JP2019065200A - Coloring composition, display filter and display - Google Patents

Abstract

To provide a coloring composition that has an absorption maximum with a maximum absorption wavelength of 500-640 nm, a transmittance at wavelength 380-450 nm of 80% or more, and suppressed fluorescence, and a display filter and a display containing the coloring composition.SOLUTION: A coloring composition contains a compound represented by formula (1) and a quencher. (R-Rindependently represent a monovalent group; M is an optionally substituted, any atom; a benzene ring in formula (1) may be further substituted with any substituent).SELECTED DRAWING: None

Description

  The present invention relates to a coloring composition, a filter for display containing the same, and a display, more specifically, a coloring composition having an absorption maximum whose maximum absorption wavelength is 500 to 640 nm and in which fluorescence emission is suppressed, The present invention relates to a display filter and display to be contained.

  In recent years, white LEDs and white OLEDs are often used as light sources for display devices. There are several types of light emission methods of white LEDs, and LEDs emitting R (red), G (green), and B (blue) light are arranged to obtain white light, or blue LEDs There is a system of obtaining white light by a combination of blue light and yellow light emission from a yellow phosphor, blue light from a blue LED, a combination of green light emission from a green phosphor and red light emission from a red phosphor. There are several types of light emission methods of white OLEDs, one in which layers emitting light of red, green and blue are laminated, and one in which layers emitting light of blue and yellow are laminated. .

  The spectrum of the obtained white light contains light exhibiting an orange color in a region around 590 nm, and it is known that the color purity is lowered when the emission intensity of the light in this region is high.

  In order to improve such a point, for example, Patent Document 1 discloses a method using a specific tetraazaporphyrin compound having an absorption maximum wavelength in a wavelength range around 570 to 620 nm.

  On the other hand, Patent Document 2 discloses a specific dipyrromethene compound as a fluorescent dye.

JP, 2016-11348, A U.S. Patent Application Publication No. 2011/0144351

  As examined by the present inventors, the tetraazaporphyrin compound described in Patent Document 1 has one absorption maximum near the wavelength of 500 to 640 nm, but has secondary absorption on the shorter wavelength side than the maximum absorption wavelength. To reduce the color reproducibility (color purity) and brightness.

  On the other hand, Patent Document 2 discloses a compound having an absorption maximum in the vicinity of a wavelength of 500 to 640 nm as a fluorescent dye, but the fluorescent dye alone has strong fluorescence of green to red, so that it alone can be used for display Was difficult to apply.

  Therefore, the present invention provides a coloring composition having an absorption maximum having a maximum absorption wavelength of 500 to 640 nm, a transmittance of 80% or more at a wavelength of 380 to 450 nm, and suppression of fluorescence emission, and the coloring composition It is an object of the present invention to provide a display filter and a display that contain

  MEANS TO SOLVE THE PROBLEM As a result of conducting earnest examination, in order to solve the said subject, the present inventors discover that the said subject can be solved by using a specific dipyrromethene compound and a quenching agent together, and came to complete this invention. That is, the present invention provides the following.

[1] A colored composition comprising a compound represented by the following general formula (1) and a quencher.

(In formula (1), R ^{1 to} R ³ each independently represent a monovalent group. M represents an optional atom which may have a substituent. The benzene ring in formula (1) is Furthermore, it may be substituted by arbitrary substituents.)

[2] The colored composition according to [1], wherein the transmittance of the compound represented by the general formula (1) at a wavelength of 380 to 450 nm is 80% or more.
[3] The coloring composition according to [1] or [2], wherein the compound represented by the general formula (1) has an absorption maximum whose maximum absorption wavelength is a wavelength of 500 to 640 nm.
[4] The colored composition according to [3], wherein the half width of the absorption maximum of the compound represented by the general formula (1) is 25 nm or less.

[5] A display filter comprising the coloring composition according to any one of [1] to [4].
[6] A display comprising the display filter according to [5].

  According to the present invention, a coloring composition having an absorption maximum having a maximum absorption wavelength of 500 to 640 nm, a transmittance of 80% or more at a wavelength of 380 to 450 nm, and a suppression of fluorescence emission, the coloring composition An object-containing filter and display can be provided.

Hereinafter, the embodiments of the present invention will be specifically described. However, the present invention is not limited to the following embodiments, and various modifications can be made within the scope of the present invention.
In the present invention, “(meth) acrylic” means “acrylic and / or methacrylic”, and the same applies to “(meth) acrylate” and “(meth) acryloyl”.
In the present invention, "total solids" means all components other than the solvent contained in the coloring composition.
Furthermore, in the present invention, the "weight average molecular weight" refers to a polystyrene-equivalent weight average molecular weight (Mw) by GPC (gel permeation chromatography).

  The coloring composition of the present invention contains a compound represented by the following formula (1) and a quencher. Moreover, you may further contain a solvent, binder resin, an adhesive, etc. as needed.

[Compound represented by General Formula (1)]
The coloring composition of the present invention contains a compound represented by the following general formula (1) (hereinafter, sometimes referred to as “compound (1)”).

In Formula (1), R ^{1 to} R ³ each independently represent a monovalent group. M represents any atom which may have a substituent. The benzene ring in Formula (1) may be further substituted by any substituent.

  Thus, by using the compound represented by the general formula (1), the β position of the pyrrole ring of the compound is substituted with a benzene ring, whereby the absorption maximum lengthens and the absorption It is considered that the gram absorption coefficient at the maximum is improved, and further, by taking a rigid chemical structure by π conjugation, it becomes possible to reduce the half width at the absorption maximum.

(R ¹ and R ² )
In Formula (1), each of R ¹ and R ² independently represents a monovalent group.
As a monovalent group in R ¹ and R ² , for example, a hydrogen atom, an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, an alkylcarbonyl group And alkoxycarbonyl groups and halogen atoms.

  Specifically, the aliphatic hydrocarbon group which may have a substituent includes, for example, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, and a substituent. And alkynyl groups which may be substituted.

The alkyl group includes a linear, branched or cyclic alkyl group. The carbon number of the alkyl group is not particularly limited, but from the viewpoint of stability, it is usually 1 or more, preferably 10 or less, more preferably 6 or less, and still more preferably 4 or less. There exists a tendency which can control the solubility of a compound by being in the said range.
Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, 2-propyl group, n-butyl group, isobutyl group, tert-butyl group, n-hexyl group, n-octyl group and the like. . Among these, from the viewpoint of suppressing molecular vibration of the alkyl chain, a linear or branched alkyl group having 4 or less carbon atoms is preferable.
The substituent which the alkyl group may have is any substituent, and among them, a hydroxyl group, a halogen atom, an alkylcarbonyl group, an alkoxycarbonyl group, an alkenyl group, an alkynyl group, an alkoxy group and the like can be mentioned.

The alkenyl group includes a linear, branched or cyclic alkenyl group. The carbon number of the alkenyl group is not particularly limited, but is usually 2 or more and 3 or more, preferably 10 or less, and more preferably 6 or less. There is a tendency that the solubility can be controlled by setting the lower limit value or more, and by setting the upper limit value or less, the molecular vibration of the alkenyl group is suppressed to suppress the side absorption and the gram absorption coefficient of the main absorption becomes high. Tend. Specific examples of the alkenyl group include vinyl, styryl and diphenylvinyl groups.
The substituent which the alkenyl group may have is any substituent, and among them, a hydroxyl group, a halogen atom, an alkylcarbonyl group, an alkoxycarbonyl group, an alkoxy group and the like can be mentioned.

The alkynyl group includes a linear, branched or cyclic alkynyl group. The carbon number of the alkynyl group is not particularly limited, but is usually 2 or more and 3 or more, preferably 10 or less, and more preferably 6 or less. There is a tendency that the solubility can be controlled by setting the lower limit value or more, and by setting the upper limit value or less, the molecular vibration of the alkynyl group is suppressed to suppress the side absorption, and the gram absorption coefficient of the main absorption becomes high. Tend. Specific examples of the alkynyl group include a methylethynyl group, a phenylethynyl group and a trimethylsilylethynyl group.
The substituent which the alkynyl group may have is any substituent, and among them, a hydroxyl group, a halogen atom, an alkylcarbonyl group, an alkoxycarbonyl group, an alkoxy group and the like can be mentioned.

The aromatic ring group includes an aromatic hydrocarbon ring group and an aromatic heterocyclic group.
The carbon number of the aromatic ring group is preferably 2 or more, more preferably 5 or more, still more preferably 6 or more, and preferably 15 or less, more preferably 12 or less, still more preferably 10 or less. There is a tendency for the compound (1) to be stabilized by setting it to the above lower limit value, and there is a tendency to suppress the control of the solubility and the side absorption by setting it to the above upper limit value.

The aromatic hydrocarbon ring group may be a single ring or a condensed ring, and examples thereof include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a pyrene ring having one free valence. Groups are mentioned.
The aromatic heterocyclic group may be a single ring or a condensed ring. For example, a furan ring, a thiophene ring, a benzothiophene ring, a pyrrole ring or a pyrazole ring having one free valence. Imidazole ring, oxadiazole ring, indole ring, carbazole ring, benzisoxazole ring, benzisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, etc. It can be mentioned.

  Thus, the aromatic ring group may be a 5- or 6-membered ring, and may be a single ring or a fused ring, but a 6-membered ring is preferred to obtain the desired maximum absorption wavelength, and the secondary absorption and fluorescence In order to suppress, a group having a substituent at the ortho position in a single ring is preferable, and an ortho position substituted benzene ring group is more preferable.

