Liquid crystal composition, and liquid crystal display element, sensor, liquid crystal lens, optical communication device and antenna using the same

Abstract

The present invention addresses the problem of providing a liquid crystal composition having a high Tni, a large Δn, a large Δεr, a small tanδiso, and favorable preservability at room temperature, and providing a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the same.　Specifically, the liquid crystal composition contains one or two or more compounds represented by general formula (i) having an alkenyl group and an isothiocyanate group (-NCS), and one or two or more compounds represented by general formula (ii) having an alkynyl group and an isothiocyanate group (-NCS).

Description

[Technical Field]

[0001] The present invention relates to a liquid crystal composition, and a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device and an antenna using the same. [Background technology]

[0002] Liquid crystals, which are widely used in displays, are attracting attention as a new application for liquid crystal antennas that transmit and receive radio waves between mobile objects such as automobiles and communication satellites. Conventionally, satellite communications have used parabolic antennas. However, when used in mobile objects such as automobiles, the parabolic antenna must be constantly pointed toward the satellite, necessitating large moving parts. However, liquid crystal antennas can change the direction of radio waves by moving the liquid crystals inside the panel. This eliminates the need to move the antenna itself, and the antenna shape can be made flat. Furthermore, to achieve high-capacity, high-speed global communications, low-earth-orbit (LOW-EO) satellite constellations with numerous low-earth-orbit satellites are being studied. Liquid crystal antennas, which can easily change the direction of radio waves, are useful for tracking low-earth-orbit satellites, which appear to be constantly moving from the ground. Generally, autonomous driving of automobiles and other vehicles requires the downloading of large amounts of high-precision 3D map information. However, by incorporating an antenna using liquid crystal into a vehicle, it becomes possible to download large amounts of data from communication satellites without any mechanical moving parts. The frequency band used in satellite communications is approximately 13 GHz, which is significantly different from the frequencies used in liquid crystal displays to date. As a result, the physical properties required of liquid crystals are also significantly different. For example, a Δn of approximately 0.4 is required for liquid crystals used in antennas, and the operating temperature range is, for example, -20 to 120°C. Additionally, infrared laser image recognition and distance measurement devices using liquid crystals are attracting attention as sensors for autonomous driving of moving objects such as automobiles. The Δn required for liquid crystals for this application is, for example, 0.3 to 0.6, and the operating temperature range is, for example, 10 to 100°C. Furthermore, it is known that many liquid crystal compounds constituting a liquid crystal composition exhibiting a high Δn of 0.2 or more have low compatibility, so it is also important to select a liquid crystal compound with high compatibility. In contrast to this, Patent Document 1, for example, is an example of a liquid crystal technology for antennas. Furthermore, Non-Patent Document 1 proposes the use of liquid crystal materials as components of high frequency devices. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2016-37607 [Non-patent literature]

[0004] [Non-Patent Document 1] Dolfi, Electronics Letters, (UK), 1993, Vol. 29, No. 10, pp. 926-928 Summary of the Invention [Problem to be solved by the invention]

[0005] The present invention is ni is high, Δn is large, and Δε r is large, and tanδ iso The present invention aims to provide a liquid crystal composition having a small viscosity and good storage stability at room temperature, and a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the same. [Means for solving the problem]

[0006] As a result of intensive investigations, the present inventors have found that the above-mentioned problems can be solved by a liquid crystal composition containing one or more compounds represented by general formula (i) having an alkenyl group and an isothiocyanate group (-NCS), and one or more compounds represented by general formula (ii) having an alkynyl group and an isothiocyanate group (-NCS), and have thus completed the present invention. An example of the configuration of the present invention that solves the above problem is as follows.

[0007] Item 1. The following general formula (i)

[0008] [ka]

[0009] (In general formula (i), R i1 represents an alkenyl group having 2 to 20 carbon atoms, one or more -CH2- in the alkenyl group may each independently be replaced by -O-, -S-, -NH-, -CO- and / or -CS-; one or more -CH2-CH2- in the alkenyl group may each independently be replaced by -CH=CH- and / or -CF=CF-; One or more hydrogen atoms in the alkenyl group may be independently substituted with a halogen atom, Oxygen atoms do not bond directly to each other, A i1 , A i2 and A i3 each independently represents a hydrocarbon ring having 3 to 16 carbon atoms or a heterocycle having 3 to 16 carbon atoms, The above A i1 , A i2 and A i3 One or more hydrogen atoms in each independently represent a substituent S i1 and optionally substituted by substituent S i1represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms; one or more -CH2- groups in the alkyl group may each independently be replaced by -O-, -S-, -NH-, -CO- and / or -CS-; One or more -CH2-CH2- groups in the alkyl group may each independently be replaced by -CH=CH-, -CF=CF- and / or -C≡C-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, Oxygen atoms do not bond directly to each other, substituent S i1 When there are multiple, they may be the same or different, Z i1 and Z i2 each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms, one or more -CH2- in the alkylene group may each independently be replaced by -O-, -CF2- and / or -CO-; One or more -CH2-CH2- in the alkylene group may each independently be substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, Oxygen atoms do not bond directly to each other, n i1 represents an integer between 0 and 1.) and one or more compounds represented by the formula: The following general formula (ii)

[0010] [ka]

[0011] (In general formula (ii), R ii1 represents an alkynyl group having 2 to 20 carbon atoms, one or more -CH2- in the alkynyl group may each independently be replaced by -O-, -S-, -NH-, -CO- and / or -CS-; One or more -CH2-CH2- in the alkynyl group may each independently be replaced by -C≡C-; One or more hydrogen atoms in the alkynyl group may be independently substituted with a halogen atom, Oxygen atoms do not bond directly to each other, A ii1 , A ii2 and A ii3 each independently represents a hydrocarbon ring having 3 to 16 carbon atoms or a heterocycle having 3 to 16 carbon atoms, The above A ii1 , A ii2 and A ii3 One or more hydrogen atoms in each independently represent a substituent S ii1 and optionally substituted by substituent S ii1 represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms; one or more -CH2- groups in the alkyl group may each independently be replaced by -O-, -S-, -NH-, -CO- and / or -CS-; One or more -CH2-CH2- groups in the alkyl group may each independently be replaced by -CH=CH-, -CF=CF- and / or -C≡C-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, Oxygen atoms do not bond directly to each other, substituent S ii1 When there are multiple, they may be the same or different, Z ii1 and Z ii2 each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms, one or more -CH2- in the alkylene group may each independently be replaced by -O-, -CF2- and / or -CO-; One or more -CH2-CH2- in the alkylene group may each independently be substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, Oxygen atoms do not bond directly to each other, n ii1 represents an integer from 0 to 2, A ii3 and Z ii2 When there are multiple, they may be the same or different.) A liquid crystal composition comprising one or more compounds represented by the following formula:

[0012] Item 2. The total content of the compounds represented by the general formula (i) in the liquid crystal composition (100% by mass) is 1 to 40% by mass, and / or Item 2. The liquid crystal composition according to item 1, wherein the total content of the compounds represented by formula (ii) in 100% by mass of the liquid crystal composition is 1 to 55% by mass.

[0013] Item 3. The compound represented by the general formula (i) is represented by the following general formulas (i-1) to (i-2):

[0014] [ka]

[0015] (In general formulas (i-1) to (i-2), R i1 , A i1 , A i2 and A i3 represents R in the above general formula (i). i1 , A i1 , A i2 and A i3 and have the same meaning.) 3. The liquid crystal composition according to item 1 or 2, wherein the compound is selected from the group consisting of compounds represented by the following formula:

[0016] Item 4. The compound represented by the general formula (ii) is represented by the following general formulas (ii-1) to (ii-3):

[0017] [ka]

[0018] (In general formulas (ii-1) to (ii-3), R ii1 , A ii1 , A ii2 and A ii3 is R in the above general formula (ii). ii1 , A ii1 , A ii2 and A ii3 and each mean the same thing, In general formula (ii-3), A ii3-2 The definition of A in the above general formula (ii) ii3-2 ) 4. The liquid crystal composition according to any one of items 1 to 3, wherein the compound is selected from the group consisting of compounds represented by the following formula:

[0019] Item 5. Furthermore, the following general formula (iii)

[0020] [ka]

[0021] (In general formula (iii), R iii1 each independently represents an alkyl group having 1 to 20 carbon atoms, one or more -CH2- groups in the alkyl group may each independently be replaced by -O-, -S-, -NH-, -CO- and / or -CS-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, Oxygen atoms do not bond directly to each other, A iii1 and A iii2 are each independently the following groups (a), (b), (c), and (d): (a) a 1,4-cyclohexylene group (in which one —CH— or two or more non-adjacent —CH— groups may be replaced by —O— and / or —S—). (b) a 1,4-phenylene group (in which one -CH= or two or more -CH= may be replaced by -N=). (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group, 2,3-dihydro-1H-indene-1,5-diyl group, 2,3-dihydro-1H-indene-2,5-diyl group, 2,3-dihydro-1H-indene-1,6-diyl group, 1 1H-indene-2,5-diyl group, 1H-indene-1,5-diyl group, 1H-indene-3,5-diyl group, 1H-indene-1,6-diyl group, 1H-indene-2,6-diyl group, 1H-indene-3,6-diyl group (one -CH= or two or more -CH= in a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, an anthracene-2,6-diyl group, an anthracene-1,4-diyl group, an anthracene-9,10-diyl group, or a phenanthrene-2,7-diyl group may be replaced by -N=). (d) a thiophene-2,5-diyl group, a benzothiophene-2,5-diyl group, a benzothiophene-2,6-diyl group, a dibenzothiophene-3,7-diyl group, a dibenzothiophene-2,6-diyl group, a thieno[3,2-b]thiophene-2,5-diyl group, or a benzo[1,2-b:4,5-b']dithiophene-2,6-diyl group (one -CH= or two or more -CH= in this group may be replaced by -N=). represents a group selected from the group consisting of The above A iii1 and A iii2 One or more hydrogen atoms in each independently represent a substituent S iii1 and optionally substituted by substituent S iii1represents any one of a halogen atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms, one or more -CH2- groups in the alkyl group may each independently be replaced by -O-, -S-, -NH-, -CO- and / or -CS-; one or more -CH2-CH2- groups in the alkyl group may each independently be replaced by -CH=CH-, -CF=CF- and / or -C≡C-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, Oxygen atoms do not bond directly to each other, substituent S iii1 When there are multiple, they may be the same or different, Z iii1 represents a single bond or an alkylene group having 1 to 20 carbon atoms, one or more -CH2- in the alkylene group may each independently be replaced by -O-, -CF2- and / or -CO-; one or more -CH2-CH2- in the alkylene group may each independently be substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-; Oxygen atoms do not bond directly to each other, n iii1 represents an integer from 1 to 4, A iii1 and Z iii1 When there are multiple, they may be the same or different.) 5. The liquid crystal composition according to any one of items 1 to 4, comprising one or more compounds represented by the following formula:

[0022] Item 6. Upper limit temperature of liquid crystal phase (T ni 6. The liquid crystal composition according to any one of items 1 to 5, wherein the temperature (Tc) of the liquid crystal composition is 120° C. or higher.

