate-based adhesives, etc. can also be used. Agent. When the above-mentioned adhesive is used, a cross-linking agent such as a metal chelate system, an isocyanate system, or an epoxy system may be used as a hardener, if necessary.

(4) The other composition includes the compound A and the resin. The compound A and the resin may be those which are not bonded by a covalent bond, or those which are bonded by a covalent bond.
For example, examples of the resin include an acrylic resin or a methacrylic resin having a reactive functional group such as an epoxy group, an amine group, a carboxyl group, and a hydroxyl group in the structure, and the resin can be formed by having a reaction with the reactive functional group. Covalently bonded compound A reacts with this resin, and is used in the form of compound A and a bonded body of the resin.
For example, in Example 1 described below, 3-bromopropanoic acid or the like may be added instead of 1,8-dibromooctane to prepare a compound A having a carboxyl group and bond it to a resin having a hydroxyl group.
A compound having a hydroxyl group may be used as the compound A and bonded to a resin having an epoxy group, an amine group, a carboxyl group, or the like.
The resin having a reactive functional group may be one having a polymerizable group or one having no polymerizable group.
As the resin having a reactive functional group, a polymer can be used. The weight-average molecular weight of such a polymer may be the same as that described in the item "(2) A polymer having no polymerizable group".
Specific examples of the polymer having a reactive functional group that can be used as the resin having a reactive functional group include ARUFON UG-4035, ARUFON UG-4010, ARUFON UG-4070, and ARUFON UH manufactured by Toa Kosei Corporation. -2000, ARUFON UH-2041, ARUFON UH-2170, ARUFON UP-1000, etc.

3. Other Ingredients Where the above composition contains the above-mentioned compound A, other ingredients may also be included as necessary. Examples of such components include ultraviolet absorbers and initiators.

(1) Ultraviolet absorbent The composition described above can stably absorb high-energy light in the ultraviolet region to around 400 nm by including an ultraviolet absorber. As a result, when the composition is used as an optical filter for preventing deterioration of an organic EL element, for example, the composition can effectively prevent the deterioration.
As the said ultraviolet absorber, it is common to use as an ultraviolet absorber. For example, those whose maximum absorption wavelength is less than 350 nm can be preferably used. The measurement method of the maximum absorption wavelength can be the same as the method described in the above-mentioned "A. Compound".

Specific examples of the ultraviolet absorber include 2-hydroxybenzophenones, 2- (2'-hydroxyphenyl) benzotriazoles, and benzene described in Japanese Patent Laid-Open No. 2017-008221. Formates, triaryls, etc., or benzotriazole-based ultraviolet absorbers and benzophenone-based ultraviolet absorbers described in Japanese Patent Laid-Open No. 2002-97224.
Moreover, as said ultraviolet absorber, a latent ultraviolet absorber which shows an ultraviolet absorption ability by heat processing etc. can also be used. As such a latent ultraviolet absorber, for example, those described in International Publication No. 2014/021023 can be used as a latent additive.

The content of the ultraviolet absorber is not limited as long as it can impart desired ultraviolet absorbency to the composition, and for example, it may be the same as that described as the content of the compound A. The mass ratio of the ultraviolet absorber to the compound A (ultraviolet absorber / compound A) may be any material capable of imparting a desired light absorbency to the composition, and there is no problem if it is 1 or more. It is set to 0.1 or more and 10 or less.

(2) Initiator The above-mentioned composition is easily used as a curable composition, for example, by including an initiator.
As such an initiator, any polymer that can polymerize a polymerizable compound may be used, and examples thereof include a radical polymerization initiator that can be added together with a radical polymerizable compound, a polymerizable compound that can be added together with a cationic polymerizable compound, Or a cationic polymerization initiator which can be added together with a photosensitive compound as an acid generator, an anionic polymerization initiator which can be added together with an anionic polymerizable compound, and the like.
As the above-mentioned radical polymerization initiator, cationic polymerization initiator, and the like, more specifically, a radical polymerization initiator and a cationic initiator described in Japanese Patent Application Laid-Open No. 2016-176009 can be used. Moreover, as said anionic polymerization initiator etc., more specifically, the photoanion polymerization initiator, thermal anion polymerization initiator, etc. which are described in Unexamined-Japanese-Patent No. 2017-073389 are mentioned.

