WO2024024519A1 - 化合物、液晶組成物並びにこれを用いた液晶表示素子、センサ、液晶レンズ、光通信機器及びアンテナ - Google Patents

化合物、液晶組成物並びにこれを用いた液晶表示素子、センサ、液晶レンズ、光通信機器及びアンテナ Download PDF

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Publication number
WO2024024519A1
WO2024024519A1 PCT/JP2023/025828 JP2023025828W WO2024024519A1 WO 2024024519 A1 WO2024024519 A1 WO 2024024519A1 JP 2023025828 W JP2023025828 W JP 2023025828W WO 2024024519 A1 WO2024024519 A1 WO 2024024519A1
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group
alkyl group
independently
general formula
substituted
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PCT/JP2023/025828
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English (en)
French (fr)
Japanese (ja)
Inventor
美花 高崎
正直 林
大樹 野呂
純一 間宮
貴哉 池内
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DIC Corp
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DIC Corp
Dainippon Ink and Chemicals Co Ltd
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Priority to CN202380044680.4A priority Critical patent/CN119452062A/zh
Priority to JP2023556818A priority patent/JP7428302B1/ja
Priority to KR1020247040116A priority patent/KR20250043333A/ko
Priority to US18/878,619 priority patent/US20250377570A1/en
Priority to JP2023200561A priority patent/JP2024019224A/ja
Publication of WO2024024519A1 publication Critical patent/WO2024024519A1/ja
Anticipated expiration legal-status Critical
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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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    • C09K19/08—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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    • C09K19/30—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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Definitions

  • the present invention relates to a compound, a liquid crystal composition, and a liquid crystal display element, sensor, liquid crystal lens, optical communication device, and antenna using the same.
  • a liquid crystal antenna that can easily change the direction of transmitting and receiving radio waves is 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 high-precision 3D map information.
  • the antenna uses a liquid crystal, by incorporating the antenna into a car, it becomes possible to download large amounts of data from a communication satellite without the need for mechanical moving parts.
  • the frequency band used for satellite communications is approximately 13 GHz, which is significantly different from the frequency used for conventional liquid crystal display applications.
  • ⁇ n required for liquid crystals for antennas is, for example, about 0.4, and the operating temperature range is, for example, -20 to 120°C.
  • ⁇ n required for a liquid crystal for this purpose is, for example, 0.3 to 0.6, and the operating temperature range is, for example, 10 to 100°C.
  • Patent Document 1 can be mentioned, for example.
  • Non-Patent Document 1 proposes the use of liquid crystal materials as constituent components of high-frequency devices.
  • the present invention provides a compound and a liquid crystal composition that can provide a liquid crystal composition that has high T ni , large ⁇ n, low V th , large ⁇ r , small tan ⁇ iso , and has good storage stability at low temperatures.
  • An object of the present invention is to provide a liquid crystal display device, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the same.
  • R i1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S-, -CO- and/or -CS-
  • One or more -CH 2 -CH 2 -CH 2 - in the alkyl group may be each independently substituted with -O-CO-O-
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S- and/or -CO-,
  • One or more -CH 2 -CH 2 -CH 2 - in the alkyl group may be each independently substituted with -O-CO-O-,
  • One or more -CH 2 -CH 2 -CH 2 -CH 2 - in the alkyl group are each independently substituted with -O-CO-O-,
  • R ii1 each independently represents an alkyl group having 1 to 20 carbon atoms
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S-, -CO- and/or -CS-
  • One or more -CH 2 -CH 2 -CH 2 - in the alkyl group may be each independently substituted with -O-CO-O-
  • One or more hydrogen atoms in the alkyl group may be each independently substituted with a halogen atom, Oxygen atoms do not bond directly, A ii
  • Item 2 The compound represented by the general formula (i) has the following general formulas (i-1) to (i-14).
  • R vt1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S-, -CO- and/or -CS-
  • One or more -CH 2 -CH 2 -CH 2 - in the alkyl group may be each independently substituted with -O-CO-O-
  • One or more hydrogen atoms in the alkyl group may be each independently substituted with a halogen atom, Oxygen atoms do not bond directly
  • R vt2 is
  • Item 5 The liquid crystal composition according to any one of Items 1 to 4, wherein ⁇ n at 25° C. and 589 nm is 0.38 or more.
  • Item 6 A liquid crystal display element using the liquid crystal composition according to any one of items 1 to 5.
  • Item 7 The liquid crystal display element according to item 6, which is driven by an active matrix method or a passive matrix method.
  • Section 8. Item 5. A liquid crystal display element in which dielectric constant is reversibly switched by reversibly changing the orientation direction of liquid crystal molecules of the liquid crystal composition according to any one of Items 1 to 5.
  • Item 9 A sensor using the liquid crystal composition according to any one of items 1 to 5.
  • Item 10 A liquid crystal lens using the liquid crystal composition according to any one of items 1 to 5.
  • Item 11 An optical communication device using the liquid crystal composition according to any one of items 1 to 5.
  • Item 12 An antenna using the liquid crystal composition according to any one of items 1 to 5.
  • Item 13 The antenna according to item 12, a first board including a plurality of slots; a second substrate facing the first substrate and provided with a power feeding 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 provided with the patch electrode; a liquid crystal layer provided between the first substrate and the third substrate, An antenna in which the liquid crystal layer contains the liquid crystal composition according to any one of Items 1 to 5.
  • R i1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S-, -CO- and/or -CS-
  • One or more -CH 2 -CH 2 -CH 2 - in the alkyl group may be each independently substituted with -O-CO-O-
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S- and/or -CO-,
  • One or more -CH 2 -CH 2 -CH 2 - in the alkyl group may be each independently substituted with -O-CO-O-,
  • One or more -CH 2 -CH 2 -CH 2 -CH 2 - in the alkyl group are each independently substituted with -O-CO-O-,
  • a good liquid crystal composition can be obtained, and the liquid crystal composition is useful for liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment, and antennas.
  • the liquid crystal composition according to the present invention contains one or more compounds represented by the general formula (i) having an indane structure and an isothiocyanate group (-NCS).
  • R i1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
  • the alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and preferably a linear alkyl group.
  • the number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S-, -CO- and/or -CS-.
  • one or more hydrogen atoms in the alkyl group may be each independently substituted with a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom. However, when the alkyl group is substituted with a predetermined group, the oxygen atoms do not bond directly.
  • R i1 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 preferably a linear alkoxy group.
  • the number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6.
  • R i1 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 preferably a linear alkylsulfanyl group.
  • the number of carbon atoms in the alkylsulfanyl group is preferably 2 to 10, preferably 2 to 6.
  • the alkenyl group is a linear, branched or cyclic alkenyl group, and preferably a linear alkenyl group.
  • the number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.
  • R i1 represents an alkynyl group having 2 to 20 carbon atoms, in which one or more -CH 2 -CH 2 - in the alkyl group is substituted with -C ⁇ C-. be able to.
  • the alkynyl group is a linear, branched or cyclic alkynyl group, and preferably a linear alkynyl group.
  • the number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.
  • the alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and preferably a linear alkenyloxy group.
  • the number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6.
  • R i1 can represent a halogenated alkyl group having 1 to 20 carbon atoms, by replacing one or more hydrogen atoms in the alkyl group with a halogen atom.
  • the halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and preferably a linear halogenated alkyl group.
  • the number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, preferably 2 to 6.
  • R i1 is a group in which one -CH 2 - in the alkyl group is substituted with -O-, and one or more hydrogen atoms in the alkyl group are substituted with a halogen atom.
  • the halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and preferably a linear halogenated alkoxy group.
  • the number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.
  • alkyl group having 1 to 20 carbon atoms (including substituted ones) in R i1 include groups represented by formulas (R i1 -1) to (R i1 -36).
  • R i1 is preferably a linear alkyl group having 2 to 6 carbon atoms from the viewpoint of ⁇ n and compatibility with other liquid crystal compounds.
  • the substitution position of R i1 in the indane structure is preferably one of the following formulas (R i1 -SP-1) to (R i1 -SP-3), and from the viewpoint of improving ⁇ n, (R i1 -SP -2) or (R i1 -SP-3) is preferred.
  • the black dot represents the bond to Z i1 .
  • One or more hydrogen atoms in A i1 and A i2 may be each independently substituted with a substituent S i1 .
  • Substituent S i1 is 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.
  • the alkyl group is a linear, branched or cyclic alkyl group, and preferably a linear alkyl group.
  • the number of carbon atoms in the alkyl group is preferably 2 to 10, preferably 3 to 6.
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S- and/or -CO-.
  • One or more hydrogen atoms in the alkyl group may be each independently 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 do not bond directly.
  • sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms do not bond directly.
  • substituent S i1 a fluorine atom is preferable.
  • at least one of A i1 and A i2 is substituted with at least one substituent S i1 .
  • a i2 is preferably substituted with at least one substituent S i1 .
