Classifications

• • C—CHEMISTRY; METALLURGY
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  • 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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  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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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
  • 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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  • C09K19/08—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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  • C09K19/10—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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  • C09K19/06—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
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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
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
  • C09K19/28—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and sulfur atoms as chain links, e.g. thioesters
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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
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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
• • 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
  • G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01Q—ANTENNAS, i.e. RADIO AERIALS
  • H01Q13/00—Waveguide horns or mouths; Slot antennas; Leaky-waveguide antennas; Equivalent structures causing radiation along the transmission path of a guided wave
  • H01Q13/20—Non-resonant leaky-waveguide or transmission-line antennas; Equivalent structures causing radiation along the transmission path of a guided wave
  • H01Q13/22—Longitudinal slot in boundary wall of waveguide or transmission line

Definitions

• the present invention relates to a liquid crystal composition and to liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas that use the same.
• Liquid crystals which are widely used in displays, are attracting attention as a new application for liquid crystal antennas that transmit and receive radio waves between mobile objects such as automobiles and communication satellites.
• satellite communications have used parabolic antennas.
• the parabolic antenna when used in mobile objects such as automobiles, the parabolic antenna must be constantly pointed toward the satellite, necessitating large moving parts.
• liquid crystal antennas can change the direction of radio waves by moving the liquid crystals inside the panel. This eliminates the need to move the antenna itself, and the antenna shape can be made flat.
• low-earth-orbit (LOW-EO) satellite constellations with numerous low-earth-orbit satellites are being studied.
• Liquid crystal antennas which can easily change the direction of radio waves, are useful for tracking low-earth-orbit satellites, which appear to be constantly moving from the ground.
• autonomous driving of automobiles and other vehicles requires the downloading of large amounts of high-precision 3D map information.
• the frequency band used in satellite communications is approximately 13 GHz, which is significantly different from the frequencies used in conventional liquid crystal display applications.
• the required physical properties of the liquid crystal are also significantly different. For example, a ⁇ n of approximately 0.4 is required for liquid crystals used in antennas, and the operating temperature range is, for example, -20 to 120°C.
• liquid crystals are attracting attention as sensors for autonomous driving of moving objects such as automobiles.
• the ⁇ n required for liquid crystals for this application 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 with 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 one embodiment of the present invention is to provide a liquid crystal composition that is excellent in properties such as T ni , ⁇ n, ⁇ 1, ⁇ r , tan ⁇ iso , and/or storage stability, and to provide a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the same.
• Another object of one embodiment of the present invention is to provide a liquid crystal composition that has high T ni , large ⁇ n, large ⁇ r , small tan ⁇ iso , and good storage stability at low temperatures, and to provide a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna each using the liquid crystal composition. Note that the description of these problems does not preclude the existence of other problems, and one embodiment of the present invention does not necessarily solve all of these problems.
• R i1 represents an alkenyl group having 2 to 20 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, Oxygen atoms do not bond directly to each other, A i1 and A i2 each independently represent 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—).
• (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthracene a naphthalene-2,7-diyl group (one -CH
• a i1 and A i2 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; one or more —CH 2 — in the alkyl group may each independently be substituted by —O—, —S—,
• R ii1 each independently represents an alkyl group having 1 to 20 carbon atoms; one or more —CH 2 — groups 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 by —CH ⁇ CH—, —CF ⁇ CF— and/or —C ⁇ C—; One or more hydrogen atoms in the alkyl 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 the following formulae (A ii1/2/3 -SP-1) to (A ii1/2/3 -SP-5):
• the white dot represents a bond of R ii1 , A ii1 , A ii2 or A ii4 ;
• the black dots represent bonds to A ii2 , A ii3 or the isothiocyanate group (-NCS).
• a ii4 represents a group selected from the group consisting of one or more hydrogen atoms in A ii4 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;
• One or more —CH 2 — in the alkyl group may each independently be substituted by —
• the total content of the compounds represented by the general formula (i) in the liquid crystal composition (100% by mass) is 1 to 50% by mass, and/or Item 2.
