Liquid crystal composition and element

Abstract

To provide a liquid crystal composition with superior balance of characteristics, which fulfills at least one of a wide nematic phase temperature range, large refractive index anisotropy in the frequency region employed for control, and small dielectric loss tangent (tanδ), as a material for an element used to control electromagnetic wave signals in the frequency range of 1 GHz to 10 THz, and to provide an element including the composition.SOLUTION: A liquid crystal composition comprising at least one compound selected from compounds represented by formula (1) and three specific N=C=S group-containing compounds, and not comprising a specific compound, wherein in formula (1), R1 is hydrogen, halogen, or a linear alkyl group having 1 to 12 carbon atoms, L11, L12, and L13 are hydrogen, halogen, an alkyl group having 1 to 3 carbon atoms, or a cycloalkyl group having 3 to 5 carbon atoms, Y11 is hydrogen or halogen, provided that at least one of L11, L12, and L13 is an alkyl group having 1 to 3 carbon atoms.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a liquid crystal composition having a nematic phase and positive dielectric anisotropy and a device containing the same, particularly to a liquid crystal composition used for controlling electromagnetic waves in the frequency range of 1 GHz to 10 THz and a device containing the same. [Background technology]

[0002] Liquid crystal compositions are widely used in displays, but as a new application, attention is being paid to their application to high frequency technology, such as antennas that transmit and receive electromagnetic waves using liquid crystal compositions.

[0003] Specifically, elements used to control electromagnetic waves in the frequency range of 1 GHz to 10 THz include millimeter-wave or microwave antenna arrays, electromagnetic wave reflectors, etc. Various types of elements are being considered, but a method using a liquid crystal composition, which is thought to be less prone to failure because it has no mechanical moving parts, has attracted attention.

[0004] High-frequency bands have not been used much in communications technology until now, but with demands for ultra-high speeds, large capacity, low latency, and multiple simultaneous connections, the millimeter wave band (24 GHz to 100 GHz) is expected to be used in particular. Frequency band allocations have begun worldwide for this use. Millimeter wave frequencies used for communications are allocated in the 24 to 29.5 GHz range in approximately 20 countries, and in the United States, the range has expanded to 37 to 40 GHz and 47.2 to 48.2 GHz. It is possible that higher frequencies will be allocated in many countries in the future. In Japan, the 27 to 29.5 GHz range is allocated to mobile phone operators for commercial use. Thus, millimeter wave use, centered on the frequency band around 28 GHz, is increasing in various countries.

[0005] A liquid crystal composition having dielectric anisotropy has different dielectric constants in the directions perpendicular to and horizontal to the orientation direction of the liquid crystal composition at frequencies (several tens of kHz to several hundred MHz or less) lower than the frequency at which orientation polarization relaxes (relaxation frequency). Even at frequencies higher than the relaxation frequency, that is, in the range from microwaves to terahertz waves (approximately 10 THz), although the value becomes smaller, a difference in dielectric constant between the perpendicular and horizontal directions relative to the alignment direction of the liquid crystal composition is observed, indicating dielectric anisotropy (Non-Patent Document 1). Therefore, the liquid crystal composition can change its dielectric constant in one direction by changing the alignment direction of the molecules in response to an external field (electric field).

[0006] By utilizing this property, the molecular orientation of the liquid crystal composition can be changed in response to an external electric field, thereby changing the dielectric constant. For example, this could lead to the realization of microwave devices that can electrically control the transmission characteristics of high-frequency transmission lines from the outside. Examples of such devices that have been reported include a voltage-controlled millimeter-wave band variable phase shifter in which a waveguide is filled with a nematic liquid crystal composition, and a wideband variable phase shifter in the microwave and millimeter-wave bands that uses a nematic liquid crystal composition as the dielectric substrate of a microstrip line (Patent Documents 1 and 2).

[0007] Recently, research has progressed on metamaterial technology, which exhibits behaviors not found in natural materials when it comes to electromagnetic waves, including light. These properties have led to applications in technical fields such as high-frequency devices, microwave devices, and antennas, and various electromagnetic wave control elements have been devised. Liquid crystal compositions, whose molecular orientation changes in response to an external electric field, allowing for the change of dielectric constant, are also being considered as capacitance control materials for transmission lines using metamaterials.

[0008] It is desirable for elements used for such electromagnetic wave control to have characteristics such as high gain and low loss. When considering the phase control of high-frequency signals, the characteristics required for a liquid crystal composition are a large dielectric anisotropy that enables large phase control in the frequency range used for phase control, and a small dielectric loss tangent (tan δ) that is proportional to the absorption energy of the electromagnetic wave signal by the liquid crystal composition (Non-Patent Document 1).

[0009] Since liquid crystal compositions are dielectrics, they undergo polarization (dielectric polarization) in response to an external field (electric field). The dielectric constant is a physical quantity that indicates the response of a dielectric to an electric field, and the magnitude of the dielectric constant is related to the dielectric polarization. The mechanisms by which dielectric polarization occurs can be broadly divided into three: electronic polarization, ionic polarization, and orientation polarization. Orientation polarization is polarization associated with the orientation of the dipole moment, and as shown above, it relaxes at frequencies from several hundred kHz to several hundred MHz, and the orientation polarization becomes smaller. As a result, at high frequencies (in the range from microwaves to terahertz waves (approximately 10 THz)), only electronic polarization and ionic polarization are involved in dielectric polarization. In lossless dielectrics, the dielectric constant and refractive index are related by the equation ε=n 2 If the ionic polarization of a liquid crystal composition is considered to be small, it is believed that the larger the refractive index anisotropy (Δn) in visible light due to electronic polarization, the larger the dielectric anisotropy (Δε) in the high frequency range (Non-Patent Document 2). Therefore, it is preferable for a liquid crystal composition to have a large refractive index anisotropy.

[0010] Furthermore, a low driving voltage is desirable to realize switching characteristics and high energy efficiency of the device, and therefore it is preferable for the liquid crystal composition to have a large dielectric anisotropy even at low frequencies (frequencies lower than the relaxation frequency).

[0011] In addition, elements used for electromagnetic wave control are required to have a wide usable temperature range and a short response time, and liquid crystal compositions are required to have properties such as a high upper limit temperature of the nematic phase, a low lower limit temperature of the nematic phase, thermal stability, and low viscosity.

[0012] Conventional liquid crystal compositions used in such devices are disclosed in Patent Documents 3 and 4. [Prior art documents] [Patent documents]

[0013] [Patent Document 1] International Publication No. 2017 / 201515 [Patent Document 2] International Publication No. 2017 / 208996 [Patent Document 3] Japanese Patent Application Laid-Open No. 2004-285085 [Patent Document 4] Japanese Patent Application Laid-Open No. 2011-74074 [Non-patent literature]

[0014] [Non-Patent Document 1] EKISHO, Vol. 23(No. 1), (2019), pp. 51-55 [Non-patent document 2] Dielectric Phenomena, Institute of Electrical Engineers of Japan, Ohmsha Co., Ltd., July 25, 1973, pp. 92-95 Summary of the Invention [Problem to be solved by the invention]

[0015] As a material for elements used for electromagnetic wave control, liquid crystal compositions are required to have a high upper limit temperature of the nematic phase and a low lower limit temperature of the nematic phase, as well as a large dielectric anisotropy (large refractive index anisotropy) in the frequency range where electromagnetic wave control is performed, a small dielectric dissipation factor (tanδ), and a large dielectric anisotropy at low frequencies for reducing the driving voltage, and more preferably, a small viscosity, a large resistivity in the driving frequency range, and thermal stability.

[0016] However, liquid crystal compositions used in conventional displays and the like are insufficient in terms of properties for use in such elements for controlling electromagnetic waves, because they have insufficient properties for use in high frequency control, such as high insertion loss and / or insufficient phase shift.

[0017] The development of liquid crystal materials for devices used in electromagnetic wave control is still in progress, and attempts are constantly being made to develop new compounds that allow the optimization of such devices in order to improve the properties of high frequency control. Specific liquid crystal media are needed for use as materials for devices used in electromagnetic wave control.

[0018] The object of the present invention is to provide a liquid crystal composition that satisfies the required characteristics described above and has an excellent balance of characteristics as a material for use in elements for controlling electromagnetic waves in the frequency range of 1 GHz to 10 THz, and an element containing this composition. [Means for solving the problem]

[0019] As a result of intensive research, the inventors have found that the above-mentioned problems can be solved by a liquid crystal composition containing at least one compound selected from compounds represented by formula (1), at least one compound selected from compounds represented by formula (2), at least one compound selected from compounds represented by formula (3), and at least one compound selected from compounds represented by formula (4), but not containing a compound represented by formula (S), and have completed the present invention.

[0020] The present invention includes the following items.

[0021] Item 1. A liquid crystal composition containing at least one compound selected from compounds represented by formula (1), at least one compound selected from compounds represented by formula (2), at least one compound selected from compounds represented by formula (3), and at least one compound selected from compounds represented by formula (4), and not containing a compound represented by formula (S). TIFF2025133005000001.tif25147 TIFF2025133005000002.tif25148 TIFF2025133005000003.tif25148 TIFF2025133005000004.tif25147 In equations (1) to (4), R 1 , R 2 , R 3 and R 4 is hydrogen, halogen, or a linear alkyl having 1 to 12 carbon atoms, in which at least one -CH2- may be replaced by -O- or -S-, and at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and in these groups at least one hydrogen may be replaced by halogen; L 11 , L 12 , L 13 , L 21 , L 22 , L 23 , L 31 , L 32 , L 33 , L 41 , L 42 , L 43 , L 44 and L 45 is hydrogen, halogen, alkyl having 1 to 3 carbon atoms, or cycloalkyl having 3 to 5 carbon atoms; Y 11 , Y 21 , Y 22 , Y 23 , Y 31 , Y 32 , Y 33 , Y 34 , Y 35 , Y 36 and Y 41 is hydrogen or halogen; However, L 11 , L 12 and L 13 At least one of the groups is alkyl having 1 to 3 carbon atoms, and L 31 , L 32 and L 33 At least one of these is alkyl having 1 to 3 carbon atoms. TIFF2025133005000005.tif26148 In formula (S), R S1is hydrogen, halogen, or alkyl having 1 to 12 carbon atoms, in which at least one -CH2- may be replaced by -O- or -S-, and at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and in these groups at least one hydrogen may be replaced by halogen; L S1 , L S2 and L S3 is hydrogen or fluorine; Y S1 is hydrogen or fluorine.

[0022] Item 2. The liquid crystal composition according to item 1, which does not contain a compound represented by formula (T). TIFF2025133005000006.tif22148 In formula (T), R T1 is hydrogen, halogen, or alkyl having 1 to 12 carbon atoms, in which at least one -CH2- may be replaced by -O- or -S-, and at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and in these groups at least one hydrogen may be replaced by halogen; Y T1 and Y T2 is hydrogen or fluorine; t is 0 or 1.

[0023] Item 3. The liquid crystal composition according to item 1 or 2, containing, as the compound represented by formula (1), at least one compound selected from the group of compounds represented by formulas (1-1) to (1-10): TIFF2025133005000007.tif213113 In formulas (1-1) to (1-10), R 1’ is a linear alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-.

[0024] Item 4. The liquid crystal composition according to any one of items 1 to 3, containing, as the compound represented by formula (2), at least one compound selected from the group of compounds represented by formulas (2-1) to (2-10): TIFF2025133005000008.tif208109 In equations (2-1) to (2-10), R 2’ is a linear alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-; Y 22’ is hydrogen, fluorine or chlorine; In equation (2-10), Y 21’ is hydrogen, fluorine or chlorine.

[0025] Item 5. The liquid crystal composition according to any one of items 1 to 4, containing at least one compound selected from the group of compounds represented by formula (3-1) to formula (3-11) as the compound represented by formula (3). TIFF2025133005000009.tif228113 TIFF2025133005000010.tif22112 In equations (3-1) to (3-11), R 3’ is a linear alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-; Y 35’ is hydrogen, fluorine or chlorine.

