Compound, and liquid crystal composition, liquid crystal display element, sensor, liquid crystal lens, optical communication device and antenna each comprising compound

Abstract

An embodiment of the present invention addresses the problem of providing a compound capable of providing a liquid crystal composition excellent in characteristics such as Tni, Δn, Δεr, tanδiso and / or preserving properties, and providing a liquid crystal composition, a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device and an antenna each comprising the compound. The present invention addresses the problem of providing a compound capable of providing a liquid crystal composition having, for example, a high Tni, a large Δn, a large Δεr, and a small tanδiso and having satisfactory preserving properties at room temperature and providing a liquid crystal composition, a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device and an antenna each comprising the compound.　Specifically, the liquid crystal composition contains one or two or more compounds represented by general formula (i) having a predetermined ring structure and an isothiocyanate group (-NCS).

Description

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

[0001] This 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.

[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 communication has used parabolic antennas, but when used in mobile vehicles such as automobiles, the parabolic antenna must be constantly pointed towards the satellite, requiring large movable parts. 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 antenna shape can be flat. In addition, 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 of automobiles and other vehicles requires the download of large amounts of high-precision 3D map data. However, with an LCD antenna, by integrating the antenna into the automobile, it becomes possible to download large amounts of data from communication satellites without mechanical moving parts. The frequency band used for satellite communication is approximately 13 GHz, which is significantly different from the frequencies used in conventional LCD display applications. Therefore, the required physical properties of liquid crystals differ greatly. For example, the required Δn for liquid crystals used in antennas is around 0.4, and the operating temperature range is, for example, -20 to 120°C. In addition, infrared laser image recognition and distance measuring devices using liquid crystals are attracting attention as sensors for autonomous driving of mobile objects such as automobiles. For this application, the required Δn 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 that constitute liquid crystal compositions exhibiting a high Δn of 0.2 or more have low compatibility. Therefore, selecting liquid crystalline compounds with high compatibility is also important. As an example of liquid crystal technology for antennas, Patent Document 1 can be cited. Non-Patent Document 1 proposes the use of liquid crystal materials as components of high-frequency devices.

[0003] Japanese Patent Publication No. 2016-37607

[0004] Dolfi, D., "Electronics Letters", (UK), 1993, Vol. 29, No. 10, p. 926-928

[0005] One aspect of the present invention is T ｎｉ , Δn, Δε ｒ , tanδ ｉｓｏ , and / or to provide a compound capable of obtaining a liquid crystal composition excellent in characteristics such as storage stability, 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 same. Also, one aspect of the present invention is T ｎｉ is high, Δn is large, Δε ｒ is large, tanδ ｉｓｏ is small, and to provide a compound capable of obtaining a liquid crystal composition having good storage stability at room temperature, 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 same. Note that the description of these problems does not prevent the existence of other problems, and one aspect of the present invention does not need to solve all of these problems.

[0006] As a result of intensive studies, the present inventors have found that a liquid crystal composition containing one or more compounds represented by the general formula (i) having a predetermined ring 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 for solving the above problems is as follows.

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

[0008] (In the general formula (i), R ｉ１ represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and one or more -CH ２ - in the alkyl group may each be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH ２ -CH ２Each of the -s may be independently substituted with -CH=CH-, -CF=CF- and / or -C≡C-, and one or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms, but oxygen atoms do not directly bond with each other. ｉ１ The following general formula (A ｉ１ -1) to (A ｉ１ -4)

[0009] (General formula (A ｉ１ -1) to (A ｉ１ -4) In the middle, the white dot is R ｉ１ The black dot represents a bond to Z. ｉ１ This represents a bonding to S Ａｉ１ 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, and one or more -CH groups in the alkyl group. ２ Each of the -s may be independently substituted with -O-, -S-, -CO- and / or -CS-, and one or more -CH groups in the alkyl group. ２ -CH ２ The hyphens may each be independently substituted with -CH=CH-, -CF=CF- and / or -C≡C-, and one or more hydrogen atoms in the alkyl group may each be independently substituted with halogen atoms, but oxygen atoms will not be directly bonded to each other.) This represents a group selected from the group consisting of the groups represented by A ｉ２ The following general formula (A ｉ２ -1) to (A ｉ２ -3)

[0010] (Formula (A ｉ２ -1) to (A ｉ２ -3) In the middle, the white dot is Z ｉ１ The black dot represents a bond to Z. ｉ２Alternatively, it represents a bond to an isothiocyanate group (-NCS). Ａｉ２ Each of these independently 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, and one or more -CH groups in the alkyl group. ２ Each of the -s may be independently substituted with -O-, -S-, -CO- and / or -CS-, and one or more -CH groups in the alkyl group. ２ -CH ２ The hyphens may each be independently substituted with -CH=CH-, -CF=CF- and / or -C≡C-, and one or more hydrogen atoms in the alkyl group may each be independently substituted with halogen atoms, but oxygen atoms will not be directly bonded to each other.) This represents a group selected from the group consisting of the groups represented by A ｉ３ Each of these independently represents either a hydrocarbon ring having 3 to 16 carbon atoms or a heterocycle having 3 to 16 carbon atoms, and A ｉ３ One or more hydrogen atoms in it are each independently S Ａｉ３ It may be replaced by S Ａｉ３ 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, and one or more -CH groups in the alkyl group. ２ Each of the -s may be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH groups in the alkyl group. ２ -CH ２Each of the -s may be independently substituted with -CH=CH-, -CF=CF- and / or -C≡C-, and one or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms, but oxygen atoms do not directly bond with each other. Ａｉ３ If there are multiple, they may be the same or different, Z ｉ１ and Z ｉ２ Each of these independently represents either a single bond or an alkylene group having 1 to 20 carbon atoms, and one or more of these alkylene groups contain -CH ２ The hyphens are, respectively, -O- and -CF. ２ - and / or -CO- may be substituted, and one or more -CH groups in the alkylene group ２ -CH ２ Each of the hyphens is independent of the other, -CH ２ -CH(CH ３ )-,-CH(CH ３ ) - CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ )-,-C(CH ３ ) may be substituted with -CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, and oxygen atoms do not directly bond with each other, n ｉ１ This represents an integer between 0 and 2, but A ｉ３ or Z ｉ２ If multiple compounds exist, they may be the same or different.) A liquid crystal composition comprising one or more compounds represented by ).

[0011] Section 2. The compound represented by the above general formula (i) is one of the following general formulas (i-1) to (i-13)

[0012]

[0013] (In general formulas (i-1) to (i-13), R ｉ１ S Ａｉ１ S Ａｉ２ and S Ａｉ３ R in the above general formula (i) ｉ１S Ａｉ１ S Ａｉ２ and S Ａｉ３ The liquid crystal composition according to item 1, selected from the group consisting of compounds represented by ).

[0014] Item 3. The liquid crystal composition according to item 1 or 2, wherein the total content of the compound represented by general formula (i) in 100% by mass of the liquid crystal composition is 1% by mass or more.

[0015] Section 4. Furthermore, the following general formula (ii)

[0016] (In general formula (ii), R ｉｉ１ Each of these independently represents an alkyl group having 1 to 20 carbon atoms, and one or more of the -CH groups within the alkyl group. ２ Each of the -s may be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH groups in the alkyl group ２ -CH ２ Each of the -s may be independently substituted with -CH=CH-, -CF=CF- and / or -C≡C-, and one or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms, but oxygen atoms do not directly bond with each other. ｉｉ１ and A ｉｉ２ These are, independently, the following groups (a), (b), (c), and (d): (a) 1,4-cyclohexylene group (one -CH group present in this group) ２ - or two or more non-adjacent -CH ２(b) 1,4-phenylene group (one or more -CH= present in 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-2,7-diyl group, 2,3-dihydro-1H-indene-1,5-diyl group, 2,3-dihydro-1H-indene-2,5-diyl group, 2,3-dihydro-1H-indene-1,6-diyl group, 1 H-indene-2,5-diyl group, 1H-indene-1,5-diyl group, 1H-indene-3,5-diyl group, 1H-indene-1,6-diyl group, 1H-indene-2,6-diyl group, 1H-indene-3,6-diyl group (one -CH= or two or more -CH= present in the 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) Represents a group selected from the group consisting of thiophene-2,5-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group, thieno[3,2-b]thiophene-2,5-diyl group, benzo[1,2-b:4,5-b']dithiophene-2,6-diyl group (one -CH= or two or more -CH= present in this group may be replaced with -N=), and A ｉｉ１ and A ｉｉ２ One or more hydrogen atoms in the middle are independently substituents S ｉｉ１ Substituents S may be substituted by ｉｉ１represents any one of a halogen atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group or an alkyl group having 1 to 20 carbon atoms, and one or more of the -CH in the alkyl group ２ - may each independently be substituted with -O-, -S-, -NH-, -CO- and / or -CS-, and one or more of the -CH in the alkyl group ２ -CH ２ - may each independently be substituted with -CH=CH-, -CF=CF- and / or -C≡C-, and one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom, but oxygen atoms do not directly bond to each other, and when there are multiple substituents S ｉｉ１ they may be the same or different, and Z ｉｉ１ represents either a single bond or an alkylene group having 1 to 20 carbon atoms, and one or more of the -CH in the alkylene group ２ - may each independently be substituted with -O-, -CF ２ - and / or -CO-, and one or more of the -CH in the alkylene group ２ -CH ２ - may each independently be substituted with -CH ２ -CH(CH ３ )-, -CH(CH ３ )-CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ )-, -C(CH ３ )=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, and oxygen atoms do not directly bond to each other, and n ｉｉ１ represents an integer from 1 to 4, and A ｉｉ１ and Z ｉｉ１If multiple compounds exist, they may be the same or different. However, this excludes compounds represented by general formula (i).) A liquid crystal composition according to any one of claims 1 to 3, comprising one or more compounds represented by ).

[0017] Section 5. tanδ at 25°C ｉｓｏ A liquid crystal composition according to any one of claims 1 to 4, wherein the value is 0.011 or less.

[0018] Item 6. A liquid crystal display element using the liquid crystal composition described in any one of items 1 to 5.

[0019] Item 7. A liquid crystal display element according to Item 6, which is driven by an active matrix or passive matrix and reversibly switches the dielectric constant.

[0020] Item 8. A sensor using a liquid crystal composition as described in any one of items 1 to 5.

[0021] Item 9. A liquid crystal lens using a liquid crystal composition described in any one of items 1 to 5.

[0022] Item 10. Optical communication equipment using a liquid crystal composition as described in any one of items 1 to 5.

[0023] Item 11. An antenna using a liquid crystal composition as described in any one of items 1 to 5.

[0024] Item 12. An antenna according to Item 11, comprising: 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 liquid crystal composition according to any one of Items 1 to 5.

