Liquid crystal composition and liquid crystal element

Abstract

To provide a liquid crystal composition which fulfills at least one property among a high upper limit temperature of a cholesteric phase, a low lower limit temperature of a cholesteric phase, small viscosity, large optical anisotropy, large dielectric anisotropy, large specific resistivity, high stability against light, high stability against heat, a proper helical pitch length, and small temperature dependence of the pitch length, or which has a proper balance concerning at least two of the properties, and to provide a cholesteric liquid crystal element including the composition.SOLUTION: The liquid crystal composition contains, as component A, a specific compound with large dielectric anisotropy, as component B, a specific compound with large optical anisotropy and dielectric anisotropy, and, as additive X, an optically active compound, and may additionally contain, as component C, a specific compound with large dielectric anisotropy, as component D, a specific compound with small viscosity or large optical anisotropy, or as component E, a specific compound with large dielectric anisotropy in the short-axis direction.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a liquid crystal composition, a liquid crystal reflective element and a liquid crystal display element containing the composition, etc. In particular, the present invention relates to a liquid crystal composition having a cholesteric phase and an element that drives the cholesteric liquid crystal composition. [Background technology]

[0002] Liquid crystal devices are classified based on the operating mode of the liquid crystal molecules, including phase change (PC), twisted nematic (TN), super twisted nematic (STN), electrically controlled birefringence (ECB), optically compensated bend (OCB), in-plane switching (IPS), vertical alignment (VA), fringe field switching (FFS), and field-induced photo-reactive alignment (FPA). They are classified based on their driving method, including passive matrix (PM) and active matrix (AM). PMs are further divided into static and multiplex, while AMs are further divided into thin film transistors (TFTs) and metal insulator metal (MIMs). TFTs are classified into amorphous silicon and polycrystalline silicon. The latter are further divided into high-temperature and low-temperature types based on the manufacturing process. They are classified based on the light source, including reflective types that use natural light, transmissive types that use backlight, and transflective types that use both natural light and backlight.

[0003] Liquid crystal compositions containing optically active compounds may exhibit a "cholesteric phase." This cholesteric phase is a liquid crystal phase in which the orientational order of the molecules rotates in a helical fashion. The helical axis is perpendicular to the direction of the orientational order. The period of this helix is called the "pitch."

[0004] Liquid crystal devices containing liquid crystal compositions that exhibit a "cholesteric phase" are known. These liquid crystal compositions have a pitch length comparable to that of visible light. Liquid crystal compositions that exhibit a cholesteric phase selectively reflect circularly polarized light, and the direction of rotation of the light vector corresponds to the handedness of the cholesteric helix. The reflected wavelength λ can be calculated from the cholesteric helix pitch P and the average birefringence index n of the cholesteric liquid crystal using equation (A). λ=n×P (A)

[0005] A cholesteric liquid crystal device contains a liquid crystal composition having a cholesteric phase, i.e., a cholesteric liquid crystal composition. This composition has suitable properties. By improving the properties of this composition, a liquid crystal device with good properties can be obtained. The relationship between the two properties is summarized in Table 1 below. The properties of the composition will be further explained based on a commercially available liquid crystal device. The temperature range of the cholesteric phase is related to the temperature range in which the device can be used. The preferred upper limit temperature of the cholesteric phase is about 70°C or higher, and the preferred lower limit temperature of the cholesteric phase is about -10°C or lower. A high resistivity in the composition contributes to a high voltage holding ratio in the device. Therefore, a composition that has a high resistivity not only at room temperature but also at temperatures close to the upper limit temperature of the cholesteric phase is preferred. A composition that has a high resistivity not only at room temperature but also at temperatures close to the upper limit temperature of the cholesteric phase after long-term use is preferred. The resistivity of the liquid crystal composition at room temperature is preferably 1×10 10 Ω·cm or more, and more preferably 1×10 12 Ω·cm or more, and more preferably 1×10 14 Ω·cm or more. TIFF2025121829000001.tif58166

[0006] The optical anisotropy of a composition is related to the brightness of the display of the device. To achieve a bright display, a liquid crystal composition with large optical anisotropy is required. The optical anisotropy at a wavelength of 589 nm (measured at 25°C) is preferably in the range of 0.10 to 0.40, more preferably in the range of 0.12 to 0.35, and even more preferably in the range of 0.15 to 0.30. A large dielectric anisotropy of the composition is desirable because it contributes to a low driving voltage of the device. The dielectric anisotropy at a frequency of 1 kHz (measured at 25°C) is preferably in the range of 10 to 100, more preferably in the range of 15 to 80, and even more preferably in the range of 25 to 60. The viscosity of the composition is related to the response time of the device. A short response time is desirable for displaying moving images with the device. A response time shorter than 1 millisecond is desirable. Therefore, a low viscosity of the composition is desirable. The viscosity at 20°C is preferably 120 mPa·s or less, more preferably 80 mPa·s or less. A small viscosity at low temperatures is more preferable. The helical pitch length in the composition is preferably such that the reflection wavelength can be adjusted to the visible region with as little added amount of optically active compound as possible so as not to impair the properties of the host nematic liquid crystal composition. Furthermore, it is preferable that the temperature dependence of the helical pitch length is almost zero or small so as not to deteriorate the display quality due to changes in environmental temperature.

[0007] The most common cholesteric liquid crystal devices are SSCT (surface stabilized cholesteric texture) and PSCT (polymer stabilized cholesteric texture) devices. SSCT and PSCT devices typically contain cholesteric liquid crystal compositions, which initially exhibit a planar structure that reflects light of a specific wavelength, and can be switched to a focal conic light-scattering structure by applying an alternating current pulse, or vice versa.

[0008] These liquid crystal devices are bistable, meaning that each state is maintained after the electric field is switched off and can only be reversed by reapplying the electric field. When a higher voltage pulse is applied, the cholesteric liquid crystal composition transitions to a homeotropic, transparent state, from which it relaxes to a planar state if the voltage is switched to zero quickly or to a focal conic state if the voltage is switched slowly. The minimum drive voltage required to return from the planar state (reflective) to the homeotropic phase (transmissive) is called the Vreset voltage. The lower this drive voltage, the less power consumed.

[0009] Cholesteric liquid crystal devices generally do not require a backlight. In the planar state, the cholesteric liquid crystal composition in a pixel selectively reflects light of a specific wavelength according to formula (A) above. As a result, the pixel appears to reflect a corresponding color, for example, against a black background. This reflected color disappears upon transition to a scattering state due to the focal conic structure or a homeotropic transparent state. For these reasons, cholesteric liquid crystal devices consume significantly less power. Furthermore, in the scattering state, they exhibit little, if any, viewing angle dependence. Therefore, these displays do not require active matrix addressing and can operate in simpler multiplex or passive matrix modes. However, due to the poor display quality, devices combining an active matrix with the aim of improving this have been reported (Patent Documents 1 and 2). [Prior art documents] [Patent documents]

[0010] [Patent Document 1] Japanese Patent Application Publication No. 7-140440 [Patent Document 2] Japanese Patent Application Laid-Open No. 2010-275463 Summary of the Invention [Problem to be solved by the invention]

[0011] An object of the present invention is to provide a liquid crystal composition that satisfies at least one of the following properties: a high maximum temperature of the cholesteric phase, a low minimum temperature of the cholesteric phase, a small viscosity, a large optical anisotropy, a positively large dielectric anisotropy, a large resistivity, high stability to light, high stability to heat, an appropriate helical pitch length, and a small temperature dependence of the pitch length. Another object is to provide a liquid crystal composition that has an appropriate balance between at least two of these properties. Another object is to provide a liquid crystal device containing such a composition. Another object is to provide a cholesteric liquid crystal device that has properties such as a short response time, a large voltage holding ratio, a low Vreset voltage (the voltage at which the liquid crystal switches from the initial reflective state to the transmissive state), a large contrast ratio, and a long lifespan. [Means for solving the problem]

[0012] The present invention relates to a liquid crystal composition having a cholesteric phase, which contains as component A at least one compound selected from compounds represented by formula (1), as component B at least one compound selected from compounds represented by formula (2), and as additive X an optically active compound, and a liquid crystal device containing the composition. TIFF2025121829000002.tif56112 In formula (1), R 1 is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms; ring A is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, or tetrahydropyran-2,5-diyl; Z 1 is a single bond, carbonyloxy, or difluoromethyleneoxy; X 1 and X 2 is hydrogen or fluorine; a is 1 or 2; In equation (2), R 2is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms; Z 2 is carbonyloxy or difluoromethyleneoxy; X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 is hydrogen or fluorine; Y 1 is fluorine, chlorine, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, alkoxy having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. [Effects of the Invention]

[0013] The present invention has the advantage of providing a liquid crystal composition that satisfies at least one of the following characteristics: a high upper limit temperature of the cholesteric phase, a low lower limit temperature of the cholesteric phase, a small viscosity, a large optical anisotropy, a positively large dielectric anisotropy, a large resistivity, high stability to light, high stability to heat, an appropriate helical pitch length, and a small temperature dependence of the pitch length. Another advantage is to provide a liquid crystal composition that has an appropriate balance between at least two of these characteristics. Another advantage is to provide a liquid crystal device containing such a composition. Another advantage is to provide a cholesteric liquid crystal device that has properties such as a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long lifespan. DETAILED DESCRIPTION OF THE INVENTION

[0014] The terms used in this specification are as follows. The terms "liquid crystal composition" and "liquid crystal display element" may be abbreviated as "composition" and "element," respectively. "Liquid crystal display element" is a general term for liquid crystal display panels and liquid crystal display modules. "Liquid crystal compound" is a general term for compounds that have a liquid crystal phase, such as a nematic phase, cholesteric phase, or smectic phase, and compounds that do not have a liquid crystal phase but are mixed into a composition for the purpose of adjusting 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 for the purpose of forming a polymer. Liquid crystal compounds containing alkenyl are not classified as polymerizable compounds in this sense.

[0015] A liquid crystal composition is prepared by mixing multiple liquid crystal compounds. Additives such as optically active compounds are added to this liquid crystal composition as needed. The proportion of the liquid crystal compounds is expressed as a mass percentage (mass%) based on the mass of the liquid crystal composition without the additives, even when additives are added. The proportion of the additives is expressed as a mass percentage (mass%) based on the mass of the liquid crystal composition without the additives. That is, the proportions of the liquid crystal compounds and additives are calculated based on the total mass of the liquid crystal compounds.

[0016] A liquid crystal composition before adding an additive such as an optically active compound is sometimes called a “host liquid crystal composition.” A liquid crystal composition that has been made to exhibit a cholesteric phase by adding an optically active compound to this host liquid crystal composition is sometimes called a “cholesteric liquid crystal” or a “cholesteric liquid crystal composition.”

