CN112470045B - Optical filter and display device - Google Patents

Optical filter and display device Download PDF

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Publication number
CN112470045B
CN112470045B CN201980048913.1A CN201980048913A CN112470045B CN 112470045 B CN112470045 B CN 112470045B CN 201980048913 A CN201980048913 A CN 201980048913A CN 112470045 B CN112470045 B CN 112470045B
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CN112470045A (en
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佐濑光敬
大家健一郎
三上智司
朴廷烋
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/007—Squaraine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/8791—Arrangements for improving contrast, e.g. preventing reflection of ambient light

Abstract

The invention provides an optical filter comprising a compound shown as a formula (I).[ in formula (I), R 1 ～R 4 Each independently represents a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent. T (T) 1 T and T 2 Each independently represents a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent. Y is Y 1 Y and Y 2 Any one of the above groups represents an optionally substituted 1-valent aromatic group, and the other group represents an optionally substituted 1-valent aromatic group, a hydrogen atom, a halogen atom, or an optionally substituted 1-valent hydrocarbon group having 1 to 6 carbon atoms (the hydrocarbon group is a group other than the 1-valent aromatic group, and the-CH contained in the hydrocarbon group) 2 -optionally substituted with-O-or-CO-. ).]。

Description

Optical filter and display device
Technical Field
The present invention relates to a filter and a display device.
Background
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 being carried out. Patent document 1 describes that a squarylium compound is used in a filter for a plasma display panel, which can effectively cut off neon emission emitted from a plasma display.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2001-183522
Disclosure of Invention
Problems to be solved by the invention
The invention aims to provide a filter and a display device which are useful for a display device and the like.
Means for solving the problems
The present invention provides a filter and a display device shown below.
[ 1 ] an optical filter comprising a compound represented by the formula (I).
[ formula, R 1 ～R 4 Each independently represents a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent.
T 1 T and T 2 Each independently represents a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent.
Y 1 Y and Y 2 Any one of them represents a 1-valent aromatic optionally having a substituentA group, the other group represents a 1-valent aromatic group optionally having a substituent, a hydrogen atom, a halogen atom, or a 1-valent hydrocarbon group having 1 to 6 carbon atoms optionally having a substituent (the hydrocarbon group is a group other than the 1-valent aromatic group, and the-CH contained in the hydrocarbon group is 2 -optionally substituted with-O-or-CO-. ).]
The optical filter according to [ 2 ], which further comprises an adhesive layer,
the adhesive layer contains the compound represented by the formula (I).
The display device of [ 3 ] is a display device having the optical filter of [ 1 ] or [ 2 ] and an image display element,
the optical filter is disposed on the visible side with respect to the image display element.
The display device according to [ 4 ], which is a liquid crystal display device or an organic electroluminescent display device.
Effects of the invention
The optical filter of the present invention can be suitably used in a display device.
Drawings
Fig. 1 (a) and (b) are schematic cross-sectional views showing an example of the filter of the present invention.
Fig. 2 (a) is a schematic cross-sectional view showing an example of the organic EL display device, and (b) is a schematic cross-sectional view showing an example of the liquid crystal display device.
Detailed Description
(Compound represented by the formula (I))
The optical filter of the present invention contains a compound represented by the following formula (I) (hereinafter, sometimes referred to as "compound (I)").
[ formula, R 1 ～R 4 Each independently represents a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent.
T 1 T and T 2 Each independently represents a hydrogen atom or an optional groupA C1-6 hydrocarbon group having a substituent.
Y 1 Y and Y 2 Any one of the above groups represents an optionally substituted 1-valent aromatic group, and the other group represents an optionally substituted 1-valent aromatic group, a hydrogen atom, a halogen atom, or an optionally substituted 1-valent hydrocarbon group having 1 to 6 carbon atoms (the hydrocarbon group is a group other than the 1-valent aromatic group, and the-CH contained in the hydrocarbon group) 2 -optionally substituted with-O-or-CO-. ).]
In the compound (I), in addition to the expression represented by the formula (I), for example, a tautomer of a resonance structure represented by the following formula is present. Compound (I) is considered to comprise all tautomers.
In the formula (I), R is 1 ～R 4 Examples of the 1-valent hydrocarbon group having 1 to 6 carbon atoms include a 1-valent saturated hydrocarbon group and a 1-valent unsaturated hydrocarbon group.
Examples of the 1-valent 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, or a hexyl group; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, or neopentyl; alicyclic saturated hydrocarbon groups such as cyclopropyl, cyclopentyl, and cyclohexyl.
Examples of the 1-valent unsaturated hydrocarbon group include phenyl groups as aromatic hydrocarbon groups; an unsaturated aliphatic hydrocarbon group having 1 valence such as vinyl, propenyl, butenyl, or pentenyl; and 1-valent alicyclic unsaturated hydrocarbon groups such as cyclopropenyl, cyclopentenyl and cyclohexenyl.
In the formula (I), R is 1 ～R 4 Examples of the substituent of the 1-valent hydrocarbon group having 1 to 6 carbon atoms which may be substituted include a halogen atom, a hydroxyl group, an amino group, a nitro group, a sulfamoyl group, and a sulfo group.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
In the formula (I)As T 1 T and T 2 The optionally substituted C1-6 hydrocarbon group includes R 1 ～R 4 The hydrocarbon groups exemplified in (a).
In the formula (I), Y 1 Y and Y 2 Any one of them may be a 1-valent aromatic group optionally having a substituent, and both may be independently a 1-valent aromatic group optionally having a substituent. In Y 1 Y and Y 2 In the case where one of them is a 1-valent aromatic group, the other may be a hydrogen atom, a halogen atom or a 1-valent hydrocarbon group having 1 to 6 carbon atoms optionally having a substituent, and the-CH contained in the hydrocarbon group may be 2 -optionally substituted with-O-or-CO-.
As Y 1 Y and Y 2 Examples of the aromatic group having 1 valence and optionally having a substituent(s) include aromatic hydrocarbon group having 1 valence and optionally having a substituent(s), and aromatic heterocyclic group having 1 valence and optionally having a substituent(s). The 1-valent aromatic group may have a monocyclic structure or a condensed ring structure.
The number of carbon atoms of the 1-valent aromatic hydrocarbon group is usually 6 to 30, preferably 6 to 20, more preferably 6 to 13. Examples of the 1-valent aromatic hydrocarbon group include phenyl groups; a naphthyl group; an anthracene group; phenanthryl; pyrenyl; fluorenyl, and the like. The 1-valent aromatic hydrocarbon group includes an alkyl group substituted with hydrogen contained in the above group (the alkyl group contains-CH 2 The group optionally substituted with a hydrocarbon group such as-O-or-CO-), an aryl group or the like may be, for example, tolyl, xylyl, mesityl, propylphenyl, butylphenyl, hexylphenyl, biphenyl, terphenyl, propylbiphenyl or the like.
The number of carbon atoms of the 1-valent aromatic heterocyclic group is usually 2 to 30, preferably 4 to 20, more preferably 4 to 10.
The heteroatom of the 1-valent aromatic heterocyclic group represents a nitrogen atom, an oxygen atom, a sulfur atom, or the like. Examples of the 1-valent aromatic heterocyclic group include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, isothiazole, imidazole, pyrazole, furazan, triazole, oxadiazole, isoxazole, tetrazole, pyran, pyridine, thiopyran, pyridazine, pyrimidine, pyrazine, triazine, benzofuran, isobenzofuran, benzothiophene, indole, isoindole, indolizine, indoline, chromene (chromene), isochromene, chromane (Chromane), isochromene, benzopyran, quinoline, isoquinoline, quinolizine, benzimidazole, benzothiazole, benzothiadiazole, indazole, naphthyridine (naphthyridine), quinoxaline, quinazoline (japanese: heterocyclic compounds such as cinch, cinnoline, phthalazine, purine, pteridine, carbazole, xanthene, phenanthridine, acridine, β -carboline, perimidine, phenanthroline, thianthrene, phenoxatin, phenoxazine, phenothiazine, phenazine, and the like, from which 1 hydrogen atom is removed. The 1-valent 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 or an aryl group, and may be a group in which 1 hydrogen atom is removed from N-biphenylcarbazole, for example.
Examples of the substituent of the 1-valent aromatic group optionally having a substituent include the halogen atom described above; a hydroxyl group; an amino group; a nitro group; an aryloxy group; an arylcarbonyl group; aryloxycarbonyl; a carboxyl group; a sulfo group; a carbamoyl group; sulfamoyl, and the like.
In the formula (I), as Y 1 Y and Y 2 The C1-C6 hydrocarbon group which is not a 1-valent aromatic group and which may have a substituent may be any one of them, and examples thereof include R 1 ～R 4 The saturated hydrocarbon group of valence 1 optionally having a substituent, the unsaturated aliphatic hydrocarbon group of valence 1 optionally having a substituent, the alicyclic unsaturated hydrocarbon group of valence 1 optionally having a substituent, or the like.
the-CH contained in the hydrocarbon group 2 The group may be replaced with-O-or-CO-, and examples of such a group include-C (=O) CH 3 、-C(＝O)-OCH 2 CH 3 。
Examples of the compound (I) include compounds represented by the following formula.
The compound (I) can be used in a filter for a display device or the like. For example, by adding the compound (I) to a layer forming the filter, a filter capable of absorbing light in the vicinity of 580nm (575 to 590 nm), preferably light having a maximum absorption wavelength of 580nm, can be produced. Thus, the light transmitted through the filter sheet can improve the separability of the green light and the red light as compared with the light incident on the filter, and can be expected to improve the color purity of the green light and the red light. Therefore, by applying the filter using the compound (I) to a display device or the like, a display device with improved color purity can be obtained.
(Compound represented by the 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 the compound (I).
[ formula, R 1 ～R 4 Each independently represents a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent.
T 1 T and T 2 Each independently represents a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent.
X 1 X is X 2 Any one of the groups (a) represents any group selected from group A, and the other represents any group selected from group A, a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent (the hydrocarbon group is a group other than a 1-valent aromatic group, and the-CH contained in the hydrocarbon group) 2 -optionally substituted with-O-or-CO-. ).
Group a: comprising halogen atoms, borate groups, and-B (OH) 2 Is a group of (a).]
In the compound (II), in addition to the expression represented by the formula (II), for example, a tautomer of a resonance structure represented by the following formula is present. Compound (II) is considered to comprise all tautomers.
