JP2020021063A - Optical filter and display device - Google Patents

Abstract

To provide an optical filter useful for a display device or the like.SOLUTION: The present invention provides an optical filter containing a compound represented by formula (I) [where R-Rindependently represent a hydrogen atom or an optionally substituted C1-6 monovalent hydrocarbon group. Tand Tindependently represent a hydrogen atom or an optionally substituted C1-6 monovalent hydrocarbon group. One of Yand Yis an optionally substituted monovalent aromatic group and the other is an optionally substituted monovalent aromatic group, a hydrogen atom, a halogen atom or an optionally substituted C1-6 monovalent hydrocarbon group (the hydrocarbon group is a group other than a monovalent aromatic group, -CH- included in the hydrocarbon group is optionally substituted with -O- or -CO-)].SELECTED DRAWING: None

Description

  The present invention relates to an optical filter and a display device.

  2. Description of the Related Art In display devices such as liquid crystal display devices and organic electroluminescence (organic EL) display devices, adjustment of color tone and improvement of color purity are performed. Patent Literature 1 discloses that a squarylium-based compound is used for a filter for a plasma display panel capable of effectively cutting neon light emitted from a plasma display.

JP 2001-183522 A

  An object of the present invention is to provide an optical filter and a display device useful for a display device and the like.

［式中、
Ｒ^１〜Ｒ^４は、それぞれ独立して、水素原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基を表す。
Ｔ^１及びＴ^２は、それぞれ独立して、水素原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基を表す。
Ｙ^１及びＹ^２は、いずれか一方が置換基を有していてもよい１価の芳香族基を表し、他方が置換基を有していてもよい１価の芳香族基、水素原子、ハロゲン原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基（該炭化水素基は１価の芳香族基以外の基であり、該炭化水素基に含まれる−ＣＨ_２−は、−Ｏ−又は−ＣＯ−に置き換わっていてもよい。）を表す。］
〔２〕 さらに、接着層を含み、
前記接着層は、前記式（Ｉ）で表される化合物を含む、〔１〕に記載の光学フィルタ。
〔３〕 〔１〕又は〔２〕に記載の光学フィルタと画像表示素子とを有する表示装置であって、
前記光学フィルタは、前記画像表示素子よりも視認側に配置される、表示装置。
〔４〕 液晶表示装置又は有機エレクトロルミネッセンス表示装置である、〔３〕に記載の表示装置。 The present invention provides an optical filter and a display device described below.
[1] An optical filter containing the compound represented by the formula (I).

[Where,
R ^{1 to} R ⁴ each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
T ¹ and T ² each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
Y ¹ and Y ² each represent a monovalent aromatic group optionally having a substituent, and the other one may represent a monovalent aromatic group optionally having a substituent, a hydrogen atom, A halogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent (the hydrocarbon group is a group other than a monovalent aromatic group, and- CH ₂ — may be replaced by —O— or —CO—. ]
[2] Furthermore, an adhesive layer is included,
The optical filter according to [1], wherein the adhesive layer includes a compound represented by the formula (I).
[3] A display device having the optical filter according to [1] or [2] and an image display element,
The display device, wherein the optical filter is disposed on a viewing side with respect to the image display element.
[4] The display according to [3], which is a liquid crystal display or an organic electroluminescence display.

  The optical filter of the present invention can be suitably used for a display device.

(A) and (b) are schematic sectional views showing an example of the optical filter of the present invention. (A) is a schematic sectional view showing an example of an organic EL display device, and (b) is a schematic sectional view showing an example of a liquid crystal display device.

［式中、
Ｒ^１〜Ｒ^４は、それぞれ独立して、水素原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基を表す。
Ｔ^１及びＴ^２は、それぞれ独立して、水素原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基を表す。
Ｙ^１及びＹ^２は、いずれか一方が置換基を有していてもよい１価の芳香族基を表し、他方が置換基を有していてもよい１価の芳香族基、水素原子、ハロゲン原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基（該炭化水素基は１価の芳香族基以外の基であり、該炭化水素基に含まれる−ＣＨ_２−は、−Ｏ−又は−ＣＯ−に置き換わっていてもよい。）を表す。］ (Compound represented by Formula (I))
The optical filter of the present invention contains a compound represented by the following formula (I) (hereinafter, may be referred to as “compound (I)”).

[Where,
R ^{1 to} R ⁴ each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
T ¹ and T ² each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
Y ¹ and Y ² each represent a monovalent aromatic group optionally having a substituent, and the other one may represent a monovalent aromatic group optionally having a substituent, a hydrogen atom, A halogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent (the hydrocarbon group is a group other than a monovalent aromatic group, and- CH ₂ — may be replaced by —O— or —CO—. ]

In the compound (I), for example, in addition to the notation represented by the formula (I), tautomers having a resonance structure represented by the following formula exist. Compound (I) is intended to include all tautomers.

In Formula (I), examples of the monovalent hydrocarbon group having 1 to 6 carbon atoms in R ^{1 to} R ⁴ include a monovalent saturated hydrocarbon group or a monovalent unsaturated hydrocarbon group.
Examples of the monovalent saturated hydrocarbon group include a linear alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group; an isopropyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. A branched alkyl group such as a group, an isopentyl group or a neopentyl group; and an alicyclic saturated hydrocarbon group such as a cyclopropyl group, a cyclopentyl group or a cyclohexyl group.
Examples of the monovalent unsaturated hydrocarbon group include a phenyl group which is an aromatic hydrocarbon group; a monovalent unsaturated aliphatic hydrocarbon group such as a vinyl group, a propenyl group, a butenyl group, or a pentenyl group; a cyclopropenyl group; Examples thereof include a monovalent alicyclic unsaturated hydrocarbon group such as a cyclopentenyl group or a cyclohexenyl group.

In the formula (I), examples of the substituent of the optionally substituted monovalent hydrocarbon group having 1 to 6 carbon atoms in R ^{1 to} R ⁴ include a halogen atom, a hydroxy group, an amino group, and a nitro group. Group, sulfamoyl group, sulfo group and the like.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

In Formula (I), examples of the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in T ¹ and T ² include those exemplified for R ^{1 to} R ⁴ .

In the formula (I), ^one of Y ¹ and Y ² may be a monovalent aromatic group which may have a substituent, and both of them independently have a substituent. It may be a monovalent aromatic group which may be substituted. When ^one of Y ¹ and Y ² is a monovalent aromatic group, the other is a hydrogen atom, a halogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent. And —CH ₂ — contained in the hydrocarbon group may be replaced by —O— or —CO—.

The monovalent aromatic group which may have a substituent in Y ¹ and Y ² includes a monovalent aromatic hydrocarbon group which may have a substituent or a monovalent aromatic hydrocarbon group which has a substituent. And a monovalent aromatic heterocyclic group which may be substituted. The monovalent aromatic group may have a single ring structure or a condensed ring structure.
The number of carbon atoms of the monovalent aromatic hydrocarbon group is usually from 6 to 30, preferably from 6 to 20, and more preferably from 6 to 13. Examples of the monovalent aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, and a fluorenyl group. Further, in the monovalent aromatic hydrocarbon group, hydrogen contained in the above group is an alkyl group (-CH _2- contained in the alkyl group may be replaced by -O- or -CO-), Including those substituted with a hydrocarbon group such as an aryl group, for example, tolyl group, xylyl group, mesityl group, propylphenyl group, butylphenyl group, hexylphenyl group, biphenyl group, terphenyl group, propylbiphenyl And the like.

The carbon number of the monovalent aromatic heterocyclic group is usually 2 to 30, preferably 4 to 20, and more preferably 4 to 10.
The hetero atom in the monovalent aromatic heterocyclic group represents a nitrogen atom, an oxygen atom, a sulfur atom or the like. Examples of the monovalent aromatic heterocyclic group include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, isothiazole, imidazole, pyrazole, furazane, triazole, oxadiazole, isoxazole, tetrazole, pyran, pyridine, thiopyran, Pyridazine, pyrimidine, pyrazine, triazine, benzofuran, isobenzofuran, benzothiophene, indole, isoindole, indolizine, indoline, isoindoline, chromene, isochromene, chroman, isochroman, benzopyran, quinoline, isoquinoline, quinolidine, benzimidazole, benzothiazole , Benzothiadiazole, indazole, naphthyridine, quinoxaline, quinazoline, quinazolidin, cinnoline, phthalazine, A group obtained by removing one hydrogen atom from a heterocyclic compound such as phosphorus, pteridine, carbazole, xanthene, phenanthridine, acridine, β-carboline, perimidine, phenanthroline, thianthrene, phenoxatiin, phenoxazine, phenothiazine, or phenazine. No. Further, the monovalent aromatic heterocyclic group includes a group in which hydrogen contained in the above-mentioned group is substituted with a hydrocarbon group such as an alkyl group and an aryl group. For example, a hydrogen atom is converted from N-biphenylcarbazole. It may be a group excluding one.

  Examples of the substituent in the optionally substituted monovalent aromatic group include the above-mentioned halogen atom; hydroxy group; amino group; nitro group; aryloxy group; arylcarbonyl group; Group; sulfo group; carbamoyl group; sulfamoyl group and the like.

In Formula (I), any one of Y ¹ and Y ² , which is a hydrocarbon group other than a monovalent aromatic group and has 1 to 6 carbon atoms which may have a substituent. Examples of the hydrocarbon group include monovalent saturated hydrocarbon groups which may have a substituent and monovalent unsaturated aliphatic hydrocarbons which may have a substituent, as exemplified in R ^{1 to} R ⁴ . And a monovalent alicyclic unsaturated hydrocarbon group which may have a group or a substituent.
—CH ₂ — contained in the hydrocarbon group may be replaced by —O— or —CO—, and examples of such a group include —C (＝ O) CH ₃ and —C (＝ O). —OCH ₂ CH ₃ is mentioned.

Examples of the compound (I) include a compound represented by the following formula.

  Compound (I) can be used for an optical filter in a display device or the like. For example, by adding the compound (I) to a layer forming an optical filter, an optical filter capable of absorbing light near 580 nm (575 to 590 nm) (preferably light having a maximum absorption wavelength of 580 nm) can be obtained. . Thereby, the light transmitted through the optical filter can increase the separability of green light and red light, and improve the color purity of green light and red light, as compared with light incident on the optical filter. Can be expected. Therefore, a display device with improved color purity can be obtained by applying an optical filter using the compound (I) to a display device or the like.

［式中、
Ｒ^１〜Ｒ^４は、それぞれ独立して、水素原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基を表す。
Ｔ^１及びＴ^２は、それぞれ独立して、水素原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基を表す。
Ｘ^１及びＸ^２は、いずれか一方が群Ａより選ばれるいずれかの基を表し、他方が群Ａより選ばれるいずれかの基、水素原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基（該炭化水素基は１価の芳香族基以外の基であり、該炭化水素基に含まれる−ＣＨ_２−は、−Ｏ−又は−ＣＯ−に置き換わっていてもよい。）を表す。
群Ａ：ハロゲン原子、ホウ酸エステル基、及び−Ｂ（ＯＨ）_２からなる群。］ (Compound represented by Formula (II))
A compound represented by the following formula (II) (hereinafter sometimes referred to as “compound (II)”) can be used as an intermediate for producing compound (I).