[0017] The "maximum temperature of a nematic or cholesteric phase" is sometimes abbreviated as the "maximum temperature." The "minimum temperature of a nematic or cholesteric phase" is sometimes abbreviated as the "minimum temperature." The expression "increasing the dielectric anisotropy" means that the value increases positively for a composition with a positive dielectric anisotropy, and that the value increases negatively for a composition with a negative dielectric anisotropy. "High resistivity" means that the composition has high resistivity not only at room temperature but also at temperatures close to the maximum temperature of the cholesteric phase in the initial stage, and that after prolonged use, it has high resistivity not only at room temperature but also at temperatures close to the maximum temperature of the cholesteric phase. "High voltage holding ratio" means that the element has high voltage holding ratio not only at room temperature but also at temperatures close to the maximum temperature of the cholesteric phase in the initial stage, and that after prolonged use, it has high voltage holding ratio not only at room temperature but also at temperatures close to the maximum temperature of the cholesteric phase.

[0018] TIFF2025121829000003.tif2693 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 any two 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.

[0019] 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, where the group represented by Ra and the group represented by Rb may be the same or different.

[0020] 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).

[0021] 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).

[0022] The alkyl of the liquid crystal compound is linear or branched, and does not include cyclic alkyl. Linear alkyl is preferred to branched alkyl. The same applies to terminal groups such as alkoxy and alkenyl. The trans configuration of 1,4-cyclohexylene is preferred over cis to increase the maximum temperature. 2-Fluoro-1,4-phenylene is asymmetric, so it exists in left-facing (L) and right-facing (R) configurations. TIFF2025121829000004.tif30133 The same applies to divalent groups such as tetrahydropyran-2,5-diyl, and to linking groups such as carbonyloxy (-COO- or -OCO-).

[0023] The present invention includes the following items.

[0024] Item 1. A liquid crystal composition having a cholesteric phase, comprising as component A at least one compound selected from compounds represented by formula (1), as component B at least one compound selected from compounds represented by formula (2), and as additive X an optically active compound. TIFF2025121829000005.tif56112 In formula (1), R 1 is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms; ring A is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, or tetrahydropyran-2,5-diyl; Z 1 is a single bond, carbonyloxy, or difluoromethyleneoxy; X 1 and X 2 is hydrogen or fluorine; a is 1 or 2; In equation (2), R 2 is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms; Z 2 is carbonyloxy or difluoromethyleneoxy; X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 is hydrogen or fluorine; Y 1is fluorine, chlorine, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, alkoxy having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine.

[0025] Item 2. The liquid crystal composition according to item 1, comprising, as component A, at least one compound selected from the compounds represented by formulas (1-1) to (1-9): TIFF2025121829000006.tif209108 In formulas (1-1) to (1-9), R 1 is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms; X 1 and X 2 is hydrogen or fluorine.

[0026] Item 3. The liquid crystal composition according to item 1 or 2, wherein the proportion of component A is in the range of 5% by mass to 50% by mass.

[0027] Item 4. The liquid crystal composition according to any one of items 1 to 3, comprising, as component B, at least one compound selected from the compounds represented by formulae (2-1) to (2-8): TIFF2025121829000007.tif201118 In formulas (2-1) to (2-8), R 2 is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms; Y 1 is fluorine, chlorine, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, alkoxy having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine.

[0028] Item 5. The liquid crystal composition according to any one of items 1 to 4, wherein the proportion of component B is in the range of 5% by mass to 50% by mass.

[0029] Item 6. The liquid crystal composition according to any one of items 1 to 5, containing at least one compound selected from the compounds represented by formula (3-1) to formula (3-7) as additive X: TIFF2025121829000008.tif221121 In formulas (3-1) to (3-7), R 3 and R 4 is hydrogen, halogen, —C≡N, —N═C═O, —N═C═S, —SF5, or alkyl having 1 to 10 carbon atoms, in which at least one —CH2— may be replaced by —O—, —COO—, —OCO—, —CH═CH—, or —C≡C—, and in these groups at least one hydrogen may be replaced by fluorine or chlorine.

[0030] Item 7. The liquid crystal composition according to any one of items 1 to 6, wherein the proportion of the additive X is in the range of 0.1% by mass to 10% by mass.

[0031] Item 8. The liquid crystal composition according to any one of items 1 to 7, comprising, as component C, at least one compound selected from compounds represented by formula (4): TIFF2025121829000009.tif23108 In equation (4), R 5 is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms; ring B is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, or tetrahydropyran-2,5-diyl; Z 3 is a single bond, ethylene, vinylene, carbonyloxy, or difluoromethyleneoxy; X 9 and X 10 is hydrogen or fluorine; Y2 is fluorine, chlorine, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, alkoxy having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine; and b is 1, 2, 3, or 4.

[0032] Item 9. The liquid crystal composition according to any one of items 1 to 8, comprising, as component C, at least one compound selected from the compounds represented by formula (4-1) to formula (4-26): TIFF2025121829000010.tif214124 TIFF2025121829000011.tif228128 TIFF2025121829000012.tif224127 In equations (4-1) to (4-26), R 5 is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms.

[0033] Item 10. The liquid crystal composition according to item 8 or 9, wherein the proportion of component C is in the range of 1% by mass to 50% by mass.

[0034] Item 11. The liquid crystal composition according to any one of items 1 to 10, comprising, as component D, at least one compound selected from compounds represented by formula (5): TIFF2025121829000013.tif13131 In equation (5), R 6 and R 7 is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine; ring C and ring D are 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene; Z 4is a single bond, ethylene, vinylene, ethynylene, methyleneoxy, or carbonyloxy; and c is 1, 2, or 3.

[0035] Item 12. The liquid crystal composition according to any one of items 1 to 11, comprising, as component D, at least one compound selected from the compounds represented by formulae (5-1) to (5-20): TIFF2025121829000014.tif231106 TIFF2025121829000015.tif135107 In equations (5-1) to (5-20), R 6 and R 7 is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen has been replaced by fluorine or chlorine.

[0036] Item 13. The liquid crystal composition according to item 11 or 12, wherein the proportion of component D is in the range of 10% by mass to 90% by mass.

[0037] Item 14. The liquid crystal composition according to any one of items 1 to 13, comprising, as component E, at least one compound selected from compounds represented by formula (6): TIFF2025121829000016.tif16111 In equation (6), R 8 and R 9is hydrogen, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkenyloxy having 2 to 12 carbon atoms, or alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine; ring E and ring G are 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl in which at least one hydrogen is replaced by fluorine or chlorine, chroman-2,6-diyl, or at least one water ring F is 2,3-difluoro-1,4-phenylene, 1,8-difluorophenanthrene-2,7-diyl, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4,5-trifluoronaphthalene-2,6-diyl, 7,8-difluorochroman-2,6-diyl, 3,4,5,6-tetrafluorofluorene-2,7-diyl, 4,6-difluorodibenzofuran-3,7-diyl, 4,6-difluorodibenzothiophene-3,7-diyl, or 1,1,6,7-tetrafluoroindan-2,5-diyl; Z is 5 and Z 6 is a single bond, ethylene, vinylene, methyleneoxy, or carbonyloxy; d is 0, 1, 2, or 3; e is 0 or 1; and the sum of d and e is 3 or less.

[0038] Item 15. The liquid crystal composition according to any one of items 1 to 14, comprising, as component E, at least one compound selected from the compounds represented by formulae (6-1) to (6-36): TIFF2025121829000017.tif226123 TIFF2025121829000018.tif230127 TIFF2025121829000019.tif230126 TIFF2025121829000020.tif59125 In equations (6-1) to (6-36), R 8 and R 9 is hydrogen, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkenyloxy having 2 to 12 carbon atoms, or alkyl having 1 to 12 carbon atoms in which at least one hydrogen has been replaced by fluorine or chlorine.

[0039] Item 16. The liquid crystal composition according to item 14 or 15, wherein the proportion of component E is in the range of 1% by mass to 10% by mass.

[0040] Item 17. The liquid crystal composition according to any one of items 1 to 16, containing, as additive Y, at least one compound selected from polymerizable compounds represented by formula (7): TIFF2025121829000021.tif3099 In formula (7), ring I and ring K are cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxan-2-yl, pyrimidin-2-yl, or pyridin-2-yl, and in these rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine; ring J is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-2,6-diyl, naphthalene-3,7-diyl, naphthalene-4,8-diyl, naphthalene-5,9-diyl, naphthalene-6,10-diyl, naphthalene-7,11-diyl, naphthalene-8,12-diyl, naphthalene-9,13-diyl, naphthalene-14,15-diyl, naphthalene-16,16-diyl, naphthalene-17,18-diyl, naphthalene-19,19-diyl, naphthalene-20,19-diyl, naphthalene-21,19-diyl, naphthalene-22,19-diyl, naphthalene-23,19-diyl, naphthalene-24,19-diyl, naphthalene-25,19-diyl, naphthalene-31,19-diyl, naphthalene-42,19-diyl, naphthalene-53,19-diyl, phthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, in which at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by fluorine; Z 7 and Z 8 represents a single bond or alkylene having 1 to 10 carbon atoms, in which at least one -CH2- may be replaced by -O-, -CO-, -COO-, or -OCO-, and at least one -CH2CH2- may be replaced by -CH=CH-, -C(CH3)=CH-, -CH=C(CH3)-, or -C(CH3)=C(CH3)-, and in these groups at least one hydrogen may be replaced by fluorine; P 1 From P 3 is a polymerizable group; Sp 1 From Sp 3 is a single bond or an alkylene having 1 to 10 carbon atoms, and Sp 1 From Sp 3wherein at least one -CH2- may be replaced by -O-, -COO-, -OCO-, or -OCOO-, at least one -CH2CH2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine; i is 0, 1, or 2; f, g, and h are 0, 1, 2, 3, or 4; and the sum of f, g, and h is 1 or greater.

[0041] Item 18. In equation (7), P 1 From P 3 Item 18. The liquid crystal composition according to item 17, wherein is a group selected from polymerizable groups represented by formulae (P-1) to (P-5): TIFF2025121829000022.tif28145 In formulas (P-1) to (P-5), M 1 From M 3 is hydrogen, fluorine, alkyl having 1 to 5 carbon atoms, or alkyl having 1 to 5 carbon atoms in which at least one hydrogen atom is replaced by fluorine, and M 1 From M 3 In the formula, at least one —CH 2 — in the alkyl may be replaced with —O—.

