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WO2007100136A1 - Composition de cristaux liquides - Google Patents

Composition de cristaux liquides Download PDF

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Publication number
WO2007100136A1
WO2007100136A1 PCT/JP2007/054166 JP2007054166W WO2007100136A1 WO 2007100136 A1 WO2007100136 A1 WO 2007100136A1 JP 2007054166 W JP2007054166 W JP 2007054166W WO 2007100136 A1 WO2007100136 A1 WO 2007100136A1
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group
molecule
composition according
substituted
liquid crystalline
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Japanese (ja)
Inventor
Takao Nakajima
Masatoshi Kidowaki
Jun Araki
Toshiyuki Kataoka
Kohzo Ito
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University of Tokyo NUC
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University of Tokyo NUC
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Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K19/24—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing nitrogen-to-nitrogen bonds
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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
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
    • C09K19/22—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 nitrogen atoms as chain links, e.g. Schiff bases
    • C—CHEMISTRY; METALLURGY
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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
    • C09K19/24—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing nitrogen-to-nitrogen bonds
    • C09K19/26—Azoxy compounds
    • C—CHEMISTRY; METALLURGY
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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
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
    • C09K19/3458—Uncondensed pyrimidines

Definitions

  • the present invention relates to a liquid crystal composition having a polymouth taxane and a liquid crystal substance, and a method for producing the same.
  • a wide variety of liquid crystals are used in recent electrical appliances, particularly displays.
  • portable terminals such as notebook computers, PDAs, and mobile phones are required to be further miniaturized, and as one form, development of, for example, wearable computers is also required. Therefore, a flexible computer display or the like is required to have flexibility and flexibility.
  • Patent Document 1 discloses a cross-linked poly-ortaxane formed by crosslinking a plurality of poly-ortaxanes in which blocking groups are arranged so that a cyclic molecule is not eliminated.
  • This cross-linked poly (taxane) taxane has viscoelasticity caused by the movement of cyclic molecules. For this reason, even if tension is applied to the cross-linked polymouth taxane, the tension can be uniformly dispersed in the cross-linked polymouth taxane by this action.
  • Patent Document 1 Japanese Patent No. 3475252.
  • an object of the present invention is to meet the above needs.
  • an object of the present invention is to provide a liquid crystal material having flexibility and Z or flexibility, and a method for producing the same.
  • the present inventors have found that a group that exhibits compatibility with a liquid crystalline substance in a cyclic molecule, for example, a poly (oral taxane) having a mesogenic group and a liquid crystalline substance. It has been found that a composition having the composition can solve the above problems. Specifically, the present inventors have found the following invention.
  • a group cathode group that exhibits compatibility with a liquid crystal substance is preferable.
  • the mesogenic group is A—X—B—C—Y— (wherein A and B are 6-membered rings, C is a single bond or a linear group, X And Y is a linking group).
  • the 6-membered rings of A and B are each independently a saturated or unsaturated homocyclic or heterocyclic ring, preferably a substituted ring. It should be a good benzene ring. More preferably, A is a P-cyanophenol group and B is an unsubstituted benzene ring.
  • C has 0 to 100 elements, preferably 0 to 70 elements, more preferably 0 to 30 elements, forming a straight chain of the C. Is good.
  • C may contain O or a benzene ring in a straight chain.
  • the “number of elements forming a straight chain” of the benzene ring is four in the present application for convenience.
  • C is a linear alkyl chain or a linear alkyl ether chain! /.
  • Y represents a single bond, O—, —CO—, 1 CO—O, 1 O—CO, 1 NH—CO, 1 CO—NH, 1 NH—CO—O— And one group power consisting of O—CO—NH— should be selected.
  • Y is selected from the group consisting of CO—O, 1 O, 1 NH—CO—O— and 1 O—CO 2, more preferably CO—O.
  • A—X—B is D—1 to D—20.
  • R 1 to R 2G are each independently a cyano group, F, Cl, a C 1-20, preferably a C 1-15 (preferably linear) alkyl group, a C 1-20, preferably C1-C15 (preferably linear) alkoxy group, C1-C20, preferably C1-C15 (preferably linear) alkylcarboxyl group or alkyloxycarbol group , A fluorocarbon having 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms (preferably linear), or a -tro group.
  • A—X—B— is D—1 to D—14, D—19 or D—20, preferably D—2 to D—14, D—19 or D—20, more preferably D—4.
  • a group that exhibits compatibility with a liquid crystalline substance for example, a mesogenic group is represented by the following formulas 1 to 3 (wherein n is 1 to M is an integer of 1 to 10, R 21 , R 23 and R 25 are each independently 0 to 5 substituents; R 22 , R 24 and R 26 are Each independently represents 0 to 4 substituents)! /, Which is a misalignment! /.
