WO2021256199A1 - Film polarisant, plaque polarisante, produit stratifié optique, plaque polarisante elliptique, dispositif d'affichage électroluminescent organique et dispositif d'affichage d'image flexible - Google Patents

Film polarisant, plaque polarisante, produit stratifié optique, plaque polarisante elliptique, dispositif d'affichage électroluminescent organique et dispositif d'affichage d'image flexible Download PDF

Info

Publication number
WO2021256199A1
WO2021256199A1 PCT/JP2021/019919 JP2021019919W WO2021256199A1 WO 2021256199 A1 WO2021256199 A1 WO 2021256199A1 JP 2021019919 W JP2021019919 W JP 2021019919W WO 2021256199 A1 WO2021256199 A1 WO 2021256199A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
liquid crystal
polarizing
film
structural unit
Prior art date
Application number
PCT/JP2021/019919
Other languages
English (en)
Japanese (ja)
Inventor
伸行 幡中
陽介 太田
耕太 村野
Original Assignee
住友化学株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 住友化学株式会社 filed Critical 住友化学株式会社
Priority to CN202180042435.0A priority Critical patent/CN115715374A/zh
Priority to KR1020227045962A priority patent/KR20230021020A/ko
Publication of WO2021256199A1 publication Critical patent/WO2021256199A1/fr

Links

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/8793—Arrangements for polarized light emission
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details

