WO2018123691A1 - Composition pour formation de film de colorant anisotrope, et film de colorant anisotrope - Google Patents

Composition pour formation de film de colorant anisotrope, et film de colorant anisotrope Download PDF

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Publication number
WO2018123691A1
WO2018123691A1 PCT/JP2017/045329 JP2017045329W WO2018123691A1 WO 2018123691 A1 WO2018123691 A1 WO 2018123691A1 JP 2017045329 W JP2017045329 W JP 2017045329W WO 2018123691 A1 WO2018123691 A1 WO 2018123691A1
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Prior art keywords
anisotropic dye
group
dye film
composition
film
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PCT/JP2017/045329
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English (en)
Japanese (ja)
Inventor
朋子 山川
輝恒 大澤
祐三 金子
太 田中
政昭 西村
直幸 内田
崇志 藤原
水上　潤二
靖 志賀
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三菱ケミカル株式会社
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Publication of WO2018123691A1 publication Critical patent/WO2018123691A1/fr

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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • 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
    • G02F1/13363—Birefringent elements, e.g. for optical compensation

Definitions

  • the present invention is useful for anisotropic dye films formed by a wet film forming method, in particular, polarizing films included in display elements of light control elements, liquid crystal elements (LCDs), and organic electroluminescence elements (OLEDs).
  • the present invention relates to a composition for forming an anisotropic dye film exhibiting high dichroism and an anisotropic dye film.
  • a linearly polarizing film and a circularly polarizing film are used to control optical rotation and birefringence in display.
  • a circularly polarizing film is used for preventing reflection of external light.
  • iodine has been widely used as a dichroic material in these polarizing films.
  • iodine has a high sublimation property, when used as a polarizing element using a polarizing film, its heat resistance and light resistance are not sufficient. Further, since the extinction color is deep blue, it cannot be said that it is an ideal achromatic polarizing element over the entire visible spectrum region.
  • anisotropic dye film using an organic dye as a dichroic material has been studied.
  • anisotropic dye films using organic dyes conventional polymers impregnated with organic dyes, methods for obtaining films by applying organic dyes on substrates, etc. And a film formed by using a film method.
  • an adhesive layer is provided on the anisotropic dye film, a protective film of the adhesive layer is bonded, and the polarizing film is bonded with the protective film.
  • Patent Document 1 discloses an anisotropic dye film forming composition containing a trisazo dye for obtaining an anisotropic dye film having a high dichroic ratio.
  • specific dyes are used in combination in order to obtain a high dichroic ratio of the anisotropic dye film.
  • an anisotropic dye film forming composition containing an azo compound having an anthraquinone ring and a disazo dye having a naphthalene ring Patent Document 2
  • Patent Document 3 an anisotropic dye film forming composition containing a disazo dye and a monoazo compound
  • Patent Documents 4 and 5 also shows that an anisotropic dye film was obtained by combining two types of disazo dyes.
  • Patent Document 6 a composition to which an amino acid or the like is added has been developed for the purpose of improving dichroism and heat resistance.
  • the addition of surfactants improves the wettability to the substrate during coating, and at the same time inhibits the anisotropy of the dye by accumulating the surfactant at the gas-liquid interface during the drying process.
  • Patent Document 7 studies have been made to improve the dichroic ratio.
  • An object is to develop a composition for forming an anisotropic dye film capable of producing an anisotropic dye film having high moisture resistance.
  • the present inventors have found that the above problem can be solved by using a composition containing a dye and a specific polymer compound. That is, the gist of the present invention is as follows.
  • An anisotropic dye film-forming composition comprising a dye and a polymer compound having an acidic group and a basic group.
  • the composition for forming an anisotropic dye film according to any one of [1] to [7] further comprising a water-soluble organic compound.
  • An anisotropic dye film comprising a dye, a polymer compound having an acidic group and a basic group, and a water-soluble organic compound.
  • An optical element comprising the anisotropic dye film according to any one of [16] to [16].
  • the present invention has the following gist.
  • An anisotropic film-forming composition comprising a filler having an average primary particle diameter of 1 nm to 500 nm.
  • a filler having an average primary particle diameter of 1 nm to 500 nm.
  • the filler is a metal oxide.
  • the metal oxide is silica and / or alumina.
  • the basic group includes an amino group.
  • acidic group contains a sulfo group.
  • composition for forming an anisotropic dye film of the present invention By using the composition for forming an anisotropic dye film of the present invention, improvement in moisture resistance of the formed anisotropic dye film can be expected. In addition to improving the margin for the storage environment at the time of manufacture, it contributes to stable manufacturing, and the storage environment can be made cheaper.
  • an embodiment of the present invention provides a composition for forming an anisotropic dye film that contains a water-soluble organic compound and has excellent storage stability and can be uniformly applied.
  • the present invention provides an anisotropic dye film that suppresses film defects over time by being excellent in moisture resistance, has high film hardness, and is excellent in dichroic ratio.
  • the anisotropic dye film forming composition of one embodiment of the present invention containing a water-soluble organic compound the moisture resistance and hardness of the formed anisotropic dye film can be improved over time. Suppression of film defects can be expected.
  • coating an anisotropic dye film composition is suppressed, and the anisotropic dye film excellent in mass-productivity is formed.
  • anisotropic dye film-forming composition of one aspect of the present invention containing a specific filler, in addition to the improvement of moisture resistance, other base materials
  • An anisotropic film having both high productivity and handling property due to suppression of adhesion and high polarization degree is provided.
  • the anisotropic dye film referred to in the present invention is an electromagnetic property in any two directions selected from a total of three directions in the three-dimensional coordinate system of the thickness direction of the anisotropic dye film and any two orthogonal in-plane directions.
  • the electromagnetic property include optical properties such as absorption and refraction, and electrical properties such as resistance and capacitance.
  • films having optical anisotropy such as absorption and refraction include polarizing films such as linearly polarizing films and circularly polarizing films, retardation films, and conductive anisotropic dye films.
  • the anisotropic dye film of the present invention is preferably used for a polarizing film, a retardation film and a conductive anisotropic dye film, and more preferably used for a polarizing film.
  • the composition for forming an anisotropic dye film of the present invention includes a dye and a polymer compound having an acidic group and a basic group.
  • the aspect of the composition for forming an anisotropic dye film is not particularly limited as long as the polymer compound and the dye described above are included.
  • the composition for forming an anisotropic dye film may be a solution, a liquid crystal, or a dispersed state.
  • the liquid crystal phase is preferably from the viewpoint that the anisotropic dye film formed after the solvent evaporates is formed with a high degree of orientation.
  • the state of the liquid crystal phase is specifically described on pages 1 to 16 of “Basics and Applications of Liquid Crystal” (Shinichi Matsumoto, Ryo Tsunoda, 1991).
  • it is a liquid crystal state exhibiting both liquid and crystal properties, which means a nematic phase, a cholesteric phase, a smectic phase, or a discotic phase.
  • the liquid crystal phase is preferably a nematic phase because the order in the solution tends to be low and the viscosity tends to be low.
  • the polymer compound that can be used in the present invention is a polymer compound having an acidic group and a basic group (hereinafter sometimes referred to as “polymer compound” in the present specification).
  • the basic group or acidic group has good compatibility with water molecules and has hygroscopicity, so that the anisotropic dye film has a property of easily adsorbing moisture.
  • the anisotropic dye film the dye forms an aggregate having a certain size in order to exhibit its anisotropy.
  • Compounds such as amino acids described in Patent Document 6 are presumed to connect and fix this dye aggregate.
  • the compounds such as amino acids that are connected to each other are bonded by weak hydrogen bonds, and the association force is weakened by absorbing moisture. For this reason, it is presumed that the movement of the dye aggregate cannot be suppressed and precipitation and cracking occur.
  • a part of a weak hydrogen bond network between compounds such as amino acids is replaced with a strong covalent bond. Therefore, it is presumed that even when moisture is adsorbed, the state in which the movement of the dye aggregate is suppressed can be maintained.
  • the anisotropic dye film formed by the dye alone tends to be brittle, the hardness is low, but by adding the above polymer compound, the brittleness is eliminated by the plasticizer effect, and the hardness is improved. Presumed.
  • the substituent which the said high molecular compound has it can explain as follows.
  • a liquid crystalline composition that does not cause phase separation.
  • a pigment may have an acidic group or a basic group. Basic groups are usually positively charged or cationic, and acidic groups are usually negatively charged or anionic. Therefore, in order for the dye and the polymer compound to form an association pair, the polymer compound needs to have a basic group or an acidic group.
  • the polymer compound when the polymer compound has only one of an acidic group and a basic group, it is presumed that either a strong association with the dye or a strong repulsion occurs.
