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

Abstract

The objective of this invention is to provide a compound, a liquid crystal composition, and liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas using the same, wherein the compound can provide T ni High, large Δn, V th Low, Δε r Large, tanδ iso Liquid crystal compositions with good preservation at low temperatures. Specifically, a liquid crystal composition comprising one or more of the compounds represented by general formula (i) having an alkynyl group and an isothiocyanate group (-NCS).

Description

Technical Field

[0001] This invention relates to a compound, a liquid crystal composition, and liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas using the same. Background Technology

[0002] As a novel application of liquid crystals (LCDs), which are mostly used in displays, the use of LCD antennas for transmitting and receiving radio waves between mobile vehicles such as automobiles and communication satellites is attracting considerable attention. Previously, satellite communication used parabolic antennas, but in mobile applications such as automobiles, these antennas had to be constantly oriented towards the satellite, requiring large movable parts. However, LCD antennas operate by changing the direction of radio wave transmission and reception through the liquid crystal within the panel, thus eliminating the need to move the antenna itself, and allowing for a planar antenna shape. Furthermore, research is underway on low-Earth orbit (LEO) satellite constellations utilizing multiple LEO satellites to achieve high-capacity, high-speed global communication. For tracking LEO satellites that appear to be constantly moving from the ground, LCD antennas that can easily change the direction of radio wave transmission and reception are useful.

[0003] Generally, the automated operation of vehicles requires downloading large amounts of high-precision three-dimensional (3D) map data. However, by using a liquid crystal antenna, and assembling the antenna within the vehicle, it is possible to download large amounts of data from communication satellites even without any moving mechanical parts. The frequency band used in satellite communication is approximately 13 GHz, which is significantly different from the frequencies used in liquid crystal displays to date. Therefore, the required physical properties of the liquid crystal are also quite different; for example, the required Δn for liquid crystals used in antennas is approximately 0.4, and the operating temperature range is -20°C to 120°C.

[0004] In addition, infrared laser image recognition and ranging devices using liquid crystals are attracting attention as sensors for the automatic operation of moving vehicles such as automobiles. For these applications, the required Δn is 0.3 to 0.6, and the operating temperature range is 10°C to 100°C.

[0005] Furthermore, it is known that liquid crystal compounds that form liquid crystal compositions exhibiting high Δn values ​​of 0.2 or higher generally have low compatibility. Therefore, it is also important to select liquid crystal compounds with high compatibility.

[0006] In this regard, for example, patent document 1 can be cited as a technology for liquid crystals used in antennas.

[0007] In addition, Non-Patent Document 1 advocates using liquid crystal materials as a component of high-frequency devices.

[0008] Existing technical documents

[0009] Patent documents

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

[0011] Non-patent literature

[0012] Non-patent literature 1: D. Dolfi, "Electronics Letters", (UK), 1993, Vol. 29, No. 10, pp. 926-927 Summary of the Invention

[0013] The problem that the invention aims to solve

[0014] The objective of this invention is to provide a compound, a liquid crystal composition, and liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas using the same, wherein the compound can provide T ni High, large Δn, V th Low, Δε r Large, tanδ iso Liquid crystal compositions that are well preserved at small and low temperatures.

[0015] Technical means to solve the problem

[0016] Through diligent research, the inventors discovered that one or more liquid crystal compositions comprising compounds represented by general formula (i) having alkynyl and isothiocyanate groups (-NCS) can solve the aforementioned problem, thus completing the present invention.

[0017] The structure of the present invention that solves the aforementioned problem is as follows.

[0018] The compounds of the present invention are those represented by the following general formula (i).

[0019] [Chemistry 1]

[0020]

[0021] (in general formula (i),

[0022] R i1 The alkynyl group represents the number of carbon atoms from 2 to 20.

[0023] One or more of the -CH2- groups in the alkynyl group may be independently replaced by -O-, -S-, -CO- and / or -CS-.

[0024] One or more of the -CH2-CH2- groups in the alkynyl group can be independently replaced 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 of the -CH2-CH2-CH2- groups in the alkynyl group can be independently replaced by -O-CO-O-.

[0026] One or more hydrogen atoms in the alkynyl group can be independently substituted by halogen atoms.

[0027] However, oxygen atoms do not bond directly to each other.

[0028] A i1 A i2 and A i3 Each can be independently represented as either a hydrocarbon ring with 3 to 16 carbon atoms or a heterocycle with 3 to 16 carbon atoms.

[0029] The A i1 A i2 and A i3 One or more hydrogen atoms can be independently replaced by substituents S. i1 replace,

[0030] Substituent S i1 It represents any one of the following: fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluoromercapto, nitro, cyano, isocyano, amino, hydroxyl, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyano, or alkyl group having 1 to 20 carbon atoms.

[0031] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, and / or -CO-.

[0032] One or more of the -CH2-CH2- groups 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-.

[0033] One or more of the -CH2-CH2-CH2- groups in the alkyl group can be independently substituted by -O-CO-O- groups.

[0034] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0035] However, oxygen atoms do not bond directly to each other.

[0036] In the substituent S i1 When multiple instances exist, these can be the same or different.

[0037] Z i1 and Zi2 Each independently represents any one of a single bond or an alkylene group having 1 to 20 carbon atoms.

[0038] One or more of the -CH2- groups in the alkylene group may be independently replaced by -O-, -CF2- and / or -CO-.

[0039] One or more of the -CH2-CH2- groups 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-.

[0040] However, oxygen atoms do not bond directly to each other.

[0041] n i1 (Represents integers from 0 to 1).

[0042] In addition, the liquid crystal composition of the present invention comprises one or more of the aforementioned compounds.

[0043] Furthermore, the liquid crystal display element of the present invention uses the liquid crystal composition.

[0044] Furthermore, the sensor of the present invention uses the liquid crystal composition described above.

[0045] Furthermore, the liquid crystal lens of the present invention uses the liquid crystal composition described above.

[0046] Furthermore, the optical communication device of the present invention uses the liquid crystal composition.

[0047] Furthermore, the antenna of the present invention uses the liquid crystal composition.

[0048] Furthermore, as an example of the structure of the present invention, it is described below.

[0049] Item 1. A liquid crystal composition comprising one or more compounds represented by the following general formula (i),

[0050] [Chemistry 2]

[0051]

[0052] (in general formula (i),

[0053] R i1 The alkynyl group represents the number of carbon atoms from 2 to 20.

[0054] One or more of the -CH2- groups in the alkynyl group may be independently replaced by -O-, -S-, -CO- and / or -CS-.

[0055] One or more of the -CH2-CH2- groups in the alkynyl group can be independently replaced by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0056] One or more of the -CH2-CH2-CH2- groups in the alkynyl group can be independently replaced by -O-CO-O-.

[0057] One or more hydrogen atoms in the alkynyl group can be independently substituted by halogen atoms.

[0058] However, oxygen atoms do not bond directly to each other.

[0059] A i1 A i2 and A i3 Each can be independently represented as either a hydrocarbon ring with 3 to 16 carbon atoms or a heterocycle with 3 to 16 carbon atoms.

[0060] The A i1 A i2 and A i3 One or more hydrogen atoms can be independently replaced by substituents S. i1 replace,

[0061] Substituent S i1 It represents any one of the following: fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluoromercapto, nitro, cyano, isocyano, amino, hydroxyl, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyano, or alkyl group having 1 to 20 carbon atoms.

[0062] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, and / or -CO-.

[0063] One or more of the -CH2-CH2- groups 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-.

[0064] One or more of the -CH2-CH2-CH2- groups in the alkyl group can be independently substituted by -O-CO-O- groups.

[0065] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0066] However, oxygen atoms do not bond directly to each other.

[0067] In the substituent S i1 When multiple instances exist, these can be the same or different.

[0068] Z i1 and Z i2 Each independently represents any one of a single bond or an alkylene group having 1 to 20 carbon atoms.

[0069] One or more of the -CH2- groups in the alkylene group may be independently replaced by -O-, -CF2- and / or -CO-.

[0070] One or more of the -CH2-CH2- groups 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-.

[0071] However, oxygen atoms do not bond directly to each other.

[0072] n i1 (Represents integers from 0 to 1).

[0073] Item 2. The liquid crystal composition according to Item 1, wherein the compound represented by general formula (i) is selected from the group consisting of compounds represented by general formulas (i-1) to (i-5).

[0074] [Chemistry 3]

[0075]

[0076] (In general formulas (i-1) to (i-5),

[0077] R i1 A i1 A i2 and A i3 R represents the expression in the general formula (i). i1 A i1 A i2 and A i3 (The meanings are the same for each).

[0078] Item 3. The liquid crystal composition according to Item 1 or Item 2 further comprises one or more compounds represented by the following general formula (ii),

[0079] [Chemistry 4]

[0080]

[0081] (in general formula (ii),

[0082] R ii1 Alkyl groups having 1 to 20 carbon atoms

[0083] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO-, and / or -CS-.

[0084] One or more of the -CH2-CH2- groups in the alkyl group may be independently substituted by -CH=CH-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CF=CF- and / or -C≡C-.

[0085] One or more of the -CH2-CH2-CH2- groups in the alkyl group can be independently substituted by -O-CO-O- groups.

[0086] One or more hydrogen atoms in the alkyl group can be independently substituted with halogen atoms.

[0087] However, oxygen atoms do not bond directly to each other.

[0088] A ii1 and A ii2 Represent the basis(a), basis(b), basis(c), and basis(d) chosen independently:

[0089] (a) 1,4-cyclohexylene (one or more non-adjacent -CH2- groups may be replaced by -O- and / or -S-)

[0090] (b) 1,4-Phenylidene (one or more -CH= groups may be substituted with -N=)

[0091] (c) 1,4-cyclohexenyl, bicyclo[2.2.2]octane-1,4-diyl, naphth-2,6-diyl, naphth-1,4-diyl, 1,2,3,4-tetrahydronaphth-2,6-diyl, 5,6,7,8-tetrahydronaphth-1,4-diyl, decahydronaphth-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene -2,7-Diyl (one 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 can be substituted with -N=)

[0092] (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 or more -CH= groups may be substituted with -N=)

[0093] The base of the group formed,

[0094] The A ii1 and A ii2 One or more hydrogen atoms can be independently replaced by substituents S. ii1 replace,

[0095] Substituent S ii1 It represents any one of the following: halogen atom, pentafluoromercapto, nitro, cyano, isocyano, amino, hydroxyl, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyano, or alkyl group having 1 to 20 carbon atoms.

[0096] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO-, and / or -CS-.

[0097] One or more of the -CH2-CH2- groups 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-.

[0098] One or more of the -CH2-CH2-CH2- groups in the alkyl group can be independently substituted by -O-CO-O- groups.

[0099] One or more hydrogen atoms in the alkyl group can be independently substituted with halogen atoms.

[0100] However, oxygen atoms do not bond directly to each other.

[0101] In the substituent S ii1 When multiple instances exist, these can be the same or different.

[0102] Z ii1 It represents any of the single bonds and alkylene groups having 1 to 20 carbon atoms.

[0103] One or more of the -CH2- groups in the alkylene group may be independently substituted by -O- groups.

[0104] One or more of the -CH2-CH2- groups 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-.

[0105] One or more of the -CH2-CH2-CH2- groups in the alkylene group can be independently substituted by -O-CO-O-.

[0106] Oxygen atoms do not bond directly to each other.

[0107] n ii1 Represents integers from 1 to 4.

[0108] In A ii1 and Z ii1 When multiple instances exist, these instances can be the same or different.

[0109] Except for compounds represented by general formula (i).

[0110] Item 4. The liquid crystal composition according to any one of items 1 to 3, wherein the compound represented by general formula (ii) is selected from the group consisting of compounds represented by general formulas (ii-1) to (ii-7).

[0111] [Chemistry 5]

[0112] R ii1 -A ii1 -A ii2 -NCS (ii-1)

[0113]

[0114] (In general formulas (ii-1) to (ii-7),

[0115] R ii1 A ii1 and A ii2 R represents the expression in general formula (ii). ii1 A ii1 and A ii2 They have the same meaning,

[0116] In general formulas (ii-3) to (ii-7), A ii1-2 The definition of A in the general formula (ii) ii1 (The definitions are the same).

[0117] Item 5. The liquid crystal composition according to any one of items 1 to 4 further comprises one or more compounds represented by the following general formula (vi).

[0118] [Chemistry 6]

[0119]

[0120] (in the general formula (vi),

[0121] R vi1 Indicates an alkyl group having 1 to 20 hydrogen atoms or carbon atoms.

[0122] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO-, and / or -CS-.

[0123] One or more of the -CH2-CH2- groups 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-.

[0124] One or more of the -CH2-CH2-CH2- groups in the alkyl group can be independently substituted by -O-CO-O- groups.

[0125] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0126] However, oxygen atoms do not bond directly to each other.

[0127] R vi2 It represents any one of the following: hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluoromercapto, nitro, cyano, isocyano, amino, hydroxyl, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, or an alkyl group having 1 to 20 carbon atoms.

[0128] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO-, and / or -CS-.

[0129] One or more of the -CH2-CH2- groups 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-.

[0130] One or more of the -CH2-CH2-CH2- groups in the alkyl group can be independently substituted by -O-CO-O- groups.

[0131] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0132] However, oxygen atoms do not bond directly to each other.

[0133] A vi1 A vi2 and A vi3 Each can be independently represented as either a hydrocarbon ring with 3 to 16 carbon atoms or a heterocycle with 3 to 16 carbon atoms.

[0134] The A vi1 A vi2 and A vi3 One or more hydrogen atoms can be independently replaced by substituents S. vi1 replace,

[0135] Substituent S vi1 It represents any one of the following: fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluoromercapto, nitro, cyano, isocyano, amino, hydroxyl, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyano, or alkyl group having 1 to 20 carbon atoms.

[0136] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, and / or -CO-.

[0137] One or more of the -CH2-CH2- groups 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-.

[0138] One or more of the -CH2-CH2-CH2- alkyl groups may be replaced by -O-CO-O-.

[0139] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0140] However, oxygen atoms do not bond directly to each other.

[0141] In the substituent S vi1 When multiple instances exist, these can be the same or different.

[0142] Z vi1 Each independently represents any one of a single bond or an alkylene group having 1 to 20 carbon atoms.

[0143] One or more of the -CH2- groups in the alkylene group may be independently replaced by -O-, -CF2- and / or -CO-.

[0144] One or more of the -CH2-CH2- groups 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-.

[0145] One or more of the -CH2-CH2-CH2- groups in the alkylene group can be independently substituted by -O-CO-O-.

[0146] However, oxygen atoms do not bond directly to each other.

[0147] n vi1 Represents integers from 1 to 3.

[0148] But in A vi1 and Z vi1 If multiple instances exist, these instances can be the same or different.

[0149] Item 6. The liquid crystal composition according to any one of items 1 to 5 further comprises one or more compounds represented by the following general formula (vii).

[0150] [Chemistry 7]

[0151] R vii1 -A vii1 -C≡CA vii2 -N=NA vii3 -R vii2 (vii)

[0152] (In the general formula (vii),

[0153] R vii1 and R vii2 Each of the following can be independently represented: a halogen atom, a cyano group, or an alkyl group with 1 to 20 carbon atoms.

[0154] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO-, and / or -CS-.

[0155] One or more of the -CH2-CH2- groups 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-.

[0156] One or more of the -CH2-CH2-CH2- groups in the alkyl group can be independently substituted by -O-CO-O- groups.

[0157] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0158] However, oxygen atoms do not bond directly to each other.

[0159] A vii1 A vii2 A vii3 Represent the basis(a), basis(b), and basis(c) chosen independently, respectively:

[0160] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups may be replaced with -O-)

[0161] (b) 1,4-phenylene (one or more -CH= groups may be substituted with -N=) and

[0162] (c) Naphthalene-1,4-diyl, naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one or more -CH= in naphthalene-1,4-diyl, naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl can be replaced by -N=)

[0163] The base of the group formed,

[0164] One or more hydrogen atoms in the groups (a), (b), and (c) may be independently substituted by a halogen atom, a cyano group, or an alkyl group having 1 to 6 carbon atoms.

[0165] Item 7. The liquid crystal composition according to any one of items 1 to 6 further comprises one or more compounds represented by the following general formula (v).

[0166] [Chemistry 8]

[0167]

[0168] (in general formula (v),

[0169] R v1 Alkyl groups having 1 to 20 carbon atoms

[0170] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO-, and / or -CS-.

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

[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] A v1 and A v2 Represent the basis(a), basis(b), basis(c), and basis(d) chosen independently:

[0175] (a) 1,4-cyclohexylene (one or more non-adjacent -CH2- groups may be replaced by -O- and / or -S-)

[0176] (b) 1,4-Phenylidene (one or more -CH= groups may be substituted with -N=)

[0177] (c) Naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one or more -CH= in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl can be replaced by -N=)

[0178] (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 or more -CH= groups may be substituted with -N=)

[0179] The base of the group formed,

[0180] The A v1 and A v2 One or more hydrogen atoms can be independently replaced by substituents S. v1 replace,

[0181] Substituent S v1 It represents any one of a halogen atom, a cyano group, or an alkyl group having 1 to 6 carbon atoms.

[0182] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO-, and / or -CS-.

[0183] One or more hydrogen atoms present in the alkyl group can be independently substituted with halogen atoms.

[0184] However, oxygen atoms do not bond directly to each other.

[0185] In the substituent S v1 When multiple instances exist, these can be the same or different.

[0186] Z v1 It represents any one of the following: single bond, -C≡C-, -CH=CH-, -CF=CF-.

[0187] But Z v1 At least one of the following is represented as -C≡C-.

[0188] n v1 Represents integers from 1 to 2.

[0189] In A v1 and Z v1 If multiple instances exist, these instances can be the same or different.

[0190] Item 8. The liquid crystal composition according to any one of items 1 to 7, comprising one or more compounds represented by general formulas (np-1) to (np-3),

[0191] [Chemistry 9]

[0192]

[0193] (In the general formulas (np-1) to (np-3),

[0194] R npi and R npii Each of the alkyl or halogen atoms, having 1 to 20 carbon atoms, can be independently represented.

[0195] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO-, and / or -CS-.

[0196] One or more of the -CH2-CH2- groups 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-.

[0197] One or more of the -CH2-CH2-CH2- groups in the alkyl group can be independently substituted by -O-CO-O- groups.

[0198] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0199] However, oxygen atoms do not bond directly to each other.

[0200] Rings A, B, C, and D independently represent the following basis(a), basis(b), basis(c), and basis(d), respectively:

[0201] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups may be replaced with -O-)

[0202] (b) 1,4-Phenylidene (one or more -CH= groups may be substituted with -N=)

[0203] (c) Naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one or more -CH= in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl can be replaced by -N=)

[0204] (d) 1,4-cyclohexenyl, 1,3-dioxane-trans-2,5-diyl, pyrimidin-2,5-diyl, or pyridine-2,5-diyl

[0205] The base of the group formed,

[0206] One or more hydrogen atoms in rings A, B, C, and D can each be independently substituted by a substituent S. npi1 replace,

[0207] Substituent S npi1 It represents any one of a halogen atom, a cyano group, or an alkyl group having 1 to 20 carbon atoms.

[0208] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO-, and / or -CS-.

[0209] One or more of the -CH2-CH2- groups 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-.

[0210] One or more of the -CH2-CH2-CH2- groups in the alkyl group can be independently substituted by -O-CO-O- groups.

[0211] Furthermore, one or more hydrogen atoms in the alkyl group can be independently substituted with halogen atoms.

[0212] However, oxygen atoms do not bond directly to each other.

[0213] In the substituent S npi1 When multiple instances exist, these can be the same or different.

[0214] Z npi Z npii and Z npiii Each independently represents any one of a single bond or an alkylene group having 1 to 20 carbon atoms.

[0215] One or more of the -CH2- groups in the alkylene group may be independently substituted by -O- groups.

[0216] One or more of the -CH2-CH2- groups 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-.

[0217] One or more of the -CH2-CH2-CH2- groups in the alkylene group can be independently substituted by -O-CO-O-.

[0218] However, oxygen atoms do not bond directly to each other.

[0219] Item 9. The liquid crystal composition according to any one of items 1 to 8, wherein Δn at 25°C and 589nm is 0.38 or more.

[0220] Item 10. A liquid crystal display element using a liquid crystal composition according to any one of items 1 to 9.

[0221] Item 11. The liquid crystal display element according to Item 10 is driven in an active matrix manner or a passive matrix manner.

[0222] Item 12. A liquid crystal display element that reversibly switches the dielectric constant by reversibly changing the orientation of liquid crystal molecules in a liquid crystal composition according to any one of items 1 to 9.

[0223] Item 13. A sensor using a liquid crystal composition according to any one of items 1 to 9.

[0224] Item 14. A liquid crystal lens using a liquid crystal composition according to any one of items 1 to 9.

[0225] Item 15. An optical communication device using a liquid crystal composition according to any one of items 1 to 9.

[0226] Item 16. An antenna using a liquid crystal composition according to any one of items 1 to 9.

[0227] Item 17. The antenna according to Item 16, comprising:

[0228] The first substrate has multiple slots;

[0229] The second substrate, facing the first substrate, is provided with a power supply section;

[0230] A first dielectric layer is disposed between the first substrate and the second substrate;

[0231] Multiple patch electrodes are configured corresponding to the multiple slots;

[0232] A third substrate, having the aforementioned patch electrode; and

[0233] A liquid crystal layer is disposed between the first substrate and the third substrate, and

[0234] The liquid crystal layer contains a liquid crystal composition according to any one of items 1 to 9.

[0235] Item 18. A compound represented by the following general formula (i).

[0236] [Chemistry 10]

[0237]

[0238] (in general formula (i),

[0239] R i1 The alkynyl group represents the number of carbon atoms from 2 to 20.

[0240] One or more of the -CH2- groups in the alkynyl group may be independently replaced by -O-, -S-, -CO- and / or -CS-.

[0241] One or more of the -CH2-CH2- groups in the alkynyl group can be independently replaced by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0242] One or more of the -CH2-CH2-CH2- groups in the alkynyl group can be independently replaced by -O-CO-O-.

[0243] One or more hydrogen atoms in the alkynyl group can be independently substituted by halogen atoms.

[0244] However, oxygen atoms do not bond directly to each other.

[0245] Ai1 A i2 and A i3 Each can be independently represented as either a hydrocarbon ring with 3 to 16 carbon atoms or a heterocycle with 3 to 16 carbon atoms.

[0246] The A i1 A i2 and A i3 One or more hydrogen atoms can be independently replaced by substituents S. i1 replace,

[0247] Substituent S i1 It represents any one of the following: fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluoromercapto, nitro, cyano, isocyano, amino, hydroxyl, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyano, or alkyl group having 1 to 20 carbon atoms.

[0248] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, and / or -CO-.

[0249] One or more of the -CH2-CH2- groups 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-.

[0250] One or more of the -CH2-CH2-CH2- groups in the alkyl group can be independently substituted by -O-CO-O- groups.

[0251] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0252] However, oxygen atoms do not bond directly to each other.

[0253] In the substituent S i1 When multiple instances exist, these can be the same or different.

[0254] Z i1 and Z i2 Each independently represents any one of a single bond or an alkylene group having 1 to 20 carbon atoms.

[0255] One or more of the -CH2- groups in the alkylene group may be independently replaced by -O-, -CF2- and / or -CO-.

[0256] One or more of the -CH2-CH2- groups 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-.

[0257] However, oxygen atoms do not bond directly to each other.

[0258] n i1 (representing integers from 0 to 1)

[0259] The effects of the invention

[0260] According to the present invention, T can be obtained by comprising one or more liquid crystal compositions containing compounds of general formula (i) having alkynyl and isothiocyanate groups (-NCS). ni High, large Δn, V th Low, Δε r Large, tanδ iso Liquid crystal compositions with good preservation at low temperatures are useful for liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas. Detailed Implementation

[0261] (The compound represented by general formula (i))

[0262] The compounds of the present invention are compounds having an alkynyl group and an isothiocyanate group (-NCS) represented by the following general formula (i).

[0263] In addition, the liquid crystal composition of the present invention comprises one or more compounds represented by general formula (i) having an alkynyl group and an isothiocyanate group (-NCS).

[0264] [Chemistry 11]

[0265]

[0266] In general formula (i), R i1 The alkynyl group represents 2 to 20 carbon atoms.

[0267] The alkynyl group with 2 to 20 carbon atoms is a straight-chain, branched, or cyclic alkynyl group, preferably a straight-chain alkynyl group.

[0268] The number of carbon atoms in the alkynyl group with 2 to 20 carbon atoms is preferably 2 to 15, and more preferably 3 to 10.

[0269] One or more of the -CH2- groups in the alkynyl group may be independently replaced by -O-, -S-, -CO- and / or -CS-.

[0270] In addition, one or more of the -CH2-CH2- groups in the alkynyl group can be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0271] In addition, one or more of the -CH2-CH2-CH2- groups in the alkynyl group can be independently substituted by -O-CO-O-.

[0272] In addition, one or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0273] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[0274] Wherein, when the alkyl group is substituted by a specified group, oxygen atoms do not bond directly to oxygen atoms.

[0275] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[0276] As an alkynyl group, from the viewpoint of ease of synthesis or elongation of the conjugated system, the following formula (R) is preferred. i1 -A) represents the alkynyl group.

[0277] [Chemistry 12]

[0278]

[0279] Formula (R) i1 In -A), R i1A Alkyl groups having 1 to 18 carbon atoms.

[0280] The alkyl group having 1 to 18 carbon atoms is a straight-chain, branched, or cyclic alkyl group, preferably a straight-chain alkyl group.

[0281] The alkyl group having 1 to 18 carbon atoms preferably has 1 to 8 carbon atoms.

[0282] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0283] In addition, one or more of the -CH2-CH2- groups 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-.

[0284] In addition, one or more of the -CH2-CH2-CH2- alkyl groups can be independently substituted by -O-CO-O-.

[0285] In addition, one or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0286] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[0287] Wherein, when the alkyl group is substituted by a specified group, oxygen atoms do not bond directly to oxygen atoms.

[0288] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[0289] In addition, formula (R) i1 In -A), the black dot represents the direction to A. i1 The bond structure.

[0290] As R i1 Specific examples of alkynyl groups (including substituted alkynyl groups) with 2 to 20 carbon atoms can be listed in formula (R). i1 -1)~Formula (R) i1 -16) represents the base level.

[0291] [Chemistry 13]

[0292]

[0293] Formula (R) i1 -1)~Formula (R) i1 In -16), the black dot represents the direction to A. i1 The bond structure.

[0294] In addition, as R i1 From the viewpoint of Δn or solubility, a straight-chain alkynyl group with 2 to 8 carbon atoms is preferred.

[0295] In general formula (i), A i1 A i2 and A i3 Each can be independently represented as either a hydrocarbon ring with 3 to 16 carbon atoms or a heterocycle with 3 to 16 carbon atoms.

[0296] Hydrocarbon rings having 3 to 16 carbon atoms or heterocycles having 3 to 16 carbon atoms, more specifically preferably represented by groups (a), (b), (c), and (d) selected from the following:

[0297] (a) 1,4-cyclohexylene (one or more non-adjacent -CH2- groups may be replaced by -O- and / or -S-)

[0298] (b) 1,4-Phenylidene (one or more -CH= groups may be substituted with -N=)

[0299] (c) 1,4-cyclohexenyl, bicyclo[2.2.2]octane-1,4-diyl, naphth-2,6-diyl, naphth-1,4-diyl, 1,2,3,4-tetrahydronaphth-2,6-diyl, 5,6,7,8-tetrahydronaphth-1,4-diyl, decahydronaphth-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene -2,7-Diyl (one 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 can be substituted with -N=)

[0300] (d) Thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thiopheno[3,2-b]thiophene-2,5-diyl, benzo[1,2-b:4,5-b']dithiophene-2,6-diyl (one -CH= or two or more non-adjacent -CH= groups may be substituted with -N=)

[0301] The base in the group formed by the group.

[0302] A i1 A i2 and A i3 One or more hydrogen atoms can be independently replaced by substituents S. i1 replace.

[0303] Substituent S i1 It represents any one of the following: fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorothiol, nitro, cyano, isocyano, amino, hydroxyl, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyano, or alkyl with 1 to 20 carbon atoms.

[0304] The alkyl group is a straight-chain, branched, or cyclic alkyl group, preferably a straight-chain alkyl group.

[0305] The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 6.

[0306] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S- and / or -CO-.

[0307] In addition, one or more of the -CH2-CH2- groups 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-.

[0308] In addition, one or more of the -CH2-CH2-CH2- alkyl groups may be replaced by -O-CO-O-.

[0309] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0310] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[0311] Wherein, when the alkyl group is substituted by a specified group, oxygen atoms do not bond directly to oxygen atoms.

[0312] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[0313] As a substituent S i1 Preferably, it is a straight-chain alkyl group with halogen atoms or 1 to 6 carbon atoms, and preferably a straight-chain alkyl group with fluorine atoms or 1 to 3 carbon atoms.

[0314] In addition, A i2 and A i3 At least one of them is preferably composed of at least one substituent S i1 The substitution is preferably made by halogen atoms, and more preferably by fluorine atoms.

[0315] Furthermore, in the substituent S i1 When multiple instances exist, these can be the same or different.

[0316] As A i1 The substituent S in i1 The replacement position is preferably that of the following formula (A) i1 -SP-1)~Form (A) i1 Any of the following (-SP-4).

[0317] [Chemistry 14]

[0318]

[0319] Formula (A) i1 -SP-1)~Form (A) i1 In -SP-4), the white dot indicates the direction to R. i1 The bond is represented by black dots indicating the Z-axis. i1 The bond structure.

[0320] As A i2 The substituent S in i1 The replacement position is preferably that of the following formula (A) i2 -SP-1)~Form (A) i2 Any of the following (-SP-3).

[0321] [Chemistry 15]

[0322]

[0323] Formula (A) i2 -SP-1)~Form (A) i2 In -SP-3), the white dot indicates the direction of Z. i1 The bond is represented by black dots indicating the Z-axis. i2 Or isothiocyanate group (-NCS) bond.

[0324] As A i3 The substituent S in i1 The replacement position is preferably that of the following formula (A) i3 -SP-1)~Form (A) i3 Any of the following (-SP-2).

[0325] [Chemistry 16]

[0326]

[0327] Formula (A) i3 -SP-1)~Form (A) i3 In -SP-2), the white dot indicates the direction of Z. i2 The black dots represent the bonds to the isothiocyanate group (-NCS).

[0328] More specifically, A i1 Preferably, it represents the following formula (A) i1 -1)~Form (A) i1 Any one of -15).

