WO2014192657A1 - Composition de cristaux liquides polymérisable, film à différence de phase, film graphique à différence de phase et film à cristaux liquides à alignement homogène - Google Patents

Composition de cristaux liquides polymérisable, film à différence de phase, film graphique à différence de phase et film à cristaux liquides à alignement homogène Download PDF

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WO2014192657A1
WO2014192657A1 PCT/JP2014/063698 JP2014063698W WO2014192657A1 WO 2014192657 A1 WO2014192657 A1 WO 2014192657A1 JP 2014063698 W JP2014063698 W JP 2014063698W WO 2014192657 A1 WO2014192657 A1 WO 2014192657A1
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group
liquid crystal
polymerizable
general formula
crystal composition
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Japanese (ja)
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秀俊 中田
桑名　康弘
長谷部　浩史
美花 山本
浩一 延藤
小谷　邦彦
小野　善之
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Dic株式会社
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Priority to JP2014557905A priority Critical patent/JPWO2014192657A1/ja
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    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C09K19/2014—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n-
    • 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
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    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
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    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
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    • C09K19/601—Azoic
    • 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
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    • G02—OPTICS
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    • 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
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    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C09K2019/2078—Ph-COO-Ph-COO-Ph
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    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K2019/528—Surfactants
    • 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
    • G02F1/133631—Birefringent elements, e.g. for optical compensation with a spatial distribution of the retardation value
    • 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
    • G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
    • G02F1/133715—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films by first depositing a monomer
    • 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
    • G02F1/133738—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers for homogeneous alignment
    • 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
    • G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
    • G02F1/133788—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation by light irradiation, e.g. linearly polarised light photo-polymerisation
    • 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
    • G02F2202/00—Materials and properties
    • G02F2202/02—Materials and properties organic material
    • G02F2202/022—Materials and properties organic material polymeric
    • G02F2202/023—Materials and properties organic material polymeric curable

Definitions

  • the present invention relates to a polymerizable liquid crystal composition, a retardation film, a retardation patterning film, and a homogeneous alignment liquid crystal film.
  • the molecular shape is made bulky (made bulky).
  • the polymerizable liquid crystal compound is made asymmetrical, which not only leads to an increase in cost, but also reduces the liquid crystallinity and causes a phenomenon in which the alignment is disturbed when polymerized.
  • Addition of a non-liquid crystalline compound also improves the solubility and storage stability, but the liquid crystallinity deteriorates and the orientation deteriorates.
  • Many chiral compounds are non-liquid crystalline by themselves. Even when these chiral compounds are added, the storage stability is improved, but there is a problem that they can be used only for polymerizable cholesteric liquid crystal materials.
  • the present invention has been made in view of the above circumstances, is a polymerizable liquid crystal composition that is excellent in storage stability and does not cause disorder in alignment when polymerized, and a position formed using the polymerizable liquid crystal composition.
  • An object is to provide a phase difference film, a phase difference patterning film, and a homogeneous alignment (horizontal alignment) liquid crystal film.
  • the first aspect of the present invention includes two or more polymerizable compounds represented by the following general formula (I) and an organic solvent, and m of any two polymerizable compounds among the polymerizable compounds is A polymerizable liquid crystal composition characterized by satisfying
  • 1 or 2 when SA and SB are satisfied, and satisfying SA + SB ⁇ 10.
  • P 1 and P 2 represent a reactive functional group
  • MG represents a mesogenic group or a mesogenic support group
  • two m represent the same numerical value of 1 to 6.
  • the second aspect of the present invention is a retardation film using the polymerizable liquid crystal composition of the first aspect.
  • the third aspect of the present invention is a retardation patterning film using the polymerizable liquid crystal composition of the first aspect.
  • a fourth aspect of the present invention is a homogeneously aligned liquid crystal film using the polymerizable liquid crystal composition of the first aspect.
  • the liquid crystal composition according to the present invention has excellent storage stability and excellent orientation when polymerized. By using this liquid crystal composition, it is possible to produce a retardation film, a retardation patterning film, and a homogeneous alignment liquid crystal film excellent in orientation.
  • the polymerizable liquid crystal composition of the first embodiment of the present invention includes two or more polymerizable compounds (polymerizable liquid crystal compounds) represented by the following general formula (I) and an organic solvent, and among the polymerizable compounds:
  • 1 or 2
  • SA + SB ⁇ 10 is satisfied.
  • P 1 and P 2 represent reactive functional groups
  • MG represents a mesogenic group or a mesogenic supporting group
  • two m represent the same numerical value of 1 to 6.
  • Examples of the reactive functional group represented by P 1 and P 2 in the general formula (I) include the following general formula (II-c), general formula (II-d), and general formula (II-e).
  • P 1 and P 2 in a single molecule are preferably the same.
  • R 21 , R 22, R 23, R 31, R 32, R 33, R 41, R 42 and R Each of 43 independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms, and n represents 0 or 1.
  • R 31 in the general formula (II-d) represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms.
  • the left end of the substituent (reactive functional group) represented by the above general formula is bonded to the carbon atom of the methylene group of the general formula (I).
  • the alkyl group is preferably a linear or branched alkyl group, and more preferably a linear alkyl group.
  • Examples of the reactive group represented by the general formula (II-c), general formula (II-d) or general formula (II-e) include the following reactive groups (P-1) and (P-2). , (P-3), (P-5), (P-6), (P-9), and (P-10). Of these reactive functional groups, the following (P-1) or (P-2) is preferred, and the following (P-1) is more preferred from the viewpoint of enhancing the polymerizability and storage stability.
