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

Abstract

The present invention addresses the problem of providing a liquid crystal composition having a high Tni, a large Δn, a large Δεr, a small tanδiso, and favorable preservability at room temperature, and providing a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the same.　Specifically, the liquid crystal composition contains one or two or more compounds represented by general formula (i) having an alkenyl group and an isothiocyanate group (-NCS), and one or two or more compounds represented by general formula (ii) having an alkynyl group and an isothiocyanate group (-NCS).

Description

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

[0001] The present invention relates to 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.

[0002] Liquid crystals, which are widely used in displays, are attracting attention as a new application for LCD antennas that transmit and receive radio waves between mobile vehicles such as automobiles and communication satellites. Traditionally, satellite communications have used parabolic antennas, but when used in mobile vehicles such as automobiles, the antennas must be constantly pointed toward the satellite, necessitating large moving parts. However, LCD antennas can change the direction of radio waves by moving the liquid crystals inside the panel, eliminating the need to move the antenna itself and allowing for flat antenna shapes. Furthermore, to achieve high-capacity, high-speed global communications, low-earth-orbit (LOW-EO) satellite constellations with numerous low-earth-orbit (LOW-EO) satellites are being studied. LCD antennas, which can easily change the direction of radio waves to track LEO satellites that appear constantly moving from the ground, are useful. Autonomous driving, such as in automobiles, generally requires the downloading of large amounts of high-precision 3D map information. However, by incorporating LCD antennas into automobiles, large amounts of data can be downloaded from communication satellites without any mechanical moving parts. The frequency band used in satellite communications is approximately 13 GHz, significantly different from the frequencies used in conventional LCD display applications. Therefore, the physical properties required for liquid crystals vary significantly. For example, a Δn of approximately 0.4 is required for liquid crystals used in antennas, with an operating temperature range of, for example, -20 to 120°C. Furthermore, infrared laser image recognition and ranging devices using liquid crystals are also attracting attention as sensors for autonomous driving of vehicles such as automobiles. Liquid crystals for this application are required to have a Δn of, for example, 0.3 to 0.6, with an operating temperature range of, for example, 10 to 100°C. Furthermore, it is known that many liquid crystal compounds that constitute liquid crystal compositions exhibiting a high Δn of 0.2 or greater have low compatibility. Therefore, it is also important to select liquid crystal compounds with high compatibility. In contrast, technology for liquid crystals used in antennas is described, for example, in Patent Document 1. Furthermore, Non-Patent Document 1 proposes the use of liquid crystal materials as components of high-frequency devices.

[0003] Japanese Patent Application Laid-Open No. 2016-37607

[0004] Dolfi, Electronics Letters, (UK), 1993, Vol. 29, No. 10, pp. 926-928

[0005] The present invention is ｎｉ is high, Δn is large, and Δε ｒ is large, and tan δ ｉｓｏ The present invention aims to provide a liquid crystal composition having a small viscosity and good storage stability at room temperature, and a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the same.

[0006] As a result of extensive investigations, the present inventors have found that the above-mentioned problems can be solved by a liquid crystal composition containing one or more compounds represented by general formula (i) having an alkenyl group and an isothiocyanate group (-NCS), and one or more compounds represented by general formula (ii) having an alkynyl group and an isothiocyanate group (-NCS), and have thus completed the present invention. An example of the configuration of the present invention that solves the above-mentioned problems is as follows.

[0007] Item 1. A compound represented by the following general formula (i):

[0008]

[0009] (In general formula (i), R ｉ１ represents an alkenyl group having 2 to 20 carbon atoms, and one or more —CH ２ - may be independently substituted by -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH ２ -CH ２ - may each independently be substituted with -CH=CH- and / or -CF=CF-, one or more hydrogen atoms in the alkenyl group may each independently be substituted with a halogen atom, but oxygen atoms are not directly bonded to each other, ｉ１ , A ｉ２ and A ｉ３ each independently represents a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms, ｉ１ , Aｉ２ and A ｉ３ One or more hydrogen atoms in each independently represent a substituent S ｉ１ and the 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, ２ - may be independently substituted by -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH 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, but oxygen atoms are not directly bonded to each other, and the substituent S ｉ１ When there are a plurality of Z, they may be the same or different; ｉ１ and Z ｉ２ each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms, and one or more —CH ２ - is independently -O-, -CF ２ - and / or -CO-, and one or more -CH ２ -CH ２ Each - is independently -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—, —C≡C—, —CO—O— and / or —O—CO—, but oxygen atoms are not directly bonded to each other, ｉ１ represents an integer of 0 to 1), and one or more compounds represented by the following general formula (ii):

[0010]

[0011] (In general formula (ii), R ｉｉ１ represents an alkynyl group having 2 to 20 carbon atoms, and one or more —CH ２ - may be independently substituted by -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH ２ -CH ２ - may each independently be substituted with -C≡C-, one or more hydrogen atoms in the alkynyl group may each independently be substituted with a halogen atom, but oxygen atoms are not directly bonded to each other, ｉｉ１ , A ｉｉ２ and A ｉｉ３ each independently represents a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms, ｉｉ１ , A ｉｉ２ and A ｉｉ３ One or more hydrogen atoms in each independently represent a substituent S ｉｉ１ and the substituent S ｉｉ１ 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, ２- may be independently substituted by -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH 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, but oxygen atoms are not directly bonded to each other, and the substituent S ｉｉ１ When there are a plurality of Z, they may be the same or different; ｉｉ１ and Z ｉｉ２ each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms, and one or more —CH ２ - is independently -O-, -CF ２ - and / or -CO-, and one or more -CH ２ -CH ２ Each - is independently -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—, —C≡C—, —CO—O— and / or —O—CO—, but oxygen atoms are not directly bonded to each other, ｉｉ１ represents an integer of 0 to 2, ｉｉ３ and Z ｉｉ２ When a plurality of compounds are present, they may be the same or different.

[0012] Item 2. The liquid crystal composition according to item 1, wherein the total content of the compounds represented by general formula (i) in 100% by mass of the liquid crystal composition is 1 to 40% by mass, and / or the total content of the compounds represented by general formula (ii) in 100% by mass of the liquid crystal composition is 1 to 55% by mass.

[0013] Item 3. The compound represented by the general formula (i) is represented by the following general formulas (i-1) to (i-2):

[0014]

[0015] (In general formulas (i-1) to (i-2), R ｉ１ , A ｉ１ , A ｉ２ and A ｉ３ represents R in the above general formula (i). ｉ１ , A ｉ１ , A ｉ２ and A ｉ３ and (iii) each have the same meaning as above. 3. The liquid crystal composition according to item 1 or 2, wherein the compound is selected from the group consisting of compounds represented by the following formula:

[0016] Item 4. The compound represented by the general formula (ii) is a compound represented by the following general formulas (ii-1) to (ii-3):

[0017]

[0018] (In general formulas (ii-1) to (ii-3), R ｉｉ１ , A ｉｉ１ , A ｉｉ２ and A ｉｉ３ represents R in the above general formula (ii). ｉｉ１ , A ｉｉ１ , A ｉｉ２ and A ｉｉ３ and in general formula (ii-3), A ｉｉ３－２ The definition of A in the above general formula (ii) ｉｉ３－２ 4. The liquid crystal composition according to any one of items 1 to 3, wherein the compound is selected from the group consisting of compounds represented by the formula:

[0019] Item 5. Furthermore, the following general formula (iii)

[0020]

[0021] (In general formula (iii), R ｉｉｉ１each independently represents an alkyl group having 1 to 20 carbon atoms, and one or more —CH ２ - may each independently be substituted with -O-, -S-, -NH-, -CO- and / or -CS-, one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom, but oxygen atoms are not directly bonded to each other, ｉｉｉ１ and A ｉｉｉ２ are each independently the following groups (a), (b), (c), and (d): (a) a 1,4-cyclohexylene group (one —CH ２ - or two or more non-adjacent -CH ２- may be replaced by -O- and / or -S-.) (b) a 1,4-phenylene group (in which one -CH= or two or more -CH= groups 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, phenanthrene-2,7-diyl group, 2,3-dihydro-1H-indene-1,5-diyl group, 2,3-dihydro-1H-indene-2,5-diyl group, 2,3-dihydro-1H-indene-1,6-diyl group, 1 1H-indene-2,5-diyl group, 1H-indene-1,5-diyl group, 1H-indene-3,5-diyl group, 1H-indene-1,6-diyl group, 1H-indene-2,6-diyl group, 1H-indene-3,6-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) represents a group selected from the group consisting of thiophene-2,5-diyl group, benzothiophene-2,5-diyl group, benzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-2,6-diyl group, thieno[3,2-b]thiophene-2,5-diyl group, and benzo[1,2-b:4,5-b']dithiophene-2,6-diyl group (one -CH= or two or more -CH= present in this group may be replaced by -N=), ｉｉｉ１ and A ｉｉｉ２ One or more hydrogen atoms in each independently represent a substituent S ｉｉｉ１ and the substituent S ｉｉｉ１represents 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, or an alkyl group having 1 to 20 carbon atoms, and one or more —CH ２ - may be independently substituted by -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH ２ -CH ２ - may each independently be substituted by -CH=CH-, -CF=CF- and / or -C≡C-, one or more hydrogen atoms in the alkyl group may each independently be substituted by a halogen atom, but oxygen atoms are not directly bonded to each other, and the substituent S ｉｉｉ１ When there are a plurality of Z, they may be the same or different; ｉｉｉ１ represents a single bond or an alkylene group having 1 to 20 carbon atoms, and one or more —CH ２ - is independently -O-, -CF ２ - and / or -CO-, and one or more -CH ２ -CH ２ Each - is independently -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—, —C≡C—, —CO—O— and / or —O—CO—, wherein an oxygen atom is not directly bonded to an oxygen atom, ｉｉｉ１ represents an integer of 1 to 4, ｉｉｉ１ and Z ｉｉｉ１(When a plurality of compounds are present, they may be the same or different.)