[0023] Item 7. A liquid crystal display device using the liquid crystal composition according to any one of items 1 to 6.

[0024] Item 8. The liquid crystal display element according to item 7, which is driven by an active matrix method or a passive matrix method.

[0025] Item 9. A liquid crystal display device in which the dielectric constant is reversibly switched by reversibly changing the alignment direction of liquid crystal molecules in the liquid crystal composition according to any one of items 1 to 6.

[0026] Item 10. A sensor using the liquid crystal composition according to any one of items 1 to 6.

[0027] Item 11. A liquid crystal lens using the liquid crystal composition according to any one of items 1 to 6.

[0028] Item 12. An optical communication device using the liquid crystal composition according to any one of items 1 to 6.

[0029] Item 13. An antenna using the liquid crystal composition according to any one of items 1 to 6.

[0030] Item 14. The antenna according to item 13, a first substrate having a plurality of slots; a second substrate facing the first substrate and provided with a power supply unit; a first dielectric layer disposed between the first substrate and the second substrate; a plurality of patch electrodes arranged corresponding to the plurality of slots; a third substrate on which the patch electrode is provided; a liquid crystal layer provided between the first substrate and the third substrate, Item 7. An antenna in which the liquid crystal layer contains the liquid crystal composition according to any one of items 1 to 6. [Effects of the Invention]

[0031] According to the present invention, a liquid crystal composition containing one or more compounds represented by general formula (i) having an alkenyl group and an isothiocyanate group (-NCS), and one or more compounds represented by general formula (ii) having an alkynyl group and an isothiocyanate group (-NCS) can be used to obtain T ni is high, Δn is large, and Δε r is large, and tanδ iso A liquid crystal composition having a small viscosity and good storage stability at room temperature can be obtained, and the liquid crystal composition is useful for liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas. DETAILED DESCRIPTION OF THE INVENTION

[0032] (Compound represented by general formula (i)) The liquid crystal composition according to the present invention contains one or more compounds represented by general formula (i) having an alkenyl group and an isothiocyanate group (-NCS).

[0033] [ka]

[0034] In general formula (i), R i1 represents an alkenyl group having 2 to 20 carbon atoms. The alkenyl group having 2 to 20 carbon atoms is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group. The alkenyl group having 2 to 20 carbon atoms preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. One or more -CH2- in the alkenyl group may each independently be substituted by -O-, -S-, -NH-, -CO- and / or -CS-. In addition, one or more -CH2-CH2- in the alkenyl group may each independently be substituted with -CH=CH- and / or -CF=CF-. Furthermore, one or more hydrogen atoms in the alkenyl group may each independently be substituted with a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom. However, when the alkenyl group is substituted with a specific group, the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms are not directly bonded to each other and / or oxygen atoms are not directly bonded to each other. R i1 Specific examples of the alkenyl group having 1 to 20 carbon atoms (including substituted ones) in the formula (R i1 -1)~(R i1 -19) and the like.

[0035] [ka]

[0036] Formula (R i1 -1)~(R i1 -19) In the middle, the black dot is A i1 Represents a bond to . In addition, R i1 As the alkyl group, a linear alkenyl group having 2 to 6 carbon atoms is preferred from the viewpoints of Δn and compatibility with other liquid crystal compounds.

[0037] In general formula (i), A i1 , A i2 and A i3 each independently represents a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms. More specifically, the hydrocarbon ring having 3 to 16 carbon atoms or the heterocyclic ring having 3 to 16 carbon atoms is the following group (a), group (b), group (c), and group (d): (a) a 1,4-cyclohexylene group (in which one —CH— or two or more non-adjacent —CH— groups may be replaced by —O— or —S—). (b) a 1,4-phenylene group (in which one —CH= or two or more non-adjacent —CH= groups may be replaced by —N=). (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthracene anthracene-2,7-diyl group (one -CH= or two or more -CH= present in a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, an anthracene-2,6-diyl group, an anthracene-1,4-diyl group, an anthracene-9,10-diyl group, or a phenanthrene-2,7-diyl group may be replaced by -N=); (d) a thiophene-2,5-diyl group, a benzothiophene-2,5-diyl group, a benzothiophene-2,6-diyl group, a dibenzothiophene-3,7-diyl group, a dibenzothiophene-2,6-diyl group, or a thieno[3,2-b]thiophene-2,5-diyl group (in this group, one —CH= or two or more non-adjacent —CH= may be replaced by —N=). It is preferred that the aryl group represents a group selected from the group consisting of:

[0038] A i1 , A i2 and A i3 One or more hydrogen atoms in each independently represent a substituent S i1 may be substituted by substituent S i1represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms. The alkyl group may be a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group. The alkyl group preferably has 2 to 10 carbon atoms, and more preferably 3 to 6 carbon atoms. One or more -CH2- groups in the alkyl group may each independently be substituted with -O-, -S-, -NH-, -CO- and / or -CS-. Furthermore, one or more -CH2-CH2- groups in the alkyl group may each independently be substituted with -CH=CH-, -CF=CF- and / or -C≡C-. Furthermore, one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted with a specific group, the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms are not directly bonded to each other and / or oxygen atoms are not directly bonded to each other. substituent S i1 As the alkyl group, a fluorine atom, a chlorine atom, a linear alkyl group having 1 to 6 carbon atoms, or a linear alkoxy group having 1 to 6 carbon atoms is preferred. Also, A i1 , A i2 and A i3 At least one of the groups has at least one substituent S i1 It is preferably substituted with Also, A i3 has at least one substituent S i1 It is preferably substituted with In addition, the substituent S i1 When there are a plurality of, they may be the same or different.

[0039] A i1 Substituent S in i1 The substitution position of the following formula (A i1 -SP-1)~(A i1 -SP-4).

[0040] [ka]

[0041] Formula (A i1 -SP-1)~(A i1 -SP-4) White points are R i1 The black dots represent bonds to Z. i1 Represents a bond to . A i2 Substituent S in i1 The substitution position of the following formula (A i2 -SP-1)~(A i2 -SP-4).

[0042] [ka]

[0043] Formula (A i2 -SP-1)~(A i2 -SP-4) White spots are Z i1 The black dots represent bonds to Z. i2 or represents a bond to an isothiocyanate group (-NCS). A i3 Substituent S in i1 The substitution position of the following formula (A i3 -SP-1)~(A i3 -SP-4).

[0044] [ka]

[0045] Formula (A i3 -SP-1)~(A i3 -SP-4) White spots are Z i2 The black dot represents a bond to the isothiocyanate group (-NCS). More specifically, A i1 is expressed by the following formula (A i1 -1)~(A i1 -11) is preferably represented by either

[0046] [ka]

[0047] Formula (A i1 -1)~(A i1 -11) In the middle, the white point is R i1 The black dots represent bonds to Z. i1 Represents a bond to . More specifically, A i2 is expressed by the following formula (A i2 -1)~(A i2 -13) is preferably represented by either

[0048] [ka]

[0049] Formula (A i2 -1)~(A i2 -13) In the middle, the white point is Z i1 The black dots represent bonds to Z. i2 or represents a bond to an isothiocyanate group (-NCS). More specifically, A i3 is expressed by the following formula (A i3 -1)~(A i3 -11) is preferably represented by either

[0050] [ka]

[0051] Formula (A i3 -1)~(A i3 -11) White point is Z i2 The black dot represents the bond to the isothiocyanate group (-NCS).

[0052] In general formula (i), Z i1 and Z i2 each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms. The alkylene group is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group. The alkylene group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. One or more -CH2- in the alkylene group may each independently be substituted with -O-, -CF2- and / or -CO-. Furthermore, one or more -CH2-CH2- in the alkylene group may each independently be substituted with -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-. However, when the alkylene group is substituted with a specific group, the oxygen atoms are not directly bonded to each other.

[0053] Specific examples of the alkylene group having 2 to 20 carbon atoms (including substituted ones) include the alkylene group represented by the formula (Z i1 / 2 -1)~(Z i1 / 2 -24).

[0054] [ka]

[0055] Formula(Z i1 / 2 -1)~(Z i1 / 2-24) Medium, white dots A i1 or A i2 The black dots represent bonds to A. i2 or A i3 Represents a bond to . From the viewpoint of improving Δn, Z i1 is the formula (Z i1 / 2 -4) (-C≡C-).

[0056] In general formula (i), n i1 represents an integer of 0 to 1. n ii1 When Z is 1, from the viewpoint of solubility and low viscosity, i2 preferably represents a single bond.

[0057] The compound represented by general formula (i) is preferably a compound represented by the following general formulas (i-1) to (i-2).

[0058] [ka]

[0059] In general formulas (i-1) to (i-2), R i1 , A i1 , A i2 and A i3 are each independently R in the general formula (i). i1 , A i1 , A i2 and A i3 It has the same meaning as:

[0060] The compound represented by general formula (i-1) is preferably a compound represented by the following general formulas (i-1-1) to (i-1-2).

[0061] [ka]

[0062] In general formulas (i-1-1) to (i-1-2), R i1 and S i1are each independently R in the general formula (i). i1 and S i1 It has the same meaning as: Specific examples of the compound represented by general formula (i-1-1) include compounds represented by the following structural formulas (i-1-1.1) to (i-1-1.8).