[0025] Item 13. The following general formula (i)

[0026] (In general formula (i), R ｉ１ represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and one or more -CH groups are present in the alkyl group.２ - may each independently be optionally substituted with -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH in the alkyl group ２ -CH ２ - may each independently be optionally substituted with -CH=CH-, -CF=CF- and / or -C≡C-, and one or more hydrogen atoms in the alkyl group may each independently be optionally substituted with a halogen atom, but oxygen atoms do not directly bond to each other, and A ｉ１ is a group selected from the group consisting of groups represented by the following general formulas (A ｉ１ -1) to (A ｉ１ -4)

[0027] (In general formulas (A ｉ１ -1) to (A ｉ１ -4), the white dots represent bonds to R ｉ１ , the black dots represent bonds to Z ｉ１ , S Ａｉ１ 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, and one or more -CH in the alkyl group ２ - may each independently be optionally substituted with -O-, -S-, -CO- and / or -CS-, and one or more -CH in the alkyl group ２ -CH ２ - may each independently be optionally substituted with -CH=CH-, -CF=CF- and / or -C≡C-, and one or more hydrogen atoms in the alkyl group may each independently be optionally substituted with a halogen atom, but oxygen atoms do not directly bond to each other.) represents a group selected from the group consisting of groups represented by the following general formulas (A ｉ２ is a group selected from the group consisting of groups represented by the following general formulas (A ｉ２ -1) to (A ｉ２ -3)

[0028] (General formula (A ｉ２ -1) to (A ｉ２ -3) In the middle, 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). Ａｉ２ Each of these independently 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, and one or more -CH groups in the alkyl group. ２ Each of the -s may be independently substituted with -O-, -S-, -CO- and / or -CS-, and one or more -CH groups in the alkyl group. ２ -CH ２ The hyphens may each be independently substituted with -CH=CH-, -CF=CF- and / or -C≡C-, and one or more hydrogen atoms in the alkyl group may each be independently substituted with halogen atoms, but oxygen atoms will not be directly bonded to each other.) This represents a group selected from the group consisting of the groups represented by A ｉ３ Each of these independently represents either a hydrocarbon ring having 3 to 16 carbon atoms or a heterocycle having 3 to 16 carbon atoms, and A ｉ３ One or more hydrogen atoms in it are each independently S Ａｉ３ It may be replaced by S Ａｉ３ 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, and one or more -CH groups in the alkyl group. ２Each of the -s may be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH groups in the alkyl group. ２ -CH ２ Each of the -s may be independently substituted with -CH=CH-, -CF=CF- and / or -C≡C-, and one or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms, but oxygen atoms do not directly bond with each other. Ａｉ３ If there are multiple, they may be the same or different, Z ｉ１ and Z ｉ２ Each of these independently represents either a single bond or an alkylene group having 1 to 20 carbon atoms, and one or more of these alkylene groups contain -CH ２ The hyphens are, respectively, -O- and -CF. ２ - and / or -CO- may be substituted, and one or more -CH groups in the alkylene group ２ -CH ２ Each of the hyphens is independent of the other, -CH ２ -CH(CH ３ )-,-CH(CH ３ ) - CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ )-,-C(CH ３ ) may be substituted with -CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, and oxygen atoms do not directly bond with each other, n ｉ１ This represents an integer between 0 and 2, but A ｉ３ or Z ｉ２ If multiple compounds exist, they may be identical or different.) A compound represented by .

[0029] According to the present invention, a liquid crystal composition comprising one or more compounds represented by general formula (i) having a predetermined ring structure and an isothiocyanate group (-NCS) is used to obtain T ｎｉ Δn, Δε ｒ , tanδ ｉｓｏ, and / or, a liquid crystal composition with excellent properties such as storage capacity can be obtained. For example, T ｎｉ When Δn is high, Δε ｒ Large, tanδ ｉｓｏ A liquid crystal composition with low tanδ can be obtained, and this liquid crystal composition is useful for liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment, and antennas. Furthermore, the liquid crystal composition according to the present invention has tanδ ｉｓｏ It excels at being small.

[0030] (Compound represented by general formula (i)) The liquid crystal composition according to the present invention comprises one or more compounds represented by general formula (i) having a predetermined ring structure and an isothiocyanate group (-NCS).

[0031]

[0032] In general formula (i), R ｉ１ This represents an alkyl group having 1 to 20 carbon atoms. The alkyl group having 1 to 20 carbon atoms can be linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, and preferably 2 to 6. One or more -CH groups in the alkyl group ２ Each of the -s may be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-. Also, 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-, 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, when the alkyl group is substituted with a predetermined group, oxygen atoms will not directly bond to each other. Also, from the viewpoint of compound stability, it is preferable that sulfur atoms and / or oxygen atoms and sulfur atoms do not directly bond to each other. For example, R ｉ１ This is one of the -CH groups in the alkyl group. ２By substituting - with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented. The alkoxy group is linear, branched, or cyclic, and a linear alkoxy group is preferred. The number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6. Also, R ｉ１ This is one of the -CH groups in the alkyl group. ２ By substituting - with -S-, an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms can be represented. The alkylsulfanyl group is a linear, branched, or cyclic alkylsulfanyl group, and a linear alkylsulfanyl group is preferred. The number of carbon atoms in the alkylsulfanyl group is preferably 2 to 10, preferably 2 to 6. Also, R ｉ１ This refers to one or more -CH groups in the alkyl group. ２ -CH ２ By substituting -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented. The alkenyl group is linear, branched, or cyclic, and a linear alkenyl group is preferred. The number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6. Also, R ｉ１ This refers to one or more -CH groups in the alkyl group. ２ -CH ２ By substituting -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented. The alkynyl group is linear, branched, or cyclic, and a linear alkynyl group is preferred. The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6. Also, R ｉ１ This is one of the -CH groups in the alkyl group. ２ - is replaced by -O- and one or more -CH ２ -CH ２By substituting -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented. 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, 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 halogenated alkyl group is preferably 2 to 10, preferably 2 to 6. Also, R ｉ１ This is one of the -CH groups in the alkyl group. ２ A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by substituting - with -O- and substituting one or more hydrogen atoms in the alkyl group with halogen atoms. The halogenated alkoxy group is linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6. ｉ１ Specific examples of alkyl groups with 1 to 20 carbon atoms in the formula (including substituted ones) include the formula (R ｉ１ -1) to (R ｉ１ Examples include the base represented by -36).

[0033]

[0034] Formula (R ｉ１ -1) to (R ｉ１ -36) Among them, black spot A ｉ１ This represents a connection to R. ｉ１ From the viewpoint of Δn and compatibility with other liquid crystal compounds, linear alkyl groups having 1 to 6 carbon atoms are preferred.

[0035] In general formula (i), A ｉ１ The following general formula (Aｉ１ -1) to (A ｉ１ This represents a group selected from the group consisting of the groups represented by -4).

[0036]

[0037] General formula (A ｉ１ -1) to (A ｉ１ -4) In the middle, the white dot is R ｉ１ The black dot represents a bond to Z. ｉ１ This represents a binding operation.

[0038] General formula (A ｉ１ -1) to (A ｉ１ -4) Medium, S Ａｉ１ 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 linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, and preferably 2 to 6. One or more -CH groups are present in the alkyl group. ２ Each of the -s may be independently substituted with -O-, -S-, -CO- and / or -CS-. Also, 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-, 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, when the alkyl group is substituted with a predetermined group, oxygen atoms will not directly bond to each other. Also, from the viewpoint of compound stability, it is preferable that sulfur atoms and / or oxygen atoms and sulfur atoms do not directly bond to each other. For example, SＡｉ１ This is one of the -CH groups in the alkyl group. ２ By substituting - with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented. 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, preferably 2 to 6. Also, S Ａｉ１ This is one of the -CH groups in the alkyl group. ２ By substituting - with -S-, an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms can be represented. The alkylsulfanyl group is a linear, branched, or cyclic alkylsulfanyl group, and a linear alkylsulfanyl group is preferred. The number of carbon atoms in the alkylsulfanyl group is preferably 2 to 10, preferably 2 to 6. Also, S Ａｉ１ This refers to one or more -CH groups in the alkyl group. ２ -CH ２ The - is replaced with -CH=CH- to represent an alkenyl group having 2 to 20 carbon atoms. The alkenyl group is linear, branched, or cyclic, and a linear alkenyl group is preferred. The number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6. Also, S Ａｉ１ This refers to one or more -CH groups in the alkyl group. ２ -CH ２ By substituting -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented. The alkynyl group is linear, branched, or cyclic, and a linear alkynyl group is preferred. The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6. Also, S Ａｉ１ This is one of the -CH groups in the alkyl group. ２ - is replaced by -O- and one or more -CH ２ -CH ２By substituting -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented. The alkenyloxy group is linear, branched, or cyclic, and a linear alkenyloxy group is preferred. The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6. Also, S Ａｉ１ 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 halogenated alkyl group is preferably 2 to 10, preferably 2 to 6. Also, S Ａｉ１ This is one of the -CH groups in the alkyl group. ２ A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by substituting a - with -O- and substituting one or more hydrogen atoms in the alkyl group with halogen atoms. The halogenated alkoxy group is linear, branched, or cyclic, and a linear halogenated alkoxy group is preferred. The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, and preferably 2 to 6.

[0039] S Ａｉ１ Specific examples of alkyl groups with 1 to 20 carbon atoms (including substituted ones) in the following formula (S Ａｉ１ -1) ~ (S Ａｉ１ Examples include the base represented by -36).

[0040]

[0041] Formula (S Ａｉ１ -1) ~ (S Ａｉ１ -36) In this example, the black dots represent bonds to the ring structure. Δn, from the viewpoint of compatibility with other liquid crystal compounds, S Ａｉ１ Each of these is preferably independently a hydrogen atom, a fluorine atom, or a linear alkyl group having 1 to 6 carbon atoms.

[0042] General formula (A ｉ１ A concrete example of the base represented by -1) is the following formula (A ｉ１ A group represented by -1-1) is preferred.

[0043]

[0044] Formula (A ｉ１ In the base represented by -1-1), the white dot is R ｉ１ The black dot represents a bond to Z. ｉ１ This represents a binding operation.

[0045] General formula (A ｉ１ A concrete example of the base represented in -2) is the following formula (A ｉ１ A group represented by -2-1) is preferred.

[0046]

[0047] Formula (A ｉ１ In the base represented by -2-1), the white dot is R ｉ１ The black dot represents a bond to Z. ｉ１ This represents a binding operation.

[0048] General formula (A ｉ１ A concrete example of the base represented in -3) is the following formula (A ｉ１ -3-1) ~ (A ｉ１ A group represented by -3-2) is preferred.

[0049]

[0050] Formula (A ｉ１ -3-1) ~ (A ｉ１ In the base represented by -3-2), the white dot is R ｉ１ The black dot represents a bond to Z. ｉ１ This represents a binding operation.

[0051] General formula (A ｉ１ A concrete example of the base represented by -4) is the following formula (A ｉ１ -4-1) ~ (A ｉ１ A group represented by -4-2) is preferred.

[0052]

[0053] Formula (A ｉ１ -4-1) ~ (A ｉ１In the base represented by -4-2), the white dot is R ｉ１ The black dot represents a bond to Z. ｉ１ This represents a binding operation.

[0054] In general formula (i), A ｉ２ The following general formula (A ｉ２ -1) to (A ｉ２ This represents a group selected from the group consisting of the groups represented by -3).

[0055]

[0056] General formula (A ｉ２ -1) to (A ｉ２ -3) In the middle, 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).

