WO2020066832A1 - 偏光フィルム及びその製造方法 - Google Patents

偏光フィルム及びその製造方法 Download PDF

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Publication number
WO2020066832A1
WO2020066832A1 PCT/JP2019/036743 JP2019036743W WO2020066832A1 WO 2020066832 A1 WO2020066832 A1 WO 2020066832A1 JP 2019036743 W JP2019036743 W JP 2019036743W WO 2020066832 A1 WO2020066832 A1 WO 2020066832A1
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Prior art keywords
meth
group
polarizer
resin layer
acrylate
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PCT/JP2019/036743
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English (en)
French (fr)
Japanese (ja)
Inventor
太田　陽介
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Priority to CN201980062452.3A priority Critical patent/CN112789527B/zh
Priority to KR1020217007731A priority patent/KR102909328B1/ko
Priority to CN202410297035.XA priority patent/CN117970552A/zh
Publication of WO2020066832A1 publication Critical patent/WO2020066832A1/ja
Anticipated expiration legal-status Critical
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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
    • G02B5/3041—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks
    • G02B5/305—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks including organic materials, e.g. polymeric layers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B32B27/308—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising acrylic (co)polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/02—Physical, chemical or physicochemical properties
    • B32B7/023—Optical properties
    • 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
    • C08F20/00—Homopolymers and 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • 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
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F220/343—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/08—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of polarising materials
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3016—Polarising elements involving passive liquid crystal elements
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/40—Properties of the layers or laminate having particular optical properties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2551/00—Optical elements

Definitions

  • the present invention relates to a polarizing film and a method for producing the same.
  • a polarizing film or the like is used for a flat panel display (FPD).
  • a polarizing film in addition to a polarizing film having a polarizer in which a dichroic dye such as iodine is orientation-adsorbed to a polyvinyl alcohol-based resin film, a polymerizable liquid crystal compound is coated on a substrate and polymerized.
  • the polarizing film which has the polarizer obtained by is known.
  • Patent Document 1 discloses a polarizing film having a dye diffusion preventing layer on both surfaces of a polarizer containing a polymer of a polymerizable liquid crystal compound and a dichroic dye.
  • An object of the present invention is to provide a polarizing film having excellent adhesion between layers and a method for producing the same.
  • the inventor of the present invention has made intensive studies to solve the above-mentioned problems.
  • the first resin layer, the polarizer, the alignment film, and the second resin layer are laminated in this order on the first resin layer, the polarizer. It has been found that the above-mentioned problems can be solved by forming the alignment film, the second resin layer, and the second resin layer with a cured product of a composition containing a compound having a (meth) acryloyl group, thereby completing the present invention. That is, the present invention includes the following embodiments.
  • a polarizing film in which a first resin layer, a polarizer, an alignment film, and a second resin layer are laminated in this order,
  • the first resin layer is a cured product of a first curable composition containing a (meth) acrylic compound
  • the polarizer is a cured product of a polarizer forming composition including a polymerizable liquid crystal compound having a (meth) acryloyl group and a dichroic dye
  • the alignment film is a cured product of the alignment film forming composition containing the (meth) acrylic compound
  • the polarizing film, wherein the second resin layer is a cured product of a second curable composition containing a (meth) acrylic compound.
  • the polyfunctional (meth) acrylate compound has a branched structure, and the number of atoms of a chain connecting the branch point closest to the (meth) acryloyl group in the branched structure and the (meth) acryloyl group is:
  • the first curable composition is applied or superimposed on the polarizer surface of a laminate in which the second resin layer, the alignment film, and the polarizer are laminated in this order, and the first curable composition is cured.
  • the first curable composition formed on the release film, the second resin layer, the alignment film, and the polarizer surface of the laminate in which the polarizer is laminated in this order are superimposed, and the release film is formed.
  • a laminate in which a release film, a first resin layer, a polarizer, an alignment film, and a second resin layer are laminated in this order is formed.
  • the polarizing film of the present invention has excellent adhesion between layers.
  • BRIEF DESCRIPTION OF THE DRAWINGS It is a schematic sectional drawing of the layer structure of the polarizing film with a front plate in which the polarizing film which is one Embodiment of this invention was laminated.
  • BRIEF DESCRIPTION OF THE DRAWINGS It is a schematic sectional drawing of the layer structure of the polarizing plate with a front plate in which the polarizing film which is one Embodiment of this invention was laminated.
  • BRIEF DESCRIPTION OF THE DRAWINGS It is a schematic sectional drawing of the layer structure of the polarizing film with a front plate which laminated
  • BRIEF DESCRIPTION OF THE DRAWINGS It is a schematic sectional drawing of the layer structure of the polarizing plate with a front plate in which the polarizing film which is one Embodiment of this invention was laminated.
  • polarizing film In the polarizing film of the present invention, a first resin layer, a polarizer, an alignment film, and a second resin layer are laminated in this order.
  • the first resin layer is a cured product of a first curable composition containing a (meth) acrylic compound
  • the polarizer is a polarizer containing a polymerizable liquid crystal compound having a (meth) acryloyl group and a dichroic dye.
  • the polarizing film of the present invention is configured such that each layer is formed of a cured product of the composition containing the compound having a (meth) acryloyl group, that is, containing the polymer of the compound having a (meth) acryloyl group.
  • the compatibility between the layers is high, and excellent adhesion between the layers can be achieved.
  • the polarizer included in the polarizing film of the present invention is formed on the surface of the alignment film opposite to the second resin layer.
  • the polarizer is a cured product of a polarizer-forming composition containing a polymerizable liquid crystal compound having a (meth) acryloyl group and a dichroic dye.
  • the dichroic dye is included in the polymerizable liquid crystal compound, and the polymerizable liquid crystal compound and the dichroic dye are polymerized in an oriented state and are cured.
  • the dichroic dye is less likely to be retained by the polymer component, and the dichroic dye is separated from the polarizer by the first resin in a high-temperature environment or the like.
  • heat is diffused into the layer or the second resin layer, and the polarization performance tends to be reduced with time.
  • a resin layer having good compatibility with the polymer of the polymerizable liquid crystal compound is simply selected in order to improve the adhesion between the layers of the polarizing film, the phase of the dichroic dye contained in the polarizer to the resin layer may be reduced.
  • the first resin layer and the second resin layer are each composed of a cured product of a curable composition containing a (meth) acrylic compound, in a mode in which a crosslinked structure can be formed, in addition to adhesion, It can also have excellent heat resistance, and can effectively suppress a decrease in the polarizing performance of the polarizing film even when exposed to a high-temperature environment for a long time.
  • the heat resistance refers to a property that can suppress a decrease in polarization performance, for example, a change in the degree of polarization or transmittance, even when exposed to a high-temperature environment for a long time, and increases heat resistance. Improving means that the decrease or change in polarization performance due to high temperature is smaller.
  • the polymerizable liquid crystal compound (hereinafter sometimes referred to as “polymerizable liquid crystal compound (A)”) contained in the polarizer-forming composition is a liquid crystal having at least one (meth) acryloyl group.
  • the compound is preferably a liquid crystal compound having two or more (meth) acryloyl groups from the viewpoint of improving the adhesion and heat resistance of the polarizing film.
  • the polymerizable liquid crystal compound (A) may contain a polymerizable group other than the (meth) acryloyl group.
  • the polymerizable group refers to a group that can participate in a polymerization reaction by an active radical or an acid generated from a polymerization initiator.
  • the polymerizable group other than the (meth) acryloyl group examples include a vinyl group, a vinyloxy group, a 1-chlorovinyl group, an isopropenyl group, a 4-vinylphenyl group, an oxiranyl group, and an oxetanyl group.
  • the polymerizable group of the polymerizable liquid crystal compound (A) is preferably composed of a (meth) acryloyl group, and composed of a (meth) acryloyloxy group. More preferably, it is performed.
  • the polymerizable liquid crystal compound (A) is preferably a compound exhibiting smectic liquid crystallinity.
  • a polarizer having a high degree of alignment order can be formed.
  • the liquid crystal state of the polymerizable liquid crystal compound (A) is a smectic phase (smectic liquid crystal state). From the viewpoint of realizing a higher degree of alignment order, the liquid crystal state is more preferably a higher-order smectic phase (higher-order smectic liquid crystal state). preferable.
  • a higher smectic phase means a smectic B phase, a smectic D phase, a smectic E phase, a smectic F phase, a smectic G phase, a smectic H phase, a smectic I phase, a smectic J phase, a smectic K phase and a smectic L phase.
  • a smectic B phase, a smectic F phase and a smectic I phase are more preferable.
  • the liquid crystal may be a thermotropic liquid crystal or a lyotropic liquid crystal, but is preferably a thermotropic liquid crystal in that the film thickness can be precisely controlled.
  • the polymerizable liquid crystal compound (A) may be a monomer, but may be an oligomer or a polymer in which a polymerizable group is polymerized.
  • the polymerizable liquid crystal compound (A) is not particularly limited as long as it has at least one (meth) acryloyl group, and a known polymerizable liquid crystal compound can be used. preferable.
  • a polymerizable liquid crystal compound for example, a compound represented by the following formula (A1) (hereinafter sometimes referred to as “polymerizable liquid crystal compound (A1)”) may be mentioned.
  • X 1 and X 2 independently represent a divalent aromatic group or a divalent alicyclic hydrocarbon group, wherein the divalent aromatic group or the divalent alicyclic hydrocarbon is
  • the hydrogen atom contained in the group may be substituted by 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, a sulfur atom, or a nitrogen atom.
  • at least one of X 1 and X 2 is a 1,4-phenylene group which may have a substituent or a cyclohexane-1,4-diyl group which may have a substituent.
  • Y 1 is a single bond or a divalent linking group.
  • n is 1 to 3, and when n is 2 or more, a plurality of X 1 may be the same as or different from each other.
  • X 2 may be the same as any or all of the plurality of X 1 , or may be different.
  • a plurality of Y 1 may be the same or different. From the viewpoint of liquid crystallinity, n is preferably 2 or more.
  • U 1 represents a hydrogen atom or a (meth) acryloyloxy group.
  • U 2 represents a (meth) acryloyloxy group.
  • W 1 and W 2 are each independently a single bond or a divalent linking group.
  • V 1 and V 2 independently represent an alkanediyl group having 1 to 20 carbon atoms which may have a substituent, wherein —CH 2 — constituting the alkanediyl group is —O—, —CO—, —S— or NH— may be substituted.
  • X 1 and X 2 are, independently of each other, preferably a 1,4-phenylene group which may have a substituent, or a group which may have a substituent.
  • a cyclohexane-1,4-diyl group, and at least one of X 1 and X 2 is a 1,4-phenylene group which may have a substituent or a
  • a cyclohexane-1,4-diyl group is preferable, and a trans-cyclohexane-1,4-diyl group is preferable.
  • Examples of the substituent which the 1,4-phenylene group which may have a substituent or the cyclohexane-1,4-diyl group which may have a substituent optionally have include a methyl group and an ethyl group.
  • Examples thereof include an alkyl group having 1 to 4 carbon atoms such as a butyl group and a butyl group, a cyano group, and a halogen atom such as a chlorine atom and a fluorine atom. Preferably it is unsubstituted.
  • the polymerizable liquid crystal compound (A1) is represented by the formula (A1-1): -(X 1 -Y 1- ) n -X 2- (A1-1) [In the formula, X 1 , Y 1 , X 2 and n each have the same meaning as described above. ] [Hereinafter referred to as a partial structure (A1-1). ] Is preferably an asymmetric structure in that smectic liquid crystallinity is easily developed.
  • Examples of the polymerizable liquid crystal compound (A1) in which the partial structure (A1-1) has an asymmetric structure include, for example, a polymerizable liquid crystal compound (A1) in which n is 1 and one X 1 and X 2 are different from each other. ).
