WO2012124400A1 - Film polarisant, liquide de revêtement et dispositif d'affichage d'image - Google Patents

Film polarisant, liquide de revêtement et dispositif d'affichage d'image Download PDF

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Publication number
WO2012124400A1
WO2012124400A1 PCT/JP2012/052362 JP2012052362W WO2012124400A1 WO 2012124400 A1 WO2012124400 A1 WO 2012124400A1 JP 2012052362 W JP2012052362 W JP 2012052362W WO 2012124400 A1 WO2012124400 A1 WO 2012124400A1
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Prior art keywords
substituted
group
polarizing film
general formula
compound
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English (en)
Japanese (ja)
Inventor
中西　貞裕
美由紀 黒木
永恵 清水
祥一 松田
亀山　忠幸
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Nitto Denko Corp
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Nitto Denko Corp
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state

Definitions

  • the present invention relates to a polarizing film having a high dichroic ratio, and a coating liquid for forming the polarizing film.
  • the polarizing film is an optical member having a function of transmitting specific linearly polarized light from polarized light or natural light.
  • a general-purpose polarizing film can be obtained, for example, by stretching a polyvinyl alcohol film dyed with iodine.
  • a polarizing film containing a disazo compound having a naphthalene ring is also known (Patent Document 1). This polarizing film is obtained by a method (solution casting method) in which a coating liquid containing the disazo compound and a solvent is applied onto a substrate. In this coating solution, the disazo compound forms a supramolecular aggregate in the solution to exhibit a liquid crystal phase.
  • a coating film in which the disazo compound is oriented is obtained.
  • the oriented disazo compound is fixed by drying the coating film.
  • the dried coating film has polarizing properties.
  • a polarizing film having a high dichroic ratio cannot be obtained.
  • Patent Document 2 discloses a polarizing film containing an azo compound having an anthraquinone ring and a disazo compound having a naphthalene ring. This polarizing film is also obtained by a method in which a coating liquid containing the two kinds of azo compounds and a solvent is applied onto a substrate.
  • a coating liquid containing the two kinds of azo compounds and a solvent is applied onto a substrate.
  • an azo compound having a large aromatic ring such as an anthraquinone ring
  • a crystal may be generated.
  • the orientation of the azo compound tends to be nonuniform. For this reason, in patent document 2, a polarizing film with a high dichroic ratio cannot be obtained.
  • the first object of the present invention is to provide a polarizing film having a high dichroic ratio.
  • the second object of the present invention is to provide a coating liquid for forming a polarizing film having a high dichroic ratio.
  • the polarizing film of the present invention contains a disazo compound represented by the following general formula (1) and a monoazo compound represented by the following general formula (2).
  • Q represents a substituted or unsubstituted aryl group
  • R 1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted acetyl group, a substituted or unsubstituted benzoyl group.
  • each M 1 independently represents a counter ion
  • m1 represents an integer of 0 to 2
  • n1 represents an integer of 0 to 6
  • m1 And at least one of n1 is not 0, o1 represents an integer of 0 to 1, and p1 represents an integer of 1 to 4.
  • R 2 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted acetyl group, a substituted or unsubstituted benzoyl group, or a substituted or unsubstituted phenyl group
  • M 2 each independently represents a counter ion
  • m 2 represents an integer of 0 to 2
  • n 2 represents an integer of 0 to 6
  • p 2 Represents an integer of 1 to 4.
  • the disazo compound is a disazo compound represented by the following general formula (3).
  • the monoazo compound is a monoazo compound represented by the following general formula (5).
  • R 2 , M 2 , m2, n2 and p2 in the general formula (5) are the same as those in the general formula (2).
  • a coating liquid is provided.
  • This coating liquid contains the disazo compound represented by the general formula (1), the monoazo compound represented by the general formula (2), and a solvent.
  • an image display device is provided.
  • This image display apparatus has any of the above polarizing films as its constituent members.
  • the polarizing film of this invention contains the disazo compound represented by General formula (1) and the monoazo compound represented by General formula (2), it has a high dichroic ratio.
  • the coating liquid of the present invention contains a disazo compound represented by the general formula (1) and a monoazo compound represented by the general formula (2). By coating this coating solution on a suitable development surface, a polarizing film having a relatively thin and high dichroic ratio can be easily obtained.