In the formula (II), R is 1 ～R 4 、T 1 T and T 2 The optionally substituted C1-6 hydrocarbon group may be the above-mentioned hydrocarbon group.
In the formula (II), X 1 X is X 2 Any one of the groups (a) represents any group selected from group a, or both groups may be any group selected from group a. At X 1 X is X 2 In the case where one of the groups is any group selected from group A, the other group may be a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent, and the group may be-CH contained in the hydrocarbon group 2 -optionally substituted with-O-or-CO-.
In the formula (II), the halogen atom in the group a may be the halogen atom described above.
As X 1 X is X 2 Examples of the borate group include groups represented by the following formula. In the following formula, the term "bond terminal".
In the formula (II), X is 1 X is X 2 The C1-C6 hydrocarbon group which is not a 1-valent aromatic group and which may have a substituent may be any one of them, and examples thereof include R 1 ～R 4 Examples of the unsaturated hydrocarbon group include a 1-valent saturated hydrocarbon group, a 1-valent unsaturated aliphatic hydrocarbon group, and a 1-valent alicyclic unsaturated hydrocarbon group.
the-CH contained in the hydrocarbon group 2 The radical is optionally replaced by-O-or-CO-, examples of which include-C (=O) CH 3 、-C(＝O)-OCH 2 CH 3 。
Examples of the compound (II) include compounds represented by the following formula.
(production method of Compound (I) [1 ])
For Y in the compound (I) 1 Y and Y 2 The method for producing a compound (hereinafter, referred to as "compound (Ia)") in which both are optionally substituted 1-valent aromatic groups will be described.
[ in the above-mentioned, a method for producing a semiconductor device,
R 1 ～R 4 each independently represents a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent.
T 1 T and T 2 Each independently represents a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent.
Y 1a Y and Y 2a Each independently represents a 1-valent aromatic group optionally having a substituent.]
In the formula (Ia), for R 1 ～R 4 、T 1 T and T 2 The optionally substituted C1-6 hydrocarbon group may be the above-mentioned hydrocarbon group.
For Y in formula (Ia) 1a Y and Y 2a Examples of the optionally substituted 1-valent aromatic group include Y in the above formula (I) 1 Y and Y 2 Illustrative examples of the 1-valent aromatic group optionally having a substituent are shown.
The method for producing the compound (Ia) may include a step of reacting the compound represented by the formula (IIa), the compound represented by the formula (III-1 a), and the compound represented by the formula (III-2 a) in the presence of a nickel catalyst or a palladium catalyst.
[ in the above-mentioned, a method for producing a semiconductor device,
R 1 ～R 4 meaning the same as above.
T 1 T and T 2 Meaning the same as above.
X 1a X is X 2a Each independently represents any group selected from group a.
Group a: comprising halogen atoms, borate groups, and-B (OH) 2 Is a group of (a).]
Y 1a -Z 1 (III-1a)
Y 2a -Z 2 (III-2a)
[ formula (III-la) and formula (III-2 a),
Y 1a Y and Y 2a Meaning the same as above.
Z 1 Z is as follows 2 Each independently represents a halogen atom, a borate group, -B (OH) 2 An alkyl sulfonate group, or an aryl sulfonate group.]
In the formula (IIa), for R 1 ～R 4 、T 1 T and T 2 The optionally substituted C1-6 hydrocarbon group may be the above-mentioned hydrocarbon group.
For X in formula (IIa) 1a X is X 2a Examples of the halogen atom and the borate group in the group A include the above-mentioned ones.
In the formula (III-1 a) and the formula (III-2 a), Z is as follows 1 Z is as follows 2 Examples of the halogen atom and the borate group include the above-mentioned ones.
As Z 1 Z is as follows 2 Examples of the alkylsulfonate group include a 1-6 carbon alkylsulfonate group optionally having a halogen atom such as a methanesulfonate group, an ethanesulfonate group, and a trifluoromethanesulfonate group. As the halogen atom, the halogen atom exemplified above can be exemplified.
As Z 1 Z is as follows 2 Examples of the arylsulfonate group include a benzenesulfonate group, a p-toluenesulfonate group and a benzylsulfonate groupAnd aryl sulfonate groups with 6-18 carbon atoms.
Z 1 Z is as follows 2 Preferably each independently is a halogen atom, a borate group, or-B (OH) 2 。
Examples of the compound represented by the formula (IIa) include compounds represented by the following formula.
Examples of the compounds represented by the formulae (III-1 a) and (III-2 a) include 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol, 3,4, 5-trimethoxyphenylboronic acid, 4-hexylphenylboronic acid, 4- (dimethylamino) phenylboronic acid, 4- (diphenylamino) phenylboronic acid, 4' -propyl-4-biphenylboronic acid, 6-ethoxy-2-naphthalene boronic acid, 9-dimethylfluorene-2-boronic acid, benzo [ b ] thiophene-2-boronic acid, 9-ethylcarbazole-3-boronic acid, 9- (4-biphenylyl) carbazole-3-boronic acid pinacol ester, 4-tert-butylphenylboronic acid, 4-methoxy-3, 5-dimethylphenylboronic acid, 4-carboxyphenylboronic acid pinacol ester, 1-thianthrenylboronic acid (Japanese text: 1-copy system ii acid), 4-methyl-naphthalene-boronic acid, and the like.
In the step of producing the compound (Ia), a method of coupling the compound of the formula (IIa), the compound of the formula (III-1 a), and the compound of the formula (III-2 a) in the presence of a palladium catalyst or in the presence of a nickel catalyst is preferable, and a coupling method in the presence of a palladium catalyst is most preferable.
Examples of the palladium catalyst include tetrakis (triphenylphosphine) palladium (0), tris (dibenzylideneacetone) dipalladium (0), palladium (II) acetate, bis (triphenylphosphine) palladium (II) dichloride, and potassium hexachloropalladium (IV) acetate.
Examples of the nickel catalyst include tetrakis (triphenylphosphine) nickel (0), [ bis (1, 5-cyclooctadiene) ] nickel (0), [1, 3-bis (diphenylphosphino) propane ] nickel (II) dichloride, bis (2, 4-pentanedionate) nickel (II), bis (triphenylphosphine) nickel (II) dichloride, and nickel (II) halide.
The amount of the palladium catalyst or the nickel catalyst to be 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-1 a) to be used is preferably 1 mol or more and 5 mol or less, more preferably 1.1 mol or more and 3 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-2 a) to be used is preferably 1 mol or more and 5 mol or less, more preferably 1.1 mol or more and 3 mol or less, based on 1 mol of the compound represented by the formula (IIa).
The reaction temperature is preferably 30℃to 180℃and more preferably 80℃to 140 ℃. The reaction time is preferably 1 to 20 hours, more preferably 3 to 15 hours.
From the viewpoint of yield, the reaction is preferably carried out in an organic solvent. Examples of the organic solvent include aromatic hydrocarbon solvents such as toluene and xylene; hydrocarbon solvents such as hexane, cyclohexane and decalin, and ether solvents such as tetrahydrofuran, 1, 4-dioxane and dimethoxyethane; halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, chloroform, etc.; alcohol solvents such as methanol, ethanol, isopropanol, butanol, etc.; nitrohydrocarbon solvents such as nitrobenzene; ketone solvents such as methyl isobutyl ketone; amide solvents such as N, N-dimethylformamide and 1-methyl-2-pyrrolidone; etc., they may be used in combination. Among them, tetrahydrofuran is preferred. Further, the reaction may be carried out in a 2-phase system or a mixed system with water, such as a coupling reaction using a palladium catalyst. The amount of the organic solvent 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, based on 1 part by mass of the compound represented by the formula (IIa).
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-la) and the compound represented by the formula (III-2 a). The base is preferably a base that is sufficiently soluble in the solvent used in the reaction. Examples of the base include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, and tripotassium phosphate; organic bases such as butyllithium, potassium t-butoxide, sodium methoxide, sodium ethoxide, tetrabutylammonium fluoride, tetrabutylammonium chloride, tetrabutylammonium bromide, tetraethylammonium hydroxide, and tetrabutylammonium hydroxide. Examples of the method of mixing the alkali include a method of adding a solution of the alkali while stirring the reaction solution under an inert atmosphere such as argon or nitrogen; and a method of adding the reaction solution to a solution of a base.
The amount of the base to be used is preferably 2 to 20 moles based on 1 mole of the compound represented by the formula (IIa).
The method for obtaining the compound (Ia) as the target compound from the reaction mixture is not particularly limited, and various known methods can be employed. For example, a method of collecting precipitated crystals by filtration after cooling may be mentioned. The crystals collected by filtration are preferably washed with water or the like, and then dried. Further, if necessary, the purified product may be purified by a known method such as recrystallization and column chromatography.
(production method of Compound (I) [2 ])
For Y in the compound (I) 1 Is an aromatic group of 1 valence optionally having a substituent, Y 2 Is a hydrogen atom or a C1-6 hydrocarbon group (the hydrocarbon group is a group other than a 1-valent aromatic group, and the-CH contained in the hydrocarbon group) 2 -optionally substituted with-O-or-CO-. ) The method for producing the compound (hereinafter, sometimes referred to as "compound (Ib)") represented by the following formula (Ib) will be described.
[ in the above-mentioned, a method for producing a semiconductor device,
R 1 ～R 4 each independently represents a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent.
T 1 T and T 2 Each independently represents a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent.
Y 1b Represents an aromatic group having a valence of 1 and optionally having a substituent.
X 2b Represents a hydrogen atom or a C1-6 hydrocarbon group (the hydrocarbon group is a group other than a 1-valent aromatic group, and the-CH contained in the hydrocarbon group) 2 -optionally substituted with-O-or-CO-. ).]
In the formula (Ib), for R 1 ～R 4 、T 1 T and T 2 Examples of the "C1-6 1 valent hydrocarbon group" which may have a substituent(s) include R in the above formula (I) 1 ～R 4 The hydrocarbon groups exemplified in (a).
In the formula (Ib), for Y 1b Examples of the optionally substituted 1-valent aromatic group include Y in the above formula (I) 1 Y and Y 2 The radicals exemplified in (a).
In the formula (Ib), for X 2b Examples of the "C1-6 1 valent hydrocarbon group" which may have a substituent(s) include R in the above formula (I) 1 ～R 4 The hydrocarbon groups exemplified in (a).
The method for producing the compound (Ib) may include a step of reacting the compound represented by the formula (IIb) with the compound represented by the formula (III-1 b) in the presence of a nickel catalyst or a palladium catalyst.