[0329] [Chemistry 17]

[0330]

[0331] Formula (A) i1 -1)~Form (A) i1 In -15), the white dot represents the direction to R. i1 The bond is represented by black dots indicating the Z-axis. i1 The bond structure.

[0332] Regarding solubility, Δn and / or Δε r From A's point of view, i1 Particularly preferred is the expression (A) i1 -2), Equation (A) i1 -3), Equation (A) i1 -6) or formula (A) i1 -8).

[0333] More specifically, A i2 Preferably, it represents the following formula (A) i2 -1)~Form (A) i2 Any one of -15).

[0334] [Chemistry 18]

[0335]

[0336] Formula (A) i2 -1)~Form (A) i2 In -15), the white dot represents the direction of Z. i1 The bond is represented by black dots indicating the Z-axis. i2 Or isothiocyanate group (-NCS) bond.

[0337] Regarding Δn and / or Δε r From A's point of view, i2 Furthermore, it is preferable to represent the formula (A) i2 -1), Equation (A) i2 -2), Equation (A) i2 -6) or formula (A) i2 -13), particularly preferred is the expression (A) i2 -1), Equation (A) i2 -13).

[0338] More specifically, A i3 Preferably, it represents the following formula (A) i3 -1)~Form (A) i3 Any of the following: -5)

[0339] [Chemistry 19]

[0340]

[0341] Formula (A) i3 -1)~Form (A) i3 In -5), the white dot represents the direction of Z.i2 The black dots represent the bonds to the isothiocyanate group (-NCS).

[0342] Regarding Δn and / or Δε r From A's point of view, i3 Furthermore, it is preferable to represent the formula (A) i3 -1), Equation (A) i3 -2) or formula (A) i3 -4), particularly preferred is the expression (A) i3 -4).

[0343] In general formula (i), Z i1 and Z i2 Each of the following can be independently represented: a single bond, or an alkylene group having 1 to 20 carbon atoms.

[0344] The alkylene group is a straight-chain, branched, or cyclic alkylene group, preferably a straight-chain alkylene group.

[0345] The alkylene group preferably has 2 to 10 carbon atoms, more preferably 2 to 6.

[0346] One or more of the -CH2- groups in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[0347] In addition, one or more of the -CH2-CH2- groups 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-.

[0348] Wherein, when the alkylene group is substituted by a specified group, oxygen atoms do not bond directly to oxygen atoms.

[0349] Specific examples of alkylene groups having 2 to 20 carbon atoms (including substituted alkylene groups) can be enumerated as (Z i1 / 2 -1)~Formula (Z) i1 / 2 -24) represents the base.

[0350] [Chemistry 20]

[0351]

[0352] Formula (Z) i1 / 2 -1)~Formula (Z) i1 / 2 In -24), the white dot represents the direction to A. i1 Or A i2The bond, the black dot indicates the bond to A i2 Or A i3 The bond structure.

[0353] Regarding Δn and / or Δε r From Z's point of view, i1 and Z i2 Each is preferably a single bond or -C≡C-, independently and preferably.

[0354] Additionally, regarding Δn and / or Δε r From Z's point of view, i1 and Z i2 At least one of them is preferably -C≡C-.

[0355] In general formula (i), n i1 Represents integers from 0 to 1.

[0356] The compounds represented by general formula (i) are preferably those represented by general formulas (i-1) to (i-5) below.

[0357] [Chemistry 21]

[0358]

[0359] In general formulas (i-1) to (i-5), R i1 A i1 A i2 and A i3 R represents the expression in the general formula (i). i1 A i1 A i2 and A i3 The terms have the same meaning, and the preferred basis also represents the same basis.

[0360] The compounds represented by general formula (i-1) are preferably those represented by general formulas (i-1-1) to (i-1-7).

[0361] [Chemistry 22]

[0362]

[0363] In general formulas (i-1-1) to (i-1-7), R i1 and S i1 Represent R independently of the general formula (i). i1 and S i1 Same meaning.

[0364] Specific examples of compounds represented by the general formula (i-1-1) include compounds represented by the following structural formulas (i-1-1.1) to (i-1-1.4).

[0365] [Chemistry 23]

[0366]

[0367] Specific examples of compounds represented by general formula (i-1-2) include compounds represented by structural formulas (i-1-2.1) to (i-1-2.5).

[0368] [Chemistry 24]

[0369]

[0370] Specific examples of compounds represented by general formula (i-1-3) include compounds represented by structural formulas (i-1-3.1) to (i-1-3.4).

[0371] [Chemistry 25]

[0372]

[0373] Specific examples of compounds represented by general formula (i-1-4) include compounds represented by structural formulas (i-1-4.1) to (i-1-4.4).

[0374] [Chemistry 26]

[0375]

[0376] Specific examples of compounds represented by general formula (i-1-5) include compounds represented by structural formulas (i-1-5.1) to (i-1-5.4).

[0377] [Chemistry 27]

[0378]

[0379] Specific examples of compounds represented by general formula (i-1-6) include compounds represented by structural formulas (i-1-6.1) to (i-1-6.4).

[0380] [Chemistry 28]

[0381]

[0382] As specific examples of compounds represented by general formula (i-1-7), compounds represented by the following structural formulas (i-1-7.1) to (i-1-7.4) can be listed.

[0383] [Chemistry 29]

[0384]

[0385] The compounds represented by general formula (i-2) are preferably those represented by general formulas (i-2-1) to (i-2-15).

[0386] [Chemistry 30]

[0387]

[0388] [Chemistry 31]

[0389]

[0390] [Chemistry 32]

[0391]

[0392] In general formulas (i-2-1) to (i-2-15), R i1 and S i1 Represent R independently of the general formula (i). i1 and S i1 Same meaning.

[0393] Specific examples of compounds represented by the general formula (i-2-1) include compounds represented by the following structural formulas (i-2-1.1) to (i-2-1.4).

[0394] [Chemistry 33]

[0395]

[0396] Specific examples of compounds represented by general formula (i-2-2) include compounds represented by structural formulas (i-2-2.1) to (i-2-2.5).

[0397] [Chemistry 34]

[0398]

[0399] Specific examples of compounds represented by general formula (i-2-3) include compounds represented by structural formulas (i-2-3.1) to (i-2-3.4).

[0400] [Chemistry 35]

[0401]

[0402] Specific examples of compounds represented by general formula (i-2-4) include compounds represented by structural formulas (i-2-4.1) to (i-2-4.9).

[0403] [Chemistry 36]

[0404]

[0405] Specific examples of compounds represented by general formula (i-2-5) include compounds represented by structural formulas (i-2-5.1) to (i-2-5.6).

[0406] [Chemistry 37]

[0407]

[0408] Specific examples of compounds represented by general formula (i-2-6) include compounds represented by structural formulas (i-2-6.1) to (i-2-6.6).

[0409] [Chemistry 38]

[0410]

[0411] Specific examples of compounds represented by general formula (i-2-7) include compounds represented by structural formulas (i-2-7.1) to (i-2-7.3).

[0412] [Chemistry 39]

[0413]

[0414] Specific examples of compounds represented by general formula (i-2-8) include compounds represented by structural formulas (i-2-8.1) to (i-2-8.4).

[0415] [Chemistry 40]

[0416]

[0417] Specific examples of compounds represented by general formula (i-2-9) include compounds represented by structural formulas (i-2-9.1) to (i-2-9.4).

[0418] [Chemistry 41]

[0419]

[0420] Specific examples of compounds represented by the general formula (i-2-10) include compounds represented by the following structural formulas (i-2-10.1) to (i-2-10.4).

[0421] [Chemistry 42]

[0422]

[0423] Specific examples of compounds represented by the general formula (i-2-11) include compounds represented by the following structural formulas (i-2-11.1) to (i-2-11.5).

[0424] [Chemistry 43]

[0425]

[0426] Specific examples of compounds represented by the general formula (i-2-12) include compounds represented by the following structural formulas (i-2-12.1) to (i-2-12.4).

[0427] [Chemistry 44]

[0428]

[0429] Specific examples of compounds represented by general formula (i-2-13) include compounds represented by structural formulas (i-2-13.1) to (i-2-13.5).

[0430] [Chemistry 45]

[0431]

[0432] Specific examples of compounds represented by general formula (i-2-14) include compounds represented by structural formulas (i-2-14.1) to (i-2-14.4).

[0433] [Chemistry 46]

[0434]

[0435] Specific examples of compounds represented by general formula (i-2-15) include compounds represented by structural formulas (i-2-15.1) to (i-2-15.6).

[0436] [Chemistry 47]

[0437]

[0438] The compounds represented by general formula (i-3) are preferably those represented by general formulas (i-3-1) to (i-3-11).

[0439] [Chemistry 48]

[0440]

[0441] [Chemistry 49]

[0442]

[0443] In general formulas (i-3-1) to (i-3-11), R i1 and S i1 Represent R independently of the general formula (i). i1 and S i1 Same meaning.

[0444] As specific examples of compounds represented by the general formula (i-3-1), compounds represented by the following structural formulas (i-3-1.1) to (i-3-1.4) can be listed.

[0445] [Transformation 50]

[0446]

[0447] Specific examples of compounds represented by general formula (i-3-2) include compounds represented by structural formulas (i-3-2.1) to (i-3-2.4).

[0448] [Chemistry 51]

[0449]

[0450] Specific examples of compounds represented by the general formula (i-3-3) include compounds represented by the following structural formulas (i-3-3.1) to (i-3-3.6).

[0451] [Chemistry 52]

[0452]

[0453] Specific examples of compounds represented by general formula (i-3-4) include compounds represented by structural formulas (i-3-4.1) to (i-3-4.7).

[0454] [Chemistry 53]

[0455]

[0456] Specific examples of compounds represented by general formula (i-3-5) include compounds represented by structural formulas (i-3-5.1) to (i-3-5.5).

[0457] [Chemistry 54]

[0458]

[0459] Specific examples of compounds represented by general formula (i-3-6) include compounds represented by structural formulas (i-3-6.1) to (i-3-6.5).

[0460] [Chemistry 55]

[0461]

[0462] Specific examples of compounds represented by general formula (i-3-7) include compounds represented by structural formulas (i-3-7.1) to (i-3-7.4).

[0463] [Chemistry 56]

[0464]

[0465] Specific examples of compounds represented by the general formula (i-3-8) include compounds represented by the following structural formulas (i-3-8.1) to (i-3-8.3).

[0466] [Chemistry 57]

[0467]

[0468] Specific examples of compounds represented by general formula (i-3-9) include compounds represented by structural formulas (i-3-9.1) to (i-3-9.3).

[0469] [Chem.58]

[0470]

[0471] Specific examples of compounds represented by the general formula (i-3-10) include compounds represented by the following structural formulas (i-3-10.1) to (i-3-10.3).

[0472] [Chemistry 59]

[0473]

[0474] Specific examples of compounds represented by the general formula (i-3-11) include compounds represented by the following structural formulas (i-3-11.1) to (i-3-11.6).

[0475] [Transformation 60]

[0476]

[0477] The compounds represented by general formula (i-4) are preferably those represented by general formulas (i-4-1) to (i-4-10).

[0478] [Chemistry 61]

[0479]

[0480] Specific examples of compounds represented by general formula (i-4-1) include compounds represented by structural formulas (i-4-1.1) to (i-4-1.4).

[0481] [Chemistry 62]

[0482]

[0483] Specific examples of compounds represented by general formula (i-4-2) include compounds represented by structural formulas (i-4-2.1) to (i-4-2.5).

[0484] [Chemistry 63]

[0485]

[0486] Specific examples of compounds represented by general formula (i-4-3) include compounds represented by structural formulas (i-4-3.1) to (i-4-3.5).

[0487] [Chemistry 64]

[0488]

[0489] Specific examples of compounds represented by the general formula (i-4-4) include compounds represented by the following structural formulas (i-4-4.1) to (i-4-4.4).

[0490] [Chemistry 65]

[0491]

[0492] Specific examples of compounds represented by general formula (i-4-5) include compounds represented by structural formulas (i-4-5.1) to (i-4-5.4).

[0493] [Chemistry 66]

[0494]

[0495] Specific examples of compounds represented by general formula (i-4-6) include compounds represented by structural formulas (i-4-6.1) to (i-4-6.6).

[0496] [Chemistry 67]

[0497]

[0498] Specific examples of compounds represented by general formula (i-4-7) include compounds represented by structural formulas (i-4-7.1) to (i-4-7.4).

[0499] [Chemistry 68]

[0500]

[0501] Specific examples of compounds represented by general formula (i-4-8) include compounds represented by structural formulas (i-4-8.1) to (i-4-8.5).

[0502] [Chemistry 69]

[0503]

[0504] Specific examples of compounds represented by general formula (i-4-9) include compounds represented by structural formulas (i-4-9.1) to (i-4-9.4).

[0505] [Chemistry 70]

[0506]

[0507] Specific examples of compounds represented by the general formula (i-4-10) include compounds represented by the following structural formulas (i-4-10.1) to (i-4-10.4).

[0508] [Chemistry 71]

[0509]

[0510] The compounds represented by general formula (i-5) are preferably those represented by general formulas (i-5-1) to (i-5-6).

[0511] [Chemistry 72]

[0512]

[0513] In general formulas (i-5-1) to (i-5-6), R i1 and S i1 Represent R independently of the general formula (i). i1 and S i1 Same meaning.

[0514] Specific examples of compounds represented by general formula (i-5-1) include compounds represented by structural formulas (i-5-1.1) to (i-5-1.4).

[0515] [Chemistry 73]

[0516]

[0517] Specific examples of compounds represented by general formula (i-5-2) include compounds represented by structural formulas (i-5-2.1) to (i-5-2.4).

[0518] [Chemistry 74]

[0519]

[0520] Specific examples of compounds represented by general formula (i-5-3) include compounds represented by structural formulas (i-5-3.1) to (i-5-3.4).

[0521] [Chemistry 75]

[0522]

[0523] Specific examples of compounds represented by general formula (i-5-4) include compounds represented by structural formulas (i-5-4.1) to (i-5-4.4).

[0524] [Chemistry 76]

[0525]

[0526] Specific examples of compounds represented by general formula (i-5-5) include compounds represented by structural formulas (i-5-5.1) to (i-5-5.4).

[0527] [Chemistry 77]

[0528]

[0529] Specific examples of compounds represented by general formula (i-5-6) include compounds represented by structural formulas (i-5-6.1) to (i-5-6.4).

[0530] [Chemistry 78]

[0531]

[0532] General formula (i), general formula (i-1) to general formula (i-5), general formula (i-1-1) to general formula (i-1-7), general formula (i-2-1) to general formula (i-2-15), general formula (i-3-1) to general formula (i-3-11), general formula (i-4-1) to general formula (i-4-10), general formula (i-5-1) to general formula (i-5-6), structural formula (i-1-1.1) to structural formula (i-1-1.4), structural formula (i-1-2.1) to structural formula (i-1-2.5), structural formula (i-1-3.1) to structural formula (i-1-3.4), structural formula (i-1-4.1) to structural formula (i-1-4.4), structural formula (i-1-5.1) to structural formula (i-1 -5.4), structure (i-1-6.1) ~ structure (i-1-6.4), structure (i-1-7.1) ~ structure (i-1-7.4), structure (i-2-1.1) ~ structure (i-2-1.4), structure (i-2-2.1) ~ structure (i-2-2.5), structure (i-2-3.1) ~ structure (i-2-3.4), structure (i-2-4.1) ~ structure (i-2-4.9), structure (i-2-5.1) ~ structure (i-2-5.6), structure (i-2-6.1) ~ structure (i-2-6.6), structure (i-2-7.1) ~ structure (i-2-7.3), structure (i-2-8) .1) ~ Structure (i-2-8.4), Structure (i-2-9.1) ~ Structure (i-2-9.4), Structure (i-2-10.1) ~ Structure (i-2-10.4), Structure (i-2-11.1) ~ Structure (i-2-11.5), Structure (i-2-12.1) ~ Structure (i-2-12.4), Structure (i-2-13.1) ~ Structure (i-2-13.5), Structure (i-2-14.1) ~ Structure (i-2-14.4), Structure (i-2-15.1) ~ Structure (i-2-15.6), Structure (i-3-1.1) ~ Structure (i-3-1.4), Structure (i-3-2.1) ~Structure (i-3-2.4), Structure (i-3-3.1) ~Structure (i-3-3.6), Structure (i-3-4.1) ~Structure (i-3-4.7), Structure (i-3-5.1) ~Structure (i-3-5.5), Structure (i-3-6.1) ~Structure (i-3-6.5), Structure (i-3-7.1) ~Structure (i-3-7.4), Structure (i-3-8.1) ~Structure (i-3-8.3), Structure (i-3-9.1) ~Structure (i-3-9.3), Structure (i-3-10.1) ~Structure (i-3-10.3), Structure (i-3-11.1) ~Structure (i-3-11).6) Structures (i-4-1.1) to (i-4-1.4), (i-4-2.1) to (i-4-2.5), (i-4-3.1) to (i-4-3.5), (i-4-4.1) to (i-4-4.4), (i-4-5.1) to (i-4-5.4), (i-4-6.1) to (i-4-6.6), (i-4-7.1) to (i-4-7.4), (i-4-8.1) to (i-4-8.5), (i-4-9.1) to (i-4-9.4). The compounds represented by structural formulas (i-4-10.1) to (i-4-10.4), (i-5-1.1) to (i-5-1.4), (i-5-2.1) to (i-5-2.4), (i-5-3.1) to (i-5-3.4), (i-5-4.1) to (i-5-4.4), (i-5-5.1) to (i-5-5.4), or (i-5-6.1) to (i-5-6.4) are used in the liquid crystal composition in one or more forms, preferably one to ten, preferably one to five, and preferably one to three.

[0533] General formula (i), general formula (i-1) to general formula (i-5), general formula (i-1-1) to general formula (i-1-7), general formula (i-2-1) to general formula (i-2-15), general formula (i-3-1) to general formula (i-3-11), general formula (i-4-1) to general formula (i-4-10), general formula (i-5-1) to general formula (i-5-6), structural formula (i-1-1.1) to structural formula (i-1-1.4), structural formula (i-1-2.1) to structural formula (i-1-2.5), structural formula (i-1-3.1) to structural formula (i-1-3.4), structural formula (i-1-4.1) to structural formula (i-1-4.4), structural formula (i-1-5.1) to structural formula (i-1 -5.4), structure (i-1-6.1) ~ structure (i-1-6.4), structure (i-1-7.1) ~ structure (i-1-7.4), structure (i-2-1.1) ~ structure (i-2-1.4), structure (i-2-2.1) ~ structure (i-2-2.5), structure (i-2-3.1) ~ structure (i-2-3.4), structure (i-2-4.1) ~ structure (i-2-4.9), structure (i-2-5.1) ~ structure (i-2-5.6), structure (i-2-6.1) ~ structure (i-2-6.6), structure (i-2-7.1) ~ structure (i-2-7.3), structure (i-2-8) .1) ~ Structure (i-2-8.4), Structure (i-2-9.1) ~ Structure (i-2-9.4), Structure (i-2-10.1) ~ Structure (i-2-10.4), Structure (i-2-11.1) ~ Structure (i-2-11.5), Structure (i-2-12.1) ~ Structure (i-2-12.4), Structure (i-2-13.1) ~ Structure (i-2-13.5), Structure (i-2-14.1) ~ Structure (i-2-14.4), Structure (i-2-15.1) ~ Structure (i-2-15.6), Structure (i-3-1.1) ~ Structure (i-3-1.4), Structure (i-3-2.1) ~Structure (i-3-2.4), Structure (i-3-3.1) ~Structure (i-3-3.6), Structure (i-3-4.1) ~Structure (i-3-4.7), Structure (i-3-5.1) ~Structure (i-3-5.5), Structure (i-3-6.1) ~Structure (i-3-6.5), Structure (i-3-7.1) ~Structure (i-3-7.4), Structure (i-3-8.1) ~Structure (i-3-8.3), Structure (i-3-9.1) ~Structure (i-3-9.3), Structure (i-3-10.1) ~Structure (i-3-10.3), Structure (i-3-11.1) ~Structure (i-3-11).6) Structure (i-4-1.1)~structure (i-4-1.4), structure (i-4-2.1)~structure (i-4-2.5), structure (i-4-3.1)~structure (i-4-3.5), structure (i-4-4.1)~structure (i-4-4.4), structure (i-4-5.1)~structure (i-4-5.4), structure (i-4-6.1)~structure (i-4-6.6), structure (i-4-7.1)~structure (i-4-7.4), structure (i-4-8.1)~structure (i-4-8.5), structure (i-4-9.1)~structure (i-4-9.4), structure (i-4-10.1)~structure (i-4-10.4), structure The lower limit of the total content of the compounds represented by formulas (i-5-1.1) to (i-5-1.4), (i-5-2.1) to (i-5-2.4), (i-5-3.1) to (i-5-3.4), (i-5-4.1) to (i-5-4.4), (i-5-5.1) to (i-5-5.4), or (i-5-6.1) to (i-5-6.4) in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, preferably 3% by mass or more, preferably 5% by mass or more, preferably 10% by mass or more, preferably 15% by mass or more, preferably 20% by mass or more, preferably 25% by mass or more, and preferably 30% by mass or more.

[0534] General formula (i), general formula (i-1) to general formula (i-5), general formula (i-1-1) to general formula (i-1-7), general formula (i-2-1) to general formula (i-2-15), general formula (i-3-1) to general formula (i-3-11), general formula (i-4-1) to general formula (i-4-10), general formula (i-5-1) to general formula (i-5-6), structural formula (i-1-1.1) to structural formula (i-1-1.4), structural formula (i-1-2.1) to structural formula (i-1-2.5), structural formula (i-1-3.1) to structural formula (i-1-3.4), structural formula (i-1-4.1) to structural formula (i-1-4.4), structural formula (i-1-5.1) to structural formula (i-1 -5.4), structure (i-1-6.1) ~ structure (i-1-6.4), structure (i-1-7.1) ~ structure (i-1-7.4), structure (i-2-1.1) ~ structure (i-2-1.4), structure (i-2-2.1) ~ structure (i-2-2.5), structure (i-2-3.1) ~ structure (i-2-3.4), structure (i-2-4.1) ~ structure (i-2-4.9), structure (i-2-5.1) ~ structure (i-2-5.6), structure (i-2-6.1) ~ structure (i-2-6.6), structure (i-2-7.1) ~ structure (i-2-7.3), structure (i-2-8) .1) ~ Structure (i-2-8.4), Structure (i-2-9.1) ~ Structure (i-2-9.4), Structure (i-2-10.1) ~ Structure (i-2-10.4), Structure (i-2-11.1) ~ Structure (i-2-11.5), Structure (i-2-12.1) ~ Structure (i-2-12.4), Structure (i-2-13.1) ~ Structure (i-2-13.5), Structure (i-2-14.1) ~ Structure (i-2-14.4), Structure (i-2-15.1) ~ Structure (i-2-15.6), Structure (i-3-1.1) ~ Structure (i-3-1.4), Structure (i-3-2.1) ~Structure (i-3-2.4), Structure (i-3-3.1) ~Structure (i-3-3.6), Structure (i-3-4.1) ~Structure (i-3-4.7), Structure (i-3-5.1) ~Structure (i-3-5.5), Structure (i-3-6.1) ~Structure (i-3-6.5), Structure (i-3-7.1) ~Structure (i-3-7.4), Structure (i-3-8.1) ~Structure (i-3-8.3), Structure (i-3-9.1) ~Structure (i-3-9.3), Structure (i-3-10.1) ~Structure (i-3-10.3), Structure (i-3-11.1) ~Structure (i-3-11).6) Structure (i-4-1.1)~structure (i-4-1.4), structure (i-4-2.1)~structure (i-4-2.5), structure (i-4-3.1)~structure (i-4-3.5), structure (i-4-4.1)~structure (i-4-4.4), structure (i-4-5.1)~structure (i-4-5.4), structure (i-4-6.1)~structure (i-4-6.6), structure (i-4-7.1)~structure (i-4-7.4), structure (i-4-8.1)~structure (i-4-8.5), structure (i-4-9.1)~structure (i-4-9.4), structure (i-4-10.1)~structure (i-4-10.4), structure The upper limit of the total content of the compounds represented by (i-5-1.1) to (i-5-1.4), (i-5-2.1) to (i-5-2.4), (i-5-3.1) to (i-5-3.4), (i-5-4.1) to (i-5-4.4), (i-5-5.1) to (i-5-5.4), or (i-5-6.1) to (i-5-6.4) in 100% by mass of the liquid crystal composition is preferably 75% by mass or less, preferably 65% ​​by mass or less, preferably 55% by mass or less, preferably 45% 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.

[0535] Regarding solubility, Δn and / or Δε rFrom the perspective of [the relevant context], the general formulas (i), (i-1) to (i-5), (i-1-1) to (i-1-7), (i-2-1) to (i-2-15), (i-3-1) to (i-3-11), (i-4-1) to (i-4-10), (i-5-1) to (i-5-6), structural formulas (i-1-1.1) to (i-1-1.4), (i-1-2.1) to (i-1-2.5), (i-1-3.1) to (i-1-3.4), (i-1-4.1) to (i-1-4.4), and (i-1-5.1) are [related to the above]. ~Structure (i-1-5.4), Structure (i-1-6.1) ~Structure (i-1-6.4), Structure (i-1-7.1) ~Structure (i-1-7.4), Structure (i-2-1.1) ~Structure (i-2-1.4), Structure (i-2-2.1) ~Structure (i-2-2.5), Structure (i-2-3.1) ~Structure (i-2-3.4), Structure (i-2-4.1) ~Structure (i-2-4.9), Structure (i-2-5.1) ~Structure (i-2-5.6), Structure (i-2-6.1) ~Structure (i-2-6.6), Structure (i-2-7.1) ~Structure (i-2-7.3) The following structures are used: (i-2-8.1) to (i-2-8.4), (i-2-9.1) to (i-2-9.4), (i-2-10.1) to (i-2-10.4), (i-2-11.1) to (i-2-11.5), (i-2-12.1) to (i-2-12.4), (i-2-13.1) to (i-2-13.5), (i-2-14.1) to (i-2-14.4), (i-2-15.1) to (i-2-15.6), and (i-3-1.1) to (i-3-1.4). Structure (i-3-2.1)~structure (i-3-2.4), structure (i-3-3.1)~structure (i-3-3.6), structure (i-3-4.1)~structure (i-3-4.7), structure (i-3-5.1)~structure (i-3-5.5), structure (i-3-6.1)~structure (i-3-6.5), structure (i-3-7.1)~structure (i-3-7.4), structure (i-3-8.1)~structure (i-3-8.3), structure (i-3-9.1)~structure (i-3-9.3), structure (i-3-10.1)~structure (i-3-10.3), structure (i-3-11).1) ~ Structure (i-3-11.6), Structure (i-4-1.1) ~ Structure (i-4-1.4), Structure (i-4-2.1) ~ Structure (i-4-2.5), Structure (i-4-3.1) ~ Structure (i-4-3.5), Structure (i-4-4.1) ~ Structure (i-4-4.4), Structure (i-4-5.1) ~ Structure (i-4-5.4), Structure (i-4-6.1) ~ Structure (i-4-6.6), Structure (i-4-7.1) ~ Structure (i-4-7.4), Structure (i-4-8.1) ~ Structure (i-4-8.5), Structure (i-4-9.1) ~ Structure (i-4-9.4), Structure (i-4-10.1) ~ Structure (i- The total content of the compounds represented by structural formulas (i-5-1.1) to (i-5-1.4), (i-5-2.1) to (i-5-2.4), (i-5-3.1) to (i-5-3.4), (i-5-4.1) to (i-5-4.4), (i-5-5.1) to (i-5-5.4), or (i-5-6.1) to (i-5-6.4) in 100% by mass of the liquid crystal composition is preferably 1% to 75% by mass, preferably 3% to 65% by mass, preferably 5% to 55% by mass, preferably 5% to 45% by mass, preferably 5% to 35% by mass, and preferably 5% to 25% by mass.

[0536] Compounds represented by general formula (i) (including sub-concepts) can be synthesized using well-known synthetic methods, several of which are exemplified below.

[0537] (Preparation Method 1) Preparation of the compound represented by the following formula (s-5)

[0538] [Chemistry 79]

[0539]

[0540] (where R is in the formula) i1A and S i1 R represents the expression in the general formula (i). i1A and S i1 (same meaning)

[0541] The compound represented by general formula (s-1) can be reacted with the compound represented by general formula (s-2) to obtain the compound represented by general formula (s-3).

[0542] Examples of reaction methods include the coupling reaction of scallions using palladium catalysts, copper catalysts, and bases.

[0543] Specific examples of palladium catalysts include: [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), tetra(triphenylphosphine)palladium(O), etc.

[0544] When using palladium(II) acetate as a palladium catalyst, ligands such as triphenylphosphine and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl can be added.

[0545] A specific example of a copper catalyst is copper iodide (I).

[0546] Specific examples of alkalis include triethylamine.

[0547] The compound represented by general formula (s-3) can be obtained by reacting the compound represented by general formula (s-4).

[0548] As a reaction method, for example, the method of Suzuki coupling in the presence of a metal catalyst and a base can be cited.

[0549] The above examples can be cited as specific examples of metal catalysts.

[0550] Specific examples of alkalis include potassium carbonate, potassium phosphate, and cesium carbonate.

[0551] Finally, the target compound (s-6) can be obtained by reacting the amino group with 1,1-thiocarbonyldiimidazole, 1,1-thiocarbonyldi-2(1H)-pyridone, phosgene, etc.

[0552] (Preparation Method 2) Preparation of the compound represented by the following formula (s-12)

[0553] [Chemistry 80]

[0554]

[0555] (where R is in the formula) i1A and S i1 R represents the expression in the general formula (i). i1A and S i1 (same meaning)

[0556] By reacting the compound represented by general formula (s-7) with the compound represented by general formula (s-8), the compound represented by general formula (s-9) can be obtained.

[0557] Examples of reaction methods include the coupling reaction of scallions using palladium catalysts, copper catalysts, and bases.

[0558] Specific examples of palladium catalysts, copper catalysts, and bases include the compounds described in (Preparation Method 1).

[0559] By reacting the compound represented by general formula (s-9) with the compound represented by general formula (s-10), the compound represented by general formula (s-11) can be obtained.

[0560] Examples of reaction methods include the coupling reaction of scallions using palladium catalysts, copper catalysts, and bases.

[0561] Specific examples of palladium catalysts, copper catalysts, and bases include the compounds described in (Preparation Method 1).

