Liquid crystal composition and liquid crystal display element

Abstract

To provide a liquid crystal composition that fulfills at least one of the following properties, or exhibits a suitable balance between at least two of them: high upper temperature limit, low lower temperature limit, low viscosity, large optical anisotropy, large negative dielectric anisotropy, high elastic constant, high specific resistivity, high light stability, and high thermal stability; and to provide an AM device containing the composition and its applications.SOLUTION: A liquid crystal composition comprising, as component A, a specific compound having large optical anisotropy and large negative dielectric anisotropy, and optionally comprising, as component B, a specific compound having a high upper temperature limit or low viscosity, as component C, a specific compound having large negative dielectric anisotropy, or as additive X, a specific compound having a polymerizable group.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a liquid crystal composition, a liquid crystal display element containing this composition, etc. In particular, it relates to a liquid crystal composition having a negative dielectric anisotropy, and a liquid crystal display element containing this composition and having modes such as IPS, VA, FFS, and FPA. It also relates to a polymer-supported alignment type liquid crystal display element.

Background Art

[0002] In liquid crystal display elements, classifications based on the operation mode of liquid crystal molecules include modes such as PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS (in-plane switching), VA (vertical alignment), FFS (fringe field switching), and FPA (field-induced photo-reactive alignment). Classifications based on the driving method of the element are PM (passive matrix) and AM (active matrix). PM is classified into static, multiplex, etc., and AM is classified into TFT (thin film transistor), MIM (metal insulator metal), etc. The classification of TFT is amorphous silicon and polycrystalline silicon. The latter is classified into a high-temperature type and a low-temperature type according to the manufacturing process. Classifications based on the light source are a reflective type using natural light, a transmissive type using a backlight, and a transflective type using both natural light and a backlight.

[0003] The liquid crystal display element contains a liquid crystal composition having a nematic phase. This composition has appropriate characteristics. By improving the characteristics of this composition, an AM element having good characteristics can be obtained. The relationships among these characteristics are summarized in Table 1 below. The characteristics of the composition will be further described based on commercially available AM elements. The temperature range of the nematic phase is related to the temperature range in which the element can be used. The preferable upper limit temperature of the nematic phase is about 70 °C or higher, and the preferable lower limit temperature of the nematic phase is about -10 °C or lower. The viscosity of the composition is related to the response time of the element. A short response time is preferable for displaying moving images on the element. A response time shorter than 1 millisecond is desirable. Therefore, a small viscosity in the composition is preferable. A small viscosity at low temperatures is more preferable.

[0004] TIFF2025113213000001.tif67154

[0005] The optical anisotropy of the composition is related to the contrast ratio of the element. Depending on the mode of the element, a large optical anisotropy or a small optical anisotropy, that is, an appropriate optical anisotropy is required. The product (Δn × d) of the optical anisotropy (Δn) of the composition and the cell gap (d) of the element is designed to maximize the contrast ratio. The appropriate value of the product depends on the type of operating mode. This value ranges from about 0.30 μm to about 0.40 μm for elements in the VA mode, and from about 0.20 μm to about 0.35 μm for elements in the IPS mode or FFS mode. In these cases, a composition having a large optical anisotropy is preferable for an element with a small cell gap. A large dielectric anisotropy in the composition contributes to a low threshold voltage, low power consumption, and a large contrast ratio in the element. Therefore, a large dielectric anisotropy is preferable. A large specific resistance in the composition contributes to a large voltage holding ratio and a large contrast ratio in the element. Therefore, a composition having a large specific resistance at the initial stage is preferable. After long-term use, a composition having a large specific resistance is preferable. The stability of the composition against light and heat is related to the lifespan of the element. When this stability is high, the lifespan of the element is long. Such characteristics are preferable for AM elements used in liquid crystal monitors, liquid crystal TVs, etc.

[0006] In a general-purpose liquid crystal display element, the vertical alignment of liquid crystal molecules is achieved by a specific polyimide alignment film. In a polymer sustained alignment (PSA) type liquid crystal display element, a polymer is combined with the alignment film. First, a composition containing a small amount of a polymerizable compound is injected into the element. Next, while applying a voltage between the substrates of this element, the composition is irradiated with ultraviolet light. The polymerizable compound polymerizes to form a polymer network structure in the composition. In this composition, since the alignment of liquid crystal molecules can be controlled by the polymer, the response time of the element is shortened and image sticking is improved. Such an effect of the polymer can be expected for elements having modes such as TN, ECB, OCB, IPS, VA, FFS, and FPA.

[0007] In an AM element having a TN mode, a composition having a positive dielectric anisotropy is used. In an AM element having a VA mode, a composition having a negative dielectric anisotropy is used. In an AM element having an IPS mode or an FFS mode, a composition having a positive or negative dielectric anisotropy is used. In a polymer sustained alignment (PSA) type AM element, a composition having a positive or negative dielectric anisotropy is used.

[0008] In order to satisfy the required characteristics of the liquid crystal display element as described above, various compounds have been studied, and in recent years, compounds having a heterocyclic ring containing sulfur have been developed (Patent Documents 1 and 2, etc.).

