WO2013132991A1 - Composé, composition de cristaux liquides, matière polymère et film - Google Patents

Composé, composition de cristaux liquides, matière polymère et film Download PDF

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WO2013132991A1
WO2013132991A1 PCT/JP2013/053807 JP2013053807W WO2013132991A1 WO 2013132991 A1 WO2013132991 A1 WO 2013132991A1 JP 2013053807 W JP2013053807 W JP 2013053807W WO 2013132991 A1 WO2013132991 A1 WO 2013132991A1
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general formula
group
liquid crystal
carbon atoms
crystal composition
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Japanese (ja)
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峻也 加藤
吉川　将
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富士フイルム株式会社
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    • 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
    • C09K19/062—Non-steroidal liquid crystal compounds containing one non-condensed benzene 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
    • C09K19/08—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
    • 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
    • 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
    • C09K19/28—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 sulfur atoms as chain links, e.g. thioesters
    • 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
    • C09K2019/0425—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a specific unit that results in a functional effect
    • C09K2019/044—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a specific unit that results in a functional effect the specific unit being a perfluoro chain used as an end group
    • 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
    • C09K19/08—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
    • C09K2019/2035—Ph-COO-Ph
    • 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
    • C09K19/08—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

Definitions

  • the present invention uses a liquid crystal composition useful for various applications including materials for various optical members such as an optically anisotropic film and a heat shielding film, a compound used in the liquid crystal composition, and these.
  • the present invention relates to a polymer material and a film.
  • a liquid crystal composition mainly containing a compound having a discotic core and a long-chain fluorinated alkyl group on the interface (air interface) side where no alignment treatment is performed even without an alignment film.
  • a technique has been developed in which alignment restriction force is applied to the air interface of the liquid crystal film to uniformly align the liquid crystal film for example, Patent Document 1).
  • the problem to be solved by the present invention is that the haze is low when a film is formed by aligning liquid crystals, and the surface energy when forming a film that can suppress repellency when forming a film laminate of two or more layers is low. It is to provide a liquid crystal composition.
  • the present invention also provides a novel compound used in the liquid crystal composition and a polymer material and a film useful for various applications including materials for various optical members such as an optically anisotropic film and a heat shielding film. The purpose is to do.
  • a liquid crystal composition comprising liquid crystal molecules and a compound represented by the following general formula (I).
  • Formula (I) (In the general formula (I), L 1 , L 2 , L 3 , L 4 , L 5 and L 6 are each independently a single bond, —O—, —S—, —CO—, —COO—, — OCO-, -SCO-, -COS-, -NRCO-, -CONR-, -OCHR, -CHRO- (wherein each R in the general formula (I) is independently a hydrogen atom or a carbon atom number of 1 to 6)
  • Sp 1 , Sp 2 , Sp 3 and Sp 4 are each independently a single bond or an alkylene group having 1 to 10 carbon atoms (provided that the hydrogen atom of the alkylene group is substituted with a fluorine atom) may be, not adjacent -CH 2 - represents a may be) replaced by -O-, a 1 represents a m + 1-valent aromatic
  • T 1 is preferably a single bond or a divalent or trivalent aromatic hydrocarbon group.
  • m is preferably 3 in the general formula (I).
  • the compound represented by the general formula (I) is preferably a compound represented by the following general formula (II).
  • L 11 , L 12 , L 13 , L 15 and L 16 are each independently a single bond, —O—, —S—, —CO—, —COO—, —OCO—, —COS—, —SCO—, —NRCO—, —CONR—, —OCHR, —CHRO— (wherein R in the general formula (II) is independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms)
  • Sp 11 , Sp 12 , Sp 13 and Sp 14 are each independently a single bond or an alkylene group having 1 to 10 carbon atoms (provided that the hydrogen atom of the alkylene group is substituted with a fluorine atom)
  • a 11 represents an m1 + 1 valent aromatic hydrocarbon group
  • T 11 represents a single bond, a divalent or a trivalent, or a non-adjacent —CH 2 — may be substituted with —O—.
  • Hb 11 and Hb 12 .M1 representing a fluoroalkyl group having 2 to 30 carbon atoms are each independently is 2 or 3, n1 is 1 or 2, satisfying the m1> n1, there are multiple brackets
  • the inner structures may be the same or different from each other.
  • m1 is 3
  • a 11 is a tetravalent aromatic represented by the following formula (II-A) carbide
  • a hydrogen group is preferred.
  • R 1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, a cyano group, or a group containing an ester structure, and p is 0 to 4 And when p is 2 or more, the plurality of R 1 may be the same or different from each other.
  • the liquid crystal molecules are preferably polymerizable rod-like liquid crystal molecules.
  • the liquid crystal composition according to any one of [1] to [8] preferably contains at least one chiral compound.
  • the film according to [11] or [12] preferably exhibits optical anisotropy.
  • the film according to any one of [11] to [13] preferably exhibits selective reflection characteristics.
  • the film according to [14] preferably exhibits selective reflection characteristics in an infrared wavelength region.
