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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
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  • C09K19/00—Liquid crystal materials
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  • 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
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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
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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
  • C09K19/18—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
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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
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
  • C09K19/22—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and nitrogen atoms as chain links, e.g. Schiff bases
• • C—CHEMISTRY; METALLURGY
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
  • C09K19/24—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing nitrogen-to-nitrogen bonds
• • C—CHEMISTRY; METALLURGY
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
• • 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
  • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
• • C—CHEMISTRY; METALLURGY
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
• • 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
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01Q—ANTENNAS, i.e. RADIO AERIALS
  • H01Q21/00—Antenna arrays or systems
  • H01Q21/06—Arrays of individually energised antenna units similarly polarised and spaced apart
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01Q—ANTENNAS, i.e. RADIO AERIALS
  • H01Q3/00—Arrangements for changing or varying the orientation or the shape of the directional pattern of the waves radiated from an antenna or antenna system
  • H01Q3/26—Arrangements for changing or varying the orientation or the shape of the directional pattern of the waves radiated from an antenna or antenna system varying the relative phase or relative amplitude of energisation between two or more active radiating elements; varying the distribution of energy across a radiating aperture
  • H01Q3/30—Arrangements for changing or varying the orientation or the shape of the directional pattern of the waves radiated from an antenna or antenna system varying the relative phase or relative amplitude of energisation between two or more active radiating elements; varying the distribution of energy across a radiating aperture varying the relative phase between the radiating elements of an array
  • H01Q3/34—Arrangements for changing or varying the orientation or the shape of the directional pattern of the waves radiated from an antenna or antenna system varying the relative phase or relative amplitude of energisation between two or more active radiating elements; varying the distribution of energy across a radiating aperture varying the relative phase between the radiating elements of an array by electrical means
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01Q—ANTENNAS, i.e. RADIO AERIALS
  • H01Q3/00—Arrangements for changing or varying the orientation or the shape of the directional pattern of the waves radiated from an antenna or antenna system
  • H01Q3/44—Arrangements for changing or varying the orientation or the shape of the directional pattern of the waves radiated from an antenna or antenna system varying the electric or magnetic characteristics of reflecting, refracting, or diffracting devices associated with the radiating element

Definitions

• the present invention relates to a liquid crystal composition and liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas that use the same.
• Liquid crystals are widely used in displays, but as a new application, liquid crystal antennas that transmit and receive radio waves between a mobile object such as a car and a communication satellite are attracting attention.
• satellite communication uses parabolic antennas, but when used in a mobile object such as a car, the parabolic antenna must be pointed toward the satellite at any time, which requires a large movable part.
• liquid crystal antennas can change the direction of radio waves by moving the liquid crystal inside the panel, so there is no need to move the antenna itself and the shape of the antenna can be made flat.
• low-orbit satellite constellations using a large number of low-orbit satellites are being studied.
• Liquid crystal antennas which can easily change the direction of radio waves, are useful for tracking low-orbit satellites that appear to be constantly moving from the ground.
• automatic driving of automobiles and the like requires downloading a large amount of data of high-precision 3D map information.
• an antenna using liquid crystal is incorporated into an automobile, it becomes possible to download a large amount of data from a communication satellite without any mechanical moving parts.
• the frequency band used in satellite communication is about 13 GHz, which is significantly different from the frequencies used for liquid crystal displays up to now. Therefore, the required physical properties of the liquid crystal are also significantly different, and the ⁇ n required for the liquid crystal for the antenna is, for example, about 0.4, and the operating temperature range is, for example, from -20 to 120°C.
• Infrared laser image recognition and distance measuring devices using liquid crystals are also attracting attention as sensors for automatic driving of moving objects such as automobiles.
• the ⁇ n required for liquid crystals for this purpose is, for example, 0.3 to 0.6, and the operating temperature range is, for example, 10 to 100°C.
• many liquid crystal compounds constituting a liquid crystal composition exhibiting a high ⁇ n of 0.2 or more have low compatibility, and therefore it is also important to select a liquid crystal compound having high compatibility.
• Patent Document 1 can be mentioned as a technique for liquid crystal for antennas.
• Non-Patent Document 1 proposes the use of liquid crystal materials as components of high frequency devices.
• An object of the present invention is to provide a liquid crystal composition having high T ni , large ⁇ n, large ⁇ r , small tan ⁇ iso and good storage stability at room temperature, and a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device and an antenna each using the same.
• a liquid crystal composition containing one or more compounds represented by general formula (i) having an alkenyl group and an isothiocyanate group (-NCS), and one or more compounds represented by general formula (ii) having an alkynyl group and an isothiocyanate group (-NCS), and have thus completed the present invention.
• An example of the configuration of the present invention that solves the above problem is as follows.
• Oxygen atoms do not bond directly to each other, n i1 represents an integer of 0 to 1. and one or more compounds represented by the formula: The following general formula (ii
• R ii1 represents an alkynyl group having 2 to 20 carbon atoms; one or more -CH 2 - in the alkynyl group may each independently be substituted by -O-, -S-, -NH-, -CO- and/or -CS-; One or more -CH 2 -CH 2 - in the alkynyl group may each independently be replaced by -C ⁇ C-; One or more hydrogen atoms in the alkynyl group may be independently substituted with a halogen atom, Oxygen atoms do not bond directly to each other, A ii1 , A ii2 and A ii3 each independently represent a hydrocarbon ring having 3 to 16 carbon atoms or a heterocycle having 3 to 16 carbon atoms; one or more hydrogen atoms in A ii1 , A ii2 and A ii3 may each independently be substituted by a substituent S ii1 ; the substituent S ii1 ; the
• n ii1 represents an integer of 0 to 2;
• n ii3 and Z ii2 may be the same or different.
• a liquid crystal composition comprising one or more compounds represented by the following formula:
• the total content of the compounds represented by the general formula (i) in the liquid crystal composition (100% by mass) is 1 to 40% by mass, and/or 2.
• Each R iii1 independently represents an alkyl group having 1 to 20 carbon atoms; One or more -CH 2 - in the alkyl group may each independently be substituted by -O-, -S-, -NH-, -CO- and/or -CS-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom.