[0057] General formula (A ｉ２ -1) to (A ｉ２ -3) Medium, S Ａｉ２ Each of these independently 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 having 1 to 20 carbon atoms is linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, and preferably 2 to 6. One or more -CH groups are present in the alkyl group. ２ Each of the -s may be independently substituted with -O-, -S-, -CO- and / or -CS-. Also, one or more -CH groups in the alkyl group. ２ -CH ２Each of the hyphens may be independently substituted with -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, when the alkyl group is substituted with a predetermined group, oxygen atoms will not directly bond to each other. Also, from the viewpoint of compound stability, it is preferable that sulfur atoms and / or oxygen atoms and sulfur atoms do not directly bond to each other. For example, S Ａｉ２ This is one of the -CH groups in the alkyl group. ２ By substituting - with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented. 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, preferably 2 to 6. Also, S Ａｉ２ This is one of the -CH groups in the alkyl group. ２ By substituting - with -S-, an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms can be represented. The alkylsulfanyl group is a linear, branched, or cyclic alkylsulfanyl group, and a linear alkylsulfanyl group is preferred. The number of carbon atoms in the alkylsulfanyl group is preferably 2 to 10, preferably 2 to 6. Also, S Ａｉ２ This refers to one or more -CH groups in the alkyl group. ２ -CH ２ The - is replaced with -CH=CH- to represent an alkenyl group having 2 to 20 carbon atoms. The alkenyl group is linear, branched, or cyclic, and a linear alkenyl group is preferred. The number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6. Also, S Ａｉ２ This refers to one or more -CH groups in the alkyl group. ２ -CH ２By substituting -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented. The alkynyl group is linear, branched, or cyclic, and a linear alkynyl group is preferred. The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6. Also, S Ａｉ２ This is one of the -CH groups in the alkyl group. ２ - is replaced by -O- and one or more -CH ２ -CH ２ By substituting -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented. The alkenyloxy group is linear, branched, or cyclic, and a linear alkenyloxy group is preferred. The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6. Also, S Ａｉ２ 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 halogenated alkyl group is preferably 2 to 10, preferably 2 to 6. Also, S Ａｉ２ This is one of the -CH groups in the alkyl group. ２ A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by substituting a - with -O- and substituting one or more hydrogen atoms in the alkyl group with halogen atoms. The halogenated alkoxy group is linear, branched, or cyclic, and a linear halogenated alkoxy group is preferred. The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, and preferably 2 to 6.

[0058] S Ａｉ２ Specific examples of alkyl groups with 1 to 20 carbon atoms (including substituted ones) in the following formula (S Ａｉ２ -1) ~ (S Ａｉ２Examples include the base represented by -36).

[0059]

[0060] Formula (S Ａｉ２ -1) ~ (S Ａｉ２ -36) In this example, the black dots represent bonds to the ring structure. Δn, from the viewpoint of compatibility with other liquid crystal compounds, S Ａｉ２ Each of these is preferably a fluorine atom or a linear alkyl group having 1 to 6 carbon atoms.

[0061] General formula (A ｉ２ A concrete example of the base represented by -1) is the following formula (A ｉ２ A group represented by -1-1) is preferred.

[0062]

[0063] Formula (A ｉ２ In the base represented by -1-1), 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).

[0064] General formula (A ｉ２ A concrete example of the base represented in -2) is the following formula (A ｉ２ A group represented by -2-1) is preferred.

[0065]

[0066] Formula (A ｉ２ In the base represented by -2-1), 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).

[0067] General formula (A ｉ２ A concrete example of the base represented in -3) is the following formula (A ｉ２ A group represented by -3-1) is preferred.

[0068]

[0069] Formula (A ｉ２ In the base represented by -3-1), the white dot is Z ｉ１ The black dot represents a bond to Z. ｉ２Alternatively, it represents a bond to an isothiocyanate group (-NCS).

[0070] In general formula (i), A ｉ３ Each of these independently represents either a hydrocarbon ring having 3 to 16 carbon atoms or a heterocycle having 3 to 16 carbon atoms. More specifically, a hydrocarbon ring having 3 to 16 carbon atoms or a heterocycle having 3 to 16 carbon atoms is defined as the following groups (a), (b), (c), and (d): (a) 1,4-cyclohexylene group (one -CH group present in this group) ２ - or two or more non-adjacent -CH ２ (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= present in 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) Represents a group selected from the group consisting of thiophene-2,5-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group, and thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= present in this group may be replaced with -N=).

[0071] Aｉ３ One or more hydrogen atoms in it are each independently S Ａｉ３ It may be replaced by S. Ａｉ３ 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, preferably 3 to 6. One or more -CH groups are present in the alkyl group. ２ Each of the -s may be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-. Also, 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-, 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, when the alkyl group is substituted with a predetermined group, oxygen atoms will not directly bond to each other. Also, from the viewpoint of compound stability, it is preferable that sulfur atoms and / or oxygen atoms and sulfur atoms do not directly bond to each other. Ａｉ３ As for Δn, a fluorine atom is preferred from the viewpoint of compatibility with other liquid crystal compounds. Ａｉ３ If there are multiple items, they may be the same or different.

[0072] A ｉ３ S in Ａｉ３ The substitution position is the following general formula (A ｉ３ -SP-1) ~ (A ｉ３ It is preferable that it be one of the following: -SP-4).

[0073]

[0074] Formula (A ｉ３ -SP-1) ~ (A ｉ３ -SP-4) 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).

[0075] More specifically, A ｉ３ The formula is as follows (A ｉ３ -1) to (A ｉ３ -11) is preferable to represent any of the above.

[0076]

[0077] Formula (A ｉ３ -1) to (A ｉ３ -11) 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).

[0078] In general formula (i), Z ｉ１ and Z ｉ２ Each of these independently represents either a single bond or an alkylene group having 1 to 20 carbon atoms. The alkylene group is linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the alkylene group is preferably 2 to 10, preferably 2 to 6. One or more -CH groups are present in the alkylene group. ２ The hyphens are, respectively, -O- and -CF. ２ It may be substituted with - and / or -CO-. Also, one or more -CH groups in the alkylene group. ２ -CH ２ Each of the hyphens is independent of the other, -CH ２ -CH(CH ３ )-,-CH(CH ３ ) - CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ )-,-C(CH ３) may be substituted with -CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-. However, when the alkylene group is substituted with a predetermined group, oxygen atoms will not directly bond with each other.

[0079] Specific examples of alkylene groups with 2 to 20 carbon atoms (including substituted ones) are given by formula (Z ｉ１／２ -1) to (Z ｉ１／２ Examples include the base represented by -24).

[0080]

[0081] Expression (Z ｉ１／２ -1) to (Z ｉ１／２ -24) Among them, the white spot is A ｉ１ A ｉ２ Or A ｉ３ This represents a connection to A, with black dots at A ｉ２ Or A ｉ３ Represents a connection to Δn and / or Δε. ｒ From the perspective of Z ｉ１ is equation ( Z ｉ１／２ -4) It is preferable that (-C ≡ C-).

[0082] In general formula (i), n ｉ１ n represents an integer between 0 and 2, preferably between 0 and 1. ｉ１ When it is 1, from the viewpoint of improving Δn, Z ｉ２ It is preferable that A represents a single bond. In general formula (i), A ｉ３ or Z ｉ２ If there are multiple instances of this, they may be identical or different.

[0083] The compound represented by general formula (i) is preferably a compound represented by the following general formulas (i-1) to (i-13).

[0084]

[0085]

[0086] In general formulas (i-1) to (i-13), R ｉ１ S Ａｉ１ S Ａｉ２and S Ａｉ３ R in the above general formula (i) ｉ１ S Ａｉ１ S Ａｉ２ and S Ａｉ３ These represent the same meaning. Specific examples of compounds represented by general formula (i-1) include the compounds represented by the following structural formulas (i-1.1) to (i-1.3).

[0087]

[0088] Specific examples of compounds represented by general formula (i-2) include the compounds represented by the following structural formulas (i-2.1) to (i-2.3).

[0089]

[0090] Specific examples of compounds represented by general formula (i-3) include the compounds represented by the following structural formulas (i-3.1) to (i-3.3).

[0091]

[0092] Specific examples of compounds represented by general formula (i-4) include the compounds represented by the following structural formulas (i-4.1) to (i-4.3).

[0093]

[0094] Specific examples of compounds represented by general formula (i-5) include the compounds represented by the following structural formulas (i-5.1) to (i-5.3).

[0095]

[0096] Specific examples of compounds represented by the general formula (i-6) include the compounds represented by the following structural formulas (i-6.1) to (i-6.3).

[0097]

[0098] Specific examples of compounds represented by the general formula (i-7) include the compounds represented by the following structural formulas (i-7.1) to (i-7.3).

[0099]

[0100] Specific examples of compounds represented by the general formula (i-8) include the compounds represented by the following structural formulas (i-8.1) to (i-8.3).

[0101]

[0102] Specific examples of compounds represented by the general formula (i-9) include the compounds represented by the following structural formulas (i-9.1) to (i-9.3).

[0103]

[0104] Specific examples of compounds represented by the general formula (i-10) include the compounds represented by the following structural formulas (i-10.1) to (i-10.3).

[0105]

[0106] Specific examples of compounds represented by the general formula (i-11) include the compounds represented by the following structural formulas (i-11.1) to (i-11.3).

[0107]

[0108] Specific examples of compounds represented by the general formula (i-12) include the compounds represented by the following structural formulas (i-12.1) to (i-12.3).

[0109]

[0110] Specific examples of compounds represented by general formula (i-13) include the compounds represented by the following structural formulas (i-13.1) to (i-13.3).

[0111]

[0112] General formula (i), General formula (i-1) to (i-13), Structural formula (i-1.1) to (i-1.3), Structural formula (i-2.1) to (i-2.3), Structural formula (i-3.1) to (i-3.3), Structural formula (i-4) .1) ~ (i-4.3), structural formula (i-5.1) ~ (i-5.3), structural formula (i-6.1) ~ (i-6.3), structural formula (i-7.1) ~ (i-7.3), structural formula (i-8.1) ~ (i-8.3) The types of compounds used in the liquid crystal composition of the compounds represented by structural formulas (i-9.1) to (i-9.3), structural formulas (i-10.1) to (i-10.3), structural formulas (i-11.1) to (i-11.3), structural formulas (i-12.1) to (i-12.3), and / or structural formulas (i-13.1) to (i-13.3) are one or more types, preferably 1 to 10 types, preferably 1 to 5 types, and preferably 1 to 3 types.

[0113] General formula (i), General formula (i-1) to (i-13), Structural formula (i-1.1) to (i-1.3), Structural formula (i-2.1) to (i-2.3), Structural formula (i-3.1) to (i-3.3), Structural formula (i-4.1) to (i-4.3), structural formula (i-5.1) to (i-5.3), structural formula (i-6.1) to (i-6.3), structural formula (i-7.1) to (i-7.3), structural formula (i-8.1) to (i-8.3), structural formula (i-9. 1) The lower limit of the total content of the compounds represented by structural formulas (i-9.3) to (i-10.1) to (i-10.3), structural formulas (i-11.1) to (i-11.3), structural formulas (i-12.1) to (i-12.3), and / or structural formulas (i-13.1) to (i-13.3) in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, preferably 3% by mass or more, and preferably 5% by mass or more.