  • Sp 11 , Sp 12 , Sp 13 and Sp 14 are each independently a single bond or an alkylene group having 1 to 10 carbon atoms (provided that the hydrogen atom of the alkylene group is substituted with a fluorine atom)
  • a 11 represents an m1 + 1 valent aromatic hydrocarbon
  • T 11 represents a single bond, a divalent or a trivalent, or a non-adjacent —CH 2 —
  • n1 is 1, and wherein the T 11 is a divalent aromatic hydrocarbon group represented by a single bond or the following general formula (II-T) [16] The compound according to [17].
  • General formula (II-T) (In the general formula (II-T), R 1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, a cyano group, or a group containing an ester structure, and p is 0 to 4 And when p is 2 or more, the plurality of R 1 may be the same or different from each other.)
  • a liquid crystal composition having a low surface energy when formed into a film that has a low haze when formed into a film by aligning liquid crystals and can suppress repelling when forming a film laminate of two or more layers.
  • the novel compound used in the liquid crystal composition of the present invention and a polymer material useful for various applications including materials for various optical members such as optically anisotropic films and heat shielding films. And films can be provided.
  • FIG. 1 represents the transmission spectrum of the film of Example 4.
  • a numerical range expressed using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
  • the liquid crystal composition of the present invention contains liquid crystal molecules and a compound represented by the following general formula (I).
  • Formula (I) (In the general formula (I), L 1 , L 2 , L 3 , L 4 , L 5 and L 6 are each independently a single bond, —O—, —S—, —CO—, —COO—, — OCO-, -SCO-, -COS-, -NRCO-, -CONR-, -OCHR, -CHRO- (wherein each R in the general formula (I) is independently a hydrogen atom or a carbon atom number of 1 to 6)
  • Sp 1 , Sp 2 , Sp 3 and Sp 4 are each independently a single bond or an alkylene group having 1 to 10 carbon atoms (provided that the hydrogen atom of the alkylene group is substituted with a fluorine atom) may be, not adjacent -CH 2 - represents a may be) replaced by -O-, a 1 represents a
  • the liquid crystal alignment accelerator means that when the compound is added to the liquid crystal composition and then cured by alignment, the liquid crystal composition is added without adding the compound and cured. Means a compound that reduces haze.
  • the liquid crystal alignment accelerator is sometimes called a haze reducing agent or a haze reducing agent.
  • the compound represented by the general formula (I) described later can be preferably added to the liquid crystal composition of the present invention as a liquid crystal alignment accelerator (that is, a haze reducing agent or a haze reducing agent).
  • the liquid crystal composition of the present invention contains a compound represented by the following general formula (I).
  • the compound represented by the following general formula (I) has a structure in which a fluorinated alkyl group is arranged at each terminal of the molecule and is asymmetrical so that the number of fluorinated alkyl groups at each terminal is different.
  • a compound having a fluorinated alkyl group at the terminal is effective as an alignment accelerator, but conventionally known alignment accelerators have a limited use concentration range and low solubility, limiting their use. It had been.
  • the compound represented by the following general formula (I) exhibits an orientation performance equal to or higher than that in a wider concentration range and good solubility, there is an advantage that a composition containing them is easy to use in production. Moreover, since it can be hardened
  • L 1 , L 2 , L 3 , L 4 , L 5 and L 6 are each independently a single bond, —O—, —S—, —CO—, —COO—, —OCO. —, —SCO—, —COS—, —NRCO—, —CONR—, —OCHR, —CHRO— (in the general formula (I), R represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms).
  • the alkyl group that R can take may be linear or branched.
  • the alkyl group that R can take is more preferably 1 to 3, and examples thereof include a methyl group, an ethyl group, and an n-propyl group.
  • R in the general formula (I) is preferably a hydrogen atom.
  • Sp 1 , Sp 2 , Sp 3 and Sp 4 each independently represents a single bond or an alkylene group having 1 to 10 carbon atoms, more preferably a single bond or an alkylene group having 1 to 7 carbon atoms, still more preferably Is a single bond or an alkylene group having 1 to 4 carbon atoms, and a non-adjacent methylene group in the alkylene may be substituted with —O—.
  • the alkylene group may or may not be branched, but a linear alkylene group having no branch is preferred.
  • a 1 is an m + 1 valent aromatic hydrocarbon.
  • the m + 1 valent aromatic hydrocarbon group preferably has 6 to 22 carbon atoms, more preferably 6 to 14, more preferably 6 to 10, still more preferably 6.
  • the m + 1 valent aromatic hydrocarbon group has 6 carbon atoms, it is preferable to have a bond at the meta position or the para position, more preferably at least a bond at the para position. It is particularly preferable to have a bond.
  • the m + 1 valent aromatic hydrocarbon group represented by A 1 may have a substituent.
  • Examples of such a substituent include an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, a cyano group, or a group containing an ester structure.
  • the substituent for the m + 1 valent aromatic hydrocarbon group represented by A 1 include a methyl group, an ethyl group, a methoxy group, an ethoxy group, a bromine atom, a chlorine atom, and a cyano group.
  • a 2 represents a group having an n + 1 valent cyclic structure.