• a iii1 and A iii2 may each independently be substituted by a substituent S iii1 ;
• Substituent S iii1 represents any one of a halogen atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms; one or more -CH 2 - in the alkyl group may each independently be substituted by -O-, -S-, -NH-, -CO- and/or
• Item 6 The liquid crystal composition according to any one of items 1 to 5, which has a liquid crystal phase upper limit temperature (T ni ) of 120° C. or higher.
• Item 7 A liquid crystal display device using the liquid crystal composition according to any one of items 1 to 6.
• Item 8 The liquid crystal display element according to item 7, which is driven by an active matrix method or a passive matrix method.
• Item 9 A liquid crystal display element that reversibly switches the dielectric constant by reversibly changing the alignment direction of the liquid crystal molecules of the liquid crystal composition according to any one of items 1 to 6.
• Item 10 A sensor using the liquid crystal composition according to any one of items 1 to 6.
• Item 11 A liquid crystal lens using the liquid crystal composition according to any one of items 1 to 6.
• Item 12 An optical communication device using the liquid crystal composition according to any one of items 1 to 6.
• Item 13 An antenna using the liquid crystal composition according to any one of items 1 to 6.
• Item 14 The antenna according to item 13, a first substrate having a plurality of slots; a second substrate facing the first substrate and provided with a power supply unit; a first dielectric layer provided between the first substrate and the second substrate; A plurality of patch electrodes arranged corresponding to the plurality of slots; a third substrate on which the patch electrode is provided; a liquid crystal layer provided between the first substrate and the third substrate; Item 7.
• liquid crystal composition containing one or more compounds represented by general formula (i) having an alkenyl group and an isothiocyanate group (-NCS), and one or more compounds represented by general formula (ii) having an alkynyl group and an isothiocyanate group (-NCS), it is possible to obtain a liquid crystal composition having high T ni , large ⁇ n, large ⁇ r , small tan ⁇ iso , and good storage stability at room temperature, and the liquid crystal composition is useful for liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas.
• the liquid crystal composition according to the present invention contains one or more compounds represented by general formula (i) having an alkenyl group and an isothiocyanate group (-NCS).
• R i1 represents an alkenyl group having 2 to 20 carbon atoms.
• the alkenyl group having 2 to 20 carbon atoms is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.
• the alkenyl group having 2 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• One or more -CH 2 - in the alkenyl group may each independently be substituted by -O-, -S-, -NH-, -CO- and/or -CS-.
• one or more hydrogen atoms in the alkenyl group may each independently be substituted with a halogen atom.
• the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.
• the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms and/or oxygen atoms are not directly bonded to each other.
• Specific examples of the alkenyl group having 1 to 20 carbon atoms for R i1 include groups represented by the formulae (R i1 -1) to (R i1 -19).
• R i1 is preferably a linear alkenyl group having 2 to 6 carbon atoms.
• a i1 , A i2 and A i3 each independently represent a hydrocarbon ring having 3 to 16 carbon atoms or a heterocycle having 3 to 16 carbon atoms. More specifically, the hydrocarbon ring having 3 to 16 carbon atoms or the heterocycle having 3 to 16 carbon atoms is the following group (a), group (b), group (c), and group (d): (a) a 1,4-cyclohexylene group (in which one —CH 2 — or two or more non-adjacent —CH 2 — groups may be replaced by —O— or —S—).
• One or more hydrogen atoms in A i1 , A i2 and A i3 may each independently be substituted with a substituent S i1 .
• the substituent S i1 represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms.
• the alkyl group may be a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.
• the alkyl group preferably has 2 to 10, preferably 3 to 6, carbon atoms.
• One or more -CH 2 - in the alkyl group may each independently be substituted by -O-, -S-, -NH-, -CO- and/or -CS-.
• one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.
• halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms and/or oxygen atoms are not directly bonded to each other.
• the substituent S i1 is preferably a fluorine atom, a chlorine atom, a linear alkyl group having 1 to 6 carbon atoms, or a linear alkoxy group having 1 to 6 carbon atoms.
• At least one of A i1 , A i2 and A i3 is preferably substituted with at least one substituent S i1 . Also, A i3 is preferably substituted with at least one substituent S i1 . When there are a plurality of substituents S i1 , they may be the same or different.
• substitution position of the substituent S i1 in A i1 is preferably any one of the following formulae (A i1 -SP-1) to (A i1 -SP-4).
• a white dot represents a bond to R i1
• a black dot represents a bond to Z i1 .
• the substitution position of the substituent S i1 in A i2 is preferably any one of the following formulae (A i2 -SP-1) to (A i2 -SP-4).
• the white dots represent bonds to Z i1
• the black dots represent bonds to Z i2 or an isothiocyanate group (-NCS).
• the substitution position of the substituent S i1 in A i3 is preferably any one of the following formulae (A i3 -SP-1) to (A i3 -SP-4).
• a i1 preferably represents any one of the following formulae (A i1 -1) to (A i1 -11).
• a white dot represents a bond to R i1
• a black dot represents a bond to Z i1 .
• a i2 preferably represents any one of the following formulae (A i2 -1) to (A i2 -13).
• the white dots represent bonds to Z i1
• the black dots represent bonds to Z i2 or an isothiocyanate group (-NCS).
• a i3 preferably represents any one of the following formulas (A i3 -1) to (A i3 -11).
• the white dots represent bonds to Z i2
• the black dots represent bonds to an isothiocyanate group (-NCS).
• Z i1 and Z i2 each independently represent a single bond or an alkylene group having 1 to 20 carbon atoms.
• the alkylene group is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.
• the alkylene group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• One or more -CH 2 - in the alkylene group may each independently be substituted with -O-, -CF 2 - and/or -CO-.
• the alkylene group is substituted with a specific group, the oxygen atoms are not directly bonded to each other.
• alkylene group having 2 to 20 carbon atoms include groups represented by the formulae (Z i1/2 -1) to (Z i1/2 -24).
• Z i1 is preferably represented by the formula (Z i1/2 ⁇ 4)( ⁇ C ⁇ C ⁇ ).
• n i1 represents an integer of 0 to 1.
• Z i2 preferably represents a single bond.