[Where,
R ^{1 to} R ⁴ each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
T ¹ and T ² each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
X ¹ and X ² each represent any group selected from group A, and the other represents any group selected from group A, a hydrogen atom or a carbon atom 1 which may have a substituent. To 6 monovalent hydrocarbon groups (the hydrocarbon group is a group other than a monovalent aromatic group, and -CH _2- contained in the hydrocarbon group is replaced by -O- or -CO-. May be used.)
Group A: a group consisting of a halogen atom, a borate group, and -B (OH) ₂ . ]

In the compound (II), in addition to the notation represented by the formula (II), for example, tautomers of a resonance structure represented by the following formula exist. Compound (II) is intended to include all tautomers.

In the formula (II), the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R ^{1 to} R ⁴ , T ¹ and T ² includes those described above.

In the formula (II), ^one of X ¹ and X ² represents any group selected from Group A, and both may be any groups selected from Group A. When ^one of X ¹ and X ² is any group selected from group A, the other is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent. And —CH ₂ — contained in the hydrocarbon group may be replaced by —O— or —CO—.

In the formula (II), examples of the halogen atom in the group A include those described above.
Examples of the borate group for X ¹ and X ² include groups represented by the following formula. In the following formula, * represents a bond.

In the formula (II), any one of X ¹ and X ² , which is a hydrocarbon group other than a monovalent aromatic group and has 1 to 6 carbon atoms which may have a substituent. Examples of the hydrocarbon group include monovalent saturated hydrocarbon groups, monovalent unsaturated aliphatic hydrocarbon groups, and monovalent alicyclic unsaturated hydrocarbon groups exemplified in R ^{1 to} R ⁴ . .
—CH ₂ — contained in the hydrocarbon group may be replaced by —O— or —CO—, and examples of such a group include —C (＝ O) CH ₃ and —C (＝ O). —OCH ₂ CH ₃ is mentioned.

Examples of the compound (II) include a compound represented by the following formula.

(Production method of compound (I) [1])
In the compound (I), when both Y ¹ and Y ² are monovalent aromatic groups which may have a substituent (compound represented by the following formula (Ia) (hereinafter referred to as “compound (Ia) "))).

［式中、
Ｒ^１〜Ｒ^４は、それぞれ独立して、水素原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基を表す。
Ｔ^１及びＴ^２は、それぞれ独立して、水素原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基を表す。
Ｙ^１ａ及びＹ^２ａは、それぞれ独立して、置換基を有していてもよい１価の芳香族基を表す。］

[Where,
R ^{1 to} R ⁴ each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
T ¹ and T ² each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
Y ^1a and Y ^2a each independently represent a monovalent aromatic group which may have a substituent. ]

In the formula (Ia), the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R ^{1 to} R ⁴ , T ¹ and T ² includes those described above.
The monovalent aromatic group which may have a substituent in Y ^1a and Y ^2a in the formula (Ia) has a substituent represented by Y ¹ and Y ² in the above formula (I). Examples of the monovalent aromatic group that may be used include those described above.

  The method for producing the compound (Ia) includes the steps of: converting a compound represented by the formula (IIa), a compound represented by the formula (III-1a), and a compound represented by the formula (III-2a) into a nickel catalyst or A step of reacting in the presence of a palladium catalyst may be included.

［式中、
Ｒ^１〜Ｒ^４は、前記と同じ意味を表す。
Ｔ^１及びＴ^２は、前記と同じ意味を表す。
Ｘ^１ａ及びＸ^２ａは、それぞれ独立して、群Ａより選ばれるいずれかの基を表す。
群Ａ：ハロゲン原子、ホウ酸エステル基、及び−Ｂ（ＯＨ）_２からなる群。］

[Where,
R ^{1 to} R ⁴ represent the same meaning as described above.
T ¹ and T ² represent the same meaning as described above.
X ^1a and X ^2a each independently represent any group selected from Group A.
Group A: a group consisting of a halogen atom, a borate group, and -B (OH) ₂ . ]

Y ^1a -Z ¹ (III-1a)
Y ^2a -Z ² (III-2a)
[In the formulas (III-1a) and (III-2a),
Y ^1a and Y ^2a have the same meaning as described above.
Z ¹ and Z ² each independently represent a halogen atom, a borate group, —B (OH) ₂ , an alkylsulfonate group, or an arylsulfonate group. ]

In the formula (IIa), the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R ^{1 to} R ⁴ , T ¹ and T ² includes those described above.
The halogen atom and the borate group in Group A of X ^1a and X ^2a in the formula (IIa) include those described above.
In the formulas (III-1a) and (III-2a), the halogen atom and the borate group in Z ¹ and Z ² are as described above.
Examples of the alkyl sulfonate group in Z ¹ and Z ^2, methanesulfonate group, ethanesulfonate group, or an alkyl sulfonate group halogen atom carbon atoms, which may have 1 to 6 such as a trifluoromethanesulfonate group. Examples of the halogen atom include those exemplified above.
Examples of the aryl sulfonate group in Z ¹ and Z ^2, a benzene sulfonate group, p- toluenesulfonate group, an aryl sulfonate group having 6 to 18 carbon atoms such as a benzyl sulfonate group.
Z ¹ and Z ² are each independently preferably a halogen atom, a borate group, or —B (OH) ₂ .

Examples of the compound represented by the formula (IIa) include a compound represented by the following formula.

  Compounds represented by the formulas (III-1a) and (III-2a) include 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborane-2) -Yl) phenol, 3,4,5-trimethoxyphenylboronic acid, 4-hexylphenylboronic acid, 4-hexyloxyphenylboronic acid, 4- (dimethylamino) phenylboronic acid, 4- (diphenylamino) phenylboron Acid, 4'-propyl-4-biphenylboronic acid, 6-ethoxy-2-naphthaleneboronic acid, 9,9-dimethylfluorene-2-boronic acid, benzo [b] thiophen-2-boronic acid, 9-ethylcarbazole -3-boronic acid, 9- (4-biphenylyl) carbazole-3-boronic acid pinacol, 4-tert-butylphenylboronic acid, 4-methoxy 3,5-dimethylphenyl boronic acid, 4-carboxyphenyl boronic acid pinacol, 1-Chi entrée alkenyl boronic acid, and 4-methyl-1-naphthalene boronic acid.

In the step of producing the compound (Ia), a compound represented by the formula (IIa), a compound represented by the formula (III-1a), and a compound represented by the formula (III-2a) are treated with a palladium catalyst A coupling method in the presence or in the presence of a nickel catalyst is preferred, and a coupling method in the presence of a palladium catalyst is most preferred.
Examples of the palladium catalyst include tetrakis (triphenylphosphine) palladium (0), tris (dibenzylideneacetone) dipalladium (0), palladium (II) acetate, dichlorobistriphenylphosphinepalladium (II) and potassium hexachloropalladium (IV). And the like.
As the nickel catalyst, tetrakis (triphenylphosphine) nickel (0), [bis (1,5-cyclooctadiene)] nickel (0), [1,3-bis (diphenylphosphino) propane] dichloronickel (II) ), Bis (2,4-pentanedionato) nickel (II), bis (triphenylphosphine) nickel (II) dichloride, nickel (II) halide and the like.
The amount of the palladium catalyst or nickel catalyst used is preferably 0.1 mol% or more and 50 mol% or less based on 1 mol of the compound represented by the formula (IIa).

The amount of the compound represented by the formula (III-1a) to be used is preferably 1 mol or more and 5 mol or less, more preferably 1.1 mol or more and 3 mol, per 1 mol of the compound represented by the formula (IIa). It is more preferred that:
The amount of the compound represented by the formula (III-2a) to be used is preferably from 1 mol to 5 mol, and more preferably from 1.1 mol to 3 mol, per 1 mol of the compound represented by the formula (IIa). It is more preferred that:

  The reaction temperature is preferably 30C to 180C, more preferably 80C to 140C. The reaction time is preferably from 1 hour to 20 hours, more preferably from 3 hours to 15 hours.

  The reaction is preferably performed in an organic solvent from the viewpoint of yield. Examples of the organic solvent include aromatic hydrocarbon solvents such as toluene and xylene; hydrocarbon solvents such as hexane, cyclohexane and decalin; ether solvents such as tetrahydrofuran, 1,4-dioxane and dimethoxyethane; chlorobenzene, dichlorobenzene, chloroform and the like. Halogenated hydrocarbon solvents; alcohol solvents such as methanol, ethanol, isopropanol and butanol; nitrohydrocarbon solvents such as nitrobenzene; ketone solvents such as methyl isobutyl ketone; N, N-dimethylformamide, 1-methyl-2-pyrrolidone Amide solvent; and these may be used as a mixture. Of these, tetrahydrofuran is preferred. Further, the reaction can be carried out by a two-phase or mixed reaction with water, such as a coupling reaction using a palladium catalyst. The amount of the organic solvent to be used is preferably 10 parts by mass or more and 200 parts by mass or less, more preferably 20 parts by mass or more and 150 parts by mass or less with respect to 1 part by mass of the compound represented by the formula (IIa). preferable.

In addition, a base may be added to the reaction of the compound represented by the formula (IIa), the compound represented by the formula (III-1a), and the compound represented by the formula (III-2a). The base is preferably one that sufficiently dissolves in the solvent used for the reaction. Examples of the base include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, tripotassium phosphate; butyllithium, potassium-tert-butoxide, sodium-tert-butoxide, sodium methoxide, Organic bases such as sodium ethoxide, tetrabutylammonium fluoride, tetrabutylammonium chloride, tetrabutylammonium bromide, tetraethylammonium hydroxide, and tetrabutylammonium hydroxide are exemplified. Examples of the method of mixing the base include a method of adding a base solution while stirring the reaction solution under an inert atmosphere such as argon or nitrogen, and a method of adding the reaction solution to the base solution.
The amount of the base to be used is preferably 2 mol or more and 20 mol or less based on 1 mol of the compound represented by the formula (IIa).

  The method for obtaining the target compound (Ia) from the reaction mixture is not particularly limited, and various known methods can be employed. For example, there is a method in which the precipitated crystals are collected by filtration after cooling. The crystals collected by filtration are preferably washed with water or the like and then dried. Further, if necessary, it may be further purified by a known method such as recrystallization, column chromatography and the like.

(Method for producing compound (I) [2])
In the compound (I), Y ¹ is a monovalent aromatic group which may have a substituent, and Y ² is a hydrogen atom or a monovalent C ¹ to C 6 which may have a substituent. (The hydrocarbon group is a group other than a monovalent aromatic group, and —CH ₂ — contained in the hydrocarbon group may be replaced by —O— or —CO—.) The method for producing the compound (wherein the compound is represented by the following formula (Ib) (hereinafter sometimes referred to as “compound (Ib)”)) is described.

［式中、
Ｒ^１〜Ｒ^４は、それぞれ独立して、水素原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基を表す。
Ｔ^１及びＴ^２は、それぞれ独立して、水素原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基を表す。
Ｙ^１ｂは、置換基を有していてもよい１価の芳香族基を表す。
Ｘ^２ｂは、水素原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基（該炭化水素基は１価の芳香族基以外の基であり、該炭化水素基に含まれる−ＣＨ_２−は、−Ｏ−又は−ＣＯ−に置き換わっていてもよい。）を表す。］

[Where,
R ^{1 to} R ⁴ each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
T ¹ and T ² each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
Y ^1b represents a monovalent aromatic group which may have a substituent.
X ^2b represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent (the hydrocarbon group is a group other than a monovalent aromatic group, and the hydrocarbon group -CH ₂ contained in the - represents may be replaced by -O- or -CO-).. ]

In the formula (Ib), the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R ^{1 to} R ⁴ , T ¹ and T ² is represented by R in the above formula (I) include those exemplified in ¹ to R ^4.
In the formula (Ib), examples of the optionally substituted monovalent aromatic group for Y ^1b include those exemplified for Y ¹ and Y ² in the above formula (I).
In the formula (Ib), the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in X ^2b is exemplified by R ^{1 to} R ⁴ in the above formula (I). No.

