WO2019124153A1 - Composition de cristaux liquides, et élément d'affichage à cristaux liquides - Google Patents

Composition de cristaux liquides, et élément d'affichage à cristaux liquides Download PDF

Info

Publication number
WO2019124153A1
WO2019124153A1 PCT/JP2018/045432 JP2018045432W WO2019124153A1 WO 2019124153 A1 WO2019124153 A1 WO 2019124153A1 JP 2018045432 W JP2018045432 W JP 2018045432W WO 2019124153 A1 WO2019124153 A1 WO 2019124153A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
liquid crystal
general formula
independently
Prior art date
Application number
PCT/JP2018/045432
Other languages
English (en)
Japanese (ja)
Inventor
純一 間宮
雄一 井ノ上
正臣 木村
淳子 山本
Original Assignee
Dic株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dic株式会社 filed Critical Dic株式会社
Priority to JP2019560991A priority Critical patent/JP6828832B2/ja
Priority to CN201880075273.9A priority patent/CN111373019B/zh
Priority to KR1020207015046A priority patent/KR20200100624A/ko
Publication of WO2019124153A1 publication Critical patent/WO2019124153A1/fr

Links

Classifications

    • 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
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • 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
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/16—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon double bonds, e.g. stilbenes
    • 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
    • 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
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • 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
    • C09K19/38—Polymers
    • 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
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers

