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

Abstract

To provide a compound that yields a liquid crystal composition having large Δn, large Δεr, and high storage stability at low temperatures, and to provide a liquid crystal composition, a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the compound.SOLUTION: The present invention provides a compound represented by general formula (i), having a predetermined side chain structure including a cyclohexenylene group, an ethynylene group (-C≡C-), and an isothiocyanate group (-NCS), and also provides a liquid crystal composition, a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the compound.SELECTED DRAWING: None

Description

Technical Field

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

Background Art

[0002] As a new application of liquid crystals widely used for display purposes, an antenna using a liquid crystal for transmitting and receiving radio waves between a moving body such as an automobile and a communication satellite has attracted attention. Conventionally, satellite communication has used a parabolic antenna. However, when used in a moving body such as an automobile, the parabolic antenna has to be directed toward the satellite at any time, and a large movable part is required. However, since the liquid crystal inside the panel of the antenna using liquid crystal can change the transmission and reception direction of radio waves by operating, there is no need to move the antenna itself, and the shape of the antenna can also be made flat. In addition, in order to realize global large-capacity and high-speed communication, studies on low-earth orbit satellite constellations using a large number of low-earth orbit satellites are underway. In order to follow a low-earth orbit satellite that always seems to be moving from the ground, a liquid crystal antenna that can easily change the transmission and reception direction of radio waves is useful. Generally, for autonomous driving of an automobile or the like, a large amount of data download of high-precision 3D map information is required. However, if an antenna using liquid crystal is used, by incorporating the antenna into an automobile, a large amount of data can be downloaded from a communication satellite without any mechanical movable parts. The frequency band used in satellite communication is about 13 GHz, which is significantly different from the frequencies used in conventional liquid crystal display applications. Therefore, the required physical properties of the liquid crystal are also significantly different. For example, the Δn required for the liquid crystal for the antenna is about 0.4, and the operating temperature range is, for example, -20 to 120°C. In addition, an infrared laser image recognition and ranging device using liquid crystal has also attracted attention as a sensor for autonomous driving of a moving body such as an automobile. For example, the Δn required for the liquid crystal for this application is 0.3 to 0.6, and the operating temperature range is, for example, 10 to 100°C. Furthermore, it is known that many liquid crystalline compounds constituting a liquid crystal composition exhibiting a high Δn of 0.2 or more have low compatibility. Therefore, it is also important to select a liquid crystalline compound with high compatibility. On the other hand, as a technology for liquid crystals for antennas, for example, Patent Document 1 can be cited. In addition, Non-Patent Document 1 proposes the use of a liquid crystal material as a constituent component of a high-frequency device.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Non-Patent Documents

[0004]

Non-Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] The present invention aims to provide a compound that can provide a liquid crystal composition having a large Δn, a large Δε, and good storage stability at low temperatures, as well as a liquid crystal composition, a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the same. r

Means for Solving the Problems

[0006] As a result of intensive studies, the present inventors have found that a compound represented by the general formula (i) having a cyclohexenylene group, an ethynylene group (-C≡C-), and a predetermined side chain structure including an isothiocyanate group (-NCS) group can solve the above problems, and have completed the present invention. As an example of the configuration of the present invention for solving the above problems, it is as follows.

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

[0008] [Chemical formula] (In general formula (i), R i1 represents an alkyl group having 1 to 20 carbon atoms, one or more of -CH2- in the alkyl group may each independently be substituted with -O-, -S-, -NH-, -CO- and / or -CS-, one or more of -CH2-CH2- in the alkyl group may each independently be substituted with -CH=CH-, -CF=CF- and / or -C≡C-, one or more hydrogen atoms in the alkenyl group may each independently be substituted with a halogen atom, oxygen atoms do not directly bond to each other, X i1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a thioisocyano group, an isothiocyanate group, an isocyanate group or an alkyl group having 1 to 20 carbon atoms, one or more of -CH2- in the alkyl group may each independently be substituted with -O-, -S-, -NH-, -CO- and / or -CS-, one or more of -CH2-CH2- in the alkyl group may each independently be substituted with -CH=CH-, -CF=CF- and / or -C≡C-, one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom, oxygen atoms do not directly bond to each other, J i1 represents a cyclohexenylene group, Ai1 , A i2 and A i3 each independently represents either a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms, provided that A i1 does not represent a 1,4 - cyclohexylene group, said J i1 , A i1 , A i2 and A i3 one or more hydrogen atoms in may each independently be substituted by a substituent S i1 and 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, one or more -CH2- in said alkyl group may each independently be substituted by -O-, -S-, -NH-, -CS- and / or -CO-, one or more -CH2-CH2- in said alkyl group may each independently be substituted by -CH=CH-, -CF=CF- and / or -C≡C-, one or more hydrogen atoms in said alkyl group may each independently be substituted by a halogen atom, provided that oxygen atoms are not directly bonded to each other, substituent S i1 when there are a plurality of them, they may be the same or different, Z i1 and Z i2 each independently represents either a single bond or an alkylene group having 1 to 20 carbon atoms, one or more -CH2- in said alkylene group may each independently be substituted by -O-, -CF2- and / or -CO-, One or more of the -CH2-CH2- groups in the alkylene group may each independently be replaced by -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N- and / or -C≡C-. Oxygen atoms are not directly bonded to each other. n i1 represents an integer from 0 to 2. n i2 represents an integer from 1 to 3. A i1 A i2 Z i1 or Z i2 When there are a plurality of them, they may be the same or different from each other.) A compound represented by

[0009] Item 2. The compound represented by the general formula (i) is one of the following general formulas (i-1) to (i-7)

[0010]

Chemical formula

[0011] Item 3. The above X i1The compound according to item 1 or 2, which represents a fluorine atom, a cyano group or an isothiocyanate group (-NCS).

[0012] Item 4. A liquid crystal composition containing one or more of the compounds described in any one of items 1 to 3.

[0013] Item 5. A liquid crystal display element using the liquid crystal composition described in item 4.

[0014] Item 6. A sensor using the liquid crystal composition described in item 4.

[0015] Item 7. A liquid crystal lens using the liquid crystal composition described in item 4.

[0016] Item 8. An optical communication device using the liquid crystal composition described in item 4.

[0017] Item 9. An antenna using the liquid crystal composition described in item 4.

[0018] Item 10. The antenna described in item 9, A first substrate having a plurality of slots, A second substrate facing the first substrate and provided with a power supply unit, 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 described in item 4.

Advantages of the Invention

[0019] According to the present invention, by using a compound represented by the general formula (i) having a cyclohexenylene group, an ethynylene group (-C≡C-), and a predetermined side chain structure including an isothiocyanate group (-NCS) group, Δn is large and Δε rA liquid crystal composition with a large [property] and good storage stability at low temperatures can be obtained, and the liquid crystal composition is useful for liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas.

Embodiments for Carrying Out the Invention

[0020] (Compound represented by general formula (i)) The compound according to the present invention is a compound represented by the following general formula (i) having a cyclohexenylene group, an ethynylene group (-C≡C-), and a predetermined side chain structure including an isothiocyanate group (-NCS) group.

[0021] In addition, the liquid crystal composition according to the present invention contains one or more compounds represented by the following general formula (i) having a cyclohexenylene group, an ethynylene group (-C≡C-), and a predetermined side chain structure including an isothiocyanate group (-NCS) group.

[0022]

Chemical formula

[0023] In general formula (i), R i1 represents an alkyl group having 1 to 20 carbon atoms. The alkyl group is a linear, branched, or cyclic alkyl group, and is preferably a linear alkyl group. The number of carbon atoms in the alkyl group is preferably 2 to 10, more preferably 2 to 6. One or more -CH2- in the alkyl group may each be independently substituted with -O-, -S-, -NH-, -CO-, and / or -CS-. In addition, one or more -CH2-CH2- in the alkyl group may be substituted with -CH=CH-, -CH=CH-, -CF=CF-, and / or -C≡C-. In addition, one or more hydrogen atoms in the alkyl group may each be independently substituted with a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted with a predetermined group, oxygen atoms are not directly bonded to each other. From the viewpoint of the stability of the compound, it is preferable that sulfur atoms are not directly bonded to each other and / or oxygen atoms are not directly bonded to sulfur atoms. For example, R i1 can represent an alkoxy group having 1 to 19 carbon atoms, wherein one -CH2- in the alkyl group is substituted with -O-. The alkoxy group is a linear, branched, or cyclic alkoxy group, and preferably a linear alkoxy group. The number of carbon atoms in the alkoxy group is preferably 2 to 10, and more preferably 2 to 6. Also, R i1 can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms, wherein one -CH2- in the alkyl group is substituted with -S-. The alkylsulfanyl group is a linear, branched, or cyclic alkylsulfanyl group, and preferably a linear alkylsulfanyl group. The number of carbon atoms in the alkylsulfanyl group is preferably 1 to 10, and more preferably 1 to 6. Also, R i1 can represent an alkenyl group having 2 to 20 carbon atoms, wherein one or more -CH2-CH2- in the alkyl group are substituted with -CH=CH-. The alkenyl group is a linear, branched, or cyclic alkenyl group, and preferably a linear alkenyl group. The number of carbon atoms in the alkenyl group is preferably 2 to 10, and more preferably 2 to 6. Also, R i1 can represent an alkynyl group having 2 to 20 carbon atoms, wherein one or more -CH2-CH2- in the alkyl group are substituted with -C≡C-. When the alkynyl group is a linear, branched or cyclic alkynyl group, it is preferably a linear alkynyl group. The number of carbon atoms in the alkynyl group is preferably 2 to 10, preferably 2 to 6. As the alkynyl group, from the viewpoints of ease of synthesis and elongation of the conjugated system, an alkynyl group represented by the following formula (R ii1 -A) is preferred.