[0022] Item 6. Liquid crystal phase upper limit temperature (T ｎｉ Item 6. The liquid crystal composition according to any one of items 1 to 5, wherein the liquid crystal temperature is 120° C. or higher.

[0023] Item 7. A liquid crystal display device using the liquid crystal composition according to any one of items 1 to 6.

[0024] Item 8. The liquid crystal display element according to item 7, which is driven by an active matrix method or a passive matrix method.

[0025] Item 9. A liquid crystal display device in which the dielectric constant is reversibly switched by reversibly changing the alignment direction of liquid crystal molecules of the liquid crystal composition according to any one of items 1 to 6.

[0026] Item 10. A sensor using the liquid crystal composition according to any one of items 1 to 6.

[0027] Item 11. A liquid crystal lens using the liquid crystal composition according to any one of items 1 to 6.

[0028] Item 12. An optical communication device using the liquid crystal composition according to any one of items 1 to 6.

[0029] Item 13. An antenna using the liquid crystal composition according to any one of items 1 to 6.

[0030] Item 14. The antenna according to item 13, comprising: a first substrate having a plurality of slots; a second substrate facing the first substrate and having a power supply section; 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 any one of items 1 to 6.

[0031] According to the present invention, a liquid crystal composition containing one or more compounds represented by general formula (i) having an alkenyl group and an isothiocyanate group (-NCS) and one or more compounds represented by general formula (ii) having an alkynyl group and an isothiocyanate group (-NCS) can be used to obtain T ｎｉ is high, Δn is large, and Δε ｒ is large, and tan δ ｉｓｏ A liquid crystal composition having a small viscosity and good storage stability at room temperature can be obtained, and the liquid crystal composition is useful for liquid crystal display elements, sensors, liquid crystal lenses, optical communication devices, and antennas.

[0032] (Compound Represented by General Formula (i)) The liquid crystal composition according to the present invention contains one or more compounds represented by general formula (i) having an alkenyl group and an isothiocyanate group (-NCS).

[0033]

[0034] In general formula (i), R ｉ１ represents an alkenyl group having 2 to 20 carbon atoms. The alkenyl group having 2 to 20 carbon atoms is a linear, branched or cyclic alkenyl group, and is preferably a linear alkenyl group. The number of carbon atoms in the alkenyl group having 2 to 20 carbon atoms is preferably 2 to 10, and more preferably 2 to 6. One or more -CH ２ Each - may be independently substituted by -O-, -S-, -NH-, -CO- and / or -CS-. In addition, one or more -CH ２ -CH ２Each - may be independently substituted with -CH=CH- and / or -CF=CF-. Furthermore, one or more hydrogen atoms in the alkenyl group may be independently substituted with a halogen atom. Examples of halogen atoms include a fluorine atom, a chlorine atom, and a bromine atom. However, when the alkenyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other. Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to each other and / or oxygen atoms are not directly bonded to each other. R ｉ１ Specific examples of the alkenyl group having 1 to 20 carbon atoms (including substituted ones) in the formula (R ｉ１ -1) to (R ｉ１ -19) and the like.

[0035]

[0036] Formula (R ｉ１ -1) to (R ｉ１ -19) In the middle, the black dot is A ｉ１ represents a bond to the ｉ１ As the alkyl group, a linear alkenyl group having 2 to 6 carbon atoms is preferred from the viewpoint of Δn and compatibility with other liquid crystal compounds.

[0037] In general formula (i), A ｉ１ , A ｉ２ and A ｉ３ each independently represents a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms. More specifically, the hydrocarbon ring having 3 to 16 carbon atoms or the heterocyclic ring having 3 to 16 carbon atoms is the following group (a), group (b), group (c), and group (d): (a) a 1,4-cyclohexylene group (one —CH ２ - or two or more non-adjacent -CH ２(b) a 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= groups in this group may be replaced by -N=) (c) a 1,4-cyclohexenylene group, a bicyclo[2.2.2]octane-1,4-diyl group, 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, a decahydronaphthalene-2,6-diyl group, an anthracene-2,6-diyl group, an anthracene-1,4-diyl group, an anthracene-9,10-diyl group, a phenanthrene 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) It is preferable that the group represented is a group selected from the group consisting of 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, and a thieno[3,2-b]thiophene-2,5-diyl group (in which one -CH= or two or more non-adjacent -CH= may be replaced by -N=).

[0038] A ｉ１ , A ｉ２ and A ｉ３ One or more hydrogen atoms in each independently represent a substituent S ｉ１ The 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, and is preferably a linear alkyl group. The number of carbon atoms in the alkyl group is preferably 2 to 10, and more preferably 3 to 6. One or more -CH ２ Each - may be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-. ２ -CH ２ Each - may be independently substituted with -CH=CH-, -CF=CF- and / or -C≡C-. Furthermore, one or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom. Examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other. Furthermore, 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 each other. Substituent S ｉ１ is preferably a fluorine atom, a chlorine atom, a linear alkyl group having 1 to 6 carbon atoms, or a linear alkoxy group having 1 to 6 carbon atoms. ｉ１ , A ｉ２ and A ｉ３ At least one of the groups has at least one substituent S ｉ１ It is preferable that A is substituted with ｉ３ is at least one substituent S ｉ１ It is preferable that the substituent S ｉ１ When there are a plurality of, they may be the same or different.

[0039] Aｉ１ Substituent S in ｉ１ The substitution position of the formula (A ｉ１ -SP-1) to (A ｉ１ -SP-4).

[0040]

[0041] Formula (A ｉ１ -SP-1) to (A ｉ１ -SP-4) White points are R ｉ１ The black dots represent bonds to Z. ｉ１ A represents a bond to ｉ２ Substituent S in ｉ１ The substitution position of the formula (A ｉ２ -SP-1) to (A ｉ２ -SP-4).

[0042]

[0043] Formula (A ｉ２ -SP-1) to (A ｉ２ -SP-4) White spots are Z ｉ１ The black dots represent bonds to Z. ｉ２ or a bond to an isothiocyanate group (-NCS). ｉ３ Substituent S in ｉ１ The substitution position of the formula (A ｉ３ -SP-1) to (A ｉ３ -SP-4).

[0044]

[0045] Formula (A ｉ３ -SP-1) to (A ｉ３ -SP-4) White spots are Z ｉ２ The black dot represents a bond to the isothiocyanate group (-NCS). ｉ１ is expressed by the following formula (A ｉ１ -1) to (A ｉ１ -11) is preferably represented by any one of the following formulas.

[0046]

[0047] Formula (Aｉ１ -1) to (A ｉ１ -11) In the middle, the white point is R ｉ１ The black dots represent bonds to Z. ｉ１ More specifically, A ｉ２ is expressed by the following formula (A ｉ２ -1) to (A ｉ２ -13) is preferably represented by any one of the following formulas.

[0048]

[0049] Formula (A ｉ２ -1) to (A ｉ２ -13) In the middle, the white point is Z ｉ１ The black dots represent bonds to Z. ｉ２ or a bond to an isothiocyanate group (-NCS). ｉ３ is expressed by the following formula (A ｉ３ -1) to (A ｉ３ -11) is preferably represented by any one of the following formulas.

[0050]

[0051] Formula (A ｉ３ -1) to (A ｉ３ -11) In the middle, the white point is Z ｉ２ The black dot represents a bond to the isothiocyanate group (-NCS).

[0052] In general formula (i), Z ｉ１ and Z ｉ２ each 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, and is preferably a linear alkylene group. The number of carbon atoms in the alkylene group is preferably 2 to 10, and more preferably 2 to 6. One or more -CH ２ - is independently -O-, -CF ２ In addition, the alkylene group may be substituted with one or more —CH ２ -CH ２ Each - is independently -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—, —C≡C—, —CO—O—, and / or —O—CO—. However, when the alkylene group is substituted with a specific group, the oxygen atoms are not directly bonded to each other.

[0053] Specific examples of the alkylene group having 2 to 20 carbon atoms (including substituted groups) include those represented by the formula (Z ｉ１／２ -1) to (Z ｉ１／２ -24).

[0054]

[0055] Expression (Z ｉ１／２ -1) to (Z ｉ１／２ -24) Medium, white point is A ｉ１ or A ｉ２ The black dot represents a bond to A. ｉ２ or A ｉ３ From the viewpoint of improving Δn, Z ｉ１ is the formula (Z ｉ１／２ -4) (-C≡C-).

[0056] In general formula (i), n ｉ１ represents an integer of 0 to 1. ｉｉ１ When Z is 1, from the viewpoint of solubility and low viscosity, ｉ２ preferably represents a single bond.

[0057] The compound represented by general formula (i) is preferably a compound represented by the following general formulas (i-1) to (i-2).

[0058]

[0059] In general formulas (i-1) to (i-2), R ｉ１ , A ｉ１ , A ｉ２ and A ｉ３ are each independently R in the general formula (i). ｉ１ , A ｉ１, A ｉ２ and A ｉ３ It has the same meaning as:

[0060] The compound represented by general formula (i-1) is preferably a compound represented by the following general formulas (i-1-1) to (i-1-2).

[0061]

[0062] In general formulas (i-1-1) to (i-1-2), R ｉ１ and S ｉ１ are each independently R in the general formula (i). ｉ１ and S ｉ１ 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-1-1.8).

[0063]

[0064] 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-1-2.6).

[0065]

[0066] The compound represented by general formula (i-2) is preferably a compound represented by the following general formulas (i-2-1) to (i-2-2).

[0067]

[0068] In general formulas (i-2-1) to (i-2-2), R ｉ１ and S ｉ１ are each independently R in the general formula (i). ｉ１ and S ｉ１ Specific examples of the compound represented by general formula (i-2-1) include compounds represented by the following structural formulas (i-2-1.1) to (i-2-1.7).

