Compounds, as well as liquid crystal compositions, liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment, and antennas using the same.

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 compounds, as well as liquid crystal compositions, liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment, and antennas using the same. [Background technology]

[0002] As a new application for liquid crystal displays (LCDs), which are widely used in displays, antennas using LCDs to transmit and receive radio waves between mobile vehicles such as automobiles and communication satellites are attracting attention. Conventionally, satellite communications have used parabolic antennas, but when used in mobile vehicles such as automobiles, the parabolic antenna must be constantly pointed towards the satellite, requiring a large movable part. However, with LCD antennas, the direction of radio wave transmission and reception can be changed by the movement of the LCD inside the panel, so there is no need to move the antenna itself, and the shape of the antenna can be made flat. Furthermore, in order to realize global high-capacity and high-speed communication, studies are underway on low-Earth orbit satellite constellations using many low-Earth orbit satellites. To track low-Earth orbit satellites, which appear to be constantly moving from the ground, LCD antennas that can easily change the direction of radio wave transmission and reception are useful. Generally, autonomous driving systems for vehicles require the download of large amounts of high-precision 3D map data. However, with an antenna using liquid crystal (LCD), by integrating the antenna into the vehicle, large amounts of data can be downloaded from communication satellites without any mechanically moving parts. The frequency band used for satellite communication is approximately 13 GHz, which is significantly different from the frequencies used for conventional LCD displays. Therefore, the required physical properties of the LCD are also significantly different; for example, the required Δn for LCD used in antennas is around 0.4, and the operating temperature range is, for example, -20 to 120°C. Furthermore, infrared laser image recognition and distance measuring devices using liquid crystals are attracting attention as sensors for autonomous driving of mobile vehicles such as automobiles. The required Δn for liquid crystals in 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 crystalline compounds constituting liquid crystal compositions exhibiting a high Δn of 0.2 or higher have low compatibility. Therefore, selecting liquid crystalline compounds with high compatibility is also important. In contrast, an example of liquid crystal technology for antennas is Patent Document 1. 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 Publication No. 2016-37607 [Non-patent literature]

[0004] [Non-Patent Document 1] Dolfi, "Electronics Letters," (UK), 1993, Vol. 29, No. 10, pp. 926-928. [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] In this invention, Δn is large and Δε r The objective is to provide a compound that can provide a liquid crystal composition with a large volume and good storage properties at low temperatures, as well as a liquid crystal composition, liquid crystal display element, sensor, liquid crystal lens, optical communication equipment, and antenna using the same. [Means for solving the problem]

[0006] As a result of diligent research, the 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 problems, and have completed the present invention. An example of the configuration of the present invention that solves the above problems is as follows.

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

[0008]

Chemical formula

[0009]

Chemical formula

[0010] Section 2. The compound represented by the above general formula (i) is one of 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 This is R in the general formula (i) above. i1 , A ibf / t , A i1 and A i2 These express the same meaning. A compound selected from the group consisting of compounds represented by the formula, as described in item 1.

[0012] Section 3. Said R i1 The compound according to item 1 or 2, wherein is any of the following: 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 comprising one or more compounds described in any one of items 1 to 3.

[0014] Item 5. A liquid crystal display element using the liquid crystal composition described in Item 4.

[0015] Item 6. A sensor using the liquid crystal composition described in Item 4.

[0016] Item 7. A liquid crystal lens using the liquid crystal composition described in Item 4.

[0017] Section 8. Optical communication equipment using the liquid crystal composition described in Section 4.

[0018] Item 9. An antenna using the liquid crystal composition described in Item 4.

[0019] Item 10. An antenna as described in Item 9, A first circuit board equipped with multiple slots, A second substrate, which is opposite the first substrate and has a power supply section, A first dielectric layer is provided between the first substrate and the second substrate, Multiple patch electrodes arranged corresponding to the multiple slots, A third substrate on which the aforementioned patch electrodes are provided, The device comprises a liquid crystal layer provided between the first substrate and the third substrate, An antenna in which the liquid crystal layer contains the liquid crystal composition described in 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), Δn is large and Δε r A liquid crystal composition with high fission and good storage properties at low temperatures can be obtained, and this liquid crystal composition is useful for liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment, and antennas. [Modes for carrying out the invention]

[0021] (Compounds 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] Furthermore, 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 This 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 a linear alkyl group is preferred. The number of carbon atoms in an alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, and more preferably 2 to 6. One or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO-, and / or -CS-. Furthermore, one or more -CH2-CH2- groups in the alkyl group may be independently substituted with -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 be independently substituted with halogen atoms. Examples of halogen atoms include fluorine, chlorine, and bromine. However, if the alkyl group is substituted with a predetermined group, oxygen atoms will not directly bond to each other. Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms do not directly bond with other sulfur atoms and / or oxygen atoms with other sulfur atoms. For example, R i1 This can represent an alkoxy group having 1 to 19 carbon atoms by substituting one -CH2- in the alkyl group with -O-. The alkoxy group is a linear, branched, or cyclic alkoxy group, and a linear alkoxy group is preferred. The number of carbon atoms in the alkoxy group is preferably 2 to 10, and more preferably 2 to 6. Also, R i1 This can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms by substituting one -CH2- in the alkyl group with -S-. The alkylsulfanil group is a linear, branched, or cyclic alkylsulfanil group, and a linear alkylsulfanil group is preferred. The number of carbon atoms in the alkylsulfanil group is preferably 2 to 10, and more preferably 2 to 6. Also, R i1This 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- groups. The alkenyl group is a linear, branched, or cyclic alkenyl group, and a linear alkenyl group is preferred. The number of carbon atoms in the alkenyl group is preferably 2 to 10, and more preferably 2 to 6. Also, R i1 This can represent an alkynyl group having 2 to 20 carbon atoms by substituting one or more -CH2-CH2- atoms in the alkyl group with -C≡C- atoms. The alkynyl group is a linear, branched, or cyclic alkynyl group, and a linear alkynyl group is preferred. The number of carbon atoms in the alkynyl group is preferably 2 to 10, and more preferably 2 to 6. As for the alkynyl group, from the viewpoint of ease of synthesis and extension of the conjugated system, the following formula (R i1 -A) is a preferred alkynyl group.