(3) Others As the other components described above, components other than the ultraviolet absorber and the initiator may be included, and examples thereof include solvents, colorants, inorganic compounds, dispersants, and chain transfer agents that disperse colorants and inorganic compounds. , Sensitizer, surfactant, silane coupling agent and other additives. About the said additive, a well-known thing can be used, For example, what is described in International Publication No. 2014/021023 can be used.
The solvent may include a solvent capable of dissolving or dispersing the above-mentioned components. The solvent is a liquid at 25 ° C. under atmospheric pressure and capable of dispersing or dissolving each component of the composition. In addition, solvents are those which do not react with compound A, resin, and the like. Therefore, for example, even if it is classified as a polymerizable compound at 25 ° C and atmospheric pressure, it is not a solvent in the composition of the present invention.
Moreover, as said other component, a matting agent and a light stabilizer may be contained.
Examples of the matting agent and light stabilizer include matting agents such as nickel derivatives described in Japanese Patent Application Laid-Open No. 2016-160387, and hindered amine compounds (HALS).

4. Composition As a method for producing the composition, as long as it is a method capable of mixing the above-mentioned components with good dispersibility, there is no limitation, and a method of mixing by a known stirring means can be used. For example, when the resin is a thermoplastic resin, a method of mixing the resin and the compound A while plasticizing the resin using an extruder or the like can be used. In the case where a polymer containing a polymerizable compound is used as a resin, a method may be mentioned in which a composition containing the above-mentioned compound A and a polymerizable compound and an optional starter is prepared, and then the composition is subjected to Hardened. As the hardening treatment, when a photopolymerization initiator is included as the initiator, exposure treatment may be mentioned, and when a thermal polymerization initiator is included as the initiator, heat treatment may be mentioned.

The use of the composition can be the same as that described in the above item "1. Compound A".

D. Optical Filter Next, the optical filter of the present invention will be described.
The optical filter of the present invention is characterized by having a light absorbing layer containing the compound A described above. When the light absorbing layer contains the compound A, the optical filter is more excellent in light absorption around 400 nm.
Hereinafter, the light absorbing layer included in the optical filter of the present invention will be described in detail.

1. Light absorbing layer The light absorbing layer includes the compound A described above.
About the said compound A, its content, etc., since it can be set as the content described in the said "C. composition" item, description here is abbreviate | omitted.
The light-absorbing layer is not limited as long as it contains Compound A, and it may also be a resin. In addition, other components may be included in addition to the compound A and the resin as necessary. Such a resin and other components may be the same as those described in the items "2. Resin" and "3. Other components" described in the above-mentioned "C. Composition".

The shape, such as the planar shape, area, and thickness of the light absorbing layer, is appropriately set depending on the application of the optical filter.
As the method for forming the light absorbing layer, any one that can form a light absorbing layer having a desired shape and thickness may be used, and a known method for forming a coating film can be used. As the formation method, for example, a method of applying the composition described in the above-mentioned "C. Composition" item, and applying a drying treatment, a hardening treatment, or the like to the coating film can be used.

2. Optical filter The optical filter may include only the light absorbing layer described above, or may include other layers other than the light absorbing layer described above. Examples of the other layers include a transparent support, an undercoat layer, an anti-reflection layer, a hard coat layer, a lubricant layer, and an adhesive layer. The contents of such layers and the method of forming them can be generally used in optical filters. For example, they can be used in Japanese Patent Laid-Open No. 2011-144280 and International Publication No. 2016/158639. The content is the same.
The light absorbing layer may be used as, for example, an adhesive layer for adhering the transparent support and any of the layers. At this time, the above-mentioned optical filter may be provided with a well-known isolation film such as a polyethylene terephthalate film which is easily adhered on the surface of the light absorbing layer as an adhesive layer.