  • the fragmentary sectional view which shows the polarizing film which concerns on one embodiment.
  • the fragmentary sectional view showing the polarizing plate concerning one embodiment.
  • the polarizing film of the present invention contains the following disazo compound and monoazo compound.
  • the polarizing film of the present invention may contain one or more selected from the following disazo compounds and one or more selected from the following monoazo compounds.
  • the description “substituted or unsubstituted” means “having a substituent or not having a substituent”.
  • the description “Y to Z” means “Y or more and Z or less”.
  • the disazo compound used in the present invention is represented by the following general formula (1).
  • Q represents a substituted or unsubstituted aryl group
  • R 1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted acetyl group, a substituted or unsubstituted benzoyl group.
  • each M 1 independently represents a counter ion
  • m1 represents an integer of 0 to 2
  • n1 represents an integer of 0 to 6
  • m1 And at least one of n1 is not 0, o1 represents an integer of 0 to 1, and
  • p1 represents an integer of 1 to 4.
  • 1 ⁇ (m1 + n1) 6
  • each R 1 may be the same or different.
  • n1 and p1 are 2 or more (that is, when the number of substitutions of SO 3 M 1 is 2 or more)
  • each M 1 may be the same or different.
  • each substituent of NHR 1 , SO 3 M 1 , OH and SO 3 M 1 may be substituted at any position of the naphthalene ring.
  • Examples of the aryl group represented by Q in the general formula (1) include a phenyl group, a phenyl group to which a heterocyclic ring is bonded, and a condensed ring group in which two or more benzene rings are condensed (for example, a naphthyl group).
  • the phenyl group includes a phenyl group in which non-adjacent carbon atoms are substituted with nitrogen atoms.
  • the aryl group represented by Q may have a substituent or may not have a substituent. Regardless of whether the aryl group is substituted or unsubstituted, the disazo compound is excellent in solubility in an aqueous solvent and is also excellent in orientation.
  • the aryl group has a substituent
  • examples of the substituent include an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a thioalkyl group having 1 to 6 carbon atoms, and a dihydroxypropyl group.
  • the substituent is a polar group.
  • the polar group means a functional group having polarity.
  • Examples of the polar group include functional groups containing oxygen and / or nitrogen having a relatively high electronegativity such as a nitro group, a cyano group, an amino group, a hydroxyl group, a sulfonic acid group, and a carboxyl group.
  • Q in the general formula (1) is preferably a phenyl group represented by the following formula (A).
  • X represents a substituent
  • x represents the number of substitutions of X and represents an integer of 0 to 5.
  • Specific examples of the substituent X are the same as the substituents in the aryl group, so refer to it.
  • X is preferably 1 or 2.
  • Q in the general formula (1) is, for example, one selected from the following formula group.
  • R 1 is preferably a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted acetyl group, and more preferably a hydrogen atom or a substituted or unsubstituted acetyl group.
  • the substituted or unsubstituted alkyl group include substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms.
  • M 1 (counter ion) of the general formula (1) is preferably a hydrogen ion; an alkali metal ion such as Li, Na, K, or Cs; an alkaline earth metal ion such as Ca, Sr, or Ba; Ions; ammonium ions optionally substituted with alkyl groups or hydroxyalkyl groups; salts of organic amines, and the like.
  • the other metal ions include Ni + , Fe 3+ , Cu 2+ , Ag + , Zn 2+ , Al 3+ , Pd 2+ , Cd 2+ , Sn 2+ , Co 2+ , Mn 2+ , and Ce 3+ .
  • Examples of the organic amine include alkylamines having 1 to 6 carbon atoms, alkylamines having 1 to 6 carbon atoms having a hydroxyl group, and alkylamines having 1 to 6 carbon atoms having a carboxyl group.
  • each M 1 may be the same or different.
  • M 1 of SO 3 M 1 is a divalent or higher cation, or the M 1 is stabilized by binding electrostatically with other anions, Alternatively, the M 1 is shared and stabilized with other azo compounds.
  • m1 is preferably 1.
  • n1 in the general formula (1) is preferably 1 or 2.
  • Such a disazo compound of the general formula (1) has an SO 3 M 1 group and an NHR 1 group, and is particularly excellent in solubility in an aqueous solvent.