[0025] [ka]

[0026] Formula (R i1 -A) Medium, R i1A This represents an alkyl group with 1 to 18 carbon atoms. The alkyl group having 1 to 18 carbon atoms is a linear, branched, or cyclic alkyl group, and a linear alkyl group is preferred. In alkyl groups with 1 to 18 carbon atoms, the number of carbon atoms is preferably 1 to 8. One or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO-, and / or -CS-. Furthermore, one or more -CH2-CH2- groups in the alkyl group may be independently substituted with -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 be independently substituted with halogen atoms. Examples of halogen atoms include fluorine, chlorine, bromine, and iodine. However, if the alkyl group is substituted with a predetermined group, oxygen atoms will not directly bond to each other. Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms do not directly bond with other sulfur atoms and / or oxygen atoms with other sulfur atoms. Also, formula (R i1 -A) In the middle, the black spot is A i1 This represents a binding operation. Also, R i1 This can represent an alkenyloxy group having 2 to 19 carbon atoms, by having one -CH2- in the alkyl group replaced with -O-, and one or more -CH2-CH2- units replaced with -CH=CH-. The alkenyloxy group is a linear, branched, or cyclic alkenyloxy group, and a linear alkenyloxy group is preferred. The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, and more preferably 2 to 6. Also, R i1 This can represent a halogenated alkyl group having 1 to 20 carbon atoms, by substituting one or more hydrogen atoms in the alkyl group with halogen atoms. The halogenated alkyl group is linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the alkyl halogen is preferably 2 to 10, and more preferably 2 to 6. Also, R i1This can represent a halogenated alkoxy group having 1 to 19 carbon atoms, by substituting one -CH2- in the alkyl group with -O-, and substituting one or more hydrogen atoms in the alkyl group with halogen atoms. The halogenated alkoxy group is a linear, branched, or cyclic halogenated alkoxy group, and a linear halogenated alkoxy group is preferred. The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, and more preferably 2 to 6. For example, R i1 This can represent an alkoxyalkyl group having 1 to 19 carbon atoms by substituting one -CH2- with -O- in the alkyl group. The alkoxyalkyl group is a linear, branched, or cyclic alkoxyalkyl group, and is preferably a linear alkoxyalkyl group. The number of carbon atoms in the alkoxyalkyl group is preferably 2 to 10, and more preferably 2 to 6. R i1 Specific examples of alkyl groups with 1 to 20 carbon atoms in the formula (including substituted ones) include the formula (R i1 -1)~(R i1 Examples of bases represented by -46) include the ones shown.

[0027] [ka]

[0028] [ka]

[0029] Formula (R i1 -1)~(R i1 -46) Among them, the sunshine is A ibf / t This represents a binding operation. Note, R i1From the viewpoint of Δn and compatibility with other liquid crystal compounds, linear or branched alkyl groups having 2 to 6 carbon atoms, linear alkoxyalkyl groups having 1 to 6 carbon atoms, and linear alkenyl groups having 2 to 6 carbon atoms are preferred.

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

[0031] [ka]

[0032] General formula (A ibf -1)~(A ibf -4) and (A ibt -1)~(A ibt -4) In the middle, the white dot is R i1 The black dot represents a bond to Z. i1 This represents a binding operation. Also, the general formula (A ibf -1)~(A ibf -4) and (A ibt -1)~(A ibt -4) Medium, L i1 and L i2 Each of these independently represents one of the following: 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 a linear alkyl group is preferred. The number of carbon atoms in an alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, and more preferably 2 to 6. One or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO-, and / or -CS- groups. Furthermore, one or more -CH2-CH2- groups in the alkyl group may be independently 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 be independently substituted with halogen atoms. Examples of halogen atoms include fluorine, chlorine, and bromine. However, if the alkyl group is substituted with a predetermined group, oxygen atoms will not directly bond to each other. Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms do not directly bond with other sulfur atoms and / or oxygen atoms with other sulfur atoms. For example, L i1 and L i2 This can represent an alkoxy group having 1 to 19 carbon atoms by substituting one -CH2- in the alkyl group with -O-. The alkoxy group is a linear, branched, or cyclic alkoxy group, and a linear alkoxy group is preferred. The number of carbon atoms in the alkoxy group is preferably 2 to 10, and more preferably 2 to 6. Also, L i1 and L i2 This can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms by substituting one -CH2- in the alkyl group with -S-. The alkylsulfanil group is a linear, branched, or cyclic alkylsulfanil group, and a linear alkylsulfanil group is preferred. The number of carbon atoms in the alkylsulfanil group is preferably 2 to 10, and more preferably 2 to 6. Also, L i1 and L i2This 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- groups. The alkenyl group is a linear, branched, or cyclic alkenyl group, and a linear alkenyl group is preferred. The number of carbon atoms in the alkenyl group is preferably 2 to 10, and more preferably 2 to 6. Also, L i1 and L i2 This can represent an alkynyl group having 2 to 20 carbon atoms by substituting one or more -CH2-CH2- atoms in the alkyl group with -C≡C- atoms. The alkynyl group is a linear, branched, or cyclic alkynyl group, and a linear alkynyl group is preferred. The number of carbon atoms in the alkynyl group is preferably 2 to 10, and more preferably 2 to 6. Also, L i1 and L i2 This can represent an alkenyloxy group having 2 to 19 carbon atoms, by having one -CH2- in the alkyl group replaced with -O-, and one or more -CH2-CH2- units replaced with -CH=CH-. The alkenyloxy group is a linear, branched, or cyclic alkenyloxy group, and a linear alkenyloxy group is preferred. The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, and more preferably 2 to 6. Also, L i1 and L i2 This can represent a halogenated alkyl group having 1 to 20 carbon atoms, by substituting one or more hydrogen atoms in the alkyl group with halogen atoms. The halogenated alkyl group is linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the alkyl halogen is preferably 2 to 10, and more preferably 2 to 6. Also, L i1and L i2 represents a halogenated alkoxy group having 1 to 19 carbon atoms, wherein one -CH2- in the alkyl group is replaced by -O-, and one or more hydrogen atoms in the alkyl group are replaced by halogen atoms. The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, preferably a linear halogenated alkoxy group. The number of carbon atoms in the halogenated alkoxy group is preferably 2 - 10, more preferably 2 - 6.