[0042] Item 19. The liquid crystal composition according to any one of items 1 to 18, containing, as additive Y, at least one compound selected from the polymerizable compounds represented by formula (7-1) to formula (7-29): TIFF2025121829000023.tif211101 TIFF2025121829000024.tif244112 TIFF2025121829000025.tif185111 In equations (7-1) to (7-29), Sp 1 From Sp 3 is a single bond or an alkylene having 1 to 10 carbon atoms, and Sp 1 From Sp 3In the formula (I), at least one -CH2- may be replaced by -O-, -COO-, -OCO-, or -OCOO-, at least one -CH2CH2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine. ;P 4 From P 6 is a polymerizable group selected from groups represented by formulas (P-1) to (P-3); TIFF2025121829000026.tif3497 In formulas (P-1) to (P-3), M 1 From M 3 is hydrogen, fluorine, alkyl having 1 to 5 carbon atoms, or alkyl having 1 to 5 carbon atoms in which at least one hydrogen atom is replaced by fluorine, and M 1 From M 3 In the formula, at least one —CH 2 — in the alkyl may be replaced with —O—.

[0043] Item 20. The liquid crystal composition according to any one of items 17 to 19, wherein the proportion of the additive Y is in the range of 0.1% by mass to 5% by mass.

[0044] Item 21. The liquid crystal composition according to any one of items 1 to 20, which has an optical anisotropy at a wavelength of 589 nm (measured at 25° C.) of 0.16 or more.

[0045] Item 22. A liquid crystal device containing the liquid crystal composition according to any one of items 1 to 21.

[0046] Item 23. The liquid crystal device according to item 22, which is a liquid crystal display device or a liquid crystal reflective device.

[0047] The present invention also includes the following: (a) the above composition containing one compound, two compounds, or three or more compounds selected from additives such as antioxidants, UV absorbers, quenchers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, and polar compounds; (b) an AM element containing the above composition; (e) an element containing the above composition and having a PC, TN, STN, ECB, OCB, IPS, VA, FFS, or FPA mode; (f) a transmission element containing the above composition; and (g) use of the above composition as a composition having a cholesteric phase.

[0048] The composition of the present invention will be described in the following order: First, the constitution of the composition will be described; Second, the main properties of the component compounds and the main effects that these compounds have on the composition and the device will be described; Third, the combination of component compounds in the composition, their preferred ratios, and the reasons therefor 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.

[0049] First, the composition will be described. This composition contains multiple liquid crystal compounds. This composition may contain additives. Additives include optically active compounds, antioxidants, UV absorbers, quenchers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, and polar compounds. This composition is classified into Composition A and Composition B based on the liquid crystal compounds. Composition A may further contain other liquid crystal compounds, other additives, and the like, in addition to compounds selected from Compound (1), Compound (2), Additive X, Compound (4), Compound (5), and Compound (6). "Other liquid crystal compounds" are liquid crystal compounds other than Compound (1), Compound (2), Compound (4), Compound (5), and Compound (6). Such compounds are mixed into the composition to further adjust its properties.

[0050] Composition B consists essentially of compounds selected from Compound (1), Compound (2), Additive X, Compound (4), Compound (5), and Compound (6). "Substantially" means that Composition B may contain other 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. Composition A is preferable to Composition B from the viewpoint of being able to further adjust the properties by mixing other liquid crystal compounds.

[0051] Second, the main properties of the component compounds and the main effects that these compounds have on the composition and device are explained. The main properties of the component compounds are summarized in Table 2. In the symbols in Table 2, 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 the symbol 0 (zero) means smaller than S.

[0052] TIFF2025121829000027.tif65164

[0053] The main effects of the component compounds are as follows: Compound (1) increases the dielectric anisotropy; Compound (2) increases the dielectric anisotropy and decreases the minimum temperature; Additive X is an optically active compound that, when added to a liquid crystal composition having a nematic phase, produces a cholesteric phase, and the desired reflection wavelength can be adjusted by adjusting the amount added; Compound (4) increases the dielectric anisotropy or increases the optical anisotropy; Compound (5) decreases the viscosity or increases the optical anisotropy; and Compound (6) increases the optical anisotropy or decreases the minimum temperature.

[0054] Third, the combinations of component compounds in the composition, their preferred ratios, and the rationale for them will be explained. Preferred combinations of component compounds in the composition are Compound (1) + Compound (2) + Additive X, Compound (1) + Compound (2) + Additive X + Compound (4), Compound (1) + Compound (2) + Additive X + Compound (5), Compound (1) + Compound (2) + Additive X + Compound (6), Compound (1) + Compound (2) + Additive X + Compound (4) + Compound (5), Compound (1) + Compound (2) + Additive X + Compound (4) + Compound (6), Compound (1) + Compound (2) + Additive X + Compound (5) + Compound (6), or Compound (1) + Compound (2) + Additive X + Compound (4) + Compound (5) + Compound (6). A particularly preferred combination is Compound (1) + Compound (2) + Additive X + Compound (4) + Compound (5).

[0055] A preferred ratio of compound (1) is about 5% by mass or more for increasing the dielectric anisotropy, and about 50% by mass or less for decreasing the minimum temperature. A more preferred ratio is from about 10% by mass to about 40% by mass. A particularly preferred ratio is from about 15% by mass to about 40% by mass.

[0056] A preferred ratio of compound (2) is about 5% by mass or more for increasing the dielectric anisotropy, and about 50% by mass or less for decreasing the minimum temperature. A more preferred ratio is from about 5% by mass to about 30% by mass. A particularly preferred ratio is from about 10% by mass to about 25% by mass.

[0057] A preferred ratio of additive X is about 0.1% by mass or more to exhibit a cholesteric phase and about 10% by mass or less to lower the minimum temperature. A more preferred ratio is in the range of about 0.5% by mass to about 7% by mass. A particularly preferred ratio is in the range of about 1% by mass to about 6% by mass.

[0058] A preferred ratio of compound (4) is about 1% by mass or more for increasing the dielectric anisotropy, and about 50% by mass or less for decreasing the minimum temperature. A more preferred ratio is from about 5% by mass to about 30% by mass. A particularly preferred ratio is from about 10% by mass to about 25% by mass.

[0059] A preferred ratio of compound (5) is about 10% by mass or more for increasing the optical anisotropy or decreasing the viscosity, and about 90% by mass or less for increasing the dielectric anisotropy. A more preferred ratio is in the range of about 15% to about 60% by mass. A particularly preferred ratio is in the range of about 20% to about 50% by mass.

[0060] A preferred ratio of compound (6) is about 1% by mass or more for increasing the optical anisotropy, and about 10% by mass or less for increasing the dielectric anisotropy. A more preferred ratio is from about 2% to about 8% by mass. A particularly preferred ratio is from about 2% to about 6% by mass.

[0061] Fourth, preferred forms of the component compounds will be described. In formula (1), formula (2), formula (3-1) to formula (3-7), formula (4), formula (5), and formula (6), R 1 is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms. 1 is alkyl having 1 to 12 carbon atoms for increasing stability, and alkenyl having 2 to 12 carbon atoms for decreasing the minimum temperature. 2 is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms. 2 is an alkyl having 1 to 12 carbon atoms to increase stability. 3 and R 4 is hydrogen, halogen, —C≡N, —N═C═O, —N═C═S, —SF5, or alkyl having 1 to 10 carbon atoms, in which at least one —CH2— may be replaced by —O—, —COO—, —OCO—, —CH═CH—, or —C≡C—, and in these groups at least one hydrogen may be replaced by fluorine or chlorine. 3 or R 4 is an alkyl having 1 to 12 carbon atoms to increase stability. 5is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms. 5 is an alkyl having 1 to 12 carbon atoms to increase stability. 6 and R 7 is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. 6 or R 7 is an alkyl having 1 to 12 carbon atoms to increase stability, or an alkenyl having 2 to 12 carbon atoms to decrease viscosity. 8 and R 9 is hydrogen, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkenyloxy having 2 to 12 carbon atoms, or alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. 8 or R 9 is an alkyl having 1 to 12 carbon atoms to increase stability, an alkenyl having 2 to 12 carbon atoms to decrease viscosity, or an alkoxy having 1 to 12 carbon atoms to increase the dielectric constant in the minor axis direction.

[0062] Preferred alkyl groups are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl, and more preferred alkyl groups are methyl, ethyl, propyl, butyl, and pentyl for decreasing the viscosity.

[0063] Preferred alkoxy is methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, or heptyloxy. For decreasing the viscosity, more preferred alkoxy is methoxy or ethoxy.

[0064] Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, and 5-hexenyl. More preferred alkenyls are vinyl, 1-propenyl, 3-butenyl, and 3-pentenyl for reducing viscosity. The preferred configuration of -CH=CH- in these alkenyls depends on the position of the double bond. For reducing viscosity, trans is preferred for alkenyls such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyl, and 3-hexenyl. Cis is preferred for alkenyls such as 2-butenyl, 2-pentenyl, and 2-hexenyl.

[0065] Preferred alkenyloxy groups are vinyloxy, allyloxy, 3-butenyloxy, 3-pentenyloxy, and 4-pentenyloxy. To decrease the viscosity, more preferred alkenyloxy groups are allyloxy and 3-butenyloxy.

[0066] Preferred examples of alkyl in which at least one hydrogen is replaced by fluorine or chlorine include fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl, 7-fluoroheptyl, and 8-fluorooctyl. More preferred examples are 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, and 5-fluoropentyl for increasing the dielectric anisotropy.

[0067] Preferred examples of alkenyl in which at least one hydrogen is replaced by fluorine or chlorine include 2,2-difluorovinyl, 3,3-difluoro-2-propenyl, 4,4-difluoro-3-butenyl, 5,5-difluoro-4-pentenyl, and 6,6-difluoro-5-hexenyl. More preferred examples are 2,2-difluorovinyl and 4,4-difluoro-3-butenyl to reduce viscosity.

[0068] Ring A is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, or tetrahydropyran-2,5-diyl. Preferred ring A is 1,4-phenylene, 2-fluoro-1,4-phenylene, or 2,6-difluoro-1,4-phenylene for increasing the optical anisotropy or the dielectric anisotropy.

[0069] Ring B is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, or tetrahydropyran-2,5-diyl. Preferred ring B is 1,4-cyclohexylene for increasing the maximum temperature, 1,4-phenylene for increasing the optical anisotropy, and 2-fluoro-1,4-phenylene or 2,6-difluoro-1,4-phenylene for increasing the dielectric anisotropy.

[0070] In ring A and ring B, tetrahydropyran-2,5-diyl is TIFF2025121829000028.tif1122 or TIFF2025121829000029.tif1122 and preferably TIFF2025121829000030.tif1122 is.

[0071] Ring C and ring D are 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene. Preferred ring C or ring D is 1,4-cyclohexylene for decreasing the viscosity or increasing the maximum temperature, and 1,4-phenylene or 2-fluoro-1,4-phenylene for increasing the optical anisotropy or decreasing the minimum temperature.

