TW201708410A - Composition containing dichroic dye, dye film produced using same, and polarizing element comprising said dye film - Google Patents

Abstract

The purpose of the present invention is to provide: a composition containing a dichroic dye, which has excellent coating workability and is useful for the formation of a dye film that enables the production of a high-quality polarizing element having excellent polarization performance; a dye film which is produced using this composition containing a dichroic dye; and a polarizing element which comprises this dye film. A composition which is characterized by containing (A) at least one dichroic dye, (B) at least one surfactant selected from the group consisting of polyoxyethylene alkyl ethers, polyoxyethylene alkylene alkyl ethers, polyoxyethylene distyrenated phenyl ethers and polyoxyethylene tribenzyl phenyl ethers, and (C) a solvent, and which is also characterized in that the surfactant has an HLB value of from 12.5 to 17.5 (inclusive).

Description

a composition containing a dichroic dye, a pigment film produced using the same, and a polarizing element having the pigment film

The present invention relates to a composition containing a dichroic dye which is useful for forming a pigment film which exhibits a high degree of polarization of a polarizing element, and a pigment film produced using the same. Further, the present invention relates to a polarizing element having the pigment film and having excellent polarizing performance.

A polarizing element used in a liquid crystal display device, a sunglass, a goggle, or the like is generally formed by adsorbing a dichroic dye such as iodine or a dichroic dye to a polymer material such as polyvinyl alcohol. The film is then produced by uniaxially stretching the obtained film to align the dichroic dye molecules in a certain direction, or uniaxially stretching the polymer film, and then adsorbing the dichroic dye. However, since the polarization axis and the absorption axis of the polarizing element obtained by such a method are perpendicular to each other, the shape of the polarizing element is usually limited to a flat plate shape. Further, in the production of the polarizing element, it is necessary to swell and dye the polyvinyl alcohol film, and then perform stretching treatment on the boric acid aqueous solution, and then, after performing the water washing treatment and the drying treatment, the protective film is pasted with an adhesive. The cumbersome steps of the resulting film Step. Further, in order to more easily mount the polarizing element in a desired portion and to manufacture various display elements including liquid crystal display, it is required to provide a polarizing element or a curved surface in which a polarizing direction in an arbitrary direction is set to a fine pattern. Polarized component.

In view of the problem of the conventional polarizing element, Non-Patent Document 1 discloses a method of producing a polarizing element by aligning dichroic dye molecules in a certain direction by a rubbing treatment. However, the coating property of the dye solution on the substrate is lowered due to damage and dust on the substrate due to the rubbing step in the rubbing treatment, and electrical damage caused by static electricity. Therefore, there is an uncoated portion on the obtained pigment film, and as a result, the quality of the polarizing performance cannot be satisfactorily obtained in the polarizing element having the dye film.

Patent Document 1 discloses a technique of obtaining a polarizing element having a higher polarizing performance by using a photo-alignment film and aligning dichroic dye molecules contacting the photo-alignment film in an arbitrary direction. However, when the surface of the dye film of the polarizing element is observed by an atomic force microscope (AFM), there is a portion in which the dichroic dye is uniformly aligned, and a portion (depression) in which the dichroic dye hardly exists and is not aligned. Therefore, the polarizing performance of the obtained polarizing element cannot be sufficiently satisfied as a practical level in a polarizing element for a display element.

In Patent Document 2, in order to further improve the uniformity of the alignment of the dichroic dye molecules and the polarizing performance of the obtained polarizing element, it is disclosed that the formation of the dichroic dye compound is improved as a whole, and the alignment of the dichroic dye compound is improved as a whole. Achieving practical standards as a display component Method of polarizing elements. In the polarizing element, a liquid crystalline polymer film having a photoactive group is used as an alignment film, and linearly polarized light is applied to the film, and the molecular axes of the photoactive groups of the polarized portion are arranged in a predetermined direction, and then interposed therebetween. a micro-patterned mask, after irradiating a linearly polarized light having a different polarization axis, applying a dichroic dye solution to the surface by applying a specific range of pressure in a direction perpendicular to the substrate It is made on the film. However, the alignment film which becomes a substrate is special and extremely expensive, and in the production of a polarizing element, it is necessary to adjust the pressing force in such a manner that a specific pressure is applied between the roller and the substrate. Therefore, it is desired to develop a polarizing element which can be manufactured using various kinds of substrates without being limited to a specific substrate.

Prior technical literature Patent literature

Patent Document 1: Japanese Patent Publication No. 7-261024

Patent Document 2: Japanese Patent No. 4175455

Non-patent literature

Non-Patent Document 1: "Thesis of the Institute of Electronic Information and Communication", 1988, JJ71-C, p.1188

The pigment film obtained by applying the composition containing the dichroic dye and the polarizing element obtained from the pigment film have not yet reached a satisfactory quality, and it is necessary to further improve the quality. In addition, It is also expected to develop a polarizing element which can be easily manufactured without using a special substrate.

In view of the above, it is an object of the present invention to provide a composition of a dichroic dye which is excellent in applicability and which is useful for forming a pigment film which is capable of producing a high-quality polarizing element having excellent polarizing properties, and is produced using the same. A pigment film and a polarizing element having the pigment film.

The present inventors have carefully studied to solve the above problems, and as a result, it has been found that (A) at least one type of dichroic dye is used, and (B) is selected from polyoxyethylene alkyl ethers and polyoxyethylene alkylenes. At least one surfactant of the group consisting of alkyl ether, polyoxyethylene distyrenated phenyl ether and polyoxyethylene tribenzyl phenyl ether, and (C) a solvent; and the HLB value of the aforementioned surfactant A composition of 12.5 or more and 17.5 or less can obtain a pigment film of a polarizing element which is capable of producing a high quality and excellent polarizing performance without polarization deterioration.

That is, the gist of the present invention is as follows.

(1) A composition comprising: (A) at least one dichroic dye, (B) selected from the group consisting of polyoxyethylene alkyl ethers, polyoxyethylene alkylene ethers, and polyoxyethylene distyrenated. At least one surfactant of the group consisting of phenyl ether and polyoxyethylene tribenzyl phenyl ether, and (C) a solvent; the HLB value of the surfactant is 12.5 or more and 17.5 or less.

(2) The composition according to (1), wherein the dichroic dye is a water-soluble azo dye.