When the above-mentioned optical filter is used for an image display device, it can usually be arranged on the front of the display. For example, there is no problem even if the optical filter is directly attached to the surface of the display. When a front panel or electromagnetic wave shield is provided on the front of the display, it can be on the front side (outside of the front panel or electromagnetic wave shield). ) Or the back side (display side) is attached with an optical filter. It can also be used as various members included in an image display device, for example, optical members such as a color filter and a polarizing plate. Furthermore, it is also possible to directly laminate each component included in the image display device.

The invention is not limited to the embodiments described above. The embodiment described above is an example, and a person having substantially the same configuration and exhibiting the same effect as the technical idea described in the patent application scope of the present invention is included in the technical scope of the present invention regardless of the form.
[Example]

Hereinafter, the present invention will be described in more detail with examples and comparative examples, but the present invention is not limited to these examples and the like.

[Example 1]
Add indole-3-formaldehyde (0.044 mol) and potassium carbonate (0.050 mol) to DMF (N, N-dimethylformamide, dimethylformamide) (25 mL), and dropwise add 1,8-dibromo Octane (0.020 mol). After heating at 80 ° C for 9 hours, the reaction solution was extracted with ethyl acetate, and the oil layer was washed with water. The precipitate from the oil layer was filtered and washed with methanol to obtain an intermediate.
Then, the intermediate (0.010 mol), malononitrile (0.022 mol), and piperidine (0.0020 mol) were added to ethanol (50 mL), and the mixture was heated at 80 ° C. for 5 hours. The reaction solution was diluted with ethanol, and the precipitate was filtered and dried to obtain a compound represented by the following formula (11) (hereinafter, sometimes referred to as compound 11).
¹ H-NMR and IR (Infrared Radiation) confirmed that the obtained solid was a target.
The ¹ H-NMR and IR measurement results of the obtained compound are shown in Tables 1 and 2 below.

[Example 2]
Except that 5-bromo-1-pentene was used instead of 1,8-dibromooctane, and ethyl cyanoacetate was used instead of malononitrile, the same procedure as in Example 1 was carried out to obtain the compound represented by the following formula (40): (Hereinafter, sometimes referred to as compound 40).
The obtained solid was confirmed to be the target by ¹ H-NMR and IR.

[Example 3]
A compound represented by the following formula (41) (hereinafter, sometimes referred to as compound 41) was obtained in the same manner as in Example 1 except that ethyl cyanoacetate was used instead of malononitrile.
The obtained solid was confirmed to be the target by ¹ H-NMR and IR.

[Example 4]
In addition to using 2-methylindole-3-carboxaldehyde instead of indole-3-carboxaldehyde, iodoethane instead of 1,8-dibromooctane, and allyl cyanoacetate instead of malononitrile, A compound represented by the following formula (62) (hereinafter, sometimes referred to as compound 62) was obtained in the same manner as in Example 1.
The obtained solid was confirmed to be the target by ¹ H-NMR and IR.

[Example 5]
Except that 2-phenylindole-3-carbaldehyde was used instead of indole-3-carbaldehyde, and ethyl 2-bromomethacrylate was used instead of 1,8-dibromooctane, in the same manner as in Example 1 A compound represented by the following formula (64) (hereinafter, sometimes referred to as compound 64) is obtained.
The obtained solid was confirmed to be the target by ¹ H-NMR and IR.

[Example 6]
A compound was obtained in the same manner as in Example 1 except that 3-bromopropanoic acid was used instead of 1,8-dibromooctane.
Then, the obtained compound, trimethylolethane (0.010 mol) and 4- (dimethylamino) pyridine (0.010 mol) were added to dichloromethane (50 mL) and cooled to 0 ° C. While stirring, dicyclohexylcarbodiimide (0.035 mol) was added thereto. Thereafter, the temperature was raised to room temperature and stirred for 5 hours. The precipitate was filtered from the reaction solution, and the filtrate was washed with dilute hydrochloric acid and a saturated aqueous sodium hydrogen carbonate solution. The organic layer was desolvated under reduced pressure, and crystallized with methanol. The precipitate was filtered and dried to obtain a compound represented by the following formula (68) (hereinafter, sometimes referred to as compound 68).
The obtained solid was confirmed to be the target by ¹ H-NMR and IR.

