WO2016056455A1 - Composition de cristaux liquides et élément d'affichage à cristaux liquides mettant en œuvre celle-ci - Google Patents

Composition de cristaux liquides et élément d'affichage à cristaux liquides mettant en œuvre celle-ci Download PDF

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WO2016056455A1
WO2016056455A1 PCT/JP2015/077919 JP2015077919W WO2016056455A1 WO 2016056455 A1 WO2016056455 A1 WO 2016056455A1 JP 2015077919 W JP2015077919 W JP 2015077919W WO 2016056455 A1 WO2016056455 A1 WO 2016056455A1
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liquid crystal
formula
group
crystal composition
carbon atoms
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PCT/JP2015/077919
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English (en)
Japanese (ja)
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小川　真治
栗山　毅
芳典 岩下
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Dic株式会社
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Priority to CN201580054713.9A priority Critical patent/CN106795434A/zh
Priority to JP2016553067A priority patent/JP6132122B2/ja
Publication of WO2016056455A1 publication Critical patent/WO2016056455A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—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
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14—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
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/18—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 triple bonds, e.g. tolans
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—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
    • C09K19/38—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
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • 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 having a negative dielectric anisotropy ( ⁇ ) useful as a liquid crystal display material and a liquid crystal display device using the same.
  • a liquid crystal composition having a negative ⁇ is used, and the display is required to have performance such as low voltage driving, high speed response, and a wide operating temperature range.
  • performance of a liquid crystal composition required for producing a display an absolute value of ⁇ is large, a viscosity ( ⁇ ) is small, and a high nematic phase-isotropic liquid phase transition temperature (T ni ) is required. Yes.
  • ⁇ n ⁇ d which is the product of ⁇ n and the cell gap (d)
  • liquid crystal display elements using a liquid crystal composition are widely used, such as VA type and IPS type, and super large size display elements having a size of 50 type or more are practically used. Became.
  • the method of injecting the liquid crystal composition into the substrate has been changed from the conventional vacuum injection method to the drop injection (ODF: One Drop Fill) method, but the liquid crystal composition is applied to the substrate.
  • ODF Drop Fill
  • R 1 represents a linear or branched alkyl group having 1 to 22 carbon atoms, and one or more CH 2 groups in the alkyl group are not directly adjacent to an oxygen atom. May be substituted with —O—, —CH ⁇ CH—, —CO—, —OCO—, —COO—, —C ⁇ C—, —CF 2 O—, —OCF 2 —, and X 1 is — One or more compounds represented by CH 2 — or an oxygen atom)
  • the liquid crystal composition having a negative ⁇ according to the present invention has a liquid crystal phase in a wide temperature range, a viscosity much lower than that of the conventional one, good solubility at low temperatures, and its specific resistance and voltage holding ratio.
  • the degree of change due to heat and light is extremely small, and particularly the change over a long period is small.
  • the liquid crystal composition of the present invention has high practical applicability to liquid crystal products, and liquid crystal display elements such as VA type, PSVA type and n type FFS type using the liquid crystal composition can achieve high-speed response. .
  • the composition of the present invention preferably exhibits a liquid crystal phase at room temperature (25 ° C.), and more preferably exhibits a nematic phase.
  • the composition of the present invention contains a dielectrically nearly neutral compound ( ⁇ value is ⁇ 2 to 2) and a negative compound ( ⁇ value is less than 2).
  • the dielectric anisotropy of the compound is a value extrapolated from a measured value of the dielectric anisotropy of a composition prepared by adding to a dielectrically nearly neutral composition at 25 ° C.
  • content is described in% below, this means mass%.
  • the compound represented by these is contained. Specifically, it is a compound represented by the following formulas (I-1) and (I-2).
  • the compound represented by the general formula (I) contains one or two compounds, preferably one to five compounds, more preferably at a low temperature. In consideration of characteristics such as solubility, transition temperature, electrical reliability, and birefringence, there are upper and lower limits for each embodiment.
  • the compound represented by the general formula (L-1-1) is a compound selected from the group of compounds represented by the formula (L-1-1.1) to the formula (L-1-1.3). And is preferably a compound represented by formula (L-1-1.2) or formula (L-1-1.3), and particularly represented by formula (L-1-1.3). It is preferable that it is a compound.
  • the lower limit of the preferable content of the compound represented by the formula (L-1-1.3) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3% 5%, 7%, and 10%.
  • the upper limit of the preferable content is 30%, 25%, 20%, 15%, 13%, and 10% with respect to the total amount of the liquid crystal composition of the present invention. 8%, 7%, 6%, 5%, 3%.
  • the compound represented by the general formula (L-1-A) is preferably a compound selected from the group of compounds represented by the general formula (L-1-2).
  • the lower limit of the preferable content of the compound represented by the formula (L-1-2) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 5%, 10%, 15 %, 17%, 20%, 23%, 25%, 27%, 30%, 35%.
  • the upper limit of the preferable content is 60%, 55%, 50%, 45%, 42%, and 40% with respect to the total amount of the liquid crystal composition of the present invention. 38%, 35%, 33%, 30%.
  • the compound represented by the general formula (L-1-A) is preferably a compound selected from the group of compounds represented by the general formulas (L-1-4) and (L-1-5).
  • the lower limit of the preferable content of the compound represented by the formula (L-1-4) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 5%, 10%, 13 %, 15%, 17%, and 20%.
  • the upper limit value of the preferable content is 25%, 23%, 20%, 17%, 15%, 13% with respect to the total amount of the liquid crystal composition of the present invention, 10%.
  • the lower limit of the preferable content of the compound represented by the formula (L-1-5) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 5%, 10%, 13 %, 15%, 17%, and 20%.
  • the upper limit value of the preferable content is 25%, 23%, 20%, 17%, 15%, 13% with respect to the total amount of the liquid crystal composition of the present invention, 10%.
  • the compounds represented by the general formulas (L-1-4) and (L-1-5) are represented by the formulas (L-1-4.1) to (L-1-5.3).