  • Examples of the mesogenic group or mesogenic support group represented by MG in the general formula (I) include groups represented by the following general formula (II-b).
  • A1, A2 and A3 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran-2,5- Diyl group, 1,3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2,6- Diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 2, 6-naphthylene group, phenanthrene-2,7-diyl group, 9,10-dihydrophenanthrene-2,7-diyl group, 1,
  • the polymerizable liquid crystal composition of this embodiment contains two or more polymerizable compounds represented by the general formula (I).
  • “m” in the general formula (I) representing the first polymerizable compound is “SA”.
  • “m” in the general formula (I) representing the second polymerizable compound is represented as “SB”, at least one set satisfying
  • 1 or 2 and satisfying SA + SB ⁇ 10 There are combinations of two polymerizable compounds.
  • the polymerizable liquid crystal composition of the present embodiment preferably contains 2 to 4 polymerizable compounds represented by the general formula (I), more preferably 2 to 3 types, more preferably 2 types. More preferably.
  • the relationship between SA and SB is established in any combination of the polymerizable compounds. If you do.
  • the polymerizable compound represented by the general formula (I) contained in the polymerizable liquid crystal composition of the present embodiment is preferably a polymerizable compound represented by the following general formula (I-1).
  • Y 21 represents a hydrogen atom or a methyl group.
  • E 21 represents an alkylene group having 1 to 8 carbon atoms.
  • Z 21 and Z 22 are each independently —COO—, —OCO—, —CH 2 CH 2 COO—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 2 —, Or it represents a single bond.
  • X 13 to X 24 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group, and 1 to 3 of X 13 to X 24 Represents a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group.
  • n 1 is 0, 1 or 2. When n 1 is 2 and a plurality of Z 21 are present, they may be the same or different, and when there are a plurality of 1,4-phenylene groups having substituents X17 to X20, they are the same. May be different.
  • Z 21 and Z 22 are preferably each independently —COO— or —OCO—.
  • Preferable specific examples represented by the general formula (I-1) include polymerizable compounds represented by the following general formulas (I-1-1) to (I-1-5).
  • Y 22 represents a hydrogen atom or a methyl group
  • RI 1 to RI 14 each independently represents a fluorine atom, a chlorine atom, a methyl group or a methoxy group.
  • Nr 1 to nr 14 are each independently an integer of 0 to 2, and when nr 1 to nr 14 is 2 and there are a plurality of RI 1 to RI 14, they may be the same or different
  • m represents an integer of 1 to 8.
  • m is preferably from 2 to 7, and more preferably from 3 to 6.
  • the bonding positions of RI 1 to RI 3 and RI 5 to RI 14 are not particularly limited, and nr 1 ⁇ nr 3, if nr 5 ⁇ nr 14 is 1, lateral position is preferred.
  • nr 1 to nr 3 and nr 5 to nr 14 are 2, arbitrary substitution positions can be combined.
  • polymerizable compounds represented by the general formulas (I-1-1) to (I-1-5) those represented by any one of the general formulas (I-1-1) to (I-1-4)
  • a polymerizable compound represented by any one of the general formulas (I-1-2) to (I-1-4) is more preferable.
  • a compound in which Y 22 is a hydrogen atom, RI 4 is a hydrogen atom or a methyl group, and nr 4 is 0 or 1 is preferable.
  • a compound in which Y 22 is a hydrogen atom and nr 5 to nr 11 are 0 is preferable.
  • the polymerizable compound represented by the general formula (I) has three ring structures, if the lateral hydrogen atom of the ring structure is substituted with a substituent, the polymerizable compound
  • the solubility of the compound in the solvent is improved, and the storage stability of the polymerizable liquid crystal composition of this embodiment is improved, which is preferable.
  • the polymerizable liquid crystal composition of the present embodiment includes the above general formulas (I-1-1) to (I-1-4) as the two or more polymerizable compounds represented by the general formula (I). Any two or more polymerizable compounds selected from the group consisting of the polymerizable compounds represented by formula (I) are preferred, and the polymerizable compounds represented by the above general formulas (I-1-2) to (I-1-4) Any two or more polymerizable compounds selected from the group consisting of are more preferred. Further, two or more compounds represented by the above general formula (I-1-2), two or more compounds represented by the above general formula (I-1-3), and the above general formula (I-1-) It is more preferable to contain two or more compounds represented by 4).
  • the total weight of the polymerizable compounds (including monofunctional compounds described later) contained in the polymerizable liquid crystal composition of the present embodiment is 100 parts by weight
  • the total of the polymerizable compounds represented by the general formula (I) The content of is preferably more than 30% by weight and less than 95% by weight, more preferably 50 to 95% by weight, still more preferably 60 to 90% by weight.
  • the total weight of the polymerizable compounds contained in the polymerizable liquid crystal composition is 100 parts by weight
  • the content of each polymerizable compound represented by the general formula (I) is independently preferably more than 30 and 60% by weight or less, more preferably more than 30 and 50% by weight or less, more than 30 and 45% by weight. The following is more preferable. When the content is in these preferred ranges, the storage stability of the polymerizable liquid crystal composition of the present embodiment is further improved.
  • the first polymerizable compound represented by the general formula (I) and the second polymerizable compound when two kinds of polymerizable compounds represented by the general formula (I) are included, the first polymerizable compound represented by the general formula (I) and the second polymerizable compound.