[0069]

[0070] Specific examples of the compound represented by general formula (i-2-1) include compounds represented by the following structural formulas (i-2-2.1) to (i-2-2.8).

[0071]

[0072] The type of compound represented by general formula (i), general formulas (i-1) to (i-2), general formulas (i-1-1) to (i-1-2), general formulas (i-2-1) to (i-2-2), structural formulas (i-1-1.1) to (i-1-1.8), structural formulas (i-1-2.1) to (i-1-2.6), structural formulas (i-2-1.1) to (i-2-1.7), or structural formulas (i-2-2.1) to (i-2-2.8) used in the liquid crystal composition is one or more types, preferably 1 to 10 types, preferably 1 to 5 types, and preferably 1 to 3 types.

[0073] The lower limit of the total content of the compounds represented by general formula (i), general formulas (i-1) to (i-2), general formulas (i-1-1) to (i-1-2), general formulas (i-2-1) to (i-2-2), structural formulas (i-1-1.1) to (i-1-1.8), structural formulas (i-1-2.1) to (i-1-2.6), structural formulas (i-2-1.1) to (i-2-1.7), or structural formulas (i-2-2.1) to (i-2-2.8) in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, preferably 3% by mass or more, preferably 5% by mass or more, preferably 10% by mass or more, preferably 15% by mass or more, preferably 20% by mass or more, preferably 25% by mass or more, and preferably 30% by mass or more.

[0074] The upper limit of the total content of the compounds represented by general formula (i), general formulas (i-1) to (i-2), general formulas (i-1-1) to (i-1-2), general formulas (i-2-1) to (i-2-2), structural formulas (i-1-1.1) to (i-1-1.8), structural formulas (i-1-2.1) to (i-1-2.6), structural formulas (i-2-1.1) to (i-2-1.7), or structural formulas (i-2-2.1) to (i-2-2.8) in 100% by mass of the liquid crystal composition is preferably 40% by mass or less, preferably 35% by mass or less, preferably 30% by mass or less, preferably 25% by mass or less, preferably 20% by mass or less, preferably 15% by mass or less, preferably 10% by mass or less, and preferably 5% by mass or less.

[0075] The total content of the compounds represented by general formula (i), general formulas (i-1) to (i-2), general formulas (i-1-1) to (i-1-2), general formulas (i-2-1) to (i-2-2), structural formulas (i-1-1.1) to (i-1-1.8), structural formulas (i-1-2.1) to (i-1-2.6), structural formulas (i-2-1.1) to (i-2-1.7), or structural formulas (i-2-2.1) to (i-2-2.8) in 100% by mass of the liquid crystal composition is determined by the following formulas: solubility, Δn and / or Δε ｒ From this viewpoint, the content is preferably 1 to 40% by mass, more preferably 3 to 35% by mass, and even more preferably 5 to 35% by mass.

[0076] The compound represented by general formula (i) (including its sub-concepts) can be synthesized using a known synthesis method. (Compound represented by general formula (ii)) The liquid crystal composition according to the present invention contains one or more compounds represented by general formula (i) having an alkynyl group and an isothiocyanate group (-NCS).

[0077]

[0078] In general formula (ii), R ｉｉ１represents an alkynyl group having 2 to 20 carbon atoms. The alkynyl group having 2 to 20 carbon atoms is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group. The number of carbon atoms in the alkynyl group having 2 to 20 carbon atoms is preferably 2 to 10, and more preferably 2 to 6. One or more -CH ２ Each - may be independently substituted by -O-, -S-, -NH-, -CO- and / or -CS-. In addition, one or more -CH ２ -CH ２ Each - may be independently substituted with -C≡C-. Furthermore, one or more hydrogen atoms in the alkynyl group may be independently substituted with a halogen atom. Examples of halogen atoms include a fluorine atom, a chlorine atom, and a bromine atom. However, when the alkynyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other. Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to each other and / or oxygen atoms are not directly bonded to each other.

[0079] As the alkynyl group, from the viewpoint of ease of synthesis and extension of the conjugated system, the following formula (R ｉｉ１ Alkynyl groups represented by -A) are preferred.

[0080]

[0081] Formula (R ｉｉ１ -A) Medium, R ｉｉ１Ａ 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 —CH ２ Each - may be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-. ２ -CH ２Each - may be independently substituted with -C≡C-. Furthermore, one or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom. Examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other. Furthermore, 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 each other. Furthermore, in the case of a compound represented by the formula (R ｉｉ１ -A) In the middle, the black dot is A ｉｉ１ Represents a bond to .

[0082] R ｉｉ１ Specific examples of the alkynyl group having 2 to 20 carbon atoms (including substituted ones) in the formula (R ｉｉ１ -1) to (R ｉｉ１ -16) and the like.

[0083]

[0084] Formula (R ｉ１ -1) to (R ｉｉ１ -16) In the middle, the black dot is A ｉｉ１ represents a bond to the ｉｉ１ From the viewpoint of Δn and solubility, a linear alkynyl group having 2 to 8 carbon atoms is preferred.

[0085] In general formula (ii), A ｉｉ１ , A ｉｉ２ and A ｉｉ３ each independently represents a hydrocarbon ring having 3 to 16 carbon atoms or a heterocyclic ring having 3 to 16 carbon atoms. More specifically, the hydrocarbon ring having 3 to 16 carbon atoms or the heterocyclic ring having 3 to 16 carbon atoms is the following group (a), group (b), group (c), and group (d): (a) a 1,4-cyclohexylene group (one —CH ２ - or two or more non-adjacent -CH ２(b) a 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= groups in this group may be replaced by -N=) (c) a 1,4-cyclohexenylene group, a bicyclo[2.2.2]octane-1,4-diyl group, 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, a decahydronaphthalene-2,6-diyl group, an anthracene-2,6-diyl group, an anthracene-1,4-diyl group, an anthracene-9,10-diyl group, a phenanthrene 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) It is preferable that the group represented is a group selected from the group consisting of 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, and a thieno[3,2-b]thiophene-2,5-diyl group (in which one -CH= or two or more non-adjacent -CH= may be replaced by -N=).

[0086] A ｉｉ１ , A ｉｉ２ and A ｉｉ３ One or more hydrogen atoms in each independently represent a substituent S ｉｉ１ The substituent S ｉｉ１represents 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, and is preferably a linear alkyl group. The number of carbon atoms in the alkyl group is preferably 2 to 10, and more preferably 3 to 6. One or more -CH ２ Each - may be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-. ２ -CH ２ Each - may be independently substituted with -CH=CH-, -CF=CF- and / or -C≡C-. Furthermore, one or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom. Examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other. Furthermore, 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 each other. Substituent S ｉｉ１ is preferably a fluorine atom, a linear alkyl group having 1 to 6 carbon atoms, or a linear alkoxy group having 1 to 6 carbon atoms. ｉｉ１ , A ｉｉ２ and A ｉｉ３ At least one of the groups has at least one substituent S ｉ１ It is preferable that A is substituted with ｉｉ３ is at least one substituent S ｉ１ It is preferable that the substituent S ｉｉ１ When there are a plurality of, they may be the same or different.

[0087] A ｉｉ１Substituent S in ｉｉ１ The substitution position of the formula (A ｉｉ１ -SP-1) to (A ｉｉ１ -SP-4).

[0088]

[0089] Formula (A ｉｉ１ -SP-1) to (A ｉｉ１ -SP-4) White points are R ｉｉ１ The black dots represent bonds to Z. ｉｉ１ A represents a bond to ｉｉ２ Substituent S in ｉ１ The substitution position of the formula (A ｉｉ２ -SP-1) to (A ｉｉ２ -SP-4).

[0090]

[0091] Formula (A ｉｉ２ -SP-1) to (A ｉｉ２ -SP-4) White spots are Z ｉｉ１ The black dots represent bonds to Z. ｉｉ２ or a bond to an isothiocyanate group (-NCS). ｉｉ３ Substituent S in ｉｉ１ The substitution position of the formula (A ｉｉ３ -SP-1) to (A ｉｉ３ -SP-4).

[0092]

[0093] Formula (A ｉｉ３ -SP-1) to (A ｉｉ３ -SP-4) White spots are Z ｉｉ２ The black dots represent bonds to Z. ｉｉ２ or a bond to an isothiocyanate group (-NCS). ｉｉ１ is expressed by the following formula (A ｉｉ１ -1) to (A ｉｉ１ -11) is preferably represented by any one of the following formulas.

[0094]

[0095] Formula (Aｉｉ１ -1) to (A ｉｉ１ -11) In the middle, the white point is R ｉｉ１ The black dots represent bonds to Z. ｉｉ１ More specifically, A ｉｉ２ is expressed by the following formula (A ｉｉ２ -1) to (A ｉｉ２ -11) is preferably represented by any one of the following formulas.

[0096]

[0097] Formula (A ｉｉ２ -1) to (A ｉｉ２ -11) In the middle, the white point is Z ｉｉ１ The black dots represent bonds to Z. ｉｉ２ or a bond to an isothiocyanate group (-NCS). ｉｉ３ is expressed by the following formula (A ｉｉ３ -1) to (A ｉｉ３ -11) is preferably represented by any one of the following formulas.

[0098]

[0099] Formula (A ｉｉ３ -1) to (A ｉｉ３ -11) In the middle, the white point is Z ｉｉ２ The black dots represent bonds to Z. ｉｉ２ or a bond of an isothiocyanate group (-NCS).

[0100] In general formula (ii), Z ｉｉ１ and Z ｉｉ２ each 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, and is preferably a linear alkylene group. The number of carbon atoms in the alkylene group is preferably 2 to 10, and more preferably 2 to 6. One or more -CH ２ - is independently -O-, -CF ２ In addition, the alkylene group may be substituted with one or more —CH ２ -CH ２ Each - is independently -CH ２ -CH(CH３ ) -, -CH(CH ３ )-CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ ) -, -C(CH ３ )═CH—, —CH═N—, —N═CH—, —N═N—, —C≡C—, —CO—O—, and / or —O—CO—. However, when the alkylene group is substituted with a specific group, the oxygen atoms are not directly bonded to each other.

