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

Abstract

The present invention aims to provide a compound, a liquid crystal composition, and a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the same, which can provide a liquid crystal composition having high Tni, large Δn, low Vth, large Δεr, small tanδiso, and good storage properties at low temperatures. Specifically, the invention comprises a compound represented by general formula (i) having an ethylene group (-C≡C-) and an isothiocyanate group (-NCS), and a liquid crystal composition comprising one or more of said compound.

Description

Technology Field

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

[0002] As a new application for liquid crystals, which are widely used in displays, LCD antennas capable of transmitting and receiving radio waves between mobile devices such as automobiles and communication satellites are attracting attention. Conventionally, satellite communication utilizes parabolic antennas; however, when used in mobile devices such as automobiles, the parabolic antenna must be frequently angled toward the satellite, requiring a large movable part. In contrast, LCD antennas can change the direction of radio wave transmission and reception by operating the liquid crystals within the panel, eliminating the need to move the antenna itself and allowing for a flat antenna shape. Furthermore, to realize global high-capacity and high-speed communication, low-orbit satellite constellations using multiple satellites are being explored. Liquid crystal antennas, which can easily change the direction of radio wave transmission and reception, are useful for tracking low-orbit satellites that appear to be constantly moving from the ground.

[0003] Generally, autonomous driving for vehicles requires the downloading of large amounts of high-precision 3D map information. However, if an antenna using liquid crystal is used, the downloading of large amounts of data from communication satellites becomes possible without mechanical moving parts by incorporating the antenna into the vehicle. The frequency band used for satellite communication is approximately 13 GHz, which is significantly different from the frequency used for liquid crystal displays to date. Consequently, the required physical properties for the liquid crystal are also significantly different, and the required Δn for the liquid crystal for the antenna is about 0.4, and the operating temperature range is -20 to 120°C.

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

[0005] In addition, it is known that many liquid crystal compounds constituting liquid crystal compositions exhibiting a high Δn of 0.2 or higher have low compatibility. Therefore, it is also important to select liquid crystal compounds with high compatibility.

[0006] Regarding this, for example, Patent Document 1 can be cited as a technology for liquid crystals for antennas.

[0007] In addition, Non-patent Literature 1 proposes the use of liquid crystal materials as components of high-frequency devices. Prior art literature

[0008] Japanese Patent Publication No. 2016-37607

[0009] D. Dolfi, Electronics Letters, (UK), 1993, Vol. 29, No. 10, pp. 926-927 The problem to be solved

[0010] The present invention is, T ni g is high, Δn is large, and V th is low, and Δε r This is large, and tanδ iso The objective is to provide a compound, a liquid crystal composition, and a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the same, which can provide a liquid crystal composition with a small size and good preservation at low temperatures. means of solving the problem

[0011] The inventors, after careful consideration, discovered that a liquid crystal composition comprising one or more compounds represented by general formula (i) having an ethylene group (-C≡C-) and an isothiocyanate group (-NCS) can solve the above problem, and thus completed the present invention.

[0012] The configuration of the present invention for solving the above problem is as follows.

[0013] The compound according to the present invention is,

[0014] The following general formula (i)

[0015]

[0016] ( Among general formula (i),

[0017] R i1 Representing silver, hydrogen atoms, halogen atoms, or alkyl groups having 1 to 20 carbon atoms,

[0018] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-, and

[0019] One or more -CH2-CH2- groups in the alkyl group may each be independently substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-, and

[0020] One or more -CH2-CH2-CH2- groups among the alkyl groups may each be independently substituted with -O-CO-O-, and

[0021] One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom,

[0022] There are no cases where oxygen atoms directly bond with each other,

[0023] A i1 , A i2 and Ai3 Each independently, the following units (a), (b), (c) and (d):

[0024] (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- in this group may be substituted with -O- and / or -S-)

[0025] (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0026] (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group(naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, One -CH= or two or more non-adjacent -CH= present in 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, or phenanthrene-2,7-diyl group may be substituted with -N=.)

[0027] (d) Thiophene-2,5-diyl group, benzothiophen-2,5-diyl group, benzothiophen-2,6-diyl group, dibenzothiophen-3,7-diyl group, dibenzothiophen-2,6-diyl group, thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0028] It represents a group selected from a group consisting of,

[0029] Above A i1There are no cases where 1,2,3,4-tetrahydronaphthalene-2,6-diyl group is represented, and

[0030] Above A i1 , A i2 and A i3 One or more hydrogen atoms among them, independently, are substituent S i1 It may be substituted by,

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

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

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

[0034] One or more -CH2-CH2-CH2- groups in the alkyl group may each be independently substituted with -O-CO-O-, and

[0035] One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom,

[0036] There are no cases where oxygen atoms directly bond with each other,

[0037] Substituent S i1In cases where there are multiple instances, they may be identical or different,

[0038] Z i1 It represents any one of a single bond, an alkylene group having 1 to 20 carbon atoms, and

[0039] One or more -CH2- groups in the alkylene group may each be independently substituted with -O-, -CF2- and / or -CO-, and

[0040] One or more -CH2-CH2- groups in the alkylene group may each be independently substituted with -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-,

[0041] There are no cases where oxygen atoms directly bond with each other.

[0042] It is characterized by being a compound represented by .

[0043] In addition, the liquid crystal composition according to the present invention is characterized by including one or two or more of the above compounds.

[0044] In addition, the liquid crystal display element according to the present invention is characterized by using the liquid crystal composition described above.

[0045] In addition, the sensor according to the present invention is characterized by using the liquid crystal composition described above.

[0046] In addition, the liquid crystal lens according to the present invention is characterized by using the liquid crystal composition described above.

[0047] In addition, the optical communication device according to the present invention is characterized by using the liquid crystal composition described above.

[0048] In addition, the antenna according to the present invention is characterized by using the liquid crystal composition described above. Effects of the invention

[0049] According to the present invention, by a liquid crystal composition comprising one or more compounds represented by general formula (i) having an ethylene group (-C≡C-) and an isothiocyanate group (-NCS), T ni g is high, Δn is large, and V th is low, and Δε r This is large, and tanδ iso A liquid crystal composition with a small size and good preservation at low temperatures can be obtained, and said liquid crystal composition is useful for liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas. Brief explanation of the drawing

[0050] FIG. 1 is an example of a schematic diagram of a vehicle equipped with an antenna according to the present invention. FIG. 2 is an example of an exploded view of an antenna according to the present invention. FIG. 3 is an example of an exploded view of an antenna body according to the present invention. FIG. 4 is an example of a top view of a slot array portion in the present invention. FIG. 5 is an example of a top view of a projection of an antenna body according to the present invention. FIG. 6 is a cross-sectional view of the antenna body of FIG. 5 cut with an AA line. Figure 7 is another form of a cross-sectional view of the antenna body of Figure 5 cut with an AA line. FIG. 8 is another example of a top view showing a projection of an antenna body according to the present invention. FIG. 9 is a cross-sectional view of the antenna body of FIG. 8 cut along the CC line. FIG. 10 is a cross-sectional view of the antenna body of FIG. 8 cut by the BB line. Specific details for implementing the invention

[0051] (Compounds represented by general formula (i))

[0052] The compound according to the present invention is a compound represented by the following general formula (i) having an ethylene group (-C≡C-) and an isothiocyanate group (-NCS).

[0053] In addition, the liquid crystal composition according to the present invention comprises one or more compounds represented by general formula (i) having an ethylene group (-C≡C-) and an isothiocyanate group (-NCS).

[0054]

[0055] Among general formula (i), R i1 It represents silver, hydrogen atoms, halogen atoms, or alkyl groups having 1 to 20 carbon atoms.

[0056] Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0057] The alkyl group having 1 to 20 carbon atoms is a straight-chain, branched, or cyclic alkyl group, and it is preferably a straight-chain alkyl group.

[0058] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.

[0059] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0060] In addition, one or more -CH2-CH2- groups among the alkyl groups may each be independently substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0061] In addition, one or more -CH2-CH2-CH2- among the alkyl groups may each be independently substituted with -O-CO-O-.

[0062] In addition, one or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[0063] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0064] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0065] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0066] For example, R i1 One -CH2- in the alkyl group can be substituted with -O- to form an alkoxy group having 1 to 19 carbon atoms.

[0067] The alkoxy group is a linear, branched, or cyclic alkoxy group, and it is preferable that it be a linear alkoxy group.

[0068] The number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0069] Also, R i1 In this case, one -CH2- in the alkyl group is substituted with -S-, thereby forming a thioalkoxy group (alkylsulfanyl group, alkylthio group) having 1 to 19 carbon atoms.

[0070] The thioalkoxy group is a linear, branched, or cyclic thioalkoxy group, and it is preferable that it be a linear thioalkoxy group.

[0071] The number of carbon atoms in the thioalkoxy group is preferably 1 to 10, preferably 1 to 6.

[0072] Also, R i1One or more -CH2-CH2- groups among the alkyl groups can be substituted with -CH=CH- to form an alkenyl group having 2 to 20 carbon atoms.

[0073] The alkenyl group is a straight-chain, branched, or cyclic alkenyl group, and it is preferable that it be a straight-chain alkenyl group.

[0074] The number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.

[0075] Also, R i1 One or more -CH2-CH2- groups among the alkyl groups can be substituted with -C≡C- to form an alkynyl group having 2 to 20 carbon atoms.

[0076] The alkynyl group is a straight, branched, or cyclic alkynyl group, and it is preferable that it be a straight alkynyl group.

[0077] The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.

[0078] Also, R i1 In this case, one -CH2- in the alkyl group is substituted with -O-, and one or more -CH2-CH2- are substituted with -CH=CH-, thereby forming an alkenyloxy group having 2 to 19 carbon atoms.

[0079] The alkenyloxy group is a straight-chain, branched, or cyclic alkenyloxy group, and it is preferable that it be a straight-chain alkenyloxy group.

[0080] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6.

[0081] Also, R i1 Silver can represent an alkyl halide group having 1 to 20 carbon atoms by substituting one or more hydrogen atoms in the alkyl group with a halogen atom.

[0082] The alkyl halide group is a straight-chain, branched, or cyclic alkyl halide group, and it is preferable that it be a straight-chain alkyl halide group.

[0083] The number of carbon atoms in the alkyl halide group is preferably 2 to 10, preferably 2 to 6.

[0084] R i1 In this case, one -CH2- in the alkyl group is substituted with -O-, and one or more hydrogen atoms in the alkyl group are substituted with a halogen atom, thereby forming a halogenated alkoxy group having 1 to 19 carbon atoms.

[0085] The halogenated alkoxy group is a straight-chain, branched, or cyclic halogenated alkoxy group, and it is preferable that it be a straight-chain halogenated alkoxy group.

[0086] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0087] R i1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) in the above include the formula (R i1 -1)~(R i1 Examples include the one indicated by -36).

[0088]

[0089] Equation (R i1 -1)~(R i1 -36) Among them, sunspots are A i1 It represents the joint hand of the row.

[0090] Also, R i1 As for solubility, a straight-chain alkyl group having 2 to 6 carbon atoms or a straight-chain thioalkoxy group having 2 to 6 carbon atoms is preferred.

[0091] Among general formula (i), A i1 , A i2 and A i3Each independently, the following units (a), (b), (c) and (d):

[0092] (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- in this group may be substituted with -O- and / or -S-)

[0093] (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0094] (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group(naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, One -CH= or two or more non-adjacent -CH= present in 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, or phenanthrene-2,7-diyl group may be substituted with -N=.)

[0095] (d) Thiophene-2,5-diyl group, benzothiophen-2,5-diyl group, benzothiophen-2,6-diyl group, dibenzothiophen-3,7-diyl group, dibenzothiophen-2,6-diyl group, thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0096] It represents a group selected from the group consisting of

[0097] However, A i1 It does not show 1,2,3,4-tetrahydronaphthalene-2,6-diyl groups.

[0098] A i1 , A i2 and A i3 One or more hydrogen atoms among them, independently, are substituent S i1 It may be substituted by.

[0099] Substituent S i1 It represents any one of silver, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, and alkyl groups having 1 to 20 carbon atoms.

[0100] The alkyl group is a straight-chain, branched, or cyclic alkyl group, and it is preferably a straight-chain alkyl group.

[0101] The number of carbon atoms in the alkyl group is preferably 2 to 10, preferably 3 to 6.

[0102] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S- and / or -CO-.

[0103] In addition, one or more -CH2-CH2- groups in the alkyl group may each be independently substituted with -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-.

[0104] In addition, one or more -CH2-CH2-CH2- in the alkyl group may be substituted with -O-CO-O-.

[0105] One or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[0106] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0107] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0108] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0109] Substituent S i1 As such, halogen atoms are preferred, and fluorine atoms are preferred.

[0110] Also, A i1 and A i2 At least one of them is at least one substituent S i1 It is preferable that it be substituted with a halogen atom, and it is preferable that it be substituted with a fluorine atom.

[0111] Also, substituent S i1 In cases where there are multiple instances, they may be identical or different.

[0112] A i1 Substituent S in i1 As for the substitution positions, the following expression (A i1 -SP-1)~(A i1 It is desirable to have one of the following: -SP-2).

[0113]

[0114] Formula (A i1 -SP-1)~(A i1 -SP-2) Among them, white spots are R i1 It represents the bond loss of the rho group, and the black spot represents the bond loss of the ethylene group (-C≡C-).

[0115] A i2 Substituent S in i1 As for the substitution positions, the following expression (A i2 -SP-1)~(A i2It is desirable to have one of the following: -SP-3).

[0116]

[0117] Formula (A i2 -SP-1)~(A i2 Among -SP-3), white spots indicate bond loss to the ethylene group (-C≡C-), and black spots are Z i1 It represents the joint hand of the row.

[0118] A i3 Substituent S in i1 As for the substitution positions, the following expression (A i3 -SP-1)~(A i3 It is desirable to have one of the following: -SP-3).

[0119]

[0120] Formula (A i3 -SP-1)~(A i3 -SP-3) Among them, white spots are Z i1 It represents the bond loss of the rheogroup, and the black spot represents the bond loss of the isothiocyanate group (-NCS).

[0121] More specifically, A i1 is, the following formula (A i1 -1)~(A i1 It is desirable to represent one of -6).

[0122]

[0123] Formula (A i1 -1)~(A i1 -6) Among them, white spots are R i1 It represents the bond loss of the rho group, and the black spot represents the bond loss of the ethylene group (-C≡C-).

[0124] A i1 In terms of solubility, the above formula (A i1 -1) or (A i1 It is particularly desirable to represent -6).

[0125] More specifically, A i2 is, the following formula (Ai2 -1)~(A i2 It is desirable to represent one of -7).

[0126]

[0127] Formula (A i2 -1)~(A i2 -7) Among them, white spots indicate bond loss to the ethylene group (-C≡C-), and black spots are Z i1 It represents the joint hand of the row.

[0128] A i2 is, Δn and / or Δε r In terms of, the above equation (A i2 -1), (A i2 -2) or (A i2 It is more desirable to represent -6), and (A i2 It is particularly desirable to represent -1).

[0129] More specifically, A i3 is, the following formula (A i3 -1)~(A i3 It is desirable to represent one of the following: -4)

[0130]

[0131] Formula (A i3 -1)~(A i3 -4) Among them, white spots are Z i1 It represents the bond loss of the rheogroup, and the black spot represents the bond loss of the isothiocyanate group (-NCS).

[0132] A i3 is, Δn and / or Δε r In terms of, the above equation (A i3 -1), (A i3 -2) or (A i3 It is more desirable to represent -3), and (A i3 It is particularly desirable to represent -3).

[0133] Among general formula (i), Z i1It represents any one of a single bond, or an alkylene group having 1 to 20 carbon atoms.

[0134] The alkylene group is a straight-chain, branched, or cyclic alkylene group, and it is preferable that it be a straight-chain alkylene group.

[0135] The number of carbon atoms in the alkylene group is preferably 2 to 10, preferably 2 to 6.

[0136] One or more -CH2- groups in the alkylene group may each be independently substituted with -O-, -CF2- and / or -CO-.

[0137] In addition, one or more -CH2-CH2- groups in the alkylene group may each be independently substituted with -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[0138] However, in cases where the alkylene group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0139] Specific examples of alkylene groups having 2 to 20 carbon atoms (including substituted ones) include the formula (Z i1 -1)~(Z i1 Examples include the one indicated by -24.

[0140]

[0141] Equation (Z i1 -1)~(Z i1 -24) Among them, white points are A i2 It represents the combined loss of the furnace, and the sunspot is A i3 It represents the connection loss to.

[0142] Δn and / or Δε r From the perspective of, Z i1 It is preferable that the bond be a single bond or -C≡C-.

[0143] As for the compound represented by general formula (i), it is preferable that it be a compound represented by the following general formulas (i-1) to (i-2).

[0144]

[0145] Among general formulas (i-1) to (i-2), R i1 , A i1 and Z i1 is R in the above general formula (i). i1 , A i1 and Z i1 Each represents the same meaning and signifies something like a desirable prayer. Specifically, R i1 In terms of solubility, a straight-chain alkyl group having 2 to 6 carbon atoms or a straight-chain thioalkoxy group having 2 to 6 carbon atoms is preferred.

[0146] Specifically, A i1 is, the following formula (A i1 -1)~(A i1 It is desirable to represent any one of -6), and the following formula (A i1 -1) or (A i1 -6) is desirable.

[0147]

[0148] Formula (A i1 -1)~(A i1 -6) Among them, white spots are R i1 It represents the bond loss of the rho group, and the black spot represents the bond loss of the ethylene group (-C≡C-).

[0149] Specifically, Z i1 Silver, single bonds, -C≡C- or -CH=CH- are preferred.

[0150] Among general formulas (i-1) to (i-2), X i-1-2-1 , X i-1-2-2 , X i-1-2-3 , X i-1-2-4 , X i-1-2-5 , X i-1-2-6 , X i-1-2-7 , X i-1-2-8 , Xi-1-3-2 , X i-1-3-3 , X i-1-3-5 , X i-1-3-6 Each independently, a hydrogen atom or a substituent S i1 It represents.

[0151] Substituent S i1 is, substituent S in the above general formula (i). i1 Each represents the same meaning and indicates something like a desirable prayer.

[0152] As for the compound represented by general formula (i-1), it is preferable that it be a compound represented by the following general formulas (i-1-1) to (i-1-43).

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159] Among general formulas (i-1-1) to (i-1-43), R i1 and S i1 R in the above general formula (i), each independently i1 and S i1 It expresses the same meaning as.

[0160] 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).

[0161]

[0162] Specific examples of compounds represented by general formula (i-1-2) include compounds represented by the following structural formulas (i-1-2.1) to (i-1-2.4).

[0163]

[0164] Specific examples of compounds represented by general formula (i-1-3) include compounds represented by the following structural formulas (i-1-3.1) to (i-1-3.4).

[0165]

[0166] Specific examples of compounds represented by the general formula (i-1-4) include compounds represented by the following structural formulas (i-1-4.1) to (i-1-4.4).

[0167]

[0168] Specific examples of compounds represented by general formula (i-1-5) include compounds represented by the following structural formulas (i-1-5.1) to (i-1-5.8).

[0169]

[0170]

[0171] Specific examples of compounds represented by general formula (i-1-6) include compounds represented by the following structural formulas (i-1-6.1) to (i-1-6.2).

[0172]

[0173] Specific examples of compounds represented by general formula (i-1-7) include compounds represented by the following structural formulas (i-1-7.1) to (i-1-7.4).

[0174]

[0175] Specific examples of compounds represented by general formula (i-1-8) include compounds represented by the following structural formulas (i-1-8.1) to (i-1-8.5).

[0176]

[0177] Specific examples of compounds represented by general formula (i-1-9) include compounds represented by the following structural formulas (i-1-9.1) to (i-1-9.4).

[0178]

[0179] Specific examples of compounds represented by the general formula (i-1-10) include compounds represented by the following structural formula (i-1-10.1).

[0180]

[0181] Specific examples of compounds represented by the general formula (i-1-11) include compounds represented by the following structural formulas (i-1-11.1) to (i-1-11.16).

[0182]

[0183]

[0184]

[0185]

[0186] Specific examples of compounds represented by the general formula (i-1-12) include compounds represented by the following structural formulas (i-1-12.1) to (i-1-12.4).

[0187]

[0188] Specific examples of compounds represented by the general formula (i-1-13) include compounds represented by the following structural formulas (i-1-13.1) to (i-1-13.4).

[0189]

[0190] Specific examples of compounds represented by the general formula (i-1-14) include compounds represented by the following structural formulas (i-1-14.1) to (i-1-14.4).

[0191]

[0192] Specific examples of compounds represented by the general formula (i-1-15) include compounds represented by the following structural formulas (i-1-15.1) to (i-1-15.4).

[0193]

[0194] Specific examples of compounds represented by the general formula (i-1-16) include compounds represented by the following structural formulas (i-1-16.1) to (i-1-16.5).

[0195]

[0196] Specific examples of compounds represented by the general formula (i-1-17) include compounds represented by the following structural formulas (i-1-17.1) to (i-1-17.2).

[0197]

[0198] Specific examples of compounds represented by the general formula (i-1-18) include compounds represented by the following structural formulas (i-1-18.1) to (i-1-18.5).

[0199]

[0200] Specific examples of compounds represented by the general formula (i-1-19) include compounds represented by the following structural formulas (i-1-19.1) to (i-1-19.14).

[0201]

[0202]

[0203]

[0204] Specific examples of compounds represented by the general formula (i-1-20) include compounds represented by the following structural formulas (i-1-20.1) to (i-1-20.4).

[0205]

[0206] Specific examples of compounds represented by the general formula (i-1-21) include compounds represented by the following structural formula (i-1-21.1).

[0207]

[0208] Specific examples of compounds represented by the general formula (i-1-22) include compounds represented by the following structural formulas (i-1-22.1) to (i-1-22.4).

[0209]

[0210] Specific examples of compounds represented by the general formula (i-1-23) include compounds represented by the following structural formulas (i-1-23.1) to (i-1-23.4).

[0211]

[0212] Specific examples of compounds represented by the general formula (i-1-24) include compounds represented by the following structural formula (i-1-24.1).

[0213]

[0214] Specific examples of compounds represented by the general formula (i-1-25) include compounds represented by the following structural formulas (i-1-25.1) to (i-1-25.4).

[0215]

[0216] Specific examples of compounds represented by the general formula (i-1-26) include compounds represented by the following structural formulas (i-1-26.1) to (i-1-26.4).

[0217]

[0218] Specific examples of compounds represented by the general formula (i-1-27) include compounds represented by the following structural formulas (i-1-27.1) to (i-1-27.19).

[0219]

[0220]

[0221]

[0222]

[0223] Specific examples of compounds represented by the general formula (i-1-28) include compounds represented by the following structural formulas (i-1-28.1) to (i-1-28.5).

[0224]

[0225] Specific examples of compounds represented by the general formula (i-1-29) include compounds represented by the following structural formulas (i-1-29.1) to (i-1-29.5).

[0226]

[0227] Specific examples of compounds represented by the general formula (i-1-30) include compounds represented by the following structural formulas (i-1-30.1) to (i-1-30.4).

[0228]

[0229] Specific examples of compounds represented by the general formula (i-1-31) include compounds represented by the following structural formula (i-1-31.1).

[0230]

[0231] Specific examples of compounds represented by the general formula (i-1-32) include compounds represented by the following structural formula (i-1-32.1).

[0232]

[0233] Specific examples of compounds represented by the general formula (i-1-33) include compounds represented by the following structural formulas (i-1-33.1) to (i-1-33.4).

[0234]

[0235] Specific examples of compounds represented by the general formula (i-1-34) include compounds represented by the following structural formulas (i-1-34.1) to (i-1-34.4).

[0236]

[0237] Specific examples of compounds represented by the general formula (i-1-35) include compounds represented by the following structural formulas (i-1-35.1) to (i-1-35.5).

[0238]

[0239] Specific examples of compounds represented by the general formula (i-1-36) include compounds represented by the following structural formulas (i-1-36.1) to (i-1-36.4).

[0240]

[0241] Specific examples of compounds represented by the general formula (i-1-37) include compounds represented by the following structural formulas (i-1-37.1) to (i-1-37.5).

[0242]

[0243] Specific examples of compounds represented by the general formula (i-1-38) include compounds represented by the following structural formulas (i-1-38.1) to (i-1-38.8).

[0244]

[0245]

[0246] Specific examples of compounds represented by the general formula (i-1-39) include compounds represented by the following structural formulas (i-1-39.1) to (i-1-39.4).

[0247]

[0248] Specific examples of compounds represented by the general formula (i-1-40) include compounds represented by the following structural formulas (i-1-40.1) to (i-1-40.4).

[0249]

[0250] Specific examples of compounds represented by the general formula (i-1-41) include compounds represented by the following structural formula (i-1-41.1).

[0251]

[0252] Specific examples of compounds represented by the general formula (i-1-42) include compounds represented by the following structural formula (i-1-42.1).

[0253]

[0254] Specific examples of compounds represented by the general formula (i-1-43) include compounds represented by the following structural formula (i-1-43.1).

[0255]

[0256] As for the compound represented by general formula (i-2), it is preferable that it be a compound represented by the following general formula (i-2-1).

[0257]

[0258] In the general formula (i-2-1), R i1 and S i1 R in the above general formula (i), each independently i1 and S i1 It expresses the same meaning as.

[0259] Specific examples of compounds represented by the general formula (i-2-1) include compounds represented by the following structural formula (i-2-1.1).

[0260]

[0261] General formula (i), General formula (i-1)~(i-2), General formula (i-1-1)~(i-1-43), General formula (i-2-1), Structure formula (i-1-1.1)~(i-1-1.4), Structure formula (i-1-2.1)~(i-1-2.4), Structure formula (i-1-3.1)~(i-1-3.4), Structure formula (i-1-4.1)~(i-1-4.4), Structure formula (i-1-5.1)~(i-1-5.8), Structure formula (i-1-6.1)~(i-1-6.2), Structure formula (i-1-7.1)~(i-1-7.4), Structure formula (i-1-8.1)~(i-1-8.5), Structure formula (i-1-9.1)~(i-1-9.4), Structure formula (i-1-10.1), Structure formula (i-1-11.1)~(i-1-11.16), Structure formula (i-1-12.1)~(i-1-12.4), Structure formula (i-1-13.1)~(i-1-13.4), Structure formula (i-1-14.1)~(i-1-14.4), Structure formula (i-1-15.1)~(i-1-15.4), Structure formula (i-1-16.1)~(i-1-16.5), Structure formula (i-1-17.1)~(i-1-17.2), Structure formula (i-1-18.1)~(i-1-18.5), Structure formula (i-1-19.1)~(i-1-19.14), Structure formula (i-1-20.1)~(i-1-20.4), Structure formula (i-1-21.1), Structure formula (i-1-22.1)~(i-1-22.4), structure formula (i-1-23.1)~(i-1-23.4), structure formula (i-1-24.1), structure formula (i-1-25.1)~(i-1-25.4), structure formula (i-1-26.1)~(i-1-26.4), structure formula (i-1-27.1)~(i-1-27.19), structure formula (i-1-28.1)~(i-1-28.5), structure formula (i-1-29.1)~(i-1-29.5), structure formula (i-1-30.1)~(i-1-30.4), structure formula (i-1-31.1), structure formula (i-1-32.1), structure formula (i-1-33.1)~(i-1-33.4), structure formula (i-1-34.1)~(i-1-34.4), structure formula (i-1-35.1)~(i-1-35.5), structure formula (i-1-36.1)~(i-1-36.4), structure formula (i-1-37.1)~(i-1-37.5), structural formulas (i-1-38.1) to (i-1-38.8), structural formulas (i-1-39.1) to (i-1-39.4), structural formulas (i-1-40.1) to (i-1-40.4), structural formulas (i-1-41.1), structural formulas (i-1-42.1), structural formulas (i-1-43.1) or structural formula (i-2-1.1). The types used in the liquid crystal composition of compounds represented by structural formulas (i-1-3) are one or two or more, preferably 1 to 5, preferably 1 to 4, and preferably 1 to 3.