• the liquid crystal composition according to item 1, wherein the total content of the compounds represented by formula (ii) in 100% by mass of the liquid crystal composition is 1 to 55% by mass.
• R i1 , A i1 and A i2 each independently represent the same meaning as R i1 , A i1 and A i2 in formula (i) above.
• the definition of A i1-2 is the same as the definition of A i1 in the above general formula (i).
• R ii1 , A ii1 , A ii2 , A ii3 and A ii4 have the same meanings as R ii1 , A ii1 , A ii2 , A ii3 and A ii4 in the general formula (ii) above.
• the liquid crystal composition according to item 1 or 2 wherein the compound is selected from the group consisting of compounds represented by the following formula:
• R iii1 each independently represents an alkyl group having 1 to 20 carbon atoms; one or more —CH 2 — groups 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 by —CH ⁇ CH—, —CF ⁇ CF— and/or —C ⁇ C—; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, Oxygen atoms do not bond directly to each other, A iii1 and A iii2 each independently represent 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
• 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; 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 item 1 or 2, having a ⁇ n of 0.40 or more at 25°C and 589 nm.
• Item 7 A liquid crystal display device using the liquid crystal composition described in 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 system or a passive matrix system and reversibly switches the dielectric constant.
• Item 9 A sensor using the liquid crystal composition described in any one of items 1 to 6.
• Item 10 A liquid crystal lens using the liquid crystal composition described in any one of items 1 to 6.
• Item 11 An optical communication device using the liquid crystal composition described in any one of items 1 to 6.
• Item 12 An antenna using the liquid crystal composition described in any one of items 1 to 6.
• Item 13 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.
• An antenna in which the liquid crystal layer contains the liquid crystal composition according to any one of items 1 to 6.
• a liquid crystal composition excellent in properties such as T ni , ⁇ n, ⁇ r , tan ⁇ iso and/or storage stability can be obtained by using 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 a directly bonded 3- or 4- ring structure and an isothiocyanate group (-NCS).
• liquid crystal composition having high Tni , large ⁇ n, large ⁇ r , small tan ⁇ iso , and good storage stability at low temperatures can be obtained, 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 — groups in the alkenyl group may each independently be substituted with —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.
• halogen atom examples 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 are not directly bonded to each other and/or oxygen atoms are not directly bonded to each other.
• Specific examples of the alkenyl group (including substituted ones) having 1 to 20 carbon atoms for R i1 include groups represented by formulae (R i1 -1) to (R i1 -22).
• R i1 is preferably a linear or branched alkenyl group having 2 to 6 carbon atoms.
• One or more hydrogen atoms in A i1 and A i2 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 carbon atoms, more preferably 3 to 6 carbon atoms.
• One or more —CH 2 — groups in the alkyl group may each independently be substituted with —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 are not directly bonded to each other and/or oxygen atoms are not directly bonded to each other.
• a fluorine atom is preferred from the viewpoint of ⁇ r .
• a i1 and A i2 are substituted with at least one substituent S i1 .
• a i2 is preferably substituted with at least one substituent S i1 .
• substituent S i1 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).
• the white dots represent bonds to R i1 or Z i1
• the black dots represent bonds 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).
• a i1 preferably represents any one of the following formulae (A i1 -1) to (A i1 -11).
• the white dots represent bonds to R i1 or Z i1
• the black dots represent bonds to Z i1
• a i2 preferably represents any one of the following formulae (A i2 -1) to (A i2 -11).
• the white dots represent bonds to Z i1
• the black dots represent bonds to the isothiocyanate group (—NCS).
• each Z i1 independently represents 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 — groups 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 formulae (Z i1 -1) to (Z i1 -24).
• Z i1 is preferably a single bond or a group represented by the formula (Z i1 -4)(-C ⁇ C-).
• n i1 represents an integer of 1 or 2.