  The method for producing the compound (Ib) includes a step of reacting the compound represented by the formula (IIb) with the compound represented by the formula (III-1b) in the presence of a nickel catalyst or a palladium catalyst. Is also good.

［式中、
Ｒ^１〜Ｒ^４は、前記と同じ意味を表す。
Ｔ^１及びＴ^２は、前記と同じ意味を表す。
Ｘ^１ｂは、群Ａより選ばれるいずれかの基を表す。
群Ａ：ハロゲン原子、ホウ酸エステル基、及び−Ｂ（ＯＨ）_２からなる群。
Ｘ^２ｂは、前記と同じ意味を表す。］

[Where,
R ^{1 to} R ⁴ represent the same meaning as described above.
T ¹ and T ² represent the same meaning as described above.
X ^1b represents any group selected from Group A.
Group A: a group consisting of a halogen atom, a borate group, and -B (OH) ₂ .
X ^2b has the same meaning as described above. ]

Y ^1b -Z ¹ (III-1b)
[Where,
Y ^1b has the same meaning as described above.
Z ¹ represents a halogen atom, a borate group, —B (OH) ₂ , an alkylsulfonate group, or an arylsulfonate group. ]

In the formulas (IIb) and (III-1b), the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R ^{1 to} R ⁴ , T ¹ and T ² , and X ^2b is And those exemplified for R ^{1 to} R ⁴ in the above formula (I).
In the formula (IIb) and the formula (III-1b), the ^optionally substituted monovalent aromatic group for Y ^1b is exemplified by the above-mentioned Y ¹ and Y ² in the formula (I). Is mentioned.
In the formula (IIb), the halogen atom and the borate group for X ^1b include those described above.

Examples of the compound represented by the formula (IIb) include a compound represented by the following formula.

  Examples of the compound represented by the formula (III-1b) include the compounds exemplified as the compounds represented by the above formulas (III-1a) and (III-2a).

  In the step of producing the compound (Ib), a method of coupling a compound represented by the formula (IIb) and a compound represented by the formula (III-1b) in the presence of a palladium catalyst or a nickel catalyst is known. Preferably, a coupling method in the presence of a palladium catalyst is most preferable. The palladium catalyst and the nickel catalyst include those described above.

The amount of the compound represented by the formula (III-1b) is preferably 1 mol or more and 5 mol or less, more preferably 1.1 mol or more and 3 mol or less, per 1 mol of the compound represented by the formula (IIb). It is more preferred that:
The use amount of the palladium catalyst or the nickel catalyst is preferably 0.1 mol% or more and 50 mol% or less based on 1 mol of the compound represented by the formula (IIb).

  The reaction temperature is preferably 30C to 180C, more preferably 80C to 140C. The reaction time is preferably from 1 hour to 20 hours, more preferably from 3 hours to 15 hours.

  The reaction is preferably performed in an organic solvent from the viewpoint of yield. Examples of the organic solvent include those exemplified above. The amount of the organic solvent to be used is preferably 10 parts by mass or more and 200 parts by mass or less, more preferably 20 parts by mass or more and 150 parts by mass or less with respect to 1 part by mass of the compound represented by the formula (IIb). preferable.

  The method for obtaining the target compound (Ib) from the reaction mixture is not particularly limited, and various known methods can be adopted, for example, the above-described methods.

(Method for producing compound (I) [3])
The production method of the compound (I) is based on the following method: (3,4-dihydroxy-3-cyclobutene-1,2-dione) represented by the formula (IV) or the compound represented by the formula (IV-1) ( Hereinafter, the compound may be referred to as a compound (IV-1).), A compound represented by the following formula (V1) (hereinafter, sometimes referred to as a "pyrrole compound (V1)"), and a compound represented by the following formula (V2). (Hereinafter, may be referred to as “pyrrole-based compound (V2)”).

［式（ＩＶ−１）、式（Ｖ１）及び式（Ｖ２）中、
Ｒ^１〜Ｒ^４は、前記と同じ意味を表す。
Ｙ^１及びＹ^２は、いずれか一方が置換基を有していてもよい１価の芳香族基を表し、他方が置換基を有していてもよい１価の芳香族基、水素原子、ハロゲン原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基（該炭化水素基は１価の芳香族基以外の基であり、該炭化水素基に含まれる−ＣＨ_２−は、−Ｏ−又は−ＣＯ−に置き換わっていてもよい。）を表す。
Ｔ^１及びＴ^２は、前記と同じ意味を表す。
Ｒ^１１及びＲ^１２は、それぞれ独立して、炭素数１〜４のアルキル基を表す。］

[In the formulas (IV-1), (V1) and (V2),
R ^{1 to} R ⁴ represent the same meaning as described above.
Y ¹ and Y ² each represent a monovalent aromatic group optionally having a substituent, and the other one may represent a monovalent aromatic group optionally having a substituent, a hydrogen atom, A halogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent (the hydrocarbon group is a group other than a monovalent aromatic group, and- CH ₂ — may be replaced by —O— or —CO—.
T ¹ and T ² represent the same meaning as described above.
R ¹¹ and R ¹² each independently represent an alkyl group having 1 to 4 carbon atoms. ]

In the formulas (V1) and (V2), the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R ^{1 to} R ⁴ , T ¹ and T ² is as described above. No.
In the formulas (V1) and (V2), a monovalent aromatic group which may have a substituent in Y ¹ and Y ² , a halogen atom, and a carbon atom having 1 to 6 carbon atoms which may have a substituent. Examples of the monovalent hydrocarbon group include those described above.

Examples of the pyrrole compound (V1) and the pyrrole compound (V2) include compounds represented by the following formulas.

  In the step of producing the compound (I), a method in which squaric acid, a pyrrole compound (V1), and a pyrrole compound (V2) are dehydrated and condensed in an organic solvent is preferable. Examples of the organic solvent include those described above, and a mixed solvent of butanol and toluene is preferable.

The amount of squaric acid used in the step of reacting squaric acid with the pyrrole compound (V1) and the pyrrole compound (V2) is based on 1 mol of the pyrrole compound (V1) and the pyrrole compound (V2) in total. , 0.45 mol or more and 0.6 mol or less, more preferably 0.47 mol or more and 0.51 mol or less.
The amount of the pyrrole compound (V2) to be used is preferably 1 mol or more and 1.5 mol or less per 1 mol of the pyrrole compound (V1).

  The reaction between the compound represented by the formula (IV) or the compound (IV-1), the pyrrole-based compound (V1), and the pyrrole-based compound (V2) is performed by the compound represented by the formula (IV) or the compound (IV -1), the pyrrole compound (V1) and the pyrrole compound (V2). In the reaction, the compound represented by the formula (IV) or the compound (IV-1), the pyrrole compound (V1), and the pyrrole compound (V2) may all be reacted together. Further, a method of mixing the compound represented by the formula (IV) or the compound (IV-1) with the pyrrole compound (1) first, and then mixing the pyrrole compound (2), A method in which the compound represented by the formula (IV) or the compound (IV-1) and the pyrrole compound (2) are mixed first, and then the pyrrole compound (1) may be mixed.

  The reaction temperature is preferably 30C to 180C, more preferably 80C to 140C. The reaction time is preferably from 1 hour to 20 hours, more preferably from 3 hours to 15 hours.

  The reaction is preferably performed in an organic solvent from the viewpoint of yield. Examples of the organic solvent include those exemplified above. The amount of the organic solvent to be used is preferably 5 parts by mass or more and 200 parts by mass or less, more preferably 8 parts by mass or more and 160 parts by mass or less with respect to 1 part by mass of squaric acid.

  The method for obtaining the target compound (I) from the reaction mixture is not particularly limited, and various known methods can be employed, and examples thereof include the methods described above.

  The pyrrole compound (V1) is obtained by reacting, for example, the following formula (V1 ′) (hereinafter sometimes referred to as “pyrrole compound (V1 ′)”) with a halogenating agent, And a compound represented by the following formula (III-1) (hereinafter sometimes referred to as “compound (III-1)”). The pyrrole-based compound (V2) is obtained by reacting, for example, a compound represented by the following formula (V2 ′) (hereinafter, sometimes referred to as “pyrrole-based compound (V2 ′)”) with a halogenating agent. Then, the reaction product can be produced by reacting the reaction product with a compound represented by the following formula (III-2) (hereinafter, sometimes referred to as “compound (III-2)”). Further, in order to react compound (III-1) and compound (III-2) at desired positions, (V1 ′) and (V2 ′) have a protecting group such as an ethoxycarbonyl group at a position not to be reacted. The desired pyrrole compound (V1) and the desired pyrrole compound (V2) can be produced by deprotection after the reaction.

［式（Ｖ１’）及び式（Ｖ２’）中、
Ｒ^１〜Ｒ^４は、前記と同じ意味を表す。
Ｔ^１及びＴ^２は、前記と同じ意味を表す。］

[In the formulas (V1 ′) and (V2 ′),
R ^{1 to} R ⁴ represent the same meaning as described above.
T ¹ and T ² represent the same meaning as described above. ]

The monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R ^{1 to} R ⁴ , T ¹ and T ² in the formulas (V1 ′) and (V2 ′) is as described above. Things.

Y ¹ -Z ¹ (III-1)
Y ² -Z ² (III-2)
[In the formulas (III-1) and (III-2),
Y ¹ and Y ² represent the same meaning as described above.
Z ¹ and Z ² each independently represent a halogen atom, a borate group, —B (OH) ₂ , an alkylsulfonate group, or an arylsulfonate group. ]

In the formulas (III-1) and (III-2), a monovalent aromatic group optionally having a substituent in Y ¹ and Y ² , a halogen atom, and a carbon atom optionally having a substituent Examples of the monovalent hydrocarbon group of Formulas 1 to 6 include those described above.
In the formulas (III-1) and (III-2), the halogen atom, the borate ester group, the alkylsulfonate group, or the arylsulfonate group in Z ¹ and Z ² include those described above.

Examples of the pyrrole compound (V1 ′) and the pyrrole compound (V2 ′) include 2,4-dimethylpyrrole.
Examples of the compound (III-1) and the compound (III-2) include 4-hexylphenylboronic acid.

  As the halogenating agent, N-fluorosuccinimide (NFS), N-chlorosuccinimide (NCS), N-bromosuccinimide (NBS), N-iodosuccinimide (NIS) represented as N-halogen succinimide (NXS), N-chlorophthalimide, N-chlorodiethylamine, N-chlorodibutylamine, N-chlorocyclohexylamine, chlorine, iodotrichloride, aluminum trichloride, tellurium (IV) chloride, molybdenum chloride, antimony chloride, iron (III) chloride , Titanium tetrachloride, phosphorus pentachloride, thionyl chloride, N-bromophthalimide, N-bromoditrifluoromethylamine, bromine, 1,2-dibromoethane, boron tribromide, copper bromide, silver bromide, bromide -T-butyl, bromine oxide and the like; Bromide is preferred.