(3) The composition of (1) or (2), wherein the dichroic dye is a compound represented by the following formula (1) or the salt,

(In the formula (1), X ₁ represents a phenyl group or a naphthyl group having one or two sulfonic acid groups, a hydroxyl group or an alkoxy group having a carbon number of 1 to 3, and X ₂ and X ₃ each independently represent a stretching. A phenyl or anthranyl group having one or two selected from the group consisting of an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a hydroxyl group, and a sulfonic acid group. One or two substituents of the group consisting of R ₁ represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an ethyl fluorenyl group, a benzamidine group, or an unsubstituted phenyl group or a carbon number of 1 to 4 a phenyl group substituted with an alkyl group, an alkoxy group having 1 to 4 carbon atoms, an amine group, a sulfonic acid group or an alkyl group having a carbon number of 1 to 4, m is 0 or 1, and n is 1 or 2).

(4) The composition of (3), wherein X ₁ is a compound represented by the following formula (3) or the salt as a substituent,

(in the formula (3), j is 1 or 2).

(5) The composition according to any one of (1) to (4) wherein the polyoxyethylene alkylene oxide is a polyoxyethylene polyoxypropylene alkyl ether or a polyoxyethylene polyoxypropylene block polymer. .

(6) The composition according to any one of (1) to (5), wherein the total amount of the dichroic dye is 0.1 to 15 parts by mass based on 100 parts by mass of the solvent.

(7) The composition according to any one of (1) to (6) wherein the solvent contains at least water.

(8) A pigment film produced by using the composition according to any one of (1) to (7).

(9) A polarizing element having a pigment film as (8).

(10) The polarizing element of (9), wherein the dichroic ratio is 5 or more.

The composition containing a dichroic dye of the present invention is excellent in coatability. Therefore, when the pigment film is produced by using the composition of the present invention, for example, even if the substrate is subjected to a rubbing treatment, a pigment film which improves the conventional coating failure of the substrate can be formed. In addition, by using the pigment As the film, a polarizing element having high quality without polarization defects and excellent polarizing performance can be obtained. Further, in the pigment film of the present invention, since the raw material of the substrate is not limited to a specific material, the pigment film and the polarizing element having the same can be produced more easily.

The invention is described in detail below. Hereinafter, the numerical range represented by "~" means a range including the numerical values described before and after "~" as the lower limit and the upper limit. Further, when not specifically stated, the compound (substituent) represented by the formula (1) to the formula (3) is represented by a free acid, and the salt of a free acid means a hydroxyl group or a sulfonic acid group. a salt of a hydrophilic group. In the following description, in order to avoid cumbersomeness, "the compound represented by the formula (1) or the salt", "the compound represented by the formula (2) or the salt", and "the formula" 3) The compound or the salt shown" is simply described as "a compound represented by the formula (1)", "a compound represented by the formula (2)", and a compound represented by the formula (3). "."

First, each component contained in the composition of the present invention will be described. The composition of the present invention comprises: (A) at least one dichroic dye, and (B) selected from the group consisting of polyoxyethylene alkyl ethers, polyoxyethylene alkylene oxides, polyoxyethylene distyryl phenyl ethers, and At least one surfactant of the group consisting of polyoxyethylene tribenzyl phenyl ether, and (C) a solvent; the surfactant having an HLB value of 12.5 or more and 17.5 or less.

(A) dichroic pigment

The composition of the present invention contains a dichroic dye as a main component for forming a pigment film. The dichroic dye is a compound which exhibits a polarizing property by arranging the particles or the aggregates in a certain direction. Examples of the dichroic dye include an azo dye, an anthraquinone dye, and a pyrazolone. A dye-based compound such as a dye, a triphenylmethane dye, a quinoline dye, an oxazine dye, a thiazine dye, or an anthraquinone dye. The dichroic dye used in the present invention is a compound which exhibits a liquid crystallinity under a certain solvent composition, a dye concentration, and a temperature condition, and is, for example, an influx of Jiang Zhenghao, "Application of Functional Pigment", No. 1 Brush release, CMC Corporation, June 2002, p. 102-104 dichroic pigment. Further, as the dichroic dye, a water-soluble azo dye is preferably used, and among them, a compound having an aromatic ring structure is particularly preferable. Examples of the aromatic ring structure include, in addition to benzene, naphthalene, anthracene, and phenanthrene, a heterocyclic ring such as thiazole, pyridine, pyrimidine, pyridazine, pyrazine or quinoline, or a fourth-order salt thereof, and the like. A condensed ring such as benzene or naphthalene is particularly preferably a hydrophilic group such as a sulfonic acid group, a carboxylic acid group, an amine group or a hydroxyl group, or a salt of a sulfonic acid group or a carboxylic acid group. Ring.

Specific examples of the dichroic dye include CIDirect Orange 39, CI Direct Orange 41, CI Direct Orange 49, CI Direct Orange 72, CI Direct Red 2, CI Direct Red 28, CI Direct Red 39, CI Direct. Red 79, CIDirect Red 81, CIDirect Red 83, CIDirect Red 89, CIDirect Violet 9, CIDirect Violet 35, CI Direct Violet 48, CIDirect Violet 57, CIDirect Blue 1, CIDirect Blue 15, CIDirect Blue 67, CIDirect Blue 78, CIDirect Blue 83, CIDirect Blue 90, CIDirect Blue 98, CIDirect Blue 151, CI Direct Blue 168, CIDirect Blue 202, CIDirect Green 42, CIDirect Green 51, CIDirect Green 59, CIDirect Green 85, CIDirect Yellow 4, CIDirect Yellow 12, CIDirect Yellow 26, CIDirect Yellow 44, CI Direct Yellow 50, mordant yellow 26, CI No. 27865, CI No. 27915, CI No. 27920, CI No. 29058, CI No. 29060, etc., and Japanese Patent Publication No. 1-161202, Japanese Special Japanese Patent Laid-Open No. Hei 1-172906, Japanese Patent Application Laid-Open No. Hei 1-172907, Japanese Patent Laid-Open No. Hei 1-183602, Japanese Patent Laid-Open No. Hei 1-248105, Japanese Patent Laid-Open No. Hei 1-265205, and Japanese Patent Laid-Open No. Hei 9-230142 The dichroic dye described in each of the publications of the Gazette.

Among the dichroic dyes shown in the above specific examples, a compound represented by the following formula (1) or (2) is particularly preferable, and a compound represented by the following formula (1) is particularly preferable. The compound represented by the formula (1) and the formula (2) is present as a free acid or a salt. The salt of the free acid is not particularly limited, and may be, for example, an alkali metal salt such as Li, Na or K or an arbitrary salt such as a 4- to ammonium salt. By using this dichroic dye, the polarizing performance of the obtained polarizing element can be improved.

