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

Abstract

The present invention addresses the problem of providing a compound, a liquid crystal composition, and a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the same, said compound being capable of providing a liquid crystal composition having high Tni, large [delta] n, low Vth, large [delta] [epsilon] r, small tan [delta] iso, and good storability at low temperatures. The present invention relates to a liquid crystal composition, and more specifically, to a liquid crystal composition comprising: one or more compounds represented by general formula (i) having an indane structure and an isothiocyanate group (-NCS); and one or more compounds represented by general formula (ii) and having an isothiocyanate group (-NCS).

Description

Technical Field

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

[0002] As a new use of liquid crystals, which are mostly used for display purposes, antennas using liquid crystals for transmitting and receiving radio waves between mobile objects such as cars and communication satellites have attracted much attention. Previously, satellite communications used parabola antennas, but when used in mobile objects such as cars, the parabola antennas must be pointed toward the satellite at all times, requiring a large movable part. However, antennas using liquid crystals can change the direction of transmitting and receiving radio waves by operating the liquid crystals inside the panel, so there is no need to move the antenna itself, and the shape of the antenna can also be flat. In addition, in order to achieve global large-capacity and high-speed communications, research is being conducted on low-orbit satellite constellations that use multiple low-orbit satellites. In order to track low-orbit satellites that appear to be constantly moving from the ground, liquid crystal antennas that can easily change the direction of transmitting and receiving radio waves are useful.

[0003] Generally speaking, for the automatic operation of automobiles, etc., it is necessary to download a large amount of data of high-precision three-dimensional (3D) map information. However, if it is an antenna using liquid crystal, by assembling the antenna in the car, a large amount of data can be downloaded from the communication satellite even without a mechanical moving part. The frequency band used in satellite communication is about 13GHz, which is very different from the frequency used in liquid crystal display applications so far. Therefore, the required physical properties of liquid crystal are also very different. The Δn required for antenna liquid crystal is, for example, about 0.4, and the operating temperature range is, for example, -20℃~120℃.

[0004] In addition, infrared laser image recognition and distance measurement devices using liquid crystals are also attracting attention as sensors for automatic operation of mobile objects such as automobiles. The Δn required for liquid crystals for such applications is, for example, 0.3 to 0.6, and the operating temperature range is, for example, 10°C to 100°C.

[0005] Furthermore, it is known that many liquid crystal compounds constituting a liquid crystal composition showing a high Δn of 0.2 or more have low compatibility. Therefore, it is also important to select a liquid crystal compound having high compatibility.

[0006] In this regard, as a technology of liquid crystal for antenna, for example, Patent Document 1 can be cited.

[0007] Furthermore, Non-Patent Document 1 proposes the use of a liquid crystal material as a constituent component of a high-frequency device.

[0008] Prior art literature

[0009] Patent Literature

[0010] Patent Document 1: Japanese Patent Application Publication No. 2016-37607

[0011] Non-patent literature

[0012] Non-patent document 1: D. Dolfi, Electronics Letters, (UK), 1993, Vol. 29, No. 10, pp. 926-928 Summary of the invention

[0013] Problems to be solved by the invention

[0014] The present invention aims to provide a compound, a liquid crystal composition, and a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the same, wherein the compound can provide T ni High, large Δn, V th Low, Δε r Large, tanδ iso A liquid crystal composition that is small and has good storage properties at low temperatures.

[0015] Technical means of solving problems

[0016] The present inventors and others have conducted diligent research and found that a liquid crystal composition can solve the above-mentioned problems, thereby completing the present invention. The liquid crystal composition comprises: one or more compounds represented by general formula (i) having an indane structure and an isothiocyanate group (-NCS); and one or more compounds represented by general formula (ii) having an isothiocyanate group (-NCS).

[0017] An example of the configuration of the present invention for solving the above-mentioned problems is as follows.

[0018] Item 1. A liquid crystal composition comprising: one or more compounds represented by the following general formula (i); and one or more compounds represented by the following general formula (ii),

[0019] [Chemistry 1]

[0020]

[0021] (In general formula (i),

[0022] R i1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms,

[0023] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0024] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-,

[0025] One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-.

[0026] One or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH-, or -O-CO-CH=CH-.

[0027] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0028] However, oxygen atoms do not bond directly to each other.

[0029] A i1 and A i2 each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms,

[0030] The A i1 and A i2 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S i1 replace,

[0031] Substituent S i1 represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms,

[0032] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S- and / or -CO-.

[0033] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-,

[0034] One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-.

[0035] One or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH- and / or -O-CO-CH=CH-,

[0036] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0037] However, oxygen atoms do not bond directly to each other.

[0038] In the substituent S i1 When there are multiple, these may be the same or different, L i1 and L i2 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto 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,

[0039] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0040] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-,

[0041] One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-.

[0042] One or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH- and / or -O-CO-CH=CH-,

[0043] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0044] However, oxygen atoms do not bond directly to each other.

[0045] Z i1 and Zi2 each independently represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms,

[0046] One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[0047] One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-,

[0048] One or more -CH2-CH2-CH2-CH2- in the alkylene group may be independently substituted by -CH=NN=CH-.

[0049] However, oxygen atoms do not bond directly to each other.

[0050] n i1 represents an integer from 0 to 3,

[0051] In A i2 or Z i2 When there are multiple, these may be the same or different).

[0052] [Chemistry 2]

[0053]

[0054] (In general formula (ii),

[0055] R ii1 each independently represents an alkyl group having 1 to 20 carbon atoms,

[0056] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0057] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-,

[0058] One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-.

[0059] One or more hydrogen atoms in the alkyl group may be independently replaced by halogen atoms.

[0060] However, oxygen atoms do not bond directly to each other.

[0061] A ii1 and A ii2 Each independently represents a group (a), a group (b), a group (c) and a group (d) selected from the following:

[0062] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- in the group may be substituted with -O- and / or -S-)

[0063] (b) 1,4-phenylene (one or two or more -CH= in the group may be substituted with -N=)

[0064] (c) 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene -2,7-diyl (one or two or more -CH= in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl may be substituted with -N=)

[0065] (d) thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl, benzo[1,2-b:4,5-b']dithiophene-2,6-diyl (one -CH= or two or more -CH= in the above group may be substituted with -N=)

[0066] The basis of the group is

[0067] The A ii1 and A ii2 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S ii1 replace,

[0068] Substituent S ii1represents any one of a halogen atom, a pentafluoromercapto 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,

[0069] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0070] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-,

[0071] One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-.

[0072] One or more hydrogen atoms in the alkyl group may be independently replaced by halogen atoms.

[0073] However, oxygen atoms do not bond directly to each other.

[0074] In the substituent S ii1 When there are multiple, these may be the same or different.

[0075] Z ii1 represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms,

[0076] One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[0077] One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-,

[0078] One or more -CH2-CH2-CH2- in the alkylene group may be independently substituted by -O-CO-O-.

[0079] Oxygen atoms do not bond directly to each other.

[0080] n ii1 represents an integer from 1 to 4,

[0081] In A ii1 and Z ii1 When there are multiple, these may be the same or different.

[0082] However, compounds represented by general formula (i) are excluded).

[0083] Item 2. The liquid crystal composition according to Item 1, wherein the compound represented by the general formula (i) is selected from the group consisting of compounds represented by the following general formulas (i-1) to (i-14),

[0084] [Chemistry 3]

[0085]

[0086] [Chemistry 4]

[0087]

[0088] (In general formula (i-1) to general formula (i-14),

[0089] R i1 , A i1 , A i2 , L i1 and L i2 represents the same as R in the general formula (i) i1 , A i1 , A i2 , L i1 and L i2 The same meaning respectively,

[0090] In the general formula (i-9), A i2-2 The definition of A in the general formula (i) is the same as i2 )

[0091] Item 3. The liquid crystal composition according to Item 1 or 2, wherein the compound represented by the general formula (ii) is selected from the group consisting of compounds represented by the following general formulas (ii-1) to (ii-8),

[0092] [Chemistry 5]

[0093] R ii1 -A ii1 -A ii2 -NCS (ii-1)

[0094]

[0095] R ii1 -A ii1 -A ii1-2 -A ii1-3 -Aii2 -NCS (ii-8)

[0096] (In general formula (ii-1) to general formula (ii-8),

[0097] R ii1 , A ii1 and A ii2 represents the same as R in the general formula (ii) ii1 , A ii1 and A ii2 The same meaning respectively,

[0098] In the general formula (ii-3) to the general formula (ii-9), A ii1-2 and A ii1-3 The definitions of are independently the same as those of A in the general formula (ii). ii1 )

[0099] Item 4. The liquid crystal composition according to any one of Items 1 to 3, further comprising one or more compounds represented by the following general formula (vt),

[0100] [Chemistry 6]

[0101]

[0102] (In the general formula (vt),

[0103] R vt1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms,

[0104] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0105] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-,

[0106] One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-.

[0107] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0108] However, oxygen atoms do not bond directly to each other.

[0109] R vt2represents any one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto 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, or an alkyl group having 1 to 20 carbon atoms,

[0110] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0111] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-,

[0112] One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-.

[0113] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0114] However, oxygen atoms do not bond directly to each other.

[0115] A vt1 , A vt2 and A vt3 each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms,

[0116] The A vt1 , A vt2 and A vt3 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S vt1 replace,

[0117] Substituent S vt1 represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms,

[0118] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S- and / or -CO-.

[0119] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-,

[0120] One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-.

[0121] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0122] However, oxygen atoms do not bond directly to each other.

[0123] In the substituent S vt1 When there are multiple, these may be the same or different.

[0124] Z vt1 each independently represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms,

[0125] One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[0126] One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-,

[0127] One or more -CH2-CH2-CH2- in the alkylene group may be independently replaced by -O-CO-O-.

[0128] However, oxygen atoms do not bond directly to each other.

[0129] n vt1 represents an integer from 1 to 3,

[0130] But in A vt3 and Z vt1 When there are multiple ones, these may be the same or different).

[0131] Item 5. The liquid crystal composition according to any one of Items 1 to 4, wherein Δn at 25° C. and 589 nm is 0.38 or more.

[0132] Item 6. A liquid crystal display element using the liquid crystal composition according to any one of Items 1 to 5.

[0133] Item 7. The liquid crystal display element according to Item 6, which is driven by an active matrix method or a passive matrix method.

[0134] Item 8. A liquid crystal display element that reversibly switches a dielectric constant by reversibly changing the alignment direction of liquid crystal molecules of the liquid crystal composition according to any one of Items 1 to 5.

[0135] Item 9. A sensor using the liquid crystal composition according to any one of Items 1 to 5.

[0136] Item 10. A liquid crystal lens using the liquid crystal composition according to any one of Items 1 to 5.

[0137] Item 11. An optical communication device using the liquid crystal composition according to any one of Items 1 to 5.

[0138] Item 12. An antenna using the liquid crystal composition according to any one of Items 1 to 5.

[0139] Item 13. The antenna according to Item 12, comprising:

[0140] A first substrate having a plurality of slots;

[0141] A second substrate, facing the first substrate, provided with a power supply portion;

[0142] A first dielectric layer is disposed between the first substrate and the second substrate;

[0143] a plurality of patch electrodes arranged corresponding to the plurality of grooves;

[0144] A third substrate, provided with the patch electrode; and

[0145] A liquid crystal layer is disposed between the first substrate and the third substrate, and

[0146] The liquid crystal layer contains the liquid crystal composition according to any one of items 1 to 5.

[0147] Item 14. A compound represented by the following general formula (i):

[0148] [Chemistry 7]

[0149]

[0150] (In general formula (i),

[0151] R i1represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms,

[0152] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0153] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-,

[0154] One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-.

[0155] One or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH-, or -O-CO-CH=CH-.

[0156] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0157] However, oxygen atoms do not bond directly to each other.

[0158] A i1 and A i2 each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms,

[0159] The A i1 and A i2 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S i1 replace,

[0160] Substituent S i1 represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms,

[0161] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S- and / or -CO-.

[0162] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-,

[0163] One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-.

[0164] One or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH- and / or -O-CO-CH=CH-,

[0165] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0166] However, oxygen atoms do not bond directly to each other.

[0167] In the substituent S i1 When there are multiple, these may be the same or different, L i1 and L i2 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto 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,

[0168] One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0169] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-,

[0170] One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-.

[0171] One or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH- and / or -O-CO-CH=CH-,

[0172] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0173] However, oxygen atoms do not bond directly to each other.

[0174] Z i1 and Z i2 each independently represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms,

[0175] One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[0176] One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-,

[0177] One or more -CH2-CH2-CH2-CH2- in the alkylene group may be independently substituted by -CH=NN=CH-.

[0178] However, oxygen atoms do not bond directly to each other.

[0179] n i1 represents an integer from 0 to 3,

[0180] In A i2 or Z i2 When there are multiple ones, these may be the same or different).

[0181] Effects of the Invention

[0182] According to the present invention, T can be obtained by using a liquid crystal composition. ni High, large Δn, V th Low, Δε r Large, tanδ iso A liquid crystal composition having a small size and good storage properties at low temperatures, wherein the liquid crystal composition is useful for liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment and antennas, and wherein the liquid crystal composition comprises: one or more compounds represented by the general formula (i) having an indane structure and an isothiocyanate group (-NCS); and one or more compounds represented by the general formula (ii) having an isothiocyanate group (-NCS). DETAILED DESCRIPTION

[0183] (Compound represented by general formula (i))

[0184] The liquid crystal composition of the present invention contains one or two or more compounds represented by the general formula (i) having an indane structure and an isothiocyanate group (—NCS).

[0185] [Chemistry 8]

[0186]

[0187] In the general formula (i), R i1 It represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.

[0188] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0189] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.

[0190] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0191] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0192] In addition, one or two or more -CH2-CH2-CH2- in the alkyl group may be independently substituted by -O-CO-O-.

[0193] In addition, one or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH-, or -O-CO-CH=CH-.

[0194] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom.

[0195] Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.

[0196] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0197] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0198] For example, Ri1 By substituting one -CH2- in the above alkyl group with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0199] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0200] The alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0201] In addition, R i1 By substituting one -CH2- in the above alkyl group with -S-, an alkylmercapto group (alkylthio group) having 1 to 19 carbon atoms can be represented.

[0202] The alkylmercapto group is a linear, branched or cyclic alkylmercapto group, and is preferably a linear alkylmercapto group.

[0203] The alkylmercapto group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0204] In addition, R i1 By replacing one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0205] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0206] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0207] In addition, R i1 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0208] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0209] The alkynyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0210] In addition, R i1 An alkenyloxy group having 2 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or more -CH2-CH2- with -CH=CH-.

[0211] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0212] The alkenyloxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0213] In addition, R i1 By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0214] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0215] The halogenated alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0216] In addition, R i1 A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or two or more hydrogen atoms in the alkyl group with halogen atoms.

[0217] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[0218] The halogenated alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0219] As R i1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: i1 -1)~Formula (R i1 -36) represented by the base, etc.

[0220] [Chemistry 9]

[0221]

[0222] Formula (R i1 -1)~Formula (R i1 -36), the black dot indicates the direction to A i1 The bond key.

[0223] In addition, as R i1 In view of Δn and compatibility with other liquid crystal compounds, a linear alkyl group having 2 to 6 carbon atoms is preferred.

[0224] As R in the indane structure i1 The substitution position is preferably the following formula (R i1 -SP-1)~Formula (R i1 -SP-3) is preferably (R i1 -SP-2) or (R i1 -SP-3).

[0225] [Chemistry 10]

[0226]

[0227] Formula (R i1 -SP-1)~Formula (R i1 -SP-3), the black dot indicates the direction of Z i1 The bond key.

[0228] In the general formula (i), A i1 and A i2 Each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms.

[0229] More specifically, the hydrocarbon ring having 3 to 16 carbon atoms or the heterocyclic ring having 3 to 16 carbon atoms preferably represents a group (a), a group (b), a group (c) and a group (d) selected from the following:

[0230] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- in the group may be substituted with -O- or -S-)

[0231] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= in the group may be substituted with -N=)

[0232] (c) 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene -2,7-diyl (one or two or more -CH= in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl may be substituted with -N=)

[0233] (d) Thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl (one -CH= or two or more non-adjacent -CH= in the above group may be substituted with -N=)

[0234] The basis of the group.

[0235] A i1 and A i2 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group Si1 replace.

[0236] Substituent S i1 It represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms.

[0237] The alkyl group is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0238] The alkyl group preferably has 2 to 10 carbon atoms, and more preferably 3 to 6 carbon atoms.

[0239] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S- and / or -CO-.

[0240] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-.

[0241] In addition, one or two or more -CH2-CH2-CH2- in the alkyl group may be independently substituted by -O-CO-O-.

[0242] In addition, one or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH- and / or -O-CO-CH=CH-.

[0243] One or two or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0244] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0245] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0246] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0247] As a substituent S i1 , preferably a fluorine atom.

[0248] In addition, A i1 and Ai2 At least one of the substituents S i1 replace.

[0249] In addition, A i2 Preferably, at least one substituent S i1 replace.

[0250] In addition, in the substituent S i1 When there are plural, these may be the same or different.

[0251] As A i1 The substituent S in i1 The substitution position is preferably the following formula (A i1 -SP-1)~Formula (A i1 -SP-3).

[0252] [Chemistry 11]

[0253]

[0254] Formula (A i1 -SP-1)~Formula (A i1 -SP-3), the white dot indicates the direction of Z i1 The black dots represent the bonds to Z i2 Or an isothiocyanate (-NCS) bond.

[0255] As A i2 The substituent S in i1 The substitution position is preferably the following formula (A i2 -SP-1)~Formula (A i2 -SP-3).

[0256] [Chemistry 12]

[0257]

[0258] Formula (A i2 -SP-1)~Formula (A i2 -SP-3), the white dot indicates the direction of Z i2 The black dots represent the bonds to Z i2 Or an isothiocyanate (-NCS) bond.

[0259] More specifically, A i1 Preferably, it is represented by the following formula (A i1 -1)~Formula (A i1 -8).

[0260] [Chemistry 13]

[0261]

[0262] Formula (A i1 -1)~Formula (A i1 -8), the white dot indicates the direction Z i1 The black dots represent the bonds to Z i2 Or an isothiocyanate (-NCS) bond.

[0263] More specifically, A i2 Preferably, it is represented by the following formula (A i2 -1)~Formula (A i2 -5) any one of.

[0264] [Chemistry 14]

[0265]

[0266] Formula (A i2 -1)~Formula (A i2 -5), the white dot indicates the direction Z i2 The black dots represent the bonds to Z i2 Or an isothiocyanate (-NCS) bond.

[0267] In the general formula (i), L i1 and L i2 Each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto 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.

[0268] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0269] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.

[0270] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0271] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-.

[0272] In addition, one or two or more -CH2-CH2-CH2- in the alkyl group may be independently substituted by -O-CO-O-.

[0273] In addition, one or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH- and / or -O-CO-CH=CH-.

[0274] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom.

[0275] Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.

[0276] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0277] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0278] For example, L i1 and L i2 By substituting one -CH2- in the above alkyl group with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0279] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0280] The alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0281] In addition, L i1 and L i2 By substituting one -CH2- in the above alkyl group with -S-, an alkylmercapto group (alkylthio group) having 1 to 19 carbon atoms can be represented.

[0282] The alkylmercapto group is a linear, branched or cyclic alkylmercapto group, and is preferably a linear alkylmercapto group.

[0283] The alkylmercapto group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0284] In addition, L i1 and L i2 By replacing one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0285] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0286] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0287] In addition, L i1 and L i2 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0288] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0289] The alkynyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0290] In addition, L i1 and L i2 An alkenyloxy group having 2 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or more -CH2-CH2- with -CH=CH-.

[0291] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0292] The alkenyloxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0293] In addition, L i1 and L i2 By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0294] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0295] The halogenated alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0296] In addition, L i1 and L i2 A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or two or more hydrogen atoms in the alkyl group with halogen atoms.

[0297] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[0298] The halogenated alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0299] As L i1 and L i2 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the formula (Li1 / 2 -1)~Formula(L i1 / 2 -36) represented by the base, etc.

[0300] [Chemistry 15]

[0301]

[0302] Formula (L i1 / 2 -1)~Formula(L i1 / 2 -36), the black dots represent the bonds to the indane structure.

[0303] From the viewpoint of compatibility with other liquid crystal compounds, L i1 and L i2 At least one of them is preferably a hydrogen atom or a fluorine atom, preferably L i1 and L i2 They are all hydrogen atoms or fluorine atoms.

[0304] Z i1 and Z i2 Each independently represents any of a single bond and an alkylene group having 1 to 20 carbon atoms.

[0305] The alkylene group is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0306] The alkylene group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0307] One or more -CH2- groups in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[0308] In addition, one or more -CH2-CH2- in the alkylene group may be independently replaced by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[0309] In addition, one or two or more -CH2-CH2-CH2-CH2- in the alkylene group may be independently substituted by -CH=NN=CH-.

[0310] However, when the alkylene group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0311] Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted alkylene groups) include the following: i1 / 2 -1)~Formula(Zi1 / 2 -24) represented by the base, etc.

[0312] [Chemistry 16]

[0313]

[0314] Formula (Z i1 / 2 -1)~Formula(Z i1 / 2 -24), the white dots represent the indane structure, A i1 or A i2 The black dots indicate the bond to A i1 or A i2 The bond key.

[0315] From the perspective of increasing Δn and reducing viscosity, Z i1 and Z i2 At least one of the formula (Z i1 / 2 -4)(-C≡C-), preferably Z i1 and Z i2 All are formula (Z i1 / 2 -4)(-C≡C-).

[0316] In the general formula (i), n i1 Indicates an integer from 0 to 3.

[0317] From the viewpoints of compatibility with other liquid crystal compounds, phase transition temperature, dielectric anisotropy, ease of synthesis, and availability of raw materials, n i1 Preferably 1 or 2.

[0318] In A i2 or Z i2 When there are plural numbers, these may be the same or different.

[0319] As the compound represented by the general formula (i), compounds represented by the following general formulas (i-1) to (i-14) are preferred.

[0320] [Chemistry 17]

[0321]

[0322] [Chemistry 18]

[0323]

[0324] In the general formulas (i-1) to (i-14), R i1 , A i1 , A i2 , L i1 and L i2 Each independently represents R i1 , Ai1 , A i2 , L i1 and L i2 Same meaning.

[0325] In the general formula (i-9), A i2-2 The definition of A in the general formula (i) is the same as i2 The definition is the same.

[0326] As the compound represented by the general formula (i-1), compounds represented by the following general formulas (i-1-1) to (i-1-2) are preferred.

[0327] [Chemistry 19]

[0328]

[0329] In the general formula (i-1-1) to the general formula (i-1-2), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0330] Specific examples of the compound represented by general formula (i-1-1) include compounds represented by the following structural formulas (i-1-1.1) to (i-1-1.3).

[0331] [Chemistry 20]

[0332]

[0333] Specific examples of the compound represented by the general formula (i-1-2) include compounds represented by the following structural formulas (i-1-2.1) to (i-1-2.3).

[0334] [Chemistry 21]

[0335]

[0336] As the compound represented by the general formula (i-2), compounds represented by the following general formulas (i-2-1) to (i-2-4) are preferred.

[0337] [Chemistry 22]

[0338]

[0339] In the general formulas (i-2-1) to (i-2-4), R i1 and S i1 Each independently represents R i1 and S i1Same meaning.

[0340] Specific examples of the compound represented by the general formula (i-2-1) include compounds represented by the following structural formulas (i-2-1.1) to (i-2-1.3).