• Z i1 preferably represents -C ⁇ C- from the viewpoint of improving ⁇ n.
• n i1 is 2, it is preferable that at least one of Z i1 represents —C ⁇ C— from the viewpoint of improving ⁇ n.
• 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 and A i2 each independently represent the same meaning as R i1 , A i1 and A i2 in the general formula (i) above.
• the definition of A i1-2 is the same as the definition of A i1 in the above general formula (i).
• the compound represented by general formula (i-1) is preferably a compound represented by the following general formula (i-1-1):
• 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-1-1.3).
• 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) above.
• 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-2-1.4).
• Specific examples of compounds represented by general formula (i-2-2) include compounds represented by the following structural formulas (i-2-2.1) to (i-2-2.5).
• the compounds represented by general formula (i), general formulas (i-1) to (i-2), general formula (i-1-1), general formulas (i-2-1) to (i-2-2), structural formulas (i-1-1.1) to (i-1-1.3), structural formulas (i-2-1.1) to (i-2-1.4), or structural formulas (i-2-2.1) to (i-2-2.5) may be used in liquid crystal compositions in one or more varieties, preferably 1 to 10 varieties, preferably 1 to 5 varieties, and preferably 1 to 3 varieties.
• the lower limit of the total content of the compounds represented by general formula (i), general formulas (i-1) to (i-2), general formula (i-1-1), general formulas (i-2-1) to (i-2-2), structural formulas (i-1-1.1) to (i-1-1.3), structural formulas (i-2-1.1) to (i-2-1.4), or structural formulas (i-2-2.1) to (i-2-2.5) in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, preferably 3% by mass or more, preferably 5% 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, and preferably 45% 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 formula (i-1-1), general formulas (i-2-1) to (i-2-2), structural formulas (i-1-1.1) to (i-1-1.3), structural formulas (i-2-1.1) to (i-2-1.4), or structural formulas (i-2-2.1) to (i-2-2.5) in 100% by mass of the liquid crystal composition is preferably 50% by mass or less, preferably 45% by mass or less, 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 formulas (i-1) to (i-2), general formula (i-1-1), general formulas (i-2-1) to (i-2-2), structural formulas (i-1-1.1) to (i-1-1.3), structural formulas (i-2-1.1) to (i-2-1.4), or structural formulas (i-2-2.1) to (i-2-2.5) in 100% by mass of the liquid crystal composition is preferably 1 to 50% by mass, more preferably 3 to 45% by mass, and even more preferably 5 to 40% by mass, from the viewpoints of solubility, ⁇ n, and/or ⁇ r .
• the compound represented by general formula (i) (including its sub-concepts) can be synthesized using known synthesis methods.
• Compound represented by general formula (ii) The liquid crystal composition according to the present invention contains one or more compounds represented by general formula (ii) having a directly bonded three or four ring structure and an isothiocyanate group (-NCS).
• R ii1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
• 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 — groups in the alkyl group may each independently be substituted with —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, 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 are not directly bonded to each other and/or oxygen atoms are not directly bonded to each other.
• R ii1 can represent an alkoxy group having 1 to 19 carbon atoms by substituting one —CH 2 — in the alkyl group with —O—.
• the alkoxy group may be a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.
• the alkoxy group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• R ii1 can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms by substituting one —CH 2 — in the alkyl group with —S—.
• the alkylsulfanyl group may be 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.
• R ii1 can represent an alkenyl group having 2 to 20 carbon atoms by substituting one or more —CH 2 —CH 2 — groups in the alkyl group with —CH ⁇ CH—.
• the alkenyl group may be a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.
• the alkenyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• R ii1 can represent an alkynyl group having 2 to 20 carbon atoms by substituting one or more —CH 2 —CH 2 — groups in the alkyl group with —C ⁇ C—.
• the alkynyl group may be a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.