  • R 22 is preferably 0.
  • the biphenyl substituent is represented by the formula 2, n is an integer of 2 to 10, preferably an integer of 3 to 8, particularly 5, and R 23 is 1. , P-position and a cyano group, and R 24 is preferably zero.
  • the biphenyl substituent is represented by the formula 3, m is an integer of 1 to 5, preferably an integer of 2 to 4, particularly 2, and R 25 is 1. , P-position and a cyano group, and R 26 is preferably 0.
  • a liquid crystalline substance In any one of the above items ⁇ 1> to ⁇ 12>, a liquid crystalline substance, an azo compound group, an azoxy compound group, a substituted group of P-substituted benzoic acid esters, a cholesteryl ester, P -Substituted biphenyls, substituted groups of cyclohexanecarboxylic acid esters, Schiff bases, P-substituted cyclohexyls -P-substituted files, 2-phenyl substituted-1,3-dioxanes It is preferable that at least one kind is selected from the group of substitutional groups and the group power that can also be ferrulemimidines.
  • Liquid Crystals force formula C 1, C -2, E, F- 1, F- 2, G or H (wherein, X 5 to X 8 And X 1G to X 19 are each independently a cyan group, F, Cl, a carbon number of 1 to 20, preferably a carbon number of 1 to 15 (preferably linear), an alkyl group (preferably linear), carbon An alkoxy group having 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms (preferably linear), 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms (preferably linear) A compound represented by an alkylcarboxyl group or an alkyloxycarbol group, a carbon number of 1 to 20, preferably a carbon number of 1 to 15 (preferably linear) fluorocarbon, or a -tro group). There must be! /.
  • liquid crystalline substance force is present in the crosslinked polyrotaxane.
  • At least a part of the polyoral taxane is a crosslinked polyoral taxane that is crosslinked with each other.
  • the linear molecule may be polybulalcol, polybulurpyrrolidone, poly (meth) acrylic acid, cellulosic resin (carboxy methinorescenellose, Hydroxyethinoresenololose, hydroxypropenoresenorelose, etc.), polyacrylamide, polyethylene oxide, polyethylene glycol, polypropylene glycol, polyvurecetal resin, polybutymethyl ether, polyamine, polyethylenimine, casein, Gelatin, starch, etc.
  • polyethylene, polypropylene, and other polyolefin resins such as polyolefin resins, polyester resins, polyvinyl chloride resins, polystyrene Or Atari Mouth-Trill One Still Acrylic resins such as polystyrene resins such as polyethylene resins, polymethylmethallate and (meth) acrylic acid ester copolymers, acrylonitrile-methylacrylate copolymer resins, polycarbonate resins, polyurethane resins Fats, salts, butyl acetates, copolymerized butter, polyvinyl butyral, etc .; and derivatives or modified products thereof, polyisobutylene, polytetrahydrofuran, polyaniline, acrylonitrile-butadiene styrene Copolymers (ABS resin), polyamides such as nylon, polyimides, polygens such as polyisoprene and polybutadiene, polysiloxanes such
  • the linear molecule has a molecular weight of 00 or more, preferably 1000 or more, more preferably 2000 or more.
  • the blocking group is dinitrophenol group, cyclodextrin, adamantane group, trityl group, fluorescein, pyrene, substituted Benzenes
  • Substituents include, but are not limited to, alkyl, alkyloxy, hydroxy, halogen, sheared sulfonyl, carboxyl, amino-substituted phenyl, etc. There are one or more substituents.
  • polynuclear aromatics that may be substituted include, but are not limited to, the same as above. One or more substituents may be present).
  • steroids include, but are not limited to, the same as above. One or more substituents may be present).
  • dinitrophenol groups, cyclodextrins, adamantane groups, trityl groups, fluoresceins, and pyrenes are preferably selected, more preferably adamantane groups or trityl groups. Is good.
  • the cyclic molecule may be substituted. It is a cyclodextrin molecule! /
  • a cyclic molecule may be substituted, and the cyclodextrin molecule may be ⁇ -cyclodextrin, ⁇ -cyclodextrin, and It is preferred to be selected from the group consisting of ⁇ -cyclodextrin and derivatives thereof.
  • the cyclic molecule may be an optionally substituted ⁇ -cyclodextrin, and the linear molecule may be polyethylene glycol.
  • ⁇ 23> The amount of cyclic molecules that can be maximally included when the cyclic molecules are included in a skewered manner by linear molecules according to ⁇ 1> to ⁇ 22> above.
  • the molecular weight is 1, the cyclic molecular force O. 01 to 0.99, preferably ⁇ or 0.1 to 0.9, more preferably ⁇ or 0.2 to 0.8 is skewered into a linear molecule. It should be included.