[0341] [Chemistry 23]

[0342]

[0343] Specific examples of the compound represented by general formula (i-2-2) include compounds represented by the following structural formulas (i-2-2.1) to (i-2-2.3).

[0344] [Chemistry 24]

[0345]

[0346] Specific examples of the compound represented by the general formula (i-2-3) include compounds represented by the following structural formulas (i-2-3.1) to (i-2-3.3).

[0347] [Chemistry 25]

[0348]

[0349] Specific examples of the compound represented by general formula (i-2-4) include compounds represented by the following structural formula (i-2-4.1).

[0350] [Chemistry 26]

[0351]

[0352] As the compound represented by the general formula (i-3), compounds represented by the following general formulas (i-3-1) to (i-3-3) are preferred.

[0353] [Chemistry 27]

[0354]

[0355] In the general formula (i-3-1) to the general formula (i-3-3), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0356] Specific examples of the compound represented by general formula (i-3-1) include compounds represented by the following structural formulas (i-3-1.1) to (i-3-1.3).

[0357] [Chemistry 28]

[0358]

[0359] Specific examples of the compound represented by general formula (i-3-2) include compounds represented by the following structural formulas (i-3-2.1) to (i-3-2.3).

[0360] [Chemistry 29]

[0361]

[0362] Specific examples of the compound represented by general formula (i-3-3) include compounds represented by the following structural formulas (i-3-3.1) to (i-3-3.3).

[0363] [Chemistry 30]

[0364]

[0365] As the compound represented by the general formula (i-4), compounds represented by the following general formulas (i-4-1) to (i-4-6) are preferred.

[0366] [Chemistry 31]

[0367]

[0368] In the general formulas (i-4-1) to (i-4-6), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0369] Specific examples of the compound represented by general formula (i-4-1) include compounds represented by the following structural formulas (i-4-1.1) to (i-4-1.3).

[0370] [Chemistry 32]

[0371]

[0372] Specific examples of the compound represented by general formula (i-4-2) include compounds represented by the following structural formulas (i-4-2.1) to (i-4-2.3).

[0373] [Chemistry 33]

[0374]

[0375] Specific examples of the compound represented by the general formula (i-4-3) include compounds represented by the following structural formulas (i-4-3.1) to (i-4-3.3).

[0376] [Chemistry 34]

[0377]

[0378] Specific examples of the compound represented by general formula (i-4-4) include compounds represented by the following structural formulas (i-4-4.1) to (i-4-4.3).

[0379] [Chemistry 35]

[0380]

[0381] Specific examples of the compound represented by general formula (i-4-5) include compounds represented by the following structural formulas (i-4-5.1) to (i-4-5.4).

[0382] [Chemistry 36]

[0383]

[0384] Specific examples of the compound represented by the general formula (i-4-6) include compounds represented by the following structural formulas (i-4-6.1) to (i-4-6.3).

[0385] [Chemistry 37]

[0386]

[0387] As the compound represented by the general formula (i-5), a compound represented by the following general formula (i-5-1) is preferred.

[0388] [Chemistry 38]

[0389]

[0390] In the general formula (i-5-1), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0391] Specific examples of the compound represented by the general formula (i-5-1) include compounds represented by the following structural formulas (i-5-1.1) to (i-5-1.2).

[0392] [Chemistry 39]

[0393]

[0394] As the compound represented by the general formula (i-6), compounds represented by the following structural formulas (i-6-1) to (i-6-2) are preferred.

[0395] [Chemistry 40]

[0396]

[0397] In the general formula (i-6-1) to the general formula (i-6-2), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0398] Specific examples of the compound represented by the general formula (i-6-1) include compounds represented by the following structural formulas (i-6-1.1) to (i-6-1.2).

[0399] [Chemistry 41]

[0400]

[0401] Specific examples of the compound represented by the general formula (i-6-2) include compounds represented by the following structural formulas (i-6-2.1) to (i-6-2.2).

[0402] [Chemistry 42]

[0403]

[0404] As the compound represented by the general formula (i-7), compounds represented by the following general formulas (i-7-1) to (i-7-2) are preferred.

[0405] [Chemistry 43]

[0406]

[0407] In the general formula (i-7-1) to the general formula (i-7-2), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0408] Specific examples of the compound represented by general formula (i-7-1) include compounds represented by the following structural formula (i-7-1.1).

[0409] [Chemistry 44]

[0410]

[0411] Specific examples of the compound represented by general formula (i-7-2) include compounds represented by the following structural formula (i-7-2.1).

[0412] [Chemistry 45]

[0413]

[0414] As the compound represented by the general formula (i-8), compounds represented by the following general formulas (i-8-1) to (i-8-5) are preferred.

[0415] [Chemistry 46]

[0416]

[0417] In the general formula (i-8-1) to the general formula (i-8-5), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0418] Specific examples of the compound represented by general formula (i-8-1) include compounds represented by the following structural formulas (i-8-1.1) to (i-8-1.2).

[0419] [Chemistry 47]

[0420]

[0421] Specific examples of the compound represented by the general formula (i-8-2) include compounds represented by the following structural formulas (i-8-2.1) to (i-8-2.2).

[0422] [Chemistry 48]

[0423]

[0424] Specific examples of the compound represented by the general formula (i-8-3) include compounds represented by the following structural formulas (i-8-3.1) to (i-8-3.4).

[0425] [Chemistry 49]

[0426]

[0427] Specific examples of the compound represented by general formula (i-8-4) include compounds represented by the following structural formulas (i-8-4.1) to (i-8-4.2).

[0428] [Chemistry 50]

[0429]

[0430] Specific examples of the compound represented by the general formula (i-8-5) include compounds represented by the following structural formulas (i-8-5.1) to (i-8-5.2).

[0431] [Chemistry 51]

[0432]

[0433] As the compound represented by the general formula (i-9), a compound represented by the following general formula (i-9-1) is preferred.

[0434] [Chemistry 52]

[0435]

[0436] In the general formula (i-9-1), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0437] Specific examples of the compound represented by the general formula (i-9-1) include compounds represented by the following structural formula (i-9-1.1).

[0438] [Chemistry 53]

[0439]

[0440] As the compound represented by the general formula (i-10), compounds represented by the following general formulas (i-10-1) to (i-10-3) are preferred.

[0441] [Chemistry 54]

[0442]

[0443] In the general formula (i-10-1) to the general formula (i-10-3), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0444] Specific examples of the compound represented by the general formula (i-10-1) include compounds represented by the following structural formulas (i-10-1.1) to (i-10-1.3).

[0445] [Chemistry 55]

[0446]

[0447] Specific examples of the compound represented by the general formula (i-10-2) include compounds represented by the following structural formulas (i-10-2.1) to (i-10-2.4).

[0448] [Chemistry 56]

[0449]

[0450] Specific examples of the compound represented by the general formula (i-10-3) include compounds represented by the following structural formulas (i-10-3.1) to (i-10-3.3).

[0451] [Chemistry 57]

[0452]

[0453] As the compound represented by the general formula (i-11), compounds represented by the following general formulas (i-11-1) to (i-11-6) are preferred.

[0454] [Chemistry 58]

[0455]

[0456] In the general formulas (i-11-1) to (i-11-6), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0457] Specific examples of the compound represented by general formula (i-11-1) include compounds represented by the following structural formulas (i-11-1.1) to (i-11-1.3).

[0458] [Chemistry 59]

[0459]

[0460] Specific examples of the compound represented by general formula (i-11-2) include compounds represented by the following structural formulas (i-11-2.1) to (i-11-2.3).

[0461] [Chemistry 60]

[0462]

[0463] Specific examples of the compound represented by the general formula (i-11-3) include compounds represented by the following structural formulas (i-11-3.1) to (i-11-3.2).

[0464] [Chemistry 61]

[0465]

[0466] Specific examples of the compound represented by general formula (i-11-4) include compounds represented by the following structural formulas (i-11-4.1) to (i-11-4.3).

[0467] [Chemistry 62]

[0468]

[0469] Specific examples of the compound represented by the general formula (i-11-5) include compounds represented by the following structural formulas (i-11-5.1) to (i-11-5.3).

[0470] [Chemistry 63]

[0471]

[0472] Specific examples of the compound represented by the general formula (i-11-6) include compounds represented by the following structural formulas (i-11-6.1) to (i-11-6.2).

[0473] [Chemistry 64]

[0474]

[0475] As the compound represented by the general formula (i-12), compounds represented by the following general formulas (i-12-1) to (i-12-4) are preferred.

[0476] [Chemistry 65]

[0477]

[0478] In the general formulas (i-12-1) to (i-12-4), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0479] Specific examples of the compound represented by the general formula (i-12-1) include compounds represented by the following structural formulas (i-12-1.1) to (i-12-1.3).

[0480] [Chemistry 66]

[0481]

[0482] Specific examples of the compound represented by the general formula (i-12-2) include compounds represented by the following structural formulas (i-12-2.1) to (i-12-2.2).

[0483] [Chemistry 67]

[0484]

[0485] Specific examples of the compound represented by the general formula (i-12-3) include compounds represented by the following structural formulas (i-12-3.1) and (i-12-3.2).

[0486] [Chemistry 68]

[0487]

[0488] Specific examples of the compound represented by the general formula (i-12-4) include compounds represented by the following structural formulas (i-12-4.1) to (i-12-4.2).

[0489]

[0490] As the compound represented by the general formula (i-13), a compound represented by the following general formula (i-13-1) is preferred.

[0491] [Chemistry 69]

[0492]

[0493] In the general formula (i-13-1), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0494] Specific examples of the compound represented by the general formula (i-13-1) include compounds represented by the following structural formulas (i-13-1.1) to (i-13-1.3).

[0495] [Chemistry 70]

[0496]

[0497] The compound represented by the general formula (i-14) is preferably a compound represented by the following general formula (i-14-1).

[0498] [Chemistry 71]

[0499]

[0500] In the general formula (i-14-1), R i1 and S i1 Each independently represents R i1 and S i1 Same meaning.

[0501] Specific examples of the compound represented by the general formula (i-14-1) include compounds represented by the following structural formulas (i-14-1.1) to (i-14-1.2).

[0502] [Chemistry 72]

[0503]

[0504] General formula (i), general formula (i-1) to general formula (i-14), general formula (i-1-1) to general formula (i-1-2), general formula (i-2-1) to general formula (i-2-4), general formula (i-3-1) to general formula (i-3-3), general formula (i-4-1) to general formula (i-4-6), general formula (i-5-1), general formula (i-6-1) to general formula (i-6-2), general formula (i-7-1) to general formula (i-7-2), general formula (i-8-1) to general formula (i-8-5), general formula (i-9-1), general formula (i-10-1) to general formula (i-10-3), general formula (i-11-1) to general formula (i-11-6), general formula (i-12-1) to general formula (i-12-4) ), general formula (i-13-1), general formula (i-14-1), structural formula (i-1-1.1) to structural formula (i-1-1.3), structural formula (i-1-2.1) to structural formula (i-1-2.3), structural formula (i-2-1.1) to structural formula (i-2-1.3), structural formula (i-2-2.1) to structural formula (i-2-2.3), structural formula (i-2-3.1) to structural formula (i-2-3.3), structural formula (i-2-4.1), structural formula (i-3-1.1) to structural formula (i-3-1.3), structural formula (i-3-2.1) to structural formula (i-3-2.3), structural formula (i-3-3.1) to structural formula (i-3-3.3), structural formula (i-4-1.1) to structural formula (i-4-1.3), structural formula (i-4-2.1) to structural formula (i-4-2.3), structural formula (i-4-3.1) to structural formula (i-4-3.3), structural formula (i-4-4.1) to structural formula (i-4-4.3), structural formula (i-4-5.1) to structural formula (i-4-5.4), structural formula (i-4-6.1) to structural formula (i-4-6.3), structural formula (i-5-1.1) to structural formula (i-5-1.2), structural formula (i-6-1.1) to structural formula (i-6-1.2), structural formula (i-6-2.1) to structural formula (i-6-2.2), structural formula (i-7-1.1), structural formula (i-7-2.1), structural formula (i-8-1.1) to structural formula (i-8-1.2), structural formula (i-8-2.1) to structural formula (i-8-2.2), structural formula (i-8-3.1) to structural formula (i-8-3.4), structural formula (i-8-4.1) to structural formula (i-8-4.2), structural formula (i-8-5.1) to structural formula (i-8-5.2), structural formula (i-9-1.1), structural formula (i-10-1.1) to structural formula (i-10-1.3), structural formula (i-10-2.1) to structural formula (i-10-2.4), structural formula (i-10-3.1) to structural formula (i-10-3.3), structural formula (i-11-1.1)~Structural formula (i-11-1.3), structural formula (i-11-2.1)~Structural formula (i-11-2.3), structural formula (i-11-3.1)~Structural formula (i-11-3.2), structural formula (i-11-4.1)~Structural formula (i-11-4.3), structural formula (i-11-5.1)~Structural formula (i-11-5.3), structural formula (i-11-6.1)~Structural formula (i-11-6.2), structural formula (i-12-1.1)~Structural formula (i-12-1.3), structural formula ( The compounds represented by formula (i-12-2.1) to formula (i-12-2.2), formula (i-12-3.1) to formula (i-12-3.2), formula (i-12-4.1) to formula (i-12-4.2), formula (i-13-1.1) to formula (i-13-1.3) or formula (i-14-1.1) to formula (i-14-1.2) are used in the liquid crystal composition in one or more kinds, preferably one to ten kinds, preferably one to five kinds, and preferably one to three kinds. .

[0505] General formula (i), general formula (i-1) to general formula (i-14), general formula (i-1-1) to general formula (i-1-2), general formula (i-2-1) to general formula (i-2-4), general formula (i-3-1) to general formula (i-3-3), general formula (i-4-1) to general formula (i-4-6), general formula (i-5-1), general formula (i-6-1) to general formula (i-6-2), general formula (i-7-1) to general formula (i-7-2), general formula (i-8-1) to general formula (i-8-5), general formula (i-9-1), general formula (i-10-1) to general formula (i-10-3), general formula (i-11-1) to general formula (i-11-6), general formula (i-12-1) to general formula (i-12-4) ), general formula (i-13-1), general formula (i-14-1), structural formula (i-1-1.1) to structural formula (i-1-1.3), structural formula (i-1-2.1) to structural formula (i-1-2.3), structural formula (i-2-1.1) to structural formula (i-2-1.3), structural formula (i-2-2.1) to structural formula (i-2-2.3), structural formula (i-2-3.1) to structural formula (i-2-3.3), structural formula (i-2-4.1), structural formula (i-3-1.1) to structural formula (i-3-1.3), structural formula (i-3-2.1) to structural formula (i-3-2.3), structural formula (i-3-3.1) to structural formula (i-3-3.3), structural formula (i-4-1.1) to structural formula (i-4-1.3), structural formula (i-4-2.1) to structural formula (i-4-2.3), structural formula (i-4-3.1) to structural formula (i-4-3.3), structural formula (i-4-4.1) to structural formula (i-4-4.3), structural formula (i-4-5.1) to structural formula (i-4-5.4), structural formula (i-4-6.1) to structural formula (i-4-6.3), structural formula (i-5-1.1) to structural formula (i-5-1.2), structural formula (i-6-1.1) to structural formula (i-6-1.2), structural formula (i-6-2.1) to structural formula (i-6-2.2), structural formula (i-7-1.1), structural formula (i-7-2.1), structural formula (i-8-1.1) to structural formula (i-8-1.2), structural formula (i-8-2.1) to structural formula (i-8-2.2), structural formula (i-8-3.1) to structural formula (i-8-3.4), structural formula (i-8-4.1) to structural formula (i-8-4.2), structural formula (i-8-5.1) to structural formula (i-8-5.2), structural formula (i-9-1.1), structural formula (i-10-1.1) to structural formula (i-10-1.3), structural formula (i-10-2.1) to structural formula (i-10-2.4), structural formula (i-10-3.1) to structural formula (i-10-3.3), structural formula (i-11-1.1) ~ Structural formula (i-11-1.3), Structural formula (i-11-2.1) ~ Structural formula (i-11-2.3), Structural formula (i-11-3.1) ~ Structural formula (i-11-3.2), Structural formula (i-11-4.1) ~ Structural formula (i-11-4.3), Structural formula (i-11-5.1) ~ Structural formula (i-11-5.3), Structural formula (i-11-6.1) ~ Structural formula (i-11-6.2), Structural formula (i-12-1.1) ~ Structural formula (i-12-1.3), Structural formula (i-12-2.1) ~ Structural formula (i-12-2.2), The lower limit of the total content of the compounds represented by formula (i-12-3.1) to formula (i-12-3.2), formula (i-12-4.1) to formula (i-12-4.2), formula (i-13-1.1) to formula (i-13-1.3) or formula (i-14-1.1) to formula (i-14-1.2) in 100% by mass of the liquid crystal composition is preferably 0.5% by mass or more, preferably 1% by mass or more, preferably 3% by mass or more, preferably 5% by mass or more, preferably 10% by mass or more, preferably 15% by mass or more, and preferably 20% by mass or more.

[0506] General formula (i), general formula (i-1) to general formula (i-14), general formula (i-1-1) to general formula (i-1-2), general formula (i-2-1) to general formula (i-2-4), general formula (i-3-1) to general formula (i-3-3), general formula (i-4-1) to general formula (i-4-6), general formula (i-5-1), general formula (i-6-1) to general formula (i-6-2), general formula (i-7-1) to general formula (i-7-2), general formula (i-8-1) to general formula (i-8-5), general formula (i-9-1), general formula (i-10-1) to general formula (i-10-3), general formula (i-11-1) to general formula (i-11-6), general formula (i-12-1) to general formula (i-12-4) ), general formula (i-13-1), general formula (i-14-1), structural formula (i-1-1.1) to structural formula (i-1-1.3), structural formula (i-1-2.1) to structural formula (i-1-2.3), structural formula (i-2-1.1) to structural formula (i-2-1.3), structural formula (i-2-2.1) to structural formula (i-2-2.3), structural formula (i-2-3.1) to structural formula (i-2-3.3), structural formula (i-2-4.1), structural formula (i-3-1.1) to structural formula (i-3-1.3), structural formula (i-3-2.1) to structural formula (i-3-2.3), structural formula (i-3-3.1) to structural formula (i-3-3.3), structural formula (i-4-1.1) to structural formula (i-4-1.3), structural formula (i-4-2.1) to structural formula (i-4-2.3), structural formula (i-4-3.1) to structural formula (i-4-3.3), structural formula (i-4-4.1) to structural formula (i-4-4.3), structural formula (i-4-5.1) to structural formula (i-4-5.4), structural formula (i-4-6.1) to structural formula (i-4-6.3), structural formula (i-5-1.1) to structural formula (i-5-1.2), structural formula (i-6-1.1) to structural formula (i-6-1.2), structural formula (i-6-2.1) to structural formula (i-6-2.2), structural formula (i-7-1.1), structural formula (i-7-2.1), structural formula (i-8-1.1) to structural formula (i-8-1.2), structural formula (i-8-2.1) to structural formula (i-8-2.2), structural formula (i-8-3.1) to structural formula (i-8-3.4), structural formula (i-8-4.1) to structural formula (i-8-4.2), structural formula (i-8-5.1) to structural formula (i-8-5.2), structural formula (i-9-1.1), structural formula (i-10-1.1) to structural formula (i-10-1.3), structural formula (i-10-2.1) to structural formula (i-10-2.4), structural formula (i-10-3.1) to structural formula (i-10-3.3), structural formula (i-11-1.1) ~ Structural formula (i-11-1.3), Structural formula (i-11-2.1) ~ Structural formula (i-11-2.3), Structural formula (i-11-3.1) ~ Structural formula (i-11-3.2), Structural formula (i-11-4.1) ~ Structural formula (i-11-4.3), Structural formula (i-11-5.1) ~ Structural formula (i-11-5.3), Structural formula (i-11-6.1) ~ Structural formula (i-11-6.2), Structural formula (i-12-1.1) ~ Structural formula (i-12-1.3), Structural formula (i-12-2.1) ~ Structural formula (i-12-2.2), The upper limit of the total content of the compounds represented by the structural formula (i-12-3.1) to the structural formula (i-12-3.2), the structural formula (i-12-4.1) to the structural formula (i-12-4.2), the structural formula (i-13-1.1) to the structural formula (i-13-1.3) or the structural formula (i-14-1.1) to the structural formula (i-14-1.2) in 100% by mass of the liquid crystal composition is 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. .

[0507] Regarding solubility, Δn and / or Δε rFrom the perspective of general formula (i), general formula (i-1) to general formula (i-14), general formula (i-1-1) to general formula (i-1-2), general formula (i-2-1) to general formula (i-2-4), general formula (i-3-1) to general formula (i-3-3), general formula (i-4-1) to general formula (i-4-6), general formula (i-5-1), general formula (i-6-1) to general formula (i-6-2), general formula (i-7-1) to general formula (i-7-2), general formula (i-8-1) to general formula (i-8-5), general formula (i-9-1), general formula (i-10-1) to general formula (i-10-3), general formula (i-11-1) to general formula (i-11-6), general formula (i-12-1) to general formula (i-12-1) 12-4), general formula (i-13-1), general formula (i-14-1), structural formula (i-1-1.1) to structural formula (i-1-1.3), structural formula (i-1-2.1) to structural formula (i-1-2.3), structural formula (i-2-1.1) to structural formula (i-2-1.3), structural formula (i-2-2.1) to structural formula (i-2-2.3), structural formula (i-2-3.1) to structural formula (i-2-3.3), structural formula (i-2-4.1), structural formula (i-3-1.1) to structural formula (i-3-1.3), structural formula (i-3-2.1) to structural formula (i-3-2.3), structural formula (i-3-3.1) to structural formula (i-3-3.3), Structural formula (i-4-1.1) to (i-4-1.3), Structural formula (i-4-2.1) to (i-4-2.3), Structural formula (i-4-3.1) to (i-4-3.3), Structural formula (i-4-4.1) to (i-4-4.3), Structural formula (i-4-5.1) to (i-4-5.4), Structural formula (i-4-6.1) to (i-4-6.3), Structural formula (i-5-1.1) to (i-5-1.2), Structural formula (i-6-1.1) to (i-6-1.2), Structural formula (i-6-2.1) to (i-6-2.2), Structural formula (i-7-1.1), Structural formula Formula (i-7-2.1), structural formula (i-8-1.1) to structural formula (i-8-1.2), structural formula (i-8-2.1) to structural formula (i-8-2.2), structural formula (i-8-3.1) to structural formula (i-8-3.4), structural formula (i-8-4.1) to structural formula (i-8-4.2), structural formula (i-8-5.1) to structural formula (i-8-5.2), structural formula (i-9-1.1), structural formula (i-10-1.1) to structural formula (i-10-1.3), structural formula (i-10-2.1) to structural formula (i-10-2.4), structural formula (i-10-3.1) to structural formula (i-10-3.3), structural formula (i-11-1.1)~Structural formula (i-11-1.3), structural formula (i-11-2.1)~Structural formula (i-11-2.3), structural formula (i-11-3.1)~Structural formula (i-11-3.2), structural formula (i-11-4.1)~Structural formula (i-11-4.3), structural formula (i-11-5.1)~Structural formula (i-11-5.3), structural formula (i-11-6.1)~Structural formula (i-11-6.2), structural formula (i-12-1.1)~Structural formula (i-12-1.3), structural formula (i-12-2. The total content of the compounds represented by formula (1) to (i-12-2.2), formula (i-12-3.1) to (i-12-3.2), formula (i-12-4.1) to (i-12-4.2), formula (i-13-1.1) to (i-13-1.3) or formula (i-14-1.1) to (i-14-1.2) in 100% by mass of the liquid crystal composition is preferably 0.5% by mass to 35% by mass, preferably 1% by mass to 30% by mass, and preferably 3% by mass to 25% by mass. .