Definitions

  • the present invention relates to a liquid crystal composition containing three or more kinds of monomers and a liquid crystal display device using the same.
  • liquid crystal display devices such as liquid crystal panels and liquid crystal displays
  • the state of alignment of liquid crystal molecules is changed by an external stimulus such as an electric field, and the change in optical characteristics accompanying this is used for display.
  • a liquid crystal display element has a configuration in which liquid crystal molecules are filled in a gap between two transparent substrates, and the liquid crystal molecules are arranged in advance in a specific direction on the surface of the substrate in contact with the liquid crystal molecules. It is general to form an alignment film for making it.
  • Patent Document 1 instead of lauryl acrylate, which has relatively weak interaction with liquid crystal molecules, a highly linear monofunctional biphenyl monomer having an octyl group and a low straight line having a stearyl group are shown.
  • a liquid crystal composition containing a spontaneous alignment material that suppresses a decrease in voltage holding ratio by a liquid crystal composition containing a functional biphenyl monomer is described.
  • Patent Document 2 discloses various liquid crystal compositions including a polymerizable self-orientation additive that controls the alignment of liquid crystal molecules without using an alignment film. Specifically, when a liquid crystal composition containing a low molecular weight non-polymerizable liquid crystal component and a polymerizable self alignment additive is filled in a test cell without a polyimide alignment layer (test cell without a pre alignment layer), It has a spontaneous homeotropic (perpendicular) orientation with respect to the substrate surface, this orientation is kept stable up to the clearing point, and the formed VA cell is described as reversibly switchable by applying a voltage. There is.
  • a composition including two hydrophobic monomers each having a long alkyl chain and a biphenyl skeleton as shown in the above-mentioned Patent Document 1 has an interaction with liquid crystal molecules of a liquid crystal layer filled between a pair of substrates. Although it is considered to be stronger than lauryl acrylate, there arises a problem that the alignment direction of liquid crystal molecules can not be regulated due to the low adsorption power to the substrate.
  • Patent Document 2 describes a mode in which a non-polymerizable self-orienting additive and one type of polymerizable monomer are mixed with a polymerizable self-orienting additive having an adsorptive group which is a hydroxyl group or an amino group. Therefore, it is considered that the molecular design is in consideration of the adsorption force to the substrate. However, if the adsorptive power of the polymerizable self-orienting additive with respect to the substrate is too high, the polymerizable self-orienting additive does not spread uniformly on the substrate, causing a problem of uneven alignment. Also, the state of the layer polymerized in the state where the polymerizable self-orienting additive is adsorbed to the substrate is not considered.
  • the composition in which the non-polymerizable self-orienting additive and the polymerizable self-orienting additive are mixed or the polymerization component is the polymerizable self-orienting additive alone or one kind of the polymerizability Because it is any of the monomers, it is difficult to form a dense layer. If the dense layer is not formed, the vertical alignment component of the self-alignment additive is not fixed, and the amount of change in the pretilt angle becomes large, which causes a problem that the image sticking property is deteriorated.
  • the problem to be solved by the present invention is to provide a liquid crystal composition excellent in vertical alignment and burn-in characteristics, and to provide a liquid crystal display device using the same.
  • Another problem to be solved by the present invention is to provide a liquid crystal composition excellent in three properties of vertical alignment, low temperature solubility and burn-in characteristics, and to provide a liquid crystal display device using the same. is there.
  • the liquid crystal composition according to the present invention exhibits excellent vertical alignment to liquid crystal molecules and excellent burn-in characteristics.
  • the liquid crystal composition according to the present invention exhibits excellent spreadability (wet spread) with respect to a substrate.
  • the liquid crystal composition according to the present invention can be free from or non-uniform in orientation.
  • the liquid crystal display element according to the present invention exhibits no alignment unevenness or reduced alignment unevenness.
  • a first aspect of the present invention is one or more kinds of spontaneously orienting monomers having a mesogenic group, at least one polymerizable group represented by the general formula (PG1), and at least one adsorptive group, It is a liquid crystal composition including two or more types of polymerizable monomers selected from the group consisting of compounds represented by the following general formula (I) having a chemical structural formula different from the spontaneously orienting monomer.
  • P 11 is any group represented by the following Formula (PI) to Formula (P-IX),
  • R p11 and R p12 each independently represent a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms, and W p11 is a single bond, —O -, - COO- or a methylene group, t pi 1 represents 0, 1 or 2, wherein one or more hydrogen atoms of the polymerizable group P 11 may be substituted with the suction group).
  • S 11 represents a single bond or an alkylene group having 1 to 15 carbon atoms, one -CH 2 in the alkylene group - or nonadjacent two or more -CH 2 - directly oxygen atom It may be substituted by -O-, -OCO- or -COO- so that it is not adjacent, and one or more hydrogen atoms of S 11 may be substituted by the adsorptive group.
  • * In the above chemical formula represents a bond.
  • R 101, R 102, R 103, R 104, R 105, R 106, R 107, R 108, R 109 and R 110 are each independently, P 21 -S 21 - And an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a halogen atom or a hydrogen atom, and P 21 represents a group represented by the above formula (RI) to a formula (R-IX) Any group represented by),
  • the above S 21 represents a single bond or an alkylene group having 1 to 15 carbon atoms, and one or more of —CH 2 — in the alkylene group is —O— such that oxygen atoms are not directly adjacent to each other.
  • n 11 represents 0, 1 or 2
  • n 12 and n 13 each independently represent 0 or 1
  • represents n 11 + n 12 + n 13 1, 2 or 3
  • a 11 is a group (a), a group (b) and a group (c) shown below:
  • (A) 1,4-cyclohexylene group this is present in the group one -CH 2 - or nonadjacent two or more -CH 2 - may be replaced by -O-.
  • the liquid crystal composition according to the present invention contains at least three kinds of monomers having different chemical structures, it is easy to correspond to various polymerization conditions, and a polymer reaction is easy to progress, so a dense polymer network layer Can be formed.
  • the liquid crystal composition according to the present invention contains at least three kinds of monomers having different chemical structures, it is easy to correspond to various polymerization conditions, and a polymer reaction is easy to progress, so a dense polymer network layer Can be formed.
  • by using two or more kinds of polymerizable monomers it is possible to include two or more kinds of monomers whose function is separated from the group of polymerizable monomers involved in the polymerization reaction and the group of polymerizable monomers contributing to the vertical alignment. Therefore, it is considered that high vertical orientation and a small amount of pretilt change can be achieved.
  • the liquid crystal composition according to the present invention contains a spontaneous alignment monomer and a polymerizable monomer which are essential components as a polymerizable component, and a non-polymerizable liquid crystal compound as a liquid crystal component.
  • a spontaneous alignment monomer and a polymerizable monomer which are essential components
  • a non-polymerizable liquid crystal compound as a liquid crystal component.
  • the spontaneous orientation monomer according to the present invention is mainly used by being added to a liquid crystal composition, and a member (electrode (for example, ITO), substrate (for example, glass substrate, acrylic) directly in contact with the liquid crystal layer containing the liquid crystal composition Interact with the substrate, transparent substrate, flexible substrate, etc., resin layer (eg, color filter, alignment film, overcoat layer, etc.), insulating film (eg, inorganic material film, It has a function of inducing homeotropic alignment or homogeneous alignment of liquid crystal molecules.
  • a member electrode (for example, ITO), substrate (for example, glass substrate, acrylic) directly in contact with the liquid crystal layer containing the liquid crystal composition Interact with the substrate, transparent substrate, flexible substrate, etc., resin layer (eg, color filter, alignment film, overcoat layer, etc.), insulating film (eg, inorganic material film, It has a function of inducing homeotropic alignment or homogeneous alignment of liquid crystal molecules.
  • the above-mentioned spontaneously orienting monomer has a polymerizable group for polymerization, a mesogenic group similar to liquid crystal molecules, and an adsorptive group capable of interacting with members directly in contact with the liquid crystal layer, and if necessary alignment of liquid crystal molecules It is preferable to further have a bending group that induces
  • Polymerizable group The polymerizable group according to the present invention is a group represented by general formula (PG1), and P 11 is selected from the group represented by the following general formula (PI) to general formula (P-IX) Group.
  • R p11 and R p12 each independently represent a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms, and W p11 is a single bond, —O -, -COO- or a methylene group, and t p11 represents 0, 1 or 2.
  • the above P 11 is preferably a group selected from the group represented by the following Formula (PI) to Formula (P-IX), and is more preferably Formula (PI).
  • P 11 -S 11- may be bonded to a mesogenic group, an adsorptive group and / or a bending group.
  • the polymerizable group is preferably bonded directly to the mesogenic group, the adsorptive group or the bending group via a spacer group, or directly to the mesogenic group or the adsorptive group. Or it is more preferable to couple
  • the hydrogen atom in P 11 -S 11- may be substituted by a polymerizable group, an adsorptive group and / or a bending group.
  • the mesogenic group refers to a group having a rigid portion, for example, one having one or more cyclic groups, and preferably has 2 to 4 cyclic groups, and is preferably a cyclic group. Is more preferably 3 to 4. If necessary, the cyclic group may be linked by a linking group.
  • the mesogenic group is preferably a skeleton similar to the liquid crystal compound used in the liquid crystal layer.
  • cyclic group refers to an atomic group in which the constituting atoms are cyclically bound, and includes a carbocyclic ring, a heterocyclic ring, a saturated or unsaturated cyclic structure, a single ring, a bicyclic structure and a polycyclic ring. Including formula structures, aromatics, non-aromatics, etc. Also, the cyclic group may contain at least one hetero atom, and may be further substituted by at least one substituent (halogen atom, reactive functional group, organic group (alkyl, aryl etc.). When the group is a single ring, the mesogenic group preferably contains two or more single rings.
  • the said mesogenic group is represented, for example by General formula (AL).
  • a AL represents a divalent cyclic group, One or
  • Z AL is preferably a single bond or an alkylene group having 2 to 20 carbon atoms, and more preferably a single bond or an alkylene group having 2 to 10 carbon atoms.
  • One or two or more non-adjacent —CH 2 — in the alkylene group may be substituted with —O—, —COO— or —OCO—.
  • the number of the single bond which is a form in which a ring and a ring are directly connected and the number of atoms directly connecting the ring and the ring is an even number. For example, in the case of —CH 2 —CH 2 COO—, the number of atoms directly linking the ring to the ring is four.
  • the cyclic group is 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran-2,5-diyl group, 1,3-dioxane -2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, thiophene-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2,6 -Diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, thiophene-2,5-diyl group-, 1,2,3,4-tetrahydro Naphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene-2,7
  • a monovalent organic group is a group having a chemical structure constituted by the organic compound being in the form of a monovalent group, and is formed by removing one hydrogen atom from the organic compound.
  • an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, an alkenyloxy group having 2 to 15 carbon atoms, etc. Preferred is an alkyl group having 1 to 15 carbon atoms or an alkoxy group having 1 to 14 carbon atoms.
  • one or two or more non-adjacent —CH 2 — in the alkyl group, the alkenyl group, the alkoxy group and the alkenyloxy group may be substituted by —O—, —COO— or —OCO—.
  • the monovalent organic group may have a role as a bending group described later.
  • m AL is preferably an integer of 2 to 4.
  • Examples of the preferred form of the mesogen group include the following formulas (me-1) to (me-42).
  • General formula (AL) is a structure where two hydrogen atoms in these structures are eliminated.
  • a particularly preferred form is represented by the following general formula (AL-1) or (AL-2), and formula (AL-2) is more preferable.
  • X a11 ⁇ X al18 are each independently a hydrogen atom, a halogen atom, P 11 -S 11 -, represents an adsorption group or bend group
  • ring A and ring B are each independently a cyclohexane ring Or a benzene ring
  • One or more of X a11 to X al 18 are substituted with the above-mentioned adsorptive group
  • One or more of X a11 to X al 18 are substituted with the above-mentioned bending group
  • the adsorptive group and the bending group wherein P 11 -S 11 - may be substituted with, Having one or more - formula (AL-1) or the each of the general formulas (AL-2) P 11 -S 11.
  • X a16 preferably more than at least one or two ⁇ X a114 is substituted with polymerizable groups, X al9 or one of X a111 is P 11 -S 11 More preferably, it is substituted by-.
  • X a11 to X a13 , X a6 to X a114 , and X a117 to X a118 be substituted with a bending group
  • X a11 to X a13, X a6 ⁇ X a19, X a111 or at least one or two ⁇ X a114 or X a117 ⁇ X a118 it is preferably substituted in the bending group.
  • X a11 is substituted with a bending group, and any one of X a6 to X a19 or X a111 to X a114 is substituted with a bending group.
  • the number of carbon atoms in the former X a11 is larger than that in the latter X a11 .
  • Bending group P 11 -S 11 - may be substituted for.
  • X a11 or X a16 ⁇ X a110 is replaced by a suction group
  • X a11 or X a18 is substituted with an adsorptive group Is more preferred.
  • the adsorption group P 11 -S 11 - may be substituted for.
  • X a18 is preferably substituted with an adsorptive group.
  • the adsorbing group according to the present invention is a group having a function of adsorbing to an adsorbent such as a substrate, a film, an electrode and the like. Adsorption is generally separated into chemical adsorption in which a chemical bond (covalent bond, ionic bond or metal bond) is formed to be adsorbed between an adsorbent and an adsorbate, or physical adsorption other than the chemical adsorption.
  • the adsorption of the paper may be either chemical adsorption or physical adsorption, but it is preferable to adsorb with the adsorbent by physical adsorption.
  • the adsorptive group according to the present invention is preferably a group capable of physically adsorbing to the adsorbent, and the adsorptive group is more preferably bonded to the adsorbent by an intermolecular force.
  • bonded with an adsorbent by the said intermolecular force it has couple
  • the adsorptive group according to the present invention may be a donor or acceptor of a proton that mediates a hydrogen bond, or both.
  • the adsorptive group according to the present invention is preferably a group containing a polar element having an atomic group in which a carbon atom and a hetero atom are linked.
  • the polar element as used herein means an atomic group in which a carbon atom and a hetero atom are directly linked.
  • the hetero atom is preferably at least one selected from the group consisting of N, O, S, P, B and Si, and is at least one selected from the group consisting of N, O and S. Is preferable, and at least one selected from the group consisting of N and O is preferable, and O is preferable.