Definitions

  • the present invention relates to a polarizing film, a polarizing plate including the polarizing film, an optical laminate, an elliptical polarizing plate, an organic EL display device, and a flexible image display device.
  • a polarizing plate is used for various image display panels such as a liquid crystal display panel and an organic electroluminescence (organic EL) display panel.
  • Such polarizing plates include a polarizing plate having a polarizing element in which a dichroic dye such as iodine is oriented and adsorbed on a polyvinyl alcohol-based resin film, and a polymerizable coating coated on a substrate via a photoalignment film.
  • a polarizing film having a polarizing element obtained by polymerizing a liquid crystal compound is known.
  • the polarizing film formed from the coating layer of the liquid crystal compound is often used in the form of a laminate having a polarizing element and an alignment film used to form the polarizing element.
  • the decrease in the adhesion between the alignment film and the polarizing element can be one of the factors that affect the optical characteristics of the polarizing film. Therefore, an object of the present invention is to provide a polarizing film having excellent adhesion between a polarizing element and an alignment film.
  • a polarizing film including a photoalignment film and a polarizing element adjacent to the photoalignment film.
  • the photoalignment film is formed of a polymer containing a structural unit having a photoreactive group and a structural unit having a polymerizable group.
  • a polarizing film, wherein the polarizing element is a cured product of a liquid crystal composition containing a liquid crystal compound and a dichroic dye, and contains a structural unit having a polymerizable group derived from the liquid crystal compound or the dichroic dye.
  • the polymer forming the photoalignment film is of formula (II) :.
  • [6] The polarizing film according to any one of [1] to [5], wherein the dichroic dye contains an azo dye.
  • [8] The polarizing film according to any one of [1] to [7], wherein the polarizing element shows a Bragg peak in X-ray diffraction measurement.
  • a polarizing plate including the polarizing film according to any one of [1] to [8] and a base material arranged on the photoalignment film side of the polarizing film.
  • An optical laminate comprising the polarizing plate according to [9] and a layer bonded to the polarizing element side of the polarizing plate via an adhesive layer.
  • An elliptical polarizing plate including the polarizing film according to any one of [1] to [8] and a retardation layer having a 1/4 wave plate function.
  • An organic EL display device including the elliptical polarizing plate according to [11].
  • a flexible image display device including the elliptical polarizing plate according to [11].
  • the flexible image display device according to [13] further including a window and a touch sensor.
  • the polarizing film of the present invention includes a light alignment film and a polarizing element adjacent to the light alignment film, and is substantially composed of a light alignment film and a polarizing element.
  • a laminate composed of a photoalignment film and a polarizing element laminated adjacent to the photoalignment film is referred to as a polarizing film, and is added to the photoalignment film and the polarizing element adjacent to the photoalignment film.
  • the base material is arranged on the photoalignment film side, the laminated body composed of each layer from the base material to the polarizing element is called a polarizing plate.
  • the photoalignment film constituting the polarizing film of the present invention is formed of a polymer containing a structural unit having a photoreactive group and a structural unit having a polymerizable group, and the structural unit having a photoreactive group and the polymerizable group. It is preferably formed from a copolymer containing a structural unit having.
  • the structural unit having a photoreactive group contributes to imparting the liquid crystal alignment ability by the action of light
  • the structural unit having a polymerizable group is a polarizing element formed on the photoalignment film. Contributes to the improvement of adhesion with.
  • the structural unit having a photoreactive group (hereinafter, also referred to as “structural unit (i)”) is derived from a monomer having at least one photoreactive group.
  • the photoreactive group is a group that produces a liquid crystal alignment ability by irradiation with light. Specifically, it means a group that induces the orientation of polymer molecules by causing a photoreaction that is the origin of the liquid crystal alignment ability by light irradiation, such as a dimerization reaction, an isomerization reaction, or a photodecomposition reaction.
  • the structural unit (i) may have one kind or two or more kinds of photoreactive groups.
  • the dimerization reaction is a reaction in which an addition reaction occurs between two groups by the action of light, and typically forms a ring structure.
  • C C bond
  • C O bond
  • a group having a cinnamoyle structure, a group having a chalcone structure, a group having a coumarin structure, a group having a benzophenone structure, a group having an anthracene structure and the like can be mentioned.
  • a group having a cinnamoyle structure and a group having a chalcone structure are preferable from the viewpoint that the amount of polarization irradiation required for photoalignment is relatively small and it is easy to obtain a photoalignment film having excellent thermal stability and temporal stability.
  • Groups with a structure are more preferred.
  • the isomerization reaction is a reaction that produces other isomers such as stereoisomerization and structural isomerization from a single compound by the action of light.
  • N N bond
  • C carbon-carbon double bond
  • a group having an azobenzene structure, a group having a stylben structure, a group having a hydrazono- ⁇ -ketoester structure (skeleton), a group having a spiropyran structure (skeleton), and the like can be mentioned.
  • the photolysis reaction is a reaction that cuts a polymer chain by the action of light and develops anisotropy.
  • the photoreactive group is preferably a group that causes a dimerization reaction and a group that causes an isomerization reaction, and more preferably a group that causes a dimerization reaction.
  • a group that causes a dimerization reaction and a group that causes an isomerization reaction are preferable from the viewpoint of reactivity and cost.
  • reactivity it is important to react photoreactivity without reacting structural units having a polymerizable group, which will be described later.
  • the structural unit having a polymerizable group (hereinafter, also referred to as “structural unit (ii)”) is derived from a monomer having at least one polymerizable group.
  • the polymerizable group means a group involved in a polymerization reaction, and examples thereof include a thermally polymerizable group and a photopolymerizable group.
  • the polymerizable group contained in the structural unit having a polymerizable group is a photopolymerizable group. Is preferable.
  • the structural unit (ii) may have one type or two or more types of polymerizable groups.
  • the polymerizable group constituting the structural unit (ii) includes a vinyl group, a vinyloxy group, a 1-chlorovinyl group, an isopropenyl group, a 4-vinylphenyl group, a (meth) acryloyl group, a (meth) acryloyloxy group, and an oxylanyl.
  • Groups, oxetanyl groups and the like can be mentioned.
  • (meth) acryloyl group, (meth) acryloyloxy group, vinyloxy group, oxylanyl group and oxetanyl group are preferable, and (meth) acryloyl group, more preferably ) Acryloyl group and (meth) acryloyloxy group, more preferably (meth) acryloyloxy group.
  • (meth) acryloyl means methacryloyl and acryloyl.
  • the photoalignment film When the photoalignment film is formed from a polymer containing a structural unit (ii) having a polymerizable group, it forms a polarizing film having excellent adhesion between the photoalignment film and a polarizing element laminated adjacent thereto. obtain.
  • a polarizing element which is a cured product of a liquid crystal composition
  • the photoalignment is accompanied by a polymerization reaction of a liquid crystal compound such as a liquid crystal compound or a dichroic dye for forming the polarizing element.
  • the polymerizable group contained in the film may react with the polymerizable group of the liquid crystal compound such as a liquid crystal compound or a dichroic dye to form a polarizing element. Therefore, when the dichroic dye or the polymerizable liquid crystal compound forming the polarizing element has the same polymerizable group as the polymerizable group of the polymer, the adhesion between the polarizing element and the photoalignment film is more likely to be improved. Become.
  • the polymer forming the photoalignment film has an unreacted polymerizable group as the structural unit (ii).
  • the structural unit (ii) may be a structural unit derived from the monomer having a polymerizable group.
  • the polymerizable group contained in at least a part of the monomers forming the polymer remains unreacted.
  • the structural unit derived from the monomer having a polymerizable group all the polymerizable groups may exist unreacted.
  • the polymerization reaction of the liquid crystal substance for forming the polarizing element at the time of forming the polarizing element produced after the formation of the photopolarizing film is performed. Since a sufficient amount of polymerizable groups that can be reacted at the same time can be present in the photoalignment film, the adhesion between the photoalignment film and the polarizing element is likely to be improved.
  • the polymer forming the photoalignment film is preferably a structural unit (i) and a structural unit (ii) because an alignment film having excellent adhesion to a polarizing element is easily formed while exhibiting a high liquid crystal alignment ability.
  • a structural unit more preferably a polymer in which a photoreactive group and a polymerizable group are respectively located at the end of the side chain of the polymer.
  • the polymer containing the structural unit (i) and the structural unit (ii) for example, a monomer that induces the structural unit (i) and a monomer that induces the structural unit (ii) are copolymerized, or the structural unit.
  • a monomer that induces the structural unit (i) and a monomer that induces the structural unit (ii) are copolymerized, or the structural unit.
  • examples thereof include a polymer obtained by introducing a polymerizable group having a structural unit (ii) into a (co) polymer containing (i).
  • Examples of such a polymer include a polymer having a structure represented by the following formula (I) as a repeating unit.
  • the structures of Mb and Mc are, for example, the (meth) acrylic acid ester unit represented by the formula (M-1) or the formula (M-2); the formula (M-3) or the formula (M-3).
  • (Methyl) styrene units, and those selected from the group consisting of vinyl ester units represented by the formula (M-9) or the formula (M-10) can be mentioned.
  • * represents a bond with SPCRb and SPCRc.
  • the main chain of the polymer is preferably composed of units selected from the above group, and among them, units selected from the group consisting of (meth) acrylic acid ester as a unit and (meth) acrylamide unit. It is more preferably composed of.
  • the "main chain of the polymer” here means the longest molecular chain among the molecular chains of the copolymer.
  • SPCRb and SPCRc include, for example, a carbonyloxy group (ester bond), an oxygen atom (ether bond), an imide group (imide bond), a carbonylimino group (amide bond), and an iminocarbonylimino group.
  • a carbonyloxy group ester bond
  • an oxygen atom ether bond
  • an imide group imide bond
  • a carbonylimino group amide bond
  • an iminocarbonylimino group Trivalent aliphatic hydrocarbon group which may have a substituent
  • a divalent aromatic hydrocarbon group which may have a substituent
  • a divalent combination of these The group can be mentioned.
  • examples thereof include a -1,4-phenylene group, a 3-ethoxy-1,4-phenylene group, and a 2,3,5-trimethoxy-1,4-phenylene group.
  • SPCRb and SPCRc are each preferably an aliphatic hydrocarbon group, and more preferably an alkanediyl group having 1 to 11 carbon atoms which may have a substituent.
  • alkanediyl group examples include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, a heptamethylene group, an octamethylene group, a nonamethylene group, a decamethylene group and an undecamethylene group. These may be linear or branched. Further, such an alkanediyl group may have a substituent. The substituent is, for example, an alkoxy group having 1 to 4 carbon atoms.
  • Examples of the ring B and the ring C in the formula (I) include ring structures represented by the formulas (X-1) to (X-5).
  • X 1 to X 38 are each independently a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom or a cyano group.
  • Examples of the alkyl group represented by X 1 to X 38 include an alkyl group having 1 to 4 carbon atoms, and examples of the alkoxy group represented by X 1 to X 38 include an alkoxy group having 1 to 4 carbon atoms.
  • Each of X 1 to X 38 is preferably a hydrogen atom or a halogen atom, and more preferably a hydrogen atom.
  • the ring B and the ring C are preferably a ring structure represented by the formula (X-1) or the formula (X-5), and more preferably a ring structure represented by the formula (X-1).
  • R 1 is preferably an alkyl group having 1 to 6 carbon atoms or a phenyl group having at least one substituent selected from a cyano group and a halogen atom, and more preferably a phenyl group having 1 to 6 carbon atoms. It is a phenyl group substituted with 1 to 6 alkyl groups and a cyano group, and more preferably an alkyl group having 1 to 6 carbon atoms.
  • the alkyl group of R 1 an alkyl group having 1 to 4 carbon atoms is preferable, and a methyl group is more preferable.
  • n and l are mole fractions of the structural unit (i) and the structural unit (ii) with respect to all the structural units of the polymer forming the photoalignment film, and 0.1 ⁇ n ⁇ 0.9. And it is preferable to satisfy the relationship of 0.1 ⁇ l ⁇ 0.9. It is preferable that the mole fraction of the structural unit (i) and the structural unit (ii) is within the above range from the viewpoint of orientation and adhesion.