[0024]

Chemical formula

[0025] In the formula (R i1 -A), R i1A represents an alkyl group having 1 to 18 carbon atoms. The alkyl group having 1 to 18 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group. The number of carbon atoms in the alkyl group having 1 to 18 carbon atoms is preferably 1 to 8. One or more -CH2- in the alkyl group may each independently be substituted with -O-, -S-, -NH-, -CO- and / or -CS-. In addition, one or more -CH2-CH2- in the alkyl group may each independently be substituted with -CH=CH-, -CF=CF- and / or -C≡C-. In addition, one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. However, when the alkyl group is substituted with a predetermined group, oxygen atoms do not directly bond to each other. Also, from the viewpoint of the stability of the compound, it is preferable that sulfur atoms do not directly bond to each other and / or oxygen atoms do not directly bond to sulfur atoms. Also, in the formula (R i1 -A), the black dot is A i1 or J i1Represents a bonding hand to Also, R i1 can represent an alkenyloxy group having 2 to 19 carbon atoms, where one -CH2- in the alkyl group is replaced by -O-, and one or two or more -CH2-CH2- are replaced by -CH=CH-. The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and is preferably a linear alkenyloxy group. The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, and preferably 2 to 6. Also, R i1 can represent a halogenated alkyl group having 1 to 20 carbon atoms, where one or two or more hydrogen atoms in the alkyl group are replaced by halogen atoms. The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group. The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, and preferably 2 to 6. Also, R i1 can represent a halogenated alkoxy group having 1 to 19 carbon atoms, where one -CH2- in the alkyl group is replaced by -O-, and one or two or more hydrogen atoms in the alkyl group are replaced by halogen atoms. The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and is preferably a linear halogenated alkoxy group. The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, and preferably 2 to 6. R i1 Specific examples of the alkyl group (including substituted ones) having 1 to 20 carbon atoms in R include groups represented by formula (R i1 -1) to (R i1 -44), etc.

[0026]

Chemical formula

[0027]

Chem.

[0028] In formula (R i1 -1) to (R i1 -44), the black dots represent bonds to A i1 or J i1 . Note that, from the viewpoints of liquid crystallinity and solubility, as R , a linear or branched alkyl group having 2 to 8 carbon atoms or a linear alkenyl group having 2 to 8 carbon atoms is preferable. i1

[0029] In general formula (i), X i1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a thioisocyano group, an isothiocyanate group, an isocyanate group, or an alkyl group having 1 to 20 carbon atoms. The alkyl group is a linear, branched, or cyclic alkyl group, and is preferably a linear alkyl group. The number of carbon atoms in the alkyl group is preferably 2 to 10, more preferably 2 to 6. One or more -CH2- in the alkyl group may each independently be substituted with -O-, -S-, -NH-, -CO- and / or -CS-. In addition, one or more -CH2-CH2- in the alkyl group may each independently be substituted with -CH=CH-, -CF=CF- and / or -C≡C-. In addition, one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted with a predetermined group, oxygen atoms do not directly bond to each other. From the viewpoint of the stability of the compound, it is preferable that a sulfur atom and a sulfur atom and / or an oxygen atom and a sulfur atom are not directly bonded to each other. For example, X i1 can represent an alkoxy group having 1 to 19 carbon atoms by substituting one -CH2- in the alkyl group with -O-. The alkoxy group is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group. The number of carbon atoms in the alkoxy group is preferably 2 to 10, and preferably 2 to 6. Also, X i1 can represent an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms by substituting one -CH2- in the alkyl group with -S-. The alkylsulfanyl group is a linear, branched or cyclic alkylsulfanyl group, and is preferably a linear alkylsulfanyl group. The number of carbon atoms in the alkylsulfanyl group is preferably 1 to 10, and preferably 1 to 6. Also, X i1 can represent an alkenyl group having 2 to 20 carbon atoms by substituting one or two or more -CH2-CH2- in the alkyl group with -CH=CH-. The alkenyl group is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group. The number of carbon atoms in the alkenyl group is preferably 2 to 10, and preferably 2 to 6. Also, X i1 can represent a halogenated alkyl group having 1 to 20 carbon atoms by substituting one or two or more hydrogen atoms in the alkyl group with a halogen atom. The halogenated alkyl group is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group. The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, and preferably 2 to 6. Also, Xi1 One -CH2- in the alkyl group is replaced by -O-, and one or more hydrogen atoms in the alkyl group are replaced by halogen atoms, whereby a halogenated alkoxy group having 1 to 19 carbon atoms can be represented. The halogenated alkoxy group is a linear, branched or cyclic halogenated alkoxy group, and preferably a linear halogenated alkoxy group. The number of carbon atoms in the halogenated alkoxy group is preferably 2 to 10, more preferably 2 to 6. X i1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted ones) in X i1 -1) to (X i1 -39) and the like.

[0030]

Chemical formula

[0031] In the formulas (X i1 -1) to (X i1 -39), the black dots represent bonds to A i3 . From the viewpoint of dielectric anisotropy, X i1 preferably represents a fluorine atom, a cyano group or an isothiocyanate group (-NCS).

[0032] In the general formula (i), J i1 represents a cyclohexenylene group. Also, in the general formula (i), A i1 , A i2 and A i3 each independently represents either a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms. However, A i1 does not represent a 1,4 - cyclohexylene group. The hydrocarbon ring having 3 to 16 carbon atoms or the heterocyclic ring having 3 to 16 carbon atoms is more specifically the following group (a), group (b), group (c) and group (d): (a) a 1,4-cyclohexylene group (in this group, one -CH2- or two or more non-adjacent -CH2- may be replaced by -O- or -S-). (b) a 1,4-phenylene group (in which one -CH= or two or more non-adjacent -CH= may be replaced by -N=). (c) 1,4-cyclohexenylene group, bicyclo[2.2.2]octane-1,4-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, decahydronaphthalene-2,6-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, phenanthracene-2,6-diyl group, a naphthalene-2,7-diyl group (one -CH= or two or more -CH= present in a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, an anthracene-2,6-diyl group, an anthracene-1,4-diyl group, an anthracene-9,10-diyl group, or a phenanthrene-2,7-diyl group may be replaced by -N=); (d) a thiophene-2,5-diyl group, a benzothiophene-2,5-diyl group, a benzothiophene-2,6-diyl group, a dibenzothiophene-3,7-diyl group, a dibenzothiophene-2,6-diyl group, or a thieno[3,2-b]thiophene-2,5-diyl group (in this group, one -CH= or two or more non-adjacent -CH= may be replaced by -N=). It is preferred that the aryl group represents a group selected from the group consisting of:

[0033] J i1 , A i1 , A i2 and A i3 One or more hydrogen atoms in each independently represent a substituent S i1 may be substituted by: substituent S i1represents 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. The alkyl group is a linear, branched or cyclic alkyl group, preferably a linear alkyl group. The number of carbon atoms in the alkyl group is preferably 2 to 10, preferably 3 to 6. One or more -CH2- in the alkyl group may each independently be substituted with -O-, -S-, -NH-, -CS- and / or -CO-. In addition, one or more -CH2-CH2- in the alkyl group may each independently be substituted with -CH=CH-, -CF=CF- and / or -C≡C-. One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted with a predetermined group, oxygen atoms do not directly bond to each other. Also, from the viewpoint of the stability of the compound, it is preferable that sulfur atoms do not directly bond to each other and / or oxygen atoms do not directly bond to sulfur atoms. Substituent S i1 is preferably a linear alkyl group having 1 to 10 carbon atoms, a chlorine atom, or a fluorine atom. Also, A i1 , A i2 and A i3 at least one of which is preferably substituted with at least one substituent S i1 . Also, A i2 is preferably substituted with at least one substituent S i1 . Also, A i3has at least one substituent S i1 It is preferably substituted with In addition, the substituent S i1 When there are multiple, they may be the same or different.

[0034] J i1 Substituent S in i1 The substitution position of the formula (J i1 -SP-1)~(J i1 -SP-3).

[0035] [ka]

[0036] Expression (J i1 -SP-1)~(J i1 -SP-3) White points are R i1 or Z i1 The black dot represents a bond to -C≡C-.

[0037] A i1 Substituent S in i1 The substitution position of the formula (A i1 -SP-1)~(A i1 -SP-4).

[0038] [ka]

[0039] Formula (A i1 -SP-1)~(A i1 -SP-4) White points are R i1 or Z i1 The black dots represent bonds to Z. i1 Represents a bond to . A i2 Substituent S in i1 The substitution position of the formula (A i2 -SP-1)~(A i2It is preferably any one of (A-SP-5).

[0040]

Chemical formula

[0041] In formula (A i2 -SP-1) to (A i2 -SP-5), the white dot represents a bond to -C≡C- or Z i2 and the black dot represents a bond to Z i2 . The substituent S i3 at the substitution position in A i1 is preferably any one of the following formulas (A i3 -SP-1) to (A i3 -SP-4).

[0042]

Chemical formula

[0043] In formula (A i3 -SP-1) to (A i3 -SP-4), the white dot represents a bond to Z i2 and the black dot represents a bond to X i1 . More specifically, J i1 preferably represents any one of the following formulas (J i1 -1) to (J i1 -6).