  • the valence of the polar element according to the present invention is not particularly limited, such as monovalent, divalent or trivalent, and the number of polar elements in the adsorptive group is also particularly limited. There is nothing to do.
  • the number of the adsorption groups is preferably 1 to 8 in one molecule, more preferably 1 to 4 and still more preferably 1 to 3.
  • the adsorptive group according to the present invention excludes P 11 -S 11 -and a bending group.
  • the adsorptive group according to the present invention contains one or more polar elements, and the adsorptive group is roughly classified into cyclic group type and chain group type.
  • a cyclic group type is a form that includes a cyclic group with a cyclic structure that includes a polar element in its structure
  • a chain group type includes a cyclic group that includes a cyclic structure that includes a polar element in its structure.
  • the chain group is a form having a polar element in a linear or branched chain group, and a part thereof may have a cyclic structure not containing a polar element.
  • the form in which the adsorptive group according to the present invention contains a cyclic group means a form in which at least one polar element is contained in a cyclic atomic arrangement.
  • the cyclic group in the present specification is as described above. Therefore, in the case where the adsorptive group according to the present invention contains a cyclic group, it only needs to contain a cyclic group containing a polar element, and the entire adsorptive group may be branched or linear. .
  • the adsorptive group according to the present invention is in the form of a chain group in that there is no cyclic atomic arrangement containing polar elements in the molecule, and at least one polar element can be linear (possibly branched) It means the form included.
  • chain group refers to an atomic group in which structural atoms have no linear atomic arrangement in the structural formula and in which the constituting atoms are linearly (or may be branched) bonded, and an acyclic group. .
  • a linear or branched aliphatic group which may contain either a saturated bond or an unsaturated bond, including, for example, alkyl, alkenyl, alkoxy, ester, ether or ketone, etc., at least one It is a concept which may be substituted by a substituent (reactive functional group (vinyl group, acryl group, methacryl group, etc.), chain organic group (alkyl, cyano, etc.). It may be linear or branched.
  • the adsorptive group according to the present invention preferably has a chain group or a cyclic group.
  • a chain group is preferable, and a cyclic group is preferable from the viewpoint of the stability to the liquid crystal composition.
  • the adsorptive group according to the present invention is a cyclic group, it has a heteroaromatic group having 3 to 20 carbon atoms (including a fused ring) or a heteroaliphatic group having 3 to 20 carbon atoms (including a fused ring) Is more preferable, a C 3-12 heteroaromatic group (including a fused ring) or a C 3-12 heteroaliphatic group (including a fused ring) is more preferable, and a 5-membered ring complex is more preferable.
  • it represents an aromatic group, a 5-membered ring heteroaliphatic group, a 6-membered ring heteroaromatic group or a 6-membered ring heteroaliphatic group, and the hydrogen atom in these ring structures is a halogen atom, the number of carbon atoms It may be substituted by 1 to 5 linear or branched alkyl groups or alkyloxy groups.
  • the adsorptive group according to the present invention is a chain group
  • a hydrogen atom or -CH 2 -in a linear or branched alkyl group having 1 to 20 carbon atoms be substituted by a polar element
  • the end portion contains a polar element or contains two or more polar elements.
  • the hydrogen atom of the adsorptive group according to the present invention may be substituted by a polymerizable group.
  • the type of polar element according to the present invention includes an oxygen atom-containing polar element (hereinafter, oxygen-containing polar element), a nitrogen atom-containing polar element (hereinafter, nitrogen-containing polar element), and a phosphorus atom Element (hereinafter, phosphorus-containing polar element), polar element including boron atom (hereinafter, boron-containing polar element), polar element including silicon atom (hereinafter, silicon-containing polar element) or polar element including sulfur atom (hereinafter, including It is preferable that it is a partial structure represented by (sulfur polar element), and from the viewpoint of adsorption capacity, nitrogen-containing polar element, nitrogen-containing polar element or oxygen-containing polar element is more preferable, and oxygen-containing polar element is even more preferable.
  • oxygen-containing polar element hereinafter, oxygen-containing polar element
  • nitrogen-containing polar element or oxygen-containing polar element is more preferable
  • oxygen-containing polar element is even more prefer
  • cyano group (-CN), primary amino group (-NH 2 ), secondary amino group (-NH-), tertiary amino group (-NRR '; however, R, R' Is at least one group selected from the group consisting of an alkyl group), pyridyl group, carbamoyl group (-CONH 2 ) and ureido group (-NHCONH 2 ), or a group in which the group is linked to a carbon atom Is preferred.
  • the boron-containing polar element is preferably a group in which a boric acid group (—B (OH) 2 ) is linked to a carbon atom.
  • silicon-containing polar element -Si (OH) 3 group or -Si (OR) (OR ') (OR''); provided that R, R' and R '' are alkyl groups, and the carbon atom is It is preferable that it is a connected group.
  • the adsorptive group according to the present invention is a group in which the cyclic group has an oxygen-containing polar element (hereinafter, an oxygen-containing cyclic group) and a group in which the cyclic group has a nitrogen atom polar element (hereinafter, a nitrogen-containing ring Formula group), a group in which the cyclic group has a phosphorus-containing polar element (hereinafter referred to as a phosphorus-containing cyclic group), a group in which the cyclic group has a boron-containing polar element (hereinafter referred to as a boron-containing cyclic group), cyclic A group having a silicon-containing polar element (hereinafter, a silicon-containing cyclic group), a group having a sulfur group containing a sulfur-containing polar element (hereinafter, a sulfur-containing cyclic group), a chain group having an oxygen-containing polar element (Hereinafter referred to as an oxygen-containing chain group), a chain
  • the above oxygen-containing cyclic group preferably has an ether group or a carbonyl group in the ring, and the ether group preferably contains the following groups.
  • the carbonyl group preferably contains any of the following groups.
  • the nitrogen-containing cyclic group preferably contains any of the following groups.
  • the above sulfur-containing cyclic group preferably contains any of the following groups.
  • the above-mentioned boron-containing cyclic group preferably contains any of the following groups.
  • the silicon-containing cyclic group preferably contains a silsesquioxane group [-(R) n (SiO 1.5 ) n-1 ].
  • the above oxygen-containing chain group preferably contains any of the following groups.
  • the above-mentioned nitrogen-containing chain group preferably contains the following groups.
  • R at , R bt , R ct and R dt each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • the above-mentioned sulfur-containing chain group preferably contains the following groups.
  • the silicon-containing chain group preferably contains —Si (OH) 3 or —Si (OR) (OR ′) (OR ′ ′), provided that R, R ′, R ′ ′ is an alkyl group).
  • the boron-containing chain group preferably contains -B (OH) 2 .
  • X t1 represents a linear or branched alkyl group having 1 to 18 carbon atoms or -NH 2
  • the hydrogen atom in the alkyl group is a cyano group
  • R t1 represents a hydrogen atom, and a carbon atom number of 1 to 5 alkyl groups or Z t1 carbon atoms which may combine with one to eight linear or branched alkylene group or Z t1 R 2 represents a linear or branched alkenylene group having 2 to 8 carbon atoms, and Z t2 represents a single bond, a linear or branched alkylene group having 1 to 18 carbon atoms, or carbon A linear or branched alkenylene group having 2 to 18 atoms is represented, and the alkylene group or -CH 2-of the alkenylene group is -O-, -COO-, -C so that the oxygen atom is not directly adjacent.
  • X t1 is -Z t2 -O-R at And when R at is an alkylene group or an alkenylene group, the hydrogen atom of Z t1 may be substituted and R t1 may be bonded to R t1, and W t0 is a linear or branched C 1-18 C atom
  • -, -OCO- may be substituted,
  • n t1 represents an integer of 0 or more and 4 or less,
  • Hydrogen atoms in the molecule of the polymerizable group P 11 -S 11 - may be substituted by, * represents a bond, mesogenic group, the polymerizable group which bonds to bend group or spacer group.
  • preferable X t1 represents a linear or branched alkyl group having 1 to 17 carbon atoms, -NH 2 or -Z t2 -O-R t1 group, and the alkyl group hydrogen atom a cyano group in, P 11 -S 11 - may be substituted by the above R t1 represents a hydrogen atom, a carbon atom bonded to an alkyl group or Z t1 of 1 to 5 carbon atoms 1 to represent the eight linear or branched alkylene group or Z t1 carbon atoms which may be coupled with 2 to 8 linear or branched alkenylene group, the Z t2 are single Represents a bond, a linear or branched alkylene group having 1 to 18 carbon atoms, or a linear or branched alkenylene group having 2 to 18 carbon atoms, and the alkylene group or —CH 2 of the corresponding alkenylene group 2 - is directly adjacent oxygen atom
  • W t2 represents a single bond or a divalent to tetravalent organic group
  • m t1 represents an integer of 1 to 3
  • hydrogen atoms in the molecule of the polymerizable group Pd-S 11 - may be substituted by
  • * represents a bond, mesogenic group, the polymerizable group, the bending group Or bond to a spacer group.
  • “-W t2 -Any” in the general formula (t) indicates that W t2 represents a single bond to a multivalent group, and the bond is monovalent to multivalent (Any).
  • a divalent to tetravalent organic group is a group having a chemical structure constituted by the organic compound being in the form of a divalent to tetravalent group, and a hydrogen atom is selected from the organic compound. It refers to an atomic group formed by removing two to four.
  • a divalent to tetravalent organic group -W t2 -Any is preferably a chain organic group, and, for example, a linear or branched C1 to C10 carbon atoms
  • the alkylene multivalent group is a trivalent or tetravalent group formed by removing one or two hydrogen atoms from the alkylene group, and a trivalent to tetravalent group having a free valence in a so-called hydrocarbon chain.
  • the group represented by the above general formula (t) is a preferred embodiment of W t0 in the general formula (T), that is, even though the adsorptive group (general formula (T)) is substituted by the adsorptive group (general formula (T))
  • W t2 is a trivalent organic group, that is, mt1 ′ is 2 and W t2 is nitrogen
  • W ta is an atom or an alkylene polyvalent group
  • the following general formula (ta) or (tb) may be mentioned.
  • R tc represents a hydrogen atom, a linear or branched carbon atoms 1 to 10 alkyl group or a polymerizable group P 11 -S 11 - Represented by Z t1 and Z t1 ′ independently represent the same meaning as Z t1 in the general formula (T), X t1 and X t1 ′ each independently represent the same meaning as Z t1 in the general formula (T), W t1 represents the same meaning as W t1 in the general formula (T), n t1 and n t1 ′ independently represent the same meaning as n t1 in the general formula (T), Hydrogen atoms in the molecule of the polymerizable group P 11 -S 11 - may be substituted by, * represents a bond, mesogenic group, the polymerizable group which bonds to bend group or spacer group.
  • Z t1 , Z t1 ′ and Z t1 ′ ′ each independently represent the same meaning as Z t1 in the general formula (T)
  • X t1 , X t1 ′ and X t1 ′ ′ each independently represent the same meaning as X t1 in the general formula (T)
  • W t1 represents the same meaning as W t1 in the general formula (T)
  • * represents a bond, which is bonded to a mesogen group, a polymerizable group, a bending group or a spacer group.
  • mt1 ′ is preferably 1 or 2, and mt1 ′ is more preferably 1. Further, among the embodiments represented by the above general formula (ta), general formula (tb) and general formula (tc), the embodiment represented by the above general formula (ta) is preferable .
  • -W t2 -Any is preferably a single bond or a divalent to trivalent organic group, and is a single bond or a linear or branched alkylene group having 1 to 8 carbon atoms
  • the —CH 2 — of the alkylene group may be substituted by —O— so that the oxygen atom is not directly adjacent to it, a linear or branched alkanetriyl group having 1 to 8 carbon atoms
  • the —CH 2 — of the alkanetriyl group may be substituted by —O— so that the oxygen atom is not directly adjacent to it, or a linear or branched alkyl-ylidene group (—CH of the alkyl-ylidene group concerned) 2- is more preferably -O- such that the oxygen atom is not directly adjacent.
  • the following groups may be mentioned.
  • R tc represents an alkyl group or a polymerizable group of 1 to 8 carbon atoms (P 11 -S 11 -) represent, NT0 is an integer of 1-7, * a is a bond . represented) Further, W polymerizable group to a hydrogen atom of t2 (P 11 -S 11 -) may be substituted.
  • mt1 preferably represents 1 or 2.
  • W t1 may be substituted for and bonded to a hydrogen atom of a mesogenic group, a polymerizable group or a bending group.
  • X t1 is a form not bound to Z t1 (chain group), and X t1 is a form (cyclic group) bound to Z t1 to form a ring Contains.
  • the former form it has 1 to 7 carbon atoms substituted with a linear or branched alkyl group having 1 to 8 carbon atoms, -NH 2 , -Z t2 -O-R t1 group or cyano group.
  • Linear or branched alkyl group is preferable, and a linear or branched alkyl group having 1 to 7 carbon atoms, a -Z t2 -O-R t1 group, or a carbon atom substituted with a cyano group
  • the linear or branched alkyl group of 1 to 7 is more preferable.
  • each R t1 independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
  • the above Z t2 is a single bond or a straight chain having 1 to 10 carbon atoms.
  • nt1 is 1 or more
  • X t1 is -Z t2 -O-R t1
  • R t1 is a linear or branched alkylene group having 1 to 7 carbon atoms or 2 carbon atoms It is preferable that R 7 be a linear or branched alkenylene group and that a hydrogen atom of Z t 1 be substituted and be bonded to R t 1 , for example, be represented by the following general formula (T ′) preferable.
  • R t1 ′ each independently represents a linear or branched alkylene group having 1 to 8 carbon atoms, or a linear or branched chain having 2 to 8 carbon atoms Represents an alkenylene group
  • Z t2 ' each independently represents a single bond, a linear or branched alkylene group having 1 to 10 carbon atoms, or a linear or branched alkenylene group having 2 to 10 carbon atoms
  • W t2 represents a single bond or a divalent to tetravalent organic group
  • -OCO- may be substituted
  • n t1 ' represents an integer of 1 or more and 4 or less
  • hydrogen atoms in the molecule of the polymerizable group P 11 -S 11 - may be substituted by
  • * represents a bond, mesogenic group, a polymerizable group, It bonds to a bending group or a spacer group.
  • the said alkylene trivalent group means the trivalent group which can remove one hydrogen atom further from an alkylene group.
  • the alkenylene trivalent group is a trivalent group obtained by further removing one hydrogen atom from an alkenylene group, a trivalent group having a free valence in a so-called hydrocarbon chain, such as an alkanetriyl group or an alkyl-ylidene group. Group etc.
  • nt1 preferably represents an integer of 0 or more and 3 or less, and more preferably nt1 represents an integer of 0 or more and 2 or less.
  • the general formula (T) is a cyclic group represented by any one of the general formulas (T-1-1) to (T-4-1) and any one of the general formulas (T-5-1) to (T-7-1) It is preferable that it is at least one selected from the group consisting of a chain group represented by When the adsorptive group represented by the general formula (T) according to the present invention selects a cyclic group, the general formula (T-1-1) or the general formula T-2-1) is preferred. When the adsorptive group represented by the general formula (T) according to the present invention selects a chain group, the general formula (T-5-1) or the general formula T-6-1) is preferred.
  • X a and X b each independently represent -O-, -S- or CH 2-
  • R t5 represents a linear or branched alkyl group having 1 to 8 carbon atoms, a cyanated alkyl group, or a linear or branched alkoxy group having 1 to 8 carbon atoms, and these alkyls