  • the polymerizable liquid crystal compound (A1), X 1 to bind to W 1 of the two X 1 is a structure that is different from the other of X 1 and X 2, the other of X 1 and X 2 and are mutually the same structure
  • R a and R b independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • Y 1 is, -CH 2 CH 2 -, - COO- or more preferably a single bond, when a plurality of Y 1 are present, Y 1 which binds to X 2 is, -CH 2 CH 2 - or CH 2 O- and it is more preferable.
  • X 1 and X 2 all have the same structure, it is preferable that two or more Y 1, which are bonding methods different from each other, exist.
  • the structure becomes an asymmetric structure, so that smectic liquid crystallinity tends to be easily exhibited.
  • U 2 is a (meth) acryloyloxy group.
  • U 1 is a hydrogen atom or a (meth) acryloyloxy group, preferably a (meth) acryloyloxy group. It is preferable that both U 1 and U 2 are (meth) acryloyloxy groups from the viewpoint of improving the adhesion between layers of the polarizing film and the heat resistance.
  • the (meth) acryloyloxy group may be in a polymerized state or an unpolymerized state, but is preferably in an unpolymerized state.
  • the alkanediyl groups represented by V 1 and V 2 include methylene, ethylene, propane-1,3-diyl, butane-1,3-diyl, butane-1,4-diyl, 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 And an icosan-1,20-diyl group.
  • V 1 and V 2 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 optionally has include a cyano group and a halogen atom, and the alkanediyl group is preferably unsubstituted, and is an unsubstituted linear alkanediyl group. Is more preferred.
  • W 1 and W 2 are each independently preferably a single bond, —O—, —S—, —COO— or OCOO—, more preferably a single bond 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 (meth) acryloyl group, and a known polymerizable liquid crystal compound can be used. It is preferable that the structure that easily exhibits smectic liquid crystallinity has an asymmetric molecular structure in the molecular structure, and specifically has the following partial structures (Aa) to (Ai)
  • the polymerizable liquid crystal compound is more preferably a polymerizable liquid crystal compound exhibiting smectic liquid crystallinity. It is more preferable to have a partial structure of (Aa), (Ab) or (Ac) from the viewpoint of easily exhibiting higher order smectic liquid crystal properties. In the following (Aa) to (Ai), * represents a bond (single bond).
  • Examples of the polymerizable liquid crystal compound (A) include compounds represented by formulas (A-1) to (A-25).
  • the polymerizable liquid crystal compound (A) has a cyclohexane-1,4-diyl group, the cyclohexane-1,4-diyl group is preferably in a trans form.
  • the formulas (A-2), (A-3), (A-4), (A-5), (A-6), (A-7), and (A- 8), at least one selected from the group consisting of compounds represented by formulas (A-13), (A-14), (A-15), (A-16) and (A-17) Species are preferred.
  • the polymerizable liquid crystal compound (A) one type may be used alone, or two or more types may be used in combination.
  • ⁇ Polymerizable liquid crystal compound (A) is described in, for example, Lub et al., Recl. Trav. Chim. Pays-Bas, 115, 321-328 (1996), or a known method described in Japanese Patent No. 4719156.
  • the polarizer-forming composition may contain a polymerizable liquid crystal compound other than the polymerizable liquid crystal compound (A), but from the viewpoint of obtaining a polarizer having a high degree of orientational order, the polarizer formation composition is preferably used.
  • the ratio of the polymerizable liquid crystal compound (A) to the total mass of the total polymerizable liquid crystal compound contained in the composition for use is preferably 51% by mass or more, more preferably 70% by mass or more, and still more preferably 90% by mass. % Or more.
  • composition for forming a polarizer contains two or more polymerizable liquid crystal compounds (A), at least one of them may be a polymerizable liquid crystal compound (A1), and all of them are polymerizable liquid crystal compounds (A1). ).
  • polymerizable liquid crystal compounds A1
  • all of them are polymerizable liquid crystal compounds (A1). ).
  • liquid crystallinity can be temporarily maintained even at a temperature lower than the liquid crystal-crystal phase transition temperature.
  • the content of the polymerizable liquid crystal compound in the polarizer-forming composition is preferably from 40 to 99.9% by mass, more preferably from 60 to 99% by mass, based on the solid content of the polarizer-forming composition. And more preferably 70 to 99% by mass.
  • solid content means the total amount of components excluding the solvent from the composition for forming a polarizer.
  • the polarizer-forming composition for forming a polarizer contains a dichroic dye.
  • the dichroic dye means a dye having a property that the absorbance in the major axis direction of the molecule is different from 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 properties, and may be a dye or a pigment. Two or more dyes or pigments may be used in combination, or a dye and a pigment may be used in combination. Further, the dichroic dye may have polymerizability or may have liquid crystallinity.
  • the dichroic dye preferably has a maximum absorption wavelength ( ⁇ MAX ) in the range of 300 to 700 nm.
  • ⁇ MAX maximum absorption wavelength
  • dichroic dyes include acridine dyes, oxazine dyes, cyanine dyes, naphthalene dyes, azo dyes and anthraquinone dyes.
  • the azo dye examples include a monoazo dye, a bisazo dye, a trisazo dye, a tetrakisazo dye and a stilbene azo dye, and a bisazo dye and a trisazo dye are preferable.
  • a compound represented by the formula (I) hereinafter, “compound” (I) ").
  • K 1 and K 3 each independently represent a phenyl group which may have a substituent, a naphthyl group which may have a substituent or a group which has a substituent. 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 heterocyclic ring which may have a substituent Represents a group.
  • p represents an integer of 1 to 4.
  • a plurality of K 2 may be the same or different from each other.
  • Examples of the monovalent heterocyclic group include groups obtained by removing one hydrogen atom from a heterocyclic compound such as quinoline, thiazole, benzothiazole, thienothiazole, imidazole, benzimidazole, oxazole, and benzoxazole.
  • Examples of the divalent heterocyclic group include groups in which two hydrogen atoms have been removed from the heterocyclic compound.
  • substituent optionally contained in the phenyl group, naphthyl group and monovalent heterocyclic group in K 1 and K 3 , and the p-phenylene group, naphthalene-1,4-diyl group and divalent heterocyclic group in K 2 are 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; and a methoxy group, an ethoxy group, a butoxy group, and the like.
  • C1-C20 alkoxy group having a polymerizable group C1-C4 fluoroalkyl group such as trifluoromethyl group; cyano group; nitro group; halogen atom; amino group, diethylamino group, pyrrolidino
  • Substituted or unsubstituted amino group such as a group (a substituted amino group is an amino group having one or two alkyl groups having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms having a polymerizable group)
  • Means one or two amino groups with or two substituted alkyl groups are bonded to one another an amino group which forms an alkanediyl group having 2 to 8 carbon atoms.
  • Unsubstituted amino groups are -NH 2 )).
  • the polymerizable group includes an acryloyl group, a methacryloyl group, an acryloyloxy group, a methacryloyloxy group, and the like.
  • B 1 to B 30 each independently represent 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, Represents an unsubstituted amino group (the definition of the substituted amino group and the unsubstituted amino group is as described above), a chlorine atom or a trifluoromethyl group.
  • N1 to n4 each independently represent an integer of 0 to 3.
  • n1 is 2 or more, a plurality of B 2 may be the same or different from each other, When n2 is 2 or more, a plurality of 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, a plurality of B 14 may be the same or different from each other. ]
  • anthraquinone dye a compound represented by the formula (I-9) is preferable.
  • R 1 ⁇ R 8 independently of one another, represent a hydrogen atom, -R x, -NH 2, -NHR x, -NR x 2, the -SR x, or a halogen atom.
  • R x represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms.
  • a compound represented by the formula (I-10) is preferable.
  • R 9 ⁇ R 15 independently of one another, represent a hydrogen atom, -R x, -NH 2, -NHR x, -NR x 2, the -SR x, or a halogen atom.
  • R x represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms.
  • a compound represented by the formula (I-11) is preferable.
  • R 16 to R 23 independently represent a hydrogen atom, -R x , -NH 2 , -NHR x , -NR x 2 , -SR x or a halogen atom.
  • R x represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms.
  • the alkyl group having 1 to 6 carbon atoms for R x a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group And a hexyl group.
  • the aryl group having 6 to 12 carbon atoms include a phenyl group, a toluyl group, a xylyl group, and a naphthyl group.
  • cyanine dye a compound represented by the formula (I-12) and a compound represented by the formula (I-13) are preferable.
  • D 1 and D 2 each independently represent a group represented by any of formulas (I-12a) to (I-12d).
  • n5 represents an integer of 1 to 3.
  • D 3 and D 4 each independently represent a group represented by any of formulas (I-13a) to (1-13h).
  • n6 represents an integer of 1 to 3.
  • the dichroic dye contained in the polarizer-forming composition for forming a polarizer is preferably an azo dye.
  • the weight average molecular weight of the dichroic dye is usually from 300 to 2,000, preferably from 400 to 1,000.
  • the weight average molecular weight of the dichroic dye is equal to or less than the above upper limit, the dichroic dye present in a state of being included in the polymerizable liquid crystal compound in the polarizer easily moves, and moves out of the polarizer due to a high temperature environment or the like. It becomes easier to spread.
  • the first resin layer and the second resin layer are each formed of a cured product of a curable composition containing a (meth) acrylic compound. Diffusion of the dye (particularly, thermal diffusion) can be effectively suppressed, and a decrease in polarization performance can be effectively suppressed.
  • the dichroic dye contained in the polarizer-forming composition for forming a polarizer is preferably hydrophobic.
  • the hydrophobic dichroic dye means a dye whose solubility in 100 g of water at 25 ° C. is 1 g or less.
  • the content of the dichroic dye in the composition for forming a polarizer can be appropriately determined according to the type of the dichroic dye to be used, and is preferably 0.1 to 100 parts by mass of the polymerizable liquid crystal compound.
  • the amount is 50 parts by mass, more preferably 0.1 to 20 parts by mass, and still more preferably 0.1 to 12 parts by mass.
  • the content of the dichroic dye is within the above range, it is difficult to disturb the alignment of the polymerizable liquid crystal compound, and a polarizer having a high degree of alignment order can be obtained.
  • the polarizer-forming composition for forming a polarizer may contain a polymerization initiator.
  • the polymerization initiator is a compound capable of initiating a polymerization reaction of the polymerizable liquid crystal compound, and a photopolymerization initiator is preferable in that the polymerization reaction can be initiated under lower temperature conditions.
  • Specific examples include a photopolymerization initiator capable of generating an active radical or an acid by the action of light, and among them, a photopolymerization initiator capable of generating a radical by the action of light is preferable.
  • the polymerization initiators can be used alone or in combination of two or more.
  • photopolymerization initiator a known photopolymerization initiator can be used.
  • photopolymerization initiator that generates an active radical a self-cleaving type photopolymerization initiator, a hydrogen abstraction type photopolymerization initiator There is.
  • self-cleavable photopolymerization initiators include self-cleavable benzoin-based compounds, acetophenone-based compounds, hydroxyacetophenone-based compounds, ⁇ -aminoacetophenone-based compounds, oxime ester-based compounds, acylphosphine oxide-based compounds, and azo-based compounds. Can be used.
  • a hydrogen abstraction type photopolymerization initiator a hydrogen abstraction type benzophenone-based compound, benzoin ether-based compound, benzyl ketal-based compound, dibenzosuberone-based compound, anthraquinone-based compound, xanthone-based compound, thioxanthone-based compound, halogenoacetophenone-based Compounds, dialkoxyacetophenone-based compounds, halogenobisimidazole-based compounds, halogenotriazine-based compounds, triazine-based compounds, and the like can be used.
  • an iodonium salt, a sulfonium salt, or the like can be used as a photopolymerization initiator that generates carboxylic acid.
