WO2019003682A1 - Copolymère photo-alignable, fil photo-aligné, stratifié optique et dispositif d'affichage d'image - Google Patents

Copolymère photo-alignable, fil photo-aligné, stratifié optique et dispositif d'affichage d'image Download PDF

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Publication number
WO2019003682A1
WO2019003682A1 PCT/JP2018/018887 JP2018018887W WO2019003682A1 WO 2019003682 A1 WO2019003682 A1 WO 2019003682A1 JP 2018018887 W JP2018018887 W JP 2018018887W WO 2019003682 A1 WO2019003682 A1 WO 2019003682A1
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group
formula
carbon atoms
repeating unit
liquid crystal
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PCT/JP2018/018887
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English (en)
Japanese (ja)
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隆史 飯泉
寛 野副
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富士フイルム株式会社
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Priority to JP2019526665A priority Critical patent/JP6837550B2/ja
Publication of WO2019003682A1 publication Critical patent/WO2019003682A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/303—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one or more carboxylic moieties in the chain
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/13363—Birefringent elements, e.g. for optical compensation
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers

Definitions

  • the present invention relates to a photoalignable copolymer, a photoalignment film, an optical laminate, and an image display device.
  • Optical films such as an optical compensation sheet and a retardation film, are used in various image display devices from the viewpoint of image coloration cancellation, viewing angle widening, and the like.
  • a stretched birefringence film has been used as an optical film, but in recent years, it has been proposed to use an optically anisotropic layer using a liquid crystalline compound in place of the stretched birefringence film.
  • Such an optically anisotropic layer is known to be provided with an alignment film on a support forming the optically anisotropic layer in order to align the liquid crystal compound, and rubbing is performed as the alignment film.
  • a photo alignment film which has been subjected to a photo alignment process instead of the process is known.
  • Patent Document 1 discloses an embodiment in which a polymer layer containing a compound containing a repeating unit having 2 to 3 photoalignable groups is used as an alignment layer ([claim 1] [claim 7] [Claim 8]).
  • Patent Document 2 discloses a liquid crystal alignment layer formed from a thermosetting film-forming composition containing an acrylic copolymer having a photodimerization site such as cinnamoyl group and a crosslinking agent ([claims] 1] [claim 3] [claim 11] ⁇ 0028>).
  • liquid crystal orientation the orientation with respect to the liquid crystal compound of the above may be inferior.
  • the present invention provides a photoalignment copolymer capable of producing a photoalignment film excellent in liquid crystal alignment properties, and a photoalignment film produced using the same, an optical laminate, and an image display device. To be an issue.
  • the present inventors prepared using a copolymer having a repeating unit containing two or more specific photoalignable groups and a repeating unit containing a crosslinkable group. It has been found that the liquid crystal alignment of the resulting photo alignment film is good, and the present invention is completed. That is, the present inventors found that the above-mentioned subject can be achieved by the following composition.
  • L 1 in the formula (1) and L 2 in the formula (2) each independently represent a linear, branched or cyclic alkylene group having 1 to 10 carbon atoms, and 6 to 12 carbon atoms
  • a in the formula (1) is a trivalent to hexavalent linking group.
  • a in the formula (1) is an m-valent hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and a part of carbon atoms constituting the hydrocarbon group is hetero.
  • a in the formula (1) is a linking group containing an alicyclic hydrocarbon group.
  • R 2 , R 3 , R 4 , R 5 and R 6 in the formula (1) each independently represent a hydrogen atom, or a halogen atom, a linear, branched or branched chain having 1 to 20 carbon atoms Cyclic alkyl group, linear halogenated alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, aryloxy group having 6 to 20 carbon atoms, cyano group
  • the photoalignable copolymer according to any one of [1] to [7], which is a substituent selected from the group consisting of an amino group and a group represented by Formula (7) described later.
  • An optical laminate comprising: the photoalignment film according to [13]; and an optically anisotropic layer formed using a liquid crystal composition containing a liquid crystalline compound.
  • An image display device having the optical laminate according to [14].
  • a photoalignment copolymer capable of producing a photoalignment film excellent in liquid crystal alignment properties, and a photoalignment film produced using the same, an optical laminate, and an image display device are provided. be able to.
  • a numerical range represented using “to” means a range including numerical values described before and after “to” as the lower limit value and the upper limit value.
  • the photoalignable copolymer of the present invention has a repeating unit A represented by the formula (1) containing a photoalignable group and a repeating unit B represented by the formula (2) containing a crosslinkable group. It is a photoalignable copolymer.
  • R 1 represents a hydrogen atom or a methyl group
  • L 1 represents a single bond or a divalent linking group
  • A represents an m-valent linking group
  • R 2 and R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or a substituent. Two adjacent groups among R 2 , R 3 , R 4 , R 5 and R 6 may be combined to form a ring.
  • m represents an integer of 3 or more
  • n represents an integer of m-1.
  • the plurality of R 2 's , R 3' s , R 4 's , R 5' s and R 6 's may be the same or different.
  • R 7 represents a hydrogen atom or a methyl group
  • L 2 represents a divalent linking group
  • X represents a crosslinkable group.