  • Such an azo compound is preferable because it forms a stable supramolecular aggregate in a liquid and exhibits a liquid crystal phase.
  • the naphthyl group of the general formula (1) (the naphthyl group represented on the right side of the formula (1)), the OH group is bonded to the ortho position with respect to the bonding portion of the azo group.
  • the hydrogen atom of the highly reactive OH group and one nitrogen of the azo group are bonded in the coating solution.
  • the planar structure of the naphthyl group is stabilized by changing the OH group and bonding the hydrogen atom to the azo group.
  • the naphthyl group of the general formula (1) (the naphthyl group represented on the right side of the formula (1)) include the following formulas (a) to (h).
  • R 1 and M 1 in the formulas (a) to (h) are the same as those in the general formula (1).
  • the disazo compound of the general formula (1) having the formula (a), the formula (b), the formula (c), or the formula (e) can be synthesized from a raw material that is distributed in large quantities in the market. For this reason, such a disazo compound is preferable because it can be obtained relatively inexpensively.
  • specific examples of the naphthylene group (naphthylene group between the two azo groups of the formula (1)) bonded to the two azo groups include, for example, the following formulas (B) to (D):
  • the naphthylene group represented is mentioned.
  • M 1 , o1 and p1 in the formulas (B) to (D) are the same as those in the general formula (1).
  • the p1 is 1 or 2.
  • naphthylene groups of the above formulas (B) to (D) naphthylene groups represented by the following formulas (E) to (H) are preferable.
  • the disazo compound of the general formula (1) having a naphthylene group of the formula (B), the formula (E) or the formula (F) is more preferable. Since this disazo compound has a 1,4-naphthylene group represented by the formula (B), formula (E) or formula (F), it has a large dielectric anisotropy in the molecular minor axis direction. Having such a 1,4-naphthylene group acts preferentially in the formation of supramolecular aggregates of disazo compounds.
  • the disazo compound preferably used in the present invention is represented by the following general formula (3) or general formula (4).
  • Q, R 1 , M 1 , m1, n1, o1, and p1 in the general formula (3) are the same as those in the general formula (1).
  • R 1 , M 1 , m1, n1 and p1 in the general formula (4) are the same as those in the general formula (1), and
  • X and x in the general formula (4) are the same as those in the formula (A). It is.
  • the disazo compounds represented by the above general formulas (1), (3) and (4) are, for example, “Toyo Hosoda,“ Theoretical Manufacturing, Dye Chemistry (5th Edition) ”(published on July 15, 1968, Gihodo, page 135). To page 152).
  • a monoazo compound is obtained by diazonium chloride of a substituted or unsubstituted aniline compound and coupling reaction with an aminonaphthalenesulfonic acid compound.
  • a disazo compound represented by the above general formulas (1), (3), and (4) can be obtained by coupling the monoazo compound with a hydroxynaphthalenesulfonic acid compound.
  • the monoazo compound used in the present invention is represented by the following general formula (2).
  • R 2 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted acetyl group, a substituted or unsubstituted benzoyl group, or a substituted or unsubstituted phenyl group
  • M 2 each independently represents a counter ion
  • m 2 represents an integer of 0 to 2
  • n 2 represents an integer of 0 to 6
  • p 2 Represents an integer of 1 to 4.
  • each R 2 may be the same or different.
  • each M 2 may be the well or be the same or different.
  • each substituent of NHR 2 , SO 3 M 2 and SO 3 M 2 may be substituted at any position of the naphthalene ring.
  • R 2 is preferably a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted acetyl group, and more preferably a hydrogen atom or a substituted or unsubstituted acetyl group.
  • the substituted or unsubstituted alkyl group include substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms.
  • Examples of M 2 in the general formula (2) include the same counter ion as M 1 in the general formula (1). Therefore, regarding M 2 in the general formula (2), refer to the description regarding M 1 above.
  • M2 in the general formula (2) is preferably 1. Further, n2 in the general formula (2) is preferably 1 or 2.
  • Such a monoazo compound of the general formula (2) has an SO 3 M 2 group and an NHR 2 group, and thus has excellent solubility in an aqueous solvent.
  • the naphthyl group represented on the right side of the formula (2) include, for example, the following formulas (i) to (p ) And the like.