  Although the substituent which the aromatic ring group may have is not particularly limited, among them, hydroxyl group, halogen atom, cyano group, nitro group, alkyl group, alkoxy group, alkoxycarbonyl group, alkylcarbonyl group and the like can be mentioned.

  The carbon number of the alkylcarbonyl group is not limited, but is usually 2 or more, preferably 10 or less, and more preferably 4 or less. There exists a tendency which solubility can be controlled by below the said upper limit carrying out. A methyl carbonyl group, an ethyl carbonyl group, isopropyl carbonyl group, 2-butyl carbonyl group, a tert- butyl carbonyl group etc. are mentioned as a specific example of an alkyl carbonyl group.

  The carbon number of the alkoxycarbonyl group is not limited, but is usually 2 or more, preferably 10 or less, and more preferably 4 or less. There exists a tendency of control of solubility by setting it below the said upper limit. Specific examples of the alkoxycarbonyl group include methoxycarbonyl group, ethoxycarbonyl group, n-butoxycarbonyl group and the like.

  As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom etc. are mentioned, Among these, a fluorine atom is preferable from a viewpoint of water resistance improvement.

(R ³ )
In Formula (1), R ³ represents a monovalent group.
Examples of the monovalent group in R ³ include a hydrogen atom, an aliphatic hydrocarbon group which may have a substituent, an aromatic ring group which may have a substituent, a nitro group, a cyano group, A halogen atom etc. are mentioned.
Among these, as the aliphatic hydrocarbon group which may have a substituent, the aromatic ring group which may have a substituent, and the halogen atom, the same ones as mentioned for R ¹ and R ^{2 can} be mentioned. The thing is mentioned. Among the aromatic ring groups, from the viewpoint of reducing the steric hindrance with the benzopyrrole ring, it is preferably a single ring, and among these, a benzene ring group and an imidazole ring group are preferable.

(Benzene ring at the β-position of pyrrole)
The benzene ring in Formula (1), that is, the benzene ring at the β-position of pyrrole, may be further substituted by any substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkoxy group, an nitro group, a cyano group and the like, and from the viewpoint of reactivity during synthesis of the dipyrrole methene skeleton, the stability of the compound From the viewpoint of maintaining the above, an unsubstituted alkyl group having 1 to 5 carbon atoms is preferable. These substituents may be directly linked to each other, or may be linked to each other via a linker. In addition, these substituents may be bonded to any ^one of R ^{1 to} R ³ .

(M)
In the formula (1), M represents an optional atom which may have a substituent.
Among the optional atoms, from the viewpoint of versatility, typical element atoms such as hydrogen atom, boron atom, magnesium atom, calcium atom, silicon atom, aluminum atom, gallium atom, indium atom, tin atom, antimony atom, bismuth atom; Transition element atom of the fourth period in the table; bivalent transition element atom of the fifth period of the periodic table; trivalent transition element atom of the fifth period of the periodic table is preferable, and from the viewpoint of heavy atom effect, platinum atom, iridium atom, etc. Transition metal atoms are more preferred.
Moreover, these arbitrary atoms may be substituted by the anion ligand, and may be substituted by another ligand. Other ligands include, for example, bipyridine, phenanthroline, phenylpyridine, phenyl azole, triphenyl phosphine and other C ^ C, C ^ N, N ^ C ^ N type ligands and the like.

  The specific example of a compound (1) is given to the following. However, it is not limited to these examples.

  Compound (1) can be synthesized by a known method. For example, it can manufacture according to the method as described in Heterocycle, 61, page 433 (2003).

  As described above, in one embodiment of the present invention, the inclusion of the compound (1) is essential, but in the other embodiments, the same effect as the compound (1) is exhibited. Compounds (hereinafter sometimes referred to as “compound” (2)) can be included.

In Formula (2), R ^{1 to} R ³ each independently represent a monovalent group. The benzene ring in Formula (2) may be further substituted by any substituent.

As the monovalent group in R ^{1 to} R ^{3, those} exemplified in the formula (1) can be preferably adopted. Further, as the optional substituent which the benzene ring at the β-position of pyrrole may have, those mentioned in the above-mentioned formula (1) can be preferably adopted.

  The specific example of a compound (2) is given to the following. However, it is not limited to these examples.

(Physical properties)
The maximum absorption wavelength (λmax) of the absorption maximum possessed by compound (1) is not particularly limited, but is preferably 500 nm or more, more preferably 550 nm or more, still more preferably 570 nm or more, and usually 640 nm or less, preferably 620 nm or less And 605 nm or less is more preferable. By setting the maximum absorption wavelength of the absorption maximum within the above range, color reproducibility tends to be improved. The maximum absorption wavelength of the absorption maximum can be calculated from an absorption spectrum prepared by measuring a solution in which the compound (1) is dissolved in a solvent such as tetrahydrofuran. As the detailed conditions, it is preferable to adopt those described in the examples.

  Furthermore, the half value width of the absorption maximum possessed by compound (1) is not particularly limited, but is preferably 35 nm or less, more preferably 30 nm or less, still more preferably 25 nm or less, and usually 13 nm or more It is. By setting the half value width of the absorption maximum to the upper limit value or less, color reproducibility of the display filter tends to be improved. The half maximum width (FWHM) of the absorption maximum reads the wavelength A1 and the wavelength A2 at which the half value of the absorbance A at the maximum absorption wavelength (λ max) is obtained in the above absorption spectrum, and calculates the absolute value of the difference between the wavelengths A1 and A2. It is obtained by

  In the compound (1), the number of absorption maxima at a wavelength of 500 to 640 nm is not particularly limited, but is preferably one from the viewpoint of suppressing a decrease in luminance. The number of absorption maxima can be calculated from the aforementioned absorption spectrum. In addition, the number of the absorption maximum in wavelength 500-640 nm means the number of the thing whose maximum absorption wavelength is contained in wavelength 500-640 nm among the absorption maximum contained in an absorption spectrum.

  On the other hand, the transmittance of the compound (1) at a wavelength of 380 to 450 nm is preferably 80% or more, more preferably 85% or more, still more preferably 90% or more, and the transmittance Is usually 100% or less. By setting the transmittance to the lower limit value or more, the color reproducibility of the display filter tends to be improved. The transmittance can be calculated from the aforementioned absorption spectrum.

[Quencher]
The coloring composition of the present invention contains a quencher. By containing the compound (1) and the quenching agent, the excited electrons or excitation energy of the compound (1) are transferred to the quenching agent by electron transfer or energy transfer to heat by the Forster mechanism or the Dexter mechanism. It is considered that the fluorescence of compound (1) is quenched by the conversion.

  The quencher is not particularly limited as long as it can quench the fluorescence of the compound (1), but since it tends to efficiently quench, it is a compound having a partial structure represented by the following general formula (i) Is preferred. The compound having a partial structure represented by the following general formula (i) is considered to effectively generate such electron transfer or energy transfer because it has an electron donating property and a suitable HOMO level. Furthermore, a compound suitable for the purpose of quenching the fluorescence of the compound (1) while suppressing the reduction of the transmittance because it has a feature of having an absorption maximum in the near infrared wavelength region and hardly absorbing in the visible light region. It is.

In formula (i), R ¹¹ and R ¹² each independently represent an arbitrary monovalent group, and R ¹¹ and R ¹² may be linked to each other to form a ring. * Represents a bond.

(R ¹¹ and R ¹² )
In formula (i), R ¹¹ and R ¹² each independently represent an arbitrary monovalent group. The optional monovalent group is not particularly limited, and includes, for example, a hydrogen atom, a halogen atom, an alkyl group which may have a substituent, an alkylthio group which may have a substituent, and a substituent And an aromatic ring group which may be substituted, and an aromatic ring thio group which may have a substituent.

As the halogen atom in R ¹¹ and R ^12, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, an effective electron-withdrawing and stability standpoint fluorine atoms Among these, preferred.

As the alkyl group in R ¹¹ and R ^12, straight-chain, for example, an alkyl group of branched or cyclic. The carbon number of the alkyl group is not particularly limited, but is preferably 30 or less, more preferably 20 or less, still more preferably 15 or less, and preferably 3 or more, more preferably 10 or more. By setting the carbon number to the upper limit value or less, the balance between the ease of synthesis and the solubility tends to be balanced.

Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, 2-propyl group, n-butyl group, isobutyl group, tert-butyl group, n-hexyl group, n-octyl group, 2-ethylhexyl Groups, cyclopentyl group, cyclohexyl group and the like. Among these, from the viewpoint of solubility, a primary or secondary branched alkyl group is preferable, and a 2-propyl group, a 2-ethylhexyl group, and the like are more preferable. Furthermore, R ¹¹ and R ¹² may be linked via a linking group to form a 5- to 10-membered ring. As a linking group in this case, -CH ₂ -CH = CH-CH _2- and the like can be mentioned. Also, one of the linking groups in the case of the alkylthio _{group, -CH 2 -CH 2 -S-CH} 2 -CH 2 - and the like.

  The substituent which the alkyl group may have is any substituent, but among them, a hydroxyl group, a halogen atom, an alkenyl group, an aliphatic hydrocarbon thio group, an aromatic hydrocarbon thio group, an aromatic heterocyclic thio group And aliphatic hydrocarbon oxy groups, aromatic hydrocarbon oxy groups, aromatic heterocyclic oxy groups, aromatic hydrocarbon groups, aromatic heterocyclic groups and the like.

The alkylthio group in R ¹¹ and R ¹² includes a linear, branched or cyclic alkylthio group. The carbon number of the alkylthio group is not particularly limited, but is preferably 30 or less, more preferably 20 or less, still more preferably 15 or less, and preferably 10 or more. By setting the carbon number to the upper limit value or less, the balance between the ease of synthesis and the solubility tends to be balanced.