[0072] Ring E and ring G are 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl in which at least one hydrogen is replaced by fluorine or chlorine, chroman-2,6-diyl, or chroman-2,6-diyl in which at least one hydrogen is replaced by fluorine or chlorine. Preferred examples of 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine include 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, or 2-chloro-3-fluoro-1,4-phenylene. An example of naphthalene-2,6-diyl in which at least one hydrogen is replaced by fluorine or chlorine is 3,4,5-trifluoronaphthalene-2,6-diyl. An example of chroman-2,6-diyl in which at least one hydrogen is replaced by fluorine or chlorine is 7,8-difluorochroman-2,6-diyl. Preferred rings E and G are 1,4-cyclohexylene for decreasing viscosity, and 1,4-phenylene for increasing optical anisotropy or decreasing the minimum temperature.

[0073] Ring F is 2,3-difluoro-1,4-phenylene, 1,8-difluorophenanthrene-2,7-diyl, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4,5-trifluoronaphthalene-2,6-diyl, 7,8-difluorochroman-2,6-diyl, 3,4,5,6-tetrafluorofluorene-2,7-diyl (FLF4), 4,6-difluorodibenzofuran-3,7-diyl (DBFF2), 4,6-difluorodibenzothiophene-3,7-diyl (DBTF2), or 1,1,6,7-tetrafluoroindan-2,5-diyl (InF4). TIFF2025121829000031.tif30167 A preferred ring F is 2,3-difluoro-1,4-phenylene for decreasing the viscosity.

[0074] Z 1 is a single bond, carbonyloxy, or difluoromethyleneoxy. 1 is a single bond to decrease the viscosity, and is carbonyloxy or difluoromethyleneoxy to increase the dielectric anisotropy. 2 is carbonyloxy or difluoromethyleneoxy. 2 is difluoromethyleneoxy to increase the dielectric anisotropy and decrease the minimum temperature. 3 is a single bond, ethylene, vinylene, carbonyloxy, or difluoromethyleneoxy. 3 is a single bond to decrease the viscosity, and is difluoromethyleneoxy to increase the dielectric anisotropy. 4 is a single bond, ethylene, vinylene, ethynylene, methyleneoxy, or carbonyloxy. 4 is a single bond to reduce viscosity. Z 5 and Z 6 is a single bond, ethylene, vinylene, methyleneoxy, or carbonyloxy. 5 or Z 6 represents a single bond for increasing the optical anisotropy or decreasing the minimum temperature.

[0075] Divalent groups such as methyleneoxy are asymmetric. In methyleneoxy, -CH2O- is preferred to -OCH2-. In carbonyloxy, -COO- is preferred to -OCO-. In difluoromethyleneoxy, -CF2O- is preferred to -OCF2-.

[0076] X 1 and X 2 is hydrogen or fluorine. 1 or X 2 is hydrogen to decrease the viscosity, and is fluorine to increase the dielectric anisotropy. 3 , X 4 , X 5 , X 6, X 7 , and X 8 is hydrogen or fluorine. 3 , X 4 , X 5 , X 6 , X 7 , or X 8 is hydrogen to decrease the viscosity, and is fluorine to increase the dielectric anisotropy. 9 and X 10 is hydrogen or fluorine. 9 or X 10 is fluorine to increase the dielectric anisotropy.

[0077] Y 1 is fluorine, chlorine, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, alkoxy having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. 1 is fluorine to increase the dielectric anisotropy. 2 is fluorine, chlorine, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, alkoxy having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. 2 is fluorine, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or alkoxy having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine in order to increase the dielectric anisotropy.

[0078] A preferred example of alkyl in which at least one hydrogen is replaced by fluorine or chlorine is trifluoromethyl. A preferred example of alkoxy in which at least one hydrogen is replaced by fluorine or chlorine is trifluoromethoxy.

[0079] a is 1 or 2. Desirable a is 1 for decreasing the viscosity, and 2 for increasing the maximum temperature or the optical anisotropy. b is 1, 2, 3, or 4. Desirable b is 1 or 2 for decreasing the viscosity, and 3 or 4 for increasing the dielectric anisotropy. c is 1, 2, or 3. Desirable c is 1 for decreasing the viscosity, and 2 or 3 for increasing the maximum temperature or the optical anisotropy. d is 0, 1, 2, or 3, and e is 0 or 1, with the sum of d and e being 3 or less. Desirable d or e is 1 for increasing the optical anisotropy and decreasing the minimum temperature.

[0080] In formula (7), ring I and ring K are cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxan-2-yl, pyrimidin-2-yl, or pyridin-2-yl, and in these rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. Preferred ring I or ring K is phenyl. Ring J is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, and tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, and in these rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. Preferred ring J is 1,4-phenylene or 2-fluoro-1,4-phenylene.

[0081] Z 7 and Z 8 is a single bond or an alkylene having 1 to 10 carbon atoms, in which at least one -CH2- may be replaced by -O-, -CO-, -COO-, or -OCO-, and at least one -CH2CH2- may be replaced by -CH=CH-, -C(CH3)=CH-, -CH=C(CH3)-, or -C(CH3)=C(CH3)-, and in these groups at least one hydrogen may be replaced by fluorine or chlorine. Preferred Z 7 or Z 8 is a single bond, -CH2CH2-, -CH2O-, -OCH2-, -COO-, or -OCO-. 7 or Z 8 is a single bond.

[0082] Sp 1 From Sp 3 is a single bond or an alkylene having 1 to 10 carbon atoms, in which at least one -CH2- may be replaced by -O-, -COO-, -OCO-, or -OCOO-, and at least one -CH2CH2- may be replaced by -CH=CH- or -C≡C-, and in these groups, at least one hydrogen may be replaced by fluorine or chlorine. 1 From Sp 3 is a single bond, -CH2CH2-, -CHO-, -OCH2-, -COO-, -OCO-, -CO-CH=CH-, or -CH=CH-CO-. 1 From Sp 3 is a single bond.

[0083] i is 0, 1, or 2. Preferably, i is 0 or 1. f, g, and h are 0, 1, 2, 3, or 4, and the sum of f, g, and h is 1 or greater. Preferably, f, g, or h is 1 or 2.

[0084] P 1 From P 3is a polymerizable group. 1 From P 3 is a polymerizable group selected from the groups represented by formulas (P-1) to (P-5). 1 From P 3 is a group represented by formula (P-1), formula (P-2), or formula (P-3). Particularly preferred P 1 From P 3 is a group represented by formula (P-1) or formula (P-2). 1 From P 3 is a group represented by formula (P-1). A preferred group represented by formula (P-1) is -OCO-CH=CH2 or -OCO-C(CH3)=CH2. The wavy lines in formulas (P-1) to (P-5) indicate the bonding site. TIFF2025121829000032.tif34166

[0085] In formulas (P-1) to (P-5), M 1 From M 3 is hydrogen, fluorine, alkyl having 1 to 5 carbon atoms, or alkyl having 1 to 5 carbon atoms in which at least one hydrogen has been replaced by fluorine or chlorine. 1 From M 3 is hydrogen or methyl to increase reactivity. More preferred M 1 is hydrogen or methyl, and more preferably M 2 or M 3 is hydrogen.

[0086] In equations (7-1) to (7-29), P 4 From P 6 is a group represented by formula (P-1) to formula (P-3). 4 From P 6 is represented by formula (P-1) or formula (P-2). More preferred formula (P-1) is -OCO-CH=CH2 or -OCO-C(CH3)=CH2. The wavy lines in formulas (P-1) to (P-3) indicate the bonding site. TIFF2025121829000033.tif3098

[0087] Fifth, preferred component compounds are shown. Preferred compound (1) is compound (1-1) to compound (1-9) described in item 2. In these compounds, at least one of component A is preferably compound (1-3), compound (1-7), or compound (1-8). It is preferred to combine two or more of compound (1-3), compound (1-7), or compound (1-8).

[0088] Preferred compounds (2) are compounds (2-1) to (2-8) described in item 4. In these compounds, it is preferred that at least one of component B is compound (2-1), compound (2-2), compound (2-3), compound (2-4), compound (2-5), compound (2-6), or compound (2-8). It is particularly preferred that at least one of component B is compound (2-1).

[0089] The combination of compound (1) and compound (2) can prepare a composition that is excellent particularly in terms of dielectric anisotropy and the minimum temperature. In this respect, the combination of compound (1-3) and compound (2-1), compound (1-7) and compound (2-1), or compound (1-8) and compound (2-1) is particularly preferred.

[0090] The additive X is an optically active compound and is not particularly limited as long as it exhibits a cholesteric phase. To avoid affecting the physical properties of the host liquid crystal composition, the content is preferably about 10% by mass or less. To achieve this, an optically active compound with a larger HTP (helical twist power) is preferred. Preferred additives X are compounds (3-1) to (3-7) described in item 6. Among these compounds, compound (3-4) is particularly preferred.

[0091] Preferred compounds (4) are compounds (4-1) to (4-26) described in item 9. In these compounds, at least one of the components C is preferably compound (4-20) or compound (4-21).

[0092] Preferred compounds (5) are compounds (5-1) to (5-20) described in item 12. In these compounds, at least one of component D is preferably compound (5-1), compound (5-10), compound (5-15), compound (5-16), compound (5-17), compound (5-19), or compound (5-20). The total proportion of compound (5-1), compound (5-10), compound (5-15), compound (5-16), compound (5-17), compound (5-18), compound (5-19), or compound (5-20) is preferably 20% by mass to 50% by mass.

[0093] Preferred compounds (6) are compounds (6-1) to (6-36) described in item 15. In these compounds, at least one of the components E is preferably compound (6-19).

[0094] Preferred compounds (7) are compounds (7-1) to (7-29) described in item 17. In these compounds, it is preferred that at least one of the additives Y is compound (7-1), compound (7-2), compound (7-24), compound (7-25), compound (7-26), or compound (7-27). It is preferred that at least two of the additives Y are a combination of compound (7-1) and compound (7-2), compound (7-1) and compound (7-18), compound (7-2) and compound (7-24), compound (7-2) and compound (7-25), compound (7-2) and compound (7-26), compound (7-25) and compound (7-26), or compound (7-18) and compound (7-24).

[0095] Sixth, additives that may be added to the composition are described below, such as antioxidants, ultraviolet absorbers, quenchers, dyes, antifoaming agents, polar compounds, etc.

[0096] In order to prevent a decrease in resistivity due to heating in the atmosphere, or to maintain a large 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 such as compounds (8-1) to (8-3) may be further added to the composition.

[0097] TIFF2025121829000034.tif87124

[0098] Because compound (8-2) has low volatility, it is 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 antioxidant content 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 content is in the range of about 100 ppm to about 300 ppm.

[0099] 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 (9-1) to (9-16). 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.