  • R 2 and M 2 in the formulas (i) to (p) are the same as those in the general formula (2).
  • the monoazo compound of the general formula (2) having the formula (i), the formula (j), the formula (k), the formula (m) or the formula (n) is derived from a raw material which is distributed in large quantities in the market Can be synthesized. For this reason, such a monoazo compound is preferable because it can be obtained relatively inexpensively.
  • the monoazo compound of the general formula (2) having a 1-naphthyl group represented by the above formula (I), formula (J) or formula (K) has a large dielectric anisotropy in the molecular minor axis direction.
  • a polarizing film having a high dichroic ratio can be obtained by mixing such a monoazo compound of the general formula (2) having a 1-naphthyl group with the disazo compound of the general formula (1).
  • the monoazo compound preferably used in the present invention is represented by the following general formula (5).
  • R 2 , M 2 , m2, n2 and p2 in the general formula (5) are the same as those in the general formula (2).
  • the monoazo compounds represented by the above general formulas (2) and (5) are, for example, Yutaka Hosoda, “Theoretical Manufacturing, Dye Chemistry (5th Edition)” (published July 15, 1968, Gihodo, pages 135-152).
  • an azo compound represented by the above general formulas (2) and (5) can be obtained by diazonium-chlorinating an aminonaphthalene sulfonic acid compound and coupling it with a hydroxy naphthalene sulfonic acid compound.
  • the polarizing film of this invention should just contain the said disazo compound and monoazo compound, and those content is not specifically limited.
  • the polarizing film of the present invention has absorption dichroism at least at a part of wavelengths between 380 nm and 780 nm.
  • the dichroic ratio of the polarizing film is preferably 15 or more, more preferably 20 or more, and particularly preferably 31 or more. However, the dichroic ratio can be determined by the method described in the following examples. According to the present invention, a polarizing film having a dichroic ratio of 40 or more can also be provided.
  • the polarization degree of the polarizing film of the present invention is preferably 97% or more, more preferably 98% or more, and particularly preferably 99% or more. The degree of polarization can be adjusted according to the thickness of the film, for example.
  • the transmittance (measured at a wavelength of 550 nm and 23 ° C.) of the polarizing film is preferably 35% or more, more preferably 40% or more.
  • the degree of polarization and transmittance can be measured using, for example, a spectrophotometer (product name “V-7100” manufactured by JASCO Corporation).
  • the present inventors estimate the reason why the polarizing film containing the disazo compound represented by the general formula (1) and the monoazo compound represented by the general formula (2) has a high dichroic ratio as follows. ing.
  • the disazo compound of the general formula (1) forms a stable planar structure by bonding a hydrogen atom of the OH group and one nitrogen of the azo group in the coating solution. For this reason, even when this disazo compound is used alone, the disazo compounds associate with each other in accordance with the hydrophobic interaction, so that they can form supramolecular aggregates in the coating solution. When the disazo compound forms a supramolecular aggregate, the coating liquid exhibits a liquid crystal phase.
  • the said supramolecular aggregate will be stabilized when the said monoazo compound enters into the fine area
  • the azo compound can be oriented substantially uniformly. Therefore, according to the present invention, a polarizing film having a high dichroic ratio can be obtained.
  • the disazo compound represented by the general formula (3) and the monoazo compound represented by the general formula (5) have a large dielectric anisotropy in the molecular minor axis direction, polarized light containing the disazo compound and the monoazo compound is included.
  • the film has a higher dichroic ratio.
  • the polarizing film of the present invention contains other azo compounds, other dyes other than azo compounds, and / or additives. May be included. These compounding quantities are not specifically limited, For example, it exceeds 0 mass% and is 50 mass% or less.
  • Examples of the other dyes include perylene compounds, quinophthalone compounds, naphthoquinone compounds, merocyanine compounds, and the like.
  • Examples of the additives include compatibilizers, surfactants, heat stabilizers, light stabilizers, lubricants, antioxidants, flame retardants, antistatic agents, and polymers such as polyvinyl alcohol and polyacrylamide.
  • a coating solution containing a disazo compound represented by the above general formula (1), a monoazo compound represented by the above general formula (2) and a solvent is applied in a thin film on an appropriate development surface. It is obtained by working and drying this coating film.
  • the polarizing film of the present invention can be preferably manufactured through the following step A and step B, and the step C below may be performed after the step B as necessary.