• the compound represented by general formula (i) is preferably a compound represented by the following general formulas (i-1) to (i-2).
• R i1 , A i1 , A i2 and A i3 each independently represent the same meaning as R i1 , A i1 , A i2 and A i3 in formula (i) above.
• the compound represented by general formula (i-1) is preferably a compound represented by the following general formulas (i-1-1) to (i-1-2).
• R i1 and S i1 each independently represent the same meaning as R i1 and S i1 in the general formula (i) above.
• Specific examples of the compound represented by general formula (i-1-1) include compounds represented by the following structural formulas (i-1-1.1) to (i-1-1.8).
• Specific examples of compounds represented by general formula (i-1-2) include compounds represented by the following structural formulas (i-1-2.1) to (i-1-2.6).
• the compound represented by general formula (i-2) is preferably a compound represented by the following general formulas (i-2-1) to (i-2-2).
• R i1 and S i1 each independently represent the same meaning as R i1 and S i1 in the general formula (i).
• Specific examples of the compound represented by general formula (i-2-1) include compounds represented by the following structural formulas (i-2-1.1) to (i-2-1.7).
• Specific examples of the compound represented by general formula (i-2-1) include the compounds represented by the following structural formulas (i-2-2.1) to (i-2-2.8).
• the compounds represented by general formula (i), general formulas (i-1) to (i-2), general formulas (i-1-1) to (i-1-2), general formulas (i-2-1) to (i-2-2), structural formulas (i-1-1.1) to (i-1-1.8), structural formulas (i-1-2.1) to (i-1-2.6), structural formulas (i-2-1.1) to (i-2-1.7) or structural formulas (i-2-2.1) to (i-2-2.8) are used in the liquid crystal composition in one or more types, preferably 1 to 10 types, preferably 1 to 5 types, preferably 1 to 3 types.
• the lower limit of the total content of the compounds represented by general formula (i), general formula (i-1) to (i-2), general formula (i-1-1) to (i-1-2), general formula (i-2-1) to (i-2-2), structural formula (i-1-1.1) to (i-1-1.8), structural formula (i-1-2.1) to (i-1-2.6), structural formula (i-2-1.1) to (i-2-1.7), or structural formula (i-2-2.1) to (i-2-2.8) in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, more preferably 3% by mass or more, more preferably 5% by mass or more, more preferably 10% by mass or more, more preferably 15% by mass or more, more preferably 20% by mass or more, more preferably 25% by mass or more, and more preferably 30% by mass or more.
• the upper limit of the total content of the compounds represented by general formula (i), general formulas (i-1) to (i-2), general formulas (i-1-1) to (i-1-2), general formulas (i-2-1) to (i-2-2), structural formulas (i-1-1.1) to (i-1-1.8), structural formulas (i-1-2.1) to (i-1-2.6), structural formulas (i-2-1.1) to (i-2-1.7), or structural formulas (i-2-2.1) to (i-2-2.8) in 100% by mass of the liquid crystal composition is preferably 40% by mass or less, preferably 35% by mass or less, preferably 30% by mass or less, preferably 25% by mass or less, preferably 20% by mass or less, preferably 15% by mass or less, preferably 10% by mass or less, and preferably 5% by mass or less.
• the total content of the compounds represented by general formula (i), general formulae (i-1) to (i-2), general formulae (i-1-1) to (i-1-2), general formulae (i-2-1) to (i-2-2), structural formulae (i-1-1.1) to (i-1-1.8), structural formulae (i-1-2.1) to (i-1-2.6), structural formulae (i-2-1.1) to (i-2-1.7), or structural formulae (i-2-2.1) to (i-2-2.8) in 100% by mass of the liquid crystal composition is preferably 1 to 40% by mass, more preferably 3 to 35% by mass, and even more preferably 5 to 35% by mass, from the viewpoints of solubility, ⁇ n, and/or ⁇ r .
• the compound represented by the general formula (i) (including its sub-concepts) can be synthesized by using a known synthesis method.
• the liquid crystal composition according to the present invention contains one or more compounds represented by general formula (i) having an alkynyl group and an isothiocyanate group (-NCS).
• R ii1 represents an alkynyl group having 2 to 20 carbon atoms.
• the alkynyl group having 2 to 20 carbon atoms is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.
• the alkynyl group having 2 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• One or more -CH 2 - in the alkynyl group may each independently be substituted by -O-, -S-, -NH-, -CO- and/or -CS-.
• one or more -CH 2 -CH 2 - in the alkynyl group may each independently be replaced by -C ⁇ C-.
• one or more hydrogen atoms in the alkynyl group may each independently be substituted with a halogen atom.
• the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.
• the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms and/or oxygen atoms are not directly bonded to each other.
• alkynyl group from the viewpoints of ease of synthesis and elongation of the conjugated system, an alkynyl group represented by the following formula (R ii1 -A) is preferred.
• R ii1A represents an alkyl group having 1 to 18 carbon atoms.
• the alkyl group having 1 to 18 carbon atoms may be a straight-chain, branched or cyclic alkyl group, and is preferably a straight-chain alkyl group.
• the alkyl group having 1 to 18 carbon atoms preferably has 1 to 8 carbon atoms.
• One or more -CH 2 - in the alkyl group may each independently be substituted by -O-, -S-, -NH-, -CO- and/or -CS-.
• one or more -CH 2 -CH 2 - in the alkyl group may each independently be substituted with -C ⁇ C-.
• one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.
• the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms and/or oxygen atoms are not directly bonded to each other.
• the black dot represents a bond to A ii1 .
• R ii1 examples include groups represented by formulae (R ii1 -1) to (R ii1 -16).
• R ii1 is preferably a linear alkynyl group having 2 to 8 carbon atoms.
• a ii1 , A ii2 and A ii3 each independently represent a hydrocarbon ring having 3 to 16 carbon atoms or a heterocycle having 3 to 16 carbon atoms. More specifically, the hydrocarbon ring having 3 to 16 carbon atoms or the heterocycle having 3 to 16 carbon atoms is the following group (a), group (b), group (c), and group (d): (a) a 1,4-cyclohexylene group (in which one —CH 2 — or two or more non-adjacent —CH 2 — groups may be replaced by —O— or —S—).