  • the site that interacts with the liquid crystal compound by increasing the concentration of photoalignable groups per unit area It is considered that the inclusion of the crosslinkable group in the repeating unit B promotes the immobilization of the alignment, and as a result, the liquid crystal alignment of the formed photo alignment film is improved.
  • linear, branched or cyclic alkylene group having 1 to 10 carbon atoms include a methylene group, an ethylene group, a propylene group, a butylene group and a pentylene group. And hexylene and decylene groups.
  • branched alkylene groups include dimethylmethylene, methylethylene, 2,2-dimethylpropylene and 2-ethyl-2-methylpropylene.
  • cyclic alkylene group specifically, for example, cyclopropylene group, cyclobutylene group, cyclopentylene group, cyclohexylene group, cyclooctylene group, cyclodecylene group, adamantane-diyl group, norbornane-diyl group And exo-tetrahydrodicyclopentadiene-diyl group etc., among which cyclohexylene group is preferable.
  • arylene group having 6 to 12 carbon atoms include phenylene group, xylylene group, biphenylene group, naphthylene group, 2,2'-methylenebisphenyl group and the like, among which phenylene group is preferable. .
  • m represents an integer of 3 or more and is preferably an integer of 3 to 6, more preferably an integer of 3 to 5, and still more preferably 3 or 4.
  • a in the above formula (1) is a substituent because the photoalignable group easily interacts with the liquid crystal compound and the liquid crystal alignment of the produced photoalignment film becomes better.
  • a hydrocarbon group of 1 to 24 carbon atoms which may have one or more carbon atoms, and part of carbon atoms constituting the hydrocarbon group may be substituted with a hetero atom (hereinafter referred to as It is preferably "m-valent hydrocarbon group A".
  • m-valent hydrocarbon group A examples include groups represented by the following formulas (a1) to (a4).
  • * L represents a bonding position to L 1 in the above formula (1)
  • * above the oxygen atom represents a carbonyl group in the above formula (1) It represents the bonding position with the constituent carbon atom.
  • a substituent which m-valent hydrocarbon group A may have, as a substituent which an alkylene group, an arylene group, and an imino group may have, for example, an alkyl group, an alkoxy group, a halogen atom, A hydroxyl group etc. are mentioned.
  • alkyl group for example, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms is preferable, and an alkyl group having 1 to 8 carbon atoms (eg, methyl group, ethyl group, propyl group, isopropyl) Group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, cyclohexyl group etc. is more preferable, an alkyl group having 1 to 4 carbon atoms is still more preferable, and a methyl group or an ethyl group is more preferable. Is particularly preferred.
  • the alkoxy group is, for example, preferably an alkoxy group having 1 to 18 carbon atoms, more preferably an alkoxy group having 1 to 8 carbon atoms (eg, methoxy group, ethoxy group, n-butoxy group, methoxyethoxy group, etc.) More preferably, it is an alkoxy group of the number 1 to 4, and particularly preferably a methoxy group or an ethoxy group.
  • a halogen atom a fluorine atom, a chlorine atom, a bromine atom, an iodine atom etc. are mentioned, for example, Especially, it is preferable that it is a fluorine atom and a chlorine atom.
  • the m-valent hydrocarbon group A is alicyclic because the photoalignment group easily interacts with the liquid crystal compound, and the liquid crystal alignment of the produced photoalignment film becomes better. It is preferably a linking group containing a hydrocarbon group, and more preferably a group represented by the above-mentioned formula (a2).
  • halogen atom a fluorine atom, a chlorine atom, a bromine atom, an iodine atom etc. are mentioned, for example, Especially, it is preferable that it is a fluorine atom and a chlorine atom.
  • the linear alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, and specifically, for example, a methyl group, Ethyl group, n-propyl group and the like can be mentioned.
  • the branched alkyl group is preferably an alkyl group having a carbon number of 3 to 6, and specific examples thereof include an isopropyl group and a tert-butyl group.
  • the cyclic alkyl group is preferably an alkyl group having a carbon number of 3 to 6, and specific examples thereof include a cyclopropyl group, a cyclopentyl group and a cyclohexyl group.
  • the linear halogenated alkyl group having 1 to 20 carbon atoms is preferably a fluoroalkyl group having 1 to 4 carbon atoms, and specifically, for example, a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group And perfluorobutyl group etc., among which trifluoromethyl group is preferable.
  • the alkoxy group having 1 to 20 carbon atoms is preferably an alkoxy group having 1 to 8 carbon atoms, and specific examples thereof include a methoxy group, an ethoxy group, an n-butoxy group, a methoxyethoxy group and the like. Methoxy or ethoxy is preferred.
  • the aryl group having 6 to 20 carbon atoms is preferably an aryl group having 6 to 12 carbon atoms, and specific examples thereof include a phenyl group, an ⁇ -methylphenyl group, and a naphthyl group. Among them, a phenyl group is preferable. preferable.
  • the aryloxy group having 6 to 20 carbon atoms is preferably an aryloxy group having 6 to 12 carbon atoms, and specific examples thereof include a phenyloxy group and a 2-naphthyloxy group. Among them, a phenyloxy group is preferable. Is preferred.
