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

Abstract

The present invention aims to provide a ni High, large Δn, V th Low, Δε r Large, tanδ iso Liquid crystal compositions that are small in size and have good storage properties at low temperatures, liquid crystal compositions, and liquid crystal display devices, sensors, liquid crystal lenses, optical communication devices, and antennas using the same. Specifically, the invention relates to a compound represented by the general formula (i) having an ethynylene group (-C≡C-) and an isothiocyanate group (-NCS), and a liquid crystal composition containing one or more such compounds.

Description

Technical Field

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

[0002] As a novel application for liquid crystals, which are often used in displays, antennas using liquid crystals for transmitting and receiving radio waves between mobile objects such as cars and communication satellites are attracting attention. Previously, satellite communications used parabolic antennas, but when used in mobile objects such as cars, the parabolic antennas had to be constantly oriented toward the satellite, requiring a large movable part. However, antennas using liquid crystals can change the direction of radio wave transmission and reception by operating the liquid crystals within the panel. This eliminates the need to move the antenna itself and allows for a flat antenna shape. Furthermore, to achieve global high-capacity and high-speed communications, research is underway to create low-orbit satellite constellations based on multiple low-orbit satellites. Liquid crystal antennas that 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 speaking, autonomous driving of vehicles and other devices requires downloading large amounts of high-precision three-dimensional map information. However, by integrating a liquid crystal antenna into a vehicle, it is possible to download large amounts of data from communication satellites without mechanically moving parts. The frequency band used in satellite communications is approximately 13 GHz, significantly different from the frequency used in liquid crystal displays. Consequently, the physical properties required of liquid crystals are also significantly different. Liquid crystals used for antennas require a Δn of approximately 0.4 and an operating temperature range of -20°C to 120°C.

[0004] Infrared laser image recognition and ranging devices using liquid crystals are also attracting attention as sensors for autonomous driving of vehicles such as automobiles. The required Δn for liquid crystals used in these applications is 0.3 to 0.6, and the operating temperature range is 10°C to 100°C.

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

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

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

[0008] Prior Art Literature

[0009] Patent Literature

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

[0011] Non-patent literature

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

[0013] Problems to be solved by the invention

[0014] The present invention aims to provide a ni High, large Δn, V th Low, Δε r Large, tanδ iso A compound for a liquid crystal composition that is small and has good storage properties at low temperatures, 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.

[0015] Means used to solve problems

[0016] As a result of diligent research, the present inventors discovered that a liquid crystal composition containing one or more compounds represented by the general formula (i) having an ethynylene group (-C≡C-) and an isothiocyanate group (-NCS) can solve the above problems, thereby completing the present invention.

[0017] The present invention for solving the above-mentioned problems has the following configuration.

[0018] The compound of the present invention is characterized by being represented by the following general formula (i).

[0019]

[0020] (In general formula (i),

[0021] R i1 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 20 carbon atoms,

[0022] One or more -CH2- groups in the alkyl group may be independently substituted by -O-, -S-, -CO- and / or -CS-.

[0023] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-,

[0024] One or more -CH2-CH2-CH2- in the alkyl group may be independently substituted by -O-CO-O-.

[0025] One or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom.

[0026] But the oxygen atoms are not directly connected to each other.

[0027] A i1 、A i2 and A i3 Each independently represents a group selected from the group consisting of the following groups (a), (b), (c) and (d):

[0028] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups in this group may be substituted with -O- and / or -S-),

[0029] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= groups in this group may be substituted with -N=.)

[0030] (c) 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene-2, 7-diyl (one -CH= or two or more non-adjacent -CH= groups in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl may be substituted with -N=),

[0031] (d) thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=);

[0032] A i1 Does not represent 1,2,3,4-tetrahydronaphthalene-2,6-diyl,

[0033] A i1 、A i2 and A i3 One or more hydrogen atoms in the group may be independently substituted by a substituent group Si1 replace,

[0034] Substituent S i1 represents any one of 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, and an alkyl group having 1 to 20 carbon atoms,

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

[0036] One or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-,

[0037] One or more -CH2-CH2-CH2- in the alkyl group may be independently substituted by -O-CO-O-.

[0038] One or two or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom.

[0039] But the oxygen atoms are not directly connected to each other.

[0040] In the substituent S i1 When there are multiple, they can be the same or different.

[0041] Z i1 represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms,

[0042] One or more -CH2- in the alkylene group may be independently substituted by -O-, -CF2- and / or -CO-.

[0043] One or more -CH2-CH2- in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-,

[0044] But the oxygen atoms are not directly connected to each other).

[0045] Furthermore, the liquid crystal composition of the present invention is characterized by containing one or more of the above-mentioned compounds.

[0046] Furthermore, the liquid crystal display element of the present invention is characterized by using the above-mentioned liquid crystal composition.

[0047] Furthermore, the sensor of the present invention is characterized by using the above-mentioned liquid crystal composition.

[0048] Furthermore, the liquid crystal lens of the present invention is characterized by using the above-mentioned liquid crystal composition.

[0049] Furthermore, an optical communication device of the present invention is characterized by using the above-mentioned liquid crystal composition.

[0050] Furthermore, the antenna of the present invention is characterized by using the above-mentioned liquid crystal composition.

[0051] Effects of the Invention

[0052] According to the present invention, a liquid crystal composition containing one or more compounds represented by the general formula (i) having an ethynylene group (-C≡C-) and an isothiocyanate group (-NCS) can be obtained. ni High, large Δn, V th Low, Δε r Large, tanδ iso A liquid crystal composition that is small and has good storage properties at low temperatures, and is useful for liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas. BRIEF DESCRIPTION OF THE DRAWINGS

[0053] [ Figure 1 ] is an example of a schematic diagram of a vehicle equipped with the antenna of the present invention.

[0054] [ Figure 2 ] is an example of a decomposition diagram of the antenna of the present invention.

[0055] [ Figure 3 ] is an example of a decomposition diagram of the antenna body of the present invention.

[0056] [ Figure 4 ] is an example of a top view of the slot array portion of the present invention.

[0057] [ Figure 5 ] is an example of a top view of the projection diagram of the antenna body of the present invention.

[0058] [ Figure 6 ] is cut along line AA Figure 5 A cross-sectional view of the antenna body.

[0059] [ Figure 7 ] is cut along line AA Figure 5 Another form of a cross-sectional view of the antenna body.

[0060] [ Figure 8 ] is another example of a top view showing a projection diagram of the antenna body of the present invention.

[0061] [ Figure 9 ] is cut along CC line Figure 8 A cross-sectional view of the antenna body.

[0062] [ Figure 10 ] is cut along line BB Figure 8 A cross-sectional view of the antenna body. DETAILED DESCRIPTION

[0063] (Compound represented by general formula (i))

[0064] The compound of the present invention is a compound represented by the following general formula (i) having an ethynylene group (—C≡C—) and an isothiocyanate group (—NCS).

[0065] The liquid crystal composition of the present invention contains one or more compounds represented by the general formula (i) having an ethynylene group (—C≡C—) and an isothiocyanate group (—NCS).

[0066]

[0067] In the general formula (i), R i1 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 20 carbon atoms.

[0068] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0069] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0070] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0071] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0072] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0073] Furthermore, one or two or more -CH2-CH2-CH2- in the alkyl group may be independently substituted with -O-CO-O-.

[0074] Furthermore, one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[0075] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0076] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0077] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0078] For example, R i1 By substituting one -CH2- in the alkyl group with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0079] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

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

[0081] In addition, R i1 By substituting one -CH2- in the alkyl group with -S-, a thioalkoxy group (alkylsulfanyl, alkylthio) having 1 to 19 carbon atoms can be represented.

[0082] The thioalkoxy group is a linear, branched or cyclic thioalkoxy group, and is preferably a linear thioalkoxy group.

[0083] The number of carbon atoms in the thioalkoxy group is preferably 1 to 10, more preferably 1 to 6.

[0084] In addition, R i1 By replacing one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0085] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

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

[0087] In addition, R i1 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0088] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0089] The number of carbon atoms in the alkynyl group is preferably 2 to 10, more preferably 2 to 6.

[0090] In addition, R i1 By substituting one -CH2- in the alkyl group with -O- and substituting one or two or more -CH2-CH2- with -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented.

[0091] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0092] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0093] In addition, R i1 By substituting one or two or more hydrogen atoms in the alkyl group with a halogen atom, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0094] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0095] The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, more preferably 2 to 6.

[0096] R i1 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 two or more hydrogen atoms in the alkyl group with halogen atoms.

[0097] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[0098] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0099] As R i1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) include the following: i1 -1)~(R i1 -36) etc.

[0100]

[0101] Formula (R i1 -1)~(R i1 -36), the black dot indicates the direction to A i1 connection key.

[0102] Furthermore, as R i1 From the viewpoint of solubility, a linear alkyl group having 2 to 6 carbon atoms or a linear thioalkoxy group having 2 to 6 carbon atoms is preferred.

[0103] In the general formula (i), A i1 、A i2 and A i3 Each independently represents a group selected from the group consisting of the following groups (a), (b), (c) and (d):

[0104] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups in the group may be substituted with -O- and / or -S-)

[0105] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=)

[0106] (c) 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene-2,6-diyl ,7-diyl (one -CH= or two or more non-adjacent -CH= groups in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl may be substituted with -N=)

[0107] (d) Thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=).

[0108] However, A i1 It does not represent 1,2,3,4-tetrahydronaphthalene-2,6-diyl.

[0109] A i1 、A i2 and A i3 One or more hydrogen atoms in the group may be independently substituted by a substituent group S i1 replace.

[0110] Substituent S i1It represents any one of 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, and an alkyl group having 1 to 20 carbon atoms.

[0111] The alkyl group is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0112] The number of carbon atoms in the alkyl group is preferably 2 to 10, more preferably 3 to 6.

[0113] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S- and / or -CO-.

[0114] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-.

[0115] Furthermore, one or two or more -CH2-CH2-CH2- groups in the alkyl group may be substituted with -O-CO-O-.

[0116] One or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[0117] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0118] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0119] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0120] As a substituent S i1 , preferably a halogen atom, preferably a fluorine atom.

[0121] In addition, A i1 and A i2 At least one of the substituents S is preferably replaced by at least one i1 Substitution is preferably by a halogen atom, preferably by a fluorine atom.

[0122] Furthermore, in the substituent S i1 When there are multiple ones, they may be the same or different.

[0123] As A i1 The substituent S in i1The substitution position is preferably the following formula (A i1 -SP-1)~(A i1 -SP-2).

[0124]

[0125] Formula (A i1 -SP-1)~(A i1 -SP-2), the white dot indicates the direction to R i1 The black dot represents the bond to the ethynylene group (-C≡C-).

[0126] As A i2 The substituent S in i1 The substitution position is preferably the following formula (A i2 -SP-1)~(A i2 -SP-3).

[0127]

[0128] Formula (A i2 -SP-1)~(A i2 -SP-3), the white dots represent the bonds to the ethynylene group (-C≡C-), and the black dots represent the bonds to Z i1 connection key.

[0129] As A i3 The substituent S in i1 The substitution position is preferably the following formula (A i3 -SP-1)~(A i3 -SP-3).

[0130]

[0131] Formula (A i3 -SP-1)~(A i3 -SP-3), the white dot indicates the direction of Z i1 The black dot represents the bond to the isothiocyanate group (-NCS).

[0132] More specifically, A i1 Preferably, it is represented by the following formula (A i1 -1)~(A i1 -6) any one.

[0133]

[0134] Formula (A i1 -1)~(A i1 -6), the white dot indicates the direction to R i1The black dot represents the bond to the ethynylene group (-C≡C-).

[0135] A i1 From the viewpoint of solubility, the compound represented by the above formula (A) is particularly preferred. i1 -1) or (A i1 -6).

[0136] More specifically, A i2 Preferably, it is represented by the following formula (A i2 -1)~(A i2 -7).

[0137]

[0138] Formula (A i2 -1)~(A i2 -7), the white dots represent the bonds to the ethynylene group (-C≡C-), and the black dots represent the bonds to Z i1 connection key.

[0139] A i2 From Δn and / or Δε r From the viewpoint of i2 -1)、(A i2 -2) or (A i2 -6), particularly preferably represents (A i2 -1).

[0140] More specifically, A i3 Preferably, it is represented by the following formula (A i3 -1)~(A i3 -Any of 4).

[0141]

[0142] Formula (A i3 -1)~(A i3 -4), the white dot indicates the direction Z i1 The black dot represents the bond to the isothiocyanate group (-NCS).

[0143] A i3 From Δn and / or Δε r From the viewpoint of i3 -1)、(A i3 -2) or (A i3 -3), particularly preferably represents (A i3 -3).

[0144] In the general formula (i), Z i1 It represents any of a single bond and an alkylene group having 1 to 20 carbon atoms.

[0145] The alkylene group is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0146] The number of carbon atoms in the alkylene group is preferably 2 to 10, more preferably 2 to 6.

[0147] One or two or more -CH2- groups in the alkylene group may be independently substituted with -O-, -CF2- and / or -CO-.

[0148] In addition, one or more -CH2-CH2- groups in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[0149] However, when the alkylene group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0150] Specific examples of the alkylene group having 2 to 20 carbon atoms (including substituted groups) include the following: i1 -1)~(Z i1 -24) represented by the base, etc.

[0151]

[0152] Formula (Z i1 -1)~(Z i1 -24), the white dot indicates the direction to A i2 The black dot indicates the connection bond to A i3 connection key.

[0153] From Δn and / or Δε r From the perspective of Z i1 It is preferably a single bond or -C≡C-.

[0154] As the compound represented by the general formula (i), compounds represented by the following general formulas (i-1) to (i-2) are preferred.

[0155]

[0156] In the general formulas (i-1) to (i-2), R i1 、A i1 and Z i1 Represents the same as R in the above general formula (i) i1 、A i1 and Z i1The same meanings are given for each group, and the preferred groups also represent the same groups. Specifically, R i1 From the viewpoint of solubility, a linear alkyl group having 2 to 6 carbon atoms or a linear thioalkoxy group having 2 to 6 carbon atoms is preferred.

[0157] Specifically, A i1 Preferably, it is represented by the following formula (A i1 -1)~(A i1 -6) is preferably the following formula (A i1 -1) or (A i1 -6).

[0158]

[0159] Formula (A i1 -1)~(A i1 -6), the white dot indicates the direction to R i1 The black dot represents the bond to the ethynylene group (-C≡C-).

[0160] Specifically, Z i1 Preferred is a single bond, -C≡C- or -CH=CH-.

[0161] In the 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 、X i-1-3-2 、X i-1-3-3 、X i-1-3-5 、X i-1-3-6 Each independently represents a hydrogen atom or a substituent S i1 .

[0162] Substituent S i1 represents the substituent S in the above general formula (i) i1 The same meanings apply to each other, and preferred groups also refer to the same groups.

[0163] As the compound represented by the general formula (i-1), compounds represented by the following general formulae (i-1-1) to (i-1-43) are preferred.

[0164]

[0165]

[0166] In the general formulas (i-1-1) to (i-1-43), R i1and S i1 Each independently represents R in the above general formula (i) i1 and S i1 Same meaning.

[0167] Specific examples of the compound represented by general formula (i-1-1) include compounds represented by the following structural formulas (i-1-1.1) to (i-1-1.4).

[0168]

[0169] Specific examples of the compound represented by general formula (i-1-2) include compounds represented by the following structural formulas (i-1-2.1) to (i-1-2.4).

[0170]

[0171] Specific examples of the compound represented by general formula (i-1-3) include compounds represented by the following structural formulas (i-1-3.1) to (i-1-3.4).

[0172]

[0173] Specific examples of the compound 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).

[0174]

[0175] Specific examples of the compound represented by General Formula (i-1-5) include compounds represented by the following structural formulas (i-1-5.1) to (i-1-5.8).

[0176]

[0177] Specific examples of the compound represented by the general formula (i-1-6) include compounds represented by the following structural formulas (i-1-6.1) to (i-1-6.2).

[0178]

[0179] Specific examples of the compound represented by general formula (i-1-7) include compounds represented by the following structural formulas (i-1-7.1) to (i-1-7.4).

[0180]

[0181] Specific examples of the compound represented by General Formula (i-1-8) include compounds represented by the following structural formulas (i-1-8.1) to (i-1-8.5).

[0182]

[0183] Specific examples of the compound represented by general formula (i-1-9) include compounds represented by the following structural formulas (i-1-9.1) to (i-1-9.4).

[0184]

[0185] Specific examples of the compound represented by General Formula (i-1-10) include compounds represented by the following Structural Formula (i-1-10.1).

[0186]

[0187] Specific examples of the compound represented by General Formula (i-1-11) include compounds represented by the following structural formulas (i-1-11.1) to (i-1-11.16).

[0188]

[0189]

[0190] Specific examples of the compound represented by General Formula (i-1-12) include compounds represented by the following structural formulas (i-1-12.1) to (i-1-12.4).

[0191]

[0192] Specific examples of the compound represented by General Formula (i-1-13) include compounds represented by the following structural formulas (i-1-13.1) to (i-1-13.4).

[0193]

[0194] Specific examples of the compound represented by General Formula (i-1-14) include compounds represented by the following structural formulas (i-1-14.1) to (i-1-14.4).

[0195]

[0196] Specific examples of the compound represented by General Formula (i-1-15) include compounds represented by the following structural formulas (i-1-15.1) to (i-1-15.4).

[0197]

[0198] Specific examples of the compound represented by General Formula (i-1-16) include compounds represented by the following structural formulas (i-1-16.1) to (i-1-16.5).

[0199]

[0200] Specific examples of the compound represented by General Formula (i-1-17) include compounds represented by the following structural formulas (i-1-17.1) to (i-1-17.2).

[0201]

[0202] Specific examples of the compound represented by General Formula (i-1-18) include compounds represented by the following structural formulas (i-1-18.1) to (i-1-18.5).

[0203]

[0204] Specific examples of the compound represented by General Formula (i-1-19) include compounds represented by the following structural formulas (i-1-19.1) to (i-1-19.14).

[0205]

[0206]

[0207] Specific examples of the compound represented by General Formula (i-1-20) include compounds represented by the following structural formulas (i-1-20.1) to (i-1-20.4).

[0208]

[0209] Specific examples of the compound represented by General Formula (i-1-21) include compounds represented by the following Structural Formula (i-1-21.1).

[0210]

[0211] Specific examples of the compound represented by General Formula (i-1-22) include compounds represented by the following structural formulas (i-1-22.1) to (i-1-22.4).

[0212]

[0213] Specific examples of the compound represented by General Formula (i-1-23) include compounds represented by the following structural formulas (i-1-23.1) to (i-1-23.4).

[0214]

[0215] Specific examples of the compound represented by General Formula (i-1-24) include compounds represented by the following structural formula (i-1-24.1).

[0216]

[0217] Specific examples of the compound represented by General Formula (i-1-25) include compounds represented by the following structural formulas (i-1-25.1) to (i-1-25.4).

[0218]

[0219] Specific examples of the compound represented by General Formula (i-1-26) include compounds represented by the following structural formulas (i-1-26.1) to (i-1-26.4).

[0220]

[0221] Specific examples of the compound represented by General Formula (i-1-27) include compounds represented by the following structural formulas (i-1-27.1) to (i-1-27.19).

[0222]

[0223]

[0224]

[0225] Specific examples of the compound represented by General Formula (i-1-28) include compounds represented by the following structural formulas (i-1-28.1) to (i-1-28.5).

[0226]

[0227] Specific examples of the compound represented by General Formula (i-1-29) include compounds represented by the following structural formulas (i-1-29.1) to (i-1-29.5).

[0228]

[0229] Specific examples of the compound represented by General Formula (i-1-30) include compounds represented by the following structural formulas (i-1-30.1) to (i-1-30.4).

[0230]

[0231] Specific examples of the compound represented by General Formula (i-1-31) include compounds represented by the following structural formula (i-1-31.1).

[0232]

[0233] Specific examples of the compound represented by General Formula (i-1-32) include compounds represented by the following structural formula (i-1-32.1).

[0234]

[0235] Specific examples of the compound represented by General Formula (i-1-33) include compounds represented by the following structural formulas (i-1-33.1) to (i-1-33.4).

[0236]

[0237] Specific examples of the compound represented by General Formula (i-1-34) include compounds represented by the following structural formulas (i-1-34.1) to (i-1-34.4).

[0238]

[0239] Specific examples of the compound represented by General Formula (i-1-35) include compounds represented by the following structural formulas (i-1-35.1) to (i-1-35.5).

[0240]

[0241] Specific examples of the compound represented by General Formula (i-1-36) include compounds represented by the following structural formulas (i-1-36.1) to (i-1-36.4).

[0242]

[0243] Specific examples of the compound represented by General Formula (i-1-37) include compounds represented by the following structural formulas (i-1-37.1) to (i-1-37.5).

[0244]

[0245] Specific examples of the compound represented by General Formula (i-1-38) include compounds represented by the following structural formulas (i-1-38.1) to (i-1-38.8).

[0246]

[0247]

[0248] Specific examples of the compound represented by General Formula (i-1-39) include compounds represented by the following structural formulas (i-1-39.1) to (i-1-39.4).

[0249]

[0250] Specific examples of the compound represented by General Formula (i-1-40) include compounds represented by the following structural formulas (i-1-40.1) to (i-1-40.4).

[0251]

[0252] Specific examples of the compound represented by General Formula (i-1-41) include compounds represented by the following Structural Formula (i-1-41.1).

[0253]

[0254] Specific examples of the compound represented by General Formula (i-1-42) include compounds represented by the following Structural Formula (i-1-42.1).

[0255]

[0256] Specific examples of the compound represented by General Formula (i-1-43) include compounds represented by the following Structural Formula (i-1-43.1).

[0257]

[0258] As the compound represented by the general formula (i-2), a compound represented by the following general formula (i-2-1) is preferable.

[0259]

[0260] In the general formula (i-2-1), R i1 and S i1 Each independently represents R in the above general formula (i) i1 and S i1 Same meaning.

[0261] Specific examples of the compound represented by General Formula (i-2-1) include compounds represented by the following structural formula (i-2-1.1).