  • W t2 represents a single bond or a monovalent to tetravalent organic group
  • W t1 represents a single bond or a linear or branched alkylene group
  • n t1 represents an integer of 0 or more and 4 or less
  • mt1 represents an integer of 1 to 3
  • hydrogen atoms in the molecule of the polymerizable group P 11 -S 11 - may be substituted by, * represents a bond, mesogenic group, the polymerizable group, the bending group Or bond to a spacer group.
  • R tc represents a hydrogen atom, C 1 -C 7 alkyl group or a polymerizable group P 11 -S 11 - represented by a hydrogen atom in the molecule of the polymerizable group P 11 -S 11 -may be substituted, and * represents a bond, which is bonded to a mesogenic group, a polymerizable group, a bending group or a spacer group.
  • T-5-1 represents the general formula (T-5-2).
  • W t1 represents the same meaning as W t1 in the general formula (T-5)
  • R tc represents a hydrogen atom, an alkyl group or a polymerizable group of 1 to 7 carbon atoms P 11 -S 11 - in represented, n t1, n t2 and n t3 each independently represents 0 or 1, the hydrogen atom in the molecule P 11 -S 11 - may be substituted for).
  • Specific examples of the above general formula (T-5-1) include the following groups.
  • R tc represents a hydrogen atom, C 1 -C 7 alkyl group or a polymerizable group P 11 -S 11 - represented by a hydrogen atom in the molecule of the polymerizable group P 11 -S 11 -may be substituted, and * represents a bond, which is bonded to a mesogenic group, a polymerizable group, a bending group or a spacer group.
  • R tc represents a hydrogen atom, C 1 -C 7 alkyl group or a polymerizable group P 11 -S 11 - represented by a hydrogen atom in the molecule of the polymerizable group P 11 -S 11 may be substituted
  • * represents a bond, and is bonded to a mesogen group, a polymerizable group, a bending group or a spacer group
  • T-6-1 specific examples of the above general formula (T-6-1).
  • R c is a hydrogen atom, C 1 -C 7 alkyl group or a polymerizable group P 11 -S 11 - represented by a hydrogen atom in the molecule of the polymerizable group P 11 -S 11 -may be substituted, and * represents a bond, which is bonded to a mesogenic group, a polymerizable group, a bending group or a spacer group.
  • T-7-1 specific examples of the above general formula (T-7-1).
  • R c is a hydrogen atom, C 1 -C 7 alkyl group or a polymerizable group P 11 -S 11 - represented by a hydrogen atom in the molecule of the polymerizable group P 11 -S 11 -may be substituted, and * represents a bond, which is bonded to a mesogenic group, a polymerizable group, a bending group or a spacer group.
  • a mode in which the polar element contained in the adsorptive group or the polar element contained in the polymerizable group is localized is preferable.
  • the adsorptive group is an important structure for vertically aligning the liquid crystal composition, and by the adsorptive group and the polymerizable group being adjacent to each other, better alignment can be obtained, and good to the liquid crystal composition can be obtained. It shows solubility. Specifically, a form having a polymerizable group and an adsorptive group on the same ring of the mesogen group is preferable.
  • one or more polymerizable groups and one or more adsorptive groups are bonded to the same ring, respectively, and at least one of at least one or more adsorptive groups of one or more polymerizable groups, It includes a form in which one is bonded to the other and has a polymerizable group and an adsorptive group on the same ring.
  • the hydrogen atom of the spacer group (S 11 ) of the polymerizable group may be substituted with the adsorptive group, and further, the hydrogen atom of the molecule of the adsorptive group is the spacer group (S 11 ) of the polymerizable group It also includes the form of bonding.
  • At least one hydrogen atom of the polymerizable group may be substituted by an adsorptive group.
  • a preferable form in this case is a form in which at least one hydrogen atom of the polymerization group P 11 or a spacer group (S 11 ) optionally linked to the polymerization group is substituted by an adsorptive group, and a more preferable form the polymerizable group (P 11 -S 11 -) 1 or more hydrogen atoms in the include forms have been replaced by adsorptive group represented by the general formula (T).
  • R t11a , R t16a and R t151a each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • R t151 b and R t151 c each independently have 1 to carbon atoms 3 alkyl group, cyanated alkyl group having 1 to 3 carbon atoms
  • X a and X b represent -O-, -S- or CH 2-
  • L t151a and L t151 b each independently represent a single bond, a methylene group, an ethylene group, a propylene group, a vinylidene group, a vinylene group, an isopropenylene group or an ethylidene group
  • n t11 c , nt 151 c , nt 16 c , nt 151 d , nt 151 e , nt 151 f and nt 151 g each independently represent 0 or 1
  • L t151a and L t151a are each independently preferably a methylene group, an ethylene group, a vinylidene group, a vinylene group, an isopropenylene group or an ethylidene group.
  • n t11a , n t11b , n t16a , n t16b , n t151 a and n t151 b is preferably an integer of 1 to 8, and more preferably an integer of 1 to 5.
  • the bending group according to the present invention has a function of inducing the alignment of liquid crystal molecules, and preferably represents a linear or branched alkylene group having 1 to 20 carbon atoms, and a linear carbon atom It is more preferable to represent an alkylene group of the number 1 to 20, and more preferable to represent a linear alkylene group having 2 to 15 carbon atoms.
  • the above-mentioned bending group is bonded to a mesogen group from the viewpoint that the spontaneous alignment monomer has a so-called amphiphilic property to the liquid crystal layer.
  • the number of the above-mentioned bending groups is preferably 1 to 6, more preferably 1 to 4, and still more preferably 1 to 3.
  • the spontaneous orientation compound according to the present invention is preferably a compound represented by the following general formula (SAL).
  • T is represents an adsorptive group represented by the general formula (T)
  • MG is the general formula (AL) It represents a mesogenic group that is, Cg is a hydrogen atom, an adsorptive group represented by the above general formula (T), the polymerizable group is a -Sp al -P al or a linear or branched carbon atoms as the bending group
  • the polymerizable group is a -Sp al -P al or a linear or branched carbon atoms as the bending group
  • the polymerizable group is a -Sp al -P al or a linear or branched carbon atoms as the bending group
  • the polymerizable group is a -Sp al -P al or a linear or branched carbon atoms as the bending group
  • the polymerizable group is a -Sp al -P al or a linear or branched carbon atoms as the bending group
  • the polymerizable group
  • R p11 and R p12 each independently represent a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms, and W p11 is a single bond, —O -, -COO- or a methylene group, and t p11 represents 0, 1 or 2.
  • R al1 , R al2 , Z al1 , Z al2 , L al1 , L al2 , L al3 , L al4 , Sp 111 , Sp 112 , Sp 113 , Sp 114 , P 111 , P 112 , P 113 , P 113 114 , mal 1 , mal 2 , mal 3 , mal 4 , n al 1 , n al 2 , n al 3 , n al 4 , P 111 and P 112 are each independently of each other R al1 represents a hydrogen atom, a halogen atom, or a linear or branched alkyl group having 1 to 20 carbon atoms, and one or more -CH 2 -or two or more not adjacent to each other in the alkyl group.
  • R al2 said polymerizable group P 11 -S 11 - represents optionally substituted adsorbing group, preferably, the polymerization group P 11 -S 11 - Table at by even better above general formula substituted in (T)
  • R al2 is at least one selected from the group consisting of general formulas (T-1-1) to (T-7-1), more preferably general formula At least one selected from the group consisting of (T-1-1), (T-2-1), (T-5-1), and (T-6-1), Still more preferably, it is at least one selected from the group consisting of formulas (T-1-1.1), (T-6-1.1) and (T-5-1.1), Rings A al1 and A al2 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a 2,6-naphthylene group or a phenanthrene-2,
  • P 111 , P 112 , P 113 and P 114 each independently represent an acryl group or a methacryl group;
  • L al1 , L al2 , L al3 and L al4 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 15 carbon
  • 20 or more alkylene groups, and one or two or more non-adjacent -CH 2- in the alkylene group may be substituted with -O-, -C
  • the hydrogen atom on the substituent is a halogen atom, an 1,4-phenylene group optionally substituted by an alkyl group or an alkoxy group, a 2,6-naphthalene group or a 1,4-cyclohexyl group, but at least one of the substituents is P 11 -S 11 - It has been replaced, If Z ad1, A ad1 and Aa ad2 is present in plural may each also being the same or different, R ad1 is a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group, or P 11 -S 11 - represents, -CH 2
  • said polymerizable group P 11 -S 11 - represents optionally substituted adsorbing group, preferably, the polymerization group P 11 -S 11 - Table at by even better above general formula substituted in (T) R al2 is at least one selected from the group consisting of general formulas (T-1-1) to (T-7-1), more preferably general formula At least one selected from the group consisting of (T-1-1), (T-2-1), (T-5-1), and (T-6-1), Still more preferably, it is at least one selected from the group consisting of formulas (T-1-1.1), (T-6-1.1) and (T-5-1.1), P 11 -S 11- represents the above polymerizable group,
  • a plurality of Z ad1 , Z ad2 , A ad1 , mad 1 and / or A ad2 are present, they may be identical to or different from each other, provided that any one of A ad1 and A ad2 is at least one One P 11
  • a al 31 and A al 34 each independently represent 1,4-cyclohexylene, 1,4-phenylene, naphthalene-2,6-diyl or phenanthrene-2,7-diyl, and at least one of these rings is at least one
  • each hydrogen atom is a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, or an alkenyloxy group having 2 to 11 carbon atoms In these groups, at least one hydrogen atom may be substituted
  • the spontaneous orientation monomer has a bending group for aligning liquid crystal molecules at one end of the mesogenic group, and a structure having a polymerizable group and an adsorptive group at the other end of the mesogenic group.
  • a substance having in one molecule a nonpolar portion having an affinity for the liquid crystal layer and a polar portion having a low affinity for the liquid crystal layer Is considered to lower the interface free energy by being aligned on the interface.
  • the lower limit of the content of the spontaneous orientation monomer in the liquid crystal composition of the present invention is preferably 0.02% by mass, preferably 0.03% by mass, preferably 0.04% by mass, and more preferably 0.05% by mass.
  • 0.06 mass% is preferable, 0.07 mass% is preferable, 0.08 mass% is preferable, 0.09 mass% is preferable, 0.1 mass% is preferable, 0.12 mass% is preferable, 0.
  • the upper limit of the content of the polymerizable monomer represented by the general formula (I) in the liquid crystal composition of the present invention is preferably 2.5% by mass, preferably 2.3% by mass, and preferably 2.1% by mass.
  • 2 mass% is preferable, 1.8 mass% is preferable, 1.6 mass% is preferable, 1.5 mass% is preferable, 1 mass% is preferable, 0.95 mass% is preferable, and 0.9 mass% is 0.85% by mass is preferable, 0.8% by mass is preferable, 0.75% by mass is preferable, 0.7% by mass is preferable, 0.65% by mass is preferable, and 0.6% by mass is preferable, 0.55 mass% is preferable, 0.5 mass% is preferable, 0.45 mass% is preferable, and 0.4 mass% is preferable.
  • a particularly preferable specific example of the spontaneous orientation monomer according to the present invention is a compound represented by the following general formula (al-1-1).
  • R ala and R alb above P 11 -S 11 - preferably represents a.
  • R al 4 is a group represented by any one of the general formulas (T-1-1) to (T-7-1) or the formula (T-1-1.1), (T-6) -1.1) or (T-5-1.1) is preferred.
  • Examples of preferable compounds represented by the above general formula (al-1) include compounds represented by the following formulas (AL-1.1) to (AL-1.18).
  • Preferred examples of the compound represented by the above general formula (al-2) include compounds represented by the following formulas (AL-2.1) to (AL-2.48).
  • the polymerizable monomer according to the present invention includes, in the liquid crystal composition, two or more selected from the group consisting of compounds represented by the following general formula (I) having a chemical structural formula different from the above-mentioned spontaneous orientation monomer.
  • R 101, R 102, R 103, R 104, R 105, R 106, R 107, R 108, R 109 and R 110 are each independently, P 21 -S 21 - And an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a halogen atom or a hydrogen atom, and P 21 represents a group represented by the following formula (PI) to formula (P-IX) Any group represented by),
  • R p11 and R p12 each independently represent a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms, and W p11 is a single bond, —O -, -COO- or a methylene group, and t p11 represents 0, 1 or 2.
  • the above S 21 represents a single bond or an alkylene group having 1 to 15 carbon atoms, and one or more of —CH 2 — in the alkylene group is —O— such that oxygen atoms are not directly adjacent to each other.
  • n 11 represents 0, 1 or 2
  • n 12 and n 13 each independently represent 0 or 1
  • represents n 11 + n 12 + n 13 1, 2 or 3
  • a 11 is a group (a), a group (b) and a group (c) shown below:
  • (A) 1,4-cyclohexylene group this is present in the group one -CH 2 - or nonadjacent two or more -CH 2 - may be replaced by -O-.
  • the tilt angle of liquid crystal molecules can be formed by the first polymerization process of the polymerizable monomer and the spontaneous alignment monomer present in the composition. It becomes easy to construct a network of polymers.
  • the liquid crystal composition at least three monomers of one or more kinds of spontaneous orientation monomers and two or more kinds of polymerizable monomers, each having a different chemical structure, are present.
  • a monomer that can trigger the polymerization reaction can promote the reaction of other monomers in response to a wide range of reaction conditions. More specifically, in the case of polymerization by UV irradiation, the chemical structure, in particular, the mesogen skeleton that most affects the absorption of light and the substituent that binds to the mesogen skeleton differ from these three, so It is believed that the monomer with the longest absorption wavelength can promote the reaction of two or more other monomers. This is considered to facilitate formation of a polymer network of a size that can form the tilt angle of liquid crystal molecules in the first polymerization process of the polymerizable monomer and the spontaneous alignment monomer present in the composition.
  • the polymerizable monomer according to the present invention includes 2 to 4 polymerizable monomers selected from the group consisting of compounds represented by the above general formula (I) having a chemical structural formula different from the above-mentioned spontaneously orienting monomer. Is preferable, 2 to 3 types are more preferable, and 2 types are particularly preferable.
  • R 101 and R 110 are each independently, P 21 -S 21 - is preferably.
  • the above P 21 is preferably a general formula (PI).
  • S 21 preferably represents a single bond or an alkylene group having 1 to 8 carbon atoms, and one or more of —CH 2 — in the alkylene group is an oxygen atom It is more preferable to represent a single bond or an alkylene group having 1 to 5 carbon atoms, which may be substituted by -O-, -OCO- or -COO-, such that is not directly adjacent.
  • a 11 is a group selected from the group consisting of 1,4-cyclohexylene group, 1,4-phenylene group, naphthalene-2,6-diyl group and 2,7-phenanthrendiyl preferably representing, the a 11 is an alkyl group having 1 to 5 carbon atoms, it may be substituted with an alkoxy group or a fluorine atom of 1 to 5 carbon atoms.
  • L 10 and L 11 are each independently a single bond, -OCH 2 -, - CH 2 O -, - C 2 H 4 -, - OC 2 H 4 O -, - COO It is preferable to represent-or -OCO-, and it is more preferable that L 10 and L 11 represent a single bond.
  • one of the polymerizable monomers represented by the general formula (I) in the above general formula (I) has n 11 of 0 and R 102 , R 103 , R 104 , any one of R 105, R 106, R 107 , R 108 or R 109 is an alkyl group having from 1 to 18 carbon atoms, independently R 101 and R 110 are each, P 21 -S 21 - in Is preferred.
  • the polymerizable monomer represented by the general formula (I) according to the present invention is represented by the following general formula (RM-1), general formula (RM-2) and general formula (RM-3) It is preferable that it is 2 or more types selected from the polymerizable monomer group.
  • R 101 is, P 33 -S 33 - represents, R 110 is, P 44 -S 44 - represents, P 33 and P 44