  • Step A A step of applying a coating liquid containing the disazo compound and monoazo compound and a solvent on the development surface to form a coating film.
  • Process B The process of drying the said coating film.
  • Step C A step of applying a water resistance treatment to the surface of the coating film dried in Step B. An alignment regulating force may be applied to the development surface.
  • the coating liquid of the present invention includes a disazo compound represented by the general formula (1), a monoazo compound represented by the general formula (2), and a solvent for dissolving or dispersing the azo compound.
  • the disazo compound to be used is not particularly limited as long as it is included in the general formula (1), and may be used alone or in combination of two or more.
  • the monoazo compound to be used will not be specifically limited if it is contained in General formula (2), You may use 1 type individually or 2 types or more from it among them.
  • the coating liquid is obtained by dissolving or dispersing the azo compound in a solvent such as an aqueous solvent. If necessary, in addition to the azo compound, other azo compounds, other dyes other than azo compounds, polymers, and / or additives may be added to the solvent.
  • the solvent is not particularly limited, and a conventionally known solvent can be used, but an aqueous solvent is preferable.
  • the aqueous solvent include water, a hydrophilic solvent, a mixed solvent of water and a hydrophilic solvent, and the like.
  • the hydrophilic solvent is a solvent that dissolves substantially uniformly in water.
  • examples of the hydrophilic solvent include alcohols such as methanol and isopropyl alcohol; glycols such as ethylene glycol; cellosolves such as methyl cellosolve and ethyl cellosolve; ketones such as acetone and methylethylketone; esters such as ethyl acetate; Is mentioned.
  • water or a mixed solvent of water and a hydrophilic solvent is preferably used.
  • the coating liquid exhibits a liquid crystal phase by changing the liquid temperature, the concentration of each azo compound, and the like. This liquid crystal phase is generated when the azo compound forms a supramolecular aggregate in the liquid.
  • the liquid crystal phase is not particularly limited, and examples thereof include a nematic liquid crystal phase, a smectic liquid crystal phase, a cholesteric liquid crystal phase, and a hexagonal liquid crystal phase.
  • the liquid crystal phase can be confirmed and identified by an optical pattern observed with a polarizing microscope.
  • the concentration of the disazo compound and the monoazo compound in the coating liquid is preferably adjusted so that it exhibits a liquid crystal phase.
  • the concentration of the disazo compound and the monoazo compound in the coating liquid is 0.05% by mass to 50% by mass, preferably 0.5% by mass to 40% by mass, more preferably 2% by mass to 30% by mass. It is. However, the concentration is a value based on the sum of the disazo compound and the monoazo compound.
  • the coating solution is adjusted to an appropriate pH.
  • the pH of the coating solution is preferably about pH 2 to 10, more preferably about pH 6 to 8.
  • the temperature of the coating solution is preferably adjusted to 10 ° C. to 40 ° C., more preferably 15 ° C. to 30 ° C.
  • the coating liquid is applied to an appropriate development surface to form a coating film.
  • the development surface is for developing the coating liquid substantially uniformly.
  • the type of the development surface is not particularly limited as long as it is suitable for this purpose.
  • Examples of the development surface include a polymer film surface, a glass plate surface, and a metal drum surface.
  • an oriented film may be used as the polymer film. Since the oriented film has orientation regulating force on its surface, the azo compound in the liquid can be surely oriented.
  • the oriented film can be obtained, for example, by applying an orientation regulating force to the film.
  • Examples of the method for imparting alignment regulating force include: rubbing the surface of the film; forming a film such as polyimide on the surface of the film, and rubbing the surface of the film; photoreactive compound on the surface of the film Forming an alignment film by irradiating the film with light.
  • a polymer film is used as the development surface, and a polymer film excellent in transparency (for example, a haze value of 3% or less) is preferable.
  • the material of the polymer film include polyesters such as polyethylene terephthalate; celluloses such as triacetyl cellulose; polycarbonates; acrylics such as polymethyl methacrylate; styrenes such as polystyrene; polypropylene, cyclic or norbornene structures. Olefins such as polyolefin; and the like. In order to satisfactorily orient the azo compound, it is preferable to use a norbornene film.
  • the coating method of the coating liquid is not particularly limited, and for example, a coating method using a conventionally known coater can be employed.