[0262] General formula (i), General formula (i-1)~(i-2), General formula (i-1-1)~(i-1-43), General formula (i-2-1), Structure formula (i-1-1.1)~(i-1-1.4), Structure formula (i-1-2.1)~(i-1-2.4), Structure formula (i-1-3.1)~(i-1-3.4), Structure formula (i-1-4.1)~(i-1-4.4), Structure formula (i-1-5.1)~(i-1-5.8), Structure formula (i-1-6.1)~(i-1-6.2), Structure formula (i-1-7.1)~(i-1-7.4), Structure formula (i-1-8.1)~(i-1-8.5), Structure formula (i-1-9.1)~(i-1-9.4), Structure formula (i-1-10.1), Structure formula (i-1-11.1)~(i-1-11.16), Structure formula (i-1-12.1)~(i-1-12.4), Structure formula (i-1-13.1)~(i-1-13.4), Structure formula (i-1-14.1)~(i-1-14.4), Structure formula (i-1-15.1)~(i-1-15.4), Structure formula (i-1-16.1)~(i-1-16.5), Structure formula (i-1-17.1)~(i-1-17.2), Structure formula (i-1-18.1)~(i-1-18.5), Structure formula (i-1-19.1)~(i-1-19.14), Structure formula (i-1-20.1)~(i-1-20.4), Structure formula (i-1-21.1), Structure formula (i-1-22.1)~(i-1-22.4), structure formula (i-1-23.1)~(i-1-23.4), structure formula (i-1-24.1), structure formula (i-1-25.1)~(i-1-25.4), structure formula (i-1-26.1)~(i-1-26.4), structure formula (i-1-27.1)~(i-1-27.19), structure formula (i-1-28.1)~(i-1-28.5), structure formula (i-1-29.1)~(i-1-29.5), structure formula (i-1-30.1)~(i-1-30.4), structure formula (i-1-31.1), structure formula (i-1-32.1), structure formula (i-1-33.1)~(i-1-33.4), structure formula (i-1-34.1)~(i-1-34.4), structure formula (i-1-35.1)~(i-1-35.5), structure formula (i-1-36.1)~(i-1-36.4), structure formula (i-1-37.1)~(i-1-37.The lower limit of the total content of the compound represented by structural formulas (i-1-38.1) to (i-1-38.8), structural formulas (i-1-39.1) to (i-1-39.4), structural formulas (i-1-40.1) to (i-1-40.4), structural formulas (i-1-41.1), structural formulas (i-1-42.1), structural formulas (i-1-43.1) or structural formula (i-2-1.1) in 100 mass% of the liquid crystal composition is preferably 3 mass% or more, preferably 5 mass% or more, preferably 10 mass% or more, preferably 15 mass% or more, preferably 20 mass% or more, preferably 25 mass% or more, preferably 30 mass% or more, and preferably 35 mass% or more.

[0263] General formula (i), General formula (i-1)~(i-2), General formula (i-1-1)~(i-1-43), General formula (i-2-1), Structure formula (i-1-1.1)~(i-1-1.4), Structure formula (i-1-2.1)~(i-1-2.4), Structure formula (i-1-3.1)~(i-1-3.4), Structure formula (i-1-4.1)~(i-1-4.4), Structure formula (i-1-5.1)~(i-1-5.8), Structure formula (i-1-6.1)~(i-1-6.2), Structure formula (i-1-7.1)~(i-1-7.4), Structure formula (i-1-8.1)~(i-1-8.5), Structure formula (i-1-9.1)~(i-1-9.4), Structure formula (i-1-10.1), Structure formula (i-1-11.1)~(i-1-11.16), Structure formula (i-1-12.1)~(i-1-12.4), Structure formula (i-1-13.1)~(i-1-13.4), Structure formula (i-1-14.1)~(i-1-14.4), Structure formula (i-1-15.1)~(i-1-15.4), Structure formula (i-1-16.1)~(i-1-16.5), Structure formula (i-1-17.1)~(i-1-17.2), Structure formula (i-1-18.1)~(i-1-18.5), Structure formula (i-1-19.1)~(i-1-19.14), Structure formula (i-1-20.1)~(i-1-20.4), Structure formula (i-1-21.1), Structure formula (i-1-22.1)~(i-1-22.4), structure formula (i-1-23.1)~(i-1-23.4), structure formula (i-1-24.1), structure formula (i-1-25.1)~(i-1-25.4), structure formula (i-1-26.1)~(i-1-26.4), structure formula (i-1-27.1)~(i-1-27.19), structure formula (i-1-28.1)~(i-1-28.5), structure formula (i-1-29.1)~(i-1-29.5), structure formula (i-1-30.1)~(i-1-30.4), structure formula (i-1-31.1), structure formula (i-1-32.1), structure formula (i-1-33.1)~(i-1-33.4), structure formula (i-1-34.1)~(i-1-34.4), structure formula (i-1-35.1)~(i-1-35.5), structure formula (i-1-36.1)~(i-1-36.4), structure formula (i-1-37.1)~(i-1-37.The upper limit of the total content of the compound represented by structural formulas (i-1-38.1) to (i-1-38.8), structural formulas (i-1-39.1) to (i-1-39.4), structural formulas (i-1-40.1) to (i-1-40.4), structural formula (i-1-41.1), structural formula (i-1-42.1), structural formula (i-1-43.1), or structural formula (i-2-1.1) in 100 mass% of the liquid crystal composition is preferably 75 mass% or less, preferably 70 mass% or less, preferably 65 mass% or less, preferably 55 mass% or less, preferably 45 mass% or less, preferably 35 mass% or less, preferably 25 mass% or less, preferably 15 mass% or less, and 10 mass% It is desirable that it be less than or equal to this.

[0264] General formula (i), General formula (i-1)~(i-2), General formula (i-1-1)~(i-1-43), General formula (i-2-1), Structure formula (i-1-1.1)~(i-1-1.4), Structure formula (i-1-2.1)~(i-1-2.4), Structure formula (i-1-3.1)~(i-1-3.4), Structure formula (i-1-4.1)~(i-1-4.4), Structure formula (i-1-5.1)~(i-1-5.8), Structure formula (i-1-6.1)~(i-1-6.2), Structure formula (i-1-7.1)~(i-1-7.4), Structure formula (i-1-8.1)~(i-1-8.5), Structure formula (i-1-9.1)~(i-1-9.4), Structure formula (i-1-10.1), Structure formula (i-1-11.1)~(i-1-11.16), Structure formula (i-1-12.1)~(i-1-12.4), Structure formula (i-1-13.1)~(i-1-13.4), Structure formula (i-1-14.1)~(i-1-14.4), Structure formula (i-1-15.1)~(i-1-15.4), Structure formula (i-1-16.1)~(i-1-16.5), Structure formula (i-1-17.1)~(i-1-17.2), Structure formula (i-1-18.1)~(i-1-18.5), Structure formula (i-1-19.1)~(i-1-19.14), Structure formula (i-1-20.1)~(i-1-20.4), Structure formula (i-1-21.1), Structure formula (i-1-22.1)~(i-1-22.4), structure formula (i-1-23.1)~(i-1-23.4), structure formula (i-1-24.1), structure formula (i-1-25.1)~(i-1-25.4), structure formula (i-1-26.1)~(i-1-26.4), structure formula (i-1-27.1)~(i-1-27.19), structure formula (i-1-28.1)~(i-1-28.5), structure formula (i-1-29.1)~(i-1-29.5), structure formula (i-1-30.1)~(i-1-30.4), structure formula (i-1-31.1), structure formula (i-1-32.1), structure formula (i-1-33.1)~(i-1-33.4), structure formula (i-1-34.1)~(i-1-34.4), structure formula (i-1-35.1)~(i-1-35.5), structure formula (i-1-36.1)~(i-1-36.4), structure formula (i-1-37.1)~(i-1-37.5), the total content in 100 mass% of the liquid crystal composition of compounds represented by structural formulas (i-1-38.1) to (i-1-38.8), structural formulas (i-1-39.1) to (i-1-39.4), structural formulas (i-1-40.1) to (i-1-40.4), structural formulas (i-1-41.1), structural formulas (i-1-42.1), structural formulas (i-1-43.1) or structural formula (i-2-1.1) is the solubility, Δn and / or Δε. r In terms of, it is preferable that the amount be 5 to 75 mass%, 10 to 70 mass%, and 15 to 65 mass%.

[0265] Compounds represented by general formula (i) (including sub-concepts) can be synthesized using known synthesis methods, and several examples are provided below.

[0266] (Preparation 1) Preparation of a compound represented by the following formula (s-6)

[0267]

[0268] (during food, R i1 and S i1 is R in the above general formula (i). i1 and S i1 It expresses the same meaning as.

[0269] A compound represented by general formula (s-3) can be obtained by reacting a compound represented by general formula (s-1) with a compound represented by general formula (s-2).

[0270] Examples of reaction methods include the Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.

[0271] Specific examples of palladium catalysts include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium acetate(II), dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0), etc.

[0272] When using palladium acetate (II) as a palladium catalyst, ligands such as triphenylphosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0273] A specific example of a copper catalyst is copper iodide (I).

[0274] Specific examples of bases include triethylamine.

[0275] A compound represented by general formula (s-5) can be obtained by reacting a compound represented by general formula (s-3) with a compound represented by general formula (s-4).

[0276] Examples of reaction methods include the Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.

[0277] Specific examples of palladium catalysts, copper catalysts, and bases include those mentioned above.

[0278] In addition, by reacting a compound represented by general formula (s-5) with 1,1-thiocarbonyldiimidazole, a target compound represented by general formula (s-6) can be obtained.

[0279] (Preparation 2) Preparation of a compound represented by the following formula (s-14)

[0280]

[0281] (during food, R i1 and S i1 is R in the above general formula (i). i1 and S i1 It expresses the same meaning as.

[0282] A compound represented by general formula (s-9) can be obtained by reacting a compound represented by general formula (s-7) with a compound represented by general formula (s-8).

[0283] Examples of reaction methods include the Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.

[0284] Specific examples of palladium catalysts include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium acetate(II), dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0), etc.

[0285] When using palladium acetate (II) as a palladium catalyst, ligands such as triphenylphosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0286] A specific example of a copper catalyst is copper iodide (I).

[0287] Specific examples of bases include triethylamine.

[0288] A compound represented by general formula (s-9) can be reacted with a compound represented by general formula (s-10), further reacted with butyllithium at cryogenic temperature (-60°C or lower), and then reacted with N,N-dimethylformamide to obtain a compound represented by general formula (s-11).

[0289] As a reaction method for reacting a compound represented by general formula (s-9) with a compound represented by general formula (s-10), for example, a hex reaction using a palladium catalyst and a base can be cited.

[0290] Specific examples of palladium catalysts and bases include those mentioned above.

[0291] For example, by reacting the compound represented by general formula (s-11) with hydroxylamine, a compound represented by general formula (s-12) can be obtained.

[0292] For example, by reacting the compound represented by general formula (s-12) with N-chlorosuccinimide, a compound represented by general formula (s-13) can be obtained.

[0293] For example, by reacting a compound represented by general formula (s-13) with thiourea, a target compound represented by general formula (s-14) can be obtained.

[0294] (Preparation 3) Preparation of a compound represented by the following formula (s-20)

[0295]

[0296] (during food, R i1 and S i1 is R in the above general formula (i). i1 and S i1 It expresses the same meaning as.

[0297] A compound represented by general formula (s-15) can be reacted with a compound represented by general formula (s-16), and then reacted with anhydrous trifluoromethanesulfonic acid to obtain a compound represented by general formula (s-17).

[0298] Examples of reaction methods include the Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.

[0299] Specific examples of palladium catalysts include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium acetate(II), dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0), etc.

[0300] When using palladium acetate (II) as a palladium catalyst, ligands such as triphenylphosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0301] A specific example of a copper catalyst is copper iodide (I).

[0302] Specific examples of bases include triethylamine.

[0303] A compound represented by general formula (s-19) can be obtained by reacting a compound represented by general formula (s-17) with a compound represented by general formula (s-18).

[0304] As an example of a reaction method, the Suzuki coupling reaction using a palladium catalyst and a base can be cited.

[0305] Specific examples of palladium catalysts and bases include those mentioned above.

[0306] In addition, by reacting a compound represented by general formula (s-19) with 1,1-thiocarbonyldiimidazole, a target compound represented by general formula (s-20) can be obtained.

[0307] (Preparation 4) Preparation of a compound represented by the following formula (s-26)

[0308]

[0309] (during food, R i1 and S i1 is R in the above general formula (i). i1 and S i1 It expresses the same meaning as.

[0310] By reacting a compound represented by general formula (s-21) with a compound represented by general formula (s-22), a compound represented by general formula (s-23) can be obtained.

[0311] Examples of reaction methods include the Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.

[0312] Specific examples of palladium catalysts include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium acetate(II), dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0), etc.

[0313] When using palladium acetate (II) as a palladium catalyst, ligands such as triphenylphosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0314] A specific example of a copper catalyst is copper iodide (I).

[0315] Specific examples of bases include triethylamine.

[0316] A compound represented by general formula (s-25) can be obtained by reacting a compound represented by general formula (s-23) with a compound represented by general formula (s-24).

[0317] As an example of a reaction method, the Suzuki coupling reaction using a palladium catalyst and a base can be cited.

[0318] Specific examples of palladium catalysts and bases include those mentioned above.

[0319] In addition, by reacting a compound represented by general formula (s-25) with 1,1-thiocarbonyldiimidazole, a target compound represented by general formula (s-26) can be obtained.

[0320] (Preparation 5) Preparation of a compound represented by the following formula (s-32)

[0321]

[0322] (during food, R i1 and S i1 is R in the above general formula (i). i1 and S i1 It expresses the same meaning as.

[0323] A compound represented by general formula (s-29) can be obtained by reacting a compound represented by general formula (s-27) with a compound represented by general formula (s-28).

[0324] Examples of reaction methods include the Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.

[0325] Specific examples of palladium catalysts include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium acetate(II), dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0), etc.

[0326] When using palladium acetate (II) as a palladium catalyst, ligands such as triphenylphosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0327] A specific example of a copper catalyst is copper iodide (I).

[0328] Specific examples of bases include triethylamine.

[0329] A compound represented by general formula (s-29) can be obtained by reacting it with a compound represented by general formula (s-30) to obtain a compound represented by general formula (s-31).

[0330] As an example of a reaction method, the Suzuki coupling reaction using a palladium catalyst and a base can be cited.

[0331] Specific examples of palladium catalysts and bases include those mentioned above.

[0332] In addition, by reacting a compound represented by general formula (s-31) with 1,1-thiocarbonyldiimidazole, a compound of the target represented by general formula (s-32) can be obtained.

[0333] (Other compounds)

[0334] (Compounds represented by general formula (ii))

[0335] The liquid crystal composition according to the present invention has solubility, Δn and / or Δε r In this regard, it may additionally include one or more compounds represented by the following general formula (ii) having an isothiocyanate group (-NCS).

[0336]

[0337] In general formula (ii), R ii1 It represents an alkyl group with 1 to 20 carbon atoms.

[0338] The alkyl group is a straight-chain, branched, or cyclic alkyl group, and it is preferably a straight-chain alkyl group.

[0339] The number of carbon atoms in the alkyl group is preferably 2 to 10, preferably 2 to 6.

[0340] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0341] In addition, one or more -CH2-CH2- groups among the alkyl groups may be substituted with -CH=CH-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0342] In addition, one or more -CH2-CH2-CH2- among the alkyl groups may be substituted with -O-CO-O-.

[0343] In addition, one or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[0344] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0345] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0346] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0347] For example, R ii1 One -CH2- in the alkyl group can be substituted with -O- to form an alkoxy group having 1 to 19 carbon atoms.

[0348] The alkoxy group is a linear, branched, or cyclic alkoxy group, and it is preferable that it be a linear alkoxy group.

[0349] The number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0350] Also, R ii1 In this case, one -CH2- in the alkyl group is substituted with -S-, thereby forming a thioalkoxy group (alkylsulfanyl group, alkylthio group) having 1 to 19 carbon atoms.

[0351] The thioalkoxy group is a linear, branched, or cyclic thioalkoxy group, and it is preferable that it be a linear thioalkoxy group.

[0352] The number of carbon atoms in the thioalkoxy group is preferably 2 to 10, preferably 2 to 6.

[0353] Also, R ii1 One or more -CH2-CH2- groups among the alkyl groups can be substituted with -CH=CH- to form an alkenyl group having 2 to 20 carbon atoms.

[0354] The alkenyl group is a straight-chain, branched, or cyclic alkenyl group, and it is preferable that it be a straight-chain alkenyl group.

[0355] The number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.

[0356] Also, R ii1 One or more -CH2-CH2- groups among the alkyl groups can be substituted with -C≡C- to form an alkynyl group having 2 to 20 carbon atoms.

[0357] The alkynyl group is a straight, branched, or cyclic alkynyl group, and it is preferable that it be a straight alkynyl group.

[0358] The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.

[0359] Also, R ii1 In this case, one -CH2- in the alkyl group is substituted with -O-, and one or more -CH2-CH2- are substituted with -CH=CH-, thereby forming an alkenyloxy group having 2 to 19 carbon atoms.

[0360] The alkenyloxy group is a straight-chain, branched, or cyclic alkenyloxy group, and it is preferable that it be a straight-chain alkenyloxy group.

[0361] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6.

[0362] Also, R ii1 Silver can represent an alkyl halide group having 1 to 20 carbon atoms by substituting one or more hydrogen atoms in the alkyl group with a halogen atom.

[0363] The alkyl halide group is a straight-chain, branched, or cyclic alkyl halide group, and it is preferable that it be a straight-chain alkyl halide group.

[0364] The number of carbon atoms in the alkyl halide group is preferably 2 to 10, preferably 2 to 6.

[0365] Also, R ii1 In this case, one -CH2- in the alkyl group is substituted with -O-, and one or more hydrogen atoms in the alkyl group are substituted with a halogen atom, thereby forming a halogenated alkoxy group having 1 to 19 carbon atoms.

[0366] The halogenated alkoxy group is a straight-chain, branched, or cyclic halogenated alkoxy group, and it is preferable that it be a straight-chain halogenated alkoxy group.

[0367] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0368] R ii1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) in the above include the formula (R ii1 -1)~(R ii1 Examples include the one indicated by -37.

[0369]

[0370] Equation (R ii1 -1)~(R ii1 -37) Among them, sunspots are A ii1 It represents the joint hand of the row.

[0371] R ii1 When the bonded ring structure is a phenyl group (aromatic), a straight-chain alkyl group having 1 to 5 carbon atoms, a straight-chain alkoxy group having 1 to 4 carbon atoms, and an alkenyl group having 4 to 5 carbon atoms are preferred, and R i1 In the case where the ring structure being bonded is a saturated ring structure such as cyclohexane, pyran, and dioxane, a straight-chain alkyl group having 1 to 5 carbon atoms, a straight-chain alkoxy group having 1 to 4 carbon atoms, and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred.

[0372] Also, R ii1 In order to stabilize the nematic phase, it is desirable that the total of carbon atoms and oxygen atoms present is 5 or less, and that it is a straight chain.

[0373] Also, R ii1 As for solubility, a straight-chain alkyl group having 2 to 8 carbon atoms, a straight-chain alkoxy group having 2 to 8 carbon atoms, or a straight-chain halogenated alkoxy group having 2 to 8 carbon atoms is preferred.

[0374] Among general formula (ii), A ii1 and A ii2are, each independently, the following units (a), (b), (c) and (d):

[0375] (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- in this group may be substituted with -O- and / or -S-)

[0376] (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0377] (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group(naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, One -CH= or two or more non-adjacent -CH= present in 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, or phenanthrene-2,7-diyl group may be substituted with -N=.)

[0378] (d) Thiophene-2,5-diyl group, benzothiophen-2,5-diyl group, benzothiophen-2,6-diyl group, dibenzothiophen-3,7-diyl group, dibenzothiophen-2,6-diyl group, thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0379] It represents a group selected from the group consisting of

[0380] A ii1 and A ii2One or more hydrogen atoms among them, independently, are substituent S ii1 It may be substituted by.

[0381] Substituent S ii1 It represents any one of silver, a halogen atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms.

[0382] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0383] The alkyl group having 1 to 20 carbon atoms is a straight-chain, branched, or cyclic alkyl group, and it is preferably a straight-chain alkyl group.

[0384] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.

[0385] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0386] In addition, one or more -CH2-CH2- groups among the alkyl groups may each be independently substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0387] One or more -CH2-CH2-CH2- groups among the alkyl groups may each be independently substituted with -O-CO-O-.

[0388] In addition, one or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[0389] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0390] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0391] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0392] Substituent S ii1 As such, fluorine atoms or chlorine atoms are preferred.

[0393] Also, A ii1 At least one of or A ii2 is at least one substituent S ii1 It is desirable to replace it with .

[0394] Also, substituent S ii1 In cases where there are multiple instances, they may be identical or different.

[0395] A ii1 Substituent S in ii1 As for the substitution positions, the following expression (A ii1 -SP-1)~(A ii1 It is desirable to have one of the following: -SP-5).

[0396]

[0397] Equation (A ii1 -SP-1)~(A ii1 -SP-5) Among them, white spots are R ii1 or Z ii1 Represents the combined loss of the furnace, and the sunspot is Z ii1 It represents the joint hand of the row.

[0398] A ii2 Substituent S in ii1 As for the substitution positions, the following expression (A ii2 -SP-1)~(A ii2 It is desirable to have one of the following: -SP-7)

[0399]

[0400] Equation (A ii2 -SP-1)~(A ii2 -SP-7) Among them, white spots are Z ii1 It represents the bond loss of the rheogroup, and the black spot represents the bond loss of the isothiocyanate group (-NCS).

[0401] More specifically, A ii1 is, the following formula (A ii1 -1)~(A ii1 It is desirable to represent one of -7).

[0402]

[0403] Equation (A ii1 -1)~(A ii1 -7) Among them, white spots are R ii1 or Z ii1 Represents the combined loss of the furnace, and the sunspot is Z ii1 It represents the joint hand of the row.

[0404] More specifically, A ii2 is, the following formula (A ii2 -1)~(A ii2 It is desirable to represent one of -6).

[0405]

[0406] Equation (A ii2 -1)~(A ii2 -6) Among them, white spots are Z ii1 It represents the bond loss of the rheogroup, and the black spot represents the bond loss of the isothiocyanate group (-NCS).

[0407] In general formula (ii), Z ii1 It represents any one of a single bond, or an alkylene group having 1 to 20 carbon atoms.

[0408] One or more -CH2- groups in the alkylene group may each be independently substituted with -O-.

[0409] In addition, one or more -CH2-CH2- groups in the alkylene group may each be independently substituted with -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[0410] In addition, one or more -CH2-CH2-CH2- groups among the alkylene groups may each be independently substituted with -O-CO-O-.

[0411] However, in the case where an alkylene group having 1 to 10 carbon atoms is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0412] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0413] Specific examples of alkylene groups having 1 to 20 carbon atoms (including substituted ones) include the formula (Z ii1 -1)~(Z ii1 Examples include the one indicated by -24.

[0414]

[0415] Equation (Z ii1 -1)~(Z ii1 -24) Among them, white points are A ii1 It represents the combined loss of the furnace, and the sunspot is A ii1 or A ii2 It represents the joint hand of the row.

[0416] Among general formula (ii), n ii1 It represents an integer of 1 to 4, preferably 1 to 2.

[0417] n ii1 In the case where this is 1, Δn and / or Δε r From the perspective of, Z ii1It is desirable to represent a single bond or -C≡C-.

[0418] Also, n ii1 In the case of these two, Δn and / or Δε r From the perspective of, Z ii1 It is desirable to represent a single bond or -C≡C-.

[0419] Also, in general formula (ii), A ii1 and Z ii1 In cases where multiple instances exist, they may each be identical or different.

[0420] However, regarding compounds represented by general formula (ii), compounds represented by general formula (i) (including sub-concepts) are excluded.

[0421] As for the compound represented by general formula (ii), it is preferable that it be a compound represented by the following general formulas (ii-1) to (ii-6).

[0422]

[0423] Among general formulas (ii-1) to (ii-6), R ii1 , A ii1 and A ii2 is R in the above general formula (ii). ii1 , A ii1 and A ii2 Each represents the same meaning.

[0424] Among general formulas (ii-3) to (ii-6), A ii1-2 The definition of is A in the above general formula (ii). ii1 It is the same as the definition of.

[0425] As for the compound represented by general formula (ii-1), it is preferable that it be a compound represented by the following general formulas (ii-1-1) to (ii-1-2).

[0426]

[0427] Among general formulas (ii-1-1) to (ii-1-2), R ii1R in the above general formula (ii), each independently ii1 Each represents the same meaning.

[0428] Specific examples of compounds represented by general formula (ii-1-1) include compounds represented by the following structural formulas (ii-1-1.1) to (ii-1-1.4).

[0429]

[0430] Specific examples of compounds represented by general formula (ii-1-2) include compounds represented by the following structural formulas (ii-1-2.1) to (ii-1-2.6).

[0431]

[0432] As for the compound represented by general formula (ii-2), it is preferable that it be a compound represented by the following general formulas (ii-2-1) to (ii-2-5).

[0433]

[0434] Among general formulas (ii-2-1) to (ii-2-5), R ii1 and S ii1 are, respectively, R in the above general formula (i). ii1 and S ii1 Each represents the same meaning.

[0435] Specific examples of compounds represented by general formula (ii-2-1) include compounds represented by the following structural formulas (ii-2-1.1) to (ii-2-1.5).

[0436]

[0437] Specific examples of compounds represented by general formula (ii-2-2) include compounds represented by the following structural formulas (ii-2-2.1) to (ii-2-2.3).

[0438]

[0439] Specific examples of compounds represented by general formula (ii-2-3) include compounds represented by the following structural formulas (ii-2-3.1) to (ii-2-3.3).

[0440]

[0441] Specific examples of compounds represented by general formula (ii-2-4) include compounds represented by the following structural formulas (ii-2-4.1) to (ii-2-4.3).

[0442]

[0443] Specific examples of compounds represented by general formula (ii-2-5) include compounds represented by the following structural formulas (ii-2-5.1) to (ii-2-5.3).

[0444]

[0445] As for the compound represented by general formula (ii-3), it is preferable that it be a compound represented by the following general formulas (ii-3-1) to (ii-3-6).