[0508] The compounds represented by the general formula (i) (including subordinate concepts) can be synthesized using known synthesis methods, and several examples are shown below.

[0509] (Preparation method 1) Preparation of a compound represented by the following formula (s-6)

[0510] [Chemistry 73]

[0511]

[0512] In the general formulas (s-1) to (s-6), R i1 , L i1 , L i2 and S i1 represents the same as R in the general formula (i) i1 , L i1 , L i2 and S i1 Same meaning.

[0513] First, by reacting a compound represented by the general formula (s-1) with a compound represented by the general formula (s-2), a compound represented by the general formula (s-3) can be obtained.

[0514] As a reaction method, for example, Suzuki coupling reaction using a metal catalyst and a base can be mentioned.

[0515] Specific examples of the metal catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0516] When palladium (II) acetate is used as the metal catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0517] Specific examples of the base include potassium carbonate, potassium phosphate, and cesium carbonate.

[0518] Next, by reacting the compound represented by the general formula (s-3) with the compound represented by the general formula (s-4), the compound represented by the general formula (s-5) can be obtained.

[0519] As a reaction method, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst and a base is mentioned, for example.

[0520] Specific examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0521] When palladium (II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0522] Specific examples of the copper catalyst include copper (I) iodide.

[0523] Specific examples of the base include triethylamine and diisopropylamine.

[0524] Finally, by reacting the compound represented by the general formula (s-5) with 1,1-thiocarbonyldiimidazole, 1,1-thiocarbonyldi-2(1H)-pyridone, thiophosgene, etc., the compound represented by the general formula (s-6) as the target product can be obtained.

[0525] (Preparation method 2) Preparation of a compound represented by the following formula (s-14)

[0526] [Chemistry 74]

[0527]

[0528] In the general formulas (s-7) to (s-14), R i1 , L i1 , Li2 and S i1 represents the same as R in the general formula (i) i1 , L i1 , L i2 and S i1 Same meaning.

[0529] First, the compound represented by the general formula (s-7) is reacted with trimethylsilyl acetylene to obtain the compound represented by the general formula (s-8).

[0530] As a reaction method, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst and a base is mentioned, for example.

[0531] Specific examples of the palladium catalyst, the copper catalyst, and the base include the compounds described in (Preparation Method 1).

[0532] Next, the compound represented by the general formula (s-8) is reacted with potassium carbonate in an alcohol solvent such as methanol to obtain a compound represented by the general formula (s-9).

[0533] Next, by reacting the compound represented by the general formula (s-9) with the compound represented by the general formula (s-10), the compound represented by the general formula (s-11) can be obtained.

[0534] As a reaction method, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst and a base is mentioned, for example.

[0535] Specific examples of the palladium catalyst, the copper catalyst, and the base include the compounds described in (Preparation Method 1).

[0536] Next, by reacting the compound represented by the general formula (s-11) with the compound represented by the general formula (s-12), the compound represented by the general formula (s-13) can be obtained.

[0537] As a reaction method, Sonogashira coupling reaction using a palladium catalyst, a copper catalyst and a base is mentioned, for example.

[0538] Specific examples of the palladium catalyst, the copper catalyst, and the base include the compounds described in (Preparation Method 1).

[0539] Finally, by reacting the compound represented by the general formula (s-13) with 1,1-thiocarbonyldiimidazole, 1,1-thiocarbonyldi-2(1H)-pyridone, thiophosgene, etc., the compound represented by the general formula (s-14) as the target product can be obtained.

[0540] (Compound represented by general formula (ii))

[0541] The liquid crystal composition of the present invention contains one or two or more compounds represented by the following general formula (ii) having an isothiocyanate group (—NCS).

[0542] [Chemistry 75]

[0543]

[0544] In the general formula (ii), R ii1 It represents an alkyl group having 1 to 20 carbon atoms.

[0545] The alkyl group is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0546] The alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0547] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0548] In addition, one or more -CH2-CH2- in the alkyl group may be substituted by -CH=CH-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CF=CF- and / or -C≡C-.

[0549] In addition, one or two or more -CH2-CH2-CH2- in the alkyl group may be substituted by -O-CO-O-.

[0550] Furthermore, one or two or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms.

[0551] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0552] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0553] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0554] For example, R ii1 By substituting one -CH2- in the above alkyl group with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0555] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0556] The alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0557] In addition, R ii1 By substituting one -CH2- in the above alkyl group with -S-, an alkylmercapto group (alkylthio group) having 1 to 19 carbon atoms can be represented.

[0558] The alkylmercapto group is a linear, branched or cyclic alkylmercapto group, and is preferably a linear alkylmercapto group.

[0559] The alkylmercapto group preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0560] In addition, R ii1 By replacing one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0561] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0562] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0563] In addition, R ii1 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0564] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0565] The alkynyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0566] The alkynyl group is preferably a group of the following formula (R ii1 -A) represents an alkynyl group.

[0567] [Chemistry 76]

[0568]

[0569] Formula (R ii1 -A), R ii1A It represents an alkyl group having 1 to 18 carbon atoms.

[0570] The alkyl group having 1 to 18 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0571] The alkyl group having 1 to 18 carbon atoms preferably has 1 to 8 carbon atoms.

[0572] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0573] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0574] In addition, one or two or more -CH2-CH2-CH2- in the alkyl group may be independently substituted by -O-CO-O-.

[0575] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom.

[0576] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0577] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0578] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0579] In addition, the formula (R ii1 -A), the black dot indicates the direction to A ii1 The bond key.

[0580] In addition, R ii1 An alkenyloxy group having 2 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or more -CH2-CH2- with -CH=CH-.

[0581] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0582] The alkenyloxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0583] In addition, R ii1 By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0584] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0585] The halogenated alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0586] In addition, R ii1A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or two or more hydrogen atoms in the alkyl group with halogen atoms.

[0587] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[0588] The halogenated alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0589] As R ii1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: ii1 -1)~Formula (R ii1 -56) etc.

[0590] [Chemistry 77]

[0591]

[0592] [Chemistry 78]

[0593]

[0594] Formula (R ii1 -1)~Formula (R ii1 -56), the black dot indicates the direction to A ii1 The bond key.

[0595] In R ii1 When the ring structure to which the bond is a phenyl group (aromatic), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. i1 When the bonded ring structure is a saturated ring structure such as cyclohexane, pyran and dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms.

[0596] In addition, as R ii1 In order to stabilize the nematic phase, the total number of carbon atoms and, if present, oxygen atoms is preferably 5 or less, and the chain is preferably straight.

[0597] In addition, as R ii1 From the viewpoint of solubility, preferably, a linear or branched alkyl group having 2 to 8 carbon atoms, a linear alkoxy group having 2 to 8 carbon atoms, a linear halogenated alkoxy group having 1 to 8 carbon atoms, a linear alkynyl group having 2 to 8 carbon atoms or a linear alkylthiol group having 1 to 6 carbon atoms.

[0598] In the general formula (ii), A ii1 and A ii2 Each independently represents a group (a), a group (b), a group (c) and a group (d) selected from the following:

[0599] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- in the group may be substituted with -O- and / or -S-)

[0600] (b) 1,4-phenylene (one or two or more -CH= in the group may be substituted with -N=)

[0601] (c) 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene -2,7-diyl (one or two or more -CH= in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl may be substituted with -N=)

[0602] (d) thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl, benzo[1,2-b:4,5-b']dithiophene-2,6-diyl (one -CH= or two or more -CH= in the above group may be substituted with -N=)

[0603] The basis of the group.

[0604] A ii1 and A ii2 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S ii1 replace.

[0605] Substituent S ii1 It represents any one of a halogen atom, a pentafluoromercapto 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.

[0606] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0607] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0608] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.

[0609] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0610] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0611] One or more -CH2-CH2-CH2- groups in the alkyl group may be independently substituted by -O-CO-O-.

[0612] Furthermore, one or two or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms.

[0613] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0614] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0615] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0616] As a substituent S ii1 , preferably a fluorine atom or a chlorine atom.

[0617] In addition, A ii1 At least one or A ii2 Preferably, at least one substituent S ii1 The substitution is preferably substitution with a halogen atom, and preferably substitution with a fluorine atom.

[0618] In addition, in the substituent S ii1 When there are plural, these may be the same or different.

[0619] As A ii1 The substituent S in ii1 The substitution position is preferably the following formula (A ii1 -SP-1)~Formula (A ii1 -SP-6).

[0620] [Chemistry 79]

[0621]

[0622] Formula (A ii1 -SP-1)~Formula (A ii1 -SP-6), the white dot indicates the direction to R ii1 or Z ii1 The black dots represent the bonds to Z ii1 The bond key.

[0623] As A ii2 The substituent S in ii1 The substitution position is preferably the following formula (A ii2 -SP-1)~Formula (A ii2 -SP-8).

[0624] [Chemistry 80]

[0625]

[0626] Formula (A ii2 -SP-1)~Formula (A ii2 -SP-8), the white dot indicates the direction of Z ii1 The black dots represent the bonds to the isothiocyanate group (-NCS).

[0627] More specifically, A ii1 Preferably, it is represented by the following formula (A ii1 -1)~Formula (A ii1 -25).

[0628] [Chemistry 81]

[0629]

[0630] Formula (A ii1 -1)~Formula (A ii1 -25), the white dot indicates the direction to R ii1 or Z ii1 The black dots represent the bonds to Z ii1 The bond key.

[0631] More specifically, A ii2 Preferably, it is represented by the following formula (A ii2 -1)~Formula (A ii2 -8).

[0632] [Chemistry 82]

[0633]

[0634] Formula (A ii2-1)~Formula (A ii2 -8), the white dot indicates the direction Z ii1 The black dots represent the bonds to the isothiocyanate group (-NCS).

[0635] In the general formula (ii), Z ii1 It represents any of a single bond and an alkylene group having 1 to 20 carbon atoms.

[0636] One or more -CH2- groups in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[0637] In addition, one or more -CH2-CH2- in the alkylene group may be independently replaced by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[0638] In addition, one or two or more -CH2-CH2-CH2- in the alkylene group may be independently substituted by -O-CO-O-.

[0639] However, when the alkylene group having 1 to 20 carbon atoms is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[0640] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0641] Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted alkylene groups) include the following: ii1 -1)~Formula(Z ii1 -24) represented by the base, etc.

[0642] [Chemistry 83]

[0643]

[0644] Formula (Z ii1 -1)~Formula(Z ii1 -24), the white dot indicates the direction to A ii1 The black dots indicate the bond to A ii1 or A ii2 The bond key.

[0645] In the general formula (ii), n ii1 It represents an integer of 1-4, preferably 1-2.

[0646] In nii1 When Δn and / or Δε is 1, r From the point of view of Z ii1 Preferably, it represents a single bond or -C≡C-.

[0647] In addition, in n ii1 When Δn and / or Δε is 2, r From the point of view of Z ii1 Preferably, it represents a single bond or -C≡C-.

[0648] In addition, in the general formula (ii), in A ii1 and Z ii1 When there are plural numbers, these may be the same or different.

[0649] However, the compounds represented by the general formula (ii) exclude the compounds represented by the general formula (i) (including subordinate concepts).

[0650] As the compound represented by the general formula (ii), compounds represented by the following general formulas (ii-1) to (ii-8) are preferred.

[0651] [Chemistry 84]

[0652] R ii1 -A ii1 -A ii2 -NCS (ii-1)

[0653]

[0654] R ii1 -A ii1 -A ii1-2 -A ii1-3 -A ii2 -NCS (ii-8)

[0655] In the general formulas (ii-1) to (ii-8), R ii1 , A ii1 and A ii2 represents the same as R in the general formula (ii) ii1 , A ii1 and A ii2 The same meaning respectively.

[0656] In the general formula (ii-3) to the general formula (ii-8), A ii1-2 and A ii1-3 The definitions of are independently the same as those of A in the general formula (ii). ii1 The definition is the same.

[0657] As the compound represented by the general formula (ii-1), compounds represented by the following general formulas (ii-1-1) to (ii-1-2) are preferred.

[0658] [Chemistry 85]

[0659]

[0660] In the general formula (ii-1-1) to the general formula (ii-1-2), R ii1 represents the same as R in the general formula (ii) ii1 The same meaning respectively.

[0661] Specific examples of the compound represented by the general formula (ii-1-1) include compounds represented by the following structural formulas (ii-1-1.1) to (ii-1-1.4).

[0662] [Chemistry 86]

[0663]

[0664] Specific examples of the compound represented by the general formula (ii-1-2) include compounds represented by the following structural formulas (ii-1-2.1) to (ii-1-2.6).

[0665] [Chemistry 87]

[0666]

[0667] As the compound represented by the general formula (ii-2), compounds represented by the following general formulas (ii-2-1) to (ii-2-10) are preferred.

[0668] [Chemistry 88]

[0669]

[0670] [Chemistry 89]

[0671]

[0672] In the general formulas (ii-2-1) to (ii-2-10), R ii1 and S ii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[0673] Specific examples of the compound represented by the general formula (ii-2-1) include compounds represented by the following structural formulas (ii-2-1.1) to (ii-2-1.4).

[0674] [Chemistry 90]

[0675]

[0676] Specific examples of the compound represented by general formula (ii-2-2) include compounds represented by the following structural formulas (ii-2-2.1) to (ii-2-2.10).

[0677] [Chemistry 91]

[0678]

[0679] Specific examples of the compound represented by the general formula (ii-2-3) include compounds represented by the following structural formulas (ii-2-3.1) to (ii-2-3.3).

[0680] [Chemistry 92]

[0681]

[0682] Specific examples of the compound represented by general formula (ii-2-4) include compounds represented by the following structural formulas (ii-2-4.1) to (ii-2-4.8).

[0683] [Chemistry 93]

[0684]

[0685] Specific examples of the compound represented by the general formula (ii-2-5) include compounds represented by the following structural formulas (ii-2-5.1) to (ii-2-5.4).

[0686] [Chemistry 94]

[0687]

[0688] Specific examples of the compound represented by the general formula (ii-2-6) include compounds represented by the following structural formulas (ii-2-6.1) to (ii-2-6.4).

[0689] [Chemistry 95]

[0690]

[0691] Specific examples of the compound represented by the general formula (ii-2-7) include compounds represented by the following structural formulas (ii-2-7.1) to (ii-2-7.3).

[0692] [Chemistry 96]

[0693]

[0694] Specific examples of the compound represented by general formula (ii-2-8) include compounds represented by the following structural formulas (ii-2-8.1) to (ii-2-8.3).

[0695] [Chemistry 97]

[0696]

[0697] Specific examples of the compound represented by the general formula (ii-2-9) include compounds represented by the following structural formulas (ii-2-9.1) to (ii-2-9.4).

[0698] [Chemistry 98]

[0699]

[0700] Specific examples of the compound represented by the general formula (ii-2-10) include compounds represented by the following structural formulas (ii-2-10.1) to (ii-2-10.4).

[0701] [Chemistry 99]

[0702]

[0703] As the compound represented by the general formula (ii-3), compounds represented by the following general formulas (ii-3-1) to (ii-3-16) are preferred.

[0704] [Chemical 100]

[0705]

[0706] [Chemistry 101]

[0707]

[0708] In the general formulas (ii-3-1) to (ii-3-16), R ii1 and S ii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[0709] Specific examples of the compound represented by general formula (ii-3-1) include compounds represented by the following structural formulas (ii-3-1.1) to (ii-3-1.4).

[0710] [Chemistry 102]

[0711]

[0712] Specific examples of the compound represented by general formula (ii-3-2) include compounds represented by the following structural formulas (ii-3-2.1) to (ii-3-2.4).

[0713] [Chemistry 103]

[0714]

[0715] Specific examples of the compound represented by general formula (ii-3-3) include compounds represented by the following structural formulas (ii-3-3.1) to (ii-3-3.7).

[0716] [Chemistry 104]

[0717]

[0718] [Chemistry 105]

[0719]

[0720] Specific examples of the compound represented by general formula (ii-3-4) include compounds represented by the following structural formulas (ii-3-4.1) to (ii-3-4.5).

[0721] [Chemistry 106]

[0722]

[0723] Specific examples of the compound represented by general formula (ii-3-5) include compounds represented by the following structural formulas (ii-3-5.1) to (ii-3-5.7).

[0724] [Chemistry 107]

[0725]

[0726] Specific examples of the compound represented by general formula (ii-3-6) include compounds represented by the following structural formulas (ii-3-6.1) to (ii-3-6.3).

[0727] [Chemistry 108]

[0728]

[0729] Specific examples of the compound represented by the general formula (ii-3-7) include compounds represented by the following structural formulas (ii-3-7.1) to (ii-3-7.7).

[0730] [Chemistry 109]

[0731]

[0732] Specific examples of the compound represented by general formula (ii-3-8) include compounds represented by the following structural formulas (ii-3-8.1) to (ii-3-8.3).

[0733] [Chemistry 110]

[0734]

[0735] Specific examples of the compound represented by general formula (ii-3-9) include compounds represented by the following structural formulas (ii-3-9.1) to (ii-3-9.4).

[0736] [Chemistry 111]

[0737]

[0738] Specific examples of the compound represented by the general formula (ii-3-10) include compounds represented by the following structural formulas (ii-3-10.1) to (ii-3-10.3).

[0739] [Chemistry 112]

[0740]

[0741] Specific examples of the compound represented by the general formula (ii-3-11) include compounds represented by the following structural formulas (ii-3-11.1) to (ii-3-11.3).

[0742] [Chemistry 113]

[0743]

[0744] Specific examples of the compound represented by general formula (ii-3-12) include compounds represented by the following structural formulas (ii-3-12.1) to (ii-3-12.3).

[0745] [Chemistry 114]

[0746]

[0747] Specific examples of the compound represented by general formula (ii-3-13) include compounds represented by the following structural formulas (ii-3-13.1) to (ii-3-13.4).

[0748] [Chemistry 115]

[0749]

[0750] Specific examples of the compound represented by the general formula (ii-3-14) include compounds represented by the following structural formulas (ii-3-14.1) to (ii-3-14.3).

[0751] [Chemistry 116]

[0752]

[0753] Specific examples of the compound represented by general formula (ii-3-15) include compounds represented by the following structural formulas (ii-3-15.1) to (ii-3-15.3).

[0754] [Chemistry 117]

[0755]

[0756] Specific examples of the compound represented by general formula (ii-3-16) include compounds represented by the following structural formulas (ii-3-16.1) to (ii-3-16.3).

[0757] [Chemistry 118]

[0758]

[0759] As the compound represented by the general formula (ii-4), compounds represented by the following general formulas (ii-4-1) to (ii-4-26) are preferred.

[0760] [Chemistry 119]

[0761]

[0762] [Chemistry 120]

[0763]

[0764] [Chemistry 121]

[0765]

[0766] In the general formula (ii-4-1) to the general formula (ii-4-26), R ii1 and S ii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[0767] Specific examples of the compound represented by general formula (ii-4-1) include compounds represented by the following structural formulas (ii-4-1.1) to (ii-4-1.4).

[0768] [Chemistry 122]

[0769]

[0770] Specific examples of the compound represented by general formula (ii-4-2) include compounds represented by the following structural formulas (ii-4-2.1) to (ii-4-2.4).

[0771] [Chemistry 123]

[0772]

[0773] Specific examples of the compound represented by the general formula (ii-4-3) include compounds represented by the following structural formulas (ii-4-3.1) to (ii-4-3.8).

[0774] [Chemistry 124]

[0775]

[0776] [Chemistry 125]

[0777]

[0778] Specific examples of the compound represented by general formula (ii-4-4) include compounds represented by the following structural formulas (ii-4-4.1) to (ii-4-4.5).

[0779] [Chemistry 126]

[0780]

[0781] Specific examples of the compound represented by general formula (ii-4-5) include compounds represented by the following structural formula (ii-4-5.1).

[0782] [Chemistry 127]

[0783]

[0784] Specific examples of the compound represented by the general formula (ii-4-6) include compounds represented by the following structural formulas (ii-4-6.1) to (ii-4-6.5).

[0785] [Chemistry 128]

[0786]

[0787] Specific examples of the compound represented by general formula (ii-4-7) include compounds represented by the following structural formula (ii-4-7.1).

[0788] [Chemistry 129]

[0789]

[0790] Specific examples of the compound represented by general formula (ii-4-8) include compounds represented by the following structural formulas (ii-4-8.1) to (ii-4-8.4).

[0791] [Chemistry 130]

[0792]

[0793] Specific examples of the compound represented by the general formula (ii-4-9) include compounds represented by the following structural formulas (ii-4-9.1) to (ii-4-9.4).

[0794] [Chemistry 131]

[0795]

[0796] Specific examples of the compound represented by the general formula (ii-4-10) include compounds represented by the following structural formulas (ii-4-10.1) to (ii-4-10.4).

[0797] [Chemistry 132]

[0798]

[0799] Specific examples of the compound represented by the general formula (ii-4-11) include compounds represented by the following structural formulas (ii-4-11.1) to (ii-4-11.5).

[0800] [Chemistry 133]

[0801]

[0802] Specific examples of the compound represented by general formula (ii-4-12) include compounds represented by the following structural formulas (ii-4-12.1) to (ii-4-12.5).

[0803] [Chemistry 134]

[0804]

[0805] Specific examples of the compound represented by the general formula (ii-4-13) include compounds represented by the following structural formulas (ii-4-13.1) to (ii-4-13.4).

[0806] [Chemistry 135]

[0807]

[0808] Specific examples of the compound represented by general formula (ii-4-14) include compounds represented by the following structural formulas (ii-4-14.1) to (ii-4-14.4).

[0809] [Chemistry 136]

[0810]

[0811] Specific examples of the compound represented by the general formula (ii-4-15) include compounds represented by the following structural formulas (ii-4-15.1) to (ii-4-15.6).

[0812] [Chemistry 137]

[0813]

[0814] Specific examples of the compound represented by general formula (ii-4-16) include compounds represented by the following structural formulas (ii-4-16.1) to (ii-4-16.3).

[0815] [Chemistry 138]

[0816]

[0817] Specific examples of the compound represented by the general formula (ii-4-17) include compounds represented by the following structural formulas (ii-4-17.1) to (ii-4-17.3).

[0818] [Chemistry 139]

[0819]

[0820] Specific examples of the compound represented by the general formula (ii-4-18) include compounds represented by the following structural formulas (ii-4-18.1) to (ii-4-18.4).

[0821] [Chemistry 140]

[0822]

[0823] Specific examples of the compound represented by the general formula (ii-4-19) include compounds represented by the following structural formulas (ii-4-19.1) to (ii-4-19.8).

[0824] [Chemistry 141]

[0825]

[0826] [Chemistry 142]

[0827]

[0828] Specific examples of the compound represented by the general formula (ii-4-20) include compounds represented by the following structural formulas (ii-4-20.1) to (ii-4-20.4).

[0829] [Chemistry 143]

[0830]

[0831] Specific examples of the compound represented by the general formula (ii-4-21) include compounds represented by the following structural formulas (ii-4-21.1) to (ii-4-21.4).

[0832] [Chemistry 144]

[0833]

[0834] Specific examples of the compound represented by general formula (ii-4-22) include compounds represented by the following structural formulas (ii-4-22.1) to (ii-4-22.3).

[0835] [Chemistry 145]

[0836]

[0837] Specific examples of the compound represented by the general formula (ii-4-23) include compounds represented by the following structural formulas (ii-4-23.1) to (ii-4-23.3).

[0838] [Chemistry 146]

[0839]

[0840] Specific examples of the compound represented by general formula (ii-4-24) include compounds represented by the following structural formulas (ii-4-24.1) to (ii-4-24.3).