[0114] General formula (i), General formula (i-1) to (i-13), Structural formula (i-1.1) to (i-1.3), Structural formula (i-2.1) to (i-2.3), Structural formula (i-3.1) to (i-3.3), Structural formula (i-4.1) to ( i-4.3), Structural formula (i-5.1) to (i-5.3), Structural formula (i-6.1) to (i-6.3), Structural formula (i-7.1) to (i-7.3), Structural formula (i-8.1) to (i-8.3), Structural formula (i-9.1) The upper limit of the total content of the compounds represented by structural formulas (i-9.3), (i-10.1) to (i-10.3), (i-11.1) to (i-11.3), (i-12.1) to (i-12.3), and / or (i-13.1) to (i-13.3) in 100% by mass of the liquid crystal composition is preferably 25% by mass or less, preferably 20% by mass or less, and preferably 15% by mass or less.

[0115] General formula (i), General formulas (i-1) to (i-13), Structural formulas (i-1.1) to (i-1.3), Structural formulas (i-2.1) to (i-2.3), Structural formulas (i-3.1) to (i-3.3), Structural formula (i-4.1) to (i-4.3), structural formula (i-5.1) to (i-5.3), structural formula (i-6.1) to (i-6.3), structural formula (i-7.1) to (i-7.3), structural formula (i- The total content of the compounds represented by structural formulas (i-9.1) to (i-8.3), (i-9.1) to (i-9.3), (i-10.1) to (i-10.3), (i-11.1) to (i-11.3), (i-12.1) to (i-12.3), and / or (i-13.1) to (i-13.3) in 100% by mass of the liquid crystal composition is solubility, Δn and / or Δε ｒ From this viewpoint, it is preferably 1 to 25% by mass, preferably 3 to 20% by mass, and preferably 5 to 15% by mass.

[0116] Compounds represented by general formula (i) (including sub-concepts) can be synthesized using known synthesis methods, some of which are given below as examples. An indane derivative (A-1), which is an intermediate for synthesizing the compound of the present invention, can be obtained, for example, by the production method shown below.

[0117]

[0118] In the formula, R ｉ１ and S Ａｉ１ R in the general formula (i) is ｉ１ and S Ａｉ１ This expresses the same meaning. The indene derivative (A-2), which is an intermediate for synthesizing the compound of the present invention, can be obtained, for example, by the production method shown below.

[0119]

[0120] In the formula, R ｉ１ and S Ａｉ１ R in the general formula (i) is ｉ１ and S Ａｉ１ This expresses the same meaning. The tetralin derivative (A-3), which is an intermediate for synthesizing the compound of the present invention, can be obtained, for example, by the production method shown below.

[0121]

[0122] In the formula, S Ａｉ１ This is S in the general formula (i) above. Ａｉ１ This expresses the same meaning. Compounds represented by general formula (i) can be manufactured, for example, as follows: (Manufacturing method 1) Manufacturing of compounds represented by the following formula (s-3)

[0123]

[0124] In the formula, R ｉ１ A ｉ２ , and S Ａｉ１ R in the general formula (i) is ｉ１ A ｉ２ and S Ａｉ１This expresses the same meaning. 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 the palladium catalyst, ligands such as triphenylphosphine and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added. Specific examples of copper catalysts include copper(I) iodide. Specific examples of bases include triethylamine. (Method 2) Preparation of the compound represented by the following formula (s-9)

[0125]

[0126] In the formula, R ｉ１ A ｉ３ S Ａｉ１ and S Ａｉ２ R in the general formula (i) is ｉ１ A ｉ３ S Ａｉ１ and S Ａｉ２This expresses the same meaning. The compound represented by general formula (s-4) can be reacted with trimethylsilylacetylene, and then reacted with potassium carbonate in an alcohol solvent (e.g., methanol) to obtain the compound represented by general formula (s-5). The reaction with trimethylsilylacetylene can be carried out by a Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base. Specific examples of the palladium catalyst, copper catalyst, and base are listed above. Next, the compound represented by general formula (s-5) can be reacted with the compound represented by general formula (s-6) to obtain the target compound represented by general formula (s-7). An example of the reaction method is a Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base. Specific examples of the palladium catalyst, copper catalyst, and base are listed above. The target product (s-9) can be obtained by reacting the compound represented by general formula (s-7) with the compound represented by general formula (s-8). An example of the reaction method is a Suzuki coupling reaction using a palladium catalyst and a base. Specific examples of the palladium catalyst are listed above. Examples of bases include potassium carbonate, sodium carbonate, and potassium phosphate. (Method 3) Preparation of the compound represented by the following formula (s-14)

[0127]

[0128] In the formula, R ｉ１ A ｉ３ S Ａｉ１ and S Ａｉ２ R in the general formula (i) is ｉ１ A ｉ３ S Ａｉ１ and S Ａｉ２This expresses the same meaning. By reacting a compound represented by general formula (S-10) with a compound represented by general formula (S-11), the target 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 the palladium catalyst, copper catalyst, and base are those listed above. Next, by reacting a compound represented by general formula (S-12) with a compound represented by general formula (S-13), the target compound represented by general formula (S-14) 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 the palladium catalyst and base are those listed above. Other reaction conditions not described in each step include, for example, the following: 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 für Literatur der Organischen Chemie, Springer-Verlag Berlin and Heidelberg GmbH & Co.K), Fiesers' Reagents for Organic Syntheses (John Wiley & Sons) Examples include those described in literature such as Sons, Inc., or those listed in databases such as SciFinder (Chemical Abstracts Service, American Chemical Society) and Reaxys (Elsevier Ltd.). When handling substances 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 in each process.Examples of the protecting group include those described in, for example, "GREENE'S PROTECTIVE GROUPS IN ORGANIC SYNTHESIS" ((Fourth Edition), co-authored by PETER G.M. WUTS and THEODORA W. GREENE, published by A John Wiley & Sons, Inc.). Further, purification may be performed as necessary in each step. Examples of the purification method include chromatography, recrystallization, distillation, sublimation, reprecipitation, adsorption, liquid separation treatment, and the like. Specific examples of the purification agent include silica gel, alumina, activated carbon, and the like.

[0129] (Compound represented by the general formula (ii)) The liquid crystal composition according to the present invention preferably contains one or more compounds represented by the following general formula (ii) having an isothiocyanate group (—NCS) from the viewpoints of solubility, Δn, and / or Δε. ｒ

[0130]

[0131] In the general formula (ii), R ｉｉ１ represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. The alkyl group having 1 to 20 carbon atoms is a linear, branched, or cyclic alkyl group, and is preferably a linear alkyl group. The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, and preferably 2 to 6. One or more —CH ２ — in the alkyl group may each be independently substituted with —O—, —S—, —NH—, —CO—, and / or —CS—. Further, one or more —CH ２ —CH ２Each of the hyphens may be independently substituted with -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, when the alkyl group is substituted with a predetermined group, oxygen atoms will not directly bond to each other. Also, from the viewpoint of compound stability, it is preferable that sulfur atoms and / or oxygen atoms and sulfur atoms do not directly bond to each other. For example, R ｉｉ１ This is one of the -CH groups in the alkyl group. ２ By substituting - with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented. The alkoxy group is linear, branched, or cyclic, and a linear alkoxy group is preferred. The number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6. Also, R ｉｉ１ This is one of the -CH groups in the alkyl group. ２ By substituting - with -S-, an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms can be represented. The alkylsulfanyl group is a linear, branched, or cyclic alkylsulfanyl group, and a linear alkylsulfanyl group is preferred. The number of carbon atoms in the alkylsulfanyl group is preferably 2 to 10, preferably 2 to 6. Also, R ｉｉ１ This refers to one or more -CH groups in the alkyl group. ２ -CH ２ By substituting -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented. The alkenyl group is linear, branched, or cyclic, and a linear alkenyl group is preferred. The number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6. Also, R ｉｉ１ This refers to one or more -CH groups in the alkyl group. ２ -CH ２By substituting -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented. The alkynyl group is linear, branched, or cyclic, and a linear alkynyl group is preferred. The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6. Also, R ｉｉ１ This is one of the -CH groups in the alkyl group. ２ - is replaced by -O- and one or more -CH ２ -CH ２ By substituting -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented. 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, preferably 2 to 6. Also, R ｉｉ１ 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 halogenated alkyl group is preferably 2 to 10, preferably 2 to 6. Also, R ｉｉ１ This is one of the -CH groups in the alkyl group. ２ A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by substituting - with -O- and substituting one or more hydrogen atoms in the alkyl group with halogen atoms. The halogenated alkoxy group is linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6. ｉｉ１ Specific examples of alkyl groups with 1 to 20 carbon atoms in the formula (including substituted ones) include the formula (R ｉｉ１ -1) to (R ｉｉ１ Examples include the base represented by -51).

[0132]

[0133]

[0134] Formula (R ｉｉ１ -1) to (R ｉｉ１ -51), the black dots represent bonds to A ｉｉ１ Note that as R ｉｉ１ , from the perspective of Δn and compatibility with other liquid crystal compounds, a linear alkyl group having 1 to 6 carbon atoms, a linear alkenyl group having 1 to 6 carbon atoms, and a linear alkynyl group having 1 to 6 carbon atoms are preferred.

[0135] In the general formula (ii), A ｉｉ１ and A ｉｉ２ are each independently one of the following groups (a), group (b), group (c), and group (d): (a) 1,4 - cyclohexylene group (one - CH ２ - or two or more non - adjacent - CH ２(b) 1,4-phenylene group (one or more -CH= present in 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-2,7-diyl group, 2,3-dihydro-1H-indene-1,5-diyl group, 2,3-dihydro-1H-indene-2,5-diyl group, 2,3-dihydro-1H-indene-1,6-diyl group, 1 H-indene-2,5-diyl group, 1H-indene-1,5-diyl group, 1H-indene-3,5-diyl group, 1H-indene-1,6-diyl group, 1H-indene-2,6-diyl group, 1H-indene-3,6-diyl group (one -CH= or two or more -CH= present in the 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) Represents a group selected from the group consisting of thiophene-2,5-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group, thieno[3,2-b]thiophene-2,5-diyl group, and benzo[1,2-b:4,5-b']dithiophene-2,6-diyl group (one or more -CH= present in this group may be replaced with -N=).