  • the liquid crystalline composition is a display material, a display element, a recording material, a lithium ion battery, a fuel cell, a solar cell, an actuator, an electric It is used for at least one selected group power consisting of double layer capacitor, light emitting element, electochromic element, sensor, iox circuit, polymer electrolyte, electrochemical material, catalyst, separation membrane, and coating agent Gayo! /
  • a method for producing a liquid crystalline composition comprising ⁇ 25> a poly (oral taxane); and a liquid crystalline substance,
  • the method comprises:
  • the above-mentioned 25> is preferably a group cathode group that exhibits compatibility with a liquid crystal substance.
  • step is performed after step v, b) and before vi ′) c) step, or vii ′) C) after step
  • the step C) is preferably performed after the step b).
  • any one of the above items 25> to ⁇ 28> it may further include e) a step of reacting or physically adsorbing the poly-oral taxanes to obtain a crosslinked poly-oral taxane.
  • the step of obtaining a crosslinked poly (oral) taxane is preferably carried out by a chemical crosslinking method using a crosslinking agent or a photocrosslinking method using light irradiation.
  • the mesogenic group is A—X—B—CY— (wherein A and B are 6-membered rings, and C is a single bond or a straight chain) And X and Y are linking groups).
  • the 6-membered rings of A and B may be each independently substituted, or a saturated or unsaturated homocyclic or heterocyclic ring, preferably substituted. You may be a benzene ring. More preferably, A is a P-cyanophenol group, and B is an unsubstituted benzene ring.
  • C has 0 to 100 elements, preferably 0 to 70 elements, more preferably 0 to 30 elements, forming the straight chain of C. Is good.
  • the straight chain may contain O or a benzene ring.
  • the “number of elements forming a straight chain” of the Zen ring is four for convenience.
  • C is a linear alkyl chain or a linear alkyl ether chain.
  • Y represents a single bond, O—, —CO, one CO—O, one O—CO, one NH—CO, one CO—NH, one NH It should be selected from the group consisting of —CO—O— and one O—CO—NH.
  • Y is selected from the group consisting of CO—O, 1 O, 1 NH—CO—O— and 1 O—CO, more preferably CO—O! / ⁇ .
  • A—X—B is a group that also includes the above D—1 to D—20 (wherein, is the same as described above).
  • the power should also be chosen.
  • R′-R 20 ⁇ each independently a cyan group, F, Cl, a C 1-20, preferably a C 1-15 (preferably linear) alkyl group, a C 1-20, preferably C1-C15 (preferably linear) alkoxy group, C1-C20, preferably C1-C15 (preferably linear) alkylcarboxyl group or alkyloxycarbol
  • the group may be a fluorocarbon having 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms (preferably linear), or a tro group.
  • A—X—B— is D—1 to D—14, D—19 or D—20, preferably 0—2 to 0—14, D—19 or D—20, more preferably D—4.
  • a group that exhibits compatibility with a liquid crystalline substance for example, a mesogenic group is represented by the above formulas 1 to 3 (wherein n, m, and R 21 to R 26 is synonymous with the above)! /, which is a deviation of the biphenyl substituent represented by
  • the biphenyl substituent is represented by the formula 1, R 21 is 1, is present at the p-position and is a cyano group, and R 22 is 0. There should be.
  • the biphenyl substituent is represented by the formula 2, n is an integer of 2 to 10, preferably an integer of 3 to 8, particularly 5, and R 23 is 1. , P-position and a cyano group, and R 24 is preferably zero.
  • the biphenyl substituent is represented by the formula 3, m is an integer of 1 to 5, preferably an integer of 2 to 4, particularly 2, and R 25 is 1. , P-position and a cyano group, and R 26 is preferably 0.
  • a liquid crystalline substance In any one of the above items ⁇ 25> to ⁇ 40>, a liquid crystalline substance, an azo compound group, an azoxy compound group, a substituted group of P-substituted benzoic acid esters, a cholesteryl ester, P -Substituted biphenyls, substituted groups of cyclohexanecarboxylic acid esters, Schiff bases, P-substituted cyclohexyls -P-substituted files, 2-phenyl substituted-1,3-dioxanes It is preferable that at least one kind is selected from the group of substitutional groups and the group power that can also be ferrulemimidines.
  • liquid crystalline material force Formula C1, C-2, E, F-1, F-2, G or H (where X 5 to X 8 and X 1C) to X 19 are as defined above).
  • the liquid crystalline substance force is present in the crosslinked poly (oral) taxane.
  • At least a part of the polyoral taxane is a cross-linked polyoral taxane that is crosslinked with each other.