  • amino group examples include: primary amino group (—NH 2 ); secondary amino group such as methylamino group; dimethylamino group, diethylamino group, dibenzylamino group, nitrogen-containing heterocyclic compound (eg, pyrrolidine) , And a tertiary amino group such as a group having a nitrogen atom of piperidine, piperazine and the like as a bond;
  • a linear or cyclic alkyl group having 1 to 20 carbon atoms can be mentioned Be
  • the linear alkyl group is preferably an alkyl group having a carbon number of 1 to 6, and specific examples thereof include a methyl group, an ethyl group and an n-propyl group. Among them, a methyl group or an ethyl group is preferable.
  • the cyclic alkyl group is preferably an alkyl group having a carbon number of 3 to 6, and specific examples thereof include a cyclopropyl group, a cyclopentyl group and a cyclohexyl group.
  • the monovalent organic group represented by R 9 in the above formula (7) may be a combination of the linear alkyl group and the cyclic alkyl group described above directly or via a single bond. Good.
  • R 2 and R 3 in the above formula (1) are preferred because the photoalignment group easily interacts with the liquid crystal compound and the liquid crystal alignment of the produced photoalignment film becomes better.
  • R 4 , R 5 and R 6 preferably at least R 4 represents the above-mentioned substituent, and further, the rigidity of the obtained photoalignable copolymer is improved, and the photoalignment is produced It is more preferable that all of R 2 , R 3 , R 5 and R 6 represent a hydrogen atom because the heat resistance of the film is further improved.
  • R 4 in the above-mentioned formula (1) is an electron donating substituent, because the reaction efficiency is improved when the resulting photo alignment film is irradiated with light.
  • the electron donating substituent refers to a substituent having a Hammett value (Hammett substituent constant ⁇ p) of 0 or less, and, for example, among the above-mentioned substituents, an alkyl group, A halogenated alkyl group, an alkoxy group, etc.
  • a cyclic alkyl group for example, a cyclohexyl group
  • an alkoxy group for example, a methoxy group
  • repeating unit A represented by the formula (1) containing a photoalignable group examples include the repeating units A-1 to A-76 shown below.
  • Me represents a methyl group
  • Et represents an ethyl group
  • i Pr represents an isopropyl group.
  • the crosslinkable group is preferably a so-called self-crosslinkable group in which crosslinking proceeds between functional groups without adding a crosslinking agent, and specifically, the following formulas (3) to (5) It is more preferable that it is a crosslinkable group represented by either of, and it is still more preferable that it is a crosslinkable group represented by following formula (3) or (4).
  • * represents a bonding position to L 2 in the above formula (2)
  • R 8 represents any of a hydrogen atom, a methyl group and an ethyl group.
  • repeating unit B represented by the formula (2) containing a photoalignable group include the following repeating units B-1 to B-3.
  • the above-mentioned content mass Y of the repeating unit B preferably satisfy the following formula (8), and the photoalignment group is likely to interact with the liquid crystal compound to be produced. It is more preferable that the following formula (9) is satisfied, because the liquid crystal alignment property of the above becomes better. 0.4 ⁇ X / (X + Y) ⁇ 0.8 (8) 0.45 ⁇ X / (X + Y) ⁇ 0.65 (9)
  • the photoalignable copolymer of the present invention may have other repeating units in addition to the above-described repeating unit A and repeating unit B, as long as the effects of the present invention are not impaired.
  • a monomer (radically polymerizable monomer) which forms such other repeating units for example, acrylic acid ester compounds, methacrylic acid ester compounds, maleimide compounds, acrylamide compounds, acrylonitrile, maleic anhydride, styrene compounds, Vinyl compounds and the like can be mentioned.
  • the synthesis method of the photoalignable copolymer of the present invention is not particularly limited.
  • a monomer forming the above-mentioned repeating unit A, a monomer forming the above-mentioned repeating unit B, and any other repeating unit are formed. These monomers can be synthesized by mixing them and polymerizing them in an organic solvent using a radical polymerization initiator.
  • the weight average molecular weight (Mw) of the photoalignable copolymer of the present invention is 10,000 to 1,000 because the rigidity of the obtained photoalignable copolymer is improved and the heat resistance of the produced photoalignment film is improved. 500,000 are preferable, and 30,000 to 200,000 are more preferable because the orientation becomes better.
  • the weight average molecular weight and the number average molecular weight in the present invention are values measured by gel permeation chromatography (GPC) under the conditions shown below.
  • the photoalignment film of the present invention is a composition for a photoalignment film containing the above-described photoalignment copolymer of the present invention (hereinafter, also formally referred to as "the composition for photoalignment film of the present invention"). It is a photo alignment film formed using.
  • the thickness of the photoalignment film is not particularly limited and may be appropriately selected depending on the purpose, but it is preferably 10 to 1000 nm, and more preferably 10 to 700 nm.
  • the content of the photoalignable copolymer of the present invention in the composition for photoalignment film of the present invention is not particularly limited, but in the case of containing an organic solvent described later, it is 0.1 to 50 with respect to 100 parts by mass of the organic solvent. It is preferable that the amount is in the range of 0.5 to 10 parts by mass.
  • the composition for a photoalignment film of the present invention preferably contains an organic solvent from the viewpoint of workability for producing a photoalignment film.
