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

Abstract

The present invention has a large Δn and a large Δε r The present invention provides a compound capable of providing a liquid crystal composition having a large molecular weight and good storage stability at low temperatures, and a liquid crystal composition, a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the compound. The present invention provides a compound represented by general formula (i) having a benzofuran structure or a benzothiophene structure and an isothiocyanate group (-NCS), as well as a liquid crystal composition, a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the compound.

Description

[Technical Field]

[0001] The present invention relates to a compound, and a liquid crystal composition, a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the compound. [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 has a large Δn and a large Δε r The present invention provides a compound capable of providing a liquid crystal composition having a large molecular weight and good storage stability at low temperatures, and a liquid crystal composition, a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the compound. [Means for solving the problem]

[0006] As a result of extensive investigations, the present inventors have found that a compound represented by general formula (i) having a benzofuran structure or a benzothiophene structure and an isothiocyanate group (-NCS) can solve the above-mentioned problems, 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] (In general formula (i), R i1 represents a hydrogen atom 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-, -CO- and / or -CS-; one or more -CH2-CH2- groups in the alkyl group may each independently be substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, Oxygen atoms do not bond directly to each other, A ibf / t is represented by the following general formula (A ibf -1)~(A ibf -4) and (A ibt -1)~(A ibt -4)

[0009] [ka] (General formula (A ibf -1)~(A ibf -4) and (A ibt -1)~(A ibt -4) Medium, The white dot is R i1 represents a bond to The black dot is Z i1 represents a bond to L i1 and L i2each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms; One or more -CH2- groups in the alkyl group may each independently be replaced by -O-, -S-, -CO- and / or -CS-; one or more -CH2-CH2- groups in the alkyl group may each independently be substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, Oxygen atoms never bond directly to each other.) represents a group selected from the group consisting of groups represented by A i1 and A i2 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 and A i2 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 -CH2- groups in the alkyl group may each independently be replaced by -O-, -S- and / or -CO-; one or more -CH2-CH2- groups in the alkyl group may each independently be substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-; 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- and / or -C≡C-; Oxygen atoms do not bond directly to each other, n i1 represents an integer between 0 and 3, A i2 or Z i2 When there are multiple, they may be the same or different.) A compound represented by the formula:

[0010] Item 2. The compound represented by the general formula (i) is represented by the following general formulas (i-1) to (i-6):

[0011] [ka] (In general formulas (i-1) to (i-6), R i1 , A ibf / t , A i1 and A i2 represents R in the above general formula (i). i1 , A ibf / t , A i1 and A i2 and have the same meaning.) Item 2. The compound according to item 1, which is a compound selected from the group consisting of compounds represented by the formula:

[0012] Section 3. Said R i1 Item 3. The compound according to item 1 or 2, wherein represents a linear or branched alkyl group having 2 to 6 carbon atoms, a linear alkoxyalkyl group having 1 to 6 carbon atoms, or a linear alkenyl group having 2 to 6 carbon atoms.

[0013] Item 4. A liquid crystal composition containing one or more compounds according to any one of items 1 to 3.

[0014] Item 5. A liquid crystal display device using the liquid crystal composition according to item 4.

[0015] Item 6. A sensor using the liquid crystal composition according to item 4.

[0016] Item 7. A liquid crystal lens using the liquid crystal composition according to item 4.

[0017] Item 8. An optical communication device using the liquid crystal composition according to item 4.

[0018] Item 9. An antenna using the liquid crystal composition according to item 4.

[0019] Item 10. The antenna according to item 9, 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 5. An antenna in which the liquid crystal layer contains the liquid crystal composition according to item 4. [Effects of the Invention]

[0020] According to the present invention, by using a compound represented by general formula (i) having a benzofuran structure or a benzothiophene structure and an isothiocyanate group (-NCS), it is possible to obtain a compound having a large Δn and a large Δε r A liquid crystal composition having a large solubility and good storage stability at low temperatures can be obtained, and the liquid crystal composition is useful for liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas. DETAILED DESCRIPTION OF THE INVENTION

[0021] (Compound represented by general formula (i)) The compound according to the present invention is a compound represented by general formula (i) having a benzofuran structure or a benzothiophene structure and an isothiocyanate group (-NCS).

[0022] The liquid crystal composition according to the present invention contains one or more compounds represented by general formula (i) having a benzofuran structure or a benzothiophene structure and an isothiocyanate group (-NCS).

[0023] [ka]

[0024] In general formula (i), R i1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and 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 substituted with -O-, -S-, -CO- and / or -CS-. Furthermore, one or more -CH2-CH2- groups in the alkyl group may each independently be substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -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, and a bromine 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 i1 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 i1 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. Also, R i1can 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. Also, R i1 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. As the alkynyl group, from the viewpoint of ease of synthesis and extension of the conjugated system, the following formula (R i1 An alkynyl group represented by -A) is preferred.

[0025] [ka]

[0026] Formula (R i1 -A) Medium, R i1A 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-, -CO- and / or -CS-. Furthermore, one or more -CH2-CH2- groups in the alkyl group may each independently be substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -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. Also, the formula (R i1 -A) In the middle, the black dot is A i1 Represents a bond to . Also, R i1 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. Also, R i1 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 i1can 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. For example, R i1 can represent an alkoxyalkyl group having 1 to 19 carbon atoms by substituting one -CH2- in the alkyl group with -O-. The alkoxyalkyl group may be linear, branched, or cyclic, and is preferably a linear alkoxyalkyl group. The alkoxyalkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms. R i1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) in the formula (R i1 -1)~(R i1 -46).

[0027] [ka]

[0028] [ka]

[0029] Formula (R i1 -1)~(R i1 -46) In the middle, black dots are A ibf / t Represents a bond to . In addition, R i1From the viewpoints of Δn and compatibility with other liquid crystal compounds, a linear or branched alkyl group having 2 to 6 carbon atoms, a linear alkoxyalkyl group having 1 to 6 carbon atoms, or a linear alkenyl group having 2 to 6 carbon atoms is preferred.

[0030] In general formula (i), A ibf / t is represented by the following general formula (A ibf -1)~(A ibf -4) and (A ibt -1)~(A ibt -4) represents a group selected from the group consisting of groups represented by the formula:

[0031] [ka]

[0032] General formula (A ibf -1)~(A ibf -4) and (A ibt -1)~(A ibt -4) Medium, white point is R i1 The black dots represent bonds to Z. i1 Represents a bond to . In addition, the general formula (A ibf -1)~(A ibf -4) and (A ibt -1)~(A ibt -4) Medium, L i1 and L i2 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms. The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and 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 substituted with -O-, -S-, -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-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-. 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, and a bromine 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, L i1 and L i2 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, L i1 and L i2 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. Also, L i1 and L i2can 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. Also, L i1 and L i2 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. Also, L i1 and L i2 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. Also, L i1 and L i2 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, L i1and L i2 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.