[0044]

Chemical formula

[0045] In formula (J i1 -1) to (J i1 -6), the white dot represents a bond to R i1 or Z i1 and the black dot represents a bond to -C≡C-. More specifically, A i1 is the following formula (A i1 -1) to (Ai1 Preferably, it represents any one of -9).

[0046]

Chemical formula

[0047] In formula (A i1 -1) to (A i1 -9), the white dot represents a bond to R i1 or Z i1 and the black dot represents a bond to Z i1 . More specifically, A i2 preferably represents any one of the following formulas (A i2 -1) to (A i2 -20).

[0048]

Chemical formula

[0049] In formula (A i2 -1) to (A i2 -20), the white dot represents a bond to -C≡C- or Z i2 and the black dot represents a bond to Z i2 . More specifically, A i3 preferably represents any one of the following formulas (A i3 -1) to (A i3 -17).

[0050]

Chemical formula

[0051] In formula (A i3 -1) to (A i3 -17), the white dot represents a bond to Z i2 and the black dot represents a bond to X i1 .

[0052] In general formula (i), Z i1 and Z i2Each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms. The alkylene group is a linear, branched or cyclic alkylene group, preferably a linear alkylene group. The number of carbon atoms in the alkylene group is preferably 2 to 10, preferably 2 to 6. One or more of the -CH2- in the alkylene group may each independently be substituted with -O-, -CF2- and / or -CO-. Also, one or more of the -CH2-CH2- in the alkylene group may each independently be substituted with -CH2-CH(CH3)-, -CH(CH3)-CH2-, -CH=CH-, -CF=CF-, -CH=C(CH3)-, -C(CH3)=CH-, -CH=N-, -N=CH-, -N=N- and / or -C≡C-. However, when the alkylene group is substituted with a predetermined group, oxygen atoms do not directly bond to each other. Specific examples of the alkylene group having 2 to 20 carbon atoms (including substituted ones) include groups represented by formula (Z i1 / 2 -1) to (Z i1 / 2 -24).

[0053]

Chemical formula

[0054] In formulas (Z i1 / 2 -1) to (Z i1 / 2 -24), the white dots represent bonds to A i1 or A i2 , and the black dots represent bonds to J i1 , A i1 , A i2 or A i3 . From the viewpoint of Δn, Z i1 and Z i2 are each independently preferably a single bond or -C≡C-.

[0055] In general formula (i), n i1represents an integer from 0 to 2, preferably an integer from 1 to 2. Also, in the general formula (i), n i2 represents an integer from 1 to 3, preferably an integer from 1 to 2. A i1 , A i2 , Z i1 or Z i2 When there are multiple occurrences, they may be the same or different from each other.

[0056] The compound represented by the general formula (i) is preferably a compound selected from the group consisting of the compounds represented by the following general formulas (i-1) to (i-7).

[0057]

Chemical formula

[0058] In the general formulas (i-1) to (i-7), R i1 , A i1 , A i2 , A i3 , S i1 and X i1 represent the same meanings as R i1 , A i1 , A i2 , A i3 , S i1 and X i1 in the general formula (i), respectively. Also, the definition of A i2-2 is the same as the definition of A i2 in the general formula (i).

[0059] The compound represented by the general formula (i-1) is preferably a compound represented by the following general formulas (i-1-1) to (i-1-10).

[0060]

Chemical formula

[0061]

Chemical formula

[0062] In general formulas (i-1-1) to (i-1-10), R i1 , X i1 and S i1 have the same meanings as R i1 , X i1 and S i1 in the general formula (i), respectively, and also represent the same preferred groups.

[0063] Specific examples of the compound represented by the general formula (i-1-1) include compounds represented by the following structural formulas (i-1-1.1) to (i-1-1.4).

[0064]

Chemical formula

[0065] Specific examples of the compound represented by the general formula (i-1-2) include compounds represented by the following structural formulas (i-1-2.1) to (i-1-2.4).

[0066]

Chemical formula

[0067] Specific examples of the compound represented by the general formula (i-1-3) include compounds represented by the following structural formulas (i-1-3.1) to (i-1-3.4).

[0068]

Chemical formula

[0069] 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-1-4.10).

[0070]

Chemical formula

[0071]

Chem.

[0072] Specific examples of the compound represented by the general formula (i-1-5) include compounds represented by the following structural formulas (i-1-5.1) to (i-1-5.4) and the like.

[0073]

Chem.

[0074] 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-1-6.4) and the like.

[0075]

Chem.

[0076]

Chem.

[0077] Specific examples of the compound represented by the general formula (i-1-7) include compounds represented by the following structural formulas (i-1-7.1) to (i-1-7.4) and the like.

[0078]

Chem.

[0079] Specific examples of the compound represented by the general formula (i-1-8) include compounds represented by the following structural formulas (i-1-8.1) to (i-1-8.4) and the like.

[0080]

Chem.

[0081] Specific examples of the compound represented by the general formula (i-1-9) include compounds represented by the following structural formulas (i-1-9.1) to (i-1-9.4).

[0082]

Chemical formula

[0083] Specific examples of the compound represented by the general formula (i-1-10) include compounds represented by the following structural formulas (i-1-10.1) to (i-1-10.4).

[0084]

Chemical formula

[0085] As the compound represented by the general formula (i-2), it is preferably a compound represented by the following general formulas (i-2-1) to (i-2-6).

[0086]

Chemical formula

[0087] In the general formulas (i-2-1) to (i-2-6), R i1 , X i1 and S i1 represent the same meanings as R i1 , X i1 and S i1 in the above general formula (i), respectively, and also represent the same preferred groups.

[0088] Specific examples of the compound represented by the general formula (i-2-1) include compounds represented by the following structural formulas (i-2-1.1) to (i-2-1.4).

[0089]

Chemical formula

[0090] Specific examples of the compound represented by the general formula (i-2-2) include compounds represented by the following structural formulas (i-2-2.1) to (i-2-2.4) and the like.

[0091]

Chemical formula

[0092] Specific examples of the compound represented by the general formula (i-2-3) include compounds represented by the following structural formulas (i-2-3.1) to (i-2-3.4) and the like.

[0093]

Chemical formula

[0094] Specific examples of the compound represented by the general formula (i-2-4) include compounds represented by the following structural formulas (i-2-4.1) to (i-2-4.4) and the like.

[0095]

Chemical formula

[0096] Specific examples of the compound represented by the general formula (i-2-5) include compounds represented by the following structural formulas (i-2-5.1) to (i-2-5.4) and the like.

[0097]

Chemical formula

[0098] Specific examples of the compound represented by the general formula (i-2-6) include compounds represented by the following structural formulas (i-2-6.1) to (i-2-6.4) and the like.

[0099]

Chemical formula

[0100] As the compound represented by the general formula (i-3), the compounds represented by the following general formulas (i-3-1) to (i-3-4) are preferable.

[0101]

Chemical formula

[0102] In the general formulas (i-3-1) to (i-3-4), R i1 , X i1 and S i1 represent the same meanings as R i1 , X i1 and S i1 in the above general formula (i), respectively, and also represent the same preferable groups.

[0103] Specific examples of the compound represented by the general formula (i-3-1) include compounds represented by the following structural formulas (i-3-1.1) to (i-3-1.4), etc.

[0104]

Chemical formula

[0105] Specific examples of the compound represented by the general formula (i-3-2) include compounds represented by the following structural formulas (i-3-2.1) to (i-3-2.4), etc.

[0106]

Chemical formula

[0107] Specific examples of the compound represented by the general formula (i-3-3) include compounds represented by the following structural formulas (i-3-3.1) to (i-3-3.4), etc.

[0108]

Chemical formula

[0109] Specific examples of the compound represented by the general formula (i-3-4) include compounds represented by the following structural formulas (i-3-4.1) to (i-3-4.4) and the like.

[0110]

Chem.

[0111] As the compound represented by the general formula (i-4), it is preferably a compound represented by the following general formulas (i-4-1) to (i-4-4).

[0112]

Chem.

[0113] In the general formulas (i-4-1) to (i-4-4), R i1 , X i1 and S i1 have the same meanings as R i1 , X i1 and S i1 in the above general formula (i), respectively, and represent the same preferred groups.

[0114] Specific examples of the compound represented by the general formula (i-4-1) include compounds represented by the following structural formulas (i-4-1.1) to (i-4-1.4) and the like.

[0115]

Chem.

[0116] Specific examples of the compound represented by the general formula (i-4-2) include compounds represented by the following structural formulas (i-4-2.1) to (i-4-2.5) and the like.

[0117]

Chem.

[0118]

Chem.

[0119] Specific examples of the compound represented by the general formula (i-4-3) include compounds represented by the following structural formulas (i-4-3.1) to (i-4-3.4).

[0120]

Chem.

[0121] Specific examples of the compound represented by the general formula (i-4-4) include compounds represented by the following structural formulas (i-4-4.1) to (i-4-4.4).

[0122]

Chem.

[0123] As the compound represented by the general formula (i-5), it is preferably a compound represented by the following general formulas (i-5-1) to (i-5-3).

[0124]

Chem.

[0125] In the general formulas (i-5-1) to (i-5-3), R i1 , X i1 and S i1 have the same meanings as R i1 , X i1 and S i1 in the above general formula (i), respectively, and represent the same preferred groups.

[0126] Specific examples of the compound represented by the general formula (i-5-1) include compounds represented by the following structural formulas (i-5-1.1) to (i-5-1.4).

[0127]

Chem.