  • a compound represented by the formula (L-1-4.2) or the formula (L-1-5.2) is preferable.
  • the lower limit of the preferable content of the compound represented by the formula (L-1-4.2) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3% 5%, 7%, 10%, 13%, 15%, 18%, and 20%.
  • the upper limit of the preferable content is 20%, 17%, 15%, 13%, 10%, 8% with respect to the total amount of the liquid crystal composition of the present invention, 7% and 6%.
  • the compound represented by the general formula (L-2-A) is preferably a compound selected from the group of compounds represented by the formula (L-2.7) to the formula (L-2.12).
  • the lower limit of the preferable content of the compound represented by the general formula (L-2-A) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, and 10%.
  • the upper limit of the preferable content is 20%, 15%, 13%, 10%, 8%, 7% with respect to the total amount of the liquid crystal composition of the present invention, 6%, 5%, 3%.
  • the compound represented by the general formula (L-3-A) is preferably a compound selected from the group of compounds represented by the formula (L-3.8) to the formula (L-3.13).
  • the lower limit of the preferable content of the compound represented by the formula (L-3-A) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5% %, 7%, and 10%.
  • the upper limit of the preferable content is 20%, 15%, 13%, 10%, 8%, 7% with respect to the total amount of the liquid crystal composition of the present invention, 6%, 5%, 3%.
  • the compound represented by the general formula (L-4-A) is preferably a compound represented by the formula (L-4.1) to the formula (L-4.3).
  • the lower limit of the preferable content of the compound represented by the general formula (L-4-A) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40%.
  • the upper limit of the preferable content of the compound represented by the formula (L-4) with respect to the total amount of the liquid crystal composition of the present invention is 50%, 40%, 35%, and 30%. Yes, 20%, 15%, 10%, 5%.
  • a preferable combination of the compounds represented by the general formula (L-4-A) is, for example, according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. Whether it contains a compound represented by L-4.1) or a compound represented by formula (L-4.2), it is represented by formula (L-4.1). Both the compound and the compound represented by (L-4.2) may be contained, or all the compounds represented by formula (L-4.1) to formula (L-4.3) It may be included.
  • the lower limit of the preferable content of the compound represented by the formula (L-4.1) or the formula (L-4.2) with respect to the total amount of the liquid crystal composition of the present invention is 3%, and 5% 7%, 9%, 11%, 12%, 13%, 18%, 21%, and a preferred upper limit is 45, 40%. Yes, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8% is there.
  • both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2) are contained, both compounds relative to the total amount of the liquid crystal composition of the present invention
  • the lower limit of the preferable content of 15%, 19%, 24%, and 30%, and the preferable upper limit is 45%, 40%, 35%, and 30%. %, 25%, 23%, 20%, 18%, 15%, 13%.
  • the compound represented by the general formula (L-5-A) is preferably a compound represented by the formula (L-5.1) or the formula (L-5.2).
  • the lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10% 14%, 16%, 20%, 23%, 26%, 30%, 35%, and 40%.
  • the upper limit of the preferable content of these compounds is 50%, 40%, 35%, 30%, 20%, 15%, 10%, and 5%. .
  • the compound represented by the general formula (L-6-A) is preferably a compound represented by the formula (L-6.10) to the formula (L-6.17).
  • the lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, and 7%.
  • the upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, and 9%.
  • the liquid crystal composition of the present invention contains one or more compounds selected from the group consisting of compounds represented by general formula (L-1) to general formula (L-6).
  • the compound represented by formula (L-1) and the compound represented by formula (L-2) are preferably contained, and the compound represented by formula (L-1) and formula
  • the compound represented by (L-3) is preferably contained, and the compound represented by formulas (L-1) and (L-4) is preferably contained, represented by formula (L-1).
  • a compound represented by the general formula (L-5) are preferably contained, and a compound represented by the general formula (L-1) and the general formula (L-6) is preferably contained.
  • the liquid crystal composition of the present invention has the general formula (N-1)
  • R N11 and R N12 each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 10 carbon atoms, and n N11 and n N12 are 0 or 1 And n N11 + n N12 represents 0 or 1.
  • the compound represented by the general formula (N-1) has two or more benzene rings, and has two fluorine groups in the benzene ring. These compounds have the property that the dielectric anisotropy ( ⁇ ) is negative and ⁇ n is large.
  • the compound represented by the general formula (N-1) is preferably a compound having an absolute value of ⁇ larger than 3.
  • R N11 and R N12 each independently represent 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 group having 2 to 8 carbon atoms is preferable, 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 alkyl group having 2 to 5 carbon atoms.
  • alkenyloxy group is preferred, an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is more preferred, and an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is further preferred.
  • An alkenyl group having 3 carbon atoms (propenyl group) is particularly preferable.
  • the ring structure to which it is bonded is a phenyl group (aromatic)
  • An alkenyl group having 4 to 5 atoms is preferable
  • straight-chain alkenyl groups having 2 to 5 carbon atoms are preferred.
  • the total of carbon atoms and oxygen atoms if present, is preferably 5 or less, and is preferably linear.
  • the alkenyl group is preferably selected from groups represented by any of the formulas (R1) to (R5). (The black dots in each formula represent carbon atoms in the ring structure.)
  • the lower limit of the preferable content of the compound represented by the formula (N-1) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 10%, 20%, 30% Yes, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%.
  • the upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.
  • R N131 and R N132 each independently represent the same meaning as R N11 and R N12 in formula (N-1)).
  • R N131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.
  • R N132 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.
  • the compound represented by the general formula (N-1-3) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-3) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 10%, 13%, 15% %, 17% and 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.
  • the compound represented by the general formula (N-1-3) is a compound selected from the group of compounds represented by the formula (N-1-3.1) to the formula (N-1-3.11).