  • when there are multiple substituents S i1 they may be the same or different.
  • substitution position of the substituent S i1 in A i1 is preferably one of the following formulas (A i1 -SP-1) to (A i1 -SP-3).
  • the white dots represent the bond to Z i1
  • the black dots represent the bond to Z i2 or the isothiocyanate group (-NCS).
  • the substitution position of the substituent S i1 in A i2 is preferably one of the following formulas (A i2 -SP-1) to (A i2 -SP-3).
  • a i1 preferably represents one of the following formulas (A i1 -1) to (A i1 -8).
  • the white dots represent the bond to Z i1
  • the black dots represent the bond to Z i2 or the isothiocyanate group (-NCS).
  • a i2 preferably represents one of the following formulas (A i2 -1) to (A i2 -5).
  • the white dots represent the bond to Z i2
  • the black dots represent the bond to Z i2 or the isothiocyanate group (-NCS).
  • L i1 and L i2 each independently represent a hydrogen atom, 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, or an alkyl group having 1 to 20 carbon atoms.
  • the alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and preferably a linear alkyl group.
  • the number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S-, -CO- and/or -CS-.
  • one or more hydrogen atoms in the alkyl group may be each independently substituted with a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom. However, when the alkyl group is substituted with a predetermined group, the oxygen atoms do not bond directly.
  • L i1 and L i2 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 preferably a linear alkoxy group.
  • the number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6.
  • L i1 and L i2 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 preferably a linear alkylsulfanyl group.
  • the number of carbon atoms in the alkylsulfanyl group is preferably 2 to 10, preferably 2 to 6.
  • the alkenyl group is a linear, branched or cyclic alkenyl group, and preferably a linear alkenyl group.
  • the number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.
  • L i1 and L i2 are alkynyl groups having 2 to 20 carbon atoms, by replacing one or more -CH 2 -CH 2 - in the alkyl group with -C ⁇ C-. can represent a group.
  • the alkynyl group is a linear, branched or cyclic alkynyl group, and preferably a linear alkynyl group.
  • the number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.
  • the alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and preferably a linear alkenyloxy group.
  • the number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6.
  • L i1 and L i2 can represent a halogenated alkyl group having 1 to 20 carbon atoms by replacing one or more hydrogen atoms in the alkyl group with a halogen atom.
  • the halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and preferably a linear halogenated alkyl group.
  • the number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, preferably 2 to 6.
  • one -CH 2 - in the alkyl group is substituted with -O-, and one or more hydrogen atoms in the alkyl group are substituted with a halogen atom.
  • the halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and preferably a linear halogenated alkoxy group.
  • the number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.
  • alkyl groups having 1 to 20 carbon atoms (including substituted ones) in L i1 and L i2 are represented by formulas (L i1/2 -1) to (L i1/2 -36). Examples include groups such as
  • the black dots represent bonds to the indane structure.
  • at least one of L i1 and L i2 is preferably a hydrogen atom or a fluorine atom, and it is preferable that both L i1 and L i2 are a hydrogen atom or a fluorine atom. preferable.
  • Z i1 and Z i2 each independently represent either 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 preferably a linear alkylene group.
  • the number of carbon atoms in the alkylene group is preferably 2 to 10, preferably 2 to 6.
  • One or more -CH 2 - in the alkylene group may be each independently substituted with -O-, -CF 2 - and/or -CO-.
  • the oxygen atoms do not bond directly.
  • alkylene groups having 1 to 20 carbon atoms include groups represented by formulas (Z i1/2 -1) to (Z i1/2 -24), etc. .
  • the white dots represent the indane structure, the bond to A i1 or A i2 , and the black dots represent the bond to A i1 or A i2 . represent.
  • Z i1/2 -4) (-C ⁇ C-) is preferred.
  • n i1 represents an integer of 0 to 3. From the viewpoints of compatibility with other liquid crystal compounds, phase transition temperature, dielectric anisotropy, ease of synthesis, and availability of raw materials, n i1 is preferably 1 or 2. When a plurality of A i2 or Z i2 exist, they may be the same or different.
  • the compound represented by the general formula (i) is preferably a compound represented by the following general formulas (i-1) to (i-14).
  • R i1 , A i1 , A i2 , L i1 and L i2 each independently represent R i1 , A i1 , A in general formula (i) It has the same meaning as i2 , L i1 and L i2 .
  • the definition of A i2-2 in general formula (i-9) is the same as the definition of A i2 in general formula (i) above.
  • the compound represented by the 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).
  • Specific examples of the compound represented by the general formula (i-1-1) include compounds represented by the following structural formulas (i-1-1.1) to (i-1-1.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-1-2) include compounds represented by the following structural formulas (i-1-2.1) to (i-1-2.3). It will be done.
  • the compound represented by the general formula (i-2) is preferably a compound represented by the following general formulas (i-2-1) to (i-2-4).
  • 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 the general formula (i-2-1) include compounds represented by the following structural formulas (i-2-1.1) to (i-2-1.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-2-2) include compounds represented by the following structural formulas (i-2-2.1) to (i-2-2.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-2-3) include compounds represented by the following structural formulas (i-2-3.1) to (i-2-3.3). It will be done.
  • the compound represented by the general formula (i-3) is preferably a compound represented by the following general formulas (i-3-1) to (i-3-3).
  • 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 the general formula (i-3-1) include compounds represented by the following structural formulas (i-3-1.1) to (i-3-1.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-3-2) include compounds represented by the following structural formulas (i-3-2.1) to (i-3-2.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-3-3) include compounds represented by the following structural formulas (i-3-3.1) to (i-3-3.3). It will be done.
  • the compound represented by the general formula (i-4) is preferably a compound represented by the following general formulas (i-4-1) to (i-4-6).
  • 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 the general formula (i-4-1) include compounds represented by the following structural formulas (i-4-1.1) to (i-4-1.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-4-2) include compounds represented by the following structural formulas (i-4-2.1) to (i-4-2.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-4-3) include compounds represented by the following structural formulas (i-4-3.1) to (i-4-3.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-4-4) include compounds represented by the following structural formulas (i-4-4.1) to (i-4-4.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-4-5) include compounds represented by the following structural formulas (i-4-5.1) to (i-4-5.4). It will be done.
  • Specific examples of the compound represented by the general formula (i-4-6) include compounds represented by the following structural formulas (i-4-6.1) to (i-4-6.3). It will be done.
  • the compound represented by the general formula (i-5) is preferably a compound represented by the following general formula (i-5-1).
  • 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 the general formula (i-5-1) include compounds represented by the following structural formulas (i-5-1.1) to (i-5-1.2). It will be done.
  • the compound represented by the general formula (i-6) is preferably a compound represented by the following general formulas (i-6-1) to (i-6-2).
  • 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 the general formula (i-6-1) include compounds represented by the following structural formulas (i-6-1.1) to (i-6-1.2). It will be done.
  • Specific examples of the compound represented by the general formula (i-6-2) include compounds represented by the following structural formulas (i-6-2.1) to (i-6-2.2). It will be done.
  • the compound represented by the general formula (i-7) is preferably a compound represented by the following general formulas (i-7-1) to (i-7-2).
  • 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 the general formula (i-7-1) include compounds represented by the following structural formula (i-7-1.1).
  • Specific examples of the compound represented by the general formula (i-7-2) include compounds represented by the following structural formula (i-7-2.1).
  • the compound represented by the general formula (i-8) is preferably a compound represented by the following general formulas (i-8-1) to (i-8-5).
  • 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 the general formula (i-8-1) include compounds represented by the following structural formulas (i-8-1.1) to (i-8-1.2). It will be done.
  • Specific examples of the compound represented by the general formula (i-8-2) include compounds represented by the following structural formulas (i-8-2.1) to (i-8-2.2). It will be done.
  • Specific examples of the compound represented by the general formula (i-8-3) include compounds represented by the following structural formulas (i-8-3.1) to (i-8-3.4). It will be done.
  • Specific examples of the compound represented by the general formula (i-8-4) include compounds represented by the following structural formulas (i-8-4.1) to (i-8-4.2). It will be done.
  • Specific examples of the compound represented by the general formula (i-8-5) include compounds represented by the following structural formulas (i-8-5.1) to (i-8-5.2). It will be done.
  • the compound represented by the general formula (i-9) is preferably a compound represented by the following general formula (i-9-1).
  • 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 the general formula (i-9-1) include compounds represented by the following structural formula (i-9-1.1).
  • the compound represented by the general formula (i-10) is preferably a compound represented by the following general formulas (i-10-1) to (i-10-3).
  • 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 the general formula (i-10-1) include compounds represented by the following structural formulas (i-10-1.1) to (i-10-1.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-10-2) include compounds represented by the following structural formulas (i-10-2.1) to (i-10-2.4). It will be done.
  • Specific examples of the compound represented by the general formula (i-10-3) include compounds represented by the following structural formulas (i-10-3.1) to (i-10-3.3). It will be done.