[0033] L i1 and L i2 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) in the formula (L i1 / 2 -1)~(L i1 / 2 -36).

[0034] [ka]

[0035] Formula (L i1 / 2 -1)~(L i1 / 2 -36), the black dots represent bonds to the benzofuran or benzothiophene structure. From the viewpoint of solubility and viscosity, L i1 and L i2 At least one of L is preferably a hydrogen atom or a fluorine atom. i1 and L i2 is more preferably a hydrogen atom or a fluorine atom. More specifically, A ibf / t is expressed by the following formula (A ibf / t -1)~(A ibf / t -10).

[0036] [ka]

[0037] Formula (A ibf / t -1)~(A ibf / t -10) White point is R i1 The black dots represent bonds to Z. i1 Represents a bond to .

[0038] In general formula (i), A i1 and A i2 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:

[0039] A i1 and A i2 One or more hydrogen atoms in each independently represent a substituent S i1 may be 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. 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- and / or -CO-. Furthermore, one or more -CH2-CH2- groups in the alkyl group may each independently be substituted with -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-. 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 linear alkyl group having 1 to 10 carbon atoms, a chlorine atom, or a fluorine atom is preferred. Also, A i1 and A i2 At least one of the groups has at least one substituent S i1 It is preferably substituted with Also, A i2 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.

[0040] A i1 Substituent S in i1 The substitution position of the following formula (A i1 -SP-1)~(A i1 -SP-4).

[0041] [ka]

[0042] Formula (A i1 -SP-1)~(A i1 -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 i2 Substituent S in i1 The substitution position of the following formula (A i2 -SP-1)~(A i2 -SP-4).

[0043] [ka]

[0044] Formula (A i2 -SP-1)~(A i2 -SP-4) White spots are Z i2 The black dots represent bonds to Z. i2 or represents a bond to an isothiocyanate group (-NCS). More specifically, A i1 is expressed by the following formula (A i1 -1)~(A i1 -10) is preferred.

[0045] [ka]

[0046] Formula (A i1 -1)~(A i1 -10) 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 i2 is expressed by the following formula (A i2 -1)~(A i2 -8) is preferred.

[0047] [ka]

[0048] Formula (A i2 -1)~(A i2 -8) Medium, white dots are Z i2 The black dots represent bonds to Z. i2 or represents a bond to an isothiocyanate group (-NCS).

[0049] 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- and / or -C≡C-. However, when the alkylene group is substituted with a specific group, the oxygen atoms are not directly bonded to each other. 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).

[0050] [ka]

[0051] Formula(Z i1 / 2 -1)~(Z i1 / 2 -24) Medium, white dots A ibf / t , A i1 or A i2 The black dot represents a bond to A. i1 or A i2 Represents a bond to . In terms of Δn, Z i1 and Z i2 are preferably each independently a single bond or -C≡C-. Also, from the viewpoint of Δn, Z i1 and Z i2 It is preferable that at least one of the groups is -C≡C-.

[0052] In general formula (i), ni1 represents an integer of 0 to 3, preferably an integer of 1 or 2. A i2 or Z i2 When there are a plurality of groups, they may be the same or different.

[0053] The compound represented by general formula (i) is preferably a compound selected from the group consisting of compounds represented by the following general formulas (i-1) to (i-6).

[0054] [ka]

[0055] In general formulas (i-1) to (i-6), R i1 , A ibf / t , A i1 and A i2 represents R in the above general formula (i). i1 , A ibf / t , A i1 and A i2 and each mean the same thing.

[0056] The compound represented by general formula (i-1) is preferably a compound represented by the following general formulas (i-1-1) to (i-1-4).

[0057] [ka]

[0058] In general formulas (i-1-1) to (i-1-4), R i1 and S i1 represents R in the above general formula (i). i1 and S i1 and the preferred groups are also the same.

[0059] 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-1-1.4).

[0060] [ka]

[0061] 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-1-2.4).

[0062] [ka]

[0063] Specific examples of the compound represented by general formula (i-1-3) include compounds represented by the following structural formulas (i-1-3.1) to (i-1-3.4).

[0064] [ka]

[0065] Specific examples of the compound represented by general formula (i-1-4) include compounds represented by the following structural formulas (i-1-4.1) to (i-1-4.4).

[0066] [ka]

[0067] The compound represented by general formula (i-2) is preferably a compound represented by the following general formulas (i-2-1) to (i-2-4).

[0068] [ka]

[0069] In general formulas (i-2-1) to (i-2-4), R i1 and S i1 represents R in the above general formula (i). i1 and S i1and the preferred groups are also the same. Specific examples of the compound represented by general formula (i-2-1) include compounds represented by the following structural formulas (i-2-1.1) to (i-2-1.4).

[0070] [ka]

[0071] Specific examples of the compound represented by general formula (i-2-2) include compounds represented by the following structural formulas (i-2-2.1) to (i-2-2.4).

[0072] [ka]

[0073] Specific examples of the compound represented by general formula (i-2-3) include compounds represented by the following structural formulas (i-2-3.1) to (i-2-3.4).

[0074] [ka]

[0075] Specific examples of the compound represented by general formula (i-2-4) include compounds represented by the following structural formulas (i-2-4.1) to (i-2-4.4).

[0076] [ka]

[0077] The compound represented by general formula (i-3) is preferably a compound represented by the following general formulas (i-3-1) to (i-3-2).

[0078] [ka]

[0079] In general formulas (i-3-1) to (i-3-2), R i1 and S i1 represents R in the above general formula (i). i1 and S i1 and the preferred groups are also the same. Specific examples of the compound represented by general formula (i-3-1) include compounds represented by the following structural formulas (i-3-1.1) to (i-3-1.4).

[0080] [ka]

[0081] Specific examples of the compound represented by general formula (i-3-2) include compounds represented by the following structural formulas (i-3-2.1) to (i-3-2.4).

[0082] [ka]

[0083] The compound represented by general formula (i-4) is preferably a compound represented by the following general formulas (i-4-1) to (i-4-9).

[0084] [ka]

[0085] [ka]

[0086] In general formulas (i-4-1) to (i-4-9), R i1 , L i1 and S i1 represents R in the above general formula (i). i1 , L i1 and S i1and the preferred groups are also the same. Specific examples of the compound represented by general formula (i-4-1) include compounds represented by the following structural formulas (i-4-1.1) to (i-4-1.4).