[0262]

[0263] General formula (i), general formula (i-1) to (i-2), general formula (i-1-1) to (i-1-43), general formula (i-2-1), structural formula (i-1-1.1) to (i-1-1.4), structural formula (i-1-2.1) to (i-1-2.4), structural formula (i-1-3.1) to (i-1-3.4), structural formula (i-1-4.1) to (i-1-4.4), structural formula (i-1-5.1) to (i-1-5.8), structural formula (i-1-6.1) to (i-1-6.2), structural formula (i-1-7.1) to (i-1-7.4), structural formula (i-1-8.1) to (i-1-8.5), structural formula (i-1-9.1) to ( i-1-9.4), structural formula (i-1-10.1), structural formula (i-1-11.1) to (i-1-11.16), structural formula (i-1-12.1) to (i-1-12.4), structural formula (i-1-13.1) to (i-1-13.4), structural formula (i-1-14.1) to (i-1-14.4), structural formula (i-1-15.1) to (i-1-15.4), structural formula (i-1-16.1) to (i-1-16.5), structural formula (i-1-17.1) to (i-1-17.2), structural formula (i-1-18.1) to (i-1-18.5), structural formula (i-1-19.1) to (i-1-19.14 )、Structural formula (i-1-20.1)~(i-1-20.4)、Structural formula (i-1-21.1)、Structural formula (i-1-22.1)~(i-1-22.4)、Structural formula (i-1-23.1)~(i-1-23.4)、Structural formula (i-1-24.1)、Structural formula (i-1-25.1)~(i-1-25.4)、Structural formula (i-1-26.1)~(i-1-26.4)、Structural formula (i-1-27.1)~(i-1-27.19)、Structural formula (i-1-28.1)~(i-1-28.5)、Structural formula (i-1-29.1)~(i-1-29.5)、Structural formula (i-1-30.1)~(i -1-30.4)、Structural formula (i-1-31.1)、Structural formula (i-1-32.1)、Structural formula (i-1-33.1)~(i-1-33.4)、Structural formula (i-1-34.1)~(i-1-34.4)、Structural formula (i-1-35.1)~(i-1-35.5)、Structural formula (i-1-36.1)~(i-1-36.4)、Structural formula (i-1-37.1)~(i-1-37.5)、Structural formula (i-1-38.1)~(i-1-38.8)、Structural formula (i-1-39.1)~(i-1-39.4)、Structural formula (i-1-40.1)~(i-1-40.4)、Structural formula (i-1-41.1) The number of compounds represented by structural formula (i-1-42.1), structural formula (i-1-43.1) or structural formula (i-2-1.1) used in the liquid crystal composition is one or more, preferably one to five, preferably one to four, and preferably one to three.

[0264] General formula (i), general formula (i-1) to (i-2), general formula (i-1-1) to (i-1-43), general formula (i-2-1), structural formula (i-1-1.1) to (i-1-1.4), structural formula (i-1-2.1) to (i-1-2.4), structural formula (i-1-3.1) to (i-1-3.4), structural formula (i-1-4.1) to (i-1-4.4), structural formula (i-1-5.1) to (i-1-5.8), structural formula (i-1-6.1) to (i-1-6.2), structural formula (i-1-7.1) to (i-1-7.4), structural formula (i-1-8.1) to (i-1-8.5), structural formula (i-1-9.1) to ( i-1-9.4), structural formula (i-1-10.1), structural formula (i-1-11.1) to (i-1-11.16), structural formula (i-1-12.1) to (i-1-12.4), structural formula (i-1-13.1) to (i-1-13.4), structural formula (i-1-14.1) to (i-1-14.4), structural formula (i-1-15.1) to (i-1-15.4), structural formula (i-1-16.1) to (i-1-16.5), structural formula (i-1-17.1) to (i-1-17.2), structural formula (i-1-18.1) to (i-1-18.5), structural formula (i-1-19.1) to (i-1-19.14 )、Structural formula (i-1-20.1)~(i-1-20.4)、Structural formula (i-1-21.1)、Structural formula (i-1-22.1)~(i-1-22.4)、Structural formula (i-1-23.1)~(i-1-23.4)、Structural formula (i-1-24.1)、Structural formula (i-1-25.1)~(i-1-25.4)、Structural formula (i-1-26.1)~(i-1-26.4)、Structural formula (i-1-27.1)~(i-1-27.19)、Structural formula (i-1-28.1)~(i-1-28.5)、Structural formula (i-1-29.1)~(i-1-29.5)、Structural formula (i-1-30.1)~(i -1-30.4)、Structural formula (i-1-31.1)、Structural formula (i-1-32.1)、Structural formula (i-1-33.1)~(i-1-33.4)、Structural formula (i-1-34.1)~(i-1-34.4)、Structural formula (i-1-35.1)~(i-1-35.5)、Structural formula (i-1-36.1)~(i-1-36.4)、Structural formula (i-1-37.1)~(i-1-37.5)、Structural formula (i-1-38.1)~(i-1-38.8)、Structural formula (i-1-39.1)~(i-1-39.4)、Structural formula (i-1-40.1)~(i-1-40.4)、Structural formula (i-1-41.1) The lower limit of the total content of the compounds represented by structural formula (i-1-42.1), structural formula (i-1-43.1) or structural formula (i-2-1.1) in 100% by mass of the liquid crystal composition is preferably 3% by mass or more, preferably 5% by mass or more, preferably 10% by mass or more, preferably 15% by mass or more, preferably 20% by mass or more, preferably 25% by mass or more, preferably 30% by mass or more, and preferably 35% by mass or more.

[0265] General formula (i), general formula (i-1) to (i-2), general formula (i-1-1) to (i-1-43), general formula (i-2-1), structural formula (i-1-1.1) to (i-1-1.4), structural formula (i-1-2.1) to (i-1-2.4), structural formula (i-1-3.1) to (i-1-3.4), structural formula (i-1-4.1) to (i-1-4.4), structural formula (i-1-5.1) to (i-1-5.8), structural formula (i-1-6.1) to (i-1-6.2), structural formula (i-1-7.1) to (i-1-7.4), structural formula (i-1-8.1) to (i-1-8.5), structural formula (i-1-9.1) to ( i-1-9.4), structural formula (i-1-10.1), structural formula (i-1-11.1) to (i-1-11.16), structural formula (i-1-12.1) to (i-1-12.4), structural formula (i-1-13.1) to (i-1-13.4), structural formula (i-1-14.1) to (i-1-14.4), structural formula (i-1-15.1) to (i-1-15.4), structural formula (i-1-16.1) to (i-1-16.5), structural formula (i-1-17.1) to (i-1-17.2), structural formula (i-1-18.1) to (i-1-18.5), structural formula (i-1-19.1) to (i-1-19.14 )、Structural formula (i-1-20.1)~(i-1-20.4)、Structural formula (i-1-21.1)、Structural formula (i-1-22.1)~(i-1-22.4)、Structural formula (i-1-23.1)~(i-1-23.4)、Structural formula (i-1-24.1)、Structural formula (i-1-25.1)~(i-1-25.4)、Structural formula (i-1-26.1)~(i-1-26.4)、Structural formula (i-1-27.1)~(i-1-27.19)、Structural formula (i-1-28.1)~(i-1-28.5)、Structural formula (i-1-29.1)~(i-1-29.5)、Structural formula (i-1-30.1)~(i -1-30.4)、Structural formula (i-1-31.1)、Structural formula (i-1-32.1)、Structural formula (i-1-33.1)~(i-1-33.4)、Structural formula (i-1-34.1)~(i-1-34.4)、Structural formula (i-1-35.1)~(i-1-35.5)、Structural formula (i-1-36.1)~(i-1-36.4)、Structural formula (i-1-37.1)~(i-1-37.5)、Structural formula (i-1-38.1)~(i-1-38.8)、Structural formula (i-1-39.1)~(i-1-39.4)、Structural formula (i-1-40.1)~(i-1-40.4)、Structural formula (i-1-41.1) The upper limit of the total content of the compounds represented by structural formula (i-1-42.1), structural formula (i-1-43.1) or structural formula (i-2-1.1) in 100% by mass of the liquid crystal composition is preferably 75% by mass or less, preferably 70% by mass or less, preferably 65% ​​by mass or less, preferably 55% by mass or less, preferably 45% by mass or less, preferably 35% by mass or less, preferably 25% by mass or less, preferably 15% by mass or less, and preferably 10% by mass or less.

[0266] General formula (i), general formula (i-1) to (i-2), general formula (i-1-1) to (i-1-43), general formula (i-2-1), structural formula (i-1-1.1) to (i-1-1.4), structural formula (i-1-2.1) to (i-1-2.4), structural formula (i-1-3.1) to (i-1-3.4), structural formula (i-1-4.1) to (i-1-4.4), structural formula (i-1-5.1) to (i-1-5.8), structural formula (i-1-6.1) to (i-1-6.2), structural formula (i-1-7.1) to (i-1-7.4), structural formula (i-1-8.1) to (i-1-8.5), structural formula (i-1-9.1) to ( i-1-9.4), structural formula (i-1-10.1), structural formula (i-1-11.1) to (i-1-11.16), structural formula (i-1-12.1) to (i-1-12.4), structural formula (i-1-13.1) to (i-1-13.4), structural formula (i-1-14.1) to (i-1-14.4), structural formula (i-1-15.1) to (i-1-15.4), structural formula (i-1-16.1) to (i-1-16.5), structural formula (i-1-17.1) to (i-1-17.2), structural formula (i-1-18.1) to (i-1-18.5), structural formula (i-1-19.1) to (i-1-19.14 )、Structural formula (i-1-20.1)~(i-1-20.4)、Structural formula (i-1-21.1)、Structural formula (i-1-22.1)~(i-1-22.4)、Structural formula (i-1-23.1)~(i-1-23.4)、Structural formula (i-1-24.1)、Structural formula (i-1-25.1)~(i-1-25.4)、Structural formula (i-1-26.1)~(i-1-26.4)、Structural formula (i-1-27.1)~(i-1-27.19)、Structural formula (i-1-28.1)~(i-1-28.5)、Structural formula (i-1-29.1)~(i-1-29.5)、Structural formula (i-1-30.1)~(i -1-30.4)、Structural formula (i-1-31.1)、Structural formula (i-1-32.1)、Structural formula (i-1-33.1)~(i-1-33.4)、Structural formula (i-1-34.1)~(i-1-34.4)、Structural formula (i-1-35.1)~(i-1-35.5)、Structural formula (i-1-36.1)~(i-1-36.4)、Structural formula (i-1-37.1)~(i-1-37.5)、Structural formula (i-1-38.1)~(i-1-38.8)、Structural formula (i-1-39.1)~(i-1-39.4)、Structural formula (i-1-40.1)~(i-1-40.4)、Structural formula (i-1-41.1) The total content of the compound represented by structural formula (i-1-42.1), structural formula (i-1-43.1) or structural formula (i-2-1.1) in 100% by mass of the liquid crystal composition is determined from the solubility, Δn and / or Δε. r From the viewpoint of the content of cellulose, the content is preferably 5 to 75% by mass, more preferably 10 to 70% by mass, and even more preferably 15 to 65% by mass.

[0267] The compound represented by the general formula (i) (including subordinate concepts) can be synthesized using a known synthesis method, and some examples are given below.

[0268] (Preparation Method 1) Preparation of a Compound Represented by the Following Formula (s-6)

[0269]

[0270] (Where R i1 and S i1 Represents the same as R in the above general formula (i) i1 and S i1 Same meaning.)

[0271] By reacting the compound represented by the general formula (s-1) with the compound represented by the general formula (s-2), the compound represented by the general formula (s-3) can be obtained.

[0272] Examples of the reaction method include a Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.

[0273] Specific examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0274] When palladium(II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0275] Specific examples of the copper catalyst include copper (I) iodide.

[0276] Specific examples of the base include triethylamine and the like.

[0277] By reacting the compound represented by the general formula (s-3) with the compound represented by the general formula (s-4), the compound represented by the general formula (s-5) can be obtained.

[0278] Examples of the reaction method include a Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.

[0279] Specific examples of the palladium catalyst, the copper catalyst, and the base include those described above.

[0280] Furthermore, by reacting the compound represented by the general formula (s-5) with 1,1-thiocarbonyldiimidazole, the target compound represented by the general formula (s-6) can be obtained.

[0281] (Preparation Method 2) Preparation of a Compound Represented by the Following Formula (s-14)

[0282]

[0283] (Where R i1 and S i1 Represents the same as R in the above general formula (i) i1 and S i1 Same meaning.)

[0284] By reacting the compound represented by the general formula (s-7) with the compound represented by the general formula (s-8), the compound represented by the general formula (s-9) can be obtained.

[0285] Examples of the reaction method include a Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.

[0286] Specific examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0287] When palladium(II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0288] Specific examples of the copper catalyst include copper (I) iodide.

[0289] Specific examples of the base include triethylamine and the like.

[0290] The compound represented by the general formula (s-9) is reacted with the compound represented by the general formula (s-10), further reacted with butyl lithium at an extremely low temperature (below -60°C), and then reacted with N,N-dimethylformamide to obtain the compound represented by the general formula (s-11).

[0291] Examples of a reaction method for reacting a compound represented by the general formula (s-9) with a compound represented by the general formula (s-10) include a Heck reaction using a palladium catalyst and a base.

[0292] Specific examples of the palladium catalyst and the base include those described above.

[0293] By reacting the compound represented by the general formula (s-11) with, for example, hydroxylamine, the compound represented by the general formula (s-12) can be obtained.

[0294] By reacting the compound represented by the general formula (s-12) with, for example, N-chlorosuccinimide, the compound represented by the general formula (s-13) can be obtained.

[0295] By reacting the compound represented by the general formula (s-13) with, for example, thiourea, the target compound represented by the general formula (s-14) can be obtained.

[0296] (Preparation Method 3) Preparation of a Compound Represented by the Following Formula (s-20)

[0297]

[0298] (Where R i1 and S i1 Represents the same as R in the above general formula (i) i1 and S i1 Same meaning.)

[0299] The compound represented by the general formula (s-15) is reacted with the compound represented by the general formula (s-16), and then reacted with trifluoromethanesulfonic anhydride to obtain the compound represented by the general formula (s-17).

[0300] Examples of the reaction method include a Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.

[0301] Specific examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0302] When palladium(II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0303] Specific examples of the copper catalyst include copper (I) iodide.

[0304] Specific examples of the base include triethylamine and the like.

[0305] By reacting the compound represented by the general formula (s-17) with the compound represented by the general formula (s-18), the compound represented by the general formula (s-19) can be obtained.

[0306] As a reaction method, Suzuki coupling reaction using a palladium catalyst and a base is mentioned, for example.

[0307] Specific examples of the palladium catalyst and the base include those described above.

[0308] Furthermore, by reacting the compound represented by the general formula (s-19) with 1,1-thiocarbonyldiimidazole, the target compound represented by the general formula (s-20) can be obtained.

[0309] (Preparation Method 4) Preparation of a Compound Represented by the Following Formula (S-26)

[0310]

[0311] (Where R i1 and S i1 Represents the same as R in the above general formula (i) i1 and S i1 Same meaning.)

[0312] By reacting the compound represented by the general formula (s-21) with the compound represented by the general formula (s-22), the compound represented by the general formula (s-23) can be obtained.

[0313] Examples of the reaction method include a Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.

[0314] Specific examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0315] When palladium(II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0316] Specific examples of the copper catalyst include copper (I) iodide.

[0317] Specific examples of the base include triethylamine and the like.

[0318] By reacting the compound represented by the general formula (s-23) with the compound represented by the general formula (s-24), the compound represented by the general formula (s-25) can be obtained.

[0319] As a reaction method, Suzuki coupling reaction using a palladium catalyst and a base is mentioned, for example.

[0320] Specific examples of the palladium catalyst and the base include those described above.

[0321] Furthermore, by reacting the compound represented by the general formula (s-25) with 1,1-thiocarbonyldiimidazole, the target compound represented by the general formula (s-26) can be obtained.

[0322] (Preparation Method 5) Preparation of a Compound Represented by the Following Formula (s-32)

[0323]

[0324] (Where R i1 and S i1 Represents the same as R in the above general formula (i) i1 and S i1 Same meaning.)

[0325] By reacting the compound represented by the general formula (s-27) with the compound represented by the general formula (s-28), the compound represented by the general formula (s-29) can be obtained.

[0326] Examples of the reaction method include a Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base.

[0327] Specific examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), and tetrakis(triphenylphosphine)palladium(0).

[0328] When palladium(II) acetate is used as the palladium catalyst, a ligand such as triphenylphosphine or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added.

[0329] Specific examples of the copper catalyst include copper (I) iodide.

[0330] Specific examples of the base include triethylamine and the like.

[0331] By reacting the compound represented by the general formula (s-29) with the compound represented by the general formula (s-30), the compound represented by the general formula (s-31) can be obtained.

[0332] As a reaction method, Suzuki coupling reaction using a palladium catalyst and a base is mentioned, for example.

[0333] Specific examples of the palladium catalyst and the base include those described above.

[0334] Furthermore, by reacting the compound represented by the general formula (s-31) with 1,1-thiocarbonyldiimidazole, the target compound represented by the general formula (s-32) can be obtained.

[0335] (Other compounds)

[0336] (Compound represented by general formula (ii))

[0337] The liquid crystal composition of the present invention is characterized by solubility, Δn and / or Δε r From the viewpoint of , one or more compounds represented by the following general formula (ii) having an isothiocyanate group (—NCS) may be further contained.

[0338]

[0339] In the general formula (ii), R ii1 It represents an alkyl group having 1 to 20 carbon atoms.

[0340] The alkyl group is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0341] The number of carbon atoms in the alkyl group is preferably 2 to 10, more preferably 2 to 6.

[0342] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0343] In addition, one or more -CH2-CH2- in the alkyl group may be substituted by -CH=CH-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0344] Furthermore, one or two or more -CH2-CH2-CH2- groups in the alkyl group may be substituted with -O-CO-O-.

[0345] Furthermore, one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[0346] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0347] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0348] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0349] For example, R ii1 When one -CH2- in the alkyl group is replaced by -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0350] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0351] The number of carbon atoms in the alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0352] In addition, R ii1 When one -CH2- in the alkyl group is replaced by -S-, a thioalkoxy group (alkylthio, alkylthio) having 1 to 19 carbon atoms can be represented.

[0353] The thioalkoxy group is a linear, branched or cyclic thioalkoxy group, and is preferably a linear thioalkoxy group.

[0354] The number of carbon atoms in the thioalkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0355] In addition, R ii1 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0356] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0357] The number of carbon atoms in the alkenyl group is preferably 2 to 10, more preferably 2 to 6.

[0358] In addition, R ii1 When one or two or more -CH2-CH2- groups in the alkyl group are replaced by -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0359] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0360] The number of carbon atoms in the alkynyl group is preferably 2 to 10, more preferably 2 to 6.

[0361] In addition, R ii1 When one -CH2- in the alkyl group is replaced by -O-, and one or two or more -CH2-CH2- are replaced by -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented.

[0362] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0363] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0364] In addition, R ii1 By substituting one or two or more hydrogen atoms in the alkyl group with a halogen atom, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0365] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0366] The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, more preferably 2 to 6.

[0367] In addition, R ii1 When one -CH2- in the alkyl group is substituted with -O-, and one or two or more hydrogen atoms in the alkyl group are substituted with halogen atoms, a halogenated alkoxy group having 1 to 19 carbon atoms can be represented.

[0368] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[0369] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0370] As R ii1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted groups) include the following: ii1 -1)~(R ii1 -37) etc.

[0371]

[0372] Formula (R ii12 -1)~(R ii1 -37), the black dot indicates the direction to A ii1 connection key.

[0373] In R ii1 When the ring structure connected is a phenyl group (aromatic group), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. i1 When the linked ring structure is a saturated ring structure such as cyclohexane, pyran, and dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms.

[0374] In addition, as R ii1 In order to stabilize the nematic phase, the total number of carbon atoms and, if present, oxygen atoms is preferably 5 or less, and a linear chain is preferred.

[0375] Furthermore, as R ii1 From the viewpoint of solubility, a linear alkyl group having 2 to 8 carbon atoms, a linear alkoxy group having 2 to 8 carbon atoms, or a linear halogenated alkoxy group having 2 to 8 carbon atoms is preferred.

[0376] In the general formula (ii), A ii1 and Aii2 Each independently represents a group selected from the group consisting of the following groups (a), (b), (c) and (d):

[0377] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups in the group may be substituted with -O- and / or -S-)

[0378] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=)

[0379] (c) 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene-2,6-diyl ,7-diyl (one -CH= or two or more non-adjacent -CH= groups in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl may be substituted with -N=)

[0380] (d) Thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=).

[0381] A ii1 and A ii2 One or more hydrogen atoms in the group may be independently substituted by a substituent group S ii1 replace.

[0382] Substituent S ii1 represents any one of a halogen atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, and an alkyl group having 1 to 20 carbon atoms.

[0383] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0384] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0385] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0386] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0387] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0388] One or two or more -CH2-CH2-CH2- groups in the alkyl group may be independently substituted with -O-CO-O-.

[0389] Furthermore, one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[0390] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0391] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0392] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0393] As a substituent S ii1 , preferably a fluorine atom or a chlorine atom.

[0394] In addition, A ii1 At least 1 or A ii2 Preferably, at least one substituent S ii1 replace.

[0395] Furthermore, in the substituent S ii1 When there are multiple ones, they may be the same or different.

[0396] As A ii1 The substituent S in ii1 The substitution position is preferably the following formula (A ii1 -SP-1)~(A ii1 -SP-5) in any one.

[0397]

[0398] Formula (A ii1 -SP-1)~(A ii1-SP-5), the white dot indicates the direction to R ii1 or Z ii1 The black dot indicates the connection key to Z ii1 connection key.

[0399] As A ii2 The substituent S in ii1 The substitution position is preferably the following formula (A ii2 -SP-1)~(A ii2 -SP-7).

[0400]

[0401] Formula (A ii2 -SP-1)~(A ii2 -SP-7), the white dot indicates the direction of Z ii1 The black dot represents the bond to the isothiocyanate group (-NCS).

[0402] More specifically, A ii1 Preferably, it is represented by the following formula (A ii1 -1)~(A ii1 -7).

[0403]

[0404] Formula (A ii1 -1)~(A ii1 -7), the white dot indicates the direction to R ii1 or Z ii1 The black dot indicates the connection key to Z ii1 connection key.

[0405] More specifically, A ii2 Preferably, it is represented by the following formula (A ii2 -1)~(A ii2 -6) any one.

[0406]

[0407] Formula (A ii2 -1)~(A ii2 -6), the white dot indicates the direction Z ii1 The black dot represents the bond to the isothiocyanate group (-NCS).