[0128] Specific examples of the compound represented by the general formula (i-5-2) include compounds represented by the following structural formulas (i-5-2.1) to (i-5-2.4) and the like.

[0129]

Chemical formula

[0130] Specific examples of the compound represented by the general formula (i-5-3) include compounds represented by the following structural formulas (i-5-3.1) to (i-5-3.4) and the like.

[0131]

Chemical formula

[0132] As the compound represented by the general formula (i-6), it is preferably a compound represented by the following general formulas (i-6-1) to (i-6-3).

[0133]

Chemical formula

[0134] In the general formulas (i-6-1) to (i-6-3), R i1 , X i1 and S i1 have the same meanings as R i1 , X i1 and S i1 in the above general formula (i), respectively, and represent the same preferred groups.

[0135] Specific examples of the compound represented by the general formula (i-6-1) include compounds represented by the following structural formulas (i-6-1.1) to (i-6-1.4) and the like.

[0136]

Chemical formula

[0137] Specific examples of the compound represented by the general formula (i-6-2) include compounds represented by the following structural formulas (i-6-2.1) to (i-6-2.4).

[0138]

Chemical formula

[0139] Specific examples of the compound represented by the general formula (i-6-3) include compounds represented by the following structural formulas (i-6-3.1) to (i-6-3.4).

[0140]

Chemical formula

[0141] The compound represented by the general formula (i-7) is preferably a compound represented by the following general formulas (i-7-1) to (i-7-4).

[0142]

Chemical formula

[0143] In the general formulas (i-7-1) to (i-7-4), R i1 , X i1 and S i1 have the same meanings as R i1 , X i1 and S i1 in the above general formula (i), respectively, and represent the same preferred groups.

[0144] Specific examples of the compound represented by the general formula (i-7-1) include compounds represented by the following structural formulas (i-7-1.1) to (i-7-1.4).

[0145]

Chemical formula

[0146] Specific examples of the compound represented by the general formula (i-7-2) include compounds represented by the following structural formulas (i-7-2.1) to (i-7-2.5) and the like.

[0147]

Chem.

[0148] Specific examples of the compound represented by the general formula (i-7-3) include compounds represented by the following structural formulas (i-7-3.1) to (i-7-3.4) and the like.

[0149]

Chem.

[0150] Specific examples of the compound represented by the general formula (i-7-4) include compounds represented by the following structural formulas (i-7-4.1) to (i-7-4.5) and the like.

[0151]

Chem.

[0152] General formula (i), general formulas (i-1) to (i-7), general formulas (i-1-1) to (i-1-10), general formulas (i-2-1) to (i-2-6), general formulas (i-3-1) to (i-3-4), general formulas (i-4-1) to (i-4-4), general formulas (i-5-1) to (i-5-3), general formulas (i-6-1) to (i-6-3), general formulas (i-7-1) to (i-7-4), structural formulas (i-1-1.1) to (i-1-1.4), structural formulas (i-1-2.1) to (i-1-2.4), structural formulas (i-1-3.1) to (i-1-3.4), structural formulas (i-1-4.1) to (i-1-4.10), structural formulas (i-1-5.1) to (i-1-5.4), structural formulas (i-1-6.1) to (i-1-6.4), structural formulas (i-1-7.1) to (i-1-7.4), structural formulas (i-1-8.1) to (i-1-8.4), structural formulas (i-1-9.1) to (i-1-9.4), structural formulas (i-1-10.1) to (i-1-10.4), structural formulas (i-2-1.1) to (i-2-1.4), structural formulas (i-2-2.1) to (i-2-2.4), structural formulas (i-2-3.1) to (i-2-3.4), structural formulas (i-2-4.1) to (i-2-4.4), structural formulas (i-2-5.1) to (i-2-5.4), structural formulas (i-2-6.1) to (i-2-6.4), structural formulas (i-3-1.1) to (i-3-1.4), structural formulas (i-3-2.1) to (i-3-2.4), structural formulas (i-3-3.1) to (i-3-3.4), structural formulas (i-3-4.1) to (i-3-4.4), structural formulas (i-4-1.1) to (i-4-1.4), structural formulas (i-4-2.1) to (i-4-2.5), structural formulas (i-4-3.1) to (i-4-3.4), structural formulas (i-4-4.1) to (i-4-4.4), structural formulas (i-5-1.1) to (i-5-1.4), structural formulas (i-5-2.1) to (i-5-2.4), structural formulas (i-5-3.1) to (i-5-3.4), structural formulas (i-6-1.1) to (i-6-1.4), structural formulas (i-6-2.1) to (i-6-2.4), structural formulas (i-6-3.1) to (i-6-3.4), structural formulas (i-7-1.1) to (i-7-1.4), structural formulas (i-7-2.1) to (i-7-2.5), structural formulas (i-7-3.1) to (i-7-3.4) or structural formulas (i-7-4.1) to (i-7-4.The types used in the liquid crystal composition of the compound represented by are one or more, preferably 1 to 10 types, preferably 1 to 5 types, preferably 1 to 3 types.

[0153] The lower limit of the total content in 100% by mass of the liquid crystal composition of the compound represented by General Formula (i), General Formulas (i-1) to (i-7), General Formulas (i-1-1) to (i-1-10), General Formulas (i-2-1) to (i-2-6), General Formulas (i-3-1) to (i-3-4), General Formulas (i-4-1) to (i-4-4), General Formulas (i-5-1) to (i-5-3), General Formulas (i-6-1) to (i-6-3), General Formulas (i-7-1) to (i-7-4), Structural Formulas (i-1-1.1) to (i-1-1.4), Structural Formulas (i-1-2.1) to (i-1-2.4), Structural Formulas (i-1-3.1) to (i-1-3.4), Structural Formulas (i-1-4.1) to (i-1-4.10), Structural Formulas (i-1-5.1) to (i-1-5.4), Structural Formulas (i-1-6.1) to (i-1-6.4), Structural Formulas (i-1-7.1) to (i-1-7.4), Structural Formulas (i-1-8.1) to (i-1-8.4), Structural Formulas (i-1-9.1) to (i-1-9.4), Structural Formulas (i-1-10.1) to (i-1-10.4), Structural Formulas (i-2-1.1) to (i-2-1.4), Structural Formulas (i-2-2.1) to (i-2-2.4), Structural Formulas (i-2-3.1) to (i-2-3.4), Structural Formulas (i-2-4.1) to (i-2-4.4), Structural Formulas (i-2-5.1) to (i-2-5.4), Structural Formulas (i-2-6.1) to (i-2-6.4), Structural Formulas (i-3-1.1) to (i-3-1.4), Structural Formulas (i-3-2.1) to (i-3-2.4), Structural Formulas (i-3-3.1) to (i-3-3.4), Structural Formulas (i-3-4.1) to (i-3-4.4), Structural Formulas (i-4-1.1) to (i-4-1.4), Structural Formulas (i-4-2.1) to (i-4-2.5), Structural Formulas (i-4-3.1) to (i-4-3.4), Structural Formulas (i-4-4.1) to (i-4-4.4), Structural Formulas (i-5-1.1) to (i-5-1.4), Structural Formulas (i-5-2.1) to (i-5-2.4), Structural Formulas (i-5-3.1) to (i-5-3.4), Structural Formulas (i-6-1.1) to (i-6-1.4), Structural Formulas (i-6-2.1) to (i-6-2.4), Structural Formulas (i-6-3.1) to (i-6-3.4), Structural Formulas (i-7-1.1) to (i-7-1.4), Structural Formulas (i-7-2.1) to (i-7-2.5), Structural Formulas (i-7-3.1) to (i-7-3.4) or Structural Formulas (i-7-4.1) to (i-7-4.5) is preferably 0.1% by mass or more, 0.It is preferably 5% by mass or more, and preferably 1% by mass or more.

[0154] General formula (i), general formulas (i-1) to (i-7), general formulas (i-1-1) to (i-1-10), general formulas (i-2-1) to (i-2-6), general formulas (i-3-1) to (i-3-4), general formulas (i-4-1) to (i-4-4), general formulas (i-5-1) to (i-5-3), general formulas (i-6-1) to (i-6-3), general formulas (i-7-1) to (i-7-4), structural formulas (i-1-1.1) to (i-1-1.4), structural formulas (i-1-2.1) to (i-1-2.4), structural formulas (i-1-3.1) to (i-1-3.4), structural formulas (i-1-4.1) to (i-1-4.10), structural formulas (i-1-5.1) to (i-1-5.4), structural formulas (i-1-6.1) to (i-1-6.4), structural formulas (i-1-7.1) to (i-1-7.4), structural formulas (i-1-8.1) to (i-1-8.4), structural formulas (i-1-9.1) to (i-1-9.4), structural formulas (i-1-10.1) to (i-1-10.4), structural formulas (i-2-1.1) to (i-2-1.4), structural formulas (i-2-2.1) to (i-2-2.4), structural formulas (i-2-3.1) to (i-2-3.4), structural formulas (i-2-4.1) to (i-2-4.4), structural formulas (i-2-5.1) to (i-2-5.4), structural formulas (i-2-6.1) to (i-2-6.4), structural formulas (i-3-1.1) to (i-3-1.4), structural formulas (i-3-2.1) to (i-3-2.4), structural formulas (i-3-3.1) to (i-3-3.4), structural formulas (i-3-4.1) to (i-3-4.4), structural formulas (i-4-1.1) to (i-4-1.4), structural formulas (i-4-2.1) to (i-4-2.5), structural formulas (i-4-3.1) to (i-4-3.4), structural formulas (i-4-4.1) to (i-4-4.4), structural formulas (i-5-1.1) to (i-5-1.4), structural formulas (i-5-2.1) to (i-5-2.4), structural formulas (i-5-3.1) to (i-5-3.4), structural formulas (i-6-1.1) to (i-6-1.4), structural formulas (i-6-2.1) to (i-6-2.4), structural formulas (i-6-3.1) to (i-6-3.4), structural formulas (i-7-1.1) to (i-7-1.4), structural formulas (i-7-2.1) to (i-7-2.5), structural formulas (i-7-3.1) to (i-7-3.4) or structural formulas (i-7-4.1) to (i-7-4.The upper limit of the total content in 100% by mass of the liquid crystal composition of the compound represented by [[5]] is preferably 95% by mass or less, preferably 90% by mass or less, preferably 85% by mass or less, preferably 30% by mass or less, and preferably 20% by mass or less.