[0087] [ka]

[0088] Specific examples of the compound represented by general formula (i-4-2) include compounds represented by the following structural formulas (i-4-2.1) to (i-4-2.4).

[0089] [ka]

[0090] Specific examples of the compound represented by general formula (i-4-3) include compounds represented by the following structural formulas (i-4-3.1) to (i-4-3.4).

[0091] [ka]

[0092] Specific examples of the compound represented by general formula (i-4-4) include compounds represented by the following structural formulas (i-4-4.1) to (i-4-4.4).

[0093] [ka]

[0094] Specific examples of the compound represented by general formula (i-4-5) include compounds represented by the following structural formulas (i-4-5.1) to (i-4-5.2).

[0095] [ka]

[0096] Specific examples of the compound represented by general formula (i-4-6) include compounds represented by the following structural formulae (i-4-6.1) to (i-4-6.2).

[0097] [ka]

[0098] Specific examples of the compound represented by general formula (i-4-7) include compounds represented by the following structural formulas (i-4-7.1) to (i-4-7.2).

[0099] [ka]

[0100] Specific examples of the compound represented by general formula (i-4-8) include compounds represented by the following structural formulas (i-4-8.1) to (i-4-8.2).

[0101] [ka]

[0102] Specific examples of the compound represented by general formula (i-4-9) include compounds represented by the following structural formulas (i-4-9.1) to (i-4-9.2).

[0103] [ka]

[0104] The compound represented by general formula (i-5) is preferably a compound represented by the following general formulas (i-5-1) to (i-5-12).

[0105] [ka]

[0106] [ka]

[0107] In general formulas (i-5-1) to (i-5-12), R i1 and S i1 represents R in the above general formula (i). i1 and S i1 and the preferred groups are also the same. Specific examples of the compound represented by general formula (i-5-1) include compounds represented by the following structural formulas (i-5-1.1) to (i-5-1.2).

[0108] [ka]

[0109] Specific examples of the compound represented by general formula (i-5-2) include compounds represented by the following structural formulas (i-5-2.1) to (i-5-2.2).

[0110] [ka]

[0111] Specific examples of the compound represented by general formula (i-5-3) include compounds represented by the following structural formulas (i-5-3.1) to (i-5-3.2).

[0112] [ka]

[0113] Specific examples of the compound represented by general formula (i-5-4) include compounds represented by the following structural formulas (i-5-4.1) to (i-5-4.2).

[0114] [ka]

[0115] Specific examples of the compound represented by general formula (i-5-5) include compounds represented by the following structural formulas (i-5-5.1) to (i-5-5.3).

[0116] [ka]

[0117] Specific examples of the compound represented by general formula (i-5-6) include compounds represented by the following structural formulae (i-5-6.1) to (i-5-6.2).

[0118] [ka]

[0119] Specific examples of the compound represented by general formula (i-5-7) include compounds represented by the following structural formulas (i-5-7.1) to (i-5-7.2).

[0120] [ka]

[0121] Specific examples of the compound represented by general formula (i-5-8) include compounds represented by the following structural formulas (i-5-8.1) to (i-5-8.2).

[0122] [ka]

[0123] Specific examples of the compound represented by general formula (i-5-9) include compounds represented by the following structural formulas (i-5-9.1) to (i-5-9.2).

[0124] [ka]

[0125] Specific examples of the compound represented by general formula (i-5-10) include compounds represented by the following structural formulas (i-5-10.1) to (i-5-10.2).

[0126] [ka]

[0127] Specific examples of the compound represented by general formula (i-5-11) include compounds represented by the following structural formulas (i-5-11.1) to (i-5-11.2).

[0128] [ka]

[0129] Specific examples of the compound represented by general formula (i-5-12) include compounds represented by the following structural formulas (i-5-12.1) to (i-5-12.2).

[0130] [ka]

[0131] The compound represented by general formula (i-6) is preferably a compound represented by the following general formulas (i-6-1) to (i-6-12).

[0132] [ka]

[0133] [ka]

[0134] In general formulas (i-6-1) to (i-6-12), R i1 and Si1 represents R in the above general formula (i). i1 and S i1 and the preferred groups are also the same. Specific examples of the compound represented by general formula (i-6-1) include compounds represented by the following structural formulas (i-6-1.1) to (i-6-1.4).

[0135] [ka]

[0136] Specific examples of the compound represented by general formula (i-6-2) include compounds represented by the following structural formulas (i-6-2.1) to (i-6-2.5).

[0137] [ka]

[0138] [ka]

[0139] Specific examples of the compound represented by general formula (i-6-3) include compounds represented by the following structural formulas (i-6-3.1) to (i-6-3.4).

[0140] [ka]

[0141] Specific examples of the compound represented by general formula (i-6-4) include compounds represented by the following structural formulas (i-6-4.1) to (i-6-4.4).

[0142] [ka]

[0143] Specific examples of the compound represented by general formula (i-6-5) include compounds represented by the following structural formulas (i-6-5.1) to (i-6-5.5).

[0144] [ka]

[0145] [ka]

[0146] Specific examples of the compound represented by general formula (i-6-6) include compounds represented by the following structural formulas (i-6-6.1) to (i-6-6.4).

[0147] [ka]

[0148] Specific examples of the compound represented by general formula (i-6-7) include compounds represented by the following structural formulas (i-6-7.1) to (i-6-7.4).

[0149] [ka]

[0150] Specific examples of the compound represented by general formula (i-6-8) include compounds represented by the following structural formulas (i-6-8.1) to (i-6-8.4).

[0151] [ka]

[0152] Specific examples of the compound represented by general formula (i-6-9) include compounds represented by the following structural formulas (i-6-9.1) to (i-6-9.4).

[0153] [ka]

[0154] Specific examples of the compound represented by general formula (i-6-10) include compounds represented by the following structural formulas (i-6-10.1) to (i-6-10.4).

[0155] [ka]

[0156] Specific examples of the compound represented by general formula (i-6-11) include compounds represented by the following structural formulae (i-6-11.1) to (i-6-11.4).

[0157] [ka]

[0158] Specific examples of the compound represented by general formula (i-6-12) include compounds represented by the following structural formulae (i-6-12.1) to (i-6-12.4).