• One or more hydrogen atoms in A ii1 , A ii2 and A ii3 may each independently be substituted by a substituent S ii1 .
• the substituent S ii1 represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms.
• the alkyl group may be a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.
• the alkyl group preferably has 2 to 10, preferably 3 to 6, carbon atoms.
• One or more -CH 2 - in the alkyl group may each independently be substituted by -O-, -S-, -NH-, -CO- and/or -CS-.
• one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.
• halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms and/or oxygen atoms are not directly bonded to each other.
• the substituent S ii1 is preferably a fluorine atom, a linear alkyl group having 1 to 6 carbon atoms, or a linear alkoxy group having 1 to 6 carbon atoms.
• At least one of A ii1 , A ii2 and A ii3 is preferably substituted with at least one substituent S i1 . Also, A ii3 is preferably substituted with at least one substituent S i1 . When there are a plurality of substituents S ii1 , they may be the same or different.
• substitution position of the substituent S ii1 in A ii1 is preferably any one of the following formulae (A ii1 -SP-1) to (A ii1 -SP-4).
• the white dots represent bonds to R ii1
• the black dots represent bonds to Z ii1 .
• the substitution position of the substituent S i1 in A ii2 is preferably any one of the following formulae (A ii2 -SP-1) to (A ii2 -SP-4).
• the white dots represent bonds to Z ii1
• the black dots represent bonds to Z ii2 or an isothiocyanate group (-NCS).
• the substitution position of the substituent S ii1 in A ii3 is preferably any one of the following formulae (A ii3 -SP-1) to (A ii3 -SP-4).
• a ii1 preferably represents any one of the following formulas (A ii1 -1) to (A ii1 -11).
• a ii2 preferably represents any one of the following formulas (A ii2 -1) to (A ii2 -11).
• a ii3 preferably represents any one of the following formulas (A ii3 -1) to (A ii3 -11).
• the white dots represent bonds to Z ii2
• the black dots represent bonds to Z ii2 or an isothiocyanate group (-NCS).
• Z ii1 and Z ii2 each independently represent a single bond or an alkylene group having 1 to 20 carbon atoms.
• the alkylene group is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.
• the alkylene group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• One or more -CH 2 - in the alkylene group may each independently be substituted with -O-, -CF 2 - and/or -CO-.
• the alkylene group is substituted with a specific group, the oxygen atoms are not directly bonded to each other.
• alkylene group having 2 to 20 carbon atoms include groups represented by the formulae (Z ii1/2 -1) to (Z ii1/2 -24).
• the white dots represent bonds to A ii1 , A ii2 or A ii3
• the black dots represent bonds to A ii2 or A ii3 .
• Z ii1 and Z ii2 each independently represent a single bond or —C ⁇ C—.
• at least one of Z ii1 and Z ii2 is —C ⁇ C—.
• n ii1 represents an integer of 0 to 2.
• Z ii1 or Z ii2 preferably represents -C ⁇ C- in view of ⁇ n and/or ⁇ r .
• n ii1 is 2, it is preferable that at least one of Z ii2 represents --C ⁇ C-- from the viewpoint of ⁇ n and/or ⁇ r .
• Z ii2 preferably represents a single bond or -C ⁇ C- from the viewpoint of ⁇ n and/or ⁇ r .
• a plurality of A ii3 and Z ii2 when a plurality of A ii3 and Z ii2 are present, they may be the same or different.
• the compound represented by general formula (ii) is preferably a compound represented by the following general formulas (ii-1) to (ii-3).
• R ii1 , A ii1 , A ii2 and A ii3 have the same meanings as R ii1 , A ii1 , A ii2 and A ii3 in the above general formula (ii), respectively.
• the definition of A ii3-2 is the same as the definition of A ii3-2 in the above general formula (ii).
• the compound represented by general formula (ii-1) is preferably a compound represented by the following general formulas (ii-1-1) to (ii-1-3).
• R ii1 and S ii1 each independently represent the same meaning as R ii1 and S ii1 in formula (ii) above.
• Specific examples of the compound represented by general formula (ii-1-1) include compounds represented by the following structural formulas (ii-1-1.1) to (ii-1-1.2).
• Specific examples of compounds represented by general formula (ii-1-2) include compounds represented by the following structural formulas (ii-1-2.1) to (ii-1-2.2).
• the compound represented by general formula (ii-2) is preferably a compound represented by the following general formulas (ii-2-1) to (ii-2-3).
• R ii1 and S ii1 each independently represent the same meaning as R ii1 and S ii1 in the general formula (ii) above.
• Specific examples of the compound represented by general formula (ii-2-1) include compounds represented by the following structural formulas (ii-2-1.1) to (ii-2-1.2).
• Specific examples of compounds represented by general formula (ii-2-2) include compounds represented by the following structural formulas (ii-2-2.1) to (ii-2-2.5).
• the compound represented by general formula (ii-3) is preferably a compound represented by the following general formula (ii-3-1):
• R ii1 and S ii1 each independently represent the same meaning as R ii1 and S ii1 in formula (ii) above.
• Specific examples of the compound represented by general formula (ii-3-1) include compounds represented by the following structural formulas (ii-3-1.1) to (ii-3-1.2).
• the type of compound represented by general formula (ii), general formulas (ii-1) to (ii-3), general formulas (ii-1-1) to (i-1-3), general formulas (ii-2-1) to (ii-2-3), general formula (ii-3-1), structural formulas (ii-1-1.1) to (ii-1-1.2), structural formulas (ii-1-2.1) to (ii-1-2.2), structural formula (ii-1-3.1), structural formulas (ii-2-1.1) to (ii-2-1.2), structural formulas (ii-2-2.1) to (ii-2-2.5), structural formulas (ii-2-3.1) or structural formulas (ii-3-1.1) to (ii-3-1.2) used in the liquid crystal composition is one or more types, preferably 1 to 10 types, preferably 1 to 5 types, and preferably 1 to 3 types.