[0155] The total content in 100% by mass of the liquid crystal composition of the compound represented by general formula (i), general formulas (i-1) to (i-7), general formulas (i-1-1) to (i-1-10), general formulas (i-2-1) to (i-2-6), general formulas (i-3-1) to (i-3-4), general formulas (i-4-1) to (i-4-4), general formulas (i-5-1) to (i-5-3), general formulas (i-6-1) to (i-6-3), general formulas (i-7-1) to (i-7-4), structural formulas (i-1-1.1) to (i-1-1.4), structural formulas (i-1-2.1) to (i-1-2.4), structural formulas (i-1-3.1) to (i-1-3.4), structural formulas (i-1-4.1) to (i-1-4.10), structural formulas (i-1-5.1) to (i-1-5.4), structural formulas (i-1-6.1) to (i-1-6.4), structural formulas (i-1-7.1) to (i-1-7.4), structural formulas (i-1-8.1) to (i-1-8.4), structural formulas (i-1-9.1) to (i-1-9.4), structural formulas (i-1-10.1) to (i-1-10.4), structural formulas (i-2-1.1) to (i-2-1.4), structural formulas (i-2-2.1) to (i-2-2.4), structural formulas (i-2-3.1) to (i-2-3.4), structural formulas (i-2-4.1) to (i-2-4.4), structural formulas (i-2-5.1) to (i-2-5.4), structural formulas (i-2-6.1) to (i-2-6.4), structural formulas (i-3-1.1) to (i-3-1.4), structural formulas (i-3-2.1) to (i-3-2.4), structural formulas (i-3-3.1) to (i-3-3.4), structural formulas (i-3-4.1) to (i-3-4.4), structural formulas (i-4-1.1) to (i-4-1.4), structural formulas (i-4-2.1) to (i-4-2.5), structural formulas (i-4-3.1) to (i-4-3.4), structural formulas (i-4-4.1) to (i-4-4.4), structural formulas (i-5-1.1) to (i-5-1.4), structural formulas (i-5-2.1) to (i-5-2.4), structural formulas (i-5-3.1) to (i-5-3.4), structural formulas (i-6-1.1) to (i-6-1.4), structural formulas (i-6-2.1) to (i-6-2.4), structural formulas (i-6-3.1) to (i-6-3.4), structural formulas (i-7-1.1) to (i-7-1.4), structural formulas (i-7-2.1) to (i-7-2.5), structural formulas (i-7-3.1) to (i-7-3.4) or structural formulas (i-7-4.1) to (i-7-4.5) is solubility, Δn and / or Δε rFrom the viewpoint of, it is preferably 0.1 to 95% by mass, more preferably 0.5 to 90% by mass, still more preferably 1 to 85% by mass, particularly preferably 1 to 30% by mass, and most preferably 1 to 20% by mass.

[0156] The compound represented by the general formula (i) (including sub-concepts) can be synthesized using known synthesis methods, and several examples are shown below.

[0157] (Production Method 1) Production of the compound represented by the following formula (s-4)

[0158] [Chemical formula]

[0159] In formulas (s-1) to (s-4), R i1 , A i2 , A i3 and X i1 represent the same meanings as R i1 , A i2 , A i3 and X i1 in the general formula (i). First, after cooling a reaction vessel containing the compound represented by the general formula (s-1), dichloromethane, and sodium carbonate to 10°C or lower, trifluoromethanesulfonic anhydride dissolved in a small amount of dichloromethane is added and reacted to obtain the compound represented by the general formula (s-2). Next, by reacting the compound represented by the general formula (s-2) with the compound represented by the general formula (s-3), the target compound represented by the general formula (s-4) can be obtained. Examples of the reaction method include the Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base. Specific examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0), and the like. When palladium(II) acetate is used as the palladium catalyst, ligands such as triphenylphosphine and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added. Specific examples of the copper catalyst include copper(I) iodide. Specific examples of the base include triethylamine and the like.

[0160] (Production Method 2) Production of the compound represented by the following formula (s-8)

[0161]

Chemical formula

[0162] In formulas (s-5) to (s-8), R i1 , A i2 , A i3 and X i1 represent the same meanings as R i1 , A i2 , A i3 and X i1 in the general formula (i). First, a reaction vessel containing the compound represented by the general formula (s-5), dichloromethane, and sodium carbonate is cooled to 10°C or lower, and then trifluoromethanesulfonic anhydride dissolved in a small amount of dichloromethane is added and reacted to obtain the compound represented by the general formula (s-6). Next, the compound represented by the general formula (s-6) is reacted with the compound represented by the general formula (s-7) to obtain the target compound represented by the general formula (s-8). Examples of the reaction method include the Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base, etc. Specific examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0), etc. When palladium(II) acetate is used as the palladium catalyst, ligands such as triphenylphosphine, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added. A specific example of the copper catalyst includes copper(I) iodide. Specific examples of the base include triethylamine, etc.

[0163] (Production Method 3) Production of the compound represented by the following formula (s-12)

[0164]

Chemical formula

[0165] In formulas (s-9) to (s-12), R i1 , A i2 , A i3 and X i1 represent the same meanings as R i1 , A i2 , A i3 and X i1 in the general formula (i). First, after cooling a reaction vessel containing the compound represented by the general formula (s-9), dichloromethane, and sodium carbonate to 10°C or lower, trifluoromethanesulfonic anhydride dissolved in a small amount of dichloromethane is added and reacted to obtain the compound represented by the general formula (s-10). Next, by reacting the compound represented by the general formula (s-10) with the compound represented by the general formula (s-11), the target compound represented by the general formula (s-12) can be obtained. Examples of the reaction method include a Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base. Specific examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0), and the like. When palladium(II) acetate is used as the palladium catalyst, ligands such as triphenylphosphine and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added. A specific example of the copper catalyst is copper(I) iodide. Specific examples of the base include triethylamine and the like.

[0166] (Production Method 4) Production of the compound represented by the following formula (s-17)

[0167] [Chemical formula]

[0168] In formulas (s-13) to (s-17), R i1 , A i2 , A i3 and X i1 represent the same meanings as R i1 , A i2 , A i3 and X i1 in the general formula (i). First, after reacting the compound represented by the general formula (s-13) with lithium diisopropylamide (LDA), methyl iodide is added to obtain the compound represented by the general formula (s-14). Next, after cooling a reaction vessel containing a compound represented by the general formula (s-14), dichloromethane, and sodium carbonate to 10°C or lower, trifluoromethanesulfonic anhydride dissolved in a small amount of dichloromethane is added and reacted to obtain a compound represented by the general formula (s-15). Furthermore, by reacting the compound represented by the general formula (s-15) with the compound represented by the general formula (s-16), the target compound represented by the general formula (s-17) can be obtained. Examples of the reaction method include the Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base. Specific examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0), and the like. When palladium(II) acetate is used as the palladium catalyst, ligands such as triphenylphosphine and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added. A specific example of the copper catalyst is copper(I) iodide. Specific examples of the base include triethylamine and the like.

[0169] (Production Method 5) Production of the compound represented by the following formula (s-22)

[0170]

Chemical Formula

[0171] In formulas (s-18) to (s-22), R i1 , A i2 , A i3 and X i1 are the same as R i1 , A i2 , A i3 and X in the general formula (i)i1 represents the same meaning. First, a mixed solution of a compound represented by the general formula (s-18), carbon tetrabromide, and dichloromethane is added to a reaction vessel containing dichloromethane and triphenylphosphine and reacted to obtain a compound represented by the general formula (s-19). Next, a mixed solution of the compound represented by the general formula (s-19) and tetrahydrofuran is cooled to -70 or lower, and a butyllithium / hexane solution is added to obtain a compound represented by the general formula (s-20). Furthermore, by reacting the compound represented by the general formula (s-20) with the compound represented by the general formula (s-21), the target compound represented by the general formula (s-22) can be obtained. Examples of the reaction method include a Sonogashira coupling reaction using a palladium catalyst, a copper catalyst, and a base. Specific examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, palladium(II) acetate, dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II), dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium(0), etc. When palladium(II) acetate is used as the palladium catalyst, ligands such as triphenylphosphine and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl may be added. A specific example of the copper catalyst is copper(I) iodide. Specific examples of the base include triethylamine, etc.