[0159] [ka]

[0160] General formula (i), general formula (i-1)~(i-6), general formula (i-1-1)~(i-1-4), general formula (i-2-1)~(i-2-4), general formula (i-3-1)~(i-3-2), general formula (i-4-1)~(i-4-9), general formula (i-5-1)~(i-5-12), general formula (i-6-1)~(i-6-12), structural formula (i-1-1.1)~(i-1-1.4), structural formula (i-1-2.1)~(i-1-2.4), structural formula (i-1-3.1)~(i-1-3.4), structural formula (i-1-4.1)~(i-1-4.4), structural formula (i-2-1.1)~(i-2- 1.4), structural formula (i-2-2.1)~(i-2-2.4), structural formula (i-2-3.1)~(i-2-3.4), structural formula (i-2-4.1)~(i-2-4.4), structural formula (i-3-1.1)~(i-3-1.4), structural formula (i-3-2.1)~(i-3-2.4), structural formula (i-4-1.1)~(i-4-1.4), structural formula (i-4-2.1)~(i-4-2.4), structural formula (i-4-3.1)~(i-4-3.4), structural formula (i-4-4.1)~(i-4-4.4), structural formula (i-4-5.1)~(i-4-5.2), structural formula (i-4-6.1)~ (i-4-6.2), structural formula (i-4-7.1)~(i-4-7.2), structural formula (i-4-8.1)~(i-4-8.2), structural formula (i-4-9.1)~(i-4-9.2), structural formula (i-5-1.1)~(i-5-1.2), structural formula (i-5-2.1)~(i-5-2.2), structural formula (i-5-3.1)~(i-5-3.2), structural formula (i-5-4.1)~(i-5-4.2), structural formula (i-5-5.1)~(i-5-5.3), structural formula (i-5-6.1)~(i-5-6.2), structural formula (i-5-7.1)~(i-5-7.2), structural formula (i-5- 8.1)~(i-5-8.2), structural formula (i-5-9.1)~(i-5-9.2), structural formula (i-5-10.1)~(i-5-10.2), structural formula (i-5-11.1)~(i-5-11.2), structural formula (i-5-12.1)~(i-5-12.2), structural formula (i-6-1.1)~(i-6-1.4), structural formula (i-6-2.1)~(i-6-2.5), structural formula (i-6-3.1)~(i-6-3.4), structural formula (i-6-4.1)~(i-6-4.4), structural formula (i-6-5.1)~(i-6-5.5), structural formula (i-6-6.1)~(i-6-6.The compounds represented by structural formulae (i-6-4), (i-6-7.1) to (i-6-7.4), (i-6-8.1) to (i-6-8.4), (i-6-9.1) to (i-6-9.4), (i-6-10.1) to (i-6-10.4), (i-6-11.1) to (i-6-11.4), or (i-6-12.1) to (i-6-12.4) may be used in liquid crystal compositions in one or more varieties, preferably 1 to 10 varieties, preferably 1 to 5 varieties, and preferably 1 to 3 varieties.

[0161] General formula (i), general formula (i-1)~(i-6), general formula (i-1-1)~(i-1-4), general formula (i-2-1)~(i-2-4), general formula (i-3-1)~(i-3-2), general formula (i-4-1)~(i-4-9), general formula (i-5-1)~(i-5-12), general formula (i-6-1)~(i-6-12), structural formula (i-1-1.1)~(i-1-1.4), structural formula (i-1-2.1)~(i-1-2.4), structural formula (i-1-3.1)~(i-1-3.4), structural formula (i-1-4.1)~(i-1-4.4), structural formula (i-2-1.1)~(i-2- 1.4), structural formula (i-2-2.1)~(i-2-2.4), structural formula (i-2-3.1)~(i-2-3.4), structural formula (i-2-4.1)~(i-2-4.4), structural formula (i-3-1.1)~(i-3-1.4), structural formula (i-3-2.1)~(i-3-2.4), structural formula (i-4-1.1)~(i-4-1.4), structural formula (i-4-2.1)~(i-4-2.4), structural formula (i-4-3.1)~(i-4-3.4), structural formula (i-4-4.1)~(i-4-4.4), structural formula (i-4-5.1)~(i-4-5.2), structural formula (i-4-6.1)~ (i-4-6.2), structural formula (i-4-7.1)~(i-4-7.2), structural formula (i-4-8.1)~(i-4-8.2), structural formula (i-4-9.1)~(i-4-9.2), structural formula (i-5-1.1)~(i-5-1.2), structural formula (i-5-2.1)~(i-5-2.2), structural formula (i-5-3.1)~(i-5-3.2), structural formula (i-5-4.1)~(i-5-4.2), structural formula (i-5-5.1)~(i-5-5.3), structural formula (i-5-6.1)~(i-5-6.2), structural formula (i-5-7.1)~(i-5-7.2), structural formula (i-5- 8.1)~(i-5-8.2), structural formula (i-5-9.1)~(i-5-9.2), structural formula (i-5-10.1)~(i-5-10.2), structural formula (i-5-11.1)~(i-5-11.2), structural formula (i-5-12.1)~(i-5-12.2), structural formula (i-6-1.1)~(i-6-1.4), structural formula (i-6-2.1)~(i-6-2.5), structural formula (i-6-3.1)~(i-6-3.4), structural formula (i-6-4.1)~(i-6-4.4), structural formula (i-6-5.1)~(i-6-5.5), structural formula (i-6-6.1)~(i-6-6.The lower limit of the total content of the compounds represented by structural formulae (i-6-4), (i-6-7.1) to (i-6-7.4), (i-6-8.1) to (i-6-8.4), (i-6-9.1) to (i-6-9.4), (i-6-10.1) to (i-6-10.4), (i-6-11.1) to (i-6-11.4), or (i-6-12.1) to (i-6-12.4) in 100% by mass of the liquid crystal composition is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1% by mass or more.