[0101] Specific examples of the alkylene group having 2 to 20 carbon atoms (including substituted groups) include those represented by the formula (Z ｉｉ１／２ -1) to (Z ｉｉ１／２ -24).

[0102]

[0103] Expression (Z ｉｉ１／２ -1) to (Z ｉｉ１／２ -24) Medium, white point is A ｉｉ１ , A ｉｉ２ or A ｉｉ３ The black dot represents a bond to A. ｉｉ２ or A ｉｉ３ represents a bond to Δn and / or Δε. ｒ From the perspective of Z ｉｉ１ and Z ｉｉ２ are each preferably independently a single bond or -C≡C-. ｒ From the perspective of Z ｉｉ１ and Z ｉｉ２ It is preferable that at least one of the groups is —C≡C—.

[0104] In general formula (ii), n ｉｉ１ represents an integer of 0 to 2. ｉｉ１ When is 1, Δn and / or Δε ｒ From the perspective of Z ｉｉ１ or Z ｉｉ２ Preferably, represents -C≡C-. ｉｉ１ When is 2, Δn and / or Δε ｒ From the perspective of Z ｉｉ２Preferably, at least one of n represents —C≡C—. ｉｉ１ When is 2, Δn and / or Δε ｒ From the perspective of Z ｉｉ２ It is preferable that A represents a single bond or —C≡C—. ｉｉ３ and Z ｉｉ２ When there are a plurality of groups, they may be the same or different.

[0105] The compound represented by general formula (ii) is preferably a compound represented by the following general formulas (ii-1) to (ii-3).

[0106]

[0107] In general formulas (ii-1) to (ii-3), R ｉｉ１ , A ｉｉ１ , A ｉｉ２ and A ｉｉ３ represents R in the above general formula (ii). ｉｉ１ , A ｉｉ１ , A ｉｉ２ and A ｉｉ３ In addition, in general formula (ii-3), A ｉｉ３－２ The definition of A in the above general formula (ii) ｉｉ３－２ is the same as the definition of

[0108] The compound represented by general formula (ii-1) is preferably a compound represented by the following general formulas (ii-1-1) to (ii-1-3).

[0109]

[0110] In general formulas (ii-1-1) to (ii-1-3), R ｉｉ１ and S ｉｉ１ are each independently R in the general formula (ii). ｉｉ１ and S ｉｉ１ Specific examples of the compound represented by general formula (ii-1-1) include compounds represented by the following structural formulas (ii-1-1.1) to (ii-1-1.2).

[0111]

[0112] 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-1-2.2).

[0113]

[0114] Specific examples of the compound represented by general formula (ii-1-3) include compounds represented by the following structural formula (ii-1-3.1).

[0115]

[0116] The compound represented by general formula (ii-2) is preferably a compound represented by the following general formulas (ii-2-1) to (ii-2-3).

[0117]

[0118] In general formulas (ii-2-1) to (ii-2-3), R ｉｉ１ and S ｉｉ１ are each independently R in the general formula (ii). ｉｉ１ and S ｉｉ１ Specific examples of the compound represented by general formula (ii-2-1) include compounds represented by the following structural formulas (ii-2-1.1) to (ii-2-1.2).

[0119]

[0120] 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-2-2.5).

[0121]

[0122] Specific examples of the compound represented by general formula (ii-2-3) include compounds represented by the following structural formula (ii-2-3.1).

[0123]

[0124] The compound represented by general formula (ii-3) is preferably a compound represented by the following general formula (ii-3-1).

[0125]

[0126] In general formula (ii-3-1), R ｉｉ１ and S ｉｉ１ are each independently R in the general formula (ii). ｉｉ１ and S ｉｉ１ Specific examples of the compound represented by general formula (ii-3-1) include compounds represented by the following structural formulas (ii-3-1.1) to (ii-3-1.2).

[0127]

[0128] The type of compound represented by general formula (ii), general formulas (ii-1) to (ii-3), general formulas (ii-1-1) to (ii-1-3), general formulas (ii-2-1) to (ii-2-3), general formula (ii-3-1), structural formulas (ii-1-1.1) to (ii-1-1.2), structural formulas (ii-1-2.1) to (ii-1-2.2), structural formula (ii-1-3.1), structural formulas (ii-2-1.1) to (ii-2-1.2), structural formulas (ii-2-2.1) to (ii-2-2.5), structural formulas (ii-2-3.1) or structural formulas (ii-3-1.1) to (ii-3-1.2) used in the liquid crystal composition is one or two or more types, preferably 1 to 10 types, preferably 1 to 5 types, and preferably 1 to 3 types.

[0129] General formula (ii), general formula (ii-1) to (ii-3), general formula (ii-1-1) to (i-1-3), general formula (ii-2-1) to (ii-2-3), general formula (ii-3-1), structural formula (ii-1-1.1) to (ii- 1-1.2), Structural formula (ii-1-2.1) to (ii-1-2.2), Structural formula (ii-1-3.1), Structural formula (ii-2-1.1) to (ii-2-1.2), Structural formula (ii-2-2.1) to (ii-2-2.5), The lower limit of the total content of the compounds represented by structural formula (ii-2-3.1) or structural formulae (ii-3-1.1) to (ii-3-1.2) in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, preferably 3% by mass or more, preferably 5% by mass or more, preferably 10% by mass or more, preferably 15% by mass or more, preferably 20% by mass or more, and preferably 25% by mass or more.

[0130] General formula (ii), general formulas (ii-1) to (ii-3), general formulas (ii-1-1) to (ii-1-3), general formulas (ii-2-1) to (ii-2-3), general formula (ii-3-1), structural formulas (ii-1-1.1) to (ii-1-1.2), structural formulas (ii-1-2.1) to (ii-1-2.2), structural formula (ii-1-3.1), structural formulas (ii-2-1.1) to (ii-2-1.2), structural formulas (ii-2-2.1) to (ii-2-2.5), structural formula (ii-2-3.1) or structural formulas (ii-3-1.1) to (ii-3-1.2) The upper limit of the total content of the compounds represented by the formula (I) in 100% by mass of the liquid crystal composition is preferably 55% by mass or less, preferably 50% by mass or less, preferably 45% by mass or less, preferably 40% by mass or less, preferably 35% by mass or less, preferably 30% by mass or less, preferably 25% by mass or less, preferably 20% by mass or less, preferably 15% by mass or less, preferably 10% by mass or less, and preferably 5% by mass or less.

[0131] The total content of the compounds represented by general formula (ii), general formulas (ii-1) to (ii-3), general formulas (ii-1-1) to (ii-1-3), general formulas (ii-2-1) to (ii-2-3), general formula (ii-3-1), structural formulas (ii-1-1.1) to (ii-1-1.2), structural formulas (ii-1-2.1) to (ii-1-2.2), structural formula (ii-1-3.1), structural formulas (ii-2-1.1) to (ii-2-1.2), structural formulas (ii-2-2.1) to (ii-2-2.5), structural formulas (ii-2-3.1) or structural formulas (ii-3-1.1) to (ii-3-1.2) in 100% by mass of the liquid crystal composition is ｒ From this viewpoint, the content is preferably 1 to 55% by mass, more preferably 3 to 50% by mass, and even more preferably 5 to 45% by mass.

[0132] The compound represented by general formula (ii) (including its sub-concepts) can be synthesized using known synthesis methods.

[0133] (Compound represented by general formula (iii)) The liquid crystal composition according to the present invention has a solubility, Δn and / or Δε ｒ From this viewpoint, it is preferable to contain one or more compounds having an isothiocyanate group (—NCS) and represented by the following general formula (iii):

[0134]

[0135] In general formula (iii), R ｉｉｉ１ represents an alkyl group having 1 to 20 carbon atoms. The alkyl group may be linear, branched, or cyclic, and is preferably a linear alkyl group. The number of carbon atoms in the alkyl group is preferably 2 to 10, and more preferably 2 to 6. One or more —CH ２Each - may be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-. Furthermore, one or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom. Examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other. Furthermore, from the viewpoint of compound stability, it is preferable that sulfur atoms are not directly bonded to each other and / or oxygen atoms are not directly bonded to each other. For example, R ｉｉｉ１ represents one —CH ２ By substituting - with -O-, an alkoxy group having 1 to 19 carbon atoms can be represented. The alkoxy group is a linear, branched or cyclic alkoxy group, and a linear alkoxy group is preferred. The number of carbon atoms in the alkoxy group is preferably 2 to 10, and more preferably 2 to 6. In addition, R ｉｉｉ１ represents one —CH ２ By substituting - with -S-, an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms can be represented. The alkylsulfanyl group is a linear, branched, or cyclic alkylsulfanyl group, and a linear alkylsulfanyl group is preferred. The number of carbon atoms in the alkylsulfanyl group is preferably 1 to 10, and more preferably 1 to 6. In addition, R ｉｉｉ１ can represent a halogenated alkyl group having 1 to 20 carbon atoms, with one or more hydrogen atoms in the alkyl group being substituted with halogen atoms. The halogenated alkyl group may be linear, branched, or cyclic, and is preferably a linear halogenated alkyl group. The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, and more preferably 2 to 6. In addition, R ｉｉｉ１ represents one —CH ２The halogenated alkoxy group may be a linear, branched, or cyclic halogenated alkoxy group, preferably a linear halogenated alkoxy group. The halogenated alkoxy group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms. R ｉｉｉ１ Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) in the formula (R ｉｉｉ１ -1) to (R ｉｉｉ１ -30).