[0841] [Chemistry 147]

[0842]

[0843] Specific examples of the compound represented by the general formula (ii-4-25) include compounds represented by the following structural formulas (ii-4-25.1) to (ii-4-25.3).

[0844] [Chemistry 148]

[0845]

[0846] Specific examples of the compound represented by general formula (ii-4-26) include compounds represented by the following structural formulas (ii-4-26.1) to (ii-4-26.3).

[0847] [Chemistry 149]

[0848]

[0849] As the compound represented by the general formula (ii-5), compounds represented by the following general formulas (ii-5-1) to (ii-5-5) are preferred.

[0850] [Chemistry 150]

[0851]

[0852] In the general formula (ii-5-1) to the general formula (ii-5-5), R ii1 and S ii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[0853] Specific examples of the compound represented by the general formula (ii-5-1) include compounds represented by the following structural formulas (ii-5-1.1) to (ii-5-1.4).

[0854] [Chemistry 151]

[0855]

[0856] Specific examples of the compound represented by general formula (ii-5-2) include compounds represented by the following structural formulas (ii-5-2.1) to (ii-5-2.4).

[0857] [Chemistry 152]

[0858]

[0859] Specific examples of the compound represented by general formula (ii-5-3) include compounds represented by the following structural formula (ii-5-3.1).

[0860] [Chemistry 153]

[0861]

[0862] Specific examples of the compound represented by general formula (ii-5-4) include compounds represented by the following structural formulas (ii-5-4.1) to (ii-5-4.3).

[0863] [Chemistry 154]

[0864]

[0865] Specific examples of the compound represented by general formula (ii-5-5) include compounds represented by the following structural formulas (ii-5-5.1) to (ii-5-5.3).

[0866] [Chemistry 155]

[0867]

[0868] As the compound represented by the general formula (ii-6), compounds represented by the following general formulas (ii-6-1) to (ii-6-33) are preferred.

[0869] [Chemistry 156]

[0870]

[0871] [Chemistry 157]

[0872]

[0873] [Chemistry 158]

[0874]

[0875] [Chemistry 159]

[0876]

[0877] In the general formula (ii-6-1) to the general formula (ii-6-33), R ii1 and S ii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[0878] Specific examples of the compound represented by general formula (ii-6-1) include compounds represented by the following structural formulas (ii-6-1.1) to (ii-6-1.4).

[0879] [Chemistry 160]

[0880]

[0881] Specific examples of the compound represented by general formula (ii-6-2) include compounds represented by the following structural formulas (ii-6-2.1) to (ii-6-2.4).

[0882] [Chemistry 161]

[0883]

[0884] Specific examples of the compound represented by the general formula (ii-6-3) include compounds represented by the following structural formulas (ii-6-3.1) to (ii-6-3.8).

[0885] [Chemistry 162]

[0886]

[0887] [Chemistry 163]

[0888]

[0889] Specific examples of the compound represented by general formula (ii-6-4) include compounds represented by the following structural formulas (ii-6-4.1) to (ii-6-4.4).

[0890] [Chemistry 164]

[0891]

[0892] Specific examples of the compound represented by general formula (ii-6-5) include compounds represented by the following structural formulas (ii-6-5.1) to (ii-6-5.4).

[0893] [Chemistry 165]

[0894]

[0895] Specific examples of the compound represented by general formula (ii-6-6) include compounds represented by the following structural formulas (ii-6-6.1) to (ii-6-6.2).

[0896] [Chemistry 166]

[0897]

[0898] Specific examples of the compound represented by general formula (ii-6-7) include compounds represented by the following structural formulas (ii-6-7.1) to (ii-6-7.8).

[0899] [Chemistry 167]

[0900]

[0901] [Chemistry 168]

[0902]

[0903] Specific examples of the compound represented by general formula (ii-6-8) include compounds represented by the following structural formulas (ii-6-8.1) to (ii-6-8.9).

[0904] [Chemistry 169]

[0905]

[0906] [Chemistry 170]

[0907]

[0908] Specific examples of the compound represented by the general formula (ii-6-9) include compounds represented by the following structural formulas (ii-6-9.1) to (ii-6-9.4).

[0909] [Chemistry 171]

[0910]

[0911] Specific examples of the compound represented by the general formula (ii-6-10) include compounds represented by the following structural formulas (ii-6-10.1) to (ii-6-10.4).

[0912] [Chemistry 172]

[0913]

[0914] Specific examples of the compound represented by the general formula (ii-6-11) include compounds represented by the following structural formulas (ii-6-11.1) to (ii-6-11.4).

[0915] [Chemistry 173]

[0916]

[0917] Specific examples of the compound represented by the general formula (ii-6-12) include compounds represented by the following structural formulas (ii-6-12.1) to (ii-6-12.4).

[0918] [Chemistry 174]

[0919]

[0920] Specific examples of the compound represented by the general formula (ii-6-13) include compounds represented by the following structural formulas (ii-6-13.1) to (ii-6-13.20).

[0921] [Chemistry 175]

[0922]

[0923] [Chemistry 176]

[0924]

[0925] [Chemistry 177]

[0926]

[0927] [Chemistry 178]

[0928]

[0929] [Chemistry 179]

[0930]

[0931] Specific examples of the compound represented by general formula (ii-6-14) include compounds represented by the following structural formulas (ii-6-14.1) to (ii-6-14.4).

[0932] [Chemistry 180]

[0933]

[0934] Specific examples of the compound represented by general formula (ii-6-15) include compounds represented by the following structural formula (ii-6-15.1).

[0935] [Chemistry 181]

[0936]

[0937] Specific examples of the compound represented by general formula (ii-6-16) include compounds represented by the following structural formulas (ii-6-16.1) to (ii-6-16.5).

[0938] [Chemistry 182]

[0939]

[0940] Specific examples of the compound represented by the general formula (ii-6-17) include compounds represented by the following structural formulas (ii-6-17.1) to (ii-6-17.4).

[0941] [Chemistry 183]

[0942]

[0943] Specific examples of the compound represented by the general formula (ii-6-18) include compounds represented by the following structural formulas (ii-6-18.1) to (ii-6-18.8).

[0944] [Chemistry 184]

[0945]

[0946] [Chemistry 185]

[0947]

[0948] Specific examples of the compound represented by general formula (ii-6-19) include compounds represented by the following structural formulas (ii-6-19.1) to (ii-6-19.4).

[0949] [Chemistry 186]

[0950]

[0951] Specific examples of the compound represented by the general formula (ii-6-20) include compounds represented by the following structural formulas (ii-6-20.1) to (ii-6-20.4).

[0952] [Chemistry 187]

[0953]

[0954] Specific examples of the compound represented by the general formula (ii-6-21) include compounds represented by the following structural formulas (ii-6-21.1) to (ii-6-21.4).

[0955] [Chemistry 188]

[0956]

[0957] Specific examples of the compound represented by general formula (ii-6-22) include compounds represented by the following structural formulas (ii-6-22.1) to (ii-6-22.14).

[0958] [Chemistry 189]

[0959]

[0960] [Chemistry 190]

[0961]

[0962] [Chemistry 191]

[0963]

[0964] Specific examples of the compound represented by the general formula (ii-6-23) include compounds represented by the following structural formulas (ii-6-23.1) to (ii-6-23.10).

[0965] [Chemistry 192]

[0966]

[0967] [Chemistry 193]

[0968]

[0969] Specific examples of the compound represented by general formula (ii-6-24) include compounds represented by the following structural formulas (ii-6-24.1) to (ii-6-24.2).

[0970] [Chemistry 194]

[0971]

[0972] Specific examples of the compound represented by the general formula (ii-6-25) include compounds represented by the following structural formulas (ii-6-25.1) to (ii-6-25.5).

[0973] [Chemistry 195]

[0974]

[0975] Specific examples of the compound represented by general formula (ii-6-26) include compounds represented by the following structural formulas (ii-6-26.1) to (ii-6-26.2).

[0976] [Chemistry 196]

[0977]

[0978] Specific examples of the compound represented by general formula (ii-6-27) include compounds represented by the following structural formula (ii-6-27.1).

[0979] [Chemistry 197]

[0980]

[0981] Specific examples of the compound represented by general formula (ii-6-28) include compounds represented by the following structural formulas (ii-6-28.1) to (ii-6-28.5).

[0982] [Chemistry 198]

[0983]

[0984] Specific examples of the compound represented by general formula (ii-6-29) include compounds represented by the following structural formula (ii-6-29.1).

[0985] [Chemistry 199]

[0986]

[0987] Specific examples of the compound represented by general formula (ii-6-30) include compounds represented by the following structural formula (ii-6-30.1).

[0988] [Chemistry 200]

[0989]

[0990] Specific examples of the compound represented by general formula (ii-6-31) include compounds represented by the following structural formulas (ii-6-31.1) to (ii-6-31.5).

[0991] [Chemistry 201]

[0992]

[0993] Specific examples of the compound represented by general formula (ii-6-32) include compounds represented by the following structural formula (ii-6-32.1).

[0994] [Chemistry 202]

[0995]

[0996] Specific examples of the compound represented by general formula (ii-6-33) include compounds represented by the following structural formulas (ii-6-33.1) to (ii-6-33.4).

[0997] [Chemistry 203]

[0998]

[0999] As the compound represented by the general formula (ii-7), a compound represented by the following general formula (ii-7-1) is preferred.

[1000] [Chemistry 204]

[1001]

[1002] In the general formula (ii-7-1), R ii1 and S ii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[1003] Specific examples of the compound represented by general formula (ii-7-1) include compounds represented by the following structural formula (ii-7-1.1).

[1004] [Chemistry 205]

[1005]

[1006] As the compound represented by the general formula (ii-8), compounds represented by the following general formulas (ii-8-1) to (ii-8-2) are preferred.

[1007] [Chemistry 206]

[1008]

[1009] In the general formula (ii-8-1) to the general formula (ii-8-2), R ii1 and S ii1 Each independently represents the same as R in the general formula (ii) ii1 and S ii1 The same meaning respectively.

[1010] Specific examples of the compound represented by general formula (ii-8-1) include compounds represented by the following structural formulas (ii-8-1.1) to (ii-8-1.3).

[1011] [Chemistry 207]

[1012]

[1013] Specific examples of the compound represented by general formula (ii-8-2) include compounds represented by the following structural formulas (ii-8-2.1) to (ii-8-2.6).

[1014] [Chemistry 208]

[1015]

[1016] General formula (ii), general formula (ii-1) to general formula (ii-8), general formula (ii-1-1) to general formula (ii-1-2), general formula (ii-2-1) to general formula (ii-2-10), general formula (ii-3-1) to general formula (ii-3-16), general formula (ii-4-1) to general formula (ii-4-26), general formula (ii-5-1) to general formula (ii-5-5), general formula (ii-6-1) to general formula (ii-6-33), general formula (ii-7-1), general formula (ii-8-1) to general formula (ii-8-2), structural formula (ii-1-1.1) to structural formula (ii-1-1.4), structural formula (ii-1-2.1) to structural formula (ii-1-2.6) )、Structural formula (ii-2-1.1) ~ structural formula (ii-2-1.4), structural formula (ii-2-2.1) ~ structural formula (ii-2-2.10), structural formula (ii-2-3.1) ~ structural formula (ii-2-3.3), structural formula (ii-2-4.1) ~ structural formula (ii-2-4.8), structural formula (ii-2-5.1) ~ structural formula (ii-2-5.4), structural formula (ii-2-6.1) ~ structural formula (ii-2-6.4), structural formula (ii-2-7.1) ~ structural formula (ii-2-7.3), structural formula (ii-2-8.1) ~ structural formula (ii-2-8.3), structural formula (ii-2-9.1) ~ structural formula (ii-2-9.4) 2-9.4), structural formula (ii-2-10.1) to structural formula (ii-2-10.4), structural formula (ii-3-1.1) to structural formula (ii-3-1.4), structural formula (ii-3-2.1) to structural formula (ii-3-2.4), structural formula (ii-3-3.1) to structural formula (ii-3-3.7), structural formula (ii-3-4.1) to structural formula (ii-3-4.5), structural formula (ii-3-5.1) to structural formula (ii-3-5.7), structural formula (ii-3-6.1) to structural formula (ii-3-6.3), structural formula (ii-3-7.1) to structural formula (ii-3-7.7), structural formula (ii-3-8.1) to structural formula Structural formula (ii-3-8.3), structural formula (ii-3-9.1) to structural formula (ii-3-9.4), structural formula (ii-3-10.1) to structural formula (ii-3-10.3), structural formula (ii-3-11.1) to structural formula (ii-3-11.3), structural formula (ii-3-12.1) to structural formula (ii-3-12.3), structural formula (ii-3-13.1) to structural formula (ii-3-13.4), structural formula (ii-3-14.1) to structural formula (ii-3-14.3), structural formula (ii-3-15.1) to structural formula (ii-3-15.3), structural formula (ii-3-16.1) to structural formula (ii-3-16.3), structural formula (ii-4-1.1) to structural formula (ii-4-1.4), structural formula (ii-4-2.1) to structural formula (ii-4-2.4), structural formula (ii-4-3.1) to structural formula (ii-4-3.8), structural formula (ii-4-4.1) to structural formula (ii-4-4.5), structural formula (ii-4-5.1), structural formula (ii-4-6.1) to structural formula (ii-4-6.5), structural formula (ii-4-7.1), structural formula (ii-4-8.1) to structural formula (ii-4-8.4), structural formula (ii-4-9.1) to structural formula (ii-4-9.4), structural formula (ii-4-10.1) to structural formula (ii-4 -10.4), structural formula (ii-4-11.1) to structural formula (ii-4-11.5), structural formula (ii-4-12.1) to structural formula (ii-4-12.5), structural formula (ii-4-13.1) to structural formula (ii-4-13.4), structural formula (ii-4-14.1) to structural formula (ii-4-14.4), structural formula (ii-4-15.1) to structural formula (ii-4-15.6), structural formula (ii-4-16.1) to structural formula (ii-4-16.3), structural formula (ii-4-17.1) to structural formula (ii-4-17.3), structural formula (ii-4-18.1) to structural formula (ii-4-18.4), structural formula (ii-4-19.1) to structural formula (ii-4-19.8), structural formula (ii-4-20.1) to structural formula (ii-4-20.4), structural formula (ii-4-21.1) to structural formula (ii-4-21.4), structural formula (ii-4-22.1) to structural formula (ii-4-22.3), structural formula (ii-4-23.1) to structural formula (ii-4-23.3), structural formula (ii-4-24.1) to structural formula (ii-4-24.3), structural formula (ii-4-25.1) to structural formula (ii-4-25.3), structural formula (ii-4-26.1) to structural formula (ii-4-26.3), structural formula (ii-5-1.1) ~Structural formula (ii-5-1.4), structural formula (ii-5-2.1) ~ structural formula (ii-5-2.4), structural formula (ii-5-3.1), structural formula (ii-5-4.1) ~ structural formula (ii-5-4.3), structural formula (ii-5-5.1) ~ structural formula (ii-5-5.3), structural formula (ii-6-1.1) ~ structural formula (ii-6-1.4), structural formula (ii-6-2.1) ~ structural formula (ii-6-2.4), structural formula (ii-6-3.1) ~ structural formula (ii-6-3.8), structural formula (ii-6-4.1) ~ structural formula (ii-6-4.4), structural formula (ii-6-5.1) ~ structural formula (ii-6-5.4), structural formula (ii-6-6.1) to structural formula (ii-6-6.2), structural formula (ii-6-7.1) to structural formula (ii-6-7.8), structural formula (ii-6-8.1) to structural formula (ii-6-8.9), structural formula (ii-6-9.1) to structural formula (ii-6-9.4), structural formula (ii-6-10.1) to structural formula (ii-6-10.4), structural formula (ii-6-11.1) to structural formula (ii-6-11.4), structural formula (ii-6-12.1) to structural formula (ii-6-12.4), structural formula (ii-6-13.1) to Structural formula (ii-6-13.20), structural formula (ii-6-14.1) to structural formula (ii-6-14.4), structural formula (ii-6-15.1), structural formula (ii-6-16.1) to structural formula (ii-6-16.5), structural formula (ii-6-17.1) to structural formula (ii-6-17.4), structural formula (ii-6-18.1) to structural formula (ii-6-18.8), structural formula (ii-6-19.1) to structural formula (ii-6-19.4), structural formula (ii-6-20.1) to structural formula (ii-6-20.4), structural formula (ii-6- 21.1) to structural formula (ii-6-21.4), structural formula (ii-6-22.1) to structural formula (ii-6-22.14), structural formula (ii-6-23.1) to structural formula (ii-6-23.10), structural formula (ii-6-24.1) to structural formula (ii-6-24.2), structural formula (ii-6-25.1) to structural formula (ii-6-25.5), structural formula (ii-6-26.1) to structural formula (ii-6-26.2), structural formula (ii-6-27.1), structural formula (ii-6-28.1) to structural formula (ii-6-28.5), structural formula The compounds represented by formula (ii-6-29.1), formula (ii-6-30.1), formula (ii-6-31.1) to formula (ii-6-31.5), formula (ii-6-32.1), formula (ii-6-33.1) to formula (ii-6-33.4), formula (ii-7-1.1), formula (ii-8-1.1) to formula (ii-8-1.3) or formula (ii-8-2.1) to formula (ii-8-2.6) are used in the liquid crystal composition in one or more kinds, preferably one to twenty kinds, and preferably two to fifteen kinds. .

[1017] General formula (ii), general formula (ii-1) to general formula (ii-8), general formula (ii-1-1) to general formula (ii-1-2), general formula (ii-2-1) to general formula (ii-2-10), general formula (ii-3-1) to general formula (ii-3-16), general formula (ii-4-1) to general formula (ii-4-26), general formula (ii-5-1) to general formula (ii-5-5), general formula (ii-6-1) to general formula (ii-6-33), general formula (ii-7-1), general formula (ii-8-1) to general formula (ii-8-2), structural formula (ii-1-1.1) to structural formula (ii-1-1.4), structural formula (ii-1-2.1) to structural formula (ii-1-2.6) )、Structural formula (ii-2-1.1) ~ structural formula (ii-2-1.4), structural formula (ii-2-2.1) ~ structural formula (ii-2-2.10), structural formula (ii-2-3.1) ~ structural formula (ii-2-3.3), structural formula (ii-2-4.1) ~ structural formula (ii-2-4.8), structural formula (ii-2-5.1) ~ structural formula (ii-2-5.4), structural formula (ii-2-6.1) ~ structural formula (ii-2-6.4), structural formula (ii-2-7.1) ~ structural formula (ii-2-7.3), structural formula (ii-2-8.1) ~ structural formula (ii-2-8.3), structural formula (ii-2-9.1) ~ structural formula (ii-2-9.4) 2-9.4), structural formula (ii-2-10.1) to structural formula (ii-2-10.4), structural formula (ii-3-1.1) to structural formula (ii-3-1.4), structural formula (ii-3-2.1) to structural formula (ii-3-2.4), structural formula (ii-3-3.1) to structural formula (ii-3-3.7), structural formula (ii-3-4.1) to structural formula (ii-3-4.5), structural formula (ii-3-5.1) to structural formula (ii-3-5.7), structural formula (ii-3-6.1) to structural formula (ii-3-6.3), structural formula (ii-3-7.1) to structural formula (ii-3-7.7), structural formula (ii-3-8.1) to structural formula Structural formula (ii-3-8.3), structural formula (ii-3-9.1) to structural formula (ii-3-9.4), structural formula (ii-3-10.1) to structural formula (ii-3-10.3), structural formula (ii-3-11.1) to structural formula (ii-3-11.3), structural formula (ii-3-12.1) to structural formula (ii-3-12.3), structural formula (ii-3-13.1) to structural formula (ii-3-13.4), structural formula (ii-3-14.1) to structural formula (ii-3-14.3), structural formula (ii-3-15.1) to structural formula (ii-3-15.3), structural formula (ii-3-16.1) to structural formula (ii-3-16.3), structural formula (ii-4-1.1) to structural formula (ii-4-1.4), structural formula (ii-4-2.1) to structural formula (ii-4-2.4), structural formula (ii-4-3.1) to structural formula (ii-4-3.8), structural formula (ii-4-4.1) to structural formula (ii-4-4.5), structural formula (ii-4-5.1), structural formula (ii-4-6.1) to structural formula (ii-4-6.5), structural formula (ii-4-7.1), structural formula (ii-4-8.1) to structural formula (ii-4-8.4), structural formula (ii-4-9.1) to structural formula (ii-4-9.4), structural formula (ii-4-10.1) to structural formula (ii-4 -10.4), structural formula (ii-4-11.1) to structural formula (ii-4-11.5), structural formula (ii-4-12.1) to structural formula (ii-4-12.5), structural formula (ii-4-13.1) to structural formula (ii-4-13.4), structural formula (ii-4-14.1) to structural formula (ii-4-14.4), structural formula (ii-4-15.1) to structural formula (ii-4-15.6), structural formula (ii-4-16.1) to structural formula (ii-4-16.3), structural formula (ii-4-17.1) to structural formula (ii-4-17.3), structural formula (ii-4-18.1) to structural formula (ii-4-18.4), structural formula (ii-4-19.1) to structural formula (ii-4-19.8), structural formula (ii-4-20.1) to structural formula (ii-4-20.4), structural formula (ii-4-21.1) to structural formula (ii-4-21.4), structural formula (ii-4-22.1) to structural formula (ii-4-22.3), structural formula (ii-4-23.1) to structural formula (ii-4-23.3), structural formula (ii-4-24.1) to structural formula (ii-4-24.3), structural formula (ii-4-25.1) to structural formula (ii-4-25.3), structural formula (ii-4-26.1) to structural formula (ii-4-26.3), structural formula (ii-5-1.1) ~Structural formula (ii-5-1.4), structural formula (ii-5-2.1) ~ structural formula (ii-5-2.4), structural formula (ii-5-3.1), structural formula (ii-5-4.1) ~ structural formula (ii-5-4.3), structural formula (ii-5-5.1) ~ structural formula (ii-5-5.3), structural formula (ii-6-1.1) ~ structural formula (ii-6-1.4), structural formula (ii-6-2.1) ~ structural formula (ii-6-2.4), structural formula (ii-6-3.1) ~ structural formula (ii-6-3.8), structural formula (ii-6-4.1) ~ structural formula (ii-6-4.4), structural formula (ii-6-5.1) ~ structural formula (ii-6-5.4), structural formula (ii-6-6.1) to structural formula (ii-6-6.2), structural formula (ii-6-7.1) to structural formula (ii-6-7.8), structural formula (ii-6-8.1) to structural formula (ii-6-8.9), structural formula (ii-6-9.1) to structural formula (ii-6-9.4), structural formula (ii-6-10.1) to structural formula (ii-6-10.4), structural formula (ii-6-11.1) to structural formula (ii-6-11.4), structural formula (ii-6-12.1) to structural formula (ii-6-12.4), structural formula Formula (ii-6-13.1) to formula (ii-6-13.20), formula (ii-6-14.1) to formula (ii-6-14.4), formula (ii-6-15.1), formula (ii-6-16.1) to formula (ii-6-16.5), formula (ii-6-17.1) to formula (ii-6-17.4), formula (ii-6-18.1) to formula (ii-6-18.8), formula (ii-6-19.1) to formula (ii-6-19.4), formula (ii-6-20.1) ~Structural formula (ii-6-20.4), structural formula (ii-6-21.1) ~ structural formula (ii-6-21.4), structural formula (ii-6-22.1) ~ structural formula (ii-6-22.14), structural formula (ii-6-23.1) ~ structural formula (ii-6-23.10), structural formula (ii-6-24.1) ~ structural formula (ii-6-24.2), structural formula (ii-6-25.1) ~ structural formula (ii-6-25.5), structural formula (ii-6-26.1) ~ structural formula (ii-6-26.2), structural formula (ii-6- 27.1), structural formula (ii-6-28.1) to structural formula (ii-6-28.5), structural formula (ii-6-29.1), structural formula (ii-6-30.1), structural formula (ii-6-31.1) to structural formula (ii-6-31.5), structural formula (ii-6-32.1), structural formula (ii-6-33.1) to structural formula (ii-6-33.4), structural formula (ii-7-1.1), structural formula (ii-8-1.1) to structural formula (ii-8-1.3) or structural formula (ii-8-2.1) to structural formula (ii-8-2.6) The lower limit of the total content of the compounds represented in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, preferably 5% by mass or more, preferably 10% by mass or more, preferably 15% by mass or more, preferably 20% by mass or more, preferably 25% by mass or more, 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 75% by mass or more, preferably 80% by mass or more, preferably 85% by mass or more.