[0562] Finally, the target compound (s-12) can be obtained by reacting the amino group with 1,1-thiocarbonyldiimidazole, 1,1-thiocarbonyldi-2(1H)-pyridone, phosgene, etc.

[0563] (Preparation Method 3) Preparation of the compound represented by the following formula (s-21)

[0564] [Chemistry 81]

[0565]

[0566] (where R is in the formula) i1A and S i1 R represents the expression in the general formula (i). i1A and S i1 (same meaning)

[0567] The compound represented by general formula (s-13) can be obtained by reacting the compound represented by general formula (s-14).

[0568] Examples of reaction methods include the coupling reaction of scallions using palladium catalysts, copper catalysts, and bases.

[0569] Specific examples of palladium catalysts, copper catalysts, and bases include the compounds described in (Preparation Method 1).

[0570] The compound represented by general formula (s-15) can be obtained by reacting the compound represented by general formula (s-16).

[0571] As a reaction method, for example, the method of Suzuki coupling in the presence of a metal catalyst and a base can be cited.

[0572] Specific examples of metal catalysts and bases include the compounds described in (Preparation Method 1).

[0573] The compound represented by general formula (s-18) can be obtained by reacting the compound represented by general formula (s-17) with trifluoromethanesulfonic anhydride, for example, in the presence of a base.

[0574] Specific examples of bases include triethylamine and pyridine.

[0575] The compound represented by general formula (s-18) can be obtained by reacting the compound represented by general formula (s-19).

[0576] Examples of reaction methods include the coupling reaction of scallions using palladium catalysts, copper catalysts, and bases.

[0577] Specific examples of palladium catalysts, copper catalysts, and bases include the compounds described in (Preparation Method 1).

[0578] Finally, the target compound (s-21) can be obtained by reacting the amino group with 1,1-thiocarbonyldiimidazole, 1,1-thiocarbonyldi-2(1H)-pyridone, phosgene, etc.

[0579] (Preparation Method 4) Preparation of the compound represented by the following formula (s-31)

[0580] [Chemistry 82]

[0581]

[0582] (where R is in the formula) i1A and S i1 R represents the expression in the general formula (i). i1A and S i1 (same meaning)

[0583] The compound represented by general formula (s-22) can be reacted with the compound represented by general formula (s-23) to obtain the compound represented by general formula (s-24).

[0584] Examples of reaction methods include the coupling reaction of scallions using palladium catalysts, copper catalysts, and bases.

[0585] Specific examples of palladium catalysts, copper catalysts, and bases include the compounds described in (Preparation Method 1).

[0586] The compound represented by general formula (s-25) can be obtained by reacting the compound represented by general formula (s-24) with trimethylsilylacetylene.

[0587] Examples of reaction methods include the coupling reaction of scallions using palladium catalysts, copper catalysts, and bases.

[0588] Specific examples of palladium catalysts, copper catalysts, and bases include the compounds described in (Preparation Method 1).

[0589] The compound represented by general formula (s-25) can be obtained by reacting it with potassium carbonate.

[0590] The compound represented by general formula (s-26) can be obtained by reacting the compound represented by general formula (s-27).

[0591] Examples of reaction methods include the coupling reaction of scallions using palladium catalysts, copper catalysts, and bases.

[0592] Specific examples of palladium catalysts, copper catalysts, and bases include the compounds described in (Preparation Method 1).

[0593] The compound represented by general formula (s-28) can be obtained by reacting the compound represented by general formula (s-29).

[0594] As a reaction method, for example, the method of Suzuki coupling in the presence of a metal catalyst and a base can be cited.

[0595] Specific examples of metal catalysts and bases include the compounds described in preparation method 1.

[0596] Finally, the target compound (s-31) can be obtained by reacting the amino group with 1,1-thiocarbonyldiimidazole, 1,1-thiocarbonyldi-2(1H)-pyridone, phosgene, etc.

[0597] Other reaction conditions not specified in the steps described can be listed as follows: those described in publications such as *Lectures on Experimental Chemistry* (edited by the Chemical Society of Japan, published by Maruzen Co., Ltd.), *Organic Syntheses* (published by John Wiley & Sons, Inc.), *Beilstein Handbook of Organic Chemistry* (Beilstein-Institut fuer Literatur der Organischen Chemie, Springer-Verlag Berlin and Heidelberg GmbH & Co.K.), and *Fiesers' Reagents for Organic Synthesis* (John Wiley & Sons, Inc.); or those described in the SciFinder (Chemical Abstracts Service, American Chemical Society) database. The criteria are included in databases such as the Society, the Reaxys database (Elsevier Ltd.), and others.

[0598] When handling substances that are unstable to oxygen and / or moisture in each step, it is preferable to operate in an inert gas such as nitrogen or argon.

[0599] Functional groups can be protected as needed during each step.

[0600] As a protecting group, examples include those described in "GREENE'S PROTECTIVE GROUPS IN ORGANIC SYNTHESIS" (Fourth Edition, co-authored by Peter GMWUTS and Theodora W. Greene, published by John Wiley & Sons, Inc.).

[0601] In addition, refining can be carried out as needed in each step.

[0602] Examples of refining methods include: chromatography, recrystallization, distillation, sublimation, reprecipitation, adsorption, and liquid-liquid separation.

[0603] Specific examples of refining agents include silica gel, alumina, and activated carbon.

[0604] (Other compounds)

[0605] (The compound represented by general formula (ii))

[0606] Regarding solubility, Δn and / or Δε r From this perspective, the liquid crystal composition of the present invention may also further comprise one or more compounds having an isothiocyanate group (-NCS) represented by the following general formula (ii).

[0607] [Chemistry 83]

[0608]

[0609] In general formula (ii), R ii1 Alkyl groups having 1 to 20 carbon atoms.

[0610] The alkyl group is a straight-chain, branched, or cyclic alkyl group, preferably a straight-chain alkyl group.

[0611] The alkyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6.

[0612] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0613] In addition, one or more of the -CH2-CH2- alkyl groups may be substituted by -CH=CH-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CF=CF- and / or -C≡C-.

[0614] In addition, one or more of the -CH2-CH2-CH2- alkyl groups may be replaced by -O-CO-O-.

[0615] In addition, one or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms.

[0616] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[0617] Wherein, when the alkyl group is substituted by a specified group, oxygen atoms do not bond directly to oxygen atoms.

[0618] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[0619] For example, R ii1 An alkoxy group with 1 to 19 carbon atoms can be represented by replacing one of the -CH2- groups with -O- groups.

[0620] The alkoxy group is a straight-chain, branched, or cyclic alkoxy group, preferably a straight-chain alkoxy group.

[0621] The alkoxy group preferably has 2 to 10 carbon atoms, more preferably 2 to 6.

[0622] Additionally, R ii1 By replacing one of the -CH2- groups in the alkyl group with -S-, an alkyl mercapto group (alkyl thio group) with 1 to 19 carbon atoms can be represented.

[0623] The alkyl thiol group is a linear, branched, or cyclic alkyl thiol group, preferably a linear alkyl thiol group.

[0624] The alkyl mercapto group preferably has 1 to 10 carbon atoms, and more preferably 1 to 6.

[0625] Additionally, R ii1 An alkenyl group with 2 to 20 carbon atoms can be represented by replacing one or more of the -CH2-CH2- groups with -CH=CH- groups.

[0626] The alkenyl group is a linear, branched, or cyclic alkenyl group, preferably a linear alkenyl group.

[0627] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6.

[0628] Additionally, R ii1 An alkynyl group with 2 to 20 carbon atoms can be represented by replacing one or more of the -CH2-CH2- groups with -C≡C- groups.

[0629] The alkynyl group is a straight-chain, branched, or cyclic alkynyl group, preferably a straight-chain alkynyl group.

[0630] The number of carbon atoms in the alkynyl group is preferably 2 to 10, and more preferably 2 to 6.

[0631] Additionally, R ii1 An alkyl group having 2 to 19 carbon atoms can be represented by replacing one of the -CH2- atoms with -O- atoms and replacing one or more of the -CH2-CH2- atoms with -CH=CH- atoms.

[0632] The olefinic group is a straight-chain, branched, or cyclic olefinic group, preferably a straight-chain olefinic group.

[0633] The number of carbon atoms in the olefinic group is preferably 2 to 10, and more preferably 2 to 6.

[0634] Additionally, R ii1 By replacing one or more hydrogen atoms of the alkyl group with halogen atoms, a alkyl halide with 1 to 20 carbon atoms can be represented.

[0635] The alkyl halide is a straight-chain, branched, or cyclic alkyl halide, preferably a straight-chain alkyl halide.

[0636] The number of carbon atoms in the alkyl halide is preferably 2 to 10, and more preferably 2 to 6.

[0637] Additionally, R ii1 A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- atom of the alkyl group with -O- atom and replacing one or more hydrogen atoms of the alkyl group with halogen atoms.

[0638] The halogenated alkoxy group is a straight-chain, branched, or cyclic halogenated alkoxy group, preferably a straight-chain halogenated alkoxy group.

[0639] The number of carbon atoms in the haloalkoxy group is preferably 2 to 10, and more preferably 2 to 6.

[0640] As R ii1 Specific examples of alkyl groups having 1 to 20 carbon atoms (including substituted alkyl groups) can be listed in formula (R). ii1 -1)~Formula (R) ii1 -37) represents the base.

[0641] [Chemistry 84]

[0642]

[0643] Formula (R) ii1 -1)~Formula (R) ii1 In -37), the black dot represents the direction to A. ii1 The bond structure.

[0644] In R ii1 When the bonded ring structure is phenyl (aromatic), it is preferably a straight-chain alkyl group with 1 to 5 carbon atoms, a straight-chain alkoxy group with 1 to 4 carbon atoms, or an alkenyl group with 4 to 5 carbon atoms. In R ii1 When the bonded ring structure is a saturated ring structure such as cyclohexane, pyran, or dioxane, it is preferably a straight-chain alkyl group with 1 to 5 carbon atoms, a straight-chain alkoxy group with 1 to 4 carbon atoms, or a straight-chain alkenyl group with 2 to 5 carbon atoms.

[0645] Additionally, as R ii1 In order to stabilize the nematic phase, the total number of carbon atoms and oxygen atoms (if present) is preferably 5 or less, and preferably linear.

[0646] In addition, as R ii1 From the viewpoint of solubility, it is preferred to use a straight-chain alkyl group with 2 to 8 carbon atoms, a straight-chain alkoxy group with 2 to 8 carbon atoms, a straight-chain haloalkoxy group with 2 to 8 carbon atoms, or a straight-chain alkyl mercapto group with 1 to 6 carbon atoms.

[0647] In general formula (ii), A ii1 and A ii2 Represent the basis(a), basis(b), basis(c), and basis(d) chosen independently:

[0648] (a) 1,4-cyclohexylene (one or more non-adjacent -CH2- groups may be replaced by -O- and / or -S-)

[0649] (b) 1,4-Phenylidene (one or more -CH= groups may be substituted with -N=)

[0650] (c) 1,4-cyclohexenyl, bicyclo[2.2.2]octane-1,4-diyl, naphth-2,6-diyl, naphth-1,4-diyl, 1,2,3,4-tetrahydronaphth-2,6-diyl, 5,6,7,8-tetrahydronaphth-1,4-diyl, decahydronaphth-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene -2,7-Diyl (one 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 can be substituted with -N=)

[0651] (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 or more -CH= groups may be substituted with -N=)

[0652] The base in the group formed by the group.

[0653] A ii1 and A ii2One or more hydrogen atoms can be independently replaced by substituents S. ii1 replace.

[0654] Substituent S ii1 It represents any one of the following: halogen atom, pentafluorothiol, nitro, cyano, isocyano, amino, hydroxyl, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyano, or alkyl group having 1 to 20 carbon atoms.

[0655] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[0656] The alkyl group having 1 to 20 carbon atoms is a straight-chain, branched, or cyclic alkyl group, preferably a straight-chain alkyl group.

[0657] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0658] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0659] In addition, one or more of the -CH2-CH2- groups 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-.

[0660] One or more of the -CH2-CH2-CH2- alkyl groups may be independently substituted by -O-CO-O-.

[0661] In addition, one or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms.

[0662] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[0663] Wherein, when the alkyl group is substituted by a specified group, oxygen atoms do not bond directly to oxygen atoms.

[0664] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[0665] As a substituent S ii1 Preferably, it contains fluorine or chlorine atoms.

[0666] In addition, A ii1 At least one or A ii2 Preferably, it consists of at least one substituent Sii1 The substitution is preferably made by halogen atoms, and more preferably by fluorine atoms.

[0667] Furthermore, in the substituent S ii1 When multiple instances exist, these can be the same or different.

[0668] As A ii1 The substituent S in ii1 The replacement position is preferably that of the following formula (A) ii1 -SP-1)~Form (A) ii1 Any of the following (-SP-5).

[0669] [Chemistry 85]

[0670]

[0671] Formula (A) ii1 -SP-1)~Form (A) ii1 In -SP-5), the white dot indicates the direction to R. ii1 or Z ii1 The bond is represented by black dots indicating the Z-axis. ii1 The bond structure.

[0672] As A ii2 The substituent S in ii1 The replacement position is preferably that of the following formula (A) ii2 -SP-1)~Form (A) ii2 Any of the following (-SP-8).

[0673] [Chemistry 86]

[0674]

[0675] Formula (A) ii2 -SP-1)~Form (A) ii2 In -SP-8), the white dot indicates the direction of Z. ii1 The black dots represent the bonds to the isothiocyanate group (-NCS).

[0676] More specifically, A ii1 Preferably, it represents the following formula (A) ii1 -1)~Form (A) ii1 Any of the following: -13)

[0677] [Chemistry 87]

[0678]

[0679] Formula (A) ii1 -1)~Form (A) ii1 In -13), the white dot represents the direction to R. ii1 or Zii1 The bond is represented by black dots indicating the Z-axis. ii1 The bond structure.

[0680] More specifically, A ii2 Preferably, it represents the following formula (A) ii2 -1)~Form (A) ii2 Any of -7).

[0681] [Chemistry 88]

[0682]

[0683] Formula (A) ii2 -1)~Form (A) ii2 In -7), the white dot represents the direction of Z. ii1 The black dots represent the bonds to the isothiocyanate group (-NCS).

[0684] In general formula (ii), Z ii1 It refers to any of the single bonds and alkylene groups with 1 to 20 carbon atoms.

[0685] One or more of the -CH2- groups in the alkylene group may be independently substituted by -O- groups.

[0686] In addition, one or more of the -CH2-CH2- groups 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-.

[0687] In addition, one or more of the -CH2-CH2-CH2- alkyl groups can be independently substituted by -O-CO-O-.

[0688] In cases where alkyl groups with 1 to 10 carbon atoms are substituted by specified groups, oxygen atoms do not bond directly to each other.

[0689] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[0690] Specific examples of alkylene groups having 1 to 20 carbon atoms (including substituted alkylene groups) can be enumerated as (Z ii1 -1)~Formula (Z) ii1 -24) represents the base.

[0691] [Chemistry 89]

[0692]

[0693] Formula (Z) ii1 -1)~Formula (Z) ii1 In -24), the white dot represents the direction to A. ii1 The bond, the black dot indicates the bond to A ii1 Or A ii2 The bond structure.

[0694] In general formula (ii), n ii1 It represents an integer from 1 to 4, preferably from 1 to 2.

[0695] In n ii1 When Δn is 1, then Δn and / or Δε r From Z's point of view, ii1 Preferably, it represents a single bond or -C≡C-.

[0696] Additionally, in n ii1 When the value is 2, then Δn and / or Δε r From Z's point of view, ii1 Preferably, it represents a single bond or -C≡C-.

[0697] Furthermore, in general formula (ii), in A ii1 and Z ii1 When multiple instances exist, these instances can be the same or different.

[0698] Among them, the compounds represented by general formula (ii) are excluded from the compounds represented by general formula (i) (including subordinate concepts).

[0699] The compounds represented by general formula (ii) are preferably those represented by general formulas (ii-1) to (ii-7).

[0700] [Chemistry 90]

[0701] R ii1 -A ii1 -A ii2 -NCS (ii-1)

[0702]

[0703] In general formulas (ii-1) to (ii-7), R ii1 A ii1 and A ii2 R represents the expression in general formula (ii). ii1 A ii1 and A ii2 They have the same meaning, respectively.

[0704] In general formulas (ii-3) to (ii-7), Aii1-2 The definition of A in the general formula (ii) ii1 The definitions are the same.

[0705] The compounds represented by general formula (ii-1) are preferably those represented by general formulas (ii-1-1) to (ii-1-2).

[0706] [Chemistry 91]

[0707]

[0708] In general formulas (ii-1-1) to (ii-1-2), R ii1 R represents the expression in general formula (ii). ii1 Same meaning.

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

[0710] [Chemistry 92]

[0711]

[0712] Specific examples of compounds represented by general formula (ii-1-2) include compounds represented by structural formulas (ii-1-2.1) to (ii-1-2.6).

[0713] [Chemistry 93]

[0714]

[0715] The compounds represented by general formula (ii-2) are preferably those represented by general formulas (ii-2-1) to (ii-2-5).

[0716] [Chemistry 94]

[0717]

[0718] In general formulas (ii-2-1) to (ii-2-5), R ii1 and S ii1 Represent R independently of the general formula (ii). ii1 and S ii1 They have the same meaning, respectively.

[0719] Specific examples of compounds represented by general formula (ii-2-1) include compounds represented by structural formulas (ii-2-1.1) to (ii-2-1.5).

[0720] [Chem. 95]

[0721]

[0722] Specific examples of compounds represented by general formula (ii-2-2) include compounds represented by structural formulas (ii-2-2.1) to (ii-2-2.3).

[0723] [Chemistry 96]

[0724]

[0725] Specific examples of compounds represented by general formula (ii-2-3) include compounds represented by structural formulas (ii-2-3.1) to (ii-2-3.3).

[0726] [Chemistry 97]

[0727]

[0728] Specific examples of compounds represented by general formula (ii-2-4) include compounds represented by structural formulas (ii-2-4.1) to (ii-2-4.3).

[0729] [Chem. 98]

[0730]

[0731] Specific examples of compounds represented by general formula (ii-2-5) include compounds represented by structural formulas (ii-2-5.1) to (ii-2-5.3).

[0732] [Chemistry 99]

[0733]

[0734] The compounds represented by general formula (ii-3) are preferably those represented by general formulas (ii-3-1) to (ii-3-6).

[0735] [Chemistry 100]

[0736]

[0737] In general formulas (ii-3-1) to (ii-3-6), R ii1 and S ii1 Represent R independently of the general formula (ii). ii1 and S ii1 They have the same meaning, respectively.

[0738] Specific examples of compounds represented by general formula (ii-3-1) include compounds represented by structural formulas (ii-3-1.1) to (ii-3-1.4).

[0739] [Chemistry 101]

[0740]

[0741] Specific examples of compounds represented by general formula (ii-3-2) include compounds represented by the following structural formulas (ii-3-2.1) to (ii-3-2.3).

[0742] [Chemistry 102]

[0743]

[0744] Specific examples of compounds represented by general formula (ii-3-3) include compounds represented by structural formulas (ii-3-3.1) to (ii-3-3.3).

[0745] [Chemistry 103]

[0746]

[0747] Specific examples of compounds represented by general formula (ii-3-4) include compounds represented by structural formulas (ii-3-4.1) to (ii-3-4.3).

[0748] [Chemistry 104]

[0749]

[0750] Specific examples of compounds represented by general formula (ii-3-5) include compounds represented by structural formulas (ii-3-5.1) to (ii-3-5.3).

[0751] [Chemistry 105]

[0752]

[0753] Specific examples of compounds represented by general formula (ii-3-6) include compounds represented by structural formulas (ii-3-6.1) to (ii-3-6.2).

[0754] [Chemistry 106]

[0755]

[0756] The compounds represented by general formula (ii-4) are preferably those represented by general formulas (ii-4-1) to (ii-4-17).

[0757] [Chemistry 107]

[0758]

[0759] [Chemistry 109]

[0760]

[0761] In general formulas (ii-4-1) to (ii-4-17), R ii1 and S ii1 Represent R independently of the general formula (ii). ii1 and S ii1 They have the same meaning, respectively.

[0762] Specific examples of compounds represented by general formula (ii-4-1) include compounds represented by structural formulas (ii-4-1.1) to (ii-4-1.3).

[0763] [Chemical 110]

[0764]

[0765] Specific examples of compounds represented by general formula (ii-4-2) include compounds represented by structural formulas (ii-4-2.1) to (ii-4-2.3).

[0766] [Chemistry 111]

[0767]

[0768] Specific examples of compounds represented by general formula (ii-4-3) include compounds represented by structural formulas (ii-4-3.1) to (ii-4-3.3).

[0769] [Chemistry 112]

[0770]

[0771] Specific examples of compounds represented by general formula (ii-4-4) include compounds represented by structural formulas (ii-4-4.1) to (ii-4-4.3).

[0772] [Chemistry 113]

[0773]

[0774] Specific examples of compounds represented by general formula (ii-4-5) include compounds represented by structural formulas (ii-4-5.1) to (ii-4-5.3).

[0775] [Chemistry 114]

[0776]

[0777] Specific examples of compounds represented by general formula (ii-4-6) include compounds represented by structural formulas (ii-4-6.1) to (ii-4-6.3).

[0778] [Chemistry 115]

[0779]

[0780] Specific examples of compounds represented by general formula (ii-4-7) include compounds represented by structural formulas (ii-4-7.1) to (ii-4-7.3).

[0781] [Chemistry 116]

[0782]

[0783] Specific examples of compounds represented by general formula (ii-4-8) include compounds represented by structural formulas (ii-4-8.1) to (ii-4-8.3).

[0784] [Chemistry 117]

[0785]

[0786] Specific examples of compounds represented by general formula (ii-4-9) include compounds represented by structural formulas (ii-4-9.1) to (ii-4-9.4).

[0787] [Chemistry 118]

[0788]

[0789] Specific examples of compounds represented by general formula (ii-4-10) include compounds represented by structural formulas (ii-4-10.1) to (ii-4-10.5).

[0790] [Chemistry 119]

[0791]

[0792] Specific examples of compounds represented by the general formula (ii-4-11) include compounds represented by the following structural formulas (ii-4-11.1) to (ii-4-11.4).

[0793] [Chemistry 120]

[0794]

[0795] Specific examples of compounds represented by general formula (ii-4-12) include compounds represented by the following structural formulas (ii-4-12.1) to (ii-4-12.5).

[0796] [Chemistry 121]

[0797]

[0798] Specific examples of compounds represented by general formula (ii-4-13) include compounds represented by the following structural formulas (ii-4-13.1) to (ii-4-13.8).

[0799] [Chemistry 122]

[0800]

[0801] [Chemistry 123]

[0802]

[0803] Specific examples of compounds represented by general formula (ii-4-14) include compounds represented by structural formulas (ii-4-14.1) to (ii-4-14.4).

[0804] [Chemistry 124]

[0805]

[0806] Specific examples of compounds represented by general formula (ii-4-15) include compounds represented by the following structural formulas (ii-4-15.1) to (ii-4-15.4).

[0807] [Chemistry 125]

[0808]

[0809] Specific examples of compounds represented by the general formula (ii-4-16) include compounds represented by the following structural formula (ii-4-16.1).

[0810] [Chemistry 126]

[0811]

[0812] As specific examples of compounds represented by the general formula (ii-4-17), compounds represented by the following structural formula (ii-4-17.1) can be listed.

[0813] [Chemistry 127]

[0814]

[0815] The compounds represented by general formula (ii-5) are preferably those represented by general formulas (ii-5-1) to (ii-5-5).

[0816] [Chemistry 128]

[0817]

[0818] In general formulas (ii-5-1) to (ii-5-5), R ii1 and S ii1 Represent R independently of the general formula (ii). ii1 and S ii1 They have the same meaning, respectively.

[0819] Specific examples of compounds represented by general formula (ii-5-1) include compounds represented by structural formulas (ii-5-1.1) to (ii-5-1.4).

[0820] [Chemistry 129]

[0821]

[0822] Specific examples of compounds represented by general formula (ii-5-2) include compounds represented by structural formulas (ii-5-2.1) to (ii-5-2.4).

[0823] [Chemistry 130]

[0824]

[0825] Specific examples of compounds represented by general formula (ii-5-3) include compounds represented by structural formulas (ii-5-3.1) to (ii-5-3.3).

[0826] [Chemistry 131]

[0827]

[0828] Specific examples of compounds represented by general formula (ii-5-4) include compounds represented by structural formulas (ii-5-4.1) to (ii-5-4.3).

[0829] [Chemistry 132]

[0830]

[0831] As specific examples of compounds represented by the general formula (ii-5-5), compounds represented by the following structural formula (ii-5-5.1) can be listed.

[0832] [Chemistry 133]

[0833]

[0834] The compounds represented by general formula (ii-6) are preferably those represented by general formulas (ii-6-1) to (ii-6-34).

[0835] [Chemistry 134]

[0836]

[0837] [Chemistry 135]

[0838]

[0839] [Chemistry 136]

[0840]

[0841] [Chemistry 137]

[0842]

[0843] [Chemistry 138]

[0844]

[0845] Specific examples of compounds represented by general formula (ii-6-1) include compounds represented by structural formulas (ii-6-1.1) to (ii-6-1.4).

[0846] [Chemistry 139]

[0847]

[0848] Specific examples of compounds represented by general formula (ii-6-2) include compounds represented by structural formulas (ii-6-2.1) to (ii-6-2.4).

[0849] [Chemistry 140]

[0850]

[0851] Specific examples of compounds represented by general formula (ii-6-3) include compounds represented by structural formulas (ii-6-3.1) to (ii-6-3.4).

[0852] [Chemistry 141]

[0853]

[0854] Specific examples of compounds represented by general formula (ii-6-4) include compounds represented by structural formulas (ii-6-4.1) to (ii-6-4.4).

[0855] [Chemistry 142]

[0856]

[0857] Specific examples of compounds represented by general formula (ii-6-5) include compounds represented by structural formulas (ii-6-5.1) to (ii-6-5.8).

[0858] [Chemistry 143]

[0859]

[0860] [Chemistry 144]

[0861]

[0862] Specific examples of compounds represented by the general formula (ii-6-6) include compounds represented by the following structural formulas (ii-6-6.1) to (ii-6-6.2).

[0863] [Chemistry 145]

[0864]

[0865] Specific examples of compounds represented by general formula (ii-6-7) include compounds represented by structural formulas (ii-6-7.1) to (ii-6-7.4).

[0866] [Chemistry 146]

[0867]

[0868] Specific examples of compounds represented by general formula (ii-6-8) include compounds represented by structural formulas (ii-6-8.1) to (ii-6-8.5).

[0869] [Chemistry 147]

[0870]

[0871] Specific examples of compounds represented by general formula (ii-6-9) include compounds represented by structural formulas (ii-6-9.1) to (ii-6-9.4).

[0872] [Chemistry 148]

[0873]

[0874] As specific examples of compounds represented by the general formula (ii-6-10), compounds represented by the following structural formula (ii-6-10.1) can be listed.

[0875] [Chemistry 149]

[0876]

[0877] Specific examples of compounds represented by general formula (ii-6-11) include compounds represented by structural formulas (ii-6-11.1) to (ii-6-11.16).

[0878] [Chemistry 150]

[0879]

[0880] [Chemistry 151]

[0881]

[0882] [Chemistry 152]

[0883]

[0884] [Chemistry 153]

[0885]

[0886] Specific examples of compounds represented by general formula (ii-6-12) include compounds represented by structural formulas (ii-6-12.1) to (ii-6-12.4).

[0887] [Chemistry 154]

[0888]

[0889] Specific examples of compounds represented by general formula (ii-6-13) include compounds represented by the following structural formulas (ii-6-13.1) to (ii-1-13.4).

[0890] [Chemistry 155]

[0891]

[0892] Specific examples of compounds represented by general formula (ii-6-14) include compounds represented by the following structural formulas (ii-6-14.1) to (ii-6-14.4).

[0893] [Chemistry 156]

[0894]

[0895] Specific examples of compounds represented by general formula (ii-6-15) include compounds represented by the following structural formulas (ii-6-15.1) to (ii-6-15.4).

[0896] [Chemistry 157]

[0897]

[0898] Specific examples of compounds represented by general formula (ii-6-16) include compounds represented by the following structural formulas (ii-1-16.1) to (ii-6-16.5).

[0899] [Chemistry 158]

[0900]

[0901] Specific examples of compounds represented by general formula (ii-6-17) include compounds represented by the following structural formulas (ii-6-17.1) to (ii-6-17.2).

[0902] [Chemistry 159]

[0903]

[0904] Specific examples of compounds represented by general formula (ii-6-18) include compounds represented by structural formulas (ii-6-18.1) to (ii-6-18.5).

[0905] [Chemistry 160]

[0906]

[0907] Specific examples of compounds represented by general formula (ii-6-19) include compounds represented by structural formulas (ii-6-19.1) to (ii-6-19.14).

[0908] [Chemistry 161]

[0909]

[0910] [Chemistry 162]

[0911]

[0912] [Chemistry 163]

[0913]

[0914] Specific examples of compounds represented by general formula (ii-6-20) include compounds represented by the following structural formulas (ii-6-20.1) to (ii-6-20.4).

[0915] [Chemistry 164]

[0916]

[0917] Specific examples of compounds represented by the general formula (ii-6-21) include compounds represented by the following structural formula (ii-6-21.1).

[0918] [Chemistry 165]

[0919]

[0920] Specific examples of compounds represented by the general formula (ii-6-22) include compounds represented by the following structural formulas (ii-6-22.1) to (ii-6-22.4).

[0921] [Chemistry 166]

[0922]

[0923] Specific examples of compounds represented by general formula (ii-6-23) include compounds represented by the following structural formulas (ii-6-23.1) to (ii-6-23.4).

[0924] [Chemistry 167]

[0925]

[0926] Specific examples of compounds represented by the general formula (ii-6-24) include compounds represented by the following structural formula (ii-6-24.1).

[0927] [Chemistry 168]

[0928]

[0929] Specific examples of compounds represented by general formula (ii-6-25) include compounds represented by the following structural formulas (ii-6-25.1) to (ii-6-25.4).

[0930] [Chemistry 169]

[0931]

[0932] Specific examples of compounds represented by general formula (ii-6-26) include compounds represented by the following structural formulas (ii-6-26.1) to (ii-6-26.4).

[0933] [Chemistry 170]

[0934]

[0935] Specific examples of compounds represented by the general formula (ii-6-27) include compounds represented by the following structural formulas (ii-6-27.1) to (ii-6-27.16).

