WO2016072436A1 - Composition de cristaux liquides photoréactifs, élément de régulation de la lumière et procédé de production d'un élément de régulation de la lumière - Google Patents

Composition de cristaux liquides photoréactifs, élément de régulation de la lumière et procédé de production d'un élément de régulation de la lumière Download PDF

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WO2016072436A1
WO2016072436A1 PCT/JP2015/081114 JP2015081114W WO2016072436A1 WO 2016072436 A1 WO2016072436 A1 WO 2016072436A1 JP 2015081114 W JP2015081114 W JP 2015081114W WO 2016072436 A1 WO2016072436 A1 WO 2016072436A1
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group
liquid crystal
ring
carbon atoms
photoreactive
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PCT/JP2015/081114
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English (en)
Japanese (ja)
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友之 佐々木
小野　浩司
喜弘 川月
耕平 後藤
悟志 南
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公立大学法人兵庫県立大学
国立大学法人長岡技術科学大学
日産化学工業株式会社
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Application filed by 公立大学法人兵庫県立大学, 国立大学法人長岡技術科学大学, 日産化学工業株式会社 filed Critical 公立大学法人兵庫県立大学
Priority to KR1020227022352A priority Critical patent/KR102541667B1/ko
Priority to JP2016557786A priority patent/JP6751348B2/ja
Priority to KR1020177014530A priority patent/KR102477725B1/ko
Priority to CN201580060542.0A priority patent/CN107075376B/zh
Publication of WO2016072436A1 publication Critical patent/WO2016072436A1/fr

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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
    • C09K19/08—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
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • 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
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • 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
    • 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
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • 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
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • 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
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/56—Aligning agents
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1334—Constructional arrangements; Manufacturing methods based on polymer dispersed liquid crystals, e.g. microencapsulated liquid crystals

Definitions

  • the present invention relates to a photoreactive liquid crystal composition, a light control device formed with the photoreactive liquid crystal composition, and a method for manufacturing the light control device.
  • the current liquid crystal display element uses a liquid crystal alignment film that has been subjected to an alignment treatment to uniformly align the liquid crystal, except for some elements such as polymer dispersed liquid crystal (PDLC) ( Non-patent document 1).
  • the alignment treatment of the liquid crystal alignment film is generally called a rubbing treatment after the liquid crystal alignment film is applied, and a method of rubbing the film surface with a roller wrapped with a cloth is used. Therefore, there is a problem that the display performance of the liquid crystal display element is deteriorated due to scratches and scraps caused by rubbing.
  • this alignment process requires a number of processes including a liquid crystal alignment film forming process, a liquid crystal alignment process process, and a liquid crystal alignment film cleaning process, which complicates the manufacturing process. For this reason, if a liquid crystal cell capable of controlling the orientation of the liquid crystal without using the liquid crystal alignment film can be produced, there are significant advantages in terms of process and cost.
  • PDLC creates a liquid crystal cell using a low-molecular liquid crystal mixed with a polymerizable compound that reacts with light in advance, and then polymerizes the polymerizable compound by irradiating ultraviolet rays from outside the cell to fix the liquid crystal.
  • Technology since the liquid crystal alignment process is not performed in the present technology, the alignment of the liquid crystal is not controlled, and the electro-optical characteristics are insufficient to apply the element to a light control element or a display element. (For example, refer nonpatent literature 1).
  • Japanese Patent Laid-Open No. 2006-201388 Japanese Patent Laid-Open No. 2003-307720.
  • an object of the present invention is to provide an element obtained by controlling the orientation of liquid crystal within the liquid crystal bulk without using a liquid crystal alignment film, specifically, a light control element, and / or the element.
  • the object is to provide a photoreactive liquid crystal composition for production.
  • the object of the present invention is to provide an element obtained by controlling the alignment of liquid crystal within the liquid crystal bulk without using a liquid crystal alignment film, specifically, dimming. It is to provide a method of manufacturing an element.
  • the composition is exposed to polarized ultraviolet light, and (A) a temperature that is 50 ° C. lower than the lower limit of the temperature range in which the photoreactive polymer liquid crystal exhibits liquid crystallinity, preferably 65 By heating the composition to ⁇ 150 ° C., more preferably 70 to 120 ° C., it is preferable that (B) the low molecular liquid crystal has a predetermined orientation.
  • (A) the photoreactive polymer liquid crystal may have (A-1) a photoreactive side chain that causes a photocrosslinking reaction.
  • the photoreactive polymer liquid crystal has the following formulas (1) to (6): (Wherein A, B and D are each independently a single bond, —O—, —CH 2 —, —COO—, —OCO—, —CONH—, —NH—CO—, —CH ⁇ CH—CO Represents —O— or —O—CO—CH ⁇ CH—; S is an alkylene group having 1 to 12 carbon atoms, and the hydrogen atom bonded thereto may be replaced by a halogen group; T is a single bond or an alkylene group having 1 to 12 carbon atoms, and a hydrogen atom bonded thereto may be replaced with a halogen group; Y 1 represents a ring selected from a monovalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring and alicyclic hydrocarbon having 5
  • R 0 is a hydrogen atom or a carbon number of 1 to 5 represents an alkyl group
  • R 0 is a hydrogen atom or a carbon number of 1 to 5 represents an alkyl group
  • Y 2 is a group selected from the group consisting of a divalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring, alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof
  • the hydrogen atom bonded to each independently represents —NO 2 , —CN, —CH ⁇ C (CN) 2 , —CH ⁇ CH—CN, a
  • R May be substituted with an alkyloxy group of R represents a hydroxy group, an alkoxy group having 1 to 6 carbon atoms, or the same definition as Y 1 ;
  • X is a single bond, —COO—, —OCO—, —N ⁇ N—, —CH ⁇ CH—, —C ⁇ C—, —CH ⁇ CH—CO—O—, or —O—CO—CH ⁇ .