  • it is a compound represented by the formulas (N-1-3.1) to (N-1-3.7), and the formula (N-1-3.1) and the formula (N -1-3.2), formula (N-1-3.3), formula (N-1-3.4) and compounds represented by formula (N-1-3.6) are preferred.
  • the compounds represented by formula (N-1-3.1) to formula (N-1-3.4) and formula (N-1-3.6) may be used alone or in combination. Is possible, but the combination of formula (N-1-3.1) and formula (N-1-3.2), formula (N-1-3.3), formula (N-1-3.4) ) And a combination of two or three selected from formula (N-1-3.6) are preferred.
  • the lower limit of the preferred content of these compounds alone or with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15%, 17%, 20% %.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.
  • R N141 and R N142 each independently represents the same meaning as R N11 and R N12 in the general formula (N-1).
  • R N141 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.
  • RN142 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.
  • the compound represented by the general formula (N-1-4) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-4) with respect to the total amount of the liquid crystal composition of the present invention is 3%, 5%, 7%, 10% %, 13%, 15%, 17%, and 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15%, 13%, 11%, 10%, 8%.
  • the compound represented by the general formula (N-1-4) is a compound selected from the group of compounds represented by the formula (N-1-4.1) to the formula (N-1-4.14).
  • it is a compound represented by the formulas (N-1-4.1) to (N-1-4.4), and the formula (N-1-4.1) and the formula (N
  • the compound represented by -1-4.2) is preferable.
  • the compounds represented by the formulas (N-1-4.1) to (N-1-4.4) can be used alone or in combination, but the liquid crystal composition of the present invention
  • the lower limit of the preferred content of these compounds alone or with respect to the total amount of is 3%, 5%, 7%, 10%, 13%, 15%, 17 % And 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15%, 13%, 11%, 10%, 8%.
  • N-1 a compound represented by the general formula (N-1-5) is also preferable.
  • R N151 and R N152 each independently represent the same meaning as R N11 and R N12 in General Formula (N).
  • R N151 and R N152 are each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, butenyl group, ethyl group, propyl Group or butyl group is preferred.
  • the compound represented by the general formula (N-1-5) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the formula (N-1-5) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 8%, 10%, 13 %, 15%, 17%, and 20%.
  • the upper limit of the preferable content is 35%, 33%, 30%, 28%, 25%, and 23% with respect to the total amount of the liquid crystal composition of the present invention, 20%, 18%, 15%, 13%.
  • the compound represented by the general formula (N-1-5) is a compound selected from the group of compounds represented by the formula (N-1-5.1) to the formula (N-1-5.6).
  • the compound represented by the formula (N-1-3.2 and the formula (N-1-3.4) is preferable.
  • the compounds represented by formula (N-1-5.2) and formula (N-1-5.4) can be used alone or in combination, but the liquid crystal composition of the present invention
  • the lower limit of the preferable content of these compounds alone or with respect to the total amount of the product is 5%, 8%, 10%, 13%, 15%, 17%, 20%.
  • the upper limit of the preferable content is 35%, 33%, 30%, 28%, 25%, and 23% with respect to the total amount of the liquid crystal composition of the present invention, 20%, 18%, 15%, 13%.
  • the liquid crystal composition of the present invention has the general formula (N-4)
  • R 41 and R 42 each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 10 carbon atoms
  • X 41 is a single bond, —CH 2 CH 2 — or —CH 2 O—
  • n N41 represents 0 or 1
  • R N111 and R N112 each independently represent the same meaning as R N41 and R N42 in formula (N-4).
  • R N111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a propyl group or a pentyl group.
  • RN112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group or a butoxy group.
  • the compound represented by the general formula (N-4-1) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the formula (N-4-1) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 10%, 13%, 15% %, 17%, 20%, 23%, 25%, 27%, 30%, 33%, and 35%.
  • the upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 30% with respect to the total amount of the liquid crystal composition of the present invention. 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3%.
  • the compound represented by the general formula (N-4-1) is a compound selected from the group of compounds represented by the formula (N-4-1.1) to the formula (N-4-1.14). Preferably, it is a compound represented by the formulas (N-4-1.1) to (N-4-1.4), and the formula (N-4-1.1) and the formula (N The compound represented by -4-1.3) is preferred.
  • the compounds represented by the formulas (N-4-1.1) to (N-4-1.4) can be used alone or in combination, but the liquid crystal composition of the present invention
  • the lower limit of the preferable content of these compounds alone or with respect to the total amount of is 5%, 10%, 13%, 15%, 17%, 20%, 23 %, 25%, 27%, 30%, 33%, and 35%.
  • the upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 30% with respect to the total amount of the liquid crystal composition of the present invention. 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3%.
  • R N121 and R N122 each independently represent the same meaning as R N41 and R N42 in formula (N-4)).
  • RN121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, a butyl group or a pentyl group.
  • RN122 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and includes a methyl group, a propyl group, a methoxy group, an ethoxy group, or a propoxy group. preferable.
  • the compound represented by the general formula (N-4-2) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the formula (N-4-2) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 7%, 10%, 13 %, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, 37 %, 40%, and 42%.
  • the upper limit of the preferred content is 50%, 48%, 45%, 43%, 40%, 38%, with respect to the total amount of the liquid crystal composition of the present invention, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%.
  • the compound represented by the general formula (N-4-2) is a compound selected from the group of compounds represented by the formula (N-4-2.1) to the formula (N-4-2.13).
  • the formula (N-4-2.3) to the formula (N-4-2.7), the formula (N-4-2.10), the formula (N-4-2.11) and the formula A compound represented by (N-4-2.13) is preferable, and when importance is placed on the improvement of ⁇ , the formula (N-4-2.3) to the formula (N-4-2.7)
  • the compound represented by formula (N-4-2.10), formula (N-4-2.11) and formula (N-4-2.13) It is preferable that it is a compound represented by these.
  • the compounds represented by the formulas (N-4-2.1) to (N-4-2.13) can be used alone or in combination.
  • the lower limit of the preferable content of these compounds alone or with respect to the total amount of the product is 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, and 35%.