  • a reaction at a low temperature is preferable from the viewpoint of preventing dissolution of the dye, and a self-cleavable photopolymerization initiator is preferable from the viewpoint of the reaction efficiency at a low temperature.
  • a self-cleavable photopolymerization initiator is preferable from the viewpoint of the reaction efficiency at a low temperature.
  • an acetophenone-based compound, a hydroxyacetophenone-based compound, and ⁇ -aminoacetophenone Compounds and oxime ester compounds are preferred.
  • Examples of the photopolymerization initiator include the following.
  • Benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin isobutyl ether; 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1,2-diphenyl-2,2-dimethoxyethan-1-one, 2-hydroxy-2-methyl-1- [4- (2- Hydroxyacetophenones such as oligomers of hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexylphenyl ketone and 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propan-1-one Compound; ⁇ -aminoacetophenones such as 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan-1-one, 2-dimethylamino-2-benzyl-1- (4-morpholinophenyl) butan-1-one Compound; 1,2-octanedione,
  • the photopolymerization initiator may be appropriately selected, for example, from the above photopolymerization initiator in relation to the polymerizable liquid crystal compound contained in the polarizer-forming composition.
  • a commercially available photopolymerization initiator may be used.
  • Commercially available polymerization initiators include Irgacure (registered trademark) 907, 184, 651, 819, 250, and 369, 379, 127, 754, OXE01, OXE02, OXE03 (manufactured by BASF); Omnirad @ BCIM, Esacure 1001M, Esacure KIP160 (manufactured by IDM Resins BV); Sequol (registered trademark) BZ, Z, and BEE (manufactured by Seiko Chemical Co., Ltd.); Kayacure (registered trademark) BP100, and UVI-6992 (Dow) Chemical Co., Ltd.); Adeka Optomer SP-152, N-1717, N-1919, SP-170, Adeka Arcles NCI-831, Adeka Arcules NCI-930 (ADEKA Corporation); TAZ-A, Fine TAZ-PP (manufactured by N
  • the content of the polymerization initiator in the polarizer-forming composition for forming the polarizer is preferably 1 to 10 parts by mass, more preferably 1 to 8 parts by mass, per 100 parts by mass of the polymerizable liquid crystal compound. Parts by weight, more preferably 2 to 8 parts by weight, particularly preferably 4 to 8 parts by weight. When the content of the polymerization initiator is within the above range, the polymerization reaction of the polymerizable liquid crystal compound can be performed without significantly disturbing the orientation of the polymerizable liquid crystal compound.
  • the polymerization rate of the polymerizable liquid crystal compound in the present invention is preferably 60% or more, more preferably 65% or more, and even more preferably 70% or more, from the viewpoint of line contamination and handling during production.
  • the composition for forming a polarizer may further contain a photosensitizer.
  • the photosensitizer By using the photosensitizer, the polymerization reaction of the polymerizable liquid crystal compound can be further promoted.
  • the photosensitizer include xanthone compounds such as xanthone and thioxanthone (eg, 2,4-diethylthioxanthone and 2-isopropylthioxanthone); anthracene compounds such as anthracene and an alkoxy group-containing anthracene (eg, dibutoxyanthracene); Phenothiazine and rubrene are exemplified.
  • the photosensitizers can be used alone or in combination of two or more.
  • the content thereof may be appropriately determined according to the types and amounts of the polymerization initiator and the polymerizable liquid crystal compound, and 100 parts by mass of the polymerizable liquid crystal compound. Is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 10 parts by mass, and still more preferably 0.5 to 8 parts by mass.
  • the composition for forming a polarizer may contain a leveling agent.
  • the leveling agent has a function of adjusting the fluidity of the composition for forming a polarizer and flattening a coating film obtained by applying the composition for forming a polarizer.
  • Agents As the leveling agent, at least one selected from the group consisting of a leveling agent mainly containing a polyacrylate compound and a leveling agent mainly containing a fluorine atom-containing compound is preferable.
  • the leveling agents can be used alone or in combination of two or more.
  • leveling agent containing a polyacrylate compound as a main component examples include “BYK-350”, “BYK-352”, “BYK-353”, “BYK-354”, “BYK-355”, and “BYK-358N”. , “BYK-361N”, “BYK-380”, “BYK-381” and “BYK-392” (BYK @ Chemie).
  • leveling agent containing a fluorine atom-containing compound as a main component examples include, for example, “Megafac (registered trademark) R-08”, “R-30”, “R-90”, “F-410”, and “F-410”.
  • the content is preferably 0.05 to 5 parts by mass, more preferably 0.05 to 3 parts by mass, based on 100 parts by mass of the polymerizable liquid crystal compound.
  • the content of the leveling agent is within the above range, the polymerizable liquid crystal compound is likely to be horizontally aligned, is less likely to cause unevenness, and tends to obtain a smoother polarizer.
  • the composition for forming a polarizer may contain other additives other than the photosensitizer and the leveling agent.
  • Other additives include antioxidants, release agents, stabilizers, coloring agents such as bluing agents, flame retardants and lubricants.
  • the content of the other additive is more than 0% and 20% by mass or less based on the solid content of the composition for forming a polarizer. Is more preferable, and more preferably more than 0% and 10% by mass or less.
  • the composition for forming a polarizer can be produced by a conventionally known method for preparing a composition for forming a polarizer, and usually includes a polymerizable liquid crystal compound and a dichroic dye, and, if necessary, a polymerization initiator and It can be prepared by mixing and stirring additives and the like.
  • a compound exhibiting smectic liquid crystallinity has a high viscosity, and therefore, from the viewpoint of improving the applicability of the polarizer forming composition and facilitating the formation of the polarizer, the viscosity is increased by adding a solvent to the polarizer forming composition. Adjustments may be made.
  • the solvent used in the polarizer-forming composition can be appropriately selected according to the solubility of the polymerizable liquid crystal compound and the dichroic dye used.
  • water alcohol solvents such as methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, methyl cellosolve, butyl cellosolve, 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, methyl amyl ketone and methyl isobutyl ketone; aliphatic hydrocarbon solvents such as pentane, hexane and heptane; toluene
  • alcohol solvents
  • the content of the solvent is preferably from 100 to 1,900 parts by mass, more preferably from 150 to 900 parts by mass, and still more preferably from 180 to 600 parts by mass, based on 100 parts by mass of the solid content of the polarizer-forming composition. Department.
  • the polarizer is preferably a polarizer having a high degree of orientational order.
  • a polarizer having a high degree of orientational order shows 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 a periodic structure of molecular orientation. Therefore, the polarizer constituting the polarizing film of the present invention preferably shows a Bragg peak in X-ray diffraction measurement.
  • the polymerizable liquid crystal compound or a polymer thereof is oriented such that the polarizer shows a Bragg peak in X-ray diffraction measurement. More preferably, the liquid crystal compound is “horizontal alignment” in which the molecules of the polymerizable liquid crystal compound are aligned in the absorbing direction. In the present invention, a polarizer having a plane period interval of molecular orientation of 3.0 to 6.0 ° is preferable. A high degree of alignment order showing a Bragg peak can be realized by controlling the type of the polymerizable liquid crystal compound, the type and the amount of the dichroic dye, the type and the amount of the polymerization initiator, and the like.
  • the polarizer forms a coating film of the composition for forming a polarizer on an alignment film, removes a solvent from the coating film, and causes the polymerizable liquid crystal compound to undergo a phase transition to a liquid phase. It can be obtained by a method comprising raising the temperature to a temperature equal to or higher than the temperature, and then lowering the temperature, thereby causing the polymerizable liquid crystal compound to undergo a phase transition to a smectic phase, and polymerizing the polymerizable liquid crystal compound while maintaining the smectic phase. .
  • a coating method such as a spin coating method, an extrusion method, a gravure coating method, a die coating method, a bar coating method, an applicator method, or a printing method such as a flexographic method.
  • a publicly known method such as a method can be used.
  • the solvent is removed by drying or the like under the condition that the polymerizable liquid crystal compound contained in the coating film obtained from the polarizer-forming composition is not polymerized, whereby a dried coating film is formed.
  • the drying method include a natural drying method, a ventilation drying method, a heating drying method, and a reduced-pressure drying method.
  • the temperature is raised to a temperature higher than the temperature at which the polymerizable liquid crystal compound undergoes a phase transition to the liquid phase, and then the temperature is lowered, and the polymerizable liquid crystal compound is converted into a smectic phase (smectic liquid crystal state).
  • a phase transition may be performed after removing the solvent in the coating film, or may be performed simultaneously with the removal of the solvent.
  • a polarizer is formed as a cured layer of the composition for forming a polarizer.
  • the polymerization method is preferably a photopolymerization method.
  • the light applied to the dried coating film includes, as the type of the polymerizable liquid crystal compound contained in the dried coating film (particularly, the type of the polymerizable group included in the polymerizable liquid crystal compound), the type of the polymerization initiator, and They are appropriately selected according to their amounts and the like.
  • At least one active energy ray or active electron ray selected from the group consisting of visible light, ultraviolet light, infrared light, X-ray, ⁇ -ray, ⁇ -ray and ⁇ -ray.
  • ultraviolet light is preferred in that it is easy to control the progress of the polymerization reaction and that a photopolymerization device that is widely used in the field can be used, and ultraviolet light is preferable, so that photopolymerization is possible.
  • the polymerization temperature can be controlled by irradiating light while cooling the dried coating film by an appropriate cooling means.
  • a patterned polarizer can be obtained by performing masking or development.
  • 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 ultra-high-pressure mercury lamp, a xenon lamp, a halogen lamp, a carbon arc lamp, a tungsten lamp, a gallium lamp, an excimer laser, and a wavelength range.
  • Examples include an LED light source that emits light at 380 to 440 nm, a chemical lamp, a black light lamp, a microwave-excited mercury lamp, and a metal halide lamp.
  • the ultraviolet irradiation intensity is usually from 10 to 3,000 mW / cm 2 .
  • the ultraviolet irradiation intensity is preferably an intensity in a wavelength region effective for activating the polymerization initiator.
  • the time for irradiating light is generally 0.1 second to 10 minutes, preferably 1 second to 5 minutes, more preferably 5 seconds to 3 minutes, and further 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 2. 2 .
  • the polymerizable liquid crystal compound is polymerized while maintaining a liquid crystal state of a smectic phase, preferably a higher order smectic phase, and a polarizer is formed.
  • a polarizer obtained by polymerizing the polymerizable liquid crystal compound while maintaining the liquid crystal state of the smectic phase, with the action of the dichroic dye, a conventional host-guest polarizing film, that is, from the liquid crystal state of the nematic phase There is an advantage that the polarization performance is higher than that of the polarizer. Further, there is an advantage that the strength is superior to that obtained by applying only a dichroic dye or a lyotropic liquid crystal.
  • the thickness of the polarizer can be appropriately selected according to the display device to be applied, and is preferably a film of 0.1 to 5 ⁇ m, more preferably 0.3 to 4 ⁇ m, and still more preferably 0.5 to 3 ⁇ m. is there.
  • the thickness of the polarizer is equal to or more than the above lower limit, it is easy to prevent the necessary light absorption from being obtained, and when the thickness is equal to or less than the above upper limit, occurrence of alignment defects due to a decrease in alignment regularity due to the alignment film. Is easy to control.
  • the polarizing film, polarizer, alignment film, first and second resin layers, and a polarizing plate described below can be measured by a laser microscope or a film thickness gauge, respectively.
  • the alignment film included in the polarizing film of the present invention is formed on the surface of the polarizer opposite to the first resin layer.
  • the alignment film has an alignment regulating force for aligning the polymerizable liquid crystal compound in a desired direction.
  • the alignment film preferably has a solvent resistance that does not dissolve by the application of the composition for forming a polarizing film or the like, and also has a heat resistance in a heat treatment for removing the solvent or aligning the polymerizable liquid crystal compound.