[0446]

[0447] Among general formulas (ii-3-1) to (ii-3-6), R ii1 and S ii1 R in the above general formula (ii), each independently ii1 and S ii1 Each represents the same meaning.

[0448] Specific examples of compounds represented by general formula (ii-3-1) include compounds represented by the following structural formulas (ii-3-1.1) to (ii-3-1.4).

[0449]

[0450] 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).

[0451]

[0452] Specific examples of compounds represented by general formula (ii-3-3) include compounds represented by the following structural formulas (ii-3-3.1) to (ii-3-3.3).

[0453]

[0454] Specific examples of compounds represented by general formula (ii-3-4) include compounds represented by the following structural formulas (ii-3-4.1) to (ii-3-4.3).

[0455]

[0456] Specific examples of compounds represented by general formula (ii-3-5) include compounds represented by the following structural formulas (ii-3-5.1) to (ii-3-5.3).

[0457]

[0458] Specific examples of compounds represented by general formula (ii-3-6) include compounds represented by the following structural formulas (ii-3-6.1) to (ii-3-6.2).

[0459]

[0460] As for the compound represented by general formula (ii-4), it is preferable that it be a compound represented by the following general formulas (ii-4-1) to (ii-4-8).

[0461]

[0462]

[0463] Among general formulas (ii-4-1) to (ii-4-8), R ii1 and S ii1 R in the above general formula (ii), each independently ii1 and S ii1 Each represents the same meaning.

[0464] Specific examples of compounds represented by general formula (ii-4-1) include compounds represented by the following structural formulas (ii-4-1.1) to (ii-4-1.3).

[0465]

[0466] Specific examples of compounds represented by general formula (ii-4-2) include compounds represented by the following structural formulas (ii-4-2.1) to (ii-4-2.3).

[0467]

[0468] Specific examples of compounds represented by general formula (ii-4-3) include compounds represented by the following structural formulas (ii-4-3.1) to (ii-4-3.3).

[0469]

[0470] Specific examples of compounds represented by general formula (ii-4-4) include compounds represented by the following structural formulas (ii-4-4.1) to (ii-4-4.3).

[0471]

[0472] Specific examples of compounds represented by general formula (ii-4-5) include compounds represented by the following structural formulas (ii-4-5.1) to (ii-4-5.3).

[0473]

[0474] Specific examples of compounds represented by general formula (ii-4-6) include compounds represented by the following structural formulas (ii-4-6.1) to (ii-4-6.3).

[0475]

[0476] Specific examples of compounds represented by general formula (ii-4-7) include compounds represented by the following structural formulas (ii-4-7.1) to (ii-4-7.3).

[0477]

[0478] Specific examples of compounds represented by general formula (ii-4-8) include compounds represented by the following structural formulas (ii-4-8.1) to (ii-4-8.3).

[0479]

[0480] As for the compound represented by general formula (ii-5), it is preferable that it be a compound represented by the following general formulas (ii-5-1) to (ii-5-5).

[0481]

[0482] Among general formulas (ii-5-1) to (ii-5-5), R ii1 and S ii1 R in the above general formula (ii), each independently ii1 and S ii1 Each represents the same meaning.

[0483] Specific examples of compounds represented by general formula (ii-5-1) include compounds represented by the following structural formulas (ii-5-1.1) to (ii-5-1.4).

[0484]

[0485] Specific examples of compounds represented by general formula (ii-5-2) include compounds represented by the following structural formulas (ii-5-2.1) to (ii-5-2.4).

[0486]

[0487] Specific examples of compounds represented by general formula (ii-5-3) include compounds represented by the following structural formulas (ii-5-3.1) to (ii-5-3.3).

[0488]

[0489] Specific examples of compounds represented by general formula (ii-5-4) include compounds represented by the following structural formulas (ii-5-4.1) to (ii-5-4.3).

[0490]

[0491] Specific examples of compounds represented by general formula (ii-5-5) include compounds represented by the following structural formula (ii-5-5.1).

[0492]

[0493] As for the compound represented by general formula (ii-6), it is preferable that it be a compound represented by the following general formulas (ii-6-1) to (ii-6-2).

[0494]

[0495] Among general formulas (ii-6-1) to (ii-6-2), R ii1 and S ii1 R in the above general formula (ii), each independently ii1 and S ii1 Each represents the same meaning.

[0496] Specific examples of compounds represented by general formula (ii-6-1) include compounds represented by the following structural formulas (ii-6-1.1) to (ii-6-1.3).

[0497]

[0498] Specific examples of compounds represented by general formula (ii-6-2) include compounds represented by the following structural formulas (ii-6-2.1) to (ii-6-2.3).

[0499]

[0500] General formula (ii), General formula (ii-1)~(ii-6), General formula (ii-1-1)~(ii-1-2), General formula (ii-2-1)~(ii-2-5), General formula (ii-3-1)~(ii-3-6), General formula (ii-4-1)~(ii-4-8), General formula (ii-5-1)~(ii-5-5), General formula (ii-6-1)~(ii-6-2), Structural formula (ii-1-1.1)~(ii-1-1.4), Structural formula (ii-1-2.1)~(ii-1-2.6), Structural formula (ii-2-1.1)~(ii-2-1.5), Structural formula (ii-2-2.1)~(ii-2-2.3), Structural formula (ii-2-3.1)~(ii-2-3.3), Structural formula (ii-2-4.1)~(ii-2-4.3), Structure formula (ii-2-5.1)~(ii-2-5.3), Structure formula (ii-3-1.1)~(ii-3-1.4), Structure formula (ii-3-2.1)~(ii-3-2.3), Structure formula (ii-3-3.1)~(ii-3-3.3), Structure formula (ii-3-4.1)~(ii-3-4.3), Structure formula (ii-3-5.1)~(ii-3-5.3), Structure formula (ii-3-6.1)~(ii-3-6.2), Structure formula (ii-4-1.1)~(ii-4-1.3), Structure formula (ii-4-2.1)~(ii-4-2.3), Structure formula (ii-4-3.1)~(ii-4-3.3), Structure formula (ii-4-4.1)~(ii-4-4.3), Structure formula (ii-4-5.1)~(ii-4-5.3), structure formula (ii-4-6.1)~(ii-4-6.3), structure formula (ii-4-7.1)~(ii-4-7.3), structure formula (ii-4-8.1)~(ii-4-8.3), structure formula (ii-5-1.1)~(ii-5-1.4), structure formula (ii-5-2.1)~(ii-5-2.4), structure formula (ii-5-3.1)~(ii-5-3.3), structure formula (ii-5-4.1)~(ii-5-4.3), structure formula (ii-5-5.1), structure formula (ii-6-1.1)~(ii-6-1.3) or structure formula (ii-6-2.1)~(ii-6-2.The types used in the liquid crystal composition of the compound represented by 3) are 1 or 2 or more, preferably 1 to 10 types, preferably 1 to 8 types, preferably 1 to 6 types, preferably 1 to 4 types, and preferably 1 to 3 types.

[0501] General formula (ii), General formula (ii-1)~(ii-6), General formula (ii-1-1)~(ii-1-2), General formula (ii-2-1)~(ii-2-5), General formula (ii-3-1)~(ii-3-6), General formula (ii-4-1)~(ii-4-8), General formula (ii-5-1)~(ii-5-5), General formula (ii-6-1)~(ii-6-2), Structural formula (ii-1-1.1)~(ii-1-1.4), Structural formula (ii-1-2.1)~(ii-1-2.6), Structural formula (ii-2-1.1)~(ii-2-1.5), Structural formula (ii-2-2.1)~(ii-2-2.3), Structural formula (ii-2-3.1)~(ii-2-3.3), Structural formula (ii-2-4.1)~(ii-2-4.3), Structure formula (ii-2-5.1)~(ii-2-5.3), Structure formula (ii-3-1.1)~(ii-3-1.4), Structure formula (ii-3-2.1)~(ii-3-2.3), Structure formula (ii-3-3.1)~(ii-3-3.3), Structure formula (ii-3-4.1)~(ii-3-4.3), Structure formula (ii-3-5.1)~(ii-3-5.3), Structure formula (ii-3-6.1)~(ii-3-6.2), Structure formula (ii-4-1.1)~(ii-4-1.3), Structure formula (ii-4-2.1)~(ii-4-2.3), Structure formula (ii-4-3.1)~(ii-4-3.3), Structure formula (ii-4-4.1)~(ii-4-4.3), Structure formula (ii-4-5.1)~(ii-4-5.3), structure formula (ii-4-6.1)~(ii-4-6.3), structure formula (ii-4-7.1)~(ii-4-7.3), structure formula (ii-4-8.1)~(ii-4-8.3), structure formula (ii-5-1.1)~(ii-5-1.4), structure formula (ii-5-2.1)~(ii-5-2.4), structure formula (ii-5-3.1)~(ii-5-3.3), structure formula (ii-5-4.1)~(ii-5-4.3), structure formula (ii-5-5.1), structure formula (ii-6-1.1)~(ii-6-1.3) or structure formula (ii-6-2.1)~(ii-6-2.The lower limit of the total content of the compound indicated by 3) in 100 mass% of the liquid crystal composition is preferably 1 mass% or more, preferably 3 mass% or more, preferably 10 mass% or more, preferably 15 mass% or more, preferably 20 mass% or more, preferably 30 mass% or more, preferably 40 mass% or more, and preferably 55 mass% or more.

[0502] General formula (ii), General formula (ii-1)~(ii-6), General formula (ii-1-1)~(ii-1-2), General formula (ii-2-1)~(ii-2-5), General formula (ii-3-1)~(ii-3-6), General formula (ii-4-1)~(ii-4-8), General formula (ii-5-1)~(ii-5-5), General formula (ii-6-1)~(ii-6-2), Structural formula (ii-1-1.1)~(ii-1-1.4), Structural formula (ii-1-2.1)~(ii-1-2.6), Structural formula (ii-2-1.1)~(ii-2-1.5), Structural formula (ii-2-2.1)~(ii-2-2.3), Structural formula (ii-2-3.1)~(ii-2-3.3), Structural formula (ii-2-4.1)~(ii-2-4.3), Structure formula (ii-2-5.1)~(ii-2-5.3), Structure formula (ii-3-1.1)~(ii-3-1.4), Structure formula (ii-3-2.1)~(ii-3-2.3), Structure formula (ii-3-3.1)~(ii-3-3.3), Structure formula (ii-3-4.1)~(ii-3-4.3), Structure formula (ii-3-5.1)~(ii-3-5.3), Structure formula (ii-3-6.1)~(ii-3-6.2), Structure formula (ii-4-1.1)~(ii-4-1.3), Structure formula (ii-4-2.1)~(ii-4-2.3), Structure formula (ii-4-3.1)~(ii-4-3.3), Structure formula (ii-4-4.1)~(ii-4-4.3), Structure formula (ii-4-5.1)~(ii-4-5.3), structure formula (ii-4-6.1)~(ii-4-6.3), structure formula (ii-4-7.1)~(ii-4-7.3), structure formula (ii-4-8.1)~(ii-4-8.3), structure formula (ii-5-1.1)~(ii-5-1.4), structure formula (ii-5-2.1)~(ii-5-2.4), structure formula (ii-5-3.1)~(ii-5-3.3), structure formula (ii-5-4.1)~(ii-5-4.3), structure formula (ii-5-5.1), structure formula (ii-6-1.1)~(ii-6-1.3) or structure formula (ii-6-2.1)~(ii-6-2.The upper limit of the total content of the compound indicated by 3) in 100 mass% of the liquid crystal composition is preferably 80 mass% or less, preferably 75 mass% or less, preferably 70 mass% or less, preferably 65 mass% or less, preferably 50 mass% or less, preferably 30 mass% or less, preferably 25 mass% or less, and preferably 15 mass% or less.

[0503] General formula (ii), General formula (ii-1)~(ii-6), General formula (ii-1-1)~(ii-1-2), General formula (ii-2-1)~(ii-2-5), General formula (ii-3-1)~(ii-3-6), General formula (ii-4-1)~(ii-4-8), General formula (ii-5-1)~(ii-5-5), General formula (ii-6-1)~(ii-6-2), Structural formula (ii-1-1.1)~(ii-1-1.4), Structural formula (ii-1-2.1)~(ii-1-2.6), Structural formula (ii-2-1.1)~(ii-2-1.5), Structural formula (ii-2-2.1)~(ii-2-2.3), Structural formula (ii-2-3.1)~(ii-2-3.3), Structural formula (ii-2-4.1)~(ii-2-4.3), Structure formula (ii-2-5.1)~(ii-2-5.3), Structure formula (ii-3-1.1)~(ii-3-1.4), Structure formula (ii-3-2.1)~(ii-3-2.3), Structure formula (ii-3-3.1)~(ii-3-3.3), Structure formula (ii-3-4.1)~(ii-3-4.3), Structure formula (ii-3-5.1)~(ii-3-5.3), Structure formula (ii-3-6.1)~(ii-3-6.2), Structure formula (ii-4-1.1)~(ii-4-1.3), Structure formula (ii-4-2.1)~(ii-4-2.3), Structure formula (ii-4-3.1)~(ii-4-3.3), Structure formula (ii-4-4.1)~(ii-4-4.3), Structure formula The total content in 100 mass% of the liquid crystal composition of compounds represented by structural formulas (ii-4-5.1) to (ii-4-5.3), structural formulas (ii-4-6.1) to (ii-4-6.3), structural formulas (ii-4-7.1) to (ii-4-7.3), structural formulas (ii-4-8.1) to (ii-4-8.3), structural formulas (ii-5-1.1) to (ii-5-1.4), structural formulas (ii-5-2.1) to (ii-5-2.4), structural formulas (ii-5-3.1) to (ii-5-3.3), structural formulas (ii-5-4.1) to (ii-5-4.3), structural formulas (ii-5-5.1), structural formulas (ii-6-1.1) to (ii-6-1.3) or structural formulas (ii-6-2.1) to (ii-6-2.3) is, solubility, Δn and / or Δε rIn terms of, it is preferable to have 10 to 80 mass%, 15 to 75 mass%, and 20 to 70 mass%.

[0504] Compounds represented by general formula (ii) (including sub-concepts) can be synthesized using known synthesis methods.

[0505] The liquid crystal composition according to the present invention is V th , Δn and / or Δε r In this regard, one or more compounds represented by the following general formula (iii) having an additional cyano group (-CN) may be included.

[0506]

[0507] In general formula (iii), R iii1 It represents an alkyl group with 1 to 20 carbon atoms.

[0508] The alkyl group is a straight-chain, branched, or cyclic alkyl group, and it is preferably a straight-chain alkyl group.

[0509] The number of carbon atoms in the alkyl group is preferably 2 to 10, preferably 2 to 6.

[0510] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0511] In addition, one or more -CH2-CH2- groups among the alkyl groups may be substituted with -CH=CH-, -CO-O-, -O-CO- and / or -C≡C-.

[0512] In addition, one or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[0513] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0514] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0515] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0516] For example, R iii1 One -CH2- in the alkyl group can be substituted with -O- to form an alkoxy group having 1 to 19 carbon atoms.

[0517] The alkoxy group is a linear, branched, or cyclic alkoxy group, and it is preferable that it be a linear alkoxy group.

[0518] The number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0519] Also, R iii1 In this case, one -CH2- in the alkyl group is substituted with -S-, thereby forming a thioalkoxy group (alkylsulfanyl group, alkylthio group) having 1 to 19 carbon atoms.

[0520] The thioalkoxy group is a linear, branched, or cyclic thioalkoxy group, and it is preferable that it be a linear thioalkoxy group.

[0521] The number of carbon atoms in the thioalkoxy group is preferably 1 to 10, preferably 1 to 6.

[0522] Also, R iii1 One or more -CH2-CH2- groups among the alkyl groups can be substituted with -CH=CH- to form an alkenyl group having 2 to 20 carbon atoms.

[0523] The alkenyl group is a straight-chain, branched, or cyclic alkenyl group, and it is preferable that it be a straight-chain alkenyl group.

[0524] The number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.

[0525] Also, R iii1 One or more -CH2-CH2- groups among the alkyl groups can be substituted with -C≡C- to form an alkynyl group having 2 to 20 carbon atoms.

[0526] The alkynyl group is a straight, branched, or cyclic alkynyl group, and it is preferable that it be a straight alkynyl group.

[0527] The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.

[0528] Also, R iii1 In this case, one -CH2- in the alkyl group is substituted with -O-, and one or more -CH2-CH2- are substituted with -CH=CH-, thereby forming an alkenyloxy group having 2 to 19 carbon atoms.

[0529] The alkenyloxy group is a straight-chain, branched, or cyclic alkenyloxy group, and it is preferable that it be a straight-chain alkenyloxy group.

[0530] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6.

[0531] Also, R iii1 Silver can represent an alkyl halide group having 1 to 20 carbon atoms by substituting one or more hydrogen atoms in the alkyl group with a halogen atom.

[0532] The alkyl halide group is a straight-chain, branched, or cyclic alkyl halide group, and it is preferable that it be a straight-chain alkyl halide group.

[0533] The number of carbon atoms in the alkyl halide group is preferably 2 to 10, preferably 2 to 6.

[0534] Also, R iii1In this case, one -CH2- in the alkyl group is substituted with -O-, and one or more hydrogen atoms in the alkyl group are substituted with a halogen atom, thereby forming a halogenated alkoxy group having 1 to 19 carbon atoms.

[0535] The halogenated alkoxy group is a straight-chain, branched, or cyclic halogenated alkoxy group, and it is preferable that it be a straight-chain halogenated alkoxy group.

[0536] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0537] R iii1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) in the above include the formula (R iii1 -1)~(R iii1 Examples include the one indicated by -36).

[0538]

[0539] Equation (R iii1 -1)~(R iii1 -36) Among them, sunspots are A iii1 It represents the joint hand of the row.

[0540] R iii1 When the bonded ring structure is a phenyl group (aromatic), a straight-chain alkyl group having 1 to 5 carbon atoms, a straight-chain alkoxy group having 1 to 4 carbon atoms, and an alkenyl group having 4 to 5 carbon atoms are preferred, and R iii1 In the case where the ring structure being bonded is a saturated ring structure such as cyclohexane, pyran, and dioxane, a straight-chain alkyl group having 1 to 5 carbon atoms, a straight-chain alkoxy group having 1 to 4 carbon atoms, and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred.

[0541] Also, R iii1 In order to stabilize the nematic phase, it is desirable that the total of carbon atoms and oxygen atoms present is 5 or less, and that it is a straight chain.

[0542] Also, R iii1 As for solubility, a straight-chain alkyl group having 2 to 8 carbon atoms is preferred.

[0543] Among general formula (iii), A iii1 , A iii2 and A iii3 Each independently, the following units (a), (b), (c) and (d):

[0544] (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- in this group may be substituted with -O- and / or -S-)

[0545] (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0546] (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (one -CH= or two or more non-adjacent -CH= present in the naphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with -N=.)

[0547] (d) Thiophene-2,5-diyl group, benzothiophen-2,5-diyl group, benzothiophen-2,6-diyl group, dibenzothiophen-3,7-diyl group, dibenzothiophen-2,6-diyl group, thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0548] It represents a group selected from the group consisting of

[0549] A iii1 , A iii2 and A iii3 One or more hydrogen atoms among them, independently, are substituent S iii1 It may be substituted by.

[0550] Substituent S iii1 It represents any one of silver, a halogen atom, a cyano group, or an alkyl group having 1 to 6 carbon atoms.

[0551] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0552] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0553] In addition, one or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[0554] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0555] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0556] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0557] Also, at least one A iii1 , A iii2 or A iii3 silver, at least one substituent S iii1 It is desirable to replace it with .

[0558] Also, A iii2 is at least one substituent S ii1 It is desirable to replace it with .

[0559] Also, substituent S iii1 In cases where there are multiple instances, they may be identical or different.

[0560] A iii2 Substituent S in iii1As for the substitution positions, in terms of solubility, the following formula (A iii2 It is desirable that it be -SP-1).

[0561]

[0562] Equation (A iii2 -SP-1) Among them, white spots are A iii1 It represents the combined loss of the furnace, and the sunspot is A iii3 It represents the connection loss to.

[0563] More specifically, A iii1 is, the following formula (A iii1 -1)~(A iii1 It is desirable to represent one of the following: -2)

[0564]

[0565] Equation (A iii1 -1)~(A iii1 -2) Among them, white spots are R iii1 or A iii1 It represents the combined loss of the furnace, and the sunspot is A iii1 or A iii2 It represents the joint hand of the row.

[0566] More specifically, A iii2 is, the following formula (A iii2 -1)~(A iii2 It is desirable to represent one of -3).

[0567]

[0568] Equation (A iii2 -1)~(A iii2 -3) Among them, white points are A iii1 It represents the combined loss of the furnace, and the sunspot is A iii3 It represents the connection loss to.

[0569] More specifically, A iii3 is, the following formula (A iii3 -1)~(A iii3 It is desirable to represent one of the following: -2)

[0570]

[0571] Equation (A iii3 -1)~(A iii3 -2) Among them, white points are A iii2 It represents the bonding loss of the rho group, and the sunspot represents the bonding loss of the cyano group (-CN).

[0572] Among general formula (iii), n iii1 represents an integer between 1 and 2.

[0573] Also, in general formula (iii), A iii1 In cases where there are multiple instances, they may be identical or different.

[0574] As for the compound represented by general formula (iii), it is preferable that it be a compound represented by the following general formula (iii-1).

[0575]

[0576] In general formula (iii-1), R iii1 , A iii1 , A iii2 and A iii3 is R in the above general formula (iii). iii1 , A iii1 , A iii2 and A iii3 Each represents the same meaning.

[0577] As for the compound represented by general formula (iii-1), it is preferable that it be a compound represented by the following general formulas (iii-1-1) to (iii-1-3).

[0578]

[0579] Among general formulas (iii-1-1) to (iii-1-3), R iii1 and S iii1 are, respectively, R in the above general formula (iii). iii1 and S iii1 Each represents the same meaning.

[0580] Specific examples of compounds represented by general formula (iii-1-1) include compounds represented by the following structural formulas (iii-1-1.1) to (iii-1-1.3).

[0581]

[0582] Specific examples of compounds represented by general formula (iii-1-2) include compounds represented by the following structural formulas (iii-1-2.1) to (iii-1-2.3).

[0583]

[0584] Specific examples of compounds represented by the general formula (iii-1-3) include compounds represented by the following structural formulas (iii-1-3.1) to (iii-1-3.3).

[0585]

[0586] The types used in the liquid crystal composition of compounds represented by general formula (iii), general formula (iii-1), general formulas (iii-1-1) to (iii-1-3), structural formulas (iii-1-1.1) to (iii-1-1.3), structural formulas (iii-1-2.1) to (iii-1-2.3) or structural formulas (iii-1-3.1) to (iii-1-3.3) are one or two or more types, preferably 1 to 5 types, preferably 1 to 4 types, preferably 1 to 3 types, preferably 1 to 2 types, and preferably 1 type.

[0587] The lower limit of the total content of a compound represented by general formula (iii), general formula (iii-1), general formulas (iii-1-1) to (iii-1-3), structural formulas (iii-1-1.1) to (iii-1-1.3), structural formulas (iii-1-2.1) to (iii-1-2.3) or structural formulas (iii-1-3.1) to (iii-1-3.3) in 100 mass% of a liquid crystal composition is preferably 1 mass% or more, preferably 2 mass% or more, and preferably 3 mass% or more.

[0588] The upper limit of the total content of compounds represented by general formula (iii), general formula (iii-1), general formulas (iii-1-1) to (iii-1-3), structural formulas (iii-1-1.1) to (iii-1-1.3), structural formulas (iii-1-2.1) to (iii-1-2.3) or structural formulas (iii-1-3.1) to (iii-1-3.3) in 100 mass% of the liquid crystal composition is preferably 20 mass% or less, preferably 15 mass% or less, and preferably 10 mass% or less.

[0589] The total content in 100 mass% of the liquid crystal composition of compounds represented by general formula (iii), general formula (iii-1), general formulas (iii-1-1) to (iii-1-3), structural formulas (iii-1-1.1) to (iii-1-1.3), structural formulas (iii-1-2.1) to (iii-1-2.3) or structural formulas (iii-1-3.1) to (iii-1-3.3) is such that solubility and / or V th In terms of, it is preferable that the amount be 1 to 15 mass%, 2 to 15 mass%, and 3 to 20 mass%.

[0590] Compounds represented by general formula (iii) (including sub-concepts) can be synthesized using known synthesis methods.

[0591] The liquid crystal composition according to the present invention is V th , Δn and / or Δε r In terms of, additionally, the alkynyl group (R iv1 It may include one or more compounds represented by the following general formula (iv) having -C≡C-) and a cyano group (-CN).

[0592]

[0593] Among general formula (iv), R iv1 It represents an alkyl group with 1 to 20 carbon atoms.

[0594] The alkyl group having 1 to 20 carbon atoms is a straight-chain, branched, or cyclic alkyl group, and it is preferably a straight-chain alkyl group.

[0595] The number of carbon atoms in the alkyl group is preferably 2 to 10, preferably 2 to 6.

[0596] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0597] In addition, one or more -CH2-CH2- groups among the alkyl groups may be substituted with -CH=CH-, -COO-, -OCO- and / or -C≡C-.

[0598] In addition, one or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[0599] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0600] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0601] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0602] For example, R iv1 One -CH2- in the alkyl group can be substituted with -O- to form an alkoxy group having 1 to 19 carbon atoms.

[0603] The alkoxy group is a linear, branched, or cyclic alkoxy group, and it is preferable that it be a linear alkoxy group.

[0604] The number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0605] Also, R iv1In this case, one -CH2- in the alkyl group is substituted with -S-, thereby forming a thioalkoxy group (alkylsulfanyl group, alkylthio group) having 1 to 19 carbon atoms.

[0606] The thioalkoxy group is a linear, branched, or cyclic thioalkoxy group, and it is preferable that it be a linear thioalkoxy group.

[0607] The number of carbon atoms in the thioalkoxy group is preferably 2 to 10, preferably 2 to 6.

[0608] Also, R iv1 One or more -CH2-CH2- groups among the alkyl groups can be substituted with -CH=CH- to form an alkenyl group having 2 to 20 carbon atoms.

[0609] The alkenyl group is a straight-chain, branched, or cyclic alkenyl group, and it is preferable that it be a straight-chain alkenyl group.

[0610] The number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.

[0611] Also, R iv1 One or more -CH2-CH2- groups among the alkyl groups can be substituted with -C≡C- to form an alkynyl group having 2 to 20 carbon atoms.

[0612] The alkynyl group is a straight, branched, or cyclic alkynyl group, and it is preferable that it be a straight alkynyl group.

[0613] The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.

[0614] Also, R iv1 In this case, one -CH2- in the alkyl group is substituted with -O-, and one or more -CH2-CH2- are substituted with -CH=CH-, thereby forming an alkenyloxy group having 2 to 19 carbon atoms.

[0615] The alkenyloxy group is a straight-chain, branched, or cyclic alkenyloxy group, and it is preferable that it be a straight-chain alkenyloxy group.

[0616] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6.

[0617] Also, R iv1 Silver can represent an alkyl halide group having 1 to 20 carbon atoms by substituting one or more hydrogen atoms in the alkyl group with a halogen atom.

[0618] The alkyl halide group is a straight-chain, branched, or cyclic alkyl halide group, and it is preferable that it be a straight-chain alkyl halide group.