[0172] As reaction conditions other than those described in each step, for example, those described in literature such as Experimental Chemistry Course (edited by The Chemical Society of Japan, published by Maruzen Co., Ltd.), Organic Syntheses (a publication of John Wiley & Sons, Inc.), Beilstein Handbook of Organic Chemistry (Beilstein-Institut fuer Literatur der Organischen Chemie, Springer-Verlag Berlin and Heidelberg GmbH & Co. K), Fiesers’ Reagents for Organic Synthesis (John Wiley & Sons, Inc.), etc., or those included in databases such as SciFinder (Chemical Abstracts Service, American Chemical Society), Reaxys (Elsevier Ltd.), etc. can be mentioned. When handling substances unstable to oxygen and / or moisture in each step, it is preferable to carry out the operation in an inert gas such as nitrogen gas, argon gas. Functional groups can be protected as needed in each step. Examples of the protecting group include protecting groups described in GREENE’S PROTECTIVE GROUPS IN ORGANIC SYNTHESIS ((Fourth Edition), co-authored by PETER G.M.WUTS and THEODORA W.GREENE, a publication of John Wiley & Sons, Inc.), etc. Also, purification may be carried out as needed in each step. Examples of the purification method include chromatography, recrystallization, distillation, sublimation, reprecipitation, adsorption, liquid separation treatment, etc. Specific examples of the purification agent include silica gel, alumina, activated carbon, etc.

[0173] <Characteristic values of the compound represented by the general formula (i) (including sub-concepts)> The characteristic values of the compound represented by the general formula (i) (including sub-concepts) can be measured as follows. First, a compound represented by the general formula (i) (including sub-concepts) is added to the host liquid crystal, and liquid crystal compositions containing 0% by mass, 5% by mass, and 10% by mass of the compound represented by the general formula (i) (including sub-concepts) in 100% by mass of the liquid crystal composition are prepared. The Δn (refractive index anisotropy) and Δε of each liquid crystal composition are r measured. Then, using the least squares method, 100% by mass of the compound represented by the general formula (i) (including sub-concepts), that is, the Δn (refractive index anisotropy) and Δε of the compound represented by the general formula (i) (including sub-concepts) are r determined from the extrapolated values.

[0174] Δn (refractive index anisotropy) correlates with the Δn in the near-infrared region used in the optical sensor described later. The larger the Δn, the greater the phase modulation power of the light at the target wavelength, so it is particularly suitable for optical sensors. The Δn at 25 °C and 589 nm is the difference (n e ) between the extraordinary refractive index (n o ) and the ordinary refractive index (n e -n o ) of the liquid crystal composition measured using an Abbe refractometer. Also, Δn can be determined from a phase difference measuring device. There is a relationship of Δn = Re / d among the phase difference Re, the thickness d of the liquid crystal layer, and Δn. The cell gap (d) is about 3.0 μm, and the liquid crystal composition is injected into a glass cell with a polyimide alignment film subjected to an anti-parallel rubbing treatment. The in-plane Re is measured with a phase difference film and optical material inspection device RETS-100 (manufactured by Otsuka Electronics Co., Ltd.). The measurement is performed under the conditions of a temperature of 25 °C and 589 nm, and the unit is dimensionless. For the compound represented by the general formula (i) according to the present invention (including sub-concepts), Δn at 25 °C and 589 nm is preferably 0.40 or more, preferably 0.40 to 0.60, preferably 0.41 to 0.55, and preferably 0.42 to 0.50 from the viewpoint of the phase modulation power of light with a wavelength.

[0175] The higher the dielectric anisotropy in the high-frequency region, the greater the phase modulation power for radio waves in the target frequency band, so it is particularly suitable for antenna applications. In addition, in antenna applications, the smaller the dielectric tangent in the high-frequency region, the smaller the energy loss in the target frequency band, so it is suitable. In the compound represented by the general formula (i) according to the present invention (including sub-concepts), the dielectric anisotropy Δε at 10 GHz is measured as a representative of the characteristics in the high-frequency region. r was measured. Δε r =(ε r∥ -ε r⊥ ). Here, "ε r " is the dielectric constant, and the subscript "∥" represents the component parallel to the liquid crystal alignment direction, and "⊥" represents the component perpendicular to the liquid crystal alignment direction.

[0176] Δε r can be measured by the following method. First, the liquid crystal composition is introduced into a capillary made of polytetrafluoroethylene (PTFE). The capillary used here has an inner radius of 0.80 mm and an outer radius of 0.835 mm, and the effective length is 4.0 cm. The capillary filled with the liquid crystal composition is introduced into the center of a cavity resonator (manufactured by EM Lab Co., Ltd.) having a resonance frequency of 10 GHz. This cavity resonator has an outer shape with a diameter of 30 mm and a width of 26 mm. Then, a signal is input, and the result of the output signal is recorded using a network analyzer (manufactured by Keysight Technologies Co., Ltd.). Using the difference between the resonance frequency etc. of a PTFE capillary without encapsulating a liquid crystal composition and the resonance frequency etc. of a PTFE capillary encapsulating a liquid crystal composition, the dielectric constant (ε r ) at 10 GHz is determined. Note that the resonance frequency etc. using a PTFE capillary encapsulating a liquid crystal composition are obtained as the values of the characteristic components perpendicular and parallel to the alignment direction of the liquid crystal molecules by controlling the alignment of the liquid crystal molecules. In order to align the liquid crystal molecules in the vertical direction (perpendicular to the effective length direction) or parallel direction (parallel to the effective length direction) of the PTFE capillary, a magnetic field of a permanent magnet or an electromagnet is used. The magnetic field is, for example, a magnetic pole distance of 45 mm and the magnetic field strength near the center is 0.23 Tesla. A desired characteristic component is obtained by rotating a PTFE capillary encapsulating a liquid crystal composition parallel or perpendicular to the magnetic field. The measurement is performed at a temperature of 25 °C, and Δε r has no unit.

[0177] The Δε r at 25 °C of the compound (including sub-concepts) represented by the general formula (i) according to the present invention is preferably larger, but from the viewpoint of the phase modulation force in the GHz band, it is preferably 0.30 or more, preferably 0.30 to 0.65, preferably 0.31 to 0.60, preferably 0.32 to 0.55, preferably 0.33 to 0.50, preferably 0.34 to 0.45, preferably 0.35 to 0.40.

[0178] (Liquid crystal composition) The liquid crystal composition according to the present invention can be produced, for example, by mixing the compound (including sub-concepts) represented by the above general formula (i), other liquid crystal compounds and additives as necessary.

[0179] Examples of the additives include stabilizers, dye compounds, polymerizable compounds, azotran compounds and the like.

[0180] Examples of stabilizers include hydroquinones, hydroquinone monoalkyl ethers, tertiary butyl catechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, hindered phenols, hindered amines, and the like. Examples of hindered phenols include hindered phenol antioxidants represented by the following structural formulas (XX-1) to (XX-3).

[0181]

Chemical formula

[0182] Examples of hindered amines include hindered amine light stabilizers represented by the following structural formulas (YY-1) to (YY-2).

[0183]

Chemical formula

[0184] When using a stabilizer, the type used in the liquid crystal composition of the stabilizer is one or more, preferably 1 to 10 types, preferably 1 to 8 types, preferably 1 to 6 types, preferably 1 to 4 types, preferably 1 to 2 types. When using a stabilizer, the total content in 100% by mass of the liquid crystal composition of the stabilizer is preferably 0.005 to 1% by mass, preferably 0.02 to 0.50% by mass, preferably 0.03 to 0.35% by mass.

[0185] (Liquid crystal display element, sensor, liquid crystal lens, optical communication device, and antenna) Hereinafter, a liquid crystal display element, sensor, liquid crystal lens, optical communication device, and antenna using the liquid crystal composition according to the present invention will be described.

[0186] The liquid crystal display element according to the present invention is characterized by using the above-described liquid crystal composition, and is preferably driven by an active matrix method or a passive matrix method. Moreover, the liquid crystal display element according to the present invention is preferably a liquid crystal display element that reversibly switches the dielectric constant by reversibly changing the alignment direction of the liquid crystal molecules of the above-described liquid crystal composition.

[0187] The sensor according to the present invention is characterized by using the above-described liquid crystal composition. For example, as its embodiments, a distance measurement sensor that uses electromagnetic waves, visible light, or infrared light, an infrared sensor that uses temperature changes, a temperature sensor that uses a change in the reflected light wavelength due to a change in the pitch of cholesteric liquid crystal, a pressure sensor that uses a change in the reflected light wavelength, an ultraviolet sensor that uses a change in the reflected light wavelength due to a composition change, an electrical sensor that uses a temperature change caused by voltage or current, a radiation sensor that uses a temperature change accompanying the track of radiation particles, an ultrasonic sensor that uses a change in the liquid crystal molecule arrangement due to the mechanical vibration of ultrasonic waves, an electromagnetic field sensor that uses a change in the reflected light wavelength due to a temperature change or a change in the liquid crystal molecule arrangement due to an electric field, etc. can be mentioned. As the distance measurement sensor, it is preferably for LiDAR (Light Detection And Ranging) using a light source. As LiDAR, those for artificial satellites, airplanes, unmanned aerial vehicles (drones), automobiles, railways, and ships are preferable. For automobiles, those for autonomous driving automobiles are particularly preferable. The light source is preferably an LED or a laser, and preferably a laser. The light used in LiDAR is preferably infrared light, and the wavelength is preferably 800 to 2000 nm. In particular, an infrared laser with a wavelength of 905 nm or 1550 nm is preferable. When emphasizing the cost of the photodetector used and the sensitivity in all weather conditions, an infrared laser with a wavelength of 905 nm is preferable, and when emphasizing the safety regarding human vision, an infrared laser with a wavelength of 1550 nm is preferable. Since the liquid crystal composition according to the present invention exhibits a high Δn, it can provide a sensor with a large phase modulation force in the visible light, infrared light, and electromagnetic wave regions and excellent detection sensitivity.