[0100] TIFF2025121829000035.tif251139 TIFF2025121829000036.tif245139

[0101] A quencher is a compound that receives light energy absorbed by a liquid crystal compound and converts it into thermal energy, thereby preventing the decomposition of the liquid crystal compound. Preferred examples of the quencher include compounds (10-1) to (10-7). The preferred proportion of these quenchers is about 50 ppm or more to obtain the desired effect, and about 20,000 ppm or less to avoid increasing the minimum temperature. A more preferred proportion is in the range of about 100 ppm to about 10,000 ppm.

[0102] TIFF2025121829000037.tif15982

[0103] 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 content of the antifoaming agent is about 1 ppm or more to achieve its effect and about 1000 ppm or less to prevent display defects. A more preferred content is about 1 ppm to about 500 ppm.

[0104] A polymerizable compound is used to adapt the polymerizable compound to a polymer-supported alignment (PSA) type element. Preferred examples of such polymerizable compounds include acrylates, methacrylates, vinyl compounds, vinyloxy compounds, propenyl ethers, epoxy compounds (oxiranes, oxetanes), and vinyl ketones. More preferred examples are acrylate or methacrylate derivatives. The preferred ratio is about 10% by mass or more based on the total mass of the polymerizable compound. A more preferred ratio is about 50% by mass or more. A particularly preferred ratio is about 80% by mass or more. The most preferred ratio is 100% by mass.

[0105] 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-t-butylcatechol, 4-methoxyphenol, phenothiazine, etc.

[0106] Polar compounds are organic compounds that have polarity. This does not include compounds with ionic bonds. Atoms such as oxygen, sulfur, and nitrogen are more electronegative and tend to 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, polar compounds have at least one of the following substructures: -OH, -COOH, -SH, -NH2, >NH, >N-.

[0107] Seventh, the synthesis methods of the component compounds will be described. These compounds can be synthesized by known methods. Examples of synthesis methods are as follows: Compound (1-7) is synthesized by the method described in JP-A-10-114733. Compound (2-1) is synthesized by the method described in JP-A-10-81679. Compound (3-4) is synthesized by the method described in WO 2014-97952. Compound (4-13) is synthesized by the method described in JP-A-10-251186. Compound (5-1) is synthesized by the method described in JP-A-9-77692. Compound (6-1) is synthesized by the method described in JP-A-2-503441. Compound (8-1) is available from Sigma-Aldrich Corporation. Compound (8-2) and the like are synthesized by the method described in US Pat. No. 3,660,505.

[0108] Compounds for which no synthetic method is described 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 can be prepared from the compounds thus obtained by known methods. For example, the component compounds can be mixed and dissolved by heating.

[0109] Finally, we will explain the uses of the composition. This composition is a liquid crystal composition with a cholesteric phase obtained by adding an optically active compound to a host liquid crystal composition with a nematic phase. In this respect, it differs from liquid crystal compositions with an optically isotropic liquid crystal phase. This composition mainly has a minimum temperature of about -10°C or less, a maximum temperature of about 60°C or more, and an optical anisotropy in the range of about 0.15 to about 0.35. Devices containing this composition have a large voltage holding ratio. [Example]

[0110] The present invention will be described in more detail with reference to examples. The present invention is not limited by these examples. The present invention includes a mixture of the composition of Example 1 and the composition of Example 2. The present invention also includes a mixture of at least two of the compositions of the examples. The synthesized compounds were identified by methods such as NMR analysis. The properties of the compounds, compositions, and devices were measured by the methods described below.

[0111] NMR analysis: For the measurement, a DRX-500 manufactured by Bruker Biospin was used. 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. 19F-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.

[0112] Gas chromatographic analysis: A Shimadzu GC-14B gas chromatograph was used for the measurements. The carrier gas was helium (2 mL / min). The sample vaporizer was set to 280 °C, and the detector (FID) was set to 300 °C. A capillary column DB-1 (30 m long, 0.32 mm inner diameter, 0.25 μm film thickness; dimethylpolysiloxane stationary phase; nonpolar) from Agilent Technologies Inc. was used to separate the component compounds. The column was held at 200 °C for 2 min and then heated to 280 °C at a rate of 5 °C / min. The sample was prepared in acetone (0.1% by mass), and 1 μL of the solution was injected into the sample vaporizer. A Shimadzu C-R5A Chromatopac or equivalent was used as the recorder. The resulting gas chromatogram showed the retention times and peak areas of the peaks corresponding to the component compounds.

[0113] Solvents such as chloroform and hexane may be used to dilute the sample. The following capillary columns may be used to separate the component compounds: HP-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm) manufactured by Agilent Technologies Inc., Rtx-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm) manufactured by Restek Corporation, and BP-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm) manufactured by SGE International Pty. Ltd. To prevent overlapping of compound peaks, Shimadzu Corporation's CBP1-M50-025 capillary column (length 50 m, inner diameter 0.25 mm, film thickness 0.25 μm) may also be used.

[0114] The proportion of the liquid crystal compound contained in the composition may be calculated by the following method. A mixture of liquid crystal compounds is analyzed by gas chromatography (FID). The peak area ratio in the gas chromatogram corresponds to the proportion of the liquid crystal compound. When the capillary column described above is used, the correction factor for each liquid crystal compound may be considered to be 1. Therefore, the proportion (mass %) of the liquid crystal compound can be calculated from the peak area ratio.

[0115] Measurement sample: When measuring the properties of a composition or device, the composition was used as the sample. When measuring the properties of a compound, the compound (15% by mass) was mixed with mother liquid crystals (85% by mass) to prepare a measurement sample. The compound's property value was calculated by extrapolation from the measured value. (Extrapolated value) = {(Measured value of sample) - 0.85 × (Measured value of mother liquid crystals)} / 0.15. When a smectic phase (or crystals) precipitated at 25°C at this ratio, the ratio of compound to mother liquid crystals was changed to 10% by mass:90% by mass, 5% by mass:95% by mass, and 1% by mass:99% by mass, in that order. The maximum temperature, optical anisotropy, viscosity, and dielectric anisotropy values for the compound were determined by this extrapolation method.

[0116] The following mother liquid crystals were used: The mother liquid crystals were a composition consisting of mixtures A, B, and C. TIFF2025121829000038.tif2770Mixture A, mixture B, and mixture C are as follows: TIFF2025121829000039.tif194109 Mixture A is a mixture of compound (a), compound (b), and compound (c) in a 1:1:1 (mass ratio). Mixture B is a mixture of compound (d), compound (e), and compound (f) in a 2:1:2 (mass ratio). Mixture C is a mixture of compound (g), compound (h), and compound (i) in a 1:1:2 (mass ratio).

[0117] Measurement methods: The characteristics were measured using the following methods. Most of these were methods described in the JEITA standard (JEITA ED-2521B) established by the Japan Electronics and Information Technology Industries Association (JEITA), or modified methods. The TN devices used for the measurements were not equipped with thin film transistors (TFTs).

[0118] (1) The maximum temperature of the nematic phase (NI; °C), the maximum temperature of the cholesteric phase (N * I): A sample was placed on the hot plate of a melting point measurement 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 the nematic or cholesteric phase to an isotropic liquid was measured. The upper limit temperature of the nematic or cholesteric phase is sometimes abbreviated as the "maximum temperature."

[0119] (2) The lowest temperature (T C ; °C): Samples with a nematic or cholesteric 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 a nematic or cholesteric phase at -20 °C and changed to a crystalline or smectic phase at -30 °C, T C When the phase changes to a crystalline or smectic phase at 0°C or 25°C (room temperature), T C are expressed as >0°C and >25°C, respectively. The lower limit temperature of the nematic phase or the cholesteric phase is sometimes abbreviated as "lower limit temperature."

[0120] (3) Viscosity (bulk viscosity; η; measured at 20°C; mPa·s): Measurement was performed using an E-type rotational viscometer manufactured by Tokyo Keiki Co., Ltd.

[0121] (4) Viscosity (rotational viscosity; γ1; measured at 25°C; mPa·s): Measurement was 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 twist angle of 0° and a cell gap of 5 μm 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) followed by no voltage application (2 seconds) was applied repeatedly. The peak current and peak time of the transient current generated by this voltage application were measured. The rotational viscosity was calculated from these measurements and equation (10) on page 40 of the paper by M. Imai et al. The value of the dielectric anisotropy required for this calculation was determined by the method described below using the device used to measure the rotational viscosity.

[0122] (5) Optical anisotropy (refractive index anisotropy; Δn; measured at 25°C): Measurements were made using light with a wavelength of 589 nm and an Abbe refractometer equipped with a polarizing plate attached to an 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 polarized light was parallel to the rubbing direction. The refractive index n⊥ was measured when the direction of polarized light was perpendicular to the rubbing direction. The optical anisotropy value was calculated from the formula Δn=n∥-n⊥.

[0123] (6) Dielectric anisotropy (Δε; measured at 25°C): A sample was placed in a TN device with a cell gap of 9 μm between two glass substrates and a twist angle of 80 degrees. A sine wave (10 V, 1 kHz) was applied to the device, and the dielectric constant (ε∥) in the long axis direction of the liquid crystal molecules was measured after 2 seconds. A sine wave (0.5 V, 1 kHz) was applied to the device, and the dielectric constant (ε⊥) in the short axis direction of the liquid crystal molecules was measured after 2 seconds. The dielectric anisotropy value was calculated using the formula Δε = ε∥ - ε⊥.

[0124] (7-1) Threshold voltage (Vth(25); measured at 25°C; V): Measurement was performed using an LCD5200 luminance meter manufactured by Otsuka Electronics Co., Ltd. A halogen lamp was used as the light source. A sample was placed in an FFS element with a cell gap of 3.2 μm between the two glass substrates. The voltage (32 Hz, square wave) applied to this element was increased in steps of 0.01 V from 0 V to 10 V. During this time, light was irradiated perpendicularly onto the element, and the amount of light transmitted through the element was measured. A voltage-transmittance curve was created in which the maximum amount of light represented 100% transmittance and the minimum amount of light represented 0% transmittance. The threshold voltage was expressed as the voltage at which the transmittance reached 95%.

[0125] (7-2) Threshold voltage (Vth(-30); measured at -30°C; V): Same as (7-1) except that it was measured at -30°C.

[0126] (8) Voltage holding ratio (VHR-1; measured at 25°C; %): The TN element used for the measurement had a polyimide alignment film, and the distance between the two glass substrates (cell gap) was 5 μm. After the sample was placed in the element by vacuum injection, the injection port was sealed with an ultraviolet-curing adhesive. A pulse voltage (1 V for 60 microseconds) was applied to the TN element to charge it. The decaying voltage was measured for 166.7 milliseconds with a high-speed voltmeter, and the area A between the voltage curve and the horizontal axis in a unit period was calculated. Area B was the area when there was no decay. The voltage holding ratio was expressed as the percentage of area A to area B.