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

[0034]

Chemical formula

[0035] In the formula (L i1 / 2 -1) to (L i1 / 2 -36), the black dots represent bonds to the benzofuran structure or benzothiophene structure. From the viewpoints of solubility and viscosity, at least one of L i1 and L i2 is preferably a hydrogen atom or a fluorine atom, and more preferably L i1 and L i2 are hydrogen atoms or fluorine atoms. More specifically, A ibf / t preferably represents any one of the groups represented by the following formula (A ibf / t -1) to (A ibf / t -10).

[0036]

Chemical formula

[0037] Formula (A ibf / t -1)~(A ibf / t -10) Among them, the white dots are R i1 The black dot represents a bond to Z. i1 This represents a binding operation.

[0038] In general formula (i), A i1 and A i2 Each of these independently represents either a hydrocarbon ring with 3 to 16 carbon atoms or a heterocycle with 3 to 16 carbon atoms. A hydrocarbon ring or heterocycle having 3 to 16 carbon atoms is more specifically defined as the following groups (a), (b), (c), and (d): (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- groups in this group may be replaced with -O- or -S-). (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= groups within this group may be replaced with -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 N-2,7-diyl group (one or more -CH= present in 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, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, or phenanthrene-2,7-diyl group may be replaced with -N=.) (d) Thiophen-2,5-diyl group, benzothiophen-2,5-diyl group, benzothiophen-2,6-diyl group, dibenzothiophen-3,7-diyl group, dibenzothiophen-2,6-diyl group, thieno[3,2-b]thiophen-2,5-diyl group (one -CH= or two or more non-adjacent -CH= groups in this group may be replaced with -N=). It is preferable to represent a group selected from the group consisting of the following:

[0039] A i1 and A i2 One or more hydrogen atoms in the molecule are independently substituents S i1 It may be replaced by this. substituent S i1 This represents one of the following: 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 is linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the alkyl group is preferably 2 to 10, and preferably 3 to 6. One or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, and / or -CO- groups. Furthermore, one or more -CH2-CH2- groups in the alkyl group may be independently 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 be independently substituted with halogen atoms. Examples of halogen atoms include fluorine, chlorine, bromine, and iodine. However, if the alkyl group is substituted with a predetermined group, oxygen atoms will not directly bond to each other. Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms do not directly bond with other sulfur atoms and / or oxygen atoms with other sulfur atoms. substituent S i1 Preferred elements include linear alkyl groups having 1 to 10 carbon atoms, chlorine atoms, and fluorine atoms. Also, A i1 and A i2 At least one of them is at least one substituent S i1 It is preferable that it is substituted with Also, A i2 is at least one substituent S i1 It is preferable that it is substituted with Note that substituent S i1 If there are multiple items, they may be identical or different.

[0040] A i1 substituent S in i1 The substitution position is as follows: (A i1 -SP-1)~(A i1 -SP-4) is preferable.

[0041] [ka]

[0042] Formula (A i1 -SP-1)~(A i1 -SP-4) White dots are Z i1 The black dot represents a bond to Z. i2 Alternatively, it represents a bond to an isothiocyanate group (-NCS). A i2 substituent S in i1 The substitution position is as follows: (A i2 -SP-1)~(A i2 -SP-4) is preferable.

[0043] [ka]

[0044] Formula (A i2 -SP-1)~(A i2 -SP-4) White dots are Z i2 The black dot represents a bond to Z. i2 Alternatively, it represents a bond to an isothiocyanate group (-NCS). More specifically, A i1 The formula is as follows (A i1 -1)~(A i1 It is preferable to represent one of the following: -10)

[0045] [ka]

[0046] Formula (A i1 -1)~(A i1 -10) Among them, the white dot is Z i1 The black dot represents a bond to Z. i2 Alternatively, it represents a bond to an isothiocyanate group (-NCS). More specifically, A i2 The formula is as follows (A i2 -1)~(A i2 It is preferable to represent one of the following (-8):

[0047] [ka]

[0048] Formula (A i2 -1)~(A i2 -8) In the middle, the white dot is Z i2 The black dot represents a bond to Z. i2 Alternatively, it represents a bond to an isothiocyanate group (-NCS).