  • the dye aggregates are cross-linked through the polymer compound, and it becomes difficult to form a uniform liquid crystal phase.
  • the polymer compound preferably has a basic group and an acidic group at the same time.
  • the basic group and acidic group possessed by the polymer compound are as follows.
  • the acidic group and the basic group are functional groups having a pKa of less than 7 and a basic group of 7 or more, respectively.
  • pKa is a logarithmic value of the reciprocal of the concentration acid dissociation constant Ka, that is, -log Ka.
  • the acidic group possessed by the polymer compound examples include a sulfo group, a carboxyl group, and a phosphate group. Among these, it is preferable that the acidic group does not have an aromatic partial structure in order to suppress the lamination failure of the dye. In view of maintaining water solubility and improving order, the acidic group preferably contains a sulfo group, and particularly preferably a sulfo group.
  • the basic group examples include nitrogen-containing basic groups (which preferably include an electron-donating nitrogen atom, and the nitrogen atom preferably has a property of being positively charged or cationic).
  • the basic group preferably does not have an aromatic partial structure, and particularly preferably includes an amino group, and particularly preferably an amino group, in order to suppress the lamination failure of the dye.
  • a part or all of the acidic group and the basic group contained in the polymer compound may take a salt form. At least a part of the acidic group may be a salt-type acidic group.
  • an alkali metal such as sodium, lithium or potassium, an ammonium which may be substituted with an alkyl group or a hydroxyalkyl group
  • organic amines include lower alkyl amines having 1 to 6 carbon atoms, hydroxy-substituted lower alkyl amines having 1 to 6 carbon atoms, carboxy-substituted lower alkyl amines having 1 to 6 carbon atoms, and the like. Is mentioned.
  • the type is not limited to one type, and a plurality of types may be mixed.
  • an alkali metal salt having a high ionization tendency is desirable.
  • lithium and / or sodium are preferable, and lithium is particularly preferable from the viewpoint of suppressing the phase separation of the composition containing the pigment and the polymer compound and improving the solubility.
  • lithium is particularly preferable from the viewpoint of increasing the dichroic ratio of a film made of a composition containing a dye and a polymer compound.
  • At least a part of the basic group may be a salt type basic group.
  • the basic group salt type include salts of inorganic acids such as hydrochloric acid and sulfuric acid, and salts of organic acids such as acetic acid and formic acid. Is mentioned.
  • the molecular weight (weight average molecular weight) of the polymer compound is usually preferably 800 or more, more preferably 1000 or more, and particularly preferably 1400 or more. Further, it is usually preferably 10,000 or less, more preferably 7000 or less, and particularly preferably 5000 or less. For example, 800 or more and 10,000 or less are preferable, 1000 or more and 7000 or less are more preferable, and 1400 or more and 5000 or less are more preferable.
  • the molecular weight is not less than the above lower limit value, moisture resistance tends to be obtained, and when the molecular weight is not more than the above upper limit value, solubility tends to be obtained.
  • the main chain of the polymer compound is not particularly limited, but from the compatibility of the dye described later, an amide bond, an ester bond, an ether bond, a —NR 1 — group (R 1 is a hydrogen atom, a methyl group or an ethyl group) And a carbon chain containing at least one selected from the group consisting of a sulfonyl group, a carbon chain consisting only of a saturated bond, and the like, particularly a carbon chain consisting only of a saturated bond, an amide bond and / or —NR. It is desirable to have a carbon chain structure containing a 1 -group.
  • the main chain may have a plurality of the bonds or the groups.
  • the unsaturated bond portion is inhibited from inhibiting the ⁇ - ⁇ stack of the dye, and the anisotropic dye film-forming composition has liquid crystallinity.
  • the degree of polarization of the anisotropic dye film tends to be improved.
  • the side chain of the polymer compound is not particularly limited as in the case of the main chain.
  • amide bond, ester bond, ether bond, —NR 1 — group R 1 represents a hydrogen atom, a methyl group or an ethyl group
  • a carbon chain containing at least one selected from the group consisting of a sulfonyl group, a carbon chain consisting only of a saturated bond, and the like are desirable.
  • the number of atoms from the side chain to the most distant atom is preferably 2 or more and 10 or less, more preferably 8 or less.
  • the ratio of the acidic group and the basic group in the same main chain is not particularly limited.
  • the numerical value of basic group / (basic group + acidic group) is preferably greater than 0.05, more preferably 0.1 or more, and even more preferably 0.2 or more. 0.8 or less, more preferably 0.7 or less, still more preferably 0.6 or less, still more preferably 0.5 or less, and even more preferably 0.4 or less.
  • more than 0.05 and 0.8 or less are preferable, 0.1 or more and 0.7 or less are more preferable, 0.2 or more and 0.6 or less are more preferable, and 0.2 or more and 0.5 or less are more preferable.
  • 0.2 to 0.4 is even more preferable.
  • the compatibility between the dye and the polymer compound tends to be improved.
  • the lamination between the dyes proceeds from the association of the dye and the polymer compound, the liquid crystallinity of the composition is improved, and the polarization degree of the anisotropic dye film tends to be improved.
  • the combination of the basic group and the acidic group of the polymer compound is not particularly limited.
  • the basic group is an amino group
  • the acidic group is a sulfo group, a carboxyl group and / or a phosphate group.
  • the basic group is an amino group and the acidic group is a sulfo group.
  • a basic group an amino group that has a small skeleton and generates a hard cation according to the HSAB rule when cationized has a strong interaction with the dye, and is less likely to cause phase separation.
  • the acidic group is preferably a sulfo group or a phosphate group.
  • the two or more groups may be the same group or different groups.
  • the polymer compound may have a random structure or a block structure, and particularly preferably has a random structure. Due to the random structure, the compatibility of the polymer compound and the dye tends to be high. Further, it may be a linear polymer or a branched polymer. Since the said high molecular compound has high hydrophilicity, when the composition for anisotropic dye film formation of this invention contains the below-mentioned filler, it is preferable from a viewpoint of improving the dispersion stability. Furthermore, the addition of a polymer compound tends to lower the refractive index and extinction coefficient of the anisotropic dye film, so it is anisotropic when the anisotropic dye film is used for a polarizing film or an antireflection film. In some cases, it is possible to reduce interface reflection between the photosensitive dye film and the adjacent layer.
  • polymer compound examples include JP-A No. 2004-027162, JP-A No. 2002-293842, JP-A No. 52-101291, JP-B No. 03-020127, JP-A No. 2004-115675, and the like. Can be produced by the method described in the above publication. Exemplary compounds of the polymer compound are shown below, but are not limited to the following structures. All counter cations are described in the form of protons, but the counter cations include those described above such as alkali metals. Moreover, the proton form and the salt form may be mixed, or a plurality of salt forms may be included. L, m, and n in the following exemplary compounds represent arbitrary integers.
  • the content of the polymer compound (% by weight in the total solid content) is not particularly limited.
  • the polymer compound is preferably 90% by weight or less, more preferably 80% by weight or less, still more preferably 70% by weight or less, based on the total solid content of the anisotropic dye film-forming composition. It is particularly preferable that it is 60% by weight or less. On the other hand, it is preferably 0.1% by weight or more, more preferably 1% by weight or more, further preferably 3% by weight or more, more preferably 5% by weight or more, more preferably 10% by weight or more, and more preferably 20% by weight or more. 30% by weight or more is particularly preferable, and 40% by weight or more is particularly preferable.
  • it is preferably 0.1% by weight or more and 90% by weight or less, more preferably 1% by weight or more and 90% by weight or less, further preferably 5% by weight or more and 80% by weight or less, and further preferably 10% by weight or more and 70% by weight or less. It is preferably 20% by weight or more and 60% by weight or less, more preferably 30% by weight or more and 60% by weight or less, still more preferably 40% by weight or more and 60% by weight or less.
  • the degree of polarization of the anisotropic dye film tends to increase.
  • By setting it to the above lower limit or more brittleness of the anisotropic dye film tends to be suppressed, the hardness is improved, and the reflectance is reduced. It exists in the tendency which is excellent in moisture resistance because it is the said range.
  • the mixing ratio of the polymer compound and the dye in the composition for forming an anisotropic dye film of the present invention is not particularly limited.
  • Dye: polymer compound 10: 90 to 99.9: 0.1 is preferable. Further, it is more preferably 20:80 to 90:10, further preferably 25:75 to 80:20, and particularly preferably 30:70 to 60:40.
  • the anisotropic dye film has excellent polarization and moisture resistance, and further tends to suppress brittleness of the anisotropic dye film and improve hardness.
  • a pigment means a substance or compound that absorbs at least a part of the wavelength in the visible light region.
  • a dye that can be used in the present invention a water-soluble organic dye or a dichroic dye is used.