  • X may be the same or different;
  • Cou represents a coumarin-6-yl group or a coumarin-7-yl group, and the hydrogen atoms bonded thereto are independently —NO 2 , —CN, —CH ⁇ C (CN) 2 , —CH ⁇ CH— May be substituted with CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms; one of q1 and q2 is 1 and the other is 0; q3 is 0 or 1; P and Q are each independently selected from the group consisting of a divalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring, alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof.
  • the photoreactive polymer liquid crystal has the following formulas (7) to (10): (Wherein A, B and D are each independently a single bond, —O—, —CH 2 —, —COO—, —OCO—, —CONH—, —NH—CO—, —CH ⁇ CH—CO Represents —O— or —O—CO—CH ⁇ CH—; Y 1 represents a ring selected from a monovalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring and alicyclic hydrocarbon having 5 to 8 carbon atoms, or the same or selected from those substituents.
  • R 0 is a hydrogen atom or a carbon number of 1 to 5 represents an alkyl group
  • R 0 is a hydrogen atom or a carbon number of 1 to 5 represents an alkyl group
  • —NO 2 is a hydrogen atom or a carbon number of 1 to 5 represents an alkyl group
  • —CN is a hydrogen atom or a carbon number of 1 to 5 represents an alkyl group
  • —NO 2 is a hydrogen atom or a carbon number of 1 to 5 represents an alkyl group
  • —CN is a hydrogen atom or a carbon number of 1 to 5 represents an alkyl group
  • X is a single bond, —COO—, —OCO—, —N ⁇ N—, —CH ⁇ CH—, —C ⁇ C—, —CH ⁇ CH—CO—O—, or —O—CO—CH ⁇ .
  • the hydrogen atom bonded to each independently represents —NO 2 , —CN, —CH ⁇ C (CN) 2 , —CH ⁇ CH—CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or 1 to 5 carbon atoms.
  • an alkyloxy group of R represents a hydroxy group, an alkoxy group having 1 to 6 carbon atoms, or the same definition as Y 1 ) It is preferable to have any one photoreactive side chain selected from the group consisting of:
  • the photoreactive polymer liquid crystal has the following formulas (11) to (13): (Wherein A is independently a single bond, —O—, —CH 2 —, —COO—, —OCO—, —CONH—, —NH—CO—, —CH ⁇ CH—CO—O—) Or represents —O—CO—CH ⁇ CH—; X is a single bond, —COO—, —OCO—, —N ⁇ N—, —CH ⁇ CH—, —C ⁇ C—, —CH ⁇ CH—CO—O—, or —O—CO—CH ⁇ .
  • X When CH is 2 and the number of X is 2, X may be the same or different; l represents an integer of 1 to 12, m represents an integer of 0 to 2, and m1 represents an integer of 1 to 3; R represents a ring selected from a monovalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring and alicyclic hydrocarbon having 5 to 8 carbon atoms, or the same or a phase selected from those substituents. Each of the hydrogen atoms bonded to them is independently —COOR 0 (wherein R 0 is a hydrogen atom or a carbon number of 1 to 5).
  • the photoreactive polymer liquid crystal has the following formula (14) or (15) (Wherein each A is independently a single bond, —O—, —CH 2 —, —COO—, —OCO—, —CONH—, —NH—CO—, —CH ⁇ CH—CO—O—, Or represents —O—CO—CH ⁇ CH—;
  • Y 1 represents a ring selected from a monovalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring and alicyclic hydrocarbon having 5 to 8 carbon atoms, or the same or selected from those substituents.
  • the photoreactive polymer liquid crystal has the following formula (16) or (17) (where A is a single bond, —O—, —CH 2 —, —COO—, —OCO—, —CONH—, Represents —NH—CO—, —CH ⁇ CH—CO—O—, or —O—CO—CH ⁇ CH—; X is a single bond, —COO—, —OCO—, —N ⁇ N—, —CH ⁇ CH—, —C ⁇ C—, —CH ⁇ CH—CO—O—, or —O—CO—CH ⁇ .
  • CH is 2 and the number of X is 2, X may be the same or different; l represents an integer of 1 to 12, and m represents an integer of 0 to 2) It is good to have the photoreactive side chain represented by these.
  • the photoreactive polymer liquid crystal has the following formula (20) (where A is a single bond, —O—, —CH 2 —, —COO—, —OCO—, —CONH—, —NH—). Represents CO—, —CH ⁇ CH—CO—O—, or —O—CO—CH ⁇ CH—; Y 1 represents a ring selected from a monovalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring and alicyclic hydrocarbon having 5 to 8 carbon atoms, or the same or selected from those substituents.
  • R 0 is a hydrogen atom or a carbon number of 1 to 5 represents an alkyl group
  • R 0 is a hydrogen atom or a carbon number of 1 to 5 represents an alkyl group
  • —NO 2 —CN, —CH ⁇ C (CN) 2 , —CH ⁇ CH—CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms May be substituted with an alkyloxy group
  • X is a single bond, —COO—, —OCO—, —N ⁇ N—, —CH ⁇ CH—, —C ⁇ C—, —CH ⁇ CH—CO—O—, or —O—CO—CH ⁇ .
  • CH is 2 and the number of X is 2, X may be the same or different; 1 represents an integer of 1 to 12, and m represents an integer of 0 to 2).
  • the step [III] is preferably performed during the step [II].
  • the step [III] is preferably performed after the step [II].