Specific examples of the alkylthio group include methylthio group, ethylthio group, n-propylthio group, 2-propylthio group, n-butylthio group, isobutylthio group, tert-butylthio group, n-hexylthio group, n-octylthio group, 2- Ethylhexylthio group, cyclopentylthio group, cyclohexylthio group and the like can be mentioned. Among these, from the viewpoint of solubility, a primary or secondary branched alkylthio group is preferable, and a 2-propylthio group, a 2-ethylhexylthio group, and the like are more preferable. Furthermore, R ¹¹ and R ¹² may be linked via a linking group to form a 5- to 10-membered ring. As a linking group in this case, -S-CH ₂ -CH ₂ -S-, -S-CH ₂ -S-CH _2- and the like can be mentioned.

  The substituent which the alkylthio group may have is any substituent, but among them, a hydroxyl group, a halogen atom, an aliphatic hydrocarbon thio group, an aromatic hydrocarbon thio group, an aromatic heterocyclic thio group, an aliphatic group A hydrocarbon oxy group, an aromatic hydrocarbon oxy group, an aromatic heterocyclic oxy group, an aromatic hydrocarbon group, an aromatic heterocyclic group and the like can be mentioned.

The aromatic ring group in R ¹¹ and R ^12, include aromatic hydrocarbon ring groups and aromatic heterocyclic group, an aromatic hydrocarbon ring group from the viewpoint of suppressing the absorption in the ultraviolet region preferably.
The carbon number of the aromatic ring group is preferably 2 or more, more preferably 5 or more, still more preferably 6 or more, and preferably 15 or less, more preferably 12 or less, still more preferably 10 or less. When the carbon number is at least the lower limit value, the aromatic ring tends to be stabilized, and when the carbon number is at the upper limit value or less, side absorption from the aromatic ring tends to be suppressed.

The ring constituting the aromatic hydrocarbon ring group may be a single ring or a condensed ring. Examples of the aromatic hydrocarbon ring group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring and a triphenylene ring, having one free valence. And groups such as acenaphthene ring, fluoranthene ring and fluorene ring.
Among these, from the viewpoint of suppressing the secondary absorption derived from the aromatic hydrocarbon ring, a phenyl group or one in which R ¹¹ and R ¹² are linked to form a 5- or 6-membered aromatic ring is preferable.

  On the other hand, the ring constituting the aromatic heterocyclic group may be a single ring or a condensed ring. As the aromatic heterocyclic group, for example, furan ring, benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, carbazole having one free valence Ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzoisoxazole ring, benzoisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, Groups such as pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, sinoline ring, quinoxaline ring, phenanthridine ring, benzimidazole ring, perimidine ring, quinazoline ring, quinazolinone ring, azulene ring and the like can be mentioned.

  The substituent which the aromatic ring group may have is not particularly limited, but among them, a hydroxyl group, a halogen atom, an aliphatic hydrocarbon thio group, an aliphatic hydrocarbon oxy group, a silyl group, an amino group, a cyano group, a nitro And aliphatic hydrocarbon groups.

Among these, from the viewpoint of diversity of synthesis and molecular design, each of R ¹¹ and R ¹² independently has a thiophene ring which may have a substituent, a benzothiophene group, or R ¹¹ and R ¹² are connected It is preferable to form a 5- or 6-membered aromatic heterocyclic ring.

As the aromatic ring thio group in R ¹¹ and R ¹² , an aromatic hydrocarbon ring thio group and an aromatic heterocyclic ring thio group can be mentioned, and from the viewpoint of suppressing the absorption in the ultraviolet region, an aromatic hydrocarbon ring thio group is preferable.
The carbon number of the aromatic ring thio group is preferably 2 or more, more preferably 5 or more, still more preferably 6 or more, and preferably 15 or less, more preferably 12 or less, still more preferably 10 or less. When the carbon number is at least the lower limit value, the aromatic ring tends to be stabilized, and when the carbon number is at the upper limit value or less, side absorption from the aromatic ring tends to be suppressed.

The ring constituting the aromatic hydrocarbon ring thio group may be a single ring or a condensed ring. Examples of the aromatic hydrocarbon ring thio group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring and a chrysene ring in a thio group having one free valence. And those having a group such as triphenylene ring, acenaphthene ring, fluoranthene ring and fluorene ring.
Among these, from the viewpoint of suppressing the secondary absorption derived from the aromatic hydrocarbon ring, a phenylthio group or one in which R ¹¹ and R ¹² are linked to form a 5- or 6-membered aromatic ring is preferable.

  On the other hand, the ring constituting the aromatic heterocyclic thio group may be a single ring or a condensed ring. The aromatic heterocyclic thio group is, for example, a thio group having one free valence, furan ring, benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, imidazole ring, oxadiazole ring, Indole ring, carbazole ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzoisoxazole ring, benzoisothiazole ring, benzimidazole ring, pyridine ring , Pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, sinoline ring, quinoxaline ring, phenanthridine ring, benzimidazole ring, perimidine ring, quinazoline ring, quinazolinone ring, azulene ring, etc. Those that can be mentioned.

  The substituent which the aromatic ring thio group and the aromatic heterocyclic ring thio group may have is not particularly limited, but among them, a hydroxyl group, a halogen atom, an aliphatic hydrocarbon thio group, an aliphatic hydrocarbon oxy group, a silyl group Amino group, cyano group, nitro group, aliphatic hydrocarbon group and the like.

Among these, from the viewpoint of diversity of synthesis and molecular design, each of R ¹¹ and R ¹² independently may be a thiophene ring thio group which may have a substituent, a benzothiophene ring thio group, or R ¹¹ It is preferable that R ¹² be linked to form a 5- or 6-membered aromatic heterocyclic ring.

  The number of the general formula (i) contained in one molecule of the quencher is not particularly limited, but usually 1 or more and 2 or more are preferable, 5 or less is preferable, and 3 or less is more preferable. By setting the amount to the lower limit or more, there is a tendency that an efficient planar π-conjugated compound can be used, and by setting the amount to the upper limit or less, ease of synthesis and solubility can be maintained.

  The molecular weight of one quencher molecule is not particularly limited, but is preferably 100 or more, more preferably 150 or more, still more preferably 200 or more, and preferably 1000 or less, more preferably 800 or less, and still more preferably 500 or less. There is a tendency that introduction of the minimum necessary unit becomes possible by setting it to the above lower limit value, and there is a tendency not to lower the thermal decomposition temperature excessively by setting it to the above upper limit value.

  Among the quenchers, from the viewpoint of the resistance of the compound in multiple components, a compound represented by the following general formula (i-1) and a compound represented by the following general formula (i-2) are preferable. The compounds represented by the following general formula (i-2) are dithiolate metal complexes and aminothio metal complexes.

In formula (i-1), R ¹¹ and R ¹² have the same meanings as in formula (i).
R ¹³ is a monovalent hydrocarbon group which may have a substituent. The —CH ₂ — contained in the hydrocarbon group is —S—, —NH—, —NR ¹⁵ —, —O—, —CO—, —COO—, —C = S—, and —C = S—. It may be substituted by at least one selected from the group consisting of S-.
R ¹⁴ represents any monovalent group. R ¹³ and R ¹⁴ may be linked to each other to form a ring.
R ¹⁵ represents a substituent alkyl group which may have a or an optionally substituted monovalent aromatic ring group.

In formula (i-2), R ¹¹ and R ¹² have the same meanings as in formula (i).
Each independently R ¹⁶ and R ^17, -S -, - NH-, or -NR ²⁰ - represents a.
Each of R ¹⁸ and R ¹⁹ independently represents an arbitrary monovalent group.
R ²⁰ represents an alkyl group which may have a substituent or a monovalent aromatic ring group which may have a substituent.
M ¹ represents a metal atom.

[Compound represented by General Formula (i-1)]

In formula (i-1), R ¹¹ and R ¹² have the same meanings as in formula (i).
R ¹³ is a monovalent hydrocarbon group which may have a substituent. The —CH ₂ — contained in the hydrocarbon group is —S—, —NH—, —NR ¹⁵ —, —O—, —CO—, —COO—, —C = S—, and —C = S—. It may be substituted by at least one selected from the group consisting of S-.
R ¹⁴ represents any monovalent group. R ¹³ and R ¹⁴ may be linked to each other to form a ring.
R ¹⁵ represents a substituent alkyl group which may have a or an optionally substituted monovalent aromatic ring group.

(R ¹³ )
In formula (i-1), R ¹³ is a monovalent hydrocarbon group which may have a substituent. Examples of the monovalent hydrocarbon group include an alkyl group, an alkenyl group and a monovalent aromatic ring group.

The alkyl group includes a linear, branched or cyclic alkyl group. The carbon number of the alkyl group is not particularly limited, but is preferably 20 or less, more preferably 15 or less, still more preferably 10 or less, and preferably 3 or more. By setting the temperature to the upper limit or less, the thermal decomposition temperature tends not to be lowered excessively, and by setting the temperature to the lower limit or more, the solubility of the compound tends to be maintained.
Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, 2-propyl group, n-butyl group, isobutyl group, tert-butyl group, n-hexyl group, n-octyl group, 2-ethylhexyl Groups, cyclopentyl group, cyclohexyl group and the like. Among these, 2-propyl, 2-butyl, n-hexyl and n-octyl groups are preferable, and 2-propyl and 2-butyl groups are more preferable, from the viewpoint of efficiently improving the solubility.
The substituent which the alkyl group may have is any substituent, but among them, a hydroxyl group, a halogen atom, a cyano group, an aliphatic hydrocarbon thio group, an aromatic hydrocarbon thio group, an aromatic heterocyclic thio group And aliphatic hydrocarbon oxy groups, aromatic hydrocarbon oxy groups, aromatic heterocyclic oxy groups, aromatic hydrocarbon groups, aromatic heterocyclic groups and the like.