[0408] In the general formula (ii), Z ii1 It represents any of a single bond and an alkylene group having 1 to 20 carbon atoms.

[0409] One or two or more -CH2- groups in the alkylene group may each independently be substituted with -O-.

[0410] In addition, one or more -CH2-CH2- groups in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[0411] Furthermore, one or two or more -CH2-CH2-CH2- in the alkylene group may be independently substituted with -O-CO-O-.

[0412] However, when the alkylene group having 1 to 10 carbon atoms is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0413] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0414] Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted groups) include the following: ii1 -1)~(Z ii1 -24) represented by the base, etc.

[0415]

[0416] Formula (Z ii1 -1)~(Z ii1 -24), the white dot indicates the direction to A ii1 The black dot indicates the connection bond to A ii1 or A ii2 connection key.

[0417] In the general formula (ii), n ii1 It represents an integer of 1 to 4, preferably 1 to 2.

[0418] In n ii1 When Δn and / or Δε is 1, r From the perspective of Z ii1 Preferably, it represents a single bond or -C≡C-.

[0419] In addition, in n ii1 When Δn and / or Δε is 2, r From the perspective of Z ii1 Preferably, it represents a single bond or -C≡C-.

[0420] Furthermore, in the general formula (ii), in A ii1 and Z ii1 When there are multiple ones, they may be the same or different.

[0421] However, the compound represented by the general formula (ii) does not include the compound represented by the general formula (i) (including the subordinate concept).

[0422] As the compound represented by the general formula (ii), compounds represented by the following general formulas (ii-1) to (ii-5) are preferred.

[0423] R ii1 -A ii1 -A ii2 -NCS (ii-1)

[0424]

[0425]

[0426]

[0427] R ii1 -A ii1 -A ii1-2 -A ii2 -NCS (ii-5)

[0428]

[0429] In the general formulas (ii-1) to (ii-6), R ii1 、A ii1 and A ii2 Represents the same as R in the above general formula (ii) ii1 、A ii1 and A ii2 Same meaning respectively.

[0430] In the general formulas (ii-3) to (ii-6), A ii1-2 The definition of A in the above general formula (ii) is ii1 The definition is the same.

[0431] As the compound represented by the general formula (ii-1), compounds represented by the following general formulas (ii-1-1) to (ii-1-2) are preferred.

[0432]

[0433]

[0434] In the general formulas (ii-1-1) to (ii-1-2), R ii1 Each independently represents R in the above general formula (ii) ii1 Same meaning respectively.

[0435] Specific examples of the compound represented by the general formula (ii-1-1) include compounds represented by the following structural formulas (ii-1-1.1) to (ii-1-1.4).

[0436]

[0437] Specific examples of the compound represented by general formula (ii-1-2) include compounds represented by the following structural formulas (ii-1-2.1) to (ii-1-2.6).

[0438]

[0439] As the compound represented by the general formula (ii-2), compounds represented by the following general formulas (ii-2-1) to (ii-2-5) are preferred.

[0440]

[0441] In the general formulas (ii-2-1) to (ii-2-5), R ii1 and S ii1 Each independently represents R in the above general formula (i) ii1 and S ii1 Same meaning respectively.

[0442] Specific examples of the compound represented by the general formula (ii-2-1) include compounds represented by the following structural formulas (ii-2-1.1) to (ii-2-1.5).

[0443]

[0444] Specific examples of the compound represented by general formula (ii-2-2) include compounds represented by the following structural formulas (ii-2-2.1) to (ii-2-2.3).

[0445]

[0446] Specific examples of the compound represented by the general formula (ii-2-3) include compounds represented by the following structural formulas (ii-2-3.1) to (ii-2-3.3).

[0447]

[0448] Specific examples of the compound represented by the general formula (ii-2-4) include compounds represented by the following structural formulas (ii-2-4.1) to (ii-2-4.3).

[0449]

[0450] Specific examples of the compound represented by the general formula (ii-2-5) include compounds represented by the following structural formulas (ii-2-5.1) to (ii-2-5.3).

[0451]

[0452] As the compound represented by the general formula (ii-3), compounds represented by the following general formulas (ii-3-1) to (ii-3-6) are preferred.

[0453]

[0454] In the general formulas (ii-3-1) to (ii-3-6), R ii1 and S ii1 Each independently represents R in the above general formula (ii) ii1 and S ii1 Same meaning respectively.

[0455] Specific examples of the compound represented by the general formula (ii-3-1) include compounds represented by the following structural formulas (ii-3-1.1) to (ii-3-1.4).

[0456]

[0457] Specific examples of the compound represented by general formula (ii-3-2) include compounds represented by the following structural formulas (ii-3-2.1) to (ii-3-2.3).

[0458]

[0459] Specific examples of the compound represented by general formula (ii-3-3) include compounds represented by the following structural formulas (ii-3-3.1) to (ii-3-3.3).

[0460]

[0461] Specific examples of the compound represented by the general formula (ii-3-4) include compounds represented by the following structural formulas (ii-3-4.1) to (ii-3-4.3).

[0462]

[0463] Specific examples of the compound represented by the general formula (ii-3-5) include compounds represented by the following structural formulas (ii-3-5.1) to (ii-3-5.3).

[0464]

[0465] Specific examples of the compound represented by the general formula (ii-3-6) include compounds represented by the following structural formulas (ii-3-6.1) to (ii-3-6.2).

[0466]

[0467] As the compound represented by the general formula (ii-4), compounds represented by the following general formulas (ii-4-1) to (ii-4-8) are preferred.

[0468]

[0469]

[0470] In the general formulas (ii-4-1) to (ii-4-8), R ii1 and S ii1 Each independently represents R in the above general formula (ii) ii1 and S ii1 Same meaning respectively.

[0471] Specific examples of the compound represented by the general formula (ii-4-1) include compounds represented by the following structural formulas (ii-4-1.1) to (ii-4-1.3).

[0472]

[0473] Specific examples of the compound represented by general formula (ii-4-2) include compounds represented by the following structural formulas (ii-4-2.1) to (ii-4-2.3).

[0474]

[0475] Specific examples of the compound represented by the general formula (ii-4-3) include compounds represented by the following structural formulas (ii-4-3.1) to (ii-4-3.3).

[0476]

[0477] Specific examples of the compound represented by general formula (ii-4-4) include compounds represented by the following structural formulas (ii-4-4.1) to (ii-4-4.3).

[0478]

[0479] Specific examples of the compound represented by general formula (ii-4-5) include compounds represented by the following structural formulas (ii-4-5.1) to (ii-4-5.3).

[0480]

[0481] Specific examples of the compound represented by the general formula (ii-4-6) include compounds represented by the following structural formulas (ii-4-6.1) to (ii-4-6.3).

[0482]

[0483] Specific examples of the compound represented by the general formula (ii-4-7) include compounds represented by the following structural formulas (ii-4-7.1) to (ii-4-7.3).

[0484]

[0485] Specific examples of the compound represented by the general formula (ii-4-8) include compounds represented by the following structural formulas (ii-4-8.1) to (ii-4-8.3).

[0486]

[0487] As the compound represented by the general formula (ii-5), compounds represented by the following general formulas (ii-5-1) to (ii-5-5) are preferred.

[0488]

[0489] In the general formulas (ii-5-1) to (ii-5-5), R ii1 and S ii1 Each independently represents R in the above general formula (ii) ii1 and S ii1 Same meaning respectively.

[0490] Specific examples of the compound represented by the general formula (ii-5-1) include compounds represented by the following structural formulas (ii-5-1.1) to (ii-5-1.4).

[0491]

[0492] Specific examples of the compound represented by general formula (ii-5-2) include compounds represented by the following structural formulas (ii-5-2.1) to (ii-5-2.4).

[0493]

[0494] Specific examples of the compound represented by the general formula (ii-5-3) include compounds represented by the following structural formulas (ii-5-3.1) to (ii-5-3.3).

[0495]

[0496] Specific examples of the compound represented by general formula (ii-5-4) include compounds represented by the following structural formulas (ii-5-4.1) to (ii-5-4.3).

[0497]

[0498] Specific examples of the compound represented by General Formula (ii-5-5) include compounds represented by the following structural formula (ii-5-5.1).

[0499]

[0500] As the compound represented by the general formula (ii-6), compounds represented by the following general formulas (ii-6-1) to (ii-6-2) are preferred.

[0501]

[0502] In the general formulas (ii-6-1) to (ii-6-2), R ii1 and S ii1 Each independently represents R in the above general formula (ii) ii1 and S ii1 Same meaning respectively.

[0503] Specific examples of the compound represented by the general formula (ii-6-1) include compounds represented by the following structural formulas (ii-6-1.1) to (ii-6-1.3).

[0504]

[0505] Specific examples of the compound represented by general formula (ii-6-2) include compounds represented by the following structural formulas (ii-6-2.1) to (ii-6-2.3).

[0506]

[0507] General formula (ii), general formula (ii-1) to (ii-6), general formula (ii-1-1) to (ii-1-2), general formula (ii-2-1) to (ii-2-5), general formula (ii-3-1) to (ii-3-6), general formula (ii-4-1) to (ii-4-8), general formula (ii-5-1) to (ii-5-5), general formula (ii-6-1) to (ii-6-2), structural formula (ii-1-1.1) to (ii-1-1.4), structural formula (ii-1-2.1) to (ii-1-2.6), structural formula (ii-2-1.1) to (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)、Structural formula (ii-2-5.1)~(ii-2-5.3)、Structural formula (ii-3-1.1)~(ii-3-1.4)、Structural formula (ii-3-2.1)~(ii-3-2.3)、Structural formula (ii-3-3.1)~(ii-3-3.3)、Structural formula (ii-3-4.1)~(ii-3-4.3)、Structural formula (ii-3-5.1)~(ii-3-5.3)、Structural formula (ii- 3-6.1)~(ii-3-6.2), structural formula (ii-4-1.1)~(ii-4-1.3), structural formula (ii-4-2.1)~(ii-4-2.3), structural formula (ii-4-3.1)~(ii-4-3.3), structural formula (ii-4-4.1)~(ii-4-4.3), structural formula (ii-4-5.1)~(ii-4-5.3), structural formula (ii-4-6.1)~(ii-4-6.3), structural formula (ii-4-7.1)~(ii-4-7.3), structural formula (ii-4-8.1)~(ii-4-8.3), structural formula (ii- The type of compounds represented by structural formula (ii-5-1.1) to (ii-5-1.4), structural formula (ii-5-2.1) to (ii-5-2.4), structural formula (ii-5-3.1) to (ii-5-3.3), structural formula (ii-5-4.1) to (ii-5-4.3), structural formula (ii-5-5.1), structural formula (ii-6-1.1) to (ii-6-1.3) or structural formula (ii-6-2.1) to (ii-6-2.3) used in the liquid crystal composition is 1 or more, preferably 1 to 10, preferably 1 to 8, preferably 1 to 6, preferably 1 to 4, and preferably 1 to 3.

[0508] General formula (ii), general formula (ii-1) to (ii-6), general formula (ii-1-1) to (ii-1-2), general formula (ii-2-1) to (ii-2-5), general formula (ii-3-1) to (ii-3-6), general formula (ii-4-1) to (ii-4-8), general formula (ii-5-1) to (ii-5-5), general formula (ii-6-1) to (ii-6-2), structural formula (ii-1-1.1) to (ii-1-1.4), structural formula (ii-1-2.1) to (ii-1-2.6), structural formula (ii-2-1.1) to (ii-2-1.5), structural formula (ii-2-2.1) to (ii- 2-2.3), structural formula (ii-2-3.1) to (ii-2-3.3), structural formula (ii-2-4.1) to (ii-2-4.3), structural formula (ii-2-5.1) to (ii-2-5.3), structural formula (ii-3-1.1) to (ii-3-1.4), structural formula (ii-3-2.1) to (ii-3-2.3), structural formula (ii-3-3.1) to (ii-3-3.3), structural formula (ii-3-4.1) to (ii-3-4.3), structural formula (ii-3-5.1) to (ii-3-5.3), structural formula (ii-3-6.1) to (ii-3-6.2), structural formula (ii-3- i-4-1.1)~(ii-4-1.3)、Structural formula (ii-4-2.1)~(ii-4-2.3)、Structural formula (ii-4-3.1)~(ii-4-3.3)、Structural formula (ii-4-4.1)~(ii-4-4.3)、Structural formula (ii-4-5.1)~(ii-4-5.3)、Structural formula (ii-4-6.1)~(ii-4-6.3)、Structural formula (ii-4-7.1)~(ii-4-7.3)、Structural formula (ii-4-8.1)~(ii-4-8.3)、Structural formula (ii-5-1.1)~(ii-5-1.4)、Structural formula (ii-5-2.1)~(i The lower limit of the total content of the compounds represented by structural formula (i-5-2.4), structural formula (ii-5-3.1) to (ii-5-3.3), structural formula (ii-5-4.1) to (ii-5-4.3), structural formula (ii-5-5.1), structural formula (ii-6-1.1) to (ii-6-1.3) or structural formula (ii-6-2.1) to (ii-6-2.3) 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.

[0509] General formula (ii), general formula (ii-1) to (ii-6), general formula (ii-1-1) to (ii-1-2), general formula (ii-2-1) to (ii-2-5), general formula (ii-3-1) to (ii-3-6), general formula (ii-4-1) to (ii-4-8), general formula (ii-5-1) to (ii-5-5), general formula (ii-6-1) to (ii-6-2), structural formula (ii-1-1.1) to (ii-1-1.4), structural formula (ii-1-2.1) to (ii-1-2.6), structural formula (ii-2-1.1) to (ii-2-1.5), structural formula (ii-2-2.1) to (ii-2 -2.3)、Structural formula (ii-2-3.1)~(ii-2-3.3)、Structural formula (ii-2-4.1)~(ii-2-4.3)、Structural formula (ii-2-5.1)~(ii-2-5.3)、Structural formula (ii-3-1.1)~(ii-3-1.4)、Structural formula (ii-3-2.1)~(ii-3-2.3)、Structural formula (ii-3-3.1)~(ii-3-3.3)、Structural formula (ii-3-4.1)~(ii-3-4.3)、Structural formula (ii-3-5.1)~(ii-3-5.3)、Structural formula (ii-3-6.1~(ii-3-6.2)、Structural formula (ii -4-1.1)~(ii-4-1.3)、Structural formula (ii-4-2.1)~(ii-4-2.3)、Structural formula (ii-4-3.1)~(ii-4-3.3)、Structural formula (ii-4-4.1)~(ii-4-4.3)、Structural formula (ii-4-5.1)~(ii-4-5.3)、Structural formula (ii-4-6.1)~(ii-4-6.3)、Structural formula (ii-4-7.1)~(ii-4-7.3)、Structural formula (ii-4-8.1)~(ii-4-8.3)、Structural formula (ii-5-1.1)~(ii-5-1.4)、Structural formula (ii-5-2.1)~(ii- The upper limit value of the total content of the compounds represented by structural formula (ii-5-2.4), structural formula (ii-5-3.1) to (ii-5-3.3), structural formula (ii-5-4.1) to (ii-5-4.3), structural formula (ii-5-5.1), structural formula (ii-6-1.1) to (ii-6-1.3) or structural formula (ii-6-2.1) to (ii-6-2.3) 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.

[0510] General formula (ii), general formulas (ii-1) to (ii-6), general formulas (ii-1-1) to (ii-1-2), general formulas (ii-2-1) to (ii-2-5), general formulas (ii-3-1) to (ii-3-6), general formulas (ii-4-1) to (ii-4-8), general formulas (ii-5-1) to (ii-5-5), general formulas (ii-6-1) to (ii-6-2), structural formulas (ii-1-1.1) to (ii-1-1.4), structural formulas (ii-1-2.1) to (ii-1-2.6), structural formulas (ii-2-1.1) to (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)、Structural formula (ii-2-5.1)~(ii-2-5.3)、Structural formula (ii-3-1.1)~(ii-3-1.4)、Structural formula (ii-3-2.1)~(ii-3-2.3)、Structural formula (ii-3-3.1)~(ii-3-3.3)、Structural formula (ii-3-4.1)~(ii-3-4.3)、Structural formula (ii-3-5.1)~(ii i-3-5.3), structural formula (ii-3-6.1) to (ii-3-6.2), structural formula (ii-4-1.1) to (ii-4-1.3), structural formula (ii-4-2.1) to (ii-4-2.3), structural formula (ii-4-3.1) to (ii-4-3.3), structural formula (ii-4-4.1) to (ii-4-4.3), structural formula (ii-4-5.1) to (ii-4-5.3), structural formula (ii-4-6.1) to (ii-4-6.3), structural formula (ii-4-7.1) to (ii-4-7.3), structural formula (ii-4 The total content of the compounds represented by the formula (ii-8.1) to (ii-4-8.3), structural formula (ii-5-1.1) to (ii-5-1.4), structural formula (ii-5-2.1) to (ii-5-2.4), structural formula (ii-5-3.1) to (ii-5-3.3), structural formula (ii-5-4.1) to (ii-5-4.3), structural formula (ii-5-5.1), structural formula (ii-6-1.1) to (ii-6-1.3) or structural formula (ii-6-2.1) to (ii-6-2.3) in 100% by mass of the liquid crystal composition is determined from the solubility, Δn and / or Δε r From the viewpoint of the content of cellulose, the content is preferably 10 to 80% by mass, more preferably 15 to 75% by mass, and even more preferably 20 to 70% by mass.

[0511] The compound represented by the general formula (ii) (including subordinate concepts) can be synthesized using a known synthesis method.

[0512] The liquid crystal composition of the present invention is prepared from V th , Δn and / or Δε r From the viewpoint of further containing one or more compounds represented by the following general formula (iii) having a cyano group (—CN).

[0513]

[0514] In the general formula (iii), R iii1 It represents an alkyl group having 1 to 20 carbon atoms.

[0515] The alkyl group is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0516] The number of carbon atoms in the alkyl group is preferably 2 to 10, more preferably 2 to 6.

[0517] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0518] Furthermore, one or two or more -CH2-CH2- groups in the alkyl group may be substituted with -CH=CH-, -CO-O-, -O-CO- and / or -C≡C-.

[0519] Furthermore, one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[0520] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0521] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0522] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0523] For example, R iii1 When one -CH2- in the alkyl group is replaced by -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0524] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0525] The number of carbon atoms in the alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0526] In addition, R iii1 When one -CH2- in the alkyl group is replaced by -S-, a thioalkoxy group (alkylthio, alkylthio) having 1 to 19 carbon atoms can be represented.

[0527] The thioalkoxy group is a linear, branched or cyclic thioalkoxy group, and is preferably a linear thioalkoxy group.

[0528] The number of carbon atoms in the thioalkoxy group is preferably 1 to 10, more preferably 1 to 6.

[0529] In addition, R iii1 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0530] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0531] The number of carbon atoms in the alkenyl group is preferably 2 to 10, more preferably 2 to 6.

[0532] In addition, R iii1 When one or two or more -CH2-CH2- groups in the alkyl group are replaced by -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0533] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0534] The number of carbon atoms in the alkynyl group is preferably 2 to 10, more preferably 2 to 6.

[0535] In addition, R iii1 When one -CH2- in the alkyl group is replaced by -O-, and one or two or more -CH2-CH2- are replaced by -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented.

[0536] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0537] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0538] In addition, R iii1 By replacing one or two or more hydrogen atoms in the alkyl group with halogen atoms, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0539] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0540] The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, more preferably 2 to 6.

[0541] In addition, R iii1When one -CH2- in the alkyl group is substituted with -O-, and one or two or more hydrogen atoms in the alkyl group are substituted with halogen atoms, a halogenated alkoxy group having 1 to 19 carbon atoms can be represented.

[0542] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[0543] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0544] As R iii1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted groups) include the following: iii1 -1)~(R iii1 -36) etc.

[0545]

[0546] Formula (R iii1 -1)~(R iii1 -36), the black dot indicates the direction to A iii1 connection key.

[0547] In R iii1 When the ring structure connected is a phenyl group (aromatic group), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. iii1 When the linked ring structure is a saturated ring structure such as cyclohexane, pyran, and dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms.

[0548] In addition, as R iii1 In order to stabilize the nematic phase, the total number of carbon atoms and, if present, oxygen atoms is preferably 5 or less, and a linear chain is preferred.

[0549] Furthermore, as R iii1 From the viewpoint of solubility, a linear alkyl group having 2 to 8 carbon atoms is preferred.

[0550] In the general formula (iii), A iii1 、A iii2 and A iii3 Each independently represents a group selected from the group consisting of the following groups (a), (b), (c) and (d):

[0551] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups in the group may be substituted with -O- and / or -S-)

[0552] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=)

[0553] (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH= or two or more non-adjacent -CH= groups in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N=)

[0554] (d) Thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=).

[0555] A iii1 、A iii2 and A iii3 One or more hydrogen atoms in the group may be independently substituted by a substituent group S iii1 replace.

[0556] Substituent S iii1 represents any one of a halogen atom, a cyano group, and an alkyl group having 1 to 6 carbon atoms.

[0557] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0558] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0559] Furthermore, one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[0560] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0561] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0562] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0563] In addition, it is preferred that at least one A iii1 、A iii2 or A iii3 Substituted by at least one S iii1 replace.

[0564] In addition, A iii2 Preferably, at least one substituent S ii1 replace.

[0565] Furthermore, in the substituent S iii1 When there are multiple ones, they may be the same or different.

[0566] As A iii2 The substituent S in iii1 The substitution position of is preferably the following formula (A iii2 -SP-1).

[0567]

[0568] Formula (A iii2 -SP-1), the white dot indicates the direction to A iii1 The black dot indicates the connection bond to A iii3 connection key.

[0569] More specifically, A iii1 Preferably, it is represented by the following formula (A iii1 -1)~(A iii1 -2) either.

[0570]

[0571] Formula (A iii1 -1)~(A iii1 -2), the white dot indicates the direction to R iii1 or A iii1 The black dot indicates the connection bond to A iii1 or A iii2 connection key.

[0572] More specifically, A iii2 Preferably, it is represented by the following formula (A iii2 -1)~(A iii2 -3) any one of.

[0573]

[0574] Formula (A iii2 -1)~(A iii2 -3), the white dot indicates the direction to A iii1 The black dot indicates the connection bond to A iii3 connection key.

[0575] More specifically, A iii3 Preferably, it is represented by the following formula (A iii3 -1)~(A iii3 -2) either.