  • the difference in the compound content is preferably 0 to 30 parts by weight, more preferably 0 to 20 parts by weight, and still more preferably 0 to 10 parts by weight.
  • the storage stability of the polymerizable liquid crystal composition of the present embodiment is further improved when the contents of the two polymerizable compounds are equal.
  • the liquid crystal composition of the present embodiment preferably includes a monofunctional compound having one reactive functional group in the molecule.
  • a monofunctional compound By containing a monofunctional compound, the storage stability of the polymerizable liquid crystal composition of the present embodiment is further improved, and the use of polymer base material lamination (for example, retardation film and retardation patterning in the field of liquid crystal display) When used for a film and a homogeneous alignment (horizontal alignment) liquid crystal film, etc., properties such as excellent alignment can be imparted.
  • the substrate on which the solution containing the polymerizable liquid crystal composition of the present invention is applied is a substrate that is usually used for liquid crystal devices, displays, optical components and optical films, and after the application of the polymerizable liquid crystal composition of the present invention.
  • a substrate that is usually used for liquid crystal devices, displays, optical components and optical films, and after the application of the polymerizable liquid crystal composition of the present invention.
  • a material having heat resistance that can withstand heating during the drying of the liquid crystal or during the manufacture of the liquid crystal device.
  • examples of such a substrate include organic materials such as a glass substrate, a metal substrate, a ceramic substrate, and a polymer substrate.
  • the polymer base material is preferable because it can be produced by roll-to-roll and is easy to handle as compared with a glass substrate or the like.
  • the base material (polymer base material) made of a polymer compound has excellent affinity with the polymerizable compound of the present embodiment, and after applying and drying a solution containing the polymerizable compound to the polymer base material,
  • the polymerizable compound of the present embodiment is also suitable for applications that are laminated on a polymer substrate because it is easy to impart excellent orientation.
  • the polymer compound constituting such a preferable polymer substrate include cellulose derivatives, polyolefin-based, polyester-based, polyethylene terephthalate, polycarbonate, polyacrylate-based, polyarylate, polyethersulfone, polyimide, polyphenylene sulfide, and polyphenylene ether. , Nylon, or polystyrene. Particularly preferred are cycloolefin polymer, triacetyl cellulose, and polymethyl methacrylate resin.
  • the substrate may be subjected to an alignment treatment so that the polymerizable liquid crystal composition is easily aligned when the polymerizable liquid crystal composition of the present invention is applied and dried.
  • an alignment treatment in addition to the method of directly rubbing the substrate, an alignment film used in a general liquid crystal device may be applied and the rubbing treatment may be performed.
  • a particularly preferable method is a publicly known method using a photo-alignment film. When the photo-alignment film is used, a patterned retardation film can be produced.
  • the polymerizable compound represented by the following general formula (X) may be referred to as a “monofunctional compound”.
  • Examples of the monofunctional compound include polymerizable compounds represented by the following general formula (X).
  • the polymerizable liquid crystal composition of the present embodiment has a polymerizable compound (monofunctional compound) represented by the following general formula (X) from the viewpoint of improving storage stability and improving alignment when polymerized. It is preferable to include one or more types, and it is more preferable to include two or more types.
  • the polymerizable liquid crystal composition of this embodiment contains two or more monofunctional compounds represented by the general formula (X), m x of any two monofunctional compounds is respectively SAx and SBx. In this case, it is preferable that 1 ⁇
  • P x represents a reactive functional group
  • m x represents an integer of 1 to 8
  • MG represents a mesogenic group or a mesogenic supporting group
  • R 1 represents a hydrogen atom, a halogen atom, A cyano group or an alkyl group having 1 to 25 carbon atoms, wherein one or more hydrogen atoms bonded to the alkyl group may be substituted with a halogen atom or CN, and one CH present in the group;
  • Two groups or two or more CH 2 groups that are not adjacent to each other are independently of each other in a form in which oxygen atoms, sulfur atoms, and oxygen atoms and sulfur atoms are not directly bonded to each other.
  • R 1 is the reactivity Except for the case of a functional group).
  • R 1 is an alkyl group having 1 to 8 carbon atoms (one CH 2 group present in this group or two or more non-adjacent CH 2 groups are independently of each other, And may be replaced by —O—, —CO—, —COO—, —OCO—, —OCOO—, —CH ⁇ CH—, or —C ⁇ C— in a form that is not directly bonded to each other. It is preferable.
  • Examples of the reactive functional group represented by P x in the general formula (X) include a substituent represented by the general formula (II-c), (II-d), or (II-e). And substituents selected from the group.
  • Examples of the mesogenic group or mesogenic supporting group represented by MG in the general formula (X) include the same groups as MG in the general formula (II-b).
  • the polymerizable liquid crystal composition of the present embodiment may contain two or more polymerizable compounds represented by the general formula (X).
  • “m x ” in the general formula (X) representing the first polymerizable compound is changed to “SA x. represents a ", if the formula representing the second polymerizable compound" m x "in (X) represented as" SB x ", 1 ⁇
  • polymerizable liquid crystal composition of the present embodiment it is preferable to contain 2 to 4 types of polymerizable compounds represented by the general formula (X), more preferably 2 to 3 types, and more preferably 2 types. More preferably.
  • the relationship between SA and SB is established in any combination of the polymerizable compounds. If you do.