[0049] In general formula (i), Z i1 and Z i2 Each of these independently represents either a single bond or an alkylene group with 1 to 20 carbon atoms. The alkylene group is a linear, branched, or cyclic alkylene group, and a linear alkylene group is preferred. The number of carbon atoms in the alkylene group is preferably 2 to 10, and more preferably 2 to 6. One or more -CH2- groups in the alkylene group may be independently substituted with -O-, -CF2-, and / or -CO-. Furthermore, one or more -CH2-CH2- groups in the alkylene group may be independently 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 predetermined group, oxygen atoms do not directly bond to each other. Specific examples of alkylene groups with 2 to 20 carbon atoms (including substituted ones) are given by formula (Z i1 / 2 -1)~(Z i1 / 2 Examples of bases represented by -24) include the ones shown.

[0050] [ka]

[0051] Formula(Z i1 / 2 -1)~(Z i1 / 2 -24) White dots are A ibf / t , A i1 Or A i2 This represents a connection to A, with the black dot being A i1 Or A i2 This represents a binding operation. From the perspective of Δn, Z i1 and Z i2 Each of these is preferably a single bond or -C≡C-. Furthermore, from the perspective of Δn, Z i1 and Z i2 It is preferable that at least one of them is -C≡C-.

[0052] In general formula (i), ni1 This represents an integer between 0 and 3, preferably between 1 and 2. A i2 or Z i2 If there are multiple instances of this, they may be identical 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 This is R in the general formula (i) above. i1 , A ibf / t , A i1 and A i2 These express the same meaning.

[0056] The compound represented by general formula (i-1) is preferably one represented by one of 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 This is R in the general formula (i) above. i1 and S i1 These terms express the same meaning, and the preferred base also represents the same thing.

[0059] Specific examples of compounds represented by the general formula (i-1-1) include the compounds represented by the following structural formulas (i-1-1.1) to (i-1-1.4).

[0060] [ka]

[0061] Specific examples of compounds represented by general formula (i-1-2) include those represented by the following structural formulas (i-1-2.1) to (i-1-2.4).

[0062] [ka]

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

[0064] [ka]

[0065] Specific examples of compounds represented by the general formula (i-1-4) include the 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 one represented by one of 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 This is R in the general formula (i) above. i1 and S i1These terms express the same meaning, and the preferred base also represents the same thing. Specific examples of compounds represented by the general formula (i-2-1) include those represented by the following structural formulas (i-2-1.1) to (i-2-1.4).

[0070] [ka]

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

[0072] [ka]

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

[0074] [ka]

[0075] Specific examples of compounds represented by the general formula (i-2-4) include those 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 the 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 This is R in the general formula (i) above. i1 and S i1 These terms express the same meaning, and the preferred base also represents the same thing. Specific examples of compounds represented by the general formula (i-3-1) include those represented by the following structural formulas (i-3-1.1) to (i-3-1.4).

[0080] [ka]

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

[0082] [ka]

[0083] The compounds represented by general formula (i-4) are preferably those 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 This is R in the general formula (i) above. i1 , L i1 and S i1These terms express the same meaning, and the preferred base also represents the same thing. Specific examples of compounds represented by the general formula (i-4-1) include those represented by the following structural formulas (i-4-1.1) to (i-4-1.4).

[0087] [ka]

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

[0089] [ka]

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

[0091] [ka]

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

[0093] [ka]

[0094] Specific examples of compounds represented by the general formula (i-4-5) include the 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 the general formula (i-4-6) include compounds represented by the following structural formulas (i-4-6.1) to (i-4-6.2).

[0097] [Chemical formula]

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

[0099] [Chemical formula]

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

[0101] [Chemical formula]

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

[0103] [Chemical formula]

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

[0105] [Chemical formula]

[0106] [ka]

[0107] In general formulas (i-5-1) to (i-5-12), R i1 and S i1 This is R in the general formula (i) above. i1 and S i1 These terms express the same meaning, and the preferred base also represents the same thing. Specific examples of compounds represented by the general formula (i-5-1) include the compounds represented by the following structural formulas (i-5-1.1) to (i-5-1.2).

[0108] [ka]

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

[0110] [ka]

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

[0112] [ka]

[0113] Specific examples of compounds represented by the general formula (i-5-4) include those 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 the general formula (i-5-5) include compounds represented by the following structural formulas (i-5-5.1) to (i-5-5.3) and the like.

[0116]

Chem.

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

[0118]

Chem.

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

[0120]

Chem.

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

[0122]

Chem.

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

[0124]

Chem.

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

[0126] [ka]

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

[0128] [ka]

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

[0130] [ka]

[0131] The compounds represented by general formula (i-6) are preferably those 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 This is R in the general formula (i) above. i1 and S i1 These terms express the same meaning, and the preferred base also represents the same thing. Specific examples of compounds represented by the general formula (i-6-1) include those represented by the following structural formulas (i-6-1.1) to (i-6-1.4).

[0135] [ka]

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

[0137] [ka]

[0138] [ka]

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

[0140] [ka]

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

[0142] [ka]

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

[0144] [ka]

[0145] [ka]

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

[0147] [ka]

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

[0149] [ka]

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

[0151] [ka]

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

[0153] [ka]

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

[0155] [ka]

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

[0157] [ka]

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

[0159] [ka]

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

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

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

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

[0164] Compounds represented by general formula (i) (including sub-concepts) can be synthesized using known synthetic methods, some of which are given below as examples. (Method 1) Preparation of the 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 R in the above general formula (i) is i1 , A i1 and L i1 It expresses the same meaning. First, by reacting a compound represented by general formula (s-1) with a compound represented by general formula (s-2), the target compound represented by general formula (s-3) can be obtained. Examples of reaction methods include the 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(O). When using palladium(II) acetate as a palladium catalyst, ligands such as triphenylphosphine and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added. A specific example of a copper catalyst is copper(I) iodide. Specific examples of bases include triethylamine.