[0576]

[0577] Formula (A iii3 -1)~(A iii3 -2) In the case of white dots, the direction to A iii2 The black dot represents the bond to the cyano group (-CN).

[0578] In the general formula (iii), n iii1 Indicates an integer from 1 to 2.

[0579] Furthermore, in the general formula (iii), in A iii1 When there are multiple ones, they may be the same or different.

[0580] As the compound represented by the general formula (iii), a compound represented by the following general formula (iii-1) is preferable.

[0581] R iii1 -A iii1 -A iii2 -A iii3 -CN (iii-1)

[0582] In the general formula (iii-1), R iii1 、A iii1 、A iii2 and A iii3 Represents the same as R in the above general formula (iii) iii1 、A iii1 、A iii2 and A iii3 Same meaning respectively.

[0583] As the compound represented by the general formula (iii-1), compounds represented by the following general formulas (iii-1-1) to (iii-1-3) are preferred.

[0584]

[0585] In the general formulas (iii-1-1) to (iii-1-3), R iii1 and S iii1 Each independently represents R in the above general formula (iii) iii1 and S iii1 Same meaning respectively.

[0586] Specific examples of the compound represented by the general formula (iii-1-1) include compounds represented by the following structural formulas (iii-1-1.1) to (iii-1-1.3).

[0587]

[0588] Specific examples of the compound represented by general formula (iii-1-2) include compounds represented by the following structural formulas (iii-1-2.1) to (iii-1-2.3).

[0589]

[0590] Specific examples of the compound 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).

[0591]

[0592] The type of compounds represented by general formula (iii), general formula (iii-1), general formula (iii-1-1) to (iii-1-3), structural formula (iii-1-1.1) to (iii-1-1.3), structural formula (iii-1-2.1) to (iii-1-2.3) or structural formula (iii-1-3.1) to (iii-1-3.3) used in the liquid crystal composition is 1 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.

[0593] The lower limit of the total content of the compounds represented by general formula (iii), general formula (iii-1), general formula (iii-1-1) to (iii-1-3), structural formula (iii-1-1.1) to (iii-1-1.3), structural formula (iii-1-2.1) to (iii-1-2.3) or structural formula (iii-1-3.1) to (iii-1-3.3) in 100 mass% of the liquid crystal composition is preferably 1 mass% or more, preferably 2 mass% or more, and preferably 3 mass% or more.

[0594] The upper limit value of the total content of the compounds represented by general formula (iii), general formula (iii-1), general formula (iii-1-1) to (iii-1-3), structural formula (iii-1-1.1) to (iii-1-1.3), structural formula (iii-1-2.1) to (iii-1-2.3) or structural formula (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.

[0595] The total content of the compounds represented by general formula (iii), general formula (iii-1), general formula (iii-1-1) to (iii-1-3), structural formula (iii-1-1.1) to (iii-1-1.3), structural formula (iii-1-2.1) to (iii-1-2.3) or structural formula (iii-1-3.1) to (iii-1-3.3) in 100% by mass of the liquid crystal composition is determined from the solubility and / or V th From the viewpoint of the content of cellulose, the content is preferably 1 to 15% by mass, more preferably 2 to 15% by mass, and even more preferably 3 to 20% by mass.

[0596] The compound represented by the general formula (iii) (including subordinate concepts) can be synthesized using a known synthesis method.

[0597] The liquid crystal composition of the present invention is characterized by Vth, Δn and / or Δε r From the perspective of iv1 A compound represented by the following general formula (iv) containing a -C≡C-) group and a cyano group (-CN).

[0598]

[0599] In the general formula (iv), R iv1 It represents an alkyl group having 1 to 20 carbon atoms.

[0600] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0601] The number of carbon atoms in the alkyl group is preferably 2 to 10, more preferably 2 to 6.

[0602] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0603] Furthermore, one or two or more -CH2-CH2- groups in the alkyl group may be substituted with -CH=CH-, -COO-, -OCO- and / or -C≡C-.

[0604] Furthermore, one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[0605] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0606] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0607] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0608] For example, R iv1 When one -CH2- in the alkyl group is replaced by -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0609] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

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

[0611] In addition, R iv1 When one -CH2- in the alkyl group is replaced by -S-, a thioalkoxy group (alkylthio, alkylthio) having 1 to 19 carbon atoms can be represented.

[0612] The thioalkoxy group is a linear, branched or cyclic thioalkoxy group, and is preferably a linear thioalkoxy group.

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

[0614] In addition, R iv1 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0615] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

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

[0617] In addition, R iv1 When one or two or more -CH2-CH2- groups in the alkyl group are replaced by -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0618] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

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

[0620] In addition, R iv1 When one -CH2- in the alkyl group is replaced by -O-, and one or two or more -CH2-CH2- are replaced by -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented.

[0621] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

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

[0623] In addition, R iv1 By substituting one or two or more hydrogen atoms in the alkyl group with a halogen atom, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0624] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0625] The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, more preferably 2 to 6.

[0626] In addition, R iv1 When one -CH2- in the alkyl group is substituted with -O-, and one or two or more hydrogen atoms in the alkyl group are substituted with halogen atoms, a halogenated alkoxy group having 1 to 19 carbon atoms can be represented.

[0627] The halogenated alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0628] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0629] As R iv1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted groups) include the following: iv1 -1)~(R iv1 -36) etc.

[0630]

[0631] Formula (R iv1 -1)~(R iv1 -36), the black dots represent the connecting bonds to -C≡C-.

[0632] Furthermore, as R iv1 From the viewpoint of solubility, a linear alkyl group having 2 to 8 carbon atoms is preferred.

[0633] In the general formula (iv), A iv1 and A iv2 Each independently represents a group selected from the group consisting of the following groups (a), (b), (c), and (d):

[0634] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups in the group may be substituted with -O- and / or -S-)

[0635] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=)

[0636] (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH= or two or more non-adjacent -CH= groups in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N=)

[0637] (d) Thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=).

[0638] A iv1 and A iv2 One or more hydrogen atoms in the group may be independently substituted by a substituent group S iv1 replace.

[0639] Substituent S iv1 represents any one of a halogen atom, a cyano group, and an alkyl group having 1 to 6 carbon atoms.

[0640] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0641] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0642] One or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[0643] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0644] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0645] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0646] In addition, it is preferred that A iv1 At least one substituted S iv1 replace.

[0647] Furthermore, in the substituent S iv1 When there are multiple ones, they may be the same or different.

[0648] As A iv1 The substituent S in iv1 The substitution position of is preferably the following formula (A iv1 -SP-1).

[0649]

[0650] Formula (A iv1 -SP-1), the white dot indicates the direction -C≡C- or A iv1 The black dot indicates the connection bond to A iv1 or A iv2 connection key.

[0651] As A iv2 The substituent S in iv1 The substitution position is preferably the following formula (A iv2 -SP-1)~(A iv2 -SP-2).

[0652]

[0653] Formula (A iv2 -SP-1)~(A iv2 -SP-2), the white dot indicates the direction to A iv1 The black dot represents the bond to the cyano group (-CN).

[0654] More specifically, A iv1 Preferably, it is represented by the following formula (A iv1 -1)~(A iv1 -3) any one of.

[0655]

[0656] Formula (A iv1 -1)~(A iv1 -3) In the figure, the white dot indicates the direction -C≡C- or A iv1 The black dot indicates the connection bond to A iv1 or A iv2 connection key.

[0657] More specifically, A iv2 Preferably, it is represented by the following formula (A iv2 -1)~(A iv2 -Any of 4).

[0658]

[0659] Formula (A iv2 -1)~(A iv2-4), the white dot indicates the direction to A iv1 The black dot represents the bond to the cyano group (-CN).

[0660] n iv1 Indicates an integer from 1 to 2.

[0661] Furthermore, in the general formula (iv), in A iv1 When there are multiple ones, they may be the same or different.

[0662] As the compound represented by the general formula (iv), a compound represented by the following general formula (iv-1) is preferable.

[0663]

[0664] In the general formula (iv-1), R iv1 、A iv1 and A iv2 Represents the same as R in the above general formula (iv) iv1 、A iv1 and A iv2 Same meaning respectively.

[0665] As the compound represented by the general formula (iv-1), compounds represented by the following general formulas (iv-1-1) to (iv-1-6) are preferred.

[0666]

[0667] In the general formulas (iv-1-1) to (iv-1-6), R iv1 and S iv1 Each independently represents R in the above general formula (iv) iv1 and S iv1 Same meaning respectively.

[0668] Specific examples of the compound represented by the general formula (iv-1-1) include compounds represented by the following structural formulas (iv-1-1.1) to (iv-1-1.2).

[0669]

[0670] Specific examples of the compound represented by the general formula (iv-1-2) include compounds represented by the following structural formulas (iv-1-2.1) to (iv-1-2.2).

[0671]

[0672] Specific examples of the compound represented by the general formula (iv-1-3) include compounds represented by the following structural formulas (iv-1-3.1) to (iv-1-3.2).

[0673]

[0674] Specific examples of the compound represented by the general formula (iv-1-4) include compounds represented by the following structural formulas (iv-1-4.1) to (iv-1-4.2).

[0675]

[0676] Specific examples of the compound represented by the general formula (iv-1-5) include compounds represented by the following structural formulas (iv-1-5.1) to (iv-1-5.2).

[0677]

[0678] Specific examples of the compound represented by the general formula (iv-1-6) include compounds represented by the following structural formulas (iv-1-6.1) to (iv-1-6.2).

[0679]

[0680] The type 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) used in the liquid crystal composition is 1 or more, preferably 1 to 5, preferably 1 to 4, preferably 1 to 3, preferably 1 to 2, and preferably 1.

[0681] The lower limit of the total content of the 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.

[0682] The upper limit value of the total content of the 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.

[0683] The total content of the 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% by mass of the liquid crystal composition is preferably 0 to 35% by mass, preferably 1 to 30% by mass, and preferably 5 to 25% by mass from the viewpoint of compatibility with other liquid crystal compounds.

[0684] The compound represented by the general formula (iv) (including subordinate concepts) can be synthesized using a known synthesis method.

[0685] The liquid crystal composition of the present invention is characterized by Vth, Δn and / or Δε r From the viewpoint of further containing one or more compounds represented by the following general formula (v) having at least one -C≡C- and a cyano group (-CN) as a linking group.

[0686]

[0687] In the general formula (v), R v1 It represents an alkyl group having 1 to 20 carbon atoms.

[0688] The alkyl group is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0689] The number of carbon atoms in the alkyl group is preferably 2 to 10, more preferably 2 to 6.

[0690] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0691] Furthermore, one or two or more -CH2-CH2- groups in the alkyl group may be independently substituted with -CH=CH-, -CO-O-, -O-CO- and / or -C≡C-.

[0692] Furthermore, one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[0693] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0694] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0695] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0696] For example, R v1 When one -CH2- in the alkyl group is replaced by -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0697] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0698] The number of carbon atoms in the alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0699] In addition, R v1 By R v1 One -CH2- in the group is substituted with -S-, which can represent a thioalkoxy group (alkylthio, alkylthio) having 1 to 19 carbon atoms.

[0700] The thioalkoxy group is a linear, branched or cyclic thioalkoxy group, and is preferably a linear thioalkoxy group.

[0701] The number of carbon atoms in the thioalkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0702] In addition, R v1 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0703] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0704] The number of carbon atoms in the alkenyl group is preferably 2 to 10, more preferably 2 to 6.

[0705] In addition, R v1 When one or two or more -CH2-CH2- groups in the alkyl group are replaced by -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0706] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0707] The number of carbon atoms in the alkynyl group is preferably 2 to 10, more preferably 2 to 6.

[0708] In addition, R v1 When one -CH2- in the alkyl group is replaced by -O-, and one or two or more -CH2-CH2- are replaced by -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented.

[0709] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0710] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0711] In addition, R v1 By substituting one or two or more hydrogen atoms in the alkyl group with a halogen atom, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0712] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0713] The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, more preferably 2 to 6.

[0714] In addition, R v1 When one -CH2- in the alkyl group is substituted with -O-, and one or two or more hydrogen atoms in the alkyl group are substituted with halogen atoms, a halogenated alkoxy group having 1 to 19 carbon atoms can be represented.

[0715] The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group.

[0716] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0717] As R v1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted groups) include the following: v1 -1)~(R v1 -36) etc.

[0718]

[0719] Formula (R v1 -1)~(R v1 -36), the black dot indicates the direction to A v1 connection key.

[0720] In R v1 When the ring structure connected is a phenyl group (aromatic group), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. v1 When the linked ring structure is a saturated ring structure such as cyclohexane, pyran, and dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms.

[0721] In addition, as R v1 In order to stabilize the nematic phase, the total number of carbon atoms and, if present, oxygen atoms is preferably 5 or less, and a linear chain is preferred.

[0722] Furthermore, as R v1 From the viewpoint of solubility, a linear alkyl group having 2 to 8 carbon atoms is preferred.

[0723] In the general formula (v), A v1 and A v2 Each independently represents a group selected from the group consisting of the following groups (a), (b), (c) and (d):

[0724] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups in the group may be substituted with -O- and / or -S-)

[0725] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=)

[0726] (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH= or two or more non-adjacent -CH= groups in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N=)

[0727] (d) Thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=).

[0728] A v1 and A v2 One or more hydrogen atoms in the group may be independently substituted by a substituent group S v1 replace.

[0729] Substituent S v1 represents any one of a halogen atom, a cyano group, and an alkyl group having 1 to 6 carbon atoms.

[0730] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0731] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0732] Furthermore, one or two or more hydrogen atoms present in the alkyl group may each independently be substituted with a halogen atom.

[0733] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0734] However, when the alkyl group having 1 to 6 carbon atoms is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0735] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0736] In addition, it is preferred that A v1 At least 1 or A v2 Substituted by at least one S v1 replace.

[0737] Furthermore, in the substituent S v1 When there are multiple ones, they may be the same or different.

[0738] As A v1 The substituent S in v1The substitution position of is preferably the following formula (A v1 -SP-1).

[0739]

[0740] Formula (A v1 -SP-1), the white dot indicates the direction to R v1 or Z v1 The black dot indicates the connection key to Z v1 connection key.

[0741] As A v2 The substituent S in v1 The substitution position is preferably the following formula (A v2 -SP-1)~(A v2 -SP-2).

[0742]

[0743] Formula (A v2 -SP-1)~(A v2 -SP-2), the white dot indicates the direction of Z v1 The black dot represents the bond to the cyano group (-CN).

[0744] More specifically, A v1 Preferably, it is represented by the following formula (A v1 -1)~(A v1 -3) any one of.

[0745]

[0746] Formula (A v1 -1)~(A v1 -3), the white dot indicates the direction to R v1 or Z v1 The black dot indicates the connection key to Z v1 connection key.

[0747] More specifically, A v2 Preferably, it is represented by the following formula (A v2 -1)~(A v2 -3) any one of.

[0748]

[0749] Formula (A v2 -1)~(A v2 -3), the white dot indicates the direction Z v1 The black dot represents the bond to the cyano group (-CN).

[0750] In the general formula (v), Z v1 It represents any one of a single bond, -C≡C-, -CH=CH-, and -CF=CF-.

[0751] However, Z v1 At least one of represents -C≡C-.

[0752] In the general formula (v), n v1 Indicates an integer from 1 to 2.

[0753] Furthermore, as general formula (v), in A v1 and Z v1 When there are multiple ones, they may be the same or different.

[0754] As the compound represented by the general formula (v), compounds represented by the following general formulas (v-1) to (v-2) are preferred.

[0755]

[0756] In the general formulas (v-1) to (v-2), R v1 、A v1 and A v2 Represents the same as R in the above general formula (v) v1 、A v1 and A v2 Same meaning respectively.

[0757] In the general formulas (v-1) to (v-2), A v1-2 The definition of A in the above general formula (v) is v1 The definition is the same.

[0758] As the compound represented by the general formula (v-1), compounds represented by the following general formulae (v-1-1) to (v-1-6) are preferred.

[0759]

[0760] In the general formulas (v-1-1) to (v-1-6), R v1 and S v1 Each independently represents R in the above general formula (v) v1 and S v1 Same meaning respectively.

[0761] Specific examples of the compound 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).

[0762]

[0763] Specific examples of the compound 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).

[0764]

[0765] Specific examples of the compound 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).

[0766]

[0767] Specific examples of the compound represented by the general formula (v-1-4) include compounds represented by the following structural formulas (v-1-4.1) to (ii-1-4.3).

[0768]

[0769] Specific examples of the compound 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).

[0770]

[0771] Specific examples of the compound 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).

[0772]

[0773] As the compound represented by the general formula (v-2), compounds represented by the following general formulas (v-2-1) to (v-2-2) are preferred.

[0774]

[0775] In the general formulas (v-2-1) to (v-2-2), R v1 and S v1 Each independently represents R in the above general formula (v) v1 and S v1 Same meaning respectively.

[0776] Specific examples of the compound 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).

[0777]

[0778] Specific examples of the compound 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).

[0779]

[0780] General formula (v), general formula (v-1) to (v-2), general formula (v-1-1) to (v-1-6), general formula (v-2-1) to (v-2-2), structural formula (v-1-1.1) to (v-1-1.3), structural formula (v-1-2.1) to (v-1-2.3), structural formula (v-1-3.1) to (v-1-3.3), structural formula (v-1-4.1) to (v-1-4.3), structural formula (v -1-5.1) ~ (v-1-5.3), structural formula (v-1-6.1) ~ (v-1-6.3), structural formula (v-2-1.1) ~ (v-2-1.3) or structural formula (v-2-2.1) ~ (v-2-2.3) The type of compounds used in the liquid crystal composition is 1 or more, preferably 1 to 5, preferably 1 to 4, preferably 1 to 3, preferably 1 to 2, and preferably 1.

[0781] General formula (v), general formula (v-1) to (v-2), general formula (v-1-1) to (v-1-6), general formula (v-2-1) to (v-2-2), structural formula (v-1-1.1) to (v-1-1.3), structural formula (v-1-2.1) to (v-1-2.3), structural formula (v-1-3.1) to (v-1-3.3), structural formula (v-1-4.1) to (v-1-4.3), structural formula The lower limit of the total content of the compounds represented by 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) in 100 mass% of the liquid crystal composition is preferably 1 mass% or more, preferably 3 mass% or more, and preferably 5 mass% or more.

[0782] General formula (v), general formula (v-1) to (v-2), general formula (v-1-1) to (v-1-6), general formula (v-2-1) to (v-2-2), structural formula (v-1-1.1) to (v-1-1.3), structural formula (v-1-2.1) to (v-1-2.3), structural formula (v-1-3.1) to (v-1-3.3), structural formula (v-1-4.1) to (v-1-4.3), structural formula The upper limit value of the total content of the compounds represented by formula (v-1-5.1) to (v-1-5.3), structural formula (v-1-6.1) to (v-1-6.3), structural formula (v-2-1.1) to (v-2-1.3) or structural formula (v-2-2.1) to (v-2-2.3) in 100 mass% of the liquid crystal composition is preferably 30 mass% or less, preferably 25 mass% or less, and preferably 20 mass% or less.

[0783] The total content of the 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) in 100% by mass of the liquid crystal composition is determined from the solubility and / or V th From the viewpoint of the content of cellulose, the content is preferably 1 to 30% by mass, more preferably 3 to 25% by mass, and even more preferably 5 to 20% by mass.

[0784] The compound represented by the general formula (v) (including subordinate concepts) can be synthesized using a known synthesis method.

[0785] The liquid crystal composition of the present invention is obtained from Δn and / or Δε r From the viewpoint of further containing one or more compounds represented by the following general formula (vi) having at least one -C≡C- as a linking group.

[0786]

[0787] In the general formula (vi), R vi1 It represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.

[0788] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0789] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0790] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0791] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0792] Furthermore, one or two or more -CH2-CH2-CH2- in the alkyl group may be independently substituted with -O-CO-O-.

[0793] Furthermore, one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[0794] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0795] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0796] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0797] For example, R vi1 When one -CH2- in the alkyl group is replaced by -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0798] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0799] The number of carbon atoms in the alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0800] In addition, R vi1 When one -CH2- in the alkyl group is replaced by -S-, a thioalkoxy group (alkylthio, alkylthio) having 1 to 19 carbon atoms can be represented.

[0801] The thioalkoxy group is a linear, branched or cyclic thioalkoxy group, and is preferably a linear thioalkoxy group.

[0802] The number of carbon atoms in the thioalkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0803] In addition, R vi1By substituting one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0804] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0805] The number of carbon atoms in the alkenyl group is preferably 2 to 10, more preferably 2 to 6.

[0806] In addition, R vi1 When one or two or more -CH2-CH2- groups in the alkyl group are replaced by -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0807] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0808] The number of carbon atoms in the alkynyl group is preferably 2 to 10, more preferably 2 to 6.

[0809] In addition, R vi1 When one -CH2- in the alkyl group is replaced by -O-, and one or two or more -CH2-CH2- are replaced by -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented.

[0810] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0811] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0812] In addition, R vi1 By substituting one or two or more hydrogen atoms in the alkyl group with a halogen atom, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0813] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0814] The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, more preferably 2 to 6.

[0815] In addition, R vi1 When one -CH2- in the alkyl group is substituted with -O-, and one or two or more hydrogen atoms in the alkyl group are substituted with halogen atoms, a halogenated alkoxy group having 1 to 19 carbon atoms can be represented.

[0816] The halogenated alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0817] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0818] As R vi1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted groups) include the following: vi1 -1)~(R vi1 -36) etc.

[0819]

[0820] Formula (R vi1 -1)~(R vi1 -36), the black dot indicates the direction to A vi1 connection key.

[0821] R vi1 When emphasis is placed on the reliability of the entire liquid crystal composition, an alkyl group having 1 to 12 carbon atoms is preferred. When emphasis is placed on reducing the viscosity of the entire liquid crystal composition, an alkenyl group having 2 to 8 carbon atoms is preferred.

[0822] In R vi1 When the ring structure connected is a phenyl group (aromatic group), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. vi1 When the linked ring structure is a saturated ring structure such as cyclohexane, pyran, and dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms.

[0823] In addition, as R vi1 In order to stabilize the nematic phase, the total number of carbon atoms and, if present, oxygen atoms is preferably 5 or less, and a linear chain is preferred.

[0824] Furthermore, as R vi1 From the viewpoint of solubility, a linear alkyl group having 2 to 6 carbon atoms is preferred.

[0825] In the general formula (vi), 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.