  • Examples of the two or more polymerizable compounds represented by the general formula (X) contained in the polymerizable liquid crystal composition of the present embodiment include the following general formulas (X-1) to (X-4) and the following general formulas: Any two or more polymerizable compounds selected from the group consisting of polymerizable compounds represented by (X-31) to (X-32) are preferred, Two or more compounds represented by the following general formula (X-1), two or more compounds represented by the following general formula (X-2), and a compound represented by the following general formula (X-3) Two or more compounds, two or more compounds represented by the following general formula (X-4), two or more compounds represented by the following general formula (X-31), or the following general formula (X-32) It is more preferable that 2 or more types of compounds represented by these are contained.
  • Y 21 , Y 31 , Y 41 , and Y 51 each independently represent a hydrogen atom or a methyl group.
  • E 21 , E 31 , E 41 , and E 51 each independently represent an alkylene group having 1 to 8 carbon atoms.
  • Z 21 , Z 22 , Z 31 , Z 32 , Z 41 , Z 42 , Z 51 , and Z 52 are each independently —COO—, —OCO—, —C ⁇ C—, —CH ⁇ CH—. , —CH 2 —CH 2 —, —CH ⁇ CH—COO—, —OCO—CH ⁇ CH—, or a single bond.
  • X 13 to X 24 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group, and 1 to 3 of X 13 to X 24 Preferably represents a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group.
  • X 25 to X 39 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group, and 1 to 3 of X 25 to X 39 Preferably represents a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group.
  • X 40 to X 53 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group, and 1 to 3 of X 40 to X 53 Preferably represents a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group.
  • X 54 to X 68 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group, and 1 to 3 of X 54 to X 68 Preferably represents a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group.
  • R 2 to R 5 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or an alkyl group having 1 to 15 carbon atoms, and one or two or more present in the alkyl group
  • the methylene group is substituted with an oxygen atom (—O—), —CO—, —OCO—, —COO—, —C ⁇ C—, or —CH ⁇ CH—, assuming that the oxygen atoms are not directly bonded to each other. (Except when R 2 to R 5 are the reactive functional group).
  • Z 21 , Z 22 , Z 31 , Z 32 , Z 41 , Z 42 , Z 51 , and Z 52 are each independently a single bond, —COO—, or —OCO—, and R 2 to R More preferably, each of 5 is independently an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms.
  • polymerizable compounds represented by the general formulas (X-1) to (X-4) polymerizable compounds represented by the following general formulas (X-5) to (X-21) Is mentioned.
  • Y 22 represents a hydrogen atom or a methyl group
  • R 21 represents an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms.
  • R 23 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms,
  • R 22 represents a fluorine atom, a chlorine atom, a methyl group, or a methoxy group
  • n 21 represents an integer of 1 to 8.
  • Y 61 and Y 71 each independently represent a hydrogen atom or a methyl group.
  • E 61 and E 71 each independently represents an alkylene group having 1 to 8 carbon atoms.
  • Z 61 represents —COO—, —OCO—, or a single bond.
  • Z 62 represents —C ⁇ C—.
  • Z 71 and Z 72 each independently represent —COO—, —OCO—, or a single bond.
  • X 71 to X 82 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group, and 1 to 3 of X 71 to X 82 Preferably represents a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group.
  • X 85 to X 96 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group.
  • R 7 to R 8 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or an alkyl group having 1 to 15 carbon atoms, and one or two or more present in the alkyl group
  • the methylene group may be substituted with an oxygen atom (—O—), —CO—, —OCO—, —COO—, or —CH ⁇ CH—, provided that the oxygen atoms are not directly bonded to each other (provided that R 7 to R 8 are the reactive functional groups).
  • Z 61 is —COO— or —OCO—
  • Z 62 is —C ⁇ C—
  • R 7 has 1 to 10 carbon atoms.
  • a compound having an alkyl group or an alkoxy group having 1 to 10 carbon atoms is more preferred.
  • Z 71 is —COO— or —OCO—
  • Z 72 is a single bond
  • R 8 is an alkyl group having 1 to 10 carbon atoms.
  • a compound which is an alkoxy group having 1 to 10 carbon atoms is more preferable.
  • polymerizable compounds represented by the general formulas (X-31) to (X-32) include polymerizable compounds represented by the following general formulas (X-33) to (X-44). Can be mentioned.
  • Y 62 and Y 72 represent a hydrogen atom or a methyl group
  • R 61 and R 63 represent an alkyl group having 1 to 10 carbon atoms or a carbon atom number of 1 to 10 represents an alkoxy group
  • R 62 and R 64 represent a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group or a methoxy group
  • n 61 represents an integer of 1 to 8.
  • polymerizable compounds represented by the general formulas (X-33) to (X-44) those represented by the general formulas (X-33), (X-34), (X-39) and (X-40) are preferred.
  • the polymerizable compound represented by the general formula (X) is preferably a compound represented by the following general formula (X-50).
  • Y 82 represents a hydrogen atom or a methyl group
  • n 81 is an integer of 0 to 8
  • n 82 is 1 or 2
  • Z 83 is —COO— or —OCO—. , —C ⁇ C—, or a single bond
  • a 83 represents a 1,4-phenylene group or a 1,4-cyclohexylene group
  • R 83 represents an alkyl group having 1 to 5 carbon atoms or an alkoxyl group.
  • Z 83 is preferably a single bond
  • a 83 is a 1,4-phenylene group
  • R 83 is a cyano group, a methyl group, an ethyl group, or a methoxy group.