  • the linear molecule may be polybulal alcohol, polybulurpyrrolidone, poly (meth) acrylic acid, cellulosic resin (carboximethinoresenololose). ), Polyacrylamide, polyethylene oxide, polyethylene glycol, polypropylene glycol, polyvurecetal resin, polybutymethyl ether, polyamine, polyethyleneimine, casein, gelatin , Starch, etc.
  • polyethylene, polypropylene, and other polyolefin resins such as polyolefin resins, polyester resins, polyvinyl chloride resins, polystyrene and atari Mouth-Trill / Still Polystyrene-based resin such as polyethylene copolymer resin, polymethyl methacrylate and ( Acrylic resin such as (meth) acrylic acid ester copolymer, acrylonitrile methyl acrylate copolymer resin, polycarbonate resin, polyurethane resin, vinyl chloride-vinyl acetate copolymer resin, polybutyl pentyl resin, etc.
  • polyolefin resins such as polyolefin resins, polyester resins, polyvinyl chloride resins, polystyrene and atari Mouth-Trill / Still Polystyrene-based resin
  • Acrylic resin such as (meth) acrylic acid ester copolymer, acrylonitrile methyl acrylate copolymer resin, polycarbonate resin,
  • polyethylene glycol, polyisoprene, polyisobutylene, polybutadiene, polypropylene glycol, polytetrahydrofuran, polydimethylsiloxane, polyethylene, and polypropylene are preferably selected.
  • Polydimethylsiloxane, polyethylene, and polypropylene are examples of polyethylene glycol, polyis
  • the linear molecule may have a molecular weight of 00 or more, preferably 1000 or more, more preferably 2000 or more.
  • the blocking group is a dinitrophenol group, cyclodextrin, adamantane group, trityl group, fluorescein, pyrene, substituted benzene (substituted)
  • the group include, but are not limited to, alkyl, alkyloxy, hydroxy, halogen, cyanide-containing sulfonyl, carboxyl, amino-containing file, etc.
  • substituents may be present.
  • Optionally substituted polynuclear aromatics substituted polynuclear aromatics (substituents may include, but are not limited to, the same as above.
  • One or more substituents may be present
  • steroids It should be chosen from the group of similar species.
  • dinitrophenol groups, cyclodextrins, adamantane groups, trityl groups, fluoresceins, and pyrenes are preferably selected, more preferably adamantane groups or trityl groups. Is good.
  • the cyclic molecule may be a cyclodextrin molecule which may be substituted.
  • the cyclic molecule may be a substituted cyclodextrin molecule, and the cyclodextrin molecule may be ⁇ -cyclodextrin, ⁇ -cyclodextrin, and ⁇ .
  • Cyclodextrin, as well as its group power, its derivative power should be selected.
  • the cyclic molecule may be an optionally substituted ⁇ -cyclodextrin, and the linear molecule may be polyethylene glycol.
  • the maximum amount of the cyclic molecule is included.
  • the cyclic molecular force is 0.01 to 0.99, preferably in the amount of 0.1 to 0.9, more preferably in the amount of 0.2 to 0.8. It should be included.
  • the liquid crystalline composition is a display material, a display element, a recording material, a lithium ion battery, a fuel cell, a solar cell, an actuator, an electric Multilayer capacitor, light emitting element, electochromic element, sensor, iotas circuit, polymer electrolyte, electrochemical material, catalyst, separation membrane, and coating force .
  • the present invention provides a liquid crystalline composition comprising a poly (oral) taxane; and a liquid crystalline substance.
  • the liquid crystalline composition of the present invention has a liquid crystalline substance.
  • a liquid crystal substance refers to a molecule or substance that can form an intermediate phase by the force of a temperature change such as heating or cooling or the action of a certain amount of solvent.
  • the liquid crystal substance is not particularly limited, and examples thereof include conventionally known liquid crystal substances and liquid crystal substances developed in the future.
  • the liquid crystal substance contained in the composition of the present invention may be one kind, two kinds or more.
  • an azo compound group As a liquid crystalline substance, an azo compound group, an azoxyhi compound group, a substituted group of P-substituted benzoic acid ester, a cholesteryl ester, a P-substituted biphenyl, a substituted product of cyclohexanecarboxylic acid ester Group, Schiff bases, P-substituted cyclohexyl-P-substituted fur, 2-phenyl substituted-1,3-dioxane substituted groups, phenyl pyrimidines, etc. Not.
  • the azo compound group is Formula A
  • the azoxy compound group is Formula B
  • the substituted group of P-substituted benzoic acid ester is Formula C 1 or C 2
  • the cholesteryl ester is Formula D.
  • P-substituted biphenyls are of formula E
  • cyclohexanecarboxylic acid ester substituents are of formula F-1 or F-2
  • Schiff bases are of formula G
  • P-substituted cyclohexyl-P- Substituted phenyls are of formula H
  • 2-phenyl substituted-1,3-dioxane substituted groups are
  • -Rupyrimidines can be represented by the formula ⁇ .