  • group consisting of n + 1 valent cyclic structure represented by A 2 alicyclic, aromatic hydrocarbon rings, may be any heterocyclic ring.
  • the group composed of an n + 1 valent cyclic structure represented by A 2 is preferably an n + 1 valent aromatic hydrocarbon group or a divalent heterocyclic group, and more preferably an n + 1 valent aromatic hydrocarbon.
  • the number of carbon atoms of the n + 1 valent aromatic hydrocarbon group is preferably 6 to 22, more preferably 6 to 14, still more preferably 6 to 10, and still more preferably 6.
  • the n + 1-valent heterocyclic group preferably has a 5-membered, 6-membered or 7-membered heterocyclic ring.
  • a 5-membered ring or a 6-membered ring is more preferable, and a 6-membered ring is most preferable.
  • the hetero atom constituting the heterocyclic ring a nitrogen atom, an oxygen atom and a sulfur atom are preferable.
  • the heterocycle is preferably an aromatic heterocycle.
  • the aromatic heterocycle is generally an unsaturated heterocycle.
  • heterocyclic rings include furan ring, thiophene ring, pyrrole ring, pyrroline ring, pyrrolidine ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, imidazoline ring, imidazolidine ring, pyrazole ring, pyrazoline Ring, pyrazolidine ring, triazole ring, triazane ring, tetrazole ring, pyran ring, thiyne ring, pyridine ring, piperidine ring, oxazine ring, morpholine ring, thiazine ring, pyridazine ring, pyrimidine ring, pyrazine ring, piperazine ring and triazine ring included.
  • the group consisting of an n + 1 valent cyclic structure represented by A 2 may have a substituent.
  • a substituent include an alkyl group having 1 to 8 carbon atoms, an alkoxy group, a halogen atom, a cyano group, or a group containing an ester structure.
  • the substituent for the group having an n + 1 valent cyclic structure include a methyl group, an ethyl group, a methoxy group, an ethoxy group, a bromine atom, a chlorine atom, and a cyano group.
  • T 1 represents a single bond or a group consisting of a divalent or trivalent cyclic structure.
  • group consisting of a divalent or trivalent cyclic structure represented by T 1 (X and R 1 are an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, a cyano group, or a group containing an ester structure. Preferably), more preferably And particularly preferably It is.
  • p represents an integer of 0 or more. When p is 2 or more, a plurality of structures in parentheses may be the same as or different from each other. p is preferably an integer of 0 to 4, more preferably 0 to 2, and particularly preferably 0 or 1.
  • X and R 1 may have an alkyl group having 1 to 8 carbon atoms, preferably 1 to 5 carbon atoms, and more preferably 1 to 3 carbon atoms.
  • the alkyl group may be linear, branched or cyclic, and is preferably linear or branched. Preferred examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group.
  • the alkyl moiety of the alkoxy groups X and R 1 may take, it is possible to refer to the description and the preferred range of the alkyl groups X and R 1 may take.
  • Examples of the halogen atom that X and R 1 can take include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a chlorine atom and a bromine atom are preferable.
  • Examples of the group containing an ester structure that X and R 1 can take include a group represented by RCOO—.
  • Examples of R include an alkyl group having 1 to 8 carbon atoms. For the description and preferred range of the alkyl group that R can take, the description and preferred range of the alkyl group that X can take can be referred to.
  • Specific examples of the ester include CH 3 COO— and C 2 H 5 COO—.
  • R 0 is a hydrogen atom
  • adjacent CH 2 is an alkyl group or a fluorinated alkyl group which may be substituted with O or S
  • -Sp 5 -P can be exemplified.
  • R 0 represents an alkyl group or fluorinated alkyl group in which adjacent CH 2 may be substituted with O or S
  • a group represented by -Sp 6- (L 7 -Sp 7 ) t -CH 3 or A group represented by —Sp 8 — (L 8 —Sp 9 ) u —Hb 0 is more preferable.
  • Sp 6 , Sp 7 , Sp 8 and Sp 9 each independently represent a single bond or an alkylene group having 1 to 10 carbon atoms, preferably a single bond or an alkylene group having 1 to 7 carbon atoms, more preferably a single bond.
  • the hydrogen atom of the alkylene group represented by Sp 6 , Sp 7 , Sp 8 , Sp 9 may be substituted with a fluorine atom, but is preferably not substituted, and the alkylene group may be branched.
  • a straight-chain alkylene group having no branching is preferable although it may be omitted.
  • L 7 and L 8 are each independently a single bond, —O—, —S—, —CO—, —COO—, —OCO—, —COS—, —SCO—, —NRCO—, —CONR— (L 7 , R in L 8 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), and —NRCO— and —CONR— have the effect of reducing solubility and increase the haze value during film formation. More preferred is —O—, —S—, —CO—, —COO—, —OCO—, —COS—, —SCO—, and more preferred is —O— from the viewpoint of the stability of the compound.
  • t represents an integer of 1 to 4, preferably an integer of 1 to 3, more preferably 2 or 3, and particularly preferably 3.
  • u represents an integer of 1 to 4, preferably an integer of 1 to 3, more preferably 1 or 2, and particularly preferably 1.