[0136] A ｉｉ１ and A ｉｉ２ One or more hydrogen atoms in the middle are independently substituents S ｉｉ１Substituent S may be substituted. ｉｉ１ This represents any of the following: a halogen atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms. Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. The alkyl group having 1 to 20 carbon atoms is linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, and preferably 2 to 6. One or more -CH groups in the alkyl group ２ Each of the -s may be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-. Also, 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-, 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, when the alkyl group is substituted with a predetermined group, oxygen atoms will not be directly bonded to each other. Also, from the viewpoint of compound stability, it is preferable that sulfur atoms and / or oxygen atoms and sulfur atoms do not directly bond to each other. For example, substituent S ｉｉ１ This is one of the -CH groups in the alkyl group. ２ By substituting - with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented. The alkoxy group is linear, branched, or cyclic, and a linear alkoxy group is preferred. The number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6. Also, substituent S ｉｉ１ This is one of the -CH groups in the alkyl group. ２By substituting - with -S-, an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms can be represented. The alkylsulfanyl group is a linear, branched, or cyclic alkylsulfanyl group, and a linear alkylsulfanyl group is preferred. The number of carbon atoms in the alkylsulfanyl group is preferably 2 to 10, preferably 2 to 6. Also, substituent S ｉｉ１ This refers to one or more -CH groups in the alkyl group. ２ -CH ２ The - is replaced with -CH=CH- to represent an alkenyl group having 2 to 20 carbon atoms. The alkenyl group is linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6. Also, substituent S ｉｉ１ This refers to one or more -CH groups in the alkyl group. ２ -CH ２ The - is substituted with -C≡C- to represent an alkynyl group having 2 to 20 carbon atoms. The alkynyl group is linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6. Also, substituent S ｉｉ１ This is one of the -CH groups in the alkyl group. ２ - is replaced by -O- and one or more -CH ２ -CH ２ The - is replaced with -CH=CH- to represent an alkenyloxy group having 2 to 19 carbon atoms. The alkenyloxy group is linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6. Also, substituent S ｉｉ１This 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 halogenated alkyl group is preferably 2 to 10, preferably 2 to 6. Also, substituent S ｉｉ１ This is one of the -CH groups in the alkyl group. ２ A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by substituting - with -O- and substituting one or more hydrogen atoms in the alkyl group with halogen atoms. The halogenated alkoxy group is linear, branched, or cyclic, and is preferably linear. The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6. Substituent S ｉｉ１ Specific examples of alkyl groups with 1 to 20 carbon atoms (including substituted ones) in the following formula (S ｉｉ１Ｒ -1) ~ (S ｉｉ１Ｒ Examples include the base represented by -36).

[0137]

[0138] Formula (S ｉｉ１Ｒ -1) ~ (S ｉｉ１Ｒ -36) Among them, black spot A ｉｉ１ Or A ｉｉ２ Represents a bond to the substituent S. ｉｉ１ As such, linear alkyl groups having 1 to 6 carbon atoms, fluorine atoms, or chlorine atoms are preferred. Also, A ｉｉ１ At least one of A ｉｉ２ is at least one substituent S ｉｉ１ It is preferable that the substituent S is substituted with a halogen atom, and it is preferable that it is substituted with a fluorine atom. ｉｉ１ If there are multiple items, they may be the same or different.

[0139] A ｉｉ１substituent S in ｉｉ１ The substitution position is the following general formula (A ｉｉ１ -SP-1) ~ (A ｉｉ１ It is preferable that it be one of the following: -SP-24).

[0140]

[0141]

[0142]

[0143]

[0144] General formula (A ｉｉ１ -SP-1) ~ (A ｉｉ１ -SP-24) Among them, the white dots are R ｉｉ１ or Z ｉｉ１ The black dot represents a bond to Z. ｉｉ１ Represents a connection to A. ｉｉ２ substituent S in ｉｉ１ The substitution position is the following general formula (A ｉｉ２ -SP-1) ~ (A ｉｉ２ It is preferable that it be one of the following: -SP-8).

[0145]

[0146] General formula (A ｉｉ２ -SP-1) ~ (A ｉｉ２ -SP-8) In the middle, the white dot is Z ｉｉ１ The black dots represent bonds to the isothiocyanate group (-NCS). More specifically, A ｉｉ１ The formula is as follows (A ｉｉ１ -1) to (A ｉｉ１ It is preferable to represent one of the following: -49)

[0147]

[0148]

[0149]

[0150]

[0151] Formula (A ｉｉ１ -1) to (A ｉｉ１ -49) Among them, the white dot is Rｉｉ１ or Z ｉｉ１ The black dot represents a bond to Z. ｉｉ１ It represents a connection to A. More specifically, A ｉｉ２ The formula is as follows (A ｉｉ2 -1) to (A ｉｉ2 It is preferable to represent one of the following: -10)

[0152]

[0153] Formula (A ｉｉ2 -1) to (A ｉｉ2 -10) In the middle, the white dot is Z ｉｉ１ The black dots represent bonds to the isothiocyanate group (-NCS).

[0154] In general formula (ii), Z ｉｉ１ This represents either a single bond or an alkylene group having 1 to 20 carbon atoms. One or more -CH groups are found within the alkylene group. ２ The hyphens are, respectively, -O- and -CF. ２ It may be substituted with - and / or -CO-. Also, one or more -CH groups in the alkylene group. ２ -CH ２ Each of the hyphens is independent of the other, -CH ２ -CH(CH ３ )-,-CH(CH ３ ) - CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ )-,-C(CH ３ ) may be substituted with -CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-. However, when an alkylene group having 1 to 20 carbon atoms is substituted with a predetermined group, oxygen atoms will not directly bond with each other. Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms and / or oxygen atoms and sulfur atoms do not directly bond with each other. Specific examples of alkylene groups having 1 to 20 carbon atoms (including substituted ones) are given by formula (Z ｉｉ１ -1) to (Z ｉｉ１ Examples include the base represented by -24).

[0155]

[0156] In formulas (Z ｉｉ１ -1) to (Z ｉｉ１ -24), the white dots represent bonds to A ｉｉ１ and the black dots represent bonds to A ｉｉ１ or A ｉｉ２ .

[0157] In general formula (ii), n ｉｉ１ represents an integer of 1 to 4, preferably 1 to 2. When n ｉｉ１ is 1, from the viewpoints of Δn and / or Δε ｒ , Z ｉｉ１ preferably represents a single bond or -C≡C-. Also, when n ｉｉ１ is 2, from the viewpoints of Δn and / or Δε ｒ , Z ｉｉ１ preferably represents a single bond or -C≡C-. In general formula (ii), when there are multiple A ｉｉ１ and Z ｉｉ１ , they may be the same or different from each other. Also, in the compound represented by general formula (ii), the compound represented by general formula (i) is excluded.

[0158] The compound represented by general formula (ii) is preferably a compound represented by the following general formulas (ii-1) to (ii-7).

[0159]

[0160] In general formulas (ii-1) to (ii-7), R ｉｉ１ , A ｉｉ１ and A ｉｉ２ have the same meanings as R ｉｉ１ , A ｉｉ１ and A ｉｉ２ in general formula (ii) respectively. In general formulas (ii-2) to (ii-7), the definitions of A ｉｉ１－２ and A ｉｉ１－３ are each independently the same as the definition of A ｉｉ１ in general formula (ii). The compound represented by general formula (ii-1) is preferably a compound represented by the following general formula (ii-1-1).

[0161]

[0162] In general formula (ii-1-1), R ｉｉ１ and S ｉｉ１ Each of these independently corresponds to R in the above general formula (ii). ｉｉ１ and S ｉｉ１ These represent the same meaning. Specific examples of compounds represented by the general formula (ii-1-1) include the compounds represented by the following structural formulas (ii-1-1.1) to (ii-1-1.6).

[0163]

[0164] The compound represented by general formula (ii-2) is preferably the compound represented by the following general formulas (ii-2-1) to (ii-2-2).

[0165]

[0166] In general formulas (ii-2-1) to (ii-2-2), R ｉｉ１ and S ｉｉ１ Each of these independently corresponds to R in the above general formula (ii). ｉｉ１ and S ｉｉ１ These represent the same meaning. Specific examples of compounds represented by the general formula (ii-2-1) include the compounds represented by the following structural formulas (ii-2-1.1) to (ii-2-1.3).

[0167]

[0168] Specific examples of compounds represented by the general formula (ii-2-2) include the compounds represented by the following structural formulas (ii-2-2.1) to (ii-2-2.6).

[0169]

[0170] The compounds represented by general formula (ii-3) are preferably those represented by the following general formulas (ii-3-1) to (ii-3-5).

[0171]

[0172] In general formulas (ii-3-1) to (ii-3-5), R ｉｉ１ and S ｉｉ１Each of these independently corresponds to R in the above general formula (ii). ｉｉ１ and S ｉｉ１ These express the same meaning.

[0173] Specific examples of compounds represented by the general formula (ii-3-1) include the compounds represented by the following structural formulas (ii-3-1.1) to (ii-3-1.3).

[0174]

[0175] Specific examples of compounds represented by the general formula (ii-3-2) include the compounds represented by the following structural formulas (ii-3-2.1) to (ii-3-2.5).

[0176]

[0177] Specific examples of compounds represented by the general formula (ii-3-3) include the compounds represented by the following structural formulas (ii-3-3.1) to (ii-3-3.5).

[0178]

[0179] Specific examples of compounds represented by the general formula (ii-3-4) include the compounds represented by the following structural formulas (ii-3-4.1) to (ii-3-4.3).

[0180]

[0181] Specific examples of compounds represented by the general formula (ii-3-5) include the compounds represented by the following structural formulas (ii-3-5.1) to (ii-3-5.3).

[0182]

[0183] The compounds represented by general formula (ii-4) are preferably those represented by the following general formulas (ii-4-1) to (ii-4-3).

[0184]

[0185] In general formulas (ii-4-1) to (ii-4-3), R ｉｉ１ and S ｉｉ１ Each of these independently corresponds to R in the above general formula (ii). ｉｉ１and S ｉｉ１ These express the same meaning.

[0186] Specific examples of compounds represented by the general formula (ii-4-1) include the compounds represented by the following structural formulas (ii-4-1.1) to (ii-4-1.3).

[0187]

[0188] Specific examples of compounds represented by the general formula (ii-4-2) include the compounds represented by the following structural formulas (ii-4-2.1) to (ii-4-2.3).

[0189]

[0190] Specific examples of compounds represented by the general formula (ii-4-3) include the compounds represented by the following structural formulas (ii-4-3.1) to (ii-4-3.5).

[0191]

[0192] The compound represented by general formula (ii-5) is preferably the compound represented by the following general formula (ii-5-1).

[0193]

[0194] In general formula (ii-5-1), R ｉｉ１ and S ｉｉ１ Each of these independently corresponds to R in the above general formula (ii). ｉｉ１ and S ｉｉ１ These express the same meaning.

[0195] Specific examples of compounds represented by the general formula (ii-5-1) include the compounds represented by the following structural formulas (ii-5-1.1) to (ii-5-1.3).

[0196]

[0197] The compound represented by general formula (ii-6) is preferably the compound represented by the following general formulas (ii-6-1) to (ii-6-2).

[0198]

[0199] In general formulas (ii-6-1) to (ii-6-2), R ｉｉ１ and S ｉｉ１ Each of these independently corresponds to R in the above general formula (ii). ｉｉ１ and S ｉｉ１ These represent the same meaning. Specific examples of compounds represented by the general formula (ii-6-1) include the compounds represented by the following structural formulas (ii-6-1.1) to (ii-6-1.3).

[0200]

[0201] Specific examples of compounds represented by the general formula (ii-6-2) include the compounds represented by the following structural formulas (ii-6-2.1) to (ii-6-2.3).

[0202]

[0203] The compounds represented by general formula (ii-7) are preferably those represented by the following general formulas (ii-7-1) to (ii-7-2).

[0204]

[0205] In general formulas (ii-7-1) to (ii-7-2), R ｉｉ１ and S ｉｉ１ Each of these independently corresponds to R in the above general formula (ii). ｉｉ１ and S ｉｉ１ These express the same meaning.

[0206] Specific examples of compounds represented by the general formula (ii-7-1) include the compounds represented by the following structural formulas (ii-7-1.1) to (ii-7-1.3).

[0207]

[0208] Specific examples of compounds represented by the general formula (ii-7-2) include the compounds represented by the following structural formulas (ii-7-2.1) to (ii-7-2.3).