  • l preferably satisfies the relationship of 0.1 ⁇ l ⁇ 0.5, more preferably 0.1 ⁇ l ⁇ 0.3.
  • the formula (I) schematically shows that the monomer for inducing the structural unit (i) and the monomer for inducing the structural unit (ii) are contained in a molar ratio of n: l, and has a structure.
  • the monomer that induces the unit (i) and the monomer that induces the structural unit (ii) do not necessarily represent that they are alternately bonded to form a copolymer. That is, the formula (I) is a copolymer obtained by polymerizing a monomer for inducing the structural unit (i) and a monomer for inducing the structural unit (ii) in a molar ratio of n: l, for example, alternating type, block type, or random. It may include any type, graft type, and the like.
  • the polymer forming the photoalignment film is preferably a structural unit having a carboxy group in addition to the structural unit (i) and the structural unit (ii) (hereinafter, “structural unit (iii)). Also called).
  • the polymer forming the photoalignment film is preferably a polymer having a structural unit (i), a structural unit (ii) and a structural unit (iii), and more.
  • a polymer in which a photoreactive group, a polymerizable group and a carboxy group are each located at the end of the polymer side chain is preferable. Since the polymer has such a structure, it is easy to form an alignment film having better adhesion to a polarizing element.
  • Examples of the polymer containing the structural unit (i), the structural unit (ii), and the structural unit (iii) include a monomer for inducing the structural unit (i), a monomer for inducing the structural unit (ii), and a structural unit (iii).
  • a monomer for inducing the structural unit (i) By copolymerizing with a monomer that induces iii) or by introducing the polymerizable group of the structural unit (ii) into the (co) polymer containing the structural unit (i) and / or the structural unit (iii).
  • Examples include the resulting polymer.
  • Examples of such a polymer include a copolymer having a structure represented by the following formula (II) as a repeating unit.
  • Examples of the structures of Ma, Mb and Mc in the formula (II) include the same structures as those exemplified as the structures of the Mb and Mc in the formula (I).
  • SPCRa, SPCRb and SPCRc in formula (II) include structures similar to those exemplified as the structures of SPCRb and SPCRc in formula (I).
  • ring A is preferably a ring structure represented by formula (X-1)
  • rings B and C are preferably represented by formula (X-1) or (X-5). It is a ring structure, more preferably a ring structure represented by the formula (X-1).
  • R 1 and R 2 in the formula (II) include structures similar to those exemplified as the structures of R 1 and R 2 in the formula (II).
  • the mole fraction of the structural unit (i), the structural unit (ii) and the structural unit (iii) is within the above range, it is preferable from the viewpoint of orientation and adhesion.
  • the formula (II) contains a monomer for inducing the structural unit (i), a monomer for inducing the structural unit (ii), and a monomer for inducing the structural unit (iii) in a molar ratio of n: l: m.
  • This is a schematic representation of this, and the monomer that induces the structural unit (i), the monomer that induces the structural unit (ii), and the monomer that induces the structural unit (iii) are not necessarily alternately bonded to form a copolymer. It does not represent composition.
  • the monomer for inducing the structural unit (i), the monomer for inducing the structural unit (ii), and the monomer for inducing the structural unit (iii) are polymerized at a molar ratio of n: l: m. It may include any of the copolymers, for example alternating, block, random, grafted and the like.
  • the polymer forming the photoalignment film has a structure other than the structural unit (i), the structural unit (ii) and the structural unit (iii) as long as it does not affect the effect of the present invention. It may include a unit (hereinafter, also referred to as “another structural unit”).
  • the polymer forming the photoalignment film preferably has a weight average molecular weight of 20,000 or more and 150,000 or less.
  • the weight average molecular weight is equal to or higher than the above lower limit, the solvent resistance becomes good, and the photoalignment film exhibiting high liquid crystal alignment ability is obtained while ensuring high adhesion to the polarizing element later formed on the photoalignment film. Easy to obtain. Further, after the photoalignment film is produced, the orientation tends to be easily obtained when the liquid crystal composition (composition for forming a polarizing element) is applied.
  • the present inventors tend to develop a higher liquid crystal alignment ability as the weight average molecular weight of the polymer forming the photoalignment film increases within the above range, and the processing temperature at the time of forming the photoalignment film. It was found that excellent liquid crystal alignment ability can be exhibited even when the amount is relatively high.
  • the weight average molecular weight of the polymer forming the photoalignment film is more preferably 30,000 or more, further preferably 50,000 or more, still more preferably 140,000 or less, still more preferably 130. It is 000 or less.
  • the weight average molecular weight of the polymer can be measured and calculated using a measuring device such as gel permeation chromatography.
  • the polymer (hereinafter, also referred to as "polymer (I')") forming the photoalignment film containing the structural unit (i) and the structural unit (ii) is a monomer and a structural unit (hereinafter, also referred to as “polymer (I')") for inducing the structural unit (i).
  • a monomer for inducing ii), a monomer for inducing a structural unit (iii) and a monomer for inducing other structural units are mixed in a predetermined amount in a solvent-free or solvent and copolymerized, or the structural unit.
  • the monomer for inducing (i) and / or the monomer for inducing the structural unit (iii) can be produced by introducing the polymerizable group of the structural unit (ii) into the (co) polymerization.
  • a method conventionally known in the art may be adopted, and examples thereof include chain polymerization such as radical polymerization, anionic polymerization and cationic polymerization, and coordination polymerization.
  • the polymerization conditions are appropriately determined so as to obtain a polymer having a desired molecular weight, depending on the type of the monomer used and the amount thereof.
  • a known organic solvent When polymerizing in a solvent, a known organic solvent can be used without particular limitation.
  • the solvent include alcohol solvents such as ethanol, propanol and butanol, ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and cyclopentanone, ethyl acetate, butyl acetate and propylene glycol monomethyl ether acetate.
  • Ester-based solvents such as diethyl ether and diglyme, hydrocarbon-based solvents such as hexane, cyclohexane, methylcyclohexane, toluene and xylene, nitrile-based solvents such as acetonitrile, N-methyl-2-pyrrolidone, dimethylacetamide and the like. Examples include amide-based solvents. Any of these solvents may be used alone, or two or more kinds may be used in combination.
  • a polymerization initiator may be used.
  • the polymerization initiator can be appropriately selected from known polymerization initiators, for example, azobisisobutyronitrile (AIBN), diethyl-2,2'-azobisisobutyrate (V-601), 2, Azo-based polymerization initiators such as 2'-azobis (2,4-dimethylvaleronitrile) and dimethylazobismethylprovionate, peroxide-based polymerization initiators such as benzoyl peroxide, hydrogen peroxide and lauroyl peroxide, and peroxides. Examples thereof include persulfate-based polymerization initiators such as potassium sulfate and ammonium persulfate. Any of these polymerization initiators may be used alone, or two or more thereof may be used in combination.
  • AIBN azobisisobutyronitrile
  • V-601 diethyl-2,2'-azobisisobutyrate
  • Azo-based polymerization initiators such as
  • the polymerization conditions are appropriately determined so as to obtain a polymer having a desired molecular weight, depending on the type of the monomer used and the amount thereof.
  • the temperature at the time of polymerization may be appropriately set depending on the type of the monomer used, the type of the polymerization solvent, the type of the polymerization initiator, etc., but is preferably in the range of 40 to 150 ° C, more preferably 50 to 120 ° C. be.
  • the photo-alignment film is based on a composition containing a polymer (I') and a solvent capable of dissolving the polymer (I') (hereinafter, also referred to as "composition for forming a photo-alignment film"). It is obtained by applying it to a surface forming a photoalignment film such as, etc., drying and removing the solvent, and then irradiating it with polarized light (preferably polarized UV).
  • the composition for forming a photoalignment film may contain a polymer material such as polyvinyl alcohol or polyimide or a photosensitizer as long as the characteristics of the photoalignment film are not significantly impaired.
  • the content of the polymer (I') in the composition for forming a photoalignment film can be appropriately adjusted depending on the structure of the polymer (I'), the thickness of the target photoalignment film, and the like, but the composition for forming a photoalignment film. It is preferably at least 0.1% by mass, more preferably 0.3 to 10% by mass, in terms of solid content with respect to the mass of the substance.
  • the solid content means the total amount of components excluding volatile components such as a solvent from the composition for forming a photoalignment film.
  • the composition for forming a polarizing element refers to the total amount of the components excluding the volatile components such as the solvent from the target composition.
  • the solvent used in the composition for forming a photoalignment film can be appropriately selected depending on the type of the polymer (I') to be used and the like.
  • water alcohol solvents such as methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, methyl cellosolve, butyl cellosolve and propylene glycol monomethyl ether; ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, ⁇ -butyrolactone, propylene glycol methyl.
  • Ester solvents such as ether acetate and ethyl lactate; ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, methylamylketone and methylisobutylketone; aliphatic hydrocarbon solvents such as pentane, hexane and heptane; Examples include aromatic hydrocarbon solvents, nitrile solvents such as acetonitrile; ether solvents such as tetrahydrofuran and dimethoxyethane; chlorine-substituted hydrocarbon solvents such as chloroform and chlorobenzene; and the like. Any of these solvents may be used alone, or two or more kinds may be used in combination.
  • Examples of the method for applying the composition for forming a photoalignment film to a substrate or the like include a spin coating method, an extrusion method, a gravure coating method, a die coating method, a bar coating method, a coating method such as an applicator method, and a flexographic method.
  • Known methods such as a printing method can be mentioned.
  • Examples of the method for drying and removing the solvent include a natural drying method, a ventilation drying method, a heat drying method, and a vacuum drying method. As a result, a dry coating film is formed.
  • the polarized light is irradiated from the side of the substrate or the like on which the dry coating film is formed. It may be a form in which polarized light is transmitted and irradiated. Further, it is particularly preferable that the polarized light is substantially parallel light.
  • the wavelength of the polarized light to be irradiated is preferably in the wavelength range in which the photoreactive group of the polymer (I') can absorb light energy. Specifically, UV (ultraviolet light) having a wavelength in the range of 250 to 400 nm is particularly preferable.
  • Examples of the light source used for the polarized light irradiation include xenon lamps, high-pressure mercury lamps, ultra-high pressure mercury lamps, metal halide lamps, ultraviolet light lasers such as KrF and ArF, and high-pressure mercury lamps, ultra-high pressure mercury lamps and metal halide lamps. preferable. These lamps are preferable because they have a high emission intensity of ultraviolet light having a wavelength of 313 nm.
  • Polarized light can be irradiated by irradiating the light from the light source through an appropriate polarizing element.
  • a polarizing element a polarizing filter, a polarizing prism such as Gran Thomson or Gran Tailor, or a wire grid type polarizing element can be used.
  • the thickness of the photoalignment film is preferably 10 to 5000 nm, more preferably 10 to 1000 nm, and even more preferably 30 to 300 nm.
  • the thickness of the photo-alignment film is within the above range, it is possible to exert an orientation-regulating force while exhibiting good adhesion to a polarizing element, and it is possible to form a polarizing element with a high orientation order.
  • the polarizing element constituting the polarizing film of the present invention is a cured product of the liquid crystal composition, that is, a coating layer formed from the liquid crystal composition.
  • the liquid crystal composition (hereinafter, also referred to as “polarizer forming composition”) that forms a polarizing element includes a liquid crystal compound and a dichroic dye.
  • the dichroic dye means a dye having different properties between the absorbance in the major axis direction and the absorbance in the minor axis direction.
  • the dichroic dye that can be used in the present invention is not particularly limited as long as it has the above-mentioned properties, and may be a dye or a pigment. Further, two or more kinds of dyes or pigments may be used in combination, or dyes and pigments may be used in combination. Further, the dichroic dye may have a polymerizable property or a liquid crystal property.