  • Hb 0 represents a perfluoroalkyl group or fluoroalkyl group having 2 to 30 carbon atoms, more preferably a perfluoroalkyl group or fluoroalkyl group having 3 to 20 carbon atoms, and further preferably a perfluoroalkyl group having 3 to 10 carbon atoms.
  • the perfluoroalkyl group or fluoroalkyl group may be linear, branched or cyclic, but is preferably linear or branched, more preferably linear. .
  • Hb 0 is preferably a perfluoroalkyl group having 2 to 30 carbon atoms.
  • R 0 represents —Sp 5 —P
  • Sp 5 represents a single bond or an alkylene group having 1 to 10 carbon atoms, preferably a single bond or an alkylene group having 1 to 7 carbon atoms, more preferably a carbon number. 1 to 4 alkylene groups.
  • the hydrogen atom of the alkylene group represented by Sp 5 may be substituted with a fluorine atom, and the alkylene group may or may not be branched, but is preferably a linear alkylene group having no branch. It is.
  • the P represents a polymerizable group, and the polymerizable group is not particularly limited, but is preferably an ethylenically unsaturated double bond group, more preferably a methacryloyl group or an acryloyl group, and an acryloyl group. It is particularly preferred.
  • Hb 1 and Hb 2 each independently represent a fluorinated alkyl group having 2 to 30 carbon atoms, more preferably a fluorinated alkyl group having 3 to 20 carbon atoms, and still more preferably a fluorinated alkyl group having 3 to 10 carbon atoms. is there.
  • the fluorinated alkyl group may or may not be substituted with hydrogen.
  • the fluorinated alkyl group may be linear, branched or cyclic, but is preferably linear or branched, and more preferably linear.
  • Preferred examples of the fluorinated alkyl group include those having a perfluoroalkyl group at the end. That is, it is preferably a group represented by the following general formula.
  • s is preferably from 1 to 30, more preferably from 1 to 20, and even more preferably from 1 to 10.
  • q is preferably from 0 to 20, more preferably from 0 to 10, and even more preferably from 0 to 5.
  • s + q is preferably 3 to 30. If Hb 1 there are a plurality, the plurality of Hb 1 may have a different structure may be the same structure, but are preferably the same structure. If Hb 2 Haga presence of a plurality, the plurality of Hb 2 may have a different structure may be the same structure, but are preferably the same structure.
  • l represents an integer of 0 to 2, preferably 0 or 1, and more preferably 0.
  • m is 2 or 3, and is preferably 3.
  • n is 1 or 2, and is preferably 1.
  • m and n satisfy m> n.
  • the compound represented by the general formula (I) has a molecular structure that does not have symmetry.
  • the symmetry here means one corresponding to any of point symmetry, line symmetry, or rotational symmetry
  • asymmetry means one not corresponding to any of point symmetry, line symmetry, or rotational symmetry.
  • Hb 1 -Sp 1 -L 1 -Sp 2 -L 2 -and -L 5 -Sp 3 -L 6 -Sp 4 -Hb 2 at the molecular terminals of the compound represented by formula (I) are each independently A group represented by any one of the following general formulas is preferable.
  • s is preferably from 1 to 30, more preferably from 1 to 20, and even more preferably from 1 to 10.
  • q is preferably from 0 to 20, more preferably from 0 to 10, and even more preferably from 0 to 5.
  • s + q is 3 to 30.
  • r is preferably from 1 to 10, and more preferably from 1 to 4.
  • a compound represented by the following general formula (II) is a novel compound and is preferable from the viewpoint of the effect of the present invention. That is, it is preferable that the compound represented by the general formula (I) is a compound represented by the following general formula (II).
  • L 11 , L 12 , L 13 , L 15 and L 16 are each independently a single bond, —O—, —S—, —CO—, —COO—, —OCO—, —COS—, —SCO—, —NRCO—, —CONR—, —OCHR, —CHRO— (wherein R in the general formula (II) is independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms)
  • Sp 11 , Sp 12 , Sp 13 and Sp 14 are each independently a single bond or an alkylene group having 1 to 10 carbon atoms (provided that the hydrogen atom of the alkylene group is substituted with a fluorine atom)
  • a 11 represents an m1 + 1 valent aromatic hydrocarbon group
  • T 11 represents a single bond, a divalent or a trivalent, or a non-adjacent —CH 2 — may be substituted with —O—.
  • Hb 11 and Hb 12 .M1 representing a fluoroalkyl group having 2 to 30 carbon atoms are each independently is 2 or 3, n1 is 1 or 2, satisfying the m1> n1, there are multiple brackets
  • the inner structures may be the same or different from each other.
  • L 11 , L 12 , L 13 , L 15 and L 16 in the general formula (II) are preferable for L 1 , L 2 , L 3 , L 5 and L 6 in the general formula (I). Similar to range.
  • the preferred ranges of Sp 11 , Sp 12 , Sp 13 and Sp 14 in the general formula (II) are the same as the preferred ranges of Sp 1 , Sp 2 , Sp 3 and Sp 4 in the general formula (I).