  • dye is a pigment
  • the pigment having liquid crystallinity means a pigment exhibiting lyotropic liquid crystallinity in a solvent.
  • the dye exhibiting lyotropic liquid crystallinity used in the present invention is preferably soluble in water or an organic solvent in order to form an anisotropic dye film by coating.
  • water-soluble means that the pigment is dissolved in water at room temperature, usually 0.1% by weight or more, preferably 1% by weight or more.
  • the above dye preferably has a molecular weight of 200 or more, particularly preferably 300 or more, in a free state that does not take a salt form. Moreover, it is preferable that it is 1500 or less, and it is especially preferable that it is 1200 or less. For example, it is preferably 200 or more and 1500 or less, and particularly preferably 300 or more and 1200 or less. Moreover, the said pigment
  • the dye examples include azo dyes (hereinafter also simply referred to as “azo dyes”), stilbene dyes, cyanine dyes, phthalocyanine dyes, condensed polycyclic dyes (perylene dyes, oxazine dyes), and the like. Can be mentioned. Among these dyes, azo dyes that can take a high molecular arrangement in the anisotropic dye film are preferable.
  • An azo dye means a dye having at least one azo group. The number of azo groups in one molecule is preferably 2 or more, preferably 6 or less, more preferably 4 or less, and even more preferably 3 or less from the viewpoint of color tone and production.
  • an azo dye having at least one group selected from the group consisting of a sulfo group, a carboxyl group, a phospho group, and a phosphinic acid group can cause the anisotropic dye film to dissolve, drop off, crack, etc. There is a tendency that it is possible to obtain the effect of suppressing the deterioration of the optical characteristics and reducing the deterioration of the optical characteristics.
  • the azo dye has a sulfo group.
  • the pigment that can be used in the present invention is not particularly limited, and a known pigment can be used.
  • the dye include, for example, JP-A-2006-0799030, JP-A-2010-168570, JP-A-2007-302807, JP-A-2008-081700, JP-A-09-230142, JP-A-2007-. No.
  • the dye used in the present invention may be used in the form of a free acid, or a part of the acid group may have a salt form. Further, a salt-type dye and a free acid-type dye may be mixed. When the dye is obtained in a salt form at the time of production, it may be used as it is or may be converted into a desired salt form (salt exchange).
  • salt exchange method a known method can be arbitrarily used, and examples thereof include the following methods.
  • a strong acid such as hydrochloric acid is added to an aqueous solution of a dye obtained in a salt form, the dye is acidified in the form of a free acid, and then the dye is added with an alkaline solution having a desired counter ion (eg, lithium hydroxide aqueous solution).
  • a desired counter ion eg, lithium hydroxide aqueous solution.
  • a method of neutralizing acidic groups and salt exchange A method in which a large excess of a neutral salt (for example, lithium chloride) having a desired counter ion is added to an aqueous dye solution obtained in a salt form, and salt exchange is performed in the form of a salting-out cake.
  • An aqueous solution of a dye obtained in a salt form is treated with a strongly acidic cation exchange resin, and the dye is acidified in the form of a free acid, and then an alkali solution having a desired counter ion (for example, an aqueous lithium hydroxide solution). ) To neutralize the acidic group of the dye and perform salt exchange. 4) A method in which an aqueous solution of a dye obtained in a salt form is allowed to act on a strongly acidic cation exchange resin that has been previously treated with an alkaline solution having a desired counter ion (for example, an aqueous lithium hydroxide solution), thereby performing salt exchange.
  • the acidic group of the dye is a free acid type or a salt type depends on the pKa of the dye and the pH of the aqueous dye solution.
  • the salt form include salts of alkali metals such as sodium, lithium and potassium, ammonium salts optionally substituted with an alkyl group or hydroxyalkyl group, and salts of organic amines.
  • the organic amine include a lower alkyl amine having 1 to 6 carbon atoms, a hydroxy-substituted lower alkyl amine having 1 to 6 carbon atoms, a carboxy-substituted lower alkyl amine having 1 to 6 carbon atoms, and the like.
  • the type is not limited to one type, and a plurality of types may be mixed.
  • dye can be used independently, these 2 or more types may be used together, and it is also possible to mix
  • pigments when blended with other pigments include C.I. I. Direct Yellow 12, C.I. I. Direct Yellow 34, C.I. I. Direct Yellow 86, C.I. I. Direct Yellow 142, C.I. I. Direct Yellow 132, C.I. I. Acid Yellow 9, C.I. I. Acid Yellow 25, C.I. I. Direct Orange 39, C.I. I. Direct Orange 72, C.I. I. Direct Orange 79, C.I. I. Acid Orange 28, C.I. I. Direct Red 39, C.I. I. Direct Red 79, C.I. I. Direct Red 81, C.I. I. Direct Red 83, C.I. I. Direct Red89, C.I. I.
  • the blending dye may include an azo dye whose free acid form is represented by the formula (I).
  • Ar 21 and Ar 22 each independently represents an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent, n represents 0 or 1.
  • Ar 21 and Ar 22 each independently represent an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent.
  • aromatic hydrocarbon group examples include groups derived from a single ring and a plurality of rings.
  • the number of rings contained in the groups derived from a plurality of rings is not particularly limited, but is usually 2 or more and 4 or less, preferably 3 or less.
  • the aromatic hydrocarbon group in Ar 22 has two free valences, benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene. Ring, acenaphthene ring, fluoranthene ring, fluorene ring and the like.
  • the aromatic hydrocarbon group may have a substituent.
  • substituents that may have include a hydrophilic group that is usually introduced to enhance the solubility of the azo compound, and an electron-withdrawing group or electron-donating group that is introduced to adjust the color tone as a dye. preferable.
  • substituent include an alkoxy group, a hydroxyl group, an amino group, an acylamino group, a carbamoyl group, a sulfamoyl group, a carboxy group, a sulfo group, a cyano group, and a phosphate group.
  • the aromatic heterocyclic group is not particularly limited, but is preferably a group derived from a monocyclic or bicyclic heterocyclic ring from the viewpoint of increasing the degree of polarization.
  • atoms other than carbon constituting the aromatic heterocyclic group include a nitrogen atom, a sulfur atom, and an oxygen atom. From the viewpoint of increasing the degree of polarization, a nitrogen atom is particularly preferable.
  • the aromatic heterocyclic group has a plurality of atoms constituting a ring other than carbon, these may be the same or different.
  • Preferable examples include pyridine ring, quinoline ring, isoquinoline ring, thiazole ring, benzothiazole ring and the like.
  • the aromatic heterocyclic group may have a substituent.
  • substituents that may be included include a hydrophilic group, an electron withdrawing group, an electron donating group, and a hydrogen bonding functional group. Specific examples include an alkyl group, an alkoxy group, an acylamino group, an amino group, a carbamoyl group, a sulfamoyl group, a nitro group, a carboxy group, a sulfo group, a hydroxyl group, a cyano group, and a halogen atom.
  • substituent groups and substituents are respectively synonymous with those mentioned as the substituents that the aromatic hydrocarbon group of Ar 21 may have, and preferred ranges and substituents that may be included. Are also synonymous.
  • azo dyes in which the form of the free acid is represented by the formula (I) include, but are not limited to, the dyes described below.
  • blending can be used individually or in mixture of 2 or more types.
  • the anisotropic dye film can be appropriately adjusted to a desired color tone by adjusting the addition amount of the compounding dye.
  • the concentration of the dye in the composition for forming an anisotropic dye film is preferably 0, although it depends on the film forming conditions of the anisotropic dye film. 0.01% by weight or more, more preferably 0.1% by weight or more, preferably 50% by weight or less, more preferably 30% by weight or less. For example, 0.01 wt% or more and 50 wt% or less are preferable, and 0.1 wt% or more and 30 wt% or less are more preferable.
  • the dye concentration is within the above range, the viscosity of the composition for forming an anisotropic dye film capable of applying a uniform thin film is obtained, and the dye does not tend to precipitate.
  • anisotropy such as a sufficient dichroic ratio tends to be obtained in the anisotropic dye film.
  • the composition for forming an anisotropic dye film of the present invention may further contain a water-soluble organic compound.
  • the water-soluble organic compound is preferably a compound excluding the above-mentioned dye (including a compounding dye when a compounding dye is used).
  • the water-soluble organic compound is not particularly limited, but is preferably a compound that can easily accumulate at the gas-liquid interface of the coating film of the composition for forming an anisotropic dye film and has an action of making the surface tension uniform.
  • a compound having a leveling action can be used.
  • the term “water-soluble” refers to a molecular state that hydrates and disperses in water.