  • the compound represented by the general formula (i-11) is preferably a compound represented by the following general formulas (i-11-1) to (i-11-6).
  • 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 the general formula (i-11-1) include compounds represented by the following structural formulas (i-11-1.1) to (i-11-1.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-11-2) include compounds represented by the following structural formulas (i-11-2.1) to (i-11-2.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-11-3) include compounds represented by the following structural formulas (i-11-3.1) to (i-11-3.2). It will be done.
  • Specific examples of the compound represented by the general formula (i-11-4) include compounds represented by the following structural formulas (i-11-4.1) to (i-11-4.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-11-5) include compounds represented by the following structural formulas (i-11-5.1) to (i-11-5.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-11-6) include compounds represented by the following structural formulas (i-11-6.1) to (i-11-6.2). It will be done.
  • the compound represented by the general formula (i-12) is preferably a compound represented by the following general formulas (i-12-1) to (i-12-4).
  • 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 the general formula (i-12-1) include compounds represented by the following structural formulas (i-12-1.1) to (i-12-1.3). It will be done.
  • Specific examples of the compound represented by the general formula (i-12-2) include compounds represented by the following structural formulas (i-12-2.1) to (i-12-2.2). It will be done.
  • Specific examples of the compound represented by the general formula (i-12-3) include compounds represented by the following structural formulas (i-12-3.1) to (i-12-3.2). It will be done.
  • Specific examples of the compound represented by the general formula (i-12-4) include compounds represented by the following structural formulas (i-12-4.1) to (i-12-4.2). It will be done.
  • the compound represented by the general formula (i-13) is preferably a compound represented by the following general formula (i-13-1).
  • 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 the general formula (i-13-1) include compounds represented by the following structural formulas (i-13-1.1) to (i-13-1.3). It will be done.
  • the compound represented by the general formula (i-14) is preferably a compound represented by the following general formula (i-14-1).
  • 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 the general formula (i-14-1) include compounds represented by the following structural formulas (i-14-1.1) to (i-14-1.2). It will be done.
  • R i1 , L i1 , L i2 and S i1 have the same meanings as R i1 , L i1 , L i2 and S i1 in the general formula (i). represent.
  • a compound represented by general formula (s-3) can be obtained by reacting a compound represented by general formula (s-1) with a compound represented by general formula (s-2). Examples of the reaction method include Suzuki coupling reaction using a metal catalyst and a base.
  • metal catalysts include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, and dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium. (II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0), and the like.
  • a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.
  • the base include potassium carbonate, potassium phosphate, cesium carbonate, and the like.
  • the compound represented by general formula (s-5) can be obtained by reacting the compound represented by general formula (s-3) with the compound represented by general formula (s-4).
  • Examples of the reaction method include Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.
  • palladium catalysts include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, and dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium. (II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0), and the like.
  • a ligand such as triphenylphosphine or 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl may be added.
  • a specific example of the copper catalyst is copper(I) iodide.
  • Specific examples of the base include triethylamine, diisopropylamine, and the like.
  • the target compound is obtained by reacting the compound represented by general formula (s-5) with 1,1-thiocarbonyldiimidazole, 1,1-thiocarbonyldi-2(1H)-pyridone, thiophosgene, etc.
  • a compound represented by general formula (s-6) can be obtained.
  • R i1 , L i1 , L i2 and S i1 have the same meanings as R i1 , L i1 , L i2 and S i1 in the above general formula (i). represent.
  • a compound represented by general formula (s-8) can be obtained by reacting a compound represented by general formula (s-7) with trimethylsilylacetylene. Examples of the reaction method include Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base. Specific examples of the palladium catalyst, copper catalyst, and base include the compounds described in (Production method 1).
  • a compound represented by general formula (s-9) can be obtained by reacting the compound represented by general formula (s-8) with potassium carbonate in an alcohol solvent such as methanol.
  • the compound represented by general formula (s-11) can be obtained by reacting the compound represented by general formula (s-9) with the compound represented by general formula (s-10).
  • the reaction method include Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base. Specific examples of the palladium catalyst, copper catalyst, and base include the compounds described in (Production method 1).
  • the compound represented by general formula (s-13) can be obtained by reacting the compound represented by general formula (s-11) with the compound represented by general formula (s-12). .
  • reaction method examples include Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.
  • specific examples of the palladium catalyst, copper catalyst, and base include the compounds described in (Production method 1).
  • the target compound is obtained by reacting the compound represented by the general formula (s-13) with 1,1-thiocarbonyldiimidazole, 1,1-thiocarbonyldi-2(1H)-pyridone, thiophosgene, etc.
  • a compound represented by general formula (s-14) can be obtained.
  • the liquid crystal composition according to the present invention contains one or more compounds represented by the following general formula (ii) having an isothiocyanate group (-NCS).
  • R ii1 represents an alkyl group having 1 to 20 carbon atoms.
  • the alkyl group is a linear, branched or cyclic alkyl group, and preferably a linear alkyl group.
  • the number of carbon atoms in the alkyl group is preferably 2 to 10, preferably 2 to 6.
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S-, -CO- and/or -CS-.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the oxygen atoms do not bond directly.
  • sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms do not bond directly.
  • R ii1 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 preferably a linear alkoxy group.
  • R ii1 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 preferably a linear alkylsulfanyl group.
  • the number of carbon atoms in the alkylsulfanyl group is preferably 1 to 10, preferably 1 to 6.
  • the alkenyl group is a linear, branched or cyclic alkenyl group, and preferably a linear alkenyl group.
  • the number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.
  • R ii1 represents an alkynyl group having 2 to 20 carbon atoms, in which one or more -CH 2 -CH 2 - in the alkyl group is substituted with -C ⁇ C-. be able to.
  • the alkynyl group is a linear, branched or cyclic alkynyl group, and preferably a linear alkynyl group.
  • the number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.
  • an alkynyl group represented by the following formula (R ii1 -A) is preferable.
  • R ii1A represents an alkyl group having 1 to 18 carbon atoms.
  • the alkyl group having 1 to 18 carbon atoms is a linear, branched or cyclic alkyl group, and preferably a linear alkyl group.
  • the number of carbon atoms in the alkyl group having 1 to 18 carbon atoms is preferably 1 to 8.
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S-, -CO- and/or -CS-.
  • one or more -CH 2 -CH 2 -CH 2 - in the alkyl group may be each independently substituted with -O-CO-O-.
  • one or more hydrogen atoms in the alkyl group may be each independently 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 do not bond directly.
  • sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms do not bond directly.
  • the black dot represents the bond to A ii1 .
  • the alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and preferably a linear alkenyloxy group.
  • the number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6.
  • R ii1 can represent a halogenated alkyl group having 1 to 20 carbon atoms, by replacing one or more hydrogen atoms in the alkyl group with a halogen atom.
  • the halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and preferably a linear halogenated alkyl group.
  • the number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, preferably 2 to 6.
  • R ii1 is obtained by replacing one -CH 2 - in the alkyl group with -O- and replacing one or more hydrogen atoms in the alkyl group with a halogen atom.
  • the halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and preferably a linear halogenated alkoxy group.
  • the number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.
  • Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) in R ii1 include groups represented by formulas (R ii1 -1) to (R ii1 -56).
  • the black dots represent the bond to A ii1 .
  • the ring structure to which R ii1 is bonded is a phenyl group (aromatic)
  • An alkenyl group having 4 to 5 carbon atoms is preferable
  • the ring structure to which R i1 is bonded is a saturated ring structure such as cyclohexane, pyran, and dioxane
  • a linear alkyl group having 1 to 5 carbon atoms, a linear A straight-chain alkoxy group having 1 to 4 carbon atoms and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred.
  • R ii1 preferably has a total of 5 or less carbon atoms and oxygen atoms when present, and is preferably linear.
  • R ii1 includes a linear or branched alkyl group having 2 to 8 carbon atoms, a linear alkoxy group having 2 to 8 carbon atoms, and a linear alkyl group having 1 to 8 carbon atoms.
  • a linear halogenated alkoxy group, a linear alkynyl group having 2 to 8 carbon atoms, or a linear alkylsulfanyl group having 1 to 6 carbon atoms is preferred.
  • One or more hydrogen atoms in A ii1 and A ii2 may be each independently substituted with a substituent S ii1 .
  • Substituent S ii1 is 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, Represents either a dimethylsilyl group, a thioisocyano group, or 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 is a linear, branched or cyclic alkyl group, and preferably a linear alkyl group.
  • the number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S-, -CO- and/or -CS-.
  • One or more -CH 2 -CH 2 -CH 2 - in the alkyl group may be each independently substituted with -O-CO-O-.
  • one or more hydrogen atoms in the alkyl group may be each independently 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 do not bond directly.
  • sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms do not bond directly.
  • the substituent S ii1 a fluorine atom or a chlorine atom is preferable.
  • At least one of A ii1 or A ii2 is preferably substituted with at least one substituent S ii1 , preferably with a halogen atom, and preferably with a fluorine atom.