[0136]

[0137] Formula (R ｉｉｉ１ -1) to (R ｉｉｉ１ -30) In the middle, black dots are A ｉｉｉ１ represents a bond to the ｉｉｉ１ From the viewpoint of solubility, the alkyl group is preferably a linear or branched alkyl group having 2 to 8 carbon atoms, a linear alkoxy group having 2 to 8 carbon atoms, a linear halogenated alkoxy group having 1 to 8 carbon atoms, or a linear alkylsulfanyl group having 1 to 6 carbon atoms.

[0138] In general formula (iii), A ｉｉｉ１ and A ｉｉｉ２ are each independently the following groups (a), (b), (c), and (d): (a) a 1,4-cyclohexylene group (one —CH ２ - or two or more non-adjacent -CH ２- may be replaced by -O- and / or -S-.) (b) a 1,4-phenylene group (in which one -CH= or two or more -CH= groups 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, phenanthrene-2,7-diyl group, 2,3-dihydro-1H-indene-1,5-diyl group, 2,3-dihydro-1H-indene-2,5-diyl group, 2,3-dihydro-1H-indene-1,6-diyl group, 1 1H-indene-2,5-diyl group, 1H-indene-1,5-diyl group, 1H-indene-3,5-diyl group, 1H-indene-1,6-diyl group, 1H-indene-2,6-diyl group, 1H-indene-3,6-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) represents a group selected from the group consisting of 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, a thieno[3,2-b]thiophene-2,5-diyl group, and a benzo[1,2-b:4,5-b']dithiophene-2,6-diyl group (one -CH= or two or more -CH= present in this group may be replaced by -N=).

[0139] A ｉｉｉ１ and A ｉｉｉ２ One or more hydrogen atoms in each independently represent a substituent S ｉｉｉ１The substituent S ｉｉｉ１ 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, or an alkyl group having 1 to 20 carbon atoms. Examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. The alkyl group having 1 to 20 carbon atoms is a linear, branched, or cyclic alkyl group, and a linear alkyl group is preferred. The number of carbon atoms in the alkyl group having 1 to 20 carbon atoms is preferably 2 to 10, and more preferably 2 to 6. One or more —CH ２ Each - may be independently substituted by -O-, -S-, -NH-, -CO- and / or -CS-. ２ -CH ２ Each - may be independently substituted with -CH=CH-, -CF=CF- and / or -C≡C-. Furthermore, one or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom. Examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. However, when the alkyl group is substituted with a specific group, oxygen atoms are not directly bonded to each other. Furthermore, 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 each other. For example, the substituent S ｉｉｉ１ represents one —CH ２ By substituting - with -O-, it can represent an alkoxy group having 1 to 19 carbon atoms. 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 more preferably 2 to 6. In addition, the substituent S ｉｉｉ１ represents one —CH ２By substituting - with -S-, an alkylsulfanyl group (alkylthio group) having 1 to 19 carbon atoms can be represented. The alkylsulfanyl group is a linear, branched or cyclic alkylsulfanyl group, and a linear alkylsulfanyl group is preferred. The number of carbon atoms in the alkylsulfanyl group is preferably 2 to 10, and more preferably 2 to 6. In addition, the substituent S ｉｉｉ１ represents one or more —CH ２ -CH ２ By substituting - with -CH=CH-, an alkenyl group having 2 to 20 carbon atoms can be represented. The alkenyl group is a linear, branched or cyclic alkenyl group, and a linear alkenyl group is preferred. The number of carbon atoms in the alkenyl group is preferably 2 to 10, and more preferably 2 to 6. In addition, the substituent S ｉｉｉ１ represents one or more —CH ２ -CH ２ By substituting - with -C≡C-, it can represent an alkynyl group having 2 to 20 carbon atoms. The alkynyl group is a linear, branched or cyclic alkynyl group, and is preferably a linear alkynyl group. The number of carbon atoms in the alkynyl group is preferably 2 to 10, and more preferably 2 to 6. In addition, the substituent S ｉｉｉ１ represents one —CH ２ - is replaced by -O- and one or more -CH ２ -CH ２ By replacing - with -CH=CH-, an alkenyloxy group having 2 to 19 carbon atoms can be represented. The alkenyloxy group is a linear, branched or cyclic alkenyloxy group, and a linear alkenyloxy group is preferred. The number of carbon atoms in the alkenyloxy group is preferably 2 to 10, and more preferably 2 to 6. In addition, the substituent S ｉｉｉ１can represent a halogenated alkyl group having 1 to 20 carbon atoms, with one or more hydrogen atoms in the alkyl group being substituted with halogen atoms. The halogenated alkyl group may be linear, branched, or cyclic, and is preferably a linear halogenated alkyl group. The number of carbon atoms in the halogenated alkyl group is preferably 2 to 10, and more preferably 2 to 6. In addition, the substituent S ｉｉｉ１ represents one —CH ２ The halogenated alkoxy group may be a linear, branched, or cyclic halogenated alkoxy group, preferably a linear halogenated alkoxy group. The halogenated alkoxy group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms. Substituent S ｉｉｉ１ Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) in the formula (S ｉｉｉ１Ｒ -1) to (S ｉｉｉ１Ｒ -36) and the like.

[0140]

[0141] Formula (S ｉｉｉ１Ｒ -1) to (S ｉｉｉ１Ｒ -36) In the middle, the black dot is A ｉｉｉ１ or A ｉｉｉ２ represents a bond to the substituent S ｉｉｉ１ is preferably a linear alkyl group having 1 to 6 carbon atoms, a fluorine atom or a chlorine atom. ｉｉｉ１ At least one of or A ｉｉｉ２ is at least one substituent S ｉｉｉ１ It is preferable that the substituent S is substituted with a halogen atom, and it is preferable that the substituent S is substituted with a fluorine atom. ｉｉｉ１ When there are a plurality of, they may be the same or different.

[0142] A ｉｉｉ１ Substituent S inｉｉｉ１ The substitution position of the formula (A ｉｉｉ１ -SP-1) to (A ｉｉｉ１ -SP-24).

[0143]

[0144]

[0145]

[0146]

[0147] Formula (A ｉｉｉ１ -SP-1) to (A ｉｉｉ１ -SP-24) White points are R ｉｉｉ１ or Z ｉｉｉ１ The black dots represent bonds to Z. ｉｉｉ１ A represents a bond to ｉｉｉ２ Substituent S in ｉｉｉ１ The substitution position of the formula (A ｉｉｉ２ -SP-1) to (A ｉｉｉ２ -SP-8).

[0148]

[0149] Formula (A ｉｉｉ２ -SP-1) to (A ｉｉｉ２ -SP-8) White spots are Z ｉｉｉ１ The black dot represents a bond to the isothiocyanate group (-NCS). ｉｉｉ１ is expressed by the following formula (A ｉｉｉ１ -1) to (A ｉｉｉ１ -49).

[0150]

[0151]

[0152]

[0153]

[0154] Formula (A ｉｉｉ１ -1) to (A ｉｉｉ１ -49) In the middle, the white point is R ｉｉｉ１ or Zｉｉｉ１ The black dots represent bonds to Z. ｉｉｉ１ More specifically, A ｉｉｉ２ is expressed by the following formula (A ｉｉｉ2 -1) to (A ｉｉｉ2 -10) is preferably represented.

[0155]

[0156] Formula (A ｉｉｉ2 -1) to (A ｉｉｉ2 -10) In the middle, the white point is Z ｉｉｉ１ The black dot represents a bond to the isothiocyanate group (-NCS).

[0157] In general formula (iii), Z ｉｉｉ１ represents a single bond or an alkylene group having 1 to 20 carbon atoms. ２ - is independently -O-, -CF ２ In addition, the alkylene group may be substituted with one or more —CH ２ -CH ２ Each - is independently -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-, -C≡C-, -CO-O- and / or -O-CO-. However, when an alkylene group having 1 to 20 carbon atoms is substituted with a specific group, oxygen atoms are not directly bonded to each other. Furthermore, 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 each other. Specific examples of alkylene groups having 1 to 20 carbon atoms (including substituted ones) include alkylene groups of the formula (Z ｉｉｉ１ -1) to (Z ｉｉｉ１ -24).

[0158]

[0159] Expression (Z ｉｉｉ１ -1) to (Z ｉｉｉ１ -24) Medium, white point is A ｉｉｉ１ The black dot represents a bond to A. ｉｉｉ１ or A ｉｉｉ２ Represents a bond to .

[0160] In general formula (iii), n ｉｉｉ１ represents an integer of 1 to 4, preferably 1 or 2. ｉｉｉ１ When is 1, Δn and / or Δε ｒ From the perspective of Z ｉｉｉ１ Preferably, n represents a single bond or —C≡C—. ｉｉｉ１ When is 2, Δn and / or Δε ｒ From the perspective of Z ｉｉｉ１ It is preferable that A represents a single bond or —C≡C—. ｉｉｉ１ and Z ｉｉｉ１ When there are a plurality of groups, they may be the same or different.

[0161] The compound represented by general formula (iii) is preferably a compound represented by the following general formulas (iii-1) to (iii-4).

[0162] In general formulas (iii-1) to (iii-4), R ｉｉｉ１ , A ｉｉｉ１ and A ｉｉｉ２ represents R in the above general formula (iii). ｉｉｉ１ , A ｉｉｉ１ and A ｉｉｉ２ In general formula (iii-4), A ｉｉｉ１－２ The definitions of each independently represent A in the general formula (ii). ｉｉｉ１ The compound represented by general formula (iii-1) is preferably a compound represented by the following general formula (iii-1-1):

[0163]

[0164] In general formula (iii-1-1), R ｉｉｉ１ and S ｉｉｉ１are each independently R in the general formula (iii). ｉｉｉ１ and S ｉｉｉ１ Specific examples of the compound represented by general formula (iii-1-1) include compounds represented by the following structural formulas (iii-1-1.1) to (iii-1-1.3).

[0165]

[0166] The compound represented by general formula (iii-2) is preferably a compound represented by the following general formulas (iii-2-1) to (iii-2-3).