  In the step of producing the pyrrole compound (V1) and the pyrrole compound (V2), a reaction product obtained by reacting the pyrrole compound (V1 ′) or the pyrrole compound (V2 ′) with a halogenating agent; The reaction with compound (III-1) or compound (III-2) is preferably performed in the presence of a palladium catalyst or in the presence of a nickel catalyst, and most preferably in the presence of a palladium catalyst. Examples of the palladium catalyst and the nickel catalyst include those described above.

A reaction product of a pyrrole compound (V1 ′) or a pyrrole compound (V2 ′) with a halogenating agent, and a reaction of the compound (III-1) or the compound (III-2) in the presence of a palladium catalyst; When the substituent introduced into the reaction product by the halogenating agent is a halogen atom, Z ¹ in compound (III-1) or Z ² in compound (III-2) is each independently a borate ester group Alternatively, it is preferably -B (OH) ₂ . When the above reaction is carried out in the presence of a nickel catalyst, and the substituent introduced into the reaction product by the halogenating agent is a halogen atom, Z ¹ and Z ² are preferably each independently a halogen atom. When the above reaction is carried out in the presence of a palladium catalyst and the substituent introduced into the reaction product by the halogenating agent is converted into a borate group or -B (OH) ₂ by a conventional method, Z ¹ and Z ² Is preferably each independently an alkylsulfonate group or an arylsulfonate group.

  The reaction between the pyrrole compound (V1 ′) or the pyrrole compound (V2 ′) and the halogenating agent is performed by reacting the halogenating agent with 1 mole of the pyrrole compound (V1 ′) or the pyrrole compound (V2 ′). It is preferably from 5 mol to 5 mol, more preferably from 1.05 mol to 3 mol.

  The reaction temperature is preferably from -80 ° C to the boiling point of the solvent. The reaction time is preferably from 1 hour to 20 hours, more preferably from 3 hours to 15 hours.

  The reaction is preferably performed in an organic solvent from the viewpoint of yield. Examples of the organic solvent include those exemplified above. The amount of the organic solvent to be used is preferably 5 parts by mass or more and 100 parts by mass or less, more preferably 8 parts by mass or more and 50 parts by mass with respect to 1 part by mass of the pyrrole compound (V1 ′) or the pyrrole compound (V2 ′). It is more preferred that:

  The method for obtaining the reaction product of the pyrrole compound (V1 ′) or the pyrrole compound (V2 ′) as the target compound from the reaction mixture and the halogenating agent is not particularly limited, and various known methods can be adopted. For example, the method described above can be used.

In the reaction of the reaction product of the pyrrole compound (V1 ′) with the halogenating agent and the compound (III-1), the amount of the compound (III-1) to be used is 1 to 1 mol of the pyrrole compound (V1 ′). It is preferably from 5 mol to 5 mol, and more preferably from 1.1 mol to 3 mol.
In the reaction of the reaction product of the pyrrole compound (V2 ') with the halogenating agent and the compound (III-2), the amount of the compound (III-2) used is based on 1 mol of the pyrrole compound (V2'). It is preferably from 1 mol to 5 mol, more preferably from 1.1 mol to 3 mol.

  The reaction temperature is preferably 30C to 180C, more preferably 80C to 140C. The reaction time is preferably from 1 hour to 20 hours, more preferably from 3 hours to 15 hours.

  The method for obtaining the pyrrole-based compound (V1) or the pyrrole-based compound (V2) as the target compound from the reaction mixture is not particularly limited, and various known techniques can be employed, and examples thereof include the above-described methods.

(Production method of compound (I) [4])
In the compound (I), a compound in which Y ¹ is a monovalent aromatic group which may have a substituent and Y ² is a halogen atom (hereinafter, may be referred to as “compound (Ic)” ))) Will be described.

Compound (Ic) can be produced by halogenating the hydrogen atom represented by X ^2b in the compound represented by the above formula (Ib) wherein X ^2b is a hydrogen atom. Halogenation can be performed, for example, using the above-mentioned halogenating agent.

［式中、
Ｒ^１〜Ｒ^４は、それぞれ独立して、水素原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基を表す。
Ｔ^１及びＴ^２は、それぞれ独立して、水素原子又は置換基を有していてもよい炭素数１〜６の１価の炭化水素基を表す。］ (Production method (1) of compound (II))
The production method of the compound (II) is, for example, when the compound (II) is a compound of the formula (II) wherein X ¹ and X ² are halogen atoms (hereinafter, sometimes referred to as “compound (IIc)”). Reacting the squaric acid represented by the above formula (IV), the pyrrole compound (V1 ′), and the pyrrole compound (V2 ′) to form a compound represented by the following formula (II ′) (Hereinafter, “compound (II ′)”) and a step of reacting compound (II ′) with a halogenating agent to obtain compound (IIc).

[Where,
R ^{1 to} R ⁴ each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
T ¹ and T ² each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent. ]

In the formula (II ′), the monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent in R ^{1 to} R ⁴ , T ¹ and T ² includes those described above.
Examples of the halogenating agent include those described above.

Examples of the compound (II ′) include a compound represented by the following formula.

The amount of squaric acid used in the step of reacting squaric acid with the pyrrole compound (V1 ′) and the pyrrole compound (V2 ′) is 1 in total of the pyrrole compound (V1 ′) and the pyrrole compound (V2 ′). It is preferably from 0.45 mol to 0.6 mol, and more preferably from 0.47 mol to 0.51 mol, based on the mol.
The amount of the pyrrole compound (V2 ') to be used is preferably 1 mol or more and 1.5 mol or less based on 1 mol of the pyrrole compound (V1').

  The reaction temperature is preferably 30C to 180C, more preferably 80C to 140C. The reaction time is preferably from 1 hour to 20 hours, more preferably from 3 hours to 15 hours.

  The reaction is preferably performed in an organic solvent from the viewpoint of yield. As the organic solvent, those exemplified above can be used. The amount of the organic solvent to be used is preferably 5 parts by mass or more and 200 parts by mass or less, more preferably 8 parts by mass or more and 100 parts by mass or less with respect to a total of 1 part by mass of the pyrrole compound (V1 ′) and the pyrrole compound (V2 ′). More preferably, the amount is not more than part by mass.

  The method for obtaining the target compound (II ') from the reaction mixture is not particularly limited, and various known methods can be employed, for example, the above-described methods can be used.

In the reaction of compound (II ′) with a halogenating agent, the halogenating agent is preferably used in an amount of 2 to 6 mol, preferably 2.2 to 5 mol, per 1 mol of compound (II ′). Preferably, there is.
The reaction temperature is preferably from -80 ° C to the boiling point of the solvent. The reaction time is preferably from 1 hour to 20 hours, more preferably from 3 hours to 15 hours.

  The reaction is preferably performed in an organic solvent from the viewpoint of yield. As the organic solvent, those exemplified above can be used. The amount of the organic solvent to be used is preferably 5 parts by mass or more and 200 parts by mass or less, more preferably 10 parts by mass or more and 100 parts by mass or less with respect to 1 part by mass of compound (II ').

  The method for obtaining the target compound (IIc) from the reaction mixture is not particularly limited, and various known methods can be employed, for example, the methods described above.

(Production method (2) of compound (II))
In the method for producing the compound (II), a compound in which X ¹ and X ² in the formula (II) are a borate group or —B (OH) ₂ (hereinafter, may be referred to as “compound (IId)”). In such a case, for example, a compound (IIc) [a compound in which X ¹ and X ² are halogen atoms in the formula (II)] is reacted with a small piece of magnesium to prepare a Grignard intermediate, and 2-isopropyloxy-4, A method of reacting 4,5,5-tetramethyl-1,3,2-dioxaborolane or the like; by reacting compound (IIc) with bis (pinacolato) diboron using a palladium catalyst in the presence of a base. , Boric acid esterification method; a method in which trimethoxyborane, triisopropyloxyborane or the like is allowed to act, and then hydrolyzed to borate. It is.

(Optical filter)
The optical filter of the present invention contains the compound (I), and the optical filter of the present invention can be used for a display device or the like. The optical filter is usually a layer formed from a composition containing a thermoplastic resin or a thermosetting resin having a light-transmitting property (preferably optically transparent), for example, a film-like material. It is. The optical filter only needs to have a layer containing the compound (I) (hereinafter, sometimes referred to as “color correction layer”), and may be a color correction film having a single-layer structure of the color correction layer. Alternatively, a laminate having a multilayer structure including a color correction layer may be used. When the optical filter has a multilayer structure, the color filter may include one color correction layer, may include two or more color correction layers, and may include the compound (I) included in the two or more layers. They may be the same or different.

  When the optical filter is a laminate, the color correction layer may be an adhesive layer or a resin layer other than the adhesive layer (hereinafter, may be simply referred to as “resin layer”). When the color correction layer is an adhesive layer, the two layers included in the optical filter may be bonded to each other, and the optical filter may be bonded to another member such as an image display device. There may be. The adhesive layer can be an adhesive layer formed of an adhesive composition, an adhesive layer formed of an adhesive composition, or a layer formed of an adhesive composition and an adhesive composition.

  When the color correction layer is an optical filter (color correction film) having a single-layer structure or a resin layer other than the adhesive layer in an optical filter having a multilayer structure, the color correction film or the resin layer contains the compound (I). There is no particular limitation on the method used. For example, [i] a method of kneading with a resin for forming a color correction film or a resin layer and heat-forming the film, [ii] a resin for forming a color correction film or a resin layer or a monomer of the resin, and a compound (I) ) Is dispersed or dissolved in an organic solvent and formed into a film by a casting method or the like. Further, a coating solution obtained by dispersing or dissolving the compound (I) in a binder resin or an organic solvent on a resin base film may be used as the resin layer, and the resin base film may be peeled from the resin layer. The resulting film may be used as a color correction film. The thickness of the color correction film or the resin layer is not particularly limited, but may be, for example, 1 μm to 200 μm.

  When the color correction film or the resin layer contains the compound (I), the content is not particularly limited. For example, the compound (I) can be used in an amount of at least 0.001 part by mass, preferably at least 0.02 part by mass, based on 100 parts by mass of the base polymer forming the color correction film or the resin layer. It is more preferably at least 05 parts by mass, and can be at most 10 parts by mass, preferably at most 3 parts by mass, more preferably at most 0.5 part by mass.

  When the color correction layer is an adhesive layer, the method for incorporating the compound (I) into the adhesive layer is not particularly limited, and when preparing the adhesive composition or the pressure-sensitive adhesive composition forming the adhesive layer, the compound (I) I) may be added. The thickness of the adhesive layer is not particularly limited, but may be, for example, 1 μm to 100 μm.

  When the adhesive layer contains the compound (I), the content is not particularly limited. For example, the compound (I) can be used in an amount of 0.01 part by mass or more based on 100 parts by mass of the base polymer constituting the adhesive composition and / or the pressure-sensitive adhesive composition contained in the adhesive layer, and 0.02 parts by mass. Is preferably at least 0.05 part by mass, and more preferably at most 10 parts by mass, and preferably at most 5 parts by mass, more preferably at most 0.5 part by mass. More preferably, there is.

  The optical filter can be used for a display device such as an organic electroluminescence (organic EL) display device or a liquid crystal display device, and can be used by being bonded to a viewing side of an image display element of the display device. In this case, the optical filter preferably has an adhesive layer and a resin layer other than the adhesive layer, and at least one of the adhesive layer and the resin layer is preferably a color correction layer containing the compound (I).