[0619] The number of carbon atoms in the alkyl halide group is preferably 2 to 10, preferably 2 to 6.

[0620] Also, R iv1 In this case, one -CH2- in the alkyl group is substituted with -O-, and one or more hydrogen atoms in the alkyl group are substituted with a halogen atom, thereby forming a halogenated alkoxy group having 1 to 19 carbon atoms.

[0621] The halogenated alkoxy group is a straight-chain, branched, or cyclic alkoxy group, and it is preferable that it be a straight-chain alkoxy group.

[0622] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0623] R iv1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) in the above include the formula (R iv1 -1)~(R iv1 Examples include the one indicated by -36).

[0624]

[0625] Equation (R iv1 -1)~(Riv1 -36) Among them, sunspots represent a bond loss of -C≡C-.

[0626] Also, R iv1 As for solubility, a straight-chain alkyl group having 2 to 8 carbon atoms is preferred.

[0627] Among general formula (iv), A iv1 and A iv2 are, each independently, the following units (a), (b), (c) and (d):

[0628] (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- in this group may be substituted with -O- and / or -S-)

[0629] (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0630] (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (one -CH= or two or more non-adjacent -CH= present in the naphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with -N=.)

[0631] (d) Thiophene-2,5-diyl group, benzothiophen-2,5-diyl group, benzothiophen-2,6-diyl group, dibenzothiophen-3,7-diyl group, dibenzothiophen-2,6-diyl group, thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0632] It represents a group selected from the group consisting of

[0633] A iv1 and A iv2 One or more hydrogen atoms among them, independently, are substituent S iv1It may be substituted by.

[0634] Substituent S iv1 It represents any one of silver, a halogen atom, a cyano group, or an alkyl group having 1 to 6 carbon atoms.

[0635] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0636] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0637] One or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[0638] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0639] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0640] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0641] Also, A iv1 At least one of them is a substituent S iv1 It is desirable to replace it with .

[0642] Also, substituent S iv1 In cases where there are multiple instances, they may be identical or different.

[0643] A iv1 Substituent S in iv1 As for the substitution positions, in terms of solubility, the following formula (A iv1 It is desirable to have one of the following: -SP-1).

[0644]

[0645] Equation (A iv1 -SP-1) Among them, white spots are -C≡C- or A iv1 It represents the combined loss of the furnace, and the sunspot is A iv1 or A iv2 It represents the joint hand of the row.

[0646] A iv2 Substituent S in iv1 As for the substitution positions, the following expression (A iv2 -SP-1)~(A iv2 It is desirable to have one of the following: -SP-2).

[0647]

[0648] Equation (A iv2 -SP-1)~(A iv2 -SP-2) Among them, white spots are A iv1 It represents the bonding loss of the rho group, and the sunspot represents the bonding loss of the cyano group (-CN).

[0649] More specifically, A iv1 is, the following formula (A iv1 -1)~(A iv1 It is desirable to represent one of -3).

[0650]

[0651] Equation (A iv1 -1)~(A iv1 -3) Among them, white spots are -C≡C- or A iv1 It represents the combined loss of the furnace, and the sunspot is A iv1 or A iv2 It represents the joint hand of the row.

[0652] More specifically, A iv2 is, the following formula (A iv2 -1)~(A iv2 It is desirable to represent one of the following: -4)

[0653]

[0654] Equation (A iv2 -1)~(A iv2 -4) Among them, white points are Aiv1 It represents the bonding loss of the rho group, and the sunspot represents the bonding loss of the cyano group (-CN).

[0655] n iv1 represents an integer between 1 and 2.

[0656] Also, in general formula (iv), A iv1 In cases where there are multiple instances, they may be identical or different.

[0657] As for the compound represented by general formula (iv), it is preferable that it be a compound represented by the following general formula (iv-1).

[0658]

[0659] In general formula (iv-1), R iv1 , A iv1 and A iv2 is R in the above general formula (iv). iv1 , A iv1 and A iv2 Each represents the same meaning.

[0660] As for the compound represented by general formula (iv-1), it is preferable that it be a compound represented by the following general formulas (iv-1-1) to (iv-1-6).

[0661]

[0662] Among general formulas (iv-1-1) to (iv-1-6), R iv1 and S iv1 R in the above general formula (iv), each independently iv1 and S iv1 Each represents the same meaning.

[0663] Specific examples of compounds represented by general formula (iv-1-1) include compounds represented by the following structural formulas (iv-1-1.1) to (iv-1-1.2).

[0664]

[0665] Specific examples of compounds represented by general formula (iv-1-2) include compounds represented by the following structural formulas (iv-1-2.1) to (iv-1-2.2).

[0666]

[0667] Specific examples of compounds represented by general formula (iv-1-3) include compounds represented by the following structural formulas (iv-1-3.1) to (iv-1-3.2).

[0668]

[0669] Specific examples of compounds represented by general formula (iv-1-4) include compounds represented by the following structural formulas (iv-1-4.1) to (iv-1-4.2).

[0670]

[0671] Specific examples of compounds represented by general formula (iv-1-5) include compounds represented by the following structural formulas (iv-1-5.1) to (iv-1-5.2).

[0672]

[0673] Specific examples of compounds represented by general formula (iv-1-6) include compounds represented by the following structural formulas (iv-1-6.1) to (iv-1-6.2).

[0674]

[0675] The types used in the liquid crystal composition of compounds represented by general formula (iv), general formula (iv-1), general formulas (iv-1-1) to (iv-1-6), structural formulas (iv-1-1.1) to (iv-1-1.2), structural formulas (iv-1-2.1) to (iv-1-2.2), structural formulas (iv-1-3.1) to (iv-1-3.2), structural formulas (iv-1-4.1) to (iv-1-4.2), structural formulas (iv-1-5.1) to (iv-1-5.2) or structural formulas (iv-1-6.1) to (iv-1-6.2) are one or two or more types, preferably 1 to 5 types, preferably 1 to 4 types, preferably 1 to 3 types, preferably 1 to 2 types, and preferably 1 type.

[0676] The lower limit of the total content of compounds represented by general formula (iv), general formula (iv-1), general formula (iv-1-1) to (iv-1-6), structural formula (iv-1-1.1) to (iv-1-1.2), structural formula (iv-1-2.1) to (iv-1-2.2), structural formula (iv-1-3.1) to (iv-1-3.2), structural formula (iv-1-4.1) to (iv-1-4.2), structural formula (iv-1-5.1) to (iv-1-5.2) or structural formula (iv-1-6.1) to (iv-1-6.2) in 100 mass% of the liquid crystal composition is preferably 0 mass% or more, preferably 1 mass% or more, and preferably 5 mass% or more.

[0677] The upper limit of the total content of compounds represented by general formula (iv), general formula (iv-1), general formula (iv-1-1) to (iv-1-6), structural formula (iv-1-1.1) to (iv-1-1.2), structural formula (iv-1-2.1) to (iv-1-2.2), structural formula (iv-1-3.1) to (iv-1-3.2), structural formula (iv-1-4.1) to (iv-1-4.2), structural formula (iv-1-5.1) to (iv-1-5.2) or structural formula (iv-1-6.1) to (iv-1-6.2) in 100 mass% of the liquid crystal composition is preferably 35 mass% or less, preferably 30 mass% or less, and preferably 25 mass% or less.

[0678] The total content of compounds represented by general formula (iv), general formula (iv-1), general formulas (iv-1-1) to (iv-1-6), structural formulas (iv-1-1.1) to (iv-1-1.2), structural formulas (iv-1-2.1) to (iv-1-2.2), structural formulas (iv-1-3.1) to (iv-1-3.2), structural formulas (iv-1-4.1) to (iv-1-4.2), structural formulas (iv-1-5.1) to (iv-1-5.2) or structural formulas (iv-1-6.1) to (iv-1-6.2) in 100 mass% of a liquid crystal composition is preferably 0 to 35 mass%, preferably 1 to 30 mass%, and preferably 5 to 25 mass% in terms of compatibility with other liquid crystal compounds.

[0679] Compounds represented by general formula (iv) (including sub-concepts) can be synthesized using known synthesis methods.

[0680] The liquid crystal composition according to the present invention is V th , Δn and / or Δε r In this regard, it may additionally include one or more compounds represented by the following general formula (v) having at least one -C≡C- and a cyano group (-CN) as a linker.

[0681]

[0682] Among the general formula (v), R v1 It represents an alkyl group with 1 to 20 carbon atoms.

[0683] The alkyl group is a straight-chain, branched, or cyclic alkyl group, and it is preferably a straight-chain alkyl group.

[0684] The number of carbon atoms in the alkyl group is preferably 2 to 10, preferably 2 to 6.

[0685] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0686] In addition, one or more -CH2-CH2- groups among the alkyl groups may each be independently substituted with -CH=CH-, -CO-O-, -O-CO- and / or -C≡C-.

[0687] In addition, one or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[0688] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0689] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0690] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0691] For example, R v1 One -CH2- in the alkyl group can be substituted with -O- to form an alkoxy group having 1 to 19 carbon atoms.

[0692] The alkoxy group is a linear, branched, or cyclic alkoxy group, and it is preferable that it be a linear alkoxy group.

[0693] The number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0694] Also, R v1 silver, R v1 One of the -CH2- groups can be substituted with -S- to form a thioalkoxy group (alkylsulfanyl group, alkylthio group) having 1 to 19 carbon atoms.

[0695] The thioalkoxy group is a linear, branched, or cyclic thioalkoxy group, and it is preferable that it be a linear thioalkoxy group.

[0696] The number of carbon atoms in the thioalkoxy group is preferably 2 to 10, preferably 2 to 6.

[0697] Also, R v1 One or more -CH2-CH2- groups among the alkyl groups can be substituted with -CH=CH- to form an alkenyl group having 2 to 20 carbon atoms.

[0698] The alkenyl group is a straight-chain, branched, or cyclic alkenyl group, and it is preferable that it be a straight-chain alkenyl group.

[0699] The number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.

[0700] Also, R v1 One or more -CH2-CH2- groups among the alkyl groups can be substituted with -C≡C- to form an alkynyl group having 2 to 20 carbon atoms.

[0701] The alkynyl group is a straight, branched, or cyclic alkynyl group, and it is preferable that it be a straight alkynyl group.

[0702] The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.

[0703] Also, R v1 In this case, one -CH2- in the alkyl group is substituted with -O-, and one or more -CH2-CH2- are substituted with -CH=CH-, thereby forming an alkenyloxy group having 2 to 19 carbon atoms.

[0704] The alkenyloxy group is a straight-chain, branched, or cyclic alkenyloxy group, and it is preferable that it be a straight-chain alkenyloxy group.

[0705] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6.

[0706] Also, R v1Silver can represent an alkyl halide group having 1 to 20 carbon atoms by substituting one or more hydrogen atoms in the alkyl group with a halogen atom.

[0707] The alkyl halide group is a straight-chain, branched, or cyclic alkyl halide group, and it is preferable that it be a straight-chain alkyl halide group.

[0708] The number of carbon atoms in the alkyl halide group is preferably 2 to 10, preferably 2 to 6.

[0709] Also, R v1 In this case, one -CH2- in the alkyl group is substituted with -O-, and one or more hydrogen atoms in the alkyl group are substituted with a halogen atom, thereby forming a halogenated alkoxy group having 1 to 19 carbon atoms.

[0710] The halogenated alkoxy group is a straight-chain, branched, or cyclic halogenated alkoxy group, and it is preferable that it be a straight-chain halogenated alkoxy group.

[0711] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0712] R v1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) in the above include the formula (R v1 -1)~(R v1 Examples include the one indicated by -36).

[0713]

[0714] Equation (R v1 -1)~(R v1 -36) Among them, sunspots are A v1 It represents the joint hand of the row.

[0715] R v1When the bonded ring structure is a phenyl group (aromatic), a straight-chain alkyl group having 1 to 5 carbon atoms, a straight-chain alkoxy group having 1 to 4 carbon atoms, and an alkenyl group having 4 to 5 carbon atoms are preferred, and R v1 In the case where the ring structure being bonded is a saturated ring structure such as cyclohexane, pyran, and dioxane, a straight-chain alkyl group having 1 to 5 carbon atoms, a straight-chain alkoxy group having 1 to 4 carbon atoms, and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred.

[0716] Also, R v1 In order to stabilize the nematic phase, it is desirable that the total of carbon atoms and oxygen atoms present is 5 or less, and that it is a straight chain.

[0717] Also, R v1 As for solubility, a straight-chain alkyl group having 2 to 8 carbon atoms is preferred.

[0718] Among the general formula (v), A v1 and A v2 are, each independently, the following units (a), (b), (c) and (d):

[0719] (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- in this group may be substituted with -O- and / or -S-)

[0720] (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0721] (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (one -CH= or two or more non-adjacent -CH= present in the naphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with -N=.)

[0722] (d) Thiophene-2,5-diyl group, benzothiophen-2,5-diyl group, benzothiophen-2,6-diyl group, dibenzothiophen-3,7-diyl group, dibenzothiophen-2,6-diyl group, thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0723] It represents a group selected from the group consisting of

[0724] A v1 and A v2 One or more hydrogen atoms among them, independently, are substituent S v1 It may be substituted by.

[0725] Substituent S v1 It represents any one of silver, a halogen atom, a cyano group, or an alkyl group having 1 to 6 carbon atoms.

[0726] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0727] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0728] In addition, one or more hydrogen atoms present in the alkyl group may each be independently substituted with a halogen atom.

[0729] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0730] However, in cases where an alkyl group having 1 to 6 carbon atoms is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0731] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0732] Also, A v1 At least one of or A v2 is at least one substituent S v1 It is desirable to replace it with .

[0733] Also, substituent S v1 In cases where there are multiple instances, they may be identical or different.

[0734] A v1 Substituent S in v1 As for the substitution positions, in terms of solubility, the following formula (A v1 It is desirable that it be -SP-1).

[0735]

[0736] Equation (A v1 -SP-1) Among them, white spots are R v1 or Z v1 Represents the combined loss of the furnace, and the sunspot is Z v1 It represents the joint hand of the row.

[0737] A v2 Substituent S in v1 As for the substitution positions, the following expression (A v2 -SP-1)~(A v2 It is desirable to have one of the following: -SP-2).

[0738]

[0739] Equation (A v2 -SP-1)~(A v2 -SP-2) Among them, white spots are Z v1 It represents the bonding loss of the rho group, and the sunspot represents the bonding loss of the cyano group (-CN).

[0740] More specifically, A v1 is, the following formula (A v1 -1)~(A v1 It is desirable to represent one of -3).

[0741]

[0742] Equation (A v1 -1)~(Av1 -3) Among them, white spots are R v1 or Z v1 Represents the combined loss of the furnace, and the sunspot is Z v1 It represents the joint hand of the row.

[0743] More specifically, A v2 is, the following formula (A v2 -1)~(A v2 It is desirable to represent one of -3).

[0744]

[0745] Equation (A v2 -1)~(A v2 -3) Among them, white spots are Z v1 It represents the bonding loss of the rho group, and the sunspot represents the bonding loss of the cyano group (-CN).

[0746] Among the general formula (v), Z v1 It represents any one of a single bond, -C≡C-, -CH=CH-, or -CF=CF-.

[0747] However, Z v1 At least one of them represents -C≡C-.

[0748] Among the general formula (v), n v1 represents an integer between 1 and 2.

[0749] Also, in the general formula (v), A v1 and Z v1 In cases where multiple instances exist, they may each be identical or different.

[0750] As for the compound represented by general formula (v), it is preferable that it be a compound represented by the following general formulas (v-1) to (v-2).

[0751]

[0752] Among the general formulas (v-1) to (v-2), R v1 , A v1 and A v2 is R in the above general formula (v). v1 , A v1 and Av2 Each represents the same meaning.

[0753] Among general formulas (v-1) to (v-2), A v1-2 The definition of is A in the above general formula (v). v1 It is the same as the definition of.

[0754] As for the compound represented by general formula (v-1), it is preferable that it be a compound represented by the following general formulas (v-1-1) to (v-1-6).

[0755]

[0756] Among the general formulas (v-1-1) to (v-1-6), R v1 and S v1 R in the above general formula (v), each independently v1 and S v1 Each represents the same meaning.

[0757] 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).

[0758]

[0759] Specific examples of compounds represented by the general formula (v-1-2) include compounds represented by the following structural formulas (v-1-2.1) to (v-1-2.3).

[0760]

[0761] Specific examples of compounds represented by the general formula (v-1-3) include compounds represented by the following structural formulas (v-1-3.1) to (v-1-3.3).

[0762]

[0763] Specific examples of compounds represented by the general formula (v-1-4) include compounds represented by the following structural formulas (v-1-4.1) to (v-1-4.3).

[0764]

[0765] Specific examples of compounds represented by the general formula (v-1-5) include compounds represented by the following structural formulas (v-1-5.1) to (v-1-5.3).

[0766]

[0767] Specific examples of compounds represented by the general formula (v-1-6) include compounds represented by the following structural formulas (v-1-6.1) to (v-1-6.3).

[0768]

[0769] As for the compound represented by general formula (v-2), it is preferable that it be a compound represented by the following general formulas (v-2-1) to (v-2-2).

[0770]

[0771] Among the general formulas (v-2-1) to (v-2-2), R v1 and S v1 R in the above general formula (v), each independently v1 and S v1 Each represents the same meaning.

[0772] 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).

[0773]

[0774] 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).

[0775]

[0776] The types used in the liquid crystal composition of compounds represented by general formula (v), general formulas (v-1) to (v-2), general formulas (v-1-1) to (v-1-6), general formulas (v-2-1) to (v-2-2), structural formulas (v-1-1.1) to (v-1-1.3), structural formulas (v-1-2.1) to (v-1-2.3), structural formulas (v-1-3.1) to (v-1-3.3), structural formulas (v-1-4.1) to (v-1-4.3), structural formulas (v-1-5.1) to (v-1-5.3), structural formulas (v-1-6.1) to (v-1-6.3), structural formulas (v-2-1.1) to (v-2-1.3) or structural formulas (v-2-2.1) to (v-2-2.3) are one or two or more, preferably There are 1 to 5 types, preferably 1 to 4 types, preferably 1 to 3 types, preferably 1 to 2 types, and preferably 1 type.

[0777] The lower limit of the total content in 100 mass% of a liquid crystal composition of a compound represented by general formula (v), general formulas (v-1) to (v-2), general formulas (v-1-1) to (v-1-6), general formulas (v-2-1) to (v-2-2), structural formulas (v-1-1.1) to (v-1-1.3), structural formulas (v-1-2.1) to (v-1-2.3), structural formulas (v-1-3.1) to (v-1-3.3), structural formulas (v-1-4.1) to (v-1-4.3), structural formulas (v-1-5.1) to (v-1-5.3), structural formulas (v-1-6.1) to (v-1-6.3), structural formulas (v-2-1.1) to (v-2-1.3) or structural formulas (v-2-2.1) to (v-2-2.3) is: It is preferable that it be 1 mass% or more, 3 mass% or more, and 5 mass% or more.

[0778] The upper limit of the total content in 100 mass% of a liquid crystal composition of a compound represented by general formula (v), general formulas (v-1) to (v-2), general formulas (v-1-1) to (v-1-6), general formulas (v-2-1) to (v-2-2), structural formulas (v-1-1.1) to (v-1-1.3), structural formulas (v-1-2.1) to (v-1-2.3), structural formulas (v-1-3.1) to (v-1-3.3), structural formulas (v-1-4.1) to (v-1-4.3), structural formulas (v-1-5.1) to (v-1-5.3), structural formulas (v-1-6.1) to (v-1-6.3), structural formulas (v-2-1.1) to (v-2-1.3) or structural formulas (v-2-2.1) to (v-2-2.3) is: It is preferable that it be 30 mass% or less, 25 mass% or less, and 20 mass% or less.

[0779] The total content in 100 mass% of a liquid crystal composition of a compound represented by general formula (v), general formulas (v-1) to (v-2), general formulas (v-1-1) to (v-1-6), general formulas (v-2-1) to (v-2-2), structural formulas (v-1-1.1) to (v-1-1.3), structural formulas (v-1-2.1) to (v-1-2.3), structural formulas (v-1-3.1) to (v-1-3.3), structural formulas (v-1-4.1) to (v-1-4.3), structural formulas (v-1-5.1) to (v-1-5.3), structural formulas (v-1-6.1) to (v-1-6.3), structural formulas (v-2-1.1) to (v-2-1.3) or structural formulas (v-2-2.1) to (v-2-2.3) is, solubility and / or V th In terms of, it is preferable that the amount be 1 to 30 mass%, 3 to 25 mass%, and 5 to 20 mass%.

[0780] Compounds represented by general formula (v) (including sub-concepts) can be synthesized using known synthesis methods.

[0781] The liquid crystal composition according to the present invention comprises Δn and / or Δε rIn this regard, one or more compounds represented by the following general formula (vi), having at least one -C≡C- as a linker, may be included.

[0782]

[0783] Among the general formula (vi), R vi1 It represents silver, hydrogen atoms, or alkyl groups having 1 to 20 carbon atoms.

[0784] The alkyl group having 1 to 20 carbon atoms is a straight-chain, branched, or cyclic alkyl group, and it is preferably a straight-chain alkyl group.

[0785] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.

[0786] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0787] In addition, one or more -CH2-CH2- groups among the alkyl groups may each be independently substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0788] In addition, one or more -CH2-CH2-CH2- among the alkyl groups may each be independently substituted with -O-CO-O-.

[0789] In addition, one or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[0790] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0791] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0792] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0793] For example, R vi1 One -CH2- in the alkyl group can be substituted with -O- to form an alkoxy group having 1 to 19 carbon atoms.

[0794] The alkoxy group is a linear, branched, or cyclic alkoxy group, and it is preferable that it be a linear alkoxy group.

[0795] The number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0796] Also, R vi1 In this case, one -CH2- in the alkyl group is substituted with -S-, thereby forming a thioalkoxy group (alkylsulfanyl group, alkylthio group) having 1 to 19 carbon atoms.

[0797] The thioalkoxy group is a linear, branched, or cyclic thioalkoxy group, and it is preferable that it be a linear thioalkoxy group.

[0798] The number of carbon atoms in the thioalkoxy group is preferably 2 to 10, preferably 2 to 6.

[0799] Also, R vi1 One or more -CH2-CH2- groups among the alkyl groups can be substituted with -CH=CH- to form an alkenyl group having 2 to 20 carbon atoms.

[0800] The alkenyl group is a straight-chain, branched, or cyclic alkenyl group, and it is preferable that it be a straight-chain alkenyl group.

[0801] The number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.

[0802] Also, R vi1 One or more -CH2-CH2- groups among the alkyl groups can be substituted with -C≡C- to form an alkynyl group having 2 to 20 carbon atoms.

[0803] The alkynyl group is a straight, branched, or cyclic alkynyl group, and it is preferable that it be a straight alkynyl group.

[0804] The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.

[0805] Also, R vi1 In this case, one -CH2- in the alkyl group is substituted with -O-, and one or more -CH2-CH2- are substituted with -CH=CH-, thereby forming an alkenyloxy group having 2 to 19 carbon atoms.

[0806] The alkenyloxy group is a straight-chain, branched, or cyclic alkenyloxy group, and it is preferable that it be a straight-chain alkenyloxy group.

[0807] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6.

[0808] Also, R vi1 Silver can represent an alkyl halide group having 1 to 20 carbon atoms by substituting one or more hydrogen atoms in the alkyl group with a halogen atom.

[0809] The alkyl halide group is a straight-chain, branched, or cyclic alkyl halide group, and it is preferable that it be a straight-chain alkyl halide group.

[0810] The number of carbon atoms in the alkyl halide group is preferably 2 to 10, preferably 2 to 6.

[0811] Also, R vi1In this case, one -CH2- in the alkyl group is substituted with -O-, and one or more hydrogen atoms in the alkyl group are substituted with a halogen atom, thereby forming a halogenated alkoxy group having 1 to 19 carbon atoms.

[0812] The halogenated alkoxy group is a straight-chain, branched, or cyclic alkoxy group, and it is preferable that it be a straight-chain alkoxy group.

[0813] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0814] R vi1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) in the above include the formula (R vi1 -1)~(R vi1 Examples include the one indicated by -36).

[0815]

[0816] Equation (R vi1 -1)~(R vi1 -36) Among them, sunspots are A vi1 It represents the joint hand of the row.

[0817] R vi1 When the reliability of the entire liquid crystal composition is important, it is preferable that the alkyl group has 1 to 12 carbon atoms, and when the reduction of the viscosity of the entire liquid crystal composition is important, it is preferable that the alkenyl group has 2 to 8 carbon atoms.

[0818] R vi1 When the bonded ring structure is a phenyl group (aromatic), a straight-chain alkyl group having 1 to 5 carbon atoms, a straight-chain alkoxy group having 1 to 4 carbon atoms, and an alkenyl group having 4 to 5 carbon atoms are preferred, and R vi1 In the case where the ring structure being bonded is a saturated ring structure such as cyclohexane, pyran, and dioxane, a straight-chain alkyl group having 1 to 5 carbon atoms, a straight-chain alkoxy group having 1 to 4 carbon atoms, and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred.

[0819] Also, R vi1 In order to stabilize the nematic phase, it is desirable that the total of carbon atoms and oxygen atoms present is 5 or less, and that it is a straight chain.

[0820] Also, R vi1 As for solubility, a straight-chain alkyl group having 2 to 6 carbon atoms is preferred.

[0821] Among the general formula (vi), R vi2 It represents any one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, or an alkyl group having 1 to 20 carbon atoms.

[0822] The alkyl group having 1 to 20 carbon atoms is a straight-chain, branched, or cyclic alkyl group, and it is preferably a straight-chain alkyl group.

[0823] The number of carbon atoms in the alkyl group is preferably 2 to 10, preferably 2 to 6.

[0824] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0825] In addition, one or more -CH2-CH2- groups among the alkyl groups may each be independently substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0826] In addition, one or more -CH2-CH2-CH2- among the alkyl groups may each be independently substituted with -O-CO-O-.

[0827] In addition, one or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[0828] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0829] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0830] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0831] For example, R vi2 One -CH2- in the alkyl group can be substituted with -O- to form an alkoxy group having 1 to 19 carbon atoms.

[0832] The alkoxy group is a linear, branched, or cyclic alkoxy group, and it is preferable that it be a linear alkoxy group.

[0833] The number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0834] Also, R vi2 One -CH2- in the alkyl group is substituted with -S-, thereby forming a thioalkoxy group (alkylsulfanyl group, alkylthio group) having 1 to 19 carbon atoms.

[0835] The thioalkoxy group is a linear, branched, or cyclic thioalkoxy group, and it is preferable that it be a linear thioalkoxy group.

[0836] The number of carbon atoms in the thioalkoxy group is preferably 2 to 10, preferably 2 to 6.

[0837] Also, R vi2One or more -CH2-CH2- groups among the alkyl groups can be substituted with -CH=CH- to represent an alkenyl group having 2 to 20 carbon atoms.

[0838] The alkenyl group is a straight-chain, branched, or cyclic alkenyl group, and it is preferable that it be a straight-chain alkenyl group.

[0839] The number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.