[0063] [ka]

[0064] Specific examples of the compound represented by general formula (i-1-2) include compounds represented by the following structural formulas (i-1-2.1) to (i-1-2.6).

[0065] [ka]

[0066] The compound represented by general formula (i-2) is preferably a compound represented by the following general formulas (i-2-1) to (i-2-2).

[0067] [ka]

[0068] In general formulas (i-2-1) to (i-2-2), R i1 and S i1 are each independently R in the general formula (i). i1 and S i1 It has the same meaning as: Specific examples of the compound represented by general formula (i-2-1) include compounds represented by the following structural formulas (i-2-1.1) to (i-2-1.7).

[0069] [ka]

[0070] Specific examples of the compound represented by general formula (i-2-1) include compounds represented by the following structural formulas (i-2-2.1) to (i-2-2.8).

[0071] [ka]

[0072] The compounds represented by general formula (i), general formulae (i-1) to (i-2), general formulae (i-1-1) to (i-1-2), general formulae (i-2-1) to (i-2-2), structural formulae (i-1-1.1) to (i-1-1.8), structural formulae (i-1-2.1) to (i-1-2.6), structural formulae (i-2-1.1) to (i-2-1.7), or structural formulae (i-2-2.1) to (i-2-2.8) may be used in a liquid crystal composition in one or more varieties, preferably 1 to 10 varieties, preferably 1 to 5 varieties, and preferably 1 to 3 varieties.

[0073] The lower limit of the total content of the compounds represented by general formula (i), general formulas (i-1) to (i-2), general formulas (i-1-1) to (i-1-2), general formulas (i-2-1) to (i-2-2), structural formulas (i-1-1.1) to (i-1-1.8), structural formulas (i-1-2.1) to (i-1-2.6), structural formulas (i-2-1.1) to (i-2-1.7), or structural formulas (i-2-2.1) to (i-2-2.8) in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, preferably 3% by mass or more, preferably 5% by mass or more, preferably 10% by mass or more, preferably 15% by mass or more, preferably 20% by mass or more, preferably 25% by mass or more, and preferably 30% by mass or more.

[0074] The upper limit of the total content of the compounds represented by general formula (i), general formulas (i-1) to (i-2), general formulas (i-1-1) to (i-1-2), general formulas (i-2-1) to (i-2-2), structural formulas (i-1-1.1) to (i-1-1.8), structural formulas (i-1-2.1) to (i-1-2.6), structural formulas (i-2-1.1) to (i-2-1.7), or structural formulas (i-2-2.1) to (i-2-2.8) in 100% by mass of the liquid crystal composition is preferably 40% by mass or less, preferably 35% by mass or less, preferably 30% by mass or less, preferably 25% by mass or less, preferably 20% by mass or less, preferably 15% by mass or less, preferably 10% by mass or less, and preferably 5% by mass or less.

[0075] The total content of the compounds represented by general formula (i), general formulas (i-1) to (i-2), general formulas (i-1-1) to (i-1-2), general formulas (i-2-1) to (i-2-2), structural formulas (i-1-1.1) to (i-1-1.8), structural formulas (i-1-2.1) to (i-1-2.6), structural formulas (i-2-1.1) to (i-2-1.7), or structural formulas (i-2-2.1) to (i-2-2.8) in 100% by mass of the liquid crystal composition is determined by the solubility, Δn and / or Δε r From this viewpoint, the content is preferably 1 to 40% by mass, more preferably 3 to 35% by mass, and even more preferably 5 to 35% by mass.

[0076] The compound represented by general formula (i) (including its sub-concepts) can be synthesized using known synthesis methods. (Compound represented by general formula (ii)) The liquid crystal composition according to the present invention contains one or more compounds represented by general formula (i) having an alkynyl group and an isothiocyanate group (-NCS).

[0077] [ka]

[0078] In general formula (ii), R ii1represents an alkynyl group having 2 to 20 carbon atoms. The alkynyl group having 2 to 20 carbon atoms is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group. The alkynyl group having 2 to 20 carbon atoms preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. One or more -CH2- in the alkynyl group may each independently be substituted by -O-, -S-, -NH-, -CO- and / or -CS-. In addition, one or more -CH2-CH2- in the alkynyl group may each independently be substituted with -C≡C-. Furthermore, one or more hydrogen atoms in the alkynyl group may each independently be substituted with a halogen atom. Examples of halogen atoms include fluorine atoms, chlorine atoms, and bromine atoms. However, when the alkynyl group is substituted with a specific group, the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms are not directly bonded to each other and / or oxygen atoms are not directly bonded to each other.

[0079] As the alkynyl group, from the viewpoint of ease of synthesis and extension of the conjugated system, the following formula (R ii1 An alkynyl group represented by -A) is preferred.

[0080] [ka]

[0081] Formula (R ii1 -A) Medium, 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 is preferably a linear alkyl group. The alkyl group having 1 to 18 carbon atoms preferably has 1 to 8 carbon atoms. One or more -CH2- groups in the alkyl group may each independently be substituted with -O-, -S-, -NH-, -CO- and / or -CS-. In addition, one or more -CH2-CH2- groups in the alkyl group may each independently be substituted with -C≡C-. Furthermore, one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted with a specific group, the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms are not directly bonded to each other and / or oxygen atoms are not directly bonded to each other. Also, the formula (R ii1 -A) In the middle, the black dot is A ii1 Represents a bond to .

[0082] R ii1 Specific examples of the alkynyl group having 2 to 20 carbon atoms (including substituted ones) in the formula (R ii1 -1)~(R ii1 -16).

[0083] [ka]

[0084] Formula (R i1 -1)~(R ii1 -16) In the middle, the black dot is A ii1 Represents a bond to . In addition, R ii1 From the viewpoint of Δn and solubility, a linear alkynyl group having 2 to 8 carbon atoms is preferred.

[0085] In general formula (ii), A ii1 , A ii2 and A ii3each independently represents a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms. More specifically, the hydrocarbon ring having 3 to 16 carbon atoms or the heterocyclic ring having 3 to 16 carbon atoms is the following group (a), group (b), group (c), and group (d): (a) a 1,4-cyclohexylene group (in which one —CH— or two or more non-adjacent —CH— groups may be replaced by —O— or —S—). (b) a 1,4-phenylene group (in which one —CH= or two or more non-adjacent —CH= groups may be replaced by —N=). (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthracene anthracene-2,7-diyl group (one -CH= or two or more -CH= present in a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, an anthracene-2,6-diyl group, an anthracene-1,4-diyl group, an anthracene-9,10-diyl group, or a phenanthrene-2,7-diyl group may be replaced by -N=); (d) a thiophene-2,5-diyl group, a benzothiophene-2,5-diyl group, a benzothiophene-2,6-diyl group, a dibenzothiophene-3,7-diyl group, a dibenzothiophene-2,6-diyl group, or a thieno[3,2-b]thiophene-2,5-diyl group (in this group, one —CH= or two or more non-adjacent —CH= may be replaced by —N=). It is preferred that the aryl group represents a group selected from the group consisting of:

[0086] A ii1 , A ii2and A ii3 One or more hydrogen atoms in each independently represent a substituent S ii1 may be substituted by substituent S ii1 represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms. The alkyl group may be a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group. The alkyl group preferably has 2 to 10 carbon atoms, and more preferably 3 to 6 carbon atoms. One or more -CH2- groups in the alkyl group may each independently be substituted with -O-, -S-, -NH-, -CO- and / or -CS-. Furthermore, one or more -CH2-CH2- groups in the alkyl group may each independently be substituted with -CH=CH-, -CF=CF- and / or -C≡C-. Furthermore, one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted with a specific group, the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms are not directly bonded to each other and / or oxygen atoms are not directly bonded to each other. substituent S ii1 As the alkyl group, a fluorine atom, a linear alkyl group having 1 to 6 carbon atoms, or a linear alkoxy group having 1 to 6 carbon atoms is preferred. Also, A ii1 , A ii2 and A ii3 At least one of the groups has at least one substituent Si1 It is preferably substituted with Also, A ii3 has at least one substituent S i1 It is preferably substituted with In addition, the substituent S ii1 When there are a plurality of, they may be the same or different.

[0087] A ii1 Substituent S in ii1 The substitution position of the following formula (A ii1 -SP-1)~(A ii1 -SP-4).

[0088] [ka]

[0089] Formula (A ii1 -SP-1)~(A ii1 -SP-4) White points are R ii1 The black dots represent bonds to Z. ii1 Represents a bond to . A ii2 Substituent S in i1 The substitution position of the following formula (A ii2 -SP-1)~(A ii2 -SP-4).

[0090] [ka]

[0091] Formula (A ii2 -SP-1)~(A ii2 -SP-4) White spots are Z ii1 The black dots represent bonds to Z. ii2 or represents a bond to an isothiocyanate group (-NCS). A ii3 Substituent S in ii1 The substitution position of the following formula (A ii3 -SP-1)~(Aii3 -SP-4).

[0092] [ka]

[0093] Formula (A ii3 -SP-1)~(A ii3 -SP-4) White spots are Z ii2 The black dots represent bonds to Z. ii2 or represents a bond to an isothiocyanate group (-NCS). More specifically, A ii1 is expressed by the following formula (A ii1 -1)~(A ii1 -11) is preferably represented by either

[0094] [ka]

[0095] Formula (A ii1 -1)~(A ii1 -11) In the middle, the white point is R ii1 The black dots represent bonds to Z. ii1 Represents a bond to . More specifically, A ii2 is expressed by the following formula (A ii2 -1)~(A ii2 -11) is preferably represented by either

[0096] [ka]

[0097] Formula (A ii2 -1)~(A ii2 -11) White spot is Z ii1 The black dots represent bonds to Z. ii2 or represents a bond to an isothiocyanate group (-NCS). More specifically, A ii3 is expressed by the following formula (A ii3 -1)~(Aii3 -11) is preferably represented by either

[0098] [ka]

[0099] Formula (A ii3 -1)~(A ii3 -11) White point is Z ii2 The black dots represent bonds to Z. ii2 or represents the bond of an isothiocyanate group (-NCS).