  • substituent S ii1 when there are multiple substituents S ii1 , they may be the same or different.
  • substitution position of the substituent S ii1 in A ii1 is preferably one of the following formulas (A ii1 -SP-1) to (A ii1 -SP-6).
  • the white dots represent the bond to R ii1 or Z ii1
  • the black dots represent the bond to Z ii1 .
  • the substitution position of the substituent S ii1 in A ii2 is preferably one of the following formulas (A ii2 -SP-1) to (A ii2 -SP-8).
  • a ii1 preferably represents one of the following formulas (A ii1 -1) to (A ii1 -25).
  • a ii2 preferably represents one of the following formulas (A ii2 -1) to (A ii2 -8).
  • Z ii1 represents either a single bond or an alkylene group having 1 to 20 carbon atoms.
  • One or more -CH 2 - in the alkylene group may be each independently substituted with -O-, -CF 2 - and/or -CO-.
  • alkylene group having 1 to 20 carbon atoms when the alkylene group having 1 to 20 carbon atoms is substituted with a predetermined group, the oxygen atoms do not bond directly. Further, from the viewpoint of stability of the compound, it is preferable that sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms do not bond directly.
  • alkylene groups having 1 to 20 carbon atoms include groups represented by formulas (Z ii1 -1) to (Z ii1 -24).
  • the white dots represent the bond to A ii1
  • the black dots represent the bond to A ii1 or A ii2 .
  • n ii1 represents an integer of 1 to 4, preferably 1 to 2.
  • Z ii1 preferably represents a single bond or -C ⁇ C- from the viewpoint of ⁇ n and/or ⁇ r .
  • Z ii1 preferably represents a single bond or -C ⁇ C- from the viewpoint of ⁇ n and/or ⁇ r .
  • a ii1 and Z ii1 may be the same or different. However, among the compounds represented by general formula (ii), the compounds represented by general formula (i) (including subordinate concepts) are excluded.
  • the compound represented by the general formula (ii) is preferably a compound represented by the following general formulas (ii-1) to (ii-8).
  • R ii1 , A ii1 and A ii2 have the same meanings as R ii1 , A ii1 and A ii2 in the above general formula (ii), respectively.
  • the definitions of A ii1-2 and A ii1-3 are each independently the same as the definition of A ii1 in the above general formula (ii).
  • the compound represented by the general formula (ii-1) is preferably a compound represented by the following general formulas (ii-1-1) to (ii-1-2).
  • R ii1 each independently represents the same meaning as R ii1 in the above general formula (ii).
  • Specific examples of the compound represented by the general formula (ii-1-1) include compounds represented by the following structural formulas (ii-1-1.1) to (ii-1-1.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-1-2) include compounds represented by the following structural formulas (ii-1-2.1) to (ii-1-2.6). It will be done.
  • the compound represented by the general formula (ii-2) is preferably a compound represented by the following general formulas (ii-2-1) to (ii-2-10).
  • R ii1 and S ii1 each independently represent the same meaning as R ii1 and S ii1 in the above general formula (ii).
  • Specific examples of the compound represented by the general formula (ii-2-1) include compounds represented by the following structural formulas (ii-2-1.1) to (ii-2-1.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-2-2) include compounds represented by the following structural formulas (ii-2-2.1) to (ii-2-2.10). It will be done.
  • Specific examples of the compound represented by the general formula (ii-2-3) include compounds represented by the following structural formulas (ii-2-3.1) to (ii-2-3.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-2-5) include compounds represented by the following structural formulas (ii-2-5.1) to (ii-2-5.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-2-6) include compounds represented by the following structural formulas (ii-2-6.1) to (ii-2-6.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-2-7) include compounds represented by the following structural formulas (ii-2-7.1) to (ii-2-7.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-2-8) include compounds represented by the following structural formulas (ii-2-8.1) to (ii-2-8.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-2-9) include compounds represented by the following structural formulas (ii-2-9.1) to (ii-2-9.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-2-10) include compounds represented by the following structural formulas (ii-2-10.1) to (ii-2-10.4). It will be done.
  • the compound represented by the general formula (ii-3) is preferably a compound represented by the following general formulas (ii-3-1) to (ii-3-16).
  • R ii1 and S ii1 each independently represent the same meaning as R ii1 and S ii1 in the above general formula (ii).
  • Specific examples of the compound represented by the general formula (ii-3-1) include compounds represented by the following structural formulas (ii-3-1.1) to (ii-3-1.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-2) include compounds represented by the following structural formulas (ii-3-2.1) to (ii-3-2.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-3) include compounds represented by the following structural formulas (ii-3-3.1) to (ii-3-3.7). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-4) include compounds represented by the following structural formulas (ii-3-4.1) to (ii-3-4.5). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-5) include compounds represented by the following structural formulas (ii-3-5.1) to (i-3-5.7). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-6) include compounds represented by the following structural formulas (ii-3-6.1) to (ii-3-6.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-7) include compounds represented by the following structural formulas (ii-3-7.1) to (ii-3-7.7). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-8) include compounds represented by the following structural formulas (ii-3-8.1) to (ii-3-8.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-9) include compounds represented by the following structural formulas (ii-3-9.1) to (ii-3-9.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-10) include compounds represented by the following structural formulas (ii-3-10.1) to (ii-3-10.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-11) include compounds represented by the following structural formulas (ii-3-11.1) to (ii-3-11.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-12) include compounds represented by the following structural formulas (ii-3-12.1) to (ii-3-12.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-13) include compounds represented by the following structural formulas (ii-3-13.1) to (ii-3-13.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-14) include compounds represented by the following structural formulas (ii-3-14.1) to (ii-3-14.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-15) include compounds represented by the following structural formulas (ii-3-15.1) to (ii-3-15.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-3-16) include compounds represented by the following structural formulas (ii-3-16.1) to (ii-3-16.3). It will be done.
  • the compound represented by the general formula (ii-4) is preferably a compound represented by the following general formulas (ii-4-1) to (ii-4-26).
  • R ii1 and S ii1 each independently represent the same meaning as R ii1 and S ii1 in the above general formula (ii).
  • Specific examples of the compound represented by the general formula (ii-4-1) include compounds represented by the following structural formulas (ii-4-1.1) to (ii-4-1.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-2) include compounds represented by the following structural formulas (ii-4-2.1) to (ii-4-2.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-3) include compounds represented by the following structural formulas (ii-4-3.1) to (ii-4-3.8). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-4) include compounds represented by the following structural formulas (ii-4-4.1) to (ii-4-4.5). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-6) include compounds represented by the following structural formulas (ii-4-6.1) to (ii-4-6.5). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-8) include compounds represented by the following structural formulas (ii-4-8.1) to (ii-4-8.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-9) include compounds represented by the following structural formulas (ii-4-9.1) to (ii-4-9.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-10) include compounds represented by the following structural formulas (ii-4-10.1) to (ii-4-10.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-11) include compounds represented by the following structural formulas (ii-4-11.1) to (i-4-11.5). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-12) include compounds represented by the following structural formulas (ii-4-12.1) to (ii-4-12.5). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-13) include compounds represented by the following structural formulas (ii-4-13.1) to (ii-4-13.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-14) include compounds represented by the following structural formulas (ii-4-14.1) to (ii-4-14.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-15) include compounds represented by the following structural formulas (ii-4-15.1) to (ii-4-15.6). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-16) include compounds represented by the following structural formulas (ii-4-16.1) to (ii-4-16.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-17) include compounds represented by the following structural formulas (ii-4-17.1) to (ii-4-17.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-18) include compounds represented by the following structural formulas (ii-4-18.1) to (ii-4-18.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-19) include compounds represented by the following structural formulas (ii-4-19.1) to (ii-4-19.8). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-20) include compounds represented by the following structural formulas (ii-4-20.1) to (ii-4-20.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-22) include compounds represented by the following structural formulas (ii-4-22.1) to (ii-4-22.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-23) include compounds represented by the following structural formulas (ii-4-23.1) to (ii-4-23.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-24) include compounds represented by the following structural formulas (ii-4-24.1) to (ii-4-24.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-25) include compounds represented by the following structural formulas (ii-4-25.1) to (ii-4-25.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-4-26) include compounds represented by the following structural formulas (ii-4-26.1) to (ii-4-26.3). It will be done.
  • the compound represented by the general formula (ii-5) is preferably a compound represented by the following general formulas (ii-5-1) to (ii-5-5).
  • R ii1 and S ii1 each independently represent the same meaning as R ii1 and S ii1 in the above general formula (ii).
  • Specific examples of the compound represented by the general formula (ii-5-1) include compounds represented by the following structural formulas (ii-5-1.1) to (ii-5-1.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-5-2) include compounds represented by the following structural formulas (ii-5-2.1) to (ii-5-2.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-5-4) include compounds represented by the following structural formulas (ii-5-4.1) to (ii-5-4.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-5-5) include compounds represented by the following structural formulas (ii-5-5.1) to (ii-5-5.3). It will be done.