[0127] (9) Voltage holding ratio (VHR-2; measured at 60°C; %): The voltage holding ratio was measured in the same manner as above, except that the measurement was performed at 60°C instead of 25°C. The obtained value was expressed as VHR-2.

[0128] (10) Voltage holding ratio (VHR-3; measured at 60°C; %): After ultraviolet irradiation, the voltage holding ratio was measured to evaluate the stability against ultraviolet rays. The TN element used for the measurement had a polyimide alignment film and a cell gap of 5 μm. A sample was injected into this element, and the irradiated light was 5 mW / cm. 2The element was irradiated with ultraviolet light of 167 minutes. The light source was a black light F40T10 / BL (peak wavelength 369 nm) manufactured by iGraphics Co., Ltd., and the distance between the element and the light source was 5 mm. In measuring VHR-3, the decaying voltage was measured over a period of 166.7 milliseconds. Compositions with a large VHR-3 have high stability against ultraviolet light.

[0129] (11) Voltage holding ratio (VHR-4; measured at 60°C; %): After the TN element into which the sample was injected was heated in a thermostatic chamber at 120°C for 20 hours, the voltage holding ratio was measured to evaluate the thermal stability. In the VHR-4 measurement, the voltage decay time was measured as 166.7 milliseconds. A composition with a large VHR-4 has high thermal stability.

[0130] (12) Voltage holding ratio (VHR-5; measured at 60°C; %): After the TN device into which the sample was injected was left standing under a backlight for two weeks, the voltage holding ratio was measured to evaluate the stability against the backlight. In the VHR-5 measurement, the voltage decay time was measured as 166.7 milliseconds. A composition with a large VHR-5 has high stability against the backlight.

[0131] (13) Response time (τ; measured at 25°C; ms): Measurements were performed using an LCD5200 luminance meter manufactured by Otsuka Electronics Co., Ltd. The light source was a halogen lamp. The low-pass filter was set to 5 kHz. The sample was placed in a TN device with a cell gap of 5 μm between two glass substrates. A square wave (60 Hz, Vth(25), 0.5 s) was applied to the device. Light was irradiated perpendicularly to the device, and the amount of light reflected from the device was measured. The maximum amount of light was considered to be 100% reflectance, and the minimum amount of light was considered to be 0% reflectance. The rise time (τr; rise time; ms) was the time required for the reflectance to change from 90% to 10%. The fall time (τf; ms) was the time required for the reflectance to change from 10% to 90%. The response time was expressed as the sum of the rise time and fall time. A voltage is applied to the element into which the sample has been injected in increments of 1 V from 0 V to 40 V, and the voltage at which the element switches from the initial reflective state to the transmissive state is defined as Vreset (V).

[0132] (14) Elastic constant (K; measured at 25°C; pN): Measurements were performed using a Yokogawa-Hewlett-Packard HP4284A LCR meter. A sample was placed in a horizontally aligned device with a cell gap of 20 μm between the two glass substrates. A charge of 0 to 20 volts was applied to the device, and the capacitance and applied voltage were measured. The measured capacitance (C) and applied voltage (V) were fitted using equations (2.98) and (2.101) on page 75 of the "Liquid Crystal Device Handbook" (Nikkan Kogyo Shimbun, Ltd.), and the values of K11 and K33 were obtained from equation (2.99). Next, K22 was calculated using equation (3.18) on page 171 of the same publication, using the previously determined values of K11 and K33. The elastic constant was expressed as the average of the values of K11, K22, and K33 thus determined.

[0133] (15) Resistivity (ρ; measured at 25°C; Ωcm): 1.0 mL of sample was poured into a container equipped with electrodes. A DC voltage (10 V) was applied to the container, and the DC current was measured after 10 seconds. The resistivity was calculated using the following formula: (resistivity) = {(voltage) × (capacity of container)} / {(DC current) × (dielectric constant of vacuum)}.

[0134] (16) Helical pitch (P; measured at room temperature; μm): The helical pitch was measured by the wedge method. See page 196 of "Liquid Crystal Handbook" (published by Maruzen in 2000). The sample was poured into a wedge-shaped cell and allowed to stand at room temperature for two hours. The distance between the disclination lines (d2 - d1) was then observed using a polarizing microscope (Nikon Corporation, MM40 / 60 series). The helical pitch (P) was calculated using the following formula, where θ is the angle of the wedge cell: P = 2 × (d2 - d1) × tan θ.

[0135] (17) Dielectric constant in the minor axis direction (ε⊥; measured at 25°C): A sample was placed in a TN device with a cell gap of 9 μm between two glass substrates and a twist angle of 80°. A sine wave (0.5 V, 1 kHz) was applied to the device, and the dielectric constant in the minor axis direction (ε⊥) of the liquid crystal molecules was measured after 2 seconds.

[0136] (18) Frequency dependence of dielectric anisotropy (F10; measured at -20°C): A sample was placed in a TN device with a cell gap of 9 μm between two glass substrates and a twist angle of 80°. Sine waves (0.5 V, 20 Hz, 50 Hz, 100 Hz, 1 kHz, 5 kHz, 10 kHz, 50 kHz, 100 kHz, 500 kHz, and 1000 kHz) were applied to the device, and the dielectric constant (ε⊥) in the minor axis direction of the liquid crystal molecules was measured after 2 seconds. F10 was defined as the frequency at which the dielectric anisotropy decreased by 10% compared to the dielectric anisotropy at 20 Hz. A larger F10 indicates smaller frequency dependence.

[0137] (19) Reflection wavelength (λ; nm): Measurements were performed using a JASCO V-700 UV-Vis-NIR spectrophotometer equipped with an ISV-922 integrating sphere unit. The sample was placed in a device with a cell gap of 5 μm between two glass substrates, and the reflection wavelength was measured at a light incident angle of 5 degrees.

[0138] Examples of compositions are shown below. Component compounds are represented by symbols based on the definitions in Table 3 below. In Table 3, the configuration of 1,4-cyclohexylene is trans. The number in parentheses after the symbolized compound indicates the chemical formula to which the compound belongs. The symbol (-) indicates other liquid crystal compounds. The proportion (percentage) of the liquid crystal compound is a mass percentage (mass %) based on the mass of the liquid crystal composition without additives. Finally, the property values of the compositions are summarized.

[0139] TIFF2025121829000040.tif250162

[0140] [Comparative Example 1] 3-GB(F,F)XB(F)B(F,F)-F (2-1) 20% 3-BB(F,F)XB(F,F)-F (4-13) 13% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 3-HH-V (5-1) 2% 2-BB(F)B-5 (5-10) 2% 1-BB(F)B-2V (5-10) 8% 2-BB(F)B-2V (5-10) 7% 5-HBB(F)B-2 (5-15) 6% 5-HBB(F)B-3 (5-15) 6% 3-BB(2F,5F)B-3 (5-16) 5% 2-BB(2F,3F)B-3 (6-19) 5% 4-GB(F)B(F,F)XB(F,F)-F (-) 8% NI=112.9℃;Δn=0.208;Δε=31.3;Tc<-20℃. The compound (3-4) of the composition was added at 3.5% by mass. N * I=108.9℃;Δε=31.3;Tc<-20℃;Δλ=414nm;Vreset=26V. TIFF2025121829000041.tif29117

[0141] [Comparative Example 2] 1V2-BEB(F,F)-C (1-3) 17% 2-BEB(F)-C (1-3) 5% 3-BB(F)BC (1-7) 8% 3-BB(2F)BC (1-8) 5% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 4-BB(F)B(F,F)XB(F,F)-F (4-20) 10% 5-BB(F)B(F,F)XB(F,F)-F (4-20) 10% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 5-HBB(F)B-2 (5-15) 6% 5-HBB(F)B-3 (5-15) 6% 3-HB(F)TB-3 (5-19) 7% 4-GB(F)B(F,F)XB(F,F)-F (-) 8% NI=124.7℃;Δn=0.234;Δε=88.6;Tc>25℃. The compound (3-4) of the composition was added at 3.5% by mass. N * I=120.8℃;Δε=88.6;Tc>0℃;Δλ=430nm;Vreset=16V. TIFF2025121829000042.tif29117

[0142] [Comparative Example 3] 1V2-BEB(F,F)-C (1-3) 17% 2-BEB(F)-C(1-3) 5% 3-BB(F)BC (1-7) 8% 3-BB(2F)BC (1-8) 5% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 4-BB(F)B(F,F)XB(F,F)-F (4-20) 10% 5-BB(F)B(F,F)XB(F,F)-F (4-20) 5% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 5-HBB(F)B-2(5-15) 6% 3-BTB-O1(5-17) 6% 3-HB(F)TB-3 (5-19) 7% 3-HB(F)TB-4 (5-19) 5% 4-GB(F)B(F,F)XB(F,F)-F(-) 8% NI=110.9°C;Δn=0.236;Δε=66.7;Tc>0°C. It has a 3.2 percent freedom in the range(3-4). N * I=107.0°C;Δε=66.7;Tc>0°C;Δλ=455nm;Vreset=16V. TIFF2025121829000043.tif29117

[0143] [Chapter 1] 1V2-BEB(F,F)-C(1-3) 17% 2-BEB(F)-C(1-3) 5% 3-BB(F)BC (1-7) 8% 3-GB(F,F)XB(F)B(F,F)-F (2-1) 20% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 3-HH-V (5-1) 2% 5-HBB(F)B-2(5-15) 6% 5-HBB(F)B-3 (5-15) 6% 3-BB(2F,5F)B-3 (5-16) 5% 2-BB(2F,3F)B-3 (6-19) 5% 4-GB(F)B(F,F)XB(F,F)-F (-) 8% NI=103.0℃;Δn=0.205;Δε=93.5;Tc<-20℃. The compound (3-4) of the composition was added at 3.5% by mass. N * I=99.1℃;Δε=93.5;Tc<-20℃;Δλ=425nm;Vreset=15V. TIFF2025121829000044.tif29117

[0144] [Example 2] 1V2-BEB(F,F)-C (1-3) 17% 2-BEB(F)-C (1-3) 5% 3-BB(F)BC (1-7) 8% 3-BB(2F)BC (1-8) 5% 3-GB(F,F)XB(F)B(F,F)-F (2-1) 15% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 5-HBB(F)B-2 (5-15) 6% 5-HBB(F)B-3 (5-15) 6% 3-HB(F)TB-3 (5-19) 7% 3-HB(F)TB-4 (5-19) 5% 4-GB(F)B(F,F)XB(F,F)-F (-) 8% NI=122.5℃;Δn=0.222;Δε=83.4;Tc<-30℃. The compound (3-4) of the composition was added at 3.2% by mass. N * I=108.6℃;Δε=83.4;Tc<-30℃;Δλ=450nm;Vreset=16V. TIFF2025121829000045.tif29117