[ in the above-mentioned, a method for producing a semiconductor device,
R 1 ～R 4 meaning the same as above.
T 1 T and T 2 Meaning the same as above.
X 1b Represents any group selected from group A.
Group a: comprising halogen atoms, borate groups, and-B (OH) 2 Is a group of (a).
X 2b Meaning the same as above.]
Y 1b -Z 1 (III-1b)
[ in the above-mentioned, a method for producing a semiconductor device,
Y 1b meaning the same as above.
Z 1 Represents a halogen atom, a borate group, -B (OH) 2 An alkyl sulfonate group, or an aryl sulfonate group.]
In the formula (IIb) and the formula (III-1 b), R is 1 ～R 4 、T 1 T and T 2 、X 2b Examples of the "C1-6 1 valent hydrocarbon group" which may have a substituent(s) include R in the above formula (I) 1 ～R 4 The hydrocarbon groups exemplified in (a).
In the formula (IIb) and the formula (III-1 b), for Y 1b Examples of the optionally substituted 1-valent aromatic group include Y in the above formula (I) 1 Y and Y 2 The radicals exemplified in (a).
In the formula (IIb), for X 1b Examples of the halogen atom and the borate group include the above-mentioned ones.
Examples of the compound represented by the formula (IIb) include compounds represented by the following formula.
As the compound represented by the formula (III-1 b), there may be mentioned compounds exemplified by the compounds represented by the above-mentioned formulas (III-1 a) and (III-2 a).
In the step of producing the compound (Ib), a method of coupling the compound represented by the formula (IIb) with the compound represented by the formula (III-1 b) in the presence of a palladium catalyst or in the presence of a nickel catalyst is preferable, and a coupling method in the presence of a palladium catalyst is most preferable. The palladium catalyst and the nickel catalyst may be the above-mentioned catalysts.
The amount of the compound represented by the formula (III-1 b) to be used is preferably 1 mol or more and 5 mol or less, more preferably 1.1 mol or more and 3 mol or less, based on 1 mol of the compound represented by the formula (IIb).
The amount of the palladium catalyst or the nickel catalyst to be used 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 30℃to 180℃and more preferably 80℃to 140 ℃. The reaction time is preferably 1 to 20 hours, more preferably 3 to 15 hours.
From the viewpoint of yield, the reaction is preferably carried out in an organic solvent. As the organic solvent, the solvents exemplified above can be exemplified. The amount of the organic solvent 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, based on 1 part by mass of the compound represented by the formula (IIb).
The method for obtaining the compound (Ib) as the target compound from the reaction mixture is not particularly limited, and various known methods can be employed, and examples thereof include the above-mentioned methods.
(production method of Compound (I) [3 ])
The method for producing the compound (I) may include a step of reacting a squaric acid (3, 4-dihydroxy-3-cyclobutene-1, 2-dione) represented by the following formula (IV) or a compound represented by the following formula (IV-1) (hereinafter, sometimes 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, sometimes referred to as a "pyrrole compound (V2)").
[ formula (IV-1), formula (V1) and formula (V2),
R 1 ～R 4 meaning the same as above.
Y 1 Y and Y 2 Any one of the above groups represents an optionally substituted 1-valent aromatic group, and the other group represents an optionally substituted 1-valent aromatic group, a hydrogen atom, a halogen atom, or an optionally substituted 1-valent hydrocarbon group having 1 to 6 carbon atoms (the hydrocarbon group is a group other than the 1-valent aromatic group, and the-CH contained in the hydrocarbon group) 2 -optionally substituted with-O-or-CO-. ).
T 1 T and T 2 Meaning the same as above.
R 11 R is R 12 Each independently represents an alkyl group having 1 to 4 carbon atoms.]
In the formula (V1) and the formula (V2), R is 1 ～R 4 、T 1 T and T 2 The optionally substituted C1-6 hydrocarbon group may be the above-mentioned hydrocarbon group.
In the formula (V1) and the formula (V2), for Y 1 Y and Y 2 Examples of the aromatic group having 1 valence and optionally having a substituent, a halogen atom, and a hydrocarbon group having 1 to 6 carbon atoms and optionally having a substituent include the above-mentioned examples.
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 of dehydrating and condensing the squaric acid, the pyrrole compound (V1), and the pyrrole compound (V2) in an organic solvent is preferable. The organic solvent may be any of the solvents 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 preferably 0.45 mol or more and 0.6 mol or less, more preferably 0.47 mol or more and 0.51 mol or less, based on 1 mol of the total of the pyrrole compound (V1) and the pyrrole compound (V2).
The amount of the azole compound (V2) to be used is preferably 1 mol or more and 1.5 mol or less based on 1 mol of the azole compound (V1).
The reaction of the compound represented by the formula (IV) or the compound (IV-1) with the pyrrole compound (V2) is carried out by mixing the compound represented by the formula (IV) or the compound (IV-1) with the pyrrole compound (V2). In the reaction, the compound represented by the formula (IV) or the compound (IV-1) and the pyrrole compound (V1) may be reacted together with the pyrrole compound (V2). The method of mixing the compound of formula (IV) or the compound (IV-1) with the pyrrole compound (1) and then mixing the pyrrole compound (2) may be performed, or the method of mixing the compound of formula (IV) or the compound (IV-1) with the pyrrole compound (2) and then mixing the pyrrole compound (1) may be performed.
The reaction temperature is preferably 30℃to 180℃and more preferably 80℃to 140 ℃. The reaction time is preferably 1 to 20 hours, more preferably 3 to 15 hours.
From the viewpoint of yield, the reaction is preferably carried out in an organic solvent. As the organic solvent, the solvents exemplified above can be exemplified. The amount of the organic solvent 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, relative to 1 part by mass of the squaric acid.
The method for obtaining the compound (I) as the target compound from the reaction mixture is not particularly limited, and various known methods can be employed, and examples thereof include the above-mentioned methods.
The azole compound (V1) can be produced, for example, by reacting the following formula (V1 ') (hereinafter, sometimes referred to as "azole compound (V1')") with a halogenating agent, and then reacting the reaction product with a compound represented by the following formula (III-1) (hereinafter, sometimes referred to as "compound (III-1)"). The azole compound (V2) can be produced, for example, by reacting a compound represented by the following formula (V2 ') (hereinafter, sometimes referred to as "azole compound (V2')") with a halogenating agent, and then reacting the reaction product with a compound represented by the following formula (III-2) (hereinafter, sometimes referred to as "compound (III-2)"). In order to react the compound (III-1) and the compound (III-2) at desired positions, (V1 ') and (V2') may have a protecting group such as an ethoxycarbonyl group at a position where the reaction is not intended, and deprotection may be performed after the reaction, whereby the desired azole compound (V1) and azole compound (V2) can be produced.
[ formula (V1 ') and formula (V2'),
R 1 ～R 4 meaning the same as above.
T 1 T and T 2 Meaning the same as above.]
For R in formula (V1 ') and formula (V2') 1 ～R 4 、T 1 T and T 2 The optionally substituted C1-6 hydrocarbon group may be the above-mentioned hydrocarbon group.
Y 1 -Z 1 (III-1)
Y 2 -Z 2 (III-2)
[ in the formula (III-1) and the formula (III-2),
Y 1 y and Y 2 Meaning the same as above.
Z 1 Z is as follows 2 Each independently represents a halogen atom, a borate group, -B (OH) 2 An alkyl sulfonate group, or an aryl sulfonate group.]
In the formula (III-1) and the formula (III-2), for Y 1 Y and Y 2 Examples of the aromatic group having 1 valence and optionally having a substituent, a halogen atom, and a hydrocarbon group having 1 to 6 carbon atoms and optionally having a substituent include the above-mentioned examples.
In the formula (III-1) and the formula (III-2), for Z 1 Z is as follows 2 Examples of the halogen atom, borate group, alkylsulfonate group, or arylsulfonate group include the above.
The pyrrole compound (V1 ') and the pyrrole compound (V2') include, for example, 2, 4-dimethylpyrrole.
Examples of the compound (III-1) and the compound (III-2) include 4-hexylphenylboronic acid.
Examples of the halogenating agent include N-fluoro-succinimide (NFS), N-chloro-succinimide (NCS), N-bromo-succinimide (NBS), N-iodo-succinimide (NIS), N-chlorophthalimide, N-chlorodiethylamine, N-chlorodibutylamine, N-chlorocyclohexylamine, chlorine, iodine trichloride, aluminum trichloride, tellurium (IV) chloride, molybdenum chloride, antimony chloride, iron (III) chloride, titanium tetrachloride, phosphorus pentachloride, thionyl chloride, N-bromophthalimide, N-bromobis (trifluoromethyl) amine, bromine, 1, 2-dibromoethane, boron tribromide, copper bromide, silver bromide, bromotertiary butane, bromine oxide, and the like, and N-halosuccinimide is preferable.
In the step of producing the pyrrole compound (V1) and the pyrrole compound (V2), the reaction product obtained by reacting the pyrrole compound (V1 ') or the pyrrole compound (V2') with the halogenating agent is preferably a method of coupling in the presence of a palladium catalyst or a nickel catalyst, and most preferably a coupling method in the presence of a palladium catalyst. Examples of the palladium catalyst and the nickel catalyst include the catalysts described above.
When the pyrrole compound (V1 ') or the reaction product of the pyrrole compound (V2') and the halogenating agent, the reaction with the compound (III-1) or the compound (III-2) are carried out in the presence of a palladium catalyst and the substituent to be introduced into the reaction product from the halogenating agent is a halogen atom, Z of the compound (III-1) 1 Or Z of the compound (III-2) 2 Preferably each independently is a borate group or-B (OH) 2 . Z is Z when the above reaction is performed in the presence of a nickel catalyst and the substituent introduced into the reaction product from the halogenating agent is a halogen atom 1 Z is as follows 2 Preferably each independently is a halogen atom. In addition, the above reaction is carried out in the presence of a palladium catalyst, and the substituent introduced into the reaction product from the halogenating agent is converted into a borate group or-B (OH) by a conventional method 2 When Z is 1 Z is as follows 2 Preferably each independently is an alkyl sulfonate group or an aryl sulfonate group.
The reaction of the pyrrole compound (V1 ') or the pyrrole compound (V2') with the halogenating agent is preferably 1 mol or more and 5 mol or less, more preferably 1.05 mol or more and 3 mol or less, based on 1 mol of the pyrrole compound (V1 ') or the pyrrole compound (V2').