[0026] Item 6. The liquid crystal composition according to any one of items 1 to 5, containing, as the compound represented by formula (4), at least one compound selected from the group of compounds represented by formulas (4-1) to (4-7): TIFF2025133005000011.tif161106 In equations (4-1) to (4-7), R 4’ is a linear alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-; L 44’ and L 45’ is hydrogen, fluorine, chlorine, methyl or ethyl; Y 41’ is hydrogen, fluorine or chlorine.

[0027] Item 7. The liquid crystal composition according to any one of items 1 to 6, wherein, based on the weight of the liquid crystal composition, the proportion of the compound represented by formula (1) is in the range of 15% by weight to 65% by weight, the proportion of the compound represented by formula (2) is in the range of 5% by weight to 40% by weight, the proportion of the compound represented by formula (3) is in the range of 10% by weight to 55% by weight, and the proportion of the compound represented by formula (4) is in the range of 5% by weight to 20% by weight.

[0028] Item 8. The liquid crystal composition according to any one of items 1 to 7, further comprising at least one compound selected from the group consisting of a compound represented by formula (5), a compound represented by formula (6), and a compound represented by formula (7). TIFF2025133005000012.tif25147 TIFF2025133005000013.tif30147 TIFF2025133005000014.tif27148 In equations (5) to (7), R 5 , R 6 , R 71 and R 72is hydrogen, halogen, or alkyl having 1 to 12 carbon atoms, in which at least one -CH2- may be replaced by -O- or -S-, and at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and in these groups at least one hydrogen may be replaced by halogen; L 51 , L 52 , L 53 , L 61 , L 62 , L 63 , L 64 , L 71 , L 72 , L 73 , L 74 , L 75 , L 76 and L 77 is hydrogen, halogen, alkyl having 1 to 3 carbon atoms, or cycloalkyl having 3 to 5 carbon atoms; Y 51 , Y 52 and Y 61 is hydrogen or halogen; Ring A is 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, or pyridine-2,5-diyl, and at least one hydrogen on these rings may be replaced by halogen or alkyl having 1 to 3 carbon atoms; Z 61 and Z 62 is a single bond, -C≡C- or -C≡CC≡C-; a is 0, 1 or 2; b is 1, 2 or 3; a+b is 3; c and d are 0 or 1; and e is 0, 1 or 2.

[0029] Item 9. The liquid crystal composition according to item 8, containing, as the compound represented by formula (5), at least one compound selected from the group of compounds represented by formulas (5-1) to (5-10): TIFF2025133005000015.tif222113 In equations (5-1) to (5-10), R 5’ is alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-; Y 51’ is hydrogen, fluorine or chlorine.

[0030] Item 10. The liquid crystal composition according to item 8 or 9, containing, as the compound represented by formula (6), at least one compound selected from the group of compounds represented by formulas (6-1) to (6-8): TIFF2025133005000016.tif210126 In equations (6-1) to (6-8), R 6’ is alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-; L 61’ , L 62’ , L 63’ and L 64’ is hydrogen, fluorine, chlorine, methyl or ethyl; Y 61’ is hydrogen, fluorine or chlorine.

[0031] Item 11. The liquid crystal composition according to any one of items 8 to 10, containing, as the compound represented by formula (7), at least one compound selected from the group of compounds represented by formulas (7-1) to (7-6): TIFF2025133005000017.tif148111In equations (7-1) to (7-6), R 71’ and R 72’ is alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-; In formula (7-1) and formula (7-2), L 75’ , L 76’ and L 77’ is hydrogen, fluorine, chlorine, methyl or ethyl: In equation (7-3), L 72’ , L 74’ , L 75’ , L 76’ and L 77’ is hydrogen, fluorine, chlorine, methyl or ethyl; In equation (7-4), L 71’ , L 73’ , L 75’ , L 76’ and L 77’ is hydrogen, fluorine, chlorine, methyl or ethyl; In equations (7-5) and (7-6), L 71’ ,L 72’ , L 73’ , L 74’ , L 75’ , L 76’ and L 77’ is hydrogen, fluorine, chlorine, methyl or ethyl.

[0032] Item 12. The liquid crystal composition according to any one of items 8 to 11, wherein, based on the weight of the liquid crystal composition, the proportion of the compound represented by formula (5) is in the range of 0% by weight to 30% by weight, the proportion of the compound represented by formula (6) is in the range of 0% by weight to 25% by weight, the proportion of the compound represented by formula (7) is in the range of 0% by weight to 50% by weight, and the total proportion of these compounds is in the range of 5% by weight to 50% by weight.

[0033] Item 13. The liquid crystal composition according to any one of items 1 to 12, wherein the refractive index anisotropy at 25° C. at a wavelength of 589 nm is 0.40 or more.

[0034] Item 14. The liquid crystal composition according to any one of items 1 to 13, wherein the dielectric anisotropy at 25° C. in a frequency range of 1 kHz is 10 or more.

[0035] Item 15. The liquid crystal composition according to any one of items 1 to 14, wherein the dielectric anisotropy at 25° C. in at least one frequency range of 1 GHz to 10 THz is in the range of 1.0 to 3.0.

[0036] Item 16. The liquid crystal composition according to any one of items 1 to 15, which contains an optically active compound.

[0037] Item 17. The liquid crystal composition according to any one of items 1 to 16, which contains a polymerizable compound.

[0038] Item 18. The liquid crystal composition according to any one of items 1 to 17, further comprising at least one of an antioxidant, an ultraviolet absorber, an antistatic agent, and a dichroic dye.

[0039] Item 19. A device containing the liquid crystal composition according to any one of items 1 to 18, which is used for switching and can reversibly control the dielectric constant by reversibly changing the alignment direction of liquid crystal molecules.

[0040] Item 20. A device used for controlling electromagnetic waves in the frequency range of 1 GHz to 10 THz, comprising the liquid crystal composition according to any one of items 1 to 18.

[0041] Item 21. A liquid crystal lens, a birefringent lens for stereoscopic image display, or a light modulation element, comprising the liquid crystal composition according to any one of items 1 to 18. [Effects of the Invention]

[0042] According to the present invention, it is possible to provide a liquid crystal composition having a high maximum temperature of the nematic phase and a low minimum temperature of the nematic phase, while also achieving high-frequency characteristics such as a large dielectric anisotropy and a small dielectric dissipation factor (tanδ) in the frequency range required for electromagnetic wave control, and a high voltage holding ratio for TFT operation. Furthermore, it is possible to provide a more preferable liquid crystal composition by further satisfying at least one of the composition characteristics, such as a large dielectric anisotropy at low frequencies for reducing the driving voltage, a small viscosity for shortening the response time, a large resistivity in the driving frequency range, and thermal stability. A device using the liquid crystal composition of the present invention exhibits excellent characteristics, such as electromagnetic wave control over a wide temperature range. DETAILED DESCRIPTION OF THE INVENTION

[0043] The terms used in this specification are as follows. The terms "liquid crystal composition" and "electromagnetic wave control element" may be abbreviated as "composition" and "element," respectively. "Electromagnetic wave control element" is a general term for electromagnetic wave control panels and electromagnetic wave control modules. "Liquid crystal compound" is a general term for compounds that have a liquid crystal phase, such as a nematic phase or a smectic phase, and compounds that do not have a liquid crystal phase but are mixed into a composition to adjust properties such as the temperature range, viscosity, and dielectric anisotropy of the liquid crystal phase. These compounds have a six-membered ring, such as 1,4-cyclohexylene or 1,4-phenylene, and their molecules (liquid crystal molecules) are rod-like. "Polymerizable compound" is a compound added to a composition to form a polymer. Liquid crystal compounds containing alkenyl are not classified as polymerizable compounds in this sense.

[0044] Liquid crystal compositions are prepared by mixing multiple liquid crystal compounds. The proportion (content) of the liquid crystal compounds is expressed as a weight percentage (wt%) based on the weight of the liquid crystal composition. Additives such as optically active compounds, antioxidants, UV absorbers, UV and heat stabilizers, quenchers, dyes (dichroic dyes), antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, antistatic agents, and magnetic compounds may be added to the liquid crystal composition as needed. The proportion (addition amount) of the additives, like the proportion of the liquid crystal compounds, is expressed as a weight percentage (wt%) based on the weight of the liquid crystal composition. Parts per million (ppm) by weight may also be used. The proportions of polymerization initiators and polymerization inhibitors are exceptionally expressed based on the weight of the polymerizable compounds.

[0045] The "maximum temperature of a nematic phase" may be abbreviated as "maximum temperature." The "minimum temperature of a nematic phase" may be abbreviated as "minimum temperature." The expression "increasing the dielectric anisotropy" means that the value increases positively in the case of a composition having a positive dielectric anisotropy, and means that the value increases negatively in the case of a composition having a negative dielectric anisotropy.

[0046] At least one compound selected from the group of compounds represented by formula (1) may be abbreviated as "compound (1)." "Compound (1)" means one compound or two or more compounds represented by formula (1). The same applies to compounds represented by other formulas. "At least one" in "may be substituted" means that not only the position but also the number may be selected without restriction.

[0047] TIFF2025133005000018.tif2063 Let's take the above compound (1z) as an example. In formula (1z), the symbols α and β enclosed in a hexagon correspond to ring α and ring β, respectively, and represent rings such as six-membered rings and fused rings. When the subscript 'x' is 2, two rings α exist. The two groups represented by the two rings α may be the same or different. This rule applies to multiple rings α when the subscript 'x' is greater than 2. This rule also applies to other symbols, such as the bonding group Z. A diagonal line across one side of ring β indicates that any hydrogen on ring β may be replaced with a substituent (-Sp-P). The subscript 'y' indicates the number of replaced substituents. When the subscript 'y' is 0, there is no such replacement. When the subscript 'y' is 2 or greater, multiple substituents (-Sp-P) exist on ring β. In this case, the "may be the same or different" rule also applies. Note that this rule also applies when the symbol Ra is used for multiple compounds.

[0048] In formula (1z), for example, an expression such as "Ra and Rb are alkyl, alkoxy, or alkenyl" means that Ra and Rb are independently selected from the group of alkyl, alkoxy, and alkenyl. Here, the group represented by Ra and the group represented by Rb may be the same or different. This rule also applies when the symbol Ra is used for multiple compounds. This rule also applies when multiple Ra are used for one compound.

[0049] At least one compound selected from the compounds represented by formula (1z) may be abbreviated as "compound (1z)." "Compound (1z)" means one compound represented by formula (1z), a mixture of two compounds, or a mixture of three or more compounds. The same applies to compounds represented by other formulas. The expression "at least one compound selected from the compounds represented by formula (1z) and formula (2z)" means at least one compound selected from the group of compound (1z) and compound (2z).

[0050] The expression "at least one 'A'" means that the number of 'A' is arbitrary. The expression "at least one 'A' may be replaced with 'B'" means that when there is one 'A', the position of 'A' is arbitrary, and when there are two or more 'As', their positions can be selected without restriction. The expression "at least one -CH2- may be replaced with -O-" is sometimes used. In this case, -CH2-CH2-CH2- may be converted to -O-CH2-O- by replacing non-adjacent -CH2- with -O-. However, adjacent -CH2- cannot be replaced with -O- because this replacement would produce -OO-CH2- (peroxide).

[0051] When the alkyl of a liquid crystal compound is simply referred to as "alkyl," it refers to a straight-chain or branched-chain alkyl and does not include a cycloalkyl unless otherwise specified. For example, an alkyl having 1 to 12 carbon atoms refers to a straight-chain or branched-chain alkyl having 1 to 12 carbon atoms. A straight-chain alkyl is preferred to a branched-chain alkyl. This also applies to terminal groups such as alkoxy and alkenyl. Regarding the configuration of 1,4-cyclohexylene, trans is preferred over cis to increase the maximum temperature. 2-Fluoro-1,4-phenylene refers to the following two divalent groups. In the chemical formula, the fluorine atom may be facing left (L) or right (R). This rule also applies to divalent groups of asymmetric rings such as 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl, and tetrahydropyran-2,5-diyl. Preferred tetrahydropyran-2,5-diyl groups are right-facing (R) groups for increasing the maximum temperature. TIFF2025133005000019.tif25122

[0052] Similarly, a linking group such as carbonyloxy may be either -COO- or -OCO-.