[0936] [Chemistry 171]

[0937]

[0938] [Chemistry 172]

[0939]

[0940] [Chemistry 173]

[0941]

[0942] [Chemistry 174]

[0943]

[0944] Specific examples of compounds represented by the general formula (ii-6-28) include compounds represented by the following structural formulas (ii-6-28.1) to (ii-6-28.5).

[0945] [Chemistry 175]

[0946]

[0947] Specific examples of compounds represented by general formula (ii-6-29) include compounds represented by the following structural formulas (ii-6-29.1) to (ii-6-29.5).

[0948] [Chemistry 176]

[0949]

[0950] Specific examples of compounds represented by general formula (ii-6-30) include compounds represented by structural formulas (ii-6-30.1) to (ii-6-30.4).

[0951] [Chemistry 177]

[0952]

[0953] As specific examples of compounds represented by the general formula (ii-6-31), compounds represented by the following structural formula (ii-6-31.1) can be listed.

[0954] [Chemistry 178]

[0955]

[0956] Specific examples of compounds represented by the general formula (ii-6-32) include compounds represented by the following structural formula (ii-6-32.1).

[0957] [Chemistry 179]

[0958]

[0959] Specific examples of compounds represented by the general formula (ii-6-33) include compounds represented by the following structural formulas (ii-6-33.1) to (ii-6-33.4).

[0960] [Chemistry 180]

[0961]

[0962] Specific examples of compounds represented by the general formula (ii-6-34) include compounds represented by the following structural formula (ii-6-34.1).

[0963] [Chemistry 181]

[0964]

[0965] The compound represented by general formula (ii-7) is preferably the compound represented by the following general formula (ii-7-1).

[0966] [Chemistry 182]

[0967]

[0968] As specific examples of compounds represented by the general formula (ii-7-1), compounds represented by the following structural formula (ii-7-1.1) can be listed.

[0969] [Chemistry 183]

[0970]

[0971] General formula (ii), General formula (ii-1) to General formula (ii-7), General formula (ii-1-1) to General formula (ii-1-2), General formula (ii-2-1) to General formula (ii-2-5), General formula (ii-3-1) to General formula (ii-3-6), General formula (ii-4-1) to General formula (ii-4-17), General formula (ii-5-1) to General formula (ii-5-5), General formula (ii-6-1) to General formula (ii-6-34), General formula (ii-7-1), 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 -1.5), structure (ii-2-2.1) ~ structure (ii-2-2.3), structure (ii-2-3.1) ~ structure (ii-2-3.3), structure (ii-2-4.1) ~ structure (ii-2-4.3), structure (ii-2-5.1) ~ structure (ii-2-5.3), structure (ii-3-1.1) ~ structure (ii-3-1.4), structure (ii-3-2.1) ~ structure (ii-3-2.3), structure (ii-3-3.1) ~ structure (ii-3-3.3), structure (ii-3-4.1) ~ structure (ii-3-4.3), structure (ii-3-5.1) ~ structure ( ii-3-5.3), structural formula (ii-3-6.1) ~ structural formula (ii-3-6.2), structural formula (ii-4-1.1) ~ structural formula (ii-4-1.3), structural formula (ii-4-2.1) ~ structural formula (ii-4-2.3), structural formula (ii-4-3.1) ~ structural formula (ii-4-3.3), structural formula (ii-4-4.1) ~ structural formula (ii-4-4.3), structural formula (ii-4-5.1) ~ structural formula (ii-4-5.3), structural formula (ii-4-6.1) ~ structural formula (ii-4-6.3), structural formula (ii-4-7.1) ~ structural formula (ii-4-7.3), structural formula (ii-4-8.1) ~ Structure (ii-4-8.3), Structure (ii-4-9.1) to Structure (ii-4-9.4), Structure (ii-4-10.1) to Structure (ii-4-10.5), Structure (ii-4-11.1) to Structure (ii-4-11.4), Structure (ii-4-12.1) to Structure (ii-4-12.5), Structure (ii-4-13.1) to Structure (ii-4-13.8), Structure (ii-4-14.1) to Structure (ii-4-14.4), Structure (ii-4-15.1) to Structure (ii-4-15.4), Structure (ii-4-16.1), Structure (ii-4-17).1) Structure (ii-5-1.1) ~ Structure (ii-5-1.4), Structure (ii-5-2.1) ~ Structure (ii-5-2.4), Structure (ii-5-3.1) ~ Structure (ii-5-3.3), Structure (ii-5-4.1) ~ Structure (ii-5-4.3), Structure (ii-5-5.1), Structure (ii-6-1.1) ~ Structure (ii-6-1.4), Structure (ii-6-2.1) ~ Structure (ii-6-2.4), Structure (ii-6-3.1) ~ Structure (ii-6-3.4), Structure (ii-6-4.1) ~ Structure (ii-6-4.4), Structure (ii-6 -5.1)~Structure (ii-6-5.8), Structure (ii-6-6.1)~Structure (ii-6-6.2), Structure (ii-6-7.1)~Structure (ii-6-7.4), Structure (ii-6-8.1)~Structure (ii-6-8.5), Structure (ii-6-9.1)~Structure (ii-6-9.4), Structure (ii-6-10.1), Structure (ii-6-11.1)~Structure (ii-6-11.16), Structure (ii-6-12.1)~Structure (ii-6-12.4), Structure (ii-6-13.1)~Structure (ii-1-13.4), Structure (ii-6-14) .1)~Structure (ii-6-14.4), Structure (ii-6-15.1)~Structure (ii-6-15.4), Structure (ii-1-16.1)~Structure (ii-6-16.5), Structure (ii-6-17.1)~Structure (ii-6-17.2), Structure (ii-6-18.1)~Structure (ii-6-18.5), Structure (ii-6-19.1)~Structure (ii-6-19.14), Structure (ii-6-20.1)~Structure (ii-6-20.4), Structure (ii-6-21.1), Structure (ii-6-22.1)~Structure (ii-6-22.4), Structure ( ii-6-23.1)~Structure (ii-6-23.4), Structure (ii-6-24.1), Structure (ii-6-25.1)~Structure (ii-6-25.4), Structure (ii-6-26.1)~Structure (ii-6-26.4), Structure (ii-6-27.1)~Structure (ii-6-27.16), Structure (ii-6-28.1)~Structure (ii-6-28.5), Structure (ii-6-29.1)~Structure (ii-6-29.5), Structure (ii-6-30.1)~Structure (ii-6-30.4), Structure (ii-6-31.1), Structure (ii-6-32).1) The compounds represented by structural formulas (ii-6-33.1) to (ii-6-33.4), (ii-6-34.1), or (ii-7-1.1) are used in the liquid crystal composition in one or more types, preferably one to fifteen types, more preferably two to ten types, and more preferably three to eight types.

[0972] General formula (ii), General formula (ii-1) to General formula (ii-7), General formula (ii-1-1) to General formula (ii-1-2), General formula (ii-2-1) to General formula (ii-2-5), General formula (ii-3-1) to General formula (ii-3-6), General formula (ii-4-1) to General formula (ii-4-17), General formula (ii-5-1) to General formula (ii-5-5), General formula (ii-6-1) to General formula (ii-6-34), General formula (ii-7-1), 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 -1.5), structure (ii-2-2.1) ~ structure (ii-2-2.3), structure (ii-2-3.1) ~ structure (ii-2-3.3), structure (ii-2-4.1) ~ structure (ii-2-4.3), structure (ii-2-5.1) ~ structure (ii-2-5.3), structure (ii-3-1.1) ~ structure (ii-3-1.4), structure (ii-3-2.1) ~ structure (ii-3-2.3), structure (ii-3-3.1) ~ structure (ii-3-3.3), structure (ii-3-4.1) ~ structure (ii-3-4.3), structure (ii-3-5.1) ~ structure ( ii-3-5.3), structural formula (ii-3-6.1) ~ structural formula (ii-3-6.2), structural formula (ii-4-1.1) ~ structural formula (ii-4-1.3), structural formula (ii-4-2.1) ~ structural formula (ii-4-2.3), structural formula (ii-4-3.1) ~ structural formula (ii-4-3.3), structural formula (ii-4-4.1) ~ structural formula (ii-4-4.3), structural formula (ii-4-5.1) ~ structural formula (ii-4-5.3), structural formula (ii-4-6.1) ~ structural formula (ii-4-6.3), structural formula (ii-4-7.1) ~ structural formula (ii-4-7.3), structural formula (ii-4-8.1) ~ Structure (ii-4-8.3), Structure (ii-4-9.1) to Structure (ii-4-9.4), Structure (ii-4-10.1) to Structure (ii-4-10.5), Structure (ii-4-11.1) to Structure (ii-4-11.4), Structure (ii-4-12.1) to Structure (ii-4-12.5), Structure (ii-4-13.1) to Structure (ii-4-13.8), Structure (ii-4-14.1) to Structure (ii-4-14.4), Structure (ii-4-15.1) to Structure (ii-4-15.4), Structure (ii-4-16.1), Structure (ii-4-17).1) Structure (ii-5-1.1) ~ Structure (ii-5-1.4), Structure (ii-5-2.1) ~ Structure (ii-5-2.4), Structure (ii-5-3.1) ~ Structure (ii-5-3.3), Structure (ii-5-4.1) ~ Structure (ii-5-4.3), Structure (ii-5-5.1), Structure (ii-6-1.1) ~ Structure (ii-6-1.4), Structure (ii-6-2.1) ~ Structure (ii-6-2.4), Structure (ii-6-3.1) ~ Structure (ii-6-3.4), Structure (ii-6-4.1) ~ Structure (ii-6-4.4), Structure (ii-6 -5.1)~Structure (ii-6-5.8), Structure (ii-6-6.1)~Structure (ii-6-6.2), Structure (ii-6-7.1)~Structure (ii-6-7.4), Structure (ii-6-8.1)~Structure (ii-6-8.5), Structure (ii-6-9.1)~Structure (ii-6-9.4), Structure (ii-6-10.1), Structure (ii-6-11.1)~Structure (ii-6-11.16), Structure (ii-6-12.1)~Structure (ii-6-12.4), Structure (ii-6-13.1)~Structure (ii-1-13.4), Structure (ii-6-14) .1)~Structure (ii-6-14.4), Structure (ii-6-15.1)~Structure (ii-6-15.4), Structure (ii-1-16.1)~Structure (ii-6-16.5), Structure (ii-6-17.1)~Structure (ii-6-17.2), Structure (ii-6-18.1)~Structure (ii-6-18.5), Structure (ii-6-19.1)~Structure (ii-6-19.14), Structure (ii-6-20.1)~Structure (ii-6-20.4), Structure (ii-6-21.1), Structure (ii-6-22.1)~Structure (ii-6-22.4), Structure ( ii-6-23.1)~Structure (ii-6-23.4), Structure (ii-6-24.1), Structure (ii-6-25.1)~Structure (ii-6-25.4), Structure (ii-6-26.1)~Structure (ii-6-26.4), Structure (ii-6-27.1)~Structure (ii-6-27.16), Structure (ii-6-28.1)~Structure (ii-6-28.5), Structure (ii-6-29.1)~Structure (ii-6-29.5), Structure (ii-6-30.1)~Structure (ii-6-30.4), Structure (ii-6-31.1), Structure (ii-6-32).1) The lower limit of the total content of the compounds represented by structural formulas (ii-6-33.1) to (ii-6-33.4), (ii-6-34.1), or (ii-7-1.1) 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 55% by mass or more, preferably 65% ​​by mass or more, preferably 75% by mass or more, preferably 85% by mass or more.

[0973] General formula (ii), General formula (ii-1) to General formula (ii-7), General formula (ii-1-1) to General formula (ii-1-2), General formula (ii-2-1) to General formula (ii-2-5), General formula (ii-3-1) to General formula (ii-3-6), General formula (ii-4-1) to General formula (ii-4-17), General formula (ii-5-1) to General formula (ii-5-5), General formula (ii-6-1) to General formula (ii-6-34), General formula (ii-7-1), 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 -1.5), structure (ii-2-2.1) ~ structure (ii-2-2.3), structure (ii-2-3.1) ~ structure (ii-2-3.3), structure (ii-2-4.1) ~ structure (ii-2-4.3), structure (ii-2-5.1) ~ structure (ii-2-5.3), structure (ii-3-1.1) ~ structure (ii-3-1.4), structure (ii-3-2.1) ~ structure (ii-3-2.3), structure (ii-3-3.1) ~ structure (ii-3-3.3), structure (ii-3-4.1) ~ structure (ii-3-4.3), structure (ii-3-5.1) ~ structure ( ii-3-5.3), structural formula (ii-3-6.1) ~ structural formula (ii-3-6.2), structural formula (ii-4-1.1) ~ structural formula (ii-4-1.3), structural formula (ii-4-2.1) ~ structural formula (ii-4-2.3), structural formula (ii-4-3.1) ~ structural formula (ii-4-3.3), structural formula (ii-4-4.1) ~ structural formula (ii-4-4.3), structural formula (ii-4-5.1) ~ structural formula (ii-4-5.3), structural formula (ii-4-6.1) ~ structural formula (ii-4-6.3), structural formula (ii-4-7.1) ~ structural formula (ii-4-7.3), structural formula (ii-4-8.1) ~ Structure (ii-4-8.3), Structure (ii-4-9.1) to Structure (ii-4-9.4), Structure (ii-4-10.1) to Structure (ii-4-10.5), Structure (ii-4-11.1) to Structure (ii-4-11.4), Structure (ii-4-12.1) to Structure (ii-4-12.5), Structure (ii-4-13.1) to Structure (ii-4-13.8), Structure (ii-4-14.1) to Structure (ii-4-14.4), Structure (ii-4-15.1) to Structure (ii-4-15.4), Structure (ii-4-16.1), Structure (ii-4-17).1) Structure (ii-5-1.1) ~ Structure (ii-5-1.4), Structure (ii-5-2.1) ~ Structure (ii-5-2.4), Structure (ii-5-3.1) ~ Structure (ii-5-3.3), Structure (ii-5-4.1) ~ Structure (ii-5-4.3), Structure (ii-5-5.1), Structure (ii-6-1.1) ~ Structure (ii-6-1.4), Structure (ii-6-2.1) ~ Structure (ii-6-2.4), Structure (ii-6-3.1) ~ Structure (ii-6-3.4), Structure (ii-6-4.1) ~ Structure (ii-6-4.4), Structure (ii-6 -5.1)~Structure (ii-6-5.8), Structure (ii-6-6.1)~Structure (ii-6-6.2), Structure (ii-6-7.1)~Structure (ii-6-7.4), Structure (ii-6-8.1)~Structure (ii-6-8.5), Structure (ii-6-9.1)~Structure (ii-6-9.4), Structure (ii-6-10.1), Structure (ii-6-11.1)~Structure (ii-6-11.16), Structure (ii-6-12.1)~Structure (ii-6-12.4), Structure (ii-6-13.1)~Structure (ii-1-13.4), Structure (ii-6-14) .1)~Structure (ii-6-14.4), Structure (ii-6-15.1)~Structure (ii-6-15.4), Structure (ii-1-16.1)~Structure (ii-6-16.5), Structure (ii-6-17.1)~Structure (ii-6-17.2), Structure (ii-6-18.1)~Structure (ii-6-18.5), Structure (ii-6-19.1)~Structure (ii-6-19.14), Structure (ii-6-20.1)~Structure (ii-6-20.4), Structure (ii-6-21.1), Structure (ii-6-22.1)~Structure (ii-6-22.4), Structure ( ii-6-23.1)~Structure (ii-6-23.4), Structure (ii-6-24.1), Structure (ii-6-25.1)~Structure (ii-6-25.4), Structure (ii-6-26.1)~Structure (ii-6-26.4), Structure (ii-6-27.1)~Structure (ii-6-27.16), Structure (ii-6-28.1)~Structure (ii-6-28.5), Structure (ii-6-29.1)~Structure (ii-6-29.5), Structure (ii-6-30.1)~Structure (ii-6-30.4), Structure (ii-6-31.1), Structure (ii-6-32).1) The upper limit of the total content of the compounds represented by structural formulas (ii-6-33.1) to (ii-6-33.4), (ii-6-34.1), or (ii-7-1.1) in 100% by mass of the liquid crystal composition is preferably 95% by mass or less, preferably 85% by mass or less, preferably 75% by mass or less, preferably 65% ​​by mass or less, preferably 55% by mass or less, preferably 45% 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.

[0974] Regarding solubility, Δn and / or Δε rFrom the perspective of [the relevant context], general formula (ii), general formula (ii-1) to general formula (ii-7), general formula (ii-1-1) to general formula (ii-1-2), general formula (ii-2-1) to general formula (ii-2-5), general formula (ii-3-1) to general formula (ii-3-6), general formula (ii-4-1) to general formula (ii-4-17), general formula (ii-5-1) to general formula (ii-5-5), general formula (ii-6-1) to general formula (ii-6-34), general formula (ii-7-1), 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), and structural formula (ii-2-1.1) to structural formula [the relevant context] (ii-2-1.5), structural formula (ii-2-2.1) ~ structural formula (ii-2-2.3), structural formula (ii-2-3.1) ~ structural formula (ii-2-3.3), structural formula (ii-2-4.1) ~ structural formula (ii-2-4.3), structural formula (ii-2-5.1) ~ structural formula (ii-2-5.3), structural formula (ii-3-1.1) ~ structural formula (ii-3-1.4), structural formula (ii-3-2.1) ~ structural formula (ii-3-2.3), structural formula (ii-3-3.1) ~ structural formula (ii-3-3.3), structural formula (ii-3-4.1) ~ structural formula (ii-3-4.3), structural formula (ii-3-5.1) ~ structural formula (ii-3-5.1) ~ structural formula (ii-3-1.4), structural formula (ii-3-2.1) ~ structural formula (ii-3-2.3), structural formula (ii-3-3.1) ~ structural formula (ii-3-4.3), structural formula (ii-3-5.1) ~ structural formula (ii-3-5.1) ~ structural formula (ii-3-2-2.3), structural formula (ii-3-3-2.3), structural formula (ii-3-4.1) ~ structural formula (ii-3-4.3), structural formula (ii-3-5.1) ~ structural formula (ii-3-2-2.3), structural formula (ii-3-2-2.3), structural formula (ii-3-3-2.3), structural formula (ii-3-3-4.1) ~ structural formula (ii-3-4.3), structural formula (ii-3-5.1) ~ structural formula (ii-3-2-2.3), structural formula (ii-2 ... Construction formula (ii-3-5.3), structural formula (ii-3-6.1) ~ structural formula (ii-3-6.2), structural formula (ii-4-1.1) ~ structural formula (ii-4-1.3), structural formula (ii-4-2.1) ~ structural formula (ii-4-2.3), structural formula (ii-4-3.1) ~ structural formula (ii-4-3.3), structural formula (ii-4-4.1) ~ structural formula (ii-4-4.3), structural formula (ii-4-5.1) ~ structural formula (ii-4-5.3), structural formula (ii-4-6.1) ~ structural formula (ii-4-6.3), structural formula (ii-4-7.1) ~ structural formula (ii-4-7.3), structural formula (ii-4-8.1) ~Structure (ii-4-8.3), Structure (ii-4-9.1) ~Structure (ii-4-9.4), Structure (ii-4-10.1) ~Structure (ii-4-10.5), Structure (ii-4-11.1) ~Structure (ii-4-11.4), Structure (ii-4-12.1) ~Structure (ii-4-12.5), Structure (ii-4-13.1) ~Structure (ii-4-13.8), Structure (ii-4-14.1) ~Structure (ii-4-14.4), Structure (ii-4-15.1) ~Structure (ii-4-15.4), Structure (ii-4-16.1), Structure (ii-4-17).1) Structure (ii-5-1.1) ~ Structure (ii-5-1.4), Structure (ii-5-2.1) ~ Structure (ii-5-2.4), Structure (ii-5-3.1) ~ Structure (ii-5-3.3), Structure (ii-5-4.1) ~ Structure (ii-5-4.3), Structure (ii-5-5.1), Structure (ii-6-1.1) ~ Structure (ii-6-1.4), Structure (ii-6-2.1) ~ Structure (ii-6-2.4), Structure (ii-6-3.1) ~ Structure (ii-6-3.4), Structure (ii-6-4.1) ~ Structure (ii-6-4.4), Structure (ii-6 -5.1)~Structure (ii-6-5.8), Structure (ii-6-6.1)~Structure (ii-6-6.2), Structure (ii-6-7.1)~Structure (ii-6-7.4), Structure (ii-6-8.1)~Structure (ii-6-8.5), Structure (ii-6-9.1)~Structure (ii-6-9.4), Structure (ii-6-10.1), Structure (ii-6-11.1)~Structure (ii-6-11.16), Structure (ii-6-12.1)~Structure (ii-6-12.4), Structure (ii-6-13.1)~Structure (ii-1-13.4), Structure (ii-6-14) .1)~Structure (ii-6-14.4), Structure (ii-6-15.1)~Structure (ii-6-15.4), Structure (ii-1-16.1)~Structure (ii-6-16.5), Structure (ii-6-17.1)~Structure (ii-6-17.2), Structure (ii-6-18.1)~Structure (ii-6-18.5), Structure (ii-6-19.1)~Structure (ii-6-19.14), Structure (ii-6-20.1)~Structure (ii-6-20.4), Structure (ii-6-21.1), Structure (ii-6-22.1)~Structure (ii-6-22.4), Structure ( ii-6-23.1)~Structure (ii-6-23.4), Structure (ii-6-24.1), Structure (ii-6-25.1)~Structure (ii-6-25.4), Structure (ii-6-26.1)~Structure (ii-6-26.4), Structure (ii-6-27.1)~Structure (ii-6-27.16), Structure (ii-6-28.1)~Structure (ii-6-28.5), Structure (ii-6-29.1)~Structure (ii-6-29.5), Structure (ii-6-30.1)~Structure (ii-6-30.4), Structure (ii-6-31.1), Structure (ii-6-32).1) The total content of the compounds represented by structural formulas (ii-6-33.1) to (ii-6-33.4), (ii-6-34.1), or (ii-7-1.1) in 100% by mass of the liquid crystal composition is preferably 10% to 95% by mass, more preferably 15% to 85% by mass, and more preferably 20% to 75% by mass.

[0975] Furthermore, it is preferred to be 1% to 50% by mass, preferably 1% to 45% by mass, preferably 3% to 40% by mass, preferably 3% to 35% by mass, preferably 3% to 25% by mass, and preferably 3% to 15% by mass.

[0976] Compounds represented by general formula (ii) (including sub-concepts) can be synthesized using well-known synthetic methods.

[0977] Regarding V th Δn and / or Δε r From this perspective, the liquid crystal composition of the present invention may also further comprise one or more compounds represented by the following general formula (v) having at least one -C≡C- and a cyano group (-CN) as a linking group.

[0978] [Chemistry 184]

[0979]

[0980] In general formula (v), R v1 Alkyl groups having 1 to 20 carbon atoms.

[0981] The alkyl group is a straight-chain, branched, or cyclic alkyl group, preferably a straight-chain alkyl group.

[0982] The alkyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6.

[0983] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0984] In addition, one or more of the -CH2-CH2- groups of the alkyl group may be independently substituted by -CH=CH-, -CO-O-, -O-CO- and / or -C≡C-.

[0985] In addition, one or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[0986] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[0987] Wherein, when the alkyl group is substituted by a specified group, oxygen atoms do not bond directly to oxygen atoms.

[0988] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[0989] For example, R v1 An alkoxy group with 1 to 19 carbon atoms can be represented by replacing one of the -CH2- groups with -O- groups.

[0990] The alkoxy group is a straight-chain, branched, or cyclic alkoxy group, preferably a straight-chain alkoxy group.

[0991] The alkoxy group preferably has 2 to 10 carbon atoms, more preferably 2 to 6.

[0992] Additionally, R v1 By R v1 One of the -CH2- groups is replaced with -S-, which can represent an alkyl mercapto (alkyl thio) group with 1 to 19 carbon atoms.

[0993] The alkyl thiol group is a linear, branched, or cyclic alkyl thiol group, preferably a linear alkyl thiol group.

[0994] The alkyl mercapto group preferably has 2 to 10 carbon atoms, more preferably 2 to 6.

[0995] Additionally, R v1 An alkenyl group with 2 to 20 carbon atoms can be represented by replacing one or more of the -CH2-CH2- groups with -CH=CH- groups.

[0996] The alkenyl group is a linear, branched, or cyclic alkenyl group, preferably a linear alkenyl group.

[0997] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6.

[0998] Additionally, R v1 An alkynyl group with 2 to 20 carbon atoms can be represented by replacing one or more of the -CH2-CH2- groups with -C≡C- groups.

[0999] The alkynyl group is a straight-chain, branched, or cyclic alkynyl group, preferably a straight-chain alkynyl group.

[1000] The number of carbon atoms in the alkynyl group is preferably 2 to 10, and more preferably 2 to 6.

[1001] Additionally, R v1An alkyl group having 2 to 19 carbon atoms can be represented by replacing one of the -CH2- atoms with -O- atoms and replacing one or more of the -CH2-CH2- atoms with -CH=CH- atoms.

[1002] The olefinic group is a straight-chain, branched, or cyclic olefinic group, preferably a straight-chain olefinic group.

[1003] The number of carbon atoms in the olefinic group is preferably 2 to 10, and more preferably 2 to 6.

[1004] Additionally, R v1 By replacing one or more hydrogen atoms of the alkyl group with halogen atoms, a alkyl halide with 1 to 20 carbon atoms can be represented.

[1005] The alkyl halide is a straight-chain, branched, or cyclic alkyl halide, preferably a straight-chain alkyl halide.

[1006] The number of carbon atoms in the alkyl halide is preferably 2 to 10, and more preferably 2 to 6.

[1007] Additionally, R v1 A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- atom of the alkyl group with -O- atom and replacing one or more hydrogen atoms of the alkyl group with halogen atoms.

[1008] The halogenated alkoxy group is a straight-chain, branched, or cyclic halogenated alkoxy group, preferably a straight-chain halogenated alkoxy group.

[1009] The number of carbon atoms in the haloalkoxy group is preferably 2 to 10, and more preferably 2 to 6.

[1010] As R v1 Specific examples of alkyl groups having 1 to 20 carbon atoms (including substituted alkyl groups) can be listed in formula (R). v1 -1)~Formula (R) v1 -36) represents the base.

[1011] [Chemistry 185]

[1012]

[1013] Formula (R) v1 -1)~Formula (R) v1 In -36), the black dot represents the direction to A. v1 The bond structure.

[1014] In R v1 When the bonded ring structure is phenyl (aromatic), it is preferably a straight-chain alkyl group with 1 to 5 carbon atoms, a straight-chain alkoxy group with 1 to 4 carbon atoms, or an alkenyl group with 4 to 5 carbon atoms. In Rv1 When the bonded ring structure is a saturated ring structure such as cyclohexane, pyran, or dioxane, it is preferably a straight-chain alkyl group with 1 to 5 carbon atoms, a straight-chain alkoxy group with 1 to 4 carbon atoms, or a straight-chain alkenyl group with 2 to 5 carbon atoms.

[1015] Additionally, as R v1 In order to stabilize the nematic phase, the total number of carbon atoms and oxygen atoms (if present) is preferably 5 or less, and preferably linear.

[1016] In addition, as R v1 From the viewpoint of solubility, a straight-chain alkyl group having 2 to 8 carbon atoms is preferred.

[1017] In general formula (v), A v1 and A v2 Represent the basis(a), basis(b), basis(c), and basis(d) chosen independently:

[1018] (a) 1,4-cyclohexylene (one or more non-adjacent -CH2- groups may be replaced by -O- and / or -S-)

[1019] (b) 1,4-Phenylidene (one or more -CH= groups may be substituted with -N=)

[1020] (c) Naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one or more -CH= in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl can be replaced by -N=)

[1021] (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 or more -CH= groups may be substituted with -N=)

[1022] The base in the group formed by the group.

[1023] A v1 and A v2 One or more hydrogen atoms can be independently replaced by substituents S. v1 replace.

[1024] Substituent S v1 It represents any one of a halogen atom, a cyano group, or an alkyl group having 1 to 6 carbon atoms.

[1025] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[1026] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[1027] In addition, one or more hydrogen atoms present in the alkyl group can be independently replaced by halogen atoms.

[1028] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[1029] In cases where alkyl groups with 1 to 6 carbon atoms are substituted by specified groups, oxygen atoms do not bond directly to each other.

[1030] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[1031] In addition, A v1 At least one or A v2 Preferably, it consists of at least one substituent S v1 replace.

[1032] Furthermore, in the substituent S v1 When multiple instances exist, these can be the same or different.

[1033] As A v1 The substituent S in v1 From the viewpoint of solubility, the substitution position is preferably that of the following formula (A) v1 -SP-1).

[1034] [Chemistry 186]

[1035]

[1036] Formula (A) v1 In -SP-1), the white dot indicates the direction to R. v1 or Z v1 The bond is represented by black dots indicating the Z-axis. v1 The bond structure.

[1037] As A v2 The substituent S in v1 The replacement position is preferably that of the following formula (A) v2 -SP-1)~Form (A) v2 Any of the following (-SP-2).

[1038] [Chemistry 187]

[1039]

[1040] Formula (A) v2 -SP-1)~Form (A) v2 In -SP-2), the white dot indicates the direction of Z. v1 The black dots represent bonds to the cyano group (-CN).

[1041] More specifically, A v1 Preferably, it represents the following formula (A) v1 -1)~Form (A) v1 Any of the following: -3)

[1042] [Chem.188]

[1043]

[1044] Formula (A) v1 -1)~Form (A) v1 In -3), the white dot represents the direction to R. v1 or Z v1 The bond is represented by black dots indicating the Z-axis. v1 The bond structure.

[1045] More specifically, A v2 Preferably, it represents the following formula (A) v2 -1)~Form (A) v2 Any of -3).

[1046] [Chemistry 189]

[1047]

[1048] Formula (A) v2 -1)~Form (A) v2 In -3), the white dot represents the direction of Z. v1 The black dots represent bonds to the cyano group (-CN).

[1049] In general formula (v), Z v1 It represents any one of the following: a single bond, -C≡C-, -CH=CH-, and -CF=CF-.

[1050] Among them, Z v1 At least one of the following is represented as -C≡C-.

[1051] In the general formula (v), n v1 Represents an integer from 1 to 2.

[1052] Furthermore, in general formula (v), in A v1 and Z v1 When multiple instances exist, these instances can be the same or different.

[1053] The compounds represented by general formula (v) are preferably those represented by general formulas (v-1) to (v-2).