[0100] In general formula (ii), Z ii1 and Z ii2 each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms. The alkylene group is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group. The alkylene group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. One or more -CH2- in the alkylene group may each independently be substituted with -O-, -CF2- and / or -CO-. Furthermore, one or more -CH2-CH2- in the alkylene group may each independently be substituted with -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-. However, when the alkylene group is substituted with a specific group, the oxygen atoms are not directly bonded to each other.

[0101] Specific examples of the alkylene group having 2 to 20 carbon atoms (including substituted ones) include the alkylene group represented by the formula (Z ii1 / 2 -1)~(Z ii1 / 2 -24).

[0102] [ka]

[0103] Formula(Z ii1 / 2 -1)~(Z ii1 / 2 -24) Medium, white dots A ii1 , A ii2 or A ii3 The black dot represents a bond to A. ii2 or A ii3 Represents a bond to . Δn and / or Δε r From the perspective of Z ii1 and Z ii2 are preferably each independently a single bond or -C≡C-. Also, Δn and / or Δε r From the perspective of Z ii1 and Z ii2 It is preferable that at least one of the groups is -C≡C-.

[0104] In general formula (ii), n ii1 represents an integer of 0 to 2. n ii1 When is 1, Δn and / or Δε r From the perspective of Z ii1 or Z ii2 Preferably, represents -C≡C-. Also, n ii1 When is 2, Δn and / or Δε r From the perspective of Z ii2 It is preferred that at least one of the groups represents -C≡C-. Also, n ii1 When is 2, Δn and / or Δε r From the perspective of Z ii2 preferably represents a single bond or -C≡C-. In the general formula (ii), A ii3 and Z ii2 When there are a plurality of groups, they may be the same or different.

[0105] The compound represented by general formula (ii) is preferably a compound represented by the following general formulas (ii-1) to (ii-3).

[0106] [ka]

[0107] In general formulas (ii-1) to (ii-3), R ii1 , A ii1 , A ii2 and A ii3 represents R in the above general formula (ii). ii1 , A ii1 , A ii2 and A ii3 and each mean the same thing. In addition, in the general formula (ii-3), A ii3-2 The definition of A in the above general formula (ii) ii3-2 is the same as the definition of

[0108] The compound represented by general formula (ii-1) is preferably a compound represented by the following general formulas (ii-1-1) to (ii-1-3).

[0109] [ka]

[0110] In general formulas (ii-1-1) to (ii-1-3), R ii1 and S ii1 are each independently R in the general formula (ii). ii1 and S ii1 It has the same meaning as: Specific examples of the compound represented by general formula (ii-1-1) include compounds represented by the following structural formulae (ii-1-1.1) to (ii-1-1.2).

[0111] [ka]

[0112] Specific examples of the compound represented by general formula (ii-1-2) include compounds represented by the following structural formulas (ii-1-2.1) to (ii-1-2.2).

[0113] [ka]

[0114] Specific examples of the compound represented by general formula (ii-1-3) include compounds represented by the following structural formula (ii-1-3.1).

[0115] [ka]

[0116] The compound represented by general formula (ii-2) is preferably a compound represented by the following general formulas (ii-2-1) to (ii-2-3).

[0117] [ka]

[0118] In general formulas (ii-2-1) to (ii-2-3), R ii1 and S ii1 are each independently R in the general formula (ii). ii1 and S ii1 It has the same meaning as: Specific examples of the compound represented by general formula (ii-2-1) include compounds represented by the following structural formulas (ii-2-1.1) to (ii-2-1.2).

[0119] [ka]

[0120] Specific examples of the compound represented by general formula (ii-2-2) include compounds represented by the following structural formulas (ii-2-2.1) to (ii-2-2.5).

[0121] [ka]

[0122] Specific examples of the compound represented by general formula (ii-2-3) include compounds represented by the following structural formula (ii-2-3.1).

[0123] [ka]

[0124] The compound represented by general formula (ii-3) is preferably a compound represented by the following general formula (ii-3-1).

[0125] [ka]

[0126] In general formula (ii-3-1), R ii1 and S ii1 are each independently R in the general formula (ii). ii1 and S ii1 It has the same meaning as: Specific examples of the compound represented by general formula (ii-3-1) include compounds represented by the following structural formulae (ii-3-1.1) to (ii-3-1.2).

[0127] [ka]

[0128] The compounds represented by general formula (ii), general formulas (ii-1) to (ii-3), general formulas (ii-1-1) to (ii-1-3), general formulas (ii-2-1) to (ii-2-3), general formula (ii-3-1), structural formulas (ii-1-1.1) to (ii-1-1.2), structural formulas (ii-1-2.1) to (ii-1-2.2), structural formula (ii-1-3.1), structural formulas (ii-2-1.1) to (ii-2-1.2), structural formulas (ii-2-2.1) to (ii-2-2.5), structural formula (ii-2-3.1), or structural formulas (ii-3-1.1) to (ii-3-1.2) may be used in a liquid crystal composition in one or more varieties, preferably 1 to 10 varieties, preferably 1 to 5 varieties, and preferably 1 to 3 varieties.

[0129] General formula (ii), General formula (ii-1)~(ii-3), General formula (ii-1-1)~(i-1-3), General formula (ii-2-1)~(ii-2-3), General formula (ii-3-1), Structural formula (ii-1-1.1)~(ii- 1-1.2), Structural formula (ii-1-2.1)~(ii-1-2.2), Structural formula (ii-1-3.1), Structural formula (ii-2-1.1)~(ii-2-1.2), Structural formula (ii-2-2.1)~(ii-2-2.5), The lower limit of the total content of the compounds represented by structural formula (ii-2-3.1) or structural formulae (ii-3-1.1) to (ii-3-1.2) in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, more preferably 3% by mass or more, more preferably 5% by mass or more, more preferably 10% by mass or more, more preferably 15% by mass or more, more preferably 20% by mass or more, and more preferably 25% by mass or more.

[0130] General formula (ii), general formulas (ii-1) to (ii-3), general formulas (ii-1-1) to (ii-1-3), general formulas (ii-2-1) to (ii-2-3), general formula (ii-3-1), structural formulas (ii-1-1.1) to (ii-1-1.2), structural formulas (ii-1-2.1) to (ii-1-2.2), structural formula (ii-1-3.1), structural formulas (ii-2-1.1) to (ii-2-1.2), structural formulas (ii-2-2.1) to (ii-2-2.5), structural formula (ii-2-3.1) or structural formulas (ii-3-1.1) to (ii-3-1.2) The upper limit of the total content of the compounds represented by () in 100% by mass of the liquid crystal composition is preferably 55% by mass or less, preferably 50% by mass or less, preferably 45% by mass or less, preferably 40% by mass or less, preferably 35% by mass or less, preferably 30% by mass or less, preferably 25% by mass or less, preferably 20% by mass or less, preferably 15% by mass or less, preferably 10% by mass or less, and preferably 5% by mass or less.

[0131] The total content of the compounds represented by general formula (ii), general formulas (ii-1) to (ii-3), general formulas (ii-1-1) to (ii-1-3), general formulas (ii-2-1) to (ii-2-3), general formula (ii-3-1), structural formulas (ii-1-1.1) to (ii-1-1.2), structural formulas (ii-1-2.1) to (ii-1-2.2), structural formula (ii-1-3.1), structural formulas (ii-2-1.1) to (ii-2-1.2), structural formulas (ii-2-2.1) to (ii-2-2.5), structural formulas (ii-2-3.1) or structural formulas (ii-3-1.1) to (ii-3-1.2) in 100% by mass of the liquid crystal composition is determined by the solubility, Δn and / or Δε r From this viewpoint, the content is preferably 1 to 55% by mass, more preferably 3 to 50% by mass, and even more preferably 5 to 45% by mass.

[0132] The compound represented by general formula (ii) (including sub-concepts) can be synthesized using known synthesis methods.

[0133] (Compound represented by general formula (iii)) The liquid crystal composition of the present invention has a solubility, Δn and / or Δε r From this viewpoint, it is preferable to include one or more compounds having an isothiocyanate group (—NCS) and represented by the following general formula (iii).

[0134] [ka]

[0135] In general formula (iii), R iii1 represents an alkyl group having 1 to 20 carbon atoms. The alkyl group may be a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group. The alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. One or more -CH2- groups in the alkyl group may each independently be substituted with -O-, -S-, -NH-, -CO- and / or -CS-. Furthermore, one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted with a specific group, the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms are not directly bonded to each other and / or oxygen atoms are not directly bonded to each other. For example, R iii1 can represent an alkoxy group having 1 to 19 carbon atoms by substituting one -CH2- in the alkyl group with -O-. The alkoxy group may be a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group. The alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. Also, R iii1can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms by substituting one -CH2- in the alkyl group with -S-. The alkylsulfanyl group may be a linear, branched or cyclic alkylsulfanyl group, and is preferably a linear alkylsulfanyl group. The alkylsulfanyl group preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms. Also, R iii1 can represent a halogenated alkyl group having 1 to 20 carbon atoms, in which one or more hydrogen atoms in the alkyl group have been substituted with halogen atoms. The halogenated alkyl group may be linear, branched, or cyclic, and is preferably a linear halogenated alkyl group. The halogenated alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. Also, R iii1 can represent a halogenated alkoxy group having 1 to 19 carbon atoms, in which one -CH2- in the alkyl group is replaced with -O- and one or more hydrogen atoms in the alkyl group are replaced with halogen atoms. The halogenated alkoxy group may be a linear, branched, or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group. The halogenated alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. R iii1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) in the formula (R iii1 -1)~(R iii1 -30).

[0136] [ka]

[0137] Formula (R iii1-1)~(R iii1 -30) In the black dot, A iii1 Represents a bond to . In addition, R iii1 From the viewpoint of solubility, the alkyl group is preferably a linear or branched alkyl group having 2 to 8 carbon atoms, a linear alkoxy group having 2 to 8 carbon atoms, a linear halogenated alkoxy group having 1 to 8 carbon atoms, or a linear alkylsulfanyl group having 1 to 6 carbon atoms.