  • the upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 30% with respect to the total amount of the liquid crystal composition of the present invention. 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3%.
  • R N1101 and R N1102 each independently represent the same meaning as R N41 and R N42 in formula (N-4).
  • R N1101 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a propenyl group, an ethyl group, a propyl group, or a butyl group.
  • R N1102 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.
  • the compound represented by the general formula (N-4-10) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the formula (N-4-10) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 10%, 13%, 15% %, 17% and 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.
  • the compound represented by the general formula (N-4-10) is a compound selected from the group of compounds represented by the formula (N-4-100.1) to the formula (N-4-10.15).
  • it is a compound represented by the formulas (N-4-10.1) to (N-4-10.5), and the formula (N-4-10.1) and the formula (N
  • the compound represented by ⁇ 4-10.2) is preferable.
  • the compounds represented by the formulas (N-4-10.1) and (N-4-10.2) can be used alone or in combination.
  • the lower limit of the preferable content of these compounds alone or with respect to the total amount of the product is 5%, 10%, 13%, 15%, 17%, and 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.
  • R N1111 and R N1112 each independently represent the same meaning as R N41 and R N42 in formula (N-4).
  • R N1111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a propenyl group, an ethyl group, a propyl group, or a butyl group.
  • R N1112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
  • the compound represented by the general formula (N-4-11) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the formula (N-4-11) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 10%, 13%, 15% %, 17% and 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.
  • the compound represented by the general formula (N-4-11) is a compound selected from the group of compounds represented by the formula (N-4-11.1) to the formula (N-4-11.15). It is preferably a compound represented by the formulas (N-4-11.1) to (N-4-11.15), and the compounds represented by the formulas (N-4-11.2 and the formula (N- The compound represented by 4-11.4) is preferable.
  • the compounds represented by the formula (N-4-11.2) and the formula (N-4-11.4) can be used alone or in combination.
  • the lower limit of the preferable content of these compounds alone or with respect to the total amount of the product is 5%, 10%, 13%, 15%, 17%, and 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.
  • R N1121 and R N1122 each independently represent the same meaning as R N41 and R N42 in Formula (N-4).
  • RN1121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.
  • RN1122 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.
  • the compound represented by the general formula (N-4-12) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the formula (N-4-12) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 10%, 13%, 15% %, 17% and 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.
  • the compound represented by the general formula (N-4-13) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.
  • the lower limit of the preferable content of the compound represented by the formula (N-4-13) with respect to the total amount of the liquid crystal composition of the present invention is 5%, 10%, 13%, 15% %, 17% and 20%.
  • the upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the liquid crystal composition of the present invention. 18%, 15% and 13%.
  • the liquid crystal composition of the present invention may contain one or more compounds selected from the compounds represented by the general formulas (N-2) and (N-3).
  • R N21 , R N22 , R N31 and R N32 each independently represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH 2 in the alkyl group Each — may be independently substituted by —CH ⁇ CH—, —C ⁇ C—, —O—, —CO—, —COO— or —OCO—,
  • a N21 , A N22 , A N31 and A N32 each independently represent (a) a 1,4-cyclohexylene group (one —CH 2 — present in this group or two or more non-adjacent — CH 2 — may be replaced by —O—) and (b) a 1,4-phenylene group (one —CH ⁇ present in this group or two or more —CH ⁇ not adjacent to each other).
  • 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, Z N21 , Z N22 , Z N31 and Z N32 are each independently a single bond —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —COO—, —OCO.
  • XN21 represents a hydrogen atom or a fluorine atom
  • T N31 represents —CH 2 — or an oxygen atom
  • n N21 , n N22 , n N31 and n N32 each independently represent an integer of 0 to 3
  • n N21 + n N22 and n N31 + n N32 are each independently 1, 2 or 3
  • the compounds represented by the general formulas (N-2) and (N-3) are preferably compounds having a negative ⁇ and an absolute value larger than 3.
  • R N21 , R N22 , R N31 and R N32 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.
  • alkenyl groups or alkenyloxy groups having 2 to 5 carbon atoms are preferable, alkyl groups having 1 to 5 carbon atoms or alkenyl groups having 2 to 5 carbon atoms are more preferable, and alkyl groups having 2 to 5 carbon atoms.
  • alkenyl group having 2 to 3 carbon atoms is more preferable, and an alkenyl group having 3 carbon atoms (propenyl group) is particularly preferable.
  • the ring structure to which it is bonded is a phenyl group (aromatic)
  • An alkenyl group having 4 to 5 atoms is preferable
  • the ring structure to which the alkenyl group is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane
  • a straight-chain alkoxy group having 1 to 4 carbon atoms and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred.
  • the total of carbon atoms and oxygen atoms, if present is preferably 5 or less, and is preferably linear.
  • the alkenyl group is preferably selected from groups represented by any of the formulas (R1) to (R5). (The black dots in each formula represent carbon atoms in the ring structure.)
  • a N21 , A N22 , A N31 and A N32 are preferably aromatic when it is required to independently increase ⁇ n, and are preferably aliphatic for improving the response speed.
  • it represents a trans-1,4-cyclohexylene group or a 1,4-phenylene group.
  • Z N21, Z N22, Z N31 and Z N32 is -CH 2 O independently -, - CF 2 O -, - CH 2 CH 2 -, - CF 2 CF 2 - or preferably a single bond, -CH 2 O -, - CH 2 CH 2 - or a single bond is more preferable, -CH 2 O-or a single bond is particularly preferred.
  • XN21 is preferably a fluorine atom.
  • T N31 is preferably an oxygen atom.
  • n N21 + n N22 and n N31 + n N32 are preferably 1 or 2, a combination in which n N21 is 1 and n N22 is 0, a combination in which n N21 is 2 and n N22 is 0, and n N31 is 1 A combination in which n N32 is 0 and a combination in which n N31 is 2 and n N32 is 0 are preferable.