  • the dichroic dye preferably has a maximum absorption wavelength ( ⁇ MAX) in the range of 300 to 700 nm.
  • dichroic dyes include acridine dyes, oxazine dyes, cyanine dyes, naphthalene dyes, azo dyes and anthraquinone dyes.
  • the azo dye since the azo dye has high linearity, it is suitable for producing a polarizing element having excellent polarization performance. Therefore, in one aspect of the present invention, the dichroic dye contained in the polarizing element forming composition that forms a polarizing element is preferably an azo dye.
  • the azo dye examples include a monoazo dye, a bisazo dye, a trisazo dye, a tetrakisazo dye, a stilbene azo dye, and the like, preferably a bisazo dye and a trisazo dye, and examples thereof include a compound represented by the formula (1).
  • K 1 (-N N-K 2 )
  • p -N N-K 3 (1)
  • K 1 and K 3 may have a phenyl group which may have a substituent, a naphthyl group which may have a substituent, or a substituent which may have a substituent independently of each other. Represents a good monovalent heterocyclic group.
  • K 2 is a p-phenylene group which may have a substituent, a naphthalene-1,4-diyl group which may have a substituent, or a divalent heterocycle which may have a substituent.
  • p represents an integer of 1 to 4.
  • the plurality of K 2s may be the same or different from each other.
  • the monovalent heterocyclic group for example, one hydrogen atom was removed from a heterocyclic compound such as quinoline, thiazole, benzothiazole, thienotiazole, imidazole, benzimidazole, oxazole, and benzoxazole.
  • a heterocyclic compound such as quinoline, thiazole, benzothiazole, thienotiazole, imidazole, benzimidazole, oxazole, and benzoxazole.
  • the group is mentioned.
  • the divalent heterocyclic group include a group obtained by removing two hydrogen atoms from the heterocyclic compound.
  • Optional substituents include an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms having a polymerizable group, an alkenyl group having 1 to 4 carbon atoms; a methoxy group, an ethoxy group, a butoxy group and the like.
  • An alkoxy group having 1 to 20 carbon atoms an alkoxy group having 1 to 20 carbon atoms having a polymerizable group; an alkyl fluoride group having 1 to 4 carbon atoms such as a trifluoromethyl group; a cyano group; a nitro group; a halogen atom; an amino Substituent or unsubstituted amino group such as group, diethylamino group, pyrrolidino group (substituted amino group is an amino group having one or two alkyl groups having 1 to 6 carbon atoms and 1 to 6 carbon atoms having a polymerizable group.
  • An unsubstituted amino group is-. NH 2 ) and the like.
  • the polymerizable group include an acryloyl group, a metaacryloyl group, an acryloyloxy group, and a metaacryloyloxy group.
  • Examples of the azo dye represented by the formula (1) include compounds represented by any of the following formulas (1-1) to (1-8). These azo dyes may be used alone or in combination of two or more.
  • B 1 to B 30 are independent of each other, a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, a nitro group, a substituent or the like.
  • Represents an unsubstituted amino group (the definition of a substituted amino group and an unsubstituted amino group is as described above), a chlorine atom or a trifluoromethyl group.
  • n1 to n4 represent integers of 0 to 3 independently of each other. If n1 is 2 or more, a plurality of B 2 may be the same or different from each other, If n2 is 2 or more, plural B 6 may be the same or different from each other, If n3 is 2 or more, plural B 9 may be the same or different from each other, When n4 is 2 or more, the plurality of B 14s may be the same or different from each other. ]
  • the polarizing element constituting the polarizing film of the present invention contains a structural unit having a polymerizable group derived from a liquid crystal compound or a dichroic dye, and when the polarizing element contains the structural unit, a weight forming a photoalignment film is formed. Since a bond can be formed between the polymerizable group of the structural unit (ii) constituting the coalesced (I'), it becomes easy to form a polarizing film having excellent adhesion between the photoalignment film and the polarizing element. Therefore, the dichroic dye in the present invention may be a dichroic dye having a polymerizable group.
  • examples of the polymerizable group include groups exemplified as the polymerizable group of the structural unit (ii) constituting the polymer (I').
  • the polymerizable group examples include groups exemplified as the polymerizable group of the structural unit (ii) constituting the polymer (I').
  • (meth) acryloyl group, (meth) acryloyloxy group, vinyloxy group, oxylanyl group and oxetanyl group are preferable, and (meth) acryloyl group and (meth) acryloyl are more preferable.
  • An oxy group more preferably a (meth) acryloyloxy group.
  • the polymerizable group in the dichroic dye may be one type alone or a combination of two or more types, but it must be the same polymerizable group as the polymerizable group possessed by the structural unit (ii). Is preferable.
  • the number of polymerizable groups contained in the dichroic dye is not particularly limited, and may be one or more.
  • dichroic dye having a polymerizable group examples include those having a polymerizable group among the compounds represented by the above formula (1) and the following formula (2):
  • m represents an integer from 0 to 3;
  • a 1 , A 2 and A 3 represent divalent aromatic groups that may have substituents independently of each other;
  • R c and R d they represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms independently of each other;
  • Z 1 represents a polymerizable group and
  • Z 2 represents a hydrogen atom or a polymerizable group;
  • Q 1 and Q 2 each independently a linear or branched alkylene group having a substituent and 1 carbon atoms which may have a 20, of the substituents to 1 carbon atoms which may have a 20 alkenylene
  • T 1 represents a single bond, -O -, - S -, - CO -, - COO -, - OCO -, - OCOO-, or -CONR f -, or represents a -NR f CO-
  • T 2 is a single bond, -O -, - S -, - CO -, - COO -, - OCO -, - OCOO -, - CONR f -, - NR f CO-, or, -NR g - represents, here In R f and R g , each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, even if the alkyl group represented by R g forms a ring with Q 1 or Q 2.
  • Z 2 represents a hydrogen atom when T 2 is -NR g-] Examples thereof include compounds represented by.
  • the content of the dichroic dye can be appropriately determined depending on the type of the dichroic dye to be used and the like. From the viewpoint of easily increasing the adhesion to the photoalignment film and the two-color ratio, it may be, for example, 1 to 99 parts by mass, preferably 2 parts by mass or more, with respect to 100 parts by mass of the solid content of the polarizing film forming composition. , More preferably 3 parts by mass or more. Further, from the viewpoint that the degree of orientation order of the polarizing element is likely to increase, it is preferably 80 parts by mass or less, more preferably 50 parts by mass or less, still more preferably 25 parts by mass or less, and particularly preferably 10 parts by mass or less.
  • the two-color ratio refers to the absorption intensity ratio of two linearly polarized lights that vibrate perpendicularly to each other for the light incident on the polarizing element. It is defined as the ratio (AV / AH) of the absorbance (AV) along the extinction axis (measured at vertical incidence) to the absorbance (AH) along the transmission axis.
  • the transmission axis refers to the polarization direction of the component transmitted through the polarizing film in the incident light on the polarizing film
  • the extinguishing axis refers to the polarization direction of the component transmitted through the polarizing film. It refers to the polarization direction of the components absorbed by the polarizing film.
  • the structural unit having a polymerizable group in the polarizing element may be derived from a liquid crystal compound having a polymerizable group.
  • the composition for forming a polarizing element preferably contains a polymerizable liquid crystal compound from the viewpoint of easily improving the adhesion to the photoalignment film and easily improving the orientation.
  • the liquid crystal compound refers to a liquid crystal substance exhibiting liquid crystallinity
  • the dichroic dye having a polymerizable group described above can also be one kind of the liquid crystal substance having a polymerizable group.
  • the liquid crystal compound does not contain a dichroic dye having a polymerizable group.
  • the polymerizable liquid crystal compound other than the dichroic dye having a polymerizable group is referred to as “polymerizable liquid crystal compound (A)”.
  • the composition for forming a substituent preferably contains a liquid crystal substance having a polymerizable group, and in one aspect of the present invention, the polymerizable liquid crystal compound (A) is used as the liquid crystal substance having a polymerizable group.
  • Examples of the polymerizable group of the polymerizable liquid crystal compound (A) include the groups exemplified as the polymerizable group of the structural unit (ii) constituting the polymer (I') forming the photoalignment film.
  • preferable polymerizable groups are (meth) acryloyl group, (meth) acryloyloxy group, vinyloxy group, oxylanyl group and oxetanyl group, and more preferably (meth) acryloyl group and (meth) acryloyl group from the viewpoint of easy control of the reaction. It is a (meth) acryloyloxy group, more preferably a (meth) acryloyloxy group.
  • the polymerizable group in the polymerizable liquid crystal compound (A) may be one kind or a combination of two or more kinds. Since a bond can be formed between the polymerizable group of the structural unit (ii) constituting the polymer (I'), it becomes easy to form a polarizing film having excellent adhesion between the photoalignment film and the substituent.
  • the polymerizable group of the polymerizable liquid crystal compound (A) is preferably the same polymerizable group as the polymerizable group in the structural unit (ii).
  • the polymerizable liquid crystal compound (A) may be a thermotropic liquid crystal or a riotropic liquid crystal, but is preferably a thermotropic liquid crystal. Further, the polymerizable liquid crystal compound (A) may be a thermotropic liquid crystal compound showing a nematic liquid crystal phase or a thermotropic liquid crystal compound showing a smectic liquid crystal phase. In the present invention, the polymerizable liquid crystal compound (A) is preferably a thermotropic liquid crystal compound exhibiting a smectic liquid crystal phase, and more preferably a thermotropic exhibiting a higher-order smectic liquid crystal phase, from the viewpoint of obtaining higher polarization characteristics. It is a liquid crystal compound.
  • thermotropic liquid crystal compounds showing smectic B phase, smectic D phase, smectic E phase, smectic F phase, smectic G phase, smectic H phase, smectic I phase, smectic J phase, smectic K phase or smectic L phase are more suitable.
  • a thermotropic liquid crystal compound showing a smectic B phase, a smectic F phase or a smectic I phase is more preferable.
  • the liquid crystal phase formed by the polymerizable liquid crystal compound (A) is these higher-order smectic phases, it becomes easier to obtain a polarizing element having higher polarization performance.
  • such a polarizing element having high polarization performance can obtain a Bragg peak derived from a higher-order structure such as a hexatic phase or a crystal phase in X-ray diffraction measurement.
  • higher polarization characteristics can be obtained by containing a polymer of such a polymerizable liquid crystal compound, preferably a polymer of a polymerizable liquid crystal compound polymerized in a smectic phase state, in the polarizing element of the present invention. preferable.
  • the polymerizable liquid crystal compound (A) is not particularly limited as long as it is a liquid crystal compound having at least one polymerizable group, and known polymerizable liquid crystal compounds can be used, but compounds exhibiting smectic liquid crystal properties are preferable.
  • Examples of such a polymerizable liquid crystal compound include a compound represented by the following formula (A1) (hereinafter, may be referred to as “polymerizable liquid crystal compound (A1)”).
  • X 1A and X 2A independently represent a divalent aromatic group or a divalent alicyclic hydrocarbon group, wherein the divalent aromatic group or a divalent alicyclic hydrocarbon is used.
  • the hydrogen atom contained in the group is substituted with a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group or a nitro group.
  • the carbon atom constituting the divalent aromatic group or the divalent alicyclic hydrocarbon group may be substituted with an oxygen atom or a sulfur atom or a nitrogen atom.
  • at least one of X 1A and X 2A is a 1,4-phenylene group which may have a substituent or a cyclohexane-1,4-diyl group which may have a substituent.
  • Y 1A is a single bond or divalent linking group.
  • n is 1 to 3, and when n is 2 or more, the plurality of X1A may be the same as each other or may be different from each other.
  • X 2A may be the same as or different from any or all of the plurality of X 1A. Further, when n is 2 or more, the plurality of Y1A may be the same as each other or may be different from each other. From the viewpoint of liquid crystallinity, n is preferably 2 or more.
  • U 1A represents a hydrogen atom or a polymerizable group.
  • U 2A represents a polymerizable group.
  • W 1A and W 2A are single-bonded or divalent linking groups independent of each other.
  • V 1A and V 2A represent an alkanediyl group having 1 to 20 carbon atoms which may have a substituent independently of each other, and -CH 2- constituting the alkanediyl group is -O-, It may be replaced with -CO-, -S- or NH-.
  • X 1A and X 2A are independent of each other and preferably have a 1,4-phenylene group or a substituent which may have a substituent. It is a good cyclohexane-1,4-diyl group, and at least one of X 1A and X 2A has a 1,4-phenylene group which may have a substituent, or a substituent. It is also a good cyclohexane-1,4-diyl group, preferably a trans-cyclohexane-1,4-diyl group.