[0138] In general formula (iii), A iii1 and A iii2 are each independently the following groups (a), (b), (c), and (d): (a) a 1,4-cyclohexylene group (in which one —CH— or two or more non-adjacent —CH— groups may be replaced by —O— and / or —S—). (b) a 1,4-phenylene group (in which one -CH= or two or more -CH= may be replaced by -N=). (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group, 2,3-dihydro-1H-indene-1,5-diyl group, 2,3-dihydro-1H-indene-2,5-diyl group, 2,3-dihydro-1H-indene-1,6-diyl group, 1 1H-indene-2,5-diyl group, 1H-indene-1,5-diyl group, 1H-indene-3,5-diyl group, 1H-indene-1,6-diyl group, 1H-indene-2,6-diyl group, 1H-indene-3,6-diyl group (one -CH= or two or more -CH= in a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, an anthracene-2,6-diyl group, an anthracene-1,4-diyl group, an anthracene-9,10-diyl group, or a phenanthrene-2,7-diyl group may be replaced by -N=). (d) a thiophene-2,5-diyl group, a benzothiophene-2,5-diyl group, a benzothiophene-2,6-diyl group, a dibenzothiophene-3,7-diyl group, a dibenzothiophene-2,6-diyl group, a thieno[3,2-b]thiophene-2,5-diyl group, or a benzo[1,2-b:4,5-b']dithiophene-2,6-diyl group (one -CH= or two or more -CH= in this group may be replaced by -N=). represents a group selected from the group consisting of:

[0139] A iii1 and A iii2 One or more hydrogen atoms in each independently represent a substituent S iii1 may be substituted by: substituent S iii1represents any one of a halogen atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms. Examples of the halogen atom 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 is preferably a linear alkyl group. The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. One or more -CH2- groups in the alkyl group may each independently be replaced by -O-, -S-, -NH-, -CO- and / or -CS-. In addition, one or more -CH2-CH2- groups in the alkyl group may each independently be substituted with -CH=CH-, -CF=CF- and / or -C≡C-. Furthermore, one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted with a specific group, the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms are not directly bonded to each other and / or oxygen atoms are not directly bonded to each other. For example, the substituent S iii1 can represent an alkoxy group having 1 to 19 carbon atoms by substituting one -CH2- in the alkyl group with -O-. The alkoxy group may be a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group. The alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. In addition, the substituent S iii1 can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms by substituting one -CH2- in the alkyl group with -S-. The alkylsulfanyl group may be a linear, branched or cyclic alkylsulfanyl group, and is preferably a linear alkylsulfanyl group. The alkylsulfanyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. In addition, the substituent S iii1 can represent an alkenyl group having 2 to 20 carbon atoms by substituting one or more -CH2-CH2- groups in the alkyl group with -CH=CH-. The alkenyl group may be a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group. The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. In addition, the substituent S iii1 can represent an alkynyl group having 2 to 20 carbon atoms by substituting one or more -CH2-CH2- in the alkyl group with -C≡C-. The alkynyl group may be a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group. The alkynyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. In addition, the substituent S iii1 can represent an alkenyloxy group having 2 to 19 carbon atoms, in which one -CH2- in the alkyl group is replaced with -O- and one or more -CH2-CH2- are replaced with -CH=CH-. The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group. The alkenyloxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. In addition, the substituent S iii1can represent a halogenated alkyl group having 1 to 20 carbon atoms, in which one or more hydrogen atoms in the alkyl group have been substituted with halogen atoms. The halogenated alkyl group may be linear, branched, or cyclic, and is preferably a linear halogenated alkyl group. The halogenated alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. In addition, the substituent S iii1 can represent a halogenated alkoxy group having 1 to 19 carbon atoms, in which one -CH2- in the alkyl group is replaced with -O- and one or more hydrogen atoms in the alkyl group are replaced with halogen atoms. The halogenated alkoxy group may be a linear, branched, or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group. The halogenated alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. substituent S iii1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include those of the formula (S iii1R -1)~(S iii1R -36).

[0140] [ka]

[0141] Formula (S iii1R -1)~(S iii1R -36) In the middle, black dots are A iii1 or A iii2 Represents a bond to . substituent S iii1 is preferably a linear alkyl group having 1 to 6 carbon atoms, a fluorine atom or a chlorine atom. Also, A iii1 At least one of or A iii2 has at least one substituent S iii1It is preferably substituted with a halogen atom, and more preferably with a fluorine atom. In addition, the substituent S iii1 When there are a plurality of, they may be the same or different.

[0142] A iii1 Substituent S in iii1 The substitution position of the following formula (A iii1 -SP-1)~(A iii1 -SP-24).

[0143] [ka]

[0144] [ka]

[0145] [ka]

[0146] [ka]

[0147] Formula (A iii1 -SP-1)~(A iii1 -SP-24) White dots are R iii1 or Z iii1 The black dots represent bonds to Z. iii1 Represents a bond to . A iii2 Substituent S in iii1 The substitution position of the following formula (A iii2 -SP-1)~(A iii2 -SP-8).

[0148] [ka]

[0149] Formula (A iii2 -SP-1)~(A iii2 -SP-8) White spots are Z iii1 The black dot represents a bond to the isothiocyanate group (-NCS). More specifically, A iii1 is expressed by the following formula (A iii1 -1)~(A iii1 -49).

[0150] [ka]

[0151] [ka]

[0152] [ka]

[0153] [ka]

[0154] Formula (A iii1 -1)~(A iii1 -49) White point is R iii1 or Z iii1 The black dots represent bonds to Z. iii1 Represents a bond to . More specifically, A iii2 is expressed by the following formula (A iii2 -1)~(A iii2 -10) is preferable.

[0155] [ka]

[0156] Formula (Aiii2 -1)~(A iii2 -10) White spot is Z iii1 The black dot represents a bond to the isothiocyanate group (-NCS).

[0157] In general formula (iii), Z iii1 represents a single bond or an alkylene group having 1 to 20 carbon atoms. One or more -CH2- in the alkylene group may each independently be substituted with -O-, -CF2- and / or -CO-. Furthermore, one or more -CH2-CH2- in the alkylene group may each independently be substituted with -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-. However, when the alkylene group having 1 to 20 carbon atoms is substituted with a specific group, the oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms are not directly bonded to each other and / or oxygen atoms are not directly bonded to each other. Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted ones) include the alkylene group represented by the formula (Z iii1 -1)~(Z iii1 -24).

[0158] [ka]

[0159] Formula(Z iii1 -1)~(Z iii1 -24) Medium, white dots A iii1 The black dot represents a bond to A. iii1 or A iii2 Represents a bond to .

[0160] In general formula (iii), n iii1represents an integer of 1 to 4, preferably 1 or 2. n iii1 When is 1, Δn and / or Δε r From the perspective of Z iii1 preferably represents a single bond or -C≡C-. Also, n iii1 When is 2, Δn and / or Δε r From the perspective of Z iii1 preferably represents a single bond or -C≡C-. In the general formula (iii), A iii1 and Z iii1 When there are a plurality of groups, they may be the same or different.

[0161] The compound represented by general formula (iii) is preferably a compound represented by the following general formulas (iii-1) to (iii-4).

[0162] [ka] In general formulas (iii-1) to (iii-4), R iii1 , A iii1 and A iii2 represents R in the above general formula (iii). iii1 , A iii1 and A iii2 and each mean the same thing. In general formula (iii-4), A iii1-2 The definitions of each independently represent A in the above general formula (ii). iii1 is the same as the definition of The compound represented by general formula (iii-1) is preferably a compound represented by the following general formula (iii-1-1).

[0163] [ka]

[0164] In general formula (iii-1-1), R iii1 and S iii1are each independently R in the general formula (iii) iii1 and S iii1 and each mean the same thing. Specific examples of the compound represented by general formula (iii-1-1) include compounds represented by the following structural formulas (iii-1-1.1) to (iii-1-1.3).

[0165] [ka]

[0166] The compound represented by general formula (iii-2) is preferably a compound represented by the following general formulas (iii-2-1) to (iii-2-3).

[0167] [ka]

[0168] In general formulas (iii-2-1) to (iii-2-3), R iii1 and S iii1 are each independently R in the general formula (iii) iii1 and S iii1 and each mean the same thing. Specific examples of the compound represented by general formula (iii-2-1) include compounds represented by the following structural formulae (iii-2-1.1) to (iii-2-1.2).

[0169] [ka]

[0170] Specific examples of the compound represented by general formula (iii-2-2) include compounds represented by the following structural formulas (iii-2-2.1) to (iii-2-2.2).

[0171] [ka]

[0172] Specific examples of the compound represented by general formula (iii-2-3) include compounds represented by the following structural formulas (iii-2-3.1) to (iii-2-3.2).

[0173] [ka]

[0174] The compound represented by general formula (iii-3) is preferably a compound represented by the following general formulas (iii-3-1) to (iii-3-2).

[0175] [ka]

[0176] In general formulas (iii-3-1) to (iii-3-2), R iii1 and S iii1 are each independently R in the general formula (iii) iii1 and S iii1 and each mean the same thing. Specific examples of the compound represented by general formula (iii-3-1) include compounds represented by the following structural formulas (iii-3-1.1) to (iii-3-1.2).

[0177] [ka]

[0178] Specific examples of the compound represented by general formula (iii-3-2) include compounds represented by the following structural formulas (iii-3-2.1) to (iii-3-2.2).

[0179] [ka]

[0180] The compound represented by general formula (iii-4) is preferably a compound represented by the following general formulas (iii-4-1) to (iii-4-3).

[0181] [ka]

[0182] In general formulas (iii-4-1) to (iii-4-3), R iii1 and S iii1 are each independently R in the general formula (iii) iii1 and S iii1 and each mean the same thing. Specific examples of the compound represented by general formula (iii-4-1) include compounds represented by the following structural formulae (iii-4-1.1) to (iii-4-1.2).

[0183] [ka]

[0184] Specific examples of the compound represented by general formula (iii-4-2) include compounds represented by the following structural formulae (iii-4-2.1) to (iii-4-2.2).

[0185] [ka]

[0186] Specific examples of the compound represented by general formula (iii-4-3) include compounds represented by the following structural formulae (iii-4-3.1) to (iii-4-3.2).