[0053] In the chemical formula of the component compound, the terminal group R 1 The symbol R is used for several compounds. In these compounds, any two R 1 The groups represented by may be the same or different. For example, R 1’ is methyl, and R 1’ In some cases, R is ethyl. 1’ is ethyl, and R 1’ In some cases, R is propyl. 2 , R 3 , R 4 , R 5 , R 6 , R 71 , R 72 This also applies to symbols such as

[0054] The present invention also includes the following: (a) the above composition further containing at least one additive selected from the group consisting of optically active compounds, antioxidants, ultraviolet absorbers, ultraviolet and heat stabilizers, quenchers, dyes (dichroic dyes), antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, antistatic agents, and magnetic compounds; (b) a device containing the above composition; (c) a device containing the above composition and used to control electromagnetic signals at any frequency from 1 GHz to 10 THz; (d) the above composition further containing a polymerizable compound, and a device containing this composition; (e) use of the above composition as a composition having a nematic phase; and (f) use of the above composition as an optically active composition by adding an optically active compound to the above composition.

[0055] The liquid crystal composition of the present invention has a large dielectric anisotropy and a small dielectric loss tangent (tan δ) at 28 GHz. It is generally known that in the frequency range of electromagnetic signals from 1 GHz to 10 THz, liquid crystal materials are not affected by orientation polarization, but are affected only by ionic and electronic polarization, resulting in constant dielectric anisotropy and dielectric loss tangent. In other words, the liquid crystal composition of the present invention can be considered to have a large dielectric anisotropy and a small dielectric loss tangent in the frequency range of electromagnetic signals from 1 GHz to 10 THz, making it suitable for use in devices involving electromagnetic waves in the range of 1 GHz to 10 THz.

[0056] The composition of the present invention will be described in the following order. First, the constitution of the component compounds in the composition will be described. Second, the main properties of the component compounds and the main effects that these compounds have on the composition will be described. Third, the combination of components in the composition, the preferred ratios of the components and the reasons for this will be described. Fourth, the preferred forms of the component compounds will be described. Fifth, preferred component compounds will be shown. Sixth, additives that may be added to the composition will be described. Seventh, a method for synthesizing the component compounds will be described. Finally, the use of the composition will be described.

[0057] First, the composition of the component compounds in the composition will be described. The composition of the present invention is classified into Composition A and Composition B. Composition A may contain liquid crystal compounds selected from Compound (1), Compound (2), Compound (3), Compound (4), Compound (5), Compound (6), and Compound (7), as well as other liquid crystal compounds, additives, etc. "Other liquid crystal compounds" are liquid crystal compounds other than Compound (1), Compound (2), Compound (3), Compound (4), Compound (5), Compound (6), and Compound (7). Such compounds are mixed into the composition for the purpose of further adjusting the properties. In order to prepare a liquid crystal composition with the desired refractive index anisotropy or dielectric anisotropy at high frequencies, it is preferable not to use liquid crystal compounds with small refractive index anisotropy, such as monocyclic compounds or bicyclic compounds without a bonding group, as "other liquid crystal compounds." The additives include optically active compounds, antioxidants, ultraviolet absorbers, stabilizers against ultraviolet light and heat, quenchers, dyes (dichroic dyes), antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, antistatic agents, and polar compounds.

[0058] Composition B consists essentially of liquid crystal compounds selected from Compound (1), Compound (2), Compound (3), Compound (4), Compound (5), Compound (6), and Compound (7). "Substantially" means that the composition may contain additives, but does not contain other liquid crystal compounds. Composition B has fewer components than Composition A. From the viewpoint of reducing costs, Composition B is preferable to Composition A. From the viewpoint of being able to further adjust the properties by mixing other liquid crystal compounds, Composition A is preferable to Composition B.

[0059] Second, the main properties of the component compounds and the main effects of these compounds on the properties of the composition are explained. The main properties of the component compounds are summarized in Table 1 based on the effects of the present invention. In the symbols in Table 1, L means large or high, M means medium, and S means small or low. The symbols L, M, and S are classifications based on qualitative comparisons between the component compounds, and 0 (zero) means that the value is approximately zero or close to zero.

[0060] Table 1. Compound properties TIFF2025133005000020.tif36148 TIFF2025133005000021.tif36146

[0061] When the component compounds are mixed into a composition, the main effects that the component compounds have on the properties of the composition are as follows: Compound (1) mainly has the effect of increasing the refractive index anisotropy, increasing the dielectric anisotropy, and decreasing the viscosity of the liquid crystal composition. From the viewpoint of decreasing the viscosity, the number of substituents is preferably 1. By controlling the number of substituents on the benzene ring of compound (1), the maximum and minimum temperatures can be controlled to some extent. That is, decreasing the number of substituents tends to increase the maximum and minimum temperatures. Increasing the number of substituents tends to decrease the maximum and minimum temperatures. From the viewpoint of decreasing the minimum temperature of the liquid crystal composition, the number of substituents is preferably 1 or 2. Compound (2) mainly has the effects of increasing the refractive index anisotropy of the liquid crystal composition, increasing the dielectric anisotropy, and decreasing tan δ at high frequencies. The relationship between the number of substituents on the benzene ring and the maximum and minimum temperatures is similar to that of compound (1), and from the viewpoint of decreasing the minimum temperature of the liquid crystal composition, the number of substituents is preferably 1 or 2. Compound (3) mainly has the effect of increasing the refractive index anisotropy, dielectric anisotropy, and maximum temperature of the liquid crystal composition. The relationship between the number of substituents on the benzene ring and the maximum and minimum temperatures is similar to that of compound (1), and from the viewpoint of decreasing the minimum temperature of the liquid crystal composition, the number of substituents is preferably 2 or 3. Compound (4) has the effect of significantly increasing the refractive index anisotropy and the dielectric anisotropy of the liquid crystal composition. The relationship between the number of substituents on the benzene ring and the maximum and minimum temperatures is similar to that of compound (1). From the viewpoint of decreasing the minimum temperature of the liquid crystal composition, the number of substituents is preferably larger, and the number of substituents is particularly preferably 2 or 3. Compound (5) has the effects of mainly increasing the dielectric anisotropy of the liquid crystal composition, decreasing tan δ at high frequencies, and decreasing the viscosity. The relationship between the number of substituents on the benzene ring and the maximum and minimum temperatures is similar to that of compound (1), and from the viewpoint of decreasing the minimum temperature of the liquid crystal composition, the number of substituents is preferably 1 or 2. Compound (6) mainly has the effect of increasing the refractive index anisotropy, dielectric anisotropy, and maximum temperature of the liquid crystal composition. From the viewpoint of increasing the refractive index anisotropy, a is preferably 0 and b is preferably 3. From the viewpoint of increasing the maximum temperature and decreasing the minimum temperature, a is preferably 1 and b is preferably 2. The relationship between the number of substituents on the benzene ring and the maximum and minimum temperatures is the same as that of compound (1), and from the viewpoint of decreasing the minimum temperature of the liquid crystal composition, the number of substituents is preferably 3 or 4. Compound (7) has the effect of expanding the temperature range of the nematic phase while mainly increasing the refractive index anisotropy. The relationship between the number of rings contained in the compound (c in formula (7)) and the maximum temperature and viscosity is such that when c is 0, the maximum temperature and viscosity tend to be low, and when c is 1, the maximum temperature and viscosity tend to be high.

[0062] Third, the combination of components in the composition, the preferred ratios of the component compounds, and the rationale for this will be explained. Preferred combinations of components in the composition are Compound (1) + Compound (2) + Compound (3) + Compound (4), Compound (1) + Compound (2) + Compound (3) + Compound (4) + Compound (5), Compound (1) + Compound (2) + Compound (3) + Compound (4) + Compound (6), Compound (1) + Compound (2) + Compound (3) + Compound (4) + Compound (7), or Compound (1) + Compound (2) + Compound (3) + Compound (4) + Compound (6) + Compound (7). A particularly preferred combination is Compound (1) + Compound (2) + Compound (3) + Compound (4), from the viewpoints of increasing the refractive index anisotropy and dielectric anisotropy and decreasing the viscosity.

[0063] A preferred ratio of compound (1) based on the weight of the liquid crystal composition is in the range of about 15% by weight to about 65% by weight in order to increase the refractive index anisotropy, increase Δε in the high-frequency region, broaden the temperature range of the nematic phase, and decrease the viscosity. A more preferred ratio is in the range of about 15% by weight to about 60% by weight. A particularly preferred ratio is in the range of about 15% by weight to about 55% by weight.

[0064] A preferred ratio of compound (2) is about 5% by weight to about 40% by weight, based on the weight of the liquid crystal composition, in order to increase the refractive index anisotropy, maintain a large Δε in the high-frequency region, reduce tanδ in the high-frequency region, and expand the temperature range of the nematic phase. A more preferred ratio is about 7% by weight to about 35% by weight. A particularly preferred ratio is about 10% by weight to about 30% by weight.

[0065] A preferred ratio of compound (3) based on the weight of the liquid crystal composition is in the range of about 10% by weight to about 55% by weight in order to increase the refractive index anisotropy, increase Δε in the high-frequency region, and broaden the temperature range of the nematic phase. A more preferred ratio is in the range of about 12% by weight to about 50% by weight. A particularly preferred ratio is in the range of about 15% by weight to about 45% by weight.

[0066] A preferred ratio of compound (4) is in the range of about 5% by weight to about 20% by weight, more preferably about 7% by weight to about 15% by weight, based on the weight of the liquid crystal composition, in order to increase the refractive index anisotropy, increase Δε in the high-frequency region, and broaden the temperature range of the nematic phase.

[0067] A preferred ratio of compound (5) is in the range of about 0% to about 30% by weight, based on the weight of the liquid crystal composition, in order to increase the refractive index anisotropy, maintain a large Δε in the high-frequency region, reduce tanδ in the high-frequency region, and expand the temperature range of the nematic phase. A more preferred ratio is in the range of about 0% to about 25% by weight. A particularly preferred ratio is in the range of about 0% to about 20% by weight.

[0068] A preferred ratio of compound (6) is in the range of about 0% to about 25% by weight, based on the weight of the liquid crystal composition, in order to increase the refractive index anisotropy, increase Δε in the high-frequency region, and broaden the temperature range of the nematic phase. A more preferred ratio is in the range of about 0% to about 20% by weight. A particularly preferred ratio is in the range of about 0% to about 15% by weight.

[0069] A preferred ratio of compound (7), based on the weight of the liquid crystal composition, is about 0% by weight or more to increase the refractive index anisotropy, decrease the viscosity, and expand the temperature range of the nematic phase, and about 50% by weight or less to increase the dielectric anisotropy. A more preferred ratio is in the range of about 0% to about 40% by weight. A particularly preferred ratio is in the range of about 0% to about 30% by weight.

[0070] Fourth, preferred forms of the component compounds will be explained. R 1 , R 2 , R 3 and R 4 is hydrogen, halogen, or a linear alkyl having 1 to 12 carbon atoms, in which at least one -CH2- may be replaced with -O- or -S-, and at least one -(CH2)2- may be replaced with -CH=CH- or -C≡C-, and in these groups at least one hydrogen may be replaced with halogen.

[0071] Preferred R 1 , R 2 , R 3 or R 4 In order to increase the stability to ultraviolet light or heat, methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, or ethoxy is preferred. In order to decrease the viscosity, methyl, ethyl, propyl, butyl, pentyl, methoxy, or ethoxy is preferred.

[0072] R 1’ , R 2’ , R 3’ and R 4’is a linear alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-.