• the total content of the compounds represented by the general formula (ii), the general formulae (ii-1) to (ii-3), the general formulae (ii-1-1) to (i-1-3), the general formulae (ii-2-1) to (ii-2-3), the general formula (ii-3-1), the structural formulae (ii-1-1.1) to (ii-1-1.2), the structural formulae (ii-1-2.1) to (ii-1-2.2), the structural formula (ii-1-3.1), the structural formulae (ii-2-1.1) to (ii-2-1.2), the structural formulae (ii-2-2.1) to (ii-2-2.5), the structural formulae (ii-2-3.1) or the structural formulae (ii-3-1.1) to (ii-3-1.2) in 100% by mass of the liquid crystal composition is determined based on the solubility, ⁇ n and/or ⁇ From the viewpoint of r , it is preferably from 1 to 55 mass %, more preferably from 3 to 50 mass %, and even more preferably from
• the compound represented by general formula (ii) (including its sub-concepts) can be synthesized using known synthesis methods.
• the liquid crystal composition according to the present invention preferably contains one or more compounds having an isothiocyanate group (—NCS) and represented by the following general formula (iii):
• R iii1 represents an alkyl group having 1 to 20 carbon atoms.
• the alkyl group may be a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.
• the alkyl group preferably has 2 to 10, preferably 2 to 6 carbon atoms.
• One or more -CH 2 - in the alkyl group may each independently be substituted by -O-, -S-, -NH-, -CO- and/or -CS-.
• one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.
• halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms and/or oxygen atoms are not directly bonded to each other.
• R iii1 can represent an alkoxy group having 1 to 19 carbon atoms by replacing one --CH 2 -- in the alkyl group with --O--.
• the alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.
• the alkoxy group preferably has 2 to 10, more preferably 2 to 6, carbon atoms.
• R iii1 can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms by replacing one —CH 2 — in the alkyl group with —S—.
• the alkylsulfanyl group is a linear, branched or cyclic alkylsulfanyl group, and is preferably a linear alkylsulfanyl group.
• the alkylsulfanyl group preferably has 1 to 10, more preferably 1 to 6, carbon atoms.
• R iii1 can represent a halogenated alkyl group having 1 to 20 carbon atoms, in which one or more hydrogen atoms in the alkyl group have been substituted with halogen atoms.
• the halogenated alkyl group may be linear, branched or cyclic, and is preferably a linear halogenated alkyl group.
• the halogenated alkyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• R iii1 can represent a halogenated alkoxy group having 1 to 19 carbon atoms, in which one —CH 2 — in the alkyl group is replaced with —O—, and one or more hydrogen atoms in the alkyl group are replaced with halogen atoms.
• the halogenated alkoxy group may be a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.
• the halogenated alkoxy group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• Specific examples of the alkyl group having 1 to 20 carbon atoms for R iii1 include groups represented by the formulae (R iii1 -1) to (R iii1 -30).
• R iii1 is preferably a linear or branched alkyl group having 2 to 8 carbon atoms, a linear alkoxy group having 2 to 8 carbon atoms, a linear halogenated alkoxy group having 1 to 8 carbon atoms, or a linear alkylsulfanyl group having 1 to 6 carbon atoms.
• One or more hydrogen atoms in A iii1 and A iii2 may each independently be substituted by a substituent S iii1 .
• the substituent S iii1 represents any one of a halogen atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms.
• halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• the alkyl group having 1 to 20 carbon atoms may be a straight-chain, branched or cyclic alkyl group, and is preferably a straight-chain alkyl group.
• the alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• One or more -CH 2 - in the alkyl group may each independently be substituted by -O-, -S-, -NH-, -CO- and/or -CS-.
• one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.
• the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms and/or oxygen atoms are not directly bonded to each other.
• the substituent S iii1 can represent an alkoxy group having 1 to 19 carbon atoms by replacing one --CH 2 -- in the alkyl group with --O--.
• the alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.
• the alkoxy group preferably has 2 to 10, more preferably 2 to 6, carbon atoms.
• the substituent S iii1 can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms by replacing one --CH 2 -- in the alkyl group with --S--.
• the alkylsulfanyl group is a linear, branched or cyclic alkylsulfanyl group, and is preferably a linear alkylsulfanyl group.
• the alkylsulfanyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• the alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.
• the alkenyl group preferably has 2 to 10, more preferably 2 to 6, carbon atoms.
• the substituent S iii1 can represent an alkynyl group having 2 to 20 carbon atoms by replacing one or more -CH 2 -CH 2 - in the alkyl group with -C ⁇ C-.
• the alkynyl group may be a straight-chain, branched or cyclic alkynyl group, and is preferably a straight-chain alkynyl group.
• the alkynyl group preferably has 2 to 10, more preferably 2 to 6, carbon atoms.
• the substituent S iii1 can represent an alkenyloxy group having 2 to 19 carbon atoms by replacing one —CH 2 — in the alkyl group with —O— and one or more —CH 2 —CH 2 — groups with —CH ⁇ CH—.
• the alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.
• the alkenyloxy group preferably has 2 to 10, more preferably 2 to 6, carbon atoms.
• the substituent S iii1 can represent a halogenated alkyl group having 1 to 20 carbon atoms by substituting one or more hydrogen atoms in the alkyl group with halogen atoms.
• the halogenated alkyl group may be linear, branched or cyclic, and is preferably a linear halogenated alkyl group.
• the halogenated alkyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• the substituent S iii1 can represent a halogenated alkoxy group having 1 to 19 carbon atoms, in which one -CH 2 - in the alkyl group is replaced with -O-, and one or more hydrogen atoms in the alkyl group are replaced with halogen atoms.
• the halogenated alkoxy group may be a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.
• the halogenated alkoxy group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) in the substituent S iii1 include groups represented by the formulae (S iii1R -1) to (S iii1R -36).
• the black dot represents a bond to A iii1 or A iii2 .
• the substituent S iii1 is preferably a linear alkyl group having 1 to 6 carbon atoms, a fluorine atom or a chlorine atom.
• at least one of A iii1 or A iii2 is preferably substituted with at least one substituent S iii1 , preferably with a halogen atom, and more preferably with a fluorine atom.
• substituents S iii1 may be the same or different.
• substitution position of the substituent S iii1 in A iii1 is preferably any one of the following formulae (A iii1 -SP-1) to (A iii1 -SP-24).
• a white dot represents a bond to R iii1 or Z iii1
• a black dot represents a bond to Z iii1 .