[0840] Also, R vi2 One or more -CH2-CH2- groups among the alkyl groups can be substituted with -C≡C- to represent an alkynyl group having 2 to 20 carbon atoms.

[0841] The alkynyl group is a straight, branched, or cyclic alkynyl group, and it is preferable that it be a straight alkynyl group.

[0842] The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.

[0843] Also, R vi2 One -CH2- in the alkyl group is substituted with -O-, and one or more -CH2-CH2- are substituted with -CH=CH-, thereby forming an alkenyloxy group having 2 to 19 carbon atoms.

[0844] The alkenyloxy group is a straight-chain, branched, or cyclic alkenyloxy group, and it is preferable that it be a straight-chain alkenyloxy group.

[0845] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6.

[0846] Also, R vi2 alkyl halide groups having 1 to 20 carbon atoms can be represented by substituting one or more hydrogen atoms in the alkyl group with a halogen atom.

[0847] The alkyl halide group is a straight-chain, branched, or cyclic alkyl halide group, and it is preferable that it be a straight-chain alkyl halide group.

[0848] The number of carbon atoms in the alkyl halide group is preferably 2 to 10, preferably 2 to 6.

[0849] Also, R vi2 A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by substituting one -CH2- in the alkyl group with -O- and substituting one or more hydrogen atoms in the alkyl group with a halogen atom.

[0850] The halogenated alkoxy group is a straight-chain, branched, or cyclic alkoxy group, and it is preferable that it be a straight-chain alkoxy group.

[0851] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0852] R vi2 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) in the above include the formula (R vi2 -1)~(R vi2 Examples include the one indicated by -36).

[0853]

[0854] Equation (R vi2 -1)~(R vi2 -36) Among them, sunspots are A vi3 It represents the connection loss to.

[0855] R vi2 When the ring structure to which is bonded is a phenyl group (aromatic), a straight-chain alkyl group having 1 to 5 carbon atoms, a straight-chain alkoxy group having 1 to 4 carbon atoms, and an alkenyl group having 4 to 5 carbon atoms are preferred, and R i1In the case where the ring structure being bonded is a saturated ring structure such as cyclohexane, pyran, and dioxane, a straight-chain alkyl group having 1 to 5 carbon atoms, a straight-chain alkoxy group having 1 to 4 carbon atoms, and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred.

[0856] Also, R vi2 In order to stabilize the nematic phase, it is desirable that the total of carbon atoms and oxygen atoms present is 5 or less, and that it is a straight chain.

[0857] Also, R vi2 As for, solubility, Δn and / or Δε r From the perspective of, a straight-chain alkyl group having 2 to 6 carbon atoms or a straight-chain thioalkoxy group having 1 to 6 carbon atoms is preferred.

[0858] Among general formula (vi), A vi1 , A vi2 and A vi3 Each independently represents either a hydrocarbon ring with 3 to 16 carbon atoms or a complex ring with 3 to 16 carbon atoms.

[0859] A hydrocarbon ring having 3 to 16 carbon atoms or a complex ring having 3 to 16 carbon atoms is, more specifically, the following groups (a), (b), (c), and (d):

[0860] (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- in this group may be substituted with -O- or -S-)

[0861] (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0862] (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group(naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, One -CH= or two or more -CH= present in 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, or phenanthrene-2,7-diyl group may be substituted with -N=.)

[0863] (d) Thiophene-2,5-diyl group, benzothiophen-2,5-diyl group, benzothiophen-2,6-diyl group, dibenzothiophen-3,7-diyl group, dibenzothiophen-2,6-diyl group, thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0864] It is desirable to represent a group selected from the group consisting of

[0865] A vi1 , A vi2 and A vi3 One or more hydrogen atoms among them, independently, are substituent S vi1 It may be substituted by.

[0866] Substituent S vi1It represents any one of silver, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, and alkyl groups having 1 to 20 carbon atoms.

[0867] The alkyl group is a straight-chain, branched, or cyclic alkyl group, and it is preferably a straight-chain alkyl group.

[0868] The number of carbon atoms in the alkyl group is preferably 2 to 10, preferably 3 to 6.

[0869] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S- and / or -CO-.

[0870] In addition, one or more -CH2-CH2- groups in the alkyl group may each be independently substituted with -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-.

[0871] In addition, one or more -CH2-CH2-CH2- in the alkyl group may be substituted with -O-CO-O-.

[0872] One or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[0873] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0874] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0875] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0876] Substituent S vi1 As for the element, a fluorine atom or a straight-chain alkyl group having 1 to 3 carbon atoms is preferred.

[0877] Also, A vi1 , A vi2 and A vi3 At least one of them is at least one substituent S vi1 It is desirable to replace it with .

[0878] Also, A vi1 silver, at least one substituent S vi1 It is desirable to replace it with .

[0879] Also, substituent S vi1 In cases where there are multiple instances, they may be identical or different.

[0880] A vi1 Substituent S in vi1 As for the substitution positions, the following expression (A vi1 -SP-1)~(A vi1 It is desirable to have one of the following: -SP-2).

[0881]

[0882] Equation (A vi1 -SP-1)~(A vi1 -SP-2) Among them, white spots are R vi1 It represents the bonding loss of, and the black spot represents the bonding loss of -C≡C-.

[0883] A vi2 Substituent S in vi1 As for the substitution positions, the following expression (A vi2 -SP-1)~(A vi2 It is preferable that any one of -SP-7) be used, and in terms of compatibility with other liquid crystal compounds, the following formula (A vi2 -SP-1)~(A vi2It is desirable to indicate one of the following: -SP-7)

[0884]

[0885] Equation (A vi2 -SP-1)~(A vi2 Among -SP-7), white spots represent -C≡C- bonding losses, and black spots are Z vi1 It represents the joint hand of the row.

[0886] A vi3 Substituent S in vi3 As for the substitution positions, the following expression (A vi3 -SP-1)~(A vi3 It is preferable that any one of -SP-7) be used, and in terms of solubility, the following formula (A vi3 -SP-1)~(A vi3 It is desirable to indicate any one of -SP-5).

[0887]

[0888] Equation (A vi3 -SP-1)~(A vi3 -SP-7) Among them, white spots are Z vi1 Represents the combined loss of the furnace, and the sunspot is Z vi1 or R vi2 It represents the joint hand of the row.

[0889] More specifically, A vi1 is, the following formula (A vi1 -1)~(A vi1 It is desirable to represent one of the following: -4)

[0890]

[0891] Equation (A vi1 -1)~(A vi1 -4) Among them, white spots are R vi1 It represents the bonding loss of, and the black spot represents the bonding loss of -C≡C-.

[0892] More specifically, A vi2 is, the following formula (A vi2 -1)~(A vi2It is desirable to represent one of -5).

[0893]

[0894] Equation (A vi2 -1)~(A vi2 -5) Among them, white spots represent the -C≡C- bonding loss, and black spots are Z i1 It represents the joint hand of the row.

[0895] More specifically, A vi3 is, the following formula (A vi3 -1)~(A vi3 It is desirable to represent one of -3).

[0896]

[0897] Equation (A vi3 -1)~(A vi3 -3) Among them, white spots are Z vi1 Represents the combined loss of the furnace, and the sunspot is Z vi1 or R vi2 It represents the joint hand of the row.

[0898] Among general formulas (vi), Z vi1 Each represents, independently, any one of a single bond and an alkylene group having 1 to 20 carbon atoms.

[0899] The alkylene group is a straight-chain, branched, or cyclic alkylene group, and it is preferable that it be a straight-chain alkylene group.

[0900] The number of carbon atoms in the alkylene group is preferably 2 to 10, preferably 2 to 6.

[0901] One or more -CH2- groups in the alkylene group may each be independently substituted with -O-, -CF2- and / or -CO-.

[0902] In addition, one or more -CH2-CH2- groups in the alkylene group may each be independently substituted with -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[0903] In addition, one or more -CH2-CH2-CH2- among the alkyl groups may each be independently substituted with -O-CO-O-.

[0904] However, in cases where the alkylene group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0905] Specific examples of alkylene groups having 2 to 20 carbon atoms (including substituted ones) include the formula (Z vi1 -1)~(Z vi1 Examples include the one indicated by -24.

[0906]

[0907] Equation (Z vi1 -1)~(Z vi1 -24) Among them, white points are A vi2 or A vi3 It represents the connection loss to, and the sunspot is A vi3 It represents the connection loss to.

[0908] n vi1 It represents an integer of 1 to 3, preferably an integer of 1 to 2.

[0909] n vi1 In the case where this is 1, Δn and / or Δε r From the perspective of, Z vi1 It is desirable to represent -C≡C-.

[0910] Also, n vi1 In the case where this is 2 or 3, Δn and / or Δε r From the perspective of, Z vi1It is desirable that at least one of them represents -C≡C-.

[0911] Also, in general formula (vi), A vi3 and Z vi1 In cases where multiple instances exist, they may each be identical or different.

[0912] As for the compound represented by general formula (vi), it is preferable that it be a compound represented by the following general formula (vi-1).

[0913]

[0914] Among the general formula (vi-1), R vi1 , R vi2 , A vi1 , A vi2 and A vi3 is R in the above general formula (vi). vi1 , R vi2 , A vi1 , A vi2 and A vi3 Each represents the same meaning.

[0915] As for the compound represented by general formula (vi-1), it is preferable that it be a compound represented by the following general formulas (vi-1-1) to (vi-1-7).

[0916]

[0917] Among general formulas (vi-1-1) to (vi-1-7), R vi1 , R vi2 and S vi1 R in the above general formula (vi), each independently vi1 , R vi2 and S vi1 Each represents the same meaning.

[0918] 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-1-1.2).

[0919]

[0920] 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-1-2.6).

[0921]

[0922] Specific examples of compounds represented by the general formula (vi-1-3) include compounds represented by the following structural formulas (vi-1-3.1) to (vi-1-3.4).

[0923]

[0924] Specific examples of compounds represented by the general formula (vi-1-4) include compounds represented by the following structural formulas (vi-1-4.1) to (vi-1-4.5).

[0925]

[0926] Specific examples of compounds represented by the general formula (vi-1-5) include compounds represented by the following structural formulas (vi-1-5.1) to (vi-1-5.4).

[0927]

[0928] Specific examples of compounds represented by the general formula (vi-1-6) include compounds represented by the following structural formulas (vi-1-6.1) to (vi-1-6.5).

[0929]

[0930] Specific examples of compounds represented by the general formula (vi-1-7) include compounds represented by the following structural formula (vi-1-7.1).

[0931]

[0932] The types used in the liquid crystal composition of compounds represented by general formula (vi), general formula (vi-1), general formulas (vi-1-1) to (vi-1-7), structural formulas (vi-1-1.1) to (vi-1-1.2), structural formulas (vi-1-2.1) to (vi-1-2.6), structural formulas (vi-1-3.1) to (vi-1-3.4), structural formulas (vi-1-4.1) to (vi-1-4.5), structural formulas (vi-1-5.1) to (i-v1-5.4), structural formulas (vi-1-6.1) to (i-v1-6.5) or structural formula (vi-1-7.1) are 1 or 2 or more, preferably 1 to 10, preferably 1 to 5, and preferably 1 to 3.

[0933] The lower limit of the total content of a compound represented by general formula (vi), general formula (vi-1), general formula (vi-1-1) to (vi-1-7), structural formula (vi-1-1.1) to (vi-1-1.2), structural formula (vi-1-2.1) to (vi-1-2.6), structural formula (vi-1-3.1) to (vi-1-3.4), structural formula (vi-1-4.1) to (vi-1-4.5), structural formula (vi-1-5.1) to (i-v1-5.4), structural formula (vi-1-6.1) to (i-v1-6.5) or structural formula (vi-1-7.1) in 100 mass% of a liquid crystal composition is preferably 1 mass% or more, preferably 3 mass% or more, and preferably 5 mass% or more.

[0934] The upper limit of the total content of a compound represented by general formula (vi), general formula (vi-1), general formula (vi-1-1) to (vi-1-7), structural formula (vi-1-1.1) to (vi-1-1.2), structural formula (vi-1-2.1) to (vi-1-2.6), structural formula (vi-1-3.1) to (vi-1-3.4), structural formula (vi-1-4.1) to (vi-1-4.5), structural formula (vi-1-5.1) to (i-v1-5.4), structural formula (vi-1-6.1) to (i-v1-6.5) or structural formula (vi-1-7.1) in 100 mass% of a liquid crystal composition is preferably 35 mass% or less, preferably 30 mass% or less, and preferably 25 mass% or less.

[0935] The total content in 100 mass% of a liquid crystal composition of a compound represented by general formula (vi), general formula (vi-1), general formulas (vi-1-1)–(vi-1-7), structural formulas (vi-1-1.1)–(vi-1-1.2), structural formulas (vi-1-2.1)–(vi-1-2.6), structural formulas (vi-1-3.1)–(vi-1-3.4), structural formulas (vi-1-4.1)–(vi-1-4.5), structural formulas (vi-1-5.1)–(i-v1-5.4), structural formulas (vi-1-6.1)–(i-v1-6.5) or structural formula (vi-1-7.1) is, in relation to solubility, Δn and / or Δε r In terms of, it is preferable that the amount be 1 to 35 mass%, 3 to 30 mass%, and 5 to 25 mass%.

[0936] Compounds represented by general formula (vi) (including sub-concepts) can be synthesized using known synthesis methods.

[0937] The liquid crystal composition according to the present invention comprises Δn and / or Δε r In this regard, one or more compounds represented by the following general formula (vii) having at least one -C≡C- and -N=N- as a linker may also be included.

[0938]

[0939] Among the general formula (vii), R vii1 and R vii2 Each represents, independently, a halogen atom, a cyano group, and an alkyl group having 1 to 20 carbon atoms.

[0940] Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0941] The alkyl group having 1 to 20 carbon atoms is a straight-chain, branched, or cyclic alkyl group, and it is preferably a straight-chain alkyl group.

[0942] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.

[0943] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0944] In addition, one or more -CH2-CH2- groups among the alkyl groups may each be independently substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0945] In addition, one or more -CH2-CH2-CH2- among the alkyl groups may each be independently substituted with -O-CO-O-.

[0946] In addition, one or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[0947] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0948] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[0949] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[0950] For example, R vii1 and R vii2 One -CH2- in the alkyl group can be substituted with -O- to form an alkoxy group having 1 to 19 carbon atoms.

[0951] The alkoxy group is a linear, branched, or cyclic alkoxy group, and it is preferable that it be a linear alkoxy group.

[0952] The number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0953] Also, R vii1 and R vii2 One -CH2- in the alkyl group is substituted with -S-, thereby forming a thioalkoxy group (alkylsulfanyl group, alkylthio group) having 1 to 19 carbon atoms.

[0954] The thioalkoxy group is a linear, branched, or cyclic thioalkoxy group, and it is preferable that it be a linear thioalkoxy group.

[0955] The number of carbon atoms in the thioalkoxy group is preferably 2 to 10, preferably 2 to 6.

[0956] Also, R vii1 and R vii2 One or more -CH2-CH2- groups among the alkyl groups can be substituted with -CH=CH- to represent an alkenyl group having 2 to 20 carbon atoms.

[0957] The alkenyl group is a straight-chain, branched, or cyclic alkenyl group, and it is preferable that it be a straight-chain alkenyl group.

[0958] The number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.

[0959] Also, R vii1and R vii2 One or more -CH2-CH2- groups among the alkyl groups can be substituted with -C≡C- to represent an alkynyl group having 2 to 20 carbon atoms.

[0960] The alkynyl group is a straight, branched, or cyclic alkynyl group, and it is preferable that it be a straight alkynyl group.

[0961] The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.

[0962] Also, R vii1 and R vii2 One -CH2- in the alkyl group is substituted with -O-, and one or more -CH2-CH2- are substituted with -CH=CH-, thereby forming an alkenyloxy group having 2 to 19 carbon atoms.

[0963] The alkenyloxy group is a straight-chain, branched, or cyclic alkenyloxy group, and it is preferable that it be a straight-chain alkenyloxy group.

[0964] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6.

[0965] Also, R vii1 and R vii2 alkyl halide groups having 1 to 20 carbon atoms can be represented by substituting one or more hydrogen atoms in the alkyl group with a halogen atom.

[0966] The alkyl halide group is a straight-chain, branched, or cyclic alkyl halide group, and it is preferable that it be a straight-chain alkyl halide group.

[0967] The number of carbon atoms in the alkyl halide group is preferably 2 to 10, preferably 2 to 6.

[0968] R vii1 and R vii2A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by substituting one -CH2- in the alkyl group with -O- and substituting one or more hydrogen atoms in the alkyl group with a halogen atom.

[0969] The halogenated alkoxy group is a straight-chain, branched, or cyclic alkoxy group, and it is preferable that it be a straight-chain alkoxy group.

[0970] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.

[0971] R vii1 and R vii2 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) in the above include the formula (R vii1 / 2 -1)~(R vii1 / 2 Examples include the one indicated by -36).

[0972]

[0973] Equation (R vii1 / 2 -1)~(R vii1 / 2 -36) Among them, sunspots are A vii1 or A vii3 It represents the connection loss to.

[0974] R vii1 When the reliability of the entire liquid crystal composition is important, it is preferable that the alkyl group has 1 to 12 carbon atoms, and when the reduction of the viscosity of the entire liquid crystal composition is important, it is preferable that the alkenyl group has 2 to 8 carbon atoms.

[0975] Also, R vii1 When the bonded ring structure is a phenyl group (aromatic), a straight-chain alkyl group having 1 to 5 carbon atoms, a straight-chain alkoxy group having 1 to 4 carbon atoms, and an alkenyl group having 4 to 5 carbon atoms are preferred, and R vii1In the case where the ring structure being bonded is a saturated ring structure such as cyclohexane, pyran, and dioxane, a straight-chain alkyl group having 1 to 5 carbon atoms, a straight-chain alkoxy group having 1 to 4 carbon atoms, and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred.

[0976] Also, R vii1 In order to stabilize the nematic phase, it is desirable that the total of carbon atoms and, if present, oxygen atoms be 5 or less, and that it be a straight chain.

[0977] R vii2 In the case where the compound represented by general formula (vii) is a so-called p-type compound with positive Δε, it is preferable that the compound be a fluorine atom, a cyano group, a trifluoromethyl group, or a trifluoromethoxy group, and a fluorine atom or a cyano group is preferred.

[0978] If the compound represented by general formula (vii) is a so-called nonpolar compound with Δε being nearly 0, then R vii2 is, R vii1 It expresses the same meaning as, R vii2 and R vii1 It may be the same or different.

[0979] Also, R vii1 / 2 As for solubility, a straight-chain alkyl group having 2 to 6 carbon atoms is preferred.

[0980] Among general formulas (vii), A vii1 , A vii2 and A vii3 Each independently, the following units (a), (b), and (c):

[0981] (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- in this group may be substituted with -O-)

[0982] (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[0983] (c) Naphthalene-1,4-diyl group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (one -CH= or two or more non-adjacent -CH= present in the naphthalene-1,4-diyl group, naphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with -N=.)

[0984] It represents a group selected from the group consisting of

[0985] In addition, one or more hydrogen atoms among the above groups (a), (b) and (c) may each be independently substituted with a halogen atom, a cyano group, or an alkyl group having 1 to 6 carbon atoms.

[0986] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms, and fluorine atoms are preferred from the perspective of stability and safety.

[0987] A vii1 , A vii2 and / or A vii3 In each case, independently, to improve the response speed, it is preferable that the group (a) be an aliphatic divalent cyclic group, and when it is required to increase Δn, it is preferable that the group (b) or group (c) be an aromatic divalent cyclic group, and independently, the following structure:

[0988]

[0989] (R represents an alkyl group having 1 to 6 carbon atoms.)

[0990] It is preferable to represent any one of the following, and it is preferable to represent any one of the 1,4-phenylene group, naphthalene-2,6-diyl group and tetrahydronaphthalene-2,6-diyl group, and one or more hydrogen atoms among the 1,4-phenylene group, naphthalene-2,6-diyl group and tetrahydronaphthalene-2,6-diyl group may each be independently substituted by a fluorine atom or an alkyl group having 1 to 6 carbon atoms.

[0991] Especially A vii1 The following (d)~(f):

[0992]

[0993] (X vii1 and X vii2 Each represents, independently, a hydrogen atom or a fluorine atom.

[0994] It is desirable to represent a group selected from the group consisting of , in terms of Δn improvement.

[0995] In addition, from the perspective of compatibility with other liquid crystal compounds, it is desirable to represent group (f).

[0996] In addition, to increase compatibility with other liquid crystal compositions, A vii1 , A vii2 and / or A vii3 It is preferable that at least one of them represents a 1,4-phenylene group substituted by an alkyl group having 1 to 6 carbon atoms, and it is more preferable that it represents a 1,4-phenylene group substituted by an ethyl group.

[0997] A, which is a ring structure in one molecule of the compound represented by the general formula (vii) in the present invention vii1 , A vii2 and / or A vii3 It is preferable to have a total of 1 to 5 fluorine atoms, and more preferable to have 1 to 4.

[0998] The compound represented by the above general formula (vii) is preferably a compound represented by the following general formulas (vii-1) to (vii-3).

[0999]

[1000] (Among the above general formulas (vii-1)) to (vii-3), R vii1 , R vii2 , A vii2 and A vii3 is R in the above general formula (vii). vii1 , R vii2 , A vii2 and A vii3 Each has the same meaning, and the desirable energy and desirable number are also the same.

[1001] Among the above general formulas (vii-1) to (vii-3), X vii1 and X vii2 Each represents, independently, a hydrogen atom or a fluorine atom.

[1002] Specific examples of compounds represented by the general formula (vii-1) include compounds represented by the following structural formulas (vii-1.1) to (vii-1.74).

[1003]

[1004]

[1005]

[1006]

[1007]

[1008] Specific examples of compounds represented by general formula (vii-2) include compounds represented by the following structural formulas (vii-2.1) to (vii-2.22).

[1009]

[1010] In the formula, X represents, respectively, a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 6 carbon atoms.

[1011]

[1012] Among the compounds represented by the above structural formulas (vii-1.1) to (vii-1.74) and (vii-2.1) to (vii-2.22), structural formulas (vii-1.1) to (vii-1.20) and structural formulas (vii-2.17) to (vii-2.22) are preferred.

[1013] The types used in the liquid crystal composition of compounds represented by general formula (vii), general formula (vii-1) to general formula (vii-3), structural formula (vii-1.1) to (vii-1.74) or structural formula (vii-2.1) to (vii-2.22) are 1 or 2 or more, preferably 1 to 10 types, preferably 1 to 5 types.

[1014] The lower limit of the total content of compounds represented by general formula (vii), general formula (vii-1) to general formula (vii-3), structural formula (vii-1.1) to (vii-1.74) or structural formula (vii-2.1) to (vii-2.22) in 100 mass% of the liquid crystal composition is preferably 5 mass%, preferably 10 mass%, and preferably 15 mass%.

[1015] The upper limit of the total content of compounds represented by general formula (vii), general formula (vii-1) to general formula (vii-3), structural formula (vii-1.1) to (vii-1.74) or structural formula (vii-2.1) to (vii-2.22) in 100 mass% of the liquid crystal composition is preferably 40 mass%, preferably 35 mass%, and preferably 30 mass%.

[1016] The total content in 100 mass% of the liquid crystal composition of compounds represented by general formula (vii), general formulas (vii-1) to (vii-3), structural formulas (vii-1.1) to (vii-1.74) or structural formulas (vii-2.1) to (vii-2.22) is, solubility, Δn and / or Δε rIn terms of, it is preferable to have 5 to 40 mass%, 10 to 35 mass%, and 15 to 30 mass%.

[1017] Compounds represented by general formula (vii) (including sub-concepts) can be prepared by known methods.

[1018] The liquid crystal composition according to the present invention may additionally include one or more compounds represented by the following general formulas (np-1) to (np-3) in terms of solubility.

[1019]

[1020] Among the general formulas (np-1) to (np-3), R npi and R npii Each represents, independently, any one of an alkyl group having 1 to 20 carbon atoms or a halogen atom.

[1021] The alkyl group having 1 to 20 carbon atoms is a straight-chain, branched, or cyclic alkyl group, and it is preferably a straight-chain alkyl group.

[1022] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.

[1023] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-.

[1024] In addition, one or more -CH2-CH2- groups among the alkyl groups may each be independently substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF- and / or -C≡C-.

[1025] In addition, one or more -CH2-CH2-CH2- among the alkyl groups may each be independently substituted with -O-CO-O-.

[1026] In addition, one or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[1027] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[1028] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[1029] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[1030] For example, R npi and R npii One -CH2- in the alkyl group can be substituted with -O- to form an alkoxy group having 1 to 19 carbon atoms.

[1031] The alkoxy group is a linear, branched, or cyclic alkoxy group, and it is preferable that it be a linear alkoxy group.

[1032] The number of carbon atoms in the alkoxy group is preferably 2 to 10, preferably 2 to 6.

[1033] Also, R npi and R npii One -CH2- in the alkyl group is substituted with -S-, thereby forming a thioalkoxy group (alkylsulfanyl group, alkylthio group) having 1 to 19 carbon atoms.

[1034] The thioalkoxy group is a linear, branched, or cyclic thioalkoxy group, and it is preferable that it be a linear thioalkoxy group.

[1035] The number of carbon atoms in the thioalkoxy group is preferably 1 to 10, preferably 1 to 6.

[1036] Also, R npi and R npiiOne or more -CH2-CH2- groups among the alkyl groups can be substituted with -CH=CH- to represent an alkenyl group having 2 to 20 carbon atoms.

[1037] The alkenyl group is a straight-chain, branched, or cyclic alkenyl group, and it is preferable that it be a straight-chain alkenyl group.

[1038] The number of carbon atoms in the alkenyl group is preferably 2 to 10, preferably 2 to 6.

[1039] Also, R npi and R npii One or more -CH2-CH2- groups among the alkyl groups can be substituted with -C≡C- to represent an alkynyl group having 2 to 20 carbon atoms.

[1040] The alkynyl group is a straight, branched, or cyclic alkynyl group, and it is preferable that it be a straight alkynyl group.

[1041] The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6.

[1042] Also, R npi and R npii One -CH2- in the alkyl group is substituted with -O-, and one or more -CH2-CH2- are substituted with -CH=CH-, thereby forming an alkenyloxy group having 2 to 19 carbon atoms.

[1043] The alkenyloxy group is a straight-chain, branched, or cyclic alkenyloxy group, and it is preferable that it be a straight-chain alkenyloxy group.

[1044] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, preferably 2 to 6.

[1045] Also, R npi and R npiialkyl halide groups having 1 to 20 carbon atoms can be represented by substituting one or more hydrogen atoms in the alkyl group with a halogen atom.

[1046] The alkyl halide group is a straight-chain, branched, or cyclic alkyl halide group, and it is preferable that it be a straight-chain alkyl halide group.

[1047] The number of carbon atoms in the alkyl halide group is preferably 2 to 10, preferably 2 to 6.

[1048] R npi and R npii A halogenated alkoxy group having 1 to 19 carbon atoms can be represented by substituting one -CH2- in the alkyl group with -O- and substituting one or more hydrogen atoms in the alkyl group with a halogen atom.

[1049] The halogenated alkoxy group is a straight-chain, branched, or cyclic alkoxy group, and it is preferable that it be a straight-chain alkoxy group.