  • an organic solvent specifically, for example, ketones (eg, acetone, 2-butanone, methyl isobutyl ketone, cyclohexanone, etc.), ethers (eg, dioxane, tetrahydrofuran etc.), aliphatic hydrocarbons (Eg, hexane), alicyclic hydrocarbons (eg, cyclohexane), aromatic hydrocarbons (eg, toluene, xylene, trimethylbenzene etc.), halogenated carbons (eg, dichloromethane, dichloroethane, di) Chlorobenzene, chlorotoluene etc., esters (eg methyl acetate, ethyl acetate, butyl acetate etc), water, alcohols (eg ethanol, isopropan
  • composition for photo alignment film of the present invention may contain other components other than the above, and examples thereof include a crosslinking catalyst, an adhesion improver, a leveling agent, a surfactant, a plasticizer and the like.
  • the photoalignment film of the present invention can be produced by a conventionally known production method except that the composition for photoalignment film of the present invention described above is used.
  • the composition for photoalignment film of the present invention described above is supported Producing by a manufacturing method including a coating step of coating on a body surface, and a light irradiation step of irradiating non-polarized light in a direction oblique to the polarized light or the coated film surface with respect to the coated film of the composition for photo alignment film it can.
  • the support will be described in the optical laminate of the present invention described later.
  • the coating method in the coating step is not particularly limited and may be appropriately selected depending on the purpose. Examples thereof include spin coating, die coating, gravure coating, flexographic printing, and inkjet printing.
  • the polarized light irradiated to the coating film of the composition for photo alignment film is not particularly limited, and examples thereof include linearly polarized light, circularly polarized light, elliptically polarized light and the like, among which linearly polarized light is preferable.
  • the “oblique direction” for irradiating non-polarized light is not particularly limited as long as it is a direction inclined at a polar angle ⁇ (0 ⁇ ⁇ 90 °) with respect to the normal direction of the coating film surface. Can be selected as appropriate, but preferably ⁇ is 20 to 80 °.
  • the wavelength in polarized light or non-polarized light is not particularly limited as long as the coating film of the composition for photo alignment film can be provided with the ability to control the alignment of liquid crystalline molecules, for example, ultraviolet light, near ultraviolet light, visible light Etc. Among them, near ultraviolet light of 250 nm to 450 nm is particularly preferable.
  • a light source for irradiating polarized light or non-polarized light for example, a xenon lamp, a high pressure mercury lamp, an ultra high pressure mercury lamp, a metal halide lamp and the like can be mentioned.
  • the wavelength range to be irradiated can be limited by using an interference filter, a color filter, or the like for ultraviolet light or visible light obtained from such a light source.
  • linearly polarized light can be obtained by using a polarizing filter or a polarizing prism for the light from these light sources.
  • the integrated light quantity of polarized light or non-polarized light is not particularly limited as long as the coating of the composition for photo alignment film can be given the ability to control the alignment of liquid crystalline molecules, and is not particularly limited. / Cm 2 is preferable, and 5 to 100 mJ / cm 2 is more preferable.
  • the illumination intensity of polarized light or non-polarized light is not particularly limited as long as the coating of the composition for photo alignment film can be provided with the ability to control the alignment of liquid crystalline molecules, but 0.1 to 300 mW / cm 2 Preferably, 1 to 100 mW / cm 2 is more preferable.
  • the optical laminate of the present invention is an optical laminate having the above-described photoalignment film of the present invention and an optically anisotropic layer formed using a liquid crystal composition containing a liquid crystalline compound.
  • the optical laminate of the present invention preferably further comprises a support, and specifically preferably comprises a support, an optical alignment film and an optically anisotropic layer in this order. .
  • optically anisotropic layer included in the optical laminate of the present invention is not particularly limited as long as it is an optically anisotropic layer containing a liquid crystalline compound, and conventionally known optically anisotropic layers may be appropriately employed and used. it can.
  • Such an optically anisotropic layer is a layer obtained by curing a composition containing a liquid crystal compound having a polymerizable group (hereinafter, also referred to as a “composition for forming an optically anisotropic layer”). And may be a single layer structure or a structure (laminated body) in which a plurality of layers are laminated.
  • the liquid crystal compound and optional additives contained in the composition for forming an optically anisotropic layer are described below.
  • the liquid crystalline compound contained in the composition for forming an optically anisotropic layer is a liquid crystalline compound having a polymerizable group.
  • liquid crystal compounds can be classified into rod-like types and discotic types according to their shapes. Furthermore, there are low molecular weight and high molecular type respectively.
  • a polymer refers to one having a degree of polymerization of 100 or more (Polymer physics / phase transition dynamics, Masao Doi, page 2, Iwanami Shoten, 1992).
  • any liquid crystal compound can be used, but it is preferable to use a rod-like liquid crystal compound or a discotic liquid crystal compound, and it is more preferable to use a rod-like liquid crystal compound.
  • liquid crystal compound having a polymerizable group is used to fix the above-mentioned liquid crystal compound, it is more preferable that the liquid crystal compound has two or more polymerizable groups in one molecule. In the case where the liquid crystal compound is a mixture of two or more types, it is preferable that at least one type of liquid crystal compound has two or more polymerizable groups in one molecule. In addition, after the liquid crystal compound is fixed by polymerization, it is no longer necessary to exhibit liquid crystallinity.