Prior Art Documents

Patent Documents

[0009]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0010] The problems of the present invention are to provide a liquid crystal composition satisfying at least one of the characteristics such as a high upper limit temperature of the nematic phase, a low lower limit temperature of the nematic phase, a small viscosity, a large optical anisotropy, a large negative dielectric anisotropy, a large elastic constant, a large specific resistance, a high stability against light, and a high stability against heat. Another problem is to provide a liquid crystal composition having an appropriate balance between at least two of these characteristics. Another problem is to provide a liquid crystal display element containing such a composition. Another problem is to provide an AM element having characteristics such as a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long life.

Means for Solving the Problems

[0011] The present invention relates to a liquid crystal composition containing at least one compound selected from the compounds represented by the formula (1) as component A and having a negative dielectric anisotropy, and a liquid crystal display element containing this composition. TIFF2025113213000002.tif20101 In formula (1), R 1 and R 2 are hydrogen, alkyl having 1 to 12 carbon atoms, cyclic alkyl having 3 to 5 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; X 1 and X 2 are O or S; L 1 and L 2is hydrogen, fluorine, or trifluoromethyl; ring A and ring B 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, chroman - 2,6 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, fluorene - 2,7 - diyl, fluorene - 2,7 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, dibenzofuran - 3,7 - diyl, dibenzofuran - 3,7 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, dibenzothiophene - 3,7 - diyl, dibenzothiophene - 3,7 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, indane - 2,5 - diyl, indane - 2,5 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, thiophene - 2,5 - diyl, or furan - 2,5 - diyl; Z 1 and Z 2 is a single bond, ethylene, vinylene, ethynylene, methyleneoxy, or carbonyloxy; a and b are 0 or 1.

Advantages of the Invention

[0012] The advantages of the present invention are to provide a liquid crystal composition that satisfies at least one of the characteristics such as a high upper limit temperature of the nematic phase, a low lower limit temperature of the nematic phase, a small viscosity, a large optical anisotropy, a large negative dielectric anisotropy, a large elastic constant, a large specific resistance, a high stability to light, and a high stability to heat. Another advantage is to provide a liquid crystal composition having an appropriate balance between at least two of these characteristics. Another advantage is to provide a liquid crystal display element containing such a composition. Another advantage is to provide an AM element having characteristics such as a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long lifespan.

Modes for Carrying Out the Invention

[0013] The usage of terms in this specification is 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 a liquid crystal display panel and a liquid crystal display module. "Liquid crystalline compound" is a general term for a compound having a liquid crystal phase such as a nematic phase or a smectic phase, and a compound that does not have a liquid crystal phase but is mixed into a composition for the purpose of adjusting properties such as the temperature range, viscosity, and dielectric anisotropy of the nematic phase. This compound has a six-membered ring such as 1,4-cyclohexylene or 1,4-phenylene, and its molecule (liquid crystal molecule) is rod-like. "Polymerizable compound" is a compound added for the purpose of forming a polymer in the composition. A liquid crystalline compound having alkenyl is not classified as a polymerizable compound in that sense.

[0014] A liquid crystal composition is prepared by mixing a plurality of liquid crystalline compounds. Additives such as an optically active compound and a polymerizable compound are added to this liquid crystal composition as necessary. The ratio of the liquid crystalline compound is expressed as a mass percentage (mass%) based on the mass of the liquid crystal composition without additives even when additives are added. The ratio of the additive is expressed as a mass percentage (mass%) based on the mass of the liquid crystal composition without additives. That is, the ratios of the liquid crystalline compound and the additive are calculated based on the total mass of the liquid crystalline compound. Parts per million by mass (ppm) may be used. The ratios of the polymerization initiator and the polymerization inhibitor are exceptionally expressed based on the mass of the polymerizable compound.

[0015] "The upper limit temperature of the nematic phase" may be abbreviated as "upper limit temperature". "The lower limit temperature of the nematic phase" may be abbreviated as "lower limit temperature". The expression "increasing the dielectric anisotropy" means that when the composition has a positive dielectric anisotropy, its value increases positively, and when the composition has a negative dielectric anisotropy, its value increases negatively. "High voltage holding ratio" means that the element has a high voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature in the initial stage, and after long-term use, it has a high voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature. The characteristics of the composition and the element may be examined by an aging test.

[0016] TIFF2025113213000003.tif2070 The above compound (1z) will be described 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 a six-membered ring and a condensed ring. 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 linking group Z. The diagonal line crossing one side of ring β indicates that any hydrogen on ring β may be replaced by 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 more, a plurality of substituents (-Sp-P) exist on ring β. Also in this case, the rule of "may be the same or different" applies. This rule also applies when the symbol Ra is used for a plurality of compounds.

[0017] In formula (1z), for example, the expression "Ra and Rb are alkyl, alkoxy, or alkenyl" means that Ra and Rb are independently selected from the group consisting of alkyl, alkoxy, and alkenyl. That is, the group represented by Ra and the group represented by Rb may be the same or different.

[0018] 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).

[0019] The expression "at least one 'A'" means that the number of 'A's is arbitrary. The expression "at least one 'A' may be replaced by 'B'" means that when the number of 'A's is one, the position of 'A' is arbitrary, and when the number of 'A's is two or more, their positions can be selected without limitation. The expression "at least one -CH2- may be replaced by -O-" may be used. In this case, -CH2CH2-CH2- may be converted to -O-CH2-O- by replacing non-adjacent -CH2- with -O-. However, adjacent -CH2- will not be replaced by -O- because this replacement would generate -O-O-CH2- (peroxide).