  • the lower limit of the preferable content of the compound represented by the formula (N-2) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 10%, 20%, 30% Yes, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%.
  • the upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.
  • the lower limit of the preferable content of the compound represented by the formula (N-3) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 10%, 20%, 30% Yes, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%.
  • the upper limit of the preferred content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20% It is.
  • the above lower limit value is preferably low and the upper limit value is preferably low. Furthermore, when the composition of the present invention keeps Tni high and a composition having good temperature stability is required, the above lower limit value is preferably low and the upper limit value is preferably low. When it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable that the above lower limit value is increased and the upper limit value is high.
  • the compound represented by the general formula (N-2) is preferably a compound selected from the group of compounds represented by the general formulas (N-2-1) to (N-2-3).
  • the compound represented by the general formula (N-2-1) is the following compound.
  • R N211 and R N212 each independently represents the same meaning as R N11 and R N12 in the general formula (N-1).
  • the compound represented by the general formula (N-2-2) is the following compound.
  • R N221 and R N222 each independently represents the same meaning as R N11 and R N12 in the general formula (N-1).
  • the compound represented by the general formula (N-2-3) is the following compound.
  • the compound represented by the general formula (N-3) is preferably a compound selected from the group of compounds represented by the general formulas (N-3-1) to (N-3-2).
  • the compound represented by the general formula (N-3-1) is the following compound.
  • R N311 and R N312 each independently represent the same meaning as R N11 and R N12 in formula (N-1)).
  • the compound represented by the general formula (N-3-2) is the following compound.
  • R N321 and R N322 each independently represent the same meaning as R N11 and R N12 in formula (N-1).
  • examples of other components include compounds represented by general formula (L-2-B).
  • R L21 and R L22 each independently represent the same meaning as R L21 and R L22 in formula (L-2).
  • R L21 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms
  • R L22 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 4 to 5 carbon atoms.
  • the compound represented by the general formula (L-2-B) is preferably a compound selected from the group of compounds represented by the formula (L-2.3) to the formula (L-2.6).
  • the compounds represented by formula (L-2.3) and formula (L-2.4) are preferable.
  • liquid crystal composition of the present invention examples of other components include compounds represented by general formula (L-7).
  • R L71 and R L72 each independently represent the same meaning as R L11 and R L12 in formula (L-1);
  • a L71 and A L72 each independently (7a) 1,4-cyclohexylene group (this is present in the group one -CH 2 - or nonadjacent two or more -CH 2 - is -O And
  • (7c) (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6- One —CH ⁇ present in a diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or two or more non-adjacent —CH ⁇ are
  • Each of the groups (7a), (7b) and (7c) is independently selected from the group consisting of: a hydrogen atom substituted with a cyano group, a fluorine atom or a chlorine atom.
  • Z L71 represents a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —OCF 2 —, —CF 2 O—.
  • R L71 and R L72 each independently represent a fluorine atom or a hydrogen atom, but at least one of them represents a hydrogen atom.
  • R L71 and R L72 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and A L71 and A L72 are each independently 1,4-cyclohexyl.
  • a silene group or a 1,4-phenylene group is preferable, and hydrogen atoms on A L71 and A L72 may be each independently substituted with a fluorine atom, and Z L71 is preferably a single bond or COO— X L71 and X L72 are preferably hydrogen atoms.
  • the kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, and four kinds.
  • the content of the compound represented by the general formula (L-7) includes solubility at low temperature, transition temperature, electrical reliability, birefringence index, process suitability, dripping marks, It is necessary to adjust appropriately according to required performance such as image sticking and dielectric anisotropy.
  • the lower limit of the preferable content of the compound represented by the formula (L-7) with respect to the total amount of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5% Yes, 7%, 10%, 14%, 16%, 20%.
  • the upper limit of the preferable content of the compound represented by the formula (L-7) with respect to the total amount of the liquid crystal composition of the present invention is 30%, 25%, 23%, 20% Yes, 18%, 15%, 10%, 5%.
  • liquid crystal composition of the present invention When a high Tni embodiment of the liquid crystal composition of the present invention is desired, it is preferable to increase the content of the compound represented by formula (L-7), and when a low viscosity embodiment is desired, It is preferable to reduce the amount.
  • the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.1) to the formula (L-7.4), and the formula (L-7. It is preferable that it is a compound represented by 2).
  • the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.11) to the formula (L-7.13). It is preferable that it is a compound represented by 11).
  • the compound represented by the general formula (L-7) is a compound represented by the formula (L-7.21) to the formula (L-7.23).
  • a compound represented by formula (L-7.21) is preferable.
  • the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.31) to the formula (L-7.34), and the formula (L-7. 31) or / and a compound represented by the formula (L-7.32).
  • the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.41) to the formula (L-7.44), and the formula (L-7. 41) or / and a compound represented by formula (L-7.42).
  • the liquid crystal composition of the present invention preferably does not contain a compound having a structure in which oxygen atoms such as a peracid (—CO—OO—) structure are bonded in the molecule.
  • the content of the compound having a carbonyl group is preferably 5% or less, and preferably 3% or less with respect to the total mass of the liquid crystal composition. Is more preferably 1% or less, and most preferably not substantially contained.
  • the content of the compound substituted with chlorine atoms is preferably 15% or less, preferably 10% or less, based on the total mass of the liquid crystal composition, It is preferably 8% or less, more preferably 5% or less, further preferably 3% or less, and still more preferably substantially not contained.
  • the content of a compound in which all the ring structures in the molecule are 6-membered rings is based on the total mass of the liquid crystal composition. It is preferably 80% or more, more preferably 90% or more, still more preferably 95% or more, and the composition is composed of only a compound in which all of the ring structures in the molecule are 6-membered rings. Most preferably, it is configured.
  • the content of the compound having a cyclohexenylene group is the total mass of the liquid crystal composition.
  • the content is preferably 10% or less, more preferably 8% or less, more preferably 5% or less, further preferably 3% or less, and still more preferably not contained.