[0145] [Chapter 3] 1V2-BEB(F,F)-C(1-3) 17% 2-BEB(F)-C(1-3) 5% 3-BB(F)BC (1-7) 8% 3-BB(2F)BC (1-8) 5% 3-GB(F,F)XB(F)B(F,F)-F (2-1) 10% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 5-HBB(F)B-2(5-15) 6% 3-BTB-O1(5-17) 6% 3-HB(F)TB-3 (5-19) 7% 3-HB(F)TB-4 (5-19) 5% 4-GB(F)B(F,F)XB(F,F)-F(-) 8% 5-GB(F)B(F,F)XB(F,F)-F(-) 5% NI=107.3°C;Δn=0.224;Δε=75.0;Tc<-30°C. It has a 3.2 percent freedom in the range(3-4). N * I=103.3°C;Δε=75.0;Tc<-30°C;Δλ=455nm;Vreset=17V. TIFF2025121829000046.tif29117

[0146] [Chapter 4] 1V2-BEB(F,F)-C(1-3) 17% 2-BEB(F)-C(1-3) 5% 3-BB(F)BC (1-7) 8% 3-BB(2F)BC (1-8) 5% 2-GB(F,F)XB(F)B(F)-F (2-2) 10% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 5-HBB(F)B-2(5-15) 6% 3-BTB-O1(5-17) 6% 3-HB(F)TB-3 (5-19) 7% 3-HB(F)TB-4 (5-19) 5% 4-GB(F)B(F,F)XB(F,F)-F(-) 8% 5-GB(F)B(F,F)XB(F,F)-F(-) 5% NI=109.1°C;Δn=0.224;Δε=74.2;Tc<-30°C. It has a 3.3 percent freedom in the range(3-4). N * I=105.4°C;Δε=75.0;Tc<-30°C;Δλ=455nm;Vreset=18V. TIFF2025121829000047.tif29117

[0147] [Chapter 5] 1V2-BEB(F,F)-C(1-3) 17% 2-BEB(F)-C(1-3) 5% 3-BB(F)BC (1-7) 8% 3-BB(2F)BC (1-8) 5% 4-GB(F)XB(F)B(F,F)-F (2-3) 10% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 5-HBB(F)B-2(5-15) 6% 3-BTB-O1(5-17) 6% 3-HB(F)TB-3 (5-19) 7% 3-HB(F)TB-4 (5-19) 5% 4-GB(F)B(F,F)XB(F,F)-F(-) 8% 5-GB(F)B(F,F)XB(F,F)-F (-) 5% NI=110.2℃;Δn=0.224;Δε=74.4;Tc<-30℃. The compound (3-4) of the composition was added at 3.3% by mass. N * I=106.2℃;Δε=74.4;Tc<-30℃;Δλ=455nm;Vreset=18V. TIFF2025121829000048.tif29117

[0148] [Example 6] 1V2-BEB(F,F)-C (1-3) 17% 2-BEB(F)-C (1-3) 5% 3-BB(F)BC (1-7) 8% 3-BB(2F)BC (1-8) 5% 4-GB(F,F)XBB(F,F)-F (2-4) 10% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 5-HBB(F)B-2 (5-15) 6% 3-BTB-O1 (5-17) 6% 3-HB(F)TB-3 (5-19) 7% 3-HB(F)TB-4 (5-19) 5% 4-GB(F)B(F,F)XB(F,F)-F (-) 8% 5-GB(F)B(F,F)XB(F,F)-F (-) 5% NI=106.4℃;Δn=0.223;Δε=74.2;Tc<-30℃. The compound (3-4) of the composition was added at 3.3% by mass. N * I=102.5℃;Δε=74.2;Tc<-30℃;Δλ=455nm;Vreset=18V. TIFF2025121829000049.tif29117

[0149] [Chapter 7] 1V2-BEB(F,F)-C(1-3) 17% 2-BEB(F)-C(1-3) 5% 3-BB(F)BC (1-7) 8% 3-BB(2F)BC (1-8) 5% 3-GB(F,F)EB(F)B(F,F)-F (2-5) 10% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 5-HBB(F)B-2(5-15) 6% 3-BTB-O1(5-17) 6% 3-HB(F)TB-3 (5-19) 7% 3-HB(F)TB-4 (5-19) 5% 4-GB(F)B(F,F)XB(F,F)-F(-) 8% 5-GB(F)B(F,F)XB(F,F)-F(-) 5% NI=112.2°C;Δn=0.227;Δε=77.0;Tc<-30°C. It has a 3.3% efficiency percentage in the range(3-4). N * I=108.3°C;Δε=77.0;Tc<-30°C;Δλ=455nm;Vreset=17V. TIFF2025121829000050.tif29117

[0150] [Chapter 8] 1V2-BEB(F,F)-C(1-3) 17% 2-BEB(F)-C(1-3) 5% 3-BB(F)BC (1-7) 8% 3-BB(2F)BC (1-8) 5% 3-GB(F)EB(F)B(F,F)-F (2-6) 10% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 5-HBB(F)B-2(5-15) 6% 3-BTB-O1(5-17) 6% 3-HB(F)TB-3 (5-19) 7% 3-HB(F)TB-4 (5-19) 5% 4-GB(F)B(F,F)XB(F,F)-F(-) 8% 5-GB(F)B(F,F)XB(F,F)-F(-) 5% NI=114.4°C;Δn=0.228;Δε=76.1;Tc<-20°C. It has a 3.3 percent freedom in the range(3-4). N * I=110.5°C;Δε=76.1;Tc<-20°C;Δλ=455nm;Vreset=17V. TIFF2025121829000051.tif29117

[0151] [Chapter 9] 1V2-BEB(F,F)-C(1-3) 17% 2-BEB(F)-C(1-3) 5% 3-BB(F)BC (1-7) 8% 3-BB(2F)BC (1-8) 5% 2-GB(F,F)EBB(F,F)-F (2-8) 10% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 5-HBB(F)B-2(5-15) 6% 3-BTB-O1(5-17) 6% 3-HB(F)TB-3 (5-19) 7% 3-HB(F)TB-4 (5-19) 5% 4-GB(F)B(F,F)XB(F,F)-F(-) 8% 5-GB(F)B(F,F)XB(F,F)-F(-) 5% NI=111.2℃;Δn=0.225;Δε=74.9;Tc<-20℃. The compound (3-4) of the composition was added at 3.3% by mass. N * I=107.2℃;Δε=74.9;Tc<-20℃;Δλ=455nm;Vreset=18V. TIFF2025121829000052.tif29117

[0152] [Example 10] 1V2-BEB(F,F)-C (1-3) 17% 2-BEB(F)-C (1-3) 5% 3-BB(F)BC (1-7) 8% 3-BB(2F)BC (1-8) 5% V2-GB(F,F)XB(F)B(F,F)-F (2-1) 10% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 5-HBB(F)B-2 (5-15) 6% 3-BTB-O1 (5-17) 6% 3-HB(F)TB-3 (5-19) 7% 3-HB(F)TB-4 (5-19) 5% 4-GB(F)B(F,F)XB(F,F)-F (-) 8% 5-GB(F)B(F,F)XB(F,F)-F (-) 5% NI=107.4℃;Δn=0.225;Δε=75.1;Tc<-30℃. The compound (3-4) of the composition was added at 3.3% by mass. N * I=103.5℃;Δε=75.1;Tc<-30℃;Δλ=455nm;Vreset=17V. TIFF2025121829000053.tif29117

[0153] [Example 11] 1V2-BEB(F,F)-C(1-3) 17% 2-BEB(F)-C(1-3) 4% 3-BB(F)BC (1-7) 3% 3-GB(F,F)XB(F)B(F,F)-F (2-1) 15% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 3-HH-V (5-1) 5% 1-BB(F)B-2V (5-10) 5% 5-HBB(F)B-2(5-15) 2% 3-HB(F)TB-3 (5-19) 5% 3-HB(F)TB-4 (5-19) 5% 3-BB(F)TB-2 (5-20) 6% 3-BB(F)TB-3 (5-20) 6% 3-BB(F)TB-4 (5-20) 6% 2-BB(2F,3F)B-3(6-19) 3% NI=106.0°C;Δn=0.233;Δε=51.7;Tc<-30°C. It has a 3.3 percent freedom in the range(3-4). N * I=102.1°C;Δε=51.7;Tc<-30°C;Δλ=455nm;Vreset=20V. TIFF2025121829000054.tif29117

[0154] [Chapter 12] 1V2-BEB(F,F)-C(1-3) 17% 2-BEB(F)-C(1-3) 5% 3-BB(F)BC (1-7) 8% 3-BB(2F)BC(1-8) 9% 3-GB(F,F)XB(F)B(F,F)-F (2-1) 10% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 4% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 5-HBB(F)B-2(5-15) 5% 3-BTB-O1(5-17) 5% 4-BTB-O2(5-17) 3% 5-BTB-O1 (5-17) 4% 3-HB(F)TB-3 (5-19) 6% 3-HB(F)TB-4 (5-19) 6% 4-GB(F)B(F,F)XB(F,F)-F(-) 3% NI=104.8°C;Δn=0.237;Δε=53.3;Tc<-30°C. It has a 3.2 percent freedom in the range(3-4). N * I=100.8°C;Δε=53.3;Tc<-30°C;Δλ=460nm;Vreset=19V. TIFF2025121829000055.tif29117

[0155] [Chapter 13] 1V2-BEB(F,F)-C(1-3) 17% 2-BEB(F)-C(1-3) 5% 3-BB(F)BC (1-7) 8% 3-BB(2F)BC(1-8) 9% 3-GB(F,F)XB(F)B(F,F)-F (2-1) 10% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 4% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 5-HBB(F)B-2(5-15) 5% 3-BTB-O1(5-17) 5% 4-BTB-O2(5-17) 3% 5-BTB-O1 (5-17) 4% 3-HB(F)TB-3 (5-19) 6% 3-HB(F)TB-4 (5-19) 6% 4-GB(F)B(F,F)XB(F,F)-F(-) 3% NI=104.8°C;Δn=0.237;Δε=53.3;Tc<-30°C. It has a 2.1 percent freedom in the range(3-4). N * I=102.3°C;Δε=53.3;Tc<-30°C;Δλ=660nm;Vreset=19V. TIFF2025121829000056.tif29117