[0020] When the alkyl of a liquid crystalline compound is simply described as "alkyl", it is linear or branched and does not include cyclic alkyl. "Alkyl" and "cyclic alkyl" are clearly distinguished. Linear alkyl is more preferred than branched alkyl. The same applies to end groups such as alkoxy and alkenyl. For the configuration regarding 1,4-cyclohexylene, trans is more preferred than cis in order to raise the upper limit temperature. Since 2-fluoro-1,4-phenylene is asymmetric, there are left-handed (L) and right-handed (R) forms. TIFF2025113213000004.tif25119 The same applies to divalent groups such as tetrahydropyran-2,5-diyl. The same also applies to linking groups such as carbonyloxy (-COO- or -OCO-).

[0021] The present invention is as follows in the following items and the like.

[0022] Item 1. A liquid crystal composition containing at least one compound selected from the compounds represented by the formula (1) as Component A and having negative dielectric anisotropy. TIFF2025113213000005.tif20101 In formula (1), R 1 and R 2 are hydrogen, alkyl having 1 to 12 carbon atoms, cyclic alkyl having 3 to 5 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; X 1 and X 2 are O or S; L 1 and L 2 are hydrogen, fluorine, or trifluoromethyl; ring A and ring B 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, chroman - 2,6 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, fluorene - 2,7 - diyl, fluorene - 2,7 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, dibenzofuran - 3,7 - diyl, dibenzofuran - 3,7 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, dibenzothiophene - 3,7 - diyl, dibenzothiophene - 3,7 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, indane - 2,5 - diyl, indane - 2,5 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, thiophene - 2,5 - diyl, or furan - 2,5 - diyl; Z 1 and Z 2is a single bond, ethylene, vinylene, ethynylene, methyleneoxy, or carbonyloxy; a and b are 0 or 1.

[0023] Item 2. In formula (1), X 1 and X 2 The liquid crystal composition according to item 1, wherein at least one of them is S.

[0024] Item 3. The liquid crystal composition according to item 1 or 2, containing at least one compound selected from the compounds represented by formulas (1-1) to (1-3) as component A. TIFF2025113213000006.tif6783 In formulas (1-1) to (1-3), R 1 and R 2 are hydrogen, alkyl having 1 to 12 carbon atoms, cyclic alkyl having 3 to 5 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; L 1 and L 2 are hydrogen, fluorine, or trifluoromethyl.

[0025] Item 4. The liquid crystal composition according to item 1 or 2, wherein the proportion of component A is in the range of 3% by mass to 20% by mass.

[0026] Item 5. The liquid crystal composition according to any one of items 1 to 4, containing at least one compound selected from the compounds represented by formula (2) as component B. TIFF2025113213000007.tif955 In formula (2), R 3 and R 4is alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, 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 3 is a single bond, ethylene, vinylene, methyleneoxy, or carbonyloxy; c is 1, 2, or 3.

[0027] 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 (2 - 1) to Formula (2 - 15) as Component B. TIFF2025113213000008.tif176108 TIFF2025113213000009.tif87106 In Formula (2 - 1) to Formula (2 - 15), R 3 and R 4 are alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine.

[0028] Item 7. The liquid crystal composition according to Item 5 or 6, wherein the proportion of Component B is in the range of 10% by mass to 90% by mass.

[0029] Item 8. The liquid crystal composition according to any one of Items 1 to 7, containing at least one compound selected from the compounds represented by Formula (3) as Component C. TIFF2025113213000010.tif1590 In Formula (3), R 5 and R 6is 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 chroman - 2,6 - diyl in which at least one hydrogen is replaced by fluorine or chlorine; ring F is 2,3 - difluoro - 1,4 - phenylene, 2 - chloro - 3 - fluoro - 1,4 - phenylene, 2,3 - difluoro - 5 - methyl - 1,4 - phenylene, 1,8 - difluorophenanthrene - 2,7 - diyl, 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, 1,1,6,7 - tetrafluoroindane - 2,5 - diyl, or 1,3,4 - thiadiazole - 2,5 - diyl; Z 4 and Z 5 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.

[0030] Item 9. The liquid crystal composition according to any one of Items 1 to 8, containing at least one compound selected from the compounds represented by Formula (3 - 1) to Formula (3 - 37) as Component C. TIFF2025113213000011.tif217106 TIFF2025113213000012.tif212109 TIFF2025113213000013.tif222108 TIFF2025113213000014.tif146108 In Formulas (3-1) to (3-37), R 5 and R 6 are 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.

[0031] Item 10. The liquid crystal composition according to Item 8 or 9, wherein the proportion of Component C is in the range of 10% by mass to 85% by mass.

[0032] Item 11. The liquid crystal composition according to any one of Items 1 to 10, which contains at least one compound selected from the polymerizable compounds represented by Formula (4) as Additive X. In formula (4) of TIFF2025113213000015, 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; 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, tetrahydropyran-2,5-diyl, 1,3-dioxan-2,5-diyl, pyrimidin-2,5-diyl, or pyridin-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; Z 6 and Z 7 is a single bond or alkylene having 1 to 10 carbon atoms, and in this alkylene, at least one -CH2- may be replaced by -O-, -CO-, -COO-, or -OCO-, 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; P 1 from P 3 is a polymerizable group; Sp 1 from Sp 3is 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; f is 0, 1, or 2; g, h, and i are 0, 1, 2, 3, or 4; and the sum of g, h, and i is 1 or more.