  • R 102 , R 104 , R 107 and R 109 each independently represent an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a fluorine atom or a hydrogen atom
  • a 11 represents a 1,4-phenylene group, a 1,4-cyclohexylene group, a naphthalene-2,6-diyl group or a 2,7-phenanthrendiyl group, and the A 11 is unsubstituted or carbon It may be substituted by an alkyl group having 1 to 5 atoms, an alkoxy group having 1 to 5 carbon atoms, or a halogen (a fluorine atom or a chlorine atom),
  • Each of R 103 , R 105 , R 106 and R 108 independently represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a fluorine atom or a hydrogen atom.
  • X M1 to X M8 each independently represent a hydrogen atom or a fluorine atom
  • S M2 and S M3 each independently represent an alkylene group having 1 to 12 carbon atoms or a single bond, and in the alkylene group, —CH 2 — in the alkylene group is an oxygen atom as —O 2 as the oxygen atom does not directly bond with each other -, -OCO- or OCOO- may be substituted
  • R M2 and R M3 represent any one of the above formulas (P-1) to (P-15).
  • the liquid crystal composition according to the present invention preferably contains at least one polymerizable monomer having a long absorption wavelength.
  • the polymerizable monomer having a long absorption wavelength is preferably a structure having a biphenyl skeleton and having two or more (meth) acrylic functional groups, and the biphenyl skeleton may be substituted with a halogen atom, an alkyl group or an alkoxy group. Good.
  • the polymerizable monomer represented by General Formula (RM-2) includes two or more types Aspect, an aspect including the polymerizable monomer represented by the general formula (RM-1) and the polymerizable monomer represented by the general formula (RM-2), or the polymerizable monomer represented by the general formula (RM-2) And three polymerizable monomers represented by formula (RM-3).
  • a liquid crystal display device using a liquid crystal composition containing a PSA process or a spontaneous alignment agent or a polymerizable monomer cures the spontaneously aligned monomer or the polymerizable monomer in the liquid crystal composition by irradiating light once or twice.
  • a polymer network is formed on the substrate surface, and the tilt angle of liquid crystal molecules is controlled by the network.
  • the amount of change in tilt angle with time in the liquid crystal display element can be reduced and burn-in can be reduced. it is conceivable that.
  • liquid crystal composition containing one or more types of spontaneous alignment monomers and two or more types of polymerizable monomers, polymerization becomes possible in the light absorption bands of these at least three monomers.
  • the reaction is likely to occur, and it is considered that the monomer having the longest absorption wavelength among the at least three monomers can promote the reaction of the other two or more monomers as a polymerization trigger (the so-called initiator role). . Therefore, it is preferable to include at least one polymerizable monomer having a long absorption wavelength.
  • an embodiment including two or more types of polymerizable monomers represented by the above general formula (RM-2), a polymerizable monomer represented by the general formula (RM-1), and the general formula (RM-2) Preferred is an embodiment including the polymerizable monomer represented by the above or an embodiment including the polymerizable monomer represented by the general formula (RM-2) and the polymerizable monomer represented by the general formula (RM-3).
  • the tilt angle of liquid crystal molecules is controlled in the first light irradiation step.
  • a polymerizable monomer having a long absorption wavelength will be used, but the polymerizable monomer having a long absorption wavelength has a structure containing a large number of aromatic rings, and thus a liquid crystal composition is obtained.
  • the desired concentration can not be added from the viewpoint of compatibility or low temperature stability.
  • the domains constituting the polymer network become sparse, so that the tilt angle with respect to the liquid crystal molecules can not be controlled. It is considered that the stability of the tilt angle is low in the method of reinforcing the polymer network by curing the polymerizable monomer and the spontaneous orientation monomer remaining after the first light irradiation step.
  • a liquid crystal composition according to the present invention as a more preferable embodiment having two or more types of polymerizable monomers, an embodiment including two or more types of polymerizable monomers represented by the following general formula (RM-2-1), the following general formula An embodiment containing a polymerizable monomer represented by (RM-1-1) and a polymerizable monomer represented by the following general formula (RM-2-1), or represented by the following general formula (RM-2-1) And the polymerizable monomer represented by the following general formula (RM-3).
  • P RM1 and P RM2 are each independently any one of the above formulas (PI) to (P-IX) Sp RM1 and Sp RM2 each independently represent a single bond or an alkylene group having 1 to 7 carbon atoms, and one or more of —CH 2 — in the alkylene group is an oxygen atom It may be substituted by -O-, -OCO- or COO-, so as not to be directly adjacent to each other, R 102 to R 109 each independently represent an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a fluorine atom or a hydrogen atom, R 111 , R 112 , R 113 and R 114 each independently represent an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a fluorine atom or a hydrogen atom.
  • RM-1-1 and P RM2 are each independently any one of the above formulas (PI) to
  • R 102 to R 114 preferably has an alkyl group having 1 to 4 carbon atoms or a fluorine atom, and R 111 to R 114 are At least one of them preferably has a fluorine atom.
  • the liquid crystal composition according to the present invention contains a liquid crystal component, and the liquid crystal component contains a non-polymerizable liquid crystal compound.
  • the liquid crystal compound as a liquid crystal component according to the present invention is a compound represented by the general formula (L), a compound represented by the general formula (J), a compound represented by the general formula (N-1), It is preferable to include one or more selected from the group consisting of a compound represented by N-2) and a compound represented by General Formula (N-3).
  • a compound represented by General Formula (L), a compound represented by General Formula (N-1), and a compound represented by General Formula (N-2) It is preferable to include one or two or more compounds selected from the group consisting of the compound represented by the general formula (N-3) and the compound represented by the general formula (N-3).
  • the entire liquid crystal composition exhibits negative dielectric anisotropy, it preferably contains a compound represented by General Formula (L) and a compound represented by General Formula (J).
  • the liquid crystal compound according to the present invention comprises, as a first component, one or two or more compounds represented by the general formula (L) of a dielectric substantially neutral compound (the value of ⁇ is ⁇ 2 to 2) It is preferable to contain.
  • a L1 , A L2 and A L3 are each independently (a) 1,4-cyclohexylene group (one —CH 2 — present in this group or two or more non-adjacent —CH 2 — groups May be replaced by -O-.)
  • the group (a), the group (b) and the group (c) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom
  • n L1 is 2 or 3 and a plurality of A L2 is present, they may be the same or different, and when n L1 is 2 or 3 and a plurality of Z L2 is present, they may be May be the same or different.
  • the liquid crystal composition according to the present invention contains a non-polymerizable liquid crystal compound, and the non-polymerizable liquid crystal compound has, as a second component, a general formula (J) of a dielectrically positive compound ( ⁇ is larger than 2). And / or compounds represented by general formulas (N-1) to (N-3) of dielectrically negative compounds (the sign of ⁇ is negative and the absolute value is larger than 2) It is preferable to contain one or more kinds.
  • the compound represented by General Formula (J) of the dielectrically positive compound ( ⁇ is larger than 2) is as follows.
  • a J1 , A J2 and A J3 are each independently (A) 1,4-cyclohexylene group (this is present in the group one -CH 2 - or nonadjacent two or more -CH 2 - may be replaced by -O-.)
  • Group (a), group (b) and group (c) are each independently a cyano group, a fluorine atom, a chlorine atom, a methyl group, a trifluoromethyl group or a trifluoro group It may be substituted by a methoxy group
  • Z J1 and Z J2 are each independently a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O -, -COO-, -OCO- or -C ⁇ C-,
  • n J1 is 2, 3 or 4 and there are a plurality of A J2 , they may be the same or different, and n J1 is 2, 3 or 4 and a plurality of Z J1 is present If they are identical or different,
  • X J1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a
  • R L1 and R L2 each independently represent the same meaning as in general formula (L), and A L1 and A L7 each independently represent the same meaning as in general formula (L);
  • the hydrogen atom on L1 and A L2 may be each independently substituted by a fluorine atom, and Z L1 has the same meaning as Z L2 in formula (L), and X L1 and X L2 are each independently Represents a fluorine atom or a hydrogen atom
  • J a compound represented by General formula (J)
  • the compound represented by General formula (M) and the compound represented by General formula (K) are preferable.
  • R M1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy having 2 to 8 carbon atoms Group is preferable, and an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms is preferable.
  • An alkyl group of 1 to 5 or an alkenyl group of 2 to 5 carbon atoms is further preferable, an alkyl group of 2 to 5 carbon atoms or an alkenyl group of 2 to 3 carbon atoms is further preferable, and an alkenyl group of 3 carbon atoms (Propenyl group) is particularly preferred.
  • R M1 is preferably an alkyl group, and when importance is attached to decrease in viscosity, it is preferably an alkenyl group.
  • the ring structure to which it is bonded is a phenyl group (aromatic)
  • a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and carbon Alkenyl group having 4 to 5 atoms is preferable
  • a linear alkyl group having 1 to 5 carbon atoms, a straight chain Preferred is an alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms.
  • the total of carbon atoms and oxygen atoms, if present is preferably 5 or less, preferably linear.
  • the alkenyl group is preferably selected from the groups represented by any one of formulas (R1) to (R5). (The black dot in each formula represents a carbon atom in a ring structure to which an alkenyl group is bonded.)
  • a M1 and A M2 are each preferably aromatic when it is required to increase ⁇ n independently, and in order to improve the response speed, it is preferably aliphatic, and trans-1,4 -Cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2 ,, 3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6- It is preferable to represent a diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and more preferable to represent the following structure,
  • Z M1 and Z M2 each independently -CH 2 O -, - CF 2 O -, - CH 2 CH 2 -, - CF 2 CF 2 - or preferably a single bond, -CF 2 O-, More preferred is —CH 2 CH 2 — or a single bond, with —CF 2 O— or a single bond being particularly preferred.
  • n M1 is preferably 0, 1, 2 or 3 and is preferably 0, 1 or 2; 0 or 1 is preferred when emphasis is placed on improvement of ⁇ , and 1 or 2 is preferred when T NI is emphasized preferable.
  • the types of compounds that can be combined are, for example, one type, two types, and three types in one embodiment of the present invention. Furthermore, in another embodiment of the present invention, there are four types, five types, six types, and seven or more types.
  • the content of the compound represented by the general formula (M) is low temperature solubility, transition temperature, electrical reliability, birefringence, process compatibility, dripping marks, image sticking, It is necessary to appropriately adjust according to the required performance such as dielectric anisotropy.
  • the lower limit of the preferable content of the compound represented by the formula (M) with respect to the total amount of the liquid crystal composition of the present invention is 1 mass%, 10 mass%, 20 mass%, and 30 mass%. %, 40% by mass, 50% by mass, 55% by mass, 60% by mass, 65% by mass, 70% by mass, 75% by mass, 80% by mass is there.
  • the upper limit value of the preferable content is, for example, 95% by mass, 85% by mass, and 75% by mass in one form of the invention with respect to the total amount of the liquid crystal composition of the present invention. Yes, 55% by weight, 45% by weight, 35% by weight, and 25% by weight.
  • the viscosity of the composition of the present invention low and lower the above lower limit and lower the upper limit when a composition having a high response speed is required. Furthermore, it is preferable to keep the TNI of the composition of the present invention high, and lower the above lower limit and lower the upper limit when a composition having good temperature stability is required. When it is desired to increase the dielectric anisotropy in order to keep the drive voltage low, it is preferable to raise the lower limit and raise the upper limit.
  • R K1 represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH 2 — in the alkyl group are each independently —CH-CH—, — It may be substituted by C ⁇ C-, -O-, -CO-, -COO- or -OCO-, n K1 represents 0, 1, 2, 3 or 4;
  • hydrogen atoms on the above groups (a) and (b) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom
  • R K1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy having 2 to 8 carbon atoms Group is preferable, and an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms is preferable.
  • An alkyl group of 1 to 5 or an alkenyl group of 2 to 5 carbon atoms is further preferable, an alkyl group of 2 to 5 carbon atoms or an alkenyl group of 2 to 3 carbon atoms is further preferable, and an alkenyl group of 3 carbon atoms (Propenyl group) is particularly preferred.
  • R K1 is preferably an alkyl group, and when importance is attached to decrease in viscosity, it is preferably an alkenyl group.
  • the ring structure to which it is bonded is a phenyl group (aromatic)
  • a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and carbon Alkenyl group having 4 to 5 atoms is preferable
  • a linear alkyl group having 1 to 5 carbon atoms, a straight chain Preferred is an alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms.
  • the total of carbon atoms and oxygen atoms, if present is preferably 5 or less, preferably linear.
  • the alkenyl group is preferably selected from the groups represented by any one of formulas (R1) to (R5). (The black dot in each formula represents a carbon atom in a ring structure to which an alkenyl group is bonded.)
  • a K1 and A K2 are each preferably aromatic when it is required to increase ⁇ n independently, and is preferably aliphatic to improve the response speed, and trans-1,4 -Cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2 ,, 3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6- It is preferable to represent a diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and more preferable to represent the following structure,
  • Z K1 and Z K2 are each independently -CH 2 O -, - CF 2 O -, - CH 2 CH 2 -, - CF 2 CF 2 - or preferably a single bond, -CF 2 O-, More preferred is —CH 2 CH 2 — or a single bond, with —CF 2 O— or a single bond being particularly preferred.
  • n K1 is preferably 0, 1, 2 or 3, preferably 0, 1 or 2, and if emphasis is placed on improvement of ⁇ , then 0 or 1 is preferred, and if emphasis is placed on T NI , 1 or 2 is preferred. preferable.
  • the types of compounds that can be combined are, for example, one type, two types, and three types in one embodiment of the present invention. Furthermore, in another embodiment of the present invention, there are four types, five types, six types, and seven or more types.
  • the content of the compound represented by the general formula (K) is low temperature solubility, transition temperature, electrical reliability, birefringence, process compatibility, dripping marks, image sticking, It is necessary to appropriately adjust according to the required performance such as dielectric anisotropy.
  • the lower limit of the preferable content of the compound represented by the general formula (K) with respect to the total amount of the liquid crystal composition of the present invention is 1% by mass, 10% by mass, 20% by mass, 30 % By mass, 40% by mass, 50% by mass, 55% by mass, 60% by mass, 65% by mass, 70% by mass, 75% by mass, 80% by mass It is.