[0187] [ka]

[0188] General formula (iii), General formula (iii-1)~(iii-4), General formula (iii-1-1), General formula (iii-2-1)~(iii-2-3), General formula (iii-3-1)~(iii-3-2), General formula (iii-4-1)~(iii- 4-3), Structural formula (iii-1-1.1)~(iii-1-1.3), Structural formula (iii-2-1.1)~(iii-2-1.2), Structural formula (iii-2-2.1)~(iii-2-2.2), Structural formula (iii-2-3.1)~(iii The compounds represented by structural formulas (iii-2-3.2), structural formulas (iii-3-1.1) to (iii-3-1.2), structural formulas (iii-3-2.1) to (iii-3-2.2), structural formulas (iii-4-1.1) to (iii-4-1.2), structural formulas (iii-4-2.1) to (iii-4-2.2), or structural formulas (iii-4-3.1) to (iii-4-3.2) may be used in a liquid crystal composition in one or more varieties, preferably 1 to 20 varieties, preferably 2 to 15 varieties, and preferably 3 to 10 varieties.

[0189] General formula (iii), General formula (iii-1)~(iii-4), General formula (iii-1-1), General formula (iii-2-1)~(iii-2-3), General formula (iii-3-1)~ (iii-3-2), general formula (iii-4-1)~(iii-4-3), structural formula (iii-1-1.1)~(iii-1-1.3), structural formula (iii-2-1.1)~(i ii-2-1.2), Structural formula (iii-2-2.1)~(iii-2-2.2), Structural formula (iii-2-3.1)~(iii-2-3.2), Structural formula (iii-3-1.1) )~(iii-3-1.2), Structural formula (iii-3-2.1)~(iii-3-2.2), Structural formula (iii-4-1.1)~(iii-4-1.2), Structural formula (iii-4 The lower limit of the total content of the compounds represented by structural formulae (iii-4-2.1) to (iii-4-2.2) or structural formulae (iii-4-3.1) to (iii-4-3.2) in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, preferably 1% by mass or more, preferably 3% by mass or more, preferably 10% by mass or more, preferably 15% by mass or more, preferably 20% by mass or more, preferably 25% by mass or more, preferably 30% by mass or more, preferably 35% by mass or more, preferably 40% by mass or more, preferably 45% by mass or more, preferably 50% by mass or more, and preferably 55% by mass or more.

[0190] General formula (iii), General formula (iii-1)~(iii-4), General formula (iii-1-1), General formula (iii-2-1)~(iii-2-3), General formula (iii-3-1)~(iii -3-2), general formula (iii-4-1)~(iii-4-3), structural formula (iii-1-1.1)~(iii-1-1.3), structural formula (iii-2-1.1)~(iii-2-1.2) , structural formula (iii-2-2.1) to (iii-2-2.2), structural formula (iii-2-3.1) to (iii-2-3.2), structural formula (iii-3-1.1) to (iii-3-1.2), structural formula (iii-3-2.1) to (iii-3-2.2), structural formula (iii-4-1.1) to (iii-4-1.2), structural formula (iii-4-2.1) to (iii-4-2.2), or The upper limit of the total content of the compounds represented by structural formulae (iii-4-3.1) to (iii-4-3.2) in 100% by mass of the liquid crystal composition is preferably 75% by mass or less, preferably 70% by mass or less, preferably 65% ​​by mass or less, preferably 60% by mass or less, preferably 55% by mass or less, preferably 50% by mass or less, preferably 45% by mass or less, preferably 40% by mass or less, preferably 35% by mass or less, preferably 30% by mass or less, preferably 25% by mass or less, preferably 20% by mass or less, preferably 15% by mass or less, preferably 10% by mass or less, and preferably 5% by mass or less.

[0191] General formula (iii), General formula (iii-1)~(iii-4), General formula (iii-1-1), General formula (iii-2-1)~(iii-2-3), General formula (iii-3-1)~(iii-3-2), General formula (iii-4-1) )~(iii-4-3), Structural formula (iii-1-1.1)~(iii-1-1.3), Structural formula (iii-2-1.1)~(iii-2-1.2), Structural formula (iii-2-2.1)~(iii-2-2.2), Structural formula (ii The total content of the compounds represented by structural formulae (iii-2-3.1) to (iii-2-3.2), structural formulae (iii-3-1.1) to (iii-3-1.2), structural formulae (iii-3-2.1) to (iii-3-2.2), structural formulae (iii-4-1.1) to (iii-4-1.2), structural formulae (iii-4-2.1) to (iii-4-2.2), or structural formulae (iii-4-3.1) to (iii-4-3.2) in 100% by mass of the liquid crystal composition is r From this viewpoint, the content is preferably 1 to 75% by mass, more preferably 3 to 70% by mass, and even more preferably 5 to 65% by mass.

[0192] The compound represented by general formula (iii) (including sub-concepts) can be synthesized using known synthesis methods.

[0193] (Liquid Crystal Composition) The liquid crystal composition according to the present invention can be produced, for example, by mixing the compound represented by the above-mentioned general formula (i), the compound represented by the general formula (ii), and, if necessary, the above-mentioned other compounds and additives.

[0194] Examples of additives include stabilizers, dye compounds, polymerizable compounds, azotolane compounds, and isothiocyanate compounds (NCS compounds).

[0195] Examples of stabilizers include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, hindered phenols, and hindered amines. Examples of the hindered phenols include hindered phenol-based antioxidants represented by the following structural formulas (XX-1) to (XX-5).

[0196] [ka]

[0197] Examples of the hindered amines include hindered amine light stabilizers represented by the following structural formulas (YY-1) to (YY-2).

[0198] [ka]

[0199] When a stabilizer is used, the type of stabilizer used in the liquid crystal composition is 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. When stabilizers are used, the total content of the stabilizers in 100% by mass of the liquid crystal composition is preferably 0.005 to 1% by mass, more preferably 0.02 to 0.50% by mass, and even more preferably 0.03 to 0.35% by mass.

[0200] The combination of compounds used in the liquid crystal composition may be determined by the solubility, Δn and / or T ni From the perspective of 1) A combination of a compound represented by general formula (i) (including sub-concepts) and a compound represented by general formula (ii) (including sub-concepts), 2) A combination of a compound represented by general formula (i) (including sub-concepts), a compound represented by general formula (ii) (including sub-concepts), and a compound represented by general formula (iii) (including sub-concepts), 3) A combination of a compound represented by general formula (i-1) (including subconcepts), a compound represented by general formula (ii-2) (including subconcepts), and a compound represented by general formula (iii-1) (including subconcepts), 4) A combination of a compound represented by general formula (i-1-2) (including subordinate concepts), a compound represented by general formula (ii-2-2) (including subordinate concepts), and a compound represented by general formula (iii-1-1) (including subordinate concepts), is preferred.

[0201] <Characteristic values ​​of liquid crystal composition> 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 The measurement is carried out by preparing a preparation in which the liquid crystal composition is sandwiched between a slide glass and a cover glass, and observing the preparation under a polarizing microscope while heating it on a hot stage. It can also be measured by differential scanning calorimetry (DSC). The unit used is "℃". T ni The higher the temperature, the more the nematic phase can be maintained even at high temperatures, and the wider the operating temperature range can be. The upper limit temperature of the liquid crystal phase (T ni ) can be appropriately set depending on whether the liquid crystal display element is used indoors, in a car, or outdoors, where the external temperature can be controlled, but from the viewpoint of the operating temperature range, it is preferably 120°C or higher, more preferably 120 to 250°C, and even more preferably 125 to 215°C.

[0202] Liquid crystal phase lower limit temperature (T →n ) is the temperature at which a liquid crystal composition undergoes a phase transition from another phase (glass phase, smectic phase, crystalline phase) to the nematic phase. T →n is measured by filling a glass capillary with the liquid crystal composition, immersing it in a refrigerant at −70° C. to cause the liquid crystal composition to undergo a phase transition to another phase, and observing the change while increasing the temperature. It can also be measured by differential scanning calorimetry (DSC). The unit used is "℃". T →nThe lower the temperature, the more the nematic phase can be maintained at low temperatures, and therefore the wider the operating temperature range can be. The liquid crystal phase lower limit temperature (T →n ) is preferably 10°C or lower, more preferably -70 to 0°C, and even more preferably -40 to -5°C, from the viewpoint of the driving temperature.

[0203] Δn (refractive index anisotropy) correlates with Δn in the near-infrared region used in the optical sensor described below. The larger the Δn, the greater the phase modulation power of light of the target wavelength, making it particularly suitable for optical sensors. Δn at 25°C and 589 nm was measured using an Abbe refractometer to determine the extraordinary refractive index (n e ) and ordinary refractive index (n o ) difference (n e -n o ) is calculated. Also, Δn can be obtained using a phase difference measuring device. The relationship Δn=Re / d holds between the retardation Re, the thickness d of the liquid crystal layer, and Δn. A liquid crystal composition is injected into a glass cell with a cell gap (d) of approximately 3.0 μm and a polyimide alignment film that has been subjected to anti-parallel rubbing treatment, and the in-plane Re is measured using a retardation film / optical material inspection system RETS-100 (manufactured by Otsuka Electronics Co., Ltd.). Measurements are performed at 25°C and 589 nm, and are unitless. The Δn of the liquid crystal composition according to the present invention at 25°C and 589 nm is preferably 0.40 or more, more preferably 0.40 to 0.65, more preferably 0.41 to 0.60, and even more preferably 0.43 to 0.55, from the viewpoint of the phase modulation power of light of that wavelength.

[0204] The higher the dielectric anisotropy in the high frequency region, the greater the phase modulation power for radio waves in the target frequency band, making it particularly suitable for antenna applications. In addition, 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. In the liquid crystal composition according to the present invention, the dielectric anisotropy Δε at 10 GHz is representative of the characteristics in the high frequency range. r and the average value of the dielectric tangent tanδ iso was measured. Δε r =(ε r∥ -ε r⊥ ) and tanδ iso =(2ε r⊥ tanδ ⊥ +ε r∥ tanδ ∥ ) / (2ε r⊥ +ε r∥ ) Here, "ε r " is the dielectric constant, "tan δ" is the dielectric loss tangent, the subscript "∥" indicates the component parallel to the alignment direction of the liquid crystal, and "⊥" indicates the component perpendicular to the alignment direction of the liquid crystal.