[Chemical 20]

[Table 1]

[Table 2]

[Example 101]
Except that 3-bromopropanoic acid was used instead of 1,8-dibromooctane, 1,4-benzenedimethanol (0.010 mol) was added to the compound (0.020 mol) obtained in the same manner as in Example 1. , THF (tetrahydrofuran, tetrahydrofuran) (50 mL), and 4- (dimethylamino) pyridine (0.010 mol), and cooled to 0 ° C. While stirring, dicyclohexylcarbodiimide (0.035 mol) was added thereto. The solvent was distilled off and purified using a silica column (chloroform / methanol = 10/1), and then, recrystallization was performed using methanol and dried to obtain a compound represented by the following formula (101) (hereinafter , Sometimes referred to as compound 101).
The obtained solid was confirmed to be the target by ¹ H-NMR and IR.

[Example 102]
A compound represented by the following formula (102) (hereinafter, sometimes referred to as compound 102) was obtained in the same manner as in Example 101 except that 1,3-propanediol was used instead of 1,4-benzenedimethanol.
The obtained solid was confirmed to be the target by ¹ H-NMR and IR.

[Example 103]
A compound represented by the following formula (103) was obtained in the same manner as in Example 101 except that 2-hydroxy-3-propenyloxypropyl methacrylate was used instead of 1,4-benzenedimethanol. , Sometimes referred to as compound 103).
The obtained solid was confirmed to be the target by ¹ H-NMR and IR.

[Example 104]
A compound represented by the following formula (104) (hereinafter, sometimes referred to as compound 104) was obtained in the same manner as in Example 101 except that pentaerythritol triacrylate was used instead of 1,4-benzenedimethanol.

[Chemical 21]

[table 3]

[Table 4]

[Comparative Example 1]
A compound (hereinafter, compound B1) represented by the following general formula (B1) was prepared.

[Chemical 22]

[Evaluation 1]
The compounds of the Examples and Comparative Examples were measured for absorption spectra, and evaluated for a 10% weight reduction temperature and absorbance maintenance rate at normal pressure.

1. Absorbance spectrum The absorbances of the compounds of Examples and Comparative Examples were measured in accordance with JIS K0115.
Specifically, it was dissolved in a solvent (chloroform) so as to have a concentration of 1.0 × 10 ^-5 mol / L, and a sample for evaluation was obtained. Next, the obtained evaluation sample is filled in a quartz cell (optical path length 10 mm, thickness 1.25 mm), and an absorbance photometer (for example, U-3900 (manufactured by Hitachi High-Tech Science)) is used for each wavelength. The absorbance was measured. The measurement results of the compounds of Example 1 and Comparative Example 1 are shown in FIG. 1 and FIG. 2, respectively. In addition, the measurement results of the maximum absorption wavelength, half-value width, and absorbance at each wavelength of the compound 11 of Example 1 as the compound of Example 103, the compound of Example 103 as the compound of Example 103, and the compound of Comparative Example as the compound B1 are shown in the following table. 3. The absorbance is measured within a range of 250 nm to 600 nm.

2. 10% weight reduction temperature under normal pressure For the compounds of Examples and Comparative Examples, the 10% weight reduction temperature was measured under the following conditions. The results are shown in Table 4 below. The higher the 10% weight reduction temperature, the lower the volatility.

(10% weight reduction temperature measurement conditions)
As a differential thermal-thermogravimetric simultaneous measurement device, a model manufactured by SII NanoTechnology: EXSTAR TG / DTA6200 was used.
Regarding the measurement conditions, a sample of about 5 mg was heated under a nitrogen atmosphere of 200 mL / min and under normal pressure at an initial temperature of 30 ° C, an end temperature of 500 ° C, and a temperature increase rate of 10 ° C / min. The sample was measured for heat loss, and the temperature at the time when the weight was reduced by 10% relative to the weight of the sample at 30 ° C was set as the 10% weight reduction temperature.