  • the type of the polymerizable group is not particularly limited, and a functional group capable of addition polymerization reaction is preferable, and a polymerizable ethylenically unsaturated group or a ring polymerizable group is preferable. More specifically, (meth) acryloyl group, vinyl group, styryl group, allyl group and the like are preferably mentioned, and (meth) acryloyl group is more preferable. In addition, a (meth) acryloyl group is a description which means a methacryloyl group or an acryloyl group.
  • rod-like liquid crystalline compound for example, those described in claim 1 of JP-A-11-513019 and paragraphs [0026] to ⁇ 0098> of JP-A-2005-289980 can be preferably used, and
  • tick liquid crystal compound for example, those described in paragraphs ⁇ 0020> to ⁇ 0067> of JP2007-108732A and paragraphs ⁇ 0013> to ⁇ 0108> of JP2010-244038A are preferably used. But not limited thereto.
  • the composition for forming an optically anisotropic layer may contain components other than the liquid crystal compound described above.
  • the composition for forming an optically anisotropic layer may contain a polymerization initiator.
  • the polymerization initiator to be used is selected according to the type of polymerization reaction, and examples thereof include a thermal polymerization initiator and a photopolymerization initiator.
  • examples of the photopolymerization initiator include ⁇ -carbonyl compounds, acyloin ethers, ⁇ -hydrocarbon substituted aromatic acyloin compounds, polynuclear quinone compounds, combinations of triarylimidazole dimers and p-aminophenyl ketones, etc.
  • Be The amount of the polymerization initiator used is preferably 0.01 to 20% by mass, and more preferably 0.5 to 5% by mass, with respect to the total solid content of the composition.
  • the composition for forming an optically anisotropic layer may contain a polymerizable monomer from the viewpoint of the uniformity of the coating film and the strength of the film.
  • the polymerizable monomer include radically polymerizable or cationically polymerizable compounds.
  • Preferred are polyfunctional radically polymerizable monomers, and those copolymerizable with the above-mentioned polymerizable group-containing liquid crystal compound.
  • the content of the polymerizable monomer is preferably 1 to 50% by mass, and more preferably 2 to 30% by mass, with respect to the total mass of the liquid crystal compound.
  • a surfactant may be contained in the composition for forming an optically anisotropic layer from the viewpoint of the uniformity of the coating film and the strength of the film.
  • a conventionally well-known compound is mentioned, especially a fluorine-type compound is preferable.
  • the compounds described in paragraphs ⁇ 0028> to ⁇ 0056> in JP 2001-330725 A the compounds described in paragraphs ⁇ 0069> to ⁇ 0126> in JP 2005-062673 A. Can be mentioned.
  • an organic solvent may be contained in the composition for forming an optically anisotropic layer.
  • an organic solvent the thing similar to what was demonstrated in the composition for photoalignment films of this invention mentioned above can be mentioned.
  • composition for forming an optically anisotropic layer a polarizer interface side vertical alignment agent, a vertical alignment promoter such as an air interface vertical side alignment agent, a polarizer interface side horizontal alignment agent, and air Various alignment agents such as a horizontal alignment promoter such as an interface-side horizontal alignment agent may be included.
  • the composition for forming an optically anisotropic layer may contain an adhesion improver, a plasticizer, a polymer and the like.
  • the formation method of the optically anisotropic layer using the composition for optically anisotropic layer formation which has such a component is not specifically limited,
  • an optically anisotropic layer The composition for formation can be applied to form a coating film, and the resulting coating film can be formed by curing treatment (irradiation with ultraviolet light (light irradiation treatment) or heat treatment).
  • the application of the composition for forming an optically anisotropic layer can be carried out by a known method (for example, a wire bar coating method, an extrusion coating method, a direct gravure coating method, a reverse gravure coating method, a die coating method).
  • the thickness of the optically anisotropic layer is not particularly limited, but is preferably 0.1 to 10 ⁇ m, and more preferably 0.5 to 5 ⁇ m.
  • the optical layered product of the present invention may have a support as a substrate for forming an optically anisotropic layer as described above.
  • a support include a polarizer, a polymer film and the like, and combinations thereof, such as a laminate of a polarizer and a polymer film, a laminate of a polymer film, a polarizer and a polymer film It may be a body or the like.
  • the support may be a temporary support which may be peeled off (hereinafter, it may simply be referred to simply as a “temporary support”) after the formation of the optically anisotropic layer.
  • the optically anisotropic layer may be provided by peeling the polymer film functioning as a temporary support from the optical laminate. For example, after preparing an optical laminate including an optically anisotropic layer and a temporary support, and bonding the optically anisotropic layer side of the optical laminate to a support including a polarizer with an adhesive or an adhesive, By peeling off the temporary support contained in the optically anisotropic layer, a laminate of a support including a polarizer and an optically anisotropic layer may be provided.
  • a polarizer is not particularly limited as long as it is a member having a function of converting light into specific linear polarization, and conventionally known absorption polarizers and reflection polarizers can be used.
  • absorption type polarizer an iodine based polarizer, a dye based polarizer using a dichroic dye, a polyene based polarizer and the like are used.
  • iodine type polarizers and dye type polarizers there are coating type polarizers and stretching type polarizers, either of which can be applied, but polarized light produced by adsorbing iodine or a dichroic dye to polyvinyl alcohol and stretching it Preferably a child.