  • the weight ratio of (A) photoreactive polymer liquid crystal to (B) low molecular liquid crystal ((A) photoreactive polymer liquid crystal: (B) The low-molecular liquid crystal) is preferably 3:97 to 20:80, preferably 4:96 to 15:85, more preferably 5:95 to 13:87.
  • (A) the photoreactive polymer liquid crystal may have (A-1) a photoreactive side chain that causes a photocrosslinking reaction.
  • the photoreactive polymer liquid crystal may have the above formulas (1) to (6) (where A, B, D, S, T, Y 1 , Y 2 , R, X, Cou, q1, q2, q3, P, Q, l1, l2, H and I have the same definition as above, and any one light selected from the group consisting of It may have reactive side chains.
  • the photoreactive polymer liquid crystal may have the above formulas (7) to (10) (where A, B, D, Y 1 , X , L, m, m1, m2, n, Y 2 and R preferably have any one photoreactive side chain selected from the group consisting of:
  • the photoreactive polymer liquid crystal may have the above formulas (11) to (13) (where A, X, l, m, m1, and R preferably has any one photoreactive side chain selected from the group consisting of: ⁇ 21>
  • the photoreactive polymer liquid crystal is represented by the above formula (14) or (15) (where A, Y 1 , l, m1, and m2 Preferably have a photoreactive side chain having the same definition as above.
  • the photoreactive polymer liquid crystal has the above formula (16) or (17) (wherein A, X, l and m are the same as those described above). It has a photoreactive side chain represented by the same definition.
  • the photoreactive polymer liquid crystal has the above formula (20) (where A, Y 1 , X, l, and m are It may have a photoreactive side chain represented by the same definition).
  • an element obtained by controlling the alignment of liquid crystal in a liquid crystal bulk without using a liquid crystal alignment film specifically a light control element, and / or for producing the element.
  • a photoreactive liquid crystal composition can be provided.
  • an element obtained by controlling the orientation of the liquid crystal in the liquid crystal bulk without using a liquid crystal alignment film, specifically, a light control element is provided.
  • a method of manufacturing can be provided.
  • FIG. 2 An example of the ultraviolet irradiation device for manufacturing the light control element of this invention is shown.
  • FIG. 2 the results of measuring the transmitted light intensity (vertical axis) when the liquid crystal cells of Example 1, Comparative Example 2, and Comparative Example 3 were rotated (horizontal axis: angle) are shown.
  • FIG. 2 the results of measuring the transmitted light intensity (vertical axis) when the liquid crystal cells of Example 2, Comparative Example 4 and Comparative Example 5 were rotated (horizontal axis: angle) are shown.
  • the present application relates to an element obtained by controlling the orientation of liquid crystal in a liquid crystal bulk without using a liquid crystal alignment film, specifically a light control element, and / or a photoreactive liquid crystal composition for producing the element. Offer things.
  • the present application provides a method for manufacturing an element, specifically a light control element, obtained by controlling the alignment of liquid crystal within a liquid crystal bulk without using a liquid crystal alignment film.
  • a photoreactive liquid crystal composition, an element obtained by the composition, specifically a light control element, and a method for producing the element will be described.
  • the photoreactive liquid crystal composition of the present invention comprises a photoreactive side chain that generates at least one reaction selected from the group consisting of (A) (A-1) photocrosslinking and (A-2) photoisomerization. And (B) a low-molecular liquid crystal.
  • the photoreactive liquid crystal composition of the present invention comprises (A) a photoreactive polymer liquid crystal; and (B) a low molecular liquid crystal; so that the properties of (A) and (B) do not change. It may consist essentially of only (A) and (B) with other components.
  • the photoreactive liquid crystal composition of the present invention may have other components in addition to (A) or (B).
  • (B) Low molecular liquid crystal As the low molecular liquid crystal (B) contained in the photoreactive liquid crystal composition of the present invention, nematic liquid crystal, ferroelectric liquid crystal and the like conventionally used for liquid crystal display elements can be used as they are. Specifically, (B) as low-molecular liquid crystals, cyanobiphenyls such as 4-cyano-4′-n-pentylbiphenyl and 4-cyano-4′-n-feptyloxybiphenyl; cholesteryl acetate, cholesteryl benzoate, etc.
  • cyanobiphenyls such as 4-cyano-4′-n-pentylbiphenyl and 4-cyano-4′-n-feptyloxybiphenyl
  • cholesteryl acetate, cholesteryl benzoate etc.
  • the (A) photoreactive polymer liquid crystal (hereinafter sometimes simply referred to as “(A) component”) contained in the photoreactive liquid crystal composition of the present invention comprises (A-1) photocrosslinking, and (A-2) There is no particular limitation as long as it has a photoreactive side chain that generates at least one reaction selected from the group consisting of photoisomerization.
  • photoreactivity refers to a property that causes either (A-1) photocrosslinking or (A-2) photoisomerization reaction; and both reactions.
  • the component (A) preferably has (A-1) a side chain that causes a photocrosslinking reaction.
  • the component (A) is i) a polymer that exhibits liquid crystallinity in a predetermined temperature range, and is a polymer having a photoreactive side chain.
  • the component (A) preferably reacts with light in the wavelength range of 250 nm to 400 nm and exhibits liquid crystallinity in the temperature range of 50 to 300 ° C.
  • the component (A) preferably has iii) a photoreactive side chain that reacts with light in the wavelength range of 250 nm to 400 nm, particularly polarized ultraviolet rays.
  • the component (A) preferably has a mesogenic group because iv) exhibits liquid crystallinity in the temperature range of 50 to 300 ° C.
  • the weight ratio of (A) photoreactive polymer liquid crystal to (B) low molecular liquid crystal is 3:97 to 20:80, preferably 4:96 to 15:85, more preferably 5:95 to 13:87.