[0033] Item 12. In formula (4), P 1 to P 3 is a group selected from polymerizable groups represented by formula (P-1) to formula (P-5), and the liquid crystal composition according to item 11. TIFF2025113213000016.tif25134 In formula (P-1) to formula (P-5), M 1 to M 3 is hydrogen, fluorine, an alkyl having 1 to 5 carbon atoms, or an alkyl having 1 to 5 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine.

[0034] Item 13. The liquid crystal composition according to any one of items 1 to 12, containing at least one compound selected from polymerizable compounds represented by formula (4-1) to formula (4-29) as additive X. TIFF2025113213000017.tif239112 TIFF2025113213000018.tif227108 TIFF2025113213000019.tif212113 In formula (4-1) to formula (4-29), Sp 1 to Sp 3is 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; P 4 from P 6 is a polymerizable group selected from the groups represented by formula (P-1) to formula (P-3); TIFF2025113213000020.tif3087 In formula (P-1) to formula (P-3), M 1 from M 3 is hydrogen, fluorine, an alkyl having 1 to 5 carbon atoms, or an alkyl having 1 to 5 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine.

[0035] Item 14. The liquid crystal composition according to any one of Items 11 to 13, wherein the proportion of additive X is in the range of 0.03% by mass to 10% by mass.

[0036] Item 15. A liquid crystal display element containing the liquid crystal composition according to any one of Items 1 to 14.

[0037] Item 16. The liquid crystal display element according to Item 15, wherein the operation mode is an IPS mode, a VA mode, a FFS mode, or a FPA mode, and the driving method is an active matrix method.

[0038] Item 17. A polymer-supported alignment type liquid crystal display element containing the liquid crystal composition according to any one of Items 11 to 14, and in which the polymerizable compound in this liquid crystal composition has polymerized.

[0039] Item 18. Use of the liquid crystal composition according to any one of Items 1 to 14 in a liquid crystal display element.

[0040] Use of the liquid crystal composition according to any one of items 11 to 14 in a polymer-supported alignment type liquid crystal display element.

[0041] The present invention also includes the following items. (a) The above composition containing one compound, two compounds, or three or more compounds selected from additives such as an optically active compound, an antioxidant, an ultraviolet absorber, a light extinction agent, a dye, an antifoaming agent, a polymerizable compound, a polymerization initiator, and a polymerization inhibitor. (b) An AM element containing the above composition. (c) The above composition further containing a polymerizable compound, and a polymer-supported alignment (PSA) type AM element containing this composition. (d) A polymer-supported alignment (PSA) type AM element containing the above composition and in which the polymerizable compound in this composition has polymerized. (e) An element containing the above composition and having a mode of PC, TN, STN, ECB, OCB, IPS, VA, FFS, or FPA. (f) A transmissive element containing the above composition. (g) Use of the above composition as a composition having a nematic phase. (h) Use of an optically active composition obtained by adding an optically active compound to the above composition.

[0042] The composition of the present invention will be described in the following order. First, the configuration of the composition will be described. Second, the main characteristics of the component compounds and the main effects of these compounds on the composition and the element will be described. Third, the combination, preferred ratio, and basis of the component compounds in the composition will be described. Fourth, the preferred forms of the component compounds will be described. Fifth, the preferred component compounds will be shown. Sixth, additives that may be added to the composition will be described. Seventh, the synthesis method of the component compounds will be described. Finally, the uses of the composition will be described.

[0043] First, the composition will be described. This composition contains a plurality of liquid crystalline compounds. This composition may contain additives. The additives are, for example, optically active compounds, antioxidants, ultraviolet absorbers, light extinction agents, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, polar compounds, and the like. This composition is classified into composition (a) and composition (b) from the perspective of liquid crystalline compounds. Composition (a) may further contain other liquid crystalline compounds, additives, etc. in addition to the liquid crystalline compounds selected from compound (1), compound (2), and compound (3). "Other liquid crystalline compounds" are liquid crystalline compounds different from compound (1), compound (2), and compound (3). Such compounds are mixed into the composition for the purpose of further adjusting the properties.

[0044] Composition (b) consists essentially of only the liquid crystalline compounds selected from compound (1), compound (2), and compound (3). "Essentially" means that composition (b) may contain additives but does not contain other liquid crystalline compounds. Composition (b) has fewer components compared to composition (a). From the perspective of cost reduction, composition (b) is more preferable than composition (a). From the perspective that the properties can be further adjusted by mixing other liquid crystalline compounds, composition (a) is more preferable than composition (b).

[0045] Second, the main properties of the component compounds and the main effects of this compound on the composition and device will be described. The main properties of the component compounds are summarized in Table 2 based on the effects of the present invention. In the symbols of 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 a qualitative comparison among the component compounds, and 0 (zero) means smaller than S.