  • a 11 in the general formula (II) is the same as the preferred range of A 1 in the general formula (I), and A 11 is a tetravalent fragrance represented by the following general formula (II-A). More preferably, it is a group hydrocarbon group.
  • T 11 in the general formula (II) is the same as the preferred range of T 1 in the general formula (I), and T 11 is a single bond or 2 represented by the following general formula (II-T) More preferably, it is a valent aromatic hydrocarbon group.
  • R 1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, a cyano group, or a group containing an ester structure, and p is 0 to 4 And when p is 2 or more, the plurality of R 1 may be the same or different from each other.
  • R 1 and p in the general formula (II-T) has the same meaning as R 1 and p in Formula (I), and preferred ranges are also the same.
  • the preferable ranges of Hb 11 and Hb 12 in the general formula (II) are the same as the preferable ranges of Hb 1 and Hb 2 in the general formula (I).
  • the preferable range of m1 in the general formula (II) is the same as the preferable range of m in the general formula (I).
  • the preferable range of n1 in the general formula (II) is the same as the preferable range of n in the general formula (I).
  • the benzoic acid chloride derivative represented by the general formula (A) can be synthesized by reacting a trisubstituted benzoic acid with a chlorinating agent as shown in, for example, Scheme A below.
  • Examples of the chlorinating agent that can be used for the synthesis of the benzoic acid chloride derivative represented by the general formula (A) include thionyl chloride, phosphoryl chloride, and oxalyl chloride.
  • the trisubstituted benzoic acid can be synthesized by the method described in the examples of the present specification.
  • the liquid crystal composition of the present invention two or more kinds of compounds represented by the general formula (I) may be used, and the compound represented by the general formula (I) and other liquid crystal alignment accelerators are used in combination. May be.
  • the compound represented by the general formula (I) is preferably used in an amount of 0.01 to 20% by mass of the amount of liquid crystal molecules.
  • the amount of the compound represented by the general formula (I) is more preferably 0.02 to 3% by mass with respect to the liquid crystal molecules.
  • the amount of the compound represented by the general formula (I) is preferably 0.03 to 1% by mass with respect to the liquid crystal molecules.
  • the amount of the compound represented by the general formula (I) is preferably 0.15 to 3% by mass with respect to the liquid crystal molecules when it is necessary to use at a high concentration.
  • the liquid crystal composition of the present invention contains liquid crystal molecules.
  • the liquid crystal molecules are preferably polymerizable liquid crystal molecules having a polymerizable group.
  • one or more kinds of polymerizable liquid crystal molecules and one or more kinds of non-polymerizable liquid crystal molecules may be used in combination.
  • polymerizable liquid crystal molecules it is preferable to use polymerizable discotic liquid crystal molecules or polymerizable rod-like liquid crystal molecules.
  • Discotic liquid crystalline molecules are described in various documents (C. Destrade et al., Mol. Crysr. Liq. Cryst., Vol. 71, page 111 (1981); edited by the Chemical Society of Japan, Quarterly Chemical Review, No. 22, Liquid Crystal Chemistry, Chapter 5, Chapter 10, Section 2 (1994); B. Kohne et al., Angew. Chem. Soc. Chem. Comm., Page 1794 (1985); J. Zhang et al., J Am. Chem. Soc., Vol. 116, page 2655 (1994)).
  • the polymerization of discotic liquid crystalline molecules is described in JP-A-8-27284.
  • the discotic liquid crystalline molecule having a polymerizable group is preferably a compound represented by the following formula.
  • D (-LQ) n In the above formula, D is a discotic core; L is a divalent linking group; Q is a polymerizable group; and n is an integer of 4 to 12.
  • LQ means a combination of a divalent linking group (L) and a polymerizable group (Q).
  • triphenylene (D4) is particularly preferable.
  • Polymerizable rod-like liquid crystalline molecules include azomethines, azoxys, cyanobiphenyls, cyanophenyl esters, benzoic acid esters, cyclohexanecarboxylic acid phenyl esters, cyanophenylcyclohexanes, cyano-substituted phenylpyrimidines, alkoxy-substituted phenyls. Pyrimidines, phenyldioxanes, tolanes and alkenylcyclohexylbenzonitriles are preferably used.
  • the birefringence of the polymerizable rod-like liquid crystal molecule is preferably 0.001 to 0.7.
  • the rod-like liquid crystal molecules preferably have a molecular structure that is substantially symmetric with respect to the minor axis direction. For that purpose, it is preferable to have a polymerizable group at both ends of the rod-like molecular structure. Specific examples of rod-like liquid crystalline molecules are shown below.
  • the liquid crystal composition may be a solvent, a compound containing an asymmetric carbon atom, or a polymerizable initiator (described later) or other additives (for example, cellulose) as necessary. Ester).
  • Optically active compound chiral agent
  • the liquid crystal composition preferably exhibits a cholesteric liquid crystal phase, and for that purpose, it preferably contains an optically active compound.
  • the rod-like liquid crystal compound is a molecule having an illegitimate carbon atom
  • a cholesteric liquid crystal phase may be stably formed without adding an optically active compound.