[0167] (Method 2) Preparation of the 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 R in the above general formula (i) is i1 , A i1 and L i1 It expresses the same meaning. By reacting the compound represented by general formula (s-4) with bispinacol diborane, a compound represented by general formula (s-5) can be obtained. This compound can then be reacted with the compound represented by general formula (s-6) to obtain the compound represented by general formula (s-7). Examples of reaction methods include the 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(O). Examples of bases include potassium carbonate, sodium carbonate, and potassium phosphate.

[0170] (Method 3) Preparation of the 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 R in the above general formula (i) is i1 , A i1 , L i1 and S i1 It expresses the same meaning. By reacting a compound represented by general formula (s-8) with a compound represented by general formula (s-9), a compound represented by general formula (s-10) can be obtained. Examples of reaction methods include the 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(O). Examples of bases include potassium carbonate, sodium carbonate, and potassium phosphate. Next, by reacting the compound represented by general formula (s-10) with the compound represented by general formula (s-11), the compound represented by general formula (s-12) can be obtained. Examples of reaction methods include the 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(O). When using palladium(II) acetate as a palladium catalyst, ligands such as triphenylphosphine and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added. A specific example of a copper catalyst is copper(I) iodide. Specific examples of bases include triethylamine.

[0173] (Method 4) Preparation of the 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 R in the above general formula (i) is i1 , A i2 , L i1 and S i1 It expresses the same meaning. A compound represented by general formula (S-14) can be obtained by reacting a compound represented by general formula (S-13) with trimethylsilylacetylene, and then reacting it with potassium carbonate in methanol. Examples of reaction methods include the 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(O). When using palladium(II) acetate as a palladium catalyst, ligands such as triphenylphosphine and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added. A specific example of a copper catalyst is copper(I) iodide. Specific examples of bases include 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). Examples of reaction methods include the Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base. Next, by reacting the compound represented by general formula (s-16) with the compound represented by general formula (s-17), the target compound represented by general formula (s-18) can be obtained. Examples of reaction methods include the Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.

[0176] Other reaction conditions not described in each step include those described in literature such as "Experimental Chemistry Course" (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 fuer 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 process, it is preferable to perform the work in an inert gas such as nitrogen gas or argon gas. Functional groups can be protected as needed at each stage of the process. Examples of protecting groups include those described in GREENE'S PROTECTIVE GROUPS IN ORGANIC SYNTHESIS (Fourth Edition), by PETER GMWUTS and THEODORA W. GREENE, published by A John Wiley & Sons, Inc. Furthermore, purification may be carried out as needed at each stage of the process. Purification methods include chromatography, recrystallization, distillation, sublimation, reprecipitation, adsorption, and liquid-liquid separation. Specific examples of purifying agents include silica gel, alumina, and activated carbon.

[0177] <Characteristic values ​​of compounds represented by general formula (i) (including sub-concepts)> The characteristic values ​​of a compound represented by general formula (i) (including its sub-concepts) can be measured as follows. First, a compound represented by general formula (i) (including its sub-concept) is added to the base liquid crystal to prepare liquid crystal compositions containing 0%, 5%, and 10% by mass of the compound represented by general formula (i) (including its sub-concept) in 100% by mass of the liquid crystal composition, respectively. The Δn (refractive index anisotropy) and Δε of each liquid crystal composition are then determined. r Measure. Then, using the least squares method, 100% by mass of the compound represented by general formula (i) (including its sub-concepts), i.e., the Δn (refractive index anisotropy) and Δε of the compound represented by general formula (i) (including its sub-concepts), are determined. r This is obtained from extrapolated values.

[0178] Δn (refractive index anisotropy) correlates with Δn in the near-infrared region used in optical sensors, which will be discussed later. A larger Δn results in greater phase modulation power for light of the target wavelength, making it particularly suitable for optical sensors. Δn at 25℃ and 589nm is the anomalous refractive index (n) of the liquid crystal composition using an Abbe refractometer. e ) and the refractive index (n o ) difference (n e -n o ) Furthermore, Δn can also be determined from the phase difference measurement device. The relationship Δn = Re / d holds between the phase difference Re, the thickness d of the liquid crystal layer, and Δn. A liquid crystal composition is injected into a glass cell with a polyimide alignment film that has undergone antiparallel rubbing treatment and has a cell gap (d) of approximately 3.0 μm. The in-plane Re is measured using a phase difference film / optical material inspection device RETS-100 (manufactured by Otsuka Electronics Co., Ltd.). The measurement was performed at a temperature of 25°C and a wavelength of 589 nm; the unit is not specified. The Δn of the compound represented by general formula (i) according to the present invention (including the sub-concept) at 25°C and 589 nm is preferably 0.35 or more, preferably 0.40 to 0.60, preferably 0.43 to 0.57, and preferably 0.45 to 0.55, from the viewpoint of the phase modulation power of light of the wavelength.