  • the compound represented by the general formula (ii-6) is preferably a compound represented by the following general formulas (ii-6-1) to (ii-6-33).
  • R ii1 and S ii1 each independently represent the same meaning as R ii1 and S ii1 in the above general formula (ii).
  • Specific examples of the compound represented by the general formula (ii-6-1) include compounds represented by the following structural formulas (ii-6-1.1) to (ii-6-1.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-2) include compounds represented by the following structural formulas (ii-6-2.1) to (ii-6-2.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-3) include compounds represented by the following structural formulas (ii-6-3.1) to (ii-6-3.8). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-4) include compounds represented by the following structural formulas (ii-6-4.1) to (ii-6-4.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-5) include compounds represented by the following structural formulas (ii-6-5.1) to (ii-6-5.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-6) include compounds represented by the following structural formulas (ii-6-6.1) to (ii-6-6.2). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-8) include compounds represented by the following structural formulas (ii-6-8.1) to (ii-6-8.9). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-9) include compounds represented by the following structural formulas (ii-6-9.1) to (ii-6-9.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-10) include compounds represented by the following structural formulas (ii-6-10.1) to (ii-6-10.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-11) include compounds represented by the following structural formulas (ii-6-11.1) to (ii-6-11.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-12) include compounds represented by the following structural formulas (ii-6-12.1) to (ii-6-12.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-13) include compounds represented by the following structural formulas (ii-6-13.1) to (ii-6-13.20). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-14) include compounds represented by the following structural formulas (ii-6-14.1) to (ii-6-14.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-16) include compounds represented by the following structural formulas (ii-1-16.1) to (ii-6-16.5). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-17) include compounds represented by the following structural formulas (ii-6-17.1) to (ii-6-17.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-18) include compounds represented by the following structural formulas (ii-6-18.1) to (ii-6-18.8). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-19) include compounds represented by the following structural formulas (ii-6-19.1) to (ii-6-19.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-20) include compounds represented by the following structural formulas (ii-6-20.1) to (ii-6-20.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-21) include compounds represented by the following structural formulas (ii-6-21.1) to (ii-6-21.4). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-22) include compounds represented by the following structural formulas (ii-6-22.1) to (ii-6-22.14). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-23) include compounds represented by the following structural formulas (ii-6-23.1) to (ii-6-23.10). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-24) include compounds represented by the following structural formulas (ii-6-24.1) to (ii-6-24.2). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-25) include compounds represented by the following structural formulas (ii-6-25.1) to (ii-6-25.5). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-26) include compounds represented by the following structural formulas (ii-6-26.1) to (ii-6-26.2). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-28) include compounds represented by the following structural formulas (ii-6-28.1) to (ii-6-28.5). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-31) include compounds represented by the following structural formulas (ii-6-31.1) to (ii-6-31.5). It will be done.
  • Specific examples of the compound represented by the general formula (ii-6-33) include compounds represented by the following structural formulas (ii-6-33.1) to (ii-6-33.4). It will be done.
  • the compound represented by the general formula (ii-7) is preferably a compound represented by the following general formula (ii-7-1).
  • R ii1 and S ii1 each independently represent the same meaning as R ii1 and S ii1 in the above general formula (ii).
  • Specific examples of the compound represented by the general formula (ii-7-1) include compounds represented by the following structural formula (ii-7-1.1).
  • the compound represented by the general formula (ii-8) is preferably a compound represented by the following general formulas (ii-8-1) to (ii-8-2).
  • R ii1 and S ii1 each independently represent the same meaning as R ii1 and S ii1 in the above general formula (ii).
  • Specific examples of the compound represented by the general formula (ii-8-1) include compounds represented by the following structural formulas (ii-8-1.1) to (ii-8-1.3). It will be done.
  • Specific examples of the compound represented by the general formula (ii-8-2) include compounds represented by the following structural formulas (ii-8-2.1) to (ii-8-2.6). It will be done.
  • It is preferably at least 15% by mass, preferably at least 20% by mass, preferably at least 25% by mass, preferably at least 30% by mass, and 35% by mass. It is preferably at least 40% by mass, preferably at least 45% by mass, preferably at least 75% by mass, preferably at least 80% by mass, and 85% by mass. It is preferable that it is above.
  • It is preferably at most 50% by mass, preferably at most 45% by mass, preferably at most 40% by mass, preferably at most 35% by mass, and preferably at most 25% by mass. It is preferably at most 15% by mass, more preferably at most 5% by mass.
  • the compound represented by general formula (ii) (including sub-concepts) can be synthesized using a known synthesis method.
  • the liquid crystal composition according to the present invention further includes one or two compounds represented by the following general formula (vt) having at least one -C ⁇ C- as a linking group. It may include the above.
  • R vt1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
  • the alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and preferably a linear alkyl group.
  • the number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S-, -CO- and/or -CS-.
  • one or more -CH 2 -CH 2 -CH 2 - in the alkyl group may be each independently substituted with -O-CO-O-.
  • one or more hydrogen atoms in the alkyl group may be each independently 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 do not bond directly.
  • sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms do not bond directly.
  • R vt1 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 preferably a linear alkoxy group.
  • R vt1 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 preferably a linear alkylsulfanyl group.
  • the number of carbon atoms in the alkylsulfanyl group is preferably 1 to 10, preferably 1 to 6.
  • the alkenyl group is a linear, branched or cyclic alkenyl group, and preferably a linear alkenyl group.
  • the number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.
  • R vt1 represents an alkynyl group having 2 to 20 carbon atoms, in which one or more -CH 2 -CH 2 - in the alkyl group is substituted with -C ⁇ C-. be able to.
  • the alkynyl group is a linear, branched or cyclic alkynyl group, and preferably a linear alkynyl group.
  • the number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.
  • the alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and preferably a linear alkenyloxy group.
  • R vt1 can represent a halogenated alkyl group having 1 to 20 carbon atoms, by replacing one or more hydrogen atoms in the alkyl group with a halogen atom.
  • the halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and preferably a linear halogenated alkyl group.
  • the number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, preferably 2 to 6.
  • R vt1 is obtained by replacing one -CH 2 - in the alkyl group with -O- and replacing one or more hydrogen atoms in the alkyl group with a halogen atom.
  • the halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and preferably a linear halogenated alkoxy group.
  • the number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.
  • Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) in R vt1 include groups represented by formulas (R vt1 -1) to (R vt1 -36).
  • R vt1 is preferably an alkyl group having 1 to 12 carbon atoms when the reliability of the entire liquid crystal composition is important, and a carbon atom when the reduction of the viscosity of the entire liquid crystal composition is important.
  • R vt1 is an alkyl group having 1 to 12 carbon atoms when the reliability of the entire liquid crystal composition is important, and a carbon atom when the reduction of the viscosity of the entire liquid crystal composition is important.
  • it is an alkenyl group of number 2 to 8.
  • a linear alkyl group having 1 to 5 carbon atoms When the ring structure to which R vt1 is bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a carbon atom An alkenyl group having 4 to 5 carbon atoms is preferable, and when the ring structure to which R vt1 is bonded is a saturated ring structure such as cyclohexane, pyran, and dioxane, a linear alkyl group having 1 to 5 carbon atoms, a linear A straight-chain alkoxy group having 1 to 4 carbon atoms and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred.
  • R vt1 preferably has a total of 5 or less carbon atoms and oxygen atoms if present, and is preferably linear.
  • R vt1 is preferably a linear alkyl group having 2 to 6 carbon atoms or a linear alkylsulfanyl group having 1 to 6 carbon atoms.
  • R vt2 is a hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methyl Represents any one of an amino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, or an alkyl group having 1 to 20 carbon atoms.
  • the alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and preferably a linear alkyl group.
  • the number of carbon atoms in the alkyl group is preferably 2 to 10, preferably 2 to 6.
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S-, -CO- and/or -CS-.
  • one or more -CH 2 -CH 2 -CH 2 - in the alkyl group may be each independently substituted with -O-CO-O-.
  • one or more hydrogen atoms in the alkyl group may be each independently 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 do not bond directly.
  • sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms do not bond directly.
  • R vt2 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 preferably a linear alkoxy group.
  • R vt2 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 preferably a linear alkylsulfanyl group.
  • the number of carbon atoms in the alkylsulfanyl group is preferably 1 to 10, preferably 1 to 6.
  • the alkenyl group is a linear, branched or cyclic alkenyl group, and preferably a linear alkenyl group.
  • the number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.
  • R vt2 represents an alkynyl group having 2 to 20 carbon atoms, in which one or more -CH 2 -CH 2 - in the alkyl group is substituted with -C ⁇ C-. be able to.
  • the alkynyl group is a linear, branched or cyclic alkynyl group, and preferably a linear alkynyl group.
  • the number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.
  • the alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and preferably a linear alkenyloxy group.