  • the alignment film is a cured product of the alignment film forming composition containing the (meth) acrylic compound, and has excellent adhesion at the interface with the polarizer and at the interface with the second resin layer.
  • the alignment film in the present invention is preferably an optical alignment film formed by curing the composition for forming an alignment film by polarized light (preferably, polarized UV) from the viewpoint of improving adhesion and heat resistance.
  • (Meth) acrylic compound refers to a compound having at least one (meth) acryloyl group, and the (meth) acrylic compound may be a monomer, oligomer or polymer. When it is an oligomer or a polymer, the double bond of the (meth) acryloyl group may be polymerized.
  • the (meth) acrylic compound contained in the composition for forming a photoalignment film preferably has a photoreactive group in addition to the (meth) acryloyl group.
  • the photoreactive group refers to a group that generates liquid crystal alignment ability when irradiated with light.
  • groups involved in a photoreaction that is a source of liquid crystal alignment capability such as alignment induction or isomerization reaction, dimerization reaction, photocrosslinking reaction or photodecomposition reaction of molecules generated by light irradiation.
  • a group that participates in a dimerization reaction or a photocrosslinking reaction is preferable in terms of excellent orientation.
  • a photoreactive group involved in the photodimerization reaction is preferable, the amount of polarized light required for photoalignment is relatively small, and a photoalignment film excellent in thermal stability and stability over time is easily obtained.
  • Cinnamoyl and chalcone groups are preferred.
  • the (meth) acrylic oligomer or polymer contained in the composition for forming a photoalignment film those having a cinnamoyl group such that the terminal of the oligomer or polymer side chain has a cinnamic acid structure are particularly preferable.
  • the photo-alignment film is obtained by applying a composition for forming a photo-alignment film containing a (meth) acrylic compound and a solvent on the second resin layer, and irradiating polarized light (preferably, polarized UV). It is obtained by doing.
  • polarized light preferably, polarized UV.
  • the solvent contained in the composition for forming a photo-alignment film include the same solvents as those exemplified above as the solvent that can be used for forming the polarizer, and are appropriately determined according to the solubility of the (meth) acrylic compound. You can choose.
  • the content of the (meth) acrylic compound in the composition for forming a photo-alignment film can be appropriately adjusted depending on the type of the (meth) acrylic compound and the thickness of the desired photo-alignment film. Is preferably at least 0.2% by mass, more preferably 0.3 to 10% by mass. As long as the properties of the photo-alignment film are not significantly impaired, the composition for forming a photo-alignment film may contain a polymer material such as polyvinyl alcohol or polyimide, or a photosensitizer.
  • a composition for forming a polarizer is applied to the alignment film.
  • the method for removing the solvent and the method for removing the solvent include the methods exemplified above.
  • Irradiation of polarized light may be performed by directly irradiating polarized light UV from the second resin layer side, even in the form of directly irradiating polarized UV to a composition obtained by removing a solvent from the composition for forming a photo-alignment film applied on the second resin layer. It may be of a type of transmitting and irradiating. It is particularly preferable that the polarized light is substantially parallel light.
  • the wavelength of the polarized light to be irradiated is preferably in a wavelength region where the photoreactive group and / or the (meth) acryloyl group of the (meth) acrylic compound can absorb light energy.
  • UV (ultraviolet light) having a wavelength in the range of 250 to 400 nm is particularly preferable.
  • the light source used for the polarized light irradiation include a xenon lamp, a high-pressure mercury lamp, an ultra-high pressure mercury lamp, a metal halide lamp, an ultraviolet laser such as KrF and ArF, and a high-pressure mercury lamp, an ultra-high pressure mercury lamp, and a metal halide lamp.
  • a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, and a metal halide lamp are preferable because of their high emission intensity of ultraviolet light having a wavelength of 313 nm.
  • polarized UV By irradiating the light from the light source through an appropriate polarizer, polarized UV can be emitted.
  • a polarizer a polarizing filter, a polarizing prism such as Glan-Thompson or Glan-Taylor, or a wire grid type polarizer can be used.
  • a plurality of regions (patterns) having different directions of liquid crystal alignment can be formed by performing masking.
  • the thickness of the alignment film is preferably from 10 to 5,000 nm, more preferably from 10 to 1,000 nm, and still more preferably from 30 to 300 nm.
  • the alignment regularity can be exhibited while exhibiting good adhesion at the interface with the polarizer or the interface with the second resin layer. Can be formed.
  • the first resin layer contained in the polarizing film of the present invention is a cured product of the first curable composition containing a (meth) acrylic compound, and is formed on the surface of the polarizer opposite to the alignment film side. .
  • both the first resin layer and the polarizer are formed from a compound having a (meth) acryloyl group, the compatibility between the layers is high, and the (meth) acrylic compound contained in the first curable composition
  • a polymerizable liquid crystal compound having a (meth) acryloyl group contained in the polarizer can form a crosslinked structure, so that excellent adhesion at the layer interface can be exhibited.
  • the second resin layer contained in the polarizing film of the present invention is a cured product of the second curable composition containing the (meth) acrylic compound, and is formed on the surface of the alignment film opposite to the polarizer. .
  • both the second resin layer and the alignment film are formed from a compound having a (meth) acryloyl group, the compatibility between the layers is high, and the (meth) acrylic compound contained in the second curable composition And the (meth) acrylic compound contained in the alignment film can form a crosslinked structure, so that excellent adhesion at the layer interface can be exhibited.
  • the (meth) acrylic compound contained in the first curable composition and the second curable composition is a compound having at least one (meth) acryloyl group, and may be a monomer, an oligomer or a polymer.
  • the (meth) acrylic compound include (meth) acrylate compounds such as monofunctional (meth) acrylate compounds and polyfunctional (meth) acrylate compounds; urethane (meth) acrylate compounds such as polyfunctional urethane (meth) acrylate compounds; Epoxy (meth) acrylate compounds such as polyfunctional epoxy (meth) acrylate compounds; carboxyl group-modified epoxy (meth) acrylate compounds and polyester (meth) acrylate compounds.
  • a polyfunctional (meth) acrylate compound or a urethane (meth) acrylate compound is preferable from the viewpoint of easily improving the adhesion, heat resistance and flexibility of the polarizing film, and the polyfunctional (meth) acrylate compound and the urethane (meth) ) It is more preferred to combine with acrylate.
  • the first curable composition (the first resin layer) and the second curable composition (the second resin layer) may have the same composition or different compositions, but may have adhesion, heat resistance, and bending. The same composition is preferred from the viewpoint of easily improving the properties.
  • the term “flexibility” means a characteristic capable of suppressing the occurrence of cracks or the like when the polarizing film is bent.
  • At least one of the first curable composition and the second curable composition contains a polyfunctional (meth) acrylate compound as the (meth) acrylic compound. This mode is advantageous from the viewpoints of adhesion, heat resistance and flexibility of the polarizing film.
  • the polyfunctional (meth) acrylate compound means a compound having two or more (meth) acryloyloxy groups in the molecule, for example, a bifunctional compound having two (meth) acryloyloxy groups in the molecule.
  • the term “(meth) acrylate” means “acrylate” or “methacrylate”
  • the term “(meth) acryloyl” also means “acryloyl” or “methacryloyl”.
  • polyfunctional (meth) acrylate compound one or more polyfunctional (meth) acrylate compounds may be contained.
  • the number of (meth) acryloyloxy groups may be the same or different between each polyfunctional (meth) acrylate compound.
  • bifunctional (meth) acrylate monomer examples include ethylene glycol di (meth) acrylate, 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, and 1,6-hexanediol diacrylate.
  • Alkylene glycol di (meth) acrylates such as (meth) acrylate, 1,9-nonanediol di (meth) acrylate and neopentyl glycol di (meth) acrylate; diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate , Dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate and polytetrame Polyoxyalkylene glycol di (meth) acrylate such as lenglycol di (meth) acrylate; di (meth) acrylate of halogen-substituted alkylene glycol such as tetrafluoroethylene glycol di (meth) acrylate; trimethylolpropane di (meth) acrylate; Di (meth) acrylate of aliphatic
  • the trifunctional (meth) acrylate monomer is a monomer having three (meth) acryloyloxy groups in the molecule, and examples thereof include glycerin tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, and ditrimethylol.
  • the tetrafunctional (meth) acrylate monomer is a monomer having four (meth) acryloyloxy groups in the molecule, and examples thereof include ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, Pentaerythritol tetra (meth) acrylate, tripentaerythritol tetra (meth) acrylate, caprolactone modified pentaerythritol tetra (meth) acrylate, caprolactone modified tripentaerythritol tetra (meth) acrylate, ethylene oxide modified pentaerythritol tetra (meth) acrylate, ethylene Oxide-modified tripentaerythritol tetra (meth) acrylate, propylene oxide-modified pentaerythritol tetra (meth)
  • pentafunctional (meth) acrylate monomer examples include dipentaerythritol penta (meth) acrylate, tripentaerythritol penta (meth) acrylate, a reaction product of dipentaerythritol penta (meth) acrylate with an acid anhydride, and caprolactone-modified dipentane.
  • Examples of the hexafunctional (meth) acrylate monomer include dipentaerythritol hexa (meth) acrylate, tripentaerythritol hexa (meth) acrylate, caprolactone-modified dipentaerythritol hexa (meth) acrylate, and caprolactone-modified tripentaerythritol hexa (meth) acrylate , Ethylene oxide-modified dipentaerythritol hexa (meth) acrylate, ethylene oxide-modified tripentaerythritol hexa (meth) acrylate, propylene oxide-modified dipentaerythritol hexa (meth) acrylate, propylene oxide-modified tripentaerythritol hexa (meth) acrylate, etc. No.
  • Examples of the heptafunctional (meth) acrylate monomer include tripentaerythritol hepta (meth) acrylate, a reaction product of tripentaerythritol hepta (meth) acrylate and an acid anhydride, caprolactone-modified tripentaerythritol hepta (meth) acrylate, and caprolactone-modified Reaction product of tripentaerythritol hepta (meth) acrylate and acid anhydride, ethylene oxide-modified tripentaerythritol hepta (meth) acrylate, reaction product of ethylene oxide-modified tripentaerythritol hepta (meth) acrylate and acid anhydride, propylene Oxide-modified tripentaerythritol hepta (meth) acrylate, propylene oxide-modified tripentaerythritol hepta (meth) acryl
  • the octafunctional (meth) acrylate monomer is a monomer having eight (meth) acryloyloxy groups in the molecule, and examples thereof include tripentaerythritol octa (meth) acrylate and caprolactone-modified tripentaerythritol octa (meth). Examples include acrylate, ethylene oxide-modified tripentaerythritol octa (meth) acrylate, and propylene oxide-modified tripentaerythritol octa (meth) acrylate. These polyfunctional (meth) acrylate compounds can be used alone or in combination of two or more.
  • the number of (meth) acryloyl groups in the polyfunctional (meth) acrylate compound is preferably 6 or more, more preferably 7 or more, and still more preferably 8 or more.
  • the upper limit of the number of the (meth) acryloyl groups is usually 20 or less.
  • the polyfunctional (meth) acrylate compound can adjust the crosslinking density of the first resin layer or the second resin layer by controlling the molecular weight between crosslinking points and the number of crosslinking points of the compound. More specifically, as the molecular weight between crosslink points decreases, the crosslink density increases, and as the number of crosslink points increases, the crosslink density increases and the heat resistance of the polarizing film can be increased.
  • the molecular weight (Mw) of the polyfunctional (meth) acrylate compound is preferably 100 or more, more preferably 200 or more, preferably 2000 or less, more preferably 1500 or less.
  • the polyfunctional (meth) acrylate compound has a branched structure, and a branch closest to the (meth) acryloyl group in the branched structure.