[0156] [Chapter 14] 1V2-BEB(F,F)-C(1-3) 17% 2-BEB(F)-C(1-3) 5% 3-GB(F,F)XB(F)B(F,F)-F (2-1) 10% 3-BB(F)B(F,F)XB(F,F)-F (4-20) 3% 3-BB(F,F)XB(F)B(F,F)-F (4-21) 15% 3-HH-V (5-1) 2% 5-HBB(F)B-2(5-15) 5% 5-HBB(F)B-3(5-15) 5% 3-BTB-O1(5-17) 5% 5-BTB-O1(5-17) 5% 3-HB(F)TB-2 (5-19) 5% 3-HB(F)TB-3 (5-19) 5% 3-HB(F)TB-4 (5-19) 5% 2-BB(2F,3F)B-3(6-19) 5% 4-GB(F)B(F,F)XB(F,F)-F(-) 8% NI=100.9°C;Δn=0.211;Δε=55.5;Tc<-30°C. It has a 3.3% efficiency percentage in the range(3-4). N * I=97.3°C;Δε=55.5;Tc<-30°C;Δλ=455nm;Vreset=20V. TIFF2025121829000057.tif29117

[0157] Comparative Example 1 is a composition that does not contain formula (1) and has a dielectric anisotropy of 31.3. Comparative Example 2 is a composition that does not contain formula (2) and has a dielectric anisotropy of 88.6, which crystallizes at 25°C. On the other hand, the composition of Example 1 has a dielectric anisotropy of 93.5 and does not crystallize even at -20°C. Similarly, the composition of Comparative Example 3 has a dielectric anisotropy of 66.7 and crystallizes at 0°C, while the composition of Example 2 has a dielectric anisotropy of 83.4 and does not crystallize even at -30°C. As such, the compositions of the present invention have large dielectric anisotropy and low minimum temperature. Therefore, it can be concluded that the composition of the present invention has excellent properties. [Industrial Applicability]

[0158] The liquid crystal composition of the present invention can be used for liquid crystal monitors, liquid crystal televisions, and the like.

Claims

1. A liquid crystal composition having a cholesteric phase, comprising at least one compound selected from compounds represented by formula (1) as component A, at least one compound selected from compounds represented by formula (2) as component B, and an optically active compound as additive X. In formula (1), R １ is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms; ring A is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, or tetrahydropyran-2,5-diyl; Z １ is a single bond, carbonyloxy, or difluoromethyleneoxy; X １ and X ２ is hydrogen or fluorine; a is 1 or 2; In formula (2), R ２ is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms; Z ２ is carbonyloxy or difluoromethyleneoxy; X ３ , X ４ , X ５ , X ６ , X ７ , and X ８ is hydrogen or fluorine; Y １ is fluorine, chlorine, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, alkoxy having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine.

2. 2. The liquid crystal composition according to claim 1, comprising, as component A, at least one compound selected from the compounds represented by formulas (1-1) to (1-9): In formulas (1-1) to (1-9), R １ is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms; X １ and X ２ is hydrogen or fluorine.

3. 3. The liquid crystal composition according to claim 1, wherein the proportion of component A is in the range of 5% by mass to 50% by mass.

4. 2. The liquid crystal composition according to claim 1, comprising, as component B, at least one compound selected from the compounds represented by formulas (2-1) to (2-8): In formulas (2-1) to (2-8), R ２ is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms; Y １ is fluorine, chlorine, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, alkoxy having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine.

5. 5. The liquid crystal composition according to claim 1, wherein the proportion of component B is in the range of 5% by mass to 50% by mass.

6. 2. The liquid crystal composition according to claim 1, comprising, as an additive X, at least one compound selected from the compounds represented by formulas (3-1) to (3-7): In formulas (3-1) to (3-7), R ３ and R ４ represents hydrogen, halogen, -C≡N, -N=C=O, -N=C=S, -SF ５ or alkyl having 1 to 10 carbon atoms, in which at least one —CH ２ - may be replaced by -O-, -COO-, -OCO-, -CH=CH- or -C≡C-, and in these groups, at least one hydrogen may be replaced by fluorine or chlorine.

7. 7. The liquid crystal composition according to claim 1, wherein the proportion of the additive X is in the range of 0.1% by mass to 10% by mass.

8. 2. The liquid crystal composition according to claim 1, comprising, as component C, at least one compound selected from compounds represented by formula (4): In formula (4), R ５ is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms; ring B is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, or tetrahydropyran-2,5-diyl; Z ３ is a single bond, ethylene, vinylene, carbonyloxy, or difluoromethyleneoxy; X ９ and X １０ is hydrogen or fluorine; Y ２ is fluorine, chlorine, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, alkoxy having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine; and b is 1, 2, 3, or 4.

9. 2. The liquid crystal composition according to claim 1, comprising, as component C, at least one compound selected from the compounds represented by formulas (4-1) to (4-26): In formulas (4-1) to (4-26), R ５ is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms.

10. The liquid crystal composition according to claim 8 , wherein the proportion of component C is in the range of 1% by mass to 50% by mass.

11. 2. The liquid crystal composition according to claim 1, comprising, as component D, at least one compound selected from compounds represented by formula (5): In formula (5), R ６ and R ７ is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine; ring C and ring D are 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene; Z ４ is a single bond, ethylene, vinylene, ethynylene, methyleneoxy, or carbonyloxy; and c is 1, 2, or 3.

12. 2. The liquid crystal composition according to claim 1, comprising, as component D, at least one compound selected from the compounds represented by formulas (5-1) to (5-20): In formulas (5-1) to (5-20), R ６ and R ７ is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine.

13. The liquid crystal composition according to claim 11, wherein the proportion of component D is in the range of 10% by mass to 90% by mass.

14. 2. The liquid crystal composition according to claim 1, comprising, as component E, at least one compound selected from compounds represented by formula (6): In formula (6), R 8 and R 9 represents hydrogen, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkenyloxy having 2 to 12 carbon atoms, or alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine; ring E and ring G represent 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl in which at least one hydrogen is replaced by fluorine or chlorine, chroman-2,6-diyl, or at least one hydrogen. ring F is 2,3-difluoro-1,4-phenylene, 1,8-difluorophenanthrene-2,7-diyl, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4,5-trifluoronaphthalene-2,6-diyl, 7,8-difluorochroman-2,6-diyl, 3,4,5,6-tetrafluorofluorene-2,7-diyl, 4,6-difluorodibenzofuran-3,7-diyl, 4,6-difluorodibenzothiophene-3,7-diyl, or 1,1,6,7-tetrafluoroindan-2,5-diyl; Z is 5 and Z 6 is a single bond, ethylene, vinylene, methyleneoxy, or carbonyloxy; d is 0, 1, 2, or 3; e is 0 or 1; and the sum of d and e is 3 or less.

15. 2. The liquid crystal composition according to claim 1, comprising, as component E, at least one compound selected from the compounds represented by formulas (6-1) to (6-36): In formulas (6-1) to (6-36), R 8 and R 9 is hydrogen, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkenyloxy having 2 to 12 carbon atoms, or alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine.

16. The liquid crystal composition according to claim 14 , wherein the proportion of component E is in the range of 1% by mass to 10% by mass.

17. 2. The liquid crystal composition according to claim 1, comprising, as an additive Y, at least one compound selected from polymerizable compounds represented by formula (7): In formula (7), ring I and ring K are cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxan-2-yl, pyrimidin-2-yl, or pyridin-2-yl, and in these rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine; ring J is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-2,6-diyl, naphthalene-3,7-diyl, naphthalene-4,8-diyl, naphthalene-5,9-diyl, naphthalene-6,10-diyl, naphthalene-7,11-diyl, naphthalene-8,12-diyl, naphthalene-9,13-diyl, naphthalene-14,15-diyl, naphthalene-16,16-diyl, naphthalene-17,18-diyl, naphthalene-19,19-diyl, naphthalene-20,19-diyl, naphthalene-21,19-diyl, naphthalene-22,19-diyl, naphthalene-23,19-diyl, naphthalene-24,19-diyl, naphthalene-25,19-diyl, naphthalene-31,19-diyl, naphthalene-26,19-diyl, naphthalene-27,19-diyl, phthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, in which at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by fluorine; Z ７ and Z ８ is a single bond or an alkylene having 1 to 10 carbon atoms, and in this alkylene, at least one —CH ２ - may be replaced by -O-, -CO-, -COO-, or -OCO-, and at least one -CH ２ CH ２ - is -CH=CH-, -C(CH ３ )=CH-, -CH=C(CH ３ ) - or -C(CH ３ )=C(CH ３ )-, in which at least one hydrogen may be replaced by fluorine; P １ From P ３ is a polymerizable group; Sp １ From Sp ３ is a single bond or an alkylene having 1 to 10 carbon atoms, and Sp １ From Sp ３ In the formula, at least one —CH ２ - may be replaced by -O-, -COO-, -OCO-, or -OCOO-, and at least one -CH ２ CH ２ - may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine; i is 0, 1, or 2; f, g, and h are 0, 1, 2, 3, or 4; and the sum of f, g, and h is 1 or greater.

18. In formula (7), P １ From P ３ The liquid crystal composition according to claim 17, wherein is a group selected from polymerizable groups represented by formulas (P-1) to (P-5): In formulas (P-1) to (P-5), M １ From M ３ is hydrogen, fluorine, alkyl having 1 to 5 carbon atoms, or alkyl having 1 to 5 carbon atoms in which at least one hydrogen atom is replaced by fluorine; １ From M ３ In the formula, at least one —CH ２ - may be replaced by -O-.

19. 2. The liquid crystal composition according to claim 1, comprising, as an additive Y, at least one compound selected from the group consisting of polymerizable compounds represented by formulas (7-1) to (7-29): In formulas (7-1) to (7-29), Sp １ From Sp ３ is a single bond or an alkylene having 1 to 10 carbon atoms, and Sp １ From Sp ３ In the formula, at least one —CH ２ - may be replaced by -O-, -COO-, -OCO-, or -OCOO-, and at least one -CH ２ CH ２ - may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine. ;P ４ From P ６ is a polymerizable group selected from groups represented by formulas (P-1) to (P-3); In formulas (P-1) to (P-3), M １ From M ３ is hydrogen, fluorine, alkyl having 1 to 5 carbon atoms, or alkyl having 1 to 5 carbon atoms in which at least one hydrogen atom is replaced by fluorine; １ From M ３ In the formula, at least one —CH ２ - may be replaced by -O-.

20. 18. The liquid crystal composition according to claim 17, wherein the proportion of the additive Y is in the range of 0.1% by mass to 5% by mass.

21. 2. The liquid crystal composition according to claim 1, wherein the optical anisotropy at a wavelength of 589 nm (measured at 25[deg.] C.) is 0.16 or more.

22. A liquid crystal device containing the liquid crystal composition according to claim 1.

23. 23. The liquid crystal device according to claim 22, which is a liquid crystal display device or a liquid crystal reflective device.

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