[1050] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, preferably 2 to 6.

[1051] R npi and R npii Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) in the above include the formula (R npi / ii -1)~(R npi / ii Examples include the one indicated by -36).

[1052]

[1053] Equation (R npi / ii -1)~(R npi / ii -36) Among them, sunspots indicate a loss of connection to ring A, ring B, ring C, or ring D.

[1054] R npi and R npiiExamples of halogen atoms in this include fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc.

[1055] Among general formulas (np-1) to (np-3), ring A, ring B, ring C, and ring D are each independently the following groups (a), (b), (c), and (d):

[1056] (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- in this group may be substituted with -O-)

[1057] (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.)

[1058] (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (one -CH= or two or more non-adjacent -CH= present in the naphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with -N=.)

[1059] (d) 1,4-cyclohexenylene group, 1,3-dioxane-trans-2,5-diyl group, pyrimidine-2,5-diyl group or pyridine-2,5-diyl group

[1060] It represents a group selected from the group consisting of

[1061] One or more hydrogen atoms among the above rings A, B, C, and D are, respectively, independently substituent S npi1 It may be substituted by.

[1062] Substituent S npi1 It represents any one of silver, a halogen atom, a cyano group, or an alkyl group having 1 to 20 carbon atoms.

[1063] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms, and fluorine atoms are preferred from the perspective of stability and safety.

[1064] The alkyl group having 1 to 20 carbon atoms is a straight-chain, branched, or cyclic alkyl group, and it is preferably a straight-chain alkyl group.

[1065] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, preferably 2 to 6.

[1066] One or more -CH2- groups in the alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-.

[1067] In addition, one or more -CH2-CH2- groups among the alkyl groups may each be independently substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[1068] One or more -CH2-CH2-CH2- groups among the alkyl groups may each be independently substituted with -O-CO-O-.

[1069] In addition, one or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom.

[1070] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[1071] However, in cases where the alkyl group is substituted by a specific group, there is no direct bonding between oxygen atoms.

[1072] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[1073] Substituent Snpi1 As, V th From the perspective of, halogen atoms are desirable, and fluorine atoms are desirable.

[1074] Also, substituent S npi1 In cases where there are multiple instances, they may be identical or different.

[1075] Substituent S in ring A npi1 As for the substitution position, it is preferable to use the following formula (A-SP-1).

[1076]

[1077] In formula (A-SP-1), white spots are R npi Represents the combined loss of the furnace, and the sunspot is Z npi It represents the joint hand of the row.

[1078] More specifically, ring A preferably represents any one of the following formulas (A-1) to (A-3).

[1079]

[1080] In formulas (A-1) to (A-3), the white point is R npi Represents the combined loss of the furnace, and the sunspot is Z npi It represents the joint hand of the row.

[1081] More specifically, ring B preferably represents any one of the following formulas (B-1) to (B-2).

[1082]

[1083] In formulas (B-1) to (B-2), the white point is Z npi It indicates the combined loss of the furnace, and the sunspot is R npii or Z npii It represents the joint hand of the row.

[1084] More specifically, ring C preferably represents any one of the following formulas (C-1) to (C-2).

[1085]

[1086] In equations (C-1) to (C-2), the white point is Z npii It indicates the combined loss of the furnace, and the sunspot is R npii or Z npiii It represents the joint hand of the row.

[1087] Among the general formulas (np-1) to (np-3), Z npi , Z npii and Z npiii Each represents, independently, any one of a single bond and an alkylene group having 1 to 20 carbon atoms.

[1088] One or more -CH2- groups in the alkylene group may each be independently substituted with -O-.

[1089] In addition, one or more -CH2-CH2- groups in the alkylene group may each be independently substituted with -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[1090] In addition, one or more -CH2-CH2-CH2- among the alkyl groups may each be independently substituted with -O-CO-O-.

[1091] However, in the case where an alkyl group having 1 to 10 carbon atoms is substituted by a specific group, there is no direct bonding between oxygen atoms.

[1092] In addition, from the perspective of compound stability, it is desirable that there are no cases where sulfur atoms and / or oxygen atoms are directly bonded to each other.

[1093] Specific examples of alkylene groups having 1 to 20 carbon atoms (including substituted ones) include the formula (Z npi / ii / iii -1)~(Z npi / ii / iii Examples include the one indicated by -24.

[1094]

[1095] Equation (Z npi / ii / iii -1)~(Z npi / ii / iii -24) Among them, white spots indicate a loss of connection to Ring A, Ring B, or Ring C, and black spots indicate a loss of connection to Ring B, Ring C, or Ring D.

[1096] Δn and / or Δε r From the perspective of, Z npi , Z npii and Z npiii It is preferable that each independently represent one of a single bond, -C≡C- and -CO-O-.

[1097] However, regarding compounds represented by general formulas (np-1) to (np-3), compounds represented by general formulas (vi) and (vii) (including sub-concepts) are excluded.

[1098] As for the compound represented by general formula (np-2), it is preferable that it be a compound represented by the following general formulas (np-2-1) to (np-2-2).

[1099]

[1100] Among the general formulas (np-2-1) to (np-2-2), R npi , R npii and S npi is R in the above general formulas (np-1) to (np-3). npi , R npii and S npi Each represents the same meaning.

[1101] Specific examples of compounds represented by the general formula (np-2-1) include compounds represented by the following structural formula (np-2-1.1).

[1102]

[1103] 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).

[1104]

[1105] The types used in the liquid crystal composition of compounds represented by general formulas (np-1) to (np-3), general formulas (np-2-1) to (np-2-2), structural formula (np-2-1.1) or structural formulas (np-2-2.1) to (np-2-2.5) are 1 or 2 or more, preferably 1 to 10 types, preferably 1 to 8 types, preferably 1 to 6 types, preferably 1 to 4 types, and preferably 1 to 2 types.

[1106] The lower limit of the total content of compounds represented by general formulas (np-1) to (np-3), general formulas (np-2-1) to (np-2-2), structural formula (np-2-1.1) or structural formulas (np-2-2.1) to (np-2-2.5) in 100 mass% of the liquid crystal composition is preferably 1 mass%, preferably 5 mass%, and preferably 10 mass%.

[1107] The upper limit of the total content of compounds represented by general formulas (np-1) to (np-3), general formulas (np-2-1) to (np-2-2), structural formula (np-2-1.1) or structural formulas (np-2-2.1) to (np-2-2.5) in 100 mass% of the liquid crystal composition is preferably 50 mass%, preferably 40 mass%, and preferably 30 mass%.

[1108] The total content in 100 mass% of a liquid crystal composition of compounds represented by general formulas (np-1) to (np-3), general formulas (np-2-1) to (np-2-2), structural formula (np-2-1.1), or structural formulas (np-2-2.1) to (np-2-2.5) is, solubility, Δn and / or Δε r In terms of, it is preferable to have 1 to 50 mass%, 5 to 40 mass%, and 10 to 30 mass%.

[1109] Compounds represented by general formulas (np-1) to (np-3), general formulas (np-2-1) to (np-2-2), structural formula (np-2-1.1), or structural formulas (np-2-2.1) to (np-2-2.5) can be prepared by known methods.

[1110] (Liquid crystal composition)

[1111] The liquid crystal composition according to the present invention can be prepared, for example, by mixing a compound represented by the general formula (i) described above, and, if necessary, other compounds and additives described above.

[1112] Examples of additives include stabilizers, pigment compounds, polymerizable compounds, etc.

[1113] Examples of stabilizers include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, hindered phenols, hindered amines, etc.

[1114] Examples of hindered phenols include hindered phenolic antioxidants represented by the following structural formulas (XX-1) to (XX-3).

[1115]

[1116] Examples of hindered amines include hindered amine-based light stabilizers represented by the following structural formulas (YY-1) to (YY-2).

[1117]

[1118] In the case of using a stabilizer, the total content of the stabilizer in 100 mass% of the liquid crystal composition is preferably 0.005 to 1 mass%, preferably 0.02 to 0.50 mass%, and preferably 0.03 to 0.35 mass%.

[1119] As a combination of compounds used in the liquid crystal composition, solubility, Δn and / or Δε rIn terms of, a combination of a compound represented by general formula (i) (including sub-concepts) and a compound represented by general formula (ii) (including sub-concepts), a combination of a compound represented by general formula (i) (including sub-concepts) and a compound represented by general formula (ii) (including sub-concepts) and a compound represented by general formula (vi) (including sub-concepts), a combination of a compound represented by general formula (i) (including sub-concepts) and a compound represented by general formula (ii) (including sub-concepts) and a compound represented by general formula (vi) (including sub-concepts) is preferred.

[1120] <Characteristic Values ​​of Liquid Crystal Composition>

[1121] Liquid crystal upper temperature limit (T ni ) is the temperature at which the liquid crystal composition transitions from the nematic phase to the isotropic phase.

[1122] T ni The liquid crystal composition is measured by preparing a slide held between a slide glass and a cover glass, and observing it under a polarizing microscope while heating it on a hot stage.

[1123] In addition, it can also be measured by differential scanning calorimetry (DSC).

[1124] The unit used is "°C".

[1125] T ni The higher the value, the more the nematic phase can be maintained even at high temperatures, and the wider the operating temperature range can be.

[1126] Upper limit temperature of the liquid crystal phase of the liquid crystal composition according to the present invention (T ni The external temperature of the liquid crystal display element can be controlled, and depending on whether it is used indoors or in a vehicle, or outdoors, it can be appropriately set. In terms of the driving temperature range, it is preferable that it be 100°C or higher, 100°C to 200°C, and 110°C to 190°C.

[1127] Liquid crystal lower limit temperature (T →N ) is the temperature at which a liquid crystal composition transitions from another phase (glass, smectic phase, crystalline phase) to a nematic phase.

[1128] T →N The liquid crystal composition is filled into a glass capillary, immersed in a refrigerant at -70°C to transition the liquid crystal composition to another phase, and measured by observing while raising the temperature.

[1129] In addition, it can also be measured by differential scanning calorimetry (DSC).

[1130] The unit used is "°C".

[1131] T →N The lower this value, the more the nematic phase can be maintained even at low temperatures, allowing for a wider operating temperature range.

[1132] Lower liquid crystal phase temperature (T) of the liquid crystal composition according to the present invention →N In terms of the operating temperature range, it is preferable that it be 10℃ or lower, -70 to 0℃, and -40 to -5℃.

[1133] Δn (refractive index anisotropy) corresponds to Δn in the near-infrared region used as an optical sensor described later.

[1134] As Δn increases, the phase modulation power of the light of the target wavelength increases, making it particularly suitable for optical sensors.

[1135] Δn at 25℃ and 589nm is the ideal light refractive index (n) of the liquid crystal composition using an Abbe refractometer. e ) and refractive index of the normal light (n o The difference of )(n e -n o Obtained from ).

[1136] In addition, Δn can also be obtained from the phase difference measuring device.

[1137] Between the phase difference Re, the thickness d of the liquid crystal layer, and Δn, the relationship Δn=Re / d holds.

[1138] A liquid crystal composition is injected into a glass cell having a polyimide alignment film that has undergone anti-parallel rubbing treatment and has a cell gap (d) of about 3.0 μm, and the Re in the plane is measured using a phase difference film / optical material inspection device RETS-100 (manufactured by Otsuka Electronics Co., Ltd.).

[1139] Measurements are performed under conditions of a temperature of 25℃ and 589nm.

[1140] There are no units.

[1141] Δn of the liquid crystal composition according to the present invention at 25°C and 589 nm is preferably 0.30 or higher, preferably 0.30 to 0.60, preferably 0.35 to 0.55, and preferably 0.38 to 0.50.

[1142] The rotational viscosity (γ1) is the viscosity related to the rotation of liquid crystal molecules.

[1143] γ1 can be measured by filling a glass cell with a liquid crystal composition with a cell gap of about 10 μm and using LCM-2 (manufactured by Toyo Technica).

[1144] A horizontally oriented cell is used when the liquid crystal composition has positive dielectric anisotropy, and a vertically oriented cell is used when the liquid crystal composition has negative dielectric anisotropy.

[1145] Measurements are performed at a temperature of 25℃.

[1146] The unit used is mPa·s.

[1147] Since the response speed of the liquid crystal composition increases as γ1 becomes smaller, it is suitable for any liquid crystal display device.

[1148] The rotational viscosity (γ1) of the liquid crystal composition according to the present invention at 25°C is preferably 150 to 2000 mPa·s, preferably 200 to 1800 mPa·s, and preferably 250 to 1500 mPa·s in terms of response speed.

[1149] Threshold voltage (V th ) depends on the driving voltage of the liquid crystal composition.

[1150] V th It can be determined from the transmittance when a liquid crystal composition is filled into a TN cell with an 8.3 μm gap and a voltage is applied.

[1151] Measurements are performed at a temperature of 25℃.

[1152] The unit used is "V".

[1153] V th The lower the value, the lower the voltage it can operate.

[1154] V at 25°C of the liquid crystal composition according to the present invention th In terms of driving voltage, it is preferable that it be 3.0V or less, 0.3 to 3.0V, 0.5 to 2.7V, 0.7 to 2.5V, 0.9 to 2.3V, 1.1 to 2.1V, and 1.3 to 2.0V.

[1155] Permittivity anisotropy in the high-frequency range is particularly suitable for antenna applications because a higher value increases the phase modulation power for radio waves in the target frequency range.

[1156] In addition, for antenna applications, it is suitable because the smaller the dielectric tangent in the high-frequency range, the smaller the energy loss in the target frequency range.

[1157] In the liquid crystal composition according to the present invention, the dielectric anisotropy Δε at 10 GHz, representing the characteristics of the high-frequency region, r and the average value of the genetic tangent tanδ isoMeasured.

[1158] Δε r =(ε r∥ -ε r⊥ ) and, tanδ iso =(2ε r⊥ tanδ ⊥ +ε r∥ tanδ ∥ ) / (2ε r⊥ +ε r∥ )am.

[1159] Here, “εr” is the dielectric constant and “tanδ” is the dielectric tangent, and the subscript “∥” indicates a component parallel to the orientation direction of the liquid crystal and “⊥” indicates a component perpendicular to the orientation direction of the liquid crystal.

[1160] Δε r and tanδ iso It can be measured by the following methods.

[1161] First, the liquid crystal composition is introduced into a polytetrafluoroethylene (PTFE) capillary tube.

[1162] The capillary tube used here has an inner radius of 0.80 mm and an outer radius of 0.835 mm, and an effective length of 4.0 cm.

[1163] A capillary containing a liquid crystal composition is introduced into the center of a cavity resonator (manufactured by EM Laboratory Co., Ltd.) having a resonance frequency of 10 GHz.

[1164] This cavity resonator has an external shape with a diameter of 30 mm and a width of 26 mm.

[1165] Then, a signal is input, and the result of the output signal is recorded using a network analyzer (manufactured by Keysight Technologies, Inc.).

[1166] By utilizing the difference between the resonance frequency of a PTFE capillary without a liquid crystal composition and the resonance frequency of a PTFE capillary with a liquid crystal composition, the dielectric constant (ε) at 10 GHz r Determine the loss angle (δ).

[1167] And, the tangent of δ obtained is the genetic tangent (tanδ).

[1168] In addition, the resonance frequency, etc., using a PTFE capillary encapsulated with a liquid crystal composition is obtained by controlling the orientation of the liquid crystal molecules, using the values ​​of characteristic components perpendicular to the orientation direction of the liquid crystal molecules and characteristic components parallel to it.

[1169] A magnetic field from a permanent magnet or an electromagnet is used to align liquid crystal molecules in a direction perpendicular to the PTFE capillary (perpendicular to the effective length direction) or in a parallel direction (parallel to the effective length direction).

[1170] For example, the magnetic field strength near the center is 0.23 Tesla, with a distance between poles of 45 mm.

[1171] Desired characteristic components are obtained by rotating a PTFE capillary containing a liquid crystal composition parallel or perpendicular to a magnetic field.

[1172] Measurements are performed at a temperature of 25℃.

[1173] Δε r and tanδ iso None of them have units.

[1174] Δε of the liquid crystal composition according to the present invention at 25°C r It is preferable that it be larger than, but from the perspective of phase modulation power in the GHz range, it is preferable that it be 0.90 or higher, 0.90 to 1.40, 0.95 to 1.40, and 1.00 to 1.40.

[1175] tanδ at 25°C of the liquid crystal composition according to the present invention isoIt is preferable that it be smaller, but from the perspective of loss in the GHz range, it is preferable that it be 0.025 or less, 0.001 to 0.025, 0.003 to 0.020, 0.005 to 0.017, 0.007 to 0.015, 0.008 to 0.013, and 0.009 to 0.012.

[1176] (Liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices and antennas)

[1177] Hereinafter, a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using a liquid crystal composition according to the present invention will be described.

[1178] The liquid crystal display element according to the present invention is characterized by using the liquid crystal composition described above, and preferably drives in an active matrix method or a passive matrix method.

[1179] In addition, the liquid crystal display element according to the present invention is preferably a liquid crystal display element that reversibly switches the dielectric constant by reversibly changing the orientation direction of the liquid crystal molecules of the liquid crystal composition described above.

[1180] The sensor according to the present invention is characterized by using the liquid crystal composition described above, and examples thereof include a distance measuring sensor using electromagnetic waves, visible light, or infrared light; an infrared sensor using a temperature change; a temperature sensor using a change in the wavelength of reflected light due to a change in the pitch of a cholesteric liquid crystal; a pressure sensor using a change in the wavelength of reflected light; an ultraviolet sensor using a change in the wavelength of reflected light due to a change in composition; an electric sensor using a temperature change due to voltage or current; a radiation sensor using a temperature change accompanied by a track of radiation particles; an ultrasonic sensor using a change in the arrangement of liquid crystal molecules due to mechanical vibration of ultrasound; and an electromagnetic sensor using a change in the wavelength of reflected light due to a temperature change or a change in the arrangement of liquid crystal molecules due to an electric field.

[1181] As for the distance measuring sensor, it is preferable to use a LiDAR (Light Detection And Ranging) sensor that utilizes a light source.

[1182] For LiDAR, applications for satellites, aircraft, unmanned aerial vehicles (drones), automobiles, railways, and ships are preferred.

[1183] For automobiles, it is particularly desirable for autonomous vehicles.

[1184] The light source is preferably an LED or a laser, and preferably a laser.

[1185] It is preferable that the light used in LiDAR be infrared light, and the wavelength be 800 to 2000 nm.

[1186] In particular, an infrared laser with a wavelength of 905 nm or 1550 nm is preferred.

[1187] When the cost of the photodetector used or sensitivity in all weather conditions is important, a 905nm infrared laser is preferred, and when safety regarding human vision is important, a 1550nm infrared laser is preferred.

[1188] The liquid crystal composition according to the present invention can provide a sensor with excellent detection sensitivity and large phase modulation power in the visible light, infrared light, and electromagnetic wave regions, in that it exhibits a high Δn.

[1189] A liquid crystal lens according to the present invention is characterized by using the liquid crystal composition described above, and, for example, as one embodiment thereof, has a first transparent electrode layer, a second transparent electrode layer, a liquid crystal layer comprising the liquid crystal composition described above installed between the first transparent electrode layer and the second transparent electrode layer, an insulating layer installed between the second transparent electrode layer and the liquid crystal layer, and a high resistance layer installed between the insulating layer and the liquid crystal layer.

[1190] The liquid crystal lens according to the present invention is used, for example, as a 2D / 3D switching lens, a lens for focusing a camera, etc.

[1191] The optical communication device according to the present invention is characterized by using the liquid crystal composition described above, and as an example, as one embodiment thereof, an LCOS (Liquid crystal on silicon) may be provided having a liquid crystal layer in which liquid crystals constituting each of a plurality of pixels are arranged in a two-dimensional shape on a reflective layer (electrode).

[1192] The optical communication device according to the present invention is used, for example, as a spatial phase modulator.

[1193] The antenna according to the present invention is characterized by using the liquid crystal composition described above.

[1194] More specifically, the antenna according to the present invention comprises a first substrate having a plurality of slots, a second substrate facing the first substrate and having a feed portion installed thereon, a first dielectric layer installed between the first substrate and the second substrate, a plurality of patch electrodes arranged corresponding to the plurality of slots, a third substrate having the patch electrodes installed thereon, and a liquid crystal layer installed between the first substrate and the third substrate, wherein the liquid crystal layer contains the liquid crystal composition described above.

[1195] As a liquid crystal composition, by using a liquid crystal composition comprising one or more compounds represented by general formula (i) having an ethylene group (-C≡C-) and an isothiocyanate group (-NCS), T ni g is high, Δn is large, and V th is low, and Δε r This is large, and tanδ iso Since it is small and has good preservation at low temperatures, it is possible to provide an antenna with high reliability against external stimuli such as heat.

[1196] By doing so, it is possible to provide an antenna that enables greater phase control for microwave or millimeter wave electromagnetic waves.

[1197] Hereinafter, an antenna according to the present invention will be described using the drawings.

[1198] As shown in FIG. 1, an antenna assembly (11) in which four antenna units (1) are connected is mounted on the roof of a vehicle (automobile) (2). The antenna unit (1) is a planar antenna, and since it is mounted on the roof, the antenna unit (1) is always oriented toward the direction of the communication satellite. By doing so, satellite communication capable of transmitting and receiving in both directions can be performed.

[1199] Additionally, the term "antenna" in this specification includes an antenna unit (1) or an antenna assembly (11) formed by connecting multiple antenna units (1).

[1200] The antenna according to the present invention preferably operates at a Ka-band frequency, a K-band frequency, or a Ku-band frequency used for satellite communication.

[1201] Next, an example of an embodiment of the components of the antenna unit (1) is shown in FIG. 2. FIG. 2 is an exploded view of the antenna unit (1) shown in FIG. 1. Specifically, the antenna unit (1) is configured to have an antenna body (10), a control panel (4) for controlling the antenna body (10), a case (3) having a recess capable of accommodating the antenna body (10) and the control panel (4), and an upper cover (5) for sealing the case (3).

[1202] A transmitter and / or receiver are installed in the control panel (4). The transmitter has a mechanism for receiving information from a signal source, such as data like voice or image, through source encoding processing, for example, voice encoding or image encoding, and then correcting errors through transmission path encoding processing, and then modulating and transmitting it as a radio wave. Meanwhile, the receiver has a mechanism for modulating incoming radio waves, correcting errors through transmission path decoding processing, and then converting them into information such as data like voice or image through source decoding processing, for example, voice decoding or image decoding. In addition, the control panel (4) is composed of a known microcomputer, such as a CPU, RAM, and ROM, and comprehensively controls the operation of each part of the antenna body (1), transmitter, and / or receiver. In the CPU or ROM provided by the control panel (4), various programs stored in advance are read into RAM and executed, thereby performing a predetermined process. The control panel (4) is equipped with functions such as a memory unit that stores various setting information or control programs, a calculation unit that performs various calculations regarding the amount of voltage and voltage direction applied to the liquid crystal layer within the antenna body (1), various calculations regarding the transmission of radio waves and / or various calculations regarding the reception of radio waves, and a detection unit that performs detection of received or transmitted radio waves or detection of the voltage applied to the liquid crystal layer.

[1203] In FIG. 2, as an example of a case (3) capable of accommodating a disc-shaped antenna body (1), a hexagonal prism-shaped case (3) and an upper cover (5) are described. Depending on the shape of the antenna body (1), the case (3) and the upper cover (5) can be appropriately changed to known shapes such as a cylindrical shape, an octagonal prism shape, or a triangular prism shape.

[1204] To explain the configuration of the antenna body (10), the following description is made using FIGS. 3 to 10. FIG. 3 is a schematic diagram showing the components of the antenna body (10) disassembled.

[1205] As shown in FIG. 3, the antenna body (10) is equipped with a slot array section (6) and a patch array section (7). In the slot array section (6), a plurality of slots (notch sections) (8) are formed on the surface of a disc-shaped conductor (P), and a feed section (12) is installed inside the center of the slot array section (6). In addition, in the patch array section (7), a plurality of rectangular patches (9) with length (L) and width (W) are formed on the disc body (Q) as an example. Furthermore, the antenna body (10) has a structure in which the patch array section (7) and the slot array section (6) are bonded together such that the patch (9) is arranged in a position opposite each slot (8) formed on the surface of the disc-shaped conductor (P), and the patch array section (7) has a plurality of patches formed thereon.

[1206] The slot array section (6) is an antenna section that utilizes an empty notch section (hereinafter, slot (8)) on the surface of a disc-shaped conductor (P) as a radiating element (or incident element). The slot array section (6) has a feed section (12) installed at the center of the slot (8) and the disc-shaped conductor (P). Generally, the slot array section (6) has a mechanism for excitation directly at the leading end of a transmission line or through a cavity formed on the back surface of the slot. The slot array section (6) can be used for feeding a patch antenna through the slot from an antenna using a base plate or a microstrip line, etc. FIG. 3 describes the form of a radial line slot array as an example of the slot array section (6), but the scope of the present invention is not limited to this.

[1207] Figure 4 shows a top view of the slot array section (6) in Figure 3. The slot array section (6) will be described below using Figure 4. The slot array section (6) has a structure that is fed by a coaxial line installed in its center. Accordingly, a power supply section (12) is installed in the center of the slot array section (6) shown in Figure 4. In addition, the slot array section (6) has a plurality of slots (8) (hereinafter referred to as "slot pairs") formed on the surface of a disc-shaped conductor (P). The slot pairs (8) have a structure in which two rectangular notches are arranged in a "Ha" shape. More specifically, two rectangular slots (8) are arranged orthogonally, and one slot of the slot pair (8) is spaced 1 / 4 wavelength apart from the other slot. By this, circularly polarized waves having different rotation directions depending on the azimuth angle of the antenna can be transmitted and received.

[1208] Additionally, in this specification, two slots (8) are referred to as a slot pair (8), one slot (8) is simply referred to as a slot (8), and the collective term for the slot and slot pair is referred to as a slot (pair) (8).

[1209] A plurality of slot pairs (8) are formed spirally outward from the center of a disc-shaped conductor substrate (P) in a radial direction. Additionally, the slot pairs (8) are formed on the surface of the disc-shaped substrate such that the distance between adjacent slot pairs (8) along the spiral is constant. As a result, the phase is formed at the front of the slot array section (6), allowing the electromagnetic fields to be strengthened against each other, thereby enabling the formation of a pencil beam at the front.

[1210] Additionally, in FIGS. 3 and 4, an example of the shape of the slot (8) is shown as a rectangular parallelepiped shape, but the shape of the slot (8) in the present invention is not limited to a rectangular parallelepiped shape and can adopt known shapes such as a circle, an ellipse, or a polygon. Also, in FIGS. 3 and 4, an example of a slot pair is shown as an example of the slot (8), but the slot (8) in the present invention is not limited to a slot pair. Furthermore, an example of the arrangement of the slot (8) on the surface of the disc-shaped conductor substrate (P) is shown as a spiral shape, but the arrangement of the slot (8) is not limited to a spiral shape, and the slot (8) may be arranged in a concentric circular shape, for example, as shown in FIG. 8 described later.