  • the upper limit value of the preferable content is, for example, 95% by mass, 85% by mass, 75% by mass, and 65% by mass with respect to the total amount of the composition of the present invention. 55% by mass, 45% by mass, 35% by mass and 25% by mass.
  • the viscosity of the liquid crystal composition of the present invention is kept low and a composition having a high response speed is required, it is preferable to lower the above lower limit and lower the upper limit. Furthermore, it is preferable to keep TNI of the liquid crystal composition of the present invention high and lower the above lower limit and lower the upper limit when a composition having good temperature stability is required. When it is desired to increase the dielectric anisotropy in order to keep the drive voltage low, it is preferable to raise the lower limit and raise the upper limit.
  • the compound represented by the above general formula (J) is preferably a compound represented by the following formulas (M-1) to (M-18).
  • X M11 ⁇ X M186 each independently represent a hydrogen atom or a fluorine atom
  • R J1 ⁇ R J181 is independently an alkyl group having 1 to 5 carbon atoms, 2 to 5 carbon atoms Or an alkoxy group having 1 to 4 carbon atoms
  • X J11 to X J 181 each represents a fluorine atom, a chlorine atom or OCF 3
  • Each of A M81 and A M82 is independently a 1,4-cyclohexylene group, a 1,4-phenylene group or
  • Examples of the compound represented by General Formula (N-1) according to the present invention include compounds represented by the following General Formulas (N-1a) to (N-1g).
  • R N11 and R N12 are as defined R N11 and R N12 in the general formula (N-1), n Na12 represents 0 or 1, n NB11 is 1 or 2, n NC11 is N Nd11 represents 1 or 2; n Ne11 represents 1 or 2; n Nf12 represents 1 or 2; n Ng11 represents 1 or 2; A Ne11 represents trans-1, 4 And A Ng11 represents a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group or a 1,4-phenylene group ; If is 1, a NG11 represents cyclohexenylene group, when n NG11 is 2, represents at least one a NG11 1,4-cyclohexenylene group, Z NE11 is a single bond Represents an ethylene group, when n NE11 is 1, Z NE11 if .n NE11 representing the ethylene group is 2, represents at least one Z NE11 ethylene group.)
  • R N211 and R N212 each independently represents the same meaning as R N21 and R N22 in the general formula (N-2).
  • R N221 and R N222 each independently represents the same meaning as R N21 and R N22 in the general formula (N-2).
  • the compound represented by General Formula (N-3) is preferably a compound selected from the group of compounds represented by General Formula (N-3-2).
  • R N321 and R N322 each independently represents the same meaning as R N31 and R N32 in the general formula (N-3).
  • the polymerizable monomer represented by the general formula (I) and the compound represented by the general formula (J) It is preferable to include one or two or more compounds selected from and a compound represented by General Formula (L).
  • the upper limit of the proportion occupied by the components consisting of only the compounds represented by general formula (I), general formula (J) and general formula (L) in the whole liquid crystal composition containing the polymerizable monomer according to the present invention The values are 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass% It is preferable that they are 88 mass%, 87 mass%, 86 mass%, 85 mass%, and 84 mass%.
  • the lower limit of the proportion of the component composed of only the compounds represented by General Formula (I), General Formula (J) and General Formula (L) in the entire polymerizable monomer-containing liquid crystal composition according to the present invention The values are 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass% 93% by weight, 94% by weight, 95% by weight, 96% by weight, 97% by weight, 98% by weight, 99% by weight.
  • the polymerizable monomer represented by the general formula (I) and the compound represented by the general formula (N-1) It is preferable to include one or two or more compounds selected from and a compound represented by General Formula (L).
  • the proportion of the component constituted only of the compound represented by General Formula (I), General Formula (N-1), and General Formula (L) The upper limit value is 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass %, 88% by mass, 87% by mass, 86% by mass, 85% by mass, 84% by mass.
  • the dielectric anisotropy ( ⁇ ) at 20 ° C. is from ⁇ 2.0 to ⁇ 8.0, but from ⁇ 2.1 to ⁇ 6. 2 is preferable, -2.2 to -5.3 is more preferable, and -2.5 to -5.0 is more preferable. -2.7 to -4.8 are particularly preferred.
  • the dielectric anisotropy ( ⁇ ) at 20 ° C. is 1.5 to 20, preferably 1.5 to 18.0. 5 to 15.0 is more preferable, 1.5 to 11 is more preferable, and 1.5 to 8 is particularly preferable.
  • the liquid crystal composition according to the present invention has a refractive index anisotropy ( ⁇ n) at 20 ° C. of 0.08 to 0.14, preferably 0.09 to 0.13, more preferably 0.09 to 0.12. Is particularly preferred. More specifically, in the case of a thin cell gap, it is preferably 0.10 to 0.13, and in the case of a thick cell gap, it is preferably 0.08 to 0.11.
  • the liquid crystal composition according to the present invention has a viscosity ( ⁇ ) at 10 ° C. of 10 to 50 mPa ⁇ s, preferably 10 to 45 mPa ⁇ s, and more preferably 10 to 40 mPa ⁇ s.
  • the viscosity is preferably 35 mPa ⁇ s, more preferably 10 to 30 mPa ⁇ s, still more preferably 10 to 25 mPa ⁇ s, and particularly preferably 10 to 22 mPa ⁇ s.
  • the liquid crystal composition according to the present invention has a rotational viscosity ( ⁇ 1 ) at 50 ° C. of 50 to 160 mPa ⁇ s, preferably 55 to 160 mPa ⁇ s, and more preferably 60 to 160 mPa ⁇ s,
  • the viscosity is preferably 60 to 150 mPa ⁇ s, preferably 60 to 140 mPa ⁇ s, preferably 60 to 130 mPa ⁇ s, and more preferably 60 to 125 mPa ⁇ s.
  • the liquid crystal composition according to the present invention has a nematic phase-isotropic liquid phase transition temperature (T ni ) of 60 ° C. to 120 ° C., preferably 70 ° C. to 100 ° C., particularly preferably 70 ° C. to 85 ° C. .
  • the liquid crystal display device using the polymerizable monomer-containing liquid crystal composition of the present invention has the remarkable feature of high-speed response, and in addition, is sufficient tilt angle obtained and there is no unreacted polymerizable monomer? Because the voltage holding ratio (VHR) is so small that there is no problem, problems such as alignment failure and display failure are sufficiently suppressed. In addition, since the tilt angle and the residual amount of the polymerizable monomer can be easily controlled, it is easy to optimize and reduce the energy cost for manufacturing, which is optimal for improvement of production efficiency and stable mass production.
  • the liquid crystal display device using the polymerizable monomer-containing liquid crystal composition of the present invention is particularly useful for a liquid crystal display device for driving an active matrix, and is a PSA mode, PSVA mode, VA mode, PS-IPS mode or PS-FFS mode It can use for the liquid crystal display element for.
  • the liquid crystal composition was filtered with a membrane filter (PTFE 13 m-0.2 ⁇ m, manufactured by Agilent Technologies), and allowed to stand for 15 minutes under vacuum reduced pressure conditions to remove dissolved air. This was washed with acetone and weighed 0.5 g in a fully dried vial, and allowed to stand in an environment of ⁇ 25 ° C. for 10 days. Then, the presence or absence of precipitation was observed visually and it determined in the following two steps.
  • PTFE 13 m-0.2 ⁇ m manufactured by Agilent Technologies
  • irradiation condition 1 Under the irradiation condition 1, a pretilt angle is given to liquid crystal molecules in the liquid crystal cell.
  • the illuminance was measured at a center wavelength of 313nm is adjusted to 3 mW / cm 2, further irradiated with ultraviolet light at an accumulated light intensity 20 J / cm 2, to obtain a liquid crystal display device .
  • the aforementioned ultraviolet irradiation conditions are referred to as irradiation conditions 2. Under the irradiation condition 2, the residual amount of the polymerizable monomer in the unreacted liquid crystal cell under the irradiation condition 1 is reduced.
  • pretilt angle of the liquid crystal display element was measured and used as a pretilt angle (initial).
  • the backlight was illuminated for 10 hours while applying a voltage of 100 Hz at a frequency of 100 Hz to the liquid crystal display element at a rectangular wave of 30 V.
  • the pretilt angle was measured and used as the pretilt angle (after the test).
  • the pretilt angle was measured using Syntech OPTIPRO.
  • the magnitude of the voltage of 30 V is several times larger than the normal drive voltage, which is an acceleration test.
  • pretilt angle change amount approaches 0 [.degree.]
  • the possibility of occurrence of display defects due to the change in pretilt angle becomes lower.
  • the measured amount of change in pretilt angle was divided into the following four stages. S: within 0.1 ° (mostly display defects do not occur) A: 0.1 ° or more and 0.3 or less (not likely to cause display defects) B: 0.3 ° or more and 0.5 ° or less (a considerable display defect occurs) C: 0.5 ° or more (display failure and unacceptable level) (Evaluation test of response characteristics)
  • the cell gap of 3.2 ⁇ m used in the above (evaluation test of formation of pretilt angle) was further irradiated for 60 minutes with a UV fluorescent lamp manufactured by Toshiba Lightech Co. (illuminance at 313 nm: 1.7 mW / cm 2 ). The response speed was measured for the cells obtained by this. The response speed was measured at Voff at 6 V using a DAM 703 manufactured by AUTRONIC-MELCHERS under a temperature condition of 25 ° C.
  • a liquid crystal composition was prepared at a mixing ratio with the compound as shown below, and the composition was designated LC-1.
  • the composition of the liquid crystal composition and the results of physical properties are shown below.
  • the nematic phase-isotropic liquid phase transition temperature (T NI ) of LC-1 is 75 ° C.
  • the solid phase-nematic phase transition temperature (T CN ) is -33 ° C.
  • the refractive index anisotropy ( ⁇ n) is 0.11.
  • the dielectric anisotropy ( ⁇ ) was ⁇ 2.8
  • the rotational viscosity ( ⁇ 1 ) was 98 mPa ⁇ s.
  • the refractive index anisotropy ( ⁇ n), the dielectric anisotropy ( ⁇ ), and the rotational viscosity ( ⁇ 1) are all measurement results at 25 ° C. (the same applies hereinafter).
  • Comparative Examples 1 to 8 Polymerization in which 1.0 part by mass of the following spontaneous orientation monomer (P-1) and 0.3 parts by mass of a compound represented by the formula (RM-1) were added, based on 100 parts by mass of LC-1 Comparative Example 1 is a liquid crystal composition containing a monomer monomer.
  • Example 2 is a liquid crystal composition containing a functional monomer.
  • Example 3 is a liquid crystal composition containing a functional monomer.
  • Example 4 is a liquid crystal composition containing a functional monomer.
  • Example 5 is a liquid crystal composition containing a functional monomer.
  • Example 6 is a liquid crystal composition containing a functional monomer.
  • Example 7 is a liquid crystal composition containing a functional monomer.
  • Example 8 is a liquid crystal composition containing a functional monomer.
  • Examples 1 to 95 Except that the spontaneous orientation monomers (P-1) to (P-41) shown below and the polymerizable monomers (RM-1) to (RM-16) were added to LC-1 in the amounts shown in the following table, respectively A liquid crystal composition was prepared in the same manner as in Comparative Example 1.
  • liquid crystal molecules are vertically aligned
  • the cell is displayed black.
  • Examples of the appropriate two types of polymerizable monomers include a combination of a bifunctional monomer having a hydrophobic group introduced in the mesogen side chain and a polymerizable monomer having absorption at 300 nm or more, and each monomer has an appropriate concentration. Good vertical alignment was confirmed by adding at.
  • Comparative Examples 1, 2, 4, 5 to 7 it was confirmed that while the pretilt change amount was relatively good by adding the polymerizable monomer, the vertical alignment was low. In Comparative Example 3, although the vertical alignment was high, the pretilt change amount was large. In Comparative Examples 6 to 7, although the addition amount of one type of polymerizable monomer was increased, the vertical alignment was not improved. From these results, it was confirmed that one type of polymerizable monomer is not a monomer capable of achieving both vertical alignment and pretilt variation.
  • the orientation and tilt stability are evaluated in a composition comprising one type of spontaneous orientation monomer and one type of polymerizable monomer, but a polymerizable monomer having absorption at a long wavelength (for example, RM)
  • a polymerizable monomer having absorption at a long wavelength for example, RM
  • the tilt stability was relatively good, but the vertical alignment was inferior.
  • the compound (RM-3) having a hydrophobic site introduced is used as the polymerizable monomer, the vertical alignment property is good, but the polymerization by the ultraviolet light irradiation does not occur sufficiently, and the network is densely formed. As a result, the tilt stability is lowered.
  • the low temperature storage stability was inferior to that of Example.
  • compositions composed of compounds and mixing ratios as shown below were prepared, and the liquid crystal compositions were designated LC-2 to LC-8.
  • Example 96 It was confirmed that even when the base composition of Example 3 was replaced with LC1 to LC2, the vertical alignment and the pretilt change amount were small, and the display unevenness and the image sticking were suppressed (Example 96). It was confirmed that even when the base composition of Example 30 was replaced with LC1 to LC3, the vertical alignment and the pretilt change amount were small, and the display unevenness and the image sticking were also suppressed (Example 97).
  • Example 98 Even when the base composition of Example 35 was replaced with LC1 to LC4, it was confirmed that the vertical alignment and the pretilt change amount were small, and the display unevenness and the image sticking were suppressed (Example 98).
  • Example 99 It was confirmed that even when the base composition of Example 36 was changed from LC1 to LC5 and the polymerizable compound was changed from P-6 to P-11, the vertical alignment and the pretilt change amount were small, and the display unevenness and the image sticking were suppressed ( Example 99).
  • Example 100 Even when the base composition of Example 41 was changed from LC1 to LC6 and the polymerizable compound was changed from P-6 to P-18, it was confirmed that the vertical alignment and the pretilt change amount were small, and the display unevenness and the image sticking were suppressed ( Example 100).
  • Example 101 Even when the base composition of Example 44 was changed from LC1 to LC7 and the polymerizable compound was changed from P-7 to P-23, it was confirmed that the vertical alignment and the pretilt change amount were small, and the display unevenness and the image sticking were suppressed ( Example 101).
  • Example 104 to 123 0.2 parts by mass of the spontaneous orientation monomer (1) and 0.4 parts by mass of the spontaneous orientation monomer (2) shown in the following table, and the polymerizable monomers (1) and (2) in the addition amounts shown in the following table
  • a liquid crystal composition was prepared in the same manner as in Comparative Example 1 except that each of the compositions LC-1 to LC-8 was added.
  • the low temperature storage property, the vertical alignment property, and the pretilt stability were evaluated by the combination of two kinds of spontaneously orienting monomers and two kinds of polymerizable monomers.
  • two types of low solubility spontaneous orientation monomers at a low concentration, it was possible to confirm the improvement of the vertical orientation while maintaining the low temperature storage property.
  • concentration of the polymerizable monomer component can be increased, and the pretilt stability can be improved.
  • the liquid crystal composition in the examples exhibited comprehensively excellent performance as a liquid crystal display element.
  • Example 124 to 149 A liquid crystal composition was prepared in the same manner as in Example 1 except that the spontaneously orienting monomers in Example 1 were replaced by P-1 to P-41 to P-66, respectively, and these were designated as Examples 124 to 149. . From the results of Examples 124 to 149, it was confirmed that the vertical alignment property and the pretilt change amount were small, and the display unevenness and the image sticking were suppressed even when various kinds of spontaneous alignment monomers were used.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Mathematical Physics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Liquid Crystal (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