[0826] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0827] The number of carbon atoms in the alkyl group is preferably 2 to 10, more preferably 2 to 6.

[0828] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0829] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0830] Furthermore, one or two or more -CH2-CH2-CH2- in the alkyl group may be independently substituted with -O-CO-O-.

[0831] Furthermore, one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[0832] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0833] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0834] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0835] For example, R vi2 When one -CH2- in the alkyl group is replaced by -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0836] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0837] The number of carbon atoms in the alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0838] In addition, R vi2 When one -CH2- in the alkyl group is replaced by -S-, a thioalkoxy group (alkylthio, alkylthio) having 1 to 19 carbon atoms can be represented.

[0839] The thioalkoxy group is a linear, branched or cyclic thioalkoxy group, and is preferably a linear thioalkoxy group.

[0840] The number of carbon atoms in the thioalkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0841] In addition, R vi2 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0842] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[0843] The number of carbon atoms in the alkenyl group is preferably 2 to 10, more preferably 2 to 6.

[0844] In addition, R vi2 When one or two or more -CH2-CH2- groups in the alkyl group are replaced by -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0845] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[0846] The number of carbon atoms in the alkynyl group is preferably 2 to 10, more preferably 2 to 6.

[0847] In addition, R vi2 When one -CH2- in the alkyl group is replaced by -O-, and one or two or more -CH2-CH2- are replaced by -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented.

[0848] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[0849] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[0850] In addition, R vi2 By substituting one or two or more hydrogen atoms in the alkyl group with a halogen atom, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0851] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0852] The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, more preferably 2 to 6.

[0853] In addition, R vi2 When one -CH2- in the alkyl group is substituted with -O-, and one or two or more hydrogen atoms in the alkyl group are substituted with halogen atoms, a halogenated alkoxy group having 1 to 19 carbon atoms can be represented.

[0854] The halogenated alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0855] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0856] As R vi2 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted groups) include the following: vi2 -1)~(Rvi2 -36) etc.

[0857]

[0858] Formula (R vi2 -1)~(R vi2 -36), the black dot indicates the direction to A vi3 connection key.

[0859] In R vi2 When the ring structure connected is a phenyl group (aromatic group), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. i1 When the linked ring structure is a saturated ring structure such as cyclohexane, pyran, and dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms.

[0860] In addition, as R vi2 In order to stabilize the nematic phase, the total number of carbon atoms and, if present, oxygen atoms is preferably 5 or less, and a linear chain is preferred.

[0861] Furthermore, as R vi2 , from solubility, Δn and / or Δε r From the viewpoint of , a linear alkyl group having 2 to 6 carbon atoms or a linear thioalkoxy group having 1 to 6 carbon atoms is preferred.

[0862] In the general formula (vi), A vi1 、A vi2 and A vi3 Each independently represents any one of a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms.

[0863] More specifically, the hydrocarbon ring having 3 to 16 carbon atoms or the heterocyclic ring having 3 to 16 carbon atoms preferably represents a group selected from the group consisting of the following groups (a), (b), (c), and (d):

[0864] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups in the group may be substituted with -O- or -S-)

[0865] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=)

[0866] (c) 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, phenanthrene -2,7-diyl (one or two or more -CH= groups present in naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl or phenanthrene-2,7-diyl may be substituted with -N=)

[0867] (d) Thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, thieno[3,2-b]thiophene-2,5-diyl (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=).

[0868] A vi1 、A vi2 and A vi3 One or more hydrogen atoms in the group may be independently substituted by a substituent group S vi1 replace.

[0869] Substituent S vi1 It represents any one of 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, and an alkyl group having 1 to 20 carbon atoms.

[0870] The alkyl group is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0871] The number of carbon atoms in the alkyl group is preferably 2 to 10, more preferably 3 to 6.

[0872] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S- and / or -CO-.

[0873] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CH=CH-, -CF=CF-, -C≡C-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH- and / or -NH-CO-.

[0874] Furthermore, one or two or more -CH2-CH2-CH2- groups in the alkyl group may be substituted with -O-CO-O-.

[0875] One or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[0876] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0877] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0878] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0879] As a substituent S vi1 , preferably a fluorine atom or a linear alkyl group having 1 to 3 carbon atoms.

[0880] In addition, it is preferred that A vi1 、A vi2 and A vi3 At least one of the substituents S vi1 replace.

[0881] In addition, A vi1 Preferably, at least one substituent S vi1 replace.

[0882] Furthermore, in the substituent S vi1 When there are multiple ones, they may be the same or different.

[0883] As A vi1 The substituent S in vi1 The substitution position is preferably the following formula (A vi1 -SP-1)~(A vi1 -SP-2).

[0884]

[0885] Formula (A vi1 -SP-1)~(A vi1 -SP-2), the white dot indicates the direction to R vi1 The black dots represent the connecting bonds to -C≡C-.

[0886] As A vi2 The substituent S in vi1 The substitution position is preferably the following formula (A vi2 -SP-1)~(A vi2-SP-7) is preferably represented by the following formula (A vi2 -SP-1)~(A vi2 -SP-7).

[0887]

[0888] Formula (A vi2 -SP-1)~(A vi2 -SP-7), white dots represent the connecting bonds to -C≡C, and black dots represent the connecting bonds to Z vi1 connection key.

[0889] As A vi3 The substituent S in vi3 The substitution position is preferably the following formula (A vi3 -SP-1)~(A vi3 -SP-7), preferably represented by the following formula (A vi3 -SP-1)~(A vi3 -SP-5) in any one.

[0890]

[0891] Formula (A vi3 -SP-1)~(A vi3 -SP-7), the white dot indicates the direction of Z vi1 The black dot indicates the connection key to Z vi1 or R vi2 connection key.

[0892] More specifically, A vi1 Preferably, it is represented by the following formula (A vi1 -1)~(A vi1 -Any of 4).

[0893]

[0894] Formula (A vi1 -1)~(A vi1 -4), the white dot indicates the direction to R vi1 The black dots represent the connecting bonds to -C≡C-.

[0895] More specifically, A vi2 Preferably, it is represented by the following formula (A vi2 -1)~(A vi2 -5) in any one of the following.

[0896]

[0897] Formula (A vi2 -1)~(A vi2 -5), the white dots represent the connecting bonds to -C≡C-, and the black dots represent the connecting bonds to Z i1 connection key.

[0898] More specifically, A vi3 Preferably, it is represented by the following formula (A vi3 -1)~(A vi3 -3) any one of.

[0899]

[0900] Formula (A vi3 -1)~(A vi3 -3), the white dot indicates the direction Z vi1 The black dot indicates the connection key to Z vi1 or R vi2 connection key.

[0901] In the general formula (vi), Z vi1 Each independently represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms.

[0902] The alkylene group is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0903] The number of carbon atoms in the alkylene group is preferably 2 to 10, more preferably 2 to 6.

[0904] One or two or more -CH2- groups in the alkylene group may be independently substituted with -O-, -CF2- and / or -CO-.

[0905] In addition, one or more -CH2-CH2- groups in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[0906] Furthermore, one or two or more -CH2-CH2-CH2- in the alkyl group may be independently substituted with -O-CO-O-.

[0907] However, when the alkylene group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0908] Specific examples of the alkylene group having 2 to 20 carbon atoms (including substituted groups) include the following: vi1 -1)~(Z vi1-24) represented by the base, etc.

[0909]

[0910] Formula (Z vi1 -1)~(Z vi1 -24), the white dot indicates the direction to A vi2 or A vi3 The black dot indicates the connection bond to A vi3 connection key.

[0911] n vi1 It is an integer of 1 to 3, preferably an integer of 1 to 2.

[0912] In n vi1 When Δn and / or Δε is 1, r From the perspective of Z vi1 Preferably, it represents -C≡C-.

[0913] In addition, in n vi1 When Δn and / or Δε are 2 or 3, r From the perspective of Z vi1 Preferably, at least one of represents -C≡C-.

[0914] Furthermore, as general formula (vi), in A vi3 and Z vi1 When there are multiple ones, they may be the same or different.

[0915] As the compound represented by the general formula (vi), a compound represented by the following general formula (vi-1) is preferable.

[0916]

[0917] In the general formula (vi-1), R vi1 、R vi2 、A vi1 、A vi2 and A vi3 Represents the same as R in the above general formula (vi) vi1 、R vi2 、A vi1 、A vi2 and A vi3 Same meaning respectively.

[0918] As the compound represented by the general formula (vi-1), compounds represented by the following general formulas (vi-1-1) to (vi-1-7) are preferred.

[0919]

[0920] In the general formulas (vi-1-1) to (vi-1-7), R vi1 、R vi2 and S vi1 Each independently represents R in the above general formula (vi) vi1 、R vi2 and S vi1 Same meaning respectively.

[0921] Specific examples of the compound represented by General Formula (vi-1-1) include compounds represented by the following structural formulas (vi-1-1.1) to (vi-1-1.2).

[0922]

[0923] Specific examples of the compound 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).

[0924]

[0925] Specific examples of the compound 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).

[0926]

[0927] Specific examples of the compound 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).

[0928]

[0929] Specific examples of the compound 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).

[0930]

[0931] Specific examples of the compound 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).

[0932]

[0933] Specific examples of the compound represented by General Formula (vi-1-7) include compounds represented by the following structural formula (vi-1-7.1).

[0934]

[0935] The type of compounds represented by general formula (vi), general formula (vi-1), general formula (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) used in the liquid crystal composition is 1 or more, preferably 1 to 10, preferably 1 to 5, and preferably 1 to 3.

[0936] The lower limit of the total content of the compounds represented by general formula (vi), general formula (vi-1), general formula (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) in 100 mass% of the liquid crystal composition is preferably 1 mass% or more, preferably 3 mass% or more, and preferably 5 mass% or more.

[0937] The upper limit value of the total content of the compounds represented by general formula (vi), general formula (vi-1), general formula (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) 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.

[0938] The total content of the compounds represented by general formula (vi), general formula (vi-1), general formula (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) in 100% by mass of the liquid crystal composition is determined from the solubility, Δn and / or Δε r From the viewpoint of the content of cellulose, the content is preferably 1 to 35% by mass, more preferably 3 to 30% by mass, and even more preferably 5 to 25% by mass.

[0939] The compound represented by the general formula (vi) (including subordinate concepts) can be synthesized using a known synthesis method.

[0940] The liquid crystal composition of the present invention is obtained from Δn and / or Δε r From the viewpoint of further containing one or more compounds represented by the following general formula (vii) having at least one -C≡C- and -N=N- as a linking group.

[0941] R vii1 -A vii1 -C≡CA vii2 -N=NA vii3 -R vii2 (Vii)

[0942] In the general formula (vii), R vii1 and R vii2 Each independently represents a halogen atom, a cyano group, or an alkyl group having 1 to 20 carbon atoms.

[0943] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0944] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0945] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0946] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO- and / or -CS-.

[0947] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[0948] Furthermore, one or two or more -CH2-CH2-CH2- in the alkyl group may be independently substituted with -O-CO-O-.

[0949] Furthermore, one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[0950] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0951] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[0952] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[0953] For example, R vii1 and R vii2 When one -CH2- in the alkyl group is replaced by -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[0954] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

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

[0956] In addition, R vii1 and R vii2 When one -CH2- in the alkyl group is replaced by -S-, a thioalkoxy group (alkylthio, alkylthio) having 1 to 19 carbon atoms can be represented.

[0957] The thioalkoxy group is a linear, branched or cyclic thioalkoxy group, and is preferably a linear thioalkoxy group.

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

[0959] In addition, R vii1 and R vii2 By substituting one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[0960] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

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

[0962] In addition, R vii1 and R vii2 When one or two or more -CH2-CH2- groups in the alkyl group are replaced by -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[0963] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

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

[0965] In addition, R vii1 and R vii2 When one -CH2- in the alkyl group is replaced by -O-, and one or two or more -CH2-CH2- are replaced by -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented.

[0966] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

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

[0968] In addition, R vii1 and R vii2 By substituting one or two or more hydrogen atoms in the alkyl group with a halogen atom, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[0969] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

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

[0971] R vii1 and R vii2 When one -CH2- in the alkyl group is substituted with -O-, and one or two or more hydrogen atoms in the alkyl group are substituted with halogen atoms, a halogenated alkoxy group having 1 to 19 carbon atoms can be represented.

[0972] The halogenated alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0973] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[0974] As R vii1 and R vii2Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted groups) include the following: vii1 / 2 -1)~(R vii1 / 2 -36) etc.

[0975]

[0976] Formula (R vii1 / 2 -1)~(R vii1 / 2 -36), the black dot indicates the direction to A vii1 or A vii3 connection key.

[0977] R vii1 When emphasis is placed on the reliability of the entire liquid crystal composition, an alkyl group having 1 to 12 carbon atoms is preferred. When emphasis is placed on reducing the viscosity of the entire liquid crystal composition, an alkenyl group having 2 to 8 carbon atoms is preferred.

[0978] In addition, in R vii1 When the ring structure connected is a phenyl group (aromatic group), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. vii1 When the linked ring structure is a saturated ring structure such as cyclohexane, pyran, and dioxane, it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms.

[0979] In addition, as R vii1 In order to stabilize the nematic phase, the total number of carbon atoms and oxygen atoms, if present, is 5 or less, and a linear chain is preferred.

[0980] R vii2 When the compound represented by general formula (vii) is a so-called p-type compound in which Δε is positive, a fluorine atom, a cyano group, a trifluoromethyl group or a trifluoromethoxy group is preferred, and a fluorine atom or a cyano group is preferred.

[0981] When the compound represented by general formula (vii) is a so-called non-polar compound in which Δε is almost 0, R vii2 Represents R vii1 Same meaning, R vii2 With R vii1 It can be the same or different.

[0982] Furthermore, as R vii1 / 2 From the viewpoint of solubility, a linear alkyl group having 2 to 6 carbon atoms is preferred.

[0983] In the general formula (vii), A vii1 、A vii2 and Avii3 Each independently represents a group selected from the group consisting of the following groups (a), (b) and (c):

[0984] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups in the group may be substituted with -O-)

[0985] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=)

[0986] (c) naphthalene-1,4-diyl, naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH= or two or more non-adjacent -CH= groups in naphthalene-1,4-diyl, naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N=).

[0987] Furthermore, one or two or more hydrogen atoms in the above-mentioned group (a), group (b) and group (c) may each independently be substituted with a halogen atom, a cyano group or an alkyl group having 1 to 6 carbon atoms.

[0988] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of stability and safety, a fluorine atom is preferred.

[0989] To improve the response speed, A vii1 、A vii2 and / or A vii3 The group (a) is preferably an aliphatic divalent cyclic group. When an increase in Δn is required, the group (b) or the group (c) is preferably a divalent cyclic group exhibiting aromaticity. Each of the groups (a) and (b) is preferably independently any one of the following structures:

[0990]

[0991] (R represents an alkyl group having 1 to 6 carbon atoms.)

[0992] Preferred is any one of 1,4-phenylene, naphthalene-2,6-diyl and tetrahydronaphthalene-2,6-diyl, wherein one or two or more hydrogen atoms in these 1,4-phenylene, naphthalene-2,6-diyl and tetrahydronaphthalene-2,6-diyl groups may each independently be substituted with a fluorine atom or an alkyl group having 1 to 6 carbon atoms.

[0993] Especially A vii1 When it represents a group selected from the group consisting of the following groups (d) to (f), it is preferred from the viewpoint of increasing Δn.

[0994]

[0995] (X vii1 and X vii2 Each independently represents a hydrogen atom or a fluorine atom.)

[0996] Furthermore, from the viewpoint of compatibility with other liquid crystal compounds, it is preferable to represent a group (f).

[0997] In addition, in order to improve the compatibility with other liquid crystal compositions, A vii1 、A vii2 and / or A vii3 At least one of them preferably represents a 1,4-phenylene group substituted by an alkyl group having 1 to 6 carbon atoms, and more preferably represents a 1,4-phenylene group substituted by an ethyl group.

[0998] The ring structure A in one molecule of the compound represented by the general formula (vii) of the present invention vii1 、A vii2 and / or A vii3 The total number of fluorine atoms is preferably 1 to 5, more preferably 1 to 4.

[0999] The compound represented by the above-mentioned general formula (vii) is preferably a compound represented by the following general formulas (vii-1) to (vii-3).

[1000]

[1001] (In the above general formulas (vii-1) to (vii-3), R vii1 、R vii2 、A vii2 and A vii3 represents the same as R in the above general formula (vii) vii1 、R vii2 、A vii2 and A vii3 They have the same meanings, and preferred groups and preferred numbers are also the same.

[1002] In the above general formulas (vii-1) to (vii-3), X vii1 and X vii2 Each independently represents a hydrogen atom or a fluorine atom.)

[1003] Specific examples of the compound represented by general formula (vii-1) include compounds represented by the following structural formulas (vii-1.1) to (vii-1.74).

[1004]

[1005]

[1006]

[1007]

[1008] Specific examples of the compound 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 each independently represents 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 number of compounds represented by general formula (vii), general formula (vii-1) to general formula (vii-3), structural formulas (vii-1.1) to (vii-1.74) or structural formulas (vii-2.1) to (vii-2.22) used in the liquid crystal composition is 1 or more, preferably 1 to 10, and preferably 1 to 5.

[1014] The lower limit of the total content of the compounds represented by general formula (vii), general formula (vii-1) to general formula (vii-3), structural formulas (vii-1.1) to (vii-1.74) or structural formulas (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 value of the total content of compounds represented by general formula (vii), general formula (vii-1) to general formula (vii-3), structural formulas (vii-1.1) to (vii-1.74) or structural formulas (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 of the 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% by mass of the liquid crystal composition is determined from the solubility, Δn and / or Δεr From the viewpoint of the content of cellulose, the content is preferably 5 to 40% by mass, more preferably 10 to 35% by mass, and even more preferably 15 to 30% by mass.

[1017] The compound represented by the general formula (vii) (including subordinate concepts) can be produced using a known method.

[1018] The liquid crystal composition of the present invention may further contain one or more compounds represented by the following general formulae (np-1) to (np-3) from the viewpoint of solubility.

[1019]

[1020] In the general formulas (np-1) to (np-3), R npi and R npii Each independently represents 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 linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[1022] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[1023] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO- and / or -CS-.

[1024] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF- and / or -C≡C-.

[1025] Furthermore, one or two or more -CH2-CH2-CH2- in the alkyl group may be independently substituted with -O-CO-O-.

[1026] Furthermore, one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[1027] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[1028] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[1029] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1030] For example, R npi and R npii When one -CH2- in the alkyl group is replaced by -O-, an alkoxy group having 1 to 19 carbon atoms can be represented.

[1031] The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[1032] The number of carbon atoms in the alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[1033] In addition, R npi and R npii When one -CH2- in the alkyl group is replaced by -S-, a thioalkoxy group (alkylthio, alkylthio) having 1 to 19 carbon atoms can be represented.

[1034] The thioalkoxy group is a linear, branched or cyclic thioalkoxy group, and is preferably a linear thioalkoxy group.

[1035] The number of carbon atoms in the thioalkoxy group is preferably 1 to 10, more preferably 1 to 6.

[1036] In addition, R npi and R npii By substituting one or two or more -CH2-CH2- groups in the alkyl group with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented.

[1037] The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group.

[1038] The number of carbon atoms in the alkenyl group is preferably 2 to 10, more preferably 2 to 6.

[1039] In addition, R npi and R npii When one or two or more -CH2-CH2- groups in the alkyl group are replaced by -C≡C-, an alkynyl group having 2 to 20 carbon atoms can be represented.

[1040] The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group.

[1041] The number of carbon atoms in the alkynyl group is preferably 2 to 10, more preferably 2 to 6.

[1042] In addition, R npi and R npii When one -CH2- in the alkyl group is replaced by -O-, and one or two or more -CH2-CH2- are replaced by -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented.

[1043] The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group.

[1044] The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, more preferably 2 to 6.

[1045] In addition, R npi and R npii By substituting one or two or more hydrogen atoms in the alkyl group with a halogen atom, a halogenated alkyl group having 1 to 20 carbon atoms can be represented.

[1046] The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[1047] The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, more preferably 2 to 6.

[1048] R npi and R npii When one -CH2- in the alkyl group is substituted with -O-, and one or two or more hydrogen atoms in the alkyl group are substituted with halogen atoms, a halogenated alkoxy group having 1 to 19 carbon atoms can be represented.

[1049] The halogenated alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[1050] The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, more preferably 2 to 6.

[1051] As R npi and R npii Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted groups) include the following: npi / ii -1)~(R npi / ii -36) etc.

[1052]

[1053] Formula (R npi / ii -1)~(R npi / ii -36), the black dots represent the bonds to ring A, ring B, ring C, or ring D.

[1054] As R npi and R npii Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[1055] In general formulae (np-1) to (np-3), ring A, ring B, ring C, and ring D each independently represent a group selected from the group consisting of the following groups (a), (b), (c), and (d):

[1056] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- groups in the group may be substituted with -O-)

[1057] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=)

[1058] (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH= or two or more non-adjacent -CH= groups in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N=)

[1059] (d) 1,4-cyclohexenylene, 1,3-dioxane-trans-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl.

[1060] One or more hydrogen atoms in the above ring A, ring B, ring C and ring D may be independently substituted with a substituent group S npi1 replace.

[1061] Substituent S npi1 represents any one of a halogen atom, a cyano group, and an alkyl group having 1 to 20 carbon atoms.

[1062] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of stability and safety, a fluorine atom is preferred.

[1063] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[1064] The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[1065] One or two or more -CH2- groups in the alkyl group may be independently substituted with -O-, -S-, -CO- and / or -CS-.

[1066] In addition, one or more -CH2-CH2- in the alkyl group may be independently substituted by -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CO-NH-, -NH-CO-, -CH=CH-, -CF=CF- and / or -C≡C-.

[1067] One or two or more -CH2-CH2-CH2- groups in the alkyl group may be independently substituted with -O-CO-O-.

[1068] Furthermore, one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[1069] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[1070] However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[1071] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1072] As a substituent S npi1 , from V th From the viewpoint of , a halogen atom is preferred, and a fluorine atom is preferred.

[1073] Furthermore, in the substituent S npi1 When there are multiple ones, they may be the same or different.

[1074] As a substituent S in ring A npi1 The substitution position is preferably the following formula (A-SP-1).

[1075]

[1076] In formula (A-SP-1), the white dot represents the direction of R npi The black dot indicates the connection key to Z npi connection key.