The alkenyl group includes a linear, branched or cyclic alkenyl group. The carbon number of the alkenyl group is not particularly limited, but is preferably 10 or less, more preferably 5 or less, still more preferably 3 or less, and preferably 2 or more. By setting the content to the upper limit or less, the solubility tends to be maintained, and by setting the content to the lower limit or more, an effective electron donor compound tends to be formed.
Specific examples of the alkenyl group include ethenyl group, propenyl group, butenyl group, hexenyl group, octenyl group, cyclohexenyl group, 1,3-butadienyl group, 1,3,5-hexatrienyl group, 1,3,5. , 7-octatetraenyl group and the like. Among these, ethenyl and cyclohexenyl are preferable from the viewpoint of the stability of the compound.
The substituent which the alkenyl group may have is any substituent, but among them, a hydroxyl group, a halogen atom, a cyano group, an aliphatic hydrocarbon thio group, an aromatic hydrocarbon thio group, an aromatic heterocyclic thio group And aliphatic hydrocarbon oxy groups, aromatic hydrocarbon oxy groups, aromatic heterocyclic oxy groups, aromatic hydrocarbon groups, aromatic heterocyclic groups and the like.

The monovalent aromatic ring group is preferably a monovalent aromatic hydrocarbon ring group from the viewpoint of suppressing absorption in the ultraviolet region.
The carbon number of the aromatic ring group is preferably 2 or more, more preferably 5 or more, still more preferably 6 or more, and preferably 15 or less, more preferably 12 or less, still more preferably 10 or less. By setting the content to the above lower limit or more, there is a tendency to be an aromatic ring having an electron donating property, and by setting the above upper limit or less, the light resistance tends to be improved.

The ring constituting the aromatic hydrocarbon ring group may be a single ring or a condensed ring. Examples of the aromatic hydrocarbon ring group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring and a triphenylene ring, having one free valence. And groups such as acenaphthene ring, fluoranthene ring and fluorene ring.
Among these, a phenyl group and a naphthyl group are preferable in terms of solubility and planarity.

  The substituent which the aromatic ring group may have is not particularly limited, but among them, a hydroxyl group, a halogen atom, an aliphatic hydrocarbon thio group, an aliphatic hydrocarbon oxy group, a silyl group, an amino group, a cyano group, a nitro And aliphatic hydrocarbon groups.

Is, -S - - -CH ₂ contained in the hydrocarbon group in ^{R 13, - NH -, -} NR 15 -, - O -, - CO -, - COO-, and -C = consist S-S- It may be substituted by at least one selected from the group. Among these, from the viewpoint of enhancing the electron donating property, it is preferable that one or more of —CH ₂ — contained in the hydrocarbon group be substituted by —S—.

-CH ₂ contained in the hydrocarbon group in R ¹³ - as has been substituted with the substituent, an aromatic heterocyclic group. The ring constituting the aromatic heterocyclic group may be a single ring or a condensed ring. As the aromatic heterocyclic group, for example, furan ring, benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, carbazole having one free valence Ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzoisoxazole ring, benzoisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, Groups such as pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, sinoline ring, quinoxaline ring, phenanthridine ring, benzimidazole ring, perimidine ring, quinazoline ring, quinazolinone ring, azulene ring and the like can be mentioned.

  Among the compounds represented by the general formula (i-1), from the viewpoint of effectively interacting with the compound (1) by the strong electron donating effect, the following general formulas (i-1-1) to (i-) The compound represented by 1-5) is preferable.

In formula (i-1-1), R ¹¹ and R ¹² have the same meaning as in formula (i).

In formula (i-1-2), R ¹¹ and R ¹² have the same meanings as in formula (i). α represents an oxygen atom or a sulfur atom.

In formula (i-1-3), R ¹¹ and R ¹² have the same meanings as in formula (i). β represents -S- or -NH-.

In formula (i-1-4), R ¹¹ and R ¹² have the same meaning as in formula (i).

In formula (i-1-5), R ¹¹ and R ¹² have the same meaning as in formula (i).

  Specific examples of the compound represented by Formula (i-1) will be given below.

[Compound Represented by General Formula (i-2)]

In formula (i-2), R ¹¹ and R ¹² have the same meanings as in formula (i).
Each independently R ¹⁶ and R ^17, -S -, - NH -, - NR 20 - represents a.
Each of R ¹⁸ and R ¹⁹ independently represents an arbitrary monovalent group.
R ²⁰ represents an alkyl group which may have a substituent or a monovalent aromatic ring group which may have a substituent.
M ¹ represents a metal atom.

(R ¹⁶ and R ¹⁷ )
Wherein (i-2), R ¹⁶ and R ¹⁷ each independently, -S -, - NH -, - NR 20 - represents a. R ²⁰ represents an alkyl group which may have a substituent or a monovalent aromatic ring group which may have a substituent.

The alkyl group for R ²⁰ includes a linear, branched or cyclic alkyl group. The carbon number of the alkyl group is not particularly limited, but is preferably 20 or less, more preferably 15 or less, still more preferably 10 or less, and preferably 4 or more. By setting the temperature to the upper limit or less, the thermal decomposition temperature tends not to be lowered excessively, and by setting the temperature to the lower limit or more, solubility tends to be maintained.
Specific examples of the alkyl group which may have a substituent include methyl group, ethyl group, n-propyl group, 2-propyl group, n-butyl group, isobutyl group, tert-butyl group and n-hexyl group , N-octyl group, 2-ethylhexyl group, cyclopentyl group, cyclohexyl group, benzyl group and the like. Among these, from the viewpoint of solubility and stability, n-butyl, n-hexyl, cyclohexyl and benzyl groups are preferable, and a benzyl group is more preferable.

  The substituent which the alkyl group may have is any substituent, but among them, a hydroxyl group, a halogen atom, a cyano group, an aliphatic hydrocarbon thio group, an aromatic hydrocarbon thio group, an aromatic heterocyclic thio group And aliphatic hydrocarbon oxy groups, aromatic hydrocarbon oxy groups, aromatic heterocyclic oxy groups, aromatic hydrocarbon groups, aromatic heterocyclic groups and the like.

Examples of the monovalent aromatic ring group for R ²⁰ include monovalent aromatic hydrocarbon ring groups and monovalent aromatic heterocyclic groups, and from the viewpoint of suppressing absorption near 400 nm, aromatic hydrocarbon ring groups are preferred. preferable.
The carbon number of the aromatic ring group is preferably 2 or more, more preferably 5 or more, still more preferably 6 or more, and preferably 15 or less, more preferably 12 or less, still more preferably 10 or less. There is a tendency of the π conjugate expansion effect by setting it to the above lower limit value, and there is a tendency to improve the light resistance by setting it to the above upper limit value.

  The ring constituting the aromatic hydrocarbon ring group may be a single ring or a condensed ring. Examples of the aromatic hydrocarbon ring group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring and a triphenylene ring, having one free valence. And groups such as acenaphthene ring, fluoranthene ring and fluorene ring.

  On the other hand, the ring constituting the aromatic heterocyclic group may be a single ring or a condensed ring. As the aromatic heterocyclic group, for example, furan ring, benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, carbazole having one free valence Ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzoisoxazole ring, benzoisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, Groups such as pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, sinoline ring, quinoxaline ring, phenanthridine ring, benzimidazole ring, perimidine ring, quinazoline ring, quinazolinone ring, azulene ring and the like can be mentioned.

  The substituent which the aromatic ring group may have is not particularly limited, but among them, a hydroxyl group, a halogen atom, an aliphatic hydrocarbon thio group, an aliphatic hydrocarbon oxy group, a silyl group, an amino group, a cyano group, a nitro And aliphatic hydrocarbon groups.

As described above, -S each independently R ¹⁶ and ^{R 17 -, - NH -,} - NR 20 - represents a view of the stability of the complex Among these, -S- or -NR ²⁰ - is preferably And -S- is more preferable.

(R ¹⁸ and R ¹⁹ )
In formula (i-2), R ¹⁸ and R ¹⁹ each represent an arbitrary monovalent group. As the optional monovalent group, those mentioned as R ¹¹ and R ¹² can be preferably used.

(M ¹ )
In formula (i-2), M ¹ represents a metal atom. M ¹ is not particularly limited as long as it is a metal atom, but from the viewpoint of suppressing absorption in the visible light region, preferably, Ni, Pd, or Pt periodical group 10 transition metal atom; Co; Fe; Cu; Ag; Au And Zn. Among these, from the viewpoint of the stability of the complex, a group 10 transition metal atom of the periodic table is more preferable, and particularly preferable is Ni or Pd.

  Among the compounds represented by the above general formula (i-2), the compounds represented by the above general formula (i-2) are described below from the viewpoint that it is difficult for the demetalation of the complex to occur by the adhesive or the like. The compound represented by general formula (i-2-1) is preferable.

In formula (i-2-1), R ²¹ and R ²² each independently represent a monovalent substituent.
Each of X ¹ and X ² independently represents a monovalent group having 4 or more constituent atoms. X ¹ and X ² may be linked to form a ring.
The benzene ring in Formula (i-2-1) may further have an arbitrary substituent, and adjacent substituents may be linked to form a ring.
M ¹ is as defined in formula (i-2).

(R ²¹ and R ²² )
In formula (i-2-1), R ²¹ and R ²² each independently represent a monovalent substituent. The monovalent substituent is not particularly limited, and examples thereof include a halogen atom, an alkyl group which may have a substituent, and an aromatic ring group which may have a substituent.