  • multilayer film which formed the polyvinyl alcohol layer on the base material patent 5048120, patent 5143918, patent 4691205, patent No. 4,751,481 and Japanese Patent No. 4,751,486 can be mentioned, and known techniques relating to these polarizers can also be preferably used.
  • a reflection type polarizer As a reflection type polarizer, a polarizer in which thin films different in birefringence are laminated, a wire grid type polarizer, a polarizer in which a cholesteric liquid crystal having a selective reflection area and a quarter wavelength plate are combined, etc. are used.
  • a polymer containing polyvinyl alcohol resin (-CH 2 -CHOH- as a repeating unit) is intended, in particular, at least one selected from the group consisting of polyvinyl alcohol and ethylene-vinyl alcohol copolymer It is preferable that it is a polarizer containing one is preferable.
  • the polarizing plate can be produced, for example, as follows.
  • the support is peeled off from the above-mentioned optical laminate, and the layer containing the optically anisotropic layer is laminated on the support containing a polarizer.
  • the above-mentioned optical laminate is laminated on a support including a polarizer, and then the peelable support contained in the optical laminate is peeled off.
  • both layers may be adhered by an adhesive or the like.
  • the adhesive is not particularly limited, but as described in JP-A-2004-245925, a curable adhesive of an epoxy compound having no aromatic ring in the molecule, as described in JP-A-2008-174667, 360 to An active energy ray-curable adhesive comprising a photopolymerization initiator having a molar absorption coefficient of 400 or more at a wavelength of 450 nm and an ultraviolet curable compound as essential components, (meth) acrylic compound described in JP-A-2008-174667 (A) a (meth) acrylic compound having two or more (meth) acryloyl groups in the molecule, and (b) a hydroxyl group in the molecule in a total amount of 100 parts by mass, and only one polymerizable double bond And (c) phenol ethylene oxide modified acrylate or nonyl phenol ethylene oxide modified acrylic Such as an active energy ray-curable adhesive containing a chromatography bets and the like.
  • the thickness of the polarizer is not particularly limited, but is preferably 1 to 60 ⁇ m, more preferably 1 to 30 ⁇ m, and still more preferably 2 to 20 ⁇ m.
  • the polymer film is not particularly limited, and a commonly used polymer film (for example, a polarizer protective film or the like) can be used.
  • a polymer which comprises a polymer film For example, A cellulose polymer; An acrylic polymer which has acrylic acid ester polymers, such as a polymethyl methacrylate and a lactone ring containing polymer; A thermoplastic norbornene-type polymer; A polycarbonate system Polymers; Polyester-based polymers such as polyethylene terephthalate and polyethylene naphthalate; Styrene-based polymers such as polystyrene and acrylonitrile-styrene copolymer (AS resin); Polyolefin-based polymers such as polyethylene, polypropylene and ethylene-propylene copolymer; Vinyl chloride Based polymers; amide based polymers such as nylon and aromatic polyamides; imide based polymers; sulfone based polymers; polyether sulf
  • a cellulose-based polymer (hereinafter, also referred to as “cellulose acylate”) represented by triacetyl cellulose can be preferably used.
  • cellulose acylate represented by triacetyl cellulose
  • acrylic polymer examples include polymethyl methacrylate, lactone ring-containing polymers described in paragraphs ⁇ 0017> to ⁇ 0107> of JP 2009-98605 A, and the like.
  • the thickness of the polymer film used for a polarizer protective film etc. is not specifically limited, 40 micrometers or less are preferable from the reasons that thickness of an optical laminated body can be made thin.
  • the lower limit is not particularly limited, but is usually 5 ⁇ m or more.
  • the glass transition temperature of the support is preferably 100 ° C. or less because the superiority of using the composition for photoalignment film of the present invention is high.
  • 20 mg of a sample of the support is placed in a measurement pan with a differential scanning calorimeter (X-DSC 7000 (manufactured by IT Measurement & Control Co., Ltd.)), and this is subjected to velocity under nitrogen retention.
  • the temperature was raised from 30 ° C. to 120 ° C. at 10 ° C./min and held for 15 minutes, and then cooled to 30 ° C. at ⁇ 20 ° C./min. Thereafter, the temperature is raised again from 30 ° C. to 250 ° C., and the temperature at which the baseline starts to change from the low temperature side is taken as the glass transition temperature Tg.
  • the thickness of the support is not particularly limited, but is preferably 1 to 100 ⁇ m, more preferably 5 to 50 ⁇ m, and still more preferably 5 to 20 ⁇ m.
  • the thickness of the said support body means the thickness of the sum total of these thickness, when it has both a polarizer and a polymer film.
  • a cellulose-based polymer or a polyester-based polymer can be preferably used.
  • the thickness of the polymer film is not particularly limited, but is preferably 5 ⁇ m to 100 ⁇ m and more preferably 20 ⁇ m to 90 ⁇ m from the viewpoint of handling at the time of production and the like.
  • the image display apparatus of the present invention is an image display apparatus having the optical laminate of the present invention.
  • the display element used for the image display device of the present invention is not particularly limited, and examples thereof include a liquid crystal cell, an organic electroluminescence (hereinafter abbreviated as “EL”) display panel, a plasma display panel and the like. Among these, a liquid crystal cell and an organic EL display panel are preferable, and a liquid crystal cell is more preferable. That is, the image display device of the present invention is preferably a liquid crystal display device using a liquid crystal cell as a display element, and an organic EL display device using an organic EL display panel as a display element. More preferable.