[0188] The liquid crystal lens according to the present invention is characterized by using the above-described liquid crystal composition. For example, as one of its embodiments, it includes a first transparent electrode layer, a second transparent electrode layer, a liquid crystal layer including the above-described liquid crystal composition provided between the first transparent electrode layer and the second transparent electrode layer, an insulating layer provided between the second transparent electrode layer and the liquid crystal layer, and a high-resistance layer provided between the insulating layer and the liquid crystal layer. The liquid crystal lens according to the present invention is used, for example, as a 2D / 3D switching lens, a lens for focus adjustment of a camera, and the like.

[0189] The optical communication device according to the present invention is characterized by using the above-described liquid crystal composition. For example, as one of its embodiments, an LCOS (Liquid Crystal on Silicon) having a configuration in which liquid crystals constituting each of a plurality of pixels are two-dimensionally arranged on a reflective layer (electrode) is mentioned. The optical communication device according to the present invention is used, for example, as a spatial phase modulator.

[0190] The antenna according to the present invention is characterized by using the above-described liquid crystal composition. More specifically, the antenna according to the present invention includes a first substrate having a plurality of slots, a second substrate facing the first substrate and provided with a power feeding 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, and the liquid crystal layer contains the above-described liquid crystal composition. By using the compound according to the present invention, an antenna having high reliability against external stimuli such as heat can be provided. Thereby, an antenna capable of performing larger phase control with respect to electromagnetic waves of microwaves or millimeter waves can be provided. The antenna according to the present invention preferably operates at a Ka-band frequency or a K-band frequency or a Ku-band frequency used for satellite communication. The antenna according to the present invention preferably has a configuration in which a radial line slot array and a patch antenna array are combined. As the structure of the antenna according to the present invention, for example, the matters described in WO 2021 / 157189 pamphlet etc. can be referred to and applied.

Example

[0191] Hereinafter, the present invention will be further described with reference to examples, but the present invention is not limited to these examples. The compositions of the following examples and comparative examples contain each compound in the ratio shown in the table, and the content is described in "mass%". In addition, compounds that can take cis and trans forms represent the trans form unless otherwise specified. (Example 1) Production of the compound represented by formula (I-1)

[0192]

Chemical formula

[0193] Under a nitrogen atmosphere, 10 g of sodium carbonate, 200 mL of dichloromethane were placed in a reaction vessel, cooled to 10°C or lower, 33 g of trifluoromethanesulfonic anhydride was added dropwise, and then 8.3 g of 4-propylcyclohexanone represented by formula (I-1-1) was slowly added dropwise and reacted while maintaining the temperature at 10°C or lower. After completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours for reaction. After completion of the reaction, the organic layer was washed with water and saturated brine, and then purified by column chromatography (silica gel, hexane) to obtain 12 g of the compound represented by formula (I-1-2). Next, under a nitrogen atmosphere, 12 g of the compound represented by the formula (I-1-2), 9.4 g of the compound represented by the formula (I-1-3), 0.4 g of copper(I) iodide, 0.6 g of bis(triphenylphosphine)palladium(II) dichloride, and 100 mL of triethylamine were added to a reaction vessel. Then, the reaction solution was heated to 60 °C and reacted for 4 hours. After the reaction was completed, a saturated aqueous ammonium chloride solution was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and then purified by column chromatography (silica gel, toluene) and (toluene / hexane = 2 / 1) to obtain 16 g of the compound represented by the formula (I-1-4). Next, 16 g of the compound represented by the formula (I-1-4), 150 mL of dichloromethane, and 9 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel, and the mixture was heated under reflux for 2 hours. After the reaction was completed, the organic layer was washed with saturated brine and then purified by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 2 / 1) to obtain 14.5 g of the compound represented by the formula (I-1). MS(EI): m / z = 393

[0194] (Example 2) Production of the compound represented by the formula (I-2)

[0195]

Chemical formula

[0196] Under a nitrogen atmosphere, 10 g of sodium carbonate, 200 mL of dichloromethane were placed in a reaction vessel and cooled to 10 °C or lower. 33 g of trifluoromethanesulfonic anhydride was added dropwise, and then 10 g of 4-pentylcyclohexanone represented by the formula (I-2-1) was slowly added dropwise while maintaining a temperature of 10 °C or lower to carry out the reaction. After the addition was completed, the mixture was stirred at room temperature for 2 hours to carry out the reaction. After the reaction was completed, the organic layer was washed with water and saturated brine and then purified by column chromatography (silica gel, hexane) to obtain 14 g of the compound represented by the formula (I-2-2). Next, under a nitrogen atmosphere, 14 g of the compound represented by the formula (I-2-2), 9.9 g of the compound represented by the formula (I-2-3), 0.4 g of copper(I) iodide, 0.6 g of bis(triphenylphosphine)palladium(II) dichloride, and 100 mL of triethylamine were added to a reaction vessel. Then, the reaction solution was heated to 60 °C and reacted for 4 hours. After completion of the reaction, a saturated aqueous ammonium chloride solution was poured into the reaction solution, and the mixture was extracted with ethyl acetate. After washing the organic layer with saturated brine, purification was performed by column chromatography (silica gel, toluene) and (toluene / hexane = 2 / 1) to obtain 18.5 g of the compound represented by the formula (I-2-4). Next, 18.5 g of the compound represented by the formula (I-2-4), 150 mL of dichloromethane, and 9.5 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel, and the mixture was heated under reflux for 2 hours. After completion of the reaction, the organic layer was washed with saturated brine, and then purification was performed by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 2 / 1) to obtain 17 g of the compound represented by the formula (I-2). MS(EI): m / z = 421

[0197] (Example 3) Production of the compound represented by the formula (I-3)

[0198] [Chemical formula]

[0199] Under a nitrogen atmosphere, 10 g of sodium carbonate, 200 mL of dichloromethane were placed in a reaction vessel and cooled to 10 °C or lower. After 33 g of trifluoromethanesulfonic anhydride was added dropwise, 8.3 g of 4-propylcyclohexanone represented by the formula (I-3-1) was slowly added dropwise and reacted while maintaining the temperature at 10 °C or lower. After completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours to react. After completion of the reaction, the organic layer was washed with water and saturated brine, and then purification was performed by column chromatography (silica gel, hexane) to obtain 12 g of the compound represented by the formula (I-3-2). Next, under a nitrogen atmosphere, 12 g of the compound represented by the formula (I-3-2), 8.9 g of the compound represented by the formula (I-3-3), 0.4 g of copper(I) iodide, 0.6 g of bis(triphenylphosphine)palladium(II) dichloride, and 100 mL of triethylamine were added to a reaction vessel. Then, the reaction solution was heated to 60 °C and reacted for 4 hours. After completion of the reaction, a saturated aqueous ammonium chloride solution was poured into the reaction solution, and the mixture was extracted with ethyl acetate. After washing the organic layer with saturated brine, purification was carried out by column chromatography (silica gel, toluene) and (toluene / hexane = 2 / 1) to obtain 14 g of the compound represented by the formula (I-3-4). Next, 14 g of the compound represented by the formula (I-3-4), 150 mL of dichloromethane, and 8.3 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel, and the mixture was heated under reflux for 2 hours. After completion of the reaction, the organic layer was washed with saturated brine, and then purification was carried out by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 2 / 1) to obtain 12 g of the compound represented by the formula (I-3). MS(EI): m / z = 375

[0200] (Example 4) Production of the compound represented by the formula (I-4)

[0201]

Chemical formula

[0202] Under a nitrogen atmosphere, 10 g of sodium carbonate, 200 mL of dichloromethane were placed in a reaction vessel, cooled to 10 °C or lower, and 33 g of trifluoromethanesulfonic anhydride was added dropwise. Then, 10 g of 4-pentylcyclohexanone represented by the formula (I-4-1) was slowly added dropwise and reacted while maintaining a temperature of 10 °C or lower. After completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours for reaction. After completion of the reaction, the organic layer was washed with water and saturated brine, and then purification was carried out by column chromatography (silica gel, hexane) to obtain 14 g of the compound represented by the formula (I-4-2). Next, under a nitrogen atmosphere, 14 g of the compound represented by the formula (I-4-2), 13 g of the compound represented by the formula (I-4-3), 0.4 g of copper(I) iodide, 0.6 g of bis(triphenylphosphine)palladium(II) dichloride, and 110 mL of triethylamine were added to a reaction vessel. Then, the reaction solution was heated to 70 °C and reacted for 4 hours. After completion of the reaction, a saturated aqueous ammonium chloride solution was poured into the reaction solution, and extraction was performed with ethyl acetate. After washing the organic layer with saturated brine, purification was carried out by column chromatography (silica gel, toluene) and (toluene / hexane = 2 / 1) to obtain 15.5 g of the compound represented by the formula (I-4-4). Next, 15.5 g of the compound represented by the formula (I-4-4), 150 mL of dichloromethane, and 7.5 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel, and heating under reflux was carried out for 2 hours. After completion of the reaction, the organic layer was washed with saturated brine, and then purification was carried out by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 2 / 1) to obtain 16 g of the compound represented by the formula (I-4). MS(EI): m / z = 459

[0203] (Example 5) Production of the compound represented by the formula (I-5)

[0204]