The reaction temperature is preferably-80℃to the boiling point of the solvent. The reaction time is preferably 1 to 20 hours, more preferably 3 to 15 hours.
From the viewpoint of yield, the reaction is preferably carried out in an organic solvent. As the organic solvent, the solvents exemplified above can be exemplified. 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 or less, based on 1 part by mass of the azole compound (V1 ') or the azole compound (V2').
The method for obtaining the reaction product of the pyrrole compound (V1 ') or the pyrrole compound (V2') as the target compound and the halogenating agent from the reaction mixture is not particularly limited, and various known methods can be employed, and examples thereof include the above-mentioned methods.
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 preferably 1 mol or more and 5 mol or less, more preferably 1.1 mol or more and 3 mol or less, based on 1 mol of the pyrrole compound (V1').
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) to be used is preferably 1 mol or more and 5 mol or less, more preferably 1.1 mol or more and 3 mol or less, based on 1 mol of the pyrrole compound (V2').
The reaction temperature is preferably 30℃to 180℃and more preferably 80℃to 140 ℃. The reaction time is preferably 1 to 20 hours, more preferably 3 to 15 hours.
The method for obtaining the pyrrole compound (V1) or the pyrrole compound (V2) as the target compound from the reaction mixture is not particularly limited, and various known methods can be employed, for example, the above-mentioned methods can be employed.
(production method of Compound (I) [4 ])
For Y in the compound (I) 1 Is an aromatic group of 1 valence optionally having a substituent, Y 2 A method for producing a compound (hereinafter, sometimes referred to as "compound (Ic)") when it is a halogen atom will be described.
The compound (Ic) can be obtained by reacting X with the compound represented by the above formula (Ib) 2b Is a compound of hydrogen atomsIn the object to the X 2b The hydrogen atom shown is halogenated. For example, halogenation can be carried out using the halogenating agents described above.
(production method of Compound (II) (1))
For the production method of the compound (II), for example, X in the case where the compound (II) is the formula (II) 1 X is X 2 In the case of a compound which is a halogen atom (hereinafter sometimes referred to as "compound (IIc)") may include: a step of reacting the squaric acid represented by the formula (IV) with the pyrrole compound (V1 ') and the pyrrole compound (V2') to obtain a compound represented by the following formula (II ') (hereinafter referred to as "compound (II')"); and a step of reacting the compound (II') with a halogenating agent to obtain the compound (IIc).
[ in the above-mentioned, a method for producing a semiconductor device,
R 1 ～R 4 each independently represents a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent.
T 1 T and T 2 Each independently represents a hydrogen atom or a C1-6 hydrocarbon group optionally having a substituent.]
In the formula (II'), for R 1 ～R 4 、T 1 T and T 2 The optionally substituted C1-6 hydrocarbon group may be the above-mentioned hydrocarbon group.
Examples of the halogenating agent include the above halogenating agents.
Examples of the compound (II') include compounds represented by the following formula.
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The amount of squaric acid used in the step of reacting squaric acid with the pyrrole compound (V1 ') and the pyrrole compound (V2') is preferably 0.45 mol or more and 0.6 mol or less, more preferably 0.47 mol or more and 0.51 mol or less, based on 1 mol of the total of the pyrrole compound (V1 ') and the pyrrole compound (V2').
The amount of the azole compound (V2 ') to be used is preferably 1 mol or more and 1.5 mol or less based on 1 mol of the azole compound (V1').
The reaction temperature is preferably 30℃to 180℃and more preferably 80℃to 140 ℃. The reaction time is preferably 1 to 20 hours, more preferably 3 to 15 hours.
From the viewpoint of yield, the reaction is preferably carried out in an organic solvent. As the organic solvent, the solvents exemplified above can be used. The amount of the organic solvent 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, relative to 1 part by mass of the total of the azole compound (V1 ') and the azole compound (V2').
The method for obtaining the compound (II') as the target compound from the reaction mixture is not particularly limited, and various known methods can be employed, and for example, the above-mentioned methods can be used.
For the reaction of the compound (II ') with the halogenating agent, the halogenating agent is preferably 2 mol or more and 6 mol or less, more preferably 2.2 mol or more and 5 mol or less, relative to 1 mol of the compound (II').
The reaction temperature is preferably-80℃to the boiling point of the solvent. The reaction time is preferably 1 to 20 hours, more preferably 3 to 15 hours.
From the viewpoint of yield, the reaction is preferably carried out in an organic solvent. As the organic solvent, the solvents exemplified above can be used. The amount of the organic solvent 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, based on 1 part by mass of the compound (II').
The method for obtaining the compound (IIc) as the target compound from the reaction mixture is not particularly limited, and various known methods can be employed, for example, the above-mentioned methods can be used.
(production method (2) of Compound (II))
In the method for producing the compound (II), X in the formula (II) is the compound (II) 1 X is X 2 Is a borate group or-B (OH) 2 In the case of the compound (hereinafter sometimes referred to as "compound (IId)"), for example, the compound (IIc) [ X in the formula (II) ") can be mentioned 1 X is X 2 Compounds being halogen atoms]A method of preparing a Grignard intermediate by reacting with a magnesium platelet, and allowing 2-isopropoxy-4, 5-tetramethyl-1, 3, 2-dioxaborane or the like to act on the Grignard intermediate; a method for boric acid esterification by reacting the compound (IIc) with bis (pinacolato) diboron in the presence of a base using a palladium catalyst; and a method in which the reaction is carried out by subjecting trimethoxyborane, triisopropoxyborane, or the like to hydrolysis to carry out boration.
(optical filter)
The optical filter of the present invention contains the compound (I), and the optical filter of the present invention can be used in a display device or the like. The optical filter is typically a layer having light transmittance (preferably optically transparent) formed of a composition containing a thermoplastic resin or a thermosetting resin, for example, a material capable of being made into a film. The filter may have a layer containing the compound (I) (hereinafter, sometimes referred to as "color correction layer") and may be a color correction film formed of a single-layer structure of the color correction layer, or may be a laminate having a multilayer structure containing the color correction layer. When the filter has a multilayer structure, 1 color correction layer may be included, or 2 or more color correction layers may be included, and the compounds (I) contained in the 2 or more layers may be the same or different from each other.
When the 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, 2 layers included in the filter may be bonded to each other, or the filter may be bonded to another member such as an image display element. The adhesive layer may be an adhesive layer formed of an adhesive composition, or a layer formed of an adhesive composition and an adhesive composition.
In the case where the color correction layer is a filter (color correction film) having a single layer structure or in the case where the filter having a multilayer structure is a resin layer other than an adhesive layer, the method of containing the compound (I) in the color correction film or the resin layer is not particularly limited. For example, a method of kneading [ i ] with a resin for forming a color correction film or a resin layer and heating to form a film; [ ii ] A method of dispersing or dissolving a resin forming a color correction film or a resin layer or a monomer of the resin and a compound (I) in an organic solvent, and forming the dispersion into a film by a casting method or the like. Further, the compound (I) may be dispersed or dissolved in a binder resin or an organic solvent, the resulting coating liquid may be applied to a resin base film to form a resin layer, the resin base film may be peeled from the resin layer, and the resulting film may be a color correction film. The thickness of the color correction film or the resin layer is not particularly limited, and may be, for example, 1 μm to 200 μm.
In the case where the color correction film or the resin layer contains the compound (I), the content thereof is not particularly limited. For example, the compound (I) may be set to 0.001 part by mass or more, preferably 0.02 part by mass or more, more preferably 0.05 part by mass or more, and 10 parts by mass or less, preferably 3 parts by mass or less, more preferably 0.5 part by mass or less, based on 100 parts by mass of the base polymer forming the color correction film or the resin layer.
In the case where the color correction layer is an adhesive layer, the method for containing the compound (I) in the adhesive layer is not particularly limited, and the compound (I) may be added when preparing an adhesive composition or an adhesive composition for forming the adhesive layer. The thickness of the adhesive layer is not particularly limited, and may be, for example, 1 μm to 100 μm.
In the case where the adhesive layer contains the compound (I), the content thereof is not particularly limited either. For example, the compound (I) may be set to 0.01 part by mass or more, preferably 0.02 part by mass or more, more preferably 0.05 part by mass or more, and further, 10 parts by mass or less, preferably 5 parts by mass or less, more preferably 0.5 parts by mass or less, relative to 100 parts by mass of the base polymer forming the adhesive composition and/or the adhesive composition contained in the adhesive layer.
The optical filter can be used in a display device such as an organic electroluminescence (organic EL) display device or a liquid crystal display device, and can be attached to the visible side of an image display element of the display device. In this case, the 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 filter is a laminate, the laminate structure is not particularly limited, and may have, for example, the laminate structure shown in fig. 1 (a) and (b). Fig. 1 (a) and (b) are schematic cross-sectional views showing an example of the filter. The filter 10 shown in fig. 1 (a) can be used in an organic EL display device. The filter 10 may include, for example, an adhesive layer 11 for an image display element, a phase difference film 12, an adhesive layer 13, a 1 st protective film 14, a polarizing film 15, and a 2 nd protective film 16 in this order. The pressure-sensitive adhesive layer 11 and the pressure-sensitive adhesive layer 13 for the image display element each correspond to the above-described adhesive layer, and the retardation film 12, the 1 st protective film 14, the polarizing film 15, and the 2 nd protective film 16 each correspond to the above-described resin layer.
The 1 st protective film 14, the polarizing film 15, and the 2 nd protective film 16 in the filter 10 form a polarizing plate, and the 1 st protective film 14 and the 2 nd protective film 16 may have an adhesive layer on the side of the bonding surface with the polarizing film 15. The adhesive layer 11 for an image display element is used for bonding to a light-emitting layer including an organic EL element as an image display element of an organic EL display device. A spacer (release film) not shown may be provided on the side of the pressure-sensitive adhesive layer 11 for image display element opposite to the retardation film 12.
The filter 20 shown in fig. 1 (b) may be used in a liquid crystal display device. The filter 20 may include, for example, an adhesive layer 21 for an image display element, a 1 st protective film 24, a polarizing film 25, and a 2 nd protective film 26 in this order. The pressure-sensitive adhesive layer 21 for an image display element corresponds to the adhesive layer, and the 1 st protective film 24, the polarizing film 25, and the 2 nd protective film 26 each correspond to the resin layer.