[0073] R 5 , R 6 , R 71 , and R 72 is hydrogen, halogen, or alkyl having 1 to 12 carbon atoms, in which at least one -CH2- may be replaced with -O- or -S-, and at least one -(CH2)2- may be replaced with -CH=CH- or -C≡C-, and in these groups at least one hydrogen may be replaced with halogen.

[0074] Preferred R 5 , R 6 , R 71 , or R 72 In order to increase the stability to ultraviolet light or heat, methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, or ethoxy is preferred. In order to decrease the viscosity, methyl, ethyl, propyl, butyl, pentyl, methoxy, or ethoxy is preferred.

[0075] R 5’ , R 6’ , R 71’ and R 72’ is alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-.

[0076] a is 0, 1 or 2, b is 1, 2 or 3, and a+b is 3. Desirable a is 0 for increasing the refractive index anisotropy, and 1 for increasing the maximum temperature and decreasing the minimum temperature. Desirable b is 1 for increasing the maximum temperature, and 3 for increasing the refractive index anisotropy.

[0077] c and d are 0 or 1, and e is 0, 1, or 2. Desirable c is 0 for decreasing the minimum temperature and the viscosity, and 1 for increasing the refractive index anisotropy and the maximum temperature. Desirable d is 0 for decreasing the viscosity, and 1 for increasing the refractive index anisotropy. Desirable e is 1 for increasing the refractive index anisotropy, and 2 for further increasing the refractive index anisotropy.

[0078] Z 61 and Z 62 is a single bond, -C≡C- or -C≡CC≡C-. Preferred Z 61 or Z 62 is a single bond to decrease the viscosity, and is -C≡C- or -C≡CC≡C- to increase the refractive index anisotropy.

[0079] Ring A is 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, or pyridine-2,5-diyl, and at least one hydrogen atom on these rings may be replaced by a halogen or an alkyl having 1 to 3 carbon atoms. Preferred examples of ring A include 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, and 1,3-dioxane-2,5-diyl, and more preferably 1,4-cyclohexylene.

[0080] L 11 , L 12 , L 13 , L 21 , L 22 , L 23 , L 31 , L 32 , L 33 , L 41 , L 42 , L 43 , L 44 , L 45 , L 51 , L 52 , L53 , L 61 , L 62 , L 63 , L 64 , L 71 , L 72 , L 73 , L 74 , L 75 , L 76 , and L 77 is hydrogen, halogen, alkyl having 1 to 3 carbon atoms, or cycloalkyl having 3 to 5 carbon atoms. 11 , L 12 , L 13 , L 21 , L 22 , L 23 , L 31 , L 32 , L 33 , L 41 , L 42 , L 43 , L 44 , L 45 , L 51 , L 52 , L 53 , L 61 , L 62 , L 63 , L 64 , L 71 , L 72 , L 73 , L 74 , L 75 , L 76 , or L 77 represents hydrogen for increasing the maximum temperature, represents fluorine or chlorine for increasing the dielectric anisotropy, and represents fluorine, chlorine, methyl, or ethyl for decreasing the minimum temperature.

[0081] L 44’ , L 45’ , L 61’ , L 62’ , L 63’ , L 64’ , L 71’ ,L 72’ , L 73’ , L 74’ , L 75’ , L 76’ and L 77’ is hydrogen, fluorine, chlorine, methyl or ethyl.

[0082] Y 11 , Y 21 , Y 22 , Y 23 , Y 31 , Y 32 , Y 33 , Y 34 , Y 35 , Y 36 , Y 41 , Y 51 , Y 52 , and Y 61 is hydrogen or halogen. 11 , Y 21 , Y 22 , Y 23 , Y 31 , Y 32 , Y 33 , Y 34 , Y 35 , Y 36 , Y 41 , Y 51 , Y 52 , or Y 61 is hydrogen for increasing the refractive index anisotropy, and is fluorine or chlorine for increasing the dielectric anisotropy and decreasing the minimum temperature.

[0083] Y 21’ , Y 22’ , Y 35’ , Y 51’ and Y 61’ is hydrogen, fluorine or chlorine.

[0084] In formula (1), L 11 , L 12 and L 13 At least one of L is alkyl having 1 to 3 carbon atoms. 11 , L 12 and L 13 At least one of these is methyl.

[0085] In equation (3), L 31 , L 32 and L 33At least one of L is alkyl having 1 to 3 carbon atoms. 31 , L 32 and L 33 At least one of these is methyl.

[0086] In equation (4), in order to lower the minimum temperature, L 41 , L 42 , L 43 , L 44 , L 45 and Y 41 At least two of the groups are preferably not hydrogen; 41 , L 42 , L 43 , L 44 , L 45 and Y 41 It is more preferable that at least two of the groups are fluorine or methyl.

[0087] In order to increase the dielectric anisotropy of the entire liquid crystal composition, L 11 and L 12 , L 13 and Y 11 , L 21 and L 22 , L 23 and Y 23 , Y 33 and Y 35 , L 31 and L 32 , L 33 and Y 36 , L 41 and L 42 , L 45 and Y 41 , L 51 and L 52 , L 53 and Y 52 , L 72 and L 73 , L 75 and L 76 , L S1 and L S2 or L S3 and Y S1 is preferably not simultaneously a halogen.

[0088] The liquid crystal composition of the present invention preferably does not contain a compound represented by formula (S) in order to have a nematic phase over a wide temperature range. In formula (S), R S1 is hydrogen, halogen, or alkyl having 1 to 12 carbon atoms, in which at least one -CH2- may be replaced by -O- or -S-, and at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and in these groups at least one hydrogen may be replaced by halogen; L S1 , L S2 and L S3 is hydrogen or fluorine; Y S1 is hydrogen or fluorine.

[0089] The liquid crystal composition of the present invention preferably does not contain a compound represented by formula (T) in order to have a high voltage holding ratio for driving a TFT. In formula (T), R T1 is hydrogen, halogen, or alkyl having 1 to 12 carbon atoms, in which at least one -CH2- may be replaced by -O- or -S-, and at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and in these groups at least one hydrogen may be replaced by halogen; Y T1 and Y T2 is hydrogen or fluorine; t is 0 or 1. Fifth, preferred component compounds are shown. Preferred compounds (1) are compounds (1-1) to (1-10).

[0090] TIFF2025133005000022.tif213113

[0091] In formulas (1-1) to (1-10), R 1’is a linear alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-.

[0092] More preferably, at least one of the compounds (1) is the compound (1-7) or the compound (1-8).

[0093] Preferred compounds (2) are compounds (2-1) to (2-10).

[0094] TIFF2025133005000023.tif214113

[0095] In equations (2-1) to (2-10), R 2’ is a linear alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-; Y 22’ is hydrogen, fluorine or chlorine; In equation (2-10), Y 21’ is hydrogen, fluorine or chlorine.

[0096] More preferably, at least one of the compounds (2) is the compound (2-2), the compound (2-5), or the compound (2-6).

[0097] Preferred compounds (3) are compounds (3-1) to (3-11).

[0098] TIFF2025133005000024.tif228113 TIFF2025133005000025.tif22112

[0099] In equations (3-1) to (3-11), R 3’is a linear alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-; Y 35’ is hydrogen, fluorine or chlorine.

[0100] At least one of the compounds (3) is more preferably the compound (3-1), the compound (3-2), the compound (3-3), the compound (3-4), or the compound (3-5), and particularly preferably the compound (3-1), the compound (3-2), or the compound (3-4).

[0101] Preferred compounds (4) are compounds (4-1) to (4-7).

[0102] TIFF2025133005000026.tif168111

[0103] In equations (4-1) to (4-7), R 4’ is a linear alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-; L 44’ and L 45’ is hydrogen, fluorine, chlorine, methyl or ethyl; Y 41’ is hydrogen, fluorine or chlorine.

[0104] More preferably, at least one of the compounds (4) is the compound (4-2).

[0105] Preferred compounds (5) are compounds (5-1) to (5-10).

[0106] TIFF2025133005000027.tif222113

[0107] In equations (5-1) to (5-10), R 5’ is alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-; Y 51’ is hydrogen, fluorine or chlorine.

[0108] More preferably, at least one of the compounds (5) is the compound (5-2), the compound (5-6), or the compound (5-7).

[0109] Preferred compounds (6) are compounds (6-1) to (6-8).

[0110] TIFF2025133005000028.tif210126

[0111] In equations (6-1) to (6-8), R 6’ is alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-; L 61’ , L 62’ , L 63’ and L 64’ is hydrogen, fluorine, chlorine, methyl or ethyl; Y 61’ is hydrogen, fluorine or chlorine.

[0112] More preferably, at least one of the compounds (6) is the compound (6-4), the compound (6-6), the compound (6-7), or the compound (6-8).

[0113] Preferred compounds (7) are compounds (7-1) to (7-6).

[0114] TIFF2025133005000029.tif148111

[0115] In equations (7-1) to (7-6), R 71’ and R 72’ is alkyl having 1 to 12 carbon atoms, in which at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-; In formula (7-1) and formula (7-2), L 75’ , L 76’ and L 77’ is hydrogen, fluorine, chlorine, methyl or ethyl: In equation (7-3), L 72’ , L 74’ , L 75’ , L 76’ and L 77’ is hydrogen, fluorine, chlorine, methyl or ethyl; In equation (7-4), L 71’ , L 73’ , L 75’ , L 76’ and L 77’ is hydrogen, fluorine, chlorine, methyl or ethyl; In equations (7-5) and (7-6), L 71’ ,L 72’ , L 73’ , L 74’ , L 75’ , L 76’ and L 77’ is hydrogen, fluorine, chlorine, methyl or ethyl.

[0116] It is more preferable that at least one of the compounds (7) is the compound (7-1), the compound (7-2), the compound (7-3), the compound (7-4), or the compound (7-6).It is particularly preferable that at least two of the compounds (7) are a combination of the compound (7-1) and the compound (7-4), the compound (7-1) and the compound (7-6), the compound (7-2) and the compound (7-4), or the compound (7-2) and the compound (7-6).

[0117] Sixth, additives that may be added to the composition will be described. Such additives include optically active compounds, antioxidants, UV absorbers, UV and heat stabilizers, quenchers, dyes (dichroic dyes), antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, antistatic agents, polar compounds, etc. In the following, unless otherwise specified, the mixing ratios of these additives are based on the weight of the liquid crystal composition (weight ratio).

[0118] The additives may be used in any combination, and for example, different types of antioxidants may be used in combination. For example, different types of additives may be used in combination, such as an antioxidant, an ultraviolet absorber, and a stabilizer.

[0119] An optically active compound is added to the composition to induce a helical structure of the liquid crystal and provide a twist angle. Examples of such compounds are compounds (8-1) to (8-5). The preferred proportion of the optically active compound is about 5% by weight or less. A more preferred proportion is in the range of about 0.01% by weight to about 2% by weight.

[0120] TIFF2025133005000030.tif148105

[0121] To prevent a decrease in resistivity due to heating in the atmosphere or to maintain a high voltage holding ratio not only at room temperature but also at temperatures close to the upper limit temperature after long-term use of the element, an antioxidant is added to the composition. Preferred examples of the antioxidant include compound (9), in which t is an integer from 1 to 9. TIFF2025133005000031.tif2399

[0122] In compound (9), t is preferably 1, 3, 5, 7, or 9. More preferably, t is 7. Compound (9) in which t is 7 has low volatility, and is therefore effective in maintaining a high voltage holding ratio not only at room temperature but also at temperatures close to the upper limit temperature after long-term use of the device. The preferred proportion of the antioxidant is about 50 ppm or more to achieve this effect, and about 600 ppm or less to avoid lowering the upper limit temperature or raising the lower limit temperature. A more preferred proportion is in the range of about 100 ppm to about 300 ppm.