3. Absorbance maintenance ratio For the compounds of Examples and Comparative Examples, the absorbance maintenance ratio was measured under the following conditions, and evaluated based on the following evaluation criteria. The results are shown in Table 5 below. The higher the absorbance maintenance rate, the better the light resistance.
＜ Evaluation criteria ＞
○: More than 60%
△: 55% or more and 60% or less ×: less than 55%

(Measurement conditions of absorbance maintenance rate)
The absorbance maintenance ratio is a method in which the following (1) to (3) are sequentially performed.
(1) A polymethylmethacrylate (PMMA) film (100 μm) to which 3.8% by mass of the compound was added was prepared as a sample for evaluation.
(2) The sample for evaluation was irradiated with xenon light for 240 hours.
(3) The absorbance change at the maximum absorption wavelength of the compound A of the evaluation sample before and after irradiation with xenon light was measured, and the absorbance maintenance ratio (absorbance after irradiation / absorbance before irradiation) was calculated.
The xenon light was irradiated using a xenon weathering tester "ATLAS Weather-Ometer Ci4000" (manufactured by Toyo Seiki Seisakusho Co., Ltd.).
The following conditions were used for the xenon light irradiation conditions.

(Xenon light irradiation conditions)
Irradiance: 0.55 W / m ² (wavelength 340 nm)
Temperature in test tank: 62 ℃
Relative humidity in the test tank: 50%

[table 5]

[TABLE 6]

[TABLE 7]

[Evaluation 2]
The polymerizable compositions using the compounds of the examples and comparative examples were evaluated for the hardenability, the compatibility between the compound and the resin, the outgassing during hardening, and the absorbance maintenance rate of the hardened product.

(Preparation of polymerizable composition)
42 parts by mass of trimethylolpropane triacrylate, 16 parts by mass of bisphenol A epoxy acrylate (EB3700 manufactured by DAICEL-ALLNEX Corporation), 42 parts by mass of tripropylene glycol diacrylate, and leveling agent (SH-29A) 0.5 parts by mass and 5 parts by mass of a radical initiator (Irgacure 907) were mixed, and then 5 parts by mass of Compound A or Compound B1 and 50 parts by mass of N, N-dimethylacetamide (DMAc) were added. The mixed solution was stirred at 40 ° C for 10 minutes to prepare a polymerizable composition.

1. Curability: The polymerizable composition was spin-coated (500 rpm, 7 seconds) on a glass substrate, and pre-baked at 90 ° C for 120 seconds using a hot plate. A high-pressure mercury lamp (20 mW / cm ² ) was used as a light source and exposure was performed at 200 mJ / cm ² to obtain a coating film for evaluation.
The presence or absence of wrinkles was confirmed about the obtained coating film for evaluation, and the curability was evaluated by the following evaluation criteria. The results are shown in Table 6 below.
＜ Evaluation criteria ＞
〇: No wrinkles.
×: Wrinkles remain.
It can be judged that the less the wrinkles, the less the hardening hindrance of the polymerizable composition caused by the compound A. Furthermore, it can be judged that as a result, a hardened material in which the compound A is stably held can be obtained.

2. Compatibility A polymerizable composition was obtained in the same manner as in the preparation of the polymerizable composition except that a solution obtained by mixing 5 parts by mass of Compound A or Compound B1 and 5 to 150 parts by mass of DMAc was used. When visually observing the obtained polymerizable composition, the compound A or the compound B1 and the resin were evaluated on the basis of the following evaluation criteria based on the amount of DMAc necessary to prepare a polymerizable composition without the precipitation of the compound A or compound B1. Of compatibility. The results are shown in Table 6 below.
〇: The amount of DMAc added is less than 10 parts by mass.
Δ: The amount of DMAc added is 10 parts by mass or more and less than 100 parts by mass.
×: The added amount of DMAc is 100 parts by mass or more.
It can be judged that the smaller the amount of DMAc added, the better the compatibility between Compound A and the resin. In addition, it can be judged that by compound A being more uniformly dispersed and held in the hardened material, a hardened material capable of stably absorbing light of a desired wavelength can be obtained.