[0162] General formula (i), general formula (i-1)~(i-6), general formula (i-1-1)~(i-1-4), general formula (i-2-1)~(i-2-4), general formula (i-3-1)~(i-3-2), general formula (i-4-1)~(i-4-9), general formula (i-5-1)~(i-5-12), general formula (i-6-1)~(i-6-12), structural formula (i-1-1.1)~(i-1-1.4), structural formula (i-1-2.1)~(i-1-2.4), structural formula (i-1-3.1)~(i-1-3.4), structural formula (i-1-4.1)~(i-1-4.4), structural formula (i-2-1.1)~(i-2- 1.4), structural formula (i-2-2.1)~(i-2-2.4), structural formula (i-2-3.1)~(i-2-3.4), structural formula (i-2-4.1)~(i-2-4.4), structural formula (i-3-1.1)~(i-3-1.4), structural formula (i-3-2.1)~(i-3-2.4), structural formula (i-4-1.1)~(i-4-1.4), structural formula (i-4-2.1)~(i-4-2.4), structural formula (i-4-3.1)~(i-4-3.4), structural formula (i-4-4.1)~(i-4-4.4), structural formula (i-4-5.1)~(i-4-5.2), structural formula (i-4-6.1)~ (i-4-6.2), structural formula (i-4-7.1)~(i-4-7.2), structural formula (i-4-8.1)~(i-4-8.2), structural formula (i-4-9.1)~(i-4-9.2), structural formula (i-5-1.1)~(i-5-1.2), structural formula (i-5-2.1)~(i-5-2.2), structural formula (i-5-3.1)~(i-5-3.2), structural formula (i-5-4.1)~(i-5-4.2), structural formula (i-5-5.1)~(i-5-5.3), structural formula (i-5-6.1)~(i-5-6.2), structural formula (i-5-7.1)~(i-5-7.2), structural formula (i-5- 8.1)~(i-5-8.2), structural formula (i-5-9.1)~(i-5-9.2), structural formula (i-5-10.1)~(i-5-10.2), structural formula (i-5-11.1)~(i-5-11.2), structural formula (i-5-12.1)~(i-5-12.2), structural formula (i-6-1.1)~(i-6-1.4), structural formula (i-6-2.1)~(i-6-2.5), structural formula (i-6-3.1)~(i-6-3.4), structural formula (i-6-4.1)~(i-6-4.4), structural formula (i-6-5.1)~(i-6-5.5), structural formula (i-6-6.1)~(i-6-6.The upper limit of the total content of the compounds represented by structural formulae (i-6-4), (i-6-7.1) to (i-6-7.4), (i-6-8.1) to (i-6-8.4), (i-6-9.1) to (i-6-9.4), (i-6-10.1) to (i-6-10.4), (i-6-11.1) to (i-6-11.4), or (i-6-12.1) to (i-6-12.4) in 100% by mass of the liquid crystal composition is preferably 95% by mass or less, more preferably 90% by mass or less, more preferably 85% by mass or less, more preferably 30% by mass or less, and more preferably 20% by mass or less.

[0163] General formula (i), general formula (i-1)~(i-6), general formula (i-1-1)~(i-1-4), general formula (i-2-1)~(i-2-4), general formula (i-3-1)~(i-3-2), general formula (i-4-1)~(i-4-9), general formula (i-5-1)~(i-5-12), general formula (i-6-1)~(i-6-12), structural formula (i-1-1.1)~(i-1-1.4), structural formula (i-1-2.1)~(i-1-2.4), structural formula (i-1-3.1)~(i-1-3.4), structural formula (i-1-4.1)~(i-1-4.4), structural formula (i-2-1.1)~(i-2- 1.4), structural formula (i-2-2.1)~(i-2-2.4), structural formula (i-2-3.1)~(i-2-3.4), structural formula (i-2-4.1)~(i-2-4.4), structural formula (i-3-1.1)~(i-3-1.4), structural formula (i-3-2.1)~(i-3-2.4), structural formula (i-4-1.1)~(i-4-1.4), structural formula (i-4-2.1)~(i-4-2.4), structural formula (i-4-3.1)~(i-4-3.4), structural formula (i-4-4.1)~(i-4-4.4), structural formula (i-4-5.1)~(i-4-5.2), structural formula (i-4-6.1)~ (i-4-6.2), structural formula (i-4-7.1)~(i-4-7.2), structural formula (i-4-8.1)~(i-4-8.2), structural formula (i-4-9.1)~(i-4-9.2), structural formula (i-5-1.1)~(i-5-1.2), structural formula (i-5-2.1)~(i-5-2.2), structural formula (i-5-3.1)~(i-5-3.2), structural formula (i-5-4.1)~(i-5-4.2), structural formula (i-5-5.1)~(i-5-5.3), structural formula (i-5-6.1)~(i-5-6.2), structural formula (i-5-7.1)~(i-5-7.2), structural formula (i-5- 8.1)~(i-5-8.2), structural formula (i-5-9.1)~(i-5-9.2), structural formula (i-5-10.1)~(i-5-10.2), structural formula (i-5-11.1)~(i-5-11.2), structural formula (i-5-12.1)~(i-5-12.2), structural formula (i-6-1.1)~(i-6-1.4), structural formula (i-6-2.1)~(i-6-2.5), structural formula (i-6-3.1)~(i-6-3.4), structural formula (i-6-4.1)~(i-6-4.4), structural formula (i-6-5.1)~(i-6-5.5), structural formula (i-6-6.1)~(i-6-6.The total content of the compounds represented by structural formulae (i-6-7.1) to (i-6-7.4), structural formulae (i-6-8.1) to (i-6-8.4), structural formulae (i-6-9.1) to (i-6-9.4), structural formulae (i-6-10.1) to (i-6-10.4), structural formulae (i-6-11.1) to (i-6-11.4), or structural formulae (i-6-12.1) to (i-6-12.4) in 100% by mass of the liquid crystal composition is determined based on the solubility, Δn and / or Δε. r From this viewpoint, the content is preferably 0.1 to 95% by mass, more preferably 0.5 to 90% by mass, even more preferably 1 to 85% by mass, even more preferably 1 to 30% by mass, and even more preferably 1 to 20% by mass.

[0164] The compound represented by general formula (i) (including its sub-concepts) can be synthesized using known synthesis methods, some of which are exemplified below. (Production Method 1) Production of a compound represented by the following formula (s-3)

[0165] [ka]

[0166] In general formulas (s-1) to (s-3), R i1 , A i1 and L i1 represents R in the general formula (i). i1 , A i1 and L i1 It has the same meaning as: First, the compound represented by general formula (s-1) is reacted with the compound represented by general formula (s-2) to obtain the target compound represented by general formula (s-3). The reaction method includes, for example, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst and a base. Specific examples of palladium catalysts include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0). When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added. A specific example of a copper catalyst is copper(I) iodide. A specific example of the base is triethylamine.

[0167] (Production Method 2) Production of a compound represented by the following formula (s-7)

[0168] [ka]

[0169] In general formulas (s-4) to (s-7), R i1 , A i1 and L i1 represents R in the general formula (i). i1 , A i1 and L i1 It has the same meaning as: A compound represented by general formula (s-4) is reacted with bispinacoldiborane to obtain a compound represented by general formula (s-5), which is then reacted with a compound represented by general formula (s-6) to obtain a compound represented by general formula (s-7). The reaction method includes, for example, Suzuki coupling reaction using a palladium catalyst and a base. Specific examples of palladium catalysts include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0). Examples of the base include potassium carbonate, sodium carbonate, potassium phosphate, and the like.