L'invention fournit une composition de cristaux liquides qui se révèle excellente en termes de propriétés d'alignement vertical et de caractéristiques de déverminage, et fournit également un élément d'affichage à cristaux liquides mettant en œuvre cette composition de cristaux liquides. Plus précisément, l'invention fournit une composition de cristaux liquides qui comprend au moins une sorte de monomère à alignement spontané possédant un premier squelette mésogène, au moins un groupe polymérisable représenté par la formule générale （ＰＧ１）, et au moins un groupe d'adsorption, et qui contient au moins deux sortes de monomère polymérisable choisies dans un groupe constitué de monomères polymérisables représentés par la formule générale (I) comportant une structure chimique différente de celle dudit monomère à alignement spontané.
PCT/JP2018/045432 2017-12-22 2018-12-11 Composition de cristaux liquides, et élément d'affichage à cristaux liquides WO2019124153A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2019560991A JP6828832B2 (ja) 2017-12-22 2018-12-11 液晶組成物及び液晶表示素子
CN201880075273.9A CN111373019B (zh) 2017-12-22 2018-12-11 液晶组合物及液晶显示元件
KR1020207015046A KR20200100624A (ko) 2017-12-22 2018-12-11 액정 조성물 및 액정 표시 소자

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2017246414 2017-12-22
JP2017-246414 2017-12-22