3. The above polymerizable composition was spin-coated (500 rpm, 7 seconds) out of gas on a glass substrate, and pre-baked at 90 ° C for 120 seconds using a hot plate. A high-pressure mercury lamp (20 mW / cm ² ) was used as a light source, and exposure was performed at 200 mJ / cm ² to obtain a cured film.
A 0.7 mm spacer and a glass substrate were placed on the cured film, and heated at 230 ° C. for 2 hours using a hot plate.
After heating, the absorption spectrum (400 nm) of the glass substrate provided on the cured film was measured. Based on the absorbance at 400 nm, the outgassing property was evaluated on the following basis. The results are shown in Table 6 below.
〇: The absorbance at 400 nm does not reach 0.1.
Δ: The absorbance at 400 nm is 0.1 or more and less than 0.5.
×: The absorbance at 400 nm is 0.5 or more.
It can be judged that the lower the absorbance at 400 nm, the lower the volatility of Compound A, and the more stable Compound A can be maintained in the hardened material.

4. The absorbance maintenance rate of the cured product is replaced by the evaluation coating film produced by the same method as the evaluation of "1. Hardenability" described above, except that "1 of" Evaluation 1 "is used. The "absorbance maintenance ratio" was obtained under the same conditions. Based on the obtained absorbance maintenance rate, the absorbance maintenance rate of the hardened | cured material was evaluated by the following evaluation criteria. The results are shown in Table 6 below.
〇: more than 60%
△: 55% or more and 60% or less ×: less than 55%
Furthermore, it can be judged that the higher the absorbance maintenance rate, the lower the volatility of the compound A in the hardened material, and the more stable the compound A can be maintained in the hardened material.

[TABLE 8]

[Summary]
From Table 3 and FIG. 1, it can be confirmed that, for example, the compound 11 of Example 1 has a higher absorbance at 400 nm than the compound B1 of Comparative Example 1, and has excellent absorbance of light near 400 nm. From Table 4, it was confirmed that the compound 11 of Example 1 and the compounds 101 to 103 of Examples 101 to 103 were excellent in heat resistance.
From Table 5, it can be confirmed that the compounds of the examples are those having excellent absorbance maintenance.
From Table 6, it can be confirmed that the polymerizable composition using the compound of the example is one having excellent curability, excellent compatibility between the compound and the resin, low volatility of the compound A, and excellent absorbance maintenance rate of the cured product.
From the above results, it was confirmed that the composition containing Compound A and the resin can stably absorb light near 400 nm. For example, when the composition is used as an optical filter, it can stably block the light near 400 nm. The transmission of light.
[Industrial availability]

The present invention exerts an effect of providing a compound having excellent light absorptivity in the vicinity of 400 nm.

FIG. 1 is an absorption spectrum of the compound of Example 1. FIG.

FIG. 2 is an absorption spectrum of the compound of Comparative Example 1. FIG.

Claims (11)