  • the number of atoms of a chain (sometimes referred to as a connecting chain) connecting the point and the (meth) acryloyl group is preferably 3 or less, more preferably 2 or less.
  • the connecting chains when there are a plurality of the connecting chains, it is sufficient that at least one connecting chain satisfies the range of the number of atoms. From the viewpoint of improving heat resistance, all the connecting chains satisfy the range of the number of atoms. Is preferred.
  • dipentaerythritol hexa (meth) acrylate and tripentaerythritol octa (meth) acrylate are preferred from the viewpoint of the heat resistance of the polarizing film.
  • the content of the polyfunctional (meth) acrylate compound is preferably at least 50 parts by mass, more preferably at least 50 parts by mass, based on 100 parts by mass of the solid content of the curable composition. Is at least 60 parts by mass, more preferably at least 70 parts by mass, preferably at most 100 parts by mass, more preferably at most 95 parts by mass, even more preferably at most 90 parts by mass.
  • the content of the polyfunctional (meth) acrylate compound is in the above range, the adhesion, heat resistance, and flexibility between the layers of the polarizing film are easily increased.
  • the solid content of the curable composition means the total amount of components obtained by removing the solvent from the curable composition.
  • At least one of the first curable composition and the second curable composition contains a urethane (meth) acrylate compound as the (meth) acrylic compound.
  • This mode is advantageous from the viewpoints of adhesion, heat resistance and flexibility of the polarizing film.
  • the polyfunctional (meth) acrylate compound is generally a (meth) acrylate compound having no urethane bond, and is different from the urethane (meth) acrylate compound.
  • the urethane (meth) acrylate compound generally means a reaction product of an isocyanate compound, a polyol compound, and a (meth) acrylate compound, and is a polyfunctional urethane (meth) acrylate having two or more (meth) acryloyloxy groups in a molecule.
  • it is a compound. Since the polyfunctional urethane (meth) acrylate compound can form a crosslinked structure, it is advantageous from the viewpoint of the heat resistance of the polarizing film and can impart appropriate toughness. For this reason, the flexibility of the polarizing film may be increased to improve the resistance to deformation due to bending or the like.
  • the urethane (meth) acrylate compound preferably has 3 or less functional groups, and more preferably 2 functional groups. Further, from the viewpoint of achieving both heat resistance and flexibility, the number of functional groups is preferably 2 to 5.
  • the weight average molecular weight (Mw) of the urethane (meth) acrylate compound is preferably 300 or more, more preferably 400 or more, preferably 10,000 or less, more preferably 7,000 or less, further preferably, in terms of polystyrene. It is 5,000 or less, particularly preferably 3,000 or less. When the Mw of the urethane (meth) acrylate compound is within the above range, the adhesion and the heat resistance are easily improved.
  • the weight average molecular weight (Mw) can be measured by, for example, gel permeation chromatography (GPC).
  • the number of (meth) acryloyl groups per unit molecular weight is preferably 15 ⁇ 10 ⁇ 4 or more, more preferably 20 ⁇ 10 ⁇ 4 or more, and more preferably 30 ⁇ 10 ⁇ 4 or more. More preferably, it is particularly preferably 40 ⁇ 10 ⁇ 4 or more.
  • the upper limit of the number of (meth) acryloyl groups per unit molecular weight is usually 20 or less, preferably 8 or less.
  • the number of (meth) acryloyl groups per unit molecular weight can be calculated by the formula: (number of (meth) acryloyl groups of urethane (meth) acrylate compound / weight average molecular weight (Mw).
  • the content of the urethane (meth) acrylate compound is preferably based on 100 parts by mass of the solid content of the curable composition. Is at least 10 parts by mass, more preferably at least 30 parts by mass, preferably at most 100 parts by mass, more preferably at most 50 parts by mass.
  • the content of the urethane (meth) acrylate compound is in the above range, the adhesion, heat resistance and flexibility of the polarizing film are easily improved.
  • the polyfunctional (meth) acrylate compound and the urethane (meth) acrylate compound are Preferably, it is contained in a ratio of 95: 5 to 50:50, more preferably 90:10 to 70:30 (polyfunctional (meth) acrylate compound: urethane (meth) acrylate compound, mass ratio).
  • a ratio of 95: 5 to 50:50 more preferably 90:10 to 70:30 (polyfunctional (meth) acrylate compound: urethane (meth) acrylate compound, mass ratio).
  • the first curable composition or the second curable composition may contain a monofunctional (meth) acrylate compound as required.
  • the monofunctional (meth) acrylate compound may be a monomer, an oligomer or a polymer, and among these, a monofunctional (meth) acrylate monomer can be suitably used.
  • Examples of monofunctional (meth) acrylate monomers include methyl (meth) acrylate, ethyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isononyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2- or 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) ) Acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, trimethylolpropane mono (meth) acrylate, pentaerythritol mono (meth) acrylate, ethyl carbitol (meth) acryl Rate, 2-phenoxyethyl (meth
  • the content of the monofunctional (meth) acrylate compound is based on 100 parts by mass of the solid content of the curable composition. , Preferably 5 parts by mass or more, more preferably 20 parts by mass or more, and preferably 50 parts by mass or less.
  • the content of the monofunctional (meth) acrylate compound is within the above range, coatability is improved from the viewpoint of adjusting the viscosity of the curable composition.
  • At least one of the first curable composition and the second curable composition preferably contains a radical polymerization initiator from the viewpoint of improving curability. More preferably, both contain a radical polymerization initiator.
  • the radical polymerization initiator is not particularly limited as long as it can initiate curing of the curable compound by irradiation with active energy rays such as visible light, ultraviolet light, X-rays, and electron beams.
  • acetophenone 3-methylacetophenone, benzyldimethylketal, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane
  • Acetophenone-based initiators such as -1-one and 2-hydroxy-2-methyl-1-phenylpropan-1-one
  • benzophenone-based initiators such as benzophenone, 4-chlorobenzophenone and 4,4'-diaminobenzophenone
  • 2-Dimethoxy-1,2-diphenylethan-1-one 1-hydroxy-cyclo Alkylphenone initiators such as sil-phenyl-ketone
  • benzoin ether initiators such as benzoin propyl ether and benzoin ethyl ether
  • thioxanthone initiators such as 4-isopropylthioxanthone; bis (2,4,6-trimethylbenzoyl
  • the content of the radical polymerization initiator is preferably 1 to 10 parts by mass relative to 100 parts by mass of the solid content of the curable compound. Parts, more preferably 2 to 8 parts by mass.
  • the content of the radical polymerization initiator is equal to or more than the above lower limit, the polymerization initiation ability is sufficiently exhibited, and the curability is improved.
  • the radical polymerization initiator is equal to or less than the above upper limit, the radical polymerization initiator hardly remains, and it is easy to suppress a decrease in visible light transmittance and the like.
  • the first curable composition or the second curable composition may contain additives other than the radical polymerization initiator, for example, an ultraviolet absorber, an antistatic agent, a stabilizer, an antioxidant, and a colorant. , A surface conditioner and the like. Other additives can be used alone or in combination of two or more. The content of the other additives is preferably about 0.1 to 20% by mass based on the mass of the solid content of the curable composition.
  • the first curable composition or the second curable composition can be prepared by mixing and stirring a (meth) acrylic compound and, if necessary, additives and the like. Further, in order to improve the coating property, the viscosity may be adjusted by adding a solvent to the first curable composition or the second curable composition.
  • Any solvent may be used as long as it can dissolve the components constituting the first curable composition or the second curable composition.
  • solvent examples thereof include aliphatic hydrocarbons such as hexane and octane; and aromatic hydrocarbons such as toluene and xylene.
  • Hydrocarbons Hydrocarbons; alcohol solvents such as ethanol, 1-propanol, isopropanol and 1-butanol; ketones such as methyl ethyl ketone and methyl isobutyl ketone; ester solvents such as ethyl acetate, butyl acetate and isobutyl acetate; ethylene glycol monomethyl ether and ethylene glycol mono Glycol ethers such as ethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, and propylene glycol monoethyl ether; ethylene glycol monomethyl ether acetate, propylene glycol Can be suitably selected from such esterification glycol ethers solvents such as monomethyl ether acetate.
  • the type and content of the solvent are appropriately selected according to the type and content of the components contained in the first curable composition or the second curable composition, the shape, the coating method, the thickness of the resin layer, and the like.
  • the content of the solvent is preferably 3 to 1000 parts by mass, more preferably 5 to 100 parts by mass, and still more preferably 7 to 50 parts by mass with respect to 100 parts by mass of the solid content of the curable composition.
  • the first resin layer is obtained by applying a first curable composition on a polarizer or a release film and curing the composition.
  • the second resin layer is obtained by applying a second curable composition on a base material, a release film or an alignment film, and curing the composition.
  • the curing of the curable composition is preferably performed by irradiating an active energy ray to polymerize a polymerizable component such as a (meth) acrylic compound contained in the composition.
  • the active energy ray is appropriately selected according to the type of the polymerizable component such as the (meth) acrylic compound, the type of the radical polymerization initiator, the amount thereof, and the like. Specific examples thereof include at least one active energy ray selected from the group consisting of visible light, ultraviolet light, infrared light, X-ray, ⁇ -ray, ⁇ -ray and ⁇ -ray.
  • ultraviolet light is preferred in that the progress of the polymerization reaction is easily controlled and that a photopolymerization apparatus widely used in the field can be used.
  • the light source of the active energy ray include the light sources exemplified in ⁇ Polarizer>.
  • the UV irradiation intensity, irradiation time, and integrated light amount the ranges of the UV irradiation intensity, irradiation time, and integrated light amount exemplified in the section ⁇ Polarizer> may be appropriately used.
  • each of the first resin layer and the second resin layer is preferably 0.1 to 10 ⁇ m, more preferably 0.2 to 5 ⁇ m, and further preferably 0.3 to 3 ⁇ m.
  • the thickness of the first resin layer or the second resin layer is in the above range, the adhesion between the first resin layer and the polarizer and the adhesion between the second resin layer and the alignment film are easily increased. Further, the diffusion of the dichroic dye contained in the polarizer is easily suppressed easily, and the heat resistance is easily increased.
  • the polarizing film of the present invention has excellent adhesion between the respective layers, and can exhibit further excellent heat resistance.
  • the polarizing film can effectively suppress the diffusion of the dichroic dye contained in the polarizer even in a high-temperature environment, and can suppress a decrease in polarization performance. Further, in a preferred embodiment, excellent flexibility can be exhibited in addition to adhesion and heat resistance. Therefore, the polarizing film can be suitably used for a display device such as an organic EL display device or a touch panel display device.
  • the method for producing a polarizing film of the present invention is not particularly limited as long as the first resin layer, the polarizer, the alignment film, and the second resin layer can be laminated in this order.
  • a second resin layer is formed, and the second resin layer is formed.
  • An alignment film is formed thereon, a polarizer is formed on the alignment film, and a second resin layer, an alignment film, and a laminate in which a polarizer is laminated in this order are obtained.
  • a method including a step of applying or laminating the first curable composition and curing the first curable composition is exemplified.
  • the polarizing film of the present invention includes a first curable composition on a polarizer surface of a laminate in which a second resin layer, an alignment film, and a polarizer are laminated on a release film. Is applied, and the first curable composition is cured by irradiating active energy rays from the first curable composition side, so that a release film, a second resin layer, an alignment film, a polarizer, and a first resin It is manufactured by a method including a step of obtaining a laminate having layers in this order and peeling a release film from the laminate.
  • the polarizing film of the present invention is a laminate in which a first curable composition formed on a release film, a second resin layer, an alignment film, and a polarizer are stacked in this order. And the first curable composition is cured by irradiating active energy rays from the release film side to thereby release the release film, the first resin layer, the polarizer, the alignment film, and the second polarizer. It is manufactured by a method including a step of obtaining a laminate in which resin layers are laminated in this order, and peeling a release film from the laminate.