(In the formula (1), X ₁ represents a phenyl group or a naphthyl group having one or two sulfonic acid groups, a hydroxyl group or an alkoxy group having a carbon number of 1 to 3, and X ₂ and X ₃ each independently represent a stretching. A phenyl or anthranyl group having one or two selected from the group consisting of an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a hydroxyl group, and a sulfonic acid group. One or two substituents of the group consisting of R ₁ represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an ethyl fluorenyl group, a benzamidine group, or an unsubstituted phenyl group or a carbon number of 1 to 4 a phenyl group substituted with an alkyl group, an alkoxy group having 1 to 4 carbon atoms, an amine group, a sulfonic acid group or an alkyl group having a carbon number of 1 to 4, m is 0 or 1, and n is 1 or 2)

(In the formula (2), Y ₁ represents a naphthyl group having one or two sulfonic acid groups, and may further have a hydroxyl group or an alkoxy group having 1 to 3 carbon atoms, and Y ₂ and Y ₃ each independently represent a benzene stretching group. a phenyl or anthranyl group having one or two selected from the group consisting of an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a hydroxyl group and a sulfonic acid group. One or two substituents of the group, R ₂ represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an ethyl fluorenyl group, a benzamidine group, or an unsubstituted phenyl group or a carbon number of 1 to 4. a phenyl group substituted with an alkyl group, an alkoxy group having 1 to 4 carbon atoms, an amine group, a sulfonic acid group or an amine group having an alkyl group having 1 to 4 carbon atoms, as a phenylazo group

Substituted by any one of the 5-, 6-, 7- or 8-position of the terminal naphthyl group, and R ₃ and R ₄ each independently represent a hydrogen atom, a hydroxyl group, a sulfonic acid group, an alkyl group having 1 to 3 carbon atoms or Alkoxy having 1 to 3 carbon atoms, q is 0 or 1, and p is 1 or 2)

Specific examples of the compound represented by the above formula (1) include, for example,

Wait.

Further, specific examples of the compound represented by the above formula (2) include, for example,

Wait.

In the compound represented by the formula (1) or the formula (2), a compound represented by the following formula (3) is used as a substituent by X ₁ in the formula (1) or Y ₁ in the formula (2) Further, the polarizing property can be further improved. Particularly, in the case of having a high dichroic ratio alone, a compound represented by the formula (1) having a compound represented by the following formula (3) as a substituent is preferably used. This substituent is the same as the compound represented by the formula (1) or the formula (2), and is present as a free acid or a salt. The salt of the free acid is not particularly limited, and may be, for example, an alkali metal salt such as Li, Na or K or an arbitrary salt such as a 4- to ammonium salt.

(in equation (3), j is 1 or 2)

The dichroic dye of the present invention may be used alone or in combination of two or more. The combination of the two or more kinds of dichroic dyes is not particularly limited, but the dichroic dye can further increase the dichroic ratio of the dichroic dye by using an additional dichroic dye. In addition, the total content of all the dichroic dyes contained in the composition of the present invention is not particularly limited, and in order to impart high anisotropy to the dye film, the total amount is 100 parts by mass of the following (C) solvent. 0.1 to 15 parts by mass, preferably 0.3 to 10 parts by mass, particularly preferably 0.5 to 7 parts by mass.

(B) surfactant

The composition of the present invention contains, as a further component in the production of the dye film, a polyoxyethylene alkyl ether, a polyoxyethylene alkylene ether, a polyoxyethylene distyryl ether, and a polyoxyethylene. At least one group consisting of benzyl phenyl ether and having an HLB value of at least 1 of 12.5 or more and 17.5 or less a surfactant. By using this surfactant, it is possible to improve the coating failure which occurs at the time of coating when the pigment film is previously formed on a substrate. Further, in the method for producing a polarizing element described in Patent Document 2, in order to reduce the shear stress parallel to the substrate during coating, it is necessary to apply a specific pressure between the roller and the substrate in the production of the polarizing element. The pressure is adjusted, but the composition of the present invention does not require this special step when the composition of the present invention is applied to a substrate by containing a specific surfactant. Further, even if the composition of the present invention is applied to a substrate after the rubbing treatment, a substrate to which the photo-alignment film is applied, a substrate damaged by friction, or a substrate after stretching, etc., In the pigment film, it is also possible to reduce the size which may be visually recognized, for example, an uncoated portion having a size of 50 μm or more, and as a result, a pigment film having improved coating failure can be produced.

The surfactant used in the present invention has an HLB value of 12.5 or more and 17.5 or less, and preferably has an HLB value of 13.0 or more and 17.0 or less. When the HLB value is less than 12.5, the coating failure occurring in the pigment film cannot be improved. On the other hand, when the HLB value is more than 17.5, the dichroic dye cannot be aligned in the pigment film. Specific examples of the polyoxyethylene alkyl ether having the above HLB value include Emulgen 1108 (HLB value 13.4) manufactured by Kao Corporation, Emulgen 1118S-70 (HLB value 16.4) manufactured by Kao Corporation, and the like.

Polyoxyethylene alkylene oxide, particularly preferably polyoxyethylene polyoxypropylene alkyl ether or polyoxyethylene polyoxypropylene block polymer. Specific examples of the polyoxyethylene alkylene alkylene ether having the above HLB value, for example, polyoxyethylene polyoxypropylene alkyl ether, Emulgen LS-106, manufactured by Kao Corporation (HLB value 12.5), Emulgen LS-110 (HLB value 13.4) manufactured by Kao Corporation, Emulgen LS-114 (HLB value 14.0) manufactured by Kao Corporation, Emulgen MS-110 (HLB value 12.7) manufactured by Kao Corporation, polyoxyethylene polyoxygen Examples of the propylene block polymer include New Pole PE-68 (HLB value 15.7) manufactured by Sanyo Chemical Co., Ltd., New Pole PE-78 (HLB value 15.6) manufactured by Sanyo Chemical Co., Ltd., and New Pole PE-108 manufactured by Sanyo Chemical Co., Ltd. ( HLB value 15.5), Sanyo Chemical Co., Ltd. New Pole PE-128 (HLB value 15.6). Among them, polyoxyethylene polyoxypropylene alkyl ether, especially Emulgen LS-106 manufactured by Kao Corporation, Emulgen LS-110 manufactured by Kao Corporation, Emulgen LS-114 manufactured by Kao Corporation, Emulgen MS-110 manufactured by Kao Corporation, polyoxyethylene polymerization The oxypropylene block polymer is preferably New Pole PE-68 manufactured by Sanyo Chemical Company.