[1018] General formula (ii), general formula (ii-1) to general formula (ii-8), general formula (ii-1-1) to general formula (ii-1-2), general formula (ii-2-1) to general formula (ii-2-10), general formula (ii-3-1) to general formula (ii-3-16), general formula (ii-4-1) to general formula (ii-4-26), general formula (ii-5-1) to general formula (ii-5-5), general formula (ii-6-1) to general formula (ii-6-33), general formula (ii-7-1), general formula (ii-8-1) to general formula (ii-8-2), structural formula (ii-1-1.1) to structural formula (ii-1-1.4), structural formula (ii-1-2.1) to structural formula (ii-1-2.6) )、Structural formula (ii-2-1.1) ~ structural formula (ii-2-1.4), structural formula (ii-2-2.1) ~ structural formula (ii-2-2.10), structural formula (ii-2-3.1) ~ structural formula (ii-2-3.3), structural formula (ii-2-4.1) ~ structural formula (ii-2-4.8), structural formula (ii-2-5.1) ~ structural formula (ii-2-5.4), structural formula (ii-2-6.1) ~ structural formula (ii-2-6.4), structural formula (ii-2-7.1) ~ structural formula (ii-2-7.3), structural formula (ii-2-8.1) ~ structural formula (ii-2-8.3), structural formula (ii-2-9.1) ~ structural formula (ii-2-9.4) 2-9.4), structural formula (ii-2-10.1) to structural formula (ii-2-10.4), structural formula (ii-3-1.1) to structural formula (ii-3-1.4), structural formula (ii-3-2.1) to structural formula (ii-3-2.4), structural formula (ii-3-3.1) to structural formula (ii-3-3.7), structural formula (ii-3-4.1) to structural formula (ii-3-4.5), structural formula (ii-3-5.1) to structural formula (ii-3-5.7), structural formula (ii-3-6.1) to structural formula (ii-3-6.3), structural formula (ii-3-7.1) to structural formula (ii-3-7.7), structural formula (ii-3-8.1) to structural formula Structural formula (ii-3-8.3), structural formula (ii-3-9.1) to structural formula (ii-3-9.4), structural formula (ii-3-10.1) to structural formula (ii-3-10.3), structural formula (ii-3-11.1) to structural formula (ii-3-11.3), structural formula (ii-3-12.1) to structural formula (ii-3-12.3), structural formula (ii-3-13.1) to structural formula (ii-3-13.4), structural formula (ii-3-14.1) to structural formula (ii-3-14.3), structural formula (ii-3-15.1) to structural formula (ii-3-15.3), structural formula (ii-3-16.1) to structural formula (ii-3-16.3), structural formula (ii-4-1.1) to structural formula (ii-4-1.4), structural formula (ii-4-2.1) to structural formula (ii-4-2.4), structural formula (ii-4-3.1) to structural formula (ii-4-3.8), structural formula (ii-4-4.1) to structural formula (ii-4-4.5), structural formula (ii-4-5.1), structural formula (ii-4-6.1) to structural formula (ii-4-6.5), structural formula (ii-4-7.1), structural formula (ii-4-8.1) to structural formula (ii-4-8.4), structural formula (ii-4-9.1) to structural formula (ii-4-9.4), structural formula (ii-4-10.1) to structural formula (ii-4 -10.4), structural formula (ii-4-11.1) to structural formula (ii-4-11.5), structural formula (ii-4-12.1) to structural formula (ii-4-12.5), structural formula (ii-4-13.1) to structural formula (ii-4-13.4), structural formula (ii-4-14.1) to structural formula (ii-4-14.4), structural formula (ii-4-15.1) to structural formula (ii-4-15.6), structural formula (ii-4-16.1) to structural formula (ii-4-16.3), structural formula (ii-4-17.1) to structural formula (ii-4-17.3), structural formula (ii-4-18.1) to structural formula (ii-4-18.4), structural formula (ii-4-19.1) to structural formula (ii-4-19.8), structural formula (ii-4-20.1) to structural formula (ii-4-20.4), structural formula (ii-4-21.1) to structural formula (ii-4-21.4), structural formula (ii-4-22.1) to structural formula (ii-4-22.3), structural formula (ii-4-23.1) to structural formula (ii-4-23.3), structural formula (ii-4-24.1) to structural formula (ii-4-24.3), structural formula (ii-4-25.1) to structural formula (ii-4-25.3), structural formula (ii-4-26.1) to structural formula (ii-4-26.3), structural formula (ii-5-1.1) ~Structural formula (ii-5-1.4), structural formula (ii-5-2.1) ~ structural formula (ii-5-2.4), structural formula (ii-5-3.1), structural formula (ii-5-4.1) ~ structural formula (ii-5-4.3), structural formula (ii-5-5.1) ~ structural formula (ii-5-5.3), structural formula (ii-6-1.1) ~ structural formula (ii-6-1.4), structural formula (ii-6-2.1) ~ structural formula (ii-6-2.4), structural formula (ii-6-3.1) ~ structural formula (ii-6-3.8), structural formula (ii-6-4.1) ~ structural formula (ii-6-4.4), structural formula (ii-6-5.1) ~ structural formula (ii-6-5.4), structural formula (ii-6-6.1) to structural formula (ii-6-6.2), structural formula (ii-6-7.1) to structural formula (ii-6-7.8), structural formula (ii-6-8.1) to structural formula (ii-6-8.9), structural formula (ii-6-9.1) to structural formula (ii-6-9.4), structural formula (ii-6-10.1) to structural formula (ii-6-10.4), structural formula (ii-6-11.1) to structural formula (ii-6-11.4), structural formula (ii-6-12.1) to structural formula (ii-6-12.4), structural formula (ii-6-13.1) to structural formula (ii-6-13.20), structural formula (ii -6-14.1) ~ Structural formula (ii-6-14.4), Structural formula (ii-6-15.1), Structural formula (ii-6-16.1) ~ Structural formula (ii-6-16.5), Structural formula (ii-6-17.1) ~ Structural formula (ii-6-17.4), Structural formula (ii-6-18.1) ~ Structural formula (ii-6-18.8), Structural formula (ii-6-19.1) ~ Structural formula (ii-6-19.4), Structural formula (ii-6-20.1) ~ Structural formula (ii-6-20.4), Structural formula (ii-6-21.1) ~ Structural formula (ii-6-21.4), Structural formula (ii-6-22.1) ~ Structural formula (ii-6- 22.14), structural formula (ii-6-23.1) to structural formula (ii-6-23.10), structural formula (ii-6-24.1) to structural formula (ii-6-24.2), structural formula (ii-6-25.1) to structural formula (ii-6-25.5), structural formula (ii-6-26.1) to structural formula (ii-6-26.2), structural formula (ii-6-27.1), structural formula (ii-6-28.1) to structural formula (ii-6-28.5), structural formula (ii-6-29.1), structural formula (ii-6-30.1), structural formula (ii-6-31.1) to structural formula (ii-6-31.5), structural formula (ii-6- The upper limit of the total content of the compounds represented by the structural formula (ii-32.1), structural formula (ii-6-33.1) to structural formula (ii-6-33.4), structural formula (ii-7-1.1), structural formula (ii-8-1.1) to structural formula (ii-8-1.3) or structural formula (ii-8-2.1) to structural formula (ii-8-2.6) in 100% by mass of the liquid crystal composition is preferably 95% by mass or less, preferably 90% 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 25% by mass or less, preferably 15% by mass or less, and preferably 5% by mass or less. .

[1019] Regarding solubility, Δn and / or Δε rFrom the perspective of general formula (ii), general formula (ii-1) to general formula (ii-8), general formula (ii-1-1) to general formula (ii-1-2), general formula (ii-2-1) to general formula (ii-2-10), general formula (ii-3-1) to general formula (ii-3-16), general formula (ii-4-1) to general formula (ii-4-26), general formula (ii-5-1) to general formula (ii-5-5), general formula (ii-6-1) to general formula (ii-6-33), general formula (ii-7-1), general formula (ii-8-1) to general formula (ii-8-2), structural formula (ii-1-1.1) to structural formula (ii-1-1.4), structural formula (ii-1-2.1) to structural formula (ii- 1-2.6), structural formula (ii-2-1.1) to structural formula (ii-2-1.4), structural formula (ii-2-2.1) to structural formula (ii-2-2.10), structural formula (ii-2-3.1) to structural formula (ii-2-3.3), structural formula (ii-2-4.1) to structural formula (ii-2-4.8), structural formula (ii-2-5.1) to structural formula (ii-2-5.4), structural formula (ii-2-6.1) to structural formula (ii-2-6.4), structural formula (ii-2-7.1) to structural formula (ii-2-7.3), structural formula (ii-2-8.1) to structural formula (ii-2-8.3), structural formula (ii-2-9.1) to structural formula (ii-2-9.4) ii-2-9.4), structural formula (ii-2-10.1) to structural formula (ii-2-10.4), structural formula (ii-3-1.1) to structural formula (ii-3-1.4), structural formula (ii-3-2.1) to structural formula (ii-3-2.4), structural formula (ii-3-3.1) to structural formula (ii-3-3.7), structural formula (ii-3-4.1) to structural formula (ii-3-4.5), structural formula (ii-3-5.1) to structural formula (ii-3-5.7), structural formula (ii-3-6.1) to structural formula (ii-3-6.3), structural formula (ii-3-7.1) to structural formula (ii-3-7.7), structural formula (ii-3-8.1) ~Structural formula (ii-3-8.3), structural formula (ii-3-9.1) ~ structural formula (ii-3-9.4), structural formula (ii-3-10.1) ~ structural formula (ii-3-10.3), structural formula (ii-3-11.1) ~ structural formula (ii-3-11.3), structural formula (ii-3-12.1) ~ structural formula (ii-3-12.3), structural formula (ii-3-13.1) ~ structural formula (ii-3-13.4), structural formula (ii-3-14.1) ~ structural formula (ii-3-14.3), structural formula (ii-3-15.1) ~ structural formula (ii-3-15.3), structural formula (ii-3-16.1) ~ structural formula (ii-3-16.3), structural formula (ii-4-1.1) to structural formula (ii-4-1.4), structural formula (ii-4-2.1) to structural formula (ii-4-2.4), structural formula (ii-4-3.1) to structural formula (ii-4-3.8), structural formula (ii-4-4.1) to structural formula (ii-4-4.5), structural formula (ii-4-5.1), structural formula (ii-4-6.1) to structural formula (ii-4-6.5), structural formula (ii-4-7.1), structural formula (ii-4-8.1) to structural formula (ii-4-8.4), structural formula (ii-4-9.1) to structural formula (ii-4-9.4), structural formula (ii-4-10.1) to structural formula (ii-4 -10.4), structural formula (ii-4-11.1) to structural formula (ii-4-11.5), structural formula (ii-4-12.1) to structural formula (ii-4-12.5), structural formula (ii-4-13.1) to structural formula (ii-4-13.4), structural formula (ii-4-14.1) to structural formula (ii-4-14.4), structural formula (ii-4-15.1) to structural formula (ii-4-15.6), structural formula (ii-4-16.1) to structural formula (ii-4-16.3), structural formula (ii-4-17.1) to structural formula (ii-4-17.3), structural formula (ii-4-18.1) to structural formula (ii-4-18.4), structural formula (ii-4-19.1) to structural formula (ii-4-19.8), structural formula (ii-4-20.1) to structural formula (ii-4-20.4), structural formula (ii-4-21.1) to structural formula (ii-4-21.4), structural formula (ii-4-22.1) to structural formula (ii-4-22.3), structural formula (ii-4-23.1) to structural formula (ii-4-23.3), structural formula (ii-4-24.1) to structural formula (ii-4-24.3), structural formula (ii-4-25.1) to structural formula (ii-4-25.3), structural formula (ii-4-26.1) to structural formula (ii-4-26.3), structural formula (ii-5-1.1) ~Structural formula (ii-5-1.4), structural formula (ii-5-2.1) ~ structural formula (ii-5-2.4), structural formula (ii-5-3.1), structural formula (ii-5-4.1) ~ structural formula (ii-5-4.3), structural formula (ii-5-5.1) ~ structural formula (ii-5-5.3), structural formula (ii-6-1.1) ~ structural formula (ii-6-1.4), structural formula (ii-6-2.1) ~ structural formula (ii-6-2.4), structural formula (ii-6-3.1) ~ structural formula (ii-6-3.8), structural formula (ii-6-4.1) ~ structural formula (ii-6-4.4), structural formula (ii-6-5.1) ~ structural formula (ii-6-5.4), structural formula (ii-6-6.1) to structural formula (ii-6-6.2), structural formula (ii-6-7.1) to structural formula (ii-6-7.8), structural formula (ii-6-8.1) to structural formula (ii-6-8.9), structural formula (ii-6-9.1) to structural formula (ii-6-9.4), structural formula (ii-6-10.1) to structural formula (ii-6-10.4), structural formula (ii-6-11.1) to structural formula (ii-6-11.4), structural formula (ii-6-12.1) to structural formula (ii-6-12.4), structural formula (ii-6-13.1) to structural formula (ii-6 -13.20), structural formula (ii-6-14.1) to structural formula (ii-6-14.4), structural formula (ii-6-15.1), structural formula (ii-6-16.1) to structural formula (ii-6-16.5), structural formula (ii-6-17.1) to structural formula (ii-6-17.4), structural formula (ii-6-18.1) to structural formula (ii-6-18.8), structural formula (ii-6-19.1) to structural formula (ii-6-19.4), structural formula (ii-6-20.1) to structural formula (ii-6-20.4), structural formula (ii-6-21.1) to structural formula (ii-6-21 .4), structural formula (ii-6-22.1) to structural formula (ii-6-22.14), structural formula (ii-6-23.1) to structural formula (ii-6-23.10), structural formula (ii-6-24.1) to structural formula (ii-6-24.2), structural formula (ii-6-25.1) to structural formula (ii-6-25.5), structural formula (ii-6-26.1) to structural formula (ii-6-26.2), structural formula (ii-6-27.1), structural formula (ii-6-28.1) to structural formula (ii-6-28.5), structural formula (ii-6-29.1), structural formula (ii-6-30. 1), the total content of the compounds represented by structural formula (ii-6-31.1) to structural formula (ii-6-31.5), structural formula (ii-6-32.1), structural formula (ii-6-33.1) to structural formula (ii-6-33.4), structural formula (ii-7-1.1), structural formula (ii-8-1.1) to structural formula (ii-8-1.3) or structural formula (ii-8-2.1) to structural formula (ii-8-2.6) in 100% by mass of the liquid crystal composition is preferably 1% by mass to 95% by mass, preferably 5% by mass to 90% by mass, preferably 5% by mass to 55% by mass, and preferably 10% by mass to 45% by mass. .

[1020] The compound represented by the general formula (ii) (including subordinate concepts) can be synthesized using a known synthesis method.

[1021] (Other compounds)

[1022] In terms of Δn and / or Δε r From the viewpoint of , the liquid crystal composition of the present invention may further contain one or more compounds represented by the following general formula (vt) having at least one -C≡C- as a linking group.

[1023] [Chemistry 209]

[1024]

[1025] In the general formula (vt), R vt1 It represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.

[1026] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[1027] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.

[1028] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[1029] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[1030] In addition, one or two or more -CH2-CH2-CH2- in the alkyl group may be independently substituted by -O-CO-O-.

[1031] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom.

[1032] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[1033] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[1034] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1035] For example, R vt1 By substituting one -CH2- in the above alkyl group with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[1036] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[1037] The alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1038] In addition, R vt1 By substituting one -CH2- in the above alkyl group with -S-, an alkylmercapto group (alkylthio group) having 1 to 19 carbon atoms can be represented.

[1039] The alkylmercapto group is a linear, branched or cyclic alkylmercapto group, and is preferably a linear alkylmercapto group.

[1040] The alkylmercapto group preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.

[1041] In addition, R vt1 By replacing one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[1042] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[1043] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1044] In addition, R vt1 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[1045] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[1046] The alkynyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1047] In addition, R vt1 An alkenyloxy group having 2 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or more -CH2-CH2- with -CH=CH-.

[1048] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[1049] The alkenyloxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1050] In addition, R vt1 By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[1051] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[1052] The halogenated alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1053] In addition, R vt1 A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or two or more hydrogen atoms in the alkyl group with halogen atoms.

[1054] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[1055] The halogenated alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1056] As R vt1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: vt1 -1)~Formula (R vt1 -36) represented by the base, etc.

[1057] [Chemistry 210]

[1058]

[1059] Formula (R vt1 -1)~Formula (R vt1 -36), the black dot indicates the direction to A vt1 The bond key.

[1060] When the reliability of the entire liquid crystal composition is emphasized, R vt1 It is preferably an alkyl group having 1 to 12 carbon atoms. When the reduction in viscosity of the entire liquid crystal composition is important, R vt1 An alkenyl group having 2 to 8 carbon atoms is preferred.

[1061] In R vt1 When the ring structure to which the bond is a phenyl group (aromatic), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. vt1 When the bonded ring structure is a saturated ring structure such as cyclohexane, pyran and dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms.

[1062] In addition, as R vt1In order to stabilize the nematic phase, the total number of carbon atoms and, if present, oxygen atoms is preferably 5 or less, and the chain is preferably straight.

[1063] In addition, as R vt1 In view of solubility, a linear alkyl group having 2 to 6 carbon atoms or a linear alkylmercapto group having 1 to 6 carbon atoms is preferred.

[1064] In the general formula (vt), R vt2 It represents any one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto 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, or an alkyl group having 1 to 20 carbon atoms.

[1065] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[1066] The alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1067] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[1068] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[1069] In addition, one or two or more -CH2-CH2-CH2- in the alkyl group may be independently substituted by -O-CO-O-.

[1070] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom.

[1071] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[1072] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[1073] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1074] For example, R vt2 By substituting one -CH2- in the above alkyl group with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[1075] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[1076] The alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1077] In addition, R vt2 By substituting one -CH2- in the above alkyl group with -S-, an alkylmercapto group (alkylthio group) having 1 to 19 carbon atoms can be represented.

[1078] The alkylmercapto group is a linear, branched or cyclic alkylmercapto group, and is preferably a linear alkylmercapto group.

[1079] The alkylmercapto group preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.

[1080] In addition, R vt2 By replacing one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[1081] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[1082] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1083] In addition, R vt2 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[1084] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[1085] The alkynyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1086] In addition, R vt2 An alkenyloxy group having 2 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or more -CH2-CH2- with -CH=CH-.

[1087] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[1088] The alkenyloxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1089] In addition, R vt2By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[1090] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[1091] The halogenated alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1092] In addition, R vt2 A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or two or more hydrogen atoms in the alkyl group with halogen atoms.

[1093] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[1094] The halogenated alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1095] As R vt2 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: vt2 -1)~Formula (R vt2 -36) represented by the base, etc.

[1096] [Chemistry 211]

[1097]

[1098] Formula (R vt2 -1)~Formula (R vt2 -36), the black dot indicates the direction to A vt3 The bond key.

[1099] In R vt2 When the ring structure to which the bond is a phenyl group (aromatic), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. vt2 When the bonded ring structure is a saturated ring structure such as cyclohexane, pyran and dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms.

[1100] In addition, as R vt2 In order to stabilize the nematic phase, the total number of carbon atoms and, if present, oxygen atoms is preferably 5 or less, and the chain is preferably straight.

[1101] In addition, as Rvt2 , in terms of solubility, Δn and / or Δε r From the viewpoint of , a fluorine atom, a cyano group, a linear alkyl group having 2 to 6 carbon atoms, a linear alkoxy group having 1 to 6 carbon atoms, or a linear alkylthiol group having 1 to 6 carbon atoms is preferred.

[1102] In the general formula (vt), A vt1 , A vt2 and A vt3 Each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms.

[1103] More specifically, the hydrocarbon ring having 3 to 16 carbon atoms or the heterocyclic ring having 3 to 16 carbon atoms preferably represents a group (a), a group (b), a group (c) and a group (d) selected from the following:

[1104] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- in the group may be substituted with -O- or -S-)

[1105] (b) 1,4-phenylene (one or two or more -CH= in the group may be substituted with -N=)

[1106] (c) 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene -2,7-diyl (one or two or more -CH= in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl may be substituted with -N=)

[1107] (d) Thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl (one -CH= or two or more -CH= in the above group may be substituted with -N=)

[1108] The basis of the group.

[1109] A vt1 , A vt2 and A vt3 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group Svt1 replace.

[1110] Substituent S vt1 It represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms.

[1111] The alkyl group is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[1112] The alkyl group preferably has 2 to 10 carbon atoms, and more preferably 3 to 6 carbon atoms.

[1113] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S- and / or -CO-.

[1114] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-.

[1115] In addition, one or two or more -CH2-CH2-CH2- in the alkyl group may be substituted by -O-CO-O-.

[1116] One or two or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[1117] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[1118] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[1119] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1120] As a substituent S vt1 , preferably a fluorine atom or a linear alkyl group having 1 to 3 carbon atoms.

[1121] In addition, A vt1 , A vt2 and A vt3 At least one of the substituents S vt1 replace.

[1122] In addition, A vt1 Preferably, at least one substituent Svt1 replace.

[1123] In addition, in the substituent S vt1 When there are plural, these may be the same or different.

[1124] As A vt1 The substituent S in vt1 The substitution position is preferably the following formula (A vt1 -SP-1)~Formula (A vt1 -SP-3).

[1125] [Chemistry 212]

[1126]

[1127] Formula (A vt1 -SP-1)~Formula (A vt1 -SP-3), the white dots represent R vt1 The black dots represent the bonds toward -C≡C-.

[1128] As A vt2 The substituent S in vt1 The substitution position is preferably the following formula (A vt2 -SP-1)~Formula (A vt2 -SP-7) is preferably represented by the following formula (A) from the viewpoint of compatibility with other liquid crystal compounds. vt2 -SP-1)~Formula (A vt2 -SP-7).

[1129] [Chemistry 213]

[1130]

[1131] Formula (A vt2 -SP-1)~Formula (A vt2 -SP-7), the white dots represent the bonding of -C≡C-, and the black dots represent the bonding of Z vt1 The bond key.

[1132] As A vt3 The substituent S in vt3 The substitution position is preferably the following formula (A vt3 -SP-1)~Formula (A vt3 -SP-8) is preferably represented by the following formula (A vt3 -SP-1)~Formula (A vt3 -SP-5) any one.

[1133] [Chemistry 214]

[1134]

[1135] Formula (A vt3 -SP-1)~Formula (A vt3 -SP-8), the white dot indicates the direction of Z vt1 The black dots represent the bonds to Z vt1 or R vt2 The bond key.