  • the polarizing film of the present invention may be formed by laminating a first resin layer, a polarizer, an alignment film, and a second resin layer in this order, and as long as the effects of the present invention are not impaired.
  • a functional layer may be included on the surface opposite to the above, the surface of the second resin layer opposite to the alignment film side, or between each layer. Examples of the functional layer include an ultraviolet absorbing layer, a hard coat layer, a primer layer, a gas barrier layer, a hue adjusting layer, a refractive index adjusting layer, an antireflection layer, an antistatic layer, an adhesive layer, and an adhesive layer. These functional layers can be used alone or in combination of two or more.
  • the polarizing film of the present invention may form a polarizing plate in combination with a retardation film. That is, the polarizing plate of the present invention includes the polarizing film and a retardation film.
  • the retardation film may be laminated on the surface of the first resin layer or the second resin layer of the polarizing film via an adhesive layer or a pressure-sensitive adhesive layer, for example. It is preferable to laminate the retardation film so that the slow axis (optical axis) of the retardation film and the absorption axis of the polarizing film (polarizer) become substantially 45 °.
  • substantially 45 ° is usually in the range of 45 ⁇ 5 °.
  • the retardation film in the polarizing plate is represented by the following formula (X): 100 ⁇ Re (550) ⁇ 180 (X) [Wherein, Re (550) represents an in-plane retardation value at a wavelength of 550 nm] It is preferable to satisfy the following.
  • the retardation film has the in-plane retardation value represented by the above (X), it functions as a so-called ⁇ / 4 plate.
  • the formula (X) preferably satisfies 100 nm ⁇ Re (550) ⁇ 180 nm, and more preferably 120 nm ⁇ Re (550) ⁇ 160 nm.
  • the retardation film has the following formula (Y): Re (450) / Re (550) ⁇ 1 (Y) [Wherein, Re (450) and Re (550) represent in-plane retardation values at wavelengths of 450 nm and 550 nm, respectively] It is preferable to satisfy the following.
  • the retardation film satisfying the above formula (Y) has so-called reverse wavelength dispersion, and shows excellent polarization performance.
  • the value of Re (450) / Re (550) is preferably 0.93 or less, more preferably 0.88 or less, further preferably 0.86 or less, preferably 0.80 or more, and more preferably 0.1 or more. 82 or more.
  • the retardation film may be a stretched film that gives a retardation by stretching a polymer, but from the viewpoint of making a polarizing plate thinner, a polymerizable liquid crystal composition containing a polymer of a polymerizable liquid crystal compound ( Hereinafter, it is also preferable to be composed of a polymerizable liquid crystal composition (B)).
  • the polymerizable liquid crystal compound is usually polymerized in an oriented state.
  • the polymerizable liquid crystal compound forming the retardation film hereinafter, also referred to as “polymerizable liquid crystal compound (B)”) means a liquid crystal compound having a polymerizable functional group, particularly a photopolymerizable functional group.
  • the photopolymerizable functional group refers to a group that can participate in a polymerization reaction by an active radical, acid, or the like generated from a photopolymerization initiator.
  • Examples of the photopolymerizable functional group include a vinyl group, a vinyloxy group, a 1-chlorovinyl group, an isopropenyl group, a 4-vinylphenyl group, an acryloyloxy group, a methacryloyloxy group, an oxiranyl group, and an oxetanyl group.
  • an acryloyloxy group, a methacryloyloxy group, a vinyloxy group, an oxiranyl group and an oxetanyl group are preferable, and an acryloyloxy group is more preferable.
  • the liquid crystallinity may be a thermotropic liquid crystal or a lyotropic liquid crystal, and the phase ordered structure may be a nematic liquid crystal or a smectic liquid crystal.
  • the polymerizable liquid crystal compound one type may be used alone, or two or more types may be used in combination.
  • polymerizable liquid crystal compound (B) As the polymerizable liquid crystal compound (B), a compound satisfying all of the following (A) to (D) is mentioned from the viewpoint of easiness of film formation and imparting retardation represented by the formula (Y). .
  • (A) a compound having a thermotropic liquid crystallinity
  • (A) The polymerizable liquid crystal compound has ⁇ electrons on the major axis direction (a).
  • the polymerizable liquid crystal compound (B) that satisfies all of the above (A) to (D) is coated on an alignment film formed by, for example, a rubbing treatment, and heated to a phase transition temperature or higher to form a nematic phase. It is possible to In the nematic phase formed by orienting the polymerizable liquid crystal compound (B), the polymerizable liquid crystal compound is usually oriented such that the major axes thereof are parallel to each other, and the major axis is oriented in the nematic phase. Becomes
  • the polymerizable liquid crystal compound (B) having the above-mentioned properties generally shows reverse wavelength dispersion in many cases.
  • the compound satisfying the above characteristics (A) to (D) specifically, for example, the following formula (II):
  • the compound represented by these is mentioned.
  • the compounds represented by the formula (II) can be used alone or in combination of two or more.
  • Ar represents a divalent aromatic group which may have a substituent.
  • the aromatic group referred to herein is a group having a planar structure having a cyclic structure, and the cyclic structure has a [pi] electron number of [4n + 2] in accordance with the Huckel rule.
  • n represents an integer.
  • the divalent aromatic group preferably contains at least one of a nitrogen atom, an oxygen atom, and a sulfur atom.
  • G 1 and G 2 each independently represent a divalent aromatic group or a divalent alicyclic hydrocarbon group.
  • the hydrogen atom contained in the divalent aromatic group or the divalent alicyclic hydrocarbon group is a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms,
  • the carbon atom constituting the divalent aromatic group or the divalent alicyclic hydrocarbon group may be substituted with an alkoxy group, a cyano group or a nitro group represented by the formulas 1 to 4, wherein an oxygen atom, a sulfur atom Alternatively, it may be substituted by a nitrogen atom.
  • L 1 , L 2 , B 1 and B 2 are each independently a single bond or a divalent linking group.
  • k and l each independently represent an integer of 0 to 3, and satisfy the relationship of 1 ⁇ k + 1.
  • B 1 and B 2 may be the same as or different from each other.
  • E 1 and E 2 each independently represent an alkanediyl group having 1 to 17 carbon atoms, wherein a hydrogen atom contained in the alkanediyl group may be substituted with a halogen atom.
  • the —CH 2 — contained in the alkanediyl group may be substituted with —O—, —S—, or —Si—.
  • P 1 and P 2 independently represent a polymerizable group or a hydrogen atom, and at least one is a polymerizable group.
  • G 1 and G 2 are preferably each independently substituted with at least one substituent selected from the group consisting of a halogen atom and an alkyl group having 1 to 4 carbon atoms.
  • a 1,4-cyclohexanediyl group which may be substituted with at least one substituent selected from the group consisting of a 1,4-phenylenediyl group, a halogen atom and an alkyl group having 1 to 4 carbon atoms, more preferably methyl
  • G 1 and G 2 is preferably a divalent alicyclic hydrocarbon group, and at least one of G 1 and G 2 bonded to L 1 or L 2.
  • One is more preferably a divalent alicyclic hydrocarbon group.
  • R a1 to R a8 each independently represent a single bond or an alkylene group having 1 to 4 carbon atoms
  • R c and R d each represent an alkyl group having 1 to 4 carbon atoms or a hydrogen atom.
  • L 1 and L 2 are each independently preferably a single bond, —OR a2-1 —, —CH 2 —, —CH 2 CH 2 —, —COOR a4-1 —, or OCOR a6-1 — .
  • R a2-1 , R a4-1 , and R a6-1 each independently represent any one of a single bond, —CH 2 —, and —CH 2 CH 2 —.
  • L 1 and L 2 are each independently preferably a single bond, —O—, —CH 2 CH 2 —, —COO—, —COOCH 2 CH 2 —, or OCO—.
  • At least one of G 1 and G 2 in the formula (II) is a divalent alicyclic hydrocarbon group, and the divalent alicyclic hydrocarbon group is And a polymerizable liquid crystal compound in which a divalent aromatic group Ar which may have a substituent is bonded to L 1 and / or L 2 which is —COO—.
  • R a9 to R a16 each independently represent a single bond or an alkylene group having 1 to 4 carbon atoms.
  • B 1 and B 2 are each independently preferably a single bond, —OR a10-1 —, —CH 2 —, —CH 2 CH 2 —, —COOR a12-1 —, or OCOR a14-1 — .
  • R a10-1 , R a12-1 , and R a14-1 each independently represent a single bond, —CH 2 —, or —CH 2 CH 2 —.
  • B 1 and B 2 are each independently more preferably a single bond, —O—, —CH 2 CH 2 —, —COO—, —COOCH 2 CH 2 —, —OCO—, or OCOCH 2 CH 2 — .
  • E 1 and E 2 are each independently preferably an alkanediyl group having 1 to 17 carbon atoms, more preferably an alkanediyl group having 4 to 12 carbon atoms.
  • examples of the polymerizable group represented by P 1 or P 2 include an epoxy group, a vinyl group, a vinyloxy group, a 1-chlorovinyl group, an isopropenyl group, a 4-vinylphenyl group, an acryloyloxy group Methacryloyloxy group, oxiranyl group, and oxetanyl group.
  • an acryloyloxy group, a methacryloyloxy group, a vinyloxy group, an oxiranyl group and an oxetanyl group are preferred, and an acryloyloxy group is more preferred.
  • Ar has at least one selected from an aromatic hydrocarbon ring which may have a substituent, an aromatic heterocyclic ring which may have a substituent, and an electron-withdrawing group. Is preferred.
  • the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, and an anthracene ring, and a benzene ring and a naphthalene ring are preferable.
  • aromatic heterocycle examples include a furan ring, a benzofuran ring, a pyrrole ring, an indole ring, a thiophene ring, a benzothiophene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a triazole ring, a triazine ring, a pyrroline ring, an imidazole ring, and a pyrazole ring.
  • a thiazole ring, a benzothiazole ring, or a benzofuran ring is preferable, and a benzothiazole group is more preferable.
  • Ar contains a nitrogen atom, the nitrogen atom preferably has ⁇ electrons.
  • 2-valent of [pi Total N [pi electrons contained in the aromatic group is preferably 8 or more represented by Ar, more preferably 10 or more, more preferably 14 or more, particularly Preferably it is 16 or more. Further, it is preferably 30 or less, more preferably 26 or less, and further preferably 24 or less.
  • Examples of the aromatic group represented by Ar include groups represented by the following formulas (Ar-1) to (Ar-23).
  • an asterisk (*) represents a connecting part
  • Z 0 , Z 1 and Z 2 each independently represent a hydrogen atom, a halogen atom, an alkyl having 1 to 12 carbons.
  • Q 1 and Q 2 are each independently —CR 2 ′ R 3 ′ —, —S—, —NH—, —NR 2 ′ —, — R represents a CO— or O—, and R 2 ′ and R 3 ′ each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • J 1 and J 2 each independently represent a carbon atom or a nitrogen atom.
  • Y 1 , Y 2 and Y 3 each independently represent an optionally substituted aromatic hydrocarbon group or aromatic heterocyclic group.
  • W 1 and W 2 each independently represent a hydrogen atom, a cyano group, a methyl group, or a halogen atom, and m represents an integer of 0 to 6.
  • Examples of the aromatic hydrocarbon group for Y 1 , Y 2 and Y 3 include an aromatic hydrocarbon group having 6 to 20 carbon atoms such as a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group and a biphenyl group. , A naphthyl group is preferred, and a phenyl group is more preferred.
  • Examples of the aromatic heterocyclic group include those having 4 to 20 carbon atoms including at least one nitrogen atom such as furyl, pyrrolyl, thienyl, pyridinyl, thiazolyl, and benzothiazolyl, and at least one heteroatom such as oxygen and sulfur.