[0205] Δε r and tanδ iso can be measured by the following method. First, the liquid crystal composition is introduced into a capillary tube made of polytetrafluoroethylene (PTFE). The capillary used here has an inner radius of 0.80 mm and an outer radius of 0.835 mm, with an effective length of 4.0 cm. The capillary tube containing the liquid crystal composition is introduced into the center of a cavity resonator (manufactured by EM Lab Co., Ltd.) having a resonance frequency of 10 GHz. The cavity has an outer diameter of 30 mm and a width of 26 mm. A signal is then input and the resulting output signal is recorded using a network analyzer (manufactured by Keysight Technologies, Inc.). The dielectric constant (ε) at 10 GHz was calculated using the difference between the resonant frequency of a PTFE capillary tube that does not contain a liquid crystal composition and the resonant frequency of a PTFE capillary tube that contains a liquid crystal composition. r ) and loss angle (δ). The tangent of the obtained δ is the dielectric loss tangent (tan δ). The resonance frequency and the like using a PTFE capillary tube filled with a liquid crystal composition are determined as values ​​of characteristic components perpendicular to and parallel to the alignment direction of the liquid crystal molecules by controlling the alignment of the liquid crystal molecules. The magnetic field of a permanent magnet or electromagnet is used to align the liquid crystal molecules in the vertical direction (perpendicular to the effective length direction) or in the parallel direction (parallel to the effective length direction) of the PTFE capillary tube. For example, the magnetic field has a pole-to-pole distance of 45 mm and a magnetic field strength of 0.23 tesla near the center. The liquid crystal composition is enclosed in a PTFE capillary tube, which is rotated parallel or perpendicular to the magnetic field to obtain the desired characteristic components. The electric field application time may be set to a condition that allows the liquid crystal to be uniformly aligned, and in the present invention, the electric field application time was set to 8 minutes. The measurement was carried out at a temperature of 25°C, and Δε r and tanδ iso Neither has a unit.

[0206] Δε at 25°C of the liquid crystal composition according to the present invention r is preferably larger, but from the viewpoint of phase modulation power in the GHz band, it is preferably 0.90 or more, more preferably 0.90 to 1.65, more preferably 0.95 to 1.60, and even more preferably 1.00 to 1.55. Tan δ of the liquid crystal composition of the present invention at 25°C iso is preferably smaller, but from the viewpoint of loss in the GHz band, it is preferably 0.025 or less, preferably 0.001 to 0.025, preferably 0.003 to 0.020, preferably 0.005 to 0.017, preferably 0.007 to 0.015, preferably 0.008 to 0.013, and preferably 0.009 to 0.012.

[0207] (Liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment and antennas) The liquid crystal display element, sensor, liquid crystal lens, optical communication device, and antenna using the liquid crystal composition according to the present invention will be described below.

[0208] The liquid crystal display element according to the present invention is characterized by using the above-mentioned liquid crystal composition, and is preferably driven by an active matrix system or a passive matrix system. The liquid crystal display element according to the present invention is preferably a liquid crystal display element in which the dielectric constant is reversibly switched by reversibly changing the alignment direction of the liquid crystal molecules of the liquid crystal composition.

[0209] The sensor according to the present invention is characterized by using the above-mentioned liquid crystal composition, and examples of its embodiments include a distance measuring sensor that uses electromagnetic waves, visible light or infrared light, an infrared sensor that uses temperature changes, a temperature sensor that uses a change in the wavelength of reflected light due to a change in the pitch of a cholesteric liquid crystal, a pressure sensor that uses a change in the wavelength of reflected light, an ultraviolet sensor that uses a change in the wavelength of reflected light due to a change in composition, an electric sensor that uses a temperature change due to a voltage or current, a radiation sensor that uses a temperature change accompanying the track of a radiation particle, an ultrasonic sensor that uses a change in the alignment of liquid crystal molecules due to mechanical vibration of ultrasonic waves, and an electromagnetic field sensor that uses a change in the wavelength of reflected light due to a change in temperature or a change in the alignment of liquid crystal molecules due to an electric field. The distance measurement sensor is preferably for LiDAR (Light Detection And Ranging) that uses a light source. As LiDAR, those for artificial satellites, aircraft, unmanned aerial vehicles (drones), automobiles, railways, and ships are preferred. For automobiles, self-driving automobiles are particularly preferred. The light source is preferably an LED or a laser, preferably a laser. The light used in LiDAR is preferably infrared light, and the wavelength is preferably 800 to 2000 nm. In particular, an infrared laser with a wavelength of 905 nm or 1550 nm is preferred. When the cost of the photodetector to be used and sensitivity in all weather conditions are important, a 905 nm infrared laser is preferred, and when safety for human vision is important, a 1550 nm infrared laser is preferred. The liquid crystal composition according to the present invention exhibits a high Δn, and therefore has a large phase modulation power in the visible light, infrared light and electromagnetic wave regions, and can provide a sensor with excellent detection sensitivity.

[0210] The liquid crystal lens according to the present invention is characterized by using the above-described liquid crystal composition, and, for example, in one embodiment, the liquid crystal lens has a first transparent electrode layer, a second transparent electrode layer, a liquid crystal layer containing the above-described liquid crystal composition and provided between the first transparent electrode layer and the second transparent electrode layer, an insulating layer provided between the second transparent electrode layer and the liquid crystal layer, and a high-resistance layer provided between the insulating layer and the liquid crystal layer. The liquid crystal lens according to the present invention is used, for example, as a 2D / 3D switching lens, a lens for adjusting the focus of a camera, and the like.

[0211] The optical communication device according to the present invention is characterized by using the above-mentioned liquid crystal composition, and one of its embodiments is, for example, LCOS (Liquid Crystal on Silicon) having a liquid crystal layer on a reflective layer (electrode), in which liquid crystals constituting each of a plurality of pixels are arranged two-dimensionally. The optical communication device according to the present invention is used, for example, as a spatial phase modulator.

[0212] The antenna according to the present invention is characterized by using the above-mentioned liquid crystal composition. More specifically, the antenna of the present invention comprises a first substrate having a plurality of slots, a second substrate facing the first substrate and having a power supply section, a first dielectric layer provided between the first substrate and the second substrate, a plurality of patch electrodes arranged corresponding to the plurality of slots, a third substrate on which the patch electrodes are provided, and a liquid crystal layer provided between the first substrate and the third substrate, wherein the liquid crystal layer contains the above-mentioned liquid crystal composition. By using the liquid crystal composition according to the present invention, it is possible to provide an antenna that is highly reliable against external stimuli such as heat. It is also possible to provide an antenna that allows greater phase control for microwave or millimeter wave electromagnetic waves. The antenna according to the present invention preferably operates in the Ka band, K band or Ku band frequencies used for satellite communications. The antenna according to the present invention preferably has a configuration in which a radial line slot array and a patch antenna array are combined. The structure of the antenna according to the present invention can be applied by taking into consideration the matters described in, for example, International Publication No. 2021 / 157189 pamphlet. [Example]

[0213] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples in any way. The compositions of the following Examples and Comparative Examples contained each compound in the proportions shown in the table, and the contents were expressed as "% by mass." The compounds are described using the following abbreviations. Compounds that can take either cis or trans forms will be referred to as trans forms unless otherwise specified. <Ring structure>

[0214] [ka]

[0215] <Terminal structure>

[0216] [Table 1] (Note that n in the table is a natural number. The alkyl group represented by n is a linear alkyl group.)

[0217] <Connection structure>

[0218] [Table 2] (Note that n in the table is a natural number. The alkylene group represented by n is a linear alkylene group.)

[0219] (hindered phenol antioxidant)

[0220] [ka]

[0221] (Hindered amine light stabilizer)

[0222] [ka]

[0223] (Preparation of Liquid Crystal Composition) LC-A to B and LC-01 to 07 shown in Table 3 were prepared.

[0224] [Table 3]

[0225] (Examples 1 to 31 and Comparative Examples 1 and 2) Liquid crystal compositions were prepared using LC-A to B and LC-01 to 07, hindered phenol antioxidants (XX-1) to (XX-3), and hindered amine light stabilizers (YY-1) to (YY-2), and their physical properties were measured and a storage stability test was carried out. The results are shown in Tables 4 to 8. Note that in Comparative Example 1, crystallization occurred at room temperature, so the high frequency characteristics (Δε r and tanδ iso ) was not measured. <Storage test> 0.5 g of the liquid crystal composition was weighed into a 1 mL sample bottle (manufactured by Maruemu Co., Ltd.) and degassed for 10 minutes at 150 to 250 Pa. The bottle was then purged with dry nitrogen and the attached lid was placed on the bottle. The bottle was then stored in a temperature-controlled thermostatic chamber (manufactured by Espec Corporation, SH-241) at 25°C for two weeks, and the occurrence of crystallization of the liquid crystal composition was visually confirmed every week.

[0226] [Table 4]

[0227] [Table 5]

[0228] [Table 6]

[0229] [Table 7]

[0230] [Table 8]

[0231] From Example 1, it can be seen that the liquid crystal composition containing one or more compounds represented by the general formula (i) and one or more compounds represented by the general formula (ii) has T ni is high, Δn is large, and Δε r is large, and tanδ iso It was confirmed that the storage stability at room temperature was good. On the other hand, from Comparative Examples 1 and 2, it was found that the liquid crystal composition not containing one or more compounds represented by the general formula (i) and one or more compounds represented by the general formula (ii) had poor storage stability or T ni The results showed that the temperature was low, below 120°C. In addition, in Comparative Example 1, it was confirmed that LC-A was crystallized one week after preparation. Furthermore, from Examples 2 to 31, it was confirmed that similar effects were obtained when various compounds were used or when a hindered phenol-based antioxidant or a hindered amine-based light stabilizer was used in combination.

[0232] The liquid crystal composition of the present invention can be used in liquid crystal display devices, sensors, liquid crystal lenses, optical communication devices and antennas.