  • the component (A) has a photoreactive side chain having photoreactivity as described above.
  • the structure of the side chain is not particularly limited, but has a structure that causes the reaction shown in the above (A-1) and / or (A-2), and (A-1) has a structure that causes a photocrosslinking reaction. Is preferred.
  • (A-1) A structure that causes a photocrosslinking reaction is preferable in that the orientation of the component (A) can be stably maintained for a long time even if the structure after the reaction is exposed to external stress such as heat.
  • mesogenic component examples include, but are not limited to, a biphenyl group, a terphenyl group, a phenylcyclohexyl group, a phenylbenzoate group, and an azobenzene group.
  • the side chain of the component (A) is preferably a side chain composed of at least one of the following formulas (1) to (6).
  • A, B, and D are each independently a single bond, —O—, —CH 2 —, —COO—, —OCO—, —CONH—, —NH—CO—, —CH ⁇ CH—CO—.
  • S is an alkylene group having 1 to 12 carbon atoms, and the hydrogen atom bonded thereto may be replaced by a halogen group;
  • T is a single bond or an alkylene group having 1 to 12 carbon atoms, and a hydrogen atom bonded thereto may be replaced with a halogen group;
  • Y 1 represents a ring selected from a monovalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring and alicyclic hydrocarbon having 5 to 8 carbon atoms, or the same or selected from those substituents.
  • R 0 is a hydrogen atom or a carbon number of 1 to 5 represents an alkyl group
  • R 0 is a hydrogen atom or a carbon number of 1 to 5 represents an alkyl group
  • Y 2 is a group selected from the group consisting of a divalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring, alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof
  • the hydrogen atom bonded to each independently represents —NO 2 , —CN, —CH ⁇ C (CN) 2 , —CH ⁇ CH—CN, a
  • R May be substituted with an alkyloxy group of R represents a hydroxy group, an alkoxy group having 1 to 6 carbon atoms, or the same definition as Y 1 ;
  • X is a single bond, —COO—, —OCO—, —N ⁇ N—, —CH ⁇ CH—, —C ⁇ C—, —CH ⁇ CH—CO—O—, or —O—CO—CH ⁇ .
  • X may be the same or different;
  • Cou represents a coumarin-6-yl group or a coumarin-7-yl group, and the hydrogen atoms bonded thereto are independently —NO 2 , —CN, —CH ⁇ C (CN) 2 , —CH ⁇ CH— May be substituted with CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms; one of q1 and q2 is 1 and the other is 0; q3 is 0 or 1; P and Q are each independently selected from the group consisting of a divalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring, alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof.
  • P or Q on the side to which —CH ⁇ CH— is bonded is an aromatic ring;
  • the Ps may be the same or different, and when the number of Q is 2 or more, the Qs may be the same or different;
  • l1 is 0 or 1;
  • l2 is an integer from 0 to 2; when l1 and l2 are both 0,
  • A represents a single bond when T is a single bond; when l1 is 1, B represents a single bond when T is a single bond;
  • H and I are each independently a group selected from a divalent benzene ring, naphthalene ring, biphenyl ring, furan ring, pyrrole ring, and combinations thereof.
  • the side chain may be any one photoreactive side chain selected from the group consisting of the following formulas (7) to (10).
  • the side chain may be any one photoreactive side chain selected from the group consisting of the following formulas (11) to (13).
  • A, X, l, m, m1 and R have the same definition as above.
  • the side chain may be a photoreactive side chain represented by the following formula (14) or (15).
  • A, Y 1 , l, m1 and m2 have the same definition as above.
  • the side chain may be a photoreactive side chain represented by the following formula (16) or (17).
  • A, X, l and m have the same definition as above.
  • the side chain may be a photoreactive side chain represented by the following formula (20).
  • A, Y 1 , X, l and m have the same definition as above.
  • the component (A) may have any one liquid crystalline side chain selected from the group consisting of the following formulas (21) to (31).
  • the component (A) is represented by the following formulas (21) to (21) It is preferable to have any one liquid crystalline side chain selected from the group consisting of 31).
  • Y 3 is a group selected from the group consisting of a monovalent benzene ring, naphthalene ring, biphenyl ring, furan ring, nitrogen-containing heterocycle, alicyclic hydrocarbon having 5 to 8 carbon atoms, and combinations thereof.
  • each hydrogen atom bonded thereto may be independently substituted with —NO 2 , —CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms;
  • R 3 is a hydrogen atom, —NO 2 , —CN, —CH ⁇ C (CN) 2 , —CH ⁇ CH—CN, halogen group, monovalent benzene ring, naphthalene ring, biphenyl ring, furan ring, nitrogen-containing Represents a heterocyclic ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms; l represents an integer of 1 to 12, m represents an integer of 0 to 2, provided that in formulas (23) to (24), the sum of all m is 2 or more, and formulas (25) to (26 ), The sum of all m is 1
  • the component (A) is a copolymer of the photoreactive side chain monomer having the photoreactive side chain and, in some cases, copolymerizing the photoreactive side chain monomer and the monomer having the liquid crystalline side chain. Can be obtained.
  • the photoreactive side chain monomer refers to a monomer that can form a polymer having a photoreactive side chain at the side chain portion of the polymer when the polymer is formed.
  • the photoreactive group possessed by the side chain the following structures and derivatives thereof are preferred.