[0167]

[0168] In general formulas (iii-2-1) to (iii-2-3), R ｉｉｉ１ and S ｉｉｉ１ are each independently R in the general formula (iii). ｉｉｉ１ and S ｉｉｉ１ Specific examples of the compound represented by general formula (iii-2-1) include compounds represented by the following structural formulas (iii-2-1.1) to (iii-2-1.2).

[0169]

[0170] Specific examples of the compound represented by general formula (iii-2-2) include compounds represented by the following structural formulas (iii-2-2.1) to (iii-2-2.2).

[0171]

[0172] Specific examples of the compound represented by general formula (iii-2-3) include compounds represented by the following structural formulas (iii-2-3.1) to (iii-2-3.2).

[0173]

[0174] The compound represented by general formula (iii-3) is preferably a compound represented by the following general formulas (iii-3-1) to (iii-3-2).

[0175]

[0176] In general formulas (iii-3-1) to (iii-3-2), R ｉｉｉ１ and S ｉｉｉ１ are each independently R in the general formula (iii). ｉｉｉ１ and S ｉｉｉ１ Specific examples of the compound represented by general formula (iii-3-1) include compounds represented by the following structural formulas (iii-3-1.1) to (iii-3-1.2).

[0177]

[0178] Specific examples of the compound represented by general formula (iii-3-2) include compounds represented by the following structural formulas (iii-3-2.1) to (iii-3-2.2).

[0179]

[0180] The compound represented by general formula (iii-4) is preferably a compound represented by the following general formulas (iii-4-1) to (iii-4-3).

[0181]

[0182] In general formulas (iii-4-1) to (iii-4-3), R ｉｉｉ１ and S ｉｉｉ１ are each independently R in the general formula (iii). ｉｉｉ１ and S ｉｉｉ１ Specific examples of the compound represented by general formula (iii-4-1) include compounds represented by the following structural formulas (iii-4-1.1) to (iii-4-1.2).

[0183]

[0184] Specific examples of the compound represented by general formula (iii-4-2) include compounds represented by the following structural formulas (iii-4-2.1) to (iii-4-2.2).

[0185]

[0186] Specific examples of the compound represented by general formula (iii-4-3) include compounds represented by the following structural formulas (iii-4-3.1) to (iii-4-3.2).

[0187]

[0188] General formula (iii), general formula (iii-1) to (iii-4), general formula (iii-1-1), general formula (iii-2-1) to (iii-2-3), general formula (iii-3-1) to (iii-3-2), general formula (iii-4-1) to (iii- 4-3), Structural formula (iii-1-1.1) to (iii-1-1.3), Structural formula (iii-2-1.1) to (iii-2-1.2), Structural formula (iii-2-2.1) to (iii-2-2.2), Structural formula (iii-2-3.1) to (iii The compounds represented by structural formulas (iii-2-3.2), structural formulas (iii-3-1.1) to (iii-3-1.2), structural formulas (iii-3-2.1) to (iii-3-2.2), structural formulas (iii-4-1.1) to (iii-4-1.2), structural formulas (iii-4-2.1) to (iii-4-2.2), or structural formulas (iii-4-3.1) to (iii-4-3.2) are used in the liquid crystal composition in the form of one or more kinds, preferably 1 to 20 kinds, preferably 2 to 15 kinds, and preferably 3 to 10 kinds.

[0189] General formula (iii), general formula (iii-1) to (iii-4), general formula (iii-1-1), general formula (iii-2-1) to (iii-2-3), general formula (iii-3-1) to (iii-3-2), general formulas (iii-4-1) to (iii-4-3), structural formulas (iii-1-1.1) to (iii-1-1.3), structural formulas (iii-2-1.1) to (i ii-2-1.2), structural formula (iii-2-2.1) to (iii-2-2.2), structural formula (iii-2-3.1) to (iii-2-3.2), structural formula (iii-3-1.1) ) ~ (iii-3-1.2), structural formula (iii-3-2.1) ~ (iii-3-2.2), structural formula (iii-4-1.1) ~ (iii-4-1.2), structural formula (iii-4 The lower limit of the total content of the compounds represented by structural formulas (iii-4-2.1) to (iii-4-2.2) or structural formulas (iii-4-3.1) to (iii-4-3.2) in 100% by mass of the liquid crystal composition is preferably 1% by mass or more, preferably 1% by mass or more, preferably 3% by mass or more, preferably 10% by mass or more, preferably 15% by mass or more, preferably 20% by mass or more, preferably 25% by mass or more, preferably 30% by mass or more, preferably 35% by mass or more, preferably 40% by mass or more, preferably 45% by mass or more, preferably 50% by mass or more, and preferably 55% by mass or more.

[0190] General formula (iii), General formula (iii-1) to (iii-4), General formula (iii-1-1), General formula (iii-2-1) to (iii-2-3), General formula (iii-3-1) to (iii -3-2), general formula (iii-4-1) to (iii-4-3), structural formula (iii-1-1.1) to (iii-1-1.3), structural formula (iii-2-1.1) to (iii-2-1.2) , structural formula (iii-2-2.1) to (iii-2-2.2), structural formula (iii-2-3.1) to (iii-2-3.2), structural formula (iii-3-1.1) to (iii-3-1.2), structural formula (iii-3-2.1) to (iii-3-2.2), structural formula (iii-4-1.1) to (iii-4-1.2), structural formula (iii-4-2.1) to (iii-4-2.2) or The upper limit of the total content of the compounds represented by structural formulas (iii-4-3.1) to (iii-4-3.2) 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 60% by mass or less, preferably 55% by mass or less, preferably 50% by mass or less, preferably 45% by mass or less, preferably 40% by mass or less, preferably 35% by mass or less, preferably 30% by mass or less, preferably 25% by mass or less, preferably 20% by mass or less, preferably 15% by mass or less, preferably 10% by mass or less, and preferably 5% by mass or less.

[0191] General formula (iii), general formula (iii-1) to (iii-4), general formula (iii-1-1), general formula (iii-2-1) to (iii-2-3), general formula (iii-3-1) to (iii-3-2), general formula (iii-4-1) ) ~ (iii-4-3), structural formula (iii-1-1.1) ~ (iii-1-1.3), structural formula (iii-2-1.1) ~ (iii-2-1.2), structural formula (iii-2-2.1) ~ (iii-2-2.2), structural formula (iii The total content of the compounds represented by structural formulas (iii-2-3.1) to (iii-2-3.2), structural formulas (iii-3-1.1) to (iii-3-1.2), structural formulas (iii-3-2.1) to (iii-3-2.2), structural formulas (iii-4-1.1) to (iii-4-1.2), structural formulas (iii-4-2.1) to (iii-4-2.2), or structural formulas (iii-4-3.1) to (iii-4-3.2) in 100% by mass of the liquid crystal composition is ｒ From this viewpoint, the content is preferably 1 to 75% by mass, more preferably 3 to 70% by mass, and even more preferably 5 to 65% by mass.

[0192] The compound represented by general formula (iii) (including its sub-concepts) can be synthesized using known synthesis methods.

[0193] (Liquid Crystal Composition) The liquid crystal composition according to the present invention can be produced, for example, by mixing the compound represented by the above-mentioned general formula (i), the compound represented by the general formula (ii), and, if necessary, the above-mentioned other compounds and additives.

[0194] Examples of the additives include stabilizers, dye compounds, polymerizable compounds, azotolane compounds, and isothiocyanate compounds (NCS compounds).

[0195] Examples of stabilizers include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, hindered phenols, hindered amines, etc. Examples of hindered phenols include hindered phenol-based antioxidants represented by the following structural formulas (XX-1) to (XX-5).

[0196]

[0197] Examples of the hindered amines include hindered amine light stabilizers represented by the following structural formulas (YY-1) and (YY-2).

[0198]

[0199] When stabilizers are used, the number of types of stabilizers used in the liquid crystal composition is one or more, preferably 1 to 10, preferably 1 to 8, preferably 1 to 6, preferably 1 to 4, preferably 1 to 2. When stabilizers are used, the total content of the stabilizers in 100% by mass of the liquid crystal composition is preferably 0.005 to 1% by mass, preferably 0.02 to 0.50% by mass, and preferably 0.03 to 0.35% by mass.

[0200] The combination of compounds used in the liquid crystal composition may be determined by the solubility, Δn and / or T ｎｉ From the viewpoint of the above, the following are preferred: 1) a combination of a compound represented by general formula (i) (including subordinate concepts) and a compound represented by general formula (ii) (including subordinate concepts); 2) a combination of a compound represented by general formula (i) (including subordinate concepts), a compound represented by general formula (ii) (including subordinate concepts), and a compound represented by general formula (iii) (including subordinate concepts); 3) a combination of a compound represented by general formula (i-1) (including subordinate concepts), a compound represented by general formula (ii-2) (including subordinate concepts), and a compound represented by general formula (iii-1) (including subordinate concepts); 4) a combination of a compound represented by general formula (i-1-2) (including subordinate concepts), a compound represented by general formula (ii-2-2) (including subordinate concepts), and a compound represented by general formula (iii-1-1) (including subordinate concepts).

[0201] <Characteristic values ​​of liquid crystal composition> Liquid crystal phase upper limit temperature (T ｎｉ ) is the temperature at which the liquid crystal composition undergoes a phase transition from a nematic phase to an isotropic phase. ｎｉThe T is measured by preparing a preparation in which the liquid crystal composition is sandwiched between a slide glass and a cover glass, and observing it under a polarizing microscope while heating it on a hot stage. It can also be measured by differential scanning calorimetry (DSC). The unit is "°C". ｎｉ The higher the upper limit temperature (T ｎｉ ) can be appropriately set depending on whether the liquid crystal display element is used indoors, in a car, or the like where the external temperature can be controlled, or whether it is used outdoors, but from the viewpoint of the operating temperature range, it is preferably 120°C or higher, more preferably 120 to 250°C, and even more preferably 125 to 215°C.