[1211] The power supply unit (12) in the present invention has the function of receiving electromagnetic waves and / or radiating electromagnetic waves. Furthermore, the power supply unit (12) in the present invention is not particularly limited as long as it is a part that transmits high-frequency power generated by detecting radio waves with a patch (9), which is a radiating element or an incident element, to a receiver, or a part that connects a radiating element and a power supply line to supply high-frequency power, and known power supply units and power supply lines may be used. In FIGS. 3 and 4, a coaxial power supply unit is shown as an example.

[1212] As shown in FIG. 3, the patch array section (7) is provided with a disc body (Q) having a plurality of rectangular patches (9) of length (L) and width (W), and a liquid crystal layer (not shown) filled between the slot array section (6). In this embodiment, the patch array section (7) is configured as a so-called microstrip antenna and is a resonator that resonates at a frequency where the length (L) corresponds to an integer multiple of half the wavelength.

[1213] In addition, FIG. 3 shows a rectangular patch (9) with length (L) and width (W) as an example of a patch (9), but the shape of the patch (9) is not limited to a rectangular shape and may be a circular patch (9). FIG. 5 shows an embodiment of a circular patch (9) as another embodiment of the present invention.

[1214] FIG. 5 is a top view of the antenna body (10) in the present invention, and more specifically, a view of the antenna body (10) as seen from the patch array section (7), and a drawing in which the patch (9), feed section (12), and slot pair (8) are projected vertically onto the main surface of the disc body (Q). For this reason, the patch (9), feed section (12), and slot pair (8) are indicated by dashed lines. Also, when the shape of the patch (9) is circular, generally, TM 11 It can be operated with an electromagnetic field distribution called a mode. As shown in FIG. 5, at the point where the projection of the patch (9) and the projection of the slot pair (8) overlap, it can be understood that the patch (9) installed on the disc body (Q) is positioned in a corresponding manner for each slot (8) formed on the surface of the disc-shaped conductor (P). By utilizing a configuration in which each patch (9) is positioned in a corresponding manner for each slot (8) in this way, power can be fed from the slot (8) to the patch (9) or radio waves arriving from the patch (9) to the slot (8) can be propagated by an electronic coupling feeding method. Therefore, an antenna capable of transmitting and / or receiving radio waves can be provided.

[1215] Generally, the method of supplying power to a radiating element (e.g., patch (9)) of a patch array section (7) using a general transmission line such as a coaxial line or a planar transmission line is broadly classified into two types: a direct supply method and an electromagnetic coupling supply method. Accordingly, the supply method in the present invention can be described as a direct supply method, which is a method of exciting a radiating element by directly connecting a transmission line to a patch (9) (radiating element), and an electromagnetic coupling supply method, which is a method of exciting a patch electrode (radiating element) by an electromagnetic field generated around a supply line that is closed open or short-circuited without directly connecting the transmission line and the patch electrode (radiating element). The present invention illustrates an embodiment of the electromagnetic coupling supply method.

[1216] In this embodiment, since the power supply line by the (coaxial) power supply unit (12) is open at the end, a current standing wave is generated where the end of the power supply line coincides with a node. As a result, a magnetic field surrounding the power supply line ((coaxial) power supply unit (12)) is generated, and as this magnetic field enters the slot (8), the slot (pair) (8) is excited. Then, as the magnetic field generated by the excitation of the slot (pair) (8) enters the patch (9), the patch (9) is excited. Since the excitation intensity is maximized when the magnetic field entering the slot (8) is at its maximum, it is preferable to form the slot (pair) (8) at the position (a multiple of the current standing wave) where the magnetic field generated from the power supply line ((coaxial) power supply unit (12)) is at its maximum.

[1217] A suitable embodiment of the antenna according to the present invention is a configuration combining a radial line slot array and a patch antenna array.

[1218] Next, an embodiment of the antenna body (10) will be described using FIG. 6, which is a cross-sectional view of the antenna body (10) shown in FIG. 5. It goes without saying that FIG. 6 is a schematic diagram showing the configuration of the antenna.

[1219] As shown in FIG. 6, the antenna body (10) has a second substrate (14) in the shape of a disc, a first substrate (13) in the shape of a disc (corresponds to a disc-shaped conductor (P) and is also called a slot array substrate) having a plurality of slots (pairs) (8) formed outwardly from the center in the radiating direction, a first dielectric layer (17) installed between the second substrate (14) and the first substrate (13), a feed portion (12) installed at the center of the first substrate (13) in the shape of a disc and the second substrate (14) in the shape of a disc, a third substrate (15) in the shape of a disc (Q) and is also called a patch substrate, a patch (9) (radiating element or incident element) mounted on the third substrate (15), and a liquid crystal layer (16) installed between the third substrate (15) and the first substrate (13). Additionally, the power supply unit (12) is electrically connected to a transmitter and / or receiver installed on a control board via a power supply line (12a). And, each patch (9) corresponds to each slot pair (8).

[1220] The phrase “(each) a patch (9) corresponds to (each) a slot pair (8)” used here means that, as described in the explanation of FIG. 5 above, the projection plane obtained by vertically projecting the patch (9) onto the main surface of the second substrate (14) overlaps with the slot (pair) (8). In other words, it means that the projection plane obtained by vertically projecting the slot (pair) (8) onto the main surface of the third substrate (15) overlaps with the patch (9).

[1221] In addition, the first substrate (13), the second substrate (14), and the third substrate (15) are preferably disc bodies having the same area.

[1222] In FIG. 6, the radio waves (arrows) fed by the (coaxial) feed unit (12) become cylindrical waves and propagate outward in the radiative direction within the first dielectric layer (17), and are transmitted from the slot (pair) (8) to the liquid crystal layer (16). Also, as shown in FIG. 4, if the slot (pair) (8) consists of two orthogonal slots arranged with a 1 / 4 wavelength offset in a so-called “Ha” shape, circular polarization can be generated. As described above, by the electronic coupling feed method, the slot (pair) (8) is excited, and the magnetic field generated from the slot (pair) (8) is incident on the patch (9), thereby exciting the patch (9). As a result, the patch (9) can radiate radio waves with high directional properties.

[1223] Meanwhile, when receiving an incoming radio wave, according to the principle of reversible transmission and reception, contrary to the above, after the patch (9) receives the incoming radio wave, the incoming radio wave is transmitted to the feed unit (12) through the slot (pair) (8) installed immediately below the patch (9).

[1224] Circular polarization, unlike linear polarization, is a radio wave in which the direction of the electric field rotates over time. It is classified into first-order circular polarization used in GPS or ETC and left-order circular polarization used in satellite radio broadcasting, and the antenna according to the present invention can receive either polarization.

[1225] By applying voltage to the liquid crystal layer (16) between the patch (9) and the first substrate (13), the orientation direction of the liquid crystal molecules in the liquid crystal layer (16) can be changed. As a result, the dielectric constant of the liquid crystal layer (16) changes, so the capacitance of the slot (pair) (8) changes, and consequently, the reactance and resonance frequency of the slot (pair) (8) can be controlled. In other words, by controlling the dielectric constant of the liquid crystal layer (16), the reactance and resonance frequency of the slot (8) can be controlled, and thus the power supply to each patch (9) can be controlled by controlling the excitation of the slot (pair) (8) and the patch (9). By doing so, it becomes possible to control the propagation of radiation through the liquid crystal layer (16). Therefore, for example, an applied voltage control means for controlling the voltage applied to the liquid crystal layer (16), such as a TFT, may be installed. In addition, by changing the orientation direction of the liquid crystal molecules of the liquid crystal layer (16), the refractive index changes, and as a result, the phase of the electromagnetic waves passing through the liquid crystal layer (16) is misaligned, and as a result of the combined effect, phased array control becomes possible.

[1226] The materials of the first substrate (13) and the second substrate (14) are not particularly limited as long as they are conductors such as copper. Also, the material of the third substrate (15) is not particularly limited, and depending on the mode of use, known materials such as glass substrates, acrylic substrates, ceramics (alumina), silicon, glass cross Teflon (registered trademark) (PTFE) may be used. The material of the first dielectric layer (17) may be selected from known materials appropriately according to the desired dielectric constant, and may be vacuum. Additionally, the material of the patch (9) is not particularly limited as long as it is a conductor such as copper or silver.

[1227] Next, another embodiment of the antenna body (10) will be described using FIG. 7. The embodiment shown in FIG. 7 is an aspect in which the slot array portion (6) of the antenna body (10) is different from the embodiment shown in FIG. 6.

[1228] In FIG. 7, the antenna body (10) has a first substrate (13) of a hollow body having a plurality of slots (pairs) (8) formed on one surface, a second substrate (14) of a disc shape accommodated inside the first substrate (13) of the hollow body, a first dielectric layer (17), a feed section (12), a third substrate (15) of a disc shape, a patch (9) mounted on the third substrate (15), and a liquid crystal layer (16) installed between the third substrate (15) and the first substrate (13). The feed section (12) is installed between the surface of the first substrate (13) of the other side where the plurality of slots (pairs) (8) are not formed and the second substrate (14), and is also installed at the center of the first substrate (13) and the second substrate (14) of the disc shape. Additionally, the power supply unit (12) is electrically connected to a transmitter and / or receiver installed on a control board via a power supply line (12a). And, each patch (9) corresponds to each slot pair (8). Also, in FIG. 7, the two side portions of the first substrate (13) of the hollow body protrude outward from the hollow body, and specifically, have an inclined surface at 45° with respect to the horizontal direction.

[1229] As shown in FIG. 7, the radio waves (arrows) fed by the (coaxial) feed unit (12) become cylindrical waves and propagate outward in the radial direction within the first dielectric layer (17). Then, as the propagated cylindrical waves are reflected from both sides of the first substrate (13) of the hollow body, the cylindrical waves that have entered around the second substrate (14) are converted into traveling waves (arrows) directed from the outer periphery of the first substrate (13) in the shape of a disc toward the center and propagate within the first dielectric layer (17). At that time, the traveling waves are transmitted from the slot (pair) (8) to the liquid crystal layer (16). By doing so, the patch (9) is excited in the same way as in the embodiment shown in FIG. 6, and can radiate radio waves with high directionality.

[1230] Meanwhile, in the same case as when receiving an incoming radio wave, after the patch (9) receives the incoming radio wave, the incoming radio wave is transmitted to the feed unit (12) through the slot (pair) (8) installed directly below the patch (9).

[1231] Next, another embodiment of the antenna body (10) will be described using FIGS. 8 to 10. In the embodiment of the antenna body (10) described above in FIGS. 5 to 7, a configuration of the antenna body (10) in which a liquid crystal layer (16) is uniformly installed between a first substrate (13) and a third substrate (15) was described. Meanwhile, in the embodiment of FIGS. 8 to 10, a configuration of the antenna body (10) in which a liquid crystal layer (16) is filled within a space (hereinafter, a sealed area (20)) respectively arranged with a patch (9) and a slot (8) will be described.

[1232] FIG. 8 is a top view showing an example of an embodiment of an antenna body (10) according to the present invention. More specifically, FIG. 8 is a drawing in which the antenna body (10) is viewed from the patch array section (7), and the patch (9), feed section (12), and slot (8) are projected vertically onto the main surface of the disc body (Q). For this reason, as in FIG. 5, the patch (9), feed section (12), and slot (8) are indicated by dashed lines. In FIG. 8, a rectangular patch (9) and a single rectangular slot (8) are arranged correspondingly in the sealing area (20). Also, as shown in FIG. 8, the slot (8) is formed directly below the patch (9) at the point where the projection of the patch (9) and the projection of the slot (8) overlap. Accordingly, the embodiment of the antenna body (10) shown in FIG. 8 can feed power from the slot (8) to the patch (9) by means of an electronic coupling feeding method, or transmit radio waves arriving from the patch (9) to the slot (8). Therefore, an antenna capable of transmitting and / or receiving radio waves can be provided.

[1233] Also, as shown in FIG. 8, in this embodiment, the patch (9) and the slot (8) are arranged in a concentric shape from the center of the disc body (Q) toward the outer circumference of the disc body (Q). Therefore, since a conical beam is produced by coaxial mode feeding, the phase is formed at the front of the disc body (Q), and the electromagnetic fields can be strengthened together.

[1234] Next, an embodiment of the antenna body (10) will be described using FIG. 9, which is a cross-sectional view of the antenna body (10) shown in FIG. 8. It goes without saying that FIG. 9 is a schematic diagram showing the configuration of the antenna.

[1235] As shown in FIG. 9, the antenna body (10) comprises a second substrate (14) in the shape of a disc, a first substrate (13) in the shape of a disc having a plurality of slots (8) formed in a concentric axis shape extending outward from the center in the radiating direction, a buffer layer (22) installed on the surface of the first substrate (13) on the side of the second substrate (14), a first dielectric layer (17) installed between the buffer layer (22) and the second substrate (14), a feed portion (12) installed at the center of the first substrate (13) in the shape of a disc and the second substrate (14) in the shape of a disc and installed to contact the first dielectric layer (17), a third substrate (15) in the shape of a disc, a patch (9) (radiating element or incident element) mounted on the third substrate (15), and a plurality of sealed regions (20) in which the patch (9) is installed and is isolated by a seal wall (24) between the third substrate (15) and the first substrate (13). It has a liquid crystal layer (16) charged to come into contact with the patch (9). Also, the power supply unit (12) is electrically connected to a transmitter and / or receiver installed on a control board via a power supply line (12a). And, each patch (9) corresponds to each slot (8), and within each sealing area (20), there is at least one patch (9), at least one slot (8), and a liquid crystal layer (16), and each of the plurality of sealing areas (20) is isolated through seal walls (21, 23, 24).

[1236] Although not shown in FIG. 9, a TFT (thin-film transistor) for controlling the voltage of the liquid crystal layer (16) within each sealed region (20) may be installed, for example, on the first substrate (13) as needed. By doing so, the application of the voltage of the liquid crystal layer (16) can be controlled in an active manner. Additionally, as needed, an alignment film may be installed within each sealed region (20) to fix the orientation direction of the liquid crystal molecules constituting the liquid crystal layer (16). As the alignment film, a homeotropic alignment film that facilitates the orientation of liquid crystal molecules in the vertical direction or a homogeneous alignment film that facilitates the orientation of liquid crystal molecules in the horizontal direction may be installed between the first substrate (13) and the liquid crystal layer (16). Examples include a polyimide alignment film and a photo-alignment film.

[1237] Next, the sealing area (20) in the present embodiment will be explained using FIG. 10, which is a cross-sectional view of the antenna body (10) shown in FIG. 8 cut along the BB line. It goes without saying that FIG. 10 is a schematic diagram showing the sealing area (20).

[1238] As shown in FIG. 10, the sealing area (20) is a sealing space enclosed in all four directions by a seal wall (24), a buffer layer (22), a first substrate (13), and a third substrate (15), and is installed within the same sealing space so as to replace at least one patch (9) and at least one slot (8), and is also filled with a liquid crystal layer (16).

[1239] In this embodiment, the seal wall (24) may be formed of a known insulator or the like. Also, the buffer layer (22) may be formed of a known dielectric material or the like.

[1240] Although not shown in FIG. 10, a TFT (thin-film transistor) for controlling the voltage of the liquid crystal layer (16) within the sealing region (20) may be installed, for example, on the first substrate (13) as needed. By doing so, the application of the voltage of the liquid crystal layer (16) can be controlled in an active manner. To explain the driving method according to the active method in more detail, for example, a method in which the patch (9) is used as a common electrode and the first substrate (13) is used as a pixel electrode, and the voltage between the patch (9) and the first substrate (13) is controlled by a TFT formed on the first substrate (13) to control the orientation of liquid crystal molecules of the liquid crystal layer (16); or a method in which the first substrate (13) is used as a pixel electrode and an electrode layer and a TFT are formed on the first substrate (13), and the voltage between the patch (9) and the first substrate (13) is controlled to control the orientation of liquid crystal molecules of the liquid crystal layer (16); or a method in which a comb electrode and a TFT are installed on the first substrate (13), and the orientation of liquid crystal molecules of the liquid crystal layer (16) is controlled by the TFT. Furthermore, the method of controlling the application of voltage to the liquid crystal layer (16) in an active manner is not limited to the above methods.

[1241] In addition, at this time, an alignment layer may be installed to fix the orientation direction of the liquid crystal molecules constituting the liquid crystal layer (16) within each sealing region (20). As the alignment layer, a homeotropic alignment layer that facilitates orientation of the liquid crystal molecules in the vertical direction or a homogeneous alignment layer that facilitates orientation of the liquid crystal molecules in the horizontal direction may be installed between the first substrate (13) and the liquid crystal layer (16).

[1242] To tune the liquid crystal layer (16), the voltage applied to the liquid crystal layer (16) between the patch (9) and the first substrate (13) may be modulated. For example, as described above, the voltage applied to the liquid crystal layer (16) is controlled using an active method, thereby changing the capacitance of the slot (8), and consequently, the reactance and resonance frequency of the slot (8) can be controlled. The resonance frequency of the slot (8) has a correlation with the energy radiated from the radio waves propagating through the line. Therefore, by adjusting the resonance frequency of the slot (8), the slot (8) is prevented from substantially coupling with the cylindrical wave energy from the feed section (12), or it is coupled with the cylindrical wave energy and radiated into free space. Such control of the reactance and resonance frequency of the slot (8) can be performed in each of the multiple formed sealing regions (20). In other words, by controlling the dielectric constant of the liquid crystal layer (16), the power supply to the patch (9) within each sealing region (20) can be controlled by the TFT. Therefore, since it is possible to control the patch (9) that transmits radio waves and the patch that does not transmit radio waves, it is possible to control the transmission and reception of radiated radio waves through the liquid crystal layer (16).

[1243] Examples

[1244] The present invention will be described in more detail below with reference to examples, but the present invention is not limited in any way to the following examples.

[1245] The compositions of the following examples and comparative examples contain each compound in the proportions shown in the table, and the content is indicated in “mass%”.

[1246] Additionally, the following abbreviations are used to describe compounds. Furthermore, compounds capable of having a cis form and a trans form are represented as the trans form unless otherwise specifically noted.

[1247] <Circular Structure>

[1248]

[1249] <Terminal structure>

[1250] [Table 1]

[1251]

[1252] (However, n in the table is a natural number.)

[1253] <Connection Structure>

[1254] [Table 2]

[1255]

[1256] (However, n in the table is a natural number.)

[1257] (Hindered phenolic antioxidant)

[1258]

[1259] (Hindered amine-based light stabilizer)

[1260]

[1261] (Preparation of liquid crystal composition)

[1262] LC-A~B and LC-1~4 listed in Table 3 were prepared.

[1263] [Table 3]

[1264]

[1265] (Examples 1–28 and Comparative Examples 1–3)

[1266] Liquid crystal compositions described in Tables 2 to 6 were prepared using LC-A to B and LC-1 to 4, hindered phenolic antioxidants (XX-1) to (XX-3), and hindered amine light stabilizers (YY-1) to (YY-2), and the physical properties were measured to perform a <storage stability test>. The results are shown in Tables 4 to 8.

[1267] <Preservation Stability Test>

[1268] 0.5 g of the liquid crystal composition was weighed into a 1 mL sample bottle (manufactured by Maru M Co., Ltd.) and degassing was performed by degassing at 150–250 Pa for 10 minutes. Afterward, the sample was purged using dry nitrogen and covered with a provided lid. This was stored for 2 weeks in a temperature-controlled constant temperature bath (manufactured by Espect, SH-241) at 0°C, and the occurrence of crystallization of the liquid crystal composition was checked visually every week.

[1269] [Table 4]

[1270]

[1271] [Table 5]

[1272]

[1273] [Table 6]

[1274]

[1275] [Table 7]

[1276]

[1277] [Table 8]

[1278]

[1279] From Examples 1 to 4, the liquid crystal composition using the compound represented by general formula (i) is T ni g is high, Δn is large, and V th is low, and Δε r This is large, and tanδ iso It was a liquid crystal composition with a small size and good preservation properties at low temperatures.

[1280] In particular, Examples 2 and 4, in particular Δn and Δε r This resulted in a great outcome.

[1281] Meanwhile, from Comparative Examples 1 to 3, the liquid crystal composition that did not use the compound represented by general formula (i) did not have good storage performance at low temperatures, or V th If is very high, or Δε r This small thing has been confirmed.

[1282] In addition, from Examples 5 to 28, even when a hindered phenol-based antioxidant or a hindered amine-based light stabilizer is used in combination, T ni g is high, Δn is large, and V th is low, and Δε r This is large, and tanδ iso It was confirmed that it is small and has good preservation properties at low temperatures.

[1283] (Examples 29–42)

[1284] In addition, LC-5 to 6 as described in Table 9 were prepared. Then, liquid crystal compositions as described in Tables 10 to 12 were prepared using LC-5 to 6, hindered phenolic antioxidants (XX-1) to (XX-3), and hindered amine light stabilizers (YY-1) to (YY-2). The physical properties were measured, and a storage stability test was performed, confirming that the same effect as in Examples 1 to 28 was observed. The results are shown in Tables 9 to 12.

[1285] [Table 9]

[1286]

[1287] [Table 10]

[1288]

[1289] [Table 11]

[1290]

[1291] [Table 12]

[1292]

[1293] (Synthesis of a compound represented by general formula (i))

[1294] (Example 29) Preparation of a compound represented by formula (I-1)

[1295]

[1296] Under a nitrogen atmosphere, 30 g of triphenylphosphine and 200 mL of dichloromethane were added to a reaction vessel and cooled to 0°C. 50 mL of a dichloromethane solution containing 15 g of 4-propylcyclohexylaldehyde and 33 g of carbon tetrabromide was added dropwise. After the reaction was complete, the precipitate was filtered, and the solution was concentrated. 100 mL of tetrahydrofuran (THF) was added to the concentrate, and the mixture was cooled to -60°C. While maintaining -60°C, 50 mL of an n-butyllithium hexane solution (1.6 M) was slowly added dropwise. After the addition was complete, the mixture was stirred at -60°C for 2 hours. After the reaction was complete, the mixture was post-treated with water and 10 mass% hydrochloric acid, extracted with hexane, and concentrated. The concentrate was purified by silica gel column chromatography (hexane), and 10 g of the compound represented by formula (1-1-1) was obtained.

[1297] Next, under a nitrogen atmosphere, 20.0 g of 1-bromo-4-iodobenzene, 0.5 g of copper(I) iodide, 0.9 g of bis(triphenylphosphine)palladium(II) dichloride, 50 mL of triethylamine, and 100 mL of THF were added to a reaction vessel. While stirring at room temperature, a solution of 10 g of the compound represented by formula (I-1-1) dissolved in 50 mL of THF was added dropwise, and the mixture was stirred at room temperature for 1 hour. 10 mass% hydrochloric acid was added to the reaction mixture, and it was extracted with toluene. The organic layer was post-treated with saline solution and purified by silica gel column chromatography (toluene). Additionally, recrystallization (toluene / hexane = 1 / 2) was performed to obtain 12 g of the compound represented by formula (I-1-2).

[1298] Next, under a nitrogen atmosphere, 12 g of the compound represented by formula (I-1-2), 0.2 g of copper(I) iodide, 0.7 g of tetrakis(triphenylphosphine)palladium, 30 mL of triethylamine, and 50 mL of N,N-dimethylformamide were added to a reaction vessel. While heating to 80°C, 20 mL of a solution of N,N-dimethylformamide containing 6.5 g of 4-amino-3,5-difluorophenylacetylene was added dropwise, and the mixture was stirred at 80°C for 2 hours. The reaction mixture was post-treated with 10 mass% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane). Additionally, recrystallization (toluene / hexane = 1 / 3) was performed to obtain 13 g of the compound represented by formula (1-1-3).

[1299] 13 g of the compound represented by formula (I-1-3), 40 ml of dichloromethane, and 7.5 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane). Additionally, recrystallization (toluene / hexane = 1 / 1) was performed to obtain 6.5 g of the compound represented by formula (I-1).

[1300] Cr 113 N 227 Iso

[1301] MS(EI): m / z=419

[1302] (Example 30) Preparation of a compound represented by formula (I-2)

[1303]

[1304] Under a nitrogen atmosphere, 10.0 g of the compound represented by formula (I-2-1), 0.2 g of copper(I) iodide, 0.7 g of bis(triphenylphosphine)dichloropalladium, 20 mL of triethylamine, and 40 mL of THF were added to a reaction vessel. While heating to 60°C, 10 mL of a THF solution containing 4.5 g of trimethylsilylacetylene was added dropwise, and the mixture was stirred at 60°C for 2 hours. After cooling the reaction mixture, it was post-treated with 100 mL of a saturated aqueous ammonium chloride solution and then extracted with toluene. The organic layer was washed with saturated saline solution and purified by silica gel column chromatography (toluene). Additionally, recrystallization (toluene / hexane = 1 / 2) was performed to obtain the target compound.

[1305] Next, under a nitrogen atmosphere, 3g of potassium carbonate was added to the obtained compound in the reaction vessel and dissolved in 100ml of methanol, and the reaction was carried out at 40°C for 2 hours. The reaction solution was extracted with toluene, the organic layer was washed with saturated saline solution, and then purified by silica gel column chromatography (toluene) to obtain 6.8g of the compound represented by formula (1-2-2).

[1306] Under a nitrogen atmosphere, 6.8 g of the compound represented by formula (I-2-2), 5 g of catecholborane, 0.5 g of bis(triphenylphosphine)palladium(II) dichloride, and 60 mL of THF were added to a reaction vessel, and the reaction was carried out by heating under reflux for 3 hours. After the reaction was completed, the mixture was post-treated with water and then extracted with ethyl acetate. The organic layer was concentrated to obtain 10.0 g of the compound represented by formula (I-2-3).

[1307] Next, under a nitrogen atmosphere, 10.0 g of the compound represented by formula (I-2-3), 6.5 g of 4-bromo-2,6-difluoroaniline, 340 mg of tetrakis(triphenylphosphine)palladium, 8.5 g of potassium carbonate, 75 mL of tetrahydrofuran, and 10 mL of water were added to a reaction vessel, and the reaction vessel was heated to 70°C. After the reaction was complete, the reaction mixture was post-treated with 100 mL of saturated ammonium chloride aqueous solution and then extracted with ethyl acetate. The organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane). Additionally, recrystallization (toluene) was performed to obtain 7.2 g of the compound represented by formula (I-2-4).

[1308] Next, under a nitrogen atmosphere, 7.2 g of the compound represented by Formula (I-2-4), 50 ml of dichloromethane, and 6 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel, and the mixture was heated under reflux for 6 hours. After the reaction was completed, the organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane). Additionally, recrystallization (toluene) was performed to obtain 4.5 g of the compound represented by Formula (I-2).

[1309] MS(EI): m / z=421

[1310] (Example 31) Preparation of a compound represented by formula (I-3)

[1311]

[1312] Under a nitrogen atmosphere, 22 g of the compound represented by formula (I-3-2), 1.0 g of copper(I) iodide, 3 g of tetrakis(triphenylphosphine)palladium, 20 mL of triethylamine, and 100 mL of N,N-dimethylformamide were added to a reaction vessel. While heating to 80°C, 20 mL of a solution of N,N-dimethylformamide containing 15 g of the compound represented by formula (I-3-1) was added dropwise, and the mixture was stirred at 80°C for 2 hours. After the reaction was complete, the reaction mixture was cooled, post-treated with 10 mass% hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane / ethyl acetate = 2 / 1). Additionally, recrystallization (toluene / hexane = 2 / 1) was performed to obtain 24 g of the compound represented by formula (1-3-3).