[0046] TIFF2025113213000021.tif67127

[0047] The main effects of the component compounds are as follows. Compound (1) raises the upper limit temperature, optical anisotropy, and dielectric anisotropy. Compound (2) raises the upper limit temperature or lowers the viscosity. Compound (3) raises the dielectric anisotropy or lowers the lower limit temperature. Compound (4) gives a polymer by polymerization. This polymer stabilizes the alignment of liquid crystal molecules, thus shortening the response time of the device and improving image burn-in.

[0048] Thirdly, explain the combination, preferred ratio, and the basis thereof of the component compounds in the composition. The preferred combinations of the component compounds in the composition are Compound (1) + Compound (2), Compound (1) + Compound (3), Compound (1) + Compound (2) + Compound (3), Compound (1) + Compound (2) + Compound (4), Compound (1) + Compound (3) + Compound (4), or Compound (1) + Compound (2) + Compound (3) + Compound (4). More preferred combinations are Compound (1) + Compound (2) or Compound (1) + Compound (2) + Compound (3).

[0049] The preferred ratio of Compound (1) is about 3% by mass or more for raising the upper limit temperature, optical anisotropy, and dielectric anisotropy, and about 20% by mass or less for lowering the lower limit temperature. A more preferred ratio is in the range of about 3% by mass to about 15% by mass. A particularly preferred ratio is in the range of about 3% by mass to about 12% by mass.

[0050] The preferred ratio of Compound (2) is about 10% by mass or more for raising the upper limit temperature or lowering the viscosity, and about 90% by mass or less for raising the dielectric anisotropy. A more preferred ratio is in the range of about 20% by mass to about 80% by mass. A particularly preferred ratio is in the range of about 30% by mass to about 70% by mass.

[0051] The preferred ratio of Compound (3) is about 10% by mass or more for raising the dielectric anisotropy or lowering the lower limit temperature, and about 85% by mass or less for lowering the viscosity. A more preferred ratio is in the range of about 20% by mass to about 75% by mass. A particularly preferred ratio is in the range of about 30% by mass to about 60% by mass.

[0052] Compound (4) is added to the composition for the purpose of adapting it to a polymer-supported alignment type element. The preferred proportion of compound (4) is at least about 0.03% by mass in order to align liquid crystal molecules, and at most about 10% by mass in order to prevent display defects of the element. A more preferred proportion is in the range of about 0.1% to about 2% by mass. A particularly preferred proportion is in the range of about 0.2% to about 1.0% by mass.

[0053] Fourthly, the preferred forms of the component compounds are described. In formula (1), formula (2), and formula (3), R 1 and R 2 are hydrogen, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 5 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. Preferred R 1 or R 2 is alkoxy having 1 to 12 carbon atoms in order to increase the dielectric anisotropy, and alkyl having 1 to 12 carbon atoms in order to increase the stability. R 3 and R 4 are alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. Preferred R 3 or R 4 is alkyl having 1 to 12 carbon atoms in order to increase the stability, and alkenyl having 2 to 12 carbon atoms in order to decrease the viscosity. R 5 and R 6 are 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. Preferred R 5 or R 6For increasing stability, it is an alkyl having 1 to 12 carbon atoms, for decreasing viscosity, it is an alkenyl having 2 to 12 carbon atoms, and for increasing dielectric anisotropy, it is an alkoxy having 1 to 12 carbon atoms.

[0054] Preferred alkyls are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, or octyl. More preferred alkyls for decreasing viscosity are methyl, ethyl, propyl, butyl, or pentyl.

[0055] Preferred cyclic alkyls are cyclopropyl, cyclobutyl, or cyclopentyl.

[0056] Preferred alkoxys are methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, or heptyloxy. More preferred alkoxys for decreasing viscosity are methoxy or ethoxy.

[0057] 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, or 5-hexenyl. More preferred alkenyls for decreasing viscosity are vinyl, 1-propenyl, 3-butenyl, or 3-pentenyl. The preferred configuration of -CH=CH- in these alkenyls depends on the position of the double bond. For alkenyls such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyl, 3-hexenyl for reasons such as decreasing viscosity, trans is preferred. For alkenyls such as 2-butenyl, 2-pentenyl, 2-hexenyl, cis is preferred.

[0058] Preferred alkenyloxy is vinyloxy, allyloxy, 3-butenyloxy, 3-pentenyloxy, or 4-pentenyloxy. To lower the viscosity, more preferred alkenyloxy is allyloxy or 3-butenyloxy.

[0059] Preferred examples of alkyl in which at least one hydrogen is replaced by fluorine or chlorine are fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl, 7-fluoroheptyl, or 8-fluorooctyl. More preferred examples are 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, or 5-fluoropentyl to increase the dielectric anisotropy.

[0060] Preferred examples of alkenyl in which at least one hydrogen is replaced by fluorine or chlorine are 2,2-difluorovinyl, 3,3-difluoro-2-propenyl, 4,4-difluoro-3-butenyloxy, 5,5-difluoro-4-pentenyl, or 6,6-difluoro-5-hexenyl. More preferred examples are 2,2-difluorovinyl or 4,4-difluoro-3-butenyloxy to lower the viscosity.