  • R vt2 can represent a halogenated alkyl group having 1 to 20 carbon atoms, by replacing one or more hydrogen atoms in the alkyl group with a halogen atom.
  • the halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and preferably a linear halogenated alkyl group.
  • the number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, preferably 2 to 6.
  • R vt2 is obtained by replacing one -CH 2 - in the alkyl group with -O- and replacing one or more hydrogen atoms in the alkyl group with a halogen atom.
  • the halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and preferably a linear halogenated alkoxy group.
  • the number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.
  • Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) in R vt2 include groups represented by formulas (R vt2 -1) to (R vt2 -36).
  • the black dots represent the bond to A vt3 .
  • the ring structure to which R vt2 is bonded is a phenyl group (aromatic)
  • An alkenyl group having 4 to 5 carbon atoms is preferable
  • the ring structure to which R vt2 is bonded is a saturated ring structure such as cyclohexane, pyran, and dioxane
  • a linear alkyl group having 1 to 5 carbon atoms, a linear A straight-chain alkoxy group having 1 to 4 carbon atoms and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred.
  • R vt2 preferably has a total of 5 or less carbon atoms and oxygen atoms if present, and is preferably linear.
  • R vt2 includes a fluorine atom, a cyano group, a linear alkyl group having 2 to 6 carbon atoms, and a linear alkyl group having 1 to 6 carbon atoms. An alkoxy group or a linear alkylsulfanyl group having 1 to 6 carbon atoms is preferred.
  • One or more hydrogen atoms in A vt1 , A vt2 and A vt3 may each be independently substituted with a substituent S vt1 .
  • Substituent S vt1 is 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.
  • the alkyl group is a linear, branched or cyclic alkyl group, and preferably a linear alkyl group.
  • the number of carbon atoms in the alkyl group is preferably 2 to 10, preferably 3 to 6.
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S- and/or -CO-.
  • one or more -CH 2 -CH 2 -CH 2 - in the alkyl group may be substituted with -O-CO-O-.
  • One or more hydrogen atoms in the alkyl group may be each independently 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 do not bond directly.
  • sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms do not bond directly.
  • the substituent S vt1 is preferably a fluorine atom or a linear alkyl group having 1 to 3 carbon atoms.
  • at least one of A vt1 , A vt2 and A vt3 is preferably substituted with at least one substituent S vt1 .
  • a vt1 is preferably substituted with at least one substituent S vt1 .
  • when there are multiple substituents S vt1 they may be the same or different.
  • substitution position of the substituent S vt1 in A vt1 is preferably one of the following formulas (A vt1 -SP-1) to (A vt1 -SP-3).
  • the white dots represent the bond of R vt1
  • the black dots represent the bond to -C ⁇ C-.
  • the substitution position of the substituent S vt1 in A vt2 is preferably one of the following formulas (A vt2 -SP-1) to (A vt2 -SP-7) from the viewpoint of compatibility with other liquid crystal compounds. Therefore, it is preferable to represent one of the following formulas (A vt2 -SP-1) to (A vt2 -SP-7).
  • the white dots represent the bond of -C ⁇ C-
  • the black dots represent the bond to Z vt1 .
  • the substitution position of the substituent S vt3 in A vt3 is preferably one of the following formulas (A vt3 -SP-1) to (A vt3 -SP-8), and from the viewpoint of solubility, the following formula ( It is preferable to represent any one of A vt3 -SP-1) to (A vt3 -SP-5).
  • a vt1 preferably represents one of the following formulas (A vt1 -1) to (A vt1 -5).
  • a vt2 preferably represents one of the following formulas (A vt2 -1) to (A vt2 -6).
  • a vt3 preferably represents one of the following formulas (A vt3 -1) to (A vt3 -5).
  • the white dots represent the bond to Z vt1
  • the black dots represent the bond to Z vt1 or R vt2 .
  • each Z vt1 independently represents either 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 preferably a linear alkylene group.
  • the number of carbon atoms in the alkylene group is preferably 2 to 10, preferably 2 to 6.
  • One or more -CH 2 - in the alkylene group may be each independently substituted with -O-, -CF 2 - and/or -CO-.
  • alkylene groups having 1 to 20 carbon atoms include groups represented by formulas (Z vt1 -1) to (Z vt1 -24).
  • the white dots represent the bond to A vt2 or A vt3
  • the black dots represent the bond to A vt3 .
  • n vt1 represents an integer of 1 to 3, preferably an integer of 1 to 2.
  • Z vt1 preferably represents -C ⁇ C- from the viewpoint of ⁇ n and/or ⁇ r .
  • n vt1 is 2 or 3, from the viewpoint of ⁇ n and/or ⁇ r , it is preferable that at least one of Z vt1 represents -C ⁇ C-.
  • a plurality of A vt3 and Z vt1 exist they may be the same or different.
  • the compound represented by the general formula (vt) is preferably a compound represented by the following general formula (vt-1).
  • R vt1 , R vt2 , A vt1 , A vt2 and A vt3 are the same as R vt1 , R vt2 , A vt1 , A vt2 and A vt3 in the above general formula (vt), respectively. express meaning.
  • the compound represented by the general formula (vt-1) is preferably a compound represented by the following general formulas (vt-1-1) to (vt-1-3).
  • R vt1 , R vt2 and S vt1 each independently represent R vt1 , R vt2 and S vt1 in the general formula (vt) above. and have the same meaning.
  • Specific examples of the compound represented by the general formula (vt-1-1) include compounds represented by the following structural formulas (vt-1-1.1) to (vt-1-1.24). It will be done.
  • vt-1-2 Specific examples of the compound represented by the general formula (vt-1-2) include compounds represented by the following structural formulas (vt-1-2.1) to (vt-1-2.8). It will be done.
  • vt-1-3 Specific examples of the compound represented by the general formula (vt-1-3) include compounds represented by the following structural formulas (vt-1-3.1) to (vt-1-3.4). It will be done.
  • the types of compounds represented by -3.1) to (vt-1-3.4) used in the liquid crystal composition are one or more types, preferably 1 to 5 types, preferably 1 to 4 types, Preferably 1 to 3 types, preferably 1 to 2 types, preferably 1 type.
  • the compound represented by the general formula (vt) (including subordinate concepts) can be synthesized using a known synthesis method.
  • the liquid crystal composition according to the present invention may further contain one or more compounds represented by the following general formulas (np-1) to (np-3).
  • R npi and R npii each independently represent either an alkyl group having 1 to 20 carbon atoms or a halogen atom.
  • the alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and preferably a linear alkyl group.
  • the number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S-, -CO- and/or -CS-.
  • one or more -CH 2 -CH 2 -CH 2 - in the alkyl group may be each independently substituted with -O-CO-O-.
  • one or more hydrogen atoms in the alkyl group may be each independently 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 do not bond directly.
  • sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms do not bond directly.
  • R npi and R npii 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 preferably a linear alkoxy group.
  • the number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6.
  • R npi and R npii can represent an alkylsulfanyl group (thioalkyl 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 preferably a linear alkylsulfanyl group.
  • the number of carbon atoms in the alkylsulfanyl group is preferably 2 to 10, preferably 2 to 6.
  • the alkenyl group is a linear, branched or cyclic alkenyl group, and preferably a linear alkenyl group.
  • the number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.
  • R npi and R npii are alkynyl groups having 2 to 20 carbon atoms, by replacing one or more -CH 2 -CH 2 - in the alkyl group with -C ⁇ C-. can represent a group.
  • the alkynyl group is a linear, branched or cyclic alkynyl group, and preferably a linear alkynyl group.
  • the number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.
  • the alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and preferably a linear alkenyloxy group.
  • the number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6.
  • R npi and R npii can represent a halogenated alkyl group having 1 to 20 carbon atoms, by replacing one or more hydrogen atoms in the alkyl group with a halogen atom.
  • the halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and preferably a linear halogenated alkyl group.
  • the number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, preferably 2 to 6.
  • R npi and R npii are such that one -CH 2 - in the alkyl group is substituted with -O-, and one or more hydrogen atoms in the alkyl group are substituted with a halogen atom.
  • the halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and preferably a linear halogenated alkoxy group.
  • the number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.
  • alkyl group having 1 to 20 carbon atoms (including substituted ones) in R npi and R npii are those represented by formulas (R npi/ii -1) to (R npi/ii -36). Examples include groups such as
  • black dots represent bonds to ring A, ring B, ring C, or ring D.
  • halogen atom in R npi and R npii include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
  • ring A, ring B, ring C and ring D each independently represent the following groups (a), group (b), group (c) and (d):
  • One or more hydrogen atoms in Ring A, Ring B, Ring C, and Ring D may each be independently substituted with a substituent S npi1 .
  • the substituent S npi1 represents either a halogen atom, a cyano group, or an alkyl group having 1 to 20 carbon atoms.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a fluorine atom being preferred from the viewpoint of stability and safety.
  • the alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and preferably a linear alkyl group.