  • the substituents arbitrarily contained in the 1,4-phenylene group which may have a substituent or the cyclohexane-1,4-diyl group which may have a substituent include a methyl group and an ethyl. Examples thereof include an alkyl group having 1 to 4 carbon atoms such as a group and a butyl group, a cyano group and a halogen atom such as a chlorine atom and a fluorine atom. It is preferably unsubstituted.
  • the polymerizable liquid crystal compound (A1) has the formula (A1-1) in the formula (A1). -(X 1A- Y 1A- ) n -X 2A- (A1-1) [In the formula, X 1A , Y 1A , X 2A and n have the same meanings as described above. ] It is preferable that the portion indicated by (hereinafter, also referred to as partial structure (A1-1)] has an asymmetric structure in that smectic liquid crystallinity is easily exhibited.
  • the polymerizable liquid crystal compound (A1) having an asymmetric structure in the partial structure (A1-1) for example, the polymerizable liquid crystal compound (A1) in which n is 1 and one X 1A and X 2A have different structures from each other. ). Further, n is 2, two Y 1A are compounds having the same structure as each other, two X 1A have the same structure as each other, and one X 2A has a different structure from these two X 1A.
  • the polymerizable liquid crystal compound (A1) X 1A is bond to W 1A of the two X 1A is the other of X 1A and X 2A are different structures from each other the same structure as the other X 1A and X 2A Also mentioned is a polymerizable liquid crystal compound (A1). Further, polymerization in which n is 3 and three Y1A are compounds having the same structure as each other, and any one of the three X1A and one X2A has a structure different from all the other three.
  • the sex liquid crystal compound (A1) can be mentioned.
  • R a and R b independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • Y 1A is, -CH 2 CH 2 -, - more preferably COO- or a single bond, when a plurality of Y 1A is present, Y 1A that binds X 2A is, -CH 2 CH 2 - or - It is more preferably CH 2 O ⁇ .
  • X 1A and X 2A all have the same structure, it is preferable that two or more Y 1A having different bonding methods are present.
  • the structure is asymmetrical, so that smectic liquid crystallinity tends to be easily exhibited.
  • U 2A is a polymerizable group.
  • U 1A is a hydrogen atom or a polymerizable group, preferably a polymerizable group. Both U 1A and U 2A are preferably polymerizable groups, and both are preferably radically polymerizable groups. Examples of the polymerizable group include the same groups as those exemplified above as the polymerizable group of the polymerizable liquid crystal compound (A).
  • the polymerizable group is the same polymerizable group as the polymerizable group in the structural unit (ii) constituting the polymer (I') forming the photoalignment film, the adhesion between the photoalignment film and the polarizing element is improved. It is preferable because it tends to improve.
  • the polymerizable group represented by U 1A and the polymerizable group represented by U 2A may be different from each other, but are preferably the same type of group. Further, it is preferable that at least one of U 1A and U 2A is a (meth) acryloyl group, and it is more preferable that both are (meth) acryloyl groups. Further, the polymerizable group may be in a polymerized state or a non-polymerized state, but is preferably in a non-polymerized state.
  • the alkanediyl group represented by V 1A and V 2A includes a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,3-diyl group, a butane-1,4-diyl group, and a pentane-. 1,5-Diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, decane-1,10-diyl group, tetradecane-1,14-diyl Examples include groups and icosan-1,20-diyl groups.
  • V 1A and V 2A are preferably an alkanediyl group having 2 to 12 carbon atoms, and more preferably an alkanediyl group having 6 to 12 carbon atoms.
  • alkanediyl group examples include a cyano group and a halogen atom, and the alkanediyl group is preferably unsubstituted and is an unsubstituted linear alkanediyl group. Is more preferable.
  • W 1A and W 2A are independent of each other, preferably single-bonded, -O-, -S-, -COO- or -OCOO-, and more preferably single-bonded or -O-.
  • the polymerizable liquid crystal compound (A) is not particularly limited as long as it is a polymerizable liquid crystal compound having at least one polymerizable group and exhibiting liquid crystallinity, and a known polymerizable liquid crystal compound can be used.
  • a polymerizable liquid crystal compound (A) a polymerizable liquid crystal compound exhibiting smectic liquid crystal property is preferable, and a compound exhibiting higher-order smectic liquid crystal property is more preferable.
  • As a structure that easily exhibits smectic liquid crystal properties it is preferable to have an asymmetric molecular structure in the molecular structure, and specifically, a polymerization having a structure represented by the following formulas (Aa) to (Ai).
  • the liquid crystal compound is a polymerizable liquid crystal compound exhibiting smectic liquid crystal properties. From the viewpoint of easily exhibiting higher-order smectic liquid crystal properties, it is more preferable to have a structure represented by any of the formulas (Aa), (Ab) and (Ac), and the formula (Aa). ) Or the structure represented by the formula (Ac) is particularly preferable. In the following formula, * represents a bond.
  • polymerizable liquid crystal compound (A) examples include compounds represented by formulas (A-1) to (A-25).
  • the cyclohexane-1,4-diyl group is preferably a trans form.
  • the polymerizable liquid crystal compound (A) one type may be used alone, or two or more types may be used in combination.
  • the polymerizable liquid crystal compound (A) may be described in, for example, Lub or the like, Recl. Trav. Chim. It can be produced by a known method described in Pays-Bas, 115, 321-328 (1996), or Japanese Patent No. 4719156.
  • the splitter forming composition contains the polymerizable liquid crystal compound (A)
  • the content thereof is, for example, 1 to 99 parts by mass with respect to 100 parts by mass of the solid content of the polarizing element forming composition. It may be any amount, preferably 40 parts by mass or more, more preferably 50 parts by mass or more, further preferably 60 parts by mass or more, particularly preferably 70 parts by mass or more, particularly preferably 80 parts by mass or more, and preferably 98 parts by mass. Parts or less, more preferably 95 parts by mass or less.
  • the composition for forming a substituent contains two or more kinds of polymerizable liquid crystal compounds (A), at least one of them may be a polymerizable liquid crystal compound (A1), and all of them may be a polymerizable liquid crystal compound (A1). ) May be.
  • the liquid crystal property may be temporarily maintained even at a temperature equal to or lower than the liquid crystal-crystal phase transition temperature.
  • the composition for forming a polarizing element may further contain a polymerization initiator.
  • the polymerization initiator is a compound that can initiate a polymerization reaction of a liquid crystal substance having a polymerizable group that can be contained in the composition for forming a polarizing element.
  • the polymerization initiator is not particularly limited as long as it is a compound capable of initiating the polymerization reaction of a liquid crystal substance having a polymerizable group, and a known polymerization initiator, preferably a photopolymerization initiator, can be used. Specific examples thereof include a photopolymerization initiator that generates an active radical by light irradiation, and a photopolymerization initiator that generates an acid.
  • the photopolymerization initiator can be used alone or in combination of two or more.
  • Examples of the photopolymerization initiator that generates an active radical include self-cleaving of a benzoin compound, an acetophenone compound, a hydroxyacetophenone compound, an ⁇ -aminoacetophenone compound, an oxime ester compound, an acylphosphine oxide compound, an azo compound and the like.
  • Type photopolymerization initiators benzophenone compounds, alkylphenone compounds, benzoin ether compounds, benzyl ketal compounds, dibenzosverone compounds, anthraquinone compounds, xanthone compounds, thioxanthone compounds, halogenoacetophenone compounds, Examples thereof include hydrogen abstraction type photopolymerization initiators such as dialkoxyacetophenone-based compounds, halogenobis imidazole-based compounds, halogenotriazine-based compounds, and triazine-based compounds.
  • Examples of the photopolymerization initiator that generates an acid include iodonium salt and sulfonium salt.
  • photopolymerization initiators a photopolymerization initiator that generates active radicals by light irradiation is preferable, and a self-cleaving type photopolymerization initiator is preferable from the viewpoint of excellent reaction efficiency at low temperatures.
  • acetophenone-based compounds, hydroxyacetophenone-based compounds, ⁇ -aminoacetophenone-based compounds, and oxime ester-based compounds are preferable.
  • benzoin compound examples include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether.
  • acetophenone compound examples include diethoxyacetophenone, 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan-1-one, and 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl).
  • Examples of the oxime ester compound include Irgacure (registered trademark) OXE-01, Irgacure (registered trademark) OXE-02, Irgacure (registered trademark) OXE-03 (above, manufactured by BASF Japan Co., Ltd.), and ADEKA PTOMER (registered).
  • Examples thereof include compounds such as N-1919 (trademark) and NCI-831 (registered trademark) NCI-831 (all manufactured by ADEKA Corporation).
  • acylphosphine oxide compound examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide and the like.
  • benzophenone compound examples include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3', 4,4'-tetra (tert-butylperoxycarbonyl). ) Benzophenone, 2,4,6-trimethylbenzophenone and the like.
  • alkylphenone compound examples include diethoxyacetophenone, 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan-1-one, and 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl).
  • triazine compound examples include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- (4-methoxy).
  • Irgacure 907 As the polymerization initiator, Irgacure 907, Irgacure 184, Irgacure 651, Irgacure 819, Irgacure 250, Irgacure 369 (all manufactured by Ciba Japan Co., Ltd.), Sakeall BZ, Sakeall Z, Sakeall BEE (all of which are manufactured by Ciba Japan Co., Ltd.).
  • the content of the polymerization initiator is the type and amount of the liquid crystal substance having a polymerizable group contained in the composition for forming a polarizing element involved in the polymerization reaction. It may be adjusted appropriately according to the above.
  • the content of the polymerization initiator is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 15 parts by mass, and even more preferably more preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the solid content of the polarizing element forming composition. It is 1 to 10 parts by mass.
  • composition for forming a polarizing element may contain an additive, if necessary, as long as the effect of the present invention is not impaired.
  • the additive include a sensitizer, a polymerization inhibitor, a leveling agent and the like.
  • the composition for forming a polarizing element may contain a sensitizer.
  • a photosensitizer is preferable.
  • the sensitizer include xanthone compounds such as xanthone or thioxanthone (eg, 2,4-diethylthioxanthone, 2-isopropylthioxanthone, etc.), anthracene compounds having substituents such as anthracene or alkyl ether (eg, dibutoxyanthracene). Etc.), phenothiazine or rubrene.
  • the polarizing element forming composition contains a sensitizer
  • the polymerization reaction of the liquid crystal substance having a polymerizable group contained in the composition is promoted, and the film strength of the obtained polarizing element is easily improved.
  • the composition for forming a polarizing element contains a photosensitizer
  • the content of the sensitizer makes it easy to promote the polymerization reaction without impairing the orientation of the obtained polarizing element.
  • the solid content is preferably 0.1 to 30 parts by mass, more preferably 0.3 to 10 parts by mass, and further preferably 0.5 to 8.0 parts by mass with respect to 100 parts by mass.
  • polymerization inhibitor examples include hydroquinones having a substituent such as hydroquinone or an alkyl ether, catechols having a substituent such as an alkyl ether such as butylcatechol, pyrogallols, 2,2,6,6-tetramethyl-1.
  • -Radical catching agents such as piperidinyloxy radicals, thiophenols, ⁇ -naphthylamines, ⁇ -naphthols and the like can be mentioned.
  • the composition for forming a polarizing element contains a polymerization inhibitor, it can be polymerized while suppressing the occurrence of misorientation of the liquid crystal substance having a polymerizable group.
  • the content of the polymerization inhibitor is the solid content of the composition for forming a substituent from the viewpoint of the effect of suppressing the orientation disorder of the liquid crystal substance having a polymerizable group. It is preferably 0.1 to 30 parts by mass, more preferably 0.3 to 10 parts by mass, and further preferably 0.5 to 8.0 parts by mass with respect to 100 parts by mass.
  • the composition for forming a polarizing element may contain a leveling agent.
  • the leveling agent is an additive having a function of adjusting the fluidity of the composition and making the film obtained by applying the composition flatter, for example, organically modified silicone oil-based, polyacrylate-based and perfluoroalkyl.
  • a system leveling agent can be mentioned.
  • DC3PA, SH7PA, DC11PA, SH28PA, SH29PA, SH30PA, ST80PA, ST86PA, SH8400, SH8700, FZ2123 (all manufactured by Toray Dow Corning Co., Ltd.), KP321, KP323, KP324, KP326, KP340, KP341, X22-161A, KF6001 (all manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (all momentive performance materials Japan GK) Fluorinert (registered trademark) FC-72, FC-40, FC-43, FC-3283 (all manufactured by Sumitomo 3M Co., Ltd.), Megafuck (registered trademark) R-08 , R-30, R-90, F-410, F-411, F-443, F-445, F-470, F-477, F-4