  • the water-soluble organic compound is not particularly limited, but preferably has both a hydrophilic group and a hydrophobic group. Since the water-soluble organic compound has a hydrophilic group and a hydrophobic group, the hydrophobic group part of the water-soluble organic compound is on the film interface side and the hydrophilic group part is on the film side when the coating film of the anisotropic dye film forming composition is dried. As a result, water-soluble organic compounds tend to accumulate at the gas-liquid interface.
  • the composition for forming the anisotropic dye film As a result, in the state of the composition for forming the anisotropic dye film, it was mixed with the anisotropic dye, but during application, phase separation occurred between the anisotropic dye layer and the water-soluble organic compound layer, and the substrate side
  • the dichroic ratio can be maintained as in the case where no polymer compound is added without impairing the order of the accumulated anisotropic dye.
  • the water-soluble organic compounds densely accumulated on the surface after drying the coating film of the anisotropic dye film-forming composition tend to prevent water from entering the anisotropic dye film and improve moisture resistance. At the same time, lower the surface tension. From these results, it is possible to achieve both the improvement of mass productivity and the maintenance of the dichroic ratio of the anisotropic dye film when applying the composition for forming an anisotropic dye film, which has been impossible in the past.
  • hydrophilic groups include nonionic groups and ionic groups.
  • the nonionic group include a hydroxy group, an alkyloxy group having 1 to 4 carbon atoms, a polyethyleneoxy group, and a polypropyleneoxy group.
  • the ionic group include an amino group, a monoalkylamino group, a dialkylamino group, a carboxy group, a sulfo group, a pyridinium group, a quaternary ammonium group, a phosphoric acid group, and a polyethyleneimino group.
  • hydrophobic group examples include a linear alkyl group, a branched alkyl group, a phenylalkyl group which may have a substituent, a perpropylene oxide, a polyorganosiloxy group, and a perfluoroalkyl group.
  • water-soluble organic compounds examples include silicone-based, fluorine-based, acrylic-based, and vinyl-based compounds.
  • silicone-based and fluorine-based compounds are particularly preferable.
  • the molecular weight of the water-soluble organic compound is not particularly limited, but is preferably 10,000 or less, more preferably 5000 or less, and still more preferably 2000 or less. Moreover, a minimum is not specifically limited.
  • water-soluble organic compound examples include the following.
  • Silicone compounds contain Si atoms in the compound, specifically polydimethylsiloxane, polyether-modified polydimethylsiloxane, polymethylalkylsiloxane, modified polysiloxane, reactive silicone, silicone surfactants, etc. Is mentioned.
  • the fluorine-based compound contains F atoms in the compound, and specifically includes fluorine group-containing oligomers or polymers, perfluoro group-containing oligomers or polymers, perfluoroalkyl group-containing carboxylates, perfluoroalkyl groups, Examples thereof include phosphoric acid-containing phosphate esters, fluorine group- and carboxyl group-containing oligomers. Moreover, the thing containing the reactive group which reacts with a heat
  • the acrylic compound is an acrylate or acrylate oligomer having a skeleton such as acrylate or methacrylate, in which a hydrogen atom of a side chain carboxy group is substituted with another functional group.
  • a hydrogen atom of a side chain carboxy group is substituted with another functional group.
  • other functional groups in which the hydrogen atom of the side chain carboxy group is substituted include reactive groups such as alkyl groups, polyethyleneoxyethyl groups, polyester groups, amino groups, and hydroxyl groups.
  • Vinyl-based is an oligomer or polymer obtained by polymerizing a compound containing a vinyl group, and specific examples include vinyl acetate.
  • the concentration of the water-soluble organic compound in the composition for forming an anisotropic dye film is not particularly limited as long as the effect of the present invention is not significantly impaired.
  • it is 0.001 mass% or more, More preferably, it is 0.003 mass% or more.
  • it is 0.1 mass% or less, More preferably, it is 0.05 mass% or less.
  • 0.001 mass% or more and 0.1 mass% or less are preferable, and 0.003 mass% or more and 0.05 mass% or less are more preferable.
  • the compounding ratio of the water-soluble organic compound and the dye in the composition for forming an anisotropic dye film of the present invention is not particularly limited.
  • the blending ratio of the dye and the water-soluble organic compound (weight ratio of the water-soluble organic compound to the dye) is preferably 0.00001 or more, more preferably 0.0001 or more, and further preferably 0.0005 or more. Further, it is preferably 0.5 or less, more preferably 0.1 or less, further preferably 0.01 or less, and still more preferably 0.005 or less.
  • 0.00001 or more and 0.5 or less are preferable, 0.00001 or more and 0.1 or less are more preferable, 0.0001 or more and 0.01 or less are more preferable, and 0.0005 or more and 0.005 or less are more preferable.
  • leveling effects can be obtained, and the orientation of the dye molecules tends not to be hindered.
  • the composition for forming an anisotropic dye film of the present invention may further contain a filler having an average primary particle diameter of 1 nm to 500 nm. Since such a composition and an anisotropic dye film formed from such a composition contain a filler on the film surface, unevenness is formed on the film surface, the adhesion area with other base materials is reduced, and adhesion is lowered. By doing so, it is considered that handling and productivity are improved. Moreover, since the elastic modulus of the anisotropic dye film is increased by adding the filler, it is considered that the adhesiveness is lowered. Further, by adding a filler, the refractive index and extinction coefficient of the anisotropic dye film are reduced.
  • the layer between the anisotropic dye film and the adjacent layer It is possible to reduce the difference in refractive index and extinction coefficient, and as a result, it is considered possible to reduce interface reflection.
  • the filler that can be used in the composition for forming an anisotropic dye film is not particularly limited, and is, for example, an inorganic filler.
  • silicon oxide silicon oxide
  • aluminum oxide alumina
  • titanium oxide antimony oxide
  • metal oxides such as tin oxide, zinc oxide, zirconium oxide, selenium oxide, yttrium oxide and cerium oxide, metal nitrides such as silicon nitride, and metal sulfides such as palladium sulfide and cadmium sulfide.
  • the filler may be composed of only one of these, or may be composed of two or more.
  • metal oxides such as silicon oxide, aluminum oxide, titanium oxide, zinc oxide, and zirconium oxide are preferable from the viewpoint of filler stability, and silicon oxide and oxidation are particularly preferable from the viewpoint of affinity with dyes and polymer compounds.
  • those containing aluminum are more preferable, and those containing silicon oxide and aluminum oxide are more preferable from the viewpoint of the stability of the composition for forming an anisotropic dye film.
  • the surface of these fillers may be modified with a specific organic substance, or may be shared with a dispersant or the like. From the viewpoint of reducing the reflectance of an anisotropic dye film and an optical element produced from such a film, silicon oxide is particularly preferable.
  • the shape of a filler is not specifically limited, A spherical shape, rod shape, plate shape, etc. are mentioned. From the viewpoint of enhancing the transparency of the anisotropic dye film, a spherical shape is preferable.
  • the method for producing the filler is not particularly limited, and the filler can be produced by any method such as a gas phase method, a sol-gel method, a molten metal spray oxidation method, a colloidal precipitation method, or arc discharge.
  • the filler may be subjected to a surface coating treatment for dispersion stability and suppression of deterioration, and the surface coating may be homogeneous or heterogeneous.
  • Specific materials for the surface coating are inorganic materials or organic materials, such as metal oxides such as zirconium oxide and silicon oxide, metal hydroxides such as aluminum hydroxide, organic acids such as organosiloxane and stearic acid, etc. 1 type or 2 types or more can be used.
  • metal oxides such as zirconium oxide and silicon oxide
  • metal hydroxides such as aluminum hydroxide
  • organic acids such as organosiloxane and stearic acid, etc. 1 type or 2 types or more can be used.
  • a metal oxide or a metal hydroxide is preferable, and a metal hydroxide is more preferable.
  • the filler may be subjected to plasma surface modification treatment or mechanochemical treatment.
  • the average primary particle size of the filler of the present invention is preferably 500 nm or less, more preferably 200 nm or less, further preferably 100 nm or less, particularly preferably 90 nm or less, particularly preferably 70 nm or less, even more preferably 50 nm or less, preferably 1 nm or more, More preferably, it is 5 nm or more, More preferably, it is 7 nm or more, Most preferably, it is 10 nm or more.
  • it is preferably 1 nm or more and 500 nm or less, more preferably 5 nm or more and 200 nm or less, further preferably 7 nm or more and 100 nm or less, still more preferably 10 nm or more and 90 nm or less, even more preferably 10 nm or more and 70 nm or less, and even more preferably 10 nm or more and 50 nm or less.
  • the adhesion of the anisotropic dye film tends to be suppressed, and the dispersion stability of the filler in the composition tends to be improved.
  • the average primary particle size of the particles is determined by confirming the primary particles from the TEM (transmission electron microscope) and SEM (scanning electron microscope) photograph images of the anisotropic dye film formed from the composition of the present invention or the composition film. , 30 average values can be obtained.