  • the photoreactive side chain monomer examples include hydrocarbon, (meth) acrylate, itaconate, fumarate, maleate, ⁇ -methylene- ⁇ -butyrolactone, styrene, vinyl, maleimide, norbornene and other radical polymerizable groups And a polymerizable group composed of at least one selected from the group consisting of siloxane and a photoreactive side chain composed of at least one of the above formulas (1) to (6), preferably, for example, the above formula ( A photoreactive side chain consisting of at least one of 7) to (10), a photoreactive side chain consisting of at least one of the above formulas (11) to (13), represented by the above formula (14) or (15)
  • the photoreactive side chain is preferably a structure having a photoreactive side chain represented by the above formula (16) or (17) and a photoreactive side chain represented by the above formula (20).
  • Examples of the photoreactive side chain monomer include the following formulas PRM-1 to PRM-11 (wherein n represents an integer of 1 to 6, m represents an integer of 0 to 4, and X represents a hydrogen atom or a methyl group)
  • R represents a hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms or an alkoxy group, a halogen atom, a cyano group, or a nitro group
  • R 1 to R 3 each independently represents a hydrogen atom , A straight-chain or branched alkyl group or alkoxy group having 1 to 3 carbon atoms, or a halogen atom
  • p is an integer of 1 to 4, but is not limited thereto. .
  • the liquid crystal side chain monomer means a monomer in which a polymer derived from the monomer exhibits liquid crystallinity and the polymer can form a mesogenic group at a side chain site. Even if the side chain has a mesogenic group such as biphenyl or phenylbenzoate alone, or a group that forms a mesogen structure by hydrogen bonding between side chains such as benzoic acid. Good. As the mesogenic group that the side chain has, the following structure is preferable.
  • liquid crystalline side chain monomers include hydrocarbon, (meth) acrylate, itaconate, fumarate, maleate, ⁇ -methylene- ⁇ -butyrolactone, styrene, vinyl, maleimide, norbornene and other radical polymerizable groups
  • a structure having a polymerizable group composed of at least one selected from the group consisting of siloxanes and a side chain composed of at least one of the above formulas (21) to (31) is preferable.
  • liquid crystalline side chain monomer for example, the following formulas LCM-1 to LCM-9 (wherein n represents an integer of 1 to 6, X represents a hydrogen atom or a methyl group, R 4 , R 6 and R 61 to R 63 each independently represent a hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms or an alkoxy group, a halogen atom, a cyano group, or a nitro group, and R 5 represents a hydrogen atom. , Represents a straight-chain or branched alkyl group having 1 to 6 carbon atoms), but is not limited thereto.
  • the component (A) can be obtained by the polymerization reaction of the above-described photoreactive side chain monomer that exhibits liquid crystallinity. Further, it can be obtained by copolymerization of a photoreactive side chain monomer that does not exhibit liquid crystallinity and a liquid crystalline side chain monomer, or by copolymerization of a photoreactive side chain monomer that exhibits liquid crystallinity and a liquid crystalline side chain monomer. it can. Furthermore, it can be copolymerized with other monomers as long as the liquid crystallinity is not impaired.
  • Examples of other monomers include industrially available monomers capable of radical polymerization reaction. Specific examples of the other monomer include unsaturated carboxylic acid, acrylic ester compound, methacrylic ester compound, maleimide compound, acrylonitrile, maleic anhydride, styrene compound and vinyl compound.
  • the unsaturated carboxylic acid include acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid and the like.
  • the acrylic ester compound include methyl acrylate, ethyl acrylate, isopropyl acrylate, benzyl acrylate, naphthyl acrylate, anthryl acrylate, anthryl methyl acrylate, phenyl acrylate, 2,2,2-trifluoroethyl acrylate, tert-butyl.
  • methacrylic acid ester compound examples include methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, benzyl methacrylate, naphthyl methacrylate, anthryl methacrylate, anthryl methyl methacrylate, phenyl methacrylate, 2,2,2-trifluoroethyl methacrylate, tert-butyl.
  • (Meth) acrylate compounds having a cyclic ether group such as glycidyl (meth) acrylate, (3-methyl-3-oxetanyl) methyl (meth) acrylate, and (3-ethyl-3-oxetanyl) methyl (meth) acrylate are also used. be able to.
  • Examples of the vinyl compound include vinyl ether, methyl vinyl ether, benzyl vinyl ether, 2-hydroxyethyl vinyl ether, phenyl vinyl ether, and propyl vinyl ether.
  • Examples of the styrene compound include styrene, methylstyrene, chlorostyrene, bromostyrene, and the like.
  • Examples of maleimide compounds include maleimide, N-methylmaleimide, N-phenylmaleimide, and N-cyclohexylmaleimide.
  • the production method of the side chain polymer of the present embodiment is not particularly limited, and a general-purpose method that is handled industrially can be used. Specifically, it can be produced by cationic polymerization, radical polymerization, or anionic polymerization using a vinyl group of a liquid crystalline side chain monomer or photoreactive side chain monomer. Among these, radical polymerization is particularly preferable from the viewpoint of ease of reaction control.
  • RAFT reversible addition-cleavage chain transfer
  • a radical thermal polymerization initiator is a compound that generates radicals when heated to a decomposition temperature or higher.
  • radical thermal polymerization initiators include ketone peroxides (methyl ethyl ketone peroxide, cyclohexanone peroxide, etc.), diacyl peroxides (acetyl peroxide, benzoyl peroxide, etc.), hydroperoxides (peroxidation).
  • the radical photopolymerization initiator is not particularly limited as long as it is a compound that initiates radical polymerization by light irradiation.