• the substitution position of the substituent S iii1 in A iii2 is preferably any one of the following formulae (A iii2 -SP-1) to (A iii2 -SP-8).
• a iii1 preferably represents any one of the following formulae (A iii1 -1) to (A iii1 -49).
• a white dot represents a bond to R iii1 or Z iii1
• a black dot represents a bond to Z iii1 .
• a iii2 preferably represents any one of the following formulas (A iii2 -1) to (A iii2 -10).
• white dots represent bonds to Z iii1
• black dots represent bonds to an isothiocyanate group (--NCS).
• Z iii1 represents a single bond or an alkylene group having 1 to 20 carbon atoms.
• One or more -CH 2 - in the alkylene group may each independently be substituted with -O-, -CF 2 - and/or -CO-.
• the alkylene group having 1 to 20 carbon atoms is substituted with a specific group, the oxygen atoms are not directly bonded to each other.
• sulfur atoms and/or oxygen atoms are not directly bonded to each other.
• alkylene group having 1 to 20 carbon atoms include groups represented by the formulae (Z iii1 -1) to (Z iii1 -24).
• n iii1 represents an integer of 1 to 4, preferably 1 or 2.
• Z iii1 preferably represents a single bond or -C ⁇ C- from the viewpoint of ⁇ n and/or ⁇ r .
• Z iii1 preferably represents a single bond or --C ⁇ C-- from the viewpoint of ⁇ n and/or ⁇ r .
• a iii1 and Z iii1 when a plurality of A iii1 and Z iii1 are present, they may be the same or different.
• the compound represented by general formula (iii) is preferably a compound represented by the following general formulas (iii-1) to (iii-4).
• R iii1 , A iii1 and A iii2 have the same meanings as R iii1 , A iii1 and A iii2 in the above general formula (iii), respectively.
• the definition of A iii1-2 is independently the same as the definition of A iii1 in general formula (ii) above.
• the compound represented by general formula (iii-1) is preferably a compound represented by the following general formula (iii-1-1):
• R iii1 and S iii1 each independently have the same meaning as R iii1 and S iii1 in general formula (iii), respectively.
• Specific examples of the compound represented by general formula (iii-1-1) include compounds represented by the following structural formulas (iii-1-1.1) to (iii-1-1.3).
• the compound represented by general formula (iii-2) is preferably a compound represented by the following general formulas (iii-2-1) to (iii-2-3).
• R iii1 and S iii1 each independently have the same meaning as R iii1 and S iii1 in the general formula (iii), respectively.
• Specific examples of the compound represented by general formula (iii-2-1) include compounds represented by the following structural formulas (iii-2-1.1) to (iii-2-1.2).
• Specific examples of compounds represented by general formula (iii-2-2) include compounds represented by the following structural formulas (iii-2-2.1) to (iii-2-2.2).
• Specific examples of compounds represented by general formula (iii-2-3) include compounds represented by the following structural formulas (iii-2-3.1) to (iii-2-3.2).
• the compound represented by general formula (iii-3) is preferably a compound represented by the following general formulas (iii-3-1) to (iii-3-2).
• R iii1 and S iii1 each independently have the same meaning as R iii1 and S iii1 in the general formula (iii), respectively.
• Specific examples of the compound represented by general formula (iii-3-1) include compounds represented by the following structural formulas (iii-3-1.1) to (iii-3-1.2).
• Specific examples of compounds represented by general formula (iii-3-2) include compounds represented by the following structural formulas (iii-3-2.1) to (iii-3-2.2).
• the compound represented by general formula (iii-4) is preferably a compound represented by the following general formulas (iii-4-1) to (iii-4-3).
• R iii1 and S iii1 each independently have the same meaning as R iii1 and S iii1 in the general formula (iii), respectively.
• Specific examples of the compound represented by general formula (iii-4-1) include compounds represented by the following structural formulas (iii-4-1.1) to (iii-4-1.2).
• Specific examples of compounds represented by general formula (iii-4-2) include compounds represented by the following structural formulas (iii-4-2.1) to (iii-4-2.2).
• Specific examples of compounds represented by general formula (iii-4-3) include compounds represented by the following structural formulas (iii-4-3.1) to (iii-4-3.2).
• the lower limit of the total content of the compounds represented by formulas (iii-4-2.1) to (iii-4-2.2) or structural formulas (iii-4-3.1) to (iii-4-3.2) in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, preferably 1% by mass or more, preferably 3% by mass or more, preferably 10% by mass or more, preferably 15% by mass or more, preferably 20% by mass or more, preferably 25% by mass or more, preferably 30% by mass or more, preferably 35% by mass or more, preferably 40% by mass or more, preferably 45% by mass or more, preferably 50% by mass or more, and preferably 55% by mass or more.
• the compound represented by general formula (iii) (including its sub-concepts) can be synthesized using known synthesis methods.
• liquid crystal composition (Liquid Crystal Composition)
• the liquid crystal composition according to the present invention can be produced, for example, by mixing the compound represented by the above-mentioned general formula (i), the compound represented by the general formula (ii), and, if necessary, the above-mentioned other compounds and additives.
• Additives include stabilizers, dye compounds, polymerizable compounds, azotolane compounds, isothiocyanate compounds (NCS compounds), etc.
• the stabilizer examples include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, ⁇ -naphthylamines, ⁇ -naphthols, nitroso compounds, hindered phenols, and hindered amines.
• the hindered phenols include hindered phenol-based antioxidants represented by the following structural formulas (XX-1) to (XX-5).
• Hindered amines include hindered amine light stabilizers represented by the following structural formulas (YY-1) to (YY-2).
• the type of stabilizer used in the liquid crystal composition is one or more, preferably 1 to 10 types, preferably 1 to 8 types, preferably 1 to 6 types, preferably 1 to 4 types, preferably 1 to 2 types.
• the total content of the stabilizer in 100% by mass of the liquid crystal composition is preferably 0.005 to 1% by mass, more preferably 0.02 to 0.50% by mass, and even more preferably 0.03 to 0.35% by mass.
• the combination of compounds used in the liquid crystal composition is preferably selected from the viewpoints of solubility, ⁇ n and/or Tni .