  When the optical filter is a laminate, the laminate structure is not particularly limited. For example, the optical filter can have a laminate structure shown in FIGS. 1A and 1B. 1A and 1B are schematic cross-sectional views illustrating an example of an optical filter. The optical filter 10 shown in FIG. 1A can be used for an organic EL display device. The optical filter 10 can include, for example, an adhesive layer 11 for an image display element, a retardation film 12, an adhesive layer 13, a first protective film 14, a polarizing film 15, and a second protective film 16 in this order. Each of the pressure-sensitive adhesive layer 11 and the pressure-sensitive adhesive layer 13 for an image display element corresponds to the above-described adhesive layer, and the retardation film 12, the first protective film 14, the polarizing film 15, and the second protective film 16 are all This corresponds to the resin layer described above.

  The first protective film 14, the polarizing film 15, and the second protective film 16 in the optical filter 10 form a polarizing plate, and the first protective film 14 and the second protective film 16 are bonded to the polarizing film 15. May have an adhesive layer. The pressure-sensitive adhesive layer 11 for an image display element is used for bonding to a light emitting layer including an organic EL element which is an image display element of an organic EL display device. A separator (release film) (not shown) may be provided on the surface of the image display element pressure-sensitive adhesive layer 11 opposite to the retardation film 12.

  The optical filter 20 shown in FIG. 1B can be used for a liquid crystal display device. The optical filter 20 can include, for example, an adhesive layer 21 for an image display element, a first protective film 24, a polarizing film 25, and a second protective film 26 in this order. The pressure-sensitive adhesive layer 21 for an image display element corresponds to the above-described adhesive layer, and the first protective film 24, the polarizing film 25, and the second protective film 26 all correspond to the above-described resin layer.

  The first protective film 24, the polarizing film 25, and the second protective film 26 in the optical filter 20 form a polarizing plate, and the first protective film 24 and the second protective film 26 are bonded to the polarizing film 25. May have an adhesive layer. The pressure-sensitive adhesive layer 21 for an image display element is used for bonding to a liquid crystal cell which is an image display element of a liquid crystal display device. A separator (release film) (not shown) may be provided on the surface of the image display element pressure-sensitive adhesive layer 21 opposite to the first protective film 24.

  The compound (I) can be contained in at least one of the resin layer and the adhesive layer constituting the optical filters 10 and 20 shown in FIGS. 1 (a) and 1 (b). In the optical filter 10 shown in FIG. 1A, for example, one or more of the pressure-sensitive adhesive layer 11 for an image display element, the pressure-sensitive adhesive layer 13, the first protective film 14, and the second protective film 16 are provided with the compound ( I). In the optical filter 20 shown in FIG. 1B, for example, one or more of the adhesive layer 21 for an image display element, the first protective film 24, and the second protective film 26 may contain the compound (I). it can.

  The optical filters 10 and 20 shown in FIGS. 1A and 1B are merely examples, and may have a laminated structure other than the above. For example, the second protective films 16 and 26 may have further layers such as a film with an anti-glare function and a film with a surface anti-reflection function on the surface opposite to the polarizing films 15 and 25. Further, the first protective films 14 and 24 may have a function as a retardation film, and the second protective films 16 and 26 may have a function as an antiglare function, a surface antireflection function, a function as a retardation film, and the like. May be provided. Further, a color correction layer containing the compound (I) may be provided at an arbitrary position separately from the layers constituting the optical filters 10 and 20 shown in FIGS. 1 (a) and 1 (b).

  Since the above optical filter contains the compound (I), it can absorb light near 580 nm (575 to 590 nm) (preferably light having a maximum absorption wavelength of 580 nm). Thereby, by laminating the optical filter on the viewing side of the image display element of the display device, light having an absorption wavelength in a wavelength range around 580 nm (575 to 590 nm) is absorbed from light incident on the optical filter. The light transmitted through the optical filter can improve the color purity of the green light and the red light as compared with the light incident on the optical filter. In a conventional display device that does not use the above-described optical filter, the separability of green light and red light is not sufficient, but in a display device that uses the above-described optical filter, green light and red light are not used. Can be expected to be improved.

Hereinafter, each member constituting the optical filter will be described in detail.
(Adhesive layer)
Examples of the adhesive composition that can be used for the adhesive layer include a water-based adhesive, an active energy ray-curable adhesive, and a combination thereof. Examples of the water-based adhesive include a polyvinyl alcohol-based resin aqueous solution, a water-based two-part urethane-based emulsion adhesive, and the like. Active energy ray-curable adhesives are adhesives that are cured by irradiating active energy rays such as ultraviolet rays, for example, those containing a polymerizable compound and a photopolymerizable initiator, those containing a photoreactive resin, Examples include those containing a binder resin and a photoreactive crosslinking agent. Examples of the polymerizable compound include photopolymerizable monomers such as photocurable epoxy monomers, photocurable (meth) acrylic monomers, and photocurable urethane monomers, and oligomers derived from these monomers. Examples of the photopolymerization initiator include those containing a substance that generates active species such as neutral radicals, anion radicals, and cation radicals upon irradiation with active energy rays such as ultraviolet rays. In this specification, “(meth) acrylic” means “at least one of acrylic and methacrylic”.

  As the pressure-sensitive adhesive composition that can be used for the adhesive layer, a conventionally known pressure-sensitive adhesive composition can be used. Examples of the adhesive composition include (meth) acrylic adhesives, urethane-based adhesives, silicone-based adhesives, polyester-based adhesives, polyamide-based adhesives, polyether-based adhesives, fluorine-based adhesives, and rubber-based adhesives. An adhesive and the like can be mentioned. Further, an energy ray-curable pressure-sensitive adhesive, a thermosetting pressure-sensitive adhesive, or the like may be used. Among these, a (meth) acrylic pressure-sensitive adhesive is preferably used from the viewpoint of transparency, adhesive strength, reliability and the like.

  The acrylic pressure-sensitive adhesive is not particularly limited, but is a polymer having (meth) acrylic acid ester as a main component (containing 50% by mass or more), and one kind of (meth) acrylic acid ester It may be a homopolymer or a copolymer of (meth) acrylate and another (meth) acrylate. As the (meth) acrylate, butyl (meth) acrylate, ethyl (meth) acrylate, methyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, (meth) acryl 2-phenoxyethyl acid. Further, a polar monomer may be copolymerized in these polymers mainly composed of (meth) acrylic acid esters. Examples of the polar monomer include (meth) acrylic acid, 2-hydroxypropyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, (meth) acrylamide, and 2- (N, N-dimethylamino) ethyl ( Monomers having a polar functional group such as a carboxy group, a hydroxyl group, an amide group, an amino group, and an epoxy group, such as meth) acrylate and glycidyl (meth) acrylate. As the (meth) acrylic resin used for the acrylic pressure-sensitive adhesive, a resin having a weight average molecular weight (Mw) of 100,000 or more can be used, and it is preferably 600,000 or more, and usually 2.5 million or less.

  These acrylic pressure-sensitive adhesives can be used alone, but are usually used in combination with a crosslinking agent. Examples of the crosslinking agent include divalent or polyvalent metal ions that form a metal carboxylate with a carboxy group, amine compounds that form an amide bond with a carboxy group, Examples include epoxy compounds and diol compounds which form an ester bond with a carboxy group, and isocyanate compounds which form an amide bond with a carboxy group. Among them, isocyanate compounds are preferably used.

Among the isocyanate compounds, xylylene diisocyanate, tolylene diisocyanate or hexamethylene diisocyanate; an adduct obtained by reacting a polyol such as glycerol or trimethylolpropane with these isocyanate compounds; dimer or trimer of these isocyanate compounds Or a mixture thereof; a mixture of two or more of the above-mentioned isocyanate compounds is preferably used.
Preferred isocyanate-based compounds include tolylene diisocyanate, adducts obtained by reacting polyol with tolylene diisocyanate, dimers of tolylene diisocyanate, and trimers of tolylene diisocyanate, and hexamethylene diisocyanate and hexamethylene diisocyanate. An adduct obtained by reacting a polyol, a dimer of hexamethylene diisocyanate, and a trimer of hexamethylene diisocyanate are exemplified.

  The content of the crosslinking agent in the acrylic pressure-sensitive adhesive is generally 0 parts by mass or more and 5 parts by mass or less, preferably 0.05 parts by mass or more and 2 parts by mass or less with respect to 100 parts by mass of the (meth) acrylic resin. .

  The acrylic pressure-sensitive adhesive can further contain a silane compound. When the acrylic pressure-sensitive adhesive contains a silane compound, the adhesiveness between the obtained pressure-sensitive adhesive layer and an optical member such as a glass substrate can be enhanced.

  Examples of the silane compound include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, and 3-glycidoxypropyl Methyldimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-gly Sidoxypropyltriethoxysilane, 3-glycidoxypropyldimethoxymethylsilane, 3-glycidoxypropylethoxydimethylsilane and the like can be mentioned. Two or more silane compounds may be used.

  The silane compound may be of the silicone oligomer type. When the silicone oligomer is shown in the form of a (monomer) oligomer, for example, 3-mercaptopropyltrimethoxysilane-tetramethoxysilane copolymer, mercaptomethyltrimethoxysilane-tetramethoxysilane copolymer, 3-glycidoxypropyltrimethoxysilane -Tetramethoxysilane copolymer, 3-methacryloyloxypropyltrimethoxysilane-tetramethoxysilane copolymer, 3-acryloyloxypropyltrimethoxysilane-tetramethoxysilane copolymer, vinyltrimethoxysilane-tetramethoxysilane copolymer, and the like.

  The content of the silane compound in the acrylic pressure-sensitive adhesive is usually 0.01 to 10 parts by mass, preferably 0.05 to 5 parts by mass, based on 100 parts by mass of the (meth) acrylic resin. It is more preferably at least 0.1 part by mass and at most 2 parts by mass. When the content of the silane compound is 0.01 parts by mass or more, the effect of improving the adhesion between the pressure-sensitive adhesive layer and an optical member such as a glass substrate is easily obtained. When the content of the silane compound is 10 parts by mass or less, bleed out of the silane compound from the pressure-sensitive adhesive layer can be suppressed.

  The acrylic pressure-sensitive adhesive may further contain an ionic compound as an antistatic agent for imparting antistatic properties. The ionic compound is a compound having an inorganic cation or an organic cation and an inorganic anion or an organic anion. The acrylic pressure-sensitive adhesive may contain two or more ionic compounds.

Examples of the inorganic cation include alkali metal ions such as lithium cation [Li ⁺ ], sodium cation [Na ⁺ ], potassium cation [K ⁺ ], beryllium cation [Be ²⁺ ], magnesium cation [Mg ²⁺ ], and calcium cation. And alkaline earth metal ions such as [Ca ²⁺ ].
Examples of the organic cation include an imidazolium cation, a pyridinium cation, a pyrrolidinium cation, an ammonium cation, a sulfonium cation, and a phosphonium cation.