[1136] More specifically, A vt1 Preferably, it is represented by the following formula (A vt1 -1)~Formula (A vt1 -5) any one of.

[1137] [Chemistry 215]

[1138]

[1139] Formula (A vt1 -1)~Formula (A vt1 -5), the white dot represents R vt1 The black dots represent the bonds toward -C≡C-.

[1140] More specifically, A vt2 Preferably, it is represented by the following formula (A vt2 -1)~Formula (A vt2 -6) any one of.

[1141] [Chemistry 216]

[1142]

[1143] Formula (A vt2 -1)~Formula (A vt2 -6), the white dots represent the bonding of -C≡C-, and the black dots represent the bonding of Z vt1 The bond key.

[1144] More specifically, A vt3 Preferably, it is represented by the following formula (A vt3 -1)~Formula (A vt3 -5) any one of.

[1145] [Chemistry 217]

[1146]

[1147] Formula (A vt3 -1)~Formula (A vt3 -5), the white dot indicates the direction Z vt1 The black dots represent the bonds to Z vt1 or Rvt2 The bond key.

[1148] In the general formula (vt), Z vt1 Each independently represents any of a single bond and an alkylene group having 1 to 20 carbon atoms.

[1149] The alkylene group is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[1150] The alkylene group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1151] One or more -CH2- groups in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[1152] In addition, one or more -CH2-CH2- in the alkylene group may be independently replaced by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[1153] In addition, one or two or more -CH2-CH2-CH2- in the alkylene group may be independently substituted by -O-CO-O-.

[1154] However, when the alkylene group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[1155] Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted alkylene groups) include the following: vt1 -1)~Formula(Z vt1 -24) represented by the base, etc.

[1156] [Chemistry 218]

[1157]

[1158] Formula (Z vt1 -1)~Formula(Z vt1 -24), the white dot indicates the direction to A vt2 or A vt3 The black dots indicate the bond to A vt3 The bond key.

[1159] In the general formula (vt), n vt1 It represents an integer of 1-3, and preferably an integer of 1-2.

[1160] In n vt1When Δn and / or Δε is 1, r From the point of view of Z vt1 Preferably, it represents -C≡C-.

[1161] In addition, in n vt1 When Δn and / or Δε is 2 or 3, r From the point of view of Z vt1 At least one of preferably represents -C≡C-.

[1162] In addition, in the general formula (vt), in A vt3 and Z vt1 When there are plural numbers, these may be the same or different.

[1163] The compound represented by the general formula (vt) is preferably a compound represented by the following general formula (vt-1).

[1164] [Chemistry 219]

[1165]

[1166] In the general formula (vt-1), R vt1 , R vt2 , A vt1 , A vt2 and A vt3 represents the same as R in the general formula (vt) vt1 , R vt2 , A vt1 , A vt2 and A vt3 The same meaning respectively.

[1167] As the compound represented by the general formula (vt-1), compounds represented by the following general formulas (vt-1-1) to (vt-1-3) are preferred.

[1168] [Chemistry 220]

[1169]

[1170] In the general formula (vt-1-1) to the general formula (vt-1-3), R vt1 , R vt2 and S vt1 Each independently represents R in the general formula (vt) vt1 , R vt2 and S vt1 The same meaning respectively.

[1171] Specific examples of the compound represented by the general formula (vt-1-1) include compounds represented by the following structural formulas (vt-1-1.1) to (vt-1-1.24).

[1172] [Chemistry 221]

[1173]

[1174] [Chemistry 222]

[1175]

[1176] [Chemistry 223]

[1177]

[1178] Specific examples of the compound represented by the general formula (vt-1-2) include compounds represented by the following structural formulas (vt-1-2.1) to (vt-1-2.8).

[1179] [Chemistry 224]

[1180]

[1181] Specific examples of the compound represented by the general formula (vt-1-3) include compounds represented by the following structural formulas (vt-1-3.1) to (vt-1-3.4).

[1182] [Chemistry 225]

[1183]

[1184] The types of compounds represented by general formula (vt), general formula (vt-1), general formula (vt-1-1) to general formula (vt-1-3), structural formula (vt-1-1.1) to structural formula (vt-1-1.24), structural formula (vt-1-2.1) to structural formula (vt-1-2.8) or structural formula (vt-1-3.1) to structural formula (vt-1-3.4) used in the liquid crystal composition are one or more, preferably one to five, preferably one to four, preferably one to three, preferably one to two, and preferably one.

[1185] The lower limit of the total content of the compounds represented by general formula (vt), general formula (vt-1), general formula (vt-1-1) to general formula (vt-1-3), structural formula (vt-1-1.1) to structural formula (vt-1-1.24), structural formula (vt-1-2.1) to structural formula (vt-1-2.8) or structural formula (vt-1-3.1) to structural formula (vt-1-3.4) in 100 mass% of the liquid crystal composition is preferably 0.1 mass% or more, preferably 0.5 mass% or more, and preferably 1 mass% or more.

[1186] The upper limit value of the total content of the compounds represented by general formula (vt), general formula (vt-1), general formula (vt-1-1) to general formula (vt-1-3), structural formula (vt-1-1.1) to structural formula (vt-1-1.24), structural formula (vt-1-2.1) to structural formula (vt-1-2.8) or structural formula (vt-1-3.1) to structural formula (vt-1-3.4) in 100 mass% of the liquid crystal composition is preferably 25 mass% or less, preferably 20 mass% or less, and preferably 15 mass% or less.

[1187] Regarding solubility, Δn and / or Δε r From the perspective of, the total content of the compounds represented by general formula (vt), general formula (vt-1), general formula (vt-1-1) to general formula (vt-1-3), structural formula (vt-1-1.1) to structural formula (vt-1-1.24), structural formula (vt-1-2.1) to structural formula (vt-1-2.8) or structural formula (vt-1-3.1) to structural formula (vt-1-3.4) in 100 mass% of the liquid crystal composition is preferably 0.1 mass% to 25 mass%, preferably 0.5 mass% to 20 mass%, and preferably 1 mass% to 15 mass%.

[1188] The compound represented by the general formula (vt) (including subordinate concepts) can be synthesized using a known synthesis method.

[1189] From the viewpoint of solubility, the liquid crystal composition of the present invention may further contain one or two or more compounds represented by the following general formula (np-1) to general formula (np-3).

[1190] [Chemistry 226]

[1191]

[1192] In the general formula (np-1) to the general formula (np-3), R npi and R npii Each independently represents an alkyl group having 1 to 20 carbon atoms or a halogen atom.

[1193] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[1194] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.

[1195] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[1196] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF- and / or -C≡C-.

[1197] In addition, one or two or more -CH2-CH2-CH2- in the alkyl group may be independently substituted by -O-CO-O-.

[1198] In addition, one or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom.

[1199] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[1200] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[1201] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1202] For example, R npi and R npii By substituting one -CH2- in the above alkyl group with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[1203] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[1204] The alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1205] In addition, R npi and R npii By substituting one -CH2- in the above alkyl group with -S-, an alkylmercapto group (thioalkyl) having 1 to 19 carbon atoms can be represented.

[1206] The alkylmercapto group is a linear, branched or cyclic alkylmercapto group, and is preferably a linear alkylmercapto group.

[1207] The alkylmercapto group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1208] In addition, R npi and R npii By replacing one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[1209] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[1210] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1211] In addition, R npi and R npii By substituting one or two or more -CH2-CH2- groups in the alkyl group with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[1212] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[1213] The alkynyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1214] In addition, R npi and R npii An alkenyloxy group having 2 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or more -CH2-CH2- with -CH=CH-.

[1215] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[1216] The alkenyloxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1217] In addition, R npi and R npii By substituting one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[1218] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[1219] The halogenated alkyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1220] R npi and R npii A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- in the alkyl group with -O- and replacing one or two or more hydrogen atoms in the alkyl group with halogen atoms.

[1221] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[1222] The halogenated alkoxy group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1223] As R npi and R npii Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: npi / ii -1)~Formula (R npi / ii -36) represented by the base, etc.

[1224] [Chemistry 227]

[1225]

[1226] Formula (R npi / ii -1)~Formula (R npi / ii -36), black dots represent bonds to ring A, ring B, ring C or ring D.

[1227] As R npi and R npii The halogen atom in ] includes a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.

[1228] In general formulae (np-1) to (np-3), ring A, ring B, ring C and ring D each independently represent a group (a), group (b), group (c) and group (d) selected from the following:

[1229] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- in the group may be substituted with -O-)

[1230] (b) 1,4-phenylene (one or two or more -CH= in the group may be substituted with -N=)

[1231] (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one or two or more -CH= in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N=)

[1232] (d) 1,4-cyclohexenylene, 1,3-dioxane-trans-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl

[1233] The basis of the group.

[1234] One or more hydrogen atoms in the ring A, ring B, ring C and ring D may be substituted independently by a substituent group S npi1 replace.

[1235] Substituent S npi1 It represents any one of a halogen atom, a cyano group or an alkyl group having 1 to 20 carbon atoms.

[1236] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of stability and safety, a fluorine atom is preferred.

[1237] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[1238] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.

[1239] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[1240] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[1241] One or more -CH2-CH2-CH2- groups in the alkyl group may be independently substituted by -O-CO-O-.

[1242] Furthermore, one or two or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms.

[1243] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[1244] However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[1245] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1246] As a substituent S npi1 , just V th From the viewpoint of , a halogen atom is preferred, and a fluorine atom is preferred.

[1247] In addition, in the substituent S npi1 When there are plural, these may be the same or different.

[1248] As a substituent S in ring A npi1 The substitution position is preferably the following formula (A-SP-1).

[1249] [Chemistry 228]

[1250]

[1251] In formula (A-SP-1), the white dots represent the npi The black dots represent the bonds to Z npi The bond key.

[1252] More specifically, ring A preferably represents any one of the following formula (A-1) to formula (A-3).

[1253] [Chemistry 229]

[1254]

[1255] In formula (A-1) to formula (A-3), the white dots represent the direction of R npi The black dots represent the bonds to Z npi The bond key.

[1256] More specifically, ring B preferably represents any one of the following formula (B-1) to formula (B-2).

[1257] [Chemistry 230]

[1258]

[1259] In formula (B-1) to formula (B-2), the white dots represent the Z direction. npi The black dots indicate the bond to R npii or Z npii The bond key.

[1260] More specifically, ring C preferably represents any one of the following formula (C-1) to formula (C-2).

[1261] [Chemistry 231]

[1262]

[1263] In formula (C-1) to formula (C-2), the white dots represent the Z direction. npii The black dots indicate the bond to R npii or Z npiii The bond key.

[1264] In the general formulas (np-1) to (np-3), Z npi , Z npii and Z npiii Each independently represents any of a single bond and an alkylene group having 1 to 20 carbon atoms.

[1265] One or more -CH2- groups in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[1266] In addition, one or more -CH2-CH2- in the alkylene group may be independently replaced by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[1267] In addition, one or two or more -CH2-CH2-CH2- in the alkylene group may be independently substituted by -O-CO-O-.

[1268] However, when the alkylene group having 1 to 20 carbon atoms is substituted with a predetermined group, oxygen atoms are not directly bonded to each other.

[1269] Furthermore, from the viewpoint of the stability of the compound, it is preferred that sulfur atoms and sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1270] Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted alkylene groups) include the following: npi / ii / iii -1)~Formula(Z npi / ii / iii -24) represented by the base, etc.

[1271] [Chemistry 232]

[1272]

[1273] Formula (Z npi / ii / iii -1)~Formula(Z npi / ii / iii -24), white dots represent bonds to ring A, ring B or ring C, and black dots represent bonds to ring B, ring C or ring D.

[1274] In terms of Δn and / or Δε r From the point of view of Z npi , Z npii and Z npiii Each independently preferably represents any one of a single bond, -C≡C- and -CO-O-.

[1275] However, among the compounds represented by general formulae (np-1) to (np-3), compounds represented by general formula (vt) (including subordinate concepts) are excluded.

[1276] As the compound represented by the general formula (np-2), compounds represented by the following general formulas (np-2-1) to (np-2-3) are preferred.

[1277] [Chemistry 233]

[1278]

[1279] In the general formula (np-2-1) to the general formula (np-2-3), R npi , R npii and S npi represents the same as R in the general formula (np-1) to the general formula (np-3) npi , R npii and S npi The same meaning respectively.

[1280] Specific examples of the compound represented by General Formula (np-2-1) include compounds represented by the following Structural Formula (np-2-1.1).

[1281] [Chemistry 234]

[1282]

[1283] Specific examples of the compound represented by general formula (np-2-2) include compounds represented by the following structural formulas (np-2-2.1) to (np-2-2.5).

[1284] [Chemistry 235]

[1285]

[1286] Specific examples of the compound represented by general formula (np-2-3) include compounds represented by the following structural formulas (np-2-3.1) to (np-2-3.3).

[1287] [Chemistry 236]

[1288]

[1289] The types of compounds represented by general formula (np-1) to general formula (np-3), general formula (np-2-1) to general formula (np-2-3), structural formula (np-2-1.1), structural formula (np-2-2.1) to structural formula (np-2-2.5) or structural formula (np-2-3.1) to structural formula (np-2-3.3) used in the liquid crystal composition are one or more, preferably one to ten, preferably one to eight, preferably one to six, preferably one to four, and preferably one to two.

[1290] The lower limit of the total content of the compounds represented by general formula (np-1) to general formula (np-3), general formula (np-2-1) to general formula (np-2-3), structural formula (np-2-1.1), structural formula (np-2-2.1) to structural formula (np-2-2.5) or structural formula (np-2-3.1) to structural formula (np-2-3.3) in 100 mass% of the liquid crystal composition is preferably 0.1 mass%, preferably 0.5 mass%, and preferably 1 mass%.

[1291] The upper limit value of the total content of the compounds represented by general formula (np-1) to general formula (np-3), general formula (np-2-1) to general formula (np-2-3), structural formula (np-2-1.1), structural formula (np-2-2.1) to structural formula (np-2-2.5) or structural formula (np-2-3.1) to structural formula (np-2-3.3) in 100 mass% of the liquid crystal composition is preferably 30 mass%, preferably 20 mass%, and preferably 15 mass%.

[1292] Regarding solubility, Δn and / or Δε r From the perspective of, the total content of the compounds represented by general formula (np-1) to general formula (np-3), general formula (np-2-1) to general formula (np-2-3), structural formula (np-2-1.1), structural formula (np-2-2.1) to structural formula (np-2-2.5) or structural formula (np-2-3.1) to structural formula (np-2-3.3) in 100 mass% of the liquid crystal composition is preferably 0.1 mass% to 30 mass%, preferably 0.5 mass% to 20 mass%, and preferably 1 mass% to 15 mass%.

[1293] The compounds represented by the general formula (np-1) to the general formula (np-3) (including subordinate concepts) can be produced by a known method.

[1294] (Liquid Crystal Composition)

[1295] The liquid crystal composition of the present invention can be produced, for example, by mixing the compound represented by the general formula (i) and the compound represented by the general formula (ii), and, if necessary, the other compounds and additives.

[1296] Examples of additives include stabilizers, pigment compounds, polymerizable compounds, and azotolane.

[1297] Examples of the stabilizer include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenes, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, hindered phenols, and hindered amines.

[1298] Examples of the hindered phenols include hindered phenol antioxidants represented by the following structural formulas (XX-1) to (XX-3).

[1299] [Chemistry 237]

[1300]

[1301] Examples of the hindered amines include hindered amine-based light stabilizers represented by the following structural formulas (YY-1) and (YY-2).

[1302] [Chemistry 238]

[1303]

[1304] When a stabilizer is used, one or more types of the stabilizer are used in the liquid crystal composition, preferably one to ten types, preferably one to eight types, preferably one to six types, preferably one to four types, and preferably one to two types.

[1305] When a stabilizer is used, the total content of the stabilizer in 100% by mass of the liquid crystal composition is preferably 0.005% by mass to 1% by mass, preferably 0.02% by mass to 0.50% by mass, and preferably 0.03% by mass to 0.35% by mass.

[1306] In addition, regarding solubility, Δn and / or Δε r From the viewpoint of , the combination of compounds used in the liquid crystal composition is preferably:

[1307] 1. A combination of a compound represented by the general formula (i) (including subordinate concepts) and a compound represented by the general formula (ii) (including subordinate concepts);

[1308] 2. A combination of a compound represented by the general formula (i) (including subordinate concepts), a compound represented by the general formula (ii-2) (including subordinate concepts) and a compound represented by the general formula (ii-3) (including subordinate concepts);

[1309] 3. A combination of a compound represented by the general formula (i-4) (including subordinate concepts), a compound represented by the general formula (ii-2) (including subordinate concepts), a compound represented by the general formula (ii-3) (including subordinate concepts), a compound represented by the general formula (ii-4) (including subordinate concepts) and a compound represented by the general formula (ii-6) (including subordinate concepts);

[1310] 4. A combination of a compound represented by the general formula (i-4) (including subordinate concepts), a compound represented by the general formula (ii-1) (including subordinate concepts), a compound represented by the general formula (ii-2) (including subordinate concepts), a compound represented by the general formula (ii-3) (including subordinate concepts) and a compound represented by the general formula (ii-5) (including subordinate concepts);

[1311] 5. A combination of a compound represented by the general formula (i-4) (including subordinate concepts), a compound represented by the general formula (ii-2) (including subordinate concepts), a compound represented by the general formula (ii-3) (including subordinate concepts) and a compound represented by the general formula (ii-6) (including subordinate concepts);

[1312] 6. A combination of a compound represented by the general formula (i-10) (including subordinate concepts), a compound represented by the general formula (ii-2) (including subordinate concepts), a compound represented by the general formula (ii-3) (including subordinate concepts), a compound represented by the general formula (ii-4) (including subordinate concepts) and a compound represented by the general formula (ii-6) (including subordinate concepts);

[1313] 7. A combination of a compound represented by the general formula (i-4) (including subordinate concepts), a compound represented by the general formula (i-11) (including subordinate concepts), a compound represented by the general formula (ii-2) (including subordinate concepts), a compound represented by the general formula (ii-3) (including subordinate concepts), a compound represented by the general formula (ii-4) (including subordinate concepts) and a compound represented by the general formula (ii-6) (including subordinate concepts);

[1314] 8. A combination of compounds represented by the general formula (i-4) (including subordinate concepts), compounds represented by the general formula (i-8) (including subordinate concepts), compounds represented by the general formula (ii-2) (including subordinate concepts), compounds represented by the general formula (ii-3) (including subordinate concepts), compounds represented by the general formula (ii-4) (including subordinate concepts) and compounds represented by the general formula (ii-6) (including subordinate concepts).

[1315] <Characteristic values ​​of liquid crystal composition>

[1316] The upper limit temperature of the 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.

[1317] T ni The measurement was performed by preparing a microscope specimen in which the liquid crystal composition was sandwiched between a slide glass and a cover glass, and observing the specimen under a polarizing microscope while heating the specimen on a heating stage.

[1318] Alternatively, the content of the carbonyl group may be measured by differential scanning calorimetry (DSC).

[1319] The unit used is "℃".

[1320] T ni The higher the value, the more the nematic phase can be maintained even at high temperatures, and the driving temperature range can be expanded.

[1321] The upper limit temperature of the liquid crystal phase of the liquid crystal composition of the present invention (T ni ) can be appropriately set depending on the use situation indoors or in a car where the external temperature of the liquid crystal display element can be controlled, or the use situation outdoors. From the perspective of the driving temperature range, it is preferably above 100°C, preferably 100°C to 200°C, and preferably 110°C to 180°C.

[1322] Liquid crystal phase lower limit temperature (T →n ) is the temperature at which a liquid crystal composition undergoes a phase transition from other phases (glass phase, smectic phase, crystalline phase) to the nematic phase.

[1323] T →n The measurement was performed by filling a glass capillary with a liquid crystal composition, immersing the capillary in a -70°C coolant, causing the liquid crystal composition to undergo a phase transition to another phase, and observing while increasing the temperature.

[1324] Alternatively, the content can be measured by differential scanning calorimetry (DSC).

[1325] The unit used is "℃".

[1326] T →n The lower the value, the more the nematic phase can be maintained even at low temperatures, thus expanding the driving temperature range.

[1327] From the viewpoint of driving temperature, the lower limit temperature (T →n ) is preferably below 10°C, preferably -70°C to 0°C, and preferably -40°C to -5°C.

[1328] Δn (refractive index anisotropy) is related to Δn in the near-infrared region used in an optical sensor described later.

[1329] The larger Δn is, the greater the phase modulation power of light of the target wavelength becomes, and thus it is particularly suitable for optical sensors.

[1330] Δn at 25°C and 589 nm was calculated using an Abbe refractometer based on the extraordinary refractive index (n e ) and the normal refractive index (n o) e -n o ) to find the answer.

[1331] Alternatively, Δn can be obtained using a phase difference measuring device.

[1332] The relationship of Δn=Re / d holds true between the phase difference Re, the thickness d of the liquid crystal layer, and Δn.

[1333] The liquid crystal composition was injected into a glass cell with a polyimide alignment film having a cell gap (d) of about 3.0 μm and subjected to an antiparallel rubbing treatment, and the in-plane Re was measured using a phase difference film-optical material testing apparatus RETS-100 (manufactured by Otsuka Electronics Co., Ltd.).

[1334] The measurement was carried out at 25°C and 589 nm and has no units.

[1335] From the viewpoint of the phase modulation power of light of a certain wavelength, the liquid crystal composition of the present invention preferably has a Δn of 0.38 or more at 25° C. and 589 nm, preferably 0.38 to 0.60, preferably 0.40 to 0.55, and preferably 0.40 to 0.50.

[1336] The rotational viscosity (γ1) is a viscosity ratio related to the rotation of liquid crystal molecules.

[1337] Regarding γ1, the liquid crystal composition can be filled into a glass cell having a cell gap of about 10 μm, and a voltage of 50 V can be applied and measured using LCM-2 (manufactured by TOYO Corporation).

[1338] In the case of a liquid crystal composition having positive dielectric anisotropy, a horizontal alignment unit is used, and in the case of a liquid crystal composition having negative dielectric anisotropy, a vertical alignment unit is used.

[1339] The measurement was performed at a temperature of 25°C, and the unit used was mPa·s.

[1340] The smaller γ1 is, the faster the response speed of the liquid crystal composition becomes, and thus the composition is suitable for any liquid crystal display element.

[1341] From the viewpoint of response speed, the rotational viscosity (γ1) of the liquid crystal composition of the present invention at 25° C. is preferably 150 to 2000 mPa·s, preferably 200 to 1500 mPa·s, and preferably 250 to 1000 mPa·s.

[1342] Threshold voltage (V th ) is related to the driving voltage of the liquid crystal composition.

[1343] About Vth , a liquid crystal composition can be filled in a TN cell with a gap of 8.3μm, and the transmittance is determined by the applied voltage.

[1344] The measurement was performed at a temperature of 25°C, and the unit used was "V".

[1345] V th The lower the voltage, the lower the drive voltage.

[1346] From the viewpoint of driving voltage, the V th It is preferably 3.0V or less, preferably 0.3V to 3.0V, preferably 0.5V to 2.7V, preferably 0.7V to 2.5V, preferably 0.9V to 2.3V, preferably 1.1V to 2.1V, and preferably 1.3V to 2.1V.

[1347] The higher the dielectric anisotropy in the high-frequency region, the greater the phase modulation force on the radio waves in the target frequency band, and therefore it is particularly suitable for antenna use.

[1348] In antenna applications, the smaller the dielectric loss tangent in the high-frequency region is, the smaller the energy loss in the target frequency band becomes, which is suitable.