[0179] Higher dielectric anisotropy in the high-frequency range results in greater phase modulation power for radio waves in the target frequency band, making it particularly suitable for antenna applications. Furthermore, for antenna applications, a smaller dielectric loss tangent in the high-frequency range is preferable because it reduces energy loss in the target frequency band. In the compound represented by general formula (i) according to the present invention (including sub-concepts), the dielectric anisotropy Δε at 10 GHz is representative of the characteristics in the high-frequency region. r We measured it. Δε r =( ε r∥ -ε r⊥ ) Here, "ε r The symbol "∥" represents the dielectric constant, and the subscript "∥" indicates a component parallel to the orientation direction of the liquid crystal, while "⊥" indicates a component perpendicular to the orientation direction of the liquid crystal.

[0180] Δε r It can be measured by the following method. First, the liquid crystal composition is introduced into a capillary tube made of polytetrafluoroethylene (PTFE). The capillary tube 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. A capillary tube containing a liquid crystal composition is introduced into the center of a cavity resonator (manufactured by EM Lab Co., Ltd.) with a resonant frequency of 10 GHz. This cavity resonator has an outer diameter of 30 mm and an outer width of 26 mm. Then, a signal is input, and the result of the output signal is recorded using a network analyzer (manufactured by Keysight Technologies, Inc.). Using the difference between the resonance frequency of a PTFE capillary tube without a liquid crystal composition and the resonance frequency of a PTFE capillary tube with a liquid crystal composition, the dielectric constant (ε) at 10 GHz is determined. r ) will be decided. Furthermore, the resonance frequency and other properties of a PTFE capillary tube containing a liquid crystal composition are determined by controlling the orientation of the liquid crystal molecules, and are obtained as the values ​​of characteristic components perpendicular to and parallel to the orientation direction of the liquid crystal molecules. A magnetic field from a permanent magnet or electromagnet is used to align liquid crystal molecules perpendicular to the PTFE capillary (perpendicular to the effective length direction) or parallel to it (parallel to the effective length direction). For example, with a magnetic pole distance of 45 mm, the magnetic field strength near the center is 0.23 Tesla. Desired characteristic components are obtained by rotating a PTFE capillary tube containing a liquid crystal composition parallel or perpendicular to a magnetic field. The measurement was performed at a temperature of 25°C, and Δε r It has no units.

[0181] Δε at 25°C for a compound (including sub-concepts) represented by general formula (i) according to the present invention r While a larger value is preferable, from the viewpoint of phase modulation power in the GHz band, it is preferably 0.30 or higher, 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 a compound represented by the above-mentioned general formula (i) (including its sub-concept), other liquid crystal compounds as needed, and additives.

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

[0184] Examples of stabilizers include hydroquinones, hydroquinone monoalkyl ethers, tertiary butylcatechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, hindered phenols, and hindered amines. Examples of hindered phenols include hindered phenol antioxidants represented by the following structural formulas (XX-1) to (XX-3).

[0185] [ka]

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

[0187] [ka]

[0188] When using stabilizers, the types of stabilizers used in the liquid crystal composition are one or more, preferably 1 to 10, preferably 1 to 8, preferably 1 to 6, preferably 1 to 4, and preferably 1 to 2. When a stabilizer is used, the total content of the stabilizer in 100% by mass of the liquid crystal composition is preferably 0.005 to 1% by mass, preferably 0.02 to 0.50% by mass, and preferably 0.03 to 0.35% by mass.

[0189] (Liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment, and antennas) The following describes liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment, and antennas using the liquid crystal composition according to the present invention.

[0190] The liquid crystal display element according to the present invention is characterized by using the above-described liquid crystal composition and is preferably driven by an active matrix or passive matrix method. Furthermore, the liquid crystal display element according to the present invention is preferably a liquid crystal display element that reversibly switches the dielectric constant by reversibly changing the orientation direction of the liquid crystal molecules of the above-mentioned liquid crystal composition.

[0191] The sensor according to the present invention is characterized by using the above-mentioned liquid crystal composition, and examples of such embodiments include a distance measuring sensor that utilizes electromagnetic waves, visible light or infrared light, an infrared sensor that utilizes temperature changes, a temperature sensor that utilizes changes in reflected light wavelength due to changes in the pitch of cholesteric liquid crystal, a pressure sensor that utilizes changes in reflected light wavelength, an ultraviolet sensor that utilizes changes in reflected light wavelength due to changes in composition, an electrical sensor that utilizes temperature changes due to voltage or current, a radiation sensor that utilizes temperature changes associated with the tracks of radiation particles, an ultrasonic sensor that utilizes changes in liquid crystal molecular arrangement due to mechanical vibrations of ultrasound, and an electromagnetic field sensor that utilizes changes in reflected light wavelength due to temperature changes or changes in liquid crystal molecular arrangement due to electric fields. For the distance measuring sensor, it is preferable to use one designed for LiDAR (Light Detection and Ranging) which uses a light source. LiDAR is preferably used for satellites, aircraft, unmanned aerial vehicles (drones), automobiles, railways, and ships. For automotive applications, it is particularly preferable for autonomous vehicles. The light source is preferably an LED or a laser, and is preferably a laser. The light used in LiDAR is preferably infrared light, and its wavelength is preferably 800 to 2000 nm. In particular, infrared lasers with wavelengths of 905 nm or 1550 nm are preferred. If the cost of the photodetector used and sensitivity in all weather conditions are important, a 905nm infrared laser is preferred, while if safety regarding human vision is important, a 1550nm infrared laser is preferred. Because the liquid crystal composition according to the present invention exhibits a high Δn, it has a large phase modulation capability 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, it comprises a first transparent electrode layer, a second transparent electrode layer, a liquid crystal layer containing the above-described liquid crystal composition provided between the first transparent electrode layer and the second transparent electrode layer, an insulating layer provided between the second transparent electrode layer and the liquid crystal layer, and a high-resistance layer provided between the insulating layer and the liquid crystal layer. The liquid crystal lens according to the present invention can be 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-described liquid crystal composition, and one example of such a device is an 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 in a two-dimensional manner. The optical communication device according to the present invention can be used, for example, as a spatial phase modulator.