[0209]

[0210] General formula (ii), General formula (ii-1) to (ii-7), General formula (ii-1-1), General formula (ii-2-1) to (ii-2-2), General formula (ii-3-1) to (ii-3-5) , general formula (ii-4-1) to (ii-4-3), general formula (ii-5-1), general formula (ii-6-1) to (ii-6-2), general formula (ii-7-1) to (ii-7-2), structure Formulas (ii-1-1.1) to (ii-1-1.6), structural formulas (ii-2-1.1) to (ii-2-1.3), structural formulas (ii-2-2.1) to (ii-2-2.6), structural formulas (i i-3-1.1) to (ii-3-1.3), structural formula (ii-3-2.1) to (ii-3-2.5), structural formula (ii-3-3.1) to (ii-3-3.5), structural formula (ii-3- 4.1) ~ (ii-3-4.3), structural formula (ii-3-5.1) ~ (ii-3-5.3), structural formula (ii-4-1.1) ~ (ii-4-1.3), structural formula (ii-4-2.1) ) ~ (ii-4-2.3), structural formula (ii-4-3.1) ~ (ii-4-3.5), structural formula (ii-5-1.1) ~ (ii-5-1.3), structural formula (ii-6-1.1) ~ ( The types of compounds used in the liquid crystal composition of compounds represented by structural formulas (ii-6-1.3), (ii-6-2.1) to (ii-6-2.3), (ii-7-1.1) to (ii-7-1.3), and / or (ii-7-2.1) to (ii-7-2.3) are one or more, preferably 1 to 20, preferably 2 to 15, and preferably 3 to 10.

[0211] General formula (ii), General formula (ii-1) to (ii-7), General formula (ii-1-1), General formula (ii-2-1) to (ii-2-2), General formula (ii-3-1) to (ii-3-5), General formula (ii-4-1) to (ii-4-3), General formula (i i-5-1), general formula (ii-6-1) to (ii-6-2), general formula (ii-7-1) to (ii-7-2), structural formula (ii-1-1.1) to (ii-1-1.6), structural formula (ii-2-1.1) to (ii-2-1.3), structural formula (ii -2-2.1) to (ii-2-2.6), structural formulas (ii-3-1.1) to (ii-3-1.3), structural formulas (ii-3-2.1) to (ii-3-2.5), structural formulas (ii-3-3.1) to (ii-3-3.5), structural formulas (ii-3-4. 1) ~ (ii-3-4.3), structural formula (ii-3-5.1) ~ (ii-3-5.3), structural formula (ii-4-1.1) ~ (ii-4-1.3), structural formula (ii-4-2.1) ~ (ii-4-2.3), structural formula (ii-4-3.1) ~ (i The lower limit of the total content of compounds represented by structural formulas (ii-4-3.5), (ii-5-1.1) to (ii-5-1.3), (ii-6-1.1) to (ii-6-1.3), (ii-6-2.1) to (ii-6-2.3), (ii-7-1.1) to (ii-7-1.3), and / or (ii-7-2.1) to (ii-7-2.3) in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, preferably 3% by mass or more, and preferably 5% by mass or more. Preferably, it is 10% by mass or more, preferably 15% by mass or more, preferably 20% by mass or more, preferably 25% by mass or more, preferably 30% by mass or more, preferably 35% by mass or more, preferably 40% by mass or more, preferably 45% by mass or more, preferably 50% by mass or more, preferably 55% by mass or more, and preferably 85% by mass or more.

[0212] General formula (ii), General formula (ii-1) to (ii-7), General formula (ii-1-1), General formula (ii-2-1) to (ii-2-2), General formula (ii-3-1) to (ii-3-5), General formula (ii-4-1) to (ii-4-3), General formula (ii-5- 1), general formulas (ii-6-1) to (ii-6-2), general formulas (ii-7-1) to (ii-7-2), structural formulas (ii-1-1.1) to (ii-1-1.6), structural formulas (ii-2-1.1) to (ii-2-1.3), structural formulas (ii-2-2.1) to ( ii-2-2.6), structural formulas (ii-3-1.1) to (ii-3-1.3), structural formulas (ii-3-2.1) to (ii-3-2.5), structural formulas (ii-3-3.1) to (ii-3-3.5), structural formulas (ii-3-4.1) to (ii-3-4.3), Structural formula (ii-3-5.1) to (ii-3-5.3), structural formula (ii-4-1.1) to (ii-4-1.3), structural formula (ii-4-2.1) to (ii-4-2.3), structural formula (ii-4-3.1) to (ii-4-3.5), structural formula (ii-5-1) 1) The upper limit of the total content of compounds represented by structural formulas (ii-5-1.3), (ii-6-1.1) to (ii-6-1.3), (ii-6-2.1) to (ii-6-2.3), (ii-7-1.1) to (ii-7-1.3), and / or (ii-7-2.1) to (ii-7-2.3) in 100% by mass of the liquid crystal composition is preferably 95% by mass or less, preferably 75% by mass or less, preferably 70% by mass or less, and preferably 65% ​​by mass or less. Preferably, it is 60% by mass or less, preferably 55% by mass or less, preferably 50% by mass or less, preferably 45% by mass or less, preferably 40% by mass or less, preferably 35% by mass or less, preferably 30% by mass or less, preferably 25% by mass or less, preferably 20% by mass or less, preferably 15% by mass or less, preferably 10% by mass or less, and preferably 5% by mass or less.

[0213] General formula (ii), General formula (ii-1) to (ii-7), General formula (ii-1-1), General formula (ii-2-1) to (ii-2-2), General formula (ii-3-1) to (ii-3) -5), general formulas (ii-4-1) to (ii-4-3), general formulas (ii-5-1), general formulas (ii-6-1) to (ii-6-2), general formulas (ii-7-1) to (ii-7) -2), Structural formula (ii-1-1.1) to (ii-1-1.6), Structural formula (ii-2-1.1) to (ii-2-1.3), Structural formula (ii-2-2.1) to (ii-2-2) .6), Structural formulas (ii-3-1.1) to (ii-3-1.3), Structural formulas (ii-3-2.1) to (ii-3-2.5), Structural formulas (ii-3-3.1) to (ii-3-3) .. 5), Structural formula (ii-3-4.1) ~ (ii-3-4.3), Structural formula (ii-3-5.1) ~ (ii-3-5.3), Structural formula (ii-4-1.1) ~ (ii-4-1) .3), Structural formulas (ii-4-2.1) to (ii-4-2.3), Structural formulas (ii-4-3.1) to (ii-4-3.5), Structural formulas (ii-5-1.1) to (ii-5-1) 3) The total content of the compounds represented by structural formulas (ii-6-1.1) to (ii-6-1.3), structural formulas (ii-6-2.1) to (ii-6-2.3), structural formulas (ii-7-1.1) to (ii-7-1.3), and / or structural formulas (ii-7-2.1) to (ii-7-2.3) 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 1 to 95% by mass, preferably 3 to 75% by mass, and preferably 5 to 70% by mass.

[0214] Compounds represented by general formula (ii) (including sub-concepts) can be synthesized using known synthetic methods.

[0215] (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), other compounds as needed (compounds represented by the above-mentioned general formula (ii)), and additives.

[0216] Examples of additives include stabilizers, dye compounds, polymerizable compounds, azotran compounds, and isothiocyanate compounds (NCS compounds).

[0217] 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-5).

[0218]

[0219] Examples of hindered amines include hindered amine-based light stabilizers represented by the following structural formulas (YY-1) to (YY-2).

[0220]

[0221] When a stabilizer is used, 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.

[0222] Furthermore, the combination of compounds used in the liquid crystal composition includes solubility and T ｎｉ Δn and / or Δε ｒFrom this perspective, 1) combinations of a compound represented by general formula (i) (including sub-concepts) and a compound represented by general formula (ii) (including sub-concepts), 2) combinations of a compound represented by general formula (i) (including sub-concepts) and a compound represented by general formula (ii-1) (including sub-concepts), 3) combinations of a compound represented by general formula (i) (including sub-concepts) and a compound represented by general formula (ii-3) (including sub-concepts), 4) combinations of a compound represented by general formula (i) (including sub-concepts) and a compound represented by general formula (ii-4) (including sub-concepts), 5) combinations of a compound represented by general formula (i-1) and / or general formula (i-8) (including sub-concepts) and a compound represented by general formula (ii-1-1) (including sub-concepts), 6) combinations of a compound represented by general formula (i-1) and / or general formula (i-8) (including sub-concepts) and a compound represented by general formula (ii-3-3) (including sub-concepts), 7) A combination of a compound represented by general formula (i-1) and / or general formula (i-8) (including a sub-concept) and a compound represented by general formula (ii-4-2) (including a sub-concept), 8) A combination of a compound represented by general formula (i-1) and / or general formula (i-8) (including a sub-concept), a compound represented by general formula (ii-1-1) (including a sub-concept), a compound represented by general formula (ii-3-3) (including a sub-concept), and a compound represented by general formula (ii-4-2) (including a sub-concept).

[0223] <Characteristic values ​​of liquid crystal composition> Upper limit temperature of liquid crystal phase (T ｎｉ ) is the temperature at which the liquid crystal composition undergoes a phase transition from the nematic phase to the isotropic phase. ｎｉ This measurement is performed by preparing a slide by sandwiching the liquid crystal composition between a glass slide and a cover slip, and then observing it under a polarizing microscope while heating it on a hot stage. It can also be measured by differential scanning calorimetry (DSC). The unit used is °C. ｎｉ The higher the value, the more the nematic phase can be maintained even at high temperatures, allowing for a wider operating temperature range. The upper limit temperature of the liquid crystal phase of the liquid crystal composition according to the present invention (T ｎｉThe temperature can be set appropriately depending on whether the liquid crystal display element is used indoors or in a car where the ambient temperature can be controlled, or outdoors. However, from the viewpoint of the operating temperature range, it is preferably 130°C or higher, preferably 130 to 180°C, and preferably 135 to 170°C.

[0224] Liquid crystal phase lower limit temperature (T →ｎ T is the temperature at which a liquid crystal composition undergoes a phase transition from another phase (glass phase, smectic phase, crystalline phase) to the nematic phase. →ｎ This method involves filling a glass capillary with a liquid crystal composition, immersing it in a -70°C refrigerant to induce a phase transition of the liquid crystal composition to another phase, and observing the results while increasing the temperature. It can also be measured using differential scanning calorimetry (DSC). The unit used is °C. →ｎ The lower the temperature (T) of the liquid crystal phase of the liquid crystal composition according to the present invention, the more the nematic phase can be maintained even at low temperatures, thus allowing for a wider operating temperature range. →ｎ From the viewpoint of operating temperature, it is preferably 10°C or lower, preferably -70 to 0°C, and preferably -50 to -5°C.

[0225] Δn (refractive index anisotropy) correlates with Δn in the near-infrared region used in optical sensors, which will be described later. A larger Δn increases the phase modulation power of light at the target wavelength, making it particularly suitable for optical sensors. At 25°C and 589 nm, Δn is measured using an Abbe refractometer to determine the anomalous photorefractive index (n) of the liquid crystal composition. ｅ ) and the refractive index (n ｏ ) difference (n ｅ -n ｏ) is determined from the above. Alternatively, Δn can be determined from a phase difference measuring 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, and 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 is performed at a temperature of 25°C and 589 nm, and there are no units. From the viewpoint of the phase modulation power of light of the wavelength, the Δn of the liquid crystal composition according to the present invention at 25°C and 589 nm is preferably 0.40 or more, preferably 0.40 to 0.65, preferably 0.41 to 0.60, preferably 0.42 to 0.55, and preferably 0.43 to 0.50.