• the alkynyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• R ii1 can represent an alkenyloxy group having 2 to 19 carbon atoms, in which one —CH 2 — in the alkyl group is replaced with —O— and one or more —CH 2 —CH 2 — are replaced 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 carbon atoms, more preferably 2 to 6 carbon atoms.
• R ii1 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 ii1 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 (including substituted ones) having 1 to 20 carbon atoms in R ii1 include groups represented by formulae (R ii1 -1) to (R ii1 -36).
• R ii1 is preferably a linear alkyl group having 1 to 6 carbon atoms.
• a ii1 , A ii2 and A ii3 each independently represent a group selected from the group consisting of groups represented by the following formulae (A ii1/2/3 -SP-1) to (A ii1/2/3 -SP-5).
• a ii4 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—).
• (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthracene a naphthalene-2,7-diyl group (one -CH
• 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 carbon atoms, more preferably 3 to 6 carbon atoms.
• One or more —CH 2 — groups in the alkyl group may each independently be substituted with —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 are not directly bonded to each other and/or oxygen atoms are not directly bonded to each other.
• a fluorine atom is preferred from the viewpoint of ⁇ r .
• At least one of A ii1 , A ii2 and A ii3 is substituted with at least one substituent S ii1 .
• a ii3 is preferably substituted with at least one substituent S ii1 .
• 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).
• substitution position of the substituent S ii1 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 A ii1
• the black dots represent bonds to A ii3 .
• the substitution position of the substituent S i1 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 formulae (A ii1 -1) to (A ii1 -11).
• the white dots represent bonds to R ii1 or A ii4
• the black dots represent bonds to A ii2 .
• a ii2 preferably represents any one of the following formulae (A ii2 -1) to (A ii2 -11).
• a ii3 preferably represents any one of the following formulae (A ii3 -1) to (A ii3 -11).
• a ii4 preferably represents any one of the following formulae (A ii4 -1) to (A ii4 -13).
• n ii1 represents an integer of 0 to 1. From the viewpoint of solubility and low viscosity, n ii1 preferably represents 0.
• the compound represented by general formula (ii) is preferably a compound represented by the following general formulas (ii-1) to (ii-2).
• R ii1 , A ii1 , A ii2 , A ii3 and A ii4 have the same meanings as R ii1 , A ii1 , A ii2 , A ii3 and A ii4 in the general formula (ii) above.
• the compound represented by general formula (ii-1) is preferably a compound represented by the following general formulas (ii-1-1) to (ii-1-5).
• 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-1-1) include compounds represented by the following structural formulas (ii-1-1.1) to (ii-1-1.3).
• 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-1-2.4).
• Specific examples of compounds represented by general formula (ii-1-3) include compounds represented by the following structural formulas (ii-1-3.1) to (ii-1-3.4).
• the compound represented by general formula (ii-1-4) is preferably a compound represented by the following general formulas (ii-1-4.1) to (ii-1-4.4).
• the compound represented by general formula (ii-1-5) is preferably a compound represented by the following general formulas (ii-1-5.1) to (ii-1-5.4).
• the compound represented by general formula (ii-2) is preferably a compound represented by the following general formulas (ii-2-1) to (ii-2-4).
• 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-2-1.4).
• Specific examples of compounds represented by general formula (ii-2-2) include compounds represented by the following structural formulas (ii-2-2.2) to (ii-2-2.4).
• Specific examples of compounds represented by general formula (ii-2-3) include compounds represented by the following structural formulas (ii-2-3.1) to (ii-2-3.4).
• Specific examples of compounds represented by general formula (ii-2-4) include compounds represented by the following structural formulas (ii-2-4.1) to (ii-2-4.4).
• the compounds represented by structural formulas (ii-1-5.1) to (ii-1-5.4), structural formulas (ii-2-1.1) to (ii-2-1.4), structural formulas (ii-2-2.2) to (ii-2-2.4), structural formulas (ii-2-3.1) to (ii-2-3.4), or structural formulas (ii-2-4.1) to (ii-2-4.4) are used in liquid crystal compositions in one or more varieties, preferably 1 to 10 varieties, preferably 1 to 5 varieties, and preferably 1 to 3 varieties.