  • the optically active compound includes various known chiral agents (eg, Liquid Crystal Device Handbook, Chapter 3-4-3, TN, chiral agent for STN, 199 pages, edited by Japan Society for the Promotion of Science, 42nd Committee, 1989). Description).
  • the optically active compound generally contains an asymmetric carbon atom, but an axially asymmetric compound or a planar asymmetric compound that does not contain an asymmetric carbon atom can also be used as a chiral agent.
  • the axial asymmetric compound or the planar asymmetric compound include binaphthyl, helicene, paracyclophane, and derivatives thereof.
  • the optically active compound (chiral agent) may have a polymerizable group.
  • the optically active compound has a polymerizable group and the rod-like liquid crystal compound used in combination also has a polymerizable group, it is derived from the rod-like liquid crystal compound by a polymerization reaction of the polymerizable optically active compound and the polymerizable rod-like liquid crystal compound.
  • a polymer having a repeating unit and a repeating unit derived from an optically active compound can be formed.
  • the polymerizable group possessed by the polymerizable optically active compound is preferably the same group as the polymerizable group possessed by the polymerizable rod-like liquid crystal compound.
  • the polymerizable group of the optically active compound is also preferably an unsaturated polymerizable group, an epoxy group or an aziridinyl group, more preferably an unsaturated polymerizable group, and an ethylenically unsaturated polymerizable group.
  • the optically active compound may be a liquid crystal compound.
  • the optically active compound in the liquid crystal composition is preferably 1 to 30% by mass with respect to the liquid crystal compound used in combination. A smaller amount of the optically active compound is preferred because it often does not affect liquid crystallinity. Therefore, the optically active compound used as the chiral agent is preferably a compound having a strong twisting power so that a twisted orientation with a desired helical pitch can be achieved even with a small amount. Examples of such a chiral agent exhibiting a strong twisting force include those described in JP-A-2003-287623, which can be preferably used in the present invention.
  • an organic solvent is preferably used as the solvent for the liquid crystal composition.
  • organic solvents include amides (eg N, N-dimethylformamide), sulfoxides (eg dimethyl sulfoxide), heterocyclic compounds (eg pyridine), hydrocarbons (eg benzene, hexane), alkyl halides (eg , Chloroform, dichloromethane), esters (eg, methyl acetate, butyl acetate), ketones (eg, acetone, methyl ethyl ketone, cyclohexanone), ethers (eg, tetrahydrofuran, 1,2-dimethoxyethane). Alkyl halides and ketones are preferred. Two or more organic solvents may be used in combination.
  • a film can be formed by forming the liquid crystal composition of the present invention by a method such as coating.
  • An optically anisotropic element can also be produced by applying a liquid crystal composition on an alignment film to form a liquid crystal layer.
  • the film of the present invention preferably exhibits optical anisotropy.
  • the liquid crystal composition can be applied by a known method (eg, extrusion coating method, direct gravure coating method, reverse gravure coating method, die coating method, bar coating method).
  • the liquid crystalline molecules are preferably fixed while maintaining the alignment state.
  • the immobilization is preferably performed by a polymerization reaction of the polymerizable group (Q) introduced into the liquid crystal molecule.
  • the polymerization reaction includes a thermal polymerization reaction using a thermal polymerization initiator and a photopolymerization reaction using a photopolymerization initiator.
  • a photopolymerization reaction is preferred.
  • photopolymerization initiators include ⁇ -carbonyl compounds (described in US Pat. Nos. 2,367,661 and 2,367,670), acyloin ether (described in US Pat. No. 2,448,828), ⁇ -hydrocarbon substituted aromatic acyloin. Compound (described in US Pat. No. 2,722,512), polynuclear quinone compound (described in US Pat. Nos.
  • the amount of the photopolymerization initiator used is preferably 0.01 to 20% by mass, more preferably 0.5 to 5% by mass, based on the solid content of the coating solution.
  • Light irradiation for polymerization of discotic liquid crystalline molecules is preferably performed using ultraviolet rays.
  • the irradiation energy is preferably 20 mJ / cm 2 to 50 J / cm 2 , and more preferably 100 to 800 mJ / cm 2 .
  • light irradiation may be performed under heating conditions.
  • the thickness of the liquid crystal layer is preferably from 0.1 to 50 ⁇ m, more preferably from 1 to 30 ⁇ m, and most preferably from 2 to 20 ⁇ m.
  • the total coating amount of the compound represented by the general formula (I) in the liquid crystal layer is preferably 0.1 to 500 mg / m 2 , and preferably 0.5 to 450 mg / m 2. m 2 is more preferable, 0.75 to 400 mg / m 2 is further preferable, and 1.0 to 350 mg / m 2 is most preferable.
  • the film of the present invention is also preferably a layer formed by fixing the cholesteric liquid crystal phase of the liquid crystal composition of the present invention, in which case it preferably exhibits selective reflection characteristics, and exhibits selective reflection characteristics in the infrared wavelength region. It is particularly preferred. Details of the light reflecting layer formed by fixing the cholesteric liquid crystal phase are described in the methods described in JP 2011-107178 A and JP 2011-018037 A, and can be preferably used in the present invention.