  • evaluation may be performed by a dynamic light scattering method.
  • the filler content (% by weight in the total solid content) with respect to the total solid content is preferably 0.1% or more, more preferably 0.5% or more, and still more preferably 0. 0.7% or more, particularly preferably 1.0% or more, preferably 50% or less, more preferably 30% or less, still more preferably 20% or less, particularly preferably 15% or less, and particularly preferably 10% or less.
  • 0.1% to 50% is preferable, 0.5% to 30% is more preferable, 0.7% to 20% is more preferable, 1.0% to 15% is more preferable, 1.0% or more and 10% or less are especially preferable.
  • the refractive index and extinction coefficient of the anisotropic dye film tend to be reduced, and the reflectance tends to be reduced. By doing so, the degree of polarization and transparency of the anisotropic dye film tend to be high.
  • the composition for forming an anisotropic dye film of the present invention contains a resin other than a low molecular dispersant, a high molecular dispersant, and a binder resin, which are usually marketed as a dispersant, in order to improve the dispersion stability of the filler. It is also possible. Among these, it is preferable to blend a polymer dispersant from the viewpoint of dispersion stability of the filler in the composition.
  • polymer dispersant examples include a urethane dispersant, a polyethyleneimine dispersant, a polyoxyethylene alkyl ether dispersant, a polyoxyethylene glycol diester dispersant, a sorbitan aliphatic ester dispersant, and an aliphatic modified polyester. And the like, and the like. These dispersants can be used alone or in admixture of two or more.
  • composition for forming an anisotropic dye film of the present invention contains a dispersant
  • its content is preferably 0.1% by weight or more, more preferably 0.5% by weight or more. More preferably 1% by weight or more, particularly preferably 2% by weight or more, preferably 50% by weight or less, more preferably 30% by weight or less, still more preferably 20% by weight or less, particularly preferably 10% by weight or less, particularly preferably. Is 5% by weight or less.
  • 0.1 wt% or more and 50 wt% or less are preferable, 0.5 wt% or more and 30 wt% or less are more preferable, 1 wt% or more and 20 wt% or less are more preferable, and 2 wt% or more and 10 wt% or less are preferable. Even more preferred is 2 wt% or more and 5 wt% or less.
  • the amount is not less than the lower limit, the dispersion stability of the filler in the composition tends to be improved, and when the amount is not more than the upper limit, the degree of polarization and the transparency of the anisotropic dye film tend to increase. is there.
  • solvent water, a water-miscible organic solvent, or a mixture thereof is suitable.
  • organic solvent include alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, and glycerin, glycols such as ethylene glycol and diethylene glycol, and cellosolves such as methyl cellosolve and ethyl cellosolve. These may be used alone or in admixture of two or more.
  • the total solid content of the composition for forming an anisotropic dye film is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, and preferably 50%.
  • % By mass or less, more preferably 40% by mass or less, further preferably 30% by mass or less, particularly preferably 25% by mass or less, for example, preferably 5% by mass to 50% by mass, more preferably 10% by mass to 40% by mass. % Or less, more preferably 15% by mass or more and 30% by mass or less, and still more preferably 15% by mass or more and 25% by mass or less.
  • an anisotropic dye film having a desired film thickness can be formed by setting it to the lower limit value or more, and a film thickness uniformity of the anisotropic dye film tends to be improved by setting the upper limit value or less. is there.
  • the composition for forming an anisotropic dye film of the present invention may or may not express a lyotropic liquid crystal phase, but only the amount of solvent in the composition for forming an anisotropic dye film when the lyotropic liquid crystal phase is not expressed. It is preferable that the lyotropic liquid crystal phase is expressed by changing the above. The expression of the lyotropic liquid crystal phase is preferable because the dye exhibits a high degree of orientation in the anisotropic dye film and a high dichroic anisotropic dye film tends to be obtained. It is more preferable that the composition for forming an anisotropic dye film expresses a lyotropic liquid crystal phase because higher orientation in the anisotropic dye film tends to be obtained.
  • the pH of the composition for forming an anisotropic dye film is not particularly limited, but is preferably 4.0 or more, more preferably 5.0 or more, and most preferably 5.5 or more. Further, it is preferably 12 or less, more preferably 11 or less, and most preferably 10 or less.
  • the pH value is less than or equal to the above upper limit value, the basic group of the polymer compound is cationized, the compatibility with the dye is improved, and phase separation (precipitation) tends to be suppressed.
  • the acidic group is anionized, and in the composition for forming an anisotropic dye film, phase separation due to excessive interaction between the dye and the polymer compound can be suppressed. There is a tendency.
  • composition for forming an anisotropic dye film may further include a surfactant, a leveling agent, a coupling agent, a pH adjuster, alanine, valine, leucine, isoleucine, glycine, glycylglycine, glycylglycyl.
  • Acidic groups and basic groups such as glycine, serine, proline, cysteine, cystine, glutamine, 6-aminohexanoic acid, amino acids described in WO 2005/069048, 3-amino-1-propanesulfonic acid, taurine, etc.
  • Additives such as low molecular weight compounds having Depending on the additive, wettability, applicability, stability of the composition for forming an anisotropic dye film, and the like may be improved.
  • the surfactant any of anionic, cationic and nonionic properties can be used.
  • the addition concentration is not particularly limited, but is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, and still more preferably as the concentration in the composition for forming an anisotropic dye film. It is 0.05 mass% or more. Moreover, Preferably it is 0.8 mass% or less, More preferably, it is 0.5 mass% or less.
  • 0.001% by mass to 0.8% by mass is preferable, 0.01% by mass to 0.5% by mass is more preferable, and 0.05% by mass to 0.5% by mass is further preferable.
  • a known pH adjuster such as acid / alkali is anisotropically used. May be added either before or after mixing the constituents of the composition for forming a functional dye film or during mixing.
  • additives other than those described above “Additive for Coating”, Edited by J. et al. Known additives described in Bieleman, Willy-VCH (2000) can also be used.
  • the method for producing the composition for forming an anisotropic dye film of the present invention is not particularly limited.
  • a dye, other additives, a solvent, and the like are mixed, and the dye is dissolved by stirring and shaking at 0 to 100 ° C.
  • a homogenizer, a bead mill disperser or the like may be used.
  • a method for removing foreign substances and the like in the composition other than filtration there is a method using centrifugation described in JP 2012-53388 A.
  • the anisotropic dye film of the present invention can be formed using the anisotropic dye film forming composition of the present invention.
  • the anisotropic dye film of the present invention may contain a dye and a polymer compound having an acidic group and a basic group.
  • the anisotropic dye film of the present invention may contain a dye, a polymer compound having an acidic group and a basic group, and a water-soluble organic compound.
  • the orientation characteristics of the anisotropic dye film can be expressed using a dichroic ratio.
  • a dichroic ratio of 8 or more functions as a polarizing element, but is preferably 15 or more, more preferably 20 or more, further preferably 25 or more, and particularly preferably 30 or more. Also, the higher the dichroic ratio, the better. When the dichroic ratio is a specific value or more, it is useful as an optical element described later, particularly as a polarizing element.
  • the dichroic ratio (D) referred to in the present invention is represented by the following formula when the pigment is uniformly oriented.
  • D Az / Ay
  • Az is the absorbance observed when the polarization direction of the light incident on the anisotropic dye film is parallel to the alignment direction of the pigment
  • Ay is the absorbance observed when the polarization direction is perpendicular.
  • Each absorbance is not particularly limited as long as the same wavelength is used, and any wavelength may be selected depending on the purpose. However, when the degree of orientation of the anisotropic dye film is expressed, the maximum absorption of the anisotropic dye film is used. It is preferable to use a value in wavelength.
  • the transmittance in the visible light wavelength region of the anisotropic dye film of the present invention is preferably 25% or more. 35% or more is more preferable, and 40% or more is particularly preferable.
  • permeability should just be an upper limit according to a use. For example, when increasing the degree of polarization, the transmittance is preferably 50% or less. When the transmittance is in a specific range, it is useful as the following optical element, and particularly useful as an optical element for a liquid crystal display used for color display.
  • the degree of polarization of the anisotropic dye film in an aspect of the present invention at a transmittance of 42.5% is preferably 80% or more, more preferably 85% or more, still more preferably 90% or more, and particularly preferably 91% or more. It is. The higher the degree of polarization, the better. When the degree of polarization is not less than a specific value, it is useful as an optical element described later, particularly as a polarizing element.
  • the anisotropic dye film of the present invention is preferably produced by a wet film forming method.
  • the wet film-forming method referred to in the present invention is a method in which a composition for forming an anisotropic dye film is applied on a substrate by any method, and a dye or the like is oriented and laminated on the substrate through a process of drying the solvent. .