  • xi x 23 each independently represents a substituent.
  • each X 23 is independently a cyan group, F, Cl, a C 1-20, preferably a C 1-15 (preferably linear) alkyl group, a C 1-20, preferably a carbon A C1-C15 (preferably linear) alkoxy group, C1-C20, preferably C1-C15 (preferably straight-chain) alkylcarbonyloxy group or alkoxycarbonyl group, carbon It is a fluorocarbon having 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms (preferably linear), or a -tro group.
  • the liquid crystal material force formula C- 1, C- 2, E, F- 1, F- 2, the compounds represented by G or H is Yogu X 5 to X 8 and X 1G to X 19 are each independently a cyano group, F, Cl, carbon number:! To 20, preferably 1 to 15 (preferably linear) alkyl group, carbon number:! To 20, preferably Is a C1-C15 (preferably linear) alkoxy group, C1-C20, preferably C1-C15 (preferably linear) alkylcarbonyloxy group or alkylo.
  • the liquid crystal substance has a weight ratio of liquid crystal substance: polymouth taxane of 0.999:
  • the polymouth taxane is arranged at both ends of the linear molecule so that the cyclic molecule, the linear molecule that includes the cyclic molecule in a skewered manner, and the linear molecular force cyclic molecule are not detached. It has a blocking group.
  • the polyoral taxane has a group in which the cyclic molecule exhibits compatibility with the liquid crystalline substance.
  • compatibility with a liquid crystal substance can be brought about in the poly (taxane) taxane.
  • the compatibility between the polyoral taxane and the liquid crystalline substance includes the case where both of them have direct compatibility, but other than that, the composition is a component other than the polyoral taxane and the liquid crystalline substance.
  • having a compatibility force S between the poly (taxane taxane) and the liquid crystalline substance via the other components examples include, but are not limited to, good solvents for both the polymouth taxane and the liquid crystal substance.
  • Other components (third component) will be described later.
  • a mesogenic group is a group that expresses the formation of an intermediate phase by the force of temperature changes such as heating and cooling, or by the action of a certain amount of solvent.
  • the mesogenic group is represented by A—X—B—CY (wherein A and B are 6-membered rings, C is a single bond or a linear group, and X and Y are linking groups). It ’s a good group.
  • the 6-membered rings of A and B may each independently be a saturated or unsaturated homocyclic or heterocyclic ring, which may be substituted, preferably an optionally substituted benzene ring. More preferably, A is a P-cyanophenol group and B is an unsubstituted benzene ring.
  • C may have a number power of elements forming a straight chain of C to 100, preferably 0 to 70, and more preferably 0 to 30.
  • C may contain O or a benzene ring in a straight chain.
  • the “number of elements forming a straight chain” of the benzene ring is four for convenience in the present application.
  • C is a linear alkyl chain or a linear alkyl ether chain.
  • Y is a single bond, one O, one CO, one CO—O, one O—CO, one NH—CO—, one It may be selected from the group consisting of CO—NH, 1 NH—CO—O and 1 O—CO—NH.
  • Y is selected from the group consisting of 1 CO— ⁇ , 1 O, 1 NH—CO—O and 1 O—CO, more preferably CO—O.
  • A—X—B is preferably selected from the group force consisting of the above-described D— 1 to D 20 (wherein R 1 ! ⁇ Is as defined above).
  • R′-R 20 ⁇ each independently a cyan group, F, Cl, a C 1-20, preferably a C 1-15 (preferably linear) alkyl group, a C 1-20, preferably C1-C15 (preferably linear) alkoxy group, C1-C20, preferably C1-C15 (preferably linear) alkylcarbonyloxy group or alkyloxycarbonyl group , A fluorocarbon having 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms (preferably linear), or a -tro group.
  • A—X—B is D—1 to D — 14, D—19 or D—20, preferably 0—2 to 0—14, D—19 or D—20, more preferably D— 4 to D-14, D-19 or D-20, especially D-6.
  • the mesogenic group is a biphenyl substituent represented by the above formula 1 to formula 3 (wherein n, m, and R 21 to R 26 are as defined above). That's it! /
  • biphenyl substituent is represented by the formula 1, wherein R 21 is 1, is present at the p-position and is a cyano group, and R 22 is 0.
  • n is an integer of 2 to 10, preferably 3 to 8, especially 5, R 23 is 1, and is present at the p-position and cyano
  • R 24 is zero.
  • the biphenyl substituent is represented by formula 3, m is an integer from 1 to 5, preferably an integer from 2 to 4, especially 2, R 25 is 1, and is present in the p position and It is a cyan group, and it is preferable that R 26 is 0.