  • n 82 is 2 and a plurality of Z 83 are present, they may be the same or different, and when a plurality of A 83 are present, they may be the same or different.
  • the compound of the general formula (X-50) is an effective compound when it is desired to reduce the viscosity. However, if too much is added, the orientation deteriorates.
  • the addition amount is preferably 0 to 30% by mass, and more preferably 0 to 10% by mass, when the total amount of the polymerizable compound is 100% by mass.
  • the polymerizable compound represented by the general formula (X) has three ring structures
  • the lateral hydrogen atom of the ring structure is substituted with a substituent
  • the polymerizable compound The solubility of the compound in the solvent is improved, and the storage stability of the polymerizable liquid crystal composition of this embodiment is improved, which is preferable.
  • the polymerizable liquid crystal composition of the present embodiment contains two or more polymerizable compounds represented by the general formula (X-5), and the polymerizable property represented by the general formula (X-12).
  • the total weight of the polymerizable compounds (including the bifunctional compound described above) contained in the polymerizable liquid crystal composition of the present embodiment is 100 parts by weight
  • the content of is preferably 5 parts by weight or more and less than 70 parts by weight, more preferably 5 to 50 parts by weight, still more preferably 10 to 40 parts by weight.
  • the total weight of the polymerizable compounds contained in the polymerizable liquid crystal composition is 100 parts by weight
  • the content of each polymerizable compound represented by the general formula (X) is preferably 5 to 70% by weight, more preferably 5 to 50% by weight, and still more preferably 10 to 40% by weight. When the content is in these preferred ranges, the storage stability of the polymerizable liquid crystal composition of the present embodiment is further improved.
  • the first polymerizable compound represented by the general formula (X) and the second polymerizable compound when two kinds of polymerizable compounds represented by the general formula (X) are included, the first polymerizable compound represented by the general formula (X) and the second polymerizable compound.
  • the difference in the compound content is preferably 0 to 30 parts by weight, more preferably 0 to 20 parts by weight, and still more preferably 0 to 10 parts by weight.
  • the storage stability of the polymerizable liquid crystal composition of the present embodiment is further improved when the contents of the two polymerizable compounds are equal.
  • the total content of the bifunctional compound represented by the general formula (I) and the monofunctional compound represented by the general formula (X) with respect to the total weight of the polymerizable liquid crystal composition of the present embodiment is 5 to 50 wt% is preferable, 10 to 40 wt% is more preferable, and 20 to 40 wt% is still more preferable.
  • the lower limit is determined from the viewpoint of improving the coating property of the composition on the substrate, and the upper limit is determined from the viewpoint of increasing the storage stability of the composition.
  • the polymerizable composition solution of the present invention may contain a polymerizable discotic liquid crystal compound in addition to the bifunctional compound represented by the general formula (I).
  • the polymerizable discotic liquid crystal compound used in the present invention preferably has one or more polymerizable functional groups. Examples of such compounds include polymerizability as described in JP-A-7-281028, JP-A-7-287120, JP-A-7-333431, and JP-A-8-27284. Examples include discotic liquid crystal compounds.
  • the compounding quantity of a polymerizable discotic liquid crystal compound can be suitably adjusted with a compound.
  • Examples of the general formula of the polymerizable discotic liquid crystal compound include general formulas (4-1) to (4-3), but are not limited to the following general formula.
  • Sp 4 represents an alkylene group having 0 to 18 carbon atoms, and the alkylene group is substituted with one or more halogen atoms, CN group, or an alkyl group having 1 to 8 carbon atoms having a polymerizable functional group.
  • a 4 represents 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran-2,5-diyl group, 1,3-dioxane-2,5-diyl group, tetrahydro Thiopyran-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2,6-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5 -Diyl group, pyrazine-2,5-diyl group, thiophene-2,5-diyl group-, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene- 2,7-diyl group, 9,10-dihydrophenanthrene-2,7-
  • P 4a represents a polymerizable functional group
  • Sp 3a represents the same meaning as Sp 1
  • P 4a preferably represents a substituent selected from the polymerizable groups represented by the following formulas (P-1) to (P-20).
  • the formula (P-1) or the formulas (P-2), (P-7), (P-12), (P-13) ) are preferred, and formulas (P-1), (P-7), and (P-12) are more preferred.
  • Specific examples of the polymerizable discotic liquid crystal compound include compounds (4-4) to (4-8), but are not limited to the following compounds.
  • q represents an integer of 1 to 18.
  • Organic solvent constituting the polymerizable liquid crystal composition of the present embodiment is not particularly limited as long as it can dissolve the general formula (I), but is a solvent that can be evaporated at a temperature of 100 ° C. or lower and dried. It is preferable that it is present, and it is preferable that the substrate used is not eroded.
  • solvents examples include aromatic hydrocarbons such as toluene, xylene, cumene, and mesitylene, ester solvents such as methyl acetate, ethyl acetate, propyl acetate, and butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclohexane, and the like.
  • Ketone solvents such as pentanone, ether solvents such as tetrahydrofuran, 1,2-dimethoxyethane and anisole, amide solvents such as N, N-dimethylformamide and N-methyl-2-pyrrolidone, propylene glycol monomethyl ether acetate, Examples include diethylene glycol monomethyl ether acetate, ⁇ -butyrolactone, and chlorobenzene. These organic solvents can be used alone or in combination of two or more.