  • the number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.
  • One or more -CH 2 - in the alkyl group may be each independently substituted with -O-, -S-, -CO- and/or -CS-.
  • One or more -CH 2 -CH 2 -CH 2 -CH 2 - in the alkyl group may be each independently substituted with -O-CO-O-.
  • one or more hydrogen atoms in the alkyl group may be each independently 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 do not bond directly.
  • sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms do not bond directly.
  • the substituent S npi1 is preferably a halogen atom, and preferably a fluorine atom.
  • substituent S npi1 when there are multiple substituents S npi1 , they may be the same or different.
  • substitution position of the substituent S npi1 in ring A is preferably the following formula (A-SP-1).
  • ring A preferably represents one of the following formulas (A-1) to (A-3).
  • ring B preferably represents one of the following formulas (B-1) to (B-2).
  • ring C preferably represents one of the following formulas (C-1) to (C-2).
  • the white dots represent the bond to Z npii
  • the black dots represent the bond to R npii or Z npiii .
  • Z npi , Z npi and Z npiii each independently represent either a single bond or an alkylene group having 1 to 20 carbon atoms.
  • One or more -CH 2 - in the alkylene group may be each independently substituted with -O-, -CF 2 - and/or -CO-.
  • alkylene group having 1 to 20 carbon atoms when the alkylene group having 1 to 20 carbon atoms is substituted with a predetermined group, the oxygen atoms do not bond directly. Further, from the viewpoint of stability of the compound, it is preferable that sulfur atoms and sulfur atoms and/or oxygen atoms and sulfur atoms do not bond directly.
  • alkylene groups having 1 to 20 carbon atoms include groups represented by formulas (Z npi/ii/ii -1) to (Z npi/ii/ii -24). etc.
  • Z npi/ii/iii -1) to (Z npi/ii/ii -24) white dots represent bonds to ring A, ring B or ring C, and black dots represent bonds to ring B, ring C or Represents the bond to ring D.
  • Z npi , Z npii and Z npiii each independently preferably represent either a single bond, -C ⁇ C- or -CO-O-.
  • the compound represented by general formula (vt) (including subordinate concepts) is excluded.
  • the compound represented by the general formula (np-2) is preferably a compound represented by the following general formulas (np-2-1) to (np-2-3).
  • R npi , R npii and S npi are R npi , R npii in general formulas (np-1) to (np-3) above. and S npi respectively.
  • Specific examples of the compound represented by the general formula (np-2-1) include compounds represented by the following structural formula (np-2-1.1).
  • np-2-2 Specific examples of the compound represented by the general formula (np-2-2) include compounds represented by the following structural formulas (np-2-2.1) to (np-2-2.5). It will be done.
  • np-2-3 Specific examples of the compound represented by the general formula (np-2-3) include compounds represented by the following structural formulas (np-2-3.1) to (np-2-3.3). It will be done.
  • General formula (np-1) to (np-3), general formula (np-2-1) to (np-2-3), structural formula (np-2-1.1), structural formula (np-2 -2.1) to (np-2-2.5) or the types of compounds represented by structural formulas (np-2-3.1) to (np-2-3.3) used in liquid crystal compositions are: , one or more types, 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 compounds represented by general formulas (np-1) to (np-3) (including subordinate concepts) can be produced by known methods.
  • liquid crystal composition (Liquid crystal composition)
  • the liquid crystal composition according to the present invention can be prepared, for example, by mixing the compound represented by the above-mentioned general formula (i) and the compound represented by the general formula (ii), and if necessary, the above-mentioned other compounds and additives. It can be manufactured by
  • additives include stabilizers, dye compounds, polymerizable compounds, azotolan compounds, and the like.
  • stabilizers examples include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, ⁇ -naphthylamines, ⁇ -naphthols, nitroso compounds, and hindered phenols. and hindered amines.
  • hindered phenols examples include hindered phenol antioxidants represented by the following structural formulas (XX-1) to (XX-3).
  • hindered amines examples include hindered amine light stabilizers represented by the following structural formulas (YY-1) to (YY-2).
  • the stabilizer used in the liquid crystal composition may be one or more types, preferably 1 to 10 types, preferably 1 to 8 types, preferably 1 to 6 types, preferably 1 to 6 types. 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, and preferably 0.02 to 0.50% by mass. , preferably 0.03 to 0.35% by mass.
  • combinations of compounds used in the liquid crystal composition include: 1. A combination of a compound represented by general formula (i) (including subordinate concepts) and a compound represented by general formula (ii) (including subordinate concepts), 2. Compounds represented by general formula (i) (including subordinate concepts), compounds represented by general formula (ii-2) (including subordinate concepts), and compounds represented by general formula (ii-3) (including subordinate concepts), 3.
  • a compound represented by general formula (i-4) (including lower concepts), a compound represented by general formula (ii-2) (including lower concepts), and a compound represented by general formula (ii-3) (including subordinate concepts), a compound represented by general formula (ii-4) (including subordinate concepts), and a compound represented by general formula (ii-6) (including subordinate concepts). combination, 4.
  • a compound represented by general formula (i-4) (including lower concepts), a compound represented by general formula (ii-1) (including lower concepts), and a compound represented by general formula (ii-2) (including subordinate concepts), the compound represented by general formula (ii-3) (including subordinate concepts), and the compound represented by general formula (ii-5) (including subordinate concepts). combination, 5.
  • a compound represented by general formula (i-4) (including lower concepts), a compound represented by general formula (ii-2) (including lower concepts), and a compound represented by general formula (ii-3) A combination of a compound (including subordinate concepts) represented by general formula (ii-6) (including subordinate concepts), 6.
  • Compounds represented by general formula (i-10) (including lower concepts) and general formula (ii-2)
  • a compound represented by general formula (ii-3) including lower concepts
  • a compound represented by general formula (ii-4) (including lower concepts), and a compound represented by general formula (ii-4) (including lower concepts).
  • a compound represented by general formula (ii-6) including subordinate concepts
  • a compound represented by general formula (i-4) (including lower concepts), a compound represented by general formula (i-11) (including lower concepts), and a compound represented by general formula (ii-2) a compound represented by general formula (ii-3) (including subordinate concepts), a compound represented by general formula (ii-4) (including subordinate concepts), A combination with a compound represented by general formula (ii-6) (including subordinate concepts), 8.
  • the liquid crystal phase upper limit temperature (T ni ) is the temperature at which the liquid crystal composition undergoes a 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 with a polarizing microscope while heating it on a hot stage. It can also be measured by differential scanning calorimetry (DSC). The unit is "°C". The higher T ni is, the more the nematic phase can be maintained even at high temperatures, and the driving temperature range can be wider.
  • the liquid crystal phase upper limit temperature (T ni ) of the liquid crystal composition according to the present invention is appropriately set depending on whether it is used indoors, in a car, etc. where the external temperature of the liquid crystal display element can be controlled, or when it is used outdoors.
  • the temperature is preferably 100°C or higher, preferably 100 to 200°C, and preferably 110 to 180°C.
  • the liquid crystal phase lower limit temperature (T ⁇ n ) is the temperature at which the liquid crystal composition undergoes a phase transition from another phase (glass phase, smectic phase, crystalline phase) to a nematic phase.
  • T ⁇ n is measured by filling a glass capillary with a liquid crystal composition, immersing it in a -70°C refrigerant to cause a phase transition of the liquid crystal composition to another phase, and observing while increasing the temperature. It can also be measured by differential scanning calorimetry (DSC). The unit is "°C".
  • the lower T ⁇ n is, the more the nematic phase can be maintained even at lower temperatures, so the driving temperature range can be wider.
  • 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, preferably -70 to 0°C, and -40 to -5°C. Preferably it is °C.
  • ⁇ n (refractive index anisotropy) correlates with ⁇ n in the near-infrared region used in an optical sensor described later.
  • a liquid crystal composition was injected into a glass cell with a cell gap (d) of approximately 3.0 ⁇ m and a polyimide alignment film that had been subjected to anti-parallel rubbing treatment, and the in-plane Re was measured using a retardation film/optical material inspection device RETS-100 ( (manufactured by Otsuka Electronics Co., Ltd.). Measurements are performed at a temperature of 25° C. and a wavelength of 589 nm, and there are no units.
  • ⁇ n of the liquid crystal composition according to the present invention at 25° C. and 589 nm is preferably 0.38 or more, and preferably 0.38 to 0.60, from the viewpoint of phase modulation power of light at the wavelength, It is preferably 0.40 to 0.55, more preferably 0.40 to 0.50.
  • the rotational viscosity ( ⁇ 1 ) is a viscosity related to rotation of liquid crystal molecules.
  • ⁇ 1 can be measured by filling a glass cell with a cell gap of about 10 ⁇ m with a liquid crystal composition, applying a voltage of 50 V, and using LCM-2 (manufactured by Toyo Technica).