[0170] (Production Method 3) Production of a compound represented by the following formula (s-12):

[0171] [ka]

[0172] In general formulas (s-8) to (s-12), R i1 , A i1 , L i1 and S i1 represents R in the general formula (i). i1 , A i1 , L i1 and S i1 It has the same meaning as: A compound represented by general formula (s-10) can be obtained by reacting a compound represented by general formula (s-8) with a compound represented by general formula (s-9). The reaction method includes, for example, Suzuki coupling reaction using a palladium catalyst and a base. Specific examples of palladium catalysts include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0). Examples of the base include potassium carbonate, sodium carbonate, potassium phosphate, and the like. Next, the compound represented by general formula (s-10) is reacted with the compound represented by general formula (s-11) to obtain the compound represented by general formula (s-12). The reaction method includes, for example, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst and a base. Specific examples of palladium catalysts include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0). When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added. A specific example of a copper catalyst is copper(I) iodide. A specific example of the base is triethylamine.

[0173] (Production Method 4) Production of a compound represented by the following formula (s-18)

[0174] [ka]

[0175] In general formulas (s-13) to (s-18), R i1 , A i2 , L i1 and S i1 represents R in the general formula (i). i1 , A i2 , L i1 and S i1 It has the same meaning as: The compound represented by general formula (s-14) can be obtained by reacting the compound represented by general formula (s-13) with trimethylsilylacetylene and then reacting it with potassium carbonate in methanol. The reaction method includes, for example, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst and a base. Specific examples of palladium catalysts include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0). When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added. A specific example of a copper catalyst is copper(I) iodide. A specific example of the base is triethylamine. Furthermore, a compound represented by general formula (s-16) can be obtained by reacting a compound represented by general formula (s-14) with a compound represented by general formula (s-15). The reaction method includes, for example, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst and a base. Next, the compound represented by general formula (s-16) is reacted with the compound represented by general formula (s-17) to obtain the target compound represented by general formula (s-18). The reaction method includes, for example, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst and a base.

[0176] Examples of reaction conditions other than those described in each step include those described in literature such as Experimental Chemistry Lectures (edited by the Chemical Society of Japan, published by Maruzen Co., Ltd.), Organic Syntheses (A John Wiley & Sons, Inc., Publication), Beilstein Handbook of Organic Chemistry (Beilstein-Institut für Literatur der Organischen Chemie, Springer-Verlag Berlin and Heidelberg GmbH & Co.K), and Fiesers' Reagents for Organic Synthesis (John Wiley & Sons, Inc.), or those listed in databases such as SciFinder (Chemical Abstracts Service, American Chemical Society) and Reaxys (Elsevier Ltd.). When handling substances that are unstable to oxygen and / or moisture in each step, it is preferable to carry out the work in an inert gas such as nitrogen gas or argon gas. In each step, functional groups can be protected as necessary. Examples of the protecting group include those described in Greene's Protective Groups in Organic Synthesis ((Fourth Edition), co-authored by Peter Gmwuts and Theodora W. Greene, A. John Wiley & Sons, Inc., Publication). Furthermore, purification may be carried out in each step as necessary. Purification methods include chromatography, recrystallization, distillation, sublimation, reprecipitation, adsorption, and liquid separation. Specific examples of the refining agent include silica gel, alumina, activated carbon, and the like.

[0177] <Characteristic values ​​of the compound represented by general formula (i) (including sub-concepts)> The characteristic values ​​of the compound represented by general formula (i) (including sub-concepts) can be measured as follows. First, a compound represented by general formula (i) (including sub-concepts) was added to a base liquid crystal to prepare liquid crystal compositions containing 0 mass %, 5 mass %, and 10 mass % of the compound represented by general formula (i) (including sub-concepts) per 100 mass % of the liquid crystal composition, and the Δn (refractive index anisotropy) and Δε of each liquid crystal composition were measured. r Measure. Then, using the least squares method, Δn (refractive index anisotropy) and Δε of 100% by mass of the compound represented by general formula (i) (including sub-concepts), that is, the compound represented by general formula (i) (including sub-concepts), r is calculated from the extrapolated value.

[0178] 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 at 25°C and 589 nm of the compound (including sub-concepts) represented by general formula (i) according to the present invention is preferably 0.35 or more, more preferably 0.40 to 0.60, more preferably 0.43 to 0.57, and even more preferably 0.45 to 0.55, from the viewpoint of the phase modulation power of light of that wavelength.

[0179] 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 compound (including sub-concepts) represented by the general formula (i) according to the present invention, the dielectric anisotropy Δε at 10 GHz is representative of the characteristics in the high frequency range. r was measured. Δε r =(ε r∥ -ε r⊥ ) Here, "ε r " is the dielectric constant, and 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.

[0180] Δε r 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 ) to determine 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 measurement was carried out at a temperature of 25°C, and Δε r has no units.

[0181] The Δε at 25°C of the compound (including sub-concepts) represented by the general formula (i) according to the present invention r is preferably larger, but from the viewpoint of phase modulation power in the GHz band, it is preferably 0.30 or more, preferably 0.30 to 0.65, preferably 0.31 to 0.60, preferably 0.32 to 0.55, preferably 0.33 to 0.50, preferably 0.34 to 0.45, and preferably 0.35 to 0.40.

[0182] (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 general formula (i) (including sub-concepts), and, if necessary, other liquid crystal compounds and additives.

[0183] Examples of the additives include stabilizers, dye compounds, polymerizable compounds, and azotolane compounds.

[0184] 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-3).

[0185] [ka]

[0186] Examples of the hindered amines include hindered amine light stabilizers represented by the following structural formulas (YY-1) to (YY-2).

[0187] [ka]

[0188] 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.

[0189] (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.

[0190] 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.

[0191] 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 the 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.

[0192] 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.

[0193] 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.

[0194] 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. As the liquid crystal composition, by using a liquid crystal composition containing one or more compounds (including sub-concepts) represented by general formula (i) having a benzofuran structure or a benzothiophene structure and an isothiocyanate group (-NCS), Δn is large and Δε r Since the capacitance is large and the storage stability at low temperatures is good, an antenna having high reliability against external stimuli such as heat can be provided. This makes it 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]

[0195] The present invention will be further described below with reference to examples, but the present invention is not limited to these examples. 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." Compounds that can take either cis or trans forms will be referred to as trans forms unless otherwise specified. (Example 1) Preparation of the compound represented by formula (I-1)

[0196] [ka]