[1313] Next, under a nitrogen atmosphere, 24 g of the compound represented by formula (I-3-3), 10 g of pyridine, and 150 mL of dichloromethane were added to a reaction vessel and cooled to 0–10°C. Then, 34 g of trifluoromethanesulfonic acid anhydride was slowly added dropwise. After the addition was finished, the reaction was carried out at room temperature for 2 hours. After the reaction was finished, the organic layer was concentrated by post-treatment with 10 mass% hydrochloric acid and washing with saturated saline solution.

[1314] Next, the concentrate was transferred to a reaction vessel, and 0.8 g of copper(I) iodide, 2.5 g of tetrakis(triphenylphosphine)palladium, 20 mL of triethylamine, and 100 mL of N,N-dimethylformamide were added under a nitrogen atmosphere. While heating the reactor to 80°C, 20 mL of a solution of N,N-dimethylformamide containing 12 g of 4-amino3,5-difluorophenylacetylene was added dropwise, and the mixture was stirred at 80°C for 2 hours. After the reaction was complete, the reaction mixture was cooled, post-treated with 10 mass% hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane / ethyl acetate = 1 / 1). Additionally, recrystallization (toluene) was performed to obtain 26 g of the compound represented by formula (1-3-4).

[1315] Next, under a nitrogen atmosphere, 26 g of the compound represented by Formula (I-3-4), 100 ml of dichloromethane, and 13 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane). Additionally, recrystallization (toluene / hexane = 2 / 1) was performed to obtain 21 g of the compound represented by Formula (I-3).

[1316] MS(EI) : m / z=445

[1317] (Example 32) Preparation of a compound represented by formula (I-4)

[1318]

[1319] Under a nitrogen atmosphere, 28 g of 1-bromo-4-iodobenzene, 1.0 g of copper(I) iodide, 3 g of tetrakis(triphenylphosphine)palladium, 20 mL of triethylamine, and 200 mL of THF were added to a reaction vessel. At room temperature, 100 mL of a THF solution containing 19 g of the compound represented by formula (I-4-1) was added dropwise, and the mixture was stirred for an additional 4 hours at room temperature. After the reaction was complete, the reaction mixture was post-treated with 10 mass% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane). Additionally, recrystallization (toluene / hexane = 1 / 4) was performed to obtain 32 g of the compound represented by formula (1-4-2).

[1320] Next, under a nitrogen atmosphere, 32 g of the compound represented by formula (I-4-2), 24 g of the compound represented by formula (I-4-3), 1 g of tetrakis(triphenylphosphine)palladium, 18 g of potassium carbonate, 150 mL of tetrahydrofuran, and 20 mL of water were added to a reaction vessel, and the reaction vessel was heated to 70°C. After the reaction was completed, the reaction solution was post-treated with 100 mL of saturated ammonium chloride aqueous solution and then extracted with ethyl acetate. The organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane / ethyl acetate = 1 / 1). Additionally, recrystallization (toluene / hexane = 2 / 1) was performed to obtain 28 g of the compound represented by formula (I-4-4).

[1321] Next, under a nitrogen atmosphere, 28 g of the compound represented by formula (I-4-4), 150 ml of dichloromethane, and 15 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel, and the mixture was heated under reflux for 6 hours. After the reaction was completed, the organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane). Additionally, recrystallization (toluene) was performed to obtain 23 g of the compound represented by formula (I-4).

[1322] Cr 91 SmA 145 N 203 Iso

[1323] MS(EI): m / z=439

[1324] (Example 33) Preparation of a compound represented by formula (I-5)

[1325]

[1326] Under a nitrogen atmosphere, 29 g of the compound represented by formula (I-5-1), 1.0 g of copper(I) iodide, 3 g of tetrakis(triphenylphosphine)palladium, 20 mL of triethylamine, and 150 mL of N,N-dimethylformamide were added to a reaction vessel. While heating the reaction vessel to 80°C, 50 mL of a solution of N,N-dimethylformamide containing 23 g of the compound represented by formula (I-5-2) was added dropwise, and the mixture was stirred at 80°C for 2 hours. After the reaction was complete, the reaction mixture was cooled, post-treated with 10 mass% hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane / ethyl acetate = 2 / 1). Additionally, recrystallization (ethanol) was performed to obtain 26 g of the compound represented by formula (1-5-3).

[1327] Next, under a nitrogen atmosphere, 26 g of the compound represented by formula (I-5-3), 12 g of pyridine, and 150 mL of dichloromethane were added to a reaction vessel and cooled to 0–10°C. Then, 30 g of trifluoromethanesulfonic acid anhydride was slowly added dropwise. After the addition was finished, the reaction was carried out at room temperature for 2 hours. After the reaction was finished, the mixture was post-treated with 10 mass% hydrochloric acid, washed with saturated saline solution, and the organic layer was concentrated.

[1328] Next, a concentrate containing the compound represented by Formula (1-5-4) was transferred to a reaction vessel. Under a nitrogen atmosphere, 26.0 g of the compound represented by Formula (I-5-5), 1 g of tetrakis(triphenylphosphine)palladium, 18 g of potassium carbonate, 150 mL of tetrahydrofuran, and 20 mL of water were added to the reaction vessel, and the reaction vessel was heated to 70°C. After the reaction was completed, the reaction mixture was post-treated with a saturated aqueous ammonium chloride solution and then extracted with ethyl acetate. The organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane / ethyl acetate = 1 / 1). Additionally, recrystallization (toluene / hexane = 3 / 1) was performed to obtain 24 g of the compound represented by Formula (I-5-6).

[1329] Next, under a nitrogen atmosphere, 24 g of the compound represented by Formula (I-5-6), 150 ml of dichloromethane, and 12 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel, and the mixture was heated under reflux for 6 hours. After the reaction was completed, the organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane). Additionally, recrystallization (toluene) was performed to obtain 23 g of the compound represented by Formula (I-5).

[1330] MS(EI) : m / z=453

[1331] (Example 34) Preparation of a compound represented by formula (I-6)

[1332]

[1333] 20g of the compound represented by formula (I-6) was obtained by the same method as in Example 32, except that 17.6g of the compound represented by formula (I-6-1) was used instead of 19g of the compound represented by formula (1-4-1) of Example 32.

[1334] MS(EI) : m / z=425

[1335] (Example 35) Preparation of a compound represented by formula (I-7)

[1336]

[1337] 23g of the compound represented by formula (I-7) was obtained by the same method as in Example 32, except that 20.5g of the compound represented by formula (I-7-1) was used instead of 19g of the compound represented by formula (1-4-1) of Example 32.

[1338] MS(EI) : m / z=453

[1339] (Example 36) Preparation of a compound represented by formula (I-8)

[1340]

[1341] 7g of the compound represented by formula (I-8) was obtained by the same method as in Example 29, except that 11g of the compound represented by formula (I-8-1) was used instead of 10g of the compound represented by formula (1-1-1) of Example 29.

[1342] MS(EI): m / z=433

[1343] (Example 37) Preparation of a compound represented by formula (I-9)

[1344]

[1345] 9g of compound represented by (I-9) was obtained by the same method as in Example 29, except that 12g of compound represented by formula (I-9-1) was used instead of 10g of compound represented by formula (1-1-1) of Example 29.

[1346] MS(EI): m / z=447

[1347] (Example 38) Preparation of a compound represented by formula (I-10)

[1348]

[1349] 23g of the compound represented by formula (I-10) was obtained by the same method as in Example 32, except that 21g of the compound represented by formula (I-10-2) was used instead of 24g of the compound represented by formula (I-4-3) of Example 32.

[1350] Cr 102 SmA 206 N 261 Iso

[1351] MS(EI): m / z=403

[1352] (Example 39) Preparation of a compound represented by formula (I-11)

[1353]

[1354] Under a nitrogen atmosphere, 30 g of the compound represented by formula (I-11-1), 26 g of the compound represented by formula (I-11-2), 1 g of tetrakis(triphenylphosphine)palladium, 20 g of potassium carbonate, 150 mL of tetrahydrofuran, and 20 mL of water were added to a reaction vessel, and the reaction vessel was heated to 70°C. After the reaction was completed, the reaction solution was post-treated with a saturated aqueous ammonium chloride solution and then extracted with ethyl acetate. The organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane / ethyl acetate = 2 / 1). Additionally, recrystallization (toluene / hexane = 1 / 2) was performed to obtain 29 g of the compound represented by formula (I-11-3).

[1355] 29 g of the compound represented by formula (I-11-3), 150 ml of dichloromethane, and 17 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel, and the mixture was heated under reflux for 6 hours. After the reaction was complete, the organic layer was washed with saturated saline solution and purified by silica gel column chromatography (dichloromethane). Additionally, recrystallization (toluene) was performed to obtain 22 g of the compound represented by formula (I-11).

[1356] Cr 77 N 210 Iso

[1357] MS(EI): m / z=395

[1358] (Example 40) Preparation of a compound represented by formula (I-12)

[1359]

[1360] 21g of the compound represented by formula (I-12) was obtained by the same method as in Example 39, except that 32g of the compound represented by formula (I-12-1) was used instead of 30g of the compound represented by formula (I-11-1) of Example 39.

[1361] MS(EI): m / z=409

[1362] Industrial applicability

[1363] 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. Explanation of the symbols

[1364] 1: Antenna unit 2: Vehicle 3: Case 4: Control Panel 5: Upper cover 6: Slot Array Section 7: Patch Array Section 8: Slot 9: Patch 10: Antenna body 11: Antenna assembly 12: Emergency Department 12a: feeder line 13: First substrate 14: Second substrate 15: Third substrate 16: Liquid crystal layer 17: First dielectric layer 20: Sealing area 21, 23, 24: Time Wall 22: Buffer layer P: Conductor Q: Disc body

Claims

Claim 1 The following general formula (i) ( among general formula (i), R i1 A represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 20 carbon atoms, wherein one or more -CH2- in the alkyl group may each independently be substituted with -O-, -S-, -CO- and / or -CS-, and one or more -CH2-CH2- in the alkyl group may each independently be substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH- and / or -CF=CF-, and one or more -CH2-CH2-CH2- in the alkyl group may each independently be substituted with -O-CO-O-, and one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom, provided that there is no direct bonding between oxygen atoms, and A i1 ...represents a 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- present in this group may be substituted with -O- and / or -S-), and A i2 and A i3 Each is independently of the following groups (a), (b), (c) and (d): (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- present in this group may be substituted with -O- and / or -S-) (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= present in this group may be substituted with -N=) (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, (d) 1 -CH= or 2 or more non-adjacent -CH= present in decahedronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group (one -CH= or two or more non-adjacent -CH= present in naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group or phenanthrene-2,7-diyl group may be substituted with -N=.) It represents a group selected from the group consisting of benzothiophen-2,5-diyl group, benzothiophen-2,6-diyl group, dibenzothiophen-3,7-diyl group, dibenzothiophen-2,6-diyl group, and thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= present in this group may be substituted with -N=), wherein A i1 , A i2 and A i3 One or more hydrogen atoms among them, independently, are substituent S i1 It may be substituted by, and substituent S i1 It represents any one of silver, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms, wherein one or more -CH2- in said alkyl group may each independently be substituted with -O-, -S- and / or -CO-, and one or more -CH2-CH2- in said alkyl group may each independently be substituted with -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or It may be substituted with -NH-CO-, and one or more -CH2-CH2-CH2- in the alkyl group may each independently be substituted with -O-CO-O-, and one or more hydrogen atoms in the alkyl group may each independently be substituted with halogen atoms, provided that there is no direct bonding between oxygen atoms, and the substituent S i1 In cases where there is a plural, they may be the same or different, Z i1 A liquid crystal composition comprising one or more compounds represented by: a compound having any one of an alkylene group having 1 to 20 carbon atoms, wherein one or more -CH2- in the alkylene group may each independently be substituted with -O-, -CF2- and / or -CO-, and one or more -CH2-CH2- in the alkylene group may each independently be substituted with -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, provided that there are no cases where oxygen atoms are directly bonded to oxygen atoms. Claim 2 In claim 1, the compound represented by the general formula (i) is the following general formulas (i-1) to (i-2) ( Among general formulas (i-1)~(i-2), R i1 , A i1 and Z i1 is R in the above general formula (i). i1 , A i1 and Z i1 and each represent the same meaning, and X i-1-2-1 , X i-1-2-2 , X i-1-2-3 , X i-1-2-4 , X i-1-2-5 , X i-1-2-6 , X i-1-2-7 , X i-1-2-8 , X i-1-3-2 , X i-1-3-3 , X i-1-3-5 , X i-1-3-6 Each independently, a hydrogen atom or a substituent S i1 Represents, and substituent S i1 is, substituent S in the above general formula (i). i1 A liquid crystal composition selected from the group consisting of compounds represented by (each having the same meaning). Claim 3 In claim 1 or claim 2, also, the following general formula (ii) (of general formula (ii), R ii1 Each represents an alkyl group having 1 to 20 carbon atoms independently, and one or more -CH2- in the alkyl group may each independently be substituted with -O-, -S-, -CO- and / or -CS-, and one or more -CH2-CH2- in the alkyl group may each independently be substituted with -CH=CH-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-, and one or more -CH2-CH2-CH2- in the alkyl group may each independently be substituted with -O-CO-O-, and one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom, and oxygen atoms and oxygen There are no cases where atoms bond directly, and A ii1 and A ii2 Each independently, the following groups (a), (b), (c) and (d): (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- present in this group may be substituted with -O- and / or -S-) (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= present in this group may be substituted with -N=) (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, (d) 1 -CH= or 2 or more non-adjacent -CH= present in decahedronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group (one -CH= or two or more non-adjacent -CH= present in naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group or phenanthrene-2,7-diyl group may be substituted with -N=.) It represents a group selected from the group consisting of benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group, and thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= present in this group may be substituted with -N=), and the above A ii1 and A ii2 One or more hydrogen atoms among them, independently, are substituent S ii1 It may be substituted by, and substituent S ii1 It represents any one of silver, a halogen atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms, wherein one or two or more -CH2- in said alkyl group may each independently be substituted with -O-, -S-, -CO- and / or -CS-, and one or two or more -CH2-CH2- in said alkyl group may each independently be substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C- ...and, one or more -CH2-CH2-CH2- in the said alkyl group may each independently be substituted with -O-CO-O-, and one or more hydrogen atoms in the said alkyl group may each independently be substituted with halogen atoms, provided that there is no direct bonding between oxygen atoms, and the substituent S ii1 In cases where there is a plural, they may be the same or different, Z ii1 ...represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms, and one or more -CH2- in the said alkylene group may each independently be substituted with -O-, and one or more -CH2-CH2- in the said alkylene group may each independently be substituted with -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, and one or more -CH2-CH2-CH2- in the said alkylene group may each independently be substituted with -O-CO-O-, and there are no direct bonds between oxygen atoms, and n ii1 represents an integer from 1 to 4, and A ii1 and Z ii1 A liquid crystal composition comprising one or more compounds represented by the formula (i), wherein, in the case of multiple compounds, they may each be identical or different. (However, the compound represented by the general formula (i) is excluded.) Claim 4 In claim 3, the compound represented by the general formula (ii) is the following general formulas (ii-1) to (ii-6) ( Among general formulas (ii-1) to (ii-6), R ii1 , A ii1 and A ii2 is R in the above general formula (ii). ii1 , A ii1 and A ii2 Each has the same meaning as and among general formulas (ii-3) to (ii-6), A ii1-2 The definition of is A in the above general formula (ii). ii1 A liquid crystal composition selected from the group consisting of compounds represented as (same as the definition of ). Claim 5 In claim 1 or claim 2, also, the following general formula (vi) ( among general formula (vi), R vi1 It represents an alkyl group having 1 to 20 carbon atoms, hydrogen atoms, or carbon atoms, and one or more -CH2- in said alkyl group may each independently be substituted with -O-, -S-, -CO- and / or -CS-, and one or more -CH2-CH2- in said alkyl group may each independently be substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-, and one or more -CH2-CH2-CH2- in said alkyl group may each independently be substituted with -O-CO-O-, and one or more hydrogen atoms in said alkyl group may each independently be substituted with halogen atoms, provided that in cases where oxygen atoms are directly bonded to each other None, R vi2 ...represents any one of a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, or an alkyl group having 1 to 20 carbon atoms, wherein one or more -CH2- in said alkyl group may each independently be substituted with -O-, -S-, -CO- and / or -CS-, and one or more -CH2-CH2- in said alkyl group may each independently be substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C- It may be substituted, and one or more -CH2-CH2-CH2- in the alkyl group may each independently be substituted with -O-CO-O-, and one or more hydrogen atoms in the alkyl group may each independently be substituted with halogen atoms, provided that there is no direct bonding between oxygen atoms, and A vi1 , A vi2 and A vi3 Each independently represents either a hydrocarbon ring having 3 to 16 carbon atoms or a complex ring having 3 to 16 carbon atoms, and the above A vi1 , A vi2 and A vi3 One or more hydrogen atoms among them, independently, are substituent S vi1 It may be substituted by, and substituent S vi1 It represents any one of silver, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms, wherein one or more -CH2- in said alkyl group may each independently be substituted with -O-, -S- and / or -CO-, and one or more -CH2-CH2- in said alkyl group may each independently be substituted with -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or It may be substituted with -NH-CO-, and one or more -CH2-CH2-CH2- in the said alkyl group may be substituted with -O-CO-O-, and one or more hydrogen atoms in the said alkyl group may each independently be substituted with a halogen atom, provided that there is no direct bonding between oxygen atoms, and the substituent S vi1 In cases where there is a plural, they may be the same or different, Z vi1 Each represents, independently, any one of a single bond and an alkylene group having 1 to 20 carbon atoms, and one or more -CH2- in said alkylene groups may each independently be substituted with -O-, -CF2- and / or -CO-, and one or more -CH2-CH2- in said alkylene groups may each independently be substituted with -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, and one or more -CH2-CH2-CH2- in said alkyl groups may each independently be substituted with -O-CO-O-, and oxygen There are no cases where the atom and the oxygen atom directly bond, and n vi1 represents an integer from 1 to 3, A vi1 and Z vi1 A liquid crystal composition comprising one or more of the compounds represented by (where multiple compounds exist, they may each be the same or different). Claim 6 In claim 1 or claim 2, also, the following general formula (vii) (among the above general formula (vii), R vii1 and R vii2 Each represents, independently, a halogen atom, a cyano group, or an alkyl group having 1 to 20 carbon atoms; one or more -CH2- in the alkyl group may each independently be substituted with -O-, -S-, -CO- and / or -CS-; one or more -CH2-CH2- in the alkyl group may each independently be substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-; one or more -CH2-CH2-CH2- in the alkyl group may each independently be substituted with -O-CO-O-; and one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom. It is possible, but there are no cases where oxygen atoms directly bond with each other, and A vii1 , A vii2 , A vii3 Each is independently of the following groups (a), (b), and (c): (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- present in this group may be substituted with -O-), (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= present in this group may be substituted with -N=), and (c) naphthalene-1,4-diyl group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (one -CH= or present in the naphthalene-1,4-diyl group, naphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group). A liquid crystal composition comprising one or more compounds represented by a group selected from the group consisting of two or more non-adjacent -CH= groups (which may be substituted with -N=), wherein one or more hydrogen atoms among the above groups (a), (b), and (c) may each be independently substituted with a halogen atom, a cyano group, or an alkyl group having 1 to 6 carbon atoms. Claim 7 In claim 1 or claim 2, also, the following general formula (v) ( among general formula (v), R v1 A represents an alkyl group having 1 to 20 carbon atoms, wherein one or more -CH2- in the alkyl group may each independently be substituted with -O-, -S-, -CO- and / or -CS-, and one or more -CH2-CH2- in the alkyl group may each independently be substituted with -CH=CH-, -CO-O-, -O-CO- and / or -C≡C-, and one or more hydrogen atoms in the alkyl group may each independently be substituted with halogen atoms, provided that there is no direct bonding between oxygen atoms, and A v1 and A v2 Each independently, the following groups (a), (b), (c), and (d): (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- present in this group may be substituted with -O- and / or -S-) (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= present in this group may be substituted with -N=) (c) naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (one -CH= or two or more non-adjacent -CH= present in the naphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with -N= (d) A group selected from the group consisting of thiophene-2,5-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group, and thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= present in this group may be substituted with -N=), and the above A v1 and A v2 One or more hydrogen atoms among them, independently, are substituent S v1 It may be substituted by, and substituent S v1 It represents any one of silver, a halogen atom, a cyano group, or an alkyl group having 1 to 6 carbon atoms, wherein one or more -CH2- in said alkyl group may each be independently substituted with -O-, -S-, -CO- and / or -CS-, and one or more hydrogen atoms present in said alkyl group may each be independently substituted with a halogen atom, provided that there is no direct bonding between oxygen atoms, and the substituent S v1 In cases where there is a plural, they may be the same or different, Z v1 It represents any one of a single bond, -C≡C-, -CH=CH-, or -CF=CF-, Z v1 At least one of represents -C≡C-, and n v1 represents an integer between 1 and 2, and A v1 and Z v1 A liquid crystal composition comprising one or more of the compounds represented by (in cases where there are multiple, they may each be the same or different). Claim 8 In claim 1 or claim 2, general formula (np-1) to (np-3) (among the above general formulas (np-1) to (np-3), R npi and R npii Each independently represents either an alkyl group having 1 to 20 carbon atoms or a halogen atom, and one or more -CH2- in the alkyl group may each independently be substituted with -O-, -S-, -CO- and / or -CS-, and one or more -CH2-CH2- in the alkyl group may each independently be substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF- and / or -C≡C-, and one or more -CH2-CH2-CH2- in the alkyl group may each independently be substituted with -O-CO-O-, and one or more hydrogen atoms in the alkyl group may each independently They may be substituted with halogen atoms, provided that there are no direct bonds between oxygen atoms, and rings A, B, C, and D each independently comprise the following groups (a), (b), (c), and (d): (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- present in this group may be substituted with -O-) (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= present in this group may be substituted with -N=) (c) naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or (1 -CH= or two or more non-adjacent -CH= present in the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with -N=.)(d) Represents a group selected from the group consisting of a 1,4-cyclohexenylene group, a 1,3-dioxane-trans-2,5-diyl group, a pyrimidine-2,5-diyl group, or a pyridine-2,5-diyl group, wherein one or more hydrogen atoms of the above-mentioned ring A, ring B, ring C, and ring D are each independently a substituent S npi1 It may be substituted by, and substituent S npi1 It represents any one of silver, a halogen atom, a cyano group, or an alkyl group having 1 to 20 carbon atoms, wherein one or more -CH2- in said alkyl group may each independently be substituted with -O-, -S-, -CO- and / or -CS-, and one or more -CH2-CH2- in said alkyl group may each independently be substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-, and one or more -CH2-CH2-CH2- in said alkyl group may each independently be substituted with -O-CO-O-, and one or more hydrogen atoms in said alkyl group may each independently be substituted with a halogen atom. However, there are no cases where oxygen atoms directly bond with each other, and the substituent S npi1 In cases where there is a plural, they may be the same or different, Z npi , Z npii and Z npiii Each represents independently any one of a single bond or an alkylene group having 1 to 20 carbon atoms, and one or more -CH2- in said alkylene groups may each independently be substituted with -O-, and one or more -CH2-CH2- in said alkylene groups may each independently be substituted with -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, and one or more -CH2-CH2-CH2- in said alkyl groups may each independently be substituted with -O-CO-O-, provided that in cases where oxygen atoms are directly bonded to each other A liquid crystal composition comprising one or more of the compounds indicated as (none). Claim 9 A liquid crystal composition according to claim 1 or claim 2, wherein Δn at 25°C and 589 nm is 0.30 or higher. Claim 10 A liquid crystal display element using the liquid crystal composition described in claim 1 or claim 2. Claim 11 A liquid crystal display element according to claim 10, driven by an active matrix method or a passive matrix method. Claim 12 A liquid crystal display element that reversibly switches the dielectric constant by reversibly changing the orientation direction of the liquid crystal molecules of the liquid crystal composition described in claim 1 or claim 2. Claim 13 A sensor using the liquid crystal composition described in claim 1 or claim 2. Claim 14 A liquid crystal lens using the liquid crystal composition described in claim 1 or claim 2. Claim 15 An optical communication device using the liquid crystal composition described in claim 1 or claim 2. Claim 16 An antenna using the liquid crystal composition described in claim 1 or claim 2. Claim 17 An antenna using a liquid crystal composition as described in claim 1 or claim 2, comprising: a first substrate having a plurality of slots; a second substrate facing the first substrate and having a feed portion installed thereon; a first dielectric layer installed between the first substrate and the second substrate; a plurality of patch electrodes arranged corresponding to the plurality of slots; a third substrate having the patch electrodes installed thereon; and a liquid crystal layer installed between the first substrate and the third substrate, wherein the liquid crystal layer contains the liquid crystal composition as described in claim 1 or claim 2. Claim 18 The following general formula (i) ( among general formula (i), R i1 A represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 20 carbon atoms, wherein one or more -CH2- in the alkyl group may each independently be substituted with -O-, -S-, -CO- and / or -CS-, and one or more -CH2-CH2- in the alkyl group may each independently be substituted with -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH- and / or -CF=CF-, and one or more -CH2-CH2-CH2- in the alkyl group may each independently be substituted with -O-CO-O-, and one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom, provided that there is no direct bonding between oxygen atoms, and A i1 ...represents a 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- present in this group may be substituted with -O- and / or -S-), and A i2 and A i3 Each is independently of the following groups (a), (b), (c) and (d): (a) 1,4-cyclohexylene group (one -CH2- or two or more non-adjacent -CH2- present in this group may be substituted with -O- and / or -S-) (b) 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= present in this group may be substituted with -N=) (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, (d) 1 -CH= or 2 or more non-adjacent -CH= present in decahedronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthrene-2,7-diyl group (one -CH= or two or more non-adjacent -CH= present in naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group or phenanthrene-2,7-diyl group may be substituted with -N=.) It represents a group selected from the group consisting of benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group, and thieno[3,2-b]thiophene-2,5-diyl group (one -CH= or two or more non-adjacent -CH= present in this group may be substituted with -N=), wherein A i1 , A i2 and A i3 One or more hydrogen atoms among them, independently, are substituent S i1 It may be substituted by, and substituent S i1 It represents any one of silver, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms, wherein one or more -CH2- in said alkyl group may each independently be substituted with -O-, -S- and / or -CO-, and one or more -CH2-CH2- in said alkyl group may each independently be substituted with -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or It may be substituted with -NH-CO-, and one or more -CH2-CH2-CH2- in the alkyl group may each independently be substituted with -O-CO-O-, and one or more hydrogen atoms in the alkyl group may each independently be substituted with halogen atoms, provided that there is no direct bonding between oxygen atoms, and the substituent S i1 In cases where there is a plural, they may be the same or different, Z i1 A compound represented by, wherein one of the alkylene groups having 1 to 20 carbon atoms, and one or more -CH2- in the alkylene group may each be independently substituted with -O-, -CF2- and / or -CO-, and one or more -CH2-CH2- in the alkylene group may each be independently substituted with -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, provided that there are no direct bonds between oxygen atoms.

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