  • the dye when the composition for forming an anisotropic dye film is applied on a substrate, the dye itself self-associates in the anisotropic dye film forming composition or in the process of drying the solvent. Causes orientation in a small area.
  • an anisotropic dye film having desired performance can be obtained by orienting in a certain direction in a macro region.
  • This is different from the method based on the principle that a so-called polyvinyl alcohol (PVA) film or the like is dyed with a solution containing a dye and stretched, and the dye is oriented only by a stretching process.
  • the external field includes the influence of the alignment treatment layer previously applied on the substrate, shear force, magnetic field, and the like, and these may be used alone or in combination.
  • the process of applying the anisotropic dye film-forming composition on the substrate to form a film, the process of aligning by applying an external field, and the process of drying the solvent may be performed sequentially or simultaneously.
  • the method for applying the composition for forming an anisotropic dye film on the substrate in the wet film forming method include a coating method, a dip coating method, an LB film forming method, a known printing method, and the like.
  • the present invention preferably uses a coating method.
  • the orientation direction of the anisotropic dye film is usually coincident with the application direction, but may be different from the application direction.
  • the orientation direction of the anisotropic dye film is, for example, a polarizing transmission axis or absorption axis in the case of a polarizing film, and a fast axis or a slow axis in the case of a retardation film. That is.
  • the anisotropic dye film in this embodiment functions as a polarizing film or retardation film that obtains linearly polarized light, circularly polarized light, elliptically polarized light, etc. by utilizing the anisotropy of light absorption, as well as a film forming process and a substrate. And by selecting a composition containing an organic compound (pigment or transparent material), it can be functionalized as various anisotropic dye films such as refractive anisotropy and conduction anisotropy.
  • the method for obtaining the anisotropic dye film by applying the composition for forming the anisotropic dye film is not particularly limited.
  • Yuji Harasaki “Coating Engineering” (Asakura Shoten Co., Ltd., March 20, 1971). Issue) Method described on pages 253 to 277, “Creation and application of molecularly coordinated materials” supervised by Kunihiro Ichimura (CMC Publishing Co., Ltd., published on March 3, 1998), pages 118 to 149, Slot die coating method, spin coating method, spray coating method, bar coating method, roll coating method, blade coating method, curtain coating method, fountain method, dipping method on a substrate having a step structure (which may be subjected to orientation treatment in advance) The method of apply
  • a die coater used in the slot die coating method generally includes a coating machine that discharges a coating solution, a so-called slit die.
  • the slit die is disclosed in, for example, JP-A-2-164480, JP-A-6-154687, JP-A-9-131559, “Basics and Applications of Dispersion / Coating / Drying” (2014, Technosystem Corporation).
  • composition for use can also be suitably used for a bar coater.
  • Examples of the substrate used for forming the anisotropic dye film of the present invention include glass, triacetate, acrylic, polyester, polyimide, triacetylcellulose, or urethane film.
  • the substrate surface is aligned by a known method described in “Liquid Crystal Handbook” Maruzen Co., Ltd., issued October 30, 2000, pages 226 to 239, etc.
  • a treatment layer (alignment film) may be provided.
  • the alignment treatment layer it is considered that the dye is oriented due to the influence of the orientation treatment of the orientation treatment layer and the shearing force applied to the composition for forming an anisotropic dye film during coating.
  • the method for supplying the composition for forming an anisotropic dye film and the supply interval when applying the composition for forming an anisotropic dye film are not particularly limited.
  • the anisotropic dye film When the anisotropic dye film is thin, it may continuously occur because the supply operation of the coating liquid becomes complicated and the coating film thickness may vary when the coating liquid starts and stops. It is desirable to apply while supplying the composition for forming an anisotropic dye film.
  • the speed at which the composition for forming an anisotropic dye film is applied is usually 1 mm / second or more, preferably 5 mm / second or more. Moreover, it is 1000 mm / sec or less normally, Preferably it is 200 mm / sec or less.
  • the coating temperature of the composition for forming an anisotropic dye film is usually 0 ° C. or higher and 80 ° C. or lower, preferably 40 ° C. or lower.
  • coating of the composition for anisotropic dye film formation becomes like this. Preferably it is 10% RH or more, More preferably, it is 30% RH or more, Preferably it is 80% RH or less.
  • the film thickness of the anisotropic dye film is preferably 10 nm or more, more preferably 50 nm or more as a dry film thickness. On the other hand, it is preferably 30 ⁇ m or less, more preferably 1 ⁇ m or less. When the film thickness of the anisotropic dye film is within an appropriate range, uniform orientation and uniform film thickness of the dye tend to be obtained in the film.
  • the anisotropic dye film may be insolubilized.
  • Insolubilization means a treatment step that increases the stability of the film by controlling the elution of the compound from the anisotropic dye film by reducing the solubility of the compound in the anisotropic dye film.
  • an ion with a lower valence is replaced with an ion with a higher valence (for example, a monovalent ion is replaced with a polyvalent ion), or an organic molecule or polymer having a plurality of ionic groups.
  • a replacement process is listed.
  • the anisotropic dye film thus obtained is treated by the method described in JP-A-2007-241267, etc. to form an anisotropic dye film that is insoluble in water. From the viewpoint of durability and the like.
  • the optical element of the present invention includes the anisotropic dye film of the present invention.
  • the optical element is a polarizing element that obtains linearly polarized light, circularly polarized light, elliptically polarized light, etc. by utilizing the anisotropy of light absorption, a retardation element, an element having functions such as refractive anisotropy and conduction anisotropy. Represents. These functions can be appropriately adjusted according to the anisotropic dye film forming process and the selection of a composition containing a substrate or an organic compound (a dye or a transparent material). In the present invention, it is most preferably used as a polarizing element.
  • the polarizing element of the present invention may have any other film (layer) as long as it has the anisotropic dye film of the present invention.
  • it can be produced by providing an alignment film on a substrate and forming an anisotropic dye film on the surface of the alignment film.
  • the polarizing element is not limited to an anisotropic dye film, but an overcoat layer having functions such as improving polarization performance and improving mechanical strength; adhesive layer or antireflection layer; alignment film; retardation film , A function as a brightness enhancement film, a function as a reflection or antireflection film, a function as a transflective film, a layer having an optical function such as a function as a diffusion film; .
  • the layers having various functions described above may be formed by lamination by coating, bonding, or the like, and used as a laminate. These layers can be provided as appropriate in accordance with the manufacturing process, characteristics, and functions, and the position and order of the layers are not particularly limited.
  • the positions where the above layers are formed may be formed on the anisotropic dye film, or may be formed on the opposite surface of the substrate provided with the anisotropic dye film.
  • the order of forming the above layers may be before or after forming the anisotropic dye film.
  • the layer having a function as a retardation film can be formed by bonding a retardation film obtained by the following method to another layer constituting the polarizing element.
  • the retardation film is subjected to, for example, a stretching process described in JP-A-2-59703, JP-A-4-230704, or a process described in JP-A-7-230007. Can be formed.
  • the layer having a function as a brightness enhancement film can be formed by bonding the brightness enhancement film obtained by the following method to another layer constituting the polarizing element.
  • the brightness enhancement film is formed by forming a fine hole by a method as described in JP-A No. 2002-169025 and JP-A No. 2003-29030, or two or more layers having different central wavelengths of selective reflection. It can be formed by superposing cholesteric liquid crystal layers.
  • a layer having a function as a reflective film or a transflective film can be formed by, for example, bonding a metal thin film obtained by vapor deposition or sputtering to another layer constituting the polarizing element. it can.
  • the layer having a function as a diffusion film can be formed, for example, by coating the other layer constituting the polarizing element with a resin solution containing fine particles.
  • the layer having a function as a retardation film or an optical compensation film is obtained by applying and aligning a liquid crystal compound such as a discotic liquid crystal compound or a nematic liquid crystal compound on another layer constituting the polarizing element. Can be formed.
  • the anisotropic dye film in the present embodiment is used as an anisotropic dye film for various display elements such as LCDs and OLEDs, it is directly anisotropic on the surface of the electrode substrate or the like constituting these display elements.
  • a dye film can be formed, or a substrate on which an anisotropic dye film is formed can be used as a constituent member of these display elements.
  • the optical element of the present invention can be suitably used for applications such as a flexible display because a polarizing element can be obtained by forming an anisotropic dye film on a substrate by coating or the like.
  • the wet cake of this monoazo compound was dissolved in 220 parts by weight of N-methylpyrrolidone and 110 parts by weight of water, diazotized by adding 3.00 parts by weight of sodium nitrite under acidic conditions of hydrochloric acid, and dissolved in 200 parts by weight of water.