  • An aromatic heterocyclic group is mentioned, and a furyl group, a thienyl group, a pyridinyl group, a thiazolyl group, and a benzothiazolyl group are preferable.
  • Y 1 and Y 2 may each independently be a polycyclic aromatic hydrocarbon group or a polycyclic aromatic heterocyclic group which may be substituted.
  • the polycyclic aromatic hydrocarbon group refers to a condensed polycyclic aromatic hydrocarbon group or a group derived from an aromatic ring assembly.
  • the polycyclic aromatic heterocyclic group refers to a condensed polycyclic aromatic heterocyclic group or a group derived from an aromatic ring assembly.
  • Z 0 , Z 1 and Z 2 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, a cyano group, a nitro group, It is preferably an alkoxy group having 1 to 12 carbon atoms, Z 0 is more preferably a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a cyano group, and Z 1 and Z 2 are a hydrogen atom, a fluorine atom, a chlorine atom. An atom, a methyl group and a cyano group are more preferred.
  • Q 1 and Q 2 are preferably -NH-, -S-, -NR 2 ' -, -O-, and R 2' is preferably a hydrogen atom. . Among them, —S—, —O—, and —NH— are particularly preferable.
  • Y 1 may form an aromatic heterocyclic group together with the nitrogen atom to which it is bound and Z 0 .
  • the aromatic heterocyclic group include those described above as the aromatic heterocyclic ring which Ar may have, for example, a pyrrole ring, an imidazole ring, a pyrroline ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, an indole Ring, quinoline ring, isoquinoline ring, purine ring, pyrrolidine ring and the like.
  • This aromatic heterocyclic group may have a substituent.
  • Y 1 may be the above-mentioned optionally substituted polycyclic aromatic hydrocarbon group or polycyclic aromatic heterocyclic group together with the nitrogen atom to which it is bonded and Z 0 .
  • a benzofuran ring, a benzothiazole ring, a benzoxazole ring and the like can be mentioned.
  • the compound represented by the formula (II) can be produced, for example, according to the method described in JP-A-2010-31223.
  • the content of the polymerizable liquid crystal compound (B) in the polymerizable liquid crystal composition (B) constituting the retardation film is, for example, 70 to 99 based on 100 parts by mass of the solid content of the polymerizable liquid crystal composition (B). It is 0.5 parts by mass, preferably 80 to 99 parts by mass, more preferably 90 to 98 parts by mass. When the content is within the above range, the orientation of the retardation film tends to increase.
  • the solid content refers to the total amount of components obtained by removing volatile components such as a solvent from the polymerizable liquid crystal composition (B).
  • the polymerizable liquid crystal composition (B) may contain a polymerization initiator for initiating a polymerization reaction of the polymerizable liquid crystal compound (B).
  • the polymerization initiator may be appropriately selected from those conventionally used in the art, and may be a thermal polymerization initiator or a photopolymerization initiator, but under a lower temperature condition.
  • a photopolymerization initiator is preferable in that the polymerization reaction can be started.
  • examples of the photopolymerization initiator that can be used in the composition for forming a polarizer include the same ones as those exemplified above.
  • the polymerizable liquid crystal composition (B) may contain, if necessary, a photosensitizer, a leveling agent, an additive exemplified as an additive included in the composition for forming a polarizer, and the like.
  • a photosensitizer exemplified as an additive included in the composition for forming a polarizer
  • the leveling agent include those similar to those exemplified above as those usable in the composition for forming a polarizer.
  • the polymerizable liquid crystal composition (B) is prepared, for example, by mixing and stirring the polymerizable liquid crystal compound (B) and, if necessary, a polymerization initiator, an additive, and the like. Further, in order to improve coatability, a viscosity may be adjusted by adding a solvent to the polymerizable liquid crystal composition (B).
  • the solvent include the solvents exemplified above as the solvent contained in the polarizer-forming composition.
  • the retardation film is obtained by coating the polymerizable liquid crystal composition (B) on a substrate or an alignment film, removing the solvent by drying, heating the polymerizable liquid crystal compound (B) in the obtained coating film, and / or Alternatively, it can be obtained by curing with an active energy ray.
  • the alignment film the same films as those exemplified above can be used when manufacturing the polarizer of the present invention.
  • the solvent used for the retardation film-forming composition, the method of applying the retardation film-forming composition, the curing conditions using active energy rays, etc., are all the same as those that can be employed in the method for producing a polarizer of the present invention. Things.
  • the thickness of the retardation film can be appropriately selected according to the display device to be applied, but is preferably from 0.1 to 10 ⁇ m, more preferably from 1 to 5 ⁇ m, from the viewpoint of thinning and flexibility. More preferably, it is 1 to 3 ⁇ m.
  • the polarizing plate in the present invention may include a layer other than the polarizing film, the retardation film and the pressure-sensitive adhesive layer or the adhesive layer, for example, a protective film.
  • the polarizing film and the retardation film are bonded via an adhesive layer or a pressure-sensitive adhesive layer.
  • the thickness of the polarizing plate of the present invention is preferably 1 to 100 ⁇ m, more preferably 2 to 70 ⁇ m, and still more preferably 3 to 60 ⁇ m, from the viewpoint of the flexibility and visibility of the display device.
  • FIG. 1 shows a schematic cross-sectional view of a layer configuration of a polarizing film with a front plate according to an embodiment of the present invention.
  • the front plate 3 is formed on the first resin layer 4 of the polarizing film 2.
  • a first resin layer 4, a polarizer 5, an alignment film 6, and a second resin layer 7 are laminated in this order from the front plate 3 side.
  • the polarizing film 1 with a front plate can provide surface hardness and light resistance by including the front plate.
  • a pressure-sensitive adhesive layer or an adhesive layer may be formed between the front plate 3 and the first resin layer 4.
  • FIG. 2 is a schematic cross-sectional view of a layer configuration of a polarizing plate with a front plate according to an embodiment of the present invention.
  • the front plate 3 is formed on the polarizing plate 9.
  • the first resin layer 4, the polarizer 5, the alignment film 6, the second resin layer 7, and the retardation film 10 are laminated in this order from the front plate 3 side.
  • the polarizing plate 8 having the front plate can impart surface hardness and light resistance.
  • an adhesive layer or an adhesive layer is formed between the front plate 3 and the first resin layer 4 and / or between the second resin layer 7 and the retardation film 10. It may be.
  • FIGS. 1 and 2 the dimensions, ratios, and the like of each layer are appropriately changed in order to make the drawings easy to see.
  • FIG. 3 shows a schematic cross-sectional view of the layer structure of a polarizing film with a front plate according to another embodiment of the present invention.
  • the front plate 3 is formed on the second resin layer 7 of the polarizing film 2.
  • a second resin layer 7, an orientation film 6, a polarizer 5, and a first resin layer 4 are laminated in this order from the front plate 3 side.
  • a pressure-sensitive adhesive layer or an adhesive layer may be formed between the front plate 3 and the second resin layer 7.
  • FIG. 4 is a schematic cross-sectional view of a layer configuration of a polarizing plate with a front plate according to another embodiment of the present invention.
  • the front plate 3 is formed on the polarizing plate 13.
  • the polarizing plate 13 has a second resin layer 7, an alignment film 6, a polarizer 5, a first resin layer 4, and a retardation film 10 laminated in this order from the front plate 3 side.
  • the polarizing plate 13 with a front plate can provide surface hardness and light resistance by including the front plate.
  • the polarizing plate 13 with a front plate has an adhesive layer or an adhesive layer formed between the front plate 3 and the second resin layer 7 and / or between the first resin layer 4 and the retardation film 10. It may be.
  • FIGS. 3 and 4 the dimensions, ratios, and the like of the respective layers are appropriately changed in order to make the drawings easy to see.
  • the polarizing film or the polarizing plate of the present invention can be applied to a display device.
  • the display device can be obtained, for example, by laminating the polarizing film or the polarizing plate of the present invention to the surface of the display device via an adhesive layer or an adhesive layer.
  • a display device is a device having a display mechanism and includes a light-emitting element or a light-emitting device as a light-emitting source.
  • Examples of the display device include a liquid crystal display device, an organic electroluminescence (EL) display device, an inorganic electroluminescence (EL) display device, a touch panel display device, an electron emission display device (eg, a field emission display device (eg, FED), and a surface field emission display device).
  • EL organic electroluminescence
  • EL inorganic electroluminescence
  • FED field emission display device
  • SED electron emission display device
  • electronic paper display using electronic ink or electrophoretic element
  • plasma display projection display (grating light valve (GLV) display, display having digital micromirror device (DMD)) Etc.) and piezoelectric ceramic displays.
  • the liquid crystal display device includes any of a transmission type liquid crystal display device, a transflective type liquid crystal display device, a reflection type liquid crystal display device, a direct view type liquid crystal display device, a projection type liquid crystal display device and the like. These display devices may be display devices that display a two-dimensional image or stereoscopic display devices that display a three-dimensional image.
  • an organic EL display device and a touch panel display device are preferable, and an organic EL display device is particularly preferable.
  • Equation 1 The following formulas (Equation 1) and (Equation 2) are used to calculate the single transmittance and the degree of polarization at each wavelength, and then perform luminosity correction using a two-degree field of view (C light source) according to JIS Z 8701 to correct luminosity
  • composition (J) for forming resin layer The following components were mixed and stirred at 23 ° C. for 4 hours to obtain a resin layer forming composition (J).
  • composition (K) for forming resin layer The following components were mixed and stirred at 23 ° C. for 4 hours to obtain a resin layer forming composition (K).
  • Components of Composition (K) for Forming Resin Layer ⁇ Celoxide 2021P: 32.5 parts of 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (manufactured by Daicel Chemical Industries, Ltd.) ⁇ EHPE3150: 1,2-bis (hydroxymethyl) -1-butanol 1 , 2-epoxy-4- (2-oxiranyl) cyclohexane adduct (manufactured by Daicel Chemical Industries, Ltd.) 17.5 parts OXT-221: bis (3-ethyl-3-oxetanylmethyl) ether (Toagosei Co., Ltd.) 50 parts CPI-100P: 50% propylene carbonate solution of triarylsulf
  • composition (L) for forming resin layer An acetoacetylated modified polyvinyl alcohol resin (Gosefimer Z200, manufactured by Nippon Synthetic Chemical Industry Co., Ltd., saponification degree: 98.5 mol% or more) is dissolved in pure water by stirring at 90 ° C. for 4 hours, An aqueous solution having a concentration of 5% by weight was prepared.
  • acetoacetylated modified polyvinyl alcohol resin (Gosefimer Z200, manufactured by Nippon Synthetic Chemical Industry Co., Ltd., saponification degree: 98.5 mol% or more) is dissolved in pure water by stirring at 90 ° C. for 4 hours, An aqueous solution having a concentration of 5% by weight was prepared.
  • aqueous solution of the polyvinyl alcohol-based resin and a 10% by weight aqueous solution of sodium glyoxylate are mixed such that the solid content weight ratio of the acetoacetyl group-modified polyvinyl alcohol-based resin: sodium glyoxylate becomes 1: 0.1, and further water is added.
  • the composition was diluted with pure water so that the weight ratio of the solid content of the polyvinyl alcohol-based resin to 100 parts was 3.0 parts to prepare a resin layer forming composition (L).
  • Polyfunctional acrylate monomer (1) dipentaerythritol hexaacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., “NK ester @ A-DPH”), a branch point closest to a (meth) acryloyl group in a branched structure, ) The number of atoms in the chain connecting the acryloyl group is 2.
  • Polyfunctional acrylate monomer (2) Ethylene oxide (6) dipentaerythritol hexaacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., "NK Ester @ A-DPH-6E"), to the (meth) acryloyl group in the branched structure
  • the number of atoms in the chain connecting the closest branch point to the (meth) acryloyl group is 5.