[0197] Under a nitrogen atmosphere, 110 mL of a 1 mol / L tetrahydrofuran (THF) solution of lithium isopropylamide (LDA) was placed in a reaction vessel and cooled to below -60 ° C. A solution of 20 g of the compound represented by formula (I-1-1) dissolved in 30 mL of THF was slowly added dropwise. After the addition was complete, the mixture was stirred at -60 ° C. or below for 1 hour and then reacted at 0 ° C. for 1 hour. Next, the reaction vessel was cooled to -78 ° C., and a solution of 17 g of 1-iodopropane dissolved in 20 mL of THF was slowly added dropwise. After the addition was complete, the mixture was reacted at -60 ° C. or below for 1 hour. After the reaction was complete, 10% by mass hydrochloric acid was poured into the reaction solution and extracted with toluene. The organic layer was washed with saturated saline and then purified by column chromatography (silica gel, hexane) to obtain 22.5 g of the compound represented by formula (I-1-2). Next, under a nitrogen atmosphere, 22.5 g of the compound represented by formula (I-1-2), 0.7 g of copper(I) iodide, 1.2 g of bis(triphenylphosphine)palladium(II) dichloride, 50 mL of triethylamine, and 150 mL of N,N-dimethylformamide (DMF) were added to a reaction vessel. Then, while heating at 80 °C, a solution of 14 g of the compound represented by formula (I-1-3) dissolved in 15 mL of N,N-dimethylformamide was added dropwise, and the mixture was stirred at 80 °C for 2 hours. After completion of the reaction, saturated aqueous ammonium chloride solution was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and then recrystallized from toluene to obtain 24.5 g of the compound represented by formula (I-1-4). A reaction vessel was charged with 24.5 g of the compound represented by formula (I-1-4), 100 mL of dichloromethane, and 13.4 g of 1,1-thiocarbonyldiimidazole, and the mixture was heated under reflux for 2 hours. After the reaction was completed, the organic layer was washed with saturated saline and then purified by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 2 / 1), yielding 23 g of the compound represented by formula (I-1). MS(EI): m / z=369 (Example 2) Preparation of the compound represented by formula (I-2)

[0198] [ka]

[0199] Under a nitrogen atmosphere, 27 g of the compound represented by formula (I-2-1), 30 g of potassium acetate, 28 g of the compound represented by formula (I-2-2), 1.6 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, and 250 mL of DMF were added to a reaction vessel, and the reaction vessel was heated to 80 ° C. for 3 hours. After completion of the reaction, 10% by mass hydrochloric acid was poured into the reaction solution, and the mixture was extracted with toluene. The organic layer was washed with saturated saline and then purified by column chromatography (silica gel, toluene) to obtain 27 g of the compound represented by formula (I-2-3). Next, under a nitrogen atmosphere, 27 g of the compound represented by formula (I-2-3), 1.1 g of tetrakis(triphenylphosphine)palladium, 20 g of potassium carbonate, 29 g of the compound represented by formula (I-2-4), 250 mL of THF, and 50 mL of water were added to a reaction vessel, and the reaction vessel was heated to 70 ° C. After completion of the reaction, 10% by mass hydrochloric acid was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, and the solvent was distilled off. The residue was dispersed and washed with toluene to obtain 31 g of the compound represented by formula (I-2-5). Next, 31 g of the compound represented by formula (I-2-5), 200 ml of dichloromethane, and 15.4 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel and heated under reflux for 2 hours. After the reaction was completed, the organic layer was washed with saturated saline and then purified by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 2 / 1) to obtain 29 g of the compound represented by formula (I-2). MS(EI): m / z=473 (Example 3) Preparation of compound represented by formula (I-3)

[0200] [ka]

[0201] Under a nitrogen atmosphere, 26 g of the compound represented by formula (I-3-1), 0.7 g of copper(I) iodide, 1.2 g of bis(triphenylphosphine)palladium(II) dichloride, 50 mL of triethylamine, and 100 mL of DMF were added to a reaction vessel. While the reaction mixture was heated at 60°C, a solution of 12 g of trimethylsilylacetylene dissolved in 15 mL of N,N-dimethylformamide was added dropwise and stirred at 60°C for 2 hours. After the reaction was completed, saturated ammonium chloride solution was poured into the reaction mixture, and the mixture was extracted with toluene. The organic layer was washed with saturated saline, and the toluene was evaporated. 100 mL of methanol and 14 g of potassium carbonate were added to the concentrate, and the mixture was heated and stirred at 50°C for 2 hours. After the reaction was completed, pure water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, and the solvent was evaporated. The mixture was purified by column chromatography (silica gel, hexane) to obtain 17 g of the compound represented by formula (I-3-2). Next, under a nitrogen atmosphere, 22 g of the compound represented by formula (I-3-3), 1 g of tetrakis(triphenylphosphine)palladium, 50 mL of triethylamine, and 100 mL of DMF were added to a reaction vessel. While the reaction solution was heated at 80 °C, a solution prepared by dissolving 17 g of the compound represented by formula (I-3-2) in 15 mL of N,N-dimethylformamide was added dropwise, and the mixture was stirred at 80 °C for 2 hours. After the reaction was completed, saturated aqueous ammonium chloride solution was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and then recrystallized from toluene to obtain 27 g of the compound represented by formula (I-3-4). Next, 27 g of the compound represented by formula (I-3-4), 200 mL of dichloromethane, and 15 g of 1,1'-thiocarbonyl-di-2(1H)pyridone were added to a reaction vessel and reacted at room temperature for 2 hours. After the reaction was completed, the organic layer was washed with saturated saline and then purified by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 2 / 1) to obtain 29 g of the compound represented by formula (I-3). MS(EI): m / z=469 (Example 4) Preparation of compound represented by formula (I-4)

[0202] [ka]

[0203] The compound represented by formula (I-4) was obtained in the same manner as in Example 3, except that the compound represented by formula (I-3-1) was replaced with the compound represented by formula (I-4-1), and the compound represented by formula (I-3-3) was replaced with the compound represented by formula (I-4-3). MS(EI): m / z=483 (Example 5) Preparation of the compound represented by formula (I-5)

[0204] [ka]

[0205] The compound represented by formula (I-5) was obtained in the same manner as in Example 3, except that the compound represented by formula (I-3-1) was replaced with the compound represented by formula (I-5-1), and the compound represented by formula (I-3-3) was replaced with the compound represented by formula (I-5-3). MS(EI): m / z=483 (Example 6) Preparation of compound represented by formula (I-6)

[0206] [ka]

[0207] The compound represented by formula (I-6) was obtained in the same manner as in Example 3, except that the compound represented by formula (I-3-1) was replaced with the compound represented by formula (I-6-1), and the compound represented by formula (I-3-3) was replaced with the compound represented by formula (I-6-3). MS(EI): m / z=467 (Example 7) Preparation of compound represented by formula (I-7)

[0208] [ka]

[0209] The compound represented by formula (I-7) was obtained in the same manner as in Example 3, except that the compound represented by formula (I-3-1) was replaced with the compound represented by formula (I-7-1), and the compound represented by formula (I-3-3) was replaced with the compound represented by formula (I-7-3). MS(EI): m / z=497 (Example 8) Preparation of compound represented by formula (I-8)