• 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 a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
• 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 — groups in the alkyl group may each independently be substituted with —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, 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 are not directly bonded to each other 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 substituting one —CH 2 — in the alkyl group with —O—.
• the alkoxy group may be a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.
• the alkoxy group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• R iii1 can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms by substituting one —CH 2 — in the alkyl group with —S—.
• the alkylsulfanyl group may be 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.
• R iii1 can represent an alkenyl group having 2 to 20 carbon atoms by substituting one or more —CH 2 —CH 2 — groups in the alkyl group with —CH ⁇ CH—.
• the alkenyl group may be a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.
• the alkenyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• R iii1 can represent an alkynyl group having 2 to 20 carbon atoms by substituting one or more —CH 2 —CH 2 — groups in the alkyl group with —C ⁇ C—.
• the alkynyl group may be a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.
• the alkynyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• R iii1 can represent an alkenyloxy group having 2 to 19 carbon atoms, in which one —CH 2 — in the alkyl group is replaced with —O— and one or more —CH 2 —CH 2 — are replaced 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 carbon atoms, more preferably 2 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 (including substituted ones) having 1 to 20 carbon atoms for R iii1 include groups represented by formulae (R iii1 -1) to (R iii1 -47).
• R iii1 -1) to (R iii1 -47) the black dot represents a bond to A iii1 .
• R iii1 is preferably a linear alkyl group having 1 to 6 carbon atoms.
• One or more hydrogen atoms in A iii1 and A iii2 may each independently be substituted with 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 — groups 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 alkyl group is substituted with a specific group, the 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 substituting one —CH 2 — in the alkyl group with —O—.
• the alkoxy group may be a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.
• the alkoxy group preferably has 2 to 10 carbon atoms, 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 substituting one —CH 2 — in the alkyl group with —S—.
• the alkylsulfanyl group may be 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 may be a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.
• the alkenyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• the substituent S iii1 can represent an alkynyl group having 2 to 20 carbon atoms by substituting one or more —CH 2 —CH 2 — groups in the alkyl group with —C ⁇ C—.
• the alkynyl group may be a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.
• the alkynyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
• the substituent S iii1 can represent an alkenyloxy group having 2 to 19 carbon atoms, in which one —CH 2 — in the alkyl group is replaced with —O— and one or more —CH 2 —CH 2 — are replaced 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 carbon atoms, more preferably 2 to 6 carbon atoms.
• the substituent S 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.
• 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.
• alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) 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 Siii1 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 formulae (A iii2 -1) to (A iii2 -10).
• the white dots represent bonds to Z iii1
• the black dots represent bonds to the isothiocyanate group (-NCS).
• Z iii1 represents a single bond or an alkylene group having 1 to 20 carbon atoms.
• One or more —CH 2 — groups 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 are not directly bonded to each other and/or oxygen atoms are not directly bonded to each other.
• alkylene group having 1 to 20 carbon atoms include groups represented by formulae (Z iii1 -1) to (Z iii1 -24).
• the white dot represents a bond to A iii1
• the black dot represents a bond to A iii1 or A iii2 .
• n iii1 represents an integer of 1 to 4, preferably 1 or 2.
• Z iii1 preferably represents a single bond or —C ⁇ C— in view of ⁇ n and/or ⁇ r .
• Z iii1 preferably represents a single bond or —C ⁇ C— in view of ⁇ n and/or ⁇ r .
• general formula (iii) when a plurality of A iii1 and Z iii1 are present, they may be the same or different.
• the compounds represented by general formula (iii) exclude compounds represented by general formula (i) or (ii).
• 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 general formula (iii), respectively.
• the definition of A iii1-2 is independently the same as the definition of A iii1 in the general formula (ii) above.