[1349] In the liquid crystal composition of the present invention, the dielectric anisotropy Δε at 10 GHz was measured as a representative of the characteristics in the high frequency region. r and the average value of dielectric loss tangent tanδ iso .

[1350] is Δε r =(ε r∥ -ε r⊥ ), and is tanδ iso =(2ε r⊥ tanδ ⊥ +ε r∥ tanδ ∥ ) / (2ε r⊥ +ε r∥ ).

[1351] Here, “ε r ” is the dielectric constant, “tan δ” is the dielectric loss tangent, the subscript “∥” indicates the component in the parallel direction relative to the orientation direction of the liquid crystal, and “⊥” indicates the component in the perpendicular direction relative to the orientation direction of the liquid crystal.

[1352] Δε r and tanδ iso It can be measured by the following method.

[1353] First, a liquid crystal composition is introduced into a capillary tube made of polytetrafluoroethylene (PTFE).

[1354] The capillary used here has an inner radius of 0.80 mm and an outer radius of 0.835 mm, and an effective length of 4.0 cm.

[1355] The capillary tube in which the liquid crystal composition was sealed was introduced into the center of a cavity resonator (manufactured by EMlabo Co., Ltd.) having a resonance frequency of 10 GHz.

[1356] The cavity resonator has a diameter of 30 mm and a width of 26 mm.

[1357] Then, a signal was input, and the result of recording the output signal was obtained using a network analyzer (manufactured by Keysight Technology Co., Ltd.).

[1358] The dielectric constant (ε) at 10 GHz was determined by using the difference between the resonance frequency and the resonance frequency of the PTFE capillary tube without the liquid crystal composition and the PTFE capillary tube with the liquid crystal composition. r ) and loss angle (δ).

[1359] Furthermore, the obtained tangent of δ is the dielectric loss tangent (tan δ).

[1360] Furthermore, the values ​​of characteristic components perpendicular to the orientation direction of the liquid crystal molecules and the values ​​of characteristic components parallel to the orientation direction of the liquid crystal molecules are determined by controlling the orientation of the liquid crystal molecules using the resonance frequency of a PTFE capillary enclosing the liquid crystal composition.

[1361] In order to align the liquid crystal molecules in the vertical direction (perpendicular to the effective length direction) or in the parallel direction (parallel to the effective length direction) of the PTFE capillary, a magnetic field of a permanent magnet or an electromagnet is used.

[1362] For example, the magnetic field has an inter-pole distance of 45 mm and a magnetic field intensity of 0.23 Tesla near the center.

[1363] By rotating the PTFE capillary tube in which the liquid crystal composition is sealed in parallel or perpendicular to the magnetic field, desired characteristic components can be obtained.

[1364] The measurement was carried out at a temperature of 25°C. r and tanδ iso There are no units.

[1365] Δε of the liquid crystal composition of the present invention at 25°C rIt is preferably larger, and from the viewpoint of the phase modulation ability in the GHz band, it is preferably 0.90 or more, preferably 0.90 to 1.40, preferably 0.95 to 1.40, and preferably 1.00 to 1.35.

[1366] Tan δ of the liquid crystal composition of the present invention at 25°C iso It is preferably smaller, and from the viewpoint of loss in the GHz band, it is preferably 0.025 or less, preferably 0.001 to 0.025, preferably 0.003 to 0.020, preferably 0.005 to 0.017, preferably 0.007 to 0.015, preferably 0.008 to 0.013, and preferably 0.009 to 0.012.

[1367] (Liquid crystal display devices, sensors, liquid crystal lenses, optical communication equipment and antennas)

[1368] Hereinafter, a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the liquid crystal composition of the present invention will be described.

[1369] The liquid crystal display element of the present invention is characterized by using the above-mentioned liquid crystal composition and preferably driven by an active matrix system or a passive matrix system.

[1370] Furthermore, the liquid crystal display element of the present invention is preferably a liquid crystal display element in which the dielectric constant is reversibly switched by reversibly changing the alignment direction of the liquid crystal molecules of the liquid crystal composition.

[1371] The sensor of the present invention is characterized in that the liquid crystal composition is used. For example, as its form, there can be listed: a distance sensor using electromagnetic waves, visible light or infrared light; an infrared sensor using temperature changes; a temperature sensor using changes in the wavelength of reflected light caused by changes in the spacing of cholesterol-type liquid crystals; a pressure sensor using changes in the wavelength of reflected light; an ultraviolet sensor using changes in the wavelength of reflected light caused by changes in composition; an electrical sensor using temperature changes caused by voltage and current; a radiation sensor using temperature changes accompanying the tracks of radioactive particles; an ultrasonic sensor using changes in the arrangement of liquid crystal molecules caused by mechanical vibrations of ultrasonic waves; an electromagnetic sensor using changes in the wavelength of reflected light caused by temperature changes or changes in the arrangement of liquid crystal molecules caused by electric fields, etc.

[1372] As the distance measuring sensor, a LiDAR (Light Detection And Ranging) sensor using a light source is preferable.

[1373] The LiDAR is preferably used for artificial satellites, airplanes, unmanned aircraft (drone), automobiles, railways, and ships.

[1374] As for automobile use, it is particularly preferable to use it for an autonomous driving car.

[1375] The light source is preferably a light-emitting diode (LED) or a laser, preferably a laser.

[1376] The light used for LiDAR is preferably infrared light, and the wavelength is preferably 800nm ​​to 2000nm.

[1377] Infrared lasers with a wavelength of 905 nm or 1550 nm are particularly preferred.

[1378] When emphasis is placed on the cost of the photodetector used or on its all-weather sensitivity, an infrared laser of 905 nm is preferred, and when emphasis is placed on safety with respect to human vision, an infrared laser of 1550 nm is preferred.

[1379] The liquid crystal composition of the present invention exhibits a high Δn, and thus can provide a sensor having a large phase modulation capability in the visible light, infrared light and electromagnetic wave regions and excellent detection sensitivity.

[1380] The liquid crystal lens of the present invention is characterized in that the liquid crystal composition is used, and for example, as one of its forms, includes: a first transparent electrode layer, a second transparent electrode layer, a liquid crystal layer containing the liquid crystal composition arranged between the first transparent electrode layer and the second transparent electrode layer, an insulating layer arranged between the second transparent electrode layer and the liquid crystal layer, and a high resistance layer arranged between the insulating layer and the liquid crystal layer.

[1381] The liquid crystal lens of the present invention is used as, for example, a two-dimensional (2D) or 3D switching lens, a focus adjustment lens for a camera, or the like.

[1382] The optical communication device of the present invention is characterized in that the liquid crystal composition is used. For example, as one of its forms, there can be listed a liquid crystal on silicon (LCOS) having the following structure, which has a liquid crystal layer on a reflective layer (electrode), and the liquid crystals constituting multiple pixels are two-dimensionally arranged in the liquid crystal layer.

[1383] The optical communication device of the present invention is used as a spatial phase modulator, for example.

[1384] The antenna of the present invention is characterized by using the liquid crystal composition.

[1385] More specifically, the antenna of the present invention includes: a first substrate having a plurality of grooves; a second substrate facing the first substrate and provided with a power supply portion; a first dielectric layer provided between the first substrate and the second substrate; a plurality of patch electrodes arranged corresponding to the plurality of grooves; a third substrate provided with the patch electrodes; and a liquid crystal layer provided between the first substrate and the third substrate, and the liquid crystal layer contains the liquid crystal composition.

[1386] By using a liquid crystal composition comprising one or more compounds (including subordinate concepts) represented by the general formula (i) having an indane structure and an isothiocyanate group (-NCS) and one or more compounds represented by the general formula (ii) having an isothiocyanate group (-NCS) as the liquid crystal composition, T ni High, large Δn, V th Low, Δε r Large, tanδ iso Since the antenna is small and has good storage properties at low temperatures, an antenna having high reliability against external stimuli such as heat can be provided.

[1387] Thus, an antenna capable of performing greater phase control on microwave or millimeter wave electromagnetic waves can be provided.

[1388] The antenna of the present invention preferably operates at Ka-band frequencies, or K-band frequencies, or Ku-band frequencies for satellite communications.

[1389] The antenna of the present invention is preferably a structure formed by combining a radial slot array and a patch antenna array.

[1390] As the structure of the antenna of the present invention, for example, matters described in the pamphlet of International Publication No. 2021 / 157189 can be referred to and applied.

[1391] Example

[1392] Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples.

[1393] The compositions of the following Examples and Comparative Examples contain each compound at the ratio shown in the table, and the content is described in "mass %".

[1394] In addition, the following abbreviations are used in describing compounds. In addition, unless otherwise specified, a compound that can take a cis-isomer and a trans-isomer may refer to the trans-isomer.

[1395] <Ring structure>

[1396] [Chemistry 239]

[1397] <Terminal structure>

[1398] [Table 1]

[1399] Abbreviation Chemical Structure -n <![CDATA[-C n H 2n+1 ]]> n- <![CDATA[C n H 2n+1 -]]> -On <![CDATA[-O-C n H 2n+1 ]]> nO- <![CDATA[C n H 2n+1 -O-]]> -Sn <![CDATA[-S-C n H 2n+1 ]]> nS- <![CDATA[C n H 2n+1 -S-]]> -V <![CDATA[-CH=CH2]]> V- <![CDATA[CH2=CH-]]> -V1 <![CDATA[-CH=CH-CH3]]> 1V- <![CDATA[CH3-CH=CH-]]> -2V <![CDATA[-CH2-CH2-CH=CH2]]> V2- <![CDATA[CH2=CH-CH2-CH2-]]> -2V1 <![CDATA[-CH2-CH2-CH=CH-CH3 <!-- 120 -->]]> 1V2- <![CDATA[CH3-CH=CH-CH2-CH2-]]> -OCF3 <![CDATA[-O-CF3]]> CF3O- <![CDATA[CF3-O-]]> -H -H H- H- -CN -CN CN- CN- -NCS -NCS NCS- NCS- -(1)4 <![CDATA[-CH2CH2CH(CH3)CH3]]> 4(1)- <![CDATA[CH3CH(CH3)CH2CH2-]]>

[1400] (In the table, n is a natural number) <Connection structure>

[1401] [Table 2]

[1402] Abbreviation Chemical Structure -n- <![CDATA[-C n H 2n -]]> -nO- <![CDATA[-C n H 2n -O-]]> -On- <![CDATA[-O-C n H 2n -]]> -COO- -C(=O)-O- -OCO- -O-C(=O)- -V- -CH=CH- -nV- <![CDATA[-C n H 2n -CH=CH-]]> -Vn- <![CDATA[-CH=CH-C n H 2n -]]> -T- -C≡C- -CF2O- <![CDATA[-CF2-O-]]> -OCF2- <![CDATA[-O-CF2-]]> -Az- -N=N-

[1403] (where n in the table is a natural number) (hindered phenol antioxidant)

[1404] [Chemistry 240]

[1405]

[1406] (Hindered amine light stabilizer)

[1407] [Chemistry 241]

[1408]

[1409] (Preparation of Liquid Crystal Composition)

[1410] LC-A to LC-B and LC-01 to LC-06 described in Table 3 were prepared.

[1411] [Table 3]

[1412] Table 3 LC-A LC-B LC-01 LC-02 LC-03 LC-04 LC-05 LC-06 3-In-Ph-T-Ph3-NCS 10 10 15 6 5 4-In-Ph-T-Ph3-NCS 10 3-In-T-Ph-Ph3-NCS 10 3-Id-Ph-T-Ph3-NCS 2 4-Id-Ph-T-Ph3-NCS 2 4-In-T-Ph1-T-Ph3-NCS 5 4-T-Ph-T-Ph-Ph3-NCS 3 5 3 5 5-T-Ph-T-Ph-Ph3-NCS 3 3 3 4-T-Ph-T-Ph1-Ph3-NCS 4 4 5 4 5 5-T-Ph-T-Ph1-Ph3-NCS 7 7 5 7 5 4-T-Pm2-Ph-T-Ph3-NCS 4 10 4 10 4-T-Ph2-T-Ph-Ph3-NCS 3 3 5 3 5 4-T-Ph1-Ph-T-Ph3-NCS 4 3 4 5-T-Ph1-Ph-T-Ph3-NCS 7 7 7 4(1)-T-Ph-Ph-T-Ph3-NCS 3 5-Ph3-T-Ph-Ph3-NCS 9 10 10 9 10 3-Cy-T-Ph-Ph3-NCS 5 3 10 4-Cy-T-Ph-Ph3-NCS 5 3 6 3-Cy-T-Ph-T-Ph3-NCS 6 6 6 6 4-Cy-T-Ph-T-Ph3-NCS 5 6 5 6 5-Cy-Ph-NCS 6 3 4-Ph-T-Pc1-NCS 11 6 4O-Ph2-T-Ph-NCS 5 5 5O-Ph2-T-Ph-NCS 5 5 5-Ph-T-Ph1-NCS 5 5 3-Ph-T-Ph3-NCS 13 17 17 17 17 12 5-Ph-T-Ph3-NCS 11 18 18 15 18 10 2-Cy-Ph-Ph3-NCS 12 6 4-Cy-Ph-Ph3-NCS 12 6 4-Cy-Ph-T-Ph1-NCS 16 16 5-Cy-Ph-T-Ph1-NCS 13 13 4-Cy-Ph-T-Ph3-NCS 14 5-Cy-Ph-T-Ph3-NCS 20 CF3O-Ph-Ph-Ph3-NCS 24 4-Ph-Ph-T-Ph3-NCS 6 5-Ph-Ph-T-Ph3-NCS 12 5-Ph-Ph5-T-Ph1-NCS 15 15 Total [mass%] 100 100 100 100 100 100 100 100

[1413] (Examples 1 to 36 and Comparative Examples 1 to 2)

[1414] Liquid crystal compositions listed in Tables 4 to 9 were prepared using LC-A to LC-B and LC-01 to LC-06, hindered phenol antioxidants (XX-1) to (XX-3), and hindered amine light stabilizers (YY-1) to (YY-2), and their physical properties were measured to perform a <storage test>. The results are shown in Tables 4 to 9. In Comparative Example 2, since crystallization was performed at room temperature, high frequency characteristics (Δε) were not tested. r and tanδ iso ) determination.

[1415] <Storage Test>

[1416] 0.5 g of the liquid crystal composition was weighed in a 1 mL sample bottle (manufactured by Maruemu), and degassed at 150 Pa to 250 Pa for 10 minutes to perform degassing. Then, it was rinsed with dry nitrogen and covered with a provided cap. It was stored in a temperature-controlled thermostatic bath (manufactured by Espec, SH-241) at -20°C for two weeks, and the crystallization of the liquid crystal composition was visually confirmed every other week.

[1417] [Table 4]

[1418]

[1419] [Table 5]

[1420]

[1421] [Table 6]

[1422]

[1423] [Table 7]

[1424]

[1425] [Table 8]

[1426]

[1427] [Table 9]

[1428]

[1429] According to Examples 1 to 6, the liquid crystal composition using the compound represented by the general formula (i) and the compound represented by the general formula (ii) is T ni High, large Δn, V th Low, Δε r Large, tanδ iso A liquid crystal composition that is small and has good storage properties at low temperatures.

[1430] In particular, Examples 1, 5, and 6 yielded the following results: Δn and Δε r Very big.

[1431] On the other hand, according to Comparative Examples 1 and 2, the liquid crystal compositions not using the compound represented by the general formula (i) had Δn of less than 0.38 or were confirmed to be crystallized at room temperature.

[1432] Furthermore, according to Examples 7 to 36, even when a hindered phenol antioxidant or a hindered amine light stabilizer is used in combination, T ni High, large Δn, V th Low, Δεr Large, tanδ iso Small size, good storage performance at low temperatures.

[1433] In addition, according to Examples 37 to 43, the same effects were confirmed even in the compositions having changed compositions. The results are shown in Tables 10 to 12.

[1434] [Table 10]

[1435] Table 10 LC-07 3-In-Ph-T-Ph3-NCS 10 5-T-Ph-T-Ph-Ph3-NCS 3 4-T-Ph-T-Ph1-Ph3-NCS 5 5-T-Ph-T-Ph1-Ph3-NCS 7 4-T-Pm2-Ph-T-Ph3-NCS 3 4-T-Ph2-T-Ph-Ph3-NCS 5 4-T-Ph-Ph2-T-Ph3-NCS 5 4-T-Ph1-Ph-T-Ph3-NCS 5 5-T-Ph1-Ph-T-Ph3-NCS 7 5-Ph3-T-Ph-Ph3-NCS 5 3-Cy-T-Ph-T-Ph3-NCS 5 4-Cy-T-Ph-T-Ph3-NCS 5 2-Ph-T-Ph3-NCS 8 3-Ph-T-Ph3-NCS 17 5-Ph-T-Ph3-NCS 10 Total [mass%] 100

[1436] [Table 11]

[1437]

[1438] [Table 12]

[1439]

[1440] The synthesis of the compound represented by the general formula (i) is described below.

[1441] (Synthesis Example 1) Preparation of the compound represented by formula (I-1)

[1442] [Chemistry 242]

[1443]

[1444] First, 50 g of 4-bromo-2,6-difluoroaniline, 65 g of bispinacol diboron, 70 g of potassium acetate, and 500 mL of N,N-dimethylformamide were added to the reaction container at room temperature under a nitrogen environment. Next, 4 g of bis(diphenylphosphino)ferrocenepalladium(II) dichloride was added and stirred at room temperature. Then, it was heated to 90°C and reacted for 4 hours. After the reaction was completed, 300 mL of saturated aqueous ammonium chloride solution was injected into the reaction solution, and 700 mL of ethyl acetate was used for extraction. After the organic layer was washed with saturated brine, it was refined by column chromatography (silica gel, ethyl acetate / hexane = 1 / 5 to 1 / 3), thereby obtaining 49 g of the compound represented by formula (I-1-1).

[1445] Next, under a nitrogen environment, 20.0 g of the compound represented by formula (I-1-1), 21 g of 1-bromo-4-iodobenzene, and 200 mL of tetrahydrofuran were added to the reaction vessel at room temperature. Next, 0.5 g of bis(triphenylphosphine)palladium(II) dichloride dichloromethane adduct was added and heated to 60°C. Next, 80 mL of a solution in which 16 g of sodium carbonate was dissolved in 80 mL of water was slowly added dropwise while stirring at 60°C, and stirred at 65°C for 2 hours. After the reaction was completed, 100 mL of a saturated aqueous ammonium chloride solution was injected into the reaction solution, and 200 mL of ethyl acetate was used for extraction. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, ethyl acetate / hexane=1 / 5~1 / 3) to obtain 22 g of the compound represented by formula (I-1-2).

[1446] Next, 22 g of the compound represented by formula (I-1-2), 0.5 g of copper (I) iodide, 1.8 g of tetrakis (triphenylphosphine) palladium (0), 50 mL of triethylamine, and 50 mL of N, N-dimethylformamide were added to the reaction container at room temperature under a nitrogen environment. Next, 20 mL of a solution prepared by dissolving 10 g of trimethylsilyl acetylene in 20 mL of N, N-dimethylformamide was added dropwise while heating at 75°C, and stirred at 75°C for 2 hours. After the reaction was completed, a saturated aqueous solution of ammonium chloride was injected into the reaction solution, and extraction was performed with hexane. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, ethyl acetate / hexane = 1 / 5 to 1 / 3), and the solvent was distilled off to obtain a concentrate. Next, the concentrate, 100 mL of methanol, and 1 g of potassium carbonate were added to the reaction container at room temperature, and stirred at room temperature. After completion of the reaction, the product was purified by column chromatography (silica gel, ethyl acetate / hexane=1 / 5 to 1 / 3) to obtain 15 g of a compound represented by formula (I-1-3).

[1447] [Chemistry 243]

[1448]

[1449] Then, under nitrogen environment, at room temperature, diisopropylamine 11g and tetrahydrofuran 150mL were added to the reaction vessel. Then, cooled to -78°C, after 46mL of n-butyllithium in n-hexane solution (2.4mol / L) was added dropwise, stirred at -10°C for 30 minutes. Then, cooled to -78°C, 40mL of a solution in which 14g of ethyl valerate was dissolved in 40mL of tetrahydrofuran was added dropwise. After the addition was completed, stirred at -78°C for 60 minutes, and then 100mL of a solution in which 25g of 4-bromobenzyl bromide was dissolved in 100mL of tetrahydrofuran was slowly added dropwise. After the addition was completed, stirred at -78°C for 1 hour, warmed to room temperature, and then stirred for 3 hours. After the reaction was completed, 10% by mass hydrochloric acid was added and extracted with 200mL of toluene. Then, the organic layer was cleaned with saturated brine and the solvent was distilled off.

[1450] Then, the obtained concentrate, 100mL of ethanol, 30mL of 10% by mass of sodium hydroxide aqueous solution were added to the reaction vessel under a nitrogen environment, and the heat was recycled for 3 hours and reacted. After the reaction was completed, 10% by mass of hydrochloric acid was added to neutralize, and 300mL of ethyl acetate was used for extraction. After the organic layer was cleaned with saturated brine, hexane was used for recrystallization, and 16g of compound represented by formula (I-1-4) was obtained.

[1451] Next, under a nitrogen environment, 16 g of the compound represented by formula (I-1-4) and 100 mL of dichloromethane were added to the reaction vessel at room temperature and cooled to below 10°C. Next, 20 mL of a solution prepared by dissolving 7.4 g of oxalic acid dichloride in 20 mL of dichloromethane was slowly added dropwise, and after the addition was completed, the mixture was reacted at room temperature for 1 hour. After the reaction was completed, the solvent and excess oxalic acid dichloride were distilled off to obtain a concentrate.

[1452] Then, under nitrogen environment, at room temperature, anhydrous aluminum chloride 10g, dichloromethane 100mL are added to the reaction vessel and cooled to 0 ° C. Then, 20mL of a solution in which the concentrate is dissolved in 20mL of dichloromethane is slowly added dropwise. After the addition is completed, react at room temperature for 2 hours. After adding 10 mass % hydrochloric acid, 300mL of dichloromethane is added and extracted. After the organic layer is cleaned with saturated brine, column chromatography (silica gel, toluene / hexane=1 / 1) is used for refinement, and 12g of compound represented by formula (I-1-5) is obtained.

[1453] Then, under nitrogen environment, at room temperature, add 12g of compound represented by formula (I-1-5), 30mL of triethylsilane, and 50mL of trifluoroacetic acid to the reaction container, and react for 24 hours. After the reaction is completed, the reaction solution is placed in an aqueous sodium carbonate solution, the pH value is adjusted to 7-8, and 200mL of toluene is used for extraction. After the organic layer is washed with saturated brine, column chromatography (silica gel, toluene / hexane=1 / 1) is used for purification, thereby obtaining 10g of compound represented by formula (I-1-6).

[1454] Next, 10 g of the compound represented by formula (I-1-6), 0.3 g of copper (I) iodide, 1.0 g of tetrakis (triphenylphosphine) palladium (0), 50 mL of triethylamine, and 50 mL of N, N-dimethylformamide were added to the reaction container under a nitrogen environment at room temperature. Then, while heating at 85°C, a solution of 11 g of the compound represented by formula (I-1-3) dissolved in 20 mL of N, N-dimethylformamide was added dropwise, and stirred at 85°C for 2 hours. After the reaction was completed, a saturated aqueous ammonium chloride solution was injected into the reaction solution, and extraction was performed with ethyl acetate. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, ethyl acetate / toluene = 0 / 10 to 1 / 5) to obtain 12 g of the compound represented by formula (I-1-7).

[1455] Next, 12 g of the compound represented by formula (I-1-7), 80 mL of dichloromethane, and 6 g of 1,1-thiocarbonyldiimidazole were added to the reaction container under a nitrogen environment at room temperature, and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and subsequent recrystallization (toluene / hexane = 1 / 1), thereby obtaining 11 g of the compound represented by formula (I-1).