[0226] High dielectric anisotropy in the high-frequency range is particularly suitable for antenna applications because a higher dielectric anisotropy results in greater phase modulation power for radio waves in the target frequency band. 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 liquid crystal composition according to the present invention, the dielectric anisotropy Δε at 10 GHz is representative of the high-frequency range characteristics. ｒ and the average value of the dielectric loss tangent, tanδ. ｉｓｏ Δε was measured. ｒ = (ε ｒ∥ -ε ｒ⊥ ) and tanδ ｉｓｏ = (2ε ｒ⊥ tanδ ⊥ +ε ｒ∥ tanδ ∥ ) / (2ε ｒ⊥ +ε ｒ∥ ) is the case here, "ε ｒ " is the dielectric constant, "tanδ" is the dielectric loss tangent, and the subscripts "∥" indicate the component parallel to the orientation direction of the liquid crystal, and "⊥" indicate the component perpendicular to the orientation direction of the liquid crystal.

[0227] Δε ｒ and tanδ ｉｓｏThe dielectric constant (ε) at 10 GHz is determined using the following method. First, the liquid crystal composition is introduced into a polytetrafluoroethylene (PTFE) capillary tube. The capillary tube used 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 resonant frequency of 10 GHz. This cavity resonator has an outer diameter of 30 mm and an outer width of 26 mm. A signal is then input, and the result of the output signal is recorded using a network analyzer (manufactured by Keysight Technologies, Inc.). The difference between the resonant frequency of the PTFE capillary tube without the liquid crystal composition and the resonant frequency of the PTFE capillary tube with the liquid crystal composition is used to determine the dielectric constant (ε) at 10 GHz. ｒ The Δε and loss angle (δ) are determined. The tangent of the obtained δ is the dielectric loss tangent (tanδ). The resonance frequency and other properties of a PTFE capillary tube containing the liquid crystal composition are determined by controlling the orientation of the liquid crystal molecules, and are obtained as the values ​​of the characteristic components perpendicular to the orientation direction of the liquid crystal molecules and the characteristic components parallel to the orientation direction of the liquid crystal molecules. A magnetic field of a permanent magnet or electromagnet is used to align the liquid crystal molecules perpendicular to the PTFE capillary tube (perpendicular to the effective length direction) or parallel to the PTFE capillary tube (parallel to the effective length direction). For example, the magnetic field has a pole distance of 45 mm and a magnetic field strength of 0.23 Tesla near the center. The desired characteristic components are obtained by rotating the PTFE capillary tube containing the liquid crystal composition parallel or perpendicular to the magnetic field. The electric field application time can be set to the conditions under which the liquid crystals are uniformly oriented, but in this invention, the electric field application time is set to 8 minutes. The measurement is performed at a temperature of 25°C, and Δε ｒ and tanδ ｉｓｏ Neither has units.

[0228] Δε at 25°C for the liquid crystal composition 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 0.90 or higher, preferably 0.90 to 1.65, preferably 0.95 to 1.60, and preferably 1.00 to 1.55. The tanδ of the liquid crystal composition according to the present invention at 25°C. ｉｓｏWhile a smaller value is preferable, from the viewpoint of loss in the GHz band, it is preferably 0.011 or less, preferably 0.001 to 0.011, preferably 0.003 to 0.010, and preferably 0.005 to 0.010.

[0229] Rotational viscosity (γ １ ) is the viscosity related to the rotation of liquid crystal molecules. γ １ The liquid crystal composition can be packed into a glass cell with a cell gap of approximately 10 μm and measured using an LCM-2 (manufactured by Toyo Technica). A horizontally aligned cell is used for liquid crystal compositions with positive dielectric anisotropy, and a vertically aligned cell is used for liquid crystal compositions with negative dielectric anisotropy. Measurements are performed at a temperature of 25°C, and the unit is mPa·s. γ １ The smaller the value, the faster the response speed of the liquid crystal composition, making it suitable for any liquid crystal display element. The rotational viscosity (γ) of the liquid crystal composition at 25°C according to the present invention １ From the viewpoint of response speed, the response speed is preferably 150 to 900 mPa·s, preferably 200 to 800 mPa·s, and preferably 400 to 700 mPa·s.

[0230] (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.

[0231] 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-described liquid crystal composition.

[0232] The sensor according to the present invention is characterized by using the above-described 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 crystals; a pressure sensor that utilizes changes in reflected light wavelength due to changes in composition; 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 and 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. The distance measuring sensor is preferably for use in LiDAR (Light Detection and Ranging) systems that use a light source. The LiDAR systems are preferably for use in artificial satellites, aircraft, unmanned aerial vehicles (drones), automobiles, railways, and ships. For automobiles, those for autonomous vehicles are particularly preferred. 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. When the cost of the photodetector and sensitivity in all weather conditions are important, an infrared laser with a wavelength of 905 nm is preferred, while when safety regarding human vision is important, an infrared laser with a wavelength of 1550 nm is preferred. The liquid crystal composition according to the present invention exhibits a high Δn, thus providing a sensor with large phase modulation capabilities in the visible light, infrared light, and electromagnetic wave regions, and excellent detection sensitivity.

[0233] 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.

[0234] The optical communication device according to the present invention is characterized by using the above-described liquid crystal composition, and as one example, one embodiment thereof 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 is used, for example, as a spatial phase modulator.

[0235] 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-described liquid crystal composition. By using the liquid crystal composition according to the present invention, it is possible to provide an antenna that has high reliability against external stimuli such as heat. Furthermore, it is 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 at Ka-band frequencies, K-band frequencies, or Ku-band frequencies used in 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. As for the structure of the antenna according to the present invention, for example, matters described in International Publication No. 2021 / 157189, etc., can be taken into consideration and applied.

[0236] The present invention will be described in more detail below with reference to examples, but the present invention is not limited in any way to the following 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%". The following abbreviations are used to indicate the compounds. Unless otherwise specified, compounds that can take both cis and trans forms are referred to as the trans form. <Ring structure>

[0237]

[0238] <Terminal structure>

[0239] (However, n in the table is a natural number. Also, the alkyl group represented by n is a linear alkyl group.)

[0240] <Connection structure>

[0241] (However, n in the table is a natural number. Also, the alkylene group represented by n is a linear alkylene group.)

[0242] (Hindered phenol antioxidants)

[0243]

[0244] (Hindered amine-based light stabilizers)

[0245]

[0246] (Preparation of liquid crystal compositions) LC-01 to LC-05 and LC-A as described in Table 3 were prepared.

[0247]

[0248] (Examples 1-50 and Comparative Example 1) Liquid crystal compositions were prepared using LC-01-05 and LC-A, hindered phenol antioxidants (XX-1)-(XX-5), and hindered amine light stabilizers (YY-1)-(YY-2). Their physical properties were measured, and a <storage test> was performed. The results are shown in Tables 4-8. <Storage Test> 0.5 g of the liquid crystal composition was weighed into a 1 mL sample bottle (manufactured by Maruemu Co., Ltd.), and degassing was performed at 150-250 Pa for 10 minutes. After that, the bottle was purged with dry nitrogen and the lid was attached. This was stored in a temperature-controlled constant temperature bath (manufactured by ESPEC, SH-241) at 25°C for two weeks, and the occurrence of crystallization of the liquid crystal composition was confirmed visually every week.

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255] From Example 1, a liquid crystal composition containing one or more compounds represented by general formula (i) is T ｎｉ When Δn is high, Δε ｒ Large, tanδ ｉｓｏ It was confirmed that the tanδ was small and that it had good storage properties at room temperature. In particular, compared to the comparative example, ｉｓｏ The value is small. On the other hand, compared to the example, the liquid crystal composition that does not contain one or more compounds represented by general formula (i) compared to Comparative Example 1 shows a tanδ ｉｓｏ The results were significantly better. Furthermore, from Examples 2 to 50, similar effects were confirmed when various compounds were used, and when hindered phenol antioxidants or hindered amine light stabilizers were used in combination.

[0256] (Examples 51-68) Furthermore, liquid crystal compositions were prepared using LC-06 to LC-08, hindered phenol antioxidants (XX-3) and (XX-5), and hindered amine light stabilizers (YY-1) to (YY-2). Their physical properties were measured, and a <storage test> was performed, confirming similar effects. The results are shown in Tables 10-14.

[0257]

[0258]

[0259]

[0260]

[0261]

[0262] The synthesis of the compound represented by general formula (i) is described below. (Synthesis Example 1) Preparation of the compound represented by formula (I-1)

[0263]

[0264] Under a nitrogen atmosphere, 25.5 g of the compound represented by formula (I-1-1), 0.75 g of copper(I) iodide, 2.2 g of tetrakis(triphenylphosphine)palladium, 50 mL of triethylamine, and 150 mL of N,N-dimethylformamide were added to the reaction vessel. Then, while heating the reaction vessel to 85°C, a solution of 20.2 g of the compound represented by formula (I-1-2) dissolved in 50 mL of N,N-dimethylformamide was added dropwise, and the mixture was stirred at 85°C for 3 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 24.5 g of the compound represented by formula (I-1-3) was obtained by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 3 / 1). Next, 24.5 g of the compound represented by formula (I-1-3), 120 ml of dichloromethane, and 26 g of 1,1-thiocarbonyl-di-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 25.2 g of the compound represented by formula (I-1). MS(EI): m / z = 353

[0265] (Synthesis Example 2) Preparation of the compound represented by formula (I-2)

[0266]

[0267] Under a nitrogen atmosphere, 25.5 g of the compound represented by formula (I-2-1), 0.75 g of copper(I) iodide, 2.2 g of tetrakis(triphenylphosphine)palladium, 50 mL of triethylamine, and 150 mL of N,N-dimethylformamide were added to the reaction vessel. Then, while heating the reaction vessel at 85°C, a solution of 21.7 g of the compound represented by formula (I-2-2) dissolved in 50 mL of N,N-dimethylformamide was added dropwise, and the mixture was stirred at 85°C for 3 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 26 g of the compound represented by formula (I-2-3) was obtained by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 3 / 1). Next, 26 g of the compound represented by formula (I-2-3), 120 ml of dichloromethane, and 27 g of 1,1-thiocarbonyl-di-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 26.5 g of the compound represented by formula (I-2). MS (EI): m / z = 367

[0268] (Synthesis Example 3) Preparation of the compound represented by formula (I-3)

[0269]

[0270] Under a nitrogen atmosphere, 28.4 g of the compound represented by formula (I-3-1), 0.75 g of copper(I) iodide, 2.2 g of tetrakis(triphenylphosphine)palladium, 50 mL of triethylamine, and 150 mL of N,N-dimethylformamide were added to the reaction vessel. Then, while heating the reaction vessel to 85°C, a solution of 25.0 g of the compound represented by formula (I-3-2) dissolved in 50 mL of N,N-dimethylformamide was added dropwise, and the mixture was stirred at 85°C for 3 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 32 g of the compound represented by formula (I-3-3) was obtained by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 3 / 1). Next, 32 g of the compound represented by formula (1-3-3), 120 ml of dichloromethane, and 23 g of 1,1-thiocarbonyl-di-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 = 445