• the compound represented by general formula (iii-1) is preferably a compound represented by the following general formulas (iii-1-1) to (iii-1-2).
• R iii1 and S iii1 each independently represent the same meaning as R iii1 and S iii1 in the general formula (iii) above.
• 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).
• Specific examples of compounds represented by general formula (iii-1-2) include compounds represented by the following structural formulas (iii-1-2.1) to (iii-1-2.3).
• the compound represented by general formula (iii-2) is preferably a compound represented by the following general formulas (iii-2-1) to (iii-2-2).
• R iii1 and S iii1 each independently represent 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).
• the compound represented by general formula (iii-3) is preferably a compound represented by the following general formulas (iii-3-1) to (iii-3-4).
• R iii1 and S iii1 each independently represent 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-3-1.4).
• 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-3-2.4).
• Specific examples of compounds represented by general formula (iii-3-3) include compounds represented by the following structural formulas (iii-3-3.1) to (iii-3-3.4).
• Specific examples of compounds represented by general formula (iii-3-4) include compounds represented by the following structural formulas (iii-3-4.1) to (iii-3-4.4).
• 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 represent 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-4-1.3).
• 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-4-2.3).
• 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-4-3.3).
• 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 general formula (i) above, the compound represented by the general formula (ii) above, and, if necessary, the other compound (compound represented by the general formula (iii)) above, and additives.
• Additives include stabilizers, dye compounds, polymerizable compounds, azotolane compounds, isothiocyanate compounds (NCS compounds), etc.
• stabilizers examples include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, ⁇ -naphthylamines, ⁇ -naphthols, nitroso compounds, hindered phenols, and hindered amines.
• 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 number of types of stabilizers used in the liquid crystal composition is one or more, preferably 1 to 10, preferably 1 to 8, preferably 1 to 6, preferably 1 to 4, preferably 1 to 2.
• 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 determined from the viewpoints of solubility, T ni , ⁇ n and/or ⁇ r as follows: 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-2) (including sub-concepts), a compound represented by general formula (ii-1) (including sub-concepts), and a compound represented by general formula (iii-1) (including sub-concepts), 4) A combination of a compound represented by general formula (i-2-1) (including subordinate concepts) or a compound represented by general formula (i-2-2) (including subordinate concepts), a
• 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 it 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 the like where the external temperature can be controlled, or whether it is used outdoors. From the viewpoint of the operating temperature range, the upper limit temperature (T ni ) of the liquid crystal phase is preferably 130°C or higher, more preferably 130 to 170°C, and even more preferably 135 to 160°C.
• the liquid crystal phase lower limit temperature is the temperature at which the liquid crystal composition undergoes phase transition from another phase (glass phase, smectic phase, crystalline phase) to the nematic phase.
• T ⁇ n is measured by filling a glass capillary with the liquid crystal composition, immersing it in a refrigerant at ⁇ 70° C. to cause the liquid crystal composition to undergo a phase transition to another phase, and observing the change while increasing the temperature. It can also be measured by differential scanning calorimetry (DSC). The unit used is "°C".
• DSC differential scanning calorimetry
• 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 -50 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 later.
• ⁇ 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 also be obtained using a phase difference measuring device.
• a liquid crystal composition is injected into a glass cell with a cell gap (d) of approximately 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 is 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 0.43 to 0.60, and even more preferably 0.45 to 0.55, from the viewpoint of the phase modulation power of light of that wavelength.
• the dielectric anisotropy in the high frequency region the greater the phase modulation power for radio waves in the target frequency band, making it particularly suitable for antenna applications.
• the smaller the dielectric loss tangent in the high frequency range the smaller the energy loss in the target frequency band, which is preferable.
• the dielectric anisotropy ⁇ r and the average value of the dielectric loss tangent tan ⁇ iso at 10 GHz were measured as representative characteristics in the high frequency range.
• ⁇ r is the dielectric constant
• tan ⁇ is the dielectric loss 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.