[1077] More specifically, ring A preferably represents any one of the following formulae (A-1) to (A-3).

[1078]

[1079] In formulas (A-1) to (A-3), the white dots represent the direction of R npi The black dot indicates the connection key to Z npi connection key.

[1080] More specifically, ring B preferably represents any one of the following formulae (B-1) to (B-2).

[1081]

[1082] In formulas (B-1) and (B-2), the white dots represent the Z direction. npi The black dot indicates the connection bond to R npii or Z npii connection key.

[1083] More specifically, ring C preferably represents any one of the following formulae (C-1) to (C-2).

[1084]

[1085] In formulas (C-1) and (C-2), the white dots represent the Z direction. npii The black dot indicates the connection bond to R npii or Z npiii connection key.

[1086] In the general formulas (np-1) to (np-3), Z npi 、Z npii and Z npiii Each independently represents any one of a single bond and an alkylene group having 1 to 20 carbon atoms.

[1087] One or two or more -CH2- groups in the alkylene group may each independently be substituted with -O-.

[1088] In addition, one or more -CH2-CH2- groups in the alkylene group may be independently substituted by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-.

[1089] Furthermore, one or two or more -CH2-CH2-CH2- in the alkyl group may be independently substituted with -O-CO-O-.

[1090] However, when the alkyl group having 1 to 10 carbon atoms is substituted with a specific group, oxygen atoms are not directly bonded to each other.

[1091] Furthermore, from the viewpoint of compound stability, it is preferred that sulfur atoms and / or oxygen atoms and sulfur atoms are not directly bonded to each other.

[1092] Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted groups) include the following: npi / ii / iii -1)~(Z npi / ii / iii -24) represented by the base, etc.

[1093]

[1094] Formula (Z npi / ii / iii -1)~(Z npi / ii / iii -24), a white dot represents a bond to ring A, ring B, or ring C, and a black dot represents a bond to ring B, ring C, or ring D.

[1095] From Δn and / or Δε r From the perspective of Z npi 、Z npii and Znpiii Each independently preferably represents any one of a single bond, -C≡C-, and -CO-O-.

[1096] However, the compounds represented by general formulae (np-1) to (np-3) do not include compounds represented by general formulae (vi) and (vii) (including subordinate concepts).

[1097] As the compound represented by the general formula (np-2), compounds represented by the following general formulas (np-2-1) to (np-2-2) are preferred.

[1098]

[1099] In the general formulas (np-2-1) to (np-2-2), R npi 、R npii and S npi Indicates the R in the above general formulas (np-1) to (np-3) npi 、R npii and S npi Same meaning respectively.

[1100] Specific examples of the compound represented by General Formula (np-2-1) include compounds represented by the following Structural Formula (np-2-1.1).

[1101]

[1102] Specific examples of the compound represented by General Formula (np-2-2) include compounds represented by the following structural formulas (np-2-2.1) to (np-2-2.5).

[1103]

[1104] The types of compounds represented by general formula (np-1) to (np-3), general formula (np-2-1) to (np-2-2), structural formula (np-2-1.1) or structural formula (np-2-2.1) to (np-2-2.5) used in the liquid crystal composition are 1 or more, preferably 1 to 10, preferably 1 to 8, preferably 1 to 6, preferably 1 to 4, and preferably 1 to 2.

[1105] The lower limit of the total content of the compounds represented by general formula (np-1) to (np-3), general formula (np-2-1) to (np-2-2), structural formula (np-2-1.1) or structural formula (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%.

[1106] The upper limit value of the total content of the compounds represented by general formula (np-1) to (np-3), general formula (np-2-1) to (np-2-2), structural formula (np-2-1.1) or structural formula (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%.

[1107] The total content of the compounds represented by general formula (np-1) to (np-3), general formula (np-2-1) to (np-2-2), structural formula (np-2-1.1) or structural formula (np-2-2.1) to (np-2-2.5) in 100% by mass of the liquid crystal composition is determined from the solubility, Δn and / or Δε r From the viewpoint of the content of cellulose, the content is preferably 1 to 50% by mass, more preferably 5 to 40% by mass, and even more preferably 10 to 30% by mass.

[1108] The compounds represented by general formulae (np-1) to (np-3), general formulae (np-2-1) to (np-2-2), structural formula (np-2-1.1), or structural formulae (np-2-2.1) to (np-2-2.5) can be produced by known methods.

[1109] (Liquid Crystal Composition)

[1110] The liquid crystal composition of the present invention can be produced by mixing, for example, the compound represented by the above-mentioned general formula (i), the above-mentioned other compounds as needed, and additives.

[1111] Examples of additives include stabilizers, pigment compounds, and polymerizable compounds.

[1112] Examples of the stabilizer include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, hindered phenols, and hindered amines.

[1113] Examples of the hindered phenols include hindered phenol-based antioxidants represented by the following structural formulas (XX-1) to (XX-3).

[1114]

[1115] Examples of the hindered amines include hindered amine-based light stabilizers represented by the following structural formulas (YY-1) to (YY-2).

[1116]

[1117] When a stabilizer is used, the total content of the stabilizer in 100% by mass of the liquid crystal composition is preferably 0.005 to 1% by mass, more preferably 0.02 to 0.50% by mass, and more preferably 0.03 to 0.35% by mass.

[1118] As a combination of compounds used in the liquid crystal composition, solubility, Δn and / or Δε r From the perspective of the present invention, it is preferred that the compound represented by the general formula (i) (including the subordinate concept) is combined with the compound represented by the general formula (ii) (including the subordinate concept); the compound represented by the general formula (i) (including the subordinate concept), the compound represented by the general formula (ii) (including the subordinate concept), and the compound represented by the general formula (vi) (including the subordinate concept); the compound represented by the general formula (i) (including the subordinate concept), the compound represented by the general formula (ii) (including the subordinate concept), the compound represented by the general formula (vi) (including the subordinate concept), and the compound represented by the general formula (vii) (including the subordinate concept).

[1119] <Characteristic Values ​​of Liquid Crystal Composition>

[1120] The upper limit temperature of the liquid crystal phase (T ni ) is the temperature at which the liquid crystal composition undergoes a phase transition from the nematic phase to the isotropic phase.

[1121] T ni The measurement was performed by preparing a product in which the liquid crystal composition was sandwiched between a slide glass and a cover glass, and observing the product under a polarizing microscope while heating the product on a hot stage.

[1122] Alternatively, the content can be measured by differential scanning calorimetry (DSC).

[1123] The unit used is "℃".

[1124] T ni The higher the value, the nematic phase can be maintained even at high temperatures, and the driving temperature range can be expanded.

[1125] The upper limit temperature of the liquid crystal phase of the liquid crystal composition of the present invention (T ni ) can be appropriately set depending on whether it is used indoors or in a car where the external temperature of the liquid crystal display element can be controlled, or when it is used outdoors, but from the perspective of the driving temperature range, it is preferably above 100°C, preferably 100-200°C, and preferably 110-190°C.

[1126] Liquid crystal phase lower limit temperature (T →N ) is the temperature at which a liquid crystal composition undergoes a phase transition from other phases (glass, smectic phase, crystalline phase) to the nematic phase.

[1127] T→N The measurement was performed by filling a glass capillary with a liquid crystal composition, immersing the capillary in a -70°C refrigerant, causing the liquid crystal composition to undergo a phase transition to another phase, and observing the phase while increasing the temperature.

[1128] Alternatively, the content can be measured by differential scanning calorimetry (DSC).

[1129] The unit used is "℃".

[1130] T →N The lower the tantalum ratio, the more the nematic phase can be maintained even at low temperatures, thus widening the driving temperature range.

[1131] The lower limit temperature of the liquid crystal phase of the liquid crystal composition of the present invention (T →N ) From the viewpoint of the driving temperature range, it is preferably 10°C or less, preferably -70 to 0°C, and preferably -40 to -5°C.

[1132] Δn (refractive index anisotropy) is related to Δn in the near-infrared region used in an optical sensor described later.

[1133] The larger Δn is, the greater the phase modulation power of light of the target wavelength is, and therefore it is particularly suitable for optical sensors.

[1134] The Δn at 25° C. and 589 nm was determined using an Abbe refractometer based on the extraordinary refractive index (n e ) and the refractive index of ordinary light (n o ) difference (n e -n o ) to obtain it.

[1135] Alternatively, Δn can be obtained using a phase difference measuring device.

[1136] The relationship between the phase difference Re, the thickness d of the liquid crystal layer, and Δn is Δn=Re / d.

[1137] The liquid crystal composition was injected into a glass cell with a polyimide alignment film having a cell gap (d) of about 3.0 μm and subjected to antiparallel rubbing treatment, and the in-plane Re was measured using a retardation film / optical material inspection apparatus RETS-100 (manufactured by Otsuka Electronics Co., Ltd.).

[1138] The measurement was performed at 25°C and 589 nm.

[1139] No unit.

[1140] The liquid crystal composition of the present invention preferably has a Δn at 25° C. and 589 nm of 0.30 or more, preferably 0.30 to 0.60, preferably 0.35 to 0.55, and preferably 0.38 to 0.50.

[1141] The rotational viscosity (γ1) is a viscosity coefficient related to the rotation of liquid crystal molecules.

[1142] γ1 can be measured by filling a glass cell having a cell gap of about 10 μm with the liquid crystal composition and using LCM-2 (manufactured by TOYO Corporation).

[1143] In the case of a liquid crystal composition having positive dielectric anisotropy, a horizontal alignment unit is used, and in the case of a liquid crystal composition having negative dielectric anisotropy, a vertical alignment unit is used.

[1144] The measurement was performed at a temperature of 25°C.

[1145] The unit used is mPa·s.

[1146] The smaller γ1 is, the faster the response speed of the liquid crystal composition becomes, and thus the liquid crystal composition is applicable to any liquid crystal display element.

[1147] The rotational viscosity (γ1) of the liquid crystal composition of the present invention at 25° C. is preferably 150 to 2000 mPa·s, preferably 200 to 1800 mPa·s, and preferably 250 to 1500 mPa·s from the viewpoint of response speed.

[1148] Threshold voltage (V th ) is related to the driving voltage of the liquid crystal composition.

[1149] V th The liquid crystal composition can be filled in a TN cell having a gap of 8.3 μm and is determined based on the transmittance when a voltage is applied.

[1150] The measurement was performed at a temperature of 25°C.

[1151] The unit is "V".

[1152] V th The lower the voltage, the lower the drive voltage.

[1153] The V of the liquid crystal composition of the present invention at 25°C th From the viewpoint of driving voltage, it is preferably 3.0 V or less, preferably 0.3 to 3.0 V, preferably 0.5 to 2.7 V, preferably 0.7 to 2.5 V, preferably 0.9 to 2.3 V, preferably 1.1 to 2.1 V, and preferably 1.3 to 2.0 V.

[1154] The higher the dielectric anisotropy in the high-frequency region, the greater the phase modulation capability for radio waves in the target frequency band becomes, and thus the dielectric anisotropy is particularly suitable for antenna applications.

[1155] Furthermore, in antenna applications, a smaller dielectric loss tangent in a high-frequency region is preferable because the energy loss in a target frequency band is reduced.

[1156] In the liquid crystal composition of the present invention, the dielectric anisotropy Δε at 10 GHz was measured as a representative of the characteristics in the high frequency region. r and the average value of dielectric loss tangent tanδ iso .

[1157] Δε r =(ε r∥ -ε r⊥ ), tanδ iso =(2ε r⊥ tanδ ⊥ +ε r∥ tanδ ∥ ) / (2ε r⊥ +ε r∥ ).

[1158] Here, “εr” is the dielectric constant, “tanδ” is the dielectric loss tangent, the subscript “∥” indicates a component parallel to the alignment direction of the liquid crystal, and “⊥” indicates a component perpendicular to the alignment direction of the liquid crystal.

[1159] Δε r and tanδ iso The measurement can be performed by the following method.

[1160] First, a liquid crystal composition is introduced into a capillary tube made of polytetrafluoroethylene (PTFE).

[1161] The capillary used here has an inner radius of 0.80 mm and an outer radius of 0.835 mm, with an effective length of 4.0 cm.

[1162] The capillary tube enclosing the liquid crystal composition was introduced into the center of a cavity resonator (manufactured by EMLabs Co., Ltd.) having a resonance frequency of 10 GHz.

[1163] The cavity resonator has a diameter of 30 mm and a width of 26 mm.

[1164] Then, a signal was input and the output signal was recorded using a network analyzer (manufactured by Keysight Technologies, Inc.).

[1165] The dielectric constant (ε) at 10 GHz was determined by using the difference between the resonance frequency of the PTFE capillary tube without the liquid crystal composition and the resonance frequency of the PTFE capillary tube with the liquid crystal composition. r ) and loss angle (δ).

[1166] Then, the obtained tangent of δ is the dielectric loss tangent (tan δ).

[1167] Furthermore, regarding the resonant frequency of a PTFE capillary tube encapsulating a liquid crystal composition, by controlling the orientation of the liquid crystal molecules, the values ​​of the characteristic components perpendicular to the orientation direction of the liquid crystal molecules and the values ​​of the characteristic components parallel to the orientation direction of the liquid crystal molecules can be obtained.

[1168] In order to align the liquid crystal molecules in a perpendicular direction (perpendicular to the effective length direction) or in a parallel direction (parallel to the effective length direction) of the PTFE capillary, a magnetic field of a permanent magnet or an electromagnet is used.

[1169] For example, the magnetic field has a magnetic field intensity of 0.23 Tesla near the center at a distance of 45 mm between magnetic poles.

[1170] By rotating the PTFE capillary tube enclosing the liquid crystal composition parallel to or perpendicular to the magnetic field, desired characteristic components can be obtained.

[1171] The measurement was performed at a temperature of 25°C.

[1172] Δε r and tanδ iso There are no units.

[1173] Δε of the liquid crystal composition of the present invention at 25°C r More preferably, from the viewpoint of phase modulation power in the GHz band, it is preferably 0.90 or more, preferably 0.90 to 1.40, preferably 0.95 to 1.40, and preferably 1.00 to 1.40.

[1174] Tan δ of the liquid crystal composition of the present invention at 25°C iso Smaller is preferred. From the viewpoint of loss in the GHz band, it is preferably 0.025 or less, preferably 0.001 to 0.025, preferably 0.003 to 0.020, preferably 0.005 to 0.017, preferably 0.007 to 0.015, preferably 0.008 to 0.013, and preferably 0.009 to 0.012.

[1175] (Liquid crystal display elements, sensors, liquid crystal lenses, optical communication equipment and antennas)

[1176] Hereinafter, a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the liquid crystal composition of the present invention will be described.

[1177] The liquid crystal display device of the present invention is characterized by using the above-mentioned liquid crystal composition and is preferably driven by an active matrix method or a passive matrix method.

[1178] Furthermore, the liquid crystal display element of the present invention is preferably a liquid crystal display element in which the dielectric constant is reversibly switched by reversibly changing the alignment direction of liquid crystal molecules in the liquid crystal composition.

[1179] The sensor of the present invention is characterized by using the above-mentioned liquid crystal composition. For example, its methods include: a distance sensor using electromagnetic waves, visible light or infrared light; an infrared sensor using temperature changes; a temperature sensor using changes in the wavelength of reflected light caused by changes in the pitch of cholesteric liquid crystals; a pressure sensor using changes in the wavelength of reflected light; an ultraviolet sensor using changes in the wavelength of reflected light caused by changes in composition; an electrical sensor using temperature changes caused by voltage or current; a radiation sensor using temperature changes accompanying the tracks of radioactive particles; an ultrasonic sensor using changes in the arrangement of liquid crystal molecules caused by mechanical vibrations of ultrasonic waves; an electromagnetic sensor using changes in the wavelength of reflected light caused by temperature changes or changes in the arrangement of liquid crystal molecules caused by electric fields, etc.

[1180] As the distance measuring sensor, a LiDAR (Light Detection and Ranging) sensor using a light source is preferable.

[1181] LiDAR is preferably used for artificial satellites, airplanes, unmanned aircraft (drones), automobiles, railways, and ships.

[1182] As for automobile use, it is particularly preferably used for self-driving cars.

[1183] The light source is preferably a light-emitting diode (LED) or a laser, preferably a laser.

[1184] The light used for LiDAR is preferably infrared light, and the wavelength is preferably 800 nm to 2000 nm.

[1185] Infrared laser light having a wavelength of 905 nm or 1550 nm is particularly preferred.

[1186] When emphasis is placed on the cost and all-weather sensitivity of the photodetector used, a 905 nm infrared laser is preferred. When emphasis is placed on safety with respect to human vision, a 1550 nm infrared laser is preferred.

[1187] The liquid crystal composition of the present invention exhibits high Δn, and thus can provide a sensor having a large phase modulation capability in the visible light, infrared light, and electromagnetic wave regions and excellent detection sensitivity.

[1188] The liquid crystal lens of the present invention is characterized by using the above-mentioned liquid crystal composition. For example, as one embodiment thereof, the liquid crystal lens comprises: a first transparent electrode layer, a second transparent electrode layer, a liquid crystal layer containing the above-mentioned liquid crystal composition and disposed between the first transparent electrode layer and the second transparent electrode layer, an insulating layer disposed between the second transparent electrode layer and the liquid crystal layer, and a high-resistance layer disposed between the insulating layer and the liquid crystal layer.

[1189] The liquid crystal lens of the present invention is used as, for example, a 2D / 3D switching lens, a camera focus adjustment lens, and the like.

[1190] The optical communication device of the present invention is characterized by using the above-mentioned liquid crystal composition. For example, as one of its methods, there can be cited a liquid crystal on silicon (LCOS) having the following structure, which has a liquid crystal layer on a reflective layer (electrode), and the liquid crystals constituting each of the plurality of pixels are two-dimensionally arranged in the above-mentioned liquid crystal layer.

[1191] The optical communication device of the present invention is used as a spatial phase modulator, for example.

[1192] The antenna of the present invention is characterized by using the above-mentioned liquid crystal composition.

[1193] More specifically, the antenna of the present invention comprises: a first substrate having a plurality of slots, a second substrate opposite to the first substrate and provided with a power supply portion, a first dielectric layer provided between the first substrate and the second substrate, a plurality of patch electrodes arranged corresponding to the plurality of slots, a third substrate provided with the patch electrodes, and a liquid crystal layer provided between the first substrate and the third substrate; the liquid crystal layer contains the liquid crystal composition.

[1194] By using a liquid crystal composition containing one or more compounds represented by the general formula (i) having an ethynylene group (-C≡C-) and an isothiocyanate group (-NCS), T ni High, large Δn, V th Low, Δε r Large, tanδ iso Because it is small and has good storage properties at low temperatures, it can provide an antenna that is highly reliable against external stimuli such as heat.

[1195] This makes it possible to provide an antenna capable of performing greater phase control on microwave or millimeter wave electromagnetic waves.

[1196] Hereinafter, the antenna of the present invention will be described with reference to the drawings.

[1197] like Figure 1As shown, an antenna assembly 11, to which four antenna units 1 are connected, is mounted on the roof of a vehicle (car) 2. The antenna units 1 are planar antennas, and since they are mounted on the roof, they are always facing the direction of the communication satellite. This enables bidirectional satellite communication.

[1198] In this specification, the “antenna” includes the antenna unit 1 or the antenna assembly 11 formed by connecting a plurality of antenna units 1 .

[1199] The antenna of the present invention preferably operates at Ka-band frequencies, or K-band frequencies, or Ku-band frequencies for satellite communications.

[1200] then, Figure 2 1 shows an example of an embodiment of the components of the antenna unit 1 . Figure 2 yes Figure 1 The antenna unit 1 is shown in exploded view. Specifically, the antenna unit 1 comprises an antenna body 10, a control board 4 for controlling the antenna body 10, a housing 3 having a recess for accommodating the antenna body 10 and the control board 4, and a top cover 5 for closing the housing 3.

[1201] The control board 4 is equipped with a transmitter and / or receiver. The transmitter has a mechanism that performs source coding, such as voice or image coding, on information from a signal source, such as data such as speech or images. It then performs error correction coding through transmission line coding, modulates the information, and transmits it as radio waves. The receiver, on the other hand, has a mechanism that modulates the incoming radio waves, performs error correction through transmission line decoding, and then converts the information into data such as speech or images through source decoding, such as voice decoding or image decoding. The control board 4 is comprised of a well-known microcomputer, such as a central processing unit (CPU), random access memory (RAM), and read-only memory (ROM). It manages and controls the operations of the antenna body 1, the transmitter, and / or the receiver. Specific processing is performed by reading various programs pre-stored in the CPU or ROM of the control board 4 into the RAM and executing them. The control board 4 has the following functions, such as a storage unit, a calculation unit, and a detection unit. The storage unit stores various setting information or control programs. The calculation unit performs various calculations related to the voltage amount and voltage direction applied to the liquid crystal layer in the antenna body 1, various calculations related to the transmission of radio waves, and / or various calculations in the reception of radio waves. The detection unit detects the reception or transmission of radio waves or the application of voltage to the liquid crystal layer.

[1202] Figure 2In the specification, as an example of a shell 3 that can accommodate a disc-shaped antenna body 1, a hexagonal shell 3 and a top cover 5 are recorded, but the shell 3 and the top cover 5 can be appropriately changed to a known shape such as a cylinder, an octagonal prism, or a triangular prism according to the shape of the antenna body 1.

[1203] To explain the structure of the antenna body 10, the following uses Figures 3 to 10 Provide explanation. Figure 3 This is a schematic diagram showing the exploded components of the antenna main body 10 .

[1204] like Figure 3 As shown, the antenna main body 10 includes a slot antenna array portion 6 and a patch array portion 7. In addition, in the slot antenna array portion 6, a plurality of slots (cutouts) 8 are formed on the surface of the circular plate-shaped conductor P, and a power supply portion 12 is provided inside the center portion of the slot antenna array portion 6. In addition, in the patch array portion 7, as an example, a plurality of square patches (patches) 9 with a length L and a width W are formed on the circular plate body Q. In addition, the antenna main body 10 has the following structure: it has a slot antenna array portion 6 and a patch array portion 7, the slot antenna array portion 6 is a circular plate-shaped conductor P with a plurality of slots 8 formed therein, the patch array portion 7 is a circular plate-shaped patch array portion 7 with a plurality of patches formed therein, and the patch array portion 7 is bonded to the slot antenna array portion 6 so that the patches 9 are arranged opposite to each other corresponding to the respective slots 8 formed on the surface of the circular plate-shaped conductor P.