Examples of the inorganic anion include a chloride anion [Cl ⁻ ], a bromide anion [Br ⁻ ], an iodide anion [I ⁻ ], a tetrachloroaluminate anion [AlCl ₄ ⁻ ], a heptachlorodialuminate anion [Al ₂ Cl ₇ ^-], tetrafluoroborate anion [BF ₄ ^-], hexafluorophosphate anion [PF ₆ ^-], perchlorate anion [ClO ₄ ^-], nitrate anion [NO ₃ ^-], hexafluoro ah cell anion [AsF ₆ ⁻ ], Hexafluoroantimonate anion [SbF ₆ ⁻ ], hexafluoroniobate anion [NbF ₆ ⁻ ], hexafluorotantalate anion [TaF ₆ ⁻ ], dicyanamide anion [(CN) ₂ N ⁻ ] and the like. Be

Examples of the organic anion include an acetate anion [CH ₃ COO ⁻ ], a trifluoroacetate anion [CF ₃ COO ⁻ ], a methanesulfonate anion [CH ₃ SO ₃ ⁻ ], a trifluoromethane sulfonate anion [CF ₃ SO ₃ ⁻ ], p- toluenesulfonate anion _{[p-CH 3 C 6 H 4} SO 3 - ], bis (fluorosulfonyl) imide anion _{[(FSO 2)} 2 N ^-], bis (trifluoromethanesulfonyl) imide anion _[(CF 3 SO ₂ ) ₂ N ^-], tris (trifluoromethanesulfonyl) meth acetonide anion _{[(CF 3 SO 2) 3 C} - ], dimethyl phosphinate anion _{[(CH 3)} 2 POO ^-], (poly) hydrofluoroether fluoride anion [ F (HF) _n ⁻ ] (N is about 1 to 3), thiocyan anion [SCN ⁻ ], perfluorobutane sulfonate anion [C ₄ F ₉ SO ₃ ⁻ ], bis (pentafluoroethane sulfonyl) imide anion [(C ₂ F ₅ SO ₂ )] ₂ N ⁻ ], perfluorobutanoate anion [C ₃ F ₇ COO ⁻ ], (trifluoromethanesulfonyl) (trifluoromethanecarbonyl) imide anion [(CF ₃ SO ₂ ) (CF ₃ CO) N ⁻ ] and the like. Can be

  Specific examples of the ionic compound can be selected from combinations of the above-mentioned cation component and anion component.

  Examples of the ionic compound having an organic cation include N-octylpyridinium hexafluorophosphate, N-octyl-4-methylpyridinium hexafluorophosphate, N-butyl-4-methylpyridinium hexafluorophosphate, N-decylpyridinium bis ( Pyridinium salts such as fluorosulfonyl) imide, N-hexylpyridinium bis (trifluoromethanesulfonyl) imide, N-octylpyridinium bis (trifluoromethanesulfonyl) imide, 1-ethyl-3-methylimidazolium hexafluorophosphate, 1-ethyl- 3-methylimidazolium p-toluenesulfonate, 1-ethyl-3-methylimidazolium bis (fluorosulfonyl) imide, 1-ethyl-3-methyl Imidazolium salts such as imidazolium bis (trifluoromethanesulfonyl) imide and 1-butyl-3-methylimidazolium methanesulfonate; N-butyl-N-methylpyrrolidinium hexafluorophosphate, N-butyl-N-methylpyrrolidide Pyrrolidinium salts such as ammonium bis (fluorosulfonyl) imide and N-butyl-N-methylpyrrolidinium bis (trifluoromethanesulfonyl) imide; quaternary ammonium salts such as tetrabutylammonium hexafluorophosphate and tetrabutylammonium p-toluenesulfonate Is mentioned.

  Examples of the ionic compound having an inorganic cation include lithium bromide, lithium iodide, sodium hexafluorophosphate, and the like.

  The ionic compound is preferably solid at room temperature from the viewpoint of maintaining antistatic performance. The ionic compound preferably has a melting point of 30 ° C. or more, more preferably 35 ° C. or more. On the other hand, if the melting point is too high, the compatibility with the (meth) acrylic resin is deteriorated. Therefore, the melting point of the ionic compound is preferably 90 ° C. or lower, more preferably 70 ° C. or lower, and further preferably 50 ° C. or lower. It is below ° C.

  The content of the ionic compound in the acrylic pressure-sensitive adhesive is preferably 0.1 to 8 parts by mass, more preferably 0.2 to 6 parts by mass, based on 100 parts by mass of the (meth) acrylic resin. Or less, more preferably 0.5 to 5 parts by mass, particularly preferably 1 to 5 parts by mass. When the content of the ionic compound is 0.1 parts by mass or more, it is advantageous for improving antistatic performance, and when it is 8 parts by mass or less, it is advantageous for maintaining the durability of the pressure-sensitive adhesive layer.

  The adhesive composition and the pressure-sensitive adhesive composition may further contain various additives. Examples of the additives include a reworking agent, a tackifying resin, an antioxidant, an ultraviolet absorber, an antifoaming agent, a corrosive, and a light diffusing agent such as fine particles.

(Resin layer)
As the resin layer, a polarizing film; a protective film provided to protect the surface of the polarizing film or the like; a retardation film; an optical compensation film other than the retardation film; A film having an anti-reflection function; a reflection film having a reflection function on the surface; a transflective film having both a reflection function and a transmission function; a light diffusion film; a hard coat film; The optical filter may include one or more resin layers described above.

  Examples of the polarizing film include a film in which iodine is oriented in a polyvinyl alcohol-based resin layer and a film in which a liquid crystal compound and a dichroic dye are oriented.

  The material when the resin layer is other than the polarizing film is not particularly limited, and examples thereof include chain polyolefin resins (polyethylene resins, polypropylene resins, etc.) and cyclic polyolefin resins (norbornene resins, etc.). Polyolefin resins; cellulose ester resins such as triacetyl cellulose, diacetyl cellulose and cellulose acetate propionate; polyester resins such as polyethylene terephthalate and polyethylene naphthalate; polycarbonate resins; (meth) acrylic acid, poly (meth) acrylic (Meth) acrylic resins such as methyl acid; vinyl alcohol resins such as polyvinyl alcohol and polyvinyl acetate; polystyrene resins; mixtures thereof, copolymers and the like. These resins may contain one or more additives such as lubricants, plasticizers, dispersants, heat stabilizers, ultraviolet absorbers, infrared absorbers, antistatic agents, antioxidants, and light diffusing agents such as fine particles. It may be contained.

(Display device)
The above-described optical filter can be suitably used for display devices such as an organic EL display device, a liquid crystal display device, an inorganic electroluminescence (inorganic EL) display device, and an electron emission display device. By arranging the optical filter on the viewing side of the image display element of the display device, light having a wavelength of about 580 nm (575 to 590 nm) (preferably light having a maximum absorption wavelength of 580 nm) among the light incident on the optical filter. Can be absorbed. Accordingly, the light transmitted through the optical filter has higher color purity of the green light and the red light as compared with the case where the light does not transmit through the optical filter, so that the color gamut that can be expressed in the display device can be expanded. . In a conventional display device not using the optical filter, the separation between green light and red light was not sufficient, but in a display device using the above-described optical filter, green light and red light were used. Can be expected to improve the separation property.

  2A and 2B are schematic cross-sectional views illustrating an example of a display device including an optical filter. The display device illustrated in FIG. 2A is an organic EL display device including the optical filter 10 illustrated in FIG. 1A and the image display device 1 that is a light emitting layer including the organic EL device. The optical filter 10 can be arranged on the viewing side of the image display element 1 via the adhesive layer 11 for the image display element.

  The display device illustrated in FIG. 2B is a liquid crystal display device including the optical filter 20 illustrated in FIG. 1B and the image display element 2 which is a liquid crystal cell including a liquid crystal layer. The optical filter 20 can be disposed on the viewing side of the image display element 2 via the adhesive layer 21 for the image display element.

  Hereinafter, the present invention will be described more specifically with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples. “%” And “parts” in Synthesis Examples, Comparative Synthesis Examples, Examples, and Comparative Examples are% by mass and parts by mass unless otherwise specified.

[Identification of compound]
The structure of the compound was identified by mass spectrometry (LC; Model 1200 manufactured by Agilent, MASS; LC / MSD model manufactured by Agilent).

[Measurement of maximum absorption wavelength]
A solution obtained by dissolving the compound (compound represented by formula (I)) obtained in the synthesis example in a solvent shown in Table 1 was applied to an ultraviolet-visible spectrophotometer (V-650DS; manufactured by JASCO Corporation). (Quartz cell, optical path length; 1 cm), the maximum absorption wavelength was measured.
The pressure-sensitive adhesive sheets obtained in Examples and Comparative Examples were also measured for the maximum absorption wavelength using the ultraviolet-visible spectrophotometer.

[Synthesis example 1 (compound represented by formula (II))]
3.0 parts of 3,4-dihydroxy-3-cyclobutene-1,2-dione (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.) and 5.0 parts of 2,4-dimethylpyrrole (manufactured by Tokyo Chemical Industry Co., Ltd.) , 1-butanol and 290 parts of toluene were mixed. The obtained mixture was stirred at a temperature of 110 ° C for 3 hours while removing generated water using a Dean-Stark tube. After completion of the reaction, the solvent was distilled off, 300 parts of ion-exchanged water was added, and the precipitated solid was collected by filtration. The solid collected by filtration was washed with methanol / ion exchanged water. The obtained solid was dried under reduced pressure at a temperature of 60 ° C. for 12 hours to obtain 4.0 parts of a compound represented by the formula (A-1).

After cooling 2.3 parts of the compound (A-1) in an ice bath in the presence of 200 parts of tetrahydrofuran, 3.2 parts of N-bromosuccinimide (manufactured by Tokyo Chemical Industry Co., Ltd.) is added, and the mixture is cooled in an ice bath. Stirred for hours. After the obtained reaction mass (reaction liquid) was heated to room temperature, an aqueous solution of sodium thiosulfate was added to quench the reaction. The solvent was distilled off, and the obtained solid was washed with methanol / ion-exchanged water. The obtained solid was dried to obtain 3.6 parts of a compound represented by the formula (A-2). The obtained compound was subjected to mass spectrometry.
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 424.9
Exact Mass: 423.9

[Synthesis Example 2 (Compound represented by Formula (I))]
0.85 part of the compound represented by the formula (A-2) obtained in Synthesis Example 1, 89 parts of tetrahydrofuran, and 70 parts of ion-exchanged water were mixed. 6 parts of 1 mol / L cesium carbonate aqueous solution, 0.37 parts of tris (dibenzylideneacetone) -dipalladium (0), 0.46 parts of tri-tert-butylphosphonium tetrafluoroborate, 2,6-dimethyl-4- ( 1.49 parts of 4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was refluxed for 2 hours. After completion of the reaction, 10% aqueous acetic acid was added to stop the reaction. A 10% saline solution was added, and after liquid separation, the organic layer was concentrated. The obtained solid was recrystallized from 100 parts of a toluene / 1-butanol = 1/1 solution to obtain 0.4 part of a compound represented by the formula (A-3). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass Spectrometry) ionization mode ^{= ESI +: m / z =} [M + H] + 509.2
Exact Mass: 508.24

[Synthesis Example 3 (compound represented by formula (I))]
Instead of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2, 3,4,5-trimethoxyphenyl Except using boronic acid, it synthesize | combined similarly to the synthesis example 2, and obtained the compound represented by Formula (A-4). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass Spectrometry) ionization mode ^{= ESI +: m / z =} [M + H] + 601.3
Exact Mass: 600.25

[Synthesis example 4 (compound represented by formula (I))]
In place of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2, 4-hexylphenylboronic acid was used. Except for this, the compound was synthesized in the same manner as in Synthesis Example 2 to obtain a compound represented by the formula (A-5). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass Spectrometry) ionization mode ^{= ESI +: m / z =} [M + H] + 589.4
Exact Mass: 588.37