• 1) A combination of a compound represented by general formula (i) (including sub-concepts) and a compound represented by general formula (ii) (including sub-concepts) 2) A combination of a compound represented by general formula (i) (including sub-concepts), a compound represented by general formula (ii) (including sub-concepts), and a compound represented by general formula (iii) (including sub-concepts), 3) A combination of a compound represented by general formula (i-1) (including subordinate concepts), a compound represented by general formula (ii-2) (including subordinate concepts), and a compound represented by general formula (iii-1) (including subordinate concepts), 4) A combination of a compound represented by general formula (i-1-2) (including subordinate concepts), a compound represented by general formula (ii-2-2) (including subordinate concepts), and a compound represented by general formula (iii
• the liquid crystal phase upper limit temperature (T ni ) is the temperature at which the liquid crystal composition undergoes phase transition from a nematic phase to an isotropic phase.
• T ni is measured by preparing a preparation in which the liquid crystal composition is sandwiched between a slide glass and a cover glass, and observing the preparation under a polarizing microscope while heating the preparation on a hot stage. It can also be measured by differential scanning calorimetry (DSC). The unit used is "°C". The higher T ni is, the more the nematic phase can be maintained even at high temperatures, and the wider the operating temperature range can be.
• the upper limit temperature (T ni ) of the liquid crystal phase of the liquid crystal composition according to the present invention can be appropriately set depending on whether the liquid crystal display element is used indoors, in a car, or outdoors, where the external temperature can be controlled, and from the viewpoint of the driving temperature range, it is preferably 120° C. or higher, more preferably 120 to 250° C., and even more preferably 125 to 215° C.
• the liquid crystal phase lower limit temperature (T ⁇ n ) of the liquid crystal composition according to the present invention is preferably 10°C or lower, more preferably -70 to 0°C, and even more preferably -40 to -5°C, from the viewpoint of driving temperature.
• ⁇ n (refractive index anisotropy) correlates with ⁇ n in the near-infrared region used in the optical sensor described below.
• ⁇ n at 25° C. and 589 nm is determined from the difference ( ne ⁇ no ) between the extraordinary refractive index ( ne ) and the ordinary refractive index ( no ) of the liquid crystal composition using an Abbe refractometer.
• ⁇ n can be obtained from a phase difference measuring device.
• a liquid crystal composition is injected into a glass cell having a cell gap (d) of about 3.0 ⁇ m and a polyimide alignment film that has been subjected to anti-parallel rubbing treatment, and the in-plane Re is measured using a retardation film/optical material inspection device RETS-100 (manufactured by Otsuka Electronics Co., Ltd.). The measurement was carried out at a temperature of 25° C. and at 589 nm, and the measurement was unitless. The ⁇ n at 25° C.
• liquid crystal composition according to the present invention is preferably 0.40 or more, more preferably 0.40 to 0.65, more preferably 0.41 to 0.60, and even more preferably 0.43 to 0.55, from the viewpoint of the phase modulation power of light of the wavelength.
• the dielectric anisotropy ⁇ r and the average value tan ⁇ iso of the dielectric tangent at 10 GHz were measured as representative characteristics in the high frequency range.
• ⁇ r is the dielectric constant
• tan ⁇ is the dielectric tangent
• the subscript " ⁇ ” indicates the component parallel to the alignment direction of the liquid crystal
• ⁇ indicates the component perpendicular to the alignment direction of the liquid crystal.
• ⁇ r and tan ⁇ iso can be measured by the following method.
• a liquid crystal composition is introduced into a capillary tube made of polytetrafluoroethylene (PTFE).
• the capillary used here has an inner radius of 0.80 mm and an outer radius of 0.835 mm, with an effective length of 4.0 cm.
• the capillary tube containing the liquid crystal composition is introduced into the center of a cavity resonator (manufactured by EM Lab Co., Ltd.) having a resonance frequency of 10 GHz.
• the cavity has an outer diameter of 30 mm and a width of 26 mm.
• a signal is then input, and the result of the output signal is recorded using a network analyzer (manufactured by Keysight Technologies, Inc.).
• the dielectric constant ( ⁇ r ) and loss angle ( ⁇ ) at 10 GHz are determined using the difference between the resonance frequency of a PTFE capillary tube containing no liquid crystal composition and the resonance frequency of a PTFE capillary tube containing a liquid crystal composition.
• the tangent of the obtained ⁇ is the dielectric tangent (tan ⁇ ).
• the resonance frequency and the like using a PTFE capillary tube filled with a liquid crystal composition are determined as values of characteristic components perpendicular to and parallel to the alignment direction of the liquid crystal molecules by controlling the alignment of the liquid crystal molecules.
• the magnetic field of a permanent magnet or electromagnet is used to align the liquid crystal molecules in the vertical direction (perpendicular to the effective length) or in the parallel direction (parallel to the effective length) of the PTFE capillary tube.
• the magnetic field has, for example, a pole-to-pole distance of 45 mm and a magnetic field strength of 0.23 Tesla near the center.
• the PTFE capillary tube containing the liquid crystal composition is rotated parallel or perpendicular to the magnetic field to obtain the desired characteristic components.
• the electric field application time may be set to a value that allows the liquid crystal to be uniformly aligned, and in the present invention, the electric field application time is set to 8 minutes. The measurements were carried out at a temperature of 25° C., and both ⁇ r and tan ⁇ iso have no unit.
• the ⁇ r at 25° C. of the liquid crystal composition according to the present invention is preferably larger, and from the viewpoint of phase modulation power in the GHz band, it is preferably 0.90 or more, more preferably 0.90 to 1.65, more preferably 0.95 to 1.60, and even more preferably 1.00 to 1.55.
• the tan ⁇ iso at 25° C. of the liquid crystal composition according to the present invention is preferably smaller, and from the viewpoint of loss in the GHz band, it is preferably 0.025 or less, more preferably 0.001 to 0.025, more preferably 0.003 to 0.020, more preferably 0.005 to 0.017, more preferably 0.007 to 0.015, more preferably 0.008 to 0.013, and more preferably 0.009 to 0.012.
• liquid crystal display elements Liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices and antennas
• a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the liquid crystal composition according to the present invention will be described below.