[0202] Liquid crystal phase lower limit temperature (T →ｎ ) is the temperature at which the liquid crystal composition undergoes a phase transition from other phases (glass phase, smectic phase, crystalline phase) to the nematic phase. →ｎ is measured by filling a glass capillary with the liquid crystal composition, immersing it in a refrigerant at -70°C to cause the liquid crystal composition to undergo a phase transition to another phase, and observing the temperature as it is raised. It can also be measured by differential scanning calorimetry (DSC). The unit is "°C". T →ｎ The lower the temperature, the more the nematic phase can be maintained at a low temperature, and therefore the wider the operating temperature range can be. →ｎ ) is preferably 10°C or lower, more preferably -70 to 0°C, and even more preferably -40 to -5°C, from the viewpoint of the driving temperature.

[0203] Δn (refractive index anisotropy) correlates with Δn in the near-infrared region used in optical sensors, which will be described later. The larger Δn is, the greater the phase modulation power of light of the target wavelength, making it particularly suitable for optical sensors. Δn at 25°C and 589 nm was determined by measuring the extraordinary refractive index (n ｅ ) and ordinary refractive index (n ｏ ) difference (n ｅ -n ｏ) Δn can also be determined using a retardation measurement device. The relationship Δn = Re / d holds between retardation Re, liquid crystal layer thickness d, and Δn. A liquid crystal composition is injected into a glass cell with a polyimide alignment film that has been subjected to anti-parallel rubbing treatment and a cell gap (d) of approximately 3.0 μm, and the in-plane Re is measured using a retardation film / optical material inspection device RETS-100 (manufactured by Otsuka Electronics Co., Ltd.). Measurements are performed at a temperature of 25°C and a wavelength of 589 nm, and are unitless. From the viewpoint of the phase modulation power of light of the wavelength, the Δn of the liquid crystal composition according to the present invention at 25°C and 589 nm is preferably 0.40 or more, more preferably 0.40 to 0.65, more preferably 0.41 to 0.60, and even more preferably 0.43 to 0.55.

[0204] The higher the dielectric anisotropy in the high frequency region, the greater the phase modulation power for radio waves in the target frequency band, making it particularly suitable for antenna applications. Furthermore, in antenna applications, the smaller the dielectric loss tangent in the high frequency region, the smaller the energy loss in the target frequency band, making it suitable. In the liquid crystal composition according to the present invention, the dielectric anisotropy Δε at 10 GHz, which represents the characteristics in the high frequency region, is ｒ and the average value of the dielectric tangent tanδ ｉｓｏ was measured. ｒ =(ε ｒ∥ -ε ｒ⊥ ) and tan δ ｉｓｏ = (2ε ｒ⊥ tan δ ⊥ +ε ｒ∥ tan δ ∥ ) / (2ε ｒ⊥ +ε ｒ∥ ) where "ε ｒ " is the dielectric constant, "tan δ" is the dielectric loss tangent, the subscript "∥" indicates the component parallel to the alignment direction of the liquid crystal, and "⊥" indicates the component perpendicular to the alignment direction of the liquid crystal.

[0205] Δε ｒ and tan δ ｉｓｏcan be measured by the following method. First, a liquid crystal composition is introduced into a capillary tube made of polytetrafluoroethylene (PTFE). The capillary tube used here has an inner radius of 0.80 mm, an outer radius of 0.835 mm, and an effective length of 4.0 cm. The capillary tube containing the liquid crystal composition is introduced into the center of a cavity resonator (manufactured by EM Lab Co., Ltd.) with a resonance frequency of 10 GHz. This cavity resonator has an outer diameter of 30 mm and a width of 26 mm. A signal is then input, and the output signal is recorded using a network analyzer (manufactured by Keysight Technologies, Inc.). The dielectric constant (ε) at 10 GHz is calculated using the difference between the resonance frequency of a PTFE capillary tube without the liquid crystal composition and the resonance frequency of a PTFE capillary tube containing the liquid crystal composition. ｒ ) and loss angle (δ) are determined. The tangent of the obtained δ is the dielectric loss tangent (tan δ). The resonance frequency and other measurements using a PTFE capillary filled with a liquid crystal composition are determined by controlling the orientation of the liquid crystal molecules, as the values ​​of characteristic components perpendicular and parallel to the orientation direction of the liquid crystal molecules. A magnetic field from a permanent magnet or electromagnet is used to align the liquid crystal molecules in the perpendicular direction (perpendicular to the effective length direction) or parallel direction (parallel to the effective length direction) of the PTFE capillary. The magnetic field has, for example, a pole-to-pole distance of 45 mm and a magnetic field strength of 0.23 Tesla near the center. The desired characteristic components are obtained by rotating the PTFE capillary filled with the liquid crystal composition parallel or perpendicular to the magnetic field. The electric field application time can be set to any condition that results in uniform alignment of the liquid crystal, but in this invention, the electric field application time was set to 8 minutes. Measurements were performed at a temperature of 25°C, and Δε ｒ and tan δ ｉｓｏ Neither has a unit.

[0206] Δε at 25° C. of the liquid crystal composition according to the present invention ｒ is preferably larger, but from the viewpoint of phase modulation power in the GHz band, it is preferably 0.90 or more, more preferably 0.90 to 1.65, more preferably 0.95 to 1.60, and even more preferably 1.00 to 1.55. ｉｓｏis preferably smaller, but 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.

[0207] (Liquid Crystal Display Element, Sensor, Liquid Crystal Lens, Optical Communication Device, and Antenna) Hereinafter, a liquid crystal display element, a sensor, a liquid crystal lens, an optical communication device, and an antenna using the liquid crystal composition according to the present invention will be described.

[0208] The liquid crystal display element of the present invention is characterized by using the above-mentioned liquid crystal composition, and is preferably driven by an active matrix system or a passive matrix system. The liquid crystal display element of 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-mentioned liquid crystal composition.

[0209] The sensor according to the present invention is characterized by using the liquid crystal composition described above. Examples of the sensor include a distance measuring 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 wavelength of reflected light due to a change in the pitch of a cholesteric liquid crystal, a pressure sensor that uses a change in the wavelength of reflected light, an ultraviolet sensor that uses a change in the wavelength of reflected light due to a change in composition, an electrical sensor that uses a temperature change due to voltage or current, a radiation sensor that uses a temperature change associated with the track of a radiation particle, an ultrasonic sensor that uses a change in the alignment of liquid crystal molecules due to mechanical vibration of ultrasound, and an electromagnetic field sensor that uses a change in the wavelength of reflected light due to a change in the alignment of liquid crystal molecules due to a temperature change or an electric field. The distance measuring sensor is preferably for LiDAR (Light Detection and Ranging) that uses a light source. LiDAR is preferably for use in artificial satellites, aircraft, unmanned aerial vehicles (drones), automobiles, railways, and ships. For automobiles, self-driving automobiles are particularly preferred. The light source is preferably an LED or a laser, and more preferably a laser. The light used in LiDAR is preferably infrared light, and preferably has a wavelength of 800 to 2000 nm. In particular, an infrared laser with a wavelength of 905 nm or 1550 nm is preferred. When the cost of the photodetector used and sensitivity in all weather conditions are important, a 905 nm infrared laser is preferred, and when safety regarding human vision is important, a 1550 nm infrared laser is preferred. The liquid crystal composition according to the present invention exhibits a high Δn, and therefore a sensor with large phase modulation power in the visible light, infrared light, and electromagnetic wave regions and excellent detection sensitivity can be provided.

[0210] The liquid crystal lens according to the present invention is characterized by using the liquid crystal composition described above, and, for example, in one embodiment, has a first transparent electrode layer, a second transparent electrode layer, a liquid crystal layer containing the liquid crystal composition described above and 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 adjusting the focus of a camera, etc.

[0211] The optical communication device according to the present invention is characterized by using the above-mentioned liquid crystal composition, and one example of the optical communication device is a liquid crystal on silicon (LCOS) structure having a liquid crystal layer on a reflective layer (electrode) in which liquid crystals constituting each of a plurality of pixels are arranged two-dimensionally. The optical communication device according to the present invention is used, for example, as a spatial phase modulator.

[0212] 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 comprises a first substrate having a plurality of slots, a second substrate facing the first substrate and having a power supply section, 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 above-described liquid crystal composition. By using the liquid crystal composition according to the present invention, an antenna having high reliability against external stimuli such as heat can be provided. Furthermore, an antenna enabling greater phase control for microwave or millimeter wave electromagnetic waves can be provided. The antenna according to the present invention preferably operates in the Ka band frequency, K band frequency, or Ku band frequency used for satellite communications. The antenna according to the present invention is preferably configured to combine a radial line slot array and a patch antenna array. The structure of the antenna according to the present invention can be applied by taking into consideration, for example, the matters described in International Publication No. 2021 / 157189 and the like.

[0213] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples in any way. The compositions of the following examples and comparative examples contain each compound at the ratio shown in the table, and the content is expressed in "mass %". The compounds are represented by the following abbreviations. Note that compounds that can take cis and trans forms represent the trans form unless otherwise specified. <Ring structure>

[0214]

[0215] <Terminal structure>

[0216] (Note that n in the table is a natural number. The alkyl group represented by n is a linear alkyl group.)

[0217] <Connection structure>

[0218] (Note that n in the table is a natural number. The alkylene group represented by n is a linear alkylene group.)

[0219] (hindered phenol antioxidant)

[0220]

[0221] (Hindered amine light stabilizer)

[0222]

[0223] (Preparation of Liquid Crystal Compositions) LC-A to B and LC-01 to 07 shown in Table 3 were prepared.