  • examples of such radical photopolymerization initiators include benzophenone, Michler's ketone, 4,4′-bis (diethylamino) benzophenone, xanthone, thioxanthone, isopropylxanthone, 2,4-diethylthioxanthone, 2-ethylanthraquinone, acetophenone, 2-hydroxy -2-methylpropiophenone, 2-hydroxy-2-methyl-4'-isopropylpropiophenone, 1-hydroxycyclohexyl phenyl ketone, isopropyl benzoin ether, isobutyl benzoin ether, 2,2-diethoxyacetophenone, 2,2 -Dimethoxy-2-phenylacetophenone, camphorquinone, benzanthrone, 2-methyl-1- [4- (
  • the radical polymerization method is not particularly limited, and an emulsion polymerization method, suspension polymerization method, dispersion polymerization method, precipitation polymerization method, bulk polymerization method, solution polymerization method and the like can be used.
  • the organic solvent used in the (A) component generation reaction is not particularly limited as long as the generated polymer is soluble. Specific examples are given below.
  • organic solvents may be used alone or in combination. Furthermore, even if it is a solvent which does not dissolve the polymer
  • the polymerization temperature at the time of radical polymerization can be selected from any temperature of 30 ° C. to 150 ° C., but is preferably in the range of 50 ° C. to 100 ° C.
  • the reaction can be carried out at any concentration, but if the concentration is too low, it is difficult to obtain a high molecular weight polymer, and if the concentration is too high, the viscosity of the reaction solution becomes too high and uniform stirring is difficult. Therefore, the monomer concentration is preferably 1% by mass to 50% by mass, more preferably 5% by mass to 30% by mass.
  • the initial stage of the reaction is carried out at a high concentration, and then an organic solvent can be added.
  • the molecular weight of the obtained polymer is decreased when the ratio of the radical polymerization initiator is large relative to the monomer, and the molecular weight of the obtained polymer is increased when the ratio is small, the ratio of the radical initiator is
  • the content is preferably 0.1 mol% to 10 mol% with respect to the monomer to be polymerized. Further, various monomer components, solvents, initiators and the like can be added during the polymerization.
  • the reaction solution is preferably put into a poor solvent.
  • the poor solvent used for precipitation include methanol, acetone, hexane, heptane, butyl cellosolve, heptane, methyl ethyl ketone, methyl isobutyl ketone, ethanol, toluene, benzene, diethyl ether, methyl ethyl ether, and water.
  • the polymer deposited in a poor solvent and precipitated can be recovered by filtration and then dried at normal temperature or under reduced pressure at room temperature or by heating.
  • the polymer collected by precipitation is redissolved in an organic solvent and reprecipitation and collection is repeated 2 to 10 times, impurities in the polymer can be reduced.
  • the poor solvent at this time include alcohols, ketones, hydrocarbons and the like, and it is preferable to use three or more kinds of poor solvents selected from these because purification efficiency is further improved.
  • the weight average molecular weight measured by GPC (Gel Permeation Chromatography) method is preferably 2000 to 1000000, more preferably 5000 to 200000.
  • the photoreactive liquid crystal composition of the present invention may have other components in addition to the component (A) or the component (B).
  • an antioxidant such as hindered amines and hindered phenols or one Examples thereof include a polymerizable compound having a photopolymerizable or photocrosslinkable group at the terminal.
  • the polymerizable compound include the following compounds (wherein V is represented by a single bond or —R 8 O—, preferably —R 8 O—, and R 8 has 1 to 10 carbon atoms, Preferably, it represents a linear or branched alkylene group having 2 to 6 carbon atoms, W is represented by a single bond or —OR 9 —, preferably —OR 9 —, and R 9 has 1 to 10 carbon atoms, preferably Represents a linear or branched alkylene group having 2 to 6 carbon atoms, and V and W may be the same or different, but can be easily synthesized if they are the same R 7 represents H or a carbon number 1 to 4 alkyl groups), but is not limited thereto.
  • This application also provides the light control element obtained by said photoreactive liquid-crystal composition, and the manufacturing method of this element.
  • the element of the present invention is formed having a liquid crystal cell having the above-described photoreactive liquid crystal composition.
  • the element of the present invention can be formed by filling a liquid crystal cell with the above-mentioned photoreactive liquid crystal composition.
  • the device of the present invention can be manufactured by the following steps. [I] (A) (A-1) a photoreactive polymer liquid crystal having a photoreactive side chain that causes at least one reaction selected from the group consisting of (A-1) photocrosslinking and (A-2) photoisomerization; And (B) filling a space formed between two transparent substrates arranged in parallel to each other with a photoreactive liquid crystal composition having a low-molecular liquid crystal; and forming a liquid crystal cell; and [II] [ A step of irradiating the liquid crystal cell obtained in I] with polarized ultraviolet light from any one of the two transparent substrates;
  • the element of the present invention specifically, the light control element can be formed.
  • the step [I] is a step of forming a liquid crystal cell by filling the above-mentioned photoreactive liquid crystal composition in a space formed between transparent substrates at least on the side irradiated with ultraviolet rays arranged in parallel and spaced apart. is there.
  • the liquid crystal cell is formed by forming a space by arranging two transparent substrates apart from each other in parallel and filling the space with the photoreactive composition described above.
  • the substrate for example, glass; plastic such as acrylic or polycarbonate, etc. can be used.
  • the substrate may have flexibility depending on the element to be formed.
  • the substrate is formed with various films on the space side, such as films formed from polyvinyl alcohol, polyether, polyethylene, PET, polyamide, polyimide, acrylic, polycarbonate, polyurea, etc. Also good.
  • membrane used here is good to show
  • the (A) photoreactive polymer liquid crystal is preferably disposed in a liquid crystal cell.
  • the photoreactive polymer liquid crystal is encapsulated in the liquid crystal cell as a composition with (B) a low molecular liquid crystal
  • (A) the molecular long axis of the photoreactive polymer liquid crystal is in the liquid crystal cell.