  • the polymouth taxane is a crosslinked polymouth taxane that is crosslinked with the same polyrotaxane.
  • the cross-linked poly (oral) taxane may be physically cross-linked or chemically cross-linked between the polyrotaxanes.
  • polycyclic taxanes are cross-linked by the cyclic molecules being bonded to each other through some group or directly bonded.
  • the poly (oral) taxane forms a crosslinked poly (oral) taxane
  • the liquid crystalline substance should be present in the crosslinked polydioxane as a solvent.
  • the linear molecule is poly (bulb alcohol), poly (buryl pyrrolidone), poly (meth) acrylic acid, cellulosic resin (carboxymethylenosolerose, hydroxye).
  • Dimethylsiloxane, polyethylene, and polypropylene group strength are also preferably selected.
  • Polypropylene glycol, polytetrahydrofuran, polydimethylsiloxane, polyethylene, and polypropylene group power are also preferably selected, especially polyethylene glycol. Good.
  • the linear molecule should have a molecular weight of 500 or more, preferably 1000 or more, more preferably 2000 or more! /.
  • the blocking group is a dinitrophenyl group. , Cyclodextrins, adamantane groups, trityl groups, fluoresceins, pyrenes, substituted benzenes (substituents include alkyl, alkyloxy, hydroxy, halogen, sheared sulfonyl, carboxyl, amino, phenol, etc.
  • the present invention is not limited thereto, and one or more substituents may be present), polynuclear aromatics that may be substituted (substituents are the same as those described above)
  • the substituent may be present in one or more substituents), and may be selected from the group consisting of steroids.
  • the cyclic molecule may be an optionally substituted cyclodextrin molecule.
  • the cyclic molecule is an optionally substituted cyclodextrin molecule, and the cyclodextrin molecule is selected from the group consisting of hycyclodextrin, ⁇ -cyclodextrin and ⁇ -cyclodextrin, and derivatives thereof. Is good.
  • the cyclic molecule may be substituted ⁇ -cyclodextrin, and the linear molecule may be polyethylene glycol.
  • the amount of the cyclic molecule that is maximally included is 1, Cyclic molecular force O. 01 to 0.99, preferably ⁇ or 0.1 to 0.9, more preferably ⁇ or 0.2 to 0.8 is included in a skewered manner in a linear molecule. Good.
  • the maximum inclusion amount of the cyclic molecule can be determined by the length of the linear molecule and the thickness of the cyclic molecule. For example, when the linear molecule is polyethylene glycol and the cyclic molecule is 0C-cyclodextrin molecule, the maximum inclusion amount is experimentally determined (
  • the composition of the present invention may contain a component other than the above-described poly (ortaxane) taxane and liquid crystalline substance (hereinafter sometimes abbreviated as "third component").
  • the third component is a solvent (including the above-mentioned good solvent for both the poly (taxane) taxane and the liquid crystalline substance), a dye, a surfactant, a plasticizer, a carbon compound such as a carbon nanotube, a salt, and various polymers.
  • the third component is a polymer
  • the polymer and the polymouth taxane in the composition of the present invention may be physically or chemically bonded.
  • a third component (for example, a polymer) and the poly (taxane taxane) may be chemically crosslinked via a cyclic molecule.
  • the liquid crystalline composition of the present invention includes a display material, a display element, a recording material, a lithium battery, a fuel cell, a solar cell, an actuator, an electric double layer capacitor, a light emitting element, an electochromism element, a sensor, and an ion.
  • -It should be used for at least one selected from the group power consisting of a Tas circuit, polymer electrolyte, electrochemical material, catalyst, separation membrane, and coating agent.
  • liquid crystalline composition can be prepared as follows, for example.
  • a cyclic molecule is not detached from the linear molecule! /, and a step of preparing a poly (taxane) taxane by arranging blocking groups at both ends of the linear molecule,
  • the method comprises:
  • the liquid crystalline composition of the present invention can be obtained by having a step of introducing the liquid crystalline substance into the system, that is, the composition.
  • Steps a) and b) can be performed by a conventionally known method. For example, it can be obtained by the methods described in Japanese Patent No. 3475252, Japanese Patent Application Laid-Open No. 2005-154675, and the like. [0061] Hereinafter, step c) will be described.
  • Step c) is a step of introducing a group that expresses compatibility with the liquid crystalline substance into the cyclic molecule, for example, a mesogenic group.
  • This step consists of i) a) before step; ii) a) during step; iii) after step a) and b) before step; iv) b) during step; or V) b) after step; However, it is preferable to carry out in step V), that is, after step b).