  • the content of a compound having a 2-methylbenzene-1,4-diyl group in the molecule, in which a hydrogen atom may be substituted with a halogen may be reduced.
  • the content of the compound having a 2-methylbenzene-1,4-diyl group in the molecule is preferably 10% or less, more preferably 8% or less with respect to the total mass of the liquid crystal composition. It is preferably 5% or less, more preferably 3% or less, and still more preferably substantially not contained.
  • substantially not contained in the present invention means that it is not contained except for unintentionally contained matter.
  • the composition of the present invention may contain a polymerizable compound in order to produce a liquid crystal display element such as a PS mode, a transverse electric field type PSA mode, or a transverse electric field type PSVA mode.
  • a polymerizable compound such as a PS mode, a transverse electric field type PSA mode, or a transverse electric field type PSVA mode.
  • the polymerizable compound that can be used include a photopolymerizable monomer that undergoes polymerization by energy rays such as light.
  • the structure has, for example, a liquid crystal skeleton in which a plurality of six-membered rings such as biphenyl derivatives and terphenyl derivatives are connected. Examples thereof include a polymerizable compound. More specifically, the general formula (XX)
  • Z 201 represents —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH
  • X 201 and X 202 are each preferably a diacrylate derivative that represents a hydrogen atom, or a dimethacrylate derivative that has a methyl group, and a compound in which one represents a hydrogen atom and the other represents a methyl group.
  • the polymerization rate of these compounds is the fastest for diacrylate derivatives, slow for dimethacrylate derivatives, and intermediate for asymmetric compounds, and a preferred embodiment can be used depending on the application.
  • a dimethacrylate derivative is particularly preferable.
  • Sp 201 and Sp 202 each independently represent a single bond, an alkylene group having 1 to 8 carbon atoms, or —O— (CH 2 ) s —, but at least one of them is a single bond in a PSA display element.
  • a compound in which both represent a single bond or one in which one represents a single bond and the other represents an alkylene group having 1 to 8 carbon atoms or —O— (CH 2 ) s — is preferable.
  • 1 to 4 alkyl groups are preferable, and s is preferably 1 to 4.
  • Z 201 represents —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 — or a single bond
  • —COO—, —OCO— or a single bond is more preferred, and a single bond is particularly preferred.
  • M 201 represents a 1,4-phenylene group, a trans-1,4-cyclohexylene group or a single bond in which any hydrogen atom may be substituted by a fluorine atom, but the 1,4-phenylene group or the single bond is preferable.
  • C represents a ring structure other than a single bond
  • Z 201 is preferably a linking group other than a single bond.
  • M 201 is a single bond
  • Z 201 is preferably a single bond.
  • the ring structure between Sp 201 and Sp 202 is specifically preferably the structure described below.
  • both ends shall be bonded to Sp 201 or Sp 202.
  • the polymerizable compounds containing these skeletons are optimal for PSA-type liquid crystal display elements because of their alignment restriction power after polymerization, and a good alignment state is obtained, so that display unevenness is suppressed or does not occur at all.
  • general formula (XX-1) to general formula (XX-4) are particularly preferable, and among them, general formula (XX-2) is most preferable.
  • Sp 20 represents an alkylene group having 2 to 5 carbon atoms.
  • the polymerization proceeds even when no polymerization initiator is present, but may contain a polymerization initiator in order to accelerate the polymerization.
  • the polymerization initiator include benzoin ethers, benzophenones, acetophenones, benzyl ketals, acylphosphine oxides, and the like.
  • composition in the present invention may further contain a compound represented by the general formula (Q) together with the compound of the general formula (I).
  • RQ represents a straight-chain alkyl group or a branched-chain alkyl group having 1 to 22 carbon atoms, and one or more CH 2 groups in the alkyl group are —O—so that oxygen atoms are not directly adjacent to each other.
  • MQ represents a trans-1,4-cyclohexylene group, a 1,4
  • the compound represented by the general formula (Q) is preferably a compound represented by the following general formula (Qa) to general formula (Qd).
  • R Q1 is preferably a linear or branched alkyl group having 1 to 10 carbon atoms
  • R Q2 is preferably a linear or branched alkyl group having 1 to 20 carbon atoms
  • R Q3 is A straight-chain alkyl group having 1 to 8 carbon atoms, a branched-chain alkyl group, a straight-chain alkoxy group or a branched-chain alkoxy group is preferred
  • L Q is preferably a straight-chain alkylene group or branched-chain alkylene group having 1 to 8 carbon atoms.
  • compounds represented by general formula (Qa) to general formula (Qd) compounds represented by general formula (Qc) and general formula (Qd) are more preferable.
  • liquid crystal composition of the present invention when the compound represented by the general formula (Q) is contained, it is preferably contained in 1 to 5 types, and the content is preferably 0.001 to 1%, 0.001 to 0.1% is more preferable, and 0.001 to 0.05% is particularly preferable.
  • the polymerizable compound contained therein is polymerized by ultraviolet irradiation to impart liquid crystal alignment ability, and the amount of transmitted light is controlled using the birefringence of the composition.
  • liquid crystal display elements As liquid crystal display elements, AM-LCD (active matrix liquid crystal display element), TN (nematic liquid crystal display element), STN-LCD (super twisted nematic liquid crystal display element), OCB-LCD and IPS-LCD (in-plane switching liquid crystal display element)
  • AM-LCD active matrix liquid crystal display element
  • TN nematic liquid crystal display element
  • STN-LCD super twisted nematic liquid crystal display element
  • OCB-LCD OCB-LCD
  • IPS-LCD in-plane switching liquid crystal display element
  • the two substrates of the liquid crystal cell used in the liquid crystal display element can be made of a transparent material having flexibility such as glass or plastic, and one of them can be an opaque material such as silicon.
  • a transparent substrate having a transparent electrode layer can be obtained, for example, by sputtering indium tin oxide (ITO) on a transparent substrate such as a glass plate.