  • the low-molecular liquid crystal is also preferably arranged in the desired state in the liquid crystal cell. That is, (A) In order to cause a photoreaction of the photoreactive polymer liquid crystal sufficiently, the direction of incident light of polarized ultraviolet light is perpendicular to the direction of the molecular long axis of (A) photoreactive polymer liquid crystal.
  • the polarized ultraviolet light it is preferable to expose the polarized ultraviolet light so that
  • the molecular major axes of both (A) the photoreactive polymer liquid crystal and (B) the low molecular liquid crystal in the photoreactive composition are the substrate surface.
  • the film of the substrate is not limited to a material as long as it is such a film.
  • the step [II] is a step of irradiating the liquid crystal cell obtained in [I] with polarized ultraviolet rays. Since the polarized ultraviolet rays are irradiated from the outside of one of the two transparent substrates, the transparent substrate is a substrate that transmits the polarized ultraviolet rays as described above. Although polarized ultraviolet rays depend on the element to be formed, ultraviolet rays having a wavelength in the range of 100 nm to 400 nm can be used. Preferably, the optimum wavelength is selected through a filter or the like depending on the type of coating film to be used.
  • ultraviolet light having a wavelength in the range of 290 nm to 400 nm can be selected and used so that the photocrosslinking reaction can be selectively induced.
  • the ultraviolet light for example, light emitted from a high-pressure mercury lamp can be used.
  • the following mechanism occurs in the liquid crystal cell when irradiated with polarized ultraviolet rays. That is, the (A) photoreactive polymer liquid crystal in the liquid crystal cell has an orientation corresponding to the polarized ultraviolet light. Further, (B) the low molecular liquid crystal is aligned according to the alignment of (A) the photoreactive polymer liquid crystal. Thereby, (A) photoreactive polymer liquid crystal and (B) low molecular liquid crystal have orientation according to polarized ultraviolet rays.
  • (A) Photoreactivity A step of heating the liquid crystal cell to a temperature that is 50 ° C. lower than the lower limit of the temperature range in which the polymer liquid crystal exhibits liquid crystallinity.
  • the heating can be performed together with the exposure to polarized ultraviolet rays and / or the heating can be performed after the exposure to polarized ultraviolet rays.
  • the heating is (A) a temperature (Tx ⁇ 50) ° C.
  • Tx lower than the lower limit (Tx) of the temperature range in which the photoreactive polymer liquid crystal exhibits liquid crystallinity (Tx ⁇ 50) ° C. or higher, preferably Is carried out at 65 to 150 ° C, more preferably 70 to 120 ° C.
  • the “light control element” refers to an element that controls transmission / non-transmission of light from the back side by driving liquid crystal with controlled orientation by applying voltage, such as a display (display element) or Includes light control film (glass) for windows.
  • Example 1 After adding 5 parts by weight of the photoreactive polymer liquid crystal represented by the following formula P6CB to 95 parts by weight of a low molecular liquid crystal (E7) manufactured by Merck Co. represented by the following formula E7, the mixture was stirred at 180 ° C. for 20 minutes. A photoreactive liquid crystal composition was obtained.
  • liquid crystal cell A1 was produced by encapsulating the photoreactive liquid crystal composition in 2 ⁇ m gap parallel plate cells composed of glass substrates with ITO on both sides of the substrate.
  • the obtained liquid crystal cell A1 was exposed to polarized ultraviolet rays while being heated to 80 ° C., thereby forming a liquid crystal cell B1 in which the alignment of the liquid crystal was controlled.
  • the photoreactive polymer liquid crystal represented by the formula P6CB exhibited liquid crystallinity at 115 ° C. or higher.
  • linearly polarized light having a wavelength of 313 nm (22 mW / cm 2 ) is set to an exposure amount of 2 J / cm 2.
  • the temperature during exposure was controlled using a temperature controller manufactured by INSTEC.
  • the uniform exposure apparatus 1 in FIG. 1 has a UV light emitting section 2 that uniformly emits UV light over the entire light emitting surface, a polarizer 3 provided below the light emitting section, and a sample stage on which a sample 4 is placed. 5 Further, the temperature controller 6 between the sample 4 and the sample stage 5 can heat the sample during the exposure and / or heat the sample after the exposure via the temperature controller 6. Be placed.
  • the 2 includes a He—Ne laser 12, a polarizer 13, an analyzer 14, and a power meter 15.
  • the laser irradiated from the He—Ne laser 12 is a polarizer 13, an analyzer. 14 and power meter 15 are arranged in order. Further, the polarizer 13 and the analyzer 14 are arranged in a crossed Nicols state.
  • the sample 16 is disposed between the polarizer 13 and the analyzer 14, and the transmitted light intensity when the sample 16 is rotated is detected by the power meter 15.
  • Example 2 A liquid crystal cell A1 was prepared in the same manner as in Example 1. After the liquid crystal cell A1 was exposed to ultraviolet light polarized at room temperature, the liquid crystal cell was heated at 80 ° C. for 30 minutes to form a liquid crystal cell B2 in which the alignment of the liquid crystal was controlled. The obtained liquid crystal cell B2 was subjected to the experiment shown in FIG. 2 and the observation with a polarizing microscope in the same manner as in Example 1 to observe the alignment state of the low molecular liquid crystals (Table 1).
  • FIG. 4 shows the measurement results of the experiment shown in FIG. 2 for the liquid crystal cell B2. From FIG. 4, it was found that the liquid crystal in the liquid crystal cell B2 was uniaxially aligned.
  • Example 1 A liquid crystal cell CE1 was prepared in the same manner as in Example 1 except that the liquid crystal composition sealed in the parallel plate cell was only E7, and the liquid crystal cell CE1 was subjected to polarized light exposure in the same manner as in Example 1 and the transmitted light intensity was measured. did. As a result, even if the temperature of the heating performed together with the polarization exposure was changed, the angle dependency of the transmitted light intensity was not observed. Further, as a result of observation with a polarizing microscope, the alignment of the liquid crystal could not be confirmed.