  • a coating method using a conventionally known coater can be employed.
  • shear stress is applied to the supramolecular aggregate of the azo compound during the flow of the coating liquid. Therefore, a coating film in which the major axis direction of the supramolecular aggregate is parallel to the flow direction of the coating liquid and the supramolecular aggregate of the azo compound is oriented can be formed on the development surface.
  • a coating film in which the azo compound is oriented substantially uniformly can be formed.
  • a magnetic field or an electric field may be applied as necessary after forming the coating film.
  • the coating film can be dried by natural drying or forced drying. Examples of forced drying include reduced pressure drying, heat drying, and reduced pressure heat drying.
  • the coating film increases in concentration in the course of drying, and the oriented azo compound is fixed. By fixing the orientation of the azo compound in the coating film, absorption dichroism, which is a characteristic of a polarizing film, is produced.
  • the obtained dried coating film can be used as a polarizing film.
  • the polarizing film of the present invention can be formed by a solution casting method using a coating liquid. Therefore, according to the present invention, it is possible to produce a very thin polarizing film.
  • the thickness of the polarizing film of the present invention is, for example, 0.1 ⁇ m to 10 ⁇ m, preferably 0.1 ⁇ m to 5 ⁇ m.
  • the following treatment may be performed. Specifically, on the surface of the dried coating film, aluminum salt, barium salt, lead salt, chromium salt, strontium salt, cerium salt, lanthanum salt, samarium salt, yttrium salt, copper salt, iron salt, and intramolecular A solution containing at least one compound salt selected from the group consisting of compound salts having two or more amino groups is contacted.
  • a layer containing the compound salt is formed on the surface of the dry coating film.
  • the surface of the dried coating film can be insolubilized or hardly soluble in water. Therefore, water resistance can be imparted to the dried coating film (polarizing film).
  • a polarizing film 1 obtained by applying the coating liquid onto a polymer film is laminated on a polymer film 2 as shown in FIG.
  • the polarizing film 1 of the present invention is usually used in a state where it is laminated on a polymer film 2. But the said polarizing film 1 can also be peeled from the said polymer film 2, and can also be used. You may laminate
  • a polarizing plate can be comprised by laminating
  • the polarizing plate 5 by which the protective film 3 was laminated
  • the polarizing plate 5 includes a polymer film 2, a polarizing film 1 laminated on the polymer film 2, and a protective film 3 laminated on the polarizing film 1.
  • the polymer film 2 has a function of protecting the polarizing film 1.
  • the protective film 3 is laminated
  • the polarizing plate 5 may be laminated with another optical film such as a retardation film.
  • any suitable adhesive layer is provided between them.
  • the material for forming the adhesive layer include an adhesive, a pressure-sensitive adhesive, and an anchor coat agent.
  • the application of the polarizing film of the present invention is not particularly limited.
  • the polarizing film of this invention is used as a structural member of image display apparatuses, such as a liquid crystal display device and an organic electroluminescence display, for example.
  • image display apparatuses such as a liquid crystal display device and an organic electroluminescence display, for example.
  • preferred applications are a television, a portable device, a video camera, and the like.
  • Example 1 The disazo compound of the above formula (1-1) and the monoazo compound of the formula (2-1) are mixed at a blending ratio (mass ratio) shown in Table 1, and dissolved in ion-exchanged water to obtain a concentration of 7 A mass% coating solution was prepared. However, the concentration is a value based on the total solid content of the disazo compound and the monoazo compound.
  • the coating liquid is applied to a bar coater (manufactured by BUSHMAN, product name “Mayer rot”). HS4 ”) and dried naturally.
  • the coating film after drying is a polarizing film.
  • the thickness of the obtained polarizing film was about 0.2 ⁇ m.
  • Table 1 shows the measurement results of the dichroic ratio of the polarizing film.
  • the disazo compound of the formula (1-1) and the monoazo compound of the formula (2-1) are mixed at a blending ratio (mass ratio) shown in Table 1, and dissolved in ion-exchanged water. Then, a liquid having a concentration of 20% by mass was prepared, and the liquid was observed at 23 ° C. according to the liquid crystal phase observation method. As a result, a nematic liquid crystal phase was shown.