[1205] The slot antenna array unit 6 is an antenna unit that uses a cutout portion (hereinafter referred to as the slot 8) on the surface of a disk-shaped conductor P as a radiating element (or incident element). Furthermore, the slot antenna array unit 6 includes the slot 8 and a power supply portion 12 disposed in the center of the disk-shaped conductor P. Generally speaking, the slot antenna array unit 6 has a mechanism for directly exciting the front end of the transmission line or exciting via a cavity disposed on the back side of the slot. Furthermore, the slot antenna array unit 6 can be used to supply power to an antenna utilizing a substrate or to a patch antenna via a microstrip line or the like through the slot. Figure 3 , as an example of the slot antenna array unit 6, a radial line slot antenna array is described, but the scope of the present invention is not limited to this.

[1206] Figure 4 Shown in Figure 3 The top view of the slot antenna array section 6 is shown below. Figure 4 The slot antenna array section 6 is described below. The slot antenna array section 6 has a structure in which power is supplied via a coaxial line provided at its center. Figure 4The slot antenna array section 6 shown is provided with a power supply 12 at its center. Furthermore, the slot antenna array section 6 has a plurality of slots 8 (hereinafter referred to as "slot pairs") formed in groups on the surface of a disk-shaped conductor P. The slot pairs 8 have two rectangular cutouts arranged in an "eight" configuration. More specifically, the two rectangular slots 8 are arranged orthogonally, with one slot of the slot pair 8 spaced 1 / 4 wavelength apart from the other. This allows for the transmission and reception of circularly polarized waves having different rotational directions depending on the antenna's azimuth angle.

[1207] In this specification, two slits 8 are referred to as a slit pair 8 , one slit 8 is simply referred to as a slit 8 , and the general term for slits and slit pairs is referred to as a slit (pair) 8 .

[1208] Multiple slot pairs 8 are formed in a spiral pattern extending radially outward from the center of the disc-shaped conductive substrate P. Furthermore, the slot pairs 8 are formed on the disc-shaped substrate surface so that the distance between adjacent slot pairs 8 along the spiral is constant. This allows the phases to be aligned in front of the slot antenna array 6, enhancing the electromagnetic field and forming a pencil beam in the front direction.

[1209] Furthermore, Figure 3 and Figure 4 In the figure, an example of the shape of the slit 8 is shown as a rectangular parallelepiped. However, the shape of the slit 8 of the present invention is not limited to a rectangular parallelepiped, and a known shape such as a circle, an ellipse, or a polygon can be used. Figure 3 and Figure 4 In the embodiment, as an example of the slits 8, a pair of slits is shown, but the slits 8 of the present invention are not limited to pairs of slits. Furthermore, an example is shown in which the slits 8 on the surface of the disk-shaped conductor substrate P are arranged in a spiral shape, but the arrangement of the slits 8 is not limited to the spiral shape. The slits 8 may also be arranged in a manner such as described later. Figure 8 Concentric circles as shown.

[1210] The power supply unit 12 of the present invention has the function of receiving and / or radiating electromagnetic waves. Furthermore, the power supply unit 12 of the present invention is not particularly limited, as long as it is a portion that transmits the high-frequency power generated by the patch 9, which serves as a radiating element or incident element, to a receiver, or a portion that connects the radiating element to the power supply line for the purpose of supplying high-frequency power. Known power supplies and power supply lines can be used. Figure 3 and Figure 4 A coaxial power feeding portion is shown as an example.

[1211] like Figure 3As shown, the patch array unit 7 comprises a circular plate Q having a plurality of square patches 9 with a length L and a width W; and a liquid crystal layer (not shown) interposed between the patch array unit 7 and the slot antenna array unit 6. The patch array unit 7 of this embodiment is a so-called microstrip antenna, a resonator that resonates at a frequency that is equal to an integer multiple of 1 / 2 wavelength and has a length L.

[1212] Furthermore, Figure 3 , as an example of the patch 9 , a square patch 9 with a length of L and a width of W is shown. However, the shape of the patch 9 is not limited to a quadrilateral, and a circular patch 9 may also be used. Figure 5 , an embodiment of a circular patch 9 is shown as another embodiment of the present invention.

[1213] Figure 5 This is a top view of the antenna body 10 of the present invention. More specifically, it is a view of the patch 9, the feed portion 12, and the slot pair 8 projected perpendicularly relative to the main surface of the circular plate body Q when the antenna body 10 is viewed from the patch array portion 7. Therefore, the patch 9, the feed portion 12, and the slot pair 8 are represented by dotted lines. In addition, when the shape of the patch 9 is circular, it can generally be arranged in accordance with the so-called TM 11 The electromagnetic field distribution of the mode is operated. Figure 5 As shown, the projection of patch 9 overlaps with the projection of slot pair 8. Therefore, it can be understood that patches 9 provided on disk Q are arranged opposite to each slot 8 formed on the surface of disk-shaped conductor P. As described above, by utilizing a configuration in which each patch 9 is arranged corresponding to each slot 8, power can be supplied from slot 8 to patch 9 via electromagnetic coupling power supply, or incident radio waves can be propagated from patch 9 to slot 8. Consequently, an antenna capable of transmitting and / or receiving radio waves can be provided.

[1214] Generally speaking, methods for powering the radiating elements (e.g., patches 9) of patch array unit 7 using conventional transmission lines such as coaxial cables or planar transmission lines can be broadly categorized into two types: direct connection power supply and electromagnetic coupling power supply. Therefore, the present invention employs two power supply methods: a direct connection power supply method, which excites the radiating elements by directly connecting the transmission line to patches 9 (radiating elements); and an electromagnetic coupling power supply method, which excites the patch electrodes (radiating elements) by using the electromagnetic field generated around the open-ended or short-circuited power supply line, rather than directly connecting the transmission line to the patch electrodes (radiating elements). The present invention utilizes the electromagnetic coupling power supply method.

[1215] In this embodiment, the power supply line utilizing the (coaxial) power supply unit 12 is open-ended, thereby generating a current standing wave where the terminal of the power supply line coincides with a node. This generates a magnetic field surrounding the power supply line ((coaxial) power supply unit 12), which is incident on the slot 8, thereby exciting the slot (pair) 8. Furthermore, the magnetic field generated by the excitation of the slot (pair) 8 is incident on the patch 9, thereby exciting the patch 9. Since the excitation intensity is greatest when the magnetic field incident on the slot 8 is at its maximum, it is preferable to form the slot (pair) 8 at the location (the antinode of the current standing wave) where the magnetic field generated from the power supply line ((coaxial) power supply unit 12) is at its maximum.

[1216] A preferred embodiment of the antenna of the present invention is a combination of a radial line slot antenna array and a patch antenna array.

[1217] Next, use Figure 5 The cross-sectional view of the antenna body 10 shown is Figure 6 The embodiment of the antenna body 10 is described below. Figure 6 This is a schematic diagram showing the structure of an antenna.

[1218] like Figure 6 As shown, the antenna body 10 comprises a circular second substrate 14, a circular first substrate 13 (corresponding to the circular conductor P; also known as a slot array substrate) with multiple slots (pairs) 8 formed radially outward from the center, a first dielectric layer 17 disposed between the second and first substrates 14, 13, a power supply unit 12 disposed at the center of the first and second circular substrates 13, 14, a circular third substrate 15 (corresponding to the circular body Q; also known as a patch substrate), patches 9 (radiating elements or incident elements) mounted on the third substrate 15, and a liquid crystal layer 16 disposed between the third and first substrates 15, 13. The power supply unit 12 is electrically connected to the transmitter and / or receiver provided on the control board via a power supply line 12a. Furthermore, each patch 9 corresponds to a corresponding slot pair 8.

[1219] Here, "(each) patch 9 corresponds to (each) slot pair 8" means that Figure 5 As described above, the projection plane of the patch 9 perpendicularly projected relative to the main surface of the second substrate 14 overlaps with the gap (pair) 8. In other words, the projection plane of the gap (pair) 8 perpendicularly projected relative to the main surface of the third substrate 15 overlaps with the patch 9.

[1220] In addition, the first substrate 13 , the second substrate 14 , and the third substrate 15 are preferably circular plates having the same area.

[1221] exist Figure 6In FIG. 1 , it is described that the electric wave (arrow) supplied by the (coaxial) power supply unit 12 becomes a cylindrical wave and propagates outward in the first dielectric layer 17 in the radial direction, and is then transmitted from the gap (pair) 8 to the liquid crystal layer 16. Figure 4 As shown, slot (pair) 8 is arranged in a so-called "eight" shape, with two orthogonal slots offset by a quarter wavelength, to generate circularly polarized waves. As described above, slot (pair) 8 is excited by electromagnetic coupling power supply, and the magnetic field generated by slot (pair) 8 is incident on patch 9, exciting it. As a result, patch 9 can emit radio waves with high directivity.

[1222] On the other hand, when receiving incident radio waves, according to the reversible theorem of transmission and reception, contrary to the above, after receiving the incident radio waves, the patch 9 transmits the incident radio waves to the power supply unit 12 through the gap (pair) 8 provided directly below the patch 9.

[1223] Circularly polarized waves, unlike linearly polarized waves, are radio waves whose electric field direction rotates over time. They are classified into right-handed circularly polarized waves used in the Global Positioning System (GPS) or electronic toll collection (ETC), and left-handed circularly polarized waves used in satellite radio broadcasting, etc. The antenna of the present invention can receive either polarized wave.

[1224] By applying a voltage to the liquid crystal layer 16 between the patch 9 and the first substrate 13, the orientation 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, and thus the electrostatic capacitance of the gap (pair) 8 changes, resulting in the control of the reactance and resonant frequency of the gap (pair) 8. In other words, by controlling the dielectric constant of the liquid crystal layer 16, the reactance and resonant frequency of the gap 8 can be adjusted, and thus the power supply to each patch 9 by adjusting the excitation of the gap (pair) 8 and the patch 9 can be controlled. In this way, the electromagnetic waves radiated through the liquid crystal layer 16 can be adjusted. Therefore, for example, a voltage adjustment means such as a thin film transistor (TFT) can be provided to adjust the voltage applied to the liquid crystal layer 16. In addition, by changing the orientation of the liquid crystal molecules in the liquid crystal layer 16, the refractive index changes, and as a result, the phase of the electromagnetic wave penetrating the liquid crystal layer 16 is shifted. As a result, phase array control can be performed.

[1225] 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. In addition, the material of the third substrate 15 is not particularly limited. Depending on the usage, known materials such as glass substrates, acrylic substrates, ceramics (alumina), silicon, glass cloth Teflon (Glass Cloth Teflon) (registered trademark) (polytetrafluoroethylene (PTFE)) can be used. The material of the first dielectric layer 17 can be selected from known materials according to the desired relative dielectric constant, and can also be a vacuum. Furthermore, the material of the patch 9 is not particularly limited as long as it is a conductor such as copper or silver.

[1226] Next, use Figure 7 Another embodiment of the antenna main body 10 will be described. Figure 7 The embodiment shown in FIG is a portion of the slot antenna array portion 6 of the antenna body 10 and Figure 6 The embodiments shown are different.

[1227] exist Figure 7 In the embodiment, the antenna body 10 has a hollow first substrate 13 with a plurality of slits (pairs) 8 formed on one surface, a circular second substrate 14 housed inside the hollow first substrate 13, a first dielectric layer 17 and a power supply unit 12, a circular third substrate 15, a patch 9 mounted on the third substrate 15, and a liquid crystal layer 16 arranged between the third substrate 15 and the first substrate 13; and the power supply unit 12 is arranged between the other surface of the first substrate 13 where the plurality of slits (pairs) 8 are not formed and the second substrate 14, and is arranged in the center of the first substrate 13 and the circular second substrate 14. In addition, the power supply unit 12 is electrically connected to the transmitter and / or receiver arranged on the control substrate via a power supply line 12a. Moreover, each patch 9 corresponds to each slit pair 8. In addition, in Figure 7 In the embodiment, both side surfaces of the first substrate 13 of the hollow body protrude outward from the hollow body, and specifically, have inclined surfaces at 45° relative to the horizontal direction.

[1228] like Figure 7 As shown in the figure, the electric wave (arrow) supplied by the (coaxial) power supply unit 12 becomes a cylindrical wave and propagates radially outward in the first dielectric layer 17. Moreover, the propagating cylindrical wave is reflected by the two side surfaces of the hollow first substrate 13, and the cylindrical wave that bypasses the second substrate 14 is converted into a traveling wave (arrow) from the outer periphery of the circular plate-shaped first substrate 13 toward the center and propagates in the first dielectric layer 17. At this time, the traveling wave is transmitted from the gap (pair) 8 to the liquid crystal layer 16. Thus, Figure 6 Similarly to the embodiment shown, the patch 9 is excited and can emit radio waves with high directivity.

[1229] On the other hand, similarly, when receiving an incident radio wave, the patch 9 receives the incident radio wave and then propagates the incident radio wave to the power supply unit 12 via the slot (pair) 8 provided immediately below the patch 9 .

[1230] Next, use Figures 8 to 10 Another embodiment of the antenna body 10 will be described. Figures 5 to 7 In the embodiment of the antenna body 10, the structure of the antenna body 10 in which the liquid crystal layer 16 is uniformly provided between the first substrate 13 and the third substrate 15 is described. Figures 8 to 10 In the embodiment, the configuration of the antenna body 10 in which the liquid crystal layer 16 is filled in the space where the patch 9 and the slot 8 are respectively arranged (hereinafter referred to as the sealed region 20) will be described.

[1231] Figure 8 1 is a top view showing an example of an embodiment of the antenna body 10 of the present invention. Figure 8 This is a diagram showing the antenna body 10 viewed from the patch array unit 7, with the patch 9, the feeding unit 12, and the slot 8 projected perpendicularly to the main surface of the disk body Q. Figure 5 Similarly, the patch 9 , the power supply portion 12 , and the slit 8 are indicated by dotted lines. Figure 8 In the embodiment, the square patch 9 and the rectangular gap 8 are respectively arranged corresponding to the sealed area 20. Figure 8 As shown, the projection of patch 9 overlaps with the projection of gap 8, so gap 8 is formed right below patch 9. Figure 8 The embodiment of the antenna body 10 shown can supply power from the slot 8 to the patch 9 by electromagnetic coupling, or propagate incident radio waves from the patch 9 to the slot 8. Thus, an antenna capable of transmitting and / or receiving radio waves can be provided.

[1232] In addition, if Figure 8 As shown in FIG, in this embodiment, the patch 9 and the slot 8 are arranged concentrically from the center of the disk Q toward the outer periphery of the disk Q. Therefore, a conical beam is generated by coaxial mode power supply, so that the phases are aligned in front of the disk Q, and the electromagnetic fields can be mutually enhanced.

[1233] Next, use Figure 8 The cross-sectional view of the antenna body 10 shown is Figure 9 Next, the embodiment of the antenna body 10 will be described. Figure 9 This is a schematic diagram showing the structure of an antenna.

[1234] like Figure 9As shown, the antenna body 10 comprises a circular second substrate 14; a circular first substrate 13 having multiple slits 8 formed concentrically from the center toward the outside in the radial direction; a buffer layer 22 provided on the surface of the first substrate 13 on the side of the second substrate 14; a first dielectric layer 17 provided between the buffer layer 22 and the second substrate 14; a power supply unit 12 provided at the center of the first and second circular substrates 13, 14, and in contact with the first dielectric layer 17; a circular third substrate 15; patches 9 (radiating elements or incident elements) mounted on the third substrate 15; and a liquid crystal layer 16, isolated by a sealing wall 24 between the third and first substrates 15, which fills multiple sealed areas 20 where the patches 9 are provided, in contact with the patches 9. The power supply unit 12 is electrically connected to the transmitter and / or receiver provided on the control board via a power supply line 12a. Moreover, each patch 9 corresponds to each gap 8, and there is at least one patch 9, at least one gap 8 and a liquid crystal layer 16 in each sealed area 20. Each sealed area 20 in the multiple sealed areas 20 is isolated by a sealing wall 21, a sealing wall 23 and a sealing wall 24.

[1235] Figure 9 Although not shown, as needed, a TFT (thin film transistor) for controlling the voltage of the liquid crystal layer 16 may be provided on, for example, the first substrate 13 in each enclosed area 20. Thus, the application of voltage to the liquid crystal layer 16 can be actively controlled. Furthermore, as needed, an alignment film may be provided in each enclosed area 20 to fix the alignment direction of the liquid crystal molecules constituting the liquid crystal layer 16. As the alignment film, a vertical alignment film that facilitates the alignment of the liquid crystal molecules in the vertical direction or a homogeneous alignment film that facilitates the alignment of the liquid crystal molecules in the horizontal direction may be provided between the first substrate 13 and the liquid crystal layer 16. Examples thereof include polyimide alignment films and photoalignment films.

[1236] Next, use Figure 8 The cross-sectional view of the antenna body 10 cut along the BB line is shown. Figure 10 The enclosed area 20 of this embodiment will be described. Figure 10 It is a schematic diagram showing the enclosed area 20.

[1237] like Figure 10 As shown, the enclosed area 20 is a closed space surrounded by a sealing wall 24, a buffer layer 22, and the first substrate 13 and the third substrate 15. Inside, at least one patch 9 and at least one gap 8 are arranged in an opposing manner in the same enclosed space and are filled with a liquid crystal layer 16.

[1238] In this embodiment, the sealing wall 24 can be formed of a known insulator, etc. In addition, the buffer layer 22 can be formed of a known dielectric material, etc.

[1239] Figure 10 Although not shown, as needed, a TFT (thin film transistor) for controlling the voltage of the liquid crystal layer 16 can be provided, for example, on the first substrate 13 within the sealed area 20. This allows the application of voltage to the liquid crystal layer 16 to be actively controlled. A more detailed description of the driving method using this active method includes, for example, the following methods: using the patch 9 as a common electrode and the first substrate 13 as a pixel electrode, and controlling the voltage between the patch 9 and the first substrate 13 by a TFT formed on the first substrate 13, thereby controlling the orientation of the liquid crystal molecules in the liquid crystal layer 16; or using the first substrate 13 as a pixel electrode, and forming an electrode layer and a TFT on the first substrate 13, and controlling the voltage between the patch 9 and the first substrate 13, thereby controlling the orientation of the liquid crystal molecules in the liquid crystal layer 16; and further, providing a comb electrode and a TFT on the first substrate 13, and controlling the orientation of the liquid crystal molecules in the liquid crystal layer 16 by the TFT. Furthermore, the method of actively controlling the application of voltage to the liquid crystal layer 16 is not limited to the above-mentioned method.

[1240] In addition, an alignment film may be provided in each sealed region 20 to fix the alignment direction of the liquid crystal molecules constituting the liquid crystal layer 16. As the alignment film, a vertical alignment film that facilitates vertical alignment of the liquid crystal molecules or a homogeneous alignment film that facilitates horizontal alignment of the liquid crystal molecules may be provided between the first substrate 13 and the liquid crystal layer 16.

[1241] To synchronize the liquid crystal layer 16, the voltage applied to the patch 9 between the first substrate 13 can be modulated. For example, as described above, by actively controlling the voltage applied to the liquid crystal layer 16, the capacitance of the slot 8 changes, resulting in control of the slot 8's reactance and resonant frequency. The resonant frequency of the slot 8 is correlated with the energy radiated from the radio waves propagating through the line. Therefore, by adjusting the resonant frequency of the slot 8, the slot 8 can be prevented from substantially coupling with the cylindrical wave energy from the power supply unit 12, or it can be coupled with the cylindrical wave energy and radiated into free space. This control of the reactance and resonant frequency of the slot 8 can be performed in each of the multiple sealed areas 20 formed. In other words, by controlling the dielectric constant of the liquid crystal layer 16, the power supply to the patch 9 within each sealed area 20 can be controlled via the TFTs. This allows control over which patch 9 transmits radio waves and which does not, thereby adjusting the transmission and reception of radio waves radiated through the liquid crystal layer 16.

[1242] Example

[1243] Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples.

[1244] The compositions of the following Examples and Comparative Examples contain the compounds in the proportions shown in the table, and the contents are described in "mass %".

[1245] In addition, the following abbreviations are used in describing compounds. Unless otherwise specified, a compound having a cis-isomer and a trans-isomer may refer to the trans-isomer.

[1246] <Ring structure>

[1247]

[1248] <Terminal structure>

[1249] [Table 1]

[1250] abbreviation Chemical structure -n <![CDATA[-C n H 2n+1 ]]> n- <![CDATA[C n H 2n+1 -]]> -On <![CDATA[-O-C n H 2n+1 ]]> nO- <![CDATA[C n H 2n+1 -O-]]> -Sn <![CDATA[-S-C n H 2n+1 ]]> nS- <![CDATA[C n H 2n+1 -S-]]> -V <![CDATA[-CH=CH2]]> V- <![CDATA[CH2=CH-]]> -V1 <![CDATA[-CH=CH-CH3]]> 1V- <![CDATA[CH3-CH=CH- <!-- 117 -->]]> -2V <![CDATA[-CH2-CH2-CH=CH2]]> V2- <![CDATA[CH2=CH-CH2-CH2-]]> -2V1 <![CDATA[-CH2-CH2-CH=CH-CH3]]> 1V2- <![CDATA[CH3-CH=CH-CH2-CH2-]]> -OCF3 <![CDATA[-O-CF3]]> CF3O- <![CDATA[CF3-O-]]> -H -H H- H- -CN -CN CN- CN- -NCS -NCS NCS- NCS-

[1251] (In the table, n is a natural number.)

[1252] <Connection Structure>

[1253] [Table 2]

[1254] abbreviation Chemical structure -n- <![CDATA[-C n H 2n -]]> -nO- <![CDATA[-C n H 2n -O-]]> -On- <![CDATA[-O-C n H 2n -]]> -COO- -C(=O)-O- -OCO- -OC(=O)- -V- -CH=CH- -nV- <![CDATA[-C n H 2n -CH=CH-]]> -Vn- <![CDATA[-CH=CH-C n H 2n -]]> -T- -C≡C- -CF2O- <![CDATA[-CF2-O-]]> -OCF2- <![CDATA[-O-CF2-]]> -Az- -N=N-

[1255] (In the table, n is a natural number.)

[1256] (Hindered phenol antioxidant)

[1257]

[1258] (Hindered Amine Light Stabilizer)

[1259]

[1260] (Preparation of Liquid Crystal Composition)

[1261] LC-A to B and LC-1 to 4 described in Table 3 were prepared.