[0224]

[0225] (Examples 1 to 31 and Comparative Examples 1 and 2) Liquid crystal compositions were prepared using LC-A to B and LC-01 to 07, hindered phenol-based antioxidants (XX-1) to (XX-3), and hindered amine-based light stabilizers (YY-1) to (YY-2), and the physical properties of the compositions were measured and a storage stability test was carried out. The results are shown in Tables 4 to 8. Note that in Comparative Example 1, crystallization occurred at room temperature, and therefore the high frequency characteristics (Δε ｒ and tan δ ｉｓｏ ) was not measured. <Storage Test> 0.5 g of the liquid crystal composition was weighed into a 1 mL sample bottle (manufactured by Maruemu Co., Ltd.), and degassing was carried out by deaerating at 150 to 250 Pa for 10 minutes. After that, the bottle was purged with dry nitrogen, and the attached lid was put on. This was stored in a temperature-controlled thermostatic chamber (SH-241, manufactured by Espec Corp.) at 25°C for 2 weeks, and the occurrence of crystallization of the liquid crystal composition was visually confirmed every week.

[0226]

[0227]

[0228]

[0229]

[0230]

[0231] From Example 1, it can be seen that the liquid crystal composition containing one or more compounds represented by the general formula (i) and one or more compounds represented by the general formula (ii) has T ｎｉ is high, Δn is large, and Δε ｒ is large, and tan δ ｉｓｏ On the other hand, it was confirmed from Comparative Examples 1 and 2 that the liquid crystal composition not containing one or more compounds represented by the general formula (i) and one or more compounds represented by the general formula (ii) did not have good storage stability or T ｎｉ The results were low, less than 120°C. In Comparative Example 1, it was confirmed that LC-A crystallized one week after preparation. Furthermore, from Examples 2 to 31, it was confirmed that the same effect was obtained when various compounds were used or when a hindered phenol-based antioxidant or a hindered amine-based light stabilizer was used in combination.

[0232] The liquid crystal composition of the present invention can be used in liquid crystal display devices, sensors, liquid crystal lenses, optical communication devices and antennas.

Claims

1. A compound represented by the following general formula (i): (In general formula (i), R ｉ１ represents an alkenyl group having 2 to 20 carbon atoms, ２ - may be independently replaced by -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH ２ -CH ２ each - may be independently replaced by -CH=CH- and / or -CF=CF-, one or more hydrogen atoms in the alkenyl group may be independently replaced by a halogen atom, but the oxygen atoms are not directly bonded to each other, ｉ１ , A ｉ２ and A ｉ３ each independently represents a hydrocarbon ring having 3 to 16 carbon atoms or a heterocycle having 3 to 16 carbon atoms; ｉ１ , A ｉ２ and A ｉ３ One or more hydrogen atoms in each independently represent a substituent S ｉ１ and the 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, ２ - may be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH ２ -CH ２ Each of the - may be independently substituted with -CH=CH-, -CF=CF- and / or -C≡C-, one or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, but the oxygen atoms are not directly bonded to each other, and the substituent S ｉ１ When there are a plurality of Z, they may be the same or different; ｉ１ and Z ｉ２ each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms, ２ Each - is independently -O- or -CF ２ - and / or -CO- may be substituted, and one or more -CH ２ -CH ２ Each - is independently -CH ２ -CH(CH ３ ) -, -CH(CH ３ )-CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ ) -, -C(CH ３ ) may be substituted by =CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, but the oxygen atoms are not directly bonded to each other, ｉ１ represents an integer of 0 to 1.) and one or more compounds represented by the following general formula (ii): (In general formula (ii), R ｉｉ１ represents an alkynyl group having 2 to 20 carbon atoms, ２ - may be independently replaced by -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH ２ -CH ２ Each of - may be independently replaced by -C≡C-, one or more hydrogen atoms in the alkynyl group may be independently replaced by a halogen atom, but the oxygen atoms are not directly bonded to each other, ｉｉ１ , A ｉｉ２ and A ｉｉ３ each independently represents a hydrocarbon ring having 3 to 16 carbon atoms or a heterocycle having 3 to 16 carbon atoms; ｉｉ１ , A ｉｉ２ and A ｉｉ３ One or more hydrogen atoms in each independently represent a substituent S ｉｉ１ and the substituent S ｉｉ１ 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, ２ - may be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH ２ -CH ２ Each of the - may be independently substituted with -CH=CH-, -CF=CF- and / or -C≡C-, one or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, but the oxygen atoms are not directly bonded to each other, and the substituent S ｉｉ１ When there are a plurality of Z, they may be the same or different; ｉｉ１ and Z ｉｉ２ each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms, ２ Each - is independently -O- or -CF ２ - and / or -CO- may be substituted, and one or more -CH ２ -CH ２ Each - is independently -CH ２ -CH(CH ３ ) -, -CH(CH ３ )-CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ ) -, -C(CH ３ ) may be substituted by =CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, but the oxygen atoms are not directly bonded to each other, ｉｉ１ represents an integer of 0 to 2; ｉｉ３ and Z ｉｉ２ When a plurality of formulas are present, they may be the same or different.

2. The liquid crystal composition according to claim 1, wherein the total content of the compounds represented by the general formula (i) in 100% by mass of the liquid crystal composition is 1 to 40% by mass, and / or the total content of the compounds represented by the general formula (ii) in 100% by mass of the liquid crystal composition is 1 to 55% by mass.

3. The compound represented by the general formula (i) is represented by the following general formulas (i-1) to (i-2): (In general formulas (i-1) to (i-2), R ｉ１ , A ｉ１ , A ｉ２ and A ｉ３ is R in the above general formula (i). ｉ１ , A ｉ１ , A ｉ２ and A ｉ３ 3. The liquid crystal composition according to claim 1, wherein the compound is selected from the group consisting of compounds represented by the formula:

4. The compound represented by the general formula (ii) is represented by the following general formulas (ii-1) to (ii-3): (In general formulas (ii-1) to (ii-3), R ｉｉ１ , A ｉｉ１ , A ｉｉ２ and A ｉｉ３ is R in the above general formula (ii). ｉｉ１ , A ｉｉ１ , A ｉｉ２ and A ｉｉ３ In general formula (ii-3), A ｉｉ３－２ The definition of A in the above general formula (ii) ｉｉ３－２ The liquid crystal composition according to claim 1 or 2, wherein the compound is selected from the group consisting of compounds represented by the formula:

5. Furthermore, the following general formula (iii) (In general formula (iii), R ｉｉｉ１ each independently represents an alkyl group having 1 to 20 carbon atoms, ２ each - may be independently substituted with -O-, -S-, -NH-, -CO- and / or -CS-; one or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom, but the oxygen atoms are not directly bonded to each other; ｉｉｉ１ and A ｉｉｉ２ each independently represents the following group (a), group (b), group (c) and group (d): (a) a 1,4-cyclohexylene group (one —CH ２ - or two or more non-adjacent -CH ２ - may be replaced by -O- and / or -S-.) (b) 1,4-phenylene group (one -CH= or two or more -CH= in this group 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, phenanthrene-2,7-diyl group, 2,3-dihydro-1H-indene-1,5-diyl group, 2,3-dihydro-1H-indene-2,5-diyl group, 2,3-dihydro-1H-indene-1,6-diyl group, 1 H-indene-2,5-diyl group, 1H-indene-1,5-diyl group, 1H-indene-3,5-diyl group, 1H-indene-1,6-diyl group, 1H-indene-2,6-diyl group, 1H-indene-3,6-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 group selected from the group consisting of 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, a thieno[3,2-b]thiophene-2,5-diyl group, and a benzo[1,2-b:4,5-b']dithiophene-2,6-diyl group (one -CH= or two or more -CH= present in this group may be replaced by -N=), ｉｉｉ１ and A ｉｉｉ２ One or more hydrogen atoms in each independently represent a substituent S ｉｉｉ１ and the substituent S ｉｉｉ１ 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, ２ - may be independently replaced by -O-, -S-, -NH-, -CO- and / or -CS-, and one or more -CH ２ -CH ２ each - may be independently substituted by -CH=CH-, -CF=CF- and / or -C≡C-, one or more hydrogen atoms in the alkyl group may be independently substituted by a halogen atom, but the oxygen atoms are not directly bonded to each other, and the substituent S ｉｉｉ１ When there are a plurality of Z, they may be the same or different; ｉｉｉ１ represents a single bond or an alkylene group having 1 to 20 carbon atoms, and one or more -CH ２ Each - is independently -O- or -CF ２ - and / or -CO- may be substituted, and one or more -CH ２ -CH ２ Each - is independently -CH ２ -CH(CH ３ ) -, -CH(CH ３ )-CH ２ -, -CH=CH-, -CF=CF-, -CH=C(CH ３ ) -, -C(CH ３ ) may be substituted by =CH-, -CH=N-, -N=CH-, -N=N-, -C≡C-, -CO-O- and / or -O-CO-, an oxygen atom is not directly bonded to an oxygen atom, ｉｉｉ１ represents an integer of 1 to 4; ｉｉｉ１ and Z ｉｉｉ１ The liquid crystal composition according to claim 1 , comprising one or more compounds represented by the following formula:

6. Upper limit temperature of liquid crystal phase (T ｎｉ 3. The liquid crystal composition according to claim 1, wherein the liquid crystal composition has a temperature of 120° C. or higher.

7. A liquid crystal display device using the liquid crystal composition according to any one of claims 1 to 6.

8. The liquid crystal display element according to claim 7, which is driven by an active matrix method or a passive matrix method.

9. A liquid crystal display device in which the dielectric constant is reversibly switched by reversibly changing the alignment direction of the liquid crystal molecules of the liquid crystal composition according to any one of claims 1 to 6.

10. A sensor using the liquid crystal composition according to any one of claims 1 to 6.

11. A liquid crystal lens using the liquid crystal composition according to any one of claims 1 to 6.

12. An optical communication device using the liquid crystal composition according to any one of claims 1 to 6.

13. An antenna using the liquid crystal composition according to any one of claims 1 to 6.

14. An antenna as described in claim 13, comprising: a first substrate having a plurality of slots; a second substrate facing the first substrate and provided with a power supply section; 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 as described in any one of claims 1 to 6.

Images