Examples of the halogen atom in R ²¹ and R ^22, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and a fluorine atom are preferred from the viewpoint of stability of effective electron-withdrawing and complexes among them.

Moreover, as an alkyl group in R ²¹ and R ²² , a linear, branched or cyclic alkyl group can be mentioned. The carbon number of the alkyl group is not particularly limited, but is preferably 30 or less, more preferably 20 or less, still more preferably 15 or less, and preferably 3 or more. By setting the carbon number to the upper limit value or less, balance of the easiness of synthesis of the complex and the solubility tends to be balanced.
Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, 2-propyl group, n-butyl group, isobutyl group, tert-butyl group, n-hexyl group, n-octyl group, 2-ethylhexyl Groups, cyclopentyl group, cyclohexyl group and the like. Among these, from the viewpoint of solubility, a primary or secondary branched alkyl group is preferable, and a 2-propyl group, a 2-ethylhexyl group, and the like are more preferable.
The substituent which the alkyl group may have is not particularly limited, but among them, a hydroxyl group, a halogen atom, an aliphatic hydrocarbon thio group, an aromatic hydrocarbon thio group, an aromatic heterocyclic thio group, an aliphatic hydrocarbon oxy Groups, aromatic hydrocarbon oxy groups, aromatic heterocyclic oxy groups, aromatic hydrocarbon groups, aromatic heterocyclic groups and the like.

The aromatic ring group in R ²¹ and R ^22, include aromatic hydrocarbon ring groups and aromatic heterocyclic group, an aromatic hydrocarbon ring group is preferred from the viewpoint of suppressing the absorption in the ultraviolet region.
The carbon number of the aromatic ring group is preferably 2 or more, more preferably 5 or more, still more preferably 6 or more, and preferably 15 or less, more preferably 12 or less, still more preferably 10 or less. When the carbon number is at least the lower limit value, the complex tends to be stabilized by the aromatic ring, and when the carbon number is at the upper limit value or less, side absorption from the aromatic ring tends to be suppressed.

The ring constituting the aromatic hydrocarbon ring group may be a single ring or a condensed ring. Examples of the aromatic hydrocarbon ring group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring and a triphenylene ring, having one free valence. Examples include acenaphthene ring, fluoranthene ring and fluorene ring.
Among the aromatic hydrocarbon ring groups, a phenyl group is preferable from the viewpoint of suppressing side absorption due to the aromatic hydrocarbon ring.

  On the other hand, the ring constituting the aromatic heterocyclic group may be a single ring or a condensed ring. As the aromatic heterocyclic group, for example, furan ring, benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, carbazole having one free valence Ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, furopyrrole ring, furofuran ring, thienofuran ring, benzoisoxazole ring, benzoisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, Groups such as pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, sinoline ring, quinoxaline ring, phenanthridine ring, benzimidazole ring, perimidine ring, quinazoline ring, quinazolinone ring, azulene ring and the like can be mentioned.

  The substituent which the aromatic ring group may have is not particularly limited, but among them, a hydroxyl group, a halogen atom, an aliphatic hydrocarbon thio group, an aliphatic hydrocarbon oxy group, a silyl group, an amino group, a cyano group, a nitro And aliphatic hydrocarbon groups.

Among these, from the viewpoint of improving the resistance of the complex, R ²¹ and R ²² are preferably each independently a phenyl group which may have a substituent.

(X ¹ and X ² )
Each of X ¹ and X ² independently represents a monovalent group having 4 or more constituent atoms. X ¹ and X ² may be linked to form a ring.

The number of constituent atoms of the monovalent group of X ¹ and X ² is not particularly limited as long as it is 4 or more, but 6 or more is preferable, 8 or more is more preferable, 10 or more is more preferable, and 30 Or less is preferable, 20 or less is more preferable, and 16 or less is more preferable. When the number of constituent atoms is at least the lower limit, the stability of the complex tends to be maintained, and when the number is at most the upper limit, the ease of taking out the synthesized complex tends to be maintained.

The type of atoms constituting the monovalent group of X ¹ and X ² is not particularly limited, but from the viewpoint of easiness of synthesis, from the group consisting of hydrogen atoms, carbon atoms, oxygen atoms, nitrogen atoms, sulfur atoms and silicon atoms It is preferable that it is at least one selected.

Examples of the monovalent group of X ¹ and X ² include a hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, a carbonyl-containing group, and a substituent. A hydrocarbon thio group which may have, a silyl group which may have a substituent, a hydrocarbon amino group which may have a substituent, a hydrocarbon oxy group which may have a substituent And optionally substituted hydrocarbon oxycarbonyloxy and the like. Note that the number of constituent atoms of the monovalent group of X ¹ and X ^2, if X ¹ and X ² has a substituent, refers to the number of total, including the constituent atoms of its substituent.

  As a hydrocarbon group, an aliphatic hydrocarbon group and an aromatic hydrocarbon ring group are mentioned. The carbon number in the hydrocarbon group is not particularly limited, but is usually 1 or more, preferably 2 or more, more preferably 3 or more, still more preferably 4 or more, and preferably 20 or less, more preferably 15 or less, and 12 or less. More preferable. When the carbon number is at least the lower limit, the resistance of the complex tends to be improved, and when the carbon number is at the upper limit or less, the synthesized complex tends to be easily taken out.

  Specific examples of the aliphatic hydrocarbon group include n-butyl group, 2-methylbutyl group, 3-methylbutyl group, cyclohexylmethyl group, neopentyl group, 2-ethylbutyl group, 2-butyl group, cyclohexyl group, 3 -Linear, branched or cyclic alkyl group such as pentyl group; alkenyl group such as 2-butenyl group, 3-butenyl group, 2,4-pentadienyl group and the like; alkadienyl group; alkynyl group such as 2-hexynyl group Etc. Among these, from the viewpoint of the resistance of the complex, it is preferably an aliphatic hydrocarbon group having 4 to 12 carbon atoms, and more preferably a branched aliphatic hydrocarbon group having 4 to 12 carbon atoms.

  The ring constituting the aromatic hydrocarbon ring group may be a single ring or a condensed ring. Specific examples of the aromatic hydrocarbon ring group include a phenyl group, a naphthyl group, an anthranyl group, a fluorenyl group, a phenanthrenyl group, an azulenyl group, a metallocenyl group and the like. Among them, from the viewpoint of suppressing the side absorption, a monocyclic or fused bicyclic aromatic hydrocarbon group having 6 to 12 carbon atoms is preferable.

The ring constituting the aromatic heterocyclic group may be a single ring or a fused ring. The carbon number of the aromatic heterocyclic group is not particularly limited, but is usually 2 or more, preferably 3 or more, more preferably 4 or more, and preferably 12 or less, more preferably 10 or less, still more preferably 6 or less, The following are particularly preferred. When the carbon number is at least the lower limit, the electron donating effect tends to be obtained, and when the carbon number is at the upper limit or less, side absorption tends to be suppressed.
Specific examples of the aromatic heterocyclic group include thienyl group, furyl group, pyrrolyl group, pyridyl group, imidazolyl group, pyrazolyl group, indolyl group, quinoxalinyl group, atalidinyl group, thiazolyl group, pyrazinyl group and the like. Among these, from the viewpoint of efficiently introducing a steric hindrance site, a monocyclic or bicyclic 5-membered heterocyclic group having 3 to 12 carbon atoms is preferable.

The carbonyl-containing group is not particularly limited as long as it is a monovalent group containing a carbonyl, and examples thereof include an acyl group (-COR), a carbamoyl group (-CONRR '), and an oxycarbonyl group having a substituent (-C (O ) OR).
Specifically, R of the acyl group (-COR) is, in addition to the same as the specific examples of the aliphatic hydrocarbon group, aromatic hydrocarbon ring group and aromatic heterocyclic group mentioned above, n-propyl And 2-propenyl group.
Moreover, R and R 'of the carbamoyl group (-CONRR') are, in addition to the same as the specific examples of the aliphatic hydrocarbon group, aromatic hydrocarbon ring group and aromatic heterocyclic group mentioned above, an ethyl group , N-propyl group, 2-propenyl group, ethynyl group and the like.
R of the substituted oxycarbonyl group (—C (O) OR) is the same as the specific examples of the aliphatic hydrocarbon group, aromatic hydrocarbon ring group and aromatic heterocyclic group described above , An ethyl group, an n-propyl group, a 2-propenyl group, a titinyl group and the like.

  R of the hydrocarbon thio group (-SR) is, in addition to the same as the specific examples of the aliphatic hydrocarbon group, aromatic hydrocarbon ring group and aromatic heterocyclic group mentioned above, n-propyl group, 2 -Propenyl group, ethynyl group etc. are mentioned.

  Examples of the silyl group include silyl groups such as t-butyldiphenylsilyl group, n-butyldimethylsilyl group, dimethylpropylsilyl group, dimethylphenylsilyl group, dimethylisopropylsilyl group and triisopropylsilyl group. Among these, from the viewpoint of solubility, an alkylsilyl group having 3 to 18 carbon atoms is preferable.

  R and R ′ of the hydrocarbon amino group (—NRR ′) are, in addition to the same as the specific examples of the aliphatic hydrocarbon group, aromatic hydrocarbon ring group and aromatic heterocyclic group mentioned above, n- A propyl group, 2-ethylhexyl group, 2-propenyl group, ethynyl group etc. are mentioned.

  R of the hydrocarbon oxy group (—OR) is not limited to the same as the specific examples of the aliphatic hydrocarbon group, aromatic hydrocarbon group and aromatic heterocyclic group mentioned above, and n-propyl group, 2- Ethylhexyl group, 2-propenyl group, ethynyl group etc. are mentioned.