In addition, specific examples of the polyoxyethylene distyrenated phenyl ether having the above HLB value include Emulgen A-60 (HLB value 12.8) manufactured by Kao Corporation and Emulgen A-90 (HLB value 14.5) manufactured by Kao Corporation. Specific examples of the polyoxyethylene tribenzyl phenyl ether having the above HLB value include Emulgen B-66 (HLB value 13.2) manufactured by Kao Corporation.

The surfactant of the present invention may be used alone or in combination of two or more. In addition, the total content of all the surfactants contained in the composition of the present invention is 0.01 to a total of 100 parts by mass of the following (C) solvent, from the viewpoint of not inhibiting the alignment of the dichroic dye. 3 parts by mass, preferably 0.05 to 2 parts by mass.

(C) solvent

The composition of the present invention contains a solvent as a coating liquid. The solvent is not particularly limited as long as it is a dichroic dye which can be used for dissolution, and examples thereof include water, alcohols, ethers, pyridine, dimethylformamide (DMF), and dimethylarylene ( DMSO), N-methylpyrrolidone (NMP), dimethylacetamide (DMAC), dimethylimidazoline (DMI), etc., among which may contain only one solvent or a plurality of solvents. In particular, when a water-soluble dichroic dye is used, water or a mixed solvent mainly containing water and the above organic solvent is preferred. The amount of the organic solvent to be mixed with water is arbitrary, and is preferably from 0 to 50% by mass, particularly preferably from 0 to 20% by mass, based on the water.

Next, a dye film and a polarizing element produced by using the composition of the present invention, and a method for producing the same will be described. The pigment film of the present invention is produced by applying the above composition to a substrate and then drying it. When the pigment film of the present invention is formed on a substrate and used as a polarizing element, a laminate composed of a substrate and a pigment film may be used as a polarizing element, or a protective layer may be further laminated on the surface of the pigment film. The laminate is used as a polarizing element. Examples of the substrate used in forming the dye film of the present invention include a glass plate such as cerium oxide-based glass or hard glass, a quartz plate, or the like, or a polyoxyalkylene resin, an ABS resin, a cycloolefin resin, or the like. Aldehyde resin, (meth)acrylic resin, cellulose acetate, cellulose acetate, chlorinated polyether, ethylene-vinyl acetate copolymer, fluororesin, ionic polymer, methylpentene polymer, nylon, poly Polyamide, polyfluorene, polycarbonate, polyethylene terephthalate, polybutylene terephthalate, etc. Imine, polyamine, polyphenylene ether, polyphenylene sulfide, polyallyl fluorene, polyarylate, polyethylene, polypropylene, polystyrene, polyfluorene, cycloolefin resin, vinyl acetate resin, partial Vinyl chloride resin, AS resin, vinyl chloride resin, alkyd resin, allyl resin, amine resin, urea resin, melamine resin, epoxy resin, phenol resin, unsaturated polyester resin, polyoxyl resin, polyamine A plastic sheet or sheet (film) of various materials such as an acid ester resin, such as a photoactive molecule (commonly referred to as a photo-alignment film) described in Patent Document 1 or Patent Document 2, or a film laminated or coated with such a resin. Or a plate, or a substrate coated with a metal oxide such as cerium oxide, tin oxide, indium oxide, aluminum oxide, titanium oxide, chromium oxide or zinc oxide, or a substrate such as tantalum nitride or tantalum carbide. Further, a substrate (film) having a metal film coating surface having a high reflection energy can also be used as the substrate. These substrates may be planar or curved. Further, the thickness of the substrate is from 1 μm to 500 μm, preferably from 10 to 100 μm.

A pigment film of the present invention having a polarizing function can be formed by rubbing, photoaligning or stretching the substrate. For the brushing, a method of wiping a substrate with a specific cloth as described in Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. 2002-90743, or Japanese Patent Application No. 2012-015492 or Japan Japanese Laid-Open Patent Publication No. 2012-064912 discloses a method of performing a uniaxial polishing process using an abrasive or a material containing an abrasive. For the light-aligning, for example, a polymer or a polymer (generally referred to as a material for a photo-alignment film) which irradiates polarized light to a photoactive group as described in Patent Document 1 or Patent Document 2, and aligns photoactive molecules. , polymerize or decompose, thereby causing the molecule to appear anisotropic on a particular axis Sex. The stretching is performed by stretching a polymer or a substrate obtained by a resin by heating or the like to align the molecules on a specific axis. Therefore, the dichroic dye applied to the substrate can be aligned by rubbing, photoaligning or stretching the substrate.

By subjecting the substrate to corona discharge treatment or ultraviolet irradiation, the dichroic ratio of the polarizing element described later can be increased, and the polarizing characteristics of the obtained polarizing element can be improved. The corona discharge treatment can be applied by using various commercially available corona discharge treatment machines as a device for performing corona discharge treatment, and a corona treatment machine having an aluminum head is particularly preferred. The conditions of the corona discharge treatment are 20 to 400 W ‧ min ‧ m ^-2 , preferably 50 to 300 W ‧ min ‧ m ^-2 at an energy density per one corona discharge treatment. Further, when the corona discharge treatment once is still insufficient, the corona discharge treatment may be performed twice or more. Ultraviolet irradiation can also be applied by using various commercially available ultraviolet irradiation devices. The wavelength of the ultraviolet light to be used is not particularly limited, and is preferably, for example, a far ultraviolet ray of 300 nm or less. Further, the ultraviolet ray irradiation is preferably carried out under a flow of oxygen, and the irradiation time of the ultraviolet ray is sufficient for only a few minutes.

A composition of the present invention containing a dichroic dye (a solution containing a dichroic dye) is dropped onto the surface of the substrate, and a uniform thickness is provided on the substrate by a coater or a spin coating method. A coating film of a coloring pigment. The method of providing the coating film of the dichroic dye is not particularly limited as long as the solution containing the dichroic dye can be applied, and examples thereof include a method of immersing the substrate in a solution containing a dichroic dye, and A method of coating a solution of a dichroic dye by a bar coater or the like, for household use A method of applying a coating method of an inkjet printer such as a piezoelectric method, a thermal method, a Bubble Jet (registered trademark) method, or a spin coating machine by a spin coater, or a roll coater Coating, quick-drying printing, screen printing, gravure printing, curtain coater coating, spray coater coating, etc., particularly preferably a roll coater coating, a curtain coater coating, and a coating method by a spray coater.