[0123] Preferred examples of ultraviolet absorbers include benzophenone derivatives, benzoate derivatives, and triazole derivatives. Light stabilizers such as sterically hindered amines are also preferred. Preferred examples of light stabilizers include compounds (10-1) to (10-16). The preferred ratio of these absorbers and stabilizers is about 50 ppm or more to obtain their effects, and about 10,000 ppm or less to avoid lowering the maximum temperature or raising the minimum temperature. A more preferred ratio is in the range of about 100 ppm to about 10,000 ppm.

[0124] TIFF2025133005000032.tif237112 TIFF2025133005000033.tif239120

[0125] A preferred additive as a stabilizer against ultraviolet light and heat is an amino-tolane compound represented by compound (11) (US Patent No. 6,495,066). TIFF2025133005000034.tif2892

[0126] In equation (11), R m and R n is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, or alkenyloxy having 2 to 12 carbon atoms; X a is -NO2, -C≡N, -N=C=S, fluorine, or -OCF3; Y a and Y bis hydrogen or fluorine. A preferred ratio of these stabilizers is in the range of 1 to 20% by weight, more preferably 5 to 10% by weight, in order to obtain the desired effect.

[0127] A quencher is a compound that receives light energy absorbed by a liquid crystal compound and converts it into thermal energy, thereby preventing decomposition of the liquid crystal compound. A preferred ratio of these quenchers is about 50 ppm or more to obtain this effect, and about 20,000 ppm or less to lower the minimum temperature. A more preferred ratio is in the range of about 100 ppm to about 10,000 ppm.

[0128] To make the composition compatible with GH (guest-host) mode devices, a dichroic dye such as an azo dye or an anthraquinone dye is added to the composition. The preferred dye content is about 0.01% by weight to about 10% by weight. To prevent foaming, an antifoaming agent such as dimethyl silicone oil or methylphenyl silicone oil is added to the composition. The preferred antifoaming agent content is about 1 ppm or more to achieve its effectiveness and about 1000 ppm or less to prevent display defects. A more preferred content is about 1 ppm to about 500 ppm.

[0129] A polymerizable compound is added to the composition to make it compatible with polymer-stabilized devices. Preferred examples of the polymerizable compound include compounds with polymerizable groups, such as acrylates, methacrylates, vinyl compounds, vinyloxy compounds, propenyl ethers, epoxy compounds (oxiranes, oxetanes), and vinyl ketones. More preferred examples include acrylate or methacrylate derivatives. The preferred proportion of the polymerizable compound is about 0.05% by weight or more to achieve its intended effect, and about 20% by weight or less to prevent an increase in operating temperature. A more preferred proportion is in the range of about 0.1% to about 10% by weight. The polymerizable compound is polymerized by ultraviolet irradiation. Polymerization may also be carried out in the presence of a polymerization initiator, such as a photoinitiator. Suitable conditions for polymerization, the appropriate type of initiator, and the appropriate amount are known to those skilled in the art and described in the literature. For example, photoinitiators Irgacure 651 (registered trademark; BASF), Irgacure 184 (registered trademark; BASF), or Darocur 1173 (registered trademark; BASF) are suitable for radical polymerization. A preferred ratio of the photopolymerization initiator is in the range of about 0.1 to about 5 parts by weight, and a more preferred ratio is in the range of about 1 to about 3 parts by weight, based on 100 parts by weight of the polymerizable compound.

[0130] When storing a polymerizable compound, a polymerization inhibitor may be added to prevent polymerization. The polymerizable compound is usually added to the composition without removing the polymerization inhibitor. Examples of polymerization inhibitors include hydroquinone, hydroquinone derivatives such as methylhydroquinone, 4-tert-butylcatechol, 4-methoxyphenol, phenothiazine, etc.

[0131] As used herein, a polar compound is an organic compound that has polarity, excluding compounds with ionic bonds. Atoms such as oxygen, sulfur, and nitrogen tend to be more electronegative and carry a partial negative charge. Carbon and hydrogen tend to be neutral or carry a partial positive charge. Polarity arises from the uneven distribution of partial charges among different atoms in a compound. For example, a polar compound has at least one of the following moieties: -OH, -COOH, -SH, -NH, >NH, >N-.

[0132] Seventh, we will explain the synthesis of the component compounds. The synthesis of compound (1) is described in the Examples section. Other compounds can be synthesized by methods described in textbooks such as Organic Syntheses (John Wiley & Sons, Inc.), Organic Reactions (John Wiley & Sons, Inc.), Comprehensive Organic Synthesis (Pergamon Press), and New Experimental Chemistry Lectures (Maruzen). Compositions are prepared from the compounds thus obtained by known methods. For example, the component compounds are mixed and dissolved by heating.

[0133] Finally, the use of the composition will be described. The composition of the present invention has a minimum temperature of about -10°C or less and a maximum temperature of about 70°C or more, and therefore can be used not only as a composition having a nematic phase, but also as an optically active composition by adding an optically active compound.

[0134] An aligned liquid crystal composition has different dielectric constants in the vertical and horizontal directions, and therefore has dielectric anisotropy as a characteristic.

[0135] Not only antenna elements, but also other elements using liquid crystal compositions generally consist of two substrates sandwiching a layer of liquid crystal composition between them. The liquid crystal molecules are aligned in one direction by an alignment film at their interface. In the absence of an external field, the liquid crystal molecules in the element are aligned in one direction due to the alignment force of the alignment film. However, when an external field is applied, the liquid crystal molecules in the element deviate from the alignment of the alignment film and orient in the direction of the external field. When the external field is removed again, the alignment force of the alignment film causes the liquid crystal molecules to return to their original aligned state. In this way, the orientation of the liquid crystal molecules in the element can be controlled by the direction and magnitude of the external field, thereby controlling the tilt (angle) of the liquid crystal molecules in the element relative to one direction. Because liquid crystal compositions have dielectric anisotropy, controlling the angle of the liquid crystal molecules in the element relative to one direction can control the dielectric constant of the liquid crystal composition layer in the element relative to that direction. For example, when the dielectric constant of a layer of a liquid crystal composition in a unidirectional element is the vertical dielectric constant of the liquid crystal composition in the absence of an external field, applying an external field perpendicular to the unidirectional direction can change the dielectric constant to the horizontal dielectric constant of the liquid crystal composition.

[0136] Thus, the liquid crystal composition of the present invention can be used as a switching element capable of reversibly controlling the dielectric constant by reversibly changing the alignment direction of the liquid crystal molecules.

[0137] The angle of the liquid crystal molecules in the element can be controlled using an electric field as an external field. The voltage required to drive the liquid crystal molecules is the driving voltage. To control the angle of the liquid crystal molecules, the liquid crystal composition is required to have a dielectric anisotropy at 25°C in a frequency range of less than 1 MHz of at least 2. To further reduce the driving voltage, the dielectric anisotropy at 25°C in a frequency range of less than 1 MHz must be made larger, preferably 5 or more, and more preferably 10 or more.

[0138] As mentioned above, the larger the refractive index anisotropy (Δn) in visible light (for example, wavelength 589 nm), the larger the dielectric anisotropy (Δε) in the high frequency range (range from microwaves to terahertz waves (approximately 10 THz)). The liquid crystal composition containing the compound represented by general formula (1) of the present invention preferably has a refractive index anisotropy (Δn) of 0.30 or more at 25°C. In particular, when used for high frequency applications, Δn is more preferably 0.40 or more, and particularly preferably 0.45 or more.

[0139] To control the phase difference in the high frequency range, the dielectric anisotropy in the high frequency range is preferably 0.5 or more. To more effectively control the phase difference, the dielectric anisotropy in the high frequency range must be increased. To achieve sufficient phase control, the dielectric anisotropy is preferably 1.0 or more, and more preferably 1.2 or more.

[0140] Furthermore, the composition of the present invention can be used in elements used to control electromagnetic waves in the frequency range of 1 GHz to 10 THz. Application examples include antenna arrays, electromagnetic wave reflectors, millimeter-wave band variable phase shifters, millimeter-wave radar, and the like. Various applications and methods of elements using the composition of the present invention have been developed. Antenna arrays that utilize metamaterial technology, and electromagnetic wave reflectors such as intelligent reflecting surfaces (IRS), reconfigurable intelligent surfaces (RIS), and frequency-selective surfaces have been developed.

[0141] A device containing this composition can be used for purposes other than electromagnetic wave control. By reversibly changing the alignment direction of the liquid crystal molecules, it is possible to control not only the dielectric constant but also the refractive index. The liquid crystal composition according to the present invention exhibits a high refractive index anisotropy (Δn), and therefore the amount of change in refractive index and the amount of phase modulation caused by changing the alignment direction of the liquid crystal molecules under visible light and infrared light are large and can be controlled.

[0142] These property control applications include, for example, birefringent lenses used to switch between 2D and 3D for stereoscopic image displays, liquid crystal lenses used for camera focus adjustment, etc. They can also be used in spatial light modulators (SLMs) used in electronic holographic displays, and in light detection and ranging (LiDAR) elements, which are distance measurement sensors. [Example]

[0143] The present invention will be explained in more detail with reference to examples. The present invention is not limited by these examples. The present invention also includes a mixture of at least two of the compositions of the examples. The synthesized compounds were identified by NMR analysis. The properties of the compositions were measured by the methods described below.

[0144] NMR analysis: The measurement device used was a DRX-500 (manufactured by Bruker Biospin Co., Ltd.). 1 For H-NMR measurements, samples were dissolved in deuterated solvents such as CDCl3, and measurements were performed at room temperature, 500 MHz, and with 16 accumulations. Tetramethylsilane was used as the internal standard. 19 F-NMR measurements were performed using CFCl3 as an internal standard with an accumulation count of 24. In describing nuclear magnetic resonance spectra, s means singlet, d means doublet, t means triplet, q means quartet, quin means quintet, sex means sextet, m means multiplet, and br means broad.

[0145] Measurement sample: When measuring the phase structure and transition temperature, the liquid crystal compound itself was used as the sample. When measuring physical properties such as the upper limit temperature of the nematic phase, viscosity, optical anisotropy, and dielectric anisotropy, a composition prepared by mixing the compound with mother liquid crystal was used as the sample.

[0146] When using a sample in which a compound was mixed with mother liquid crystals, the measurement was carried out by the following method. A sample was prepared by mixing 20% ​​by weight of the compound with 80% by weight of the mother liquid crystals. From the measured value of this sample, an extrapolated value was calculated according to the extrapolation method represented by the following formula, and this value was recorded. <Extrapolated value> = (100 x <Measured value of sample> - <weight % of mother liquid crystals> x <Measured value of mother liquid crystals>) / <weight % of compound>

[0147] Even when the ratio of the compound to the mother liquid crystals was this ratio, if crystals (or a smectic phase) precipitated at 25° C., the ratio of the compound to the mother liquid crystals was changed in the order of 10 wt%:90 wt%, 5 wt%:95 wt%, and 1 wt%:99 wt%, and the physical properties of the sample were measured at the ratio at which crystals (or a smectic phase) no longer precipitated at 25° C. Unless otherwise specified, the ratio of the compound to the mother liquid crystals was 20 wt%:80 wt%.

[0148] The following base liquid crystal (i) was used as the base liquid crystal. The ratio of the components of the base liquid crystal (i) in weight percent was show.

[0149] TIFF2025133005000035.tif67166

[0150] Measurement methods: The characteristics were measured using the following methods. Most of these methods were either methods described in the JEITA standard (JEITA ED-2521B) established by the Japan Electronics and Information Technology Industries Association (JEITA), or modified versions of these methods. The TN devices used for the measurements were not equipped with thin film transistors (TFTs).

[0151] Nematic phase upper limit temperature (NI; °C): The sample was placed on a hot plate of a melting point measuring apparatus equipped with a polarizing microscope and heated at a rate of 1°C / min. The temperature at which a part of the sample changed from a nematic phase to an isotropic liquid was measured.