  • the liquid crystal display device which is an example of the image display device of this invention is a liquid crystal display device which has an optical laminated body of this invention mentioned above, and a liquid crystal cell.
  • the optical laminate of the present invention it is preferable to use the optical laminate of the present invention as a polarizing plate on the front side.
  • the liquid crystal cell constituting the liquid crystal display device will be described in detail.
  • the liquid crystal cell used for the liquid crystal display device is preferably a VA (Vertical Alignment) mode, an OCB (Optically Compensated Bend) mode, an IPS (In-Plane-Switching) mode, or a TN (Twisted Nematic) mode. It is not limited to In the TN mode liquid crystal cell, rod-like liquid crystalline molecules (rod-like liquid crystalline compounds) are substantially horizontally aligned when no voltage is applied, and are further twisted at 60 to 120 °.
  • the TN mode liquid crystal cell is most frequently used as a color TFT liquid crystal display device, and is described in many documents.
  • VA mode liquid crystal cell rod-like liquid crystalline molecules are substantially vertically aligned when no voltage is applied.
  • a narrow definition VA mode liquid crystal cell in which rod-like liquid crystalline molecules are substantially vertically aligned when no voltage is applied and substantially horizontally aligned when a voltage is applied
  • a liquid crystal cell (in multi-domain vertical alignment (MVA) mode) liquid crystal cell (SID 97, Digest of tech. Papers (preliminary paper)) in which the VA mode is multi-domained in order to widen the viewing angle.
  • n-ASM mode Analy symmetric aligned microcell
  • LCD International Liquid Crystal Display
  • PSA Polymer-Sustained Alignment
  • JP-A-2006-215326 and JP-A-2008-538819 The details of these modes are described in detail in JP-A-2006-215326 and JP-A-2008-538819.
  • the liquid crystal cell of the IPS mode rod-like liquid crystalline molecules are aligned substantially parallel to the substrate, and the liquid crystalline molecules respond in a planar manner by the application of an electric field parallel to the substrate surface.
  • black is displayed when no electric field is applied, and the absorption axes of the pair of upper and lower polarizing plates are orthogonal to each other.
  • Japanese Patent Application Laid-Open Nos. 10-54982, 11-202323 and 9-292522 are methods for reducing the leaked light during black display in an oblique direction using an optical compensation sheet to improve the viewing angle. No. 11-133408, 11-305217, 10-307291 and the like.
  • the reaction solution was cooled to room temperature, 250 mL of ethyl acetate and 250 mL of water were added, and the organic phase was separated and washed in order of 240 mL of 1N hydrochloric acid, 240 mL of saturated aqueous sodium bicarbonate and 240 mL of water.
  • the organic phase is dried over magnesium sulphate and the solvent is distilled off.
  • the concentrate was purified by column chromatography to give 55.20 g of Intermediate 2 (yield 62%).
  • a monomer mA-71 forming the above-described repeating unit A-71 was obtained by the same method as the above-described monomer mA-32 except that Intermediate 4 was used in the synthesis of the monomer mA-32.
  • the above-mentioned monomers mC-1 and mC-2 correspond to monomers forming the repeating units C-1 and C-2 shown below, respectively.
  • Example 1 In a flask equipped with a condenser, a thermometer and a stirrer, 5 parts by mass of 2-butanone as a solvent was charged, and the flask was heated to reflux with a nitrogen bath flowing at 5 mL / min.
  • 6 parts by mass of monomer mA-1, 4 parts by mass of monomer mB-2, 1 part by mass of 2,2'-azobis (isobutyronitrile) as a polymerization initiator, and 5 parts of 2-butanone as a solvent The solution which mixed parts was dripped over 3 hours, and it stirred, maintaining reflux condition for another 3 hours.
  • reaction solution was allowed to cool to room temperature, and 30 parts by mass of 2-butanone was added and diluted to obtain a polymer solution of about 20% by mass.
  • the resulting polymer solution is poured into a large excess of methanol to precipitate the polymer, and the collected precipitate is separated by filtration, washed with a large amount of methanol and then air-dried at 50 ° C. for 12 hours, A polymer P-1 having a photoalignable group was obtained.
  • Example 1 except that the above-mentioned respective monomers were used as the monomers forming the repeating unit shown in the following Table 1, and the blending amounts of the respective monomers were changed so as to satisfy “X / (X + Y)” shown in the following Table 1.
  • the polymer was synthesized in the same manner as the polymer P-1 synthesized in
  • composition for photo alignment film 1 part by mass of the polymer P-1 synthesized in Example 1 and 0.05 parts by mass of a thermal acid generator represented by the following structural formula are added to 100 parts by mass of tetrahydrofuran, and a composition for photo alignment film Prepared.
  • a composition for a photoalignment film was prepared by adding 1 part by mass with respect to 100 parts by mass of tetrahydrofuran for each of the polymers synthesized in Examples 2 to 20 and Comparative Examples 1 to 3.
  • the liquid crystal director is significantly disordered and the surface condition is not stable, and the display performance is extremely poor
  • the planar shape is intended to be a state in which there is no defect such as unevenness or alignment failure when the optical laminated body is placed and observed between two polarizing plates arranged in crossed Nicols.