Next, the substrate after the application of the solution of the dichroic dye is dried to form a layer of a dichroic dye in a solid state, whereby the pigment film of the present invention is obtained. The drying conditions vary depending on the type of the solvent, the type of the dichroic dye, the amount of the solution containing the dichroic dye applied, and the concentration of the dichroic dye, but the drying temperature may be room temperature to 100 ° C. Preferably, the temperature is from room temperature to 50 ° C, and the humidity is from 20 to 95% RH, preferably from 30 to 90% RH.

The thickness of the pigment film of the present invention is preferably from 0.001 to 10 μm, particularly preferably from 0.05 to 2 μm, from the viewpoint of improving the polarization characteristics. Further, in order to form the dye film of the present invention in the range of the thickness, the thickness of the coating film after applying the solution containing the dichroic dye is preferably 2 to 10 μm, particularly preferably 3 to 5 μm.

Further, the substrate coated with the solution containing the dichroic dye may be further subjected to heat treatment and/or humidification treatment. By applying heat treatment and/or humidification treatment, the adhesion of the dichroic dye to the substrate, the polarizing performance of the obtained polarizing element, and the dichroic ratio or durability can be improved. The temperature of the heat treatment is from room temperature to 110 ° C, preferably from 60 to 90 ° C, and the humidity of the humidification treatment is from 40 to 95% RH, preferably from 50 to 90% RH.

The pigment film of the present invention thus obtained can be used as polarized light element. The polarizing element of the present invention has a dichroic ratio (Rd), which is generally defined as the ratio of the absorbance along the absorption axis to the absorbance along the transmission axis. The dichroic ratio of the polarizing element of the present invention is calculated by the following formula (4), and when the dichroic ratio is 5 or more, it means that the polarizing function can be exhibited. The dichroic ratio of the polarizing element of the present invention is 5 or more, preferably 10 or more, particularly preferably 15 or more, and more preferably 20 or more. When the two-color ratio is less than 5, the degree of polarization is less than 65%, and the function as a polarizing element is insufficient. The degree of polarization of the polarizing element is usually required to be 65% or more, preferably 70% or more, and particularly preferably 80% or more. The degree of polarization refers to the ratio of the light intensity of the polarized component to the total light intensity. The higher the degree of polarization, the higher the polarizing performance. In the following formula (4), Ky is a transmittance which is the most capable of transmitting light when the polarized light is incident, and Kz is a transmittance which is the most absorbable light axis when the polarized light is incident.

[Number 1] Rd=Log(Kz/100)/Log(Ky/100)‧‧‧(4)

Further, by increasing the dichroic ratio of the polarizing element of the present invention, the surface of the stretched film which becomes the substrate can be imparted to the stretched film in the same direction as the stretching axis of the film. The molecular anisotropy of the surface is more molecularly anisotropic, thereby further enhancing the dichroic ratio. A method of exhibiting a greater molecular anisotropy than a film after stretching may, for example, be a method of rubbing a stretched film. The brush is exemplified by, for example, Japanese Laid-Open Patent Publication No. Hei 06-110059, and No. 2002-90743. The measurement of the molecular anisotropy of the surface of the stretched film is not particularly The measurement can be measured, for example, by a measurement method used for anchor measurement of an alignment film for liquid crystal. Further, the apparatus for measuring the molecular anisotropy is not particularly limited, and for example, Lay Scan manufactured by MARITEX SCOTT Co., Ltd. or the like can be used.

A polarizing element which exhibits molecular anisotropy in the long axis direction can be produced on the surface of a film having a phase difference axis (slow axis or fast axis) at a different angle from the long axis direction of the film. Specifically, the molecular anisotropy is imparted to the surface of the stretched film having the phase difference axis at an arbitrary angle with respect to the long-axis direction of the film, whereby the polarized light of the polarizing element can be arbitrarily controlled. Shaft or absorption axis. In other words, by using a polarizing element having a phase difference axis at an angle different from the angle with respect to the longitudinal direction of the film and exhibiting molecular anisotropy on the surface in the long axis direction, it can be produced as a substrate. The stretched film has a phase difference axis and a polarizing element having an absorption axis or a polarization axis at an angle different from the phase difference axis. The angle formed by the phase difference axis of the stretched film to be the substrate and the absorption axis or the polarization axis of the polarizing element is preferably any one of 15°, 45°, 75°, and 90°. This angle is preferred because it is known. Generally, when the linear polarization is to be controlled to be circularly polarized, a film having a phase difference of 1/4 is set relative to the length of the wavelength to be controlled. The absorption axis of the polarizing element is 45°. Further, the polarization axis of the linearly polarized light is reversed, and it is known that the film having a phase difference of 1/2 is set to 90° with respect to the length of the wavelength to be controlled. The film is set to have a phase difference of 15 or 75 with respect to the absorption axis or the polarization axis of the polarizing element, and the angle is a phase difference of 1/4 with respect to a wide range of wavelengths (generally also referred to as The axis angle used in the wide-band area achromatic phase difference plate). Thereby, the polarization axis or the absorption axis of the polarizing element can be arbitrarily controlled.

The pigment film of the present invention produced as described above is in a solid state such as amorphous or crystalline, but the dye film usually has poor mechanical strength. Therefore, the surface of the pigment film is subjected to a lake treatment, depending on the decane coupling agent. Cross-link processing, or set the protection layer. The lake treatment means that the metal ions are electrically coupled to the water-soluble dichromatic pigment. In some cases, the dye of the dichroic dye is also referred to as lake deposition or insolubilization. Examples of the compound suitable for the lake include aluminum chloride, iron chloride, calcium chloride, barium chloride, nickel chloride, magnesium chloride, copper chloride, barium acetate, nickel acetate, etc., but metal ions and the like may be used. It is not particularly limited as long as it is electrically bonded to the dichroic dye and the dichroic dye is insoluble in water. In addition, the crosslinking treatment of the decane coupling agent is not particularly limited. For example, the decane coupling agent described in JP-A-2011-53234 can be used, and the crosslinking treatment can be carried out by heating or the like to fix the dye film. Further, the protective layer is usually applied to the pigment film by a UV-curable or thermosetting transparent polymer film, or a transparent polymer film such as a polyester film or a cellulose acetate film. Set by the coating method such as lamination. The protective layer may also be provided as a coating layer formed of a polymer or a laminated layer of a film. The transparent polymer or film forming the transparent protective layer is preferably a transparent polymer or film having high mechanical strength and good thermal stability. As the substance for the transparent protective layer, for example, cellulose acetate cellulose such as cellulose triacetate or cellulose diacetate or the film, acrylic resin or the film, polyvinyl chloride resin or the film, nylon resin or The film, polyester resin or the thin a film, a polyarylate resin or the film, a cyclic polyolefin resin having a decene-like cyclic olefin as a monomer, or the film, polyethylene, polypropylene, ring system or polyolefin having a norbornene skeleton or The copolymer, main chain or side chain is a resin of ruthenium and/or guanamine or the polymer or the film or the like. Further, a resin having liquid crystallinity or the film may be provided as a transparent protective layer. The thickness of the protective layer is, for example, about 0.5 to 200 μm. The resin or film to be a protective layer may be provided on one or both sides of the polarizing element in one or more layers, and when a plurality of protective layers are used, the protective layers may be the same or different.