[0152] The lowest temperature of the nematic phase (T C ;℃): Samples with a nematic phase were placed in glass bottles and stored in freezers at 0°C, -10°C, -20°C, -30°C, and -40°C for 10 days, after which the liquid crystal phase was observed. For example, when a sample remained in the nematic phase at -20°C and changed to a crystalline or smectic phase at -30°C, T C was described as <-20°C.

[0153] Viscosity (bulk viscosity; η; measured at 20°C; mPa s): For the measurement, an E-type rotational viscometer manufactured by Tokyo Keiki Co., Ltd. was used.

[0154] Viscosity (rotational viscosity; γ1; measured at 25°C; mPa·s): Measurements were performed according to the method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). A sample was placed in a TN device with a 0° twist angle and a 5 μm cell gap between the two glass substrates. A voltage was applied to this device in 0.5 V increments ranging from 16 V to 19.5 V. After a 0.2-second period without voltage application, a single square wave (rectangular pulse; 0.2 seconds) was applied, followed by a 2-second period without voltage application. The peak current and peak time of the transient current generated by this application were measured. The rotational viscosity was calculated from these measurements and equation (8) on page 40 of the paper by M. Imai et al. The dielectric anisotropy required for this calculation was determined using the device used to measure the rotational viscosity, as described below.

[0155] Refractive index anisotropy (Δn<0.30; measured at 25°C): Measurements were performed using light with a wavelength of 589 nm and an Abbe refractometer with a polarizing plate attached to the eyepiece. After rubbing the surface of the main prism in one direction, a sample was dropped onto the main prism. The refractive index n ∥ was measured when the direction of the polarized light was parallel to the rubbing direction. ⊥was measured when the direction of polarized light was perpendicular to the rubbing direction. The refractive index anisotropy value was Δn = n ∥ -n ⊥ , was calculated from the formula.

[0156] Refractive index anisotropy (Δn≧0.30; measured at 25℃): A sample was placed in an element consisting of two glass substrates and aligned in an anti-parallel manner. The retardation (Rth) in the thickness direction of this element was measured using a retardation film / optical material inspection device (manufactured by Otsuka Electronics Co., Ltd., product name: RETS-100), and the refractive index anisotropy (Δn) was calculated using the following formula from the retardation value (Rth) and the distance between the glass substrates (d: cell gap). The wavelength of the light used was 589 nm. Rth =Δn d

[0157] Dielectric anisotropy (Δε; measured at 25°C): The sample was placed in a TN device with a cell gap of 9 μm between the two glass substrates and a twist angle of 80 degrees. A sine wave (10 V, 1 kHz) was applied to the device, and after 2 seconds, the dielectric constant (ε) of the liquid crystal molecules in the long axis direction was measured. ∥ A sine wave (0.5 V, 1 kHz) was applied to this device, and the dielectric constant (ε ⊥ The dielectric anisotropy value was measured as Δε = ε ∥ -ε ⊥ , was calculated from the formula.

[0158] Voltage Holding Ratio (VHR; measured at 25°C; %): The cell used for the measurements had the following structure: an ITO electrode and a rubbed polyimide alignment film were arranged on each substrate in that order. The two substrates were then bonded together with the alignment film facing inward, so that the angle between the rubbing directions of the upper and lower substrates was 90 degrees. The distance between the two glass substrates (cell gap) was 5 μm. A liquid crystal composition was sealed in the cell. The TN device was charged by applying a pulse voltage (5 V for 60 microseconds). The decaying voltage was measured for 16.7 milliseconds using a high-speed voltmeter, and the area A between the voltage curve and the horizontal axis in the unit period was calculated. Area B was the area when no decay occurred. The voltage retention rate was expressed as the percentage of area A relative to area B.

[0159] Dielectric anisotropy at 28GHz (measured at 25℃): The dielectric anisotropy at 28 GHz (Δε@28 GHz) was measured using the method disclosed in Applied Optics, Vol. 44, No. 7, p. 1150 (2005). A variable short-circuit waveguide with a window was filled with liquid crystal and held in a static magnetic field of 0.3 T for 3 minutes. A 28 GHz microwave was input into the waveguide, and the amplitude ratio of the reflected wave to the incident wave was measured. Measurements were made by changing the direction of the static magnetic field and the length of the short-circuit tube, and the refractive index (n:ne,no) and loss parameters (α:αe,αo) were determined. The complex dielectric constant (ε', ε") was calculated using the calculated refractive index and loss parameters and the following relational expression: ε'=n 2 -κ 2 ε”=2nκ α=2ωκ / c where c is the speed of light in a vacuum, ω is the angular velocity, and κ is the extinction coefficient. e From ε' ∥ , n o From ε' ⊥ The dielectric anisotropy (Δε@28GHz) is calculated as ε' ∥ -ε' ⊥ It was calculated from.

[0160] Dielectric loss tangent (tanδ) at 28GHz (measured at room temperature): The dielectric loss tangent at 28GHz (tanδ@28GHz) was calculated from ε" / ε' using the complex dielectric constants (ε', ε"). Since anisotropy also appears in tanδ, the larger value is listed.

[0161] The compounds in the examples are represented by symbols based on the definitions in Table 2. The number in parentheses after the symbol corresponds to the compound number. The symbol (-) means other liquid crystal compounds. The proportion (percentage) of the liquid crystal compound is a weight percentage (% by weight) based on the weight of the liquid crystal composition. Finally, the property values ​​of the compositions are summarized.

[0162] TIFF2025133005000036.tif249148

[0163] Comparative Example 1 Liquid Crystal Composition C1 3-BTB(2Me)-NCS (1-7) 15% 4-BTB(2Me)-NCS (1-7) 10% 5-BTB(2Me)-NCS (1-7) 10% 3-BB(F)B(F,F)-NCS (2-2) 5% 3-BB(F)B(Me)-NCS (2-6) 10% 3-BB(F)TB(Me)-NCS (3-2) 5% 5-BB(F)TB(Me)-NCS (3-2) 10% 5-BB(F)TB(2Me,5Me)-NCS (3-3) 5% 3-BB(F)TB(2Me,5F)-NCS (3-4) 10% 3-BTB(2Me,5F)TB-NCS (4-2) 10% 3-BTB(2Me,5F)B(F)-NCS (S) 10% NI=110.4℃;Tc<-30℃;Δn=0.470;Δε=15.1 The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition C1 were as follows. Δε@28GHz=1.26 tanδ@28GHz=0.007

[0164] Example 1 Liquid Crystal Composition M1 3-BTB(2Me)-NCS (1-7) 15% 4-BTB(2Me)-NCS (1-7) 10% 5-BTB(2Me)-NCS (1-7) 10% 3-BB(F)B(F,F)-NCS (2-2) 5% 3-BB(F)B(Me)-NCS (2-6) 10% 3-BB(F)TB(Me)-NCS (3-2) 13% 5-BB(F)TB(Me)-NCS (3-2) 12% 5-BB(F)TB(2Me,5Me)-NCS (3-3) 5% 3-BB(F)TB(2Me,5F)-NCS (3-4) 10% 3-BTB(2Me,5F)TB-NCS (4-2) 10% NI=115.2℃;Tc<-40℃;Δn=0.475;Δε=14.9 The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M1 were as follows. Δε@28GHz=1.28 tanδ@28GHz=0.006

[0165] The composition of Comparative Example 1, excluding Compound S, and composed of Compounds (1) to (4), corresponds to Example 1. The Δε@28GHz of the composition of Comparative Example 1 was 1.26, and the Δε@28GHz of the composition of Example 1 was 1.28, both of which can be considered large. The tan δ@28GHz were 0.007 and 0.006, respectively, and the composition of Example 1 was slightly smaller. Furthermore, the upper limit temperature of Comparative Example 1 was 110.4°C and the lower limit temperature was <−30°C, while the upper limit temperature of Example 1 was 115.2°C and the lower limit temperature was <−40°C. It was confirmed that a liquid crystal composition having a nematic phase over a wider temperature range could be obtained without using Compound (S).

[0166] Comparative Example 2 Liquid Crystal Composition C2 3-BTB(2Me)-NCS (1-7) 20% 5-BTB(2Me)-NCS (1-7) 10% 3-BB(F)TB(Me)-NCS (3-2) 10% 5-BB(F)TB(Me)-NCS (3-2) 10% 5-BB(F)TB(2Me,5Me)-NCS (3-3) 10% 5-B(F)TB(F)-TC (T) 10% 5-BTB(F)-TC (T) 15% 3-BB(F)TB-TC (T) 10% 5-BB(F)TB-TC (T) 5% NI=131.5℃;Tc<-30℃;Δn=0.496;Δε=21.6;VHR=73.9%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition C2 were as follows. Δε@28GHz=1.25 tanδ@28GHz=0.009

[0167] [Example 2] Liquid crystal composition M2 3-BTB(2Me)-NCS (1-7) 18% 4-BTB(2Me)-NCS (1-7) 10% 5-BTB(2Me)-NCS (1-7) 17% 3-BB(F)B(F,F)-NCS (2-2) 15% 3-BB(F)TB(Me)-NCS (3-2) 13% 5-BB(F)TB(Me)-NCS (3-2) 7% 3-BB(F)TB(2Me,5F)-NCS (3-4) 10% 3-BTB(2Me,5F)TB-NCS (4-2) 10% NI=100.1℃;Tc<-40℃;Δn=0.465;Δε=15.1;VHR=99.1%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M2 were as follows. Δε@28GHz=1.24 tanδ@28GHz=0.006

[0168] The composition of Comparative Example 2, excluding Compound T, and composed of Compounds (1) to (4), corresponds to Example 2. The Δε@28GHz of the composition of Comparative Example 2 was 1.25, and the Δε@28GHz of the composition of Example 2 was 1.24, both of which can be considered large. Meanwhile, the tan δ@28GHz values ​​were 0.009 and 0.006, respectively, making the composition of Example 2 significantly smaller. Furthermore, the VHR values ​​were 73.9% and 99.1%, respectively, making the composition of Comparative Example 2 unsuitable for TFT operation. This confirms that the composition composed of Compounds (1) to (4) is effective in reducing tan δ@28GHz and has a very high VHR.

[0169] [Example 3] Liquid crystal composition M3 3-BTB(2Me)-NCS (1-7) 20% 4-BTB(2Me)-NCS (1-7) 10% 5-BTB(2Me)-NCS (1-7) 16% 3-BB(F)B(F,F)-NCS (2-2) 9% 3-BB(F)TB(Me)-NCS (3-2) 13% 5-BB(F)TB(Me)-NCS (3-2) 7% 3-BB(F)TB(2Me,5F)-NCS (3-4) 15% 3-BTB(2Me,5F)TB-NCS (4-2) 10% NI=100.0℃;Tc<-20℃;Δn=0.468;Δε=14.7;VHR=99.2%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M3 were as follows. Δε@28GHz=1.28 tanδ@28GHz=0.006

[0170] [Example 4] Liquid crystal composition M4 3-BTB(2Me)-NCS (1-7) 20% 4-BTB(2Me)-NCS (1-7) 10% 5-BTB(2Me)-NCS (1-7) 15% 3-BB(F)B(F,F)-NCS (2-2) 17% 3-BB(F)TB(Me)-NCS (3-2) 13% 3-BB(F)TB(2Me,5F)-NCS (3-4) 15% 3-BTB(2Me,5F)TB-NCS (4-2) 10% NI=100.1℃;Tc<-20℃;Δn=0.467;Δε=15.7;VHR=99.3%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M4 were as follows. Δε@28GHz=1.26 tanδ@28GHz=0.006

[0171] [Example 5] Liquid crystal composition M5 3-BTB(2Me)-NCS (1-7) 18% 4-BTB(2Me)-NCS (1-7) 10% 5-BTB(2Me)-NCS (1-7) 16% 3-BB(F)B(F,F)-NCS (2-2) 15% 3-BB(F)TB(2Me)-NCS (3-1) 8% 3-BB(F)TB(Me)-NCS (3-2) 13% 3-BB(F)TB(2Me,5F)-NCS (3-4) 10% 3-BTB(2Me,5F)TB-NCS (4-2) 10% NI=102.5℃;Tc<-40℃;Δn=0.459;Δε=15.5;VHR=99.2%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M5 were as follows. Δε@28GHz=1.20 tanδ@28GHz=0.006