Publications (1)

Publication Number Publication Date
WO2019124153A1 true WO2019124153A1 (fr) 2019-06-27

Family

ID=66994625

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2018/045432 WO2019124153A1 (fr) 2017-12-22 2018-12-11 Composition de cristaux liquides, et élément d'affichage à cristaux liquides

Country Status (5)

Country Link
JP (1) JP6828832B2 (fr)
KR (1) KR20200100624A (fr)
CN (1) CN111373019B (fr)
TW (1) TWI774891B (fr)
WO (1) WO2019124153A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020008896A1 (fr) * 2018-07-03 2020-01-09 Dic株式会社 Auxilliaire d'alignement, composition de cristaux liquides et dispositif d'affichage à cristaux liquides
WO2020075509A1 (fr) * 2018-10-11 2020-04-16 Dic株式会社 Composition de cristaux liquides polymérisable et élément d'affichage à cristaux liquides
CN111040780A (zh) * 2019-12-27 2020-04-21 Tcl华星光电技术有限公司 自取向液晶、显示装置及其制备方法
CN111073664A (zh) * 2019-12-13 2020-04-28 Tcl华星光电技术有限公司 液晶材料、液晶显示面板的制备方法及显示面板
WO2020209035A1 (fr) * 2019-04-09 2020-10-15 Jnc株式会社 Composé, composition à cristaux liquides, et élément d'affichage à cristaux liquides
WO2020230480A1 (fr) * 2019-05-15 2020-11-19 Dic株式会社 Composition de cristaux liquides polymérisables et élément d'affichage à cristaux liquides, ainsi que composé
CN112210388A (zh) * 2019-07-10 2021-01-12 北京八亿时空液晶科技股份有限公司 一种聚合物稳定型液晶组合物及其应用
CN112852444A (zh) * 2019-11-27 2021-05-28 Dic株式会社 液晶组合物和使用其的液晶显示元件
JP2021084870A (ja) * 2019-11-27 2021-06-03 Dic株式会社 安定剤化合物、液晶組成物および表示素子
US11274254B2 (en) * 2018-02-05 2022-03-15 Merck Patent Gmbh Compounds for the homeotropic alignment of liquid-crystalline media

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110621761A (zh) * 2017-06-29 2019-12-27 Dic株式会社 液晶组合物及液晶显示元件

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015513577A (ja) * 2012-02-22 2015-05-14 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ 液晶媒体
WO2017068875A1 (fr) * 2015-10-23 2017-04-27 Jnc株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides
WO2017130566A1 (fr) * 2016-01-29 2017-08-03 Jnc株式会社 Composition de cristaux liquides, et élément d'affichage à cristaux liquides
WO2018105726A1 (fr) * 2016-12-08 2018-06-14 Jnc株式会社 Dispositif à cristaux liquides en mode inverse
JP2018163271A (ja) * 2017-03-24 2018-10-18 Jnc株式会社 液晶表示素子
WO2018221236A1 (fr) * 2017-06-01 2018-12-06 Dic株式会社 Monomère polymérisable, composition de cristaux liquides utilisant un monomère polymérisable et dispositif d'affichage à cristaux liquides
WO2019003935A1 (fr) * 2017-06-29 2019-01-03 Dic株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI635164B (zh) * 2012-04-24 2018-09-11 迪愛生股份有限公司 Liquid crystal composition containing polymerizable compound and liquid crystal display element using same
WO2014061755A1 (fr) 2012-10-19 2014-04-24 シャープ株式会社 Dispositif d'affichage à cristaux liquides et procédé de fabrication d'un dispositif d'affichage à cristaux liquides
JP2015152745A (ja) * 2014-02-13 2015-08-24 大日本印刷株式会社 光配向性を有する熱硬化性組成物、配向層、配向層付基材、位相差板およびデバイス
EP3730590A1 (fr) * 2014-03-10 2020-10-28 Merck Patent GmbH Milieux cristallins liquides à orientation homéotrope
US10294426B2 (en) 2014-07-28 2019-05-21 Merck Patent Gmbh Liquid crystalline media having homeotropic alignment
KR20170107436A (ko) * 2015-01-20 2017-09-25 제이엔씨 주식회사 액정 조성물 및 액정 표시 소자
JP2018534380A (ja) * 2015-09-09 2018-11-22 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ 液晶媒体
US10921650B2 (en) * 2015-12-28 2021-02-16 Nissan Chemical Industries, Ltd. Liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display element
WO2017145611A1 (fr) * 2016-02-25 2017-08-31 Jnc株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides
CN106833677A (zh) * 2016-12-29 2017-06-13 深圳市华星光电技术有限公司 一种垂直取向剂材料
JP6624305B2 (ja) * 2017-06-01 2019-12-25 Dic株式会社 重合性モノマー、それを用いた液晶組成物及び液晶表示素子
KR20200100034A (ko) * 2017-12-21 2020-08-25 디아이씨 가부시끼가이샤 액정 조성물

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015513577A (ja) * 2012-02-22 2015-05-14 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ 液晶媒体
WO2017068875A1 (fr) * 2015-10-23 2017-04-27 Jnc株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides
WO2017130566A1 (fr) * 2016-01-29 2017-08-03 Jnc株式会社 Composition de cristaux liquides, et élément d'affichage à cristaux liquides
WO2018105726A1 (fr) * 2016-12-08 2018-06-14 Jnc株式会社 Dispositif à cristaux liquides en mode inverse
JP2018163271A (ja) * 2017-03-24 2018-10-18 Jnc株式会社 液晶表示素子
WO2018221236A1 (fr) * 2017-06-01 2018-12-06 Dic株式会社 Monomère polymérisable, composition de cristaux liquides utilisant un monomère polymérisable et dispositif d'affichage à cristaux liquides
WO2019003935A1 (fr) * 2017-06-29 2019-01-03 Dic株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11274254B2 (en) * 2018-02-05 2022-03-15 Merck Patent Gmbh Compounds for the homeotropic alignment of liquid-crystalline media
JPWO2020008896A1 (ja) * 2018-07-03 2021-03-11 Dic株式会社 配向助剤、液晶組成物および液晶表示素子
WO2020008896A1 (fr) * 2018-07-03 2020-01-09 Dic株式会社 Auxilliaire d'alignement, composition de cristaux liquides et dispositif d'affichage à cristaux liquides
CN112313310A (zh) * 2018-07-03 2021-02-02 Dic株式会社 取向助剂、液晶组合物及液晶显示元件
JPWO2020075509A1 (ja) * 2018-10-11 2021-02-15 Dic株式会社 重合性液晶組成物及び液晶表示素子
WO2020075509A1 (fr) * 2018-10-11 2020-04-16 Dic株式会社 Composition de cristaux liquides polymérisable et élément d'affichage à cristaux liquides
WO2020209035A1 (fr) * 2019-04-09 2020-10-15 Jnc株式会社 Composé, composition à cristaux liquides, et élément d'affichage à cristaux liquides
WO2020230480A1 (fr) * 2019-05-15 2020-11-19 Dic株式会社 Composition de cristaux liquides polymérisables et élément d'affichage à cristaux liquides, ainsi que composé
CN112210388A (zh) * 2019-07-10 2021-01-12 北京八亿时空液晶科技股份有限公司 一种聚合物稳定型液晶组合物及其应用
CN112852444A (zh) * 2019-11-27 2021-05-28 Dic株式会社 液晶组合物和使用其的液晶显示元件
JP2021084870A (ja) * 2019-11-27 2021-06-03 Dic株式会社 安定剤化合物、液晶組成物および表示素子
JP7363414B2 (ja) 2019-11-27 2023-10-18 Dic株式会社 安定剤化合物、液晶組成物および表示素子
JP7380136B2 (ja) 2019-11-27 2023-11-15 Dic株式会社 液晶組成物およびそれを用いた液晶表示素子
CN111073664A (zh) * 2019-12-13 2020-04-28 Tcl华星光电技术有限公司 液晶材料、液晶显示面板的制备方法及显示面板
CN111040780A (zh) * 2019-12-27 2020-04-21 Tcl华星光电技术有限公司 自取向液晶、显示装置及其制备方法

Also Published As

Publication number Publication date
KR20200100624A (ko) 2020-08-26
CN111373019A (zh) 2020-07-03
TW201939136A (zh) 2019-10-01
CN111373019B (zh) 2023-10-03
TWI774891B (zh) 2022-08-21
JPWO2019124153A1 (ja) 2020-05-28
JP6828832B2 (ja) 2021-02-10

Similar Documents

Publication Publication Date Title
JP6828832B2 (ja) 液晶組成物及び液晶表示素子
JP6493775B1 (ja) 液晶組成物及び液晶表示素子
JP4360444B2 (ja) 高分子安定化液晶組成物、液晶表示素子、液晶表示素子の製造方法
US11312906B2 (en) Polymerizable monomer, liquid crystal composition using polymerizable monomer, and liquid crystal display device
TWI589683B (zh) 液晶介質及液晶顯示器
JP6801796B2 (ja) 重合性液晶組成物及び液晶表示素子ならびに重合性化合物
WO2019124093A1 (fr) Composition de cristaux liquides
JP2020196827A (ja) 液晶組成物及び液晶表示素子
JP2019194331A (ja) 重合性モノマー、それを用いた液晶組成物及び液晶表示素子
JP6808916B2 (ja) 液晶表示素子
JP2021089419A (ja) 液晶表示素子
JP7288166B2 (ja) 液晶組成物
WO2019098115A1 (fr) Composé polymérisable, composition de cristaux liquides l'utilisant, et élément d'affichage à cristaux liquides
WO2019124094A1 (fr) Composition de cristaux liquides
JP7472606B2 (ja) 液晶組成物及び液晶表示素子
JP6844749B2 (ja) 重合性液晶組成物及び液晶表示素子
WO2019082839A1 (fr) Composition de cristaux liquides polymérisable, et élément d'affichage à cristaux liquides
JP2020200428A (ja) 重合性化合物含有液晶組成物及び液晶表示素子
JP6828852B2 (ja) 配向助剤、液晶組成物及び液晶表示素子
JP7472607B2 (ja) 液晶組成物及び液晶表示素子
JP2020050871A (ja) 配向助剤、液晶組成物及び液晶表示素子
TW202134409A (zh) 含聚合性化合物之液晶組成物及液晶顯示元件
JP2020002065A (ja) 重合性化合物並びにそれを使用した液晶組成物及び液晶表示素子
JP2020100600A (ja) 重合性安定剤及びそれを用いた液晶組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18891695

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2019560991

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18891695

Country of ref document: EP

Kind code of ref document: A1