  • a liquid crystal director intends a vector in a direction (alignment main axis) in which the major axis of liquid crystalline molecules is aligned.
  • a photoalignment film using a copolymer having a repeating unit A represented by the formula (1) containing a photoalignable group and a repeating unit B represented by the formula (2) containing a crosslinkable group In each case, it was found that the liquid crystal alignment and the heat resistance were good (Examples 1 to 20). In particular, it was found from the results of Examples 2 to 4 that when R 4 in the above-mentioned formula (1) is an electron donating substituent, the liquid crystalline orientation becomes better. Further, from the results of Examples 5, 14 and 16, it was found that when A in the above-mentioned formula (1) is a linking group containing an alicyclic hydrocarbon group, the liquid crystalline orientation becomes better. .

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Nonlinear Science (AREA)
  • Optics & Photonics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Mathematical Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Liquid Crystal (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polarising Elements (AREA)
  • Laminated Bodies (AREA)

Abstract

L'invention concerne un copolymère photo-alignable qui est susceptible de fabriquer un film photo-aligné présentant une excellente aptitude à l'alignement de cristaux liquides, et un film photo-aligné, un stratifié optique, et un dispositif d'affichage d'image l'utilisant. Le copolymère photo-alignable comprend un motif répétitif A représenté par la formule (1) comprenant un groupe photo-alignable, et un motif répétitif B représenté par la formule (2) comprenant un groupe réticulable. Le film photo-aligné est formé par utilisation d'une composition de film photo-aligné contenant le copolymère photo-alignable. Le stratifié optique comprend le film photo-aligné et une couche optiquement anisotrope formée par utilisation d'une composition de cristal liquide contenant un composé cristal liquide. Le dispositif d'affichage d'image comprend le stratifié optique.
PCT/JP2018/018887 2017-06-30 2018-05-16 Copolymère photo-alignable, fil photo-aligné, stratifié optique et dispositif d'affichage d'image WO2019003682A1 (fr)

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WO2019225632A1 (fr) * 2018-05-25 2019-11-28 富士フイルム株式会社 Copolymère photo-alignable, film de photo-alignement et stratifié optique
WO2020175620A1 (fr) * 2019-02-28 2020-09-03 富士フイルム株式会社 Composition de résine de photo-alignement, film de photo-alignement et stratifié
JPWO2020179864A1 (fr) * 2019-03-07 2020-09-10
WO2021157480A1 (fr) * 2020-02-06 2021-08-12 富士フイルム株式会社 Composé, composition de cristaux liquides, et film à cristaux liquides
WO2022210326A1 (fr) * 2021-03-30 2022-10-06 東ソー株式会社 Résine fluorée, composition, produit photoréticulé et dispositif électronique équipé de celle-ci
WO2024070915A1 (fr) * 2022-09-26 2024-04-04 東ソー株式会社 Résine, composition, produit photoréticulé, motif, et dispositif électronique les comprenant

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JP7033198B2 (ja) 2018-05-25 2022-03-09 富士フイルム株式会社 光配向性共重合体、光配向膜および光学積層体
US11914248B2 (en) 2018-05-25 2024-02-27 Fujifilm Corporation Photo-alignment copolymer, photo-alignment film, and optical laminate
WO2019225632A1 (fr) * 2018-05-25 2019-11-28 富士フイルム株式会社 Copolymère photo-alignable, film de photo-alignement et stratifié optique
JPWO2019225632A1 (ja) * 2018-05-25 2021-05-13 富士フイルム株式会社 光配向性共重合体、光配向膜および光学積層体
WO2020175620A1 (fr) * 2019-02-28 2020-09-03 富士フイルム株式会社 Composition de résine de photo-alignement, film de photo-alignement et stratifié
JPWO2020175620A1 (fr) * 2019-02-28 2020-09-03
KR102525275B1 (ko) 2019-02-28 2023-04-25 후지필름 가부시키가이샤 광배향막용 조성물, 광배향막, 적층체
KR20210114476A (ko) * 2019-02-28 2021-09-23 후지필름 가부시키가이샤 광배향막용 조성물, 광배향막, 적층체
JP7212136B2 (ja) 2019-02-28 2023-01-24 富士フイルム株式会社 光配向膜用組成物、光配向膜、積層体
WO2020179864A1 (fr) * 2019-03-07 2020-09-10 富士フイルム株式会社 Élément de polarisation et dispositif d'affichage d'image
CN113544554A (zh) * 2019-03-07 2021-10-22 富士胶片株式会社 偏振元件及图像显示装置
CN113544554B (zh) * 2019-03-07 2023-06-20 富士胶片株式会社 偏振元件及图像显示装置
JP7317939B2 (ja) 2019-03-07 2023-07-31 富士フイルム株式会社 偏光素子および画像表示装置
JPWO2020179864A1 (fr) * 2019-03-07 2020-09-10
WO2021157480A1 (fr) * 2020-02-06 2021-08-12 富士フイルム株式会社 Composé, composition de cristaux liquides, et film à cristaux liquides
WO2022210326A1 (fr) * 2021-03-30 2022-10-06 東ソー株式会社 Résine fluorée, composition, produit photoréticulé et dispositif électronique équipé de celle-ci
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