[0172] [Example 6] Liquid crystal composition M6 3-BTB(2Me)-NCS (1-7) 20% 5-BTB(2Me)-NCS (1-7) 15% 3-BTB(Me)-NCS (1-8) 10% 3-BB(F)B(F,F)-NCS (2-2) 10% 3-BB(F)TB(2Me)-NCS (3-1) 12% 3-BB(F)TB(Me)-NCS (3-2) 13% 3-BB(F)TB(2Me,5F)-NCS (3-4) 10% 3-BTB(2Me,5F)TB-NCS (4-2) 10% NI=101.2℃;Tc<-40℃;Δn=0.471;Δε=14.6;VHR=99.2%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M6 were as follows. Δε@28GHz=1.27 tanδ@28GHz=0.006

[0173] [Example 7] Liquid crystal composition M7 3-BTB(2Me)-NCS (1-7) 17% 4-BTB(2Me)-NCS (1-7) 8% 5-BTB(2Me)-NCS (1-7) 15% 3-BBB(2Me)-NCS (2-5) 15% 3-BB(F)TB(Me)-NCS (3-2) 5% 5-BB(F)TB(Me)-NCS (3-2) 15% 5-BB(F)TB(2Me,5Me)-NCS (3-3) 5% 3-BB(F)TB(2Me,5F)-NCS (3-4) 10% 3-BTB(2Me,5F)TB-NCS (4-2) 10% NI=106.6℃;Tc<-40℃;Δn=0.460;Δε=15.5;VHR=99.2%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M7 were as follows. Δε@28GHz=1.25 tanδ@28GHz=0.006

[0174] [Example 8] Liquid crystal composition M8 3-BTB(2Me)-NCS (1-7) 15% 4-BTB(2Me)-NCS (1-7) 10% 5-BTB(2Me)-NCS (1-7) 15% 3-BB(F)B(F,F)-NCS (2-2) 15% 4-BB(F)B(F,F)-NCS (2-2) 10% 3-BB(F)TB(Me)-NCS (3-2) 5% 5-BB(F)TB(Me)-NCS (3-2) 15% 5-BB(F)TB(2Me,5Me)-NCS (3-3) 5% 5-BTB(F)TB(2Me,5F)-NCS (4-1) 10% NI=102.5℃;Tc<-40℃;Δn=0.445;Δε=15.9;VHR=99.0%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M8 were as follows. Δε@28GHz=1.19 tanδ@28GHz=0.006

[0175] [Example 9] Liquid crystal composition M9 3-BTB(2Me)-NCS (1-7) 18% 4-BTB(2Me)-NCS (1-7) 9% 5-BTB(2Me)-NCS (1-7) 18% 3-BB(F)B(F,F)-NCS (2-2) 14% 3-BB(F)TB(Me)-NCS (3-2) 10% 5-BB(F)TB(Me)-NCS (3-2) 8% 3-BB(F)TB(2Me,5F)-NCS (3-4) 13% 5-BTB(2Me,5Me)TB-NCS (4-4) 10% NI=101.4℃;Tc<-40℃;Δn=0.464;Δε=15.2;VHR=99.0%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M9 were as follows. Δε@28GHz=1.25 tanδ@28GHz=0.006

[0176] [Example 10] Liquid crystal composition M10 3-BTB(2Me,5F)-NCS (1-3) 10% 3-BTB(2Me)-NCS (1-7) 18% 5-BTB(2Me)-NCS (1-7) 17% 3-BB(F)B(F,F)-NCS (2-2) 18% 3-BB(F)TB(Me)-NCS (3-2) 9% 5-BB(F)TB(Me)-NCS (3-2) 3% 3-BB(F)TB(2Me,5F)-NCS (3-4) 13% 3-BTB(2Me,5F)TB-NCS (4-2) 12% NI=101.0℃;Tc<-30℃;Δn=0.461;Δε=15.5;VHR=99.1%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M10 were as follows. Δε@28GHz=1.23 tanδ@28GHz=0.006

[0177] [Example 11] Liquid crystal composition M11 3-BTB(2Me)-NCS (1-7) 18% 4-BTB(2Me)-NCS (1-7) 9% 5-BTB(2Me)-NCS (1-7) 18% 3-BB(F)B(F,F)-NCS (2-2) 14% 3-BB(F)TB(Me)-NCS (3-2) 5% 5-BB(F)TB(Me)-NCS (3-2) 5% 3-BB(F)TB(2Me,5F)-NCS (3-4) 13% 3-BTB(2Me,5F)TB-NCS (4-2) 13% 3-HBB(F,F)-NCS (5-2) 5% NI=102.6℃;Tc<-20℃;Δn=0.453;Δε=15.6;VHR=99.1%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M11 were as follows. Δε@28GHz=1.24 tanδ@28GHz=0.006

[0178] [Example 12] Liquid crystal composition M12 3-BTB(2Me)-NCS (1-7) 15% 4-BTB(2Me)-NCS (1-7) 10% 5-BTB(2Me)-NCS (1-7) 15% 3-BB(F)B(F,F)-NCS (2-2) 15% 3-BB(F)TB(Me)-NCS (3-2) 5% 5-BB(F)TB(Me)-NCS (3-2) 15% 5-BB(F)TB(2Me,5Me)-NCS (3-3) 5% 3-BTB(2Me,5F)TB-NCS (4-2) 10% 3-HBB(F,F)-NCS (5-2) 10% NI=119.7℃;Tc<-40℃;Δn=0.448;Δε=17.2;VHR=99.0%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M12 were as follows. Δε@28GHz=1.17 tanδ@28GHz=0.006

[0179] [Example 13] Liquid crystal composition M13 3-BTB(2Me)-NCS (1-7) 17% 4-BTB(2Me)-NCS (1-7) 11% 5-BTB(2Me)-NCS (1-7) 17% 3-BB(F)B(F,F)-NCS (2-2) 12% 3-BB(F)TB(Me)-NCS (3-2) 10% 3-BB(F)TB(2Me,5F)-NCS (3-4) 13% 3-BTB(2Me,5F)TB-NCS (4-2) 10% 3-HBB(F,F)-NCS (5-2) 10% NI=102.5℃;Tc<-30℃;Δn=0.444;Δε=15.6;VHR=99.2%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M13 were as follows. Δε@28GHz=1.18 tanδ@28GHz=0.006

[0180] [Example 14] Liquid crystal composition M14 3-BTB(2Me)-NCS (1-7) 17% 4-BTB(2Me)-NCS (1-7) 11% 5-BTB(2Me)-NCS (1-7) 17% 3-BB(F)B(F,F)-NCS (2-2) 17% 3-BB(F)TB(Me)-NCS (3-2) 5% 3-BB(F)TB(2Me,5F)-NCS (3-4) 13% 3-BTB(2Me,5F)TB-NCS (4-2) 10% 3-HBB(F,F)-NCS (5-2) 10% NI=101.1℃;Tc<-30℃;Δn=0.438;Δε=16.0;VHR=99.3%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M14 were as follows. Δε@28GHz=1.20 tanδ@28GHz=0.006

[0181] [Example 15] Liquid crystal composition M15 3-BTB(2Me)-NCS (1-7) 20% 4-BTB(2Me)-NCS (1-7) 10% 5-BTB(2Me)-NCS (1-7) 14% 3-BB(F)B(F,F)-NCS (2-2) 16% 3-BB(F)TB(Me)-NCS (3-2) 13% 5-BB(F)TB(Me)-NCS (3-2) 12% 3-BTB(2Me,5F)TB-NCS (4-2) 10% 5-BB(F)TB(2Me)B(F,F)-NCS (6-6) 5% NI=106.6℃;Tc<-20℃;Δn=0.464;Δε=15.3;VHR=99.2%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M15 were as follows. Δε@28GHz=1.25 tanδ@28GHz=0.006

[0182] [Example 16] Liquid crystal composition M16 3-BTB(2Me)-NCS (1-7) 20% 4-BTB(2Me)-NCS (1-7) 10% 5-BTB(2Me)-NCS (1-7) 14% 3-BB(F)B(F,F)-NCS (2-2) 16% 3-BB(F)TB(Me)-NCS (3-2) 13% 5-BB(F)TB(Me)-NCS (3-2) 12% 3-BTB(2Me,5F)TB-NCS (4-2) 10% 5-BB(F)TB(2F,5Me)TB-NCS (6-8) 5% NI=108.6℃;Tc<-30℃;Δn=0.470;Δε=14.8;VHR=99.2%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M16 were as follows. Δε@28GHz=1.26 tanδ@28GHz=0.006

[0183] [Example 17] Liquid crystal composition M17 3-BTB(2Me)-NCS (1-7) 14% 5-BTB(2Me)-NCS (1-7) 13% 3-BB(F)B(F,F)-NCS (2-2) 18% 3-BB(F)TB(Me)-NCS (3-2) 15% 5-BB(F)TB(Me)-NCS (3-2) 15% 3-BB(F)TB(2Me,5F)-NCS (3-4) 15% 3-BTB(2Me,5F)TB-NCS (4-2) 10% NI=137.3℃;Tc<-40℃;Δn=0.496;Δε=17.6;VHR=99.3%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M17 were as follows. Δε@28GHz=1.35 tanδ@28GHz=0.006

[0184] [Example 18] Liquid crystal composition M18 3-BTB(2Me)-NCS (1-7) 17% 4-BTB(2Me)-NCS (1-7) 10% 5-BTB(2Me)-NCS (1-7) 15% 3-BB(F)B(F,F)-NCS (2-2) 18% 3-BB(F)TB(Me)-NCS (3-2) 9% 5-BB(F)TB(Me)-NCS (3-2) 5% 3-BB(F)TB(2Me,5F)-NCS (3-4) 9% 3-BTB(2Me,5F)TB-NCS (4-2) 7% 1-BB(F)B-2V (7-3) 5% 2-BB(F)B-2V (7-3) 5% NI=102.0℃;Tc<-30℃;Δn=0.437;Δε=14.0;VHR=99.5%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M18 were as follows. Δε@28GHz=1.20 tanδ@28GHz=0.007

[0185] [Example 19] Liquid crystal composition M19 3-BTB(2Me)-NCS (1-7) 18% 4-BTB(2Me)-NCS (1-7) 10% 5-BTB(2Me)-NCS (1-7) 18% 3-BB(F)B(F,F)-NCS (2-2) 10% 3-BB(F)TB(Me)-NCS (3-2) 5% 5-BB(F)TB(Me)-NCS (3-2) 3% 3-BB(F)TB(2Me,5F)-NCS (3-4) 10% 3-BTB(2Me,5F)TB-NCS (4-2) 10% 3-HBB(F,F)-NCS (5-2) 16% NI=100.8℃;Tc<-40℃;Δn=0.430;Δε=15.1;VHR=99.2%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M19 were as follows. Δε@28GHz=1.21 tanδ@28GHz=0.006

[0186] [Example 20] Liquid crystal composition M20 3-BTB(2Me)-NCS (1-7) 20% 4-BTB(2Me)-NCS (1-7) 10% 5-BTB(2Me)-NCS (1-7) 15% 3-BB(F)B(F,F)-NCS (2-2) 10% 3-BB(F)TB(Me)-NCS (3-2) 10% 5-BB(F)TB(Me)-NCS (3-2) 10% 3-BB(F)TB(2Me,5F)-NCS (3-4) 5% 3-BTB(2Me,5F)TB-NCS (4-2) 10% 3-BB(F)TB-4 (7-4) 10% NI=101.9℃;Tc<-40℃;Δn=0.446;Δε=12.9;VHR=99.5%. The dielectric anisotropy at 28 GHz (Δε@28 GHz) and the dielectric loss tangent (tan δ@28 GHz) of the liquid crystal composition M20 were as follows. Δε@28GHz=1.20 tanδ@28GHz=0.006

[0187] The compositions of Examples 1 to 20 each contain Compound (1) to Compound (4), but do not contain Compound (S). The greater the content of Compound (1) to Compound (4) as a component of the composition, the greater the dielectric anisotropy at high frequencies. In particular, the smaller the value of tan δ@28 GHz. The liquid crystal compositions containing compounds (1) to (4) but not containing compound (S) were able to maintain the basic performance of the liquid crystal composition while maintaining a large Δε@28GHz and a small value of tanδ@28GHz.