[1054] [Chemistry 190]

[1055]

[1056] In general formulas (v-1) to (v-2), R v1 A v1 and A v2 R represents the expression in the general formula (v). v1 A v1 and A v2 They have the same meaning, respectively.

[1057] In general formulas (v-1) to (v-2), A v1-2 The definition of A in the general formula (v) v1 The definitions are the same.

[1058] The compounds represented by general formula (v-1) are preferably those represented by general formulas (v-1-1) to (v-1-6).

[1059] [Chemistry 191]

[1060]

[1061] In general formulas (v-1-1) to (v-1-6), R v1 and S v1 Each independently represents R in the general formula (v). v1 and S v1 They have the same meaning, respectively.

[1062] Specific examples of compounds represented by the general formula (v-1-1) include compounds represented by the following structural formulas (v-1-1.1) to (v-1-1.3).

[1063] [Chemistry 192]

[1064]

[1065] Specific examples of compounds represented by general formula (v-1-2) include compounds represented by structural formulas (v-1-2.1) to (v-1-2.3).

[1066] [Chemistry 193]

[1067]

[1068] Specific examples of compounds represented by general formula (v-1-3) include compounds represented by structural formulas (v-1-3.1) to (v-1-3.3).

[1069] [Chemistry 194]

[1070]

[1071] Specific examples of compounds represented by general formula (v-1-4) include compounds represented by the following structural formulas (v-1-4.1) to (ii-1-4.3).

[1072] [Chemistry 195]

[1073]

[1074] Specific examples of compounds represented by general formula (v-1-5) include compounds represented by the following structural formulas (v-1-5.1) to (v-1-5.3).

[1075] [Chemistry 196]

[1076]

[1077] Specific examples of compounds represented by general formula (v-1-6) include compounds represented by structural formulas (v-1-6.1) to (v-1-6.3).

[1078] [Chemistry 197]

[1079]

[1080] The compounds represented by general formula (v-2) are preferably those represented by general formulas (v-2-1) to (v-2-2).

[1081] [Chemistry 198]

[1082]

[1083] In general formulas (v-2-1) to (v-2-2), R v1 and S v1 Each independently represents R in the general formula (v). v1 and S v1 They have the same meaning, respectively.

[1084] Specific examples of compounds represented by the general formula (v-2-1) include compounds represented by the following structural formulas (v-2-1.1) to (v-2-1.3).

[1085] [Chemistry 199]

[1086]

[1087] Specific examples of compounds represented by the general formula (v-2-2) include compounds represented by the following structural formulas (v-2-2.1) to (v-2-2.3).

[1088] [Chem.200]

[1089]

[1090] General formula (v), general formula (v-1) to general formula (v-2), general formula (v-1-1) to general formula (v-1-6), general formula (v-2-1) to general formula (v-2-2), structural formula (v-1-1.1) to structural formula (v-1-1.3), structural formula (v-1-2.1) to structural formula (v-1-2.3), structural formula (v-1-3.1) to structural formula (v-1-3.3), structural formula (v-1-4.1) to structural formula (v-1-4.3), structural formula The compounds represented by (v-1-5.1) to (v-1-5.3), (v-1-6.1) to (v-1-6.3), (v-2-1.1) to (v-2-1.3), or (v-2-2.1) to (v-2-2.3) are used in the liquid crystal composition in one or more types, preferably one to five types, preferably one to four types, preferably one to three types, preferably one to two types, and preferably one type.

[1091] General formula (v), general formula (v-1) to general formula (v-2), general formula (v-1-1) to general formula (v-1-6), general formula (v-2-1) to general formula (v-2-2), structural formula (v-1-1.1) to structural formula (v-1-1.3), structural formula (v-1-2.1) to structural formula (v-1-2.3), structural formula (v-1-3.1) to structural formula (v-1-3.3), structural formula (v-1-4.1) to structural formula (v-1-4.3). The lower limit of the total content of the compounds represented by structural formulas (v-1-5.1) to (v-1-5.3), (v-1-6.1) to (v-1-6.3), (v-2-1.1) to (v-2-1.3), or (v-2-2.1) to (v-2-2.3) in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, preferably 3% by mass or more, and preferably 5% by mass or more.

[1092] General formula (v), general formula (v-1) to general formula (v-2), general formula (v-1-1) to general formula (v-1-6), general formula (v-2-1) to general formula (v-2-2), structural formula (v-1-1.1) to structural formula (v-1-1.3), structural formula (v-1-2.1) to structural formula (v-1-2.3), structural formula (v-1-3.1) to structural formula (v-1-3.3), structural formula (v-1-4.1) to structural formula (v-1-4.3) The upper limit of the total content of the compounds represented by structural formulas (v-1-5.1) to (v-1-5.3), (v-1-6.1) to (v-1-6.3), (v-2-1.1) to (v-2-1.3), or (v-2-2.1) to (v-2-2.3) in 100% by mass of the liquid crystal composition is preferably 30% by mass or less, preferably 25% by mass or less, and preferably 20% by mass or less.

[1093] Regarding solubility and / or V th From this perspective, the general formulas (v), (v-1) to (v-2), (v-1-1) to (v-1-6), (v-2-1) to (v-2-2), (v-1-1.1) to (v-1-1.3), (v-1-2.1) to (v-1-2.3), (v-1-3.1) to (v-1-3.3), and (v-1-4.1) to (v-1-4.3) are all related to this concept. The total content of the compounds represented by structural formulas (v-1-5.1) to (v-1-5.3), (v-1-6.1) to (v-1-6.3), (v-2-1.1) to (v-2-1.3), or (v-2-2.1) to (v-2-2.3) in 100% by mass of the liquid crystal composition is preferably 1% to 30% by mass, preferably 3% to 25% by mass, and preferably 5% to 20% by mass.

[1094] Compounds represented by general formula (v) (including sub-concepts) can be synthesized using well-known synthetic methods.

[1095] Regarding Δn and / or Δε r From this perspective, the liquid crystal composition of the present invention may also further comprise one or more compounds represented by the following general formula (vi) having at least one -C≡C- as a linking group.

[1096] [Chemical Engineering 201]

[1097]

[1098] In general formula (vi), Rvi1 An alkyl group having 1 to 20 hydrogen or carbon atoms.

[1099] The alkyl group having 1 to 20 carbon atoms is a straight-chain, branched, or cyclic alkyl group, preferably a straight-chain alkyl group.

[1100] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1101] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[1102] In addition, one or more of the -CH2-CH2- groups 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-.

[1103] In addition, one or more of the -CH2-CH2-CH2- alkyl groups can be independently substituted by -O-CO-O-.

[1104] In addition, one or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[1105] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[1106] Wherein, when the alkyl group is substituted by a specified group, oxygen atoms do not bond directly to oxygen atoms.

[1107] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[1108] For example, R vi1 An alkoxy group with 1 to 19 carbon atoms can be represented by replacing one of the -CH2- groups with -O- groups.

[1109] The alkoxy group is a straight-chain, branched, or cyclic alkoxy group, preferably a straight-chain alkoxy group.

[1110] The alkoxy group preferably has 2 to 10 carbon atoms, more preferably 2 to 6.

[1111] Additionally, R vi1 By replacing one of the -CH2- groups in the alkyl group with -S-, an alkyl mercapto group (alkyl thio group) with 1 to 19 carbon atoms can be represented.

[1112] The alkyl thiol group is a linear, branched, or cyclic alkyl thiol group, preferably a linear alkyl thiol group.

[1113] The alkyl mercapto group preferably has 1 to 10 carbon atoms, and more preferably 1 to 6.

[1114] Additionally, R vi1 An alkenyl group with 2 to 20 carbon atoms can be represented by replacing one or more of the -CH2-CH2- groups with -CH=CH- groups.

[1115] The alkenyl group is a linear, branched, or cyclic alkenyl group, preferably a linear alkenyl group.

[1116] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6.

[1117] Additionally, R vi1 An alkynyl group with 2 to 20 carbon atoms can be represented by replacing one or more of the -CH2-CH2- groups with -C≡C- groups.

[1118] The alkynyl group is a straight-chain, branched, or cyclic alkynyl group, preferably a straight-chain alkynyl group.

[1119] The number of carbon atoms in the alkynyl group is preferably 2 to 10, and more preferably 2 to 6.

[1120] Additionally, R vi1 An alkyl group having 2 to 19 carbon atoms can be represented by replacing one of the -CH2- atoms with -O- atoms and replacing one or more of the -CH2-CH2- atoms with -CH=CH- atoms.

[1121] The olefinic group is a straight-chain, branched, or cyclic olefinic group, preferably a straight-chain olefinic group.

[1122] The number of carbon atoms in the olefinic group is preferably 2 to 10, and more preferably 2 to 6.

[1123] Additionally, R vi1 By replacing one or more hydrogen atoms of the alkyl group with halogen atoms, a alkyl halide with 1 to 20 carbon atoms can be represented.

[1124] The alkyl halide is a straight-chain, branched, or cyclic alkyl halide, preferably a straight-chain alkyl halide.

[1125] The number of carbon atoms in the alkyl halide is preferably 2 to 10, and more preferably 2 to 6.

[1126] Additionally, R vi1A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- atom of the alkyl group with -O- atom and replacing one or more hydrogen atoms of the alkyl group with halogen atoms.

[1127] The halogenated alkoxy group is a straight-chain, branched, or cyclic halogenated alkoxy group, preferably a straight-chain halogenated alkoxy group.

[1128] The number of carbon atoms in the haloalkoxy group is preferably 2 to 10, and more preferably 2 to 6.

[1129] As R vi1 Specific examples of alkyl groups having 1 to 20 carbon atoms (including substituted alkyl groups) can be listed in formula (R). vi1 -1)~Formula (R) vi1 -36) represents the base.

[1130] [Chemical Engineering 202]

[1131]

[1132] Formula (R) vi1 -1)~Formula (R) vi1 In -36), the black dot represents the direction to A. vi1 The bond structure.

[1133] While prioritizing the overall reliability of the liquid crystal composition, R vi1 Preferably, it is an alkyl group having 1 to 12 carbon atoms. While prioritizing the reduction of the overall viscosity of the liquid crystal composition, R... vi1 Preferably, it is an alkenyl group with 2 to 8 carbon atoms.

[1134] In R vi1 When the bonded ring structure is phenyl (aromatic), it is preferably a straight-chain alkyl group with 1 to 5 carbon atoms, a straight-chain alkoxy group with 1 to 4 carbon atoms, or an alkenyl group with 4 to 5 carbon atoms. In R vi1 When the bonded ring structure is a saturated ring structure such as cyclohexane, pyran, or dioxane, it is preferably a straight-chain alkyl group with 1 to 5 carbon atoms, a straight-chain alkoxy group with 1 to 4 carbon atoms, or a straight-chain alkenyl group with 2 to 5 carbon atoms.

[1135] Additionally, as R vi1 In order to stabilize the nematic phase, the total number of carbon atoms and oxygen atoms (if present) is preferably 5 or less, and preferably linear.

[1136] In addition, as R vi1 From the viewpoint of solubility, linear alkyl groups with 2 to 6 carbon atoms or linear alkyl mercapto groups with 1 to 6 carbon atoms are preferred.

[1137] In general formula (vi), R vi2 It represents any one of the following: hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorothiol, nitro, cyano, isocyano, amino, hydroxyl, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, or alkyl group having 1 to 20 carbon atoms.

[1138] The alkyl group having 1 to 20 carbon atoms is a straight-chain, branched, or cyclic alkyl group, preferably a straight-chain alkyl group.

[1139] The alkyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6.

[1140] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[1141] In addition, one or more of the -CH2-CH2- groups 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-.

[1142] In addition, one or more of the -CH2-CH2-CH2- alkyl groups can be independently substituted by -O-CO-O-.

[1143] In addition, one or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[1144] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[1145] Wherein, when the alkyl group is substituted by a specified group, oxygen atoms do not bond directly to oxygen atoms.

[1146] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[1147] For example, R vi2 An alkoxy group with 1 to 19 carbon atoms can be represented by replacing one of the -CH2- groups with -O- groups.

[1148] The alkoxy group is a straight-chain, branched, or cyclic alkoxy group, preferably a straight-chain alkoxy group.

[1149] The alkoxy group preferably has 2 to 10 carbon atoms, more preferably 2 to 6.

[1150] Additionally, R vi2By replacing one of the -CH2- groups in the alkyl group with -S-, an alkyl mercapto group (alkyl thio group) with 1 to 19 carbon atoms can be represented.

[1151] The alkyl thiol group is a linear, branched, or cyclic alkyl thiol group, preferably a linear alkyl thiol group.

[1152] The alkyl mercapto group preferably has 1 to 10 carbon atoms, and more preferably 1 to 6.

[1153] Additionally, R vi2 An alkenyl group with 2 to 20 carbon atoms can be represented by replacing one or more of the -CH2-CH2- groups with -CH=CH- groups.

[1154] The alkenyl group is a linear, branched, or cyclic alkenyl group, preferably a linear alkenyl group.

[1155] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6.

[1156] Additionally, R vi2 An alkynyl group with 2 to 20 carbon atoms can be represented by replacing one or more of the -CH2-CH2- groups with -C≡C- groups.

[1157] The alkynyl group is a straight-chain, branched, or cyclic alkynyl group, preferably a straight-chain alkynyl group.

[1158] The number of carbon atoms in the alkynyl group is preferably 2 to 10, and more preferably 2 to 6.

[1159] Additionally, R vi2 An alkyl group having 2 to 19 carbon atoms can be represented by replacing one of the -CH2- atoms with -O- atoms and replacing one or more of the -CH2-CH2- atoms with -CH=CH- atoms.

[1160] The olefinic group is a straight-chain, branched, or cyclic olefinic group, preferably a straight-chain olefinic group.

[1161] The number of carbon atoms in the olefinic group is preferably 2 to 10, and more preferably 2 to 6.

[1162] Additionally, R vi2 By replacing one or more hydrogen atoms of the alkyl group with halogen atoms, a alkyl halide with 1 to 20 carbon atoms can be represented.

[1163] The alkyl halide is a straight-chain, branched, or cyclic alkyl halide, preferably a straight-chain alkyl halide.

[1164] The number of carbon atoms in the alkyl halide is preferably 2 to 10, and more preferably 2 to 6.

[1165] Additionally, R vi2 A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- atom of the alkyl group with -O- atom and replacing one or more hydrogen atoms of the alkyl group with halogen atoms.

[1166] The halogenated alkoxy group is a straight-chain, branched, or cyclic halogenated alkoxy group, preferably a straight-chain halogenated alkoxy group.

[1167] The number of carbon atoms in the haloalkoxy group is preferably 2 to 10, and more preferably 2 to 6.

[1168] As R vi2 Specific examples of alkyl groups having 1 to 20 carbon atoms (including substituted alkyl groups) can be listed in formula (R). vi2 -1)~Formula (R) vi2 -36) represents the base.

[1169] [Chemical Engineering 203]

[1170]

[1171] Formula (R) vi2 -1)~Formula (R) vi2 In -36), the black dot represents the direction to A. vi3 The bond structure.

[1172] In R vi2 When the bonded ring structure is phenyl (aromatic), it is preferably a straight-chain alkyl group with 1 to 5 carbon atoms, a straight-chain alkoxy group with 1 to 4 carbon atoms, or an alkenyl group with 4 to 5 carbon atoms. In R vi1 When the bonded ring structure is a saturated ring structure such as cyclohexane, pyran, or dioxane, it is preferably a straight-chain alkyl group with 1 to 5 carbon atoms, a straight-chain alkoxy group with 1 to 4 carbon atoms, or a straight-chain alkenyl group with 2 to 5 carbon atoms.

[1173] Additionally, as R vi2 In order to stabilize the nematic phase, the total number of carbon atoms and oxygen atoms (if present) is preferably 5 or less, and preferably linear.

[1174] In addition, as R vi2 Regarding solubility, Δn and / or Δε r From this perspective, the preferred groups are fluorine atoms, cyano groups, straight-chain alkyl groups with 2 to 6 carbon atoms, straight-chain alkoxy groups with 1 to 6 carbon atoms, or straight-chain alkyl mercapto groups with 1 to 6 carbon atoms.

[1175] In the general formula (vi), A vi1 A vi2 and A vi3Each can be independently represented as either a hydrocarbon ring with 3 to 16 carbon atoms or a heterocycle with 3 to 16 carbon atoms.

[1176] Hydrocarbon rings having 3 to 16 carbon atoms or heterocycles having 3 to 16 carbon atoms, more specifically preferably represented by groups (a), (b), (c), and (d) selected from the following:

[1177] (a) 1,4-cyclohexylene (one or more non-adjacent -CH2- groups may be replaced by -O- or -S-).

[1178] (b) 1,4-Phenylidene (one or more -CH= groups may be substituted with -N=)

[1179] (c) 1,4-cyclohexenyl, bicyclo[2.2.2]octane-1,4-diyl, naphth-2,6-diyl, naphth-1,4-diyl, 1,2,3,4-tetrahydronaphth-2,6-diyl, 5,6,7,8-tetrahydronaphth-1,4-diyl, decahydronaphth-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene -2,7-Diyl (one 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 can be substituted with -N=)

[1180] (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 or more -CH= groups may be substituted with -N=)

[1181] The base in the group formed by the group.

[1182] A vi1 A vi2 and A vi3 One or more hydrogen atoms can be independently replaced by substituents S. vi1 replace.

[1183] Substituent S vi1 It represents any one of the following: fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorothiol, nitro, cyano, isocyano, amino, hydroxyl, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyano, or alkyl with 1 to 20 carbon atoms.

[1184] The alkyl group is a straight-chain, branched, or cyclic alkyl group, preferably a straight-chain alkyl group.

[1185] The alkyl group preferably has 2 to 10 carbon atoms, and more preferably 3 to 6.

[1186] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S- and / or -CO-.

[1187] In addition, one or more of the -CH2-CH2- groups 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-.

[1188] In addition, one or more of the -CH2-CH2-CH2- alkyl groups may be replaced by -O-CO-O-.

[1189] One or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[1190] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[1191] Wherein, when the alkyl group is substituted by a specified group, oxygen atoms do not bond directly to oxygen atoms.

[1192] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[1193] As a substituent S vi1 Preferably, it is a straight-chain alkyl group with fluorine atoms or 1 to 3 carbon atoms.

[1194] In addition, A vi1 A vi2 and A vi3 At least one of them is preferably composed of at least one substituent S vi1 replace.

[1195] In addition, A vi1 Preferably, it consists of at least one substituent S vi1 replace.

[1196] Furthermore, in the substituent S vi1 When multiple instances exist, these can be the same or different.

[1197] As A vi1 The substituent S in vi1 The replacement position is preferably that of the following formula (A) vi1-SP-1)~Form (A) vi1 Any of the following (-SP-3).

[1198] [Chemical 204]

[1199]

[1200] Formula (A) vi1 -SP-1)~Form (A) vi1 In -SP-3), the white dot represents R. vi1 The black dots represent the bonds between -C≡C-.

[1201] As A vi2 The substituent S in vi1 The replacement position is preferably that of the following formula (A) vi2 -SP-1)~Form (A) vi2 From the viewpoint of compatibility with other liquid crystal compounds, any one of (-SP-7) is preferred, which represents the following formula (A) vi2 -SP-1)~Form (A) vi2 Any of the following (-SP-7).

[1202] [Chemical Engineering 205]

[1203]

[1204] Formula (A) vi2 -SP-1)~Form (A) vi2 In -SP-7), white dots represent -C≡C- bonds, and black dots represent Z-bonds. vi1 The bond structure.

[1205] As A vi3 The substituent S in vi3 The replacement position is preferably that of the following formula (A) vi3 -SP-1)~Form (A) vi3 Any of the following (-SP-8), from the viewpoint of solubility, is preferred to represent the following formula (A) vi3 -SP-1)~Form (A) vi3 Any of the following (-SP-5).

[1206] [Chemical Engineering 206]

[1207]

[1208] Formula (A) vi3 -SP-1)~Form (A) vi3 In -SP-8), the white dot indicates the direction of Z. vi1 The bond is represented by black dots indicating the Z-axis. vi1 Or R vi2 The bond structure.

[1209] More specifically, A vi1 Preferably, it represents the following formula (A) vi1 -1)~Form (A) vi1 Any of the following: -5)

[1210] [Chemical Engineering 207]

[1211]

[1212] Formula (A) vi1 -1)~Form (A) vi1 In -5), the white dot represents R. vi1 The black dots represent the bonds between -C≡C-.

[1213] More specifically, A vi2 Preferably, it represents the following formula (A) vi2 -1)~Form (A) vi2 Any of the following: -5)

[1214] [Chemical Engineering 208]

[1215]

[1216] Formula (A) vi2 -1)~Form (A) vi2 In -5), white dots represent -C≡C- bonds, and black dots represent Z-bonds. i1 The bond structure.

[1217] More specifically, A vi3 Preferably, it represents the following formula (A) vi3 -1)~Form (A) vi3 Any of the following: -5)

[1218] [Chemical Engineering 209]

[1219]

[1220] Formula (A) vi3 -1)~Form (A) vi3 In -5), the white dot represents the direction of Z. vi1 The bond is represented by black dots indicating the Z-axis. vi1 Or R vi2 The bond structure.

[1221] In the general formula (vi), Z vi1 Each of the following can be independently represented: a single bond, or an alkylene group having 1 to 20 carbon atoms.

[1222] The alkylene group is a straight-chain, branched, or cyclic alkylene group, preferably a straight-chain alkylene group.

[1223] The alkylene group preferably has 2 to 10 carbon atoms, more preferably 2 to 6.

[1224] One or more of the -CH2- groups in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[1225] In addition, one or more of the -CH2-CH2- groups 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-.

[1226] In addition, one or more of the -CH2-CH2-CH2- alkyl groups can be independently substituted by -O-CO-O-.

[1227] Wherein, when the alkylene group is substituted by a specified group, oxygen atoms do not bond directly to oxygen atoms.

[1228] Specific examples of alkylene groups having 2 to 20 carbon atoms (including substituted alkylene groups) can be enumerated as (Z vi1 -1)~Formula (Z) vi1 -24) represents the base.

[1229] [Chemical 210]

[1230]

[1231] Formula (Z) vi1 -1)~Formula (Z) vi1 In -24), the white dot represents the direction to A. vi2 Or A vi3 The bond, the black dot indicates the bond to A vi3 The bond structure.

[1232] In the general formula (vi), n vi1 It represents an integer from 1 to 3, preferably an integer from 1 to 2.

[1233] In n vi1 When Δn is 1, then Δn and / or Δε r From Z's point of view, vi1 Preferably, it represents -C≡C-.

[1234] Additionally, in n vi1 In the case of 2 or 3, then Δn and / or Δε r From Z's point of view, vi1 At least one of them is preferably represented as -C≡C-.

[1235] Furthermore, in the general formula (vi), in A vi3 and Z vi1 When multiple instances exist, these instances can be the same or different.

[1236] The compound represented by the general formula (vi) is preferably the compound represented by the following general formula (vi-1).

[1237] [Chemistry 211]

[1238]

[1239] In general formula (vi-1), R vi1 R vi2 A vi1 A vi2 and A vi3 R in the general formula (vi) vi1 R vi2 A vi1 A vi2 and A vi3 They have the same meaning, respectively.

[1240] The compounds represented by general formula (vi-1) are preferably those represented by general formulas (vi-1-1) to (vi-1-12).

[1241] [Chemistry 212]

[1242]

[1243] [Chemistry 213]

[1244]

[1245] In general formulas (vi-1-1) to (vi-1-12), R vi1 R vi2 and S vi1 Each independently represents R in the general formula (vi). vi1 R vi2 and S vi1 They have the same meaning, respectively.

[1246] Specific examples of compounds represented by the general formula (vi-1-1) include compounds represented by the following structural formulas (vi-1-1.1) to (vi-1-1.24).

[1247] [Chemistry 214]

[1248]

[1249] [Chemical 215]

[1250]

[1251] [Chemistry 216]

[1252]

[1253] Specific examples of compounds represented by the general formula (vi-1-2) include compounds represented by the following structural formulas (vi-1-2.1) to (vi-1-2.8).

[1254] [Chemistry 217]

[1255]

[1256] Specific examples of compounds represented by general formula (vi-1-3) include compounds represented by structural formulas (vi-1-3.1) to (vi-1-3.8).

[1257] [Chemistry 218]

[1258]

[1259] Specific examples of compounds represented by general formula (vi-1-4) include compounds represented by structural formulas (vi-1-4.1) to (vi-1-4.8).

[1260] [Chemistry 219]

[1261]

[1262] Specific examples of compounds represented by general formula (vi-1-5) include compounds represented by the following structural formulas (vi-1-5.1) to (vi-1-5.8).

[1263] [Chem.220]

[1264]

[1265] Specific examples of compounds represented by general formula (vi-1-6) include compounds represented by structural formulas (vi-1-6.1) to (vi-1-6.8).

[1266] [Chemistry 221]

[1267]

[1268] Specific examples of compounds represented by general formula (vi-1-7) include compounds represented by the following structural formulas (vi-1-7.1) to (vi-1-7.8).

[1269] [Chemistry 222]

[1270]

[1271] Specific examples of compounds represented by general formula (vi-1-8) include compounds represented by structural formulas (vi-1-8.1) to (vi-1-8.8).

[1272] [Chemistry 223]

[1273]

[1274] Specific examples of compounds represented by general formula (vi-1-9) include compounds represented by the following structural formulas (vi-1-9.1) to (vi-1-9.5).

[1275] [Chemistry 224]

[1276]

[1277] Specific examples of compounds represented by the general formula (vi-1-10) include compounds represented by the following structural formulas (vi-1-10.1) to (vi-1-10.4).

[1278] [Chemistry 225]

[1279]

[1280] Specific examples of compounds represented by the general formula (vi-1-11) include compounds represented by the following structural formulas (vi-1-11.1) to (vi-1-11.4).

[1281] [Chemistry 226]

[1282]

[1283] Specific examples of compounds represented by the general formula (vi-1-12) include compounds represented by the following structural formulas (vi-1-12.1) to (vi-1-12.4).

[1284] [Chemistry 227]

[1285]

[1286] General formula (vi), general formula (vi-1), general formula (vi-1-1) to general formula (vi-1-12), structural formula (vi-1-1.1) to structural formula (vi-1-1.24), structural formula (vi-1-2.1) to structural formula (vi-1-2.8), structural formula (vi-1-3.1) to structural formula (vi-1-3.8), structural formula (vi-1-4.1) to structural formula (vi-1-4.8), structural formula (vi-1-5.1) to structural formula (vi-1-5.8), structural formula (vi-1-6.1) to structural formula (vi-1-6.8), structural formula (vi-1-7.1) to structural formula The compounds represented by (vi-1-7.8), (vi-1-8.1) to (vi-1-8.8), (vi-1-9.1) to (vi-1-9.5), (vi-1-10.1) to (vi-1-10.4), (vi-1-11.1) to (vi-1-11.4), or (vi-1-12.1) to (vi-1-12.4) are used in the liquid crystal composition in one or more types, preferably one to five types, preferably one to four types, preferably one to three types, preferably one to two types, and preferably one type.

[1287] General formula (vi), general formula (vi-1), general formula (vi-1-1) to general formula (vi-1-12), structural formula (vi-1-1.1) to structural formula (vi-1-1.24), structural formula (vi-1-2.1) to structural formula (vi-1-2.8), structural formula (vi-1-3.1) to structural formula (vi-1-3.8), structural formula (vi-1-4.1) to structural formula (vi-1-4.8), structural formula (vi-1-5.1) to structural formula (vi-1-5.8), structural formula (vi-1-6.1) to structural formula (vi-1-6.8), structural formula (vi-1-7.1) The lower limit of the total content of the compounds represented by structural formulas (vi-1-7.8), (vi-1-8.1), (vi-1-8.8), (vi-1-9.1), (vi-1-9.5), (vi-1-10.1), (vi-1-10.4), (vi-1-11.1), (vi-1-11.4), or (vi-1-12.1) to (vi-1-12.4) in 100% by mass of the liquid crystal composition is preferably 0.5% by mass or more, preferably 1% by mass or more, and preferably 3% by mass or more.

[1288] General formula (vi), general formula (vi-1), general formula (vi-1-1) to general formula (vi-1-12), structural formula (vi-1-1.1) to structural formula (vi-1-1.24), structural formula (vi-1-2.1) to structural formula (vi-1-2.8), structural formula (vi-1-3.1) to structural formula (vi-1-3.8), structural formula (vi-1-4.1) to structural formula (vi-1-4.8), structural formula (vi-1-5.1) to structural formula (vi-1-5.8), structural formula (vi-1-6.1) to structural formula (vi-1-6.8), structural formula (vi-1-7.1) The upper limit of the total content of the compounds represented by structural formulas (vi-1-7.8), (vi-1-8.1), (vi-1-8.8), (vi-1-9.1), (vi-1-9.5), (vi-1-10.1), (vi-1-10.4), (vi-1-11.1), (vi-1-11.4), or (vi-1-12.1) to (vi-1-12.4) in 100% by mass of the liquid crystal composition is preferably 25% by mass or less, preferably 20% by mass or less, and preferably 15% by mass or less.

[1289] Regarding solubility, Δn and / or Δε r From the perspective of [the relevant context], the general formula (vi), general formula (vi-1), general formula (vi-1-1) to general formula (vi-1-12), structural formula (vi-1-1.1) to structural formula (vi-1-1.24), structural formula (vi-1-2.1) to structural formula (vi-1-2.8), structural formula (vi-1-3.1) to structural formula (vi-1-3.8), structural formula (vi-1-4.1) to structural formula (vi-1-4.8), structural formula (vi-1-5.1) to structural formula (vi-1-5.8), structural formula (vi-1-6.1) to structural formula (vi-1-6.8), and structural formula (vi-1-7.1) are all [related to the above]. The total content of the compounds represented by structural formulas (vi-1-7.8), (vi-1-8.1) to (vi-1-8.8), (vi-1-9.1) to (vi-1-9.5), (vi-1-10.1) to (vi-1-10.4), (vi-1-11.1) to (vi-1-11.4), or (vi-1-12.1) to (vi-1-12.4) in 100% by mass of the liquid crystal composition is preferably 0.5% to 25% by mass, preferably 1% to 20% by mass, and preferably 3% to 15% by mass.

[1290] Compounds represented by general formula (vi) (including sub-concepts) can be synthesized using well-known synthetic methods.

[1291] Regarding Δn and / or Δε r From the perspective of the present invention, the liquid crystal composition may also further comprise one or more compounds represented by the following general formula (vii) having at least one -C≡C- and -N=N- as linking groups.