  • the precipitate was taken out by salting out. It is dissolved in water, neutralized with sodium hydroxide, isopropyl alcohol is added, the precipitated solid is filtered and separated, and the resulting wet cake is dried to obtain an azo dye represented by the following formula (I-1). 31.1 parts by weight of sodium salt were obtained.
  • aqueous solution of a sodium salt of a trisazo dye represented by the formula (I-2) is passed through a cation exchange resin (SK1BH manufactured by Mitsubishi Chemical Corporation) to make an aqueous solution of a free acid, neutralized with an aqueous lithium hydroxide solution, concentrated and dried.
  • a lithium salt of a trisazo dye represented by the following formula Dye-1 was obtained.
  • composition A2 An anisotropic dye film-forming composition A2 was prepared in the same manner as in Comparative Example A1, except that sodium polyacrylate (weight average molecular weight: 5000) was used instead of sodium polystyrene sulfonate in Comparative Example A1. Thereafter, liquid crystal properties were confirmed at room temperature, and it was confirmed that the liquid crystal portion and the non-liquid crystal portion were in a phase separated state.
  • sodium polyacrylate weight average molecular weight: 5000
  • composition A3 An anisotropic dye film-forming composition A3 was prepared in the same manner as in Comparative Example A1, except that polyallylamine (weight average molecular weight: 3000) was used instead of sodium polystyrene sulfonate in Comparative Example A1. Thereafter, liquid crystal properties were confirmed at room temperature, and it was confirmed that there was no liquid crystal properties.
  • polyallylamine weight average molecular weight: 3000
  • Example A1 Polymer compound (polymer AA) having an acidic group and a basic group, which is a copolymer containing allylamine and sodium allylsulfonate in a molar ratio of 4: 6 instead of sodium polystyrenesulfonate in Comparative Example A1 (weight)
  • An anisotropic dye film-forming composition A4 was produced in the same manner as in Comparative Example A1, except that the average molecular weight was 1700). Then, when liquid crystal property was confirmed at normal temperature, it was confirmed that the liquid crystal state was uniform.
  • Example A2 In the same manner as in Example A1, except that the ratio of Dye-1 to polymer AA in Example A1 was changed to 60:40, and the counter cation of polymer AA was changed to polymer AB salt-exchanged with lithium, an anisotropic dye A film-forming composition A5 was produced.
  • the polymer AA is replaced with a lithium salt by passing an aqueous solution of the polymer AA (sodium salt) through a cation exchange resin (SK1BH, manufactured by Mitsubishi Chemical Corporation) to obtain an aqueous solution of free acid, and then the pH of the aqueous solution is increased with an aqueous lithium hydroxide solution. This was carried out by neutralizing to 7.0 and concentrating to dryness. Then, when liquid crystal property was confirmed at normal temperature, it was confirmed that the liquid crystal state was uniform.
  • Example A4 An anisotropic dye film-forming composition A6 was produced in the same manner as in Example A2, except that all of the polymer AB in Example A2 was replaced with L-(+)-Lysine. Then, when liquid crystal property was confirmed at normal temperature, it was confirmed that the liquid crystal state was uniform.
  • a saturated aqueous solution of potassium sulfide was prepared to create a constant humidity environment. At this time, when the hygrometer was confirmed, it was kept at 97% humidity at 25 ° C.
  • composition of the present invention containing a dye and a specific polymer compound can form an anisotropic dye film because it maintains a uniform liquid crystal state. Moreover, it was shown that the obtained anisotropic pigment
  • Reference Example B2 an anisotropic dye film-forming composition B2 was prepared in the same manner as in Reference Example B1, except that water was mixed so that the solution had a solid concentration of 17%.
  • liquid crystallinity was confirmed at normal temperature (25 ° C.) using a polarizing microscope, it was confirmed that the liquid crystal state was uniform.
  • the isotropic phase appearance temperature when the temperature was raised was 46.4 ° C.
  • the viscosity at normal temperature was measured with an E-type viscometer, it was 111 cP under the condition of the rotor rotation speed of 10 rpm.
  • Example B1 In Reference Example B1, 0.02% of a fluorine-based water-soluble organic compound (Megafac F-444 manufactured by DIC Corporation, having an ethylene oxide group as a hydrophilic group) based on the solid content of the composition for forming an anisotropic dye film
  • an anisotropic dye film-forming composition B4 having a solid content concentration of 18% was prepared in the same manner as in Reference Example B1, except that perfluoroalkyl was further added as a hydrophobic group.
  • perfluoroalkyl was further added as a hydrophobic group.
  • Example B2 In Reference Example B1, 0.02% of a fluorine-based water-soluble organic compound (Megafac F-477 manufactured by DIC Corporation, having a hydrophilic group and a hydrophobic group) based on the solid content of the composition for forming an anisotropic dye film A composition B5 for forming an anisotropic dye film having a solid content concentration of 18% was prepared in the same manner as in Reference Example B1, except that a fluorine group was further added.
  • liquid crystallinity was confirmed at normal temperature (25 ° C.) using a polarizing microscope, it was confirmed that the liquid crystal state was uniform.
  • the isotropic phase appearance temperature when the temperature was raised was 48.3 ° C. Further, when the viscosity at normal temperature was measured with an E-type viscometer, it was 112 cP under the condition of the rotor rotation speed of 10 rpm.
  • Example B3 In Reference Example B1, 0.02% of a fluorine-based water-soluble organic compound (Megafac F-553 manufactured by DIC Corporation, having a hydrophilic group and a hydrophobic group) based on the solid content of the composition for forming an anisotropic dye film
  • the composition B6 for forming an anisotropic dye film having a solid content concentration of 18% was prepared in the same manner as in Reference Example B1, except that a fluorine group was further added.
  • liquid crystallinity was confirmed at normal temperature (25 ° C.) using a polarizing microscope, it was confirmed that the liquid crystal state was uniform.
  • the isotropic phase appearance temperature when the temperature was raised was 56.8 ° C. Further, when the viscosity at normal temperature was measured with an E-type viscometer, it was 108 cP under the condition of the rotor rotation speed of 10 rpm.
  • Example B4 In Reference Example B1, 0.02% of a fluorine-based water-soluble organic compound (Megafac F-556 manufactured by DIC Corporation, having a hydrophilic group and a hydrophobic group) based on the solid content of the composition for forming an anisotropic dye film
  • the composition B7 for forming an anisotropic dye film having a solid content concentration of 18% was prepared in the same manner as in Reference Example B1, except that a fluorine group was further added.
  • liquid crystallinity was confirmed at normal temperature (25 ° C.) using a polarizing microscope, it was confirmed that the liquid crystal state was uniform.
  • the isotropic phase appearance temperature when the temperature was raised was 49.8 ° C. Further, when the viscosity at normal temperature was measured with an E-type viscometer, it was 108 cP under the condition of the rotor rotation speed of 10 rpm.
  • Example B5 In Reference Example B1, 0.02% of a silicone-based water-soluble organic compound (BYK-348 manufactured by BYK-Chemie Co., Ltd., having a polyether group as a hydrophilic group and hydrophobic An anisotropic dye film-forming composition B8 having a solid content concentration of 18% was prepared in the same manner as in Reference Example B1, except that a siloxane group was added as a group.
  • a siloxane group was added as a group.
  • the isotropic phase appearance temperature when the temperature was raised was 51.2 ° C. Further, when the viscosity at normal temperature was measured with an E-type viscometer, it was 112 cP under the condition of the rotor rotation speed of 10 rpm.
  • Example B6 In Reference Example B1, 0.02% of a silicone-based water-soluble organic compound (BYK-349 manufactured by BYK-Chemie Co., Ltd. based on the solid content of the anisotropic dye film-forming composition.
  • An anisotropic dye film-forming composition B9 having a solid content concentration of 18% was prepared in the same manner as in Reference Example B1, except that a siloxane group was added as a group.
  • liquid crystallinity was confirmed at normal temperature (25 ° C.) using a polarizing microscope, it was confirmed that the liquid crystal state was uniform.
  • the isotropic phase appearance temperature when the temperature was raised was 51.5 ° C. Further, when the viscosity at normal temperature was measured with an E-type viscometer, it was 103 cP under the condition of the rotor rotation speed of 10 rpm.
  • Example B7 In Reference Example B1, 0.02% of a silicone-based water-soluble organic compound (KP-104 manufactured by Shin-Etsu Chemical Co., Ltd. having a polyol group as a hydrophilic group) based on the solid content of the composition for forming an anisotropic dye film
  • An anisotropic dye film-forming composition B10 having a solid content concentration of 18% was prepared in the same manner as in Reference Example B1, except that a siloxane group as a hydrophobic group was further added.
  • liquid crystallinity was confirmed at normal temperature (25 ° C.) using a polarizing microscope, it was confirmed that the liquid crystal state was uniform.