[0210] [ka]

[0211] The compound represented by formula (I-8) was obtained in the same manner as in Example 3, except that the compound represented by formula (I-3-1) was replaced with the compound represented by formula (I-8-1), and the compound represented by formula (I-3-3) was replaced with the compound represented by formula (I-8-3). MS(EI): m / z=481 (Example 9) Preparation of compound represented by formula (I-9)

[0212] [ka]

[0213] The compound represented by formula (I-9) was obtained in the same manner as in Example 3, except that the compound represented by formula (I-3-1) was replaced with the compound represented by formula (I-9-1), and the compound represented by formula (I-3-3) was replaced with the compound represented by formula (I-9-3). MS(EI): m / z=483 (Example 10) Preparation of compound represented by formula (I-10)

[0214] [ka]

[0215] The compound represented by formula (I-10) was obtained in the same manner as in Example 3, except that the compound represented by formula (I-3-1) was replaced with the compound represented by formula (I-10-1), and the compound represented by formula (I-3-3) was replaced with the compound represented by formula (I-10-3). MS(EI): m / z=483

[0216] (Preparation and Evaluation of Liquid Crystal Compositions) A base liquid crystal (LC-1) was prepared that exhibited the following physical properties. All values ​​were measured. T n-i (Nematic-isotropic liquid phase transition temperature): 74.0℃ Δε (dielectric anisotropy at 25°C and 1 kHz): 5.11 Δn (refractive index anisotropy at 25 ° C. and 589 nm): 0.141 γ1 (Rotational viscosity coefficient at 25°C): 107 mPa·s

[0217] Compounds (I-1) to (I-10) obtained in the examples and compounds represented by formulas (C-1) to (C-2) that do not adopt a benzofuran structure or a benzothiophene structure were added to the base liquid crystal (LC-1) to prepare liquid crystal compositions containing 0 mass%, 5 mass%, and 10 mass% of each compound, respectively, based on 100 mass% of the liquid crystal composition. Then, the Δn and Δε at 100% by mass of each compound were calculated using the least squares method. r The results are shown in Table 1. In addition, since compound (C-2) precipitated, Δn and Δε r It was not possible to obtain an extrapolated value.

[0218] (Storage stability test) Compounds (I-1) to (I-10) obtained in the examples and compounds represented by formulas (C-1) to (C-2) that do not adopt a benzofuran structure or a benzothiophene structure were added to the base liquid crystal (LC-1), and liquid crystal compositions containing 5% by mass of each compound in 100% by mass of the liquid crystal composition were prepared. 0.5 g of the prepared liquid crystal composition was weighed into a 1 mL sample bottle (Maruem Co., Ltd.) and degassed for 10 minutes at 150°C and 250 Pa. The vial was then purged with dry nitrogen and the provided lid was placed on the vial. The vial was then stored in a temperature-controlled thermostatic chamber (Espec Corp., SH-241) at 0°C for two weeks, and the occurrence of crystallization of the liquid crystal composition was visually confirmed every day. Crystals that did not show any visible crystallization for more than a week were marked "Good," crystals that showed crystallization after the fourth day were marked "Good," and crystals that showed crystallization by the third day were marked "Poor." The results are shown in Table 1.

[0219] [ka]

[0220] [Table 1]

[0221] From Example 11, Comparative Example 1, Examples 17, 18 and Comparative Example 2, it was found that the compound represented by the general formula (i) having a benzofuran structure, a benzothiophene structure and an isothiocyanate group (-NCS) has a Δn and Δε r It was confirmed that the solubility of the polymer was large and that the storage stability at low temperatures was relatively good. [Industrial Applicability]

[0222] The compound of the present invention can be used in liquid crystal compositions, liquid crystal display devices, sensors, liquid crystal lenses, optical communication devices and antennas.

Claims

1. The following general formula (i) 【Chemical 1】 (In general formula (i), R ｉ１ represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, One or more —CH ２ - may be independently substituted by -O-, -S-, -CO- and / or -CS-; One or more —CH ２ -CH ２ - may be each independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, Oxygen atoms do not bond directly to each other, A ｉｂｆ／ｔ is represented by the following general formula (A ｉｂｆ -1) to (A ｉｂｆ -4) and (A ｉｂｔ -1) to (A ｉｂｔ -4) 【Chemistry 2】 (General formula (A ｉｂｆ -1) to (A ｉｂｆ -4) and (A ｉｂｔ -1) to (A ｉｂｔ -4) Medium, The white dot is R ｉ１ represents a bond to The black dot is Z ｉ１ represents a bond to L ｉ１ and L ｉ２ each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms; One or more —CH in the alkyl group ２ - may be independently substituted by -O-, -S-, -CO- and / or -CS-; One or more —CH in the alkyl group ２ -CH ２ - may be each independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, Oxygen atoms never bond directly to each other.) represents a group selected from the group consisting of groups represented by A ｉ１ and A ｉ２ 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 and A ｉ２ 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- and / or -CO-; One or more —CH in the alkyl group ２ -CH ２ - may be each independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-; 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 )=CH—, —CH═N—, —N═CH—, —N═N— and / or —C≡C—; Oxygen atoms do not bond directly to each other, n ｉ１ represents an integer from 0 to 3, A ｉ２ or Z ｉ２ When there are multiple, they may be the same or different.) A compound represented by the formula:

2. The compound represented by the general formula (i) is represented by the following general formulas (i-1) to (i-6): 【Chemistry 3】 (In general formulas (i-1) to (i-6), R ｉ１ , A ｉｂｆ／ｔ , A ｉ１ and A ｉ２ represents R in the above general formula (i). ｉ１ , A ｉｂｆ／ｔ , A ｉ１ and A ｉ２ and have the same meaning.) The compound according to claim 1, which is a compound selected from the group consisting of compounds represented by the formula:

3. The R ｉ１ represents a linear or branched alkyl group having 2 to 6 carbon atoms, a linear alkoxyalkyl group having 1 to 6 carbon atoms, or a linear alkenyl group having 2 to 6 carbon atoms.

4. A liquid crystal composition comprising one or more compounds according to any one of claims 1 to 3.

5. A liquid crystal display device using the liquid crystal composition according to claim 4.

6. A sensor using the liquid crystal composition according to claim 4.

7. A liquid crystal lens using the liquid crystal composition according to claim 4.

8. An optical communication device using the liquid crystal composition according to claim 4.

9. An antenna using the liquid crystal composition according to claim 4.

10. 10. The antenna of claim 9, 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 4 .

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