[1262] [Table 3]

[1263] Table 3 LC-A LC-B LC-C LC-1 LC-2 LC-3 LC-4 4-Ph3-T-Ph-Ph-NCS 4 3-Ph3-T-Ph-Ph3-NCS 8 4-Ph3-T-Ph-Ph3-NCS 15 8 5 5 5-Ph3-T-Ph-Ph3-NCS 5 3-Cy-T-Ph-Ph3-NCS 15 10 15 8 4-Cy-T-Ph-Ph3-NCS 10 16 3-Cy-T-Ph-T-Ph3-NCS 5 5 8 4-Cy-T-Ph-T-Ph3-NCS 5 5-Cy-T-Ph-T-Ph3-NCS 5 5-Cy-Ph-NCS 6 3 7-Ph-Ph1-NCS 8 4-Ph-T-Pc1-NCS 10 4O-Ph2-T-Ph-NCS 5 4 5 5O-Ph2-T-Ph-NCS 4 5 5-Ph-T-Ph1-NCS 4 4O-Ph-T-Ph1-NCS 2 5 5 3-Ph-T-Ph3-NCS 6 13 10 17 9 5-Ph-T-Ph3-NCS 10 13 10 17 10 2-Cy-Ph-Ph3-NCS 26 10 10 4-Cy-Ph-Ph3-NCS 20 10 10 4-Cy-Ph-T-Ph1-NCS 16 5-Cy-Ph-T-Ph1-NCS 13 CF3O-Ph-Ph-Ph3-NCS 22 4-Ph-Ph-T-Ph3-NCS 6 5-Ph-Ph-T-Ph3-NCS 10 5-Ph-Ph5-T-Ph1-NCS 40 3-Tet3-T-Ph-T-Ph1-NCS 7 5 5 3-Ph-T-Ph1-Ph-CN 12 3-Ph-T-Ph1-T-Ph-2 8 3-Ph-T-Ph1-T-Ph-3 7 3-Ph-T-Ph1-T-Ph-5 8 3-Ph-T-Pm1-T-Ph-2 7 4-Ph-T-Pm1-T-Ph-3 7 4-Ph3-T-Pm2-T-Ph-S1 7 3-Tet3-T-Ph-T-Ph-2 10 5 3-Tet3-T-Ph-T-Ph-4 8 2-Ph3-T-Ph-Az-Ph-2 5 3-Ph3-T-Ph-Az-Ph-2 8 3-Tet3-T-Ph-Az-Ph-2 5 3-Tet3-T-Ph-Az-Ph-4 5 3-Cy-COO-Ph-T-Ph-5 3 2-Ph3-T-Ph-Ph-3 5 2-Ph3-T-Ph-Ph-4 11 3-Ph3-T-Ph-Ph-2 11 3-Ph3-T-Ph-Ph-4 9 4-Ph3-T-Ph-Ph-3 16 Total (mass %) 100 100 100 100 100 100 100

[1264] (Examples 1 to 28 and Comparative Examples 1 to 3)

[1265] Using LC-A to LC-B and LC-1 to LC-4, hindered phenol antioxidants (XX-1) to (XX-3), and hindered amine light stabilizers (YY-1) to (YY-2), the liquid crystal compositions listed in Tables 2 to 6 were prepared, and their physical properties were measured and subjected to a "Storage Stability Test." The results are shown in Tables 4 to 8.

[1266] <Storage stability test>

[1267] 0.5 g of the liquid crystal composition was weighed into a 1 mL sample bottle (manufactured by Maruemu) and degassed at 150-250 Pa for 10 minutes. The bottle was then purged with dry nitrogen and the included cap was replaced. The bottle was stored in a 0°C temperature-controlled thermostat (manufactured by Espec, SH-241) for 2 weeks, with the occurrence of crystallization of the liquid crystal composition visually inspected every week.

[1268] [Table 4]

[1269]

[1270] [Table 5]

[1271]

[1272] [Table 6]

[1273]

[1274] [Table 7]

[1275]

[1276] [Table 8]

[1277]

[1278] According to Examples 1 to 4, the liquid crystal composition using the compound represented by the general formula (i) is T ni High, large Δn, V th Low, Δε r Large, tanδ iso A liquid crystal composition that is small and has good storage properties at low temperatures.

[1279] In particular, Examples 2 and 4 are particularly Δn and Δε r Big results.

[1280] On the other hand, according to Comparative Examples 1 to 3, the liquid crystal compositions not using the compound represented by the general formula (i) were found to have poor storage properties at low temperatures or V th Very high, Δε r Small.

[1281] Furthermore, according to Examples 5 to 28, it was confirmed that even when a hindered phenol antioxidant or a hindered amine light stabilizer was used in combination, the T ni High, large Δn, V th Low, Δε r Large, tanδ iso Small and good storage performance at low temperatures.

[1282] (Examples 29 to 42)

[1283] Furthermore, LC-5 and LC-6 described in Table 9 were prepared. Then, using LC-5 and LC-6, hindered phenol-based antioxidants (XX-1) to (XX-3), and hindered amine-based light stabilizers (YY-1) to (YY-2), the liquid crystal compositions described in Tables 10 to 12 were prepared. The physical properties of these compositions were measured, and storage stability tests were conducted. The results confirmed the same effects as in Examples 1 to 28. The results are shown in Tables 9 to 12.

[1284] [Table 9]

[1285] Table 9 LC-5 LC-6 4-Ph3-T-Ph-Ph-NCS 3-Ph3-T-Ph-Ph3-NCS 4-Ph3-T-Ph-Ph3-NCS 5 5-Ph3-T-Ph-Ph3-NCS 8.5 3-Cy-T-Ph-Ph3-NCS 8 12 4-Cy-T-Ph-Ph3-NCS 12 3-Cy-T-Ph-T-Ph3-NCS 8 5 4-Cy-T-Ph-T-Ph3-NCS 5 5-Cy-T-Ph-T-Ph3-NCS 5-Cy-Ph-NCS 7-Ph-Ph1-NCS 4-Ph-T-Pc1-NCS 4O-Ph2-T-Ph-NCS 5O-Ph2-T-Ph-NCS 5-Ph-T-Ph1-NCS 4O-Ph-T-Ph1-NCS 3-Ph-T-Ph3-NCS 9 12 5-Ph-T-Ph3-NCS 10 5.5 2-Cy-Ph-Ph3-NCS 20 4-Cy-Ph-Ph3-NCS 20 4-Cy-Ph-T-Ph1-NCS 5-Cy-Ph-T-Ph1-NCS CF3O-Ph-Ph-Ph3-NCS 4-Ph-Ph-T-Ph3-NCS 5-Ph-Ph-T-Ph3-NCS 5-Ph-Ph5-T-Ph1-NCS 3-Tet3-T-Ph-T-Ph1-NCS 5 3-Ph-T-Ph1-Ph-CN 12 3-Ph-T-Ph1-T-Ph-2 3-Ph-T-Ph1-T-Ph-3 3-Ph-T-Ph1-T-Ph-5 3-Ph-T-Pm1-T-Ph-2 4-Ph-T-Pm1-T-Ph-3 4-Ph3-T-Pm2-T-Ph-S1 4-Ph3-T-Pm1-T-Ph-S1 7 3-Tet3-T-Ph-T-Ph-2 5 3-Tet3-T-Ph-T-Ph-4 8 2-Ph3-T-Ph-Az-Ph-2 5 3-Ph3-T-Ph-Az-Ph-2 8 3-Tet3-T-Ph-Az-Ph-2 5 3-Tet3-T-Ph-Az-Ph-4 5 3-Cy-COO-Ph-T-Ph-5 2-Ph3-T-Ph-Ph-3 2-Ph3-T-Ph-Ph-4 3-Ph3-T-Ph-Ph-2 3-Ph3-T-Ph-Ph-4 4-Ph3-T-Ph-Ph-3 Total (mass %) 100 100

[1286] [Table 10]

[1287]

[1288] [Table 11]

[1289]

[1290] [Table 12]

[1291]

[1292] (Synthesis of the Compound Represented by General Formula (i))

[1293] (Example 29) Production of the compound represented by formula (I-1)

[1294] Under a nitrogen atmosphere, 30g of triphenylphosphine and 200mL of dichloromethane were added to a reaction vessel and cooled to 0°C. 50mL of a dichloromethane solution of 15g of 4-propylcyclohexanal and 33g of carbon tetrabromide were added dropwise. After the reaction was completed, the precipitate was filtered and the solution was concentrated. 100mL of tetrahydrofuran (THF) was added to the concentrate and cooled to -60°C. While maintaining at -60°C, 50mL of n-butyllithium hexane solution (1.6M) was slowly added dropwise. After the addition was completed, it was stirred at -60°C for 2 hours. After the reaction was completed, it was post-treated with water and 10% by mass hydrochloric acid, then extracted and concentrated with hexane. The concentrate was purified by silica gel column chromatography (hexane) to obtain 10g of compound represented by formula (I-1-1).

[1295] Then, under a nitrogen atmosphere, 1-bromo-4-iodobenzene 20.0g, copper iodide (I) 0.5g, bis(triphenylphosphine) palladium dichloride (II) 0.9g, triethylamine 50mL, THF100mL are added into a reaction vessel. While stirring at room temperature, a solution obtained by dissolving 10g of the compound represented by formula (I-1-1) in THF50mL is added dropwise, and stirred at room temperature for 1 hour. 10% by mass of hydrochloric acid is injected into the reaction solution and extracted with toluene. The organic layer is post-treated with saline and then purified by silica gel column chromatography (toluene). Further, recrystallization (toluene / hexane=1 / 2) is carried out to obtain 12g of the compound represented by formula (I-1-2).

[1296] Then, under a nitrogen atmosphere, 12g of the compound represented by formula (I-1-2), 0.2g of copper (I) iodide, 0.7g of tetrakis (triphenylphosphine) palladium, 30mL of triethylamine, and 50mL of N,N-dimethylformamide were added to the reaction vessel. While heating at 80°C, 20mL of an N,N-dimethylformamide solution of 6.5g of 4-amino-3,5-difluorophenylacetylene was added dropwise and stirred at 80°C for 2 hours. The reaction solution was post-treated with 10% by mass of hydrochloric acid and then extracted with ethyl acetate. After the organic layer was washed with saturated brine, it was purified by silica gel column chromatography (dichloromethane). Further, recrystallization (toluene / hexane = 1 / 3) was performed to obtain 13g of the compound represented by formula (1-1-3).

[1297] 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 brine and purified by silica gel column chromatography (dichloromethane). Further recrystallization (toluene / hexane = 1 / 1) was performed to obtain 6.5 g of the compound represented by formula (I-1).

[1298] Cr 113N 227Iso

[1299] MS (EI): m / z = 419

[1300] (Example 30) Production of the compound represented by formula (I-2)

[1301]

[1302] 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 the reaction vessel. While heating at 60 ° C, a THF10 mL solution of 4.5 g of trimethylsilyl acetylene was added dropwise and stirred at 60 ° C for 2 hours. The reaction solution was cooled, then post-treated with 100 mL of saturated ammonium chloride aqueous solution, and then extracted with toluene. After washing the organic layer with saturated brine, it was purified by silica gel column chromatography (toluene). Further, recrystallization (toluene / hexane = 1 / 2) was performed to obtain the target compound.

[1303] Next, under a nitrogen atmosphere, the obtained compound and 3 g of potassium carbonate were added to a reaction vessel, dissolved in 100 ml of methanol, and reacted at 40°C for 2 hours. The reaction solution was extracted with toluene, and the organic layer was washed with saturated brine and purified by silica gel column chromatography (toluene) to obtain 6.8 g of the compound represented by formula (1-2-2).

[1304] 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 heated under reflux for 3 hours to react. After completion of the reaction, post-treatment with water was performed, and then extraction with ethyl acetate was performed. The organic layer was concentrated to obtain 10.0 g of the compound represented by formula (I-2-3).

[1305] Then, 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 the 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. After washing the organic layer with saturated brine, it was purified by silica gel column chromatography (dichloromethane). Further, recrystallization (toluene) was performed to obtain 7.2 g of the compound represented by formula (I-2-4).

[1306] 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 the reaction vessel and heated under reflux for 6 hours. After the reaction, the organic layer was washed with saturated brine and then purified by silica gel column chromatography (dichloromethane). Further recrystallization (toluene) was performed to obtain 4.5 g of the compound represented by formula (I-2).

[1307] MS (EI): m / z = 421

[1308] (Example 31) Production of the compound represented by formula (I-3)

[1309]

[1310] Under a nitrogen atmosphere, 22g of the compound represented by formula (I-3-2), 1.0g of copper (I) iodide, 3g of tetrakis (triphenylphosphine) palladium, 20mL of triethylamine and 100mL of N,N-dimethylformamide were added to the reaction vessel. While heating at 80°C, a 20mL solution of 15g of the compound represented by formula (I-3-1) in N,N-dimethylformamide was added dropwise and stirred at 80°C for 2 hours. After the reaction, the reaction solution was cooled, post-treated with 10% by mass hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with saturated brine and then purified by silica gel column chromatography (dichloromethane / ethyl acetate = 2 / 1). Further, recrystallization (toluene / hexane = 2 / 1) was performed to obtain 24g of the compound represented by formula (1-3-3).

[1311] 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. 34 g of trifluoromethanesulfonic anhydride was then slowly added dropwise. After the addition was complete, the mixture was allowed to react at room temperature for 2 hours. After the reaction was completed, post-treatment was performed with 10% by mass hydrochloric acid, followed by washing with saturated brine, and the organic layer was concentrated.

[1312] Next, the concentrate was moved 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 at 80 ° C, a 20 mL solution of 12 g of 4-amino-3,5-difluorophenylacetylene in N, N-dimethylformamide was added dropwise and stirred at 80 ° C for 2 hours. After the reaction was completed, the reaction solution was cooled, post-treated with 10% by mass of hydrochloric acid, and then extracted with ethyl acetate. After washing the organic layer with saturated brine, it was purified by silica gel column chromatography (dichloromethane / ethyl acetate = 1 / 1). Further, recrystallization (toluene) was performed to obtain 26 g of compound represented by formula (1-3-4).

[1313] 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 the reaction vessel and stirred at room temperature. After the reaction was completed, the organic layer was washed with saturated brine and then purified by silica gel column chromatography (dichloromethane). Further recrystallization (toluene / hexane = 2 / 1) was performed to obtain 21 g of the compound represented by formula (I-3).

[1314] MS (EI): m / z = 445

[1315] (Example 32) Production of the compound represented by formula (I-4)

[1316]

[1317] Under a nitrogen atmosphere, 1-bromo-4-iodobenzene 28g, copper iodide (I) 1.0g, tetrakis (triphenylphosphine) palladium 3g, triethylamine 20mL, THF 200mL are added into a reaction vessel. A THF 100mL solution of 19g of the compound represented by the formula (I-4-1) is added dropwise at room temperature and further stirred at room temperature for 4 hours. After the reaction is completed, the reaction solution is post-treated with 10% by mass of hydrochloric acid and then extracted with ethyl acetate. After the organic layer is washed with saturated brine, it is purified by silica gel column chromatography (dichloromethane). Further, recrystallization (toluene / hexane = 1 / 4) is carried out to obtain 32g of the compound represented by the formula (1-4-2).

[1318] Then, under a nitrogen atmosphere, 32g of the compound represented by formula (I-4-2), 24g of the compound represented by formula (I-4-3), 1g of tetrakis(triphenylphosphine)palladium, 18g of potassium carbonate, 150mL of tetrahydrofuran and 20mL of water were added to the reaction vessel, and the reaction vessel was heated to 70°C. After the reaction was completed, the reaction solution was post-treated with 100mL of saturated aqueous ammonium chloride solution and then extracted with ethyl acetate. After washing the organic layer with saturated brine, it was purified by silica gel column chromatography (dichloromethane / ethyl acetate = 1 / 1). Further, recrystallization (toluene / hexane = 2 / 1) was performed to obtain 28g of the compound represented by formula (I-4-4).

[1319] 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 the reaction vessel and heated under reflux for 6 hours. After the reaction, the organic layer was washed with saturated brine and then purified by silica gel column chromatography (dichloromethane). Further, recrystallization (toluene) was performed to obtain 23 g of the compound represented by formula (I-4).

[1320] Cr 91SmA 145N 203Iso

[1321] MS (EI): m / z = 439

[1322] (Example 33) Production of the compound represented by formula (I-5)

[1323]

[1324] Under a nitrogen atmosphere, 29g of the compound represented by formula (I-5-1), 1.0g of copper (I) iodide, 3g of tetrakis (triphenylphosphine) palladium, 20mL of triethylamine and 150mL of N,N-dimethylformamide were added to the reaction vessel. While heating the reaction vessel at 80°C, a 50mL solution of 23g of the compound represented by formula (I-5-2) in N,N-dimethylformamide was added dropwise and stirred at 80°C for 2 hours. After the reaction was completed, the reaction solution was cooled, post-treated with 10% by mass of hydrochloric acid, and then extracted with ethyl acetate. After washing the organic layer with saturated brine, it was purified by silica gel column chromatography (dichloromethane / ethyl acetate = 2 / 1). Further, recrystallization (ethanol) was performed to obtain 26g of the compound represented by formula (1-5-3).

[1325] 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 anhydride was slowly added dropwise. After the addition was completed, the mixture was reacted at room temperature for 2 hours. After the reaction was completed, post-treatment was performed with 10% by mass hydrochloric acid, followed by washing with saturated brine, and the organic layer was concentrated.

[1326] Next, the concentrate containing the compound represented by formula (1-5-4) was transferred to a reaction vessel, and 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 solution was post-treated with a saturated aqueous ammonium chloride solution and then extracted with ethyl acetate. After the organic layer was washed with saturated brine, it was purified by silica gel column chromatography (dichloromethane / ethyl acetate = 1 / 1). Further, recrystallization (toluene / hexane = 3 / 1) was performed to obtain 24 g of the compound represented by formula (I-5-6).

[1327] Then, 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 the reaction vessel and heated under reflux for 6 hours. After the reaction, the organic layer was washed with saturated brine and then purified by silica gel column chromatography (dichloromethane). Further, recrystallization (toluene) was performed to obtain 23 g of the compound represented by formula (I-5).

[1328] MS (EI): m / z = 453

[1329] (Example 34) Production of the compound represented by formula (I-6)

[1330]

[1331] 20 g of the compound represented by formula (I-6) was obtained by the same method as in Example 32, except that 17.6 g of the compound represented by formula (I-6-1) was used instead of 19 g of the compound represented by formula (1-4-1) in Example 32.

[1332] MS (EI): m / z = 425

[1333] (Example 35) Production of a compound represented by formula (I-7)

[1334]

[1335] 23 g of a compound represented by formula (I-7) was obtained by the same method as in Example 32, except that 20.5 g of a compound represented by formula (I-7-1) was used instead of 19 g of the compound represented by formula (1-4-1) in Example 32.

[1336] MS (EI): m / z = 453

[1337] (Example 36) Production of the compound represented by formula (I-8)

[1338]

[1339] 7g of compound represented by formula (I-8) was obtained by the same method as in Example 29, except that 11g of compound represented by formula (I-8-1) was used instead of 10g of compound represented by formula (I-1-1) in Example 29.

[1340] MS (EI): m / z = 433

[1341] (Example 37) Production of the compound represented by formula (I-9)

[1342]

[1343] 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 (I-1-1) in Example 29.

[1344] MS (EI): m / z = 447

[1345] (Example 38) Production of a compound represented by formula (I-10)

[1346]

[1347] A compound 23g represented by the formula (I-10) was obtained by the same method as in Example 32, except that the compound 21g represented by the formula (I-10-2) was used instead of the compound 24g represented by the formula (I-4-3) in Example 32.

[1348] Cr 102SmA 206N 261Iso

[1349] MS (EI): m / z = 403

[1350] (Example 39) Production of a compound represented by formula (I-11)

[1351]

[1352] Under a nitrogen atmosphere, 30g of the compound represented by the formula (I-11-1), 26g of the compound represented by the formula (I-11-2), 1g of tetrakis(triphenylphosphine)palladium, 20g of potassium carbonate, 150mL of tetrahydrofuran and 20mL of water were added to the 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. After the organic layer was washed with saturated brine, it was purified by silica gel column chromatography (dichloromethane / ethyl acetate = 2 / 1). Further, recrystallization (toluene / hexane = 1 / 2) was performed to obtain 29g of the compound represented by the formula (I-11-3).

[1353] 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 heated under reflux for 6 hours. After the reaction, the organic layer was washed with saturated brine and then purified by silica gel column chromatography (dichloromethane). Further, recrystallization (toluene) was performed to obtain 22 g of the compound represented by formula (I-11).

[1354] Cr 77N 210Iso

[1355] MS (EI): m / z = 395

[1356] (Example 40) Production of a compound represented by formula (I-12)

[1357]

[1358] 21 g of compound represented by formula (I-12) was obtained by the same method as in Example 39, except that 32 g of compound represented by formula (I-12-1) was used instead of 30 g of compound represented by formula (I-11-1) in Example 39.

[1359] MS (EI): m / z = 409

[1360] Industrial applicability

[1361] The compound and liquid crystal composition of the present invention can be used in liquid crystal display devices, sensors, liquid crystal lenses, optical communication devices, and antennas.

[1362] Explanation of symbols

[1363] 1: Antenna unit; 2: Vehicle; 3: Housing; 4: Control panel; 5: Top cover; 6: Slot antenna array section; 7: Patch array section; 8: Slot; 9: Patch; 10: Antenna body; 11: Antenna assembly; 12: Power supply section; 12a: Power supply line; 13: First substrate; 14: Second substrate; 15: Third substrate; 16: Liquid crystal layer; 17: First dielectric layer; 20: Enclosed area; 21, 23, 24: Sealing wall; 22: Buffer layer; P: Conductor; Q: Circular plate.

Claims

1. A compound represented by the following general formula (i): In general formula (i), R i1 represents an alkyl group having 1 to 6 carbon atoms, A i1 represents 1,4-cyclohexylene, A i2 and A i3 each independently represents 1,4-phenylene, The A i1 、A i2 and A i3 One or more hydrogen atoms in the group may be independently substituted by a substituent group S i1 replace, Substituent S i1 represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, In the substituent S i1 When there are multiple, they can be the same or different. Z i1 Indicates -C≡C-.

2. The compound according to claim 1, which is selected from the group consisting of compounds represented by the following structural formula:

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