  • the isotropic phase appearance temperature when the temperature was raised was 51.0 ° C. Further, when the viscosity at normal temperature was measured with an E-type viscometer, it was 116 cP under the condition of the rotor rotation speed of 10 rpm.
  • Example B8 In Reference Example B2, 0.01% of a silicone-based water-soluble organic compound (BYK-349, manufactured by BYK Chemie Co., Ltd., having a polyether group as a hydrophilic group and hydrophobic An anisotropic dye film-forming composition B11 having a solid concentration of 17% was prepared in the same manner as in Reference Example B2, except that a siloxane group was added as a group.
  • a siloxane group was added as a group.
  • the isotropic phase appearance temperature when the temperature was raised was 45.1 ° C.
  • the viscosity at normal temperature was measured with an E-type viscometer, it was 110 cP under the condition of the rotor rotation speed of 10 rpm.
  • Example B9 In Reference Example B2, 0.01% acrylic water-soluble organic compound (BYK-380N manufactured by BYK-Chemie Co., Ltd. having a hydrophilic group and a hydrophobic group based on the solid content of the composition for forming an anisotropic dye film.
  • a composition B12 for forming an anisotropic dye film having a solid content concentration of 17% was prepared in the same manner as in Reference Example B2, except that it was further added.
  • liquid crystallinity was confirmed at normal temperature (25 ° C.) using a polarizing microscope, it was confirmed that the liquid crystal state was uniform.
  • the isotropic phase appearance temperature when the temperature was raised was 45.5 ° C. Further, when the viscosity at normal temperature was measured with an E-type viscometer, it was 111 cP under the condition of the rotor rotation speed of 10 rpm.
  • Example B10 In Reference Example B3, 0.006% of a silicone-based water-soluble organic compound (BYK-348 manufactured by BYK-Chemie Co., Ltd., having a polyether group as a hydrophilic group, hydrophobic An anisotropic dye film-forming composition B13 having a solid content concentration of 17% was prepared in the same manner as in Reference Example B3 except that an alkyl group was added as a group.
  • an alkyl group was added as a group.
  • the isotropic phase appearance temperature when the temperature was raised was 30.7 ° C. Further, when the viscosity at room temperature was measured with an E-type viscometer, it was 134 cP under the condition of the rotor rotation speed of 10 rpm.
  • Example B11 In Reference Example B3, 0.006% of a silicone-based water-soluble organic compound (BYK-349 manufactured by BYK-Chemie Co., Ltd. based on the solid content of the anisotropic dye film-forming composition.
  • An anisotropic dye film-forming composition B14 having a solid content concentration of 17% was prepared in the same manner as in Reference Example B3 except that a siloxane group was added as a group.
  • liquid crystallinity was confirmed at normal temperature (25 ° C.) using a polarizing microscope, it was confirmed that the liquid crystal state was uniform.
  • the isotropic phase appearance temperature when the temperature was raised was 30.4 ° C. Further, the viscosity at room temperature was measured with an E-type viscometer.
  • Example B12 In Reference Example B3, 0.006% acrylic water-soluble organic compound (BYK-380N manufactured by BYK-Chemie Co., Ltd., having a hydrophilic group and a hydrophobic group based on the solid content of the composition for forming an anisotropic dye film.
  • the composition B15 for forming an anisotropic dye film having a solid content concentration of 17% was prepared in the same manner as in Reference Example B3, except that it was added in the form of a block structure.
  • liquid crystallinity was confirmed at normal temperature (25 ° C.) using a polarizing microscope, it was confirmed that the liquid crystal state was uniform.
  • the isotropic phase appearance temperature when the temperature was raised was 32.0 ° C. Further, when the viscosity at room temperature was measured with an E-type viscometer, it was 158 cP under the condition of the rotor rotation speed of 10 rpm.
  • the anisotropic dye film-forming compositions of Reference Examples B1 to B3 and Examples B1 to B12 of the present invention containing a dye and a specific polymer compound are all in a uniform liquid crystal state at room temperature.
  • the moisture resistance was improved.
  • the composition for forming an anisotropic dye film of Examples B1 to B12 which is a composition for forming an anisotropic dye film of one embodiment of the present invention containing a water-soluble organic compound, significantly reduces coating stripes, and , Transferability to film was significantly reduced. Furthermore, the liquid crystallinity (isotropic phase appearance temperature) of the anisotropic dye film-forming composition and the optical characteristics of the anisotropic dye film were maintained without greatly increasing the viscosity.
  • Example C1 Filler CB1 (BYK-3600, average primary particle size 40 nm, manufactured by Big Chemie Japan Co., Ltd.) is 5% in the total solid content while maintaining the mixing ratio of the pigment and polymer compound in Reference Example C1 at 30:70 (weight ratio). Then, ion-exchanged water was added so that the solution had a solid content concentration of 16.5%. Then, it stirred for 90 minutes at 80 degreeC, and it was made to melt
  • Example C2 Filler CB2 (manufactured by Nissan Chemical Industries, Snowtex CM, average primary particle size 20) with the mixing ratio of Dye-1, polymer compound CC1 and additive CD1 in Reference Example C2 being 30:60:10 (weight ratio) ⁇ 25 nm) was added to 1% of the total solids, and ion-exchanged water was added so as to obtain a solution having a solids concentration of 17.7%. Then, it stirred for 90 minutes at 80 degreeC, and it was made to melt
  • Example 3 An anisotropic dye film-forming composition C5 was produced in the same manner as in Example C2, except that the amount of filler CB2 added to the total solid content was 5% and the solid content concentration was changed to 18.8%.
  • Example C4 An anisotropic dye film-forming composition C6 was produced in the same manner as in Example C3 except that the amount of filler CB2 added to the total solid content was changed to 10%.
  • Example C5 Similar to Example C4 except that filler CB1 was replaced with filler CB3 (Nissan Chemical Industries, Snowtex C, average primary particle size 10-15 nm) and the solid content concentration was changed to 17.1%.
  • the composition C7 for forming a functional dye film was prepared.
  • Example C6 Similar to Example C2, except that filler CB1 was replaced with filler CB4 (manufactured by Nissan Chemical Industries, Snowtex 20L, average primary particle size 40-50 nm), and the solid content concentration was changed to 16.9%.
  • the composition C8 for forming a functional dye film was prepared.
  • the anisotropic dye film-forming compositions prepared in Examples C1 to C6 and Reference Examples C1 to C2 were each coated on a glass substrate using an applicator and then air-dried to prepare anisotropic dye films.
  • the transmittance and polarization degree of the obtained anisotropic dye film were measured using a spectrophotometer (product name “RETS-100” manufactured by Otsuka Electronics Co., Ltd.) equipped with a Gram Thomson polarizer. The following is shown from the transmittance wavelength dependence (Ty ( ⁇ ), Tz ( ⁇ ), Tm ( ⁇ )) of 400 nm to 800 nm obtained by making linearly polarized measuring light incident on the anisotropic dye film.
  • the anisotropic dye film-forming compositions prepared in Examples C1 to C6 and Reference Examples C1 to C2 were each coated on a glass substrate using an applicator and then air-dried to prepare anisotropic dye films.
  • the obtained anisotropic dye film was allowed to stand for 1 day in an atmosphere of 71% relative humidity at room temperature. Thereafter, the PET film was pressed against the coating film with a load of 0.025 kgf / mm 2 , and the adhesion of the coating film to the PET film after peeling was observed and evaluated according to the following criteria.
  • B When there is much adhesion
  • A When there is almost no adhesion
  • the anisotropic dye film-forming compositions of the present invention of Reference Examples C1 to C2 and Examples C1 to C6 containing a dye and a specific polymer compound are all in a uniform liquid crystal state at room temperature and have moisture resistance. It was improved. In Example C1 to which the filler was added, the degree of polarization was only reduced by 0.5% with respect to Reference Example 1, and the adhesion could be further reduced. In Examples C2 to C6 to which the filler was added, the degree of polarization was only reduced by 0.1 to 0.4% with respect to Reference Example 2, and the adhesion could be further reduced. From these results, it was shown that the composition for forming an anisotropic dye film of one embodiment of the present invention containing a filler can further reduce adhesion while maintaining a high degree of polarization.

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  • Physics & Mathematics (AREA)
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  • General Physics & Mathematics (AREA)
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Abstract

L'invention a pour objet de fournir une composition pour formation de film de colorant anisotrope qui permet de fabriquer un film de colorant anisotrope de résistance élevée à l'humidité. Plus précisément, l'invention fournit une composition pour formation de film de colorant anisotrope qui contient un colorant, et un composé polymère possédant un groupe acide et un groupe basique.
PCT/JP2017/045329 2016-12-27 2017-12-18 Composition pour formation de film de colorant anisotrope, et film de colorant anisotrope WO2018123691A1 (fr)

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