  • the film of the present invention is also preferably a laminate comprising a plurality of layers formed by fixing the cholesteric liquid crystal phase of the liquid crystal composition of the present invention. Since the liquid crystal composition of the present invention has good lamination properties, such a laminate can be easily formed.
  • the alignment film is an organic compound (eg, ⁇ -tricosanoic acid) formed by rubbing treatment of an organic compound (preferably polymer), oblique deposition of an inorganic compound, formation of a layer having a microgroove, or Langmuir-Blodgett method (LB film). , Dioctadecylmethylammonium chloride, methyl stearylate). Furthermore, an alignment film in which an alignment function is generated by application of an electric field, application of a magnetic field or light irradiation is also known. An alignment film formed by a polymer rubbing treatment is particularly preferable.
  • an organic compound eg, ⁇ -tricosanoic acid
  • the rubbing treatment is carried out by rubbing the surface of the polymer layer several times in a certain direction with paper or cloth.
  • the type of polymer used for the alignment film is determined according to the alignment (particularly the average tilt angle) of the liquid crystal molecules.
  • a polymer that does not decrease the surface energy of the alignment film ordinary alignment film polymer
  • a polymer that lowers the surface energy of the alignment film is used.
  • the thickness of the alignment film is preferably 0.01 to 5 ⁇ m, and more preferably 0.05 to 1 ⁇ m.
  • the liquid crystal layer may be transferred onto the transparent support.
  • the liquid crystalline molecules fixed in the alignment state can maintain the alignment state even without the alignment film. In the case of orientation with an average inclination angle of less than 5 °, rubbing treatment is unnecessary and an orientation film is unnecessary.
  • an alignment film (described in JP-A-9-152509) forming a chemical bond with the liquid crystalline molecules at the interface may be used.
  • an alignment film is used for the purpose of improving adhesion, rubbing treatment need not be performed.
  • the liquid crystal layer formed on the transparent support can also function as an alignment film for the liquid crystal layer provided thereon.
  • the optically anisotropic element having the film of the present invention or the film of the present invention may have a transparent support.
  • a transparent support a glass plate or a polymer film, preferably a polymer film is used. That the support is transparent means that the light transmittance is 80% or more.
  • an optically isotropic polymer film is used as the transparent support.
  • the optical isotropy preferably has an in-plane retardation (Re) of less than 10 nm, more preferably less than 5 nm.
  • the thickness direction retardation (Rth) is preferably less than 10 nm, more preferably less than 5 nm.
  • the in-plane retardation (Re) and the thickness direction retardation (Rth) of the transparent support are respectively defined by the following formulas.
  • Re (nx ⁇ ny) ⁇ d
  • Rth [ ⁇ (nx + ny) / 2 ⁇ -nz] ⁇ d
  • nx and ny are in-plane refractive indexes of the transparent support
  • nz is the refractive index in the thickness direction of the transparent support
  • d is the thickness of the transparent support.
  • the transparent support preferably has optical uniaxiality or optical biaxiality.
  • optical uniaxial support even if it is optically positive (the refractive index in the optical axis direction is larger than the refractive index in the direction perpendicular to the optical axis), it is negative (the refractive index in the optical axis direction is It may be smaller than the refractive index in the vertical direction.
  • refractive indices nx, ny and nz in the above formula are all different values (nx ⁇ ny ⁇ nz).
  • the in-plane retardation (Re) of the optically anisotropic transparent support is preferably 10 to 1000 nm, more preferably 15 to 300 nm, and most preferably 20 to 200 nm.
  • the thickness direction retardation (Rth) of the optically anisotropic transparent support is preferably 10 to 1000 nm, more preferably 15 to 300 nm, and further preferably 20 to 200 nm.
  • the material for forming the transparent support is determined depending on whether it is an optical isotropic support or an optical anisotropic support.
  • an optically isotropic support glass or cellulose ester is generally used.
  • an optically anisotropic support a synthetic polymer (eg, polycarbonate, polysulfone, polyethersulfone, polyacrylate, polymethacrylate, norbornene resin) is generally used.
  • optical properties may be reduced by (1) using a retardation increasing agent, (2) reducing the acetylation degree of cellulose acetate, or (3) producing a film by the cooling dissolution method described in the specification of European Patent 0911656A2.
  • An isotropic (high retardation) cellulose ester film can also be produced.
  • the transparent support made of a polymer film is preferably formed by a solvent cast method.
  • an optically anisotropic transparent support it is preferable to perform a stretching process on the polymer film.
  • a normal uniaxial stretching process or biaxial stretching process may be performed.
  • an optical biaxial support it is preferable to perform an unbalanced biaxial stretching process.
  • unbalanced biaxial stretching the polymer film is stretched in a certain direction (for example, 3 to 100%, preferably 5 to 30%) and further in the direction perpendicular thereto (for example, 6 to 200%, preferably 10 to 90%).
  • the bi-directional stretching process may be performed simultaneously.
  • the stretching direction (the direction in which the stretching ratio is high in unbalanced biaxial stretching) and the slow axis in the plane of the stretched film are substantially the same direction.