  • the color filter can be prepared by, for example, a pigment dispersion method, a printing method, an electrodeposition method, or a dyeing method.
  • a method for producing a color filter by a pigment dispersion method will be described as an example.
  • a curable coloring composition for a color filter is applied on the transparent substrate, subjected to patterning treatment, and cured by heating or light irradiation. By performing this process for each of the three colors red, green, and blue, a pixel portion for a color filter can be created.
  • a pixel electrode provided with an active element such as a TFT, a thin film diode, or a metal insulator metal specific resistance element may be provided on the substrate.
  • the substrate is opposed so that the transparent electrode layer is on the inside.
  • the thickness of the obtained light control layer is 1 to 100 ⁇ m. More preferably, the thickness is 1.5 to 10 ⁇ m.
  • the polarizing plate it is preferable to adjust the product of the refractive index anisotropy ⁇ n of the liquid crystal and the cell thickness d so that the contrast is maximized.
  • the polarizing axis of each polarizing plate can be adjusted so that the viewing angle and contrast are good.
  • a retardation film for widening the viewing angle can also be used.
  • the spacer examples include columnar spacers made of glass particles, plastic particles, alumina particles, a photoresist material, and the like. Thereafter, a sealant such as an epoxy thermosetting composition is screen-printed on the substrates with a liquid crystal inlet provided, the substrates are bonded together, and heated to thermally cure the sealant.
  • a sealant such as an epoxy thermosetting composition is screen-printed on the substrates with a liquid crystal inlet provided, the substrates are bonded together, and heated to thermally cure the sealant.
  • the above-described components include a substrate having a common electrode made of a transparent conductive material, a pixel electrode made of a transparent conductive material, and a thin film transistor for controlling the pixel electrode provided in each pixel.
  • a substrate having a common electrode made of a transparent conductive material By sandwiching the liquid crystal composition of the present invention between the substrates and setting the liquid crystal molecules in the liquid crystal composition to be substantially vertical when no voltage is applied, it is useful to achieve both high-speed response and suppression of display defects.
  • a VA mode liquid crystal display element can be obtained.
  • substantially vertical includes a state having a desired pretilt angle from the vertical direction. The pretilt angle is preferably inclined by 1 ° from the vertical direction, and more preferably by 0.5 °.
  • liquid crystal composition of the present invention is sandwiched between a common electrode made of a transparent conductive material and a pixel electrode for each pixel on one substrate, and the other substrate is a transparent insulating substrate, Useful IPS mode or FFS mode which has both high-speed response and suppression of display failure by setting the alignment film layer to induce homogeneous alignment on the substrate and setting the alignment direction of each alignment film to be parallel
  • IPS mode or FFS mode which has both high-speed response and suppression of display failure by setting the alignment film layer to induce homogeneous alignment on the substrate and setting the alignment direction of each alignment film to be parallel
  • the liquid crystal display element can be obtained.
  • a normal vacuum injection method or an ODF method can be used as a method for sandwiching the polymerizable compound-containing composition between the two substrates.
  • a display element manufactured using the ODF method In the ODF liquid crystal display device manufacturing process, a sealant such as epoxy photothermal combination curing is drawn on a backplane or frontplane substrate using a dispenser in a closed-loop bank shape, and then removed.
  • a liquid crystal display element can be manufactured by bonding a front plane and a back plane after dropping a predetermined amount of the composition under air.
  • the composition of the present invention can be suitably used because the composition can be stably dropped in the ODF process.
  • an appropriate polymerization rate is desirable in order to obtain good alignment performance of liquid crystals. Therefore, active energy rays such as ultraviolet rays or electron beams are irradiated singly or in combination or sequentially.
  • the method of polymerizing by is preferred.
  • ultraviolet rays When ultraviolet rays are used, a polarized light source or a non-polarized light source may be used.
  • the polymerization is carried out in a state where the polymerizable compound-containing composition is sandwiched between two substrates, at least the substrate on the irradiated surface side must be given adequate transparency to the active energy rays. Don't be.
  • the orientation state of the unpolymerized part is changed by changing conditions such as an electric field, a magnetic field, or temperature, and further irradiation with active energy rays is performed. Then, it is possible to use a means for polymerization.
  • a means for polymerization In particular, when ultraviolet exposure is performed, it is preferable to perform ultraviolet exposure while applying an alternating electric field to the polymerizable compound-containing composition.
  • the alternating electric field to be applied is preferably an alternating current having a frequency of 10 Hz to 10 kHz, more preferably a frequency of 60 Hz to 10 kHz, and the voltage is selected depending on a desired pretilt angle of the liquid crystal display element.
  • the pretilt angle of the liquid crystal display element can be controlled by the applied voltage.
  • the pretilt angle is preferably controlled from 80 degrees to 89.9 degrees from the viewpoint of alignment stability and contrast.
  • the intensity of the irradiated ultraviolet light is preferably 0.1 mW / cm 2 to 100 W / cm 2, more preferably 2 mW / cm 2 to 50 W / cm 2.
  • the amount of energy of ultraviolet rays to be irradiated can be adjusted as appropriate, but is preferably 10 mJ / cm 2 to 500 J / cm 2, and more preferably 100 mJ / cm 2 to 200 J / cm 2.
  • the intensity may be changed.
  • the time for irradiating with ultraviolet rays is appropriately selected depending on the intensity of the irradiated ultraviolet rays, but is preferably from 10 seconds to 3600 seconds, and more preferably from 10 seconds to 600 seconds.
  • the liquid crystal display device using the liquid crystal composition of the present invention is useful for achieving both high-speed response and suppression of display failure, and is particularly useful for a liquid crystal display device for active matrix driving, including VA mode, PSVA mode, It can be applied to PSA mode, IPS mode or ECB mode liquid crystal display elements.
  • the measured characteristics are as follows.