[0188] The characteristics required for a liquid crystal composition are a large dielectric anisotropy (Δε) that enables large phase control in the frequency range used for phase control, and a small dielectric dissipation factor (tanδ), which is proportional to the absorption energy of the electromagnetic signal. The results of the examples and comparative examples demonstrate that the composition of the present invention has a large dielectric anisotropy (Δε @ 28 GHz) and a small dielectric dissipation factor (tanδ @ 28 GHz). Generally, a small tanδ results in a low absorption energy of the electromagnetic wave. Therefore, a liquid crystal composition using a compound represented by formula (1) can reduce the absorption energy of the electromagnetic signal and minimize the loss of the electromagnetic signal. From the above, it can be concluded that the liquid crystal composition of the present invention can transmit electromagnetic signals more efficiently. [Industrial Applicability]

[0189] The liquid crystal composition of the present invention has a high upper limit temperature of the nematic phase and a low lower limit temperature of the nematic phase, while satisfying high-frequency characteristics such as a large refractive index anisotropy and a small dielectric loss tangent (tan δ) in the frequency range required for controlling electromagnetic signals. Furthermore, the composition can further satisfy at least one of the following characteristics: a large dielectric anisotropy at low frequencies for reducing driving voltage, a small viscosity, a large resistivity in the driving frequency range, and thermal stability, thereby providing a more preferable liquid crystal composition. A device containing this composition can be used to control electromagnetic signals in the frequency range from 1 GHz to 10 THz.

Claims

1. A liquid crystal composition containing at least one compound selected from compounds represented by formula (1), at least one compound selected from compounds represented by formula (2), at least one compound selected from compounds represented by formula (3), and at least one compound selected from compounds represented by formula (4), and not containing a compound represented by formula (S). In formulas (1) to (4), R １ , R ２ , R ３ and R ４ is hydrogen, halogen, or a linear alkyl having 1 to 12 carbon atoms, and in this alkyl, at least one —CH ２ - may be replaced by -O- or -S-, and at least one -(CH ２ ) ２ - may be replaced by -CH=CH- or -C≡C-, and in these groups, at least one hydrogen may be replaced by halogen; L １１ , L １２ , L １３ , L ２１ , L ２２ , L ２３ , L ３１ , L ３２ , L ３３ , L ４１ , L ４２ , L ４３ , L ４４ and L ４５ is hydrogen, halogen, alkyl having 1 to 3 carbon atoms, or cycloalkyl having 3 to 5 carbon atoms; Y １１ , Y ２１ , Y ２２ , Y ２３ , Y ３１ , Y ３２ , Y ３３ , Y ３４ , Y ３５ , Y ３６ and Y ４１ is hydrogen or halogen; However, L １１ , L １２ and L １３ At least one of the groups is alkyl having 1 to 3 carbon atoms, and L ３１ , L ３２ and L ３３ At least one of these is alkyl having 1 to 3 carbon atoms. In formula (S), R Ｓ１ is hydrogen, halogen, or alkyl having 1 to 12 carbon atoms, and in this alkyl, at least one —CH ２ - may be replaced by -O- or -S-, and at least one -(CH ２ ) ２ - may be replaced by -CH=CH- or -C≡C-, and in these groups, at least one hydrogen may be replaced by halogen; L Ｓ１ , L Ｓ２ and L Ｓ３ is hydrogen or fluorine; Y Ｓ１ is hydrogen or fluorine.

2. The liquid crystal composition according to claim 1 , which does not contain a compound represented by formula (T): In formula (T), R Ｔ１ is hydrogen, halogen, or alkyl having 1 to 12 carbon atoms, and in this alkyl, at least one —CH ２ - may be replaced by -O- or -S-, and at least one -(CH ２ ) ２ - may be replaced by -CH=CH- or -C≡C-, and in these groups, at least one hydrogen may be replaced by halogen; Y Ｔ１ and Y Ｔ２ is hydrogen or fluorine; t is 0 or 1.

3. The liquid crystal composition according to claim 1, comprising, as the compound represented by formula (1), at least one compound selected from the group of compounds represented by formulas (1-1) to (1-10): In formulas (1-1) to (1-10), R １’ is a linear alkyl having 1 to 12 carbon atoms, and in this alkyl, at least one -(CH ２ ) ２ - may be replaced by -CH=CH- or -C≡C-.

4. The liquid crystal composition according to claim 1, comprising, as the compound represented by formula (2), at least one compound selected from the group of compounds represented by formulas (2-1) to (2-10): In the formulas (2-1) to (2-10), R ２’ is a linear alkyl having 1 to 12 carbon atoms, and in this alkyl, at least one -(CH ２ ) ２ - may be replaced by -CH=CH- or -C≡C-; Y ２２’ is hydrogen, fluorine or chlorine; In formula (2-10), Y ２１’ is hydrogen, fluorine or chlorine.

5. The liquid crystal composition according to claim 1, comprising, as the compound represented by formula (3), at least one compound selected from the group of compounds represented by formulas (3-1) to (3-11): In the formulas (3-1) to (3-11), R ３’ is a linear alkyl having 1 to 12 carbon atoms, and in this alkyl, at least one -(CH ２ ) ２ - may be replaced by -CH=CH- or -C≡C-; Y ３５’ is hydrogen, fluorine or chlorine.

6. The liquid crystal composition according to claim 1, comprising, as the compound represented by formula (4), at least one compound selected from the group of compounds represented by formulas (4-1) to (4-7): In the formulas (4-1) to (4-7), R ４’ is a linear alkyl having 1 to 12 carbon atoms, and in this alkyl, at least one -(CH ２ ) ２ - may be replaced by -CH=CH- or -C≡C-; L ４４’ and L ４５’ is hydrogen, fluorine, chlorine, methyl or ethyl; Y ４１’ is hydrogen, fluorine or chlorine.

7. 2. The liquid crystal composition according to claim 1, wherein, based on the weight of the liquid crystal composition, the proportion of the compound represented by formula (1) is in the range of 15% by weight to 65% by weight, the proportion of the compound represented by formula (2) is in the range of 5% by weight to 40% by weight, the proportion of the compound represented by formula (3) is in the range of 10% by weight to 55% by weight, and the proportion of the compound represented by formula (4) is in the range of 5% by weight to 20% by weight.

8. 2. The liquid crystal composition according to claim 1, further comprising at least one compound selected from the group consisting of a compound represented by formula (5), a compound represented by formula (6), and a compound represented by formula (7): In equations (5) to (7), R ５ , R ６ , R ７１ and R ７２ is hydrogen, halogen, or alkyl having 1 to 12 carbon atoms, and in this alkyl, at least one —CH ２ - may be replaced by -O- or -S-, and at least one -(CH ２ ) ２ - may be replaced by -CH=CH- or -C≡C-, and in these groups, at least one hydrogen may be replaced by halogen; L ５１ , L ５２ , L ５３ , L ６１ , L ６２ , L ６３ , L ６４ , L ７１ , L ７２ , L ７３ , L ７４ , L ７５ , L ７６ and L ７７ is hydrogen, halogen, alkyl having 1 to 3 carbon atoms, or cycloalkyl having 3 to 5 carbon atoms; Y ５１ , Y ５２ and Y ６１ is hydrogen or halogen; Ring A is 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, or pyridine-2,5-diyl, and at least one hydrogen on these rings may be replaced by halogen or alkyl having 1 to 3 carbon atoms; Z ６１ and Z ６２ is a single bond, —C≡C— or —C≡C-C≡C—; a is 0, 1 or 2; b is 1, 2 or 3; a+b is 3; c and d are 0 or 1; and e is 0, 1 or 2.

9. The liquid crystal composition according to claim 8, comprising, as the compound represented by formula (5), at least one compound selected from the group of compounds represented by formulas (5-1) to (5-10): In the formulas (5-1) to (5-10), R ５’ is an alkyl having 1 to 12 carbon atoms, and in this alkyl, at least one —(CH ２ ) ２ - may be replaced by -CH=CH- or -C≡C-; Y ５１’ is hydrogen, fluorine or chlorine.

10. The liquid crystal composition according to claim 8, comprising, as the compound represented by formula (6), at least one compound selected from the group of compounds represented by formulas (6-1) to (6-8): In the formulas (6-1) to (6-8), R ６’ is an alkyl having 1 to 12 carbon atoms, and in this alkyl, at least one —(CH ２ ) ２ - may be replaced by -CH=CH- or -C≡C-; L ６１’ , L ６２’ , L ６３’ and L ６４’ is hydrogen, fluorine, chlorine, methyl or ethyl; Y ６１’ is hydrogen, fluorine or chlorine.

11. The liquid crystal composition according to claim 8, comprising, as the compound represented by formula (7), at least one compound selected from the group of compounds represented by formulas (7-1) to (7-6): In the formulas (7-1) to (7-6), R ７１’ and R ７２’ is an alkyl having 1 to 12 carbon atoms, and in this alkyl, at least one —(CH ２ ) ２ - may be replaced by -CH=CH- or -C≡C-; In formula (7-1) and formula (7-2), L ７５’ , L ７６’ and L ７７’ is hydrogen, fluorine, chlorine, methyl or ethyl: In formula (7-3), L ７２’ , L ７４’ , L ７５’ , L ７６’ and L ７７’ is hydrogen, fluorine, chlorine, methyl or ethyl; In formula (7-4), L ７１’ , L ７３’ , L ７５’ , L ７６’ and L ７７’ is hydrogen, fluorine, chlorine, methyl or ethyl; In the formula (7-5) and the formula (7-6), L ７１’ , L ７２’ , L ７３’ , L ７４’ , L ７５’ , L ７６’ and L ７７’ is hydrogen, fluorine, chlorine, methyl or ethyl.

12. 9. The liquid crystal composition according to claim 8, wherein, based on the weight of the liquid crystal composition, the proportion of the compound represented by formula (5) is in the range of 0% by weight to 30% by weight, the proportion of the compound represented by formula (6) is in the range of 0% by weight to 25% by weight, the proportion of the compound represented by formula (7) is in the range of 0% by weight to 50% by weight, and the total proportion of these compounds is in the range of 5% by weight to 50% by weight.

13. 2. The liquid crystal composition according to claim 1, wherein the refractive index anisotropy at 25[deg.] C. at a wavelength of 589 nm is 0.40 or more.

14. 2. The liquid crystal composition according to claim 1, wherein the dielectric anisotropy at 25° C. at a frequency of 1 kHz is 10 or more.

15. 2. The liquid crystal composition according to claim 1, wherein the dielectric anisotropy at 25° C. in at least one frequency range of 1 GHz to 10 THz is in the range of 1.0 to 3.

0.

16. The liquid crystal composition according to claim 1 , comprising an optically active compound.

17. The liquid crystal composition according to claim 1 , comprising a polymerizable compound.

18. 2. The liquid crystal composition according to claim 1, further comprising at least one of an antioxidant, an ultraviolet absorber, an antistatic agent, and a dichroic dye.

19. 10. An element containing the liquid crystal composition according to claim 1, wherein the dielectric constant can be reversibly controlled by reversibly changing the alignment direction of liquid crystal molecules, and the element is used for switching.

20. 10. A device used for controlling electromagnetic waves in the frequency range of 1 GHz to 10 THz, comprising the liquid crystal composition according to claim 1.

21. A liquid crystal lens, a birefringent lens for stereoscopic image display, or a light modulation element, comprising the liquid crystal composition according to claim 1.

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