  • LCM-2 manufactured by Toyo Technica
  • a horizontal alignment cell is used, and in the case of a liquid crystal composition having a negative dielectric constant anisotropy, a vertical alignment cell is used.
  • the measurement is performed 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 2000 mPa ⁇ s, and preferably 200 to 1500 mPa ⁇ s, from the viewpoint of response speed. , 250 to 1000 mPa ⁇ s.
  • the threshold voltage (V th ) is correlated to the driving voltage of the liquid crystal composition.
  • V th can be determined from the transmittance when a voltage is applied to a TN cell with a gap of 8.3 ⁇ m filled with a liquid crystal composition. The measurement is performed at a temperature of 25° C., and the unit is “V”.
  • V th at 25° C. of the liquid crystal composition according to the present invention is preferably 3.0 V or less, preferably 0.3 to 3.0 V, and 0.5 to 2.0 V. 7V is preferable, 0.7 to 2.5V is preferable, 0.9 to 2.3V is preferable, 1.1 to 2.1V is preferable, 1.3 to 2.1V is preferable. Preferably it is 2.1V.
  • the dielectric anisotropy in the high frequency region the greater the phase modulation force for radio waves in the target frequency band, and therefore it is particularly suitable for antenna applications. Furthermore, in 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 tan ⁇ iso of the dielectric loss tangent at 10 GHz were measured as representative characteristics in a high frequency region.
  • ⁇ r is the dielectric constant
  • tan ⁇ is the dielectric loss tangent
  • the subscript " ⁇ ” is the direction parallel to the alignment direction of the liquid crystal
  • ⁇ is the direction 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, and the effective length is 4.0 cm.
  • a capillary tube containing a liquid crystal composition is introduced into the center of a cavity resonator (manufactured by EM Lab Co., Ltd.) having a resonant frequency of 10 GHz.
  • This cavity resonator has an outer diameter of 30 mm and a width of 26 mm.
  • a signal is 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, etc. of a PTFE capillary tube without a liquid crystal composition encapsulated therein and the resonance frequency, etc. of a PTFE capillary tube encapsulated 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 by controlling the orientation of liquid crystal molecules as values of characteristic components perpendicular to and parallel to the orientation direction of the liquid crystal molecules.
  • a magnetic field from a permanent magnet or an electromagnet is used to align the liquid crystal molecules in the vertical direction (perpendicular to the effective length direction) or parallel direction (parallel to the effective length direction) of the PTFE capillary.
  • the magnetic field has, for example, a distance between magnetic poles of 45 mm, and a magnetic field strength near the center of 0.23 Tesla.
  • a desired characteristic component is obtained by rotating a PTFE capillary tube containing a liquid crystal composition in parallel or perpendicular to a magnetic field. The measurement was performed 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, but from the viewpoint of phase modulation power in the GHz band, it is preferably 0.90 or more, and 0.90 to 1.40. It is preferably from 0.95 to 1.40, and preferably from 1.00 to 1.35.
  • the tan ⁇ iso at 25° C. of the liquid crystal composition according to the present invention is preferably smaller, but from the viewpoint of loss in the GHz band, it is preferably 0.025 or less, and preferably 0.001 to 0.025. preferably from 0.003 to 0.020, preferably from 0.005 to 0.017, preferably from 0.007 to 0.015, and from 0.008 to 0.013 It is preferably from 0.009 to 0.012.
  • liquid crystal display elements Liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment 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 explained.
  • a 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 method or a passive matrix method. Further, the liquid crystal display element according to the present invention is preferably a liquid crystal display element that reversibly switches the dielectric constant by reversibly changing the orientation 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 includes, for example, a distance measuring sensor that uses electromagnetic waves, visible light or infrared light, an infrared sensor that uses temperature change, and a cholesteric sensor that uses a temperature change.
  • Temperature sensors that use changes in the wavelength of reflected light due to changes in the pitch of liquid crystals, pressure sensors that use changes in the wavelength of reflected light, ultraviolet sensors that use changes in the wavelength of reflected light due to changes in composition, electrical sensors that use changes in temperature due to voltage and current, Radiation sensors that utilize temperature changes associated with the trajectory of radiation particles; Ultrasonic sensors that utilize changes in liquid crystal molecule alignment due to mechanical vibrations of ultrasonic waves; Ultrasonic sensors that utilize changes in reflected light wavelength due to temperature changes or liquid crystal molecule alignment changes due to electric fields. Examples include electromagnetic field sensors.
  • the ranging sensor is preferably for LiDAR (Light Detection and Ranging) using a light source.
  • LiDAR is preferably used for artificial satellites, aircraft, unmanned aerial vehicles (drones), automobiles, railways, and ships.
  • the light source is an LED or a laser, preferably a laser.
  • the light used for LiDAR is preferably infrared light, and preferably has a wavelength of 800 to 2000 nm.
  • an infrared laser with a wavelength of 905 nm or 1550 nm is preferred.
  • a 905 nm infrared laser is preferable when the cost of the photodetector used and sensitivity in all weathers are important, and a 1550 nm infrared laser is preferable when safety regarding human vision is important.
  • the liquid crystal composition according to the present invention exhibits a high ⁇ n, it has a large phase modulation power in 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, as one aspect thereof, a first transparent electrode layer, a second transparent electrode layer, and a first transparent electrode layer are provided.
  • a liquid crystal layer containing the above-described liquid crystal composition provided between the transparent electrode layer and the second transparent electrode layer; an insulating layer provided between the second transparent electrode layer and the liquid crystal layer;
  • the liquid crystal display device includes an insulating layer and a high resistance layer provided between the liquid crystal layer.
  • the liquid crystal lens according to the present invention is used, for example, as a 2D/3D switching lens, a focus adjustment lens for a camera, and the like.
  • An optical communication device is characterized by using the above-mentioned liquid crystal composition.
  • a liquid crystal constituting each of a plurality of pixels is disposed on a reflective layer (electrode).
  • An example is an LCOS (Liquid crystal on silicon) having a two-dimensionally arranged liquid crystal layer.
  • 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 includes: a first substrate including a plurality of slots; a second substrate facing the first substrate and provided with a power feeding section; a first dielectric layer provided between the two substrates; a plurality of patch electrodes disposed corresponding to the plurality of slots; a third substrate provided with the patch electrodes; a liquid crystal layer provided between the third substrate and the liquid crystal layer, the liquid crystal layer containing the above-mentioned liquid crystal composition.
  • the liquid crystal composition includes one or more compounds (including subordinate concepts) represented by the general formula (i) having an indane structure and an isothiocyanate group (-NCS), and an isothiocyanate group (-NCS). ) by using a liquid crystal composition containing one or more compounds represented by general formula (ii), T ni is high, ⁇ n is large, V th is low, ⁇ r is large, Since tan ⁇ iso is small and storage stability at low temperatures is good, it is possible to provide an antenna with high reliability against external stimuli such as heat. Thereby, it is possible to provide an antenna that enables greater phase control of microwave or millimeter wave electromagnetic waves.
  • the antenna according to the present invention operates at Ka-band frequencies, K-band frequencies, or Ku-band frequencies used for satellite communications.
  • the antenna according to the present invention preferably has a configuration that combines a radial line slot array and a patch antenna array.
  • the matters described in, for example, International Publication No. 2021/157189 pamphlet, etc. can be taken into consideration and applied.
  • n in the table is a natural number.
  • n in the table is a natural number.
  • Examples 1 to 36 and Comparative Examples 1 to 2 LC-A to B and LC-01 to 06, hindered phenolic antioxidants (XX-1) to (XX-3), and hindered amine light stabilizers (YY-1) to (YY-2).
  • the liquid crystal compositions listed in Tables 4 to 9 were prepared using the following methods, their physical properties were measured, and a ⁇ storability test> was conducted. The results are shown in Tables 4-9. Note that in Comparative Example 2, the high frequency characteristics ( ⁇ r and tan ⁇ iso ) were not measured because the crystallization occurred at room temperature.
  • ⁇ Storability test> 0.5 g of the liquid crystal composition was weighed into a 1 mL sample bottle (manufactured by Maruem Co., Ltd.), and defoaming was performed at 150 to 250 Pa for 10 minutes. It was then purged with dry nitrogen and the provided lid was placed. This was stored for two weeks in a -20°C temperature-controlled thermostat (manufactured by Espec, SH-241), and the occurrence of crystallization of the liquid crystal composition was visually confirmed every week.
  • the liquid crystal compositions using the compound represented by the general formula (i) and the compound represented by the general formula (ii) have a high T ni , a large ⁇ n, and a low V th . , ⁇ r were large, tan ⁇ iso was small, and the liquid crystal composition had good storage stability at low temperatures.
  • Examples 1, 5, and 6 had particularly large results in ⁇ n and ⁇ r .
  • liquid crystal compositions that did not use the compound represented by general formula (i) had ⁇ n of less than 0.38, or crystallization was confirmed at room temperature.
  • the compound and liquid crystal composition of the present invention can be used in liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment, and antennas.

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