  • Example 2 A liquid crystal cell A1 was prepared in the same manner as in Example 1.
  • the liquid crystal cell A1 was exposed to polarized ultraviolet rays while being heated at 30 ° C. to form a liquid crystal cell CE2.
  • the obtained liquid crystal cell CE2 was subjected to the experiment shown in FIG. 2 and the observation with a polarizing microscope in the same manner as in Example 1 to observe the alignment state of the low molecular liquid crystals (Table 1, FIG. 3).
  • the angle dependency of the transmitted light intensity was small, and sufficient uniaxial alignment of the liquid crystal could not be confirmed. Further, as a result of observation with a polarizing microscope, the alignment of the liquid crystal was insufficient.
  • Example 3 A liquid crystal cell A1 was prepared in the same manner as in Example 1. The liquid crystal cell A1 was exposed to polarized ultraviolet rays while being heated at 50 ° C. to form a liquid crystal cell CE3. The obtained liquid crystal cell CE3 was subjected to the experiment shown in FIG. 2 and the observation with a polarizing microscope in the same manner as in Example 1 for the alignment state of the low molecular liquid crystals (Table 1, FIG. 3). As a result, the angle dependency of the transmitted light intensity was small, and sufficient uniaxial alignment of the liquid crystal could not be confirmed. Further, as a result of observation with a polarizing microscope, the alignment of the liquid crystal was insufficient.
  • Example 4 A liquid crystal cell A1 was prepared in the same manner as in Example 1. After the liquid crystal cell A1 was exposed to ultraviolet light polarized at room temperature, the liquid crystal cell was heated at 30 ° C. for 30 minutes to form a liquid crystal cell CE4. The obtained liquid crystal cell CE4 was subjected to the experiment shown in FIG. 2 and the observation with a polarizing microscope in the same manner as in Example 1 for the alignment state of the low molecular liquid crystals (Table 1, FIG. 4). As a result, the angle dependency of the transmitted light intensity was small, and sufficient uniaxial alignment of the liquid crystal could not be confirmed. Further, as a result of observation with a polarizing microscope, the alignment of the liquid crystal was insufficient.
  • Example 5 A liquid crystal cell A1 was prepared in the same manner as in Example 1. After exposing the liquid crystal cell A1 to ultraviolet light polarized at room temperature, the liquid crystal cell was heated at 50 ° C. for 30 minutes to form a liquid crystal cell CE5. The obtained liquid crystal cell CE5 was subjected to the experiment shown in FIG. 2 and the observation with a polarizing microscope in the same manner as in Example 1 to observe the alignment state of the low molecular liquid crystals (Table 1, FIG. 4). As a result, the angle dependency of the transmitted light intensity was small, and sufficient uniaxial alignment of the liquid crystal could not be confirmed. Further, as a result of observation with a polarizing microscope, the alignment of the liquid crystal was insufficient.
  • the liquid crystal compositions of Examples 1 and 2 having the liquid crystal composition of the present invention that is, (A) a photoreactive polymer liquid crystal; and (B) a low molecular liquid crystal. While having photoreactivity, it was found that the liquid crystal composition of Comparative Example 1 did not exhibit photoreactivity. In addition, it was found that by using the liquid crystal composition of Example 1, a liquid crystal cell in which liquid crystals were uniaxially aligned could be produced. Further, comparing Examples 1 and 2 with Comparative Examples 2 to 5, it was found that by having a predetermined heating step, a liquid crystal cell in which liquid crystals were uniaxially aligned could be produced.

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Abstract

La présente invention concerne un élément et, plus précisément, un élément de régulation de la lumière qui est obtenu en régulant l'alignement des cristaux liquides au sein de cristaux liquides en vrac sans utiliser de film d'alignement de cristaux liquides ; et/ou une composition de cristaux liquides photoréactifs permettant de produire ledit élément. La présente invention concerne, donc, une composition de cristaux liquides photoréactifs qui contient (A) un cristal liquide photoréactif de poids moléculaire élevé comportant une chaîne latérale photoréactive qui subit au moins une réaction choisie dans le groupe constitué de (A-1) une photoréticulation et (A-2) une photoisomérisation, et (B) un cristal liquide de faible poids moléculaire, composition dans laquelle le rapport pondéral entre le composant (A) et le composant (B), c'est-à-dire composant (A) : composant (B) varie de 3 : 97 à 20 : 80 ; et un élément de régulation de la lumière qui est formé de façon à comporter une cellule à cristaux liquides comprenant ladite composition.
PCT/JP2015/081114 2014-11-06 2015-11-05 Composition de cristaux liquides photoréactifs, élément de régulation de la lumière et procédé de production d'un élément de régulation de la lumière WO2016072436A1 (fr)

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* Cited by examiner, † Cited by third party
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WO2018105312A1 (fr) * 2016-12-06 2018-06-14 Jnc株式会社 Composite de cristaux liquides et élément gradateur à cristaux liquides
CN109844066A (zh) * 2016-12-06 2019-06-04 捷恩智株式会社 液晶复合体及液晶调光元件
JPWO2018105312A1 (ja) * 2016-12-06 2019-10-24 Ｊｎｃ株式会社 液晶複合体および液晶調光素子
JP7036029B2 (ja) 2016-12-06 2022-03-15 Jnc株式会社 液晶複合体および液晶調光素子
CN109844066B (zh) * 2016-12-06 2023-09-19 捷恩智株式会社 液晶复合体及其用途、液晶调光元件、调光窗及智能窗户

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TW202244246A (zh) 2022-11-16
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