  In addition to the same as the specific examples of the aliphatic hydrocarbon group, the aromatic hydrocarbon ring group and the aromatic heterocyclic group mentioned above, R of the hydrocarbon oxycarbonyloxy group (—OC (O) OR) is, An ethyl group, 2-ethylhexyl group, 2-propenyl group, ethynyl group etc. are mentioned.

  When the above monovalent group has a substituent, the type of the substituent is not particularly limited as long as it does not affect the fluorescence quenching of the compound (1). For example, halogen atom, hydroxyl group, nitro group, cyano group, alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, heteroaryl group, alkoxy group, aryloxy group, heteroaryloxy group, alkylthio group, arylthio group, heteroaryl group Luthio group, amino group, acyl group, aminoacyl group, ureido group, sulfonamide group, carbamoyl group, sulfamoyl group, sulfamoylamino group, alkoxycarbonyl group, aryloxycarbonyl group, heteroaryloxycarbonyl group, alkylsulfonyl group, And arylsulfonyl group, heteroarylsulfonyl group, imide group and silyl group.

  Specifically, an alkyl group having 1 to 6 carbon atoms such as a methyl group or an ethyl group; an alkenyl group having 1 to 6 carbon atoms such as an ethynyl group or a propynyl group; an alkynyl group having 1 to 6 carbon atoms such as an acetylenyl group; , An aryl group having 6 to 20 carbon atoms such as naphthyl group; a heteroaryl group having 6 to 20 carbon atoms such as thienyl group, furyl group and pyridyl group; an alkoxy group having 1 to 6 carbon atoms such as ethoxy group and propoxy group; An aryloxy group having 6 to 20 carbon atoms such as phenoxy group and naphthoxy group; a C 3 to 20 heteroaryloxy group such as pyridyloxy group and thienyloxy group; 1 to 6 carbon atoms such as methylthio group and ethylthio group Alkylthio group having 6 to 20 carbon atoms such as phenylthio group and naphthylthio group; carbon such as pyridylthio group and thienylthio group Heteroarylthio group having a number of 3 to 20; an amino group having 1 to 20 carbon atoms which may have a substituent such as dimethylamino group or diphenylamino group; or 2 to 20 carbon atoms having an acetyl group or pivaloyl group. Acyl groups of 2 to 20 carbon atoms such as acetylamino and propyloxyamino; ureido groups of 2 to 20 carbons such as 3-methylureido; and such as methanesulfonamido and benzenesulfonamido C1-C20 sulfonamido group; C1-C20 carbamoyl group such as dimethylcarbamoyl group and ethylcarbamoyl group; C1-C20 sulfamoyl group such as ethylsulfamoyl group; dimethylsulfamoylamino group Sulfamoylamino group having 1 to 20 carbon atoms, such as; methoxycarbonyl group, ethoxycarbonyl group Which C2-C6 alkoxycarbonyl group; a C7-C20 aryloxycarbonyl group such as a phenoxy carboni group, a naphthoxycarbonyl group; a C6-C20 heteroaryloxycarbonyl group such as a pyridyloxycarbonyl group Alkylsulfonyl group having 1 to 6 carbon atoms such as methanesulfonyl group, ethanesulfonyl group, trifluoromethanesulfonyl group; arylsulfonyl group having 6 to 20 carbon atoms such as benzenesulfonyl group and monofluorobenzenesulfonyl group; thienylsulfonyl group and the like Heteroarylsulfonyl groups having 3 to 20 carbon atoms; Imde groups having 4 to 20 carbon atoms such as phthalimide; silyl groups substituted at three positions with a substituent selected from the group consisting of alkyl groups and aryl groups Be

  Among these, an alkyl group, an alkoxy group, an alkylthio group, and an amino group having a substituent are preferable from the viewpoint of the balance between steric hindrance and solubility.

The benzene ring in formula (i-2-1) may further have an optional substituent. The type of the optional substituent is not particularly limited as long as it does not affect the fluorescence quenching of the compound (1), and for example, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an alkyl group, an alkenyl group, an alkynyl group , Aryl group, heteroaryl group, alkoxy group, aryloxy group, heteroaryloxy group, alkylthio group, arylthio group, heteroarylthio group, amino group, acyl group, aminoacyl group, ureido group, sulfonamide group, carbamoyl group And sulfamoyl group, sulfamoylamino group, alkoxycarbonyl group, aryloxycarbonyl group, heteroaryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl group, heteroarylsulfonyl group, imide group and silyl group. Specifically, it is the same as the specific example mentioned above as the substituent which the monovalent group of X ¹ and X ² may have.
When the benzene ring in the formula (i-2-1) further has an arbitrary substituent, the number thereof is not particularly limited, but is preferably 1 or more, 4 or less, 3 or less, more preferably 2 or less. Is more preferred.

The substitution position of these optional substituents is also not particularly limited, but from the viewpoint of imparting further steric hindrance, the ortho position is preferable. On the other hand, the meta position is preferred from the viewpoint of achieving both steric hindrance and easiness of synthesis.
Incidentally, the carbon atom to the benzene ring in formula (i-2-1) has a substituent other than X ¹ and X ^2, the optional substituents are adjacent to X ^1, X ² on the benzene ring When substituted, this group and X ¹ and X ² may combine to form a ring fused to a benzene ring.

  The compound represented by general formula (i-2-1) may be coordinated to be in a salt form. From the viewpoint of solubility in a particular solvent, preferred is a salt with a counter cation containing a Group 15 atom of the periodic table, and more preferred is a salt with a quaternary ammonium salt.

  In the present invention, the compound of the formula (i-2-1) may include the following two kinds of regioisomeric structures, but they are defined as the same without distinction.

  Specific examples of the compound represented by Formula (i-2) will be given below.

  Although the manufacturing method of the compound represented by Formula (i-1) is not specifically limited, For example, the method as described in Chemical Reviews, 104, 5151-5184 (2004) is employable. Moreover, although the manufacturing method of the compound represented by Formula (i-2) is not specifically limited, For example, the method as described in international publication 2006/118277 pamphlet can be employ | adopted.

[Other ingredients]
The coloring composition of the present invention contains the compound (1) and a quencher, and may further contain other components as necessary. Other components include binder resins, adhesives, solvents, and other additives.

(Binder resin)
Although it does not specifically limit as binder resin, Resins, such as (meth) acrylic-type resin (PMMA etc.), polyamide-type resin, polyurethane-type resin, polyolefin-type resin, polycarbonate resin, etc. are mentioned.

(Adhesive)
The adhesive is not particularly limited, and examples thereof include acrylics, polyesters, polyamides, polyurethanes, polyolefins, polycarbonates, rubbers, silicone resins, and the like. Among these, acrylic pressure-sensitive adhesives and silicone resin pressure-sensitive adhesives are preferable.

  The adhesive may be one obtained by crosslinking the resin component by heating or the like, or one before the crosslinking.

As a resin component constituting the pressure-sensitive adhesive, it is preferable to use a (meth) acrylic copolymer from the viewpoint of optical properties, particularly transparency. As a monomer which comprises a (meth) acrylic-type copolymer, (meth) acrylic-acid alkylester, a carboxyl group-containing monomer, etc. are mentioned.
The weight average molecular weight (Mw) of the (meth) acrylic copolymer measured by gel permeation chromatography (GPC) method is, in terms of polystyrene, preferably 500,000 or more, more preferably 600,000 or more, and 700,000 The above is more preferable, 800,000 or more is further preferable, 900,000 or more is particularly preferable, 1,000,000 or more is most preferable, 3,000,000 or less is preferable, 2,500,000 or less is more preferable, and 2,000,000 or less is more preferable. The durability of the compound (1) tends to be improved by setting the Mw to the above lower limit value, and the workability as an adhesive tends to improve by setting the Mw to the above upper limit value or less.
Further, the glass transition temperature (Tg) of the (meth) acrylic copolymer is preferably 0 ° C. or less, more preferably −5 ° C. or less, still more preferably −10 ° C. or less, and usually −100 ° C. or more. By setting the Tg to the upper limit value or less, a composition having excellent adhesiveness at a normal temperature tends to be obtained.

Moreover, the adhesive may contain components, such as a crosslinking agent and a silane coupling agent, other than the said resin component. As a crosslinking agent, an isocyanate compound, a metal chelate compound, an epoxy compound etc. are mentioned.
As each component which comprises the adhesive mentioned above, the thing as described in Unexamined-Japanese-Patent No. 2017-53878, Unexamined-Japanese-Patent No. 2017-58422, Unexamined-Japanese-Patent No. 2017-71730 etc. is employable, for example.

(solvent)
The solvent is not particularly limited, but alkanes such as butane, pentane, hexane, heptane and octane; cycloalkanes such as cyclopentane, cyclohexane, cycloheptane and cyclooctane; ethanol, propanol, butanol and amyl Alcohols such as alcohol, hexanol, heptanol, octanol, decanol, undecanol, diacetone alcohol, furfuryl alcohol; Cellosolves such as methyl cellosolve, ethyl cellosolve, butyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate; Propylene glycol monomethyl ether, propylene Glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate Propylene glycols such as propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate and dipropylene glycol dimethyl ether; ketones such as acetone, methyl amyl ketone, cyclohexanone and acetophenone; ethers such as dioxane and tetrahydrofuran; butyl acetate, Esters such as amyl acetate, ethyl butyrate, butyl butyrate, diethyl oxalate, ethyl pyruvate, ethyl 2-hydroxybutyrate, ethyl acetoacetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate and the like; chloroform, methylene chloride , Halogenated hydrocarbons such as tetrachloroethane; aromatic hydrocarbons such as benzene, toluene, xylene and the like; Amides, such as highly polar solvents such as N- methylpyrrolidone.