The polarizing element of the present invention can be used for polarized sunglasses or goggles. In the polarizing element of the present invention, it is possible to impart a tone to itself in the process, or to give a pattern having a plurality of polarization axes. The tone of the tone is displayed as a polarizing element or a polarizing plate. When the polarizing pattern is developed on the photoactive molecular layer, it can be manufactured by applying linear polarized light having a negative mask pattern or a negative photo of the photo. . Further, a multiaxial polarizing element or a polarizing plate having a plurality of polarizing axes can be produced by irradiating a polarizing pattern to a photoactive molecular layer by irradiating different portions of linear polarized light having different polarization axes. This additional function can be imparted only when a solution containing a dichroic dye is applied as compared with a case where a polyvinyl alcohol-based film is usually used. Therefore, a desired polarizing plate can be obtained without causing dimensional change or shrinkage. Those who do not have a dimensional change are particularly effective for displays that have to be provided with a polarizing element on one side, such as a flexible display or an organic electroluminescent display (known as OLED). Further, unlike the polarizing plates up to the present, the application of the dye does not require difficult conditions, and it is easy to obtain a desired polarizing element only by coating, and therefore, the production of the polarizing element is extremely easy.

Example Example

Hereinafter, the present invention will be described in more detail by way of examples, but the invention is not limited thereto. The evaluation of the transmittance shown in the examples was carried out in the following manner.

The transmittance of each wavelength was measured using a spectrophotometer ("U-4100" manufactured by Hitachi, Ltd.). The transmittance at each wavelength when the pigment film is measured in one sheet is the transmittance Ts, and the transmittance at the time of overlapping the two pigment films in the same direction of the absorption axis is set as parallel penetration. The rate Tp is a transmittance at which the two dye films are superimposed so that the absorption axis direction is orthogonal to the orthogonal bit transmittance Tc.

The degree of polarization ρ is obtained from the parallel bit transmittance Tp and the orthogonal bit transmittance Tc by the equation (5).

[Number 2] ρ = {(Tp-Tc) / (Tp + Tc)} ^1/2 × 100 Equation (5)

The dichroic ratio (Rd) was measured using V-7100 manufactured by JASCO Corporation, and the obtained value was used as a measurement result.

Example 1

By winding a roller with a brush cloth (MK0012 manufactured by Taenaka Pile Fabrics Co., Ltd.) at a speed of 100 rpm and a load of 5 kgf, The non-easy-adhesive surface of polyethylene terephthalate (A-4100 manufactured by Toyobo Co., Ltd., hereinafter abbreviated as "PET film") having a thickness of 100 μm of the substrate was subjected to a rubbing treatment. 5 parts by mass of CIDirect Blue 67 as a dichroic dye and polyoxyethylene as a surfactant were used in a coater equipped with a glass rod attached to the PET film at a distance of 3 μm. 0.1 parts by mass of oxypropylene alkyl ether (Emulgen LS-106: HLB value: 12.5) and 100 parts by mass of water as a solvent were applied to the PET film surface after the rubbing treatment. The obtained coating film was allowed to stand in an environment of 25 ° C and a humidity of 70% for 1 minute to dry the solvent. Then, the dried coating film was subjected to heat treatment and humidification treatment for 5 minutes in an environment of 60° C. and a humidity of 90% to obtain a pigment film of the present invention formed only of the dye molecules. An acrylic resin-based ultraviolet curable resin composition (SPC-920C manufactured by Nippon Kayaku Co., Ltd.) was applied onto the obtained pigment film by a spin coater so that the thickness of the cured protective layer was 3 μm, followed by irradiation. Ultraviolet rays harden the resin composition, and a protective layer is provided on the pigment film. The polarizing element thus obtained was used as a measurement sample.

Example 2

Emulgen LS-106 used as a surfactant in Example 1 was changed to polyoxyethylene polyoxypropylene alkyl ether (Emulgen MS-110 manufactured by Kao Corporation) having an HLB value of 12.7, and the content was changed to 0.05 parts by mass. A measurement sample was prepared in the same manner as in Example 1 except for the above.

Example 3

In the composition used in Example 1, the content of CIDirect Blue 67 as a dichroic dye was changed to 3 parts by mass, and Emulgen LS-106 as a surfactant was changed to polyoxyethylene having an HLB value of 12.7. A measurement sample was prepared in the same manner as in Example 1 except that polyoxypropylene alkyl ether (Emulgen MS-110 manufactured by Kao Corporation) was used.

Example 4

The Emulgen LS-106 used as the surfactant used in Example 1 was changed to a polyoxyethylene polyoxypropylene alkyl ether having an HLB value of 12.7 (Emulgen MS-110 manufactured by Kao Corporation), and other examples and examples. A measurement sample was prepared in the same manner.

Example 5

In the dye composition used in Example 1, two kinds of dichroic dyes of 5 parts by mass of CIDirect Blue 67 and 1 part by mass of CIDirect Orange 72 were used in combination as a dichroic dye, and A measurement sample was prepared in the same manner as in Example 1 except that the Emulgen LS-106 of the active agent was changed to a polyoxyethylene polyoxypropylene alkyl ether having an HLB value of 12.7 (Emulgen MS-110 manufactured by Kao Corporation).

Example 6

Emulgen LS- used as a surfactant in Example 1 106. The measurement was carried out in the same manner as in Example 1 except that the polyoxyethylene polyoxypropylene alkyl ether having an HLB value of 12.7 (Emulgen MS-110 manufactured by Kao Corporation) was changed to 1.0 part by mass. Sample.