  • the step of introducing a group that exhibits compatibility with the liquid crystalline substance for example, a mesogenic group
  • the conditions used in the introduction step depend on the type of mesogenic group to be introduced and the type of polyortaxane, but are not particularly limited, and various reaction methods and reaction conditions can be used.
  • the mesogenic group bonding group for example, Y
  • ether group one O—
  • the following may be mentioned.
  • a technique in which an appropriate base coexists with a halide in a polar solvent such as dimethylsulfoxide or dimethylformamide is used.
  • the mesogenic group can be introduced by reacting an acid chloride that can be a mesogenic group in the presence of triethylamine.
  • the groups represented by the formulas 1 to 3 are introduced as mesogenic groups, the acid chloride derivatives of those groups are preferably reacted with a polyditaxane in the presence of triethylamine.
  • Step d) is a step of introducing a liquid crystalline substance into the system, that is, into the composition.
  • This step is i ') a) before step; ii') a) during step; iii ') after a) step, b) before step; iv,) b) during step; v,) b) after step Vi,) c) before step; or vii,) c) after step.
  • it is carried out after step v,) b) and before step vi ′) c), or after step vii ′) c), step c) after step b).
  • the d) step depends on the type of liquid crystalline substance to be used and the polymouth taxane. This can be done under the following conditions.
  • the step d) can be performed by mixing the liquid crystalline substance and the polyditaxane by various methods. Specifically, a method in which both the liquid crystalline substance and the Z or polymouth taxane are heated and mixed in a fluid state; a method in which both are dissolved and mixed in a good solvent for the liquid crystalline substance and the polymouth taxane, etc. However, it is not limited to these.
  • the method of the present invention preferably further includes the step of e) reacting or physically adsorbing the polypolytaxanes to obtain a crosslinked polyrotaxane.
  • the step e) is preferably performed after the above step.
  • Step e) can be performed by a chemical bridge method using a crosslinking agent or the like, or a photocrosslinking method by irradiating light.
  • a conventionally known method for example, a method described in Japanese Patent No. 3475252, Japanese Patent Laid-Open No. 2005-154675, or the like is used. It is out.
  • the polymouth taxane was prepared according to the method described in JP-A-2005-154675, and was actually purchased from Advanced Soft Materials and used as it was.
  • the linear molecule is PEG (weight average molecular weight 35000)
  • the cyclic molecule is ⁇ -cyclodextrin
  • the blocking group is adamantane group
  • the number of included cyclodextrins is 90 ⁇ : LOO per molecule.
  • the amount of inclusion was 0.25 to 0.3 when the maximum amount included was 1.
  • Other chemicals were purchased from Wako Pure Chemicals, Aldrich, Tokyo Chemical Industry, etc., and used without further purification.
  • CNBP-C-COOH (2.48 mmol) was dissolved in 5 ml of chlorochloride, and argon was added. The mixture was stirred at room temperature for 4 hours under flow, and then the excess salt was distilled off by evaporation to give 6- (4-cyanobiphenol-4, -yloxy) hexanoic acid chloride (hereinafter CNB PC-COC1 and Obtained). The obtained CNBP-C-COC1 was further purified.
  • the whole amount was used as it was for the following binding reaction.
  • Anhydrous lithium chloride (1.13g) was dissolved in dehydrated dimethylacetamide (11.4g), and poly (polytaxane) (126mg) was added thereto and dissolved at a temperature of room temperature to 60 ° C. Thereafter, the obtained mixture was cooled to room temperature and mixed with triethylamine (0.345 ml).
  • a solution obtained by dissolving CNBP-C-COC1 obtained above in 3 ml of dehydrated dimethylacetamide is used.
  • the polymouth taxane CNBP-C APR obtained above is a low-molecular liquid crystal substance at high temperatures.
  • Figure 1 shows the temperature change of CNBP-C APRZ5CB composition. Up to 55 ° C
  • This poly-ortaxane CNBP-C APR is tetrahydrofuran (hereinafter abbreviated as “THF”).
  • composition thus obtained was cast on a glass slide and dried on a hot plate at 50 ° C. to form a film.
  • Figure 2 shows the temperature change of CNBP-C APRZ5CB mixed film.
  • This film was white at room temperature, but became transparent when heated above 37 ° C, and became cloudy again when the temperature was lowered to room temperature. All of these changes were completed within a few seconds and showed rapid temperature response.
  • this film was placed between crossed polarizers and the temperature responsiveness was observed in the same way, it showed birefringence at room temperature, but the birefringence decreased at 37 ° C or higher. Since 5 CB transitions to an isotropic phase of nematic phase at 35 ° C, it was suggested that the properties of this film reflect the liquid crystal properties of 5CB contained in the film.
  • a composition containing 5CB as a solvent was prepared.