  • F-483 (all manufactured by DIC Co., Ltd.), Ftop (trade name) EF301, EF303, EF351, EF352 (all manufactured by Mitsubishi Materials Electronics Chemical Co., Ltd.), Surflon (registered) Trademarks) S-381, S-382, S-383, S-393, SC-101, SC-105, KH-40, SA-100 (all manufactured by AGC Seimi Chemical Co., Ltd.) , Product name E1830, E5844 (manufactured by Daikin Fine Chemical Laboratory Co., Ltd.), BM-1000, BM-1100, BYK-352, BYK-353 and BYK-361N (all trade names: manufactured by BM Chemie), etc. Can be mentioned. Of these, polyacrylate-based leveling agents and perfluoroalkyl-based leveling agents are preferable.
  • the polarizing element-forming composition contains a leveling agent, it is preferably 0. It is 01 to 30 parts by mass, more preferably 0.03 to 10 parts by mass, and further preferably 0.05 to 8.0 parts by mass.
  • the leveling agent may be used alone or in combination of two or more.
  • the polymerization inhibitor and the leveling agent which may be contained in the composition for forming a polarizing element, for example, a colorant such as an antioxidant, a mold release agent, a stabilizer and a brewing agent, and difficulty Examples include flame retardants and lubricants.
  • a colorant such as an antioxidant, a mold release agent, a stabilizer and a brewing agent
  • difficulty Examples include flame retardants and lubricants.
  • the total mass of the additive content is more than 0% and 20% by mass or less with respect to the solid content of the polarizing element forming composition. It is preferable, more preferably more than 0% and 10% by mass or less.
  • the composition for forming a polarizing element can be produced by a conventionally known preparation method, and is usually mixed with a dichroic dye, a polymerizable liquid crystal compound (A), a polymerization initiator, the above-mentioned additives and the like, if necessary. It can be prepared by stirring. Further, since a compound exhibiting smectic liquid crystal property generally has a high viscosity, a solvent is added to the polarizing element forming composition from the viewpoint of improving the coatability of the polarizing element forming composition and facilitating the formation of the polarizing element. The viscosity may be adjusted by
  • an organic solvent capable of dissolving the components contained in the composition for forming a polarizing element and being inert to the polymerization reaction is preferable.
  • alcohol solvents such as methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, methyl cellosolve, butyl cellosolve or propylene glycol monomethyl ether; ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, ⁇ -butyrolactone, Ester solvents such as propylene glycol methyl ether acetate or ethyl lactate; ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, methylamylketone or methylisobutylketone; non-chlorine aliphatic hydrocarbon solvents such as pentane, hexane or heptane
  • the solid content concentration of the polarizing element forming composition is preferably 2% by mass or more, more preferably 5% by mass or more, still more preferably 10% by mass or more, and also. It is preferably 50% by mass or less, more preferably 40% by mass or less, and further preferably 30% by mass or less.
  • the solid content concentration is at least the above lower limit, the obtained polarizing element is not too thin, and the dichroism required for the polarizing element can be easily obtained.
  • the viscosity of the polarizing element forming composition tends to be low, and the thickness of the coating film of the composition tends to be less likely to be uneven.
  • the viscosity of the polarizing element forming composition is preferably 0.1 to 10 mPa ⁇ s, more preferably 0.1 to 7 mPa ⁇ s, and even more preferably 0.1 to 5 mPa ⁇ s.
  • the viscosity of the polarizing element forming composition is within the above range, the composition is excellent in handleability and coatability, and the thickness of the obtained polarizing element can be easily made uniform.
  • the polarizing element is a cured product of a liquid crystal composition (composition for forming a polarizing element), and can be obtained by polymerizing a liquid crystal substance contained in the composition.
  • the polarizing element is a substance that decomposes unpolarized incident light into two orthogonal polarizing components, transmits one of the polarizing components, and absorbs the other polarizing component.
  • the axial direction of the transmitted polarized light component is called the transmission axis
  • the absorption axis the axial direction of the absorbed polarized light component
  • the polarizing element is adjacent to the photoalignment film and can exhibit high adhesion to the photoalignment film.
  • One of the factors that cause such an effect is that when a polarizing element, which is a cured product of a liquid crystal composition, is formed, light is used together with a polymerization reaction of a liquid crystal compound or a dichroic dye having a polymerizable group for forming the polarizing element.
  • the polymerizable group contained in the polymer (I') constituting the alignment film reacts and binds to the polymerizable group of the liquid crystal compound or the dichroic dye that forms the polarizing element, whereby the polarizing element and the photoalignment film are formed. It is conceivable that tighter bonds may occur between them.
  • the photoalignment film formed from the polymer (I') since the photoalignment film formed from the polymer (I') has excellent solvent resistance, it exhibits a high liquid crystal alignment ability and easily forms a polarizing element having a high degree of orientation order.
  • a polarizing element having a high degree of orientation order can obtain a Bragg peak derived from a higher-order structure such as a hexatic phase or a crystal phase in X-ray diffraction measurement.
  • the Bragg peak means a peak derived from the plane periodic structure of molecular orientation, and it is preferable that the polarizing element constituting the polarizing film of the present invention shows the Bragg peak in the X-ray diffraction measurement.
  • the polymerizable liquid crystal compound or a polymer thereof is oriented so that the polarizing element shows a Bragg peak in the X-ray diffraction measurement, and the light is emitted. It is more preferable to have a "horizontal orientation" in which the molecules of the polymerizable liquid crystal compound are oriented in the absorption direction.
  • a modulator having a plane period interval of molecular orientation of 3.0 to 6.0 ⁇ is preferable.
  • a high degree of orientation order indicating a Bragg peak can be realized by controlling the type of the polymerizable liquid crystal compound used, the type and amount of the dichroic dye, the type and amount of the polymerization initiator, and the like.
  • the thickness of the polarizing element can be appropriately determined depending on the application of the optical laminate incorporating the polarizing film, but is preferably 0.1 ⁇ m to 10 ⁇ m, more preferably 0.3 ⁇ m to 5 ⁇ m, and further preferably 0.5 ⁇ m to 3 ⁇ m. Is.
  • the thickness of the polarizing element is at least the above lower limit, the liquid crystal substance is difficult to be oriented in the vertical direction, so that the orientation order is likely to be improved. Further, when the thickness of the polarizing element is not more than the above upper limit, it is difficult for the liquid crystal substance to be randomly oriented, so that the orientation order is likely to be improved.
  • the thickness of the polarizing element can be measured using an interference film thickness meter, a laser microscope, a stylus type film thickness meter, or the like.
  • the polarizing element can be obtained, for example, by a method including applying a polarizing element forming composition on a photoalignment film and curing the applied polarizing element forming composition.
  • a method including applying a polarizing element forming composition on a photoalignment film and curing the applied polarizing element forming composition.
  • the polarizing element forming composition contains a solvent
  • the solvent contained in the composition is removed, and the solvent is removed for the polarizing element forming.
  • Polarizers may be formed by curing the composition.
  • the temperature is raised to a temperature equal to or higher than the temperature at which the polymerizable liquid crystal compound undergoes a phase transition to a liquid phase, and then the temperature is lowered to obtain the polymerizable liquid crystal compound.
  • the temperature is raised to a temperature equal to or higher than the temperature at which the polymerizable liquid crystal compound undergoes a phase transition to a liquid phase, and then the temperature is lowered to obtain the polymerizable liquid crystal compound.
  • Examples of the method for applying the polarizing element forming composition onto the photoalignment film include a spin coating method, an extrusion method, a gravure coating method, a die coating method, a bar coating method, a coating method such as an applicator method, and a flexographic method.
  • Known methods such as a printing method can be mentioned.
  • a dry coating film is formed by removing the solvent by drying or the like, preferably under the condition that the polymerizable liquid crystal compound contained in the coating film of the polarizing element forming composition does not polymerize.
  • the drying method include a natural drying method, a ventilation drying method, a heat drying method and a vacuum drying method.
  • the drying temperature may be, for example, 50 to 200 ° C., preferably 100 ° C. or higher, more preferably 110 ° C. or higher, still more preferably 120 ° C. or higher, and preferably 150 ° C. or lower.
  • the drying time is preferably 20 seconds to 10 minutes, more preferably 30 seconds to 5 minutes.
  • phase transition When the liquid crystal substance undergoes a phase transition to the liquid phase, such a phase transition may be performed after removing the solvent in the coating film, or may be performed at the same time as removing the solvent.
  • a polarizing element By polymerizing a liquid crystal substance while maintaining the liquid crystal state, a polarizing element is formed as a cured product of the composition for forming a polarizing element.
  • the polymerization method may be appropriately selected from a photopolymerization method, a thermal polymerization method and the like, depending on the type of the polymerizable group.
  • the photopolymerization method is preferable as the polymerization method in one aspect of the present invention because the polymerization can be carried out at a low temperature and the production is easy industrially.
  • the light irradiating the dry coating film is the type of the polymerizable liquid crystal compound or the like contained in the dry coating film (particularly, the type of the polymerizable group of the polymerizable liquid crystal compound or the like) and the polymerization initiator. It is appropriately selected according to the type and the amount thereof. Specific examples thereof include one or more types of active energy rays and active electron beams selected from the group consisting of visible light, ultraviolet light, infrared light, X-rays, ⁇ rays, ⁇ rays and ⁇ rays.
  • ultraviolet light is preferable because it is easy to control the progress of the polymerization reaction and it is possible to use a photopolymerization apparatus widely used in the art, so that photopolymerization can be performed by ultraviolet light. It is preferable to select the type of the polymerizable liquid crystal compound or the polymerization initiator contained in the composition for forming a substituent. Further, at the time of polymerization, the polymerization temperature can be controlled by irradiating light while cooling the dry coating film by an appropriate cooling means. A patterned polarizing element can also be obtained by masking or developing during photopolymerization.
  • Examples of the light source of the active energy ray include a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a xenon lamp, a halogen lamp, a carbon arc lamp, a tungsten lamp, a gallium lamp, an excima laser, and a wavelength range.
  • Examples thereof include LED light sources that emit light of 380 to 440 nm, chemical lamps, black light lamps, microwave-excited mercury lamps, metal halide lamps, and the like.
  • the ultraviolet irradiation intensity is usually 10 to 3,000 mW / cm 2 .
  • the ultraviolet irradiation intensity is preferably the intensity in the wavelength region effective for activating the polymerization initiator.
  • the time for irradiating with light is usually 0.1 seconds to 10 minutes, preferably 1 second to 5 minutes, more preferably 5 seconds to 3 minutes, and even more preferably 10 seconds to 1 minute.
  • the integrated light amount is 10 to 3,000 mJ / cm 2 , preferably 50 to 2,000 mJ / cm 2 , and more preferably 100 to 1,000 mJ / cm. It is 2.
  • the composition for forming a polarizing element contains a polymerizable liquid crystal compound (A)
  • the polymerizable liquid crystal compound (A) is subjected to photopolymerization to obtain a liquid crystal state of a liquid crystal phase, particularly a smectic phase, preferably a higher-order smectic phase. It is polymerized while being held, and a stator is formed.
  • the polarizing element obtained by polymerizing the polymerizable liquid crystal compound while maintaining the liquid crystal state of the smectic phase is obtained from the conventional host-guest type polarizing film, that is, the liquid crystal state of the nematic phase due to the action of the dichroic dye.
  • the polarization performance is high as compared with the polarizing element.
  • the strength is excellent as compared with the one coated only with the dichroic dye or the lyotropic liquid crystal.
  • the present invention also includes a polarizing plate including the polarizing film of the present invention and a substrate arranged on the photoalignment film side of the polarizing film.