Claims

1. The following general formula (i) 【Chemistry 1】 (In general formula (i), R ｉ１ are represented by the following formulas (R i1 -1) to (R i1 -5): 【Chemistry 2】 represents a group selected from the group consisting of groups represented by A ｉ１ is the formula (A ｉ１ -1), formula (A ｉ１ -SP-2), formula (A ｉ１ -SP-4), group (c) and group (d): Formula (A ｉ１ -1), Formula (A ｉ１ -SP-2), Formula (A ｉ１ -SP-4) 【Transformation 3】 (Formula (A)) ｉ１ -1), Formula (A) ｉ１ -SP-2), formula (A ｉ１ -SP-4) The white dot is R ｉ１ represents a bond to The black dot is Z ｉ１ represents a bond to .) (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group (d) thiophene-2,5-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group, thieno[3,2-b]thiophene-2,5-diyl group represents a group selected from the group consisting of A ｉ２ and A ｉ３ are each independently the following groups (a), (b), (c), and (d): (a) a 1,4-cyclohexylene group (one —CH ２ - or two or more non-adjacent -CH ２ - may be replaced with -O- or -S-.) (b) a 1,4-phenylene group (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group (d) thiophene-2,5-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group, thieno[3,2-b]thiophene-2,5-diyl group represents a group selected from the group consisting of The above A ｉ２ and A ｉ３ One or more hydrogen atoms in each independently represent a substituent S ｉ１ and optionally substituted by Substituent S ｉ１ represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms; One or more —CH in the alkyl group ２ - may be independently substituted by -O-, -S-, -NH-, -CO- and / or -CS-; One or more —CH in the alkyl group ２ -CH ２ - may each independently be substituted by -CH=CH-, -CF=CF- and / or -C≡C-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, Oxygen atoms do not bond directly to each other, Substituent S ｉ１ When there are multiple, they may be the same or different, Z ｉ１ and Z ｉ２ each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms, One or more —CH ２ - is independently -O-, -CF ２ may be substituted with - and / or -CO-, One or more —CH ２ -CH ２ Each - is independently -CH ２ -CH(CH ３ ) -, -CH(CH ３ )-CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ ) -, -C(CH ３ ) may be substituted by —CH—, —CH═N—, —N═CH—, —N═N—, —C≡C—, —CO—O— and / or —O—CO—, Oxygen atoms do not bond directly to each other, n ｉ１ represents an integer of 0 to 1.) and one or more compounds represented by the formula: The following general formula (ii): 【Chemistry 4】 (In general formula (ii), R ｉｉ１ is represented by the following formula (R ii1 -A): 【Transformation 5】 (In formula (R ii1 -A), R ii1A represents an alkyl group having 1 to 18 carbon atoms; one or more —CH 2 — in the alkyl group may each independently be substituted by —O—, —S—, —NH—, —CO— and / or —CS—; one or more —CH 2 —CH 2 — in the alkyl group may each independently be replaced by —C≡C—; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, When the alkyl group is substituted with a specific group, the oxygen atoms are not directly bonded to each other, The black dots represent bonds to A ii1 .) represents an alkynyl group represented by the formula: A ｉｉ１ , A ｉｉ２ and A ｉｉ３ each independently represents a hydrocarbon ring having 3 to 16 carbon atoms or a heterocycle having 3 to 16 carbon atoms; The above A ｉｉ１ , A ｉｉ２ and A ｉｉ３ One or more hydrogen atoms in each independently represent a substituent S ｉｉ１ and optionally substituted by Substituent S ｉｉ１ represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms; One or more —CH in the alkyl group ２ - may be independently substituted by -O-, -S-, -NH-, -CO- and / or -CS-; One or more —CH in the alkyl group ２ -CH ２ - may each independently be substituted by -CH=CH-, -CF=CF- and / or -C≡C-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, Oxygen atoms do not bond directly to each other, Substituent S ｉｉ１ When there are multiple, they may be the same or different, Z ｉｉ１ and Z ｉｉ２ each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms, One or more —CH ２ - is independently -O-, -CF ２ may be substituted with - and / or -CO-, One or more —CH ２ -CH ２ Each - is independently -CH ２ -CH(CH ３ ) -, -CH(CH ３ )-CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ ) -, -C(CH ３ ) may be substituted by —CH—, —CH═N—, —N═CH—, —N═N—, —C≡C—, —CO—O— and / or —O—CO—, Oxygen atoms do not bond directly to each other, n ｉｉ１ represents an integer from 0 to 2, A ｉｉ３ and Z ｉｉ２ When there are multiple, they may be the same or different.) A liquid crystal composition containing one or more compounds represented by the total content of the compounds represented by the general formula (i) in the liquid crystal composition (100% by mass) is 10 to 40% by mass, A liquid crystal composition in which the total content of the compounds represented by the general formula (ii) is 1 to 55% by mass based on 100% by mass of the liquid crystal composition.

2. The compound represented by the general formula (i) is represented by the following general formulas (i-1) to (i-2): 【Transformation 6】 (In general formulas (i-1) to (i-2), R ｉ１ , A ｉ１ , A ｉ２ and A ｉ３ represents R in the above general formula (i). ｉ１ , A ｉ１ , A ｉ２ and A ｉ３ and have the same meaning.) 2. The liquid crystal composition according to claim 1, wherein the compound is selected from the group consisting of compounds represented by the formula:

3. The compound represented by the general formula (ii) is represented by the following general formulas (ii-1) to (ii-3): 【Transformation 7】 (In general formulas (ii-1) to (ii-3), R ｉｉ１ , A ｉｉ１ , A ｉｉ２ and A ｉｉ３ represents R in the above general formula (ii). ｉｉ１ , A ｉｉ１ , A ｉｉ２ and A ｉｉ３ and each mean the same thing, In general formula (ii-3), A ｉｉ３－２ The definition of A in the above general formula (ii) ｉｉ３－２ (This is the same as the definition of 3. The liquid crystal composition according to claim 1, wherein the compound is selected from the group consisting of compounds represented by the formula:

4. Furthermore, the compound represented by the following general formula (iii): 【Transformation 8】 (In general formula (iii), R ｉｉｉ１ each independently represents an alkyl group having 1 to 20 carbon atoms, One or more —CH ２ - may be independently substituted by -O-, -S-, -NH-, -CO- and / or -CS-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, Oxygen atoms do not bond directly to each other, A ｉｉｉ１ and A ｉｉｉ２ are each independently the following groups (a), (b), (c), and (d): (a) a 1,4-cyclohexylene group (one —CH ２ - or two or more non-adjacent -CH ２ - may be replaced by -O- and / or -S-.) (b) a 1,4-phenylene group (in which one —CH= or two or more —CH= groups may be replaced by —N=). (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group, 2,3-dihydro-1H-indene-1,5-diyl group, 2,3-dihydro-1H-indene-2,5-diyl group, 2,3-dihydro-1H-indene-1,6-diyl group, 1 1H-indene-2,5-diyl group, 1H-indene-1,5-diyl group, 1H-indene-3,5-diyl group, 1H-indene-1,6-diyl group, 1H-indene-2,6-diyl group, 1H-indene-3,6-diyl group (one -CH= or two or more -CH= present in a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, an anthracene-2,6-diyl group, an anthracene-1,4-diyl group, an anthracene-9,10-diyl group, or a phenanthrene-2,7-diyl group may be replaced by -N=). (d) a thiophene-2,5-diyl group, a benzothiophene-2,5-diyl group, a benzothiophene-2,6-diyl group, a dibenzothiophene-3,7-diyl group, a dibenzothiophene-2,6-diyl group, a thieno[3,2-b]thiophene-2,5-diyl group, or a benzo[1,2-b:4,5-b']dithiophene-2,6-diyl group (one -CH= or two or more -CH= present in this group may be replaced by -N=). represents a group selected from the group consisting of The above A ｉｉｉ１ and A ｉｉｉ２ One or more hydrogen atoms in each independently represent a substituent S ｉｉｉ１ and optionally substituted by Substituent S ｉｉｉ１ represents any one of a halogen atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms, One or more —CH ２ - may be independently substituted by -O-, -S-, -NH-, -CO- and / or -CS-; One or more —CH ２ -CH ２ - may each independently be substituted by -CH=CH-, -CF=CF- and / or -C≡C-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, Oxygen atoms do not bond directly to each other, Substituent S ｉｉｉ１ When there are multiple, they may be the same or different, Z ｉｉｉ１ represents a single bond or an alkylene group having 1 to 20 carbon atoms, One or more —CH ２ - is independently -O-, -CF ２ may be substituted with - and / or -CO-, One or more —CH ２ -CH ２ Each - is independently -CH ２ -CH(CH ３ ) -, -CH(CH ３ )-CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ ) -, -C(CH ３ )═CH—, —CH═N—, —N═CH—, —N═N—, —C≡C—, —CO—O— and / or —O—CO—, Oxygen atoms do not bond directly to each other, n ｉｉｉ１ represents an integer from 1 to 4, A ｉｉｉ１ and Z ｉｉｉ１ When there are multiple, they may be the same or different.) The liquid crystal composition according to claim 1 or 2, comprising one or more compounds represented by the following formula:

5. The upper limit temperature of the liquid crystal phase of the liquid crystal composition (T ｎｉ 3. The liquid crystal composition according to claim 1, wherein the temperature at which the liquid crystal layer is heated is 131° C. or higher, and Δn at 25° C. and 589 nm is 0.43 or higher.

6. A liquid crystal display device using the liquid crystal composition according to claim 1 or 2.

7. 8. The liquid crystal display element according to claim 7, which is driven by an active matrix method or a passive matrix method.

8. 3. A liquid crystal display device in which the dielectric constant is reversibly switched by reversibly changing the alignment direction of the liquid crystal molecules of the liquid crystal composition according to claim 1 or 2.

9. A sensor using the liquid crystal composition according to claim 1 or 2.

10. A liquid crystal lens using the liquid crystal composition according to claim 1 or 2.

11. An optical communication device using the liquid crystal composition according to claim 1 or 2.

12. An antenna using the liquid crystal composition according to claim 1 or 2.

13. 13. The antenna of claim 12, a first substrate having a plurality of slots; a second substrate facing the first substrate and provided with a power supply unit; a first dielectric layer provided between the first substrate and the second substrate; a plurality of patch electrodes arranged corresponding to the plurality of slots; a third substrate on which the patch electrode is provided; a liquid crystal layer provided between the first substrate and the third substrate; An antenna, wherein the liquid crystal layer contains the liquid crystal composition according to claim 1 .

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