• the liquid crystal composition is introduced into a capillary tube made of polytetrafluoroethylene (PTFE).
• PTFE polytetrafluoroethylene
• 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 input and 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 resonant frequency of a PTFE capillary tube without a liquid crystal composition and the resonant frequency of a PTFE capillary tube with a liquid crystal composition.
• the tangent of the obtained ⁇ is the dielectric loss 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 direction) or in the parallel direction (parallel to the effective length direction) of the PTFE capillary tube.
• the magnetic field has a pole-to-pole distance of 45 mm and a magnetic field strength of 0.23 tesla near the center, for example.
• the PTFE capillary tube containing the liquid crystal composition is rotated parallel or perpendicular to the magnetic field to obtain the desired characteristic component.
• the electric field application time may be set to a condition that allows the liquid crystal to be uniformly aligned, and in the present invention, the electric field application time was set to 8 minutes. The measurement was carried out at a temperature of 25° C., and both ⁇ r and tan ⁇ iso have no units.
• 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.
• the rotational viscosity ( ⁇ 1 ) is the viscosity related to the rotation of the liquid crystal molecules.
• ⁇ 1 can be measured by filling a liquid crystal composition into a glass cell with a cell gap of about 10 ⁇ m and using LCM-2 (manufactured by Toyo Corporation).
• LCM-2 manufactured by Toyo Corporation
• a horizontally aligned cell is used, and in the case of a liquid crystal composition having a negative dielectric anisotropy, a vertically aligned cell is used.
• the measurement is carried out at a temperature of 25° C., and the unit is mPa ⁇ s.
• the rotational viscosity ( ⁇ 1 ) of the liquid crystal composition according to the present invention at 25° C. is preferably 150 to 850 mPa ⁇ s, more preferably 200 to 750 mPa ⁇ s, and even more preferably 400 to 650 mPa ⁇ s, from the viewpoint of response speed.
• liquid crystal display elements Liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices and antennas
• the liquid crystal display element, sensor, liquid crystal lens, optical communication device, and 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 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 temperature changes, 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 electric sensor that uses a temperature change 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 alignment 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 alignment of liquid crystal molecules due to an electric field.
• a distance measuring sensor that uses electromagnetic waves, visible light or
• the distance measurement sensor is preferably for LiDAR (Light Detection and Ranging) that uses a light source.
• LiDAR is preferably used for 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 the 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, 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-described 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-described 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-described liquid crystal composition, and one embodiment thereof is, for example, a liquid crystal on silicon (LCOS) structure having a liquid crystal layer on a reflective layer (electrode), in which liquid crystals constituting each of a plurality of pixels are two-dimensionally arranged.
• 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 according to 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 provided thereon, 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 electrodes are provided, 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 present invention preferably operates in the Ka band frequencies, or the K band frequencies or the 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 pamphlet.
• 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.
• Liquid crystal compositions were prepared using LC-01 to LC-07 and LC-A and LC-B, hindered phenol antioxidants (XX-1) to (XX-5), 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.
• ⁇ 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 Corporation, SH-241) at ⁇ 20°C for two weeks, and the occurrence of crystallization of the liquid crystal composition was visually confirmed every week.
• Example 1 From Example 1, it was confirmed that a liquid crystal composition containing one or more compounds represented by general formula (i) and one or more compounds represented by general formula (ii) has high Tni , large ⁇ n, large ⁇ r , small tan ⁇ iso , and good storage stability at low temperatures.
• Comparative Examples 1 and 2 it was found that the liquid crystal compositions not containing one or more compounds represented by general formula (i) and one or more compounds represented by general formula (ii) had poor storage stability. In Comparative Examples 1 and 2, precipitation was observed after 3 days. Furthermore, from Examples 2 to 43, it was confirmed that similar 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.
• Liquid crystal compositions were prepared using LC-08 to LC-09, hindered phenol-based antioxidants (XX-1) to (XX-5), and hindered amine-based 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 10 to 12.
• 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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