[0061] Ring A and ring B 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, chroman-2,6-diyl in which at least one hydrogen is replaced by fluorine or chlorine, fluorene-2,7-diyl, fluorene-2,7-diyl in which at least one hydrogen is replaced by fluorine or chlorine, dibenzofuran-3,7-diyl, dibenzofuran-3,7-diyl in which at least one hydrogen is replaced by fluorine or chlorine, dibenzothiophene-3,7-diyl, dibenzothiophene-3,7-diyl in which at least one hydrogen is replaced by fluorine or chlorine, indane-2,5-diyl, indane-2,5-diyl in which at least one hydrogen is replaced by fluorine or chlorine, thiophene-2,5-diyl, or furan-2,5-diyl. Preferred ring A or ring B is 1,4-cyclohexylene for reducing viscosity and 1,4-phenylene or 2-fluoro-1,4-phenylene for increasing optical anisotropy.

[0062] 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 reducing viscosity and 1,4-phenylene or 2-fluoro-1,4-phenylene for increasing optical anisotropy.

[0063] 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" are 2 - fluoro - 1,4 - phenylene, 2,3 - difluoro - 1,4 - phenylene or 2 - chloro - 3 - fluoro - 1,4 - phenylene. Preferred ring E or ring G is 1,4 - cyclohexylene for reducing viscosity, tetrahydropyran - 2,5 - diyl for increasing dielectric anisotropy, and 1,4 - phenylene for increasing optical anisotropy.

[0064] The tetrahydropyran - 2,5 - diyl in ring A, ring B, ring E, and ring G is TIFF2025113213000022.tif1323 or TIFF2025113213000023.tif1323 and preferably TIFF2025113213000024.tif1323 is.

[0065] Ring F is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 1,8-difluorophenanthrene-2,7-diyl, 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), 1,1,6,7-tetrafluoroindane-2,5-diyl (InF4), or 1,3,4-thiadiazole-2,5-diyl. TIFF2025113213000025.tif28166 Preferred ring F is 2,3-difluoro-1,4-phenylene for lowering viscosity, and 1,8-difluorophenanthrene-2,7-diyl or 4,6-difluorodibenzothiophene-3,7-diyl for increasing dielectric anisotropy.

[0066] Z 1 and Z 2 are a single bond, ethylene, vinylene, ethynylene, methyleneoxy, or carbonyloxy. Preferred Z 1 or Z 2 is a single bond for lowering viscosity and methyleneoxy for increasing dielectric anisotropy. Z 3 is a single bond, ethylene, vinylene, methyleneoxy, or carbonyloxy. Preferred Z 3 is a single bond for lowering viscosity. Z 4 and Z 5 are a single bond, ethylene, vinylene, methyleneoxy, or carbonyloxy. Preferred Z 4 or Z 5 is a single bond for lowering viscosity, ethylene for increasing elastic constant, and methyleneoxy for increasing dielectric anisotropy.

[0067] Divalent groups such as methyleneoxy are left - right asymmetric. In methyleneoxy, -CH2O- is more preferred than -OCH2-. In carbonyloxy, -COO- is more preferred than -OCO-.

[0068] L 1 and L 2 is hydrogen, fluorine, or trifluoromethyl. Preferred L 1 or L 2 is fluorine to lower the viscosity and increase the dielectric anisotropy.

[0069] X 1 and X 2 is O or S. To widen the temperature range of the nematic phase, at least one of X 1 and X 2 is preferably S. It is particularly preferred that one of X 1 and X 2 is S and the other is O.

[0070] a and b are 0 or 1. Preferred a or b is 0 to lower the viscosity and the lower limit temperature. It is particularly preferred that both a and b are 0. Preferred c is 1 to lower the viscosity and 2 or 3 to raise the upper limit temperature. d is 0, 1, 2, or 3, e is 0 or 1, and the sum of d and e is 3 or less. Preferred d is 0 or 1 to lower the viscosity and 2 to raise the upper limit temperature. Preferred e is 0 to lower the viscosity and 1 to raise the upper limit temperature.

[0071] In formula (4), 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, tetrahydropyran-2,5-diyl, 1,3-dioxan-2,5-diyl, pyrimidin-2,5-diyl, or pyridin-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.

[0072] Z 6 and Z 7 is a single bond or alkylene having 1 to 10 carbon atoms, and in this alkylene, at least one -CH2- may be replaced by -O-, -CO-, -COO-, or -OCO-, 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 6 or Z 7is a single bond, -CH2CH2-, -CH2O-, -OCH2-, -COO-, or -OCO-. More preferably, Z 6 or Z 7 is a single bond.

[0073] 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. Preferably, Sp 1 from Sp 3 is a single bond, -CH2CH2-, -CH2O-, -OCH2-, -COO-, -OCO-, -CO-CH=CH-, or -CH=CH-CO-. More preferably, Sp 1 from Sp 3 is a single bond.

[0074] f is 0, 1, or 2. Preferably, f is 0 or 1. g, h, and i are 0, 1, 2, 3, or 4, and the sum of g, h, and i is 1 or more. Preferably, g, h, or i is 1 or 2.