  • the angle between the stretching direction and the slow axis is preferably less than 10 °, more preferably less than 5 °, and most preferably less than 3 °.
  • the thickness of the transparent support is preferably 10 to 500 ⁇ m, more preferably 50 to 200 ⁇ m.
  • surface treatment eg, glow discharge treatment, corona discharge treatment, ultraviolet light ( UV) treatment, flame treatment.
  • An ultraviolet absorber may be added to the transparent support.
  • An adhesive layer undercoat layer
  • the adhesive layer is described in JP-A-7-333433.
  • the thickness of the adhesive layer is preferably from 0.1 to 2 ⁇ m, and more preferably from 0.2 to 1 ⁇ m.
  • a coating solution having the following composition was prepared.
  • the concentration of the liquid crystal alignment accelerator was adjusted to 0.03 parts by mass, 0.05 parts by mass, 0.10 parts by mass, and 0.20 parts by mass with respect to the rod-like liquid crystal compound.
  • the following rod-like liquid crystal compound 1 100 parts by mass
  • the coating solution prepared above was weighed out in a volume of 50 ⁇ l using a micropipette and dropped onto glass with alignment film (SE-130) and spin-coated at a rotation speed of 2000 rpm. After heating at 85 ° C. for 2 minutes and allowing to cool for 1 minute, ultraviolet irradiation (ultraviolet light intensity: 500 mJ / m 2 ) is performed in a nitrogen atmosphere to form films of Examples and Comparative Examples showing optical anisotropy. did.
  • the film thicknesses of the films of Examples and Comparative Examples showing optical anisotropy were both about 5 ⁇ m.
  • the transmission spectrum of the film of Example 4 was measured using a spectrophotometer UV-3100PC manufactured by SHIMADZU. The results are shown in FIG. 1 that the film prepared in Example 4 is a selective reflection film having a central wavelength in the near-infrared region near 900 nm and exhibits optical anisotropy.
  • Example 106 (Synthesis of Compound (27)) Using the benzoic acid chloride derivative (2DA) obtained in the middle of the synthesis of the compound (17) in Example 101, the compound (27) used for the production of the film of Example 6 was synthesized according to the above-mentioned Scheme 4. did. 1 H NMR (400 MHz, CDCl 3 ) ⁇ 2.33-2.60 (m, 8H), 2.70-2.80 (m, 6H), 2.90-3.00 (m, 6H), 3. 77-3.85 (m, 4H), 4.35-4.52 (m, 8H), 7.84 (s, 2H)
  • ester (3b) 2- (perfluorohexyl) ethanol (18.2 g, 50 mmol) and tetrabutylammonium bromide (1.61 g, 5 mmol) were added to toluene, and sodium hydroxide 3. 5 g / 3.5 ml water was added.
  • Acrylic acid tertiary butyl ester (10.3 ml, 70 mmol) was slowly added dropwise in a 40 ° C. water bath and stirred at the same temperature for 1 hour. The reaction mixture was quenched by adding dilute hydrochloric acid, and the mixture was separated with an ethyl acetate / water system and concentrated by a rotary evaporator. Purification by column chromatography gave ester (3b) (19.0 g, 77% yield).

Abstract

L'invention concerne une composition de cristaux liquides qui contient des molécules de cristaux liquides et un composé représenté par la formule représentée ci-après. Si cette composition de cristaux liquides est soumise à un alignement de cristaux et transformée en un film, le film résultant a un faible trouble tout en ayant une faible énergie de surface, de telle sorte que le caractère répulsif peut être supprimé quand un stratifié de film composé de deux ou plus de couches est formé à base de celle-ci. (Dans la formule représentée ci-après, chacun parmi L1-L6 représente une simple liaison, -O-, -S-, -CO-, -COO-, -OCO-, -SCO-, -COS-, -NRCO-, -CONR-, -OCHR- ou -CHRO- ; chacun parmi Sp1-Sp4 représente une simple liaison ou un groupe alkylène ayant de 1 à 10 atomes de carbone ; A1 représente un groupe hydrocarboné aromatique (m + 1) valent ; A2 représente un groupe (n + 1) valent qui est formé d'une structure cyclique ; T1 représente une simple liaison ou un groupe divalent ou trivalent qui est formé d'une structure cyclique ; chacun parmi Hb1 et Hb2 représente un groupe fluoroalkyle ayant 2-30 atomes de carbone ; l est un nombre de 0 à 2 ; m est 2 ou 3 ; n est 1 ou 2 ; et m > n). (Hb1-Sp1-L1-Sp2-L2)m-A1-L3-T1-(L4-A2)l-(L5-Sp3-L6-Sp4-Hb2)n
PCT/JP2013/053807 2012-03-08 2013-02-18 Composé, composition de cristaux liquides, matière polymère et film WO2013132991A1 (fr)

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US11834441B2 (en) 2019-12-06 2023-12-05 Vertex Pharmaceuticals Incorporated Substituted tetrahydrofurans as modulators of sodium channels
US11919887B2 (en) 2019-12-06 2024-03-05 Vertex Pharmaceuticals Incorporated Substituted tetrahydrofurans as modulators of sodium channels
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