Example 7

The PET film as the substrate used in Example 1 was changed to a cellulose triacetate film (TD-80U manufactured by Fuji Film Co., Ltd.) having a thickness of 80 μm, and then used as a composition in the composition used in Example 1. The content of CIDirect Blue 67 of the coloring pigment was changed to 10 parts by mass, and Emulgen LS-106 as a surfactant was changed to polyoxyethylene polyoxypropylene alkyl ether having an HLB value of 12.7 (Emulgen MS-110 manufactured by Kao Corporation) A measurement sample was prepared in the same manner as in Example 1 except for the above.

Example 8

Emulgen LS-106 used as a surfactant in Example 1 was changed to a polyoxyethylene polyoxypropylene glycol block copolymer having an HLB value of 15.7 (New Pole PE-68 manufactured by Sanyo Chemical Industries Co., Ltd.). A measurement sample was prepared in the same manner as in Example 1.

Example 9

The Emulgen LS-106 used as the surfactant used in Example 1 was changed to a polyoxyethylene alkyl ether having an HLB value of 16.4 (Emulgen 1118S-70 manufactured by Kao Corporation), and otherwise the same as Example 1. A measurement sample was prepared.

Example 10

In the dye composition used in Example 1, two kinds of dichroic dyes of 4 parts by mass of CIDirect Blue 67 and 4 parts by mass of CIDirect Orange 72 were used in combination as a dichroic dye, and The Emulgen LS-106 of the active agent was changed to polyoxyethylene alkyl ether polyoxyethylene distyryl phenyl ether (Emulgen A-90 manufactured by Kao Corporation) having an HLB value of 14.5, and the content was changed to 0.2 parts by mass. A measurement sample was prepared in the same manner as in Example 1 except that it was the same.

Example 11

Emulgen A-90 used as a surfactant in Example 10 was changed to polyoxyethylene alkyl ether polyoxyethylene distyryl phenyl ether (Emulgen A-60 manufactured by Kao Corporation) having an HLB value of 12.8. A measurement sample was prepared in the same manner as in Example 10 except that the measurement was carried out.

Example 12

Emulgen A-90 as a surfactant used in Example 10 was changed to polyoxyethylene tribenzyl phenyl ether (Emulgen B-66 manufactured by Kao Corporation) having an HLB value of 12.8, and the content was changed to 0.1 part by mass. A measurement sample was prepared in the same manner as in Example 10 except for the above.

Example 13

Dissolving 4-methylpropenyloxy azobenzene in benzene to form a 20% by mass solution, using azobisisobutyronitrile as a starter, and deactivating the azobenzene at 60 ° C for 12 hours under degassing Aggregation. The solution of 10 parts by mass of the obtained azobenzene-containing polymer and 90 parts by mass of toluene was spin-coated on the PET film used in Example 1 so that the film thickness after drying became a film thickness of 0.1 μm. Then, the PET film substrate was heated at 100 ° C for 1 minute to be dried. A 500 W/h ultra-high pressure mercury lamp was prepared, and the cut light was set to visible light (>400 nm) with a cut-off filter, and further polarized to form a linearly polarized light. The linear light was polarized and irradiated to a coated surface of the substrate placed parallel to the polarizing axis of the polarizing plate for 1 minute from a distance of 50 cm from the coated surface at room temperature. 5 parts by mass of polyoxyethylene polyoxypropylene alkyl ether containing CIDirect Blue 67 as a dichroic dye, using a coater equipped with a glass rod attached to the substrate at a distance of 3 μm ( A composition of Emulgen MS-110: HLB value 12.7) 0.1 parts by mass and 100 parts by mass of water was applied to the surface of the substrate subjected to photo-alignment treatment. The obtained coating film was allowed to stand in an environment of 25 ° C and a humidity of 70% for 1 minute to dry the solvent. Then, the dried coating film was subjected to heat treatment and humidification treatment in an environment of 60 ° C and a humidity of 90% for 5 minutes to obtain a pigment film of the present invention. On the obtained pigment film, the same protective layer as in Example 1 was provided. The polarizing element thus obtained was used as a measurement sample.

Comparative example 1

The Emulgen LS-106 used as the surfactant in Example 1 was changed to the nonionic surfactant used in Example 1 of the above Patent Document 1, that is, the polyoxyethylene lauryl ether having an HLB value of 12.1 (Kao Wang) A measurement sample was prepared in the same manner as in Example 1 except that Emulgen 108) was produced, and a comparative sample was formed.

Comparative example 2

In the composition used in Example 1, the content of CIDirect Blue 67 as a dichroic dye was changed to 10 parts by mass, and Emulgen LS-106 as a surfactant was changed to the nonionic interface of Comparative Example 1. The active agent (Emulgen 108 manufactured by Kao Corporation) was changed to 1 part by mass, and a dichroic dye aqueous solution similar to that of Example 1 of Patent Document 1 was produced, and a measurement sample was prepared in the same manner as in Example 1. And form a comparative sample.

Comparative example 3

The Emulgen LS-106 used as the surfactant used in Example 1 was changed to the anionic surfactant used in the production of the aggregation dichroic dye film of Patent Document 2, that is, the aggregation of HLB value 25 A measurement sample was prepared in the same manner as in Example 1 except that oxyethylene lauryl ether sulfate (Emal 20C manufactured by Kao Corporation) was used to form a comparative sample.

Comparative example 4

A measurement sample was prepared in the same manner as in Example 1 except that Emulgen LS-106 as a surfactant used in Example 1 was not used, and a comparative sample was formed.

Comparative Example 5

Emulgen LS-106 as a surfactant used in Example 1 was not used, and the content of CIDirect Blue 67 as a dichroic dye was changed to 2 parts by mass, and was used to be spaced apart from the PET film. A dye film and a measurement sample were prepared in the same manner as in Example 1 except that a coating liquid containing a dichroic dye was applied to a coating machine of a glass rod to be mounted in a manner of 7 μm, and a comparative sample was formed.

Comparative Example 6

Emulgen LS-106 used as a surfactant in Example 1 was changed to polyoxyethylene distyrenated phenyl ether having an HLB value of 18.0 (Emulgen A-500 manufactured by Kao Corporation), and other implementations were carried out. In the same manner as in Example 1, a measurement sample was prepared to form a comparative sample.

Comparative Example 7

The same procedure as in Example 1 was carried out except that Emulgen LS-106 as a surfactant used in Example 1 was changed to a polyoxyethylene alkyl ether having an HLB value of 18.5 (Emulgen 1150S-60 manufactured by Kao Corporation). A measurement sample was prepared to form a comparative sample.