[0194] The antenna according to the present invention is characterized by using the above-described liquid crystal composition. More specifically, the antenna according to the present invention comprises a first substrate having a plurality of slots, a second substrate facing the first substrate and provided with 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 a liquid crystal composition, by using a liquid crystal composition containing one or more compounds represented by general formula (i) having a benzofuran structure or a benzothiophene structure and an isothiocyanate group (-NCS) (including sub-concepts), Δn is large and Δε r Because it is large and has good storage properties at low temperatures, it can provide an antenna that is highly reliable against external stimuli such as heat. This makes it possible to provide an antenna that enables 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 that combines a radial line slot array and a patch antenna array. The antenna structure according to the present invention can be applied by taking into consideration, for example, matters described in International Publication No. 2021 / 157189, etc. [Examples]

[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 contain each compound in the proportions shown in the table, and the content is indicated in "mass%". Note that compounds that can exist as both cis and trans isomers will be referred to as the trans isomer 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 charged into 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 below -60°C 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 below -60°C for 1 hour. After the reaction was complete, 10% by mass hydrochloric acid was poured into the reaction mixture and extracted with toluene. The organic layer was washed with saturated brine 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 the 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 the reaction was complete, saturated aqueous ammonium chloride solution was poured into the reaction mixture and extracted with ethyl acetate. The organic layer was washed with saturated brine, and then recrystallized with toluene to obtain 24.5 g of the compound represented by formula (I-1-4). 24.5 g of the compound represented by formula (I-1-4), 100 mL of dichloromethane, and 13.4 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel and heated and refluxed for 2 hours. After the reaction was complete, the organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 2 / 1) to obtain 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 was carried out for 3 hours while heating the reaction vessel to 80°C. After the reaction was complete, 10% by mass hydrochloric acid was poured into the reaction mixture and extracted with toluene. The organic layer was washed with saturated brine 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 the reaction vessel, and the reaction vessel was heated to 70°C. After the reaction was complete, 10% by mass hydrochloric acid was poured into the reaction mixture and extracted with ethyl acetate. The organic layer was washed with saturated brine, the solvent was removed by distillation, and dispersion washing with toluene was performed 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 the reaction vessel and heated and refluxed for 2 hours. After the reaction was complete, the organic layer was washed with saturated brine, 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 the 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 heating the reaction mixture at 60°C, a solution of 12 g of trimethylsilylacetylene dissolved in 15 mL of N,N-dimethylformamide was added dropwise, and the mixture was stirred at 60°C for 2 hours. After the reaction was complete, saturated ammonium chloride solution was poured into the reaction mixture and extracted with toluene. The organic layer was washed with saturated brine, and the toluene was removed by distillation. 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 complete, pure water was poured into the reaction mixture and extracted with ethyl acetate. The organic layer was washed with saturated brine, the solvent was removed by distillation, and 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 the reaction vessel. While heating the reaction mixture at 80°C, a solution of 17 g of the compound represented by formula (I-3-2) dissolved 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 complete, saturated aqueous ammonium chloride solution was poured into the reaction mixture and extracted with ethyl acetate. The organic layer was washed with saturated brine, and then recrystallized with 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'-thiocarboniludi-2(1H)pyridone were added to the reaction vessel and reacted at room temperature for 2 hours. After the reaction was complete, the organic layer was washed with saturated brine, 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 the compound represented by formula (I-4)

[0202] [ka]

[0203] The compound represented by formula (I-4) was obtained by the same method 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 by the same method 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 the compound represented by formula (I-6)

[0206] [ka]

[0207] The compound represented by formula (I-6) was obtained by the same method 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 the compound represented by formula (I-7)

[0208] [ka]

[0209] The compound represented by formula (I-7) was obtained by the same method 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 the compound represented by formula (I-8)

[0210] [ka]

[0211] The compound represented by formula (I-8) was obtained by the same method 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 the compound represented by formula (I-9)

[0212] [ka]

[0213] The compound represented by formula (I-9) was obtained by the same method 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 the compound represented by formula (I-10)

[0214] [ka]

[0215] The compound represented by formula (I-10) was obtained by the same method 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) exhibiting the following physical properties was prepared. All values ​​are measured values. T n-i (Nematic phase-isotropic liquid phase transition temperature): 74.0℃ Δε (dielectric anisotropy at 25℃, 1kHz): 5.11 Δn (refractive index anisotropy at 25℃, 589nm): 0.141 γ1 (rotational viscosity coefficient at 25°C): 107 mPa·s

[0217] Compounds (I-1) to (I-10) obtained in the examples, as well as compounds represented by formulas (C-1) to (C-2) that do not employ benzofuran and benzothiophene structures, were added to the base liquid crystal (LC-1) to prepare liquid crystal compositions containing 0%, 5%, and 10% by mass of each compound, respectively, in a total liquid crystal composition of 100% by mass. Then, using the least squares method, Δn and Δε at 100% mass of each compound are determined. r The extrapolated value was calculated. The results are shown in Table 1. Furthermore, since compound (C-2) precipitated, Δn and Δε r We were unable to find the extrapolated value.