The 1 st protective film 24, the polarizing film 25, and the 2 nd protective film 26 in the filter 20 form a polarizing plate, and the 1 st protective film 24 and the 2 nd protective film 26 may have an adhesive layer on the side of the bonding surface with the polarizing film 25. The pressure-sensitive adhesive layer 21 for an image display element is used for bonding to a liquid crystal cell that is an image display element of a liquid crystal display device. A spacer (release film) not shown may be provided on the surface of the pressure-sensitive adhesive layer 21 for image display element opposite to the 1 st protective film 24.
The compound (I) may be contained in at least any one of the resin layers and the adhesive layers forming the filters 10 and 20 shown in fig. 1 (a) and (b). In the filter 10 shown in fig. 1 (a), for example, the compound (I) may be contained in 1 or more of the pressure-sensitive adhesive layer 11, the pressure-sensitive adhesive layer 13, the 1 st protective film 14, and the 2 nd protective film 15 for an image display element. In the filter 20 shown in fig. 1 (b), for example, the compound (I) may be contained in 1 or more of the pressure-sensitive adhesive layer 21 for an image display element, the 1 st protective film 24, and the 2 nd protective film 25.
The filters 10 and 20 shown in fig. 1 (a) and (b) are merely examples, and may have a laminated structure other than the above. For example, the 2 nd protective films 16 and 26 may have more layers such as a film having an antiglare function, a film having an antireflection function, and the like on the surface opposite to the polarizing films 15 and 25. The 1 st protective films 15 and 25 may have a function as a retardation film, and the 2 nd protective films 16 and 26 may have an antiglare function, a surface reflection preventing function, a function as a retardation film, and the like. In addition, a color correction layer containing the compound (I) may be provided at an arbitrary position in addition to the layers forming the filters 10 and 20 shown in fig. 1 (a) and (b).
The filter described above contains the compound (I) and is therefore capable of absorbing light in the vicinity of 580nm (575 to 590 nm) (preferably light having a maximum absorption wavelength of 580 nm). Thus, by stacking the above-described filter on the visible side of the image display element of the display device, light having an absorption wavelength in a wavelength region in the vicinity of 580nm (575 to 590 nm) can be absorbed from the light entering the filter, and the color purity of the light transmitted through the filter can be improved as compared with the light entering the filter. In the conventional display device using no filter as described above, the separability of green light and red light is insufficient, and in the display device using the filter as described above, improvement of the separability of green light and red light can be expected.
Hereinafter, each member forming the 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 aqueous adhesive include an aqueous polyvinyl alcohol resin solution and an aqueous two-part urethane emulsion adhesive. The active energy ray-curable adhesive is an adhesive cured by irradiation with active energy rays such as ultraviolet rays, and examples thereof include adhesives containing a polymerizable compound and a photopolymerization initiator, adhesives containing a photoreactive resin, adhesives containing a binder resin and a photoreactive crosslinking agent, and the like. 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 active species such as neutral radicals, anionic radicals, and cationic radicals generated by irradiation with active energy rays such as ultraviolet rays. In the present specification, the term "(meth) acrylic" means "at least 1 of acrylic and methacrylic".
As the adhesive composition that can be used for the adhesive layer, conventionally known adhesive compositions can be used. Examples of the adhesive composition include (meth) acrylic adhesives, urethane adhesives, silicone adhesives, polyester adhesives, polyamide adhesives, polyether adhesives, fluorine adhesives, and rubber adhesives. In addition, an energy ray curable adhesive, a thermosetting adhesive, or the like may be used. Among them, a (meth) acrylic adhesive is preferably used from the viewpoints of transparency, adhesion, reliability, and the like.
The acrylic pressure-sensitive adhesive is not particularly limited, but a polymer (containing 50 mass% or more) containing (meth) acrylic acid ester as a main component may be a homopolymer of 1 kind of (meth) acrylic acid ester or a copolymer of (meth) acrylic acid ester and other (meth) acrylic acid ester. Examples of the (meth) acrylic acid ester include butyl (meth) acrylate, ethyl (meth) acrylate, methyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, and 2-phenoxyethyl (meth) acrylate. In addition, the polar monomer may be copolymerized in a polymer mainly composed of these (meth) acrylic esters. Examples of the polar monomer include monomers having a polar functional group such as a carboxyl group, a hydroxyl group, an amide group, an amino group, and an epoxy group, such as 2-hydroxypropyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, acrylamide, 2- (N, N-dimethylamino) ethyl (meth) acrylate, and glycidyl (meth) acrylate. The (meth) acrylic resin used for the acrylic adhesive may be a (meth) acrylic resin having a weight average molecular weight (Mw) of 10 ten thousand or more, preferably 60 ten thousand or more, and usually 250 ten thousand or less.
These acrylic adhesives may also be used alone, however, are generally used in combination with a crosslinking agent. Examples of the crosslinking agent include a crosslinking agent which is a 2-valent or polyvalent metal ion and which forms a metal carboxylate between the metal ion and the carboxyl group; a crosslinking agent which is an amine compound and forms an amide bond with a carboxyl group; a crosslinking agent which is an epoxy compound, a diol compound, and forms an ester bond with a carboxyl group; and a crosslinking agent which is an isocyanate compound and forms an amide bond with a carboxyl group. Among them, an isocyanate compound is preferably used.
Among the isocyanate-based compounds, xylylene diisocyanate, toluene diisocyanate or hexamethylene diisocyanate is preferably used; adducts obtained by reacting these isocyanate compounds with polyhydric alcohols such as glycerin and trimethylolpropane; a compound obtained by preparing these isocyanate compounds into dimers, trimers or the like, or a mixture thereof; a mixture of 2 or more of the above-mentioned isocyanate compounds, and the like.
Examples of suitable isocyanate compounds include toluene diisocyanate, an adduct obtained by reacting a polyol with toluene diisocyanate, a dimer of toluene diisocyanate, a trimer of toluene diisocyanate, and hexamethylene diisocyanate, an adduct obtained by reacting a polyol with hexamethylene diisocyanate, a dimer of hexamethylene diisocyanate, and a trimer of hexamethylene diisocyanate.
The content of the crosslinking agent in the acrylic pressure-sensitive adhesive is usually 0 part by mass or more and 5 parts by mass or less, preferably 0.05 part by mass or more and 2 parts by mass or less, relative to 100 parts by mass of the (meth) acrylic resin.
The acrylic adhesive may further contain a silane compound. When the acrylic pressure-sensitive adhesive contains a silane compound, the adhesion between the pressure-sensitive adhesive layer obtained and an optical member such as a glass substrate can be improved.
Examples of the silane compound include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyl trimethoxysilane, 3-glycidoxypropyl methyldimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyl trimethoxysilane, 3-mercaptopropyl trimethoxysilane, 3-glycidoxypropyl triethoxysilane, 3-glycidoxypropyl dimethoxysilane, 3-glycidoxypropyl ethoxydimethylsilane, and 3-glycidoxypropyl ethoxydimethylsilane. More than 2 silane compounds may be used.
The silane compound may be a silicone oligomer type silane compound. When the silicone oligomer is represented as a (monomeric) oligomer, examples thereof include 3-mercaptopropyl trimethoxysilane-tetramethoxysilane copolymer, mercaptomethyl trimethoxysilane-tetramethoxysilane copolymer, 3-glycidoxypropyl trimethoxysilane-tetramethoxysilane copolymer, 3-methacryloxypropyl trimethoxysilane-tetramethoxysilane copolymer, 3-acryloxypropyl trimethoxysilane-tetramethoxysilane copolymer, vinyl trimethoxysilane-tetramethoxysilane copolymer, and the like.
The content of the silane compound in the acrylic adhesive is usually 0.01 parts by mass or more and 10 parts by mass or less, preferably 0.05 parts by mass or more and 5 parts by mass or less, more preferably 0.1 parts by mass or more and 2 parts by mass or less, relative to 100 parts by mass of the (meth) acrylic resin. When the content of the silane compound is 0.01 parts by mass or more, the effect of improving the adhesion between the adhesive layer and an optical member such as a glass substrate can be easily obtained. In addition, if the content of the silane compound is 10 parts by mass or less, bleeding of the silane compound from the adhesive layer can be suppressed.
The acrylic 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 adhesive may contain 2 or more ionic compounds.
Examples of the inorganic cation include lithium cations [ Li ] + Sodium cations [ Na ] + Potassium cation [ K ] + Alkali metal ion such as beryllium cation [ Be ] 2+ Magnesium cations [ Mg) 2+ Calcium cation [ Ca ] 2+ Alkaline earth metal ions such as aluminum, and the like.
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 anions include chloride anions [ Cl ] - Bromine anions [ Br ] - Iodine anions [ I ] - Tetrachloroaluminate anions [ AlCl ] 4 - Heptachlorodialuminate anions [ Al ] 2 Cl 7 - Tetrafluoroborate anions [ BF ] 4 - Hexafluorophosphate anions [ PF 6 - Perchlorate anions [ ClO ] 4 - Nitrate anions [ NO ] 3 - Hexafluoroarsenate anions [ AsF 6 - Hexafluoroantimonate anions [ SbF 6 - Hexafluoroniobate anions [ NbF) 6 - Hexafluorotantalate anions [ TaF 6 - Dicyandiamide anion [ (CN) 2 N - And the like.
Examples of the organic anions include acetate anions [ CH ] 3 COO - Trifluoroacetate anions [ CF) 3 COO - Methanesulfonate anion [ CH ] 3 SO 3 - Triflate anions [ CF 3 SO 3 - Para-toluenesulfonate anion [ p-CH ] 3 C 6 H 4 SO 3 - Bis (fluorosulfonyl) imide anions [ (FSO) 2 ) 2 N - Bis (trifluoromethanesulfonyl) imide anions [ (CF) 3 SO 2 ) 2 N - Tris (trifluoromethanesulfonyl) methanation anion [ (CF) 3 SO 2 ) 3 C - Dimethyl phosphinate anion [ (CH) 3 ) 2 POO - (Poly) hydrofluoroanions [ F (HF) ] n - (n is 1 or more and 3 or less), thiocyanate anion [ SCN - Perfluoro-butanesulfonate anion [ C ] 4 F 9 SO 3 - Bis (pentafluoroethylsulfonyl) imide anions [ (C) 2 F 5 SO 2 ) 2 N - Perfluoro butyrate anions [ C ] 3 F 7 COO - (trifluoromethanesulfonyl) (trifluoromethanecarbonyl) imine anion [ (CF) 3 SO 2 )(CF 3 CO)N - And the like.
Specific examples of the ionic compound may be selected from the combinations of the cationic component and the anionic component.