[0075] P 1 from P 3 is a polymerizable group. Preferably, P 1 from P 3 is a polymerizable group selected from the groups represented by formula (P-1) to formula (P-5). More preferably, P 1 from P 3 is a group represented by formula (P-1), formula (P-2), or formula (P-3). Particularly preferably, P 1 from P 3 is a group represented by formula (P-1) or formula (P-2). Most preferably, P 1 from P 3is a group represented by formula (P-1). Preferred groups represented by formula (P-1) are -OCO-CH=CH2 or -OCO-C(CH3)=CH2. The wavy lines from formula (P-1) to formula (P-5) indicate the bonding sites. TIFF2025113213000026.tif34166

[0076] In formulas (P-1) to (P-5), M 1 to M 3 is hydrogen, fluorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. Preferred M 1 to M 3 is hydrogen or methyl in order to increase reactivity. More preferred M 1 is hydrogen or methyl, and even more preferred M 2 or M 3 is hydrogen.

[0077] In formulas (4-1) to (4-29), P 4 to P 6 is a group represented by formulas (P-1) to (P-3). Preferred P 4 to P 6 is formula (P-1) or formula (P-2). A more preferred formula (P-1) is -OCO-CH=CH2 or -OCO-C(CH3)=CH2. The wavy lines from formula (P-1) to formula (P-3) indicate the bonding sites. TIFF2025113213000027.tif3197

[0078] Fifthly, preferred component compounds are shown. Preferred compound (1) is compounds (1-1) to (1-3) described in item 3. In these compounds, it is preferable that at least one of component A is compound (1-1) or compound (1-2). From the viewpoint of lowering the lower limit temperature, it is preferable to use a plurality of compounds (1-1), a plurality of compounds (1-2), or a combination of compound (1-1) and compound (1-2).

[0079] Preferred compound (2) is compound (2-1) to compound (2-15) described in item 6. In these compounds, at least one of component B is preferably compound (2-1), compound (2-2), compound (2-3), compound (2-4), compound (2-5), compound (2-7), compound (2-8), or compound (2-12). It is more preferable that at least one of component B is compound (2-1), compound (2-4), or compound (2-7), and it is preferable that their total is 35% by mass or more. R 3 and R 4 Compound (2) in which at least one of them is alkenyl having 2 to 4 carbon atoms is preferable, and it is preferable that their total is 35% by mass or more. It is preferable that at least two of component B are compound (2-1) and compound (2-4), compound (2-1) and compound (2-7), or compound (2-1) and compound (2-12).

[0080] Preferred compound (3) is compound (3-1) to compound (3-36) described in item 9. In these compounds, at least one of component C is preferably compound (3-1), compound (3-6), compound (3-8), compound (3-9), compound (3-10), compound (3-14), compound (3-19), or compound (3-36). It is preferable that the total ratio of compound (3-1), compound (3-6), compound (3-8), compound (3-14), and compound (3-36) is in the range of 40% by mass to 60% by mass. It is also preferable that the total ratio of compound (3-9), compound (3-10), and compound (3-36) is 30% by mass or more. It is particularly preferable that at least one of component C is compound (3-36), and it is preferable that the ratio of compound (3-36) is in the range of 5% by mass to 10% by mass. It is preferable that at least two of component C are a combination of compound (3-1) and compound (3-36), compound (3-6) and compound (3-36), compound (3-8) and compound (3-36), compound (3-9) and compound (3-36), compound (3-10) and compound (3-36), or compound (3-14) and compound (3-36).

[0081] The preferred compound (4) is compounds (4-1) to (4-29) described in item 13. Among these compounds, it is preferable that at least one of the additives X is compound (4-1), compound (4-2), compound (4-24), compound (4-25), compound (4-26), or compound (4-27). It is preferable that at least two of the additives X are a combination of compound (4-1) and compound (4-2), compound (4-1) and compound (4-18), compound (4-2) and compound (4-24), compound (4-2) and compound (4-25), compound (4-2) and compound (4-26), compound (4-25) and compound (4-26), or compound (4-18) and compound (4-24).

[0082] Sixthly, additives that may be added to the composition are described. Such additives include optically active compounds, antioxidants, ultraviolet absorbers, light extenders, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, polar compounds, etc. Optically active compounds are added to the composition for the purpose of inducing a helical structure of liquid crystal molecules and giving a twist angle. Examples of such compounds are compounds (5-1) to (5-5). The preferred proportion of the optically active compound is about 5% by mass or less. A more preferred proportion is in the range of about 0.01% by mass to about 2% by mass. TIFF2025113213000028.tif92130 TIFF2025113213000029.tif51127

[0083] In order to prevent a decrease in specific resistance due to heating in the atmosphere, or to maintain a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature after the device has been used for a long time, antioxidants such as compounds (6-1) to (6-3) may be further added to the composition. TIFF2025113213000030.tif89125

[0084] Since compound (6-2) has low volatility, it is effective in maintaining a large voltage retention rate not only at room temperature but also at a temperature close to the upper limit temperature after long-term use of the device. The preferred proportion of the antioxidant is about 50 ppm or more in order to obtain its effect, and about 600 ppm or less so as not to lower the upper limit temperature or raise the lower limit temperature. A more preferred proportion is in the range of about 100 ppm to about 300 ppm.