A compound represented by the following general formula (A): (In the formula, Ar is an indole ring, and R ¹ represents cyano, -COOR, -OCOR, -CONHR, -NHCOR, -COONHR, -NHCOOR, -COR, -SO ₂ R, -SOR, -SO ₂ NRR ' , Halogen atom, nitro or phosphino, R and R 'each independently represent a hydrogen atom, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an arane having 7 to 30 carbon atoms Or a heterocyclic group containing 2 to 20 carbon atoms, R ² represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, carbon Aralkyl groups having 7 to 30 atoms or heterocyclic groups having 2 to 20 carbon atoms, alkyl groups, aryl groups, aralkyl groups, and methylene groups containing heterocyclic groups represented by R and R ′ and R ² Can be substituted with carbon-carbon double bonds, -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -O-CO-O- , -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-,- NR ''-,> P = O, -SS-, -SO ₂ -or a combination thereof, R '' represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and R and R 'and R ² represent Hydrogen atoms in alkyl, aryl, aralkyl and heterocyclic groups can be substituted with ethylenically unsaturated groups, halogens Element atom, fluorenyl, fluorenyloxy, substituted amine, sulfonamido, sulfonium, carboxyl, cyano, sulfo, hydroxyl, nitro, thiol, sulfinolimino, carbamoyl, sulfonium Amine group, phosphonic acid group, phosphate group, or salt of carboxyl group, sulfo group, phosphonic acid group or phosphate group, n represents an integer of 1 to 10, and X represents an n-valent group). The compound according to claim 1, wherein the compound is a compound represented by the following general formula (A1), (A2) or (A3): [化 2] ^{(Wherein, R 1, R 2, R} , R ', n and X-based formula (A), the ^{R 1, R 2, R,} R', and n and X, R ³ and R ⁴ represent hydrogen Atom, halogen atom, cyano, nitro, alkyl group with 1 to 40 carbon atoms, aryl group with 6 to 30 carbon atoms, aralkyl group with 7 to 30 carbon atoms or 2 to 20 carbon atoms Heterocyclic groups, R ⁵ and R ⁵⁵ each independently represent a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an arane having 7 to 30 carbon atoms Or a heterocyclic group containing 2 to 20 carbon atoms, and the alkyl group, aryl group, aralkyl group, and methylene group in the heterocyclic group group represented by R ³ and R ⁴ and R ⁵ and R ⁵⁵ may be substituted Carbon-carbon double bond, -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -O-CO-O-, -S- CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NR ''- ,> P = O, -SS-, -SO ₂ -or a combination thereof, R "represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and R ³ and R ⁴ and R ⁵ and R ⁵⁵ represent Hydrogen atoms in alkyl, aryl, aralkyl, and heterocyclic groups can be substituted with ethylenically unsaturated groups, halogen atoms, fluorenyl, and fluorene Group, substituted amino group, sulfoamido group, sulfoamido group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, mercapto group, fluorenimine group, carbamate group, sulfonamido group, phosphonic acid group, phosphoric acid 5a represents an integer of 0 to 4 and 55a represents an integer of 0 to 3), or a salt of a carboxyl group, a carboxyl group, a sulfo group, a phosphonic acid group, or a phosphate group. For example, the compound of claim 1, wherein the 10% weight reduction temperature of the above-mentioned compound under normal pressure is 250 ° C or more. The compound of claim 1, wherein n is an integer of 2-10. The compound of claim 4, wherein X is an aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a methylene group in these groups is substituted with -O-,- S-, -CO-, -COO-, -OCO-. The compound of claim 2, wherein at least one of the above R ³ , R ⁴ , R ⁵ and R ⁵⁵ is an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 7 to 30 carbon atoms. An aralkyl group of 30 or a hydrogen atom in a heterocyclic group containing 2 to 20 carbon atoms is substituted with an ethylenically unsaturated group, or an alkyl group having 1 to 40 carbon atoms and 6 to 6 carbon atoms An aryl group of 30, an aralkyl group of 7 to 30 carbon atoms, or a methylene group in a heterocyclic group containing 2 to 20 carbon atoms is substituted with a carbon-carbon double bond. For example, the compound of claim 2, wherein the above compound satisfies the following (1) or (2): (1) is a compound represented by the above general formula (A1), and n is an integer of 2 or 3, and X is carbon An aliphatic hydrocarbon group having 1 to 35 atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or a methylene group in these groups is substituted with -O-, -S-, -CO-, -COO-,- OCO-based group; (2) is a compound represented by the above general formula (A3), and n is 1, R ⁴ is an alkyl group having 1 to 10 carbon atoms or one hydrogen atom of these groups is A group substituted with an ethylenically unsaturated group or a methylene group in an alkyl group having 1 to 40 carbon atoms is replaced with -COO- or -OCO- and a hydrogen atom in the group is replaced with an ethylenically unsaturated group Base into base. For example, the compound of claim 1, wherein the maximum absorption wavelength of the above compound in a range of 250 nm to 600 nm is 350 nm to 420 nm. A light absorbent containing the compound according to any one of claims 1 to 8. A composition containing the compound according to any one of claims 1 to 8, and Resin. An optical filter having a light absorbing layer containing the compound according to any one of claims 1 to 8.