Examples of the ionic compound having an organic cation include pyridinium salts such as N-octylpyridinium hexafluorophosphate, N-octyl-4-methylpyridinium hexafluorophosphate, N-butyl-4-methylpyridinium hexafluorophosphate, N-decylpyridinium bis (fluorosulfonyl) imide salt, N-hexylpyridinium bis (trifluoromethanesulfonyl) imide salt, N-octylpyridinium bis (trifluoromethanesulfonyl) imide salt, 1-ethyl-3-methylimidazolium hexafluorophosphate, 1-ethyl-3-methylimidazolium p-toluenesulfonate, 1-ethyl-3-methylimidazolium bis (fluorosulfonyl) imide salt, 1-ethyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt, and 1-butyl-3-methylimidazolium methanesulfonate; salt pyrrolidinium salts such as N-butyl-N-methylpyrrolidinium hexafluorophosphate, N-butyl-N-methylpyrrolidinium bis (fluorosulfonyl) imide salt, and N-butyl-N-methylpyrrolidinium bis (trifluoromethylsulfonyl) imide; quaternary ammonium salts such as tetrabutylammonium hexafluorophosphate and tetrabutylammonium p-toluenesulfonate.
Examples of the ionic compound having an inorganic cation include lithium bromide, lithium iodide, sodium hexafluorophosphate, and the like.
From the viewpoint of maintaining antistatic properties, the ionic compound is preferably solid at room temperature. The ionic compound preferably has a melting point of 30 ℃ or higher, more preferably 35 ℃ or higher. On the other hand, if the melting point is too high, the compatibility with the (meth) acrylic resin is deteriorated, and therefore the melting point of the ionic compound is preferably 90 ℃ or less, more preferably 70 ℃ or less, and still more preferably less than 50 ℃.
The content of the ionic compound in the acrylic pressure-sensitive adhesive is preferably 0.1 part by mass or more and 8 parts by mass or less, more preferably 0.2 part by mass or more and 6 parts by mass or less, still more preferably 0.5 part by mass or more and 5 parts by mass or less, particularly preferably 1 part by mass or more and 5 parts by mass or less, relative to 100 parts by mass of the (meth) acrylic resin. If the content of the ionic compound is 0.1 part by mass or more, it is advantageous to improve the antistatic property, and if it is 8 parts by mass or less, it is advantageous to maintain the durability of the adhesive layer.
Various additives may be further blended into the adhesive composition and the pressure-sensitive adhesive composition. Examples of the additives include a reworking agent (Japanese text: ヮ), a tackifying resin, an antioxidant, an ultraviolet absorber, a defoaming agent, a corrosive agent, and a light diffusing agent such as fine particles.
(resin layer)
The resin layer may be a polarizing film; a protective film provided for protecting the surface of the polarizing film or the like; a phase difference film; an optical compensation film other than the retardation film; a film having an antiglare function and a film having an antireflection function, which have a concave-convex shape on the surface; a reflective film having a reflective function on a surface thereof; a semi-transmission reflective film having both a reflection function and a transmission function; a light diffusion film; a hard coat film; color correction films, and the like. The filter may include 1 or 2 or more of the above resin layers.
Examples of the polarizing film include a polarizing film in which iodine is aligned in a polyvinyl alcohol resin layer, a polarizing film in which a liquid crystal compound and a dichroic dye are aligned, and the like.
The material of the resin layer other than the polarizing film is not particularly limited, and examples thereof include polyolefin resins such as chain polyolefin resins (polyethylene resins, polypropylene resins, etc.), cyclic polyolefin resins (norbornene resins, etc.); cellulose ester resins such as triacetyl cellulose, diacetyl cellulose and cellulose acetate propionate; polyester resins such as polyethylene terephthalate and polyethylene naphthalate; a polycarbonate resin; (meth) acrylic resins such as (meth) acrylic acid and polymethyl (meth) acrylate; vinyl alcohol resins such as polyvinyl alcohol and polyvinyl acetate; a polystyrene resin; mixtures, copolymers, and the like thereof. These resins may contain 1 or 2 or more additives such as lubricants, plasticizers, dispersants, heat stabilizers, ultraviolet absorbers, infrared absorbers, antistatic agents, antioxidants, and light diffusion agents such as fine particles.
(display device)
The above-described filter can be suitably used in display devices such as organic EL display devices, liquid crystal display devices, inorganic electroluminescence (inorganic EL) display devices, and electron emission display devices. By disposing the filter on the visible side with respect to the image display element of the display device, light having a wavelength of around 580nm (575 to 590 nm) among light entering the filter (preferably light having a maximum absorption wavelength of 580 nm) can be absorbed. As a result, the color purity of the green light and the red light is higher in the light transmitted through the filter than in the case where the filter is not provided, and therefore the color gamut that can be expressed in the display device can be enlarged. In a conventional display device using no such filter, the separation of green light and red light is insufficient, but in a display device using such filter, it is expected to improve the separation of green light and red light.
Fig. 2 (a) and (b) are schematic cross-sectional views showing an example of a display device including a filter. The display device shown in fig. 2 (a) is an organic EL display device including the optical filter 10 shown in fig. 1 (a) and the image display element 1, and the image display element 1 is a light-emitting layer including an organic EL element. The filter 10 may be disposed on the visible side of the image display element 1 via the pressure-sensitive adhesive layer 11 for image display element.
The display device shown in fig. 2 (b) is a liquid crystal display device including the optical filter 20 shown in fig. 1 (b) and the image display element 2, and the image display element 2 is a liquid crystal cell including a liquid crystal layer. The filter 20 may be disposed on the visible side of the image display element 2 via the image display element adhesive layer 21.
Examples
Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples, but the present invention is not limited to these examples. In synthesis examples, comparative synthesis examples, and comparative examples, "%" and "parts" are mass% and parts unless otherwise specified.
[ identification of Compounds ]
The structure of the compounds was identified by MASS spectrometry (LC: model 1200 from Agilent: LC/MSD from Agilent).
[ measurement of maximum absorption wavelength ]
The maximum absorption wavelength of 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 measured using an ultraviolet-visible spectrophotometer (V-650 DS; manufactured by Japanese Spectroscopy Co., ltd.) (quartz cell, optical path length: 1 em).
The maximum absorption wavelength of the adhesive sheets obtained in examples and comparative examples was also measured using the above-mentioned uv-vis spectrophotometer.
[ Synthesis example 1 (Compound represented by formula (II))
3.0 parts of 3, 4-dihydroxy-3-cyclobutene-1, 2-dione (Fuji film and Wako pure chemical industries, ltd.), 5.0 parts of 2, 4-dimethylpyrrole (Tokyo chemical industries, ltd.), 175 parts of 1-butanol and 290 parts of toluene were mixed. The resulting mixture was stirred at a temperature of 110℃for 3 hours while removing the water formed using a Dean-Stark tube. After the completion of the reaction, the solvent was distilled off, 300 parts of ion-exchanged water was added thereto, 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℃for 12 hours to obtain 4.0 parts of the compound represented by the formula (A-1).
After 2.3 parts of Compound (A-1) was cooled 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.) was added thereto, and the mixture was stirred under an ice bath for 3 hours. After the obtained reaction mass (reaction solution) was warmed to room temperature, an aqueous sodium thiosulfate solution was added thereto to quench the reaction. The solvent was distilled off, and the resulting solid was washed with methanol/ion-exchanged water. The obtained solid was dried to obtain 3.6 parts of the compound represented by the formula (A-2). Mass spectrometry was performed on the resulting compound.
Ionization mode = esi+: m/z= [ m+h ]] + 424.9
Exact molecular weight (Exact Mass): 423.9
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[ 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 a cesium carbonate aqueous solution, 0.37 part of tris (dibenzylideneacetone) -dipalladium (0), 0.46 part of tri-t-butylphosphonium tetrafluoroborate and 1.49 parts of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol (manufactured by Tokyo chemical industries, ltd.) were added thereto and the mixture was refluxed for 2 hours. After the completion of the reaction, 10% acetic acid water was added thereto to stop the reaction. 10% saline was added thereto, and after separation, the organic layer was concentrated. The obtained solid was recrystallized from 100 parts of a solution of toluene/1-butanol=1/1 to obtain 0.4 parts of the compound represented by the formula (a-3). The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 509.2
Exact molecular weight (Exact Mass): 508.24
[ Synthesis example 3 (Compound represented by formula (I))
A compound represented by the formula (A-4) was synthesized in the same manner as in Synthesis example 2, except that 3,4, 5-trimethoxyphenylboronic acid was used in place of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2. The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 601.3
Exact molecular weight (Exact Mass): 600.25
[ Synthesis example 4 (Compound represented by formula (I))
Synthesis example 2 was repeated in the same manner with the exception that 4-hexylphenylboronic acid was used in place of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2 to obtain a compound represented by formula (A-5). The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 589.4
Exact molecular weight (Exact Mass): 588.37
[ Synthesis example 5 (Compound represented by formula (I))
A compound represented by the formula (A-6) was synthesized in the same manner as in Synthesis example 2, except that 4-hexyloxyphenylboronic acid was used in place of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2. The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 621.4
Exact molecular weight (Exact Mass): 620.36
[ Synthesis example 6 (Compound represented by formula (I))
A compound represented by the formula (A-7) was synthesized in the same manner as in Synthesis example 2, except that 4- (dimethylamino) phenylboronic acid was used in place of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2. The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 507.3
Exact molecular weight (Exact Mass): 506.27
[ Synthesis example 7 (Compound represented by formula (I))
A compound represented by the formula (A-8) was synthesized in the same manner as in Synthesis example 2, except that 4- (diphenylamino) phenylboronic acid was used in place of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2. The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 754.3
Exact molecular weight (Exact Mass): 754.33
[ Synthesis example 8 (Compound represented by formula (I))
Synthesis example 2 was repeated in the same manner with the exception that 4' -propyl-4-biphenylboronic acid was used in place of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2 to obtain a compound represented by formula (A-9). The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 657.3
Exact molecular weight (Exact Mass): 656.34
[ Synthesis example 9 (Compound represented by formula (I))
A compound represented by the formula (A-10) was synthesized in the same manner as in Synthesis example 2, except that 6-ethoxy-2-naphthalene boric acid was used in place of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2. The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 609.3
Exact molecular weight (Exact Mass): 608.27
[ Synthesis example 10 (Compound represented by formula (I))
Synthesis example 2 was repeated in the same manner with the exception that 9, 9-dimethylfluorene-2-boronic acid was used instead of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2 to obtain a compound represented by formula (A-11). The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 653.3
Exact molecular weight (Exact Mass): 652.31
[ Synthesis example 11 (Compound represented by formula (I))
Synthesis example 2 was repeated in the same manner with the exception that benzo [ b ] thiophene-2-boronic acid was used in place of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2 to obtain a compound represented by formula (A-12). The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 533.1
Exact molecular weight (Exact Mass): 532.13
[ Synthesis example 12 (Compound represented by formula (I))
The synthesis was performed in the same manner as in Synthesis example 2 except that 9-ethylcarbazole-3-boric acid was used in place of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2, to obtain a compound represented by the formula (A-13). The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 655.3
Exact molecular weight (Exact Mass): 654.30
[ Synthesis example 13 (Compound represented by formula (I))
Synthesis example 2 was repeated in the same manner with the exception that 9- (4-biphenylyl) carbazole-3-boronic acid pinacol ester was used instead of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2 to obtain a compound represented by formula (A-14). The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 903.4
Exact molecular weight (Exact Mass): 902.36
[ Synthesis comparative example 1 ]
The compound represented by the formula (B-1) was synthesized in the same manner as the compound represented by the formula (A-1) except that 3-ethyl-2, 4-dimethylpyrrole was used in place of the 2, 4-dimethylpyrrole used in the synthesis of the compound represented by the formula (A-1) in synthesis example 1. The maximum absorption wavelength was measured for the resulting compound. The measured maximum absorption wavelengths are given in table 1.