[1292] [Chemistry 228]

[1293] R vii1 -A vii1 -C≡CA vii2 -N=NA vii3 -R vii2 (vii)

[1294] In general formula (vii), R vii1 and R vii2 Each of the following can be independently represented: halogen atom, cyano group, and alkyl group with 1 to 20 carbon atoms.

[1295] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[1296] The alkyl group having 1 to 20 carbon atoms is a straight-chain, branched, or cyclic alkyl group, preferably a straight-chain alkyl group.

[1297] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1298] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[1299] In addition, one or more of the -CH2-CH2- groups 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-.

[1300] In addition, one or more of the -CH2-CH2-CH2- alkyl groups can be independently substituted by -O-CO-O-.

[1301] In addition, one or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[1302] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[1303] Wherein, when the alkyl group is substituted by a specified group, oxygen atoms do not bond directly to oxygen atoms.

[1304] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[1305] For example, R vii1 and R vii2 An alkoxy group with 1 to 19 carbon atoms can be represented by replacing one of the -CH2- groups with -O- groups.

[1306] The alkoxy group is a straight-chain, branched, or cyclic alkoxy group, preferably a straight-chain alkoxy group.

[1307] The alkoxy group preferably has 2 to 10 carbon atoms, more preferably 2 to 6.

[1308] Additionally, R vii1 and R vii2 By replacing one of the -CH2- groups in the alkyl group with -S-, an alkyl mercapto group (alkyl thio group) with 1 to 19 carbon atoms can be represented.

[1309] The alkyl thiol group is a linear, branched, or cyclic alkyl thiol group, preferably a linear alkyl thiol group.

[1310] The alkyl mercapto group preferably has 2 to 10 carbon atoms, more preferably 2 to 6.

[1311] Additionally, R vii1 and R vii2 An alkenyl group with 2 to 20 carbon atoms can be represented by replacing one or more of the -CH2-CH2- groups with -CH=CH- groups.

[1312] The alkenyl group is a linear, branched, or cyclic alkenyl group, preferably a linear alkenyl group.

[1313] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6.

[1314] Additionally, R vii1 and R vii2 An alkynyl group with 2 to 20 carbon atoms can be represented by replacing one or more of the -CH2-CH2- groups with -C≡C- groups.

[1315] The alkynyl group is a straight-chain, branched, or cyclic alkynyl group, preferably a straight-chain alkynyl group.

[1316] The number of carbon atoms in the alkynyl group is preferably 2 to 10, and more preferably 2 to 6.

[1317] Additionally, R vii1 and Rvii2 An alkyl group having 2 to 19 carbon atoms can be represented by replacing one of the -CH2- atoms with -O- atoms and replacing one or more of the -CH2-CH2- atoms with -CH=CH- atoms.

[1318] The olefinic group is a straight-chain, branched, or cyclic olefinic group, preferably a straight-chain olefinic group.

[1319] The number of carbon atoms in the olefinic group is preferably 2 to 10, and more preferably 2 to 6.

[1320] Additionally, R vii1 and R vii2 By replacing one or more hydrogen atoms of the alkyl group with halogen atoms, a alkyl halide with 1 to 20 carbon atoms can be represented.

[1321] The alkyl halide is a straight-chain, branched, or cyclic alkyl halide, preferably a straight-chain alkyl halide.

[1322] The number of carbon atoms in the alkyl halide is preferably 2 to 10, and more preferably 2 to 6.

[1323] R vii1 and R vii2 A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- atom of the alkyl group with -O- atom and replacing one or more hydrogen atoms of the alkyl group with halogen atoms.

[1324] The halogenated alkoxy group is a straight-chain, branched, or cyclic halogenated alkoxy group, preferably a straight-chain halogenated alkoxy group.

[1325] The number of carbon atoms in the haloalkoxy group is preferably 2 to 10, and more preferably 2 to 6.

[1326] As R vii1 and R vii2 Specific examples of alkyl groups having 1 to 20 carbon atoms (including substituted alkyl groups) can be listed in formula (R). vii1 / 2 -1)~Formula (R) vii1 / 2 -36) represents the base.

[1327] [Chemistry 229]

[1328]

[1329] Formula (R) vii1 / 2 -1)~Formula (R) vii1 / 2 In -36), the black dot represents the direction to A. vii1 Or A vii3 The bond structure.

[1330] While prioritizing the overall reliability of the liquid crystal composition, R vii1 Preferably, it is an alkyl group having 1 to 12 carbon atoms. While prioritizing the reduction of the overall viscosity of the liquid crystal composition, R... vii1 Preferably, it is an alkenyl group with 2 to 8 carbon atoms.

[1331] Additionally, in R vii1 When the bonded ring structure is phenyl (aromatic), it is preferably a straight-chain alkyl group with 1 to 5 carbon atoms, a straight-chain alkoxy group with 1 to 4 carbon atoms, or an alkenyl group with 4 to 5 carbon atoms. In R vii1 When the bonded ring structure is a saturated ring structure such as cyclohexane, pyran, or dioxane, it is preferably a straight-chain alkyl group with 1 to 5 carbon atoms, a straight-chain alkoxy group with 1 to 4 carbon atoms, or a straight-chain alkenyl group with 2 to 5 carbon atoms.

[1332] Additionally, as R vii1 In order to stabilize the nematic phase, the total number of carbon atoms and oxygen atoms (if present) is preferably 5 or less, and preferably linear.

[1333] In the case that the compound represented by general formula (vii) is a so-called p-type compound with positive Δε, R vii2 Preferably, it is composed of a fluorine atom, a cyano group, a trifluoromethyl group, or a trifluoromethoxy group, with a fluorine atom or a cyano group being more preferred.

[1334] In the case where the compound represented by general formula (vii) is a so-called non-polar compound with approximately zero Δε, R vii2 Indicates with R vii1 The same meaning, R vii2 With R vii1 They can be the same or different.

[1335] In addition, as R vii1 / 2 From the viewpoint of solubility, a straight-chain alkyl group having 2 to 6 carbon atoms is preferred.

[1336] In general formula (vii), A vii1 A vii2 and A vii3 Represent the basis(a), basis(b), and basis(c) chosen independently, respectively:

[1337] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups may be replaced with -O-)

[1338] (b) 1,4-Phenylidene (one or more -CH= groups may be substituted with -N=)

[1339] (c) Naphthalene-1,4-diyl, naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one or more -CH= in naphthalene-1,4-diyl, naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl can be replaced by -N=)

[1340] The base in the group formed by the group.

[1341] In addition, one or more hydrogen atoms of the groups (a), (b) and (c) may be independently substituted by halogen atoms, cyano groups or alkyl groups having 1 to 6 carbon atoms.

[1342] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine, with fluorine being preferred from the viewpoint of stability and safety.

[1343] To improve response speed, A vii1 A vii2 and / or A vii3 Each group is preferably an aliphatic divalent cyclic group (a), and when an increase in Δn is required, it is preferably a divalent cyclic group exhibiting aromaticity (b) or (c), each preferably representing the following structure:

[1344] [Chemistry 230]

[1345]

[1346] (R represents an alkyl group with 1 to 6 carbon atoms)

[1347] Any of the following, preferably any of 1,4-phenylene, naphthalene-2,6-diyl and tetrahydronaphthalene-2,6-diyl, wherein one or more hydrogen atoms of these 1,4-phenylene, naphthalene-2,6-diyl and tetrahydronaphthalene-2,6-diyl groups may be independently substituted by fluorine atoms or alkyl groups having 1 to 6 carbon atoms.

[1348] In particular, from the perspective of Δn increase, A vii1 Preferably, the basis(d) to basis(f) selected are chosen from the following:

[1349] [Chemistry 231]

[1350]

[1351] (X vii1 and X vii2 (Each can be used to independently represent a hydrogen atom or a fluorine atom)

[1352] The base in the group formed by the group.

[1353] Furthermore, from the viewpoint of compatibility with other liquid crystal compounds, the expression group (f) is preferred.

[1354] In addition, to improve compatibility with other liquid crystal compositions, A vii1 A vii2 and / or A vii3 At least one of them preferably represents 1,4-phenylene substituted with an alkyl group having 1 to 6 carbon atoms, more preferably 1,4-phenylene substituted with an ethyl group.

[1355] The ring structure in a molecule of the compound represented by general formula (vii) in this invention, i.e., A vii1 A vii2 and / or A vii3 Preferably, it has one to five fluorine atoms in total, more preferably one to four.

[1356] The compound represented by the general formula (vii) is preferably a compound represented by the following general formulas (vii-1) to (vii-3).

[1357] [Chemistry 232]

[1358]

[1359] (In the general formulas (vii-1) to (vii-3), R) vii1 R vii2 A vii2 and A vii3 R represents the expression in the general formula (vii). vii1 R vii2 A vii2 and A vii3 They have the same meaning, and the preferred base and the number of preferred bases are also the same.

[1360] In the general formulas (vii-1) to (vii-3), X vii1 and X vii2 (Each can be used to independently represent a hydrogen atom or a fluorine atom)

[1361] As specific examples of compounds represented by general formula (vii-1), compounds represented by the following structural formulas (vii-1.1) to (vii-1.74) can be listed.

[1362] [Chemistry 233]

[1363]

[1364] [Chemistry 234]

[1365]

[1366] [Chemistry 235]

[1367]

[1368] [Chemistry 236]

[1369]

[1370] [Chemistry 237]

[1371]

[1372] As specific examples of compounds represented by general formula (vii-2), compounds represented by the following structural formulas (vii-2.1) to (vii-2.22) can be listed.

[1373] [Chemistry 238]

[1374]

[1375] [Chemistry 239]

[1376]

[1377] The compounds represented by structural formulas (vii-1.1) to (vii-1.74) and (vii-2.1) to (vii-2.22) are preferably those represented by structural formulas (vii-1.1) to (vii-1.20) and (vii-2.17) to (vii-2.22).

[1378] The compounds represented by general formula (vii), general formula (vii-1) to general formula (vii-3), structural formula (vii-1.1) to structural formula (vii-1.74) or structural formula (vii-2.1) to structural formula (vii-2.22) are used in the liquid crystal composition in one or more kinds, preferably one to ten kinds, and more preferably one to five kinds.

[1379] The lower limit of the total content of the compounds represented by general formula (vii), general formula (vii-1) to general formula (vii-3), structural formula (vii-1.1) to structural formula (vii-1.74) or structural formula (vii-2.1) to structural formula (vii-2.22) in 100% by mass of the liquid crystal composition is preferably 1% by mass, preferably 3% by mass, and preferably 5% by mass.

[1380] The upper limit of the total content of the compounds represented by general formula (vii), general formula (vii-1) to general formula (vii-3), structural formula (vii-1.1) to structural formula (vii-1.74) or structural formula (vii-2.1) to structural formula (vii-2.22) in 100% by mass of the liquid crystal composition is preferably 30% by mass, preferably 25% by mass, and preferably 20% by mass.

[1381] Regarding solubility, Δn and / or Δε r From this perspective, the total content of the compounds represented by general formula (vii), general formula (vii-1) to general formula (vii-3), structural formula (vii-1.1) to structural formula (vii-1.74) or structural formula (vii-2.1) to structural formula (vii-2.22) in 100% by mass of the liquid crystal composition is preferably 1% to 30% by mass, preferably 3% to 25% by mass, and preferably 5% to 20% by mass.

[1382] The compounds represented by general formula (vii) (including sub-concepts) can be manufactured using known methods.

[1383] From the viewpoint of solubility, the liquid crystal composition of the present invention may also further comprise one or more compounds represented by the following general formulas (np-1) to (np-3).

[1384] [Chemistry 240]

[1385]

[1386] In general formulas (np-1) to (np-3), R npi and R npii Each of the alkyl or halogen atoms, having 1 to 20 carbon atoms, can be used independently.

[1387] The alkyl group having 1 to 20 carbon atoms is a straight-chain, branched, or cyclic alkyl group, preferably a straight-chain alkyl group.

[1388] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1389] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[1390] In addition, one or more of the -CH2-CH2- groups 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-.

[1391] In addition, one or more of the -CH2-CH2-CH2- alkyl groups can be independently substituted by -O-CO-O-.

[1392] In addition, one or more hydrogen atoms in the alkyl group may be independently substituted by halogen atoms.

[1393] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[1394] Wherein, when the alkyl group is substituted by a specified group, oxygen atoms do not bond directly to oxygen atoms.

[1395] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[1396] For example, R npi and R npii An alkoxy group with 1 to 19 carbon atoms can be represented by replacing one of the -CH2- groups with -O- groups.

[1397] The alkoxy group is a straight-chain, branched, or cyclic alkoxy group, preferably a straight-chain alkoxy group.

[1398] The alkoxy group preferably has 2 to 10 carbon atoms, more preferably 2 to 6.

[1399] Additionally, R npi and R npii By replacing one of the -CH2- groups in the alkyl group with -S-, an alkyl mercapto group (thioalkyl) with 1 to 19 carbon atoms can be represented.

[1400] The alkyl thiol group is a linear, branched, or cyclic alkyl thiol group, preferably a linear alkyl thiol group.

[1401] The alkyl mercapto group preferably has 2 to 10 carbon atoms, more preferably 2 to 6.

[1402] Additionally, R npi and R npii An alkenyl group with 2 to 20 carbon atoms can be represented by replacing one or more of the -CH2-CH2- groups with -CH=CH- groups.

[1403] The alkenyl group is a linear, branched, or cyclic alkenyl group, preferably a linear alkenyl group.

[1404] The alkenyl group preferably has 2 to 10 carbon atoms, and more preferably 2 to 6.

[1405] Additionally, R npi and Rnpii An alkynyl group with 2 to 20 carbon atoms can be represented by replacing one or more of the -CH2-CH2- groups with -C≡C- groups.

[1406] The alkynyl group is a straight-chain, branched, or cyclic alkynyl group, preferably a straight-chain alkynyl group.

[1407] The number of carbon atoms in the alkynyl group is preferably 2 to 10, and more preferably 2 to 6.

[1408] Additionally, R npi and R npii An alkyl group having 2 to 19 carbon atoms can be represented by replacing one of the -CH2- atoms with -O- atoms and replacing one or more of the -CH2-CH2- atoms with -CH=CH- atoms.

[1409] The olefinic group is a straight-chain, branched, or cyclic olefinic group, preferably a straight-chain olefinic group.

[1410] The number of carbon atoms in the olefinic group is preferably 2 to 10, and more preferably 2 to 6.

[1411] Additionally, R npi and R npii By replacing one or more hydrogen atoms of the alkyl group with halogen atoms, a alkyl halide with 1 to 20 carbon atoms can be represented.

[1412] The alkyl halide is a straight-chain, branched, or cyclic alkyl halide, preferably a straight-chain alkyl halide.

[1413] The number of carbon atoms in the alkyl halide is preferably 2 to 10, and more preferably 2 to 6.

[1414] R npi and R npii A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by replacing one -CH2- atom of the alkyl group with -O- atom and replacing one or more hydrogen atoms of the alkyl group with halogen atoms.

[1415] The halogenated alkoxy group is a straight-chain, branched, or cyclic halogenated alkoxy group, preferably a straight-chain halogenated alkoxy group.

[1416] The number of carbon atoms in the haloalkoxy group is preferably 2 to 10, and more preferably 2 to 6.

[1417] As R npi and R npii Specific examples of alkyl groups having 1 to 20 carbon atoms (including substituted alkyl groups) can be listed in formula (R). npi / ii -1)~Formula (R) npi / ii -36) represents the base.

[1418] [Chemistry 241]

[1419]

[1420] Formula (R) npi / ii -1)~Formula (R) npi / ii In -36), black dots represent bonds to rings A, B, C, or D.

[1421] As R npi and R npii Halogen atoms in halogen atoms include: fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc.

[1422] In general formulas (np-1) to (np-3), rings A, B, C, and D independently represent the following basis(a), basis(b), basis(c), and basis(d), respectively:

[1423] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups may be replaced with -O-)

[1424] (b) 1,4-Phenylidene (one or more -CH= groups may be substituted with -N=)

[1425] (c) Naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one or more -CH= in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl can be replaced by -N=)

[1426] (d) 1,4-cyclohexenyl, 1,3-dioxane-trans-2,5-diyl, pyrimidin-2,5-diyl, or pyridine-2,5-diyl

[1427] The base in the group formed by the group.

[1428] One or more hydrogen atoms in rings A, B, C, and D can each be independently substituted by a substituent S. npi1 replace.

[1429] Substituent S npi1 It represents any one of a halogen atom, a cyano group, or an alkyl group having 1 to 20 carbon atoms.

[1430] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine, with fluorine being preferred from the viewpoint of stability and safety.

[1431] The alkyl group having 1 to 20 carbon atoms is a straight-chain, branched, or cyclic alkyl group, preferably a straight-chain alkyl group.

[1432] The alkyl group having 1 to 20 carbon atoms preferably has 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms.

[1433] One or more of the -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[1434] In addition, one or more of the -CH2-CH2- groups 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-.

[1435] One or more of the -CH2-CH2-CH2- alkyl groups may be independently substituted by -O-CO-O-.

[1436] In addition, one or more hydrogen atoms in the alkyl group may be independently substituted with halogen atoms.

[1437] Examples of halogen atoms include: fluorine, chlorine, bromine, and iodine.

[1438] Wherein, when the alkyl group is substituted by a specified group, oxygen atoms do not bond directly to oxygen atoms.

[1439] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[1440] As a substituent S npi1 , just V th From this perspective, halogen atoms are preferred, and fluorine atoms are even more preferred.

[1441] Furthermore, in the substituent S npi1 When multiple instances exist, these can be the same or different.

[1442] S, a substituent in ring A npi1 The preferred substitution position is the one described in the following formula (A-SP-1).

[1443] [Chemistry 242]

[1444]

[1445] In formula (A-SP-1), the white dot represents the direction to R. npi The bond is represented by black dots indicating the Z-axis. npi The bond structure.

[1446] More specifically, ring A is preferably represented by any one of the following formulas (A-1) to (A-3).

[1447] [Chemistry 243]

[1448]

[1449] In equations (A-1) to (A-3), the white dots represent the direction to R. npi The bond is represented by black dots indicating the Z-axis. npi The bond structure.

[1450] More specifically, ring B is preferably represented by any one of the following formulas (B-1) to (B-2).

[1451] [Chemistry 244]

[1452]

[1453] In equations (B-1) to (B-2), the white dots represent the direction of Z. npi The black dot represents the bond to R. npii or Z npii The bond structure.

[1454] More specifically, ring C is preferably represented by any one of the following formulas (C-1) to (C-2).

[1455] [Chemistry 245]

[1456]

[1457] In equations (C-1) to (C-2), the white dots represent the direction of Z. npii The black dot represents the bond to R. npii or Z npiii The bond structure.

[1458] In general formulas (np-1) to (np-3), Z npi Z npii and Z npiii Each of the following can be independently represented: a single bond, or an alkylene group having 1 to 20 carbon atoms.

[1459] One or more of the -CH2- groups in the alkylene group may be independently substituted by -O- groups.

[1460] In addition, one or more of the -CH2-CH2- groups 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-.

[1461] In addition, one or more of the -CH2-CH2-CH2- alkyl groups can be independently substituted by -O-CO-O-.

[1462] In cases where alkyl groups with 1 to 10 carbon atoms are substituted by specified groups, oxygen atoms do not bond directly to each other.

[1463] Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to sulfur atoms and / or oxygen atoms are not directly bonded to sulfur atoms.

[1464] Specific examples of alkylene groups having 1 to 20 carbon atoms (including substituted alkylene groups) can be enumerated as (Z npi / ii / iii -1)~Formula (Z) npi / ii / iii -24) represents the base.

[1465] [Chemistry 246]

[1466]

[1467] Formula (Z) npi / ii / iii -1)~Formula (Z) npi / ii / iii In -24), white dots represent bonds to loop A, loop B, or loop C, and black dots represent bonds to loop B, loop C, or loop D.

[1468] Regarding Δn and / or Δε r From Z's point of view, npi Z npii and Z npiii Each of the following is preferred to represent a single bond, -C≡C-, and -CO-O-.

[1469] Among them, the compounds represented by general formulas (np-1) to (np-3) are excluded from the compounds represented by general formulas (vi) and (vii) (including subordinate concepts).

[1470] The preferred compounds are those represented by the general formula (np-2), which are those represented by the general formulas (np-2-1) to (np-2-2).

[1471] [Chemistry 247]

[1472]

[1473] In general formulas (np-2-1) to (np-2-2), R npi R npii and S npi R represents the expression in general formulas (np-1) to (np-3). npi R npii and S npi They have the same meaning, respectively.

[1474] Specific examples of compounds represented by the general formula (np-2-1) include compounds represented by the following structural formula (np-2-1.1).

[1475] [Chemistry 248]

[1476]

[1477] Specific examples of compounds represented by the general formula (np-2-2) include compounds represented by the following structural formulas (np-2-2.1) to (np-2-2.5).

[1478] [Chemistry 249]

[1479]

[1480] Specific examples of compounds represented by the general formula (np-2-3) include compounds represented by the following structural formulas (np-2-3.1) to (np-2-3.5).

[1481] [Chemistry 250]

[1482]

[1483] The compounds represented by general formulas (np-1) to (np-3), (np-2-1) to (np-2-3), (np-2-1.1), (np-2-2.1) to (np-2-2.5), or (np-2-3.1) to (np-2-3.3) are used in the liquid crystal composition in one or more types, 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.

[1484] The lower limit of the total content of the compounds represented by general formulas (np-1) to (np-3), (np-2-1) to (np-2-3), (np-2-1.1), (np-2-2.1) to (np-2-2.5), or (np-2-3.1) to (np-2-3.3) in 100% by mass of the liquid crystal composition is preferably 0.5% by mass, preferably 1% by mass, and preferably 3% by mass.

[1485] The upper limit of the total content of the compounds represented by general formulas (np-1) to (np-3), (np-2-1) to (np-2-3), (np-2-1.1), (np-2-2.1) to (np-2-2.5), or (np-2-3.1) to (np-2-3.3) in 100% by mass of the liquid crystal composition is preferably 45% by mass, preferably 35% by mass, and preferably 25% by mass.

[1486] Regarding solubility, Δn and / or Δε r From this perspective, the total content of the compounds represented by general formulas (np-1) to (np-3), (np-2-1) to (np-2-3), (np-2-1.1), (np-2-2.1) to (np-2-2.5), or (np-2-3.1) to (np-2-3.3) in 100% by mass of the liquid crystal composition is preferably 0.5% to 45% by mass, preferably 1% to 35% by mass, and preferably 3% to 25% by mass.

[1487] Compounds represented by general formulas (np-1) to (np-3) (including sub-concepts) can be manufactured by known methods.

[1488] (Liquid Crystal Composition)

[1489] The liquid crystal composition of the present invention can be manufactured, for example, by mixing the compound represented by the general formula (i), other compounds as needed, and additives.

[1490] Examples of additives include stabilizers, pigment compounds, and polymerizing compounds.

[1491] Examples of stabilizers include: hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenes, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, hindered phenols, and hindered amines.

[1492] As hindered phenols, examples include hindered phenolic antioxidants represented by the following structural formulas (XX-1) to (XX-3).

[1493] [Chemistry 251]

[1494]

[1495] As hindered amines, examples include hindered amine light stabilizers represented by the following structural formulas (YY-1) to (YY-2).

[1496] [Chemistry 252]

[1497]

[1498] 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.

[1499] Regarding solubility, Δn and / or Δε r From this perspective, the preferred combination of compounds used in the liquid crystal composition is: 1) a combination of compounds represented by general formula (i) (including subordinate concepts), compounds represented by general formula (ii) (including subordinate concepts), compounds represented by general formula (v) (including subordinate concepts), compounds represented by general formula (vi) (including subordinate concepts), and compounds represented by general formula (vii) (including subordinate concepts); 2) a combination of compounds represented by general formula (i) (including subordinate concepts), compounds represented by general formula (ii) (including subordinate concepts), compounds represented by general formula (vi) (including subordinate concepts), and compounds represented by general formula (vii) (including subordinate concepts). 3) Combinations of compounds represented by general formula (i) (including hyponyms) and compounds represented by general formula (ii) (including hyponyms); 4) Combinations of compounds represented by general formula (i) (including hyponyms), compounds represented by general formula (ii) (including hyponyms), compounds represented by general formula (v) (including hyponyms), compounds represented by general formula (vi) (including hyponyms) and compounds represented by general formulas (np-1) to (np-3) (including hyponyms); 5) Combinations of compounds represented by general formula (i) (including hyponyms) and compounds represented by general formula (ii) (including hyponyms).

[1500] Regarding Δn and / or Δε rFrom the perspective of the present invention, the liquid crystal composition preferably comprises one or more compounds represented by general formula (i) (including subordinate concepts) and three or more compounds represented by general formula (ii-6-27) (including subordinate concepts).

[1501] Additionally, regarding Δn and / or Δε r From the perspective of the present invention, the liquid crystal composition preferably comprises one or more compounds represented by general formula (i-2-11) (including subordinate concepts) and three or more compounds represented by general formula (ii-6-27) (including subordinate concepts).

[1502] Furthermore, from the viewpoint of solubility, the liquid crystal composition of the present invention preferably comprises one or more compounds represented by general formula (i) (including subordinate concepts), and three or more compounds represented by general formula (ii-5-2) (including subordinate concepts) and / or compounds represented by general formula (ii-6-5) (including subordinate concepts).

[1503] Furthermore, from the viewpoint of low viscosity, the liquid crystal composition of the present invention preferably contains one or more compounds represented by general formula (i) (including sub-concepts) and one or more compounds represented by general formulas (np-1) to (np-3) (including sub-concepts), and the total content of the compounds represented by general formulas (np-1) to (np-3) (including sub-concepts) in 100% by mass of the liquid crystal composition is 1% to 30% by mass, more preferably 5% to 25% by mass.

[1504] <Characteristics of Liquid Crystal Compositions>

[1505] Liquid crystal phase upper limit temperature (T) ni () is the temperature at which the liquid crystal composition undergoes a phase transition from the nematic phase to the isotropic phase.

[1506] T ni The determination was performed as follows: a microscope specimen containing a liquid crystal composition was prepared by holding it in a slide and a cover glass, and observed under a polarizing microscope while it was heated on a heated stage.

[1507] Alternatively, it can also be measured using differential scanning calorimetry (DSC).

[1508] The unit is "℃".

[1509] T niThe higher the temperature, the better the nematic phase can be maintained even at high temperatures, and the wider the driving temperature range can be expanded.

[1510] The upper limit temperature (T) of the liquid crystal phase of the liquid crystal composition of the present invention ni The temperature range can be appropriately set depending on whether the device is used indoors or in a car where the external temperature of the liquid crystal display element can be controlled, or whether it is used outdoors. From the viewpoint of the driving temperature range, it is preferably 100°C or higher, preferably 100°C to 200°C, and preferably 110°C to 180°C.

[1511] Liquid crystal phase lower limit temperature (T) →n The phase transition temperature (TRT) is the temperature at which a liquid crystal composition undergoes a phase transition from other phases (glass, laminated phase, crystalline phase) to a nematic phase.

[1512] T →n The determination was performed as follows: a liquid crystal composition was filled into a glass capillary and immersed in a coolant at -70°C to induce a phase transition of the liquid crystal composition to other phases. The temperature was increased while the results were observed.

[1513] Alternatively, it can also be measured by differential scanning calorimetry (DSC).

[1514] The unit is "℃".

[1515] T →n The lower the temperature, the better the nematic phase can be maintained even at low temperatures, thus expanding the driving temperature range.

[1516] From the viewpoint of driving temperature, the lower limit temperature of the liquid crystal phase (T) of the liquid crystal composition of the present invention is... →n The temperature is preferably below 10℃, preferably -70℃ to 0℃, and preferably -40℃ to -5℃.

[1517] Δn (refractive index anisotropy) is related to Δn in the near-infrared region used in optical sensors, as described later.

[1518] The larger Δn is, the greater the phase modulation power of the light of the wavelength of the object becomes, making it particularly suitable for optical sensors.

[1519] Δn at 25℃ and 589nm was determined using an Abbe refractometer and based on the anomalous refractive index (n) of the liquid crystal composition. e ) and constant refractive index (n o The difference (n) e -n o Find the answer.

[1520] Alternatively, Δn can be determined using a phase difference measuring device.

[1521] The relationship Δn = Re / d holds true between the phase difference Re, the thickness d of the liquid crystal layer, and Δn.

[1522] A liquid crystal composition was injected into a glass cell with a polyimide alignment film and an anti-parallel rubbing treatment, with a cell gap (d) of approximately 3.0 μm. The in-plane Re was measured using a phase difference film-optical material inspection device RETS-100 (manufactured by Otsuka Electronics Co., Ltd.).

[1523] The measurement was performed at a temperature of 25℃ and a wavelength of 589nm, and the measurement was unitless.

[1524] From the viewpoint of the phase modulation power of light of 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.

[1525] Rotational viscosity (γ1) is the viscosity rate related to the rotation of liquid crystal molecules.

[1526] Regarding γ1, the liquid crystal composition can be filled into a glass cell with a cell gap of about 10 μm and measured using LCM-2 (manufactured by TOYO Corporation).

[1527] In the case of a liquid crystal composition with positive dielectric anisotropy, a horizontal alignment unit is used; in the case of a liquid crystal composition with negative dielectric anisotropy, a vertical alignment unit is used.

[1528] The measurement was conducted at a temperature of 25°C, and the unit is mPa·s.

[1529] The smaller γ1 is, the faster the response speed of the liquid crystal composition becomes, and therefore it is suitable for any liquid crystal display element.

[1530] 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 mPa·s to 2000 mPa·s, preferably 200 mPa·s to 1500 mPa·s, and preferably 250 mPa·s to 1250 mPa·s.

[1531] Threshold voltage (V) th It is related to the driving voltage of the liquid crystal composition.

[1532] About V th The liquid crystal composition can be filled in TN cells with an 8.3 μm gap, and the transmittance is determined according to the applied voltage.

[1533] The measurement was conducted at a temperature of 25°C, and the unit is "V".

[1534] V thThe lower the value, the more it can be driven at low voltages.

[1535] From the viewpoint of driving voltage, the V of the liquid crystal composition of the present invention at 25°C th Preferably, the voltage is below 3.0V, 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.

[1536] The higher the dielectric constant anisotropy in the high-frequency region, the greater the phase modulation force of the radio waves in the target frequency band, making it particularly suitable for antenna applications.

[1537] In addition, in antenna applications, the smaller the dielectric loss tangent in the high-frequency region, the smaller the energy loss in the target frequency band, making it suitable.