[0271] (Synthesis Example 4) Preparation of the compound represented by formula (I-4)

[0272]

[0273] Under a nitrogen atmosphere, 20.8 g of the compound represented by formula (I-4-1), 0.75 g of copper(I) iodide, 2.2 g of tetrakis(triphenylphosphine)palladium, 50 mL of triethylamine, and 150 mL of N,N-dimethylformamide were added to the reaction vessel. Then, while heating the reaction vessel at 85°C, a solution of 25.7 g of the compound represented by formula (I-4-2) dissolved in 50 mL of N,N-dimethylformamide was added dropwise, and the mixture was stirred at 85°C for 3 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 29 g of the compound represented by formula (I-4-3) was obtained by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 3 / 1). Next, 29 g of the compound represented by formula (1-4-3), 120 ml of dichloromethane, and 22 g of 1,1-thiocarbonyl-di-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 26 g of the compound represented by formula (I-4). MS (EI): m / z = 403

[0274] (Synthesis Example 5) Preparation of the compound represented by formula (I-5)

[0275]

[0276] Under a nitrogen atmosphere, 28.4 g of the compound represented by formula (I-5-1), 0.75 g of copper(I) iodide, 2.2 g of tetrakis(triphenylphosphine)palladium, 50 mL of triethylamine, and 150 mL of N,N-dimethylformamide were added to the reaction vessel. Then, while heating the reaction vessel at 85°C, a solution of 20.2 g of the compound represented by formula (I-5-2) dissolved in 50 mL of N,N-dimethylformamide was added dropwise, and the mixture was stirred at 85°C for 3 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 31 g of the compound represented by formula (I-5-3) was obtained by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 3 / 1). Next, 31 g of the compound represented by formula (1-5-3), 120 ml of dichloromethane, and 23 g of 1,1-thiocarbonyl-di-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 30 g of the compound represented by formula (I-5). MS (EI): m / z = 429

[0277] (Synthesis Example 6) Preparation of the compound represented by formula (I-6)

[0278]

[0279] Under a nitrogen atmosphere, 25 g of the compound represented by formula (I-6-1), 0.76 g of copper(I) iodide, 2.3 g of tetrakis(triphenylphosphine)palladium, 50 mL of triethylamine, and 150 mL of N,N-dimethylformamide were added to the reaction vessel. Then, while heating the reaction vessel at 85°C, a solution of 28.6 g of the compound represented by formula (I-6-2) dissolved in 50 mL of N,N-dimethylformamide was added dropwise, and the mixture was stirred at 85°C for 3 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 23 g of the compound represented by formula (I-6-3) was obtained by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 2 / 1). Then, 23 g of the compound represented by formula (I-6-3), 125 mL of dichloromethane, and 26 g of 1,1-thiocarbonyl-di-2(1H)pyridone were added to the reaction vessel, and the mixture was 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 = 1 / 1) to obtain 21.5 g of the compound represented by formula (I-6). MS (EI): m / z = 353

[0280] 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

The following general formula (i) (In general formula (i), R ｉ１ This represents a hydrogen atom 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-, -NH-, -CO- and / or -CS-. One or more -CH groups in the alkyl group ２ -CH ２ The hyphens may be independently substituted by -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 ｉ１ The following general formula (A ｉ１ -1) to (A ｉ１ -4) (General form (A) ｉ１ -1) ~ (A ｉ１ -4) Middle White dots are R ｉ１ This represents a bonding action to, Black spot Z ｉ１ This represents a bonding action to, S Ａｉ１ 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 The hyphens may be independently substituted by -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. This represents a group selected from the group consisting of groups represented by , A ｉ２ The following general formula (A ｉ２ -1) to (A ｉ２ -3) (Formula (A)) ｉ２ -1) ~ (A ｉ２ -3) Middle White spot Z ｉ１ This represents a bonding action to, Black spot Z ｉ２ Alternatively, it represents a bond to an isothiocyanate group (-NCS). S Ａｉ２ Each of these independently 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. 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 The hyphens may be independently substituted by -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. This represents a group selected from the group consisting of groups represented by , A ｉ３ 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 ｉ３ One or more hydrogen atoms in it are each independently S Ａｉ３ It may also be replaced by, S Ａｉ３ 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-, -NH-, -CO- and / or -CS-. One or more -CH groups in the alkyl group ２ -CH ２ The hyphens may be independently substituted by -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. S Ａｉ３ If there are multiple items, they may be the same or different. Z ｉ１ and Z ｉ２ Each of these independently represents either a single bond or an alkylene group with 1 to 20 carbon atoms. One or more -CH groups in the alkylene group ２ The hyphens are, respectively, -O- and -CF. ２ It may also be substituted with - and / or -CO-, One or more -CH groups in the alkylene group ２ -CH ２ Each of the hyphens is independent of the other, -CH ２ -CH(CH ３ )-,-CH(CH ３ ) - CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ )-,-C(CH ３ ) may be substituted with CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, Oxygen atoms do not directly bond with each other. n ｉ１ This represents an integer between 0 and 2, A ｉ３ or Z ｉ２ If multiple instances exist, they may be identical or different. A liquid crystal composition comprising one or more compounds represented by [the specified formula]. 　 The compound represented by the above general formula (i) is the one shown in the following general formulas (i-1) to (i-13). (In general formulas (i-1) to (i-13), R ｉ１ S Ａｉ１ S Ａｉ２ and S Ａｉ３ R in the above general formula (i) ｉ１ S Ａｉ１ S Ａｉ２ and S Ａｉ３ These express the same meaning. The liquid crystal composition according to claim 1, selected from the group consisting of compounds represented by [the specified compound]. 　 The liquid crystal composition according to claim 1 or 2, wherein the total content of the compound represented by general formula (i) in 100% by mass of the liquid crystal composition is 1% by mass or more. 　 Furthermore, the following general formula (ii) (In general formula (ii), R ｉｉ１ Each of these independently 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-, -NH-, -CO- and / or -CS-. One or more -CH groups in the alkyl group ２ -CH ２ The hyphens may be independently substituted with -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 ｉｉ１ and A ｉｉ２ These are, independently, the following bases (a), (b), (c), and (d): (a) 1,4-cyclohexylene group (one -CH group present in this group) ２ - or two or more non-adjacent -CH ２ (The dash may be replaced with -O- and / or -S-.) (b) 1,4-phenylene group (one or more -CH= groups in this group may be replaced with -N= groups.) (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group, 2,3-dihydro-1H-indene-1,5-diyl group, 2,3-dihydro-1H-indene-2,5-diyl group, 2,3-dihydro-1H-indene-1,6-diyl group, 1 H-indene-2,5-diyl group, 1H-indene-1,5-diyl group, 1H-indene-3,5-diyl group, 1H-indene-1,6-diyl group, 1H-indene-2,6-diyl group, 1H-indene-3,6-diyl group (one -CH= or two or more -CH= present in the 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, benzo[1,2-b:4,5-b']dithiophen-2,6-diyl group (one or more -CH= present in this group may be replaced with -N=). This represents a base selected from the group consisting of, A ｉｉ１ and A ｉｉ２ One or more hydrogen atoms in the middle are independently substituents S ｉｉ１ It may be replaced by, Substituent S ｉｉ１ This represents any of the following: a halogen atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms. One or more -CH groups in the alkyl group ２ Each of the hyphens may be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-. One or more -CH groups in the alkyl group ２ -CH ２ The hyphens may be independently substituted by -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. Substituent S ｉｉ１ If there are multiple items, they may be the same or different. Z ｉｉ１ This represents either a single bond or an alkylene group with 1 to 20 carbon atoms. One or more -CH groups in the alkylene group ２ The hyphens are, respectively, -O- and -CF. ２ It may also be substituted with - and / or -CO-, One or more -CH groups in the alkylene group ２ -CH ２ Each of the hyphens is independent of the other, -CH ２ -CH(CH ３ )-,-CH(CH ３ ) - CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ )-,-C(CH ３ ) may be substituted with CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, Oxygen atoms do not directly bond with each other. n ｉｉ１ This represents an integer from 1 to 4, A ｉｉ１ and Z ｉｉ１ If there are multiple instances of this, they may be identical or different. However, this excludes compounds represented by general formula (i). A liquid crystal composition according to any one of claims 1 to 3, comprising one or more compounds represented by . tanδ at 25°C ｉｓｏ The liquid crystal composition according to any one of claims 1 to 4, wherein the coefficient is 0.011 or less. 　 A liquid crystal display element using the liquid crystal composition described in any one of claims 1 to 5. 　 A liquid crystal display element according to claim 6, which is driven by an active matrix or passive matrix and reversibly switches the dielectric constant. 　 A sensor using the liquid crystal composition according to any one of claims 1 to 5. 　 A liquid crystal lens using the liquid crystal composition described in any one of claims 1 to 5. 　 An optical communication device using the liquid crystal composition described in any one of claims 1 to 5. 　 An antenna using the liquid crystal composition according to any one of claims 1 to 5. 　 The antenna according to claim 11, 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 according to any one of claims 1 to 5. 　 The following general formula (i) (In general formula (i), R ｉ１ This represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. When one or more of the -CH in the alkyl group ２ - may each independently be substituted with -O-, -S-, -NH-, -CO- and / or -CS- One or more -CH groups in the alkyl group ２ -CH ２ The hyphens may be independently substituted by -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 ｉ１ The following general formula (A ｉ１ -1) to (A ｉ１ -4) (General form (A) ｉ１ -1) ~ (A ｉ１ -4) Middle White dots are R ｉ１ This represents a bonding action to, Black spot Z ｉ１ This represents a bonding action to, S Ａｉ１ 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 The hyphens may be independently substituted by -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. This represents a group selected from the group consisting of groups represented by , A ｉ２ The following general formula (A ｉ２ -1) to (A ｉ２ -3) (Formula (A)) ｉ２ -1) ~ (A ｉ２ -3) Middle White spot Z ｉ１ This represents a bonding action to, Black spot Z ｉ２ Alternatively, it represents a bond to an isothiocyanate group (-NCS). S Ａｉ２ Each of these independently 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. 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 The hyphens may be independently substituted by -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. This represents a group selected from the group consisting of groups represented by , A ｉ３ 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 ｉ３ One or more hydrogen atoms in it are each independently S Ａｉ３ It may also be replaced by, S Ａｉ３ 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-, -NH-, -CO- and / or -CS-. One or more -CH groups in the alkyl group ２ -CH ２ The hyphens may be independently substituted by -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. S Ａｉ３ If there are multiple items, they may be the same or different. Z ｉ１ and Z ｉ２ Each of these independently represents either a single bond or an alkylene group with 1 to 20 carbon atoms. One or more -CH groups in the alkylene group ２ The hyphens are, respectively, -O- and -CF. ２ It may also be substituted with - and / or -CO-, One or more -CH groups in the alkylene group ２ -CH ２ Each of the hyphens is independent of the other, -CH ２ -CH(CH ３ )-,-CH(CH ３ ) - CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ )-,-C(CH ３ ) may be substituted with CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, Oxygen atoms do not directly bond with each other. n ｉ１ This represents an integer between 0 and 2, A ｉ３ or Z ｉ２ If multiple instances exist, they may be identical or different. A compound represented by the formula.

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