  • Example 2 A polarizing film having a thickness of about 0.2 ⁇ m was produced in the same manner as in Example 1 except that the monoazo compound of the formula (2-2) was used instead of the monoazo compound of the formula (2-1).
  • Table 1 shows the blending ratio (mass ratio) and the measurement results of the dichroic ratio of the polarizing film.
  • Example 3 A polarizing film having a thickness of about 0.2 ⁇ m was prepared in the same manner as in Example 1 except that the monoazo compound of formula (2-3) was used instead of the monoazo compound of formula (2-1).
  • Table 1 shows the blending ratio (mass ratio) and the measurement results of the dichroic ratio of the polarizing film.
  • Example 4 A polarizing film having a thickness of about 0.2 ⁇ m was produced in the same manner as in Example 1 except that the monoazo compound of the formula (2-4) was used instead of the monoazo compound of the formula (2-1).
  • Table 1 shows the blending ratio (mass ratio) and the measurement results of the dichroic ratio of the polarizing film.
  • Example 5 A polarizing film having a thickness of about 0.2 ⁇ m was produced in the same manner as in Example 1 except that the monoazo compound of the formula (2-5) was used instead of the monoazo compound of the formula (2-1).
  • Table 1 shows the blending ratio (mass ratio) and the measurement results of the dichroic ratio of the polarizing film.
  • Example 6 The disazo compound of the formula (1-2) was used in place of the disazo compound of the formula (1-1), and the monoazo of the formula (2-2) was used instead of the monoazo compound of the formula (2-1).
  • a polarizing film having a thickness of about 0.2 ⁇ m was produced in the same manner as in Example 1 except that the compound was used.
  • Table 1 shows the blending ratio (mass ratio) and the measurement results of the dichroic ratio of the polarizing film.
  • Example 7 The disazo compound of the formula (1-2) was used instead of the disazo compound of the formula (1-1), and the monoazo of the formula (2-3) instead of the monoazo compound of the formula (2-1)
  • a polarizing film having a thickness of about 0.2 ⁇ m was produced in the same manner as in Example 1 except that the compound was used.
  • Table 1 shows the blending ratio (mass ratio) and the measurement results of the dichroic ratio of the polarizing film.
  • Example 8 The disazo compound of the formula (1-3) was used in place of the disazo compound of the formula (1-1), and the monoazo of the formula (2-3) was replaced with the monoazo compound of the formula (2-1)
  • a polarizing film having a thickness of about 0.2 ⁇ m was produced in the same manner as in Example 1 except that the compound was used.
  • Table 1 shows the blending ratio (mass ratio) and the measurement results of the dichroic ratio of the polarizing film.
  • Example 9 The disazo compound of the formula (1-4) was used in place of the disazo compound of the formula (1-1), and the monoazo of the formula (2-5) instead of the monoazo compound of the formula (2-1)
  • a polarizing film having a thickness of about 0.2 ⁇ m was produced in the same manner as in Example 1 except that the compound was used.
  • Table 1 shows the blending ratio (mass ratio) and the measurement results of the dichroic ratio of the polarizing film.
  • Example 1 In the same manner as in Example 1 except that only the disazo compound of the formula (1-1) was used instead of the mixture of the disazo compound of the formula (1-1) and the monoazo compound of the formula (2-1). A polarizing film having a thickness of about 0.2 ⁇ m was prepared. Table 1 shows the measurement results of the dichroic ratio of the polarizing film.
  • Example 2 In the same manner as in Example 1 except that only the disazo compound of the formula (1-2) was used instead of the mixture of the disazo compound of the formula (1-1) and the monoazo compound of the formula (2-1). A polarizing film having a thickness of about 0.2 ⁇ m was prepared. Table 1 shows the measurement results of the dichroic ratio of the polarizing film.
  • Example 1 was repeated except that only the monoazo compound of the formula (2-1) was used instead of the mixture of the disazo compound of the formula (1-1) and the monoazo compound of the formula (2-1).
  • a polarizing film having a thickness of about 0.2 ⁇ m was prepared. Table 1 shows the measurement results of the dichroic ratio of the polarizing film.
  • Example 6 In the same manner as in Example 1 except that only the monoazo compound of the formula (2-2) was used instead of the mixture of the disazo compound of the formula (1-1) and the monoazo compound of the formula (2-1). A polarizing film having a thickness of about 0.2 ⁇ m was prepared. Table 1 shows the measurement results of the dichroic ratio of the polarizing film.