  • the base material examples include a glass base material and a film base material, and a film base material is preferable.
  • the resin constituting the film substrate include polyolefins such as polyethylene, polypropylene, and norbornene-based polymers; cyclic olefin-based resins; polyvinyl alcohol; polyethylene terephthalates; polymethacrylic acid esters; polyacrylic acid esters; triacetyl cellulose and diacetyl cellulose. And resins such as cellulose esters such as cellulose acetate propionate; polyethylene naphthalate; polycarbonate; polysulfones; polyethersulfones; polyether ketones; polyphenylene sulfides and polyphenylene oxides;
  • cellulose ester base materials examples include “Fujitac Film” (manufactured by Fuji Photo Film Co., Ltd.); “KC8UX2M”, “KC8UY” and “KC4UY” (manufactured by Konica Minolta Opto Co., Ltd.).
  • Commercially available cyclic olefin resins include “Topas” (registered trademark) (Ticona (Germany)), “Arton” (registered trademark) (JSR Corporation), “ZEONOR” (registered trademark), and the like.
  • Such a cyclic olefin resin can be formed into a film by a known means such as a solvent casting method and a melt extrusion method to form a base material.
  • a commercially available cyclic olefin resin base material can also be used.
  • cyclic olefin resin base materials include “Scina” (registered trademark), “SCA40” (registered trademark) (above, manufactured by Sekisui Chemical Industry Co., Ltd.), and “Zeonoa Film” (registered trademark) (manufactured by Optes Co., Ltd.). ) And “Arton Film” (registered trademark) (manufactured by JSR Corporation).
  • the characteristics required for the base material differ depending on the configuration of the polarizing plate, but usually, a base material having as little retardation as possible is preferable.
  • a base material having the smallest possible phase difference include cellulose ester films having no phase difference such as Zero Tuck (Konica Minolta Opto Co., Ltd.) and Z Tuck (Fuji Film Co., Ltd.).
  • an unstretched cyclic olefin resin base material is also preferable.
  • a hard coat treatment, an antireflection treatment, an antistatic treatment, or the like may be applied to the surface of the base material on which the polarizing film is not laminated.
  • the thickness of the base material is preferably thin from the viewpoint of practical handleability, but is preferably thick from the viewpoint of strength and processability.
  • the thickness of the substrate is preferably 5 ⁇ m to 300 ⁇ m, more preferably 20 ⁇ m to 200 ⁇ m.
  • the present invention also includes an optical laminate including the polarizing plate of the present invention and a layer bonded to the polarizing element side of the polarizing plate via an adhesive layer.
  • Examples of the layer bonded to the polarizing element of the present invention in such an optical laminate include various optical layers and protective layers.
  • the various optical layers are layers that function for displaying an image (display screen, etc.) (for example, a layer that functions to improve the visibility of an image), and various optics that can be incorporated into an image display device. Examples include films having characteristics.
  • Such an optical layer may be, for example, a single-layer structure (for example, an optical functional film such as a retardation film, a brightness improving film, an antiglare film, an antireflection film, a diffusion film, a light-collecting film, etc.), and may have multiple layers. It may be a structure (for example, a retardation plate).
  • an optical functional film such as a retardation film, a brightness improving film, an antiglare film, an antireflection film, a diffusion film, a light-collecting film, etc.
  • It may be a structure (for example, a retardation plate).
  • the adhesive layer for adhesively adhering a polarizing element and a layer bonded to the polarizing element is a layer formed of an adhesive.
  • the adhesive adhesive for forming the adhesive layer those conventionally known in the art can be used depending on the type of the layer bonded to the polarizing element, the layer structure of the optical laminate, and the like.
  • the thickness of the adhesive layer may be appropriately determined depending on the layer structure of the optical laminate and the like, and may be, for example, 0.1 to 30 ⁇ m.
  • the present invention also includes an elliptical polarizing plate including the polarizing film of the present invention and a retardation layer having a 1/4 wave plate function (hereinafter, also referred to as “ ⁇ / 4 retardation layer”).
  • the (elliptical) circularly polarizing plate is a functional layer having a function of transmitting only the right or left circularly polarized light component by laminating a ⁇ / 4 retardation plate on a linearly polarizing plate.
  • the elliptical polarizing plate of the present invention may be provided with a ⁇ / 4 retardation layer on either side of the polarizing film of the present invention.
  • the ⁇ / 4 retardation layer constituting the elliptical polarizing plate of the present invention preferably satisfies the optical characteristics represented by the following formulas (a), (b) and (c).
  • Re ( ⁇ ) represents the in-plane retardation value of the retardation layer at the wavelength ⁇ nm
  • Re (nx ( ⁇ ) ⁇ ny ( ⁇ )) ⁇ d (d is the thickness of the retardation layer).
  • Nx represents the main refractive index at a wavelength of ⁇ nm in the direction parallel to the plane of the retardation layer in the refractive index ellipse formed by the retardation layer
  • ny represents the refractive index ellipse formed by the retardation layer. Represents the refractive index at a wavelength of ⁇ nm, which is parallel to the plane of the retardation layer and orthogonal to the nx direction).
  • the retardation layer When the retardation layer satisfies the equations (a) and (b), the retardation layer has a so-called inverse wavelength dispersion in which the in-plane retardation value at a short wavelength is smaller than the in-plane retardation value at a long wavelength.
  • Re (450) / Re (550) is preferably 0.70 or more, more preferably 0, because the reverse wavelength dispersibility is improved and the optical characteristics when incorporated into an image display device or the like are more likely to be improved. It is .78 or more, preferably 0.92 or less, more preferably 0.90 or less, still more preferably 0.87 or less, particularly preferably 0.86 or less, and even more preferably 0.85 or less.
  • Re (650) / Re (550) is preferably 1.0 or more, more preferably 1.01 or more, and further preferably 1.02 or more.
  • the retardation layer may be a stretched film that gives a retardation by stretching a polymer, or may be a liquid crystal cured layer made of a cured product of a liquid crystal composition containing a polymerizable liquid crystal compound.
  • These ⁇ / 4 retardation layers can be manufactured by appropriately selecting and adopting materials and methods conventionally known in the art.
  • the thickness of the ⁇ / 4 retardation layer is not particularly limited, and may be, for example, 100 ⁇ m or less, and is preferably 0.5 ⁇ m to 20 ⁇ m from the viewpoint of reducing the thickness of the image display device or the like incorporating the ⁇ / 4 retardation layer. It is preferably 1 ⁇ m to 3 ⁇ m.
  • a very thin retardation layer having a thickness of 1 ⁇ m to 3 ⁇ m can be produced by a liquid crystal cured layer cured in a state where the polymerizable liquid crystal compound is oriented.
  • the slow axis (optical axis) of the ⁇ / 4 retardation layer and the absorption axis of the substituent are laminated so as to be substantially 45 °. It is preferable to do so.
  • the slow axis (optical axis) of the retardation layer and the absorption axis of the polarizing element so as to be substantially 45 °, the function as an elliptical polarizing plate can be obtained. It should be noted that substantially 45 ° is usually in the range of 45 ⁇ 5 °.
  • the elliptical polarizing plate of the present invention may have a configuration as that of a conventional general elliptical polarizing plate and / or a retardation film.
  • a configuration includes, for example, for the purpose of protecting the surface of an adhesive layer (sheet) for attaching an elliptical polarizing plate to a display element of an optical display, a polarizing element, and a retardation layer from scratches and stains. Examples include the protective film used.
  • the elliptical polarizing plate of the present invention can be used in various display devices.
  • the display device is a device having a display element, and includes a light emitting element or a light emitting device as a light emitting source.
  • Display devices include a liquid crystal display device, an organic electroluminescence (EL) display device, an inorganic electroluminescence (EL) display device, a flexible image display device, a touch panel display device, an electron emission display device (for example, an electric field emission display device (FED)).
  • EL organic electroluminescence
  • EL inorganic electroluminescence
  • FED electric field emission display device
  • the liquid crystal display device includes a transmissive liquid crystal display device, a semi-transmissive liquid crystal display device, a reflective liquid crystal display device, a direct-view type liquid crystal display device, and a projection type liquid crystal display device.
  • These display devices may be display devices that display two-dimensional images, or may be stereoscopic display devices that display three-dimensional images.
  • the elliptical polarizing plate of the present invention can be suitably used for an organic electroluminescence (EL) display device.
  • the display device is preferably a flexible image display device, and the present invention also includes a flexible image display device including the elliptical polarizing plate of the present invention.
  • the flexible image display device having the elliptical polarizing plate of the present invention preferably further has a window and a touch sensor.
  • the flexible image display device is composed of, for example, a laminated body for a flexible image display device and an organic EL display panel, and the laminated body for the flexible image display device is arranged on the visual side with respect to the organic EL display panel and is configured to be bendable. Has been done.
  • the laminated body for a flexible image display device may include a window, a (touch panel) touch sensor, and the like in addition to the elliptical polarizing plate of the present invention described above.
  • the stacking order thereof is arbitrary, but it is preferable that they are stacked in the order of the window, the elliptical polarizing plate, and the touch sensor, or the window, the touch sensor, and the elliptical polarizing plate in this order from the viewing side.
  • the elliptical polarizing plate is present on the visual side of the touch sensor because the pattern of the touch sensor is difficult to be visually recognized and the visibility of the displayed image is improved.
  • Each member can be laminated using an adhesive, an adhesive, or the like.
  • the laminated body for a flexible image display device can be provided with a light-shielding pattern formed on at least one surface of any one of the windows, the elliptical polarizing plate, and the touch sensor.
  • the window is placed on the visual side of the flexible image display device and plays a role of protecting other components from external impacts or environmental changes such as temperature and humidity.
  • glass has been used as such a protective layer, but a window in a flexible image display device is not rigid and rigid like glass, but has flexible characteristics.
  • the window is made of a flexible transparent substrate and may include a hardcourt layer on at least one surface.
  • the window, touch sensor, etc. constituting the laminated body for the flexible image display device are not particularly limited, and conventionally known ones can be adopted.
  • Example 1 Preparation of composition for forming a photoalignment film A copolymer (1) (polymer) was prepared by the following procedure. Copolymer (1)
  • a chlorodimethyl ether was added dropwise to a solution of 4-((6- (methacryloyloxy) hexyl) oxy) benzoic acid in toluene together with an amine catalyst, and then the reaction was allowed to proceed by heating and maintaining at 40 ° C. After cooling the reaction solution, water was added. A 50% aqueous acetic acid solution was added to the separated organic layer and the mixture was stirred. The separated organic layer was concentrated to obtain methoxymethyl 4-((6- (methacryloyloxy) hexyl) oxy) benzoate.
  • copolymer (1) The polymer obtained in this example is referred to as "copolymer (1)”. May be referred to as).
  • the weight average molecular weight of the copolymer (1) was measured by GPC. The results are shown in Table 1.
  • a polarized UV irradiation device SPOT CURE SP-7 with a polarizing element unit; Ushio Denki Co., Ltd.
  • a polarized UV exposure was carried out with an integrated light amount of 100 mJ / cm 2 to form a photoalignment film.
  • the thickness of the obtained photoalignment film was measured with an ellipsometer M-220 (manufactured by JASCO Corporation) and found to be 100 nm.
  • composition for forming a polarizing element was applied onto the obtained photoalignment film using a bar coater, and then dried in a drying oven set at 100 ° C. for 1 minute.
  • Examples 2 to 7 and Comparative Example 1 A polarizing plate was prepared in the same manner as in Example 1 except that the composition of the polymer forming the photoalignment film was changed as shown in Table 1, and the adhesion and orientation were evaluated. The results are shown in Table 1.
  • the polymers prepared in Examples 2 to 7 are referred to as copolymers (2) to copolymers (7), respectively, and the polymers prepared in Comparative Example 1 are referred to as copolymers (8).
  • the structures of the structural unit (i), the structural unit (ii), and the structural unit (iii) are each derived from the following structures.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • General Physics & Mathematics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polarising Elements (AREA)
  • Electroluminescent Light Sources (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Liquid Crystal (AREA)