[1456] MS (EI): m / z = 429

[1457] (Synthesis Example 2) Preparation of the compound represented by formula (I-2)

[1458] [Chemistry 244]

[1459]

[1460] Under a nitrogen environment and at room temperature, add 10 g of the compound represented by formula (I-2-1), 12 g of bispinacol diboron, 15 g of potassium acetate, and 100 mL of N,N-dimethylformamide to the reaction container. Then, add 1 g of bis(diphenylphosphino)ferrocenepalladium(II) dichloride at room temperature and stir. Then, heat to 90°C and react for 4 hours. After the reaction is completed, inject 100 mL of saturated aqueous ammonium chloride into the reaction solution and extract with 200 mL of ethyl acetate. After washing the organic layer with saturated brine, refine it by column chromatography (silica gel, hexane / toluene = 2 / 1) to obtain 11 g of the compound represented by formula (I-2-2).

[1461] Next, under a nitrogen environment, 11 g of the compound represented by the formula (I-2-2), 11 g of 1-bromo-4-iodobenzene, and 120 mL of tetrahydrofuran were added to the reaction container at room temperature. Next, 0.2 g of bis(triphenylphosphine)palladium(II) dichloride dichloromethane adduct was added and the reaction container was heated to 60°C. Next, 40 mL of a solution in which 8 g of sodium carbonate was dissolved in 40 mL of water was slowly added dropwise while stirring at 60°C, and stirred at 65°C for 2 hours. After the reaction was completed, 100 mL of a saturated aqueous ammonium chloride solution was injected into the reaction solution, and 200 mL of ethyl acetate was used for extraction. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, hexane / toluene = 1 / 3 to 1 / 2) to obtain 9 g of the compound represented by the formula (I-2-3).

[1462] In a nitrogen environment, 9 g of the compound represented by formula (I-2-3), 0.25 g of copper (I) iodide, 0.8 g of tetrakis (triphenylphosphine) palladium (0), 25 mL of triethylamine, and 50 mL of N, N-dimethylformamide were added to the reaction container at room temperature. Then, the mixture was heated to 85°C, and 10 mL of a solution prepared by dissolving 5 g of the compound represented by formula (I-2-4) in 10 mL of N, N-dimethylformamide was added dropwise, and stirred at 85°C for 2 hours. After the reaction was completed, a saturated aqueous solution of ammonium chloride was injected into the reaction solution, and extraction was performed with ethyl acetate. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, ethyl acetate / toluene = 1 / 5 to 1 / 3) to obtain 10.5 g of the compound represented by formula (I-2-5).

[1463] Next, 10.5 g of the compound represented by formula (I-2-5), 80 mL of dichloromethane, and 7.7 g of 1,1-thiocarbonyldiimidazole were added to the reaction container under a nitrogen environment at room temperature, and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and subsequent recrystallization (toluene / hexane = 1 / 1), thereby obtaining 9.5 g of the compound represented by formula (I-2).

[1464] MS (EI): m / z = 429

[1465] (Synthesis Example 3) Preparation of the compound represented by formula (I-3)

[1466] [Chemistry 245]

[1467]

[1468] Under nitrogen environment, 10 g of the compound represented by formula (I-3-1) synthesized by the same method as in Synthesis Example 2, 10 g of 1-bromo-4-iodobenzene, and 120 mL of tetrahydrofuran were added to the reaction container at room temperature. Next, 0.2 g of bis(triphenylphosphine)palladium(II) dichloride dichloromethane adduct was added and heated to 60°C. Next, 40 mL of a solution in which 7.5 g of sodium carbonate was dissolved in 40 mL of water was slowly added dropwise while stirring at 60°C, and stirred at 65°C for 2 hours. After the reaction was completed, 100 mL of saturated aqueous ammonium chloride solution was injected into the reaction solution, and extraction was performed using 200 mL of ethyl acetate. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, hexane / toluene = 1 / 3 to 1 / 2) to obtain 8 g of the compound represented by formula (I-3-2).

[1469] In a nitrogen environment, 8 g of the compound represented by formula (I-3-2), 0.23 g of copper (I) iodide, 0.7 g of tetrakis (triphenylphosphine) palladium (0), 25 mL of triethylamine, and 50 mL of N, N-dimethylformamide were added to the reaction container at room temperature. Then, the mixture was heated to 85°C, and a solution prepared by dissolving 4.5 g of the compound represented by formula (I-3-3) in 10 mL of N, N-dimethylformamide was added dropwise, and stirred at 85°C for 2 hours. After the reaction was completed, a saturated aqueous solution of ammonium chloride was injected into the reaction solution, and extraction was performed with ethyl acetate. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, ethyl acetate / toluene = 1 / 5 to 1 / 3) to obtain 8.5 g of the compound represented by formula (I-3-4).

[1470] Next, 8.5 g of the compound represented by formula (I-3-4), 80 mL of dichloromethane, and 4.5 g of 1,1-thiocarbonyldiimidazole were added to the reaction container under a nitrogen environment at room temperature, and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and subsequent recrystallization (toluene / hexane = 1 / 1), thereby obtaining 8 g of the compound represented by formula (I-3).

[1471] MS (EI): m / z = 443

[1472] (Synthesis Example 4) Preparation of the compound represented by formula (I-4)

[1473] [Chemistry 246]

[1474]

[1475] Under nitrogen environment, 11 g of compound represented by formula (I-4-1), 11 g of 1-bromo-4-iodobenzene, and 120 mL of tetrahydrofuran were added to the reaction container at room temperature. Next, 0.2 g of bis(triphenylphosphine)palladium(II) dichloride dichloromethane adduct was added and heated to 60°C. Next, 40 mL of a solution in which 8 g of sodium carbonate was dissolved in 40 mL of water was slowly added dropwise while stirring at 60°C, and stirred at 65°C for 2 hours. After the reaction was completed, 100 mL of saturated aqueous ammonium chloride solution was injected into the reaction solution, and 200 mL of ethyl acetate was used for extraction. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, hexane / toluene = 1 / 3 to 1 / 2) to obtain 9 g of compound represented by formula (I-4-2).

[1476] In a nitrogen environment, 9 g of the compound represented by formula (I-4-2), 0.25 g of copper (I) iodide, 0.8 g of tetrakis (triphenylphosphine) palladium (0), 25 mL of triethylamine, and 50 mL of N, N-dimethylformamide were added to the reaction container at room temperature. Then, the mixture was heated to 85°C, and 10 mL of a solution prepared by dissolving 5 g of the compound represented by formula (I-4-3) in 10 mL of N, N-dimethylformamide was added dropwise, and stirred at 85°C for 2 hours. After the reaction was completed, a saturated aqueous solution of ammonium chloride was injected into the reaction solution, and extraction was performed with ethyl acetate. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, ethyl acetate / toluene = 1 / 5 to 1 / 3) to obtain 10 g of the compound represented by formula (I-4-4).

[1477] Next, 10 g of the compound represented by formula (I-4-4), 80 mL of dichloromethane, and 7.6 g of 1,1-thiocarbonyldiimidazole were added to the reaction container under a nitrogen environment at room temperature, and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and subsequent recrystallization (toluene / hexane = 1 / 1), thereby obtaining 8.5 g of the compound represented by formula (I-4).

[1478] MS (EI): m / z = 429

[1479] (Synthesis Example 5) Preparation of the compound represented by formula (I-5)

[1480] [Chemistry 247]

[1481]

[1482] Under nitrogen environment, 10 g of the compound represented by formula (I-5-1) synthesized by the same method as in Synthesis Example 2, 10 g of 1-bromo-4-iodobenzene, and 120 mL of tetrahydrofuran were added to the reaction container at room temperature. Next, 0.2 g of bis(triphenylphosphine)palladium(II) dichloride dichloromethane adduct was added and heated to 60°C. Then, 40 mL of a solution in which 7.5 g of sodium carbonate was dissolved in 40 mL of water was slowly added dropwise while stirring at 60°C, and stirred at 65°C for 2 hours. After the reaction was completed, 100 mL of saturated aqueous ammonium chloride solution was injected into the reaction solution, and extraction was performed using 200 mL of ethyl acetate. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, hexane / toluene = 1 / 3 to 1 / 2) to obtain 8 g of the compound represented by formula (I-5-2).

[1483] Next, 8 g of the compound represented by formula (I-5-2), 0.23 g of copper (I) iodide, 0.7 g of tetrakis (triphenylphosphine) palladium (0), 25 mL of triethylamine, and 50 mL of N, N-dimethylformamide were added to the reaction container at room temperature under a nitrogen environment. Then, the mixture was heated to 85°C, and 10 mL of a solution prepared by dissolving 4.5 g of the compound represented by formula (I-5-3) in 10 mL of N, N-dimethylformamide was added dropwise, and stirred at 85°C for 2 hours. After the reaction was completed, a saturated aqueous ammonium chloride solution was injected into the reaction solution, and extraction was performed with ethyl acetate. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, ethyl acetate / toluene = 1 / 5 to 1 / 3) to obtain 8.2 g of the compound represented by formula (I-5-4).

[1484] Next, 8.2 g of the compound represented by formula (I-5-4), 80 mL of dichloromethane, and 4.4 g of 1,1-thiocarbonyldiimidazole were added to the reaction container under a nitrogen environment at room temperature, and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and subsequent recrystallization (toluene / hexane = 1 / 1), thereby obtaining 7.8 g of the compound represented by formula (I-5).

[1485] MS (EI): m / z = 443

[1486] (Synthesis Example 6) Preparation of the compound represented by formula (I-6)

[1487] [Chemistry 248]

[1488]

[1489] In a nitrogen environment, 15 g of 1-bromo-4-iodo-3-methylbenzene, 0.3 g of copper (I) iodide, 1.8 g of tetrakis (triphenylphosphine) palladium (0), 50 mL of triethylamine, and 50 mL of N, N-dimethylformamide were added to a reaction container at room temperature. Then, the mixture was heated to 85°C, and a solution of 8.5 g of the compound represented by formula (I-6-1) dissolved in 20 mL of N, N-dimethylformamide was added dropwise, and stirred at 85°C for 2 hours. After the reaction was completed, 100 mL of saturated aqueous ammonium chloride solution was injected into the reaction solution, and extraction was performed with 200 mL of ethyl acetate. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, ethyl acetate / toluene = 1 / 5 to 1 / 3), thereby obtaining 13.6 g of the compound represented by formula (I-6-2).

[1490] Next, 13.6 g of the compound represented by formula (I-6-2), 0.5 g of copper (I) iodide, 1 g of tetrakis (triphenylphosphine) palladium (0), 50 mL of triethylamine, and 50 mL of N, N-dimethylformamide were added to the reaction container under a nitrogen environment at room temperature. Next, the mixture was heated to 75°C, and 10 mL of a solution prepared by dissolving 5.5 g of trimethylsilyl acetylene in 10 mL of N, N-dimethylformamide was added dropwise, and the mixture was stirred at 75°C for 2 hours. After the reaction was completed, a saturated aqueous ammonium chloride solution was injected into the reaction solution, and the mixture was extracted with 200 mL of ethyl acetate. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, ethyl acetate / hexane = 1 / 5 to 1 / 3), the solvent was distilled off, and the mixture was concentrated to obtain a concentrate. Next, the concentrate, 100 mL of methanol, and 2.5 g of potassium carbonate were added to the reaction container at room temperature, and the mixture was stirred at room temperature. After completion of the reaction, the product was purified by column chromatography (silica gel, ethyl acetate / hexane=1 / 5 to 1 / 3) to obtain 9.5 g of a compound represented by formula (I-6-3).

[1491] Then, under nitrogen environment, 9 g of the compound represented by formula (I-6-4), 0.3 g of copper (I) iodide, 1.8 g of tetrakis (triphenylphosphine) palladium (0), 50 mL of triethylamine, and 50 mL of N, N-dimethylformamide were added to the reaction container at room temperature. Then, the mixture was heated to 85°C, and 20 mL of a solution prepared by dissolving 9.5 g of the compound represented by formula (I-6-3) in 20 mL of N, N-dimethylformamide was added dropwise, and stirred at 85°C for 2 hours. After the reaction was completed, 100 mL of a saturated aqueous ammonium chloride solution was injected into the reaction solution, and extraction was performed using 200 mL of ethyl acetate. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, ethyl acetate / toluene = 1 / 5 to 1 / 3), thereby obtaining 13 g of the compound represented by formula (I-6-5).

[1492] Next, 13 g of the compound represented by formula (I-6-5), 90 mL of dichloromethane, and 5.5 g of 1,1-thiocarbonyldiimidazole were added to the reaction vessel under a nitrogen environment at room temperature, and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and subsequent recrystallization (toluene / hexane = 1 / 1), thereby obtaining 12 g of the compound represented by formula (I-6).

[1493] MS (EI): m / z = 495

[1494] (Synthesis Example 7) Preparation of the compound represented by formula (I-7)

[1495] [Chemistry 249]

[1496]

[1497] Under nitrogen environment, 15 g of 1-bromo-3-fluoro-4-iodobenzene, 0.3 g of copper (I) iodide, 1.9 g of tetrakis (triphenylphosphine) palladium (0), 50 mL of triethylamine, and 50 mL of N, N-dimethylformamide were added to the reaction container at room temperature. Then, the mixture was heated to 85°C, and 20 mL of a solution prepared by dissolving 8.3 g of the compound represented by formula (I-7-1) in 20 mL of N, N-dimethylformamide was added dropwise, and stirred at 85°C for 2 hours. After the reaction was completed, 100 mL of saturated aqueous ammonium chloride solution was injected into the reaction solution, and extraction was performed with 200 mL of ethyl acetate. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, ethyl acetate / toluene = 1 / 5 to 1 / 3), thereby obtaining 13 g of the compound represented by formula (I-7-2).

[1498] Next, 13 g of the compound represented by formula (I-7-2), 0.4 g of copper (I) iodide, 0.9 g of tetrakis (triphenylphosphine) palladium (0), 50 mL of triethylamine, and 50 mL of N, N-dimethylformamide were added to the reaction container under a nitrogen environment at room temperature. Next, the mixture was heated to 75°C, and 10 mL of a solution prepared by dissolving 5.2 g of trimethylsilyl acetylene in 10 mL of N, N-dimethylformamide was added dropwise, and stirred at 75°C for 2 hours. After the reaction was completed, a saturated aqueous ammonium chloride solution was injected into the reaction solution, and 200 mL of ethyl acetate was used for extraction. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, ethyl acetate / hexane = 1 / 5 to 1 / 3), the solvent was distilled off and concentrated to obtain a concentrate. Next, the concentrate, 100 mL of methanol, and 2.5 g of potassium carbonate were added to the reaction container at room temperature, and stirred at room temperature. After completion of the reaction, the product was purified by column chromatography (silica gel, ethyl acetate / hexane=1 / 5 to 1 / 3) to obtain 9 g of a compound represented by formula (I-7-3).

[1499] Then, 8.4 g of the compound represented by formula (I-7-4), 0.2 g of copper (I) iodide, 1.5 g of tetrakis (triphenylphosphine) palladium (0), 50 mL of triethylamine, and 50 mL of N, N-dimethylformamide were added to the reaction container at room temperature under a nitrogen environment. Next, the mixture was heated to 85°C, and 20 mL of a solution prepared by dissolving 9 g of the compound represented by formula (I-7-3) in 20 mL of N, N-dimethylformamide was added dropwise, and stirred at 85°C for 2 hours. After the reaction was completed, 100 mL of a saturated aqueous ammonium chloride solution was injected into the reaction solution, and extraction was performed using 200 mL of ethyl acetate. After the organic layer was washed with saturated brine, it was purified by column chromatography (silica gel, ethyl acetate / toluene = 1 / 5 to 1 / 3), thereby obtaining 12 g of the compound represented by formula (I-7-5).

[1500] Next, 12 g of the compound represented by formula (I-7-5), 90 mL of dichloromethane, and 5 g of 1,1-thiocarbonyldiimidazole were added to the reaction vessel at room temperature under a nitrogen environment, and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and subsequent recrystallization (toluene / hexane = 1 / 1), thereby obtaining 11 g of the compound represented by formula (I-7).

[1501] MS (EI): m / z = 485

[1502] Industrial Applicability

[1503] The compound and liquid crystal composition of the present invention can be used for liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices and antennas.

Claims

1. A liquid crystal composition comprising: one or more compounds represented by the following general formula (i); and one or more compounds represented by the following general formula (ii), [Chemistry 1] (In general formula (i), R i1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-, One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-. One or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH-, or -O-CO-CH=CH-. One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. However, oxygen atoms do not bond directly to each other. A i1 and A i2 each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms, The A i1 and A i2 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S i1 replace, Substituent S i1 represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S- and / or -CO-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-, One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-. One or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH- and / or -O-CO-CH=CH-, One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. However, oxygen atoms do not bond directly to each other. In the substituent S i1 When there are multiple, these may be the same or different, L i1 and L i2 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group or an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-, One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-. One or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH- and / or -O-CO-CH=CH-, One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. However, oxygen atoms do not bond directly to each other. Z i1 and Z i2 each independently represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms, One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-. One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, One or more -CH2-CH2-CH2-CH2- in the alkylene group may be independently substituted by -CH=NN=CH-. However, oxygen atoms do not bond directly to each other. n i1 represents an integer from 0 to 3, In A i2 or Z i2 When there are multiple, these may be the same or different). [Chemistry 2] (In general formula (ii), R ii1 each independently represents an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-, One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-. One or more hydrogen atoms in the alkyl group may be independently replaced by halogen atoms. However, oxygen atoms do not bond directly to each other. A ii1 and A ii2 Each independently represents a group (a), a group (b), a group (c) and a group (d) selected from the following: (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- in the group may be substituted with -O- and / or -S-) (b) 1,4-phenylene (one or two or more -CH= in the group may be substituted with -N=) (c) 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene -2,7-diyl (one or two or more -CH= in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl may be substituted with -N=) (d) thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl, benzo[1,2-b:4,5-b']dithiophene-2,6-diyl (one -CH= or two or more -CH= in the above group may be substituted with -N=) The basis of the group is The A ii1 and A ii2 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S ii1 replace, Substituent S ii1 represents any one of a halogen atom, a pentafluoromercapto group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-, One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-. One or more hydrogen atoms in the alkyl group may be independently replaced by halogen atoms. However, oxygen atoms do not bond directly to each other. In the substituent S ii1 When there are multiple, these may be the same or different. Z ii1 represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms, One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-. One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, One or more -CH2-CH2-CH2- in the alkylene group may be independently substituted by -O-CO-O-. Oxygen atoms do not bond directly to each other. n ii1 represents an integer from 1 to 4, In A ii1 and Z ii1 When there are multiple, these may be the same or different. in, (excluding compounds represented by general formula (i)).

2. The liquid crystal composition according to claim 1, wherein the compound represented by the general formula (i) is selected from the group consisting of compounds represented by the following general formulas (i-1) to (i-14), [Chemistry 3] [Chemistry 4] (In general formula (i-1) to general formula (i-14), R i1 , A i1 , A i2 , L i1 and L i2 represents the same as R in the general formula (i) i1 , A i1 , A i2 , L i1 and L i2 The same meaning respectively, In the general formula (i-9), A i2-2 The definition of A in the general formula (i) is the same as i2 ) 3. The liquid crystal composition according to claim 1 or 2, wherein the compound represented by the general formula (ii) is selected from the group consisting of compounds represented by the following general formulas (ii-1) to (ii-8), [Chemistry 5] R ii1- A ii1 -A ii2 -NCS (ii-1) R ii1 -A ii1 -A ii1-2 -A ii2 -NCS (ii-5) R ii1 -A ii1 -A ii1 - 2 -A ii1-3 -A ii2 -NCS (ii-8) (In general formula (ii-1) to general formula (ii-8), R ii1 , A ii1 and A ii2 represents the same as R in the general formula (ii) ii1 , A ii1 and A ii2 The same meaning respectively, In the general formula (ii-3) to the general formula (ii-9), A ii1-2 and A ii1-3 The definitions of are independently the same as those of A in the general formula (ii). ii1 ) 4. The liquid crystal composition according to claim 1 or 2, further comprising one or more compounds represented by the following general formula (vt): [Chemistry 6] (In the general formula (vt), R vt1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-, One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-. One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. However, oxygen atoms do not bond directly to each other. R vt2 represents any one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto 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, or an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-, One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-. One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. However, oxygen atoms do not bond directly to each other. A vt1 , A vt2 and A vt3 each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms, The A vt1 , A vt2 and A vt3 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S vt1 replace, Substituent S vt1 represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S- and / or -CO-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-, One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-. One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. However, oxygen atoms do not bond directly to each other. In the substituent S vt1 When there are multiple, these may be the same or different. Z vt1 each independently represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms, One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-. One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, One or more -CH2-CH2-CH2- in the alkylene group may be independently replaced by -O-CO-O-. However, oxygen atoms do not bond directly to each other. n vt1 represents an integer from 1 to 3, But in A vt3 and Z vt1 When there are multiple ones, these may be the same or different). The liquid crystal composition according to claim 1 or 2, wherein Δn at 25°C and 589 nm is 0.38 or more. 6 . A liquid crystal display element using the liquid crystal composition according to claim 1 .

7. The liquid crystal display element according to claim 6, which is driven by an active matrix method or a passive matrix method. 8 . A liquid crystal display element that reversibly switches a dielectric constant by reversibly changing the alignment direction of liquid crystal molecules of the liquid crystal composition according to claim 1 . 9 . A sensor using the liquid crystal composition according to claim 1 . 10 . A liquid crystal lens using the liquid crystal composition according to claim 1 .

11. An optical communication device using the liquid crystal composition according to any one of claims 1 to 5. 12 . An antenna using the liquid crystal composition according to claim 1 .

13. The antenna according to claim 12, comprising: A first substrate having a plurality of grooves; A second substrate, facing the first substrate, provided with a power supply portion; A first dielectric layer is disposed between the first substrate and the second substrate; a plurality of patch electrodes, arranged corresponding to the plurality of grooves; A third substrate is provided with the patch electrode; as well as A liquid crystal layer is disposed between the first substrate and the third substrate, and The liquid crystal layer contains the liquid crystal composition according to any one of claims 1 to 5.

14. A compound represented by the following general formula (i): [Chemistry 7] (In general formula (i), R i1 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-, One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-. One or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH-, or -O-CO-CH=CH-. One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. However, oxygen atoms do not bond directly to each other. A i1 and A i2 each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms, The A i1 and A i2 One or more hydrogen atoms in the molecule may be independently substituted by a substituent group S i1 replace, Substituent S i1 represents any one of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S- and / or -CO-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-, One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-. One or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH- and / or -O-CO-CH=CH-, One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. However, oxygen atoms do not bond directly to each other. In the substituent S i1 When there are multiple, these may be the same or different, L i1 and L i2 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluoromercapto group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group or an alkyl group having 1 to 20 carbon atoms, One or more -CH2- in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-. One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-, One or more -CH2-CH2-CH2- in the alkyl group may be independently replaced by -O-CO-O-. One or more -CH2-CH2-CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH- and / or -O-CO-CH=CH-, One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms. However, oxygen atoms do not bond directly to each other. Z i1 and Z i2 each independently represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms, One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-. One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, One or more -CH2-CH2-CH2-CH2- in the alkylene group may be independently substituted by -CH=NN=CH-. However, oxygen atoms do not bond directly to each other. n i1 represents an integer from 0 to 3, In A i2 or Z i2 When there are multiple ones, these may be the same or different).

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