  • T NI Nematic phase-isotropic liquid phase transition temperature (° C) ⁇ n: refractive index anisotropy at 25 ° C. ⁇ : dielectric anisotropy at 25 ° C. ⁇ : viscosity at 20 ° C. (mPa ⁇ s) ⁇ 1: rotational viscosity at 25 ° C. (mPa ⁇ s) VHR: Voltage holding ratio (%) at 60 ° C. under conditions of frequency 60 Hz and applied voltage 1 V After 1000 hours VHR: Voltage holding ratio (%) at 60 ° C.
  • Burn-in evaluation of the liquid crystal display element is based on the following four-level evaluation of the afterimage level of the fixed pattern when the predetermined fixed pattern is displayed in the display area for 1000 hours and then the entire screen is uniformly displayed. went.
  • Example 1 Example 2, Comparative Example 1 and Comparative Example 2
  • a liquid crystal composition X shown below was prepared.
  • the physical properties of the liquid crystal composition X were as follows.
  • liquid crystal composition 1 was prepared in which all the compounds having an alkenyl side chain group in the liquid crystal composition X were replaced with compounds having an alkyl side chain group.
  • the physical properties of the liquid crystal composition 1 were as follows.
  • liquid crystal composition 1 containing a compound having an alkenyl side chain group has a rotational viscosity ⁇ 1 of about 15% lower than that of the liquid crystal composition X not containing it.
  • Composition A (Example 1)
  • Composition B (Example 2)
  • Liquid crystal composition 1 containing no compound of general formula (I) (Comparative Example 1)
  • Liquid crystal composition containing no compound of general formula (I) The results of evaluation of VHR, afterimage and dropping marks of product X (Comparative Example 2) are shown in the following table.
  • a long-time high-temperature test of the liquid crystal composition 1 shown in Comparative Example 1 shows that the VHR has decreased from the initial stage, and the residual evaluation and drop mark evaluation are inferior, but the compound of the general formula (I) is added.
  • the decrease in VHR was suppressed, and the residual evaluation and drop mark evaluation also showed good results.
  • Even in the liquid crystal composition X not containing a compound having an alkenyl side chain group a decrease in VHR was observed, and the residual evaluation and drop mark evaluation were inferior.
  • Examples 3 to 6 and Comparative Examples 3 to 4 Liquid crystal compositions 2 and 3 shown in the following table were prepared.
  • compositions in which 0.03% of the compound represented by formula (I-1-1) or formula (I-2-1) is added to 99.97% of liquid crystal composition 2 and liquid crystal composition 3 C to Composition F were prepared.
  • the physical properties of the composition to which the compound represented by formula (I-1-1) or formula (I-2-1) was added were almost unchanged from the original liquid crystal composition.
  • composition C (Example 3), Composition D (Example 4), Composition E (Example 5), Composition F (Example 6), Liquid crystal composition 2 containing no compound of general formula (I)
  • the following table shows the results of evaluation of VHR, afterimages and dropping marks of the liquid crystal composition 3 (Comparative Example 4) not containing the compound of Comparative Example 3 and the general formula (I).
  • composition containing the compound of the general formula (I) was able to suppress a decrease in VHR due to a long-time high-temperature test as compared with a composition other than that, and showed good results in residual evaluation and drop mark evaluation.
  • Examples 7 to 10 and Comparative Examples 5 to 6 Liquid crystal compositions 4 and 5 shown in the following table were prepared.
  • compositions in which 0.03% of the compound represented by formula (I-1-1) or formula (I-2-1) is added to 99.97% of liquid crystal composition 4 and liquid crystal composition 5 G to Composition J were prepared.
  • the physical properties of the composition to which the compound represented by formula (I-1-1) or formula (I-2-1) was added were almost unchanged from the original liquid crystal composition.
  • composition G (Example 7), Composition H (Example 8), Composition I (Example 9), Composition J (Example 10), Liquid crystal composition 4 containing no compound of general formula (I)
  • the following table shows the results of evaluation of VHR, afterimages and dropping marks of the liquid crystal composition 5 (Comparative Example 6) not containing the compound of (Comparative Example 5) and the general formula (I).
  • composition containing the compound of the general formula (I) was able to suppress a decrease in VHR due to a long-time high-temperature test as compared with a composition other than that, and showed good results in residual evaluation and drop mark evaluation.

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Abstract

　L'invention concerne une composition de cristaux liquides nématiques d'anisotropie de constante diélectrique (Δε) négative utile en tant que matériau d'affichage à cristaux liquides, ainsi qu'un élément d'affichage à cristaux liquides mettant en œuvre cette composition. Cette composition de cristaux liquides possède une grande valeur absolue de ladite anisotropie de constante diélectrique et une faible viscosité. Elle fait preuve d'une bonne solubilité à faible température, d'une résistance spécifique et d'un taux de maintien de la tension élevés, ainsi que d'une bonne stabilité face à la chaleur et à la lumière. En outre, l'élément d'affichage à cristaux liquides mettant en œuvre cette composition, permet d'obtenir un affichage à contrastes élevés, à réponse rapide, et simultanément excellent en termes de qualité d'affichage, présentant peu de risque que des défauts d'affichage tels que ombres ou gouttes ne surviennent. Cet élément d'affichage à cristaux liquides mettant en œuvre cette composition est avantageux en ce qu'il combine une réponse rapide et une inhibition des défauts d'affichage, est plus particulièrement avantageux en tant que dispositif d'affichage à cristaux liquides pour entraînement de matrice active, et est adapté à un élément d'affichage à cristaux liquides de type à orientation verticale (VA), PSA, ou similaire.
PCT/JP2015/077919 2014-10-10 2015-10-01 Composition de cristaux liquides et élément d'affichage à cristaux liquides mettant en œuvre celle-ci WO2016056455A1 (fr)

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WO2019102859A1 (fr) * 2017-11-21 2019-05-31 Dic株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides

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WO2019102859A1 (fr) * 2017-11-21 2019-05-31 Dic株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides

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