  • the solubility of the polymerizable compound represented by the general formula (I) is excellent, the orientation of the film obtained by polymerizing the composition is also excellent, and it is easy to dry at 100 ° C. or less. More preferred are toluene, ethyl acetate, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, propylene glycol monomethyl ether acetate, and N-methyl-2-pyrrolidone and combinations thereof.
  • the content of the organic solvent relative to the total weight of the polymerizable liquid crystal composition of the present embodiment is preferably a content that facilitates application of the composition to a substrate, for example, 40 to 90% by weight. Preferably, it is 50 to 80% by weight.
  • the polymerizable liquid crystal composition of the present embodiment preferably contains at least one polymerization initiator.
  • the polymerization initiator is a useful compound for efficiently polymerizing the polymerizable liquid crystal composition.
  • a photopolymerization initiator is preferable, and specifically, the following compounds are preferable. Irgacure 651, Irgacure 184, Irgacure 907, Irgacure 127, Irgacure 369, Irgacure 379, Irgacure 819, Irgacure OXE01, Irgacure OXE02, Lucyrin TPO, Darocur 1173 manufactured by BASF.
  • These polymerization initiators may be used alone or in combination of two or more, and a sensitizer or the like may be added.
  • the content of the polymerization initiator with respect to the total weight of the polymerizable liquid crystal composition of the present embodiment is, for example, preferably 0.1 to 10% by weight, more preferably 1 to 7% by weight, and still more preferably 3 to 7% by weight. .
  • the polymerizable liquid crystal composition of this embodiment preferably contains a surfactant or a compound having a repeating unit represented by the following general formula (3) and having a weight average molecular weight of 100 or more.
  • R 11 , R 12 , R 13 and R 14 each independently represents a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and one or more hydrogen atoms in the hydrocarbon group
  • the atom may be substituted with a halogen atom.
  • the surfactant and the compound represented by the general formula (3) impart an effect of reducing the tilt angle of the liquid crystal compound at the air interface.
  • surfactant examples include alkyl carboxylates, alkyl phosphates, alkyl sulfonates, fluoroalkyl carboxylates, fluoroalkyl phosphates, fluoroalkyl sulfonates, polyoxyethylene derivatives, fluoroalkylethylene oxide derivatives, Examples include polyethylene glycol derivatives, alkyl ammonium salts, fluoroalkyl ammonium salts, silicone derivatives, and the like. Of these, fluorine-containing surfactants and silicone derivatives are particularly preferable.
  • MEGAFAC F-110 “MEGAFACCF-113”, “MEGAFAC F-120”, “MEGAFAC F-812”, “MEGAFAC F-142D”, “MEGAFAC F-144D”, “MEGAFAC F-” 150 “,” MEGAFAC F-171 “,” MEGAFACF-173 “,” MEGAFAC F-177 “,” MEGAFAC F-183 “,” MEGAFAC F-195 “,” MEGAFAC F-824 “,” MEGAFAC F-833 “ , “MEGAFAC F-114”, “MEGAFAC F-410”, “MEGAFAC F-493”, “MEGAFAC F-494”, “MEGAFAC F-443”, “MEGAFAC F-444”, “MEGAFAC F-445”, “ME “GAFAC F-446”, “MEGAFAC F-470”, “MEGAFAC F-471”, “MEGAFAC F-474”, “MEGAFAC F-475”, “MEGAFAC F-477”, “MEGAFAC F-110
  • the weight average molecular weight of the compound represented by the general formula (3) is preferably 200 to 100,000, more preferably 300 to 10,000, and further preferably 500 to 5,000.
  • the surfactant and the compound represented by the general formula (3) may be used singly or in combination of two or more. Moreover, you may use combining the said surfactant and the compound represented by the said General formula (3).
  • the total content of the surfactant and the compound represented by the general formula (3) with respect to the total weight of the polymerizable liquid crystal composition of the present embodiment is preferably 0.01 to 1% by weight, More preferably, it is 0.05 to 0.6% by weight.
  • a chain transfer agent is preferably added to the polymerizable liquid crystal composition of the present embodiment as another component in order to further improve the adhesion to the substrate.
  • the chain transfer agent is preferably a thiol compound, more preferably a monothiol, dithiol, trithiol, or tetrathiol compound, and even more preferably a trithiol compound.
  • compounds represented by the following general formulas (5-1) to (5-12) are preferable.
  • the content of these thiol compounds is preferably 0.5 to 5.0% by weight, more preferably 1.0 to 3.0% by weight, based on the total weight of the composition. .
  • R 66 is a carbon Represents an alkylene group having 2 to 18 atoms, and one or more methylene groups in the alkylene group are oxygen atoms, sulfur atoms, —CO—, —OCO on the assumption that an oxygen atom and a sulfur atom are not directly bonded to each other. It may be substituted with —, —COO—, or —CH ⁇ CH—.
  • a polymerization inhibitor an antioxidant or the like in order to improve storage stability.
  • examples of such compounds include hydroquinone derivatives and hindered phenol antioxidants. More specifically, p-methoxyphenol, IRGANOX1010, IRGANOX1035, IRGANOX1076, IRGANOX1098, IRGANOX1135, IRGANOX1325, IRGANOX1520, IRGANOX2457, IRGANOX3957, IRGANOX3590, IRGANOX3590, IRGANOX3590, IRGANOX3590, IRGANOX3590, IRGANOX3590, IRGANOX3590, IRGANOX3590, IRGANOX3590, IRGANOX3590, IRGANOX3590, IRGANOX3590, IRGANOX3590, IRGANOX3590, IRGANOX3590, IRGANOX3590, IRGANOX
  • the content of the polymerization inhibitor and the antioxidant is preferably 0.01 to 1.0% by mass, and 0.05 to 0.2% by mass with respect to the total weight of the composition. It is more preferable.