(Other additives)
Although it does not specifically limit as another additive, Additives, such as a near-infrared absorber, a ultraviolet absorber, an antistatic agent, an antioxidant, a dispersing agent, a flame retardant, a lubricant, a plasticizer, etc. are mentioned.

(Content ratio of each component in the coloring composition)
The content ratio of the compound (1) in the coloring composition of the present invention is not particularly limited, but in the case of a coloring resin composition containing a binder resin and an adhesive, 0.001% by mass or more is preferable in the total solid content. .005 mass% or more is more preferable, 0.01 mass% or more is more preferable, 0.1 mass% or more is particularly preferable, 10 mass% or less is preferable, 5 mass% or less is more preferable, 1 mass% or less Is more preferably 0.5% by mass or less. There is a tendency that the composition becomes stable by setting the content ratio of the compound (1) to the above lower limit value, and the precipitation of the compound (1) can be suppressed by setting the content ratio to the above upper limit value.
On the other hand, in the case of a coloring composition which does not contain a binder resin or an adhesive, the content ratio of the compound (1) is preferably 0.01% by mass or more in the total solid, more preferably 0.1% by mass or more, 1 % By mass or more is more preferable, 5% by mass or more is particularly preferable, 20% by mass or less is preferable, and 10% by mass or less is more preferable. There is a tendency that the composition becomes stable by setting the content ratio of the compound (1) to the above lower limit value, and the precipitation of the compound (1) can be suppressed by setting the content ratio to the above upper limit value.

Although the content ratio of the quenching agent in the coloring composition of the present invention is not particularly limited, in the case of a coloring resin composition containing a binder resin and an adhesive, 0.001% by mass or more is preferable in the total solid content, and 0.01 More preferably, it is 0.05% by mass or more, still more preferably 0.1% by mass or more, particularly preferably 0.2% by mass or more, and preferably 2% by mass or less. The following are more preferable. When the content ratio of the quencher is at least the lower limit value, the quenching action of the compound (1) tends to be easily exhibited, and when it is at the upper limit value or less, the absorption in the visible region of the quencher is reduced. Tend.
On the other hand, in the case of the coloring composition which does not contain a binder resin and an adhesive, 0.01 mass% or more is preferable in a total solid, and, as for the content rate of a quenching agent, 0.1 mass% or more is more preferable, and 1 mass% The above is more preferable, 10 mass% or more is further preferable, 30 mass% or more is particularly preferable, 80 mass% or less is preferable, 60 mass% or less is more preferable, and 40 mass% or less is more preferable. When the content ratio of the quencher is at least the lower limit value, the quenching action of the compound (1) tends to be easily exhibited. When the content ratio is at most the upper limit value, absorption in the visible region of the quencher is reduced. Tend.

  Moreover, 10 mass parts or more are preferable with respect to 100 mass parts of compounds (1), as for the content rate of the quenching agent in a coloring composition, 20 mass parts or more are more preferable, 50 mass parts or more are more preferable, 100 mass parts The above is even more preferable, 200 parts by mass or more is particularly preferable, 300 parts by mass or more is the most preferable, and 2000 parts by mass or less is preferable, 1000 parts by mass or less is more preferable, 800 parts by mass or less is more preferable, 600 parts by mass The following are particularly preferred. When the content ratio of the quencher to 100 parts by mass of the compound (1) is at least the lower limit value, the quenching action tends to be easily exhibited, and when the content ratio is at most the upper limit value, the absorption in the visible region of the quencher is It tends to be reduced.

  Although the content rate is not specifically limited when the coloring composition of this invention contains binder resin, 1 mass% or more is preferable in a total solid, 10 mass% or more is more preferable, 50 mass% or more is more preferable. 70 mass% or more is still more preferable, 80 mass% or more is especially preferable, and it is usually 99.9 mass% or less. There is a tendency that precipitation of the compound (1) and the quenching agent can be suppressed by setting the content ratio of the binder resin to the lower limit value or more.

  When the coloring composition of the present invention contains a pressure-sensitive adhesive, the content is not particularly limited, but 1% by mass or more is preferable, 10% by mass or more is more preferable, 50% by mass or more is more preferable. 70 mass% or more is still more preferable, 80 mass% or more is especially preferable, and it is usually 99.9 mass% or less. By setting the content ratio of the pressure-sensitive adhesive to the lower limit value or more, precipitation of the compound (1) and the quenching agent tends to be suppressed.

  When the coloring composition of the present invention contains a solvent, the solid content concentration is not particularly limited, but 1 mass% or more is preferable, 5 mass% or more is more preferable, 10 mass% or more is more preferable, 15 mass% or more In particular, 90% by mass or less is preferable, 70% by mass or less is more preferable, 50% by mass or less is more preferable, and 30% by mass or less is particularly preferable. When the solid content concentration is at least the lower limit value, the solution stability tends to be good, and when the solid content concentration is at most the upper limit value, the performance of the resulting coating film tends to be improved.

[Filter and display for display]
The display filter of the present invention contains the coloring composition of the present invention. That is, the display filter of the present invention contains at least the compound (1) and a quencher.
The filter for display of the present invention is, for example, one used as a band pass filter outside the display construction, or one used for color reproduction or color gamut expansion inside the display construction.

The following aspects may be mentioned as specific examples of the configuration of the display filter.
(Filter A): A filter on which a coating layer containing the coloring composition of the present invention is applied on a resin film (Filter B): A filter in which the coloring composition of the present invention is contained in the adhesive layer of the resin film ): Filter in which the coloring composition of the present invention is contained in a resin film Hereinafter, when saying "the filter of the present invention", it shall refer to all the above-mentioned filters A to C unless otherwise specified. Similarly, a filter in which the coloring composition of the present invention is contained in a plurality of locations of a coating layer, a pressure-sensitive adhesive layer and a resin film on a resin film is also included in the “filter of the present invention”.

One aspect of the filter of the present invention is a color correction filter for use in a display, that is, a color purity improving filter, characterized in that it comprises the coloring composition of the present invention.
In particular, from the viewpoint of color purity, it can be suitably used for a display using a white LED as a light source. Among them, from the viewpoint of excluding orange light, the white LED has a light source of a method of obtaining white light by a combination of a blue LED and a yellow phosphor, and a method of obtaining white light by a combination of a blue LED, a green phosphor and a red phosphor A display is preferred.

  The installation position of the color correction filter is not particularly limited as long as it is disposed between the light source as the backlight and the viewer. For example, it may be a color correction coating layer or a color correction adhesive layer applied to a glass plate of a display, a polarizing plate or the like, or a color correction film attached to the surface of a glass plate of a display, a polarizing plate or the like. May be

In addition, it may be a color correction coating layer or a color correction adhesive layer applied to the surface of a plate-like polymer molded body provided in a display, and the color correction film attached to the surface of the polymer molded body It may be Moreover, the form in which the colored composition of this invention is contained in the plate-like polymer molded body itself may be sufficient. Examples of the polymer molded body include polyethylene terephthalate, triacetyl cellulose, polycarbonate and the like.
The position of the color correction filter may be on the light source side or on the viewer side of the front and back of the glass plate or the polymer molded body.

Another aspect of the filter of the present invention is a color correction filter used in a lighting device. Light sources include the same as those listed for the display.
In this case, the installation position of the color correction filter is not particularly limited as long as it is disposed between the light source and the viewer. For example, it may be a color correction coating layer applied to the outer surface or the inner surface of the outermost case (glass, plastic, etc.) of a lighting device such as a bulb type illumination or a straight tube type illumination. It may be a color correction film attached to the outer surface or the inner surface.

The housing is a portion from which light is emitted, and is also called a cover, a hood, or the like.
Moreover, the form in which the coloring composition of this invention is contained in housing | casing itself may be sufficient. In this case, examples of the material of the housing include high-molecular-weight molded articles such as polyethylene terephthalate, triacetyl cellulose, and polycarbonate.

As a lighting device, a bulb-type illumination using a white LED as a light source, a straight tube type illumination, a ceiling light, a spotlight, a downlight, a floodlight, a street light, a desk light and the like can be mentioned.
In addition, the type of white of the lighting device is not particularly limited, and light bulb color (color temperature 2600 to 3250 K), warm white (color temperature 3250 to 3800 K), white (color temperature 3800 to 4500 K), daylight white (color) A lighting device of a color such as a temperature of 4600 to 5500 K and a daylight color (color temperature of 5700 to 7100 K) is used. The classification of the color temperature is based on the standard of JIS Z 9112.

  On the other hand, as another embodiment of the filter of the present invention, an external light correction filter can be mentioned. The external light correction filter of the present invention may be any one containing the coloring composition of the present invention and disposed between external light such as natural light and ambient light and the viewer, and the form and position thereof are particularly limited. It is not something to be done.

For example, a color correction coating layer containing the coloring composition of the present invention, a color correction adhesive layer containing the coloring composition of the present invention, and a color correction coating layer containing the coloring composition of the present invention on a resin film An external light correction film (hereinafter, external light correction film A), an external light correction film (hereinafter, external light correction film B) in which the coloring composition of the present invention is contained in the adhesive layer of the resin film The form of an external light correction film (hereinafter, an external light correction film C) or the like in which the coloring composition is contained is mentioned.
Hereinafter, the term "external light correction film of the present invention" refers to all of the above-mentioned external light correction films A to C unless otherwise specified. Moreover, the film in which the coloring composition of this invention was contained in multiple places among the coating layer on a resin film, an adhesive layer, and a resin film shall also be included in "the exterior light correction film of this invention."