[1538] In the liquid crystal composition of the present invention, taking the characteristics of the high-frequency region as an example, the dielectric constant anisotropy Δε at 10 GHz was measured. r and the average value of the dielectric loss tangent tanδ iso .

[1539] For Δε r =(ε r∥ -ε r⊥ ), and is tanδ iso =(2ε r⊥ tanδ ⊥ +ε r∥ tanδ ∥ ) / (2ε r⊥ +ε r∥ ).

[1540] Here, “ε r “ is the dielectric constant, “tanδ” is the dielectric loss tangent, the subscript “∥” indicates the component that is parallel to the orientation direction of the liquid crystal, and “⊥” indicates the component that is perpendicular to the orientation direction of the liquid crystal.

[1541] Δε r and tanδ iso The following methods can be used to determine this.

[1542] First, the liquid crystal composition is introduced into a capillary made of polytetrafluoroethylene (PTFE).

[1543] The capillary tube used here has an inner radius of 0.80 mm and an outer radius of 0.835 mm, with an effective length of 4.0 cm.

[1544] A capillary containing a liquid crystal composition is introduced into the center of a cavity resonator (manufactured by EMlabo Inc.) with a resonant frequency of 10 GHz.

[1545] The cavity resonator has a diameter of 30 mm and a width of 26 mm.

[1546] Then, the input signal is used, and the output signal is recorded using a network analyzer (manufactured by Keysight Technology Inc.).

[1547] The difference between the resonant frequency of a PTFE capillary without a liquid crystal composition and that of a PTFE capillary with a liquid crystal composition determines the dielectric constant (ε) at 10 GHz. r ) and loss angle (δ).

[1548] Moreover, the obtained tangent of δ is the dielectric loss tangent (tanδ).

[1549] 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 obtained by controlling the orientation of the liquid crystal molecules using the resonant frequency of the PTFE capillary containing the liquid crystal composition.

[1550] To align liquid crystal molecules in the PTFE capillary in a direction perpendicular to the effective length direction or in a direction parallel to the effective length direction, a magnetic field of a permanent magnet or electromagnet is used.

[1551] For example, the magnetic field has a pole spacing of 45 mm and a strength of 0.23 tesla near the center.

[1552] The desired characteristic composition is obtained by rotating a PTFE capillary containing a liquid crystal composition parallel or perpendicular to a magnetic field.

[1553] The measurement was conducted at a temperature of 25°C, Δε r and tanδ iso There are no units listed.

[1554] Δε of the liquid crystal composition of the present invention at 25°C r Preferably, it is larger; from the viewpoint of phase modulation force 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.

[1555] tanδ of the liquid crystal composition of the present invention at 25°C isoPreferably, it is smaller; from the viewpoint of GHz band loss, 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.

[1556] (Liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment and antennas)

[1557] Hereinafter, liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas using the liquid crystal composition of the present invention will be described.

[1558] The liquid crystal display element of the present invention uses the liquid crystal composition, preferably driven in an active matrix or a passive matrix manner.

[1559] Furthermore, the liquid crystal display element of the present invention is preferably a liquid crystal display element whose dielectric constant can be reversibly switched by reversibly changing the orientation direction of the liquid crystal molecules in the liquid crystal composition.

[1560] The sensors of the present invention utilize the liquid crystal composition, and examples of its forms include: ranging sensors utilizing electromagnetic waves, visible light, or infrared light; infrared sensors utilizing temperature changes; temperature sensors utilizing changes in the wavelength of reflected light caused by changes in the spacing of cholesteric liquid crystals; pressure sensors utilizing changes in the wavelength of reflected light; ultraviolet sensors utilizing changes in the wavelength of reflected light caused by changes in composition; electrical sensors utilizing temperature changes caused by voltage or current; radiation sensors utilizing temperature changes accompanying the tracks of radioactive particles; ultrasonic sensors utilizing changes in the arrangement of liquid crystal molecules caused by mechanical vibrations of ultrasonic waves; and electromagnetic sensors utilizing changes in the wavelength of reflected light caused by temperature changes or changes in the arrangement of liquid crystal molecules caused by an electric field.

[1561] As a ranging sensor, a light-detection and ranging (LiDAR) sensor using a light source is preferred.

[1562] As a LiDAR, it is preferably used in artificial satellites, aircraft, unmanned aerial vehicles (UAVs), automobiles, railways, and ships.

[1563] For automotive use, it is particularly preferred for use in autonomous vehicles.

[1564] The light source is preferably a light-emitting diode (LED) or a laser, with a laser being more preferred.

[1565] The light used for LiDAR is preferably infrared light, with a wavelength preferably between 800 nm and 2000 nm.

[1566] Infrared lasers with wavelengths of 905nm or 1550nm are particularly preferred.

[1567] When considering the cost of the photodetector used or its sensitivity in all weather conditions, a 905nm infrared laser is preferred; when considering safety related to human vision, a 1550nm infrared laser is preferred.

[1568] The liquid crystal composition of the present invention exhibits high Δn, thus providing a sensor with high phase modulation power and excellent detection sensitivity in the visible light, infrared light and electromagnetic wave regions.

[1569] The liquid crystal lens of the present invention uses the liquid crystal composition, for example, as one of its forms, including: a first transparent electrode layer, a second transparent electrode layer, a liquid crystal layer containing the liquid crystal composition disposed between the first transparent electrode layer and the second transparent electrode layer, an insulating layer disposed between the second transparent electrode layer and the liquid crystal layer, and a high-resistivity layer disposed between the insulating layer and the liquid crystal layer.

[1570] The liquid crystal lens of the present invention can be used, for example, as a two-dimensional (2D) switching lens, a 3D switching lens, or a lens for adjusting the focus of a camera.

[1571] The optical communication device of the present invention uses the liquid crystal composition. For example, as one of its forms, a liquid crystal on silicon (LCOS) with the following structure can be cited, which has a liquid crystal layer on a reflective layer (electrode) in which liquid crystals constituting multiple pixels are arranged in a two-dimensional manner.

[1572] The optical communication device of the present invention can be used, for example, as a spatial phase modulator.

[1573] The antenna of the present invention uses the liquid crystal composition.

[1574] More specifically, the antenna of the present invention includes: a first substrate having a plurality of slots; a second substrate facing the first substrate and having a power supply section disposed thereon; a first dielectric layer disposed between the first substrate and the second substrate; a plurality of patch electrodes disposed corresponding to the plurality of slots; a third substrate having the patch electrodes disposed thereon; and a liquid crystal layer disposed between the first substrate and the third substrate, wherein the liquid crystal layer contains the liquid crystal composition.

[1575] By using one or more liquid crystal compositions comprising compounds (including lower-level concepts) of general formula (i) having alkynyl and isothiocyanate groups (-NCS) as liquid crystal compositions, T ni High, large Δn, Vth Low, Δε r Large, tanδ iso Small size and good preservation at low temperatures, thus providing antennas with high reliability against external stimuli such as heat.

[1576] Therefore, an antenna capable of greater phase control over microwave or millimeter-wave electromagnetic waves can be provided.

[1577] The antenna of the present invention is preferably operated at a Ka-band frequency, a K-band frequency, or a Ku-band frequency used for satellite communication.

[1578] The antenna of the present invention is preferably a structure composed of a radial slot array and a patch antenna array.

[1579] As for the structure of the antenna of the present invention, reference may be made to, for example, the matters described in International Publication No. 2021 / 157189, etc.

[1580] Example

[1581] The present invention will be described in more detail below with examples, but the present invention is not limited to any of the examples described below.

[1582] The compositions of the following examples and comparative examples contain each compound in the proportions shown in the table, and the content is stated as "mass %".

[1583] In addition, the following abbreviations are used to describe the compounds. Furthermore, unless otherwise specified, the trans form may be represented by both cis and trans forms.

[1584] <Ring Structure>

[1585] [Chemistry 253]

[1586]

[1587] <End Structure> [Table 1]

[1588] -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]]> 1V2- <![CDATA[CH3-CH=CH-CH2-CH2-]]> -OCF3 <![CDATA[-O-CF3 <!-- 157 -->]]> 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-]]>

[1589] (Where, n in the table is a natural number)

[1590] <Connection Structure>

[1591] [Table 2]

[1592] -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-

[1593] (Where, n in the table is a natural number)

[1594] (Hindered phenolic antioxidants)

[1595] [Chemistry 254]

[1596]

[1597] (Hindered amine light stabilizers)

[1598] [Chemistry 255]

[1599]

[1600] (Preparation of liquid crystal compositions)

[1601] Prepare LC-A to LC-B and LC-01 to LC-09 as described in Tables 3 and 4.

[1602] [Table 3]

[1603] 4-T-Ph-T-Ph3-NCS 5 10 10 5-T-Ph-T-Ph3-NCS 5 4-T-Ph-Ph-T-Ph3-NCS 12 7 4-T-Ph-T-Ph-Ph3-NCS 4-T-Ph-T-Ph1-Ph3-NCS 5-T-Ph-T-Ph-Ph3-NCS 10 10 5-T-Ph-T-Ph1-Ph3-NCS 6-T-Ph-T-Ph-Ph3-NCS 4-T-Pm1-T-Th-Ph3-NCS 5-T-Pm1-T-Th-Ph3-NCS 3-Ph3-T-Ph-Ph3-NCS 3 5 3 5 4-Ph3-T-Ph-Ph3-NCS 10 10 8 10 5-Ph3-T-Ph-Ph3-NCS 10 10 8 13 3-Cy-T-Ph-Ph3-NCS 6 10 4-Cy-T-Ph-Ph3-NCS 5 5-Cy-T-Ph-Ph3-NCS 3-Cy-T-Ph-T-Ph3-NCS 4-Cy-T-Ph-T-Ph3-NCS 5-Cy-Ph-NCS 6 4-Ph-T-Pc1-NCS 11 4O-Ph2-T-Ph-NCS 5 5O-Ph2-T-Ph-NCS 5 5-Ph-T-Ph1-NCS 5 3-Ph-T-Ph3-NCS 13 17 17 17 17 5-Ph-T-Ph3-NCS 11 12 12 12 5 2-Cy-Ph-Ph3-NCS 12 14 4-Cy-Ph-Ph3-NCS 12 14 4-Cy-Ph-T-Ph1-NCS 16 5-Cy-Ph-T-Ph1-NCS 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 3-Ph-T-Ph1-Ph-CN 6 12 4-Ph3-T-Pm1-T-Ph-S1 7 7 7 2-Ph3-T-Ph-Az-Ph-2 5 5 5 3-Ph3-T-Ph-Az-Ph-2 8 8 8 3-Cy-Cy-Ph-1 3-Cy-Cy-Ph-2 3-Cy-Cy-Ph-3 Total [mass%] 100 100 100 100 100 100

[1604] [Table 4]

[1605] 4-T-Ph-T-Ph3-NCS 5 5 5 5-T-Ph-T-Ph3-NCS 5 5 4-T-Ph-Ph-T-Ph3-NCS 5 10 5 10 10 4-T-Ph-T-Ph-Ph3-NCS 5 4-T-Ph-T-Ph1-Ph3-NCS 5 10 7 5-T-Ph-T-Ph-Ph3-NCS 10 7 5-T-Ph-T-Ph1-Ph3-NCS 10 7 6-T-Ph-T-Ph-Ph3-NCS 7 4-T-Pm1-T-Th-Ph3-NCS 4 5-T-Pm1-T-Th-Ph3-NCS 4 3-Ph3-T-Ph-Ph3-NCS 4 3 5 5 4-Ph3-T-Ph-Ph3-NCS 4 3 10 10 5-Ph3-T-Ph-Ph3-NCS 4 3 10 10 3-Cy-T-Ph-Ph3-NCS 3 3 5 5 4-Cy-T-Ph-Ph3-NCS 3 3 5 5 5-Cy-T-Ph-Ph3-NCS 3 5 3-Cy-T-Ph-T-Ph3-NCS 4 4 4-Cy-T-Ph-T-Ph3-NCS 5 5-Cy-Ph-NCS 3 4-Ph-T-Pc1-NCS 6 4O-Ph2-T-Ph-NCS 5 5O-Ph2-T-Ph-NCS 5 5-Ph-T-Ph1-NCS 5 3-Ph-T-Ph3-NCS 6 4 10 10 5-Ph-T-Ph3-NCS 6 4 10 10 2-Cy-Ph-Ph3-NCS 6 2 4-Cy-Ph-Ph3-NCS 6 2 4-Cy-Ph-T-Ph1-NCS 16 5-Cy-Ph-T-Ph1-NCS 13 4-Cy-Ph-T-Ph3-NCS 5-Cy-Ph-T-Ph3-NCS CF3O-Ph-Ph-Ph3-NCS 4-Ph-Ph-T-Ph3-NCS 5-Ph-Ph-T-Ph3-NCS 5-Ph-Ph5-T-Ph1-NCS 15 3-Ph-T-Ph1-Ph-CN 8 8 4-Ph3-T-Pm1-T-Ph-S1 7 6 8 8 2-Ph3-T-Ph-Az-Ph-2 5 5 3-Ph3-T-Ph-Az-Ph-2 8 8 3-Cy-Cy-Ph-1 5 5 3-Cy-Cy-Ph-2 5 3-Cy-Cy-Ph-3 5 Total [mass %] 100 100 100 100 100

[1606] (Examples 1 to 39 and Comparative Examples 1 to 2)

[1607] Liquid crystal compositions described in Tables 5 to 11 were prepared using LC-A to LC-B, LC-01 to LC-09, hindered phenolic antioxidants (XX-1) to hindered phenolic antioxidants (XX-3), and hindered amine light stabilizers (YY-1) to hindered amine light stabilizers (YY-2). Their physical properties were measured, and a <shelf life test> was performed. The results are shown in Tables 5 to 11. Furthermore, in Comparative Example 2, crystallization was performed at room temperature; therefore, high-frequency characteristics (Δε) were not tested. r and tanδ iso The determination of ).

[1608] <Preservation Test>

[1609] 0.5 g of the liquid crystal composition was weighed into a 1 mL sample vial (manufactured by Maruemu) and degassed by degassing at 150 Pa–250 Pa for 10 minutes. The vial was then rinsed with dry nitrogen and capped. It was stored in a temperature-controlled thermostat (manufactured by Espec, SH-241) at 0 °C for two weeks, with visual inspection every week to confirm the formation of crystallization in the liquid crystal composition.

[1610] [Table 5]

[1611]

[1612] [Table 6]

[1613]

[1614] [Table 7]

[1615]

[1616] [Table 8]

[1617]

[1618] [Table 9]

[1619]

[1620] [Table 10]

[1621]

[1622] [Table 11]

[1623]

[1624] According to Examples 1 to 9, the liquid crystal composition using the compound represented by general formula (i) is T ni High, large Δn, V th Low, Δε r Large, tanδ iso Liquid crystal compositions that are well preserved at small and low temperatures.

[1625] In particular, Examples 1, 6, and 7 yielded the following results: Δn and Δε r It's extremely large.

[1626] On the other hand, according to Comparative Examples 1 to 2, the liquid crystal composition that did not use the compound represented by general formula (i) had a Δn of less than 0.38, or crystallization was confirmed at room temperature.

[1627] Furthermore, according to Examples 10 to 39, even when hindered phenolic antioxidants or hindered amine light stabilizers were used in combination, T was confirmed. ni High, large Δn, V th Low, Δε r Large, tanδ iso It has good preservation properties at small and low temperatures.

[1628] (Examples 40 to 69)

[1629] Furthermore, the liquid crystal compositions described in Tables 12 to 17 were prepared using LC-10 to LC-15, hindered phenolic antioxidants (XX-1) to hindered phenolic antioxidants (XX-3), and hindered amine light stabilizers (YY-1) to hindered amine light stabilizers (YY-2). Their physical properties were measured, and a <shelfability test> was conducted, yielding the same results. The results are shown in Tables 12 to 17.

[1630] [Table 12]

[1631] 4-T-Ph-T-Ph3-NCS 5-T-Ph-T-Ph3-NCS 4-T-Ph-Ph-T-Ph3-NCS 4-T-Ph-T-Ph-Ph3-NCS 5 4-T-Ph-T-Ph1-Ph3-NCS 5 5-T-Ph-T-Ph-Ph3-NCS 5 5 5 4 5 5-T-Ph-T-Ph1-Ph3-NCS 3 3 3 5 6-T-Ph-T-Ph-Ph3-NCS 4-T-Pm1-T-Th-Ph3-NCS 5-T-Pm1-T-Th-Ph3-NCS 4-T-Pm2-Ph-T-Ph3-NCS 4 10 10 4-T-Pm1-Ph-T-Ph3-NCS 5 4-T-Ph2-T-Ph-Ph3-NCS 4 4-T-Ph1-Ph-T-Ph3-NCS 4 5 5-T-Ph1-Ph-T-Ph3-NCS 4 4(1)-T-Ph-Ph-T-Ph3-NCS 4 3-Ph3-T-Ph-Ph3-NCS 4-Ph3-T-Ph-Ph3-NCS 5-Ph3-T-Ph-Ph3-NCS 10 10 10 10 10 10 3-Cy-T-Ph-Ph3-NCS 15 15 15 15 15 10 4-Cy-T-Ph-Ph3-NCS 15 15 15 15 15 6 5-Cy-T-Ph-Ph3-NCS 3-Cy-T-Ph-T-Ph3-NCS 6 4 6 6 6 6 4-Cy-T-Ph-T-Ph3-NCS 6 6 6 6 6 5-Cy-Ph-NCS 4-Ph-T-Pc1-NCS 4O-Ph2-T-Ph-NCS 5O-Ph2-T-Ph-NCS 5-Ph-T-Ph1-NCS 3-Ph-T-Ph3-NCS 11 11 11 11 11 12 5-Ph-T-Ph3-NCS 10 10 10 10 10 10 2-Cy-Ph-Ph3-NCS 8 8 8 8 8 4-Cy-Ph-Ph3-NCS 7 7 7 7 7 4-Cy-Ph-T-Ph1-NCS 5-Cy-Ph-T-Ph1-NCS 4-Cy-Ph-T-Ph3-NCS 5-Cy-Ph-T-Ph3-NCS CF3O-Ph-Ph-Ph3-NCS 4-Ph-Ph-T-Ph3-NCS 5-Ph-Ph-T-Ph3-NCS 5-Ph-Ph5-T-Ph1-NCS 3-Tet3-T-Ph-T-Ph1-NCS 10 3-Ph-T-Ph1-Ph-CN 4-Ph3-T-Pm1-T-Ph-S1 2-Ph3-T-Ph-Az-Ph-2 3-Ph3-T-Ph-Az-Ph-2 3-Cy-Cy-Ph-1 3-Cy-Cy-Ph-2 3-Cy-Cy-Ph-3 Total [mass%] 100 100 100 100 100 100

[1632] [Table 13]

[1633]

[1634] [Table 14]

[1635]

[1636] [Table 15]

[1637]

[1638] [Table 16]

[1639]

[1640] [Table 17]

[1641]

[1642] The synthesis of compounds represented by general formula (i) will be described below.

[1643] (Synthetic Example 1) Preparation of the compound represented by formula (I-1)

[1644] [Chemistry 256]

[1645]

[1646] Under nitrogen and at room temperature, 150.0 g of the compound represented by formula (I-1-1), 4.0 g of copper iodide (I), 7.4 g of bis(triphenylphosphine)palladium dichloride (II), 222 mL of triethylamine, and 375 mL of tetrahydrofuran were added to a reaction vessel. Then, while stirring at room temperature, a solution containing 52.3 g of 1-hexyne dissolved in 375 mL of tetrahydrofuran was added dropwise, and the mixture was stirred for 1 hour at room temperature. After the reaction was complete, 10% hydrochloric acid was injected into the reaction solution, and extraction was performed using toluene. After washing the organic layer with saturated brine, purification was performed using column chromatography (silica gel, hexane) to obtain 125.0 g of the compound represented by formula (I-1-2).

[1647] Next, under nitrogen and at room temperature, 15.0 g of the compound represented by formula (I-1-2), 0.5 g of copper iodide (I), 1.5 g of tetrakis(triphenylphosphine)palladium (0), 60 mL of triethylamine, and 30 mL of N,N-dimethylformamide were added to the reaction vessel. Then, while heating at 75°C, a solution containing 11.6 g of the compound represented by formula (I-1-3) dissolved in 30 mL of N,N-dimethylformamide was added dropwise, and the mixture was stirred at 75°C for 2 hours. After the reaction was complete, a saturated aqueous solution of ammonium chloride was added to the reaction solution, and extraction was performed using toluene. After washing the organic layer with saturated brine, purification was performed using column chromatography (aminosilica gel, toluene / hexane = 1 / 9 to 1 / 1) and subsequent recrystallization (toluene / hexane = 1 / 3), thereby obtaining 10.8 g of the compound represented by formula (I-1-4).

[1648] Next, under nitrogen conditions and at room temperature, 10.8 g of the compound represented by formula (I-1-4), 54 mL of dichloromethane, and 9.7 g of 1,1-thiocarbonyldiimidazole were added to the reaction vessel, and the mixture was 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) to obtain 8.5 g of the compound represented by formula (I-1).

[1649] Mass spectrometry (MS) (electron impact (EI)): m / z = 351

[1650] (Synthetic Example 2) Preparation of the compound represented by formula (I-2)

[1651] [Chemistry 257]

[1652]

[1653] In a nitrogen environment at room temperature, 20.0 g of the compound represented by formula (I-2-1), 14.0 g of 4-hydroxyphenylboronic acid, 2.9 g of dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphine]palladium(II), 26.8 g of sodium carbonate, 80 mL of ethanol, and 120 mL of water were added to a reaction vessel, and the mixture was stirred at 70 °C. After the reaction was completed, 10% hydrochloric acid was injected into the reaction solution, and extraction was performed using ethyl acetate. After washing the organic layer with saturated brine, the mixture was purified by column chromatography (silica gel, hexane) to obtain 21.0 g of the compound represented by formula (I-2-2).

[1654] Next, under nitrogen conditions and at room temperature, 21.0 g of the compound represented by formula (I-2-2), 13.3 g of pyridine, and 100 mL of dichloromethane were added to the reaction vessel. Then, while stirring at 0°C, 28.6 g of trifluoromethanesulfonic anhydride was added dropwise, and the mixture was stirred at 0°C for 1 hour. After the reaction was completed, 10% hydrochloric acid was injected into the reaction solution, and extraction was performed using dichloromethane. After washing the organic layer with saturated brine, the solution was purified by column chromatography (silica gel, dichloromethane) to obtain 31.8 g of the compound represented by formula (I-2-3).

[1655] Next, under nitrogen conditions and at room temperature, 20.0 g of the compound represented by formula (I-2-3), 0.4 g of copper iodide (I), 1.2 g of tetrakis(triphenylphosphine)palladium (0), 6.4 g of 2-aminoethanol, and 50 mL of N,N-dimethylformamide were added to the reaction vessel. While heating at 75°C, a solution was added dropwise to dissolve 9.6 g of the compound represented by formula (I-2-4) in 50 mL of N,N-dimethylformamide, and the mixture was stirred at 75°C for 2 hours. After the reaction was complete, the solution was filtered and purified by column chromatography (aminosilica gel, toluene) to obtain 9.8 g of the compound represented by formula (I-2-5).

[1656] Next, under nitrogen conditions and at room temperature, 9.8 g of the compound represented by formula (I-2-5), 50 mL of dichloromethane, and 7.0 g of 1,1-thiocarbonyldiimidazole were added to the reaction vessel, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed, the mixture was filtered and purified by column chromatography (silica gel, toluene) and subsequent recrystallization (toluene / hexane = 1 / 1) to obtain 3.7 g of the compound represented by formula (I-2).

[1657] MS(EI): m / z = 427

[1658] (Synthetic Example 3) Preparation of the compound represented by formula (I-3)

[1659] [Chemistry 258]

[1660]

[1661] In a nitrogen environment at room temperature, 25.0 g of the compound represented by formula (I-3-1), 0.8 g of copper iodide (I), 2.4 g of tetrakis(triphenylphosphine)palladium (0), 100 mL of triethylamine, and 50 mL of N,N-dimethylformamide were added to a reaction vessel. While heating at 75°C, a solution prepared by dissolving 12.4 g of trimethylsilylacetylene in 50 mL of N,N-dimethylformamide was added dropwise, and the mixture was stirred at 75°C for 2 hours. After the reaction was complete, 10% hydrochloric acid was injected into the reaction solution, and extraction was performed using toluene. After washing the organic layer with saturated brine, purification was performed using column chromatography (silica gel, toluene / hexane = 0 / 1 to 1 / 9) to obtain 26.3 g of the compound represented by formula (I-3-2).

[1662] Next, 26.3 g of the compound represented by formula (I-3-2), 125 mL of methanol, and 4.7 g of potassium carbonate were added to the reaction vessel at room temperature, and the mixture was stirred at room temperature. After the reaction was completed, the mixture was purified by column chromatography (silica gel, dichloromethane) to obtain 18.0 g of the compound represented by formula (I-3-3).

[1663] Next, under nitrogen and at room temperature, 25.0 g of 4-bromoiodobenzene, 0.7 g of copper iodide (I), 1.2 g of bis(triphenylphosphine)palladium dichloride (II), 44.7 g of triethylamine, and 62 mL of tetrahydrofuran were added to the reaction vessel. While stirring at room temperature, a solution containing 18.0 g of the compound represented by formula (I-3-3) dissolved in 62 mL of tetrahydrofuran was added dropwise, and the mixture was stirred at room temperature for 1 hour. 10% hydrochloric acid was injected into the reaction solution, and extraction was performed using toluene. After washing the organic layer with saturated brine, purification was performed using column chromatography (silica gel, toluene / hexane = 0 / 1 to 1 / 9) to obtain 24.4 g of the compound represented by formula (I-3-4).

[1664] Next, under nitrogen conditions and at room temperature, 9.0 g of the compound represented by formula (I-3-4), 7.1 g of the compound represented by formula (I-3-5), 94 mg of dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphine]palladium(II), 4.2 g of sodium carbonate, 40 mL of tetrahydrofuran, and 20 mL of water were added to the reaction vessel, and the mixture was stirred at 75 °C for 2 hours. After the reaction was completed, the mixture was filtered and purified by column chromatography (aminosilica gel, toluene) to obtain 7.3 g of the compound represented by formula (I-3-6).

[1665] Next, under nitrogen conditions and at room temperature, 7.3 g of the compound represented by formula (I-3-6), 35 mL of dichloromethane, and 4.1 g of 1,1-thiocarbonyldiimidazole were added to the reaction vessel, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed, the mixture was filtered and purified by column chromatography (silica gel, toluene) and subsequent recrystallization (toluene / hexane = 1 / 1) to obtain 5.6 g of the compound represented by formula (I-3).

[1666] MS(EI): m / z = 427

[1667] (Synthetic Example 4) Preparation of the compound represented by formula (I-4)

[1668] [Chemistry 259]

[1669]

[1670] In a nitrogen environment at room temperature, 10.0 g of the compound represented by formula (I-4-1), 0.3 g of copper iodide (I), 0.9 g of tetrakis(triphenylphosphine)palladium (0), 40 mL of triethylamine, and 20 mL of N,N-dimethylformamide were added to a reaction vessel. While heating at 75°C, a solution prepared by dissolving 4.7 g of trimethylsilylacetylene in 20 mL of N,N-dimethylformamide was added dropwise, and the mixture was stirred at 75°C for 2 hours. After the reaction was complete, 10% hydrochloric acid was injected into the reaction solution, and extraction was performed using toluene. After washing the organic layer with saturated brine, purification was performed using column chromatography (silica gel, toluene / hexane = 0 / 1 to 1 / 9) to obtain 8.1 g of the compound represented by formula (I-4-2).

[1671] Next, 8.1 g of the compound represented by formula (I-4-2), 40 mL of methanol, and 1.4 g of potassium carbonate were added to the reaction vessel at room temperature, and the mixture was stirred at room temperature. After the reaction was completed, the mixture was purified by column chromatography (silica gel, dichloromethane) to obtain 5.1 g of the compound represented by formula (I-4-3).

[1672] Next, under nitrogen and at room temperature, 4.7 g of the compound represented by formula (I-4-4), 0.2 g of copper iodide (I), 0.5 g of tetrakis(triphenylphosphine)palladium (0), 20 mL of triethylamine, and 10 mL of N,N-dimethylformamide were added to the reaction vessel. While heating at 75°C, a solution containing 5.1 g of the compound represented by formula (I-4-3) dissolved 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 complete, 10% hydrochloric acid was injected into the reaction solution, and extraction was performed using toluene. After washing the organic layer with saturated brine, purification was performed using column chromatography (silica gel, toluene / hexane = 1 / 9 to 1 / 4) to obtain 6.2 g of the compound represented by formula (I-4-5).

[1673] Next, under nitrogen conditions and at room temperature, 6.2 g of the compound represented by formula (I-4-5) and 70 mL of dichloromethane were added to the reaction vessel. While cooling in an ice bath, 4.2 g of N-bromosuccinimide was added in small increments, and the mixture was stirred at room temperature for 5 hours. After the reaction was complete, the reaction solution was injected into water and separated. The organic layer was washed with saturated brine and purified using column chromatography (silica gel, dichloromethane / hexane = 1 / 9 to 1 / 4) to obtain 6.5 g of the compound represented by formula (I-4-6).

[1674] Next, under nitrogen conditions and at room temperature, 6.5 g of the compound represented by formula (I-4-6), 4.2 g of the compound represented by formula (I-4-7), 0.1 g of dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphine]palladium(II), 3.3 g of sodium carbonate, 30 mL of tetrahydrofuran, and 15 mL of water were added to the reaction vessel, and the mixture was stirred at 75°C for 2 hours. After the reaction was completed, the mixture was filtered and purified by column chromatography (aminosilica gel, toluene) to obtain 5.2 g of the compound represented by formula (I-4-8).

[1675] Next, under nitrogen conditions and at room temperature, 5.2 g of the compound represented by formula (I-4-8), 25 mL of dichloromethane, and 2.4 g of 1,1-thiocarbonyldiimidazole were added to the reaction vessel, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed, the mixture was filtered and purified by column chromatography (silica gel, toluene) and subsequent recrystallization (toluene / hexane = 1 / 1) to obtain 3.2 g of the compound represented by formula (I-4).

[1676] MS(EI): m / z = 503

[1677] (Synthetic Example 5) Preparation of the compound represented by formula (I-5)

[1678] [Chemistry 260]

[1679]

[1680] Except that the compound represented by formula (I-1-3) was replaced with the compound represented by formula (I-5-3) in synthesis Example 1, the compound represented by formula (I-5) was prepared by the same method.