  • a non-polymerizable liquid crystal compound, a non-liquid crystal polymerizable compound, or the like can be added as necessary.
  • the content of these compounds is preferably 20% by weight or less, more preferably 10% by weight or less, and still more preferably 5% by weight or less based on the total weight of the composition.
  • optical anisotropic body manufacturing method (Optical anisotropic)
  • the optical anisotropic body of the present invention is obtained by sequentially laminating a base material, an orientation film as necessary, and a polymer of a polymerizable composition solution.
  • a base material, an orientation film as necessary, and a polymerization composition solution of a polymerizable composition solution are sequentially laminated, and an orientation film and a polymerizable composition that may be different from the above or above as necessary.
  • a product solution is sequentially laminated.
  • an alignment film and a polymerizable composition solution that may be different from the above or the above may be sequentially laminated thereon as necessary.
  • the base material used for the optical anisotropic body of the present invention is a base material usually used for liquid crystal devices, displays, optical elements, optical components, colorants, security markings, laser emission members, and optical films.
  • the material is not particularly limited as long as it is a material having heat resistance capable of withstanding heating during drying after the application of the polymerizable composition solution of the present invention.
  • Examples of such a substrate include organic materials such as a glass substrate, a metal substrate, a ceramic substrate, and a plastic substrate.
  • the substrate when the substrate is an organic material, examples thereof include cellulose derivatives, polyolefins, polyesters, polyolefins, polycarbonates, polyacrylates, polyarylates, polyether sulfones, polyimides, polyphenylene sulfides, polyphenylene ethers, nylons, and polystyrenes.
  • plastic substrates such as polyester, polystyrene, polyolefin, cellulose derivatives, polyarylate, and polycarbonate are preferable.
  • surface treatment of these substrates may be performed.
  • the surface treatment examples include ozone treatment, plasma treatment, corona treatment, silane coupling treatment, and the like.
  • an organic thin film, an inorganic oxide thin film, a metal thin film, etc. are provided on the surface of the substrate by a method such as vapor deposition, or in order to add optical added value.
  • the material may be a pickup lens, a rod lens, an optical disk, a retardation film, a light diffusion film, a color filter, or the like. Among these, a pickup lens, a retardation film, a light diffusion film, and a color filter that have higher added value are preferable.
  • the alignment treatment include stretching treatment, rubbing treatment, polarized ultraviolet visible light irradiation treatment, ion beam treatment, and the like.
  • the alignment film a known and conventional alignment film is used.
  • alignment films include polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene ether, polyarylate, polyethylene terephthalate, polyether sulfone, epoxy resin, epoxy acrylate resin, acrylic resin, coumarin compound, chalcone.
  • the compound examples include compounds, cinnamate compounds, fulgide compounds, anthraquinone compounds, azo compounds, and arylethene compounds.
  • the compound subjected to the alignment treatment by rubbing is preferably an alignment treatment or a compound in which crystallization of the material is promoted by inserting a heating step after the alignment treatment.
  • an applicator method As an application method for obtaining the optical anisotropic body of the present invention, an applicator method, a bar coating method, a spin coating method, a gravure printing method, a flexographic printing method, an ink jet method, a die coating method, a cap coating method, dipping, etc. are known. Conventional methods can be performed. The polymerizable composition solution is applied and then dried.
  • the polymerization treatment of the dried polymerizable composition is generally performed by irradiation with light such as ultraviolet rays or heating in a state where the polymerizable compound represented by the general formula (1) in the polymerizable composition is planarly aligned.
  • light irradiation specifically, it is preferable to irradiate ultraviolet light having a wavelength of 390 nm or less, and most preferable to irradiate light having a wavelength of 250 to 370 nm.
  • the polymerizable composition causes decomposition or the like due to ultraviolet light of 390 nm or less, it may be preferable to perform polymerization treatment with ultraviolet light of 390 nm or more. This light is preferably diffused light and unpolarized light.
  • the retardation film of the present invention is prepared in the same manner as the optical anisotropic body of the present invention.
  • the polymerizable compound represented by the general formula (1) in the polymerizable composition is polymerized in a planar alignment state, a retardation film having in-plane birefringence with respect to the substrate is obtained.
  • the retardation film can be used as a homogeneous liquid crystal film.
  • the polymerizable compound represented by the general formula (1) in the polymerizable composition and the polymerizable chiral compound are polymerized in a planar alignment state, the birefringence is out of plane with respect to the substrate. A phase difference film is obtained.
  • the polymerizable compound represented by the general formula (1) in the polymerizable composition containing a polymerizable discotic compound is polymerized in a planar orientation state, it is compounded both in-plane and out-of-plane with respect to the substrate.
  • a retardation film having refractive properties can be obtained.
  • the substrate has a retardation
  • a retardation film having birefringence obtained by adding the birefringence of the substrate and the birefringence of the retardation film of the present invention can be obtained.
  • the birefringence of the base material and the birefringence of the retardation film may be in the same direction or different directions in the plane of the base material.