  • Polyfunctional acrylate monomer (3) Ethylene oxide (12) dipentaerythritol hexaacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., "NK Ester @ A-DPH-12E"), to the (meth) acryloyl group in the branched structure
  • the number of atoms in the chain connecting the closest branch point to the (meth) acryloyl group is eight.
  • Polyfunctional acrylate monomer (4) Tripentaerythritol octaacrylate (manufactured by Koei Chemical Co., Ltd., "TPEA"), the branch point closest to the (meth) acryloyl group in the branched structure and the (meth) acryloyl group The number of atoms in the linking chain is two.
  • Urethane acrylate polymer (1) urethane acrylate ("Evecryl 4858", manufactured by Daicel Ornex Co., Ltd.), the number of functional groups is 2, the weight average molecular weight Mw is 450, and the number of functional groups per unit molecular weight is 44.4 ⁇ 10 ⁇ . 4 .
  • Urethane acrylate polymer (2) urethane acrylate (manufactured by Nippon Synthetic Chemical Industry Co., Ltd., "Shikko UV-7650"), the number of functional groups is 4 to 5, the weight average molecular weight Mw is 2,300, and the number of functional groups per unit molecular weight is 19 0.6 ⁇ 10 ⁇ 4 .
  • Radical polymerization initiator (1) phenylbis (2,4,6-trimethylbenzoyl) phosphine oxide (“Irgacure 819” manufactured by BASF) Radical polymerization initiator (2): 1-hydroxycyclohexyl phenyl ketone (“IRGACURE 184” manufactured by BASF) Radical polymerization initiator (3): 2- [4- (methylthio) benzoyl] -2- (4-morpholinyl) propane (“Irgacure 907” manufactured by BASF)
  • composition for forming polarizing film ⁇ Preparation of composition for forming polarizing film> The following components were mixed and stirred at 80 ° C. for 1 hour to obtain a composition for forming a polarizing film.
  • dichroic dye an azo dye described in Examples of JP-A-2013-101328 was used.
  • Polymerizable liquid crystal compound ⁇ Polymerizable liquid crystal compound:
  • Photopolymerization initiator 2-dimethylamino-2-benzyl-1- (4-morpholinophenyl) butan-1-one (Irgacure 369; Ciba Specialty Chemicals Co., Ltd.) 6 parts ⁇ Leveling agent: 1.2 parts of polyacrylate compound (BYK-361N; manufactured by BYK-Chemie), solvent: o-xylene 400 parts
  • Example 1 (2) Preparation of Second Resin Layer After a corona treatment was applied to the release-treated surface of a release-treated polyethylene terephthalate film (SP-PLR382050, manufactured by Lintec Co., Ltd.), the second curability was obtained.
  • the composition (A) for forming a resin layer is applied as a composition by a bar coating method (# 2 30 mm / s), and the exposure amount is 500 mJ using a UV irradiation apparatus (SPOT CURE SP-7; manufactured by Ushio Inc.).
  • a release film with a resin layer having a second resin layer formed on the surface of the release film was obtained.
  • the thickness of the second resin layer was 1.5 ⁇ m.
  • composition for forming a polarizing film is applied to the surface of the photo-alignment film of the laminate A obtained as described above by a bar coating method (# 930 mm / s), and dried at 120 ° C.
  • the polymerizable liquid crystal compound was phase-transformed into a liquid phase by heating and drying in an oven for 1 minute, and then cooled to room temperature to cause the polymerizable liquid crystal compound to undergo a phase transition to a smectic liquid crystal state.
  • the layer formed from the composition for forming a polarizing film is irradiated with ultraviolet light having an exposure amount of 1000 mJ / cm 2 (based on 365 nm).
  • the polymerizable liquid crystal compound contained in the dried film was polymerized while maintaining the smectic liquid crystal state of the polymerizable liquid crystal compound, and a polarizer (polarizing film) was formed from the dried film.
  • the thickness of the polarizer was 2.3 ⁇ m.
  • the resin layer-forming composition (A) was used as a first curable composition.
  • a UV coating system SPDOT CURE SP-7; manufactured by Ushio Inc.
  • a bar coating method # 2 30 mm / s.
  • a laminate C having a release film, a second resin layer, a photo-alignment film, a polarizer, and a first resin layer in this order was obtained.
  • a polarizing film having a second resin layer, a photo-alignment film, a polarizer, and a first resin layer in this order was obtained.
  • the thickness of the first resin layer was 1.5 ⁇ m.
  • Examples 1 to 9 and Comparative Examples 1 and 2 As shown in Table 2, in the same manner as in Example 1 except that the resin layer forming compositions (B) to (K) were used instead of the resin layer forming composition (A), respectively. The polarizing films of Examples 1 to 9 and Comparative Examples 1 and 2 were obtained.
  • composition for forming a polarizing film is applied to the surface of the photo-alignment film of the laminate K obtained as described above by a bar coating method (# 930 mm / s), and dried at 120 ° C.
  • the polymerizable liquid crystal compound was phase-transformed into a liquid phase by heating and drying in an oven for 1 minute, and then cooled to room temperature to cause the polymerizable liquid crystal compound to undergo a phase transition to a smectic liquid crystal state.
  • the layer formed from the composition for forming a polarizing film is irradiated with ultraviolet light having an exposure amount of 1000 mJ / cm 2 (based on 365 nm).
  • the polymerizable liquid crystal compound contained in the dried film was polymerized while maintaining the smectic liquid crystal state of the polymerizable liquid crystal compound, and a polarizer (polarizing film) was formed from the dried film.
  • the thickness of the polarizer was 2.3 ⁇ m.
  • the resin layer forming composition (L) is used as a first curable composition.
  • a release film, a second resin layer, a photo-alignment film, a polarizer, and a first resin layer are provided in this order.
  • a laminate M was obtained.
  • a polarizing film having a second resin layer, a photo-alignment film, a polarizer, and a first resin layer in this order was obtained.
  • the thickness of the first resin layer was 1.5 ⁇ m.
  • the polarizing films obtained in Examples 1 to 9 and Comparative Examples 1 to 3 were evaluated as having a good adhesion evaluation result, indicating that the interlayer adhesion was excellent. Further, ⁇ Ty and ⁇ Py, which are the amounts of change in Ty and Py before and after the heat resistance test, were close to 0, and it was also confirmed that the heat resistance was excellent. On the other hand, the polarizing films obtained in Comparative Examples 1 to 3 were evaluated as having poor adhesion, indicating poor adhesion.
  • the polarizing films obtained in Examples 5 and 8 were evaluated as ⁇ in the flexibility, indicating that the polarizing films had excellent flexibility in addition to adhesion and heat resistance.

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021235330A1 (ja) * 2020-05-20 2021-11-25 コニカミノルタ株式会社 偏光板、表示装置及び偏光板ロールの製造方法
CN114879296A (zh) * 2021-02-05 2022-08-09 住友化学株式会社 偏振元件及其制造方法
WO2023090051A1 (ja) * 2021-11-22 2023-05-25 住友化学株式会社 光学積層体

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20230107594A (ko) * 2020-11-27 2023-07-17 미쯔비시 케미컬 주식회사 광학 이방성 적층체 및 광학 소자
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JP7636249B2 (ja) 2021-04-16 2025-02-26 住友化学株式会社 光学積層体
CN115537213B (zh) * 2021-06-30 2025-08-01 石家庄诚志永华显示材料有限公司 可聚合组合物、偏光膜及偏光膜制备方法、显示元件及显示器
CN115537212B (zh) * 2021-06-30 2026-03-06 石家庄诚志永华显示材料有限公司 可聚合组合物、偏光膜及偏光膜制备方法、显示元件及显示器
CN120703890A (zh) 2024-03-26 2025-09-26 住友化学株式会社 偏振板、具备偏振板的圆偏振板以及具备偏振板或圆偏振板的显示装置
JP2025149918A (ja) 2024-03-26 2025-10-08 住友化学株式会社 偏光板およびこれを含む円偏光板

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015180929A (ja) * 2014-03-05 2015-10-15 富士フイルム株式会社 ハードコートフィルム、これを含む偏光板および画像表示装置、ならびにハードコートフィルムの製造方法
JP2017083843A (ja) * 2015-10-30 2017-05-18 住友化学株式会社 偏光板
JP2017194687A (ja) * 2012-06-04 2017-10-26 大日本印刷株式会社 光学積層体及び画像表示装置
WO2018016360A1 (ja) * 2016-07-21 2018-01-25 住友化学株式会社 楕円偏光板
JP2018128573A (ja) * 2017-02-08 2018-08-16 住友化学株式会社 偏光フィルム、円偏光板および表示装置
JP2019168690A (ja) * 2018-03-23 2019-10-03 東洋紡株式会社 エレクトロルミネッセンス表示装置

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101932960B (zh) * 2008-02-04 2013-03-13 住友化学株式会社 偏振板、光学构件及液晶显示装置
JP5267919B2 (ja) * 2008-08-06 2013-08-21 住友化学株式会社 偏光板、光学部材および液晶表示装置
JP5267920B2 (ja) * 2008-08-06 2013-08-21 住友化学株式会社 偏光板およびその製造方法、ならびに液晶表示装置
JP5120715B2 (ja) * 2008-09-10 2013-01-16 住友化学株式会社 偏光板およびその製造方法、ならびに光学部材、液晶表示装置
JP6171276B2 (ja) * 2011-07-12 2017-08-02 住友化学株式会社 偏光子及びその製造方法
JP2013137521A (ja) * 2011-11-30 2013-07-11 Sumitomo Chemical Co Ltd 複合位相差板及びそれを用いた複合偏光板
JP6268730B2 (ja) * 2012-03-30 2018-01-31 住友化学株式会社 円偏光板及びその製造方法
KR102508041B1 (ko) * 2014-08-29 2023-03-08 스미또모 가가꾸 가부시키가이샤 광학 필름의 제조 방법
KR101802562B1 (ko) * 2014-08-29 2017-11-29 삼성에스디아이 주식회사 편광판, 이를 위한 편광판용 보호층 조성물 및 이를 포함하는 광학표시장치
KR20160092163A (ko) * 2015-01-27 2016-08-04 동우 화인켐 주식회사 보호층을 포함하는 편광판 및 이를 포함하는 표시장치
WO2017061541A1 (ja) * 2015-10-07 2017-04-13 日産化学工業株式会社 液晶配向膜製造用組成物、該組成物を用いた液晶配向膜及びその製造方法、並びに液晶配向膜を有する液晶表示素子及びその製造方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017194687A (ja) * 2012-06-04 2017-10-26 大日本印刷株式会社 光学積層体及び画像表示装置
JP2015180929A (ja) * 2014-03-05 2015-10-15 富士フイルム株式会社 ハードコートフィルム、これを含む偏光板および画像表示装置、ならびにハードコートフィルムの製造方法
JP2017083843A (ja) * 2015-10-30 2017-05-18 住友化学株式会社 偏光板
WO2018016360A1 (ja) * 2016-07-21 2018-01-25 住友化学株式会社 楕円偏光板
JP2018128573A (ja) * 2017-02-08 2018-08-16 住友化学株式会社 偏光フィルム、円偏光板および表示装置
JP2019168690A (ja) * 2018-03-23 2019-10-03 東洋紡株式会社 エレクトロルミネッセンス表示装置

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021235330A1 (ja) * 2020-05-20 2021-11-25 コニカミノルタ株式会社 偏光板、表示装置及び偏光板ロールの製造方法
JPWO2021235330A1 (https=) * 2020-05-20 2021-11-25
CN114879296A (zh) * 2021-02-05 2022-08-09 住友化学株式会社 偏振元件及其制造方法
WO2023090051A1 (ja) * 2021-11-22 2023-05-25 住友化学株式会社 光学積層体
JP2023076153A (ja) * 2021-11-22 2023-06-01 住友化学株式会社 光学積層体

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