The external light correction film of the present invention can be suitably used as an intake port for taking in external light, for example, windshields of transportation machines such as glasses, automobiles, etc., glass of heavy construction equipment, window glass in buildings, etc. . By applying the ambient light correction film of the present invention to an inlet for taking in ambient light, etc., it is possible to improve the visibility of the worker who works in the environment where the ambient light is inserted. The position of the outside light correction filter may be the outside light side or the viewer side among the front and back of the glass and the window glass.
Moreover, it can also be used for a spectacle lens, a member for windows, etc. by knead | mixing the coloring composition of this invention with polymer resin, and heat-forming it.

The binder resin constituting the filter of the present invention and the extraneous light correction filter of the present invention is not particularly limited, but (meth) acrylic resins (PMMA etc.), polyamide resins, polyurethane resins, polyolefins Resins, such as system resin and polycarbonate resin, are mentioned.
The adhesive is not particularly limited, and examples thereof include acrylics, polyesters, polyamides, polyurethanes, polyolefins, polycarbonates, rubbers, silicone resins, and the like. Among these, acrylic pressure-sensitive adhesives and silicone resin pressure-sensitive adhesives are preferable.
Moreover, as a resin film, the various plastic materials which have transparency are mentioned. For example, polyester resins such as polyethylene terephthalate and polyethylene naphthalate, acetate resins, polyether sulfone resins, polycarbonate resins, polyamide resins, polyimide resins, polyolefin resins, (meth) acrylic resins, polyvinyl chloride Examples thereof include system resins, polyvinylidene chloride resins, polystyrene resins, polyvinyl alcohol resins, polyarylate resins, and polyphenylene sulfide resins.

When the color correction coating layer is provided by mixing the compound (1), the quenching agent and the binder resin, the content ratio of the compound (1) is 0.01 to 10 parts by mass with respect to 100 parts by mass of the binder resin preferable.
When the color correction adhesive layer is provided by mixing the compound (1), the quenching agent and the adhesive, the content ratio of the compound (1) is 0.01 to 10 parts by mass with respect to 100 parts by mass of the adhesive. It is desirable to have.

  When the color correction coating layer and the color correction pressure-sensitive adhesive layer are applied to a resin film or the like (including a housing, a glass plate, a polarizing plate, a polymer molded article, etc.), the coloring composition is spin-coated, spray, bar-coated, It is possible to use a method of coating by a known coating method such as flow coating, gravure coating, roll coating, blade coating, die coater or the like.

Moreover, when manufacturing the filter in which the coloring composition of this invention is contained in a resin film and a polymeric molded object, a coloring composition is mix | blended in resin at the time of shaping | molding of a resin film and a polymeric molded object. , Molding of a resin film and molding of a polymer molded article.
When manufacturing a filter in which the colored composition of the present invention is contained in a resin film or a polymer molded body, the content ratio of the compound (1) is 0.0001 to 1 parts by mass with respect to 100 parts by mass of the resin Is preferred.

  Further, the filter and the ambient light correction filter of the present invention may further contain other additives. For example, additives, such as a near-infrared absorber, an ultraviolet absorber, an antistatic agent, an antioxidant, a dispersant, a flame retardant, a lubricant, and a plasticizer, can be mentioned.

  EXAMPLES Hereinafter, the coloring composition of the present invention will be described with reference to specific examples, but the present invention is not limited to the following examples as long as the gist of the present invention is not exceeded.

(Dipyrromethene compound 1)
As a compound (1), 1.4 g of dipyrromethene compound 1 having the following chemical structure was obtained by the method described in Heterocycle, vol. 61, p. 433 (2003).

(Dipyrromethene compound 2)
As a compound (1), 240 mg of a dipyrromethene compound 2 having the following chemical structure was obtained by the method described in Heterocycle, vol. 61, p. 433 (2003).

(Dipyrromethene compound 3)
As a compound (1), 215 mg of a dipyrromethene compound 3 having the following chemical structure was obtained by the method described in Heterocycle, vol. 61, p. 433 (2003).

(Quenching agent 1)
As a quenching agent, 2.1 g of dithiolate metal complex 1 having the following chemical structure was obtained by the method described in WO 2006/118277.

(Quencher 2)
As a quencher, tetrathiafulvalene (manufactured by Tokyo Chemical Industry Co., Ltd.) having the following chemical structure was prepared.

(Quenching agent 3)
As a quencher, phenothiazine (made by Tokyo Chemical Industry Co., Ltd.) having the following chemical structure was prepared.

(Evaluation of Compound (1))
The maximum absorption wavelength (λmax) of each obtained dipyrromethene compound is tetrahydrofuran adjusted to have an absorbance of 1 at the maximum absorption wavelength using a JASCO V-670 ultraviolet-visible spectrometer (manufactured by JASCO Corporation) The solution was prepared and read from the measured absorption spectrum.
For the half width, the wavelength A1 and the wavelength A2 at which the absorbance A at the maximum absorption wavelength is half are read from the absorption spectrum, and the absolute value of the difference between the wavelength A1 and the wavelength A2 is taken as the half width (FWHM).
Furthermore, the transmittance | permeability of wavelength 380-450 nm was measured using the said tetrahydrofuran solution using the same apparatus. The results are shown in Table 1.

[Examples 1 to 9 and Comparative Example 1]
(Preparation of dye film test piece 1)
2 g of Dianal (registered trademark) BR-80 (manufactured by Mitsubishi Chemical Corporation) is dissolved in 8 g of a mixed solvent in which toluene and THF (tetrahydrofuran) are mixed at a mass ratio of 6: 4, and dipyrromethene compound 0 described in Table 2 .002 g and dithiolate metal complex 0.008 g are added and stirred well (however, in all of Comparative Examples 1 to 3 no dithiolate metal complex is added); Examples 1, 4, 7 and Comparative Example 1 The coloring composition (resin liquid) of -3 was produced.
Each obtained resin solution was applied onto a polyethylene terephthalate film and dried at 80 ° C. for 2 minutes to form a film of 5 μm in thickness to prepare a dye film test piece.

(Preparation of dye film test piece 2)
2 g of Dianal (registered trademark) BR-100 (manufactured by Mitsubishi Chemical Corporation) is dissolved in 8 g of a mixed solvent in which toluene and THF (tetrahydrofuran) are mixed at a mass ratio of 6: 4, and dipyrromethene compound 0 described in Table 2 .002 g and 0.008 g of the quenching agent described in Table 2 were added and stirred well to prepare colored compositions (resin liquids) of Examples 2, 3, 5, 6, 8, and 9.
The resulting resin solutions were each coated on a polyethylene terephthalate film and dried at 80 ° C. for 3 minutes to form a 7 μm thick film, and a dye film test piece was prepared.

(Fluorescent observation)
When a dye film test piece is observed on white paper, both absorption and fluorescence are observed, and it is difficult to determine the presence or absence of fluorescence. Therefore, in order to reduce the influence of absorption and observe the presence or absence of fluorescence, the dye film test piece was placed on a black paper, and the presence or absence of fluorescence was evaluated under a fluorescent lamp. The results are shown in Table 2.
○: Can not confirm fluorescence visually.
X: The fluorescence can be confirmed visually.

(Measurement of maximum absorption wavelength)
The transmission spectrum of the dye film test piece of each of Examples 1 to 9 was measured at a wavelength of 380 to 780 nm using a spectrophotometer U-4100 (manufactured by Hitachi, Ltd.) with a polyethylene terephthalate film as a reference. Also in the example, a sharp absorption peak with a maximum absorption wavelength of 500 to 640 nm derived from the dipyrromethene compound was confirmed.

(Heat test)
Next, the dye film test piece was placed in an 80 ° C. thermostat and exposed for 96 hours. Using a spectrophotometer U-4100 (manufactured by Hitachi, Ltd.) with the polyethylene terephthalate film as a reference, measure the absorption spectrum of the test piece before and after exposure, and change rate of maximum absorption intensity of absorption maximum at wavelength 500 to 640 nm ( = Maximum absorption intensity after exposure-Maximum absorption intensity before exposure x 100 (%)) The heat resistance was evaluated by evaluating the following criteria. The results are shown in Table 2.
◎: The rate of change of the maximum absorption intensity of the absorption maximum is 80% or more ○: The rate of change of the maximum absorption intensity of the absorption maximum is 10% to less than 80% ×: The rate of change of the maximum absorption intensity of absorption maximum is less than 10%

  As is apparent from Table 2, the coloring compositions of Examples 1 to 9 have both absorption peak having a maximum absorption wavelength of 500 to 640 nm, by including both the compound (1) and the quenching agent, and have a wavelength of 380 Since the transmittance of ̃450 nm is 80% or more and the fluorescence emission is suppressed, it is possible to obtain a display filter and a display excellent in reproducibility.

Claims (6)

The coloring composition characterized by containing the compound represented by following General formula (1), and a quenching agent.

(In formula (1), R ^{1 to} R ³ each independently represent a monovalent group. M represents an optional atom which may have a substituent. The benzene ring in formula (1) is Furthermore, it may be substituted by arbitrary substituents.)   The coloring composition of Claim 1 whose transmittance | permeability in wavelength 380-450 nm of the compound represented by the said General formula (1) is 80% or more.   The coloring composition of Claim 1 or 2 in which the compound represented by the said General formula (1) has an absorption maximum whose maximum absorption wavelength is wavelength 500-640 nm.   The coloring composition of Claim 3 whose half value width of the said absorption maximum which the compound represented by the said General formula (1) has is 25 nm or less.   The filter for displays which contains the coloring composition of any one of Claims 1-4.   A display comprising the display filter according to claim 5.