  • the liquid crystal device, the display, the optical element, the optical component, the colorant, the marking for security, the member for laser emission, the optical film, and the compensation film are applied in a form suitable for the application.
  • the retardation patterning film of the present invention is obtained by sequentially laminating a base material, an alignment film, and a polymer of a polymerizable composition solution in the same manner as the optical anisotropic body of the present invention. Are patterned so as to obtain different phase differences.
  • the patterning may be in different directions, such as linear patterning, lattice patterning, circular patterning, polygonal patterning, and the like.
  • the liquid crystal device, display, optical element, optical component, colorant, security marking, laser emission member, optical film, compensation film, and the like are used.
  • an alignment film is provided on the substrate, and the polymerizable composition solution of the present invention is applied and dried during the alignment treatment so that the polymerizable composition is patterned and aligned.
  • an alignment treatment include a fine rubbing treatment, a polarized ultraviolet visible light irradiation treatment through a photomask, and a fine shape processing treatment.
  • the alignment film known and conventional ones are used.
  • Such alignment films include polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene ether, polyarylate, polyethylene terephthalate, polyether sulfone, epoxy resin, epoxy acrylate resin, acrylic resin, coumarin compound, chalcone.
  • the compound include compounds, cinnamate compounds, fulgide compounds, anthraquinone compounds, azo compounds, and arylethene compounds.
  • the compound subjected to the alignment treatment by fine rubbing is preferably an alignment treatment or a compound in which crystallization of the material is promoted by adding a heating step after the alignment treatment.
  • homogeneous alignment is achieved by appropriately selecting a polymerizable liquid crystal compound and adjusting the amount of the surfactant or the compound having a repeating unit represented by the general formula (3) and having a weight average molecular weight of 100 or more. can do.
  • a UCL composition was prepared by mixing each compound at the ratio shown in the following table. Each additive was further added to the UCL solution in which 30 parts by weight of the UCL composition and 70 parts by weight of each solvent were mixed to prepare sample solutions for the examples and comparative examples.
  • composition A After dissolving 0.5 parts by weight of the compound represented by the above formula (A) in 49.5 parts by weight of 2- (2-ethoxyethoxy) ethanol, 49 parts by weight of 2-butoxyethanol is added to form a photo-alignment film. A solution of composition A was obtained. This solution was filtered through a 0.45 ⁇ m membrane filter to obtain a composition (A-1) for photo-alignment films.
  • the composition for photo-alignment film (A-1) was applied onto a film made of an 80 ⁇ m triacetyl cellulose derivative as a base material with a bar coater and dried at 80 ° C. for 2 minutes. The dry film thickness at this time was 15 nm.
  • the ultra-high pressure mercury lamp is passed through a wavelength cut filter, a band-pass filter, and a polarizing filter, and visible ultraviolet light having a wavelength of around 365 nm (irradiation intensity: 20 mW / cm 2 ) is applied to the substrate as linearly polarized parallel light.
  • the photo-alignment film was obtained by irradiating from the vertical direction. The irradiation amount was 100 mJ / cm 2 .
  • the polymerizable liquid crystal composition according to the present invention is widely applicable in the field of liquid crystal displays.

Abstract

La présente invention concerne une composition de cristaux liquides polymérisable qui présente une excellente stabilité au stockage, et dans laquelle aucune désorganisation de l'alignement ne se produit à la polymérisation ; et un film à différence de phase, un film graphique à différence de phase et un film à cristaux liquides à alignement homogène (alignement horizontal) qui sont formés à l'aide de la composition de cristaux liquides polymérisable. La composition de cristaux liquides polymérisable est caractérisée en ce que : elle comprend deux composés polymérisables ou plus représentés par la formule générale (I), et un solvant organique ; et elle satisfait |SA-SB|=1,2, et SA+SB ≤ 10, SA et SB étant respectivement un nombre m de l'un quelconque de deux composés polymérisables choisis parmi les composés polymérisables (dans la formule, P1 et P2 représentent des groupes fonctionnels réactifs, MG représente un groupe mésogénique ou un groupe supportant la mésogénité et les deux m représentent la même valeur numérique de 1 à 6).
PCT/JP2014/063698 2013-05-29 2014-05-23 Composition de cristaux liquides polymérisable, film à différence de phase, film graphique à différence de phase et film à cristaux liquides à alignement homogène WO2014192657A1 (fr)

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US10787608B2 (en) 2016-05-18 2020-09-29 Jnc Corporation Liquid crystal display device including liquid crystal medium containing low molecular weight polar compound for homogeneously aligning liquid crystal medium
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WO2017199513A1 (fr) * 2016-05-18 2017-11-23 Jnc株式会社 Composé polaire à faible poids moléculaire destiné à l'alignement homogène d'un milieu à cristaux liquides, et milieu à cristaux liquides le contenant
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US10787608B2 (en) 2016-05-18 2020-09-29 Jnc Corporation Liquid crystal display device including liquid crystal medium containing low molecular weight polar compound for homogeneously aligning liquid crystal medium
US10865344B2 (en) 2016-05-18 2020-12-15 Jnc Corporation Low molecular weight polar compound for homogeneously aligning liquid crystal medium, and liquid crystal medium containing same
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JP6414367B2 (ja) * 2016-06-28 2018-10-31 Dic株式会社 重合性液晶組成物
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CN113260909A (zh) * 2018-12-27 2021-08-13 日产化学株式会社 液晶取向处理剂、液晶取向膜以及液晶显示元件

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