[0085] Preferred examples of the ultraviolet absorber are benzophenone derivatives, benzoate derivatives, triazole derivatives, etc. Light stabilizers such as sterically hindered amines are also preferred. Preferred examples of the light stabilizer are compounds (7-1) to compounds (7-16), etc. The preferred proportion in these absorbers and stabilizers is about 50 ppm or more in order to obtain their effect, and about 10000 ppm or less so as not to lower the upper limit temperature or raise the lower limit temperature. A more preferred proportion is in the range of about 100 ppm to about 10000 ppm. TIFF2025113213000031.tif254140 TIFF2025113213000032.tif252142

[0086] The quencher is a compound that prevents the decomposition of the liquid crystalline compound by receiving the light energy absorbed by the liquid crystalline compound and converting it into thermal energy. Preferred examples of the quencher are compounds (8-1) to compounds (8-7), etc. The preferred proportion in these quenchers is about 50 ppm or more in order to obtain their effect, and about 20000 ppm or less so as not to raise the lower limit temperature. A more preferred proportion is in the range of about 100 ppm to about 10000 ppm. TIFF2025113213000033.tif15879

[0087] To adapt to the element in the GH (guest host) mode, dichroic dyes such as azo dyes and anthraquinone dyes are added to the composition. The preferred proportion of the dye ranges from about 0.01% by mass to about 10% by mass. To prevent foaming, an antifoaming agent such as dimethyl silicone oil or methylphenyl silicone oil is added to the composition. The preferred proportion of the antifoaming agent is about 1 ppm or more to obtain the effect and about 1000 ppm or less to prevent display defects. A more preferred proportion ranges from about 1 ppm to about 500 ppm.

[0088] A polymerizable compound is used to adapt to the polymer support alignment (PSA) type element. Compound (4) is suitable for this purpose. A polymerizable compound different from compound (4) may be added to the composition together with compound (4). Preferred examples of such polymerizable compounds are compounds such as acrylate, methacrylate, vinyl compound, vinyloxy compound, propenyl ether, epoxy compound (oxirane, oxetane), and vinyl ketone. More preferred examples are derivatives of acrylate or methacrylate. The preferred proportion of compound (4) is 10% by mass or more based on the total mass of the polymerizable compound. A more preferred proportion is 50% by mass or more. A particularly preferred proportion is 80% by mass or more. The most preferred proportion is 100% by mass.

[0089] A polymerizable compound such as compound (4) polymerizes by ultraviolet irradiation. Polymerization may be carried out in the presence of a suitable initiator such as a photoinitiator. Appropriate conditions for polymerization, the appropriate type of initiator, and the appropriate amount are known to those skilled in the art and are described in the literature. For example, Irgacure651 (registered trademark; BASF), Irgacure184 (registered trademark; BASF), or Darocur1173 (registered trademark; BASF), which are photoinitiators, are suitable for radical polymerization. The preferred proportion of the photoinitiator ranges from about 0.1% by mass to about 5% by mass based on the total mass of the polymerizable compound. A more preferred proportion ranges from about 1% by mass to about 3% by mass.

[0090] When storing a polymerizable compound such as compound (4), 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 the polymerization inhibitor include hydroquinone, hydroquinone derivatives such as methylhydroquinone, 4-t-butylcatechol, 4-methoxyphenol, phenothiazine, and the like.

[0091] Seventhly, the synthesis methods of the component compounds will be described. These compounds can be synthesized by known methods. Examples of the synthesis methods will be given. The synthesis example of compound (1) is described in the Examples section. Compound (2-1) is synthesized by the method described in JP-A-9-77692. Compound (3-1) is synthesized by the method described in JP-T-2-503441. Compound (4-18) is synthesized by the method described in JP-A-7-101900. The antioxidant is commercially available. Compound (6-1) is available from Aldrich (Sigma-Aldrich Corporation). Compounds such as compound (6-2) are synthesized by the method described in U.S. Patent No. 3,660,505.

[0092] Compounds for which the synthesis method is not described can be synthesized by the methods described in books such as Organic Syntheses (John Wiley & Sons, Inc.), Organic Reactions (John Wiley & Sons, Inc.), Comprehensive Organic Synthesis (Pergamon Press), and New Experimental Chemistry Course (Maruzen). The composition is prepared from the compounds thus obtained by known methods. For example, the component compounds are mixed and dissolved in each other by heating.

[0093] Finally, the uses of the composition are described. This composition mainly has a lower limit temperature of about -10°C or lower, an upper limit temperature of about 70°C or higher, and an optical anisotropy in the range of about 0.07 to about 0.20. By controlling the ratio of the component compounds or by mixing other liquid crystalline compounds, a composition having an optical anisotropy in the range of about 0.08 to about 0.25 may be prepared. By trial and error, a composition having an optical anisotropy in the range of about 0.10 to about 0.30 may be prepared. The device containing this composition has a large voltage holding ratio. This composition is suitable for AM devices. This composition is particularly suitable for transmissive AM devices. This composition can be used as a composition having a nematic phase and as an optically active composition by adding an optically active compound.

[0094] This composition can be used in AM devices. Furthermore, it can also be used in PM devices. This composition can be used in AM devices and PM devices having modes such as PC, TN, STN, ECB, OCB, IPS, FFS, VA, and FPA. Use in AM devices having TN, OCB, IPS modes or FFS modes is particularly preferred. In AM devices having IPS modes or FFS modes, when no voltage is applied, the alignment of liquid crystal molecules may be parallel or perpendicular to the glass substrate. These devices may be reflective, transmissive, or transflective. Use in transmissive devices is preferred. Use in amorphous silicon-TFT devices or polycrystalline silicon-TFT devices is also possible