  • Figure 3 shows the temperature change of the composition obtained. At 20 ° C, it is contained as a solvent, and since the 5CB is a nematic phase, the clouding force of 5CB becomes isotropic and transparent at 50 ° C.
  • FIG. 4 shows a similar composition observed between crossed polarizers. It can be seen that the composition exhibits birefringence at 20 ° C, whereas the birefringence disappears at 50 ° C.
  • low molecular liquid crystals such as 5CB and cross-linked poly-ortaxane CL— CNBP- C AP
  • composition of this example having R exhibits liquid crystallinity.
  • composition of the present invention Has a cross-linked poly oral taxane CL- CNBP-CAPR
  • the cyclic molecule has a pulley effect produced by sliding on a straight-chain molecule (see Japanese Patent No. 3475252).
  • FIG. 1 is a graph showing the temperature change of the composition obtained in Example 1.
  • FIG. 2 is a view showing a temperature change of the composition obtained in Example 2. (a) is observed under normal light, and (b) is observed between orthogonal polarizers.
  • FIG. 3 is a view showing a temperature change of the composition obtained in Example 3 observed under normal light.
  • FIG. 4 is a view showing a temperature change of the composition obtained in Example 3 observed between crossed polarizers.

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Abstract

L'invention concerne une composition de cristaux liquides dotée de souplesse et/ou apte au pliage, ainsi qu'un procédé pour la produire. La composition décrite par l'invention comprend : un polyrotaxane, comportant une molécule cyclique, une molécule à chaîne linéaire s'enfilant dans la molécule cyclique de manière à former un clathrate, et des groupes bloquants placés à chaque extrémité de la molécule à chaîne linéaire afin d'empêcher la molécule cyclique de sortir de ladite molécule linéaire ; et une substance de cristaux liquides, la polyrotaxane comprenant un groupe conférant à la molécule cyclique une compatibilité avec la substance de cristaux liquides, par exemple un groupe mésogène, et en particulier l'un quelconque des biphényles répondant aux formules (1) à (3).
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CN105219007A (zh) * 2015-09-11 2016-01-06 上海天封科技有限公司 一种剃须刀用润滑条
US9349778B2 (en) 2013-05-09 2016-05-24 Lg Chem, Ltd. Polymer film, flexible light emitting element display device, and rollable display device
EP2619284B1 (fr) 2010-09-25 2017-04-12 Merck Patent GmbH Écrans à base de cristaux liquides et fluides cristallins liquides à orientation homéotrope
CN107674409A (zh) * 2017-09-19 2018-02-09 暨南大学 一种聚氨酯/液晶复合生物材料及其制备方法、应用
KR101876945B1 (ko) * 2011-09-23 2018-07-11 삼성디스플레이 주식회사 표시 패널 및 이의 제조 방법
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Cited By (13)

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Publication number Priority date Publication date Assignee Title
JP2009124875A (ja) * 2007-11-15 2009-06-04 Toyoda Gosei Co Ltd アクチュエータ
US11015121B2 (en) 2010-09-25 2021-05-25 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid crystal displays and liquid crystalline media with homeotropic alignment
EP2619284B1 (fr) 2010-09-25 2017-04-12 Merck Patent GmbH Écrans à base de cristaux liquides et fluides cristallins liquides à orientation homéotrope
US10273409B2 (en) 2010-09-25 2019-04-30 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid crystal displays and liquid crystalline media with homeotropic alignment
EP2619284B2 (fr) † 2010-09-25 2022-12-28 Merck Patent GmbH Écrans à base de cristaux liquides et fluides cristallins liquides à orientation homéotrope
KR101876945B1 (ko) * 2011-09-23 2018-07-11 삼성디스플레이 주식회사 표시 패널 및 이의 제조 방법
US9349778B2 (en) 2013-05-09 2016-05-24 Lg Chem, Ltd. Polymer film, flexible light emitting element display device, and rollable display device
CN105219007B (zh) * 2015-09-11 2018-01-02 上海天封科技有限公司 一种剃须刀用润滑条
CN105219007A (zh) * 2015-09-11 2016-01-06 上海天封科技有限公司 一种剃须刀用润滑条
CN107674409A (zh) * 2017-09-19 2018-02-09 暨南大学 一种聚氨酯/液晶复合生物材料及其制备方法、应用
CN107674409B (zh) * 2017-09-19 2020-06-16 暨南大学 一种聚氨酯/液晶复合生物材料及其制备方法、应用
CN116003865A (zh) * 2023-02-24 2023-04-25 北京百奥纳芯生物科技有限公司 一种柔性醛基基片、制备方法与生物芯片
CN116003865B (zh) * 2023-02-24 2023-06-09 北京百奥纳芯生物科技有限公司 一种柔性醛基基片、制备方法与生物芯片

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