[ Synthesis comparative example 2 ]
The compound represented by the formula (A-1) was obtained by the steps of the synthesis method of the compound represented by the formula (A-1) of synthesis example 1. The maximum absorption wavelength was measured for the resulting compound. The measured maximum absorption wavelengths are given in table 1.
[ Synthesis example 14 (Compound represented by formula (I))
A compound represented by the formula (A-15) was synthesized in the same manner as in Synthesis example 2, except that 4-tert-butylphenylboronic acid was used in place of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2. The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 533.3
Exact molecular weight (Exact Mass): 532.3
[ Synthesis example 15 (Compound represented by formula (I))
Synthesis example 2 was repeated in the same manner with the exception that 4-methoxy-3, 5-dimethylphenylboronic acid was used instead of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2 to obtain a compound represented by formula (A-16). The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode (mass analysis)＝ESI+：m/z＝[M+H] + 537.2
Exact molecular weight (Exact Mass): 536.3
[ Synthesis example 16 (Compound represented by formula (I))
Synthesis example 2 was repeated in the same manner with the exception that 4-carboxyphenylboronic acid pinacol ester was used instead of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2 to obtain a compound represented by the formula (A-17). The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 509.5
Exact molecular weight (Exact Mass): 508.2
[ Synthesis example 17 (Compound represented by formula (I))
A compound represented by the formula (A-18) was synthesized in the same manner as in Synthesis example 2, except that 1-thianthrene-based boric acid was used in place of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2. The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 697.2
Exact molecular weight (Exact Mass): 696.1
[ Synthesis example 18 (Compound represented by formula (I))
A compound represented by the formula (A-19) was synthesized in the same manner as in Synthesis example 2, except that 4-methyl-1-naphthaleneboric acid was used in place of 2, 6-dimethyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborane-2-yl) phenol in Synthesis example 2. The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 549.2
Exact molecular weight (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 ℃. 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 and refluxed for 3 hours. The resulting mixture was cooled to room temperature, the precipitated crystals were filtered and the solution was separated from the crystals. The obtained crystals were subjected to repulping washing with 327 parts of hexane, and as a result, pale green solid was obtained.
48.3 parts of acetic acid and the solid were mixed with an aqueous solution prepared by mixing 7.1 parts of concentrated hydrochloric acid and 40 parts of distilled water, and heated and refluxed at 110℃for 2 hours, whereby a change in color from pale green to pale orange occurred, and the reaction was stopped.
The resulting reaction solution was cooled to room temperature, and a pale orange powder was filtered. 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 a 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 35.7 parts of toluene were mixed and heated to reflux at 110℃for 3 hours. The obtained 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 with 327 parts of hexane to obtain 0.96 parts (yield 85.3%) of a purple compound represented by formula (C-2).
0.80 part of the compound represented by the formula (C-2) and 59.5 parts of dehydrated tetrahydrofuran were mixed, and stirred for 30 minutes while nitrogen substitution was performed below the freezing point (5 ℃).
To the resulting mixture, 0.94 parts of N-bromosuccinimide was added and stirred for 2 hours below the freezing point (5 ℃ C.). Pure water was added to the obtained reaction solution, and the mixture was filtered to separate and collect crystals. After the obtained crystals were dissolved in tetrahydrofuran again, pure water was added thereto, and the crystals were precipitated again to obtain 0.91 part (yield 90.7%) of a compound represented by the formula (A-20) in black-violet. The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 389.2
Exact molecular weight (Exact Mass): 388.04
[ Synthesis example 20 (Compound represented by formula (I))
Into a four-necked flask, 0.195 part of the compound represented by the formula (A-20), 22.2 parts of tetrahydrofuran and 17.5 parts of pure water were charged, and nitrogen gas was introduced at 80℃for 60 minutes to carry out bubbling. To the resultant mixture were added 0.092 parts of tris (dibenzylideneacetone) palladium, 0.116 parts of tri-t-butylphosphonium tetrafluoroborate, and 1.5 parts of a 1mol/L aqueous cesium carbonate solution. While stirring the reaction solution at 80℃in an oil bath, a solution obtained by dissolving 0.243 parts of benzofuran-2-boronic acid (manufactured by Tokyo chemical industries, ltd.) in 6.66 parts of tetrahydrofuran was added dropwise over 10 minutes, followed by stirring for 2 hours. To the resultant mixture was added 100 parts by mass of a 10% aqueous acetic acid solution, and the mixture was stirred under a nitrogen atmosphere for 15 minutes.
To the resulting mixture, 0.3 part of 10% saline was added and the mixture was subjected to a liquid separation operation, whereby the organic layer was separated and collected. The organic layer was dried using an evaporator to give crude product 1 as tar. The crude product 1 was subjected to extraction with methanol, after which methanol was removed, thereby obtaining a crude product 2. The obtained crude product 2 was dissolved by heating using 100 parts of a toluene/butanol=1/1 solution and recrystallized, whereby 0.07 parts (yield 32.8%) of a compound represented by the formula (a-21) was obtained.
The resulting compound was mass-analyzed and the maximum absorption wavelength was measured. The measured maximum absorption wavelengths are given in table 1.
Ionization mode = ESI +: m/z= [ m+h ]] + 427.1
Exact molecular weight (Exact Mass): 426.16
TABLE 1
TABLE 1
Compounds of formula (I) Maximum absorption wavelength [ nm ]] Solvent(s)
Synthesis example 2 (A-3) 580 CHCl 3
Synthesis example 3 (A-4) 579 CHCl 3
Synthesis example 4 (A-5) 578 CHCl 3
Synthesis example 5 (A-6) 580 CHCl 3
Synthesis example 6 (A-7) 591 CHCl 3
Synthesis example 7 (A-8) 589 CHCl 3
Synthesis example 8 (A-9) 581 CHCl 3
Synthesis example 9 (A-10) 584 CHCl 3
Synthesis example 1O (A-11) 585 CHCl 3
Synthesis example 11 (A-12) 588 CHCl 3
Synthesis example 12 (A-13) 586 CHCl 3
Synthesis example 13 (A-14) 586 CHCl 3
Synthesis example 14 (A-15) 578 CHCl 3
Synthesis example 15 (A-16) 578 CHCl 3
Synthesis example 16 (A-17) 573 CH 3 OH
Synthesis example 17 (A-18) 573 CHCl 3
Synthesis example 18 (A-19) 575 CHCl 3
Synthesis example 2O (A-21) 589 CHCl 3
Comparative Synthesis example 1 (B-1) 564 CHCl 3
Comparative Synthesis example 2 (A-1) 555 CHCl 3
[ example 1]
((production of (meth) acrylic resin)
To a reaction vessel equipped with a condenser, nitrogen inlet, thermometer and stirrer, a mixed solution of 81.8 parts of ethyl acetate as a solvent, 69.8 parts of butyl acrylate as a monomer, 20 parts of methyl acrylate, 1 part of 2-hydroxyethyl acrylate, 8 parts of 2-phenoxyethyl acrylate, 1 part of 2-methoxyethyl acrylate and 0.2 part of acrylic acid was added, and the air in the reaction vessel was replaced with nitrogen to remove oxygen, and the internal temperature was raised to 55 ℃. To the resultant mixed solution, the entire amount of a solution obtained by dissolving 0.14 part of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added. The resulting mixture was kept at an internal temperature of 55℃for 1 hour, and ethyl acetate was continuously added to the reaction vessel at an addition rate of 17.3 parts/hr while keeping the internal temperature at 55℃and polymerized for 8 hours after stopping the addition of ethyl acetate at a point in time when the concentration of the (meth) acrylic resin reached 35%. Finally, ethyl acetate was added so that the concentration of the (meth) acrylic resin was 20%, and an ethyl acetate solution of the (meth) acrylic resin was prepared. The weight average molecular weight (Mw) and polydispersity (Mw/Mn) of the resulting (meth) acrylic resin were measured, and as a result, the weight average molecular weight (Mw) was 140 ten thousand and the polydispersity (Mw/Mn) was 5.1.
(formulation of adhesive composition 1)
To 100 parts of the solid content of the (meth) acrylic resin obtained in the production of the (meth) acrylic resin, 0.6 part of a crosslinking agent ("coronete HXR" (isocyanurate modified product of hexamethylene diisocyanate) obtained from Tosoh, inc.), 0.5 part of a silane compound ("KBM-403" (3-glycidoxypropyl trimethoxysilane) obtained from the letter chemical industry, inc.), 3 parts of N-hexyl-4-methylpyridinium hexafluorophosphate as an antistatic agent, and 0.1 part of a compound represented by the formula (a-5) were mixed, and ethyl acetate was added so that the solid content concentration was 14%, to prepare a solution of the adhesive composition 1.