  • Example 7 In the same manner as in Example 1 except that only the monoazo compound of the formula (2-3) was used instead of the mixture of the disazo compound of the formula (1-1) and the monoazo compound of the formula (2-1). A polarizing film having a thickness of about 0.2 ⁇ m was prepared. Table 1 shows the measurement results of the dichroic ratio of the polarizing film.
  • Example 8 In the same manner as in Example 1 except that only the monoazo compound of the formula (2-4) was used instead of the mixture of the disazo compound of the formula (1-1) and the monoazo compound of the formula (2-1). A polarizing film having a thickness of about 0.2 ⁇ m was prepared. Table 1 shows the measurement results of the dichroic ratio of the polarizing film.
  • Example 9 In the same manner as in Example 1 except that only the monoazo compound of the formula (2-5) was used instead of the mixture of the disazo compound of the formula (1-1) and the monoazo compound of the formula (2-1). A polarizing film having a thickness of about 0.2 ⁇ m was prepared. Table 1 shows the measurement results of the dichroic ratio of the polarizing film.
  • the polarizing film of this invention can be utilized for the structural member of a liquid crystal display device, polarized sunglasses, etc., for example.
  • the coating liquid of the present invention can be used as a material for forming a polarizing film.
  • Polarizing film 1 ... Polarizing film, 2 ... Base material, 3 ... Protective film, 5 ... Polarizing plate

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Polarising Elements (AREA)
  • Liquid Crystal (AREA)

Abstract

L'invention a pour objet un film polarisant qui a un rapport dichroïque élevé. Le film polarisant selon la présente invention comprend un composé bisazoïque représenté par la formule générale (1) et un composé monoazoïque représenté par la formule générale (2). Dans la formule générale (1) et la formule générale (2), Q représente un groupe aryle substitué ou non substitué; R1 et R2 représentent chacun un atome d'hydrogène, un groupe alkyle substitué ou non substitué, un groupe acétyle substitué ou non substitué, un groupe benzoyle substitué ou non substitué ou un groupe phényle substitué ou non substitué; M1 et M2 représentent chacun un contre-ion; m1 et m2 représentent chacun un nombre entier de 0-2; n1 et n2 représentent chacun un nombre entier de 0-6; o1 représente un nombre entier de 0-1; et p1 et p2 représentent chacun un nombre entier de 1-4.
PCT/JP2012/052362 2011-03-16 2012-02-02 Film polarisant, liquide de revêtement et dispositif d'affichage d'image Ceased WO2012124400A1 (fr)

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CN111226159A (zh) * 2017-11-09 2020-06-02 日东电工株式会社 抬头显示器装置

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KR102170099B1 (ko) 2013-12-13 2020-10-26 미쯔비시 케미컬 주식회사 이방성 색소막용 조성물, 이방성 색소막 및 광학 소자
KR20250079038A (ko) * 2017-10-19 2025-06-04 닛토덴코 가부시키가이샤 헤드업 디스플레이 장치
JP7253893B2 (ja) * 2017-10-19 2023-04-07 日東電工株式会社 ヘッドアップディスプレイ装置
JP2019079042A (ja) * 2017-10-19 2019-05-23 日東電工株式会社 ヘッドアップディスプレイ装置
KR20250079039A (ko) * 2017-10-19 2025-06-04 닛토덴코 가부시키가이샤 헤드업 디스플레이 장치
JP7309264B2 (ja) * 2017-10-19 2023-07-18 日東電工株式会社 ヘッドアップディスプレイ装置
WO2019078192A1 (fr) * 2017-10-19 2019-04-25 日東電工株式会社 Appareil d'affichage tête haute
WO2019093079A1 (fr) * 2017-11-09 2019-05-16 日東電工株式会社 Dispositif d'affichage tête haute

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WO2011004759A1 (fr) * 2009-07-10 2011-01-13 日東電工株式会社 Solution de revêtement à cristaux liquides et film polarisant

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CN111226159A (zh) * 2017-11-09 2020-06-02 日东电工株式会社 抬头显示器装置
CN111226159B (zh) * 2017-11-09 2022-12-13 日东电工株式会社 抬头显示器装置
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