Chemical formula

[0205] Under a nitrogen atmosphere, 10 g of the compound represented by the formula (I-5-1), 9.6 g of the compound represented by the formula (I-5-2), 0.2 g of copper(I) iodide, 0.5 g of bis(triphenylphosphine)palladium(II) dichloride, and 100 mL of triethylamine were added to a reaction vessel. Then, the reaction solution was heated to 70 °C and reacted for 4 hours. After completion of the reaction, a saturated aqueous ammonium chloride solution was poured into the reaction solution, and extraction was performed with ethyl acetate. After washing the organic layer with saturated brine, purification was carried out by column chromatography (silica gel, toluene) and (toluene / hexane = 2 / 1) to obtain 11 g of the compound represented by the formula (I-5-3). Next, 11 g of the compound represented by the formula (I-5-3), 150 mL of dichloromethane, and 6.2 g of 1,1 - thiocarbonyldiimidazole were added to the reaction vessel, and the mixture was heated under reflux for 2 hours. After completion of the reaction, the organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 2 / 1) to obtain 10.7 g of the compound represented by the formula (I-5). MS(EI): m / z = 423

[0206] (Example 6) Production of the compound represented by the formula (I-6)

[0207]

Chemical formula

[0208] Under a nitrogen atmosphere, 10 g of the compound represented by the formula (I-6-1), 7.8 g of the compound represented by the formula (I-6-2), 0.2 g of copper(I) iodide, 0.5 g of bis(triphenylphosphine)palladium(II) dichloride, and 100 mL of triethylamine were added to the reaction vessel. Then, the reaction solution was heated to 70 °C and reacted for 4 hours. After completion of the reaction, a saturated aqueous ammonium chloride solution was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then purified by column chromatography (silica gel, toluene) and (toluene / hexane = 2 / 1) to obtain 9.5 g of the compound represented by the formula (I-6). MS(EI): m / z = 455

[0209] (Example 7) Production of the compound represented by the formula (I-7)

[0210]

Chemical formula

[0211] In a nitrogen atmosphere, 10 g of the compound represented by the formula (I-7-1), 11 g of the compound represented by the formula (I-7-2), 0.3 g of copper(I) iodide, 0.5 g of bis(triphenylphosphine)palladium(II) dichloride, and 100 mL of triethylamine were added to a reaction vessel. Then, the reaction solution was heated to 70 °C and reacted for 4 hours. After completion of the reaction, a saturated aqueous ammonium chloride solution was poured into the reaction solution, and extraction was performed with ethyl acetate. After washing the organic layer with saturated brine, purification was carried out by column chromatography (silica gel, toluene) and (toluene / hexane = 2 / 1) to obtain 12.5 g of the compound represented by the formula (I-7-3). Next, 12.5 g of the compound represented by the formula (I-7-3), 150 mL of dichloromethane, and 6 g of 1,1-thiocarbonyldiimidazole were added to a reaction vessel, and heating under reflux was carried out for 2 hours. After completion of the reaction, the organic layer was washed with saturated brine, and then purification was carried out by column chromatography (silica gel, toluene) and recrystallization (toluene / hexane = 2 / 1) to obtain 10.2 g of the compound represented by the formula (I-7). MS(EI): m / z = 457

[0212] (Preparation and Evaluation of Liquid Crystal Composition) A parent liquid crystal (LC-1) having the following physical property values was prepared. All the values are measured values. T n-i (nematic phase-isotropic liquid phase transition temperature): 74.0 °C Δε (dielectric anisotropy at 25 °C and 1 kHz): 5.11 Δn (refractive index anisotropy at 25 °C and 589 nm): 0.141 γ1 (rotational viscosity coefficient at 25 °C): 107 mPa·s

[0213] To the parent liquid crystal (LC-1), the compounds (I-1) to (I-7) obtained in the examples and the compound represented by the formula (C-1) not employing a cyclohexenylene group were added, and liquid crystal compositions containing 0 mass%, 5 mass%, and 10 mass% of each compound in 100 mass% of the liquid crystal composition were prepared. Then, Δn and Δε at 100 mass% of each compound were determined using the least squares method rThe extrapolated value was obtained. The results are shown in Table 1.

[0214] (Storage stability test) To the host liquid crystal (LC-1), the compounds (I-1) to (I-7) obtained in the examples and the compound represented by the formula (C-1) that does not employ a cyclohexenylene group were added, and a liquid crystal composition containing 5% by mass of each compound in 100% by mass of the liquid crystal composition was prepared. 0.5 g of the prepared liquid crystal composition was weighed into a 1 mL sample bottle (manufactured by Maruemu Co., Ltd.), and degassing by evacuation was carried out at 150 °C and 250 Pa for 10 minutes. Then, it was purged with dry nitrogen and covered with the attached lid. This was stored in a temperature-controlled constant temperature bath (manufactured by Espec Co., Ltd., SH-241) at 0 °C for 2 weeks, and the occurrence of crystallization of the liquid crystal composition was visually confirmed every week. Those in which crystallization was not confirmed visually in the first week were marked as "〇", and those in which crystallization was confirmed were marked as "×". The results are shown in Table 1.

[0215] [Chemical formula]

[0216] [Table 1]

[0217] From Example 8 and Comparative Example 1, it was confirmed that the compound represented by the general formula (i) that employs a cyclohexenylene group has a large Δn, a large Δε r and good storage stability at low temperatures. Also, from Examples 9 to 14, the same effects were confirmed in various structures of the compound represented by the general formula (i). [Industrial applicability]

[0218] The compound of the present invention can be used in liquid crystal compositions, liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas.

Claims

1. The following general formula (i): 【Chemical 1】 (In general formula (i), R ｉ１ represents an alkyl group having 1 to 20 carbon atoms, When one or more of the -CH in the alkyl group ２ - may each independently be substituted with -O-, -S-, -NH-, -CO- and / or -CS- When one or more of the -CH in the alkyl group ２ -CH ２ - may each independently be substituted with -CH=CH-, -CF=CF- and / or -C≡C-. one or more hydrogen atoms in the alkenyl group may each independently be substituted with a halogen atom, provided that oxygen atoms do not directly bond to each other, X ｉ１ represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a thioisocyano group, an isothiocyanate group, an isocyanate group or an alkyl group having 1 to 20 carbon atoms, When one or more of the -CH in the alkyl group ２ - may each independently be substituted with -O-, -S-, -NH-, -CO- and / or -CS- When one or more of the -CH in the alkyl group ２ -CH ２ - may each independently be substituted with -CH=CH-, -CF=CF- and / or -C≡C-. one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom, provided that oxygen atoms do not directly bond to each other, J ｉ１ represents a cyclohexenylene group, A ｉ１ 、 A ｉ２ and A ｉ３ each independently represents either a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms, provided that A ｉ１ does not represent a 1,4-cyclohexylene group, Said J ｉ１ , A ｉ１ , A ｉ２ and A ｉ３ one or more hydrogen atoms in may each independently be substituted by a substituent S ｉ１ and may be substituted by a substituent S 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, One or more —CH in the alkyl group ２ — may each independently be optionally substituted with —O—, —S—, —NH—, —CS— and / or —CO—, One or more —CH in the alkyl group ２ —CH ２ — may each independently be substituted with —CH═CH—, —CF═CF— and / or —C≡C—. one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom, provided that oxygen atoms do not directly bond to each other, Substituent S ｉ１ When there are a plurality of them, they may be the same or different, Z ｉ１ and Z ｉ２ each independently represents either a single bond or an alkylene group having 1 to 20 carbon atoms, One or more of the -CH in the alkylene group ２ - may each independently be replaced by -O-, -CF ２ - and / or -CO- and may be substituted, When one or more of the -CH in the alkylene group ２ -CH ２ - may each independently be -CH ２ -CH(CH ３ )-, -CH(CH ３ )-CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ )-, -C(CH ３ )=CH-, -CH=N-, -N=CH-, -N=N- and / or -C≡C- and may be substituted, oxygen atoms do not directly bond to each other, n ｉ１ represents an integer from 0 to 2, n ｉ２ represents an integer from 1 to 3, A ｉ１ 、 A ｉ２ 、 Z ｉ１ or Z ｉ２ If there are a plurality of them, they may be the same as each other or different from each other. A compound represented by the formula.)

2. The compound represented by the general formula (i) is a compound selected from the group consisting of the following general formulas (i-1) to (i-7): 【Chemical 2】 (In general formulas (i-1) to (i-7), R ｉ１ 、A ｉ１ 、A ｉ２ 、A ｉ３ 、S ｉ１ and X ｉ１ are the same as R ｉ１ 、A ｉ１ 、A ｉ２ 、A ｉ３ 、S ｉ１ and X ｉ１ in the general formula (i) respectively, and represent the same meaning, A ｉ２－２ is defined in the same way as A in the general formula (i) above. ｉ２ (The definition is the same.) The compound according to claim 1.)

3. Said X ｉ１ The compound according to claim 1 or 2, wherein X represents a fluorine atom, a cyano group or an isothiocyanate group (—NCS).

4. A liquid crystal composition containing one or more of the compounds according to any one of claims 1 to 3.

5. A liquid crystal display element using the liquid crystal composition according to claim 4.

6. A sensor using the liquid crystal composition according to claim 4.

7. A liquid crystal lens using the liquid crystal composition according to claim 4.

8. An optical communication device using the liquid crystal composition according to claim 4.

9. An antenna using the liquid crystal composition according to claim 4.

10. The antenna according to claim 9, comprising a first substrate provided with a plurality of slots, a second substrate facing the first substrate and provided with a power supply unit, 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, wherein the liquid crystal layer contains the liquid crystal composition according to claim 4.)

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