[1681] MS(EI): m / z = 333

[1682] (Synthetic Example 6) Preparation of the compound represented by formula (I-6)

[1683] [Chemistry 261]

[1684]

[1685] Except for replacing 1-hexyne with 1-heptyne in Synthesis Example 1, the compounds represented by formula (I-6) were prepared by the same method.

[1686] MS(EI): m / z = 365

[1687] (Synthetic Example 7) Preparation of the compound represented by formula (I-7)

[1688] [Chemistry 262]

[1689]

[1690] Except that the compound represented by formula (I-2-1) was replaced with the compound represented by formula (I-7-1) in synthesis example 2, the compound represented by formula (I-7) was prepared by the same method.

[1691] MS(EI): m / z = 445

[1692] (Synthetic Example 8) Preparation of the compound represented by formula (I-8)

[1693] [Chemistry 263]

[1694]

[1695] Except that the compound represented by formula (I-3-1) was replaced with the compound represented by formula (I-8-1) in synthesis example 3, the compound represented by formula (I-8) was prepared by the same method.

[1696] MS(EI): m / z = 441

[1697] (Synthetic Example 9) Preparation of the compound represented by formula (I-9)

[1698] [Chemistry 264]

[1699]

[1700] Except that in Synthesis Example 3, the compound represented by formula (I-9) was substituted with the compound represented by formula (I-9-1), the compound represented by formula (I-9) was prepared by the same method.

[1701] MS(EI): m / z = 455

[1702] (Synthetic Example 10) Preparation of the compound represented by formula (I-10)

[1703] [Chemistry 265]

[1704]

[1705] Except for replacing 4-bromoiodobenzene with 1-bromo-2-fluoro-4-iodobenzene in Synthesis Example 3, the compound represented by formula (I-10) was prepared by the same method.

[1706] MS(EI): m / z = 445

[1707] (Synthetic Example 11) Preparation of the compound represented by formula (I-11)

[1708] [Chemistry 266]

[1709]

[1710] Except that the compound represented by formula (I-10-1) was replaced with the compound represented by formula (I-11-1) in synthesis example 10, the compound represented by formula (I-11) was prepared by the same method.

[1711] MS(EI): m / z = 459

[1712] (Synthetic Example 12) Preparation of the compound represented by formula (I-12)

[1713] [Chemistry 267]

[1714]

[1715] In a nitrogen environment at room temperature, 15.0 g of the compound represented by formula (I-12-1), 0.3 g of copper iodide (I), 0.9 g of tetrakis(triphenylphosphine)palladium (0), 4.8 g of 2-aminoethanol, and 30 mL of N,N-dimethylformamide were added to a reaction vessel. While heating at 75°C, a solution prepared by dissolving 4.6 g of trimethylsilylacetylene in 30 mL of N,N-dimethylformamide was added dropwise, and the mixture was stirred at 75°C for 2 hours. After the reaction was complete, the solution was filtered and purified by column chromatography (silica gel, toluene / hexane = 0 / 1 to 1 / 9) to obtain 11.7 g of the compound represented by formula (I-12-2).

[1716] Next, 11.7 g of the compound represented by formula (I-12-2), 60 mL of methanol, and 1.6 g of potassium carbonate were added to the reaction vessel at room temperature, and the mixture was stirred at room temperature. After the reaction was completed, the mixture was purified by column chromatography (silica gel, dichloromethane) to obtain 8.4 g of the compound represented by formula (I-12-3).

[1717] Next, under nitrogen conditions and at room temperature, 8.4 g of the compound represented by formula (I-12-3), 3.9 g of catechol borane, 2.3 g of bis(triphenylphosphine)palladium(II) dichloride, and 80 mL of tetrahydrofuran were added to the reaction vessel, and the mixture was heated under reflux for 3 hours to allow the reaction to proceed. After the reaction was complete, the mixture was post-treated with water and then extracted with ethyl acetate. The organic layer was concentrated to obtain 8.2 g of the compound represented by formula (I-12-4).

[1718] Next, under nitrogen conditions and at room temperature, 8.2 g of the compound represented by formula (I-12-4), 4.3 g of the compound represented by formula (I-12-5), 0.1 g of dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphine]palladium(II), 4.4 g of sodium carbonate, 20 mL of tetrahydrofuran, and 20 mL of water were added to the reaction vessel, and the mixture was stirred at 75°C for 2 hours. After the reaction was completed, the mixture was filtered and purified by column chromatography (silica gel, toluene) to obtain 6.2 g of the compound represented by formula (I-12-6).

[1719] Next, under nitrogen conditions and at room temperature, 6.2 g of the compound represented by formula (I-12-6), 30 mL of dichloromethane, and 3.0 g of 1,1-thiocarbonyldiimidazole were added to the reaction vessel, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed, the mixture was filtered and purified by column chromatography (silica gel, toluene) and subsequent recrystallization (toluene / hexane = 1 / 1) to obtain 4.6 g of the compound represented by formula (I-12).

[1720] MS(EI): m / z = 429

[1721] (Synthetic Example 13) Preparation of the compound represented by formula (I-13)

[1722] [Chemistry 268]

[1723]

[1724] Except that in Example 4, the compound represented by formula (I-4-1) was replaced with the compound represented by formula (I-13-1), the compound represented by formula (I-13) was prepared by the same method.

[1725] MS(EI): m / z = 517

[1726] (Synthetic Example 14) Preparation of the compound represented by formula (I-14)

[1727] [Chemistry 269]

[1728]

[1729] In a nitrogen environment at room temperature, 50.0 g of the compound represented by formula (I-14-1), 2.0 g of copper iodide (I), 6.0 g of tetrakis(triphenylphosphine)palladium (0), 200 mL of triethylamine, and 100 mL of N,N-dimethylformamide were added to a reaction vessel. Then, while heating at 75°C, a solution prepared by dissolving 30.5 g of trimethylsilylacetylene in 100 mL of N,N-dimethylformamide was added dropwise, and the mixture was stirred at 75°C for 2 hours. After the reaction was complete, a saturated aqueous solution of ammonium chloride was injected into the reaction solution, and extraction was performed using hexane. After washing the organic layer with saturated brine, purification was performed using column chromatography (silica gel, ethyl acetate / hexane = 0 / 1 to 1 / 9) to obtain 54.1 g of the compound represented by formula (I-14-2).

[1730] Next, 10.0 g of the compound represented by formula (I-14-2) and 100 mL of tetrahydrofuran were added to the reaction vessel under nitrogen and at room temperature. Then, while cooling to -78°C, 22 mL of n-butyllithium (2.6 mol / L n-hexane solution) was added dropwise, and the mixture was stirred at -78°C for 1 hour. Next, a solution containing 15.7 g of iodine dissolved in 32 mL of tetrahydrofuran was added dropwise, and the mixture was stirred at -78°C for 1 hour, then at room temperature for 1 hour. After the reaction was complete, 10% hydrochloric acid was injected into the reaction solution, and extraction was performed using hexane. After washing the organic layer with saturated brine, purification was performed using column chromatography (silica gel, ethyl acetate / hexane = 0 / 1 to 1 / 9) to obtain 13.3 g of the compound represented by formula (I-14-3).

[1731] Next, under nitrogen conditions and at room temperature, 13.3 g of the compound represented by formula (I-14-3), 0.3 g of copper iodide (I), 0.9 g of bis(triphenylphosphine)palladium dichloride (II), 20.0 g of triethylamine, and 33 mL of tetrahydrofuran were added to the reaction vessel. Then, while stirring at 60 °C, a solution containing 4.9 g of 1-hexyne dissolved in 33 mL of tetrahydrofuran was added dropwise, and the mixture was stirred at 75 °C for 10 hours. After the reaction was complete, 10% hydrochloric acid was injected into the reaction solution, and extraction was performed using toluene. After washing the organic layer with saturated brine, purification was performed using column chromatography (silica gel, ethyl acetate / hexane = 0 / 1 to 1 / 9) to obtain 10.3 g of the compound represented by formula (I-14-4).

[1732] Next, 10.3 g of the compound represented by formula (I-14-4), 52 mL of methanol, and 1.6 g of potassium carbonate were added to the reaction vessel at room temperature, and the mixture was stirred at room temperature. After the reaction was completed, the mixture was purified by column chromatography (silica gel, dichloromethane) to obtain 7.0 g of the compound represented by formula (I-14-5).

[1733] Next, under nitrogen and at room temperature, 5.0 g of 1-bromo-4-iodobenzene, 0.1 g of copper iodide (I), 0.2 g of bis(triphenylphosphine)palladium dichloride (II), 8.9 g of triethylamine, and 13 mL of tetrahydrofuran were added to the reaction vessel. Then, while stirring at room temperature, a solution containing 4.2 g of the compound represented by formula (I-14-5) dissolved in 13 mL of tetrahydrofuran was added dropwise, and the mixture was stirred at room temperature for 1 hour. After the reaction was complete, 10% hydrochloric acid was injected into the reaction solution, and extraction was performed using toluene. After washing the organic layer with saturated brine, purification was performed using column chromatography (silica gel, toluene / hexane = 0 / 1 to 1 / 7) to obtain 6.6 g of the compound represented by formula (I-14-6).

[1734] Next, under nitrogen conditions and at room temperature, 6.6 g of the compound represented by formula (I-14-6), 4.8 g of the compound represented by formula (I-14-7), 0.7 g of bis(triphenylphosphine)palladium(II) dichloride, 3.8 g of sodium carbonate, 35 mL of tetrahydrofuran, and 18 mL of water were added to the reaction vessel, and the mixture was stirred at 75°C for 2 hours. After the reaction was completed, the mixture was filtered and purified by column chromatography (aminosilica gel, toluene) to obtain 5.3 g of the compound represented by formula (I-14-8).

[1735] Next, under nitrogen conditions and at room temperature, 5.3 g of the compound represented by formula (I-14-8), 30 mL of dichloromethane, and 2.7 g of 1,1-thiocarbonyldiimidazole were added to the reaction vessel, and the mixture was 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) to obtain 3.3 g of the compound represented by formula (I-14).

[1736] MS(EI): m / z = 463

[1737] (Synthetic Example 15) Preparation of the compound represented by formula (I-15)

[1738] [Chemistry 270]

[1739]

[1740] Except that the compound represented by formula (I-15-1) was replaced with the compound represented by formula (I-15-1) in synthesis example 1, the compound represented by formula (I-15-2) was obtained by the same method.

[1741] Next, except that the compound represented by formula (I-3-1) was replaced with the compound represented by formula (I-15-2) in synthesis example 3, the compound represented by formula (I-15) was prepared by the same method.

[1742] MS(EI): m / z = 445

[1743] (Synthetic Example 16) Preparation of the compound represented by formula (I-16)

[1744] [Chemistry 271]

[1745]

[1746] In a nitrogen environment at room temperature, 50 g of the compound represented by formula (I-16-1), 1.4 g of copper iodide (I), 2.5 g of bis(triphenylphosphine)palladium dichloride (II), 53.7 g of triethylamine, and 125 mL of tetrahydrofuran were added to a reaction vessel. Then, while stirring at room temperature, a solution containing 30.0 g of the compound represented by formula (I-16-2) dissolved in 125 mL of tetrahydrofuran was added dropwise, and the mixture was stirred at room temperature for 1 hour. After the reaction was complete, a saturated aqueous solution of ammonium chloride was added to the reaction mixture, and extraction was performed using toluene. After washing the organic layer with saturated brine, purification was performed using column chromatography (aminosilica gel, toluene / hexane = 1 / 8 to 1 / 0) to obtain 50.3 g of the compound represented by formula (I-16-3).

[1747] Next, under nitrogen conditions and at room temperature, 42.0 g of the compound represented by formula (I-16-3), 36.3 g of bis(pinacolato)diboron, 40.1 g of potassium acetate, 2.2 g of [1,1'-bis(diphenylphosphine)ferrocene]palladium(II)dichloromethane adduct, and 420 mL of dimethyl sulfoxide were added to the reaction vessel, and the mixture was stirred at 90 °C. After the reaction was complete, a saturated aqueous solution of ammonium chloride was added to the reaction solution, and extraction was performed using toluene. After washing the organic layer with saturated brine, the mixture was purified by column chromatography (alumina silica gel, toluene) to obtain 36.6 g of the compound represented by formula (I-16-4).

[1748] Next, under nitrogen conditions and at room temperature, 6 g of the compound represented by formula (I-16-5), 7.5 g of the compound represented by formula (I-16-4), 0.1 g of bis(triphenylphosphine)palladium(II) dichloride, 4.3 g of sodium carbonate, 30 mL of tetrahydrofuran, and 20 mL of water were added to the reaction vessel, and the mixture was stirred at 75°C for 2 hours. After the reaction was completed, the mixture was filtered and purified by column chromatography (aminosilica gel, toluene / hexane = 2 / 3 to 1 / 0) to obtain 4.1 g of the compound represented by formula (I-16-6).

[1749] Next, under nitrogen and at room temperature, 4.0 g of the compound represented by formula (I-16-6), 76 mg of copper iodide (I), 0.2 g of tetra(triphenylphosphine)palladium (0), 1.2 g of 2-aminoethanol, and 10 mL of tetrahydrofuran were added to the reaction vessel. Then, while heating at 75°C, a solution containing 1.2 g of 1-hexyne dissolved in 10 mL of tetrahydrofuran was added dropwise, and the mixture was stirred at 75°C for 2 hours. After the reaction was complete, a saturated aqueous solution of ammonium chloride was injected into the reaction mixture, and extraction was performed using toluene. After washing the organic layer with saturated brine, purification was performed using column chromatography (aminosilica gel, toluene / hexane = 0 / 1 to 1 / 1) to obtain 3.3 g of the compound represented by formula (I-16-7).

[1750] Next, under nitrogen conditions and at room temperature, 3.3 g of the compound represented by formula (I-16-7), 17 mL of dichloromethane, and 1.8 g of 1,1-thiocarbonyldiimidazole were added to the reaction vessel, and the mixture was 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) to obtain 1.4 g of the compound represented by formula (I-16).

[1751] MS(EI): m / z = 441

[1752] (Synthetic Example 17) Preparation of the compound represented by formula (I-17)

[1753] [Chemistry 272]

[1754]

[1755] Using 5.7 g of 1-bromo-4-iodobenzene instead of 6 g of (I-16-5) in synthesis example 16, 3.8 g of formula (I-17-1) was obtained by the same method.

[1756] Next, under nitrogen conditions and at room temperature, 3.8 g of the compound represented by formula (I-17-1), 76 mg of copper iodide (I), 0.2 g of tetra(triphenylphosphine)palladium (0), 1.2 g of 2-aminoethanol, and 10 mL of tetrahydrofuran were added to the reaction vessel. Then, while heating at 75°C, a solution prepared by dissolving 1.4 g of 5-methylhexyne in 10 mL of tetrahydrofuran was added dropwise, and the mixture was stirred at 75°C for 2 hours. After the reaction was complete, a saturated aqueous solution of ammonium chloride was injected into the reaction solution, and extraction was performed using toluene. After washing the organic layer with saturated brine, purification was performed using column chromatography (aminosilica gel, toluene / hexane = 0 / 1 to 1 / 1) to obtain 2.8 g of the compound represented by formula (I-17-2).

[1757] Next, under nitrogen conditions and at room temperature, 2.8 g of the compound represented by formula (I-17-2), 17 mL of dichloromethane, and 1.5 g of 1,1-thiocarbonyldiimidazole were added to the reaction vessel, and the mixture was 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) to obtain 2.2 g of the compound represented by formula (I-17).

[1758] MS(EI): m / z = 441

[1759] (Synthetic Example 18) Preparation of the compound represented by formula (I-18)

[1760] [Chemistry 273]

[1761]

[1762] Under nitrogen conditions, 2.4 g of sodium hydride and 40 mL of tetrahydrofuran were added, and the reaction vessel was kept below 10°C. Then, 10 mL of a tetrahydrofuran solution containing 5.6 g of propargyl alcohol was slowly added dropwise, and the reaction was continued at 10°C for 1 hour after the addition was complete. Next, 30 mL of a tetrahydrofuran solution containing 20 g of ethyl iodide was slowly added dropwise. After the addition was complete, the reaction vessel was returned to room temperature, and the reaction was continued for 2 hours. Then, the reaction vessel was kept below 10°C, and 50 mL of 5% hydrochloric acid was slowly added dropwise for neutralization. After extraction of the reaction solution with ethyl acetate and washing of the organic layer with water and saturated brine, the organic solvent was removed by distillation, yielding 8 g of 3-ethoxyprop-1-yne.

[1763] Subsequently, 5.7 g of 4-iodo-1-bromobenzene was used to replace 6 g of (I-16-5) in synthesis Example 16, and 3.8 g of formula (I-18-1) was obtained by the same method.

[1764] Next, under nitrogen and at room temperature, 3.8 g of the compound represented by formula (I-18-1), 76 mg of copper iodide (I), 0.2 g of tetra(triphenylphosphine)palladium (0), 1.2 g of 2-aminoethanol, and 10 mL of tetrahydrofuran were added to the reaction vessel. Then, while heating at 75°C, a solution prepared by dissolving 1.1 g of 3-ethoxyprop-1-yne in 10 mL of tetrahydrofuran was added dropwise, and the mixture was stirred at 75°C for 2 hours. After the reaction was complete, a saturated aqueous solution of ammonium chloride was injected into the reaction solution, and extraction was performed using toluene. After washing the organic layer with saturated brine, purification was performed using column chromatography (aminosilica gel, toluene / hexane = 0 / 1 to 1 / 1), thereby obtaining 2.3 g of the compound represented by formula (I-18-2).

[1765] Next, under nitrogen conditions and at room temperature, 2.3 g of the compound represented by formula (I-18-2), 17 mL of dichloromethane, and 1.7 g of 1,1'-thiocarbonyl-di-2-(1H)pyridone were added to the reaction vessel, and the mixture was stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated brine and purified by column chromatography (silica gel, toluene) and subsequent recrystallization (toluene / hexane = 1 / 1) to obtain 2.0 g of the compound represented by formula (I-18).

[1766] MS(EI): m / z = 429

[1767] (Synthetic Example 19) Preparation of the compound represented by formula (I-19)

[1768] [Chemistry 274]

[1769]

[1770] Using 6g of 4-bromo-1-iodo-2-methylbenzene instead of 6g of (I-16-5) in Synthesis Example 16, 3.5g of formula (I-19-1) was obtained by the same method.

[1771] Next, under nitrogen and at room temperature, 3.5 g of the compound represented by formula (I-17-1), 76 mg of copper iodide (I), 0.2 g of tetra(triphenylphosphine)palladium (0), 1.1 g of 2-aminoethanol, and 10 mL of tetrahydrofuran were added to the reaction vessel. Then, while heating at 75°C, a solution prepared by dissolving 1.3 g of 5-methylhexyne in 10 mL of tetrahydrofuran was added dropwise, and the mixture was stirred at 75°C for 2 hours. After the reaction was complete, a saturated aqueous solution of ammonium chloride was injected into the reaction solution, and extraction was performed using toluene. After washing the organic layer with saturated brine, purification was performed using column chromatography (aminosilica gel, toluene / hexane = 0 / 1 to 1 / 1) to obtain 2.6 g of the compound represented by formula (I-19-2).

[1772] Next, under nitrogen conditions and at room temperature, 2.6 g of the compound represented by formula (I-19-2), 17 mL of dichloromethane, and 1.5 g of 1,1-thiocarbonyldiimidazole were added to the reaction vessel, and the mixture was 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) to obtain 2.0 g of the compound represented by formula (I-19).

[1773] MS(EI): m / z = 441

[1774] (Synthetic Example 20) Preparation of the compound represented by formula (I-20)

[1775] [Chemistry 275]

[1776]

[1777] Using 6.2 g of 4-bromo-2-fluoro-1-iodobenzene instead of 6 g of (I-16-5) in Synthesis Example 16, 4.3 g of formula (I-20-1) was obtained by the same method.

[1778] Next, under nitrogen and at room temperature, 4.3 g of the compound represented by formula (I-20-1), 76 mg of copper iodide (I), 0.2 g of tetra(triphenylphosphine)palladium (0), 1.2 g of 2-aminoethanol, and 10 mL of tetrahydrofuran were added to the reaction vessel. Then, while heating at 75°C, a solution prepared by dissolving 1.5 g of 1-heptyne in 10 mL of tetrahydrofuran was added dropwise, and the mixture was stirred at 75°C for 2 hours. After the reaction was complete, a saturated aqueous solution of ammonium chloride was injected into the reaction solution, and extraction was performed using toluene. After washing the organic layer with saturated brine, purification was performed using column chromatography (aminosilica gel, toluene / hexane = 0 / 1 to 1 / 1) to obtain 3.4 g of the compound represented by formula (I-20-2).

[1779] Next, under nitrogen conditions and at room temperature, 3.4 g of the compound represented by formula (I-20-2), 17 mL of dichloromethane, and 1.9 g of 1,1-thiocarbonyldiimidazole were added to the reaction vessel, and the mixture was 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) to obtain 1.6 g of the compound represented by formula (I-20).

[1780] MS(EI): m / z = 459

[1781] Industrial availability

[1782] The compounds and liquid crystal compositions of the present invention can be used in 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), In general formula (i), R i1 The basis represented is chosen freely according to the following formula (R) i1 -1) ~ Formula (R) i1 In the group consisting of -16), Formula (R) i1 -1) ~ Formula (R) i1 In -16), The black dot indicates the direction to A. i1 The key bond, A i1 The basis represented is chosen freely according to the following formula (A) i1 -2), Equation (A) i1 -SP-1), Formula (A) i1 -SP-2), Formula (A) i1 -SP-3) and formula (A i1 In the group consisting of -SP-4), Formula (A) i1 -2), Equation (A) i1 -SP-1), Formula (A) i1 -SP-2), Formula (A) i1 -SP-3) and formula (A i1 In -SP-4), The white dot indicates the direction of R. i1 The key bond, The black dot represents Z. i1 The key bond, A i2 The basis represented is chosen freely according to the following formula (A) i2 -2), Equation (A) i2 -14), Equation (A) i2 -SP-1), Formula (A) i2 -SP-2) and formula (A) i2 In the group consisting of -SP-3), Formula (A) i2 -2), Equation (A) i2 -14), Equation (A) i2 -SP-1), Formula (A) i2 -SP-2) and formula (A) i2 In -SP-3), The white dot indicates Z. i1 The key bond, The black dot represents Z. i2 Or the bond formed by the isothiocyanate group, A i3 The basis represented is chosen freely according to the following formula (A) i3 -1), Equation (A) i3 -SP-1) and formula (A) i3 In the group consisting of -SP-2), Formula (A) i3 -1), Equation (A) i3 -SP-1) and formula (A) i3 In -SP-2), The white dot indicates Z. i2 The key bond, The black dots represent bonds to the isothiocyanate groups. Substituent S i1 It represents any one of the following: fluorine atom, chlorine atom, bromine atom, iodine atom, or alkyl group having 1 to 6 carbon atoms. In the substituent S i1 When multiple instances exist, these can be the same or different. Z i1 and Z i2 Each of the following can be independently represented: a single bond, -CH=CH-, or -C≡C-. n i1 An integer representing 1.

2. The liquid crystal composition according to claim 1, wherein the compound represented by general formula (i) is selected from the group consisting of compounds represented by the following structural formulas: (i-3-3.2), (i-2-3.2), (i-2-11.2), (i-3-6.1), (i-2-3.3), (i-2-3.4), (i-2-4.2), (i-2-4.3), (i-5-1.2), (i-2-11.3), (i-2-14.2), (i-2-15.5), (i-3-11.2), (i-3-3.5), (i-3-3.6), (i-3-6.3), and (i-3-6.2). 。 3. The liquid crystal composition according to claim 1 or 2, wherein the total content of the compound represented by the general formula (i) in 100% by mass of the liquid crystal composition is 5% to 75% by mass.

4. The liquid crystal composition according to claim 1 or 2, further comprising one or more of the following structural formulas (ii-6-27.2), (ii-6-27.3), (ii-6-27.4), (ii-6-5.2), (ii-6-5.3), (ii-6-5.4), (ii-4-13.2), (ii-4-13.3), (ii-1-1.2), (ii-2-1.3), (ii-2-2.2), (ii-2-2.3), and structural formulas. Compounds in the group consisting of compounds represented by formula (ii-2-1.1), structural formula (ii-2-3.1), structural formula (ii-2-3.3), structural formula (ii-5-2.1), structural formula (ii-5-2.3), structural formula (ii-3-1.3), structural formula (ii-3-1.4), structural formula (ii-3-3.2), structural formula (ii-3-3.3), structural formula (ii-5-5.1), structural formula (ii-3-6.1), structural formula (ii-3-6.2), structural formula (ii-3-2.3), and structural formula (ii-4-5.1). 。 5. The liquid crystal composition according to claim 4, wherein the structural formulas (ii-6-27.2), (ii-6-27.3), (ii-6-27.4), (ii-6-5.2), (ii-6-5.3), (ii-6-5.4), (ii-4-13.2), (ii-4-13.3), (ii-1-1.2), (ii-2-1.3), (ii-2-2.2), (ii-2-2.3), (ii-2-1.1), and (i-6-27.2) are... The total content of the compounds represented by the structural formulas (ii-2-3.1), (ii-2-3.3), (ii-5-2.1), (ii-5-2.3), (ii-3-1.3), (ii-3-1.4), (ii-3-3.2), (ii-3-3.3), (ii-5-5.1), (ii-3-6.1), (ii-3-6.2), (ii-3-2.3), and (ii-4-5.1) in the liquid crystal composition is 25% to 95% by mass.

6. The liquid crystal composition according to claim 1 or 2 further comprises one or more compounds selected from the group consisting of compounds represented by the following structural formulas (np-2-3.1) to (np-2-3.3). 。 7. The liquid crystal composition according to claim 1 or 2 further comprises a stabilizer selected from the group consisting of compounds represented by the following structural formulas (XX-1) to (XX-3) and (YY-1) to (YY-2). 。 8. The liquid crystal composition according to claim 7, wherein the total content of the stabilizer in 100% by mass of the liquid crystal composition is 0.03% to 0.35% by mass.

9. The liquid crystal composition according to claim 1 or 2, wherein Δn at 25°C and 589 nm is 0.40 to 0.

50.

10. The liquid crystal composition according to claim 1 or 2, wherein the upper limit temperature of the liquid crystal phase is 110°C to 180°C.

11. The liquid crystal composition according to claim 1 or 2, wherein the V at 25°C th The voltage range is 1.3 V to 2.1 V.

12. The liquid crystal composition according to claim 1 or 2, wherein Δε at 25°C r It ranges from 1.00 to 1.

35.

13. The liquid crystal composition according to claim 1 or 2, wherein the tanδ at 25°C iso The value ranges from 0.001 to 0.

025.

14. The liquid crystal composition according to claim 1 or 2, wherein the rotational viscosity at 25°C is 250 mPa·s to 1250 mPa·s.

15. A liquid crystal display element using a liquid crystal composition as described in any one of claims 1 to 14.

16. The liquid crystal display element according to claim 15, driven in an active matrix manner or a passive matrix manner.

17. A liquid crystal display element that reversibly switches its dielectric constant by reversibly changing the orientation of liquid crystal molecules in a liquid crystal composition as described in any one of claims 1 to 14.

18. A sensor using a liquid crystal composition as described in any one of claims 1 to 14.

19. A liquid crystal lens using a liquid crystal composition as described in any one of claims 1 to 14.

20. An optical communication device using a liquid crystal composition as described in any one of claims 1 to 14.

21. An antenna using a liquid crystal composition as described in any one of claims 1 to 14.

22. The antenna according to claim 21, comprising: The first substrate has multiple grooves; The second substrate, facing the first substrate, is provided with a power supply section; A first dielectric layer is disposed between the first substrate and the second substrate; Multiple patch electrodes are configured corresponding to the multiple slots; The 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 as described in any one of claims 1 to 14.

23. A compound represented by the following general formula (i), In general formula (i), R i1 The basis represented is chosen freely according to the following formula (R) i1 -1) ~ Formula (R) i1 In the group consisting of -16), Formula (R) i1 -1) ~ Formula (R) i1 In -16), The black dot indicates the direction to A. i1 The key bond, A i1 The basis represented is chosen freely according to the following formula (A) i1 -2), Equation (A) i1 -SP-1), Formula (A) i1 -SP-2), Formula (A) i1 -SP-3) and formula (A i1 In the group consisting of -SP-4), Formula (A) i1 -2), Equation (A) i1 -SP-1), Formula (A) i1 -SP-2), Formula (A) i1 -SP-3) and formula (A i1 In -SP-4), The white dot indicates the direction of R. i1 The key bond, The black dot represents Z. i1 The key bond, A i2 The basis represented is chosen freely according to the following formula (A) i2 -2), Equation (A) i2 -14), Equation (A) i2 -SP-1), Formula (A) i2 -SP-2) and formula (A) i2 In the group consisting of -SP-3), Formula (A) i2 -2), Equation (A) i2 -14), Equation (A) i2 -SP-1), Formula (A) i2 -SP-2) and formula (A) i2 In -SP-3), The white dot indicates Z. i1 The key bond, The black dot represents Z. i2 Or the bond formed by the isothiocyanate group, A i3 The basis represented is chosen freely according to the following formula (A) i3 -1), Equation (A) i3 -SP-1) and formula (A) i3 In the group consisting of -SP-2), Formula (A) i3 -1), Equation (A) i3 -SP-1) and formula (A) i3 In -SP-2), The white dot indicates Z. i2 The key bond, The black dots represent bonds to the isothiocyanate groups. Substituent S i1 It represents any one of the following: fluorine atom, chlorine atom, bromine atom, iodine atom, or alkyl group having 1 to 6 carbon atoms. In the substituent S i1 When multiple instances exist, these can be the same or different. Z i1 and Z i2 Each of the following can be independently represented: a single bond, -CH=CH-, or -C≡C-. n i1 An integer representing 1.

24. The compound according to claim 23, wherein the compound represented by general formula (i) is selected from the group consisting of compounds represented by the following structural formulas: (i-3-3.2), (i-2-3.2), (i-2-11.2), (i-3-6.1), (i-2-3.3), (i-2-3.4), (i-2-4.2), (i-2-4.3), (i-5-1.2), (i-2-11.3), (i-2-14.2), (i-2-15.5), (i-3-11.2), (i-3-3.5), (i-3-3.6), (i-3-6.3), and (i-3-6.2). 。

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