(production of adhesive sheet 1)
The release treated surface of the 1 st separator film (PLR-382190 from LINTEC Co., ltd.) formed of a polyethylene terephthalate film after the release treatment was coated with the adhesive composition 1 by using an applicator and dried at 100℃for 1 minute to prepare an adhesive layer. The thickness of the resulting adhesive layer was 20. Mu.m. A release-treated surface of a release-treated 2 nd separator film (PLR-251130, available from LINTEC Co., ltd.) formed of a polyethylene terephthalate film was bonded to the obtained pressure-sensitive adhesive layer to prepare a pressure-sensitive adhesive sheet 1. One of the separator films of the obtained adhesive sheet 1 was peeled off and bonded to one surface of an alkali-free glass (EagleXG, manufactured by CORNING corporation), and the maximum absorption wavelength was measured by an ultraviolet-visible spectrophotometer (UV-2450, manufactured by shimadzu corporation). The results are shown in Table 2. The absorbance at the wavelength of 400nm to 700nm of the spacer film and the alkali-free glass was substantially 0.
[ example 2 ]
Adhesive composition 2 was prepared by the same method as that for adhesive composition 1, except that the compound represented by formula (A-6) was used instead of the compound represented by formula (A-5). The adhesive sheet 2 was produced by the same method as the production of the adhesive sheet 1 except that the obtained adhesive composition 2 was used, and the maximum absorption wavelength was measured. The results are shown in Table 2.
Examples 3 to 11
Adhesive compositions 5 to 11 were prepared by the same method as that for the preparation of adhesive composition 1, except that the compound shown in Table 2 was used in place of the compound shown in formula (A-5). The adhesive sheets 5 to 11 were produced by the same method as the production of the adhesive sheet 1 except that the obtained adhesive compositions 5 to 11 were used, and the maximum absorption wavelength was measured. The results are shown in Table 2.
Comparative example 1
Adhesive composition 3 was prepared by the same method as that for adhesive composition 1, except that the compound represented by formula (B-1) was used instead of the compound represented by formula (A-5). The adhesive sheet 3 was produced by the same method as that for producing the adhesive sheet 1 except that the obtained adhesive composition 3 was used, and the maximum absorption wavelength was measured. The results are shown in Table 2.
Comparative example 2
Adhesive composition 4 was prepared by the same method as that for adhesive composition 1, except that the compound represented by formula (A-1) was used instead of the compound represented by formula (A-5). The adhesive sheet 4 was produced by the same method as the production of the adhesive sheet 1 except that the obtained adhesive composition 4 was used, and the maximum absorption wavelength was measured. The results are shown in Table 2.
TABLE 2
TABLE 2
Compounds of formula (I) Adhesive sheet Maximum absorption wavelength [ nm ]]
Example 1 (A-5) Adhesive sheet 1 583
Example 2 (A-6) Adhesive sheet 2 586
Example 3 (A-4) Adhesive sheet 5 586
Example 4 (A-7) Adhesive sheet 6 597
Example 5 (A-14) Adhesive sheet 7 592
Example 6 (A-15) Adhesive sheet 8 583
Example 7 (A-16) Adhesive sheet 9 584
Example 8 (A-17) Adhesive sheet 10 586
Example 9 (A-18) Adhesive sheet 11 579
Example 10 (A-19) Adhesive sheet 12 582
Example 11 (A-21) Adhesive sheet 13 593
Comparative example 1 (B-1) Adhesive sheet 3 569
Comparative example 2 (A-1) Adhesive sheet 4 559
[ comparative example 3 ]
Adhesive composition 14 was prepared by the same method as that for adhesive composition 1, except that the compound represented by formula (a-5) was not used. The adhesive sheet 14 was produced by the same method as the production of the adhesive sheet 1, except that the obtained adhesive composition 14 was used.
(calculation of reproducible color gamut)
When the adhesive sheet 5 was applied to a panel having a general backlight and a general color filter based on the absorption spectrum obtained for the adhesive sheet 5 of application example 3, the reproducible color gamut range [% ] in the panel was calculated by simulation. The backlight used in the simulation is a backlight in which a YAG phosphor is mixed with a Blue LED, and the color filter is a standard display according to sRGB. In addition, for the reproducible color gamut range [% ], a color reproducible range with respect to the DCI P3 color standard was calculated using the CIE1976 color system and compared.
The same applies to the case where the adhesive sheet 14 is applied instead of the adhesive sheet 5. The color reproduction-capable range is calculated based on the following equation with the color reproduction-capable range of the adhesive sheet 14 as a reference.
Color reproduction capable range [% ] =
(color reproduction capable range when the adhesive sheet 5 is applied)/(color reproduction capable range when the adhesive sheet 14 is applied) ×100
The reproducible color gamut ranges are calculated for the adhesive sheet 3 and the adhesive sheet 4 in the same manner as described above. The results are shown in Table 3.
(calculation of transmittance of backlight)
The transmission amount of the backlight when the adhesive sheet 5 was applied to a panel having a common backlight and a common color filter was calculated by simulation. The backlight used in the simulation is a backlight in which a YAG phosphor is mixed with a Blue LED, and the color filter is a standard display according to sRGB.
The same applies to the case where the pressure-sensitive adhesive sheet 14 is used instead of the pressure-sensitive adhesive sheet 5. The transmittance of the backlight when the adhesive sheet 5 is applied to the panel is calculated based on the following calculation formula with reference to the transmittance of the backlight when the adhesive sheet 14 is applied. The results are shown in Table 3.
Transmittance of backlight [% ] =
(transmission amount of backlight when the adhesive sheet 5 is applied)/(transmission amount of backlight when the adhesive sheet 14 is applied) ×100
The transmittance of the backlight was calculated for each of the adhesive sheet 3 and the adhesive sheet 4 in the same manner as described above. The results are shown in Table 3.
TABLE 3
TABLE 3 Table 3
By mixing the compound (I) with a (meth) acrylic resin solution to prepare a pressure-sensitive adhesive sheet, a filter having a maximum absorption wavelength in a wavelength region around 580nm (wavelength 575 to 590 nm) can be produced. In addition, by applying the adhesive sheet (filter) containing the compound (I) to a display device, the separability of green light and red light in transmitted light can be improved, and therefore, the reproducible color gamut can be widened. In addition, a decrease in transmittance of the backlight can be suppressed.
Example 12 (preparation of photocurable adhesive liquid 1)
A photocurable adhesive liquid 1 was prepared by mixing 80 parts of 3',4' -epoxycyclohexylmethyl 3, 4-epoxycyclohexane carboxylate, 20 parts of 1, 4-butanediol diglycidyl ether, 3 parts of a photo-cationic polymerization initiator, and 1 part of a compound represented by the formula (A-16) and defoaming the mixture.
Example 13 (preparation of photocurable adhesive liquid 2)
The same preparation as that of the photocurable adhesive liquid 1 was carried out except that the compound represented by the formula (A-18) was added in place of the compound represented by the formula (A-16), thereby preparing the photocurable adhesive liquid 2.
Example 14 (preparation of polarizing plate 1)
The surface of a triacetyl cellulose film having a thickness of 60 μm containing an ultraviolet absorber (trade name "FUJITAC TG60UL", manufactured by fuji film co., ltd.) was subjected to corona discharge treatment, and the photocurable adhesive liquid 1 prepared above was applied to the corona discharge treated surface by a bar coater so that the film thickness after curing was about 2 μm. A polyvinyl alcohol-iodine-based polarizing plate having a thickness of 28 μm was bonded to the adhesive layer formed by the coating. The surface of a retardation film (trade name "ZEONOR", manufactured by ZEON corporation) having a thickness of 50 μm formed of a cyclic polyolefin resin was subjected to corona discharge treatment, and the photocurable adhesive liquid 1 was applied to the corona discharge treated surface so that the film thickness after curing was about 2 μm using a bar coater. A laminate was produced by bonding the adhesive layer formed by the coating to the polarizer side of the polarizer having a triacetyl cellulose film bonded to one surface. From the retardation film side of the laminate, an ultraviolet irradiation device with a conveyor belt (a lamp using a "D bulb" manufactured by FUSION UV SYSTYM Co., ltd.) was used so that the cumulative light amount was 200mJ/cm 2 The adhesive is cured by irradiation of ultraviolet rays. In this way, a polarizer with protective films bonded to both sides of the polarizer was producedA plate 1. The obtained polarizing plate was cut into 40mm×40mm, and the polarizing plate was placed so as to emit measurement light from the surface opposite to the retardation film, and the transmission spectrum measurement was performed in the transmission axis direction of the polarizing plate in the wavelength range of 400nm to 700nm using an ultraviolet-visible spectrophotometer (UV-2450 manufactured by shimadzu corporation). In the obtained spectrum, a wavelength at which the transmittance reaches a minimum is set as the maximum absorption wavelength. The results are shown in Table 4.
Example 15 (preparation of polarizing plate 2)
Except that the photocurable adhesive liquid 2 was used instead of the photocurable adhesive liquid 1, a polarizing plate 2 having protective films bonded to both surfaces of the polarizing plate was produced by the same method as that for producing the polarizing plate 1. The obtained polarizing plate was cut into 40mm×40mm, and the maximum absorption wavelength was determined by the same method as that of the polarizing plate 1. The results are shown in Table 4.
TABLE 4
TABLE 4 Table 4
Compounds of formula (I) Polarizing plate Maximum absorption wavelength [ nm ]]
Example 14 (A-16) Polarizing plate 1 583
Example 15 (A-18) Polarizing plate 2 573
Description of the reference numerals
1. 2 image display element, 10 filter, 11 image display element adhesive layer, 12 retardation film, 13 adhesive layer, 14 1 st protective film, 15 polarizing film, 16 2 nd protective film, 20 optical laminate, 21 image display element adhesive layer, 24 1 st protective film, 25 polarizing film, 26 nd protective film.

Claims (4)

1. An optical filter comprising a compound represented by formula (I):
in the formula (I) of the present invention,
R 1 ～R 4 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms which may be substituted;
T 1 t and T 2 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms which may be substituted;
Y 1 y and Y 2 Any one of the (C) and (C) is an optionally substituted 1-valent aromatic group, and the other is an optionally substituted 1-valent aromatic group or an optionally substituted 1-valent hydrocarbon group having 1 to 6 carbon atoms, which is a group other than the 1-valent aromatic group, and which contains-CH 2 -optionally substituted with-O-or-CO-,
the filter has a maximum absorption wavelength in a wavelength region of wavelengths 575 to 590 nm.
2. The filter of claim 1, further comprising an adhesive layer,
the adhesive layer contains the compound represented by the formula (I).
3. A display device having the optical filter according to claim 1 or 2 and an image display element,
the optical filter is disposed on the visible side with respect to the image display element.
4. A display device according to claim 3, which is a liquid crystal display device or an organic electroluminescent display device.
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