• the liquid crystal display element according to the present invention is characterized by using the above-mentioned liquid crystal composition, and is preferably driven by an active matrix system or a passive matrix system.
• the liquid crystal display element according to the present invention is preferably a liquid crystal display element in which the dielectric constant is reversibly switched by reversibly changing the alignment direction of the liquid crystal molecules of the above-mentioned liquid crystal composition.
• the sensor according to the present invention is characterized by using the above-mentioned liquid crystal composition, and examples of its embodiments include a distance measuring sensor that uses electromagnetic waves, visible light or infrared light, an infrared sensor that uses a change in temperature, a temperature sensor that uses a change in the wavelength of reflected light due to a change in the pitch of a cholesteric liquid crystal, a pressure sensor that uses a change in the wavelength of reflected light, an ultraviolet sensor that uses a change in the wavelength of reflected light due to a change in composition, an electrical sensor that uses a change in temperature due to a voltage or current, a radiation sensor that uses a temperature change accompanying the track of a radiation particle, an ultrasonic sensor that uses a change in the arrangement of liquid crystal molecules due to mechanical vibration of ultrasonic waves, and an electromagnetic field sensor that uses a change in the wavelength of reflected light due to a change in temperature or a change in the arrangement of liquid crystal molecules due to an electric field.
• a distance measuring sensor that uses electromagnetic waves
• the distance measurement sensor is preferably for use in LiDAR (Light Detection and Ranging) that uses a light source.
• LiDAR is preferably used for artificial satellites, aircraft, unmanned aerial vehicles (drones), automobiles, railways, and ships.
• the light source is preferably an LED or a laser, preferably a laser.
• the light used in LiDAR is preferably infrared light, and its wavelength is preferably 800 to 2000 nm. In particular, an infrared laser with a wavelength of 905 nm or 1550 nm is preferred.
• the liquid crystal composition according to the present invention exhibits a high ⁇ n value, and therefore has a large phase modulation power in the visible light, infrared light and electromagnetic wave regions, and can provide a sensor with excellent detection sensitivity.
• the liquid crystal lens according to the present invention is characterized by using the above-mentioned liquid crystal composition, and for example, in one embodiment thereof, has a first transparent electrode layer, a second transparent electrode layer, a liquid crystal layer containing the above-mentioned liquid crystal composition provided between the first transparent electrode layer and the second transparent electrode layer, an insulating layer provided between the second transparent electrode layer and the liquid crystal layer, and a high-resistance layer provided between the insulating layer and the liquid crystal layer.
• the liquid crystal lens according to the present invention is used, for example, as a 2D/3D switching lens, a lens for adjusting the focus of a camera, and the like.
• the optical communication device is characterized by using the above-mentioned liquid crystal composition.
• one of the embodiments thereof is a liquid crystal on silicon (LCOS) structure having a liquid crystal layer, in which liquid crystals constituting each of a plurality of pixels are two-dimensionally arranged on a reflective layer (electrode).
• LCOS liquid crystal on silicon
• the optical communication device according to the present invention is used, for example, as a spatial phase modulator.
• the antenna according to the present invention is characterized by using the above-mentioned liquid crystal composition. More specifically, the antenna of the present invention comprises a first substrate having a plurality of slots, a second substrate facing the first substrate and having a power supply section, a first dielectric layer provided between the first substrate and the second substrate, a plurality of patch electrodes arranged corresponding to the plurality of slots, a third substrate having the patch electrodes provided thereon, and a liquid crystal layer provided between the first substrate and the third substrate, wherein the liquid crystal layer contains the above-mentioned liquid crystal composition.
• the liquid crystal composition according to the present invention it is possible to provide an antenna that is highly reliable against external stimuli such as heat.
• the antenna according to the invention preferably operates in the Ka or K or Ku band frequencies used for satellite communications.
• the antenna according to the present invention preferably has a configuration in which a radial line slot array and a patch antenna array are combined.
• the structure of the antenna according to the present invention can be applied by taking into consideration the matters described in, for example, International Publication No. 2021/157189.
• n in the table is a natural number.
• the alkyl group represented by n is a linear alkyl group.
• n in the table is a natural number.
• the alkylene group represented by n is a linear alkylene group.
• Examples 1 to 31 and Comparative Examples 1 and 2 Liquid crystal compositions were prepared using LC-A to B and LC-01 to 07, hindered phenol antioxidants (XX-1) to (XX-3), and hindered amine light stabilizers (YY-1) to (YY-2), and the physical properties of the compositions were measured and a storage stability test was carried out. The results are shown in Tables 4 to 8. Note that in Comparative Example 1, the high frequency characteristics ( ⁇ r and tan ⁇ iso ) were not measured because the crystallization occurred at room temperature.
• ⁇ Storage test> 0.5 g of the liquid crystal composition was weighed into a 1 mL sample bottle (manufactured by Maruemu Co., Ltd.), and degassed for 10 minutes at 150 to 250 Pa. The bottle was then purged with dry nitrogen and the attached lid was placed on the bottle. The bottle was then stored in a temperature-controlled thermostatic chamber (manufactured by Espec Corp., SH-241) at 25°C for two weeks, and the occurrence of crystallization of the liquid crystal composition was visually confirmed every week.
• a temperature-controlled thermostatic chamber manufactured by Espec Corp., SH-241
• Example 1 From Example 1, it was confirmed that a liquid crystal composition containing one or more compounds represented by the general formula (i) and one or more compounds represented by the general formula (ii) has high T ni , large ⁇ n, large ⁇ r , small tan ⁇ iso , and good storage stability at room temperature. On the other hand, from Comparative Examples 1 and 2, it was found that liquid crystal compositions not containing one or more compounds represented by the general formula (i) and one or more compounds represented by the general formula (ii) had poor storage stability or a low Tni of less than 120°C. In addition, in Comparative Example 1, it was confirmed that LC-A was crystallized one week after preparation. Furthermore, from Examples 2 to 31, it was confirmed that the same effects were obtained when various compounds were used or when a hindered phenol-based antioxidant or a hindered amine-based light stabilizer was used in combination.
• the liquid crystal composition of the present invention can be used in liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices and antennas.

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