Comparative Example 8

The same procedure as in Example 1 was carried out except that Emulgen LS-106 as a surfactant used in Example 1 was changed to a polyoxyethylene alkyl ether having an HLB value of 17.9 (Emulgen 1150S-70 manufactured by Kao Corporation). A measurement sample was prepared to form a comparative sample.

Table 1 shows Ts, Tp, Tc, ρ, and Rd at the wavelengths at which the polarization obtained by the samples obtained in Examples 1 to 13 and Comparative Examples 1 to 8 was the highest. Further, the coatability of the obtained pigment film was evaluated. The applicability was observed in a 10 cm square pigment film, and the uncoated portion having a size of 50 μm or more was visually observed. When 10 or more were observed, coating defects were caused in the dye film. In Table 1, "×" It indicates that a coating failure occurred, and "○" indicates that no coating failure occurred.

From the results of Table 1, it was found that the pigment film produced by using the composition of the present invention was applied to the substrate as in Examples 1 to 12. Since the coating treatment does not cause coating failure, the coating composition of the present invention is excellent in coating property, and the pigment film after the coating failure can be further improved. In addition, it was found that even when the substrate was subjected to photo-alignment treatment as in Example 13, a composition excellent in coating properties similar to those of Examples 1 to 12 was obtained, and a pigment film having improved coating failure was further obtained. Further, as shown in Examples 1 to 13, the polarizing element having the pigment film of the present invention exhibits a high degree of polarization (ρ) and a high dichroic ratio (Rd) in addition to high-transmission green (Ts). Therefore, in the present invention, as the coating failure of the pigment film is improved, it is known that the polarizing failure of the polarizing element is also improved.

On the other hand, as a surfactant, a sample of Comparative Examples 1 and 2 in which the HLB value is a polyoxyethylene alkylene alkyl ether other than the one specified in the present invention is used, and the HLB value is used in addition to the provisions of the present invention and is not the present invention. The sample of Comparative Example 3 and the sample of Comparative Example 4 in which the surfactant was not used as the surfactant of the specific surfactant produced a coating failure on each of the pigment films. From this content, it was found that the coating failure of the pigment film of these samples was not improved, and the polarizing element having the pigment film also caused a polarization defect.

Further, the sample of Comparative Example 5 containing no surfactant as in Comparative Example 4 and having a relatively thick pigment film was calculated from the parallel transmittance (Tp) and the orthogonal transmittance (Tc). The comparison of the polarizing elements was about 2, and the sample of Comparative Example 6 containing the composition of the polyoxyethylene distyrenated phenyl ether having the HLB value other than the specification of the present invention and the use of the HLB-containing value were used. For the samples of Comparative Examples 7 and 8 of the composition of the polyoxyethylene alkyl ether, the comparison was about 1. From this content, it can be seen that even if this polarizing element is applied to a display, it is almost never presented. The contrasting polarizing element of the display. Further, in the samples of Comparative Examples 5 to 8, the degree of polarization (ρ) was less than 65%, and the dichroic ratio (Rd) was less than 5, and it was found that the function as a polarizing element was insufficient.

From the above results, it was found that the dye film produced by using the composition of the present invention can improve the coating failure at the time of application of the pigment film obtained by coating the composition containing the dichroic dye in the past, and as a result, unpolarized light can be obtained. A poorly-performing polarizing element with high quality and excellent polarizing performance.

[Industrial Applicability]

The polarizing element of the present invention is not a polarizing element using a polyvinyl alcohol resin film as in the case of the conventional polarizing element, but a solution containing a dichroic dye can be applied to a polarizing element made of a base material after rubbing, so that the polarizing element is not used. It is not necessary to carry out the processes of swelling, dyeing, stretching, and the like required in the previous steps. Further, since the film of the polarizing element can be produced only by the dichroic dye as a component for exhibiting the polarizing function, a polarizing element of the ultrathin film can be formed. Further, since the polarizing element can be produced by coating a solution containing a dichroic dye, it is not limited to the shape of a flat polarizing element such as the polarizing plate of the prior art, and may be formed into a curved shape or a spherical shape. Polarized component. In particular, the conventional stretched film can only form a polarizing plate that passes polarized light perpendicular to the stretching direction. However, the polarizing element of the present invention can be arbitrarily set in the alignment direction with respect to the base material after the brushing. A polarizing element provided with a fine pattern or a polarization in any direction is formed.

Claims (10)

A composition comprising: (A) at least one dichroic dye, (B) selected from the group consisting of polyoxyethylene alkyl ethers, polyoxyethylene alkyl alkyl ethers, polyoxyethylene distyryl phenyl ethers, and At least one surfactant of the group consisting of polyoxyethylene tribenzyl phenyl ether, and (C) a solvent; the surfactant has an HLB value of 12.5 or more and 17.5 or less. The composition of claim 1, wherein the dichroic dye is a water-soluble azo dye. The composition of claim 1 or 2, wherein the dichroic dye is a compound represented by the following formula (1) or the salt, (In the formula (1), X ₁ represents a phenyl group or a naphthyl group having one or two sulfonic acid groups, a hydroxyl group or an alkoxy group having a carbon number of 1 to 3, and X ₂ and X ₃ each independently represent a stretching. A phenyl or anthranyl group having one or two selected from the group consisting of an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a hydroxyl group, and a sulfonic acid group. One or two substituents of the group consisting of R ₁ represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an ethyl fluorenyl group, a benzamidine group, or an unsubstituted phenyl group or a carbon number of 1 to 4 a phenyl group substituted with an alkyl group, an alkoxy group having 1 to 4 carbon atoms, an amine group, a sulfonic acid group or an alkyl group having a carbon number of 1 to 4, m is 0 or 1, and n is 1 or 2). The composition of claim 3, wherein X ₁ is a compound represented by the following formula (3) or a salt thereof as a substituent, (in the formula (3), j is 1 or 2). The composition of any one of claims 1 to 4, wherein the polyoxyethylene alkylene oxide is a polyoxyethylene polyoxypropylene alkyl ether or a polyoxyethylene polyoxypropylene block polymer. The composition according to any one of claims 1 to 5, wherein the total amount of the dichroic dye is 0.1 to 15 parts by mass based on 100 parts by mass of the solvent. The composition of any one of claims 1 to 6, wherein the solvent contains at least water. A pigment film produced by using the composition according to any one of claims 1 to 7. A polarizing element having the pigment film of claim 8. The polarizing element of claim 9, wherein the dichroic ratio is 5 or more.