[0218] (Storage stability test) Compounds (I-1) to (I-10) obtained in the examples, as well as compounds represented by formulas (C-1) to (C-2) that do not employ benzofuran and benzothiophene structures, were added to the base liquid crystal (LC-1) to prepare a liquid crystal composition containing 5% by mass of each compound in 100% by mass of the liquid crystal composition. 0.5 g of the prepared liquid crystal composition was weighed into a 1 mL sample vial (Maruemu Co., Ltd.) and degassed at 150°C and 250 Pa for 10 minutes. The vial was then purged with dry nitrogen and the lid was attached. This was stored in a 0°C temperature-controlled constant temperature bath (ESPEC Corporation, SH-241) for two weeks, and the crystallization of the liquid crystal composition was visually checked daily. Samples where no crystallization was observed after one week were marked "○", those where crystallization was observed after the fourth day were marked "△", and those where crystallization was observed by the third day were marked "×". The results are shown in Table 1.

[0219] [ka]

[0220] [Table 1]

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

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

Claims

1. The following general formula (i) 【Chemistry 1】 (In general formula (i), R ｉ１ This represents an alkyl group having 1 to 20 carbon atoms. One or more -CH groups in the alkyl group ２ Each of the hyphens may be independently substituted with -O-, -S-, -CO- and / or -CS-. One or more -CH groups in the alkyl group ２ -CH ２ Each of the hyphens may be independently substituted with -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 halogen atoms, Oxygen atoms do not directly bond with each other. A ｉｂｆ／ｔ The following general formula (A ｉｂｆ -1) and (A ｉｂｔ -1) 【Chemistry 2】 (General formula (A ｉｂｆ -1) and (A ｉｂｔ -1), White dots are R ｉ１ This represents a bonding action to, Black spot Z ｉ１ This represents a bonding action to, L ｉ１ and L ｉ２ Each of these 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 groups in the alkyl group ２ Each of the hyphens may be independently substituted with -O-, -S-, -CO- and / or -CS-. One or more -CH groups in the alkyl group ２ -CH ２ Each of the hyphens may be independently 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 be independently substituted with halogen atoms, Oxygen atoms do not directly bond with each other. This represents a group selected from the group consisting of groups represented by , A ｉ１ The formula is as follows (A ｉ１ -1), (A ｉ１ -SP-1), (A ｉ１ -SP-2), (A ｉ１ -SP-3), (A ｉ１ -SP-4) 【Chemistry 2】 (Formula (A ｉ１ - 1), (A ｉ１ - SP - 1), (A ｉ１ - SP - 2), (A ｉ１ - SP - 3), (A ｉ１ - SP - 4), among White spot Z ｉ１ This represents a bonding action to, Black spot Z ｉ２ Alternatively, it represents a bond to an isothiocyanate group (-NCS). This represents a group selected from the group consisting of groups represented by , A ｉ２ The formula is as follows (A ｉ２ -1), (A ｉ２ -SP-1), (A ｉ２ -SP-2), (A ｉ２ -SP-3), (A ｉ２ -SP-4) 【Chemistry 2】 (Formula (A ｉ２ - 1), (A ｉ２ - SP - 1), (A ｉ２ - SP - 2), (A ｉ２ - SP - 3), (A ｉ２ - SP - 4), among White spot Z ｉ２ This represents a bonding action to, Black spot Z ｉ２ Alternatively, it represents a bond to an isothiocyanate group (-NCS). This represents a group selected from the group consisting of groups represented by , Substituent S ｉ１ This represents any of the following: 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 groups in the alkyl group ２ Each of the hyphens may be independently substituted with -O-, -S-, and / or -CO-. One or more -CH groups in the alkyl group ２ -CH ２ Each of the hyphens may be independently 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 be independently substituted with halogen atoms, Oxygen atoms do not directly bond with each other. Substituent S ｉ１ If there are multiple items, they may be the same or different. Z ｉ１ and Z ｉ２ Each of these independently represents a single bond or -C≡C-, Z ｉ１ and Z ｉ２ At least one of them represents -C≡C-, n ｉ１ This represents an integer from 0 to 3, A ｉ２ or Z ｉ２ If multiple instances exist, they may be identical or different. A compound represented by, The following general formulas (i-2), (i-4), (i-5), and (i-6) 【Transformation 3】 (In general formulas (i-2), (i-4), (i-5), and (i-6), R i1, A ibf / t, A i1, and A i2 have the same meanings as R i1, A ibf / t, A i1, and A i2 in the general formula (i) above. A compound selected from the group consisting of compounds represented by [the formula].

2. The aforementioned R ｉ１ The compound according to claim 1, wherein is any of the following: 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.

3. A liquid crystal composition comprising one or more compounds according to claim 1 or 2.

4. A liquid crystal display element using the liquid crystal composition described in claim 3.

5. A sensor using the liquid crystal composition described in claim 3.

6. A liquid crystal lens using the liquid crystal composition described in claim 3.

7. An optical communication device using the liquid crystal composition described in claim 3.

8. An antenna using the liquid crystal composition described in claim 3.

9. The antenna according to claim 8, A first circuit board equipped with multiple slots, A second substrate, which is opposite the first substrate and has a power supply section, A first dielectric layer is provided between the first substrate and the second substrate, Multiple patch electrodes arranged corresponding to the multiple slots, A third substrate on which the patch electrode is provided, The device comprises a liquid crystal layer provided between the first substrate and the third substrate, An antenna in which the liquid crystal layer contains the liquid crystal composition described in claim 3.

Images