Abstract

La présente invention concerne un film polarisant comprenant : un film de photo-alignement ; et un polariseur adjacent au film de photo-alignement, le film de photo-alignement étant constitué d'un polymère contenant une unité structurale ayant un groupe photoréactif et une unité structurale ayant un groupe polymérisable, et le polariseur étant un produit durci d'une composition de cristaux liquides qui contient un composé de cristaux liquides et un colorant dichroïque, et contenant une unité structurale ayant un groupe polymérisable dérivé du composé de cristaux liquides ou du colorant dichroïque.
PCT/JP2021/019919 2020-06-15 2021-05-26 Film polarisant, plaque polarisante, produit stratifié optique, plaque polarisante elliptique, dispositif d'affichage électroluminescent organique et dispositif d'affichage d'image flexible WO2021256199A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202180042435.0A CN115715374A (zh) 2020-06-15 2021-05-26 偏光膜、偏光板、光学层叠体、椭圆偏光板、有机el显示装置及柔性图像显示装置
KR1020227045962A KR20230021020A (ko) 2020-06-15 2021-05-26 편광막, 편광판, 광학 적층체, 타원 편광판, 유기 el 표시 장치 및 플렉시블 화상 표시 장치

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2020103151A JP2021196514A (ja) 2020-06-15 2020-06-15 偏光膜、偏光板、光学積層体、楕円偏光板、有機ｅｌ表示装置およびフレキシブル画像表示装置
JP2020-103151 2020-06-15

Publications (1)

Publication Number Publication Date
WO2021256199A1 true WO2021256199A1 (fr) 2021-12-23

Family

ID=79195405

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2021/019919 WO2021256199A1 (fr) 2020-06-15 2021-05-26 Film polarisant, plaque polarisante, produit stratifié optique, plaque polarisante elliptique, dispositif d'affichage électroluminescent organique et dispositif d'affichage d'image flexible

Country Status (5)

Country Link
JP (1) JP2021196514A (fr)
KR (1) KR20230021020A (fr)
CN (1) CN115715374A (fr)
TW (1) TW202204453A (fr)
WO (1) WO2021256199A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005326439A (ja) * 2004-05-12 2005-11-24 Fuji Photo Film Co Ltd 位相差板材料、重合体、位相差板および画像表示装置
CN101935368A (zh) * 2010-09-27 2011-01-05 上海交通大学 含有双光敏单元的液晶超分子材料的合成方法
JP2013033249A (ja) * 2011-07-07 2013-02-14 Sumitomo Chemical Co Ltd 偏光素子、円偏光板及びそれらの製造方法
WO2017065202A1 (fr) * 2015-10-16 2017-04-20 Dic株式会社 Polymère pour film de photo-alignement, solution polymère, film de photo-alignement, corps anisotrope optique et élément d'affichage à cristaux liquides
WO2017065079A1 (fr) * 2015-10-16 2017-04-20 Dic株式会社 Polymère pour film de photo-alignement, solution polymère, film de photo-alignement, corps anisotrope optique et élément d'affichage à cristaux liquides
WO2019131943A1 (fr) * 2017-12-28 2019-07-04 富士フイルム株式会社 Procédé de fabrication d'un stratifié optique, stratifié optique, et dispositif d'affichage d'images

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005326439A (ja) * 2004-05-12 2005-11-24 Fuji Photo Film Co Ltd 位相差板材料、重合体、位相差板および画像表示装置
CN101935368A (zh) * 2010-09-27 2011-01-05 上海交通大学 含有双光敏单元的液晶超分子材料的合成方法
JP2013033249A (ja) * 2011-07-07 2013-02-14 Sumitomo Chemical Co Ltd 偏光素子、円偏光板及びそれらの製造方法
WO2017065202A1 (fr) * 2015-10-16 2017-04-20 Dic株式会社 Polymère pour film de photo-alignement, solution polymère, film de photo-alignement, corps anisotrope optique et élément d'affichage à cristaux liquides
WO2017065079A1 (fr) * 2015-10-16 2017-04-20 Dic株式会社 Polymère pour film de photo-alignement, solution polymère, film de photo-alignement, corps anisotrope optique et élément d'affichage à cristaux liquides
WO2019131943A1 (fr) * 2017-12-28 2019-07-04 富士フイルム株式会社 Procédé de fabrication d'un stratifié optique, stratifié optique, et dispositif d'affichage d'images

Also Published As

Publication number Publication date
KR20230021020A (ko) 2023-02-13
JP2021196514A (ja) 2021-12-27
TW202204453A (zh) 2022-02-01
CN115715374A (zh) 2023-02-24

Similar Documents

Publication Publication Date Title
JP2023009102A (ja) 長尺偏光フィルムの製造方法
JP6299367B2 (ja) パターン偏光フィルムの製造方法
JP2022008866A (ja) パターン偏光フィルム
JP2023080141A (ja) 偏光フィルム及びその製造方法
JP2021182144A (ja) 複合偏光板および液晶表示装置
JP7281953B2 (ja) 積層体
JP7198683B2 (ja) 積層体
TW202032177A (zh) 積層體及圖像顯示裝置
JP7313153B2 (ja) 重合性液晶組成物、偏光膜およびその製造方法、偏光板ならびに表示装置
JP7287896B2 (ja) 偏光フィルムの製造方法及び偏光フィルム
CN111279233B (zh) 偏光膜的制造方法及偏光膜
WO2020170697A1 (fr) Stratifié et dispositif d'affichage d'image
WO2021193350A1 (fr) Composition pour former un film polarisant, et film polarisant
WO2020022009A1 (fr) Stratifié
WO2021256199A1 (fr) Film polarisant, plaque polarisante, produit stratifié optique, plaque polarisante elliptique, dispositif d'affichage électroluminescent organique et dispositif d'affichage d'image flexible
WO2019198697A1 (fr) Composition de cristaux liquides polymérisable
WO2020022010A1 (fr) Corps stratifié
WO2020195881A1 (fr) Procédé de fabrication de film polarisant, et film polarisant
WO2022163398A1 (fr) Composition de cristaux liquides polymérisable, membrane de polarisation, film polarisant, plaque de polarisation circulaire et dispositif d'affichage

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21824915

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 20227045962

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21824915

Country of ref document: EP

Kind code of ref document: A1