[Synthesis Example 5 (compound represented by formula (I))]
4-hexyloxyphenylboronic acid was used in place of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2. Except for the above, the compound was synthesized in the same manner as in Synthesis Example 2 to obtain a compound represented by the formula (A-6). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass Spectrometry) ionization mode ^{= ESI +: m / z =} [M + H] + 621.4
Exact Mass: 620.36

[Synthesis Example 6 (compound represented by formula (I))]
Instead of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2, 4- (dimethylamino) phenylboronic acid Compound (A-7) was synthesized in the same manner as in Synthesis Example 2 except that was used to obtain a compound represented by the formula (A-7). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass Spectrometry) ionization mode ^{= ESI +: m / z =} [M + H] + 507.3
Exact Mass: 506.27

[Synthesis Example 7 (compound represented by formula (I))]
Instead of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2, 4- (diphenylamino) phenylboronic acid Compound (A-8) was synthesized in the same manner as in Synthesis Example 2 except that was used to obtain a compound represented by the formula (A-8). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass Spectrometry) ionization mode ^{= ESI +: m / z =} [M + H] + 754.3
Exact Mass: 754.33

[Synthesis Example 8 (Compound represented by Formula (I))]
4'-propyl-4-biphenylborone instead of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2 Except that an acid was used, synthesis was performed in the same manner as in Synthesis Example 2 to obtain a compound represented by the formula (A-9). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass Spectrometry) ionization mode ^{= ESI +: m / z =} [M + H] + 657.3
Exact Mass: 656.34

[Synthesis example 9 (compound represented by formula (I))]
Instead of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2, 6-ethoxy-2-naphthaleneboronic acid Compound (A-10) was synthesized in the same manner as in Synthesis Example 2 except that was used to obtain a compound represented by the formula (A-10). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass Spectrometry) ionization mode ^{= ESI +: m / z =} [M + H] + 609.3
Exact Mass: 608.27

[Synthesis Example 10 (compound represented by formula (I))]
Instead of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2, 9,9-dimethylfluoren-2-yl Except using boronic acid, it synthesize | combined similarly to the synthesis example 2, and obtained the compound represented by Formula (A-11). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass Spectrometry) ionization mode ^{= ESI +: m / z =} [M + H] + 653.3
Exact Mass: 652.31

[Synthesis Example 11 (compound represented by formula (I))]
Instead of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2, benzo [b] thiophen-2-boron Except for using an acid, the same synthesis as in Synthesis Example 2 was performed to obtain a compound represented by the formula (A-12). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 533.1
Exact Mass: 532.13

[Synthesis Example 12 (compound represented by formula (I))]
Instead of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2, 9-ethylcarbazole-3-boronic acid Compound (A-13) was synthesized in the same manner as in Synthesis Example 2 except that was used to obtain a compound represented by the formula (A-13). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass Spectrometry) ionization mode ^{= ESI +: m / z =} [M + H] + 655.3
Exact Mass: 654.30

[Synthesis Example 13 (compound represented by formula (I))]
Instead of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2, 9- (4-biphenylyl) carbazole- Except for using 3-boronic acid pinacol, the synthesis was performed in the same manner as in Synthesis Example 2 to obtain a compound represented by the formula (A-14). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass Spectrometry) ionization mode ^{= ESI +: m / z =} [M + H] + 903.4
Exact Mass: 902.36

[Synthesis Comparative Example 1]
In the synthesis method of the compound represented by the formula (A-1) of Synthesis Example 1, except that 3-ethyl-2,4-dimethylpyrrole was used instead of 2,4-dimethylpyrrole. The compound represented by the formula (B-1) was synthesized in the same manner as in the compound represented by the formula (1). The maximum absorption wavelength of the obtained compound was measured. Table 1 shows the measured maximum absorption wavelengths.

[Synthesis Comparative Example 2]
The compound represented by the formula (A-1) was obtained by the procedure of the synthesis method of the compound represented by the formula (A-1) in Synthesis Example 1. The maximum absorption wavelength of the obtained compound was measured. Table 1 shows the measured maximum absorption wavelengths.

[Synthesis Example 14 (compound represented by formula (I))]
Instead of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2, 4-tert-butylphenylboronic acid was used. Except for using the compound, it was synthesized in the same manner as in Synthesis Example 2 to obtain a compound represented by the formula (A-15). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass Spectrometry) ionization mode ^{= ESI +: m / z =} [M + H] + 533.3
Exact Mass: 532.3

[Synthesis Example 15 (compound represented by formula (I))]
Instead of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2, 4-methoxy-3,5-dimethyl Except that phenylboronic acid was used, synthesis was carried out in the same manner as in Synthesis Example 2 to obtain a compound represented by the formula (A-16). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass spectrometry) ionization mode = ESI +: m / z = [M + H] ⁺ 537.2
Exact Mass: 536.3

[Synthesis Example 16 (compound represented by formula (I))]
Instead of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2, 4-carboxyphenylboronic acid pinacol was used. Except for the above, the compound was synthesized in the same manner as in Synthesis Example 2 to obtain a compound represented by the formula (A-17). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass Spectrometry) ionization mode ^{= ESI +: m / z =} [M + H] + 509.5
Exact Mass: 508.2

[Synthesis Example 17 (compound represented by formula (I))]
1-thianthrenylboronic acid was used in place of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2. Except for the above, the compound was synthesized in the same manner as in Synthesis Example 2 to obtain a compound represented by the formula (A-18). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass Spectrometry) ionization mode ^{= ESI +: m / z =} [M + H] + 697.2
Exact Mass: 696.1

[Synthesis example 18 (compound represented by formula (I))]
Instead of 2,6-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) phenol in Synthesis Example 2, 4-methyl-1-naphthaleneboronic acid Compound (A-19) was synthesized in the same manner as in Synthesis Example 2 except that was used to obtain a compound represented by the formula (A-19). About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 549.2
Exact Mass: 548.3

[Synthesis example 19 (compound represented by formula (II))]
11.89 parts of 3,4-dibutoxy-3-cyclobutene-1,2-dione (manufactured by Tokyo Chemical Industry Co., Ltd.) and 38.9 parts of 1-butanol were mixed and heated and stirred at 110 ° C. To the obtained mixture, 5.0 parts of 2,4-dimethylpyrrole (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise over 10 minutes, and the mixture was heated under reflux for 3 hours. The obtained mixture was cooled to room temperature, and the precipitated crystals were filtered to separate the solution from the crystals. When the obtained crystals were subjected to repulping washing using 327 parts of hexane, a pale green solid was obtained.
48.3 parts of acetic acid and the above solid were mixed with an aqueous solution adjusted with 7.1 parts of concentrated hydrochloric acid and 40 parts of distilled water, and the mixture was heated under reflux at 110 ° C. for 2 hours, and the color changed from pale green to pale orange. Occurred and the reaction stopped.
The obtained reaction solution was cooled to room temperature, and a pale orange powder was separated by filtration. The obtained powder was subjected to repulping washing with 164 parts of hexane to obtain 5.65 parts (yield: 56.2%) of a pale yellow compound represented by the formula (C-1).

1.39 parts of the compound represented by the formula (C-1), 1.0 part of 3-acetyl-2,4-dimethylpyrrole (manufactured by Tokyo Chemical Industry Co., Ltd.), 21.6 parts of 1-butanol, and toluene 35 And then heated and refluxed at 110 ° C. for 3 hours. The resulting reaction solution was cooled to room temperature, and the precipitated crystals were filtered to separate the solution from the crystals. The crystals were subjected to repulping washing using 327 parts of hexane to obtain 0.96 parts (yield: 85.3%) of a compound represented by the formula (C-2) in purple.

0.80 part of the compound represented by the formula (C-2) and 59.5 parts of dehydrated tetrahydrofuran were mixed, and the mixture was stirred at an ice temperature (5 ° C) for 30 minutes while purging with nitrogen.
0.94 parts of N-bromosuccinimide was added to the obtained mixture, and the mixture was stirred at an ice temperature (5 ° C) for 2 hours. Pure water was added to the obtained reaction solution, and the mixture was filtered to collect crystals. After redissolving the obtained crystals in tetrahydrofuran, pure water was added to precipitate the crystals again, and 0.91 parts of a compound represented by the formula (A-20) in black purple color was obtained (yield: 90.7 parts). %)Obtained. About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 389.2
Exact Mass: 388.04

[Synthesis Example 20 (Compound represented by Formula (I))]
0.195 parts of the compound represented by the formula (A-20), 22.2 parts of tetrahydrofuran, and 17.5 parts of pure water were added to a four-necked flask, and nitrogen gas was introduced at 80 ° C for 60 minutes to perform bubbling. went. 0.092 parts of tris (dibenzylideneacetone) palladium, 0.116 parts of [tri (tertiarybutyl) phosphonium] tetrafluoroborate and 1.5 parts of a 1 mol / L cesium carbonate aqueous solution were added to the obtained mixture. . The reaction solution is obtained by dissolving 0.243 parts of benzofuran-2-boronic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) in 6.66 parts of tetrahydrofuran while stirring the reaction solution at an oil bath temperature of 80 ° C. The solution was added dropwise over 10 minutes and stirred for 2 hours. To the obtained mixture, 100 parts of a 10% by mass acetic acid aqueous solution was added, and the mixture was stirred under a nitrogen atmosphere for 15 minutes.
To the obtained mixture, 0.3 parts of 10% saline was added, and a liquid separation operation was performed to separate an organic layer. The organic layer was dried using an evaporator to obtain a tar-like crude product 1. The crude product 1 was subjected to extraction using methanol, and then methanol was removed to obtain a crude product 2. The obtained crude product 2 was heated and dissolved using 100 parts of a toluene / butanol = 1/1 solution, and recrystallized to obtain 0.07 part of a compound represented by the formula (A-21) ( Yield 32.8%).
About the obtained compound, while performing mass spectrometry, the maximum absorption wavelength was measured. Table 1 shows the measured maximum absorption wavelengths.
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 427.1
Exact Mass: 426.16

[Example 1]
(Production of (meth) acrylic resin)
In a reaction vessel equipped with a cooling pipe, a nitrogen introduction pipe, a thermometer and a stirrer, 81.8 parts of ethyl acetate as a solvent, 69.8 parts of butyl acrylate as a monomer, 20 parts of methyl acrylate, and 2 parts of acrylic acid -A mixture of 1 part of hydroxyethyl, 8 parts of 2-phenoxyethyl acrylate, 1 part of 2-methoxyethyl acrylate and 0.2 part of acrylic acid is charged, and the air in the reaction vessel is replaced with nitrogen gas to remove oxygen. The internal temperature was raised to 55 ° C. while containing the mixture. To the resulting mixed solution, a solution prepared by dissolving 0.14 parts of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added in total. The obtained mixture is maintained at an internal temperature of 55 ° C. for 1 hour, and then, while maintaining the internal temperature at 55 ° C., ethyl acetate is continuously added into the reaction vessel at an addition rate of 17.3 parts / hr, to give (meth) When the concentration of the acrylic resin reached 35%, the addition of ethyl acetate was stopped and polymerization was carried out for 8 hours. Finally, ethyl acetate was added so that the concentration of the (meth) acrylic resin became 20% to prepare a solution of the (meth) acrylic resin in ethyl acetate. When the weight average molecular weight (Mw) and polydispersity (Mw / Mn) of the obtained (meth) acrylic resin were measured, the weight average molecular weight (Mw) was 1.4 million, and the polydispersity (Mw / Mn) was found. ) Was 5.1.

(Preparation of adhesive composition 1)
A crosslinking agent ("Coronate HXR" (isocyanurate-modified hexamethylene diisocyanate) obtained from Tosoh Corporation) was used for 100 parts of the solid content of the (meth) acrylic resin obtained in the production of the (meth) acrylic resin. ), 0.5 part of a silane compound ("KBM-403" (3-glycidoxypropyltrimethoxysilane) obtained from Shin-Etsu Chemical Co., Ltd.), and N-hexyl-4 as an antistatic agent. -Methylpyridinium Phosphorus hexafluoride (3 parts), the compound represented by the formula (A-5) (0.1 part) were mixed, and ethyl acetate was added so that the solid content became 14%. A solution of product 1 was prepared.

(Preparation of adhesive sheet 1)
Using an applicator, apply the pressure-sensitive adhesive composition 1 to the release-treated surface of a first separator film ("PLR-382190" obtained from Lintec Corporation) made of a polyethylene terephthalate film subjected to a release treatment. Then, it was dried at 100 ° C. for 1 minute to prepare an adhesive layer. The thickness of the obtained pressure-sensitive adhesive layer was 20 μm. On the obtained pressure-sensitive adhesive layer, a release-treated surface of a second separator film ("PLR-251130" obtained from Lintec Co., Ltd.) made of a polyethylene terephthalate film subjected to a release treatment was bonded. Sheet 1 was obtained. One of the separator films of the obtained pressure-sensitive adhesive sheet 1 was peeled off, bonded to one surface of non-alkali glass (EagleXG manufactured by Corning), and using an ultraviolet-visible spectrophotometer (UV-2450 manufactured by Shimadzu Corporation). The maximum absorption wavelength was measured. Table 2 shows the results. The absorbance of the above-described separator film and alkali-free glass at a wavelength of 400 nm to 700 nm is almost 0.

[Example 2]
Pressure-sensitive adhesive composition 2 was prepared in the same manner as in preparation of pressure-sensitive adhesive composition 1, except that the compound represented by formula (A-6) was used instead of the compound represented by formula (A-5). A pressure-sensitive adhesive sheet 2 was prepared in the same manner as in the preparation of the pressure-sensitive adhesive sheet 1 except that the obtained pressure-sensitive adhesive composition 2 was used, and the maximum absorption wavelength was measured. Table 2 shows the results.

[Examples 3 to 11]
Pressure-sensitive adhesive compositions 5 to 11 were prepared in the same manner as in the preparation of pressure-sensitive adhesive composition 1, except that the compounds shown in Table 2 were used instead of the compound represented by the formula (A-5). Except that the obtained pressure-sensitive adhesive compositions 5 to 11 were used, pressure-sensitive adhesive sheets 5 to 11 were prepared in the same manner as in the preparation of pressure-sensitive adhesive sheet 1, and the maximum absorption wavelength was measured. Table 2 shows the results.

[Comparative Example 1]
Pressure-sensitive adhesive composition 3 was prepared in the same manner as in preparation of pressure-sensitive adhesive composition 1, except that the compound represented by formula (B-1) was used instead of the compound represented by formula (A-5). A pressure-sensitive adhesive sheet 3 was prepared in the same manner as in the preparation of the pressure-sensitive adhesive sheet 1 except that the obtained pressure-sensitive adhesive composition 3 was used, and the maximum absorption wavelength was measured. Table 2 shows the results.

[Comparative Example 2]
Pressure-sensitive adhesive composition 4 was prepared in the same manner as in the preparation of pressure-sensitive adhesive composition 1, except that the compound represented by formula (A-1) was used instead of the compound represented by formula (A-5). The pressure-sensitive adhesive sheet 4 was prepared in the same manner as in the preparation of the pressure-sensitive adhesive sheet 1 except that the obtained pressure-sensitive adhesive composition 4 was used, and the maximum absorption wavelength was measured. Table 2 shows the results.

[Comparative Example 3]
Pressure-sensitive adhesive composition 14 was prepared in the same manner as in the preparation of pressure-sensitive adhesive composition 1, except that the compound represented by the formula (A-5) was not used. The pressure-sensitive adhesive sheet 14 was produced in the same manner as in the production of the pressure-sensitive adhesive sheet 1 except that the obtained pressure-sensitive adhesive composition 14 was used.

(Calculation of reproducible color gamut)
Based on the absorption spectrum obtained for the pressure-sensitive adhesive sheet 5 of Application Example 3, when the pressure-sensitive adhesive sheet 5 is applied to a panel having a general-purpose backlight and a general-purpose color filter, a color gamut range that can be reproduced on the panel [%] Was calculated by simulation. The general-purpose backlight used for the simulation is a mixture of a Blue LED and a YAG phosphor, and the general-purpose color filter is an sRGB compliant standard display. Regarding the reproducible color gamut range [%], a color reproducible range with respect to the DCIP3 color standard was calculated using the CIE1976 color system and compared.
The same calculation was performed when the pressure-sensitive adhesive sheet 14 was used instead of the pressure-sensitive adhesive sheet 5. Based on the color reproducible range of the pressure-sensitive adhesive sheet 14, the color reproducible range was calculated based on the following equation.
Color reproduction range [%] =
(Color reproducible range when adhesive sheet 5 is applied) / (color reproducible range when adhesive sheet 14 is applied) × 100

  The reproducible color gamut ranges of the pressure-sensitive adhesive sheets 3 and 4 were calculated in the same manner as described above. Table 3 shows the results.

(Calculation of backlight transmittance)
The amount of transmission of the backlight when the pressure-sensitive adhesive layer sheet 5 was applied to a panel having a general-purpose backlight and a general-purpose color filter was calculated by simulation. The general-purpose backlight used for the simulation is a mixture of a Blue LED and a YAG phosphor, and the general-purpose color filter is an sRGB compliant standard display.
The same calculation was performed when the pressure-sensitive adhesive sheet 14 was used instead of the pressure-sensitive adhesive sheet 5. Based on the amount of transmission of the backlight when the pressure-sensitive adhesive sheet 14 was applied, the transmittance of the backlight when the pressure-sensitive adhesive sheet 5 was applied to the panel was calculated based on the following calculation formula. Table 3 shows the results.
Backlight transmittance [%] =
(Transmission amount of backlight when pressure-sensitive adhesive sheet 5 is applied) / (Transmission amount of backlight when pressure-sensitive adhesive sheet 14 is applied) × 100

  The backlight transmittance of each of the pressure-sensitive adhesive sheets 3 and 4 was calculated in the same manner as described above. Table 3 shows the results.

  By mixing the compound (I) with a (meth) acrylic resin solution to prepare an adhesive sheet, an optical filter having a maximum absorption wavelength in a wavelength range around 580 nm (wavelength 575 to 590 nm) can be manufactured. Was. In addition, by applying the pressure-sensitive adhesive sheet (optical filter) containing the compound (I) to a display device, the separation between green light and red light in transmitted light can be improved, and thus, reproducibility can be improved. The gamut range could be expanded. In addition, a decrease in the transmittance of the backlight could be suppressed.

[Example 12 (Preparation of photocurable adhesive liquid 1)]
3 ′, 4′-Epoxycyclohexylmethyl To 80 parts of 3,4-epoxycyclohexanecarboxylate, 20 parts of 1,4-butanediol diglycidyl ether, 3 parts of a cationic photopolymerization initiator, the formula (A-16) Was mixed and defoamed to prepare a photocurable adhesive liquid 1.

[Example 13 (Preparation of photocurable adhesive liquid 2)]
Photocurable adhesive liquid 2 was prepared by performing the same preparation as photocurable adhesive liquid 1 except that the compound represented by formula (A-18) was added instead of the compound represented by formula (A-16). did.

[Example 14 (production of polarizing plate 1)]
A surface of a 60 μm-thick triacetylcellulose film (trade name “Fujitack TG60UL”, manufactured by Fuji Film Co., Ltd.) containing an ultraviolet absorber is subjected to corona discharge treatment, and the corona discharge-treated surface is subjected to the photocuring prepared above The adhesive liquid 1 was applied using a bar coater so that the film thickness after curing was about 2 μm. A 28 μm-thick polyvinyl alcohol-iodine polarizer was bonded to the adhesive layer formed by this coating. In addition, a corona discharge treatment is applied to the surface of a 50 μm-thick retardation film (trade name “ZEONOR”, manufactured by Zeon Corporation) made of a cyclic polyolefin resin, and the photocurable adhesive is applied to the corona discharge treatment surface. Liquid 1 was applied using a bar coater so that the film thickness after curing was about 2 μm. The polarizer side of the polarizer having the above-prepared triacetylcellulose film bonded on one side was bonded to the adhesive layer formed by this coating to prepare a laminate. Ultraviolet light was irradiated from the retardation film side of this laminate using an ultraviolet irradiation device with a belt conveyor (the lamp used was a “D bulb” manufactured by Fusion UV Systems) so that the integrated light amount became 200 mJ / cm ^2. The adhesive was cured. Thus, a polarizing plate 1 in which protective films were bonded to both surfaces of the polarizer was produced. The obtained polarizing plate was cut into a size of 40 mm × 40 mm, and arranged so that measurement light was incident from the surface opposite to the retardation film, and using an ultraviolet-visible spectrophotometer (UV-2450 manufactured by Shimadzu Corporation). The transmission spectrum of the polarizing plate in the transmission axis direction in the wavelength range of 400 nm to 700 nm was measured. In the obtained spectrum, the wavelength at which the transmittance becomes minimum was defined as the maximum absorption wavelength. Table 4 shows the results.

[Example 15 (production of polarizing plate 2)]
A polarizing plate 2 having a protective film attached to both surfaces of a polarizer was prepared in the same manner as in the production of the polarizing plate 1 except that the photocurable adhesive solution 2 was used instead of the photocurable adhesive solution 1. Produced. The obtained polarizing plate was cut into 40 mm × 40 mm, and the maximum absorption wavelength was obtained by using the same method as that for the polarizing plate 1. Table 4 shows the results.

  1, 2 image display element, 10 optical filter, 11 adhesive layer for image display element, 12 retardation film, 13 adhesive layer, 14 first protective film, 15 polarizing film, 16 second protective film, 20 optical laminate , 21 adhesive layer for image display element, 24 first protective film, 25 polarizing film, 26 second protective film.

Claims (4)

An optical filter containing the compound represented by the formula (I).

[Where,
R ^{1 to} R ⁴ each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
T ¹ and T ² each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent.
Y ¹ and Y ² each represent a monovalent aromatic group optionally having a substituent, and the other one may represent a monovalent aromatic group optionally having a substituent, a hydrogen atom, A halogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms which may have a substituent (the hydrocarbon group is a group other than a monovalent aromatic group, and- CH ₂ — may be replaced by —O— or —CO—. ] In addition, including an adhesive layer,
The optical filter according to claim 1, wherein the adhesive layer includes a compound represented by the formula (I). A display device comprising the optical filter and the image display element according to claim 1 or 2,
The display device, wherein the optical filter is arranged on a viewing side with respect to the image display element.   The display device according to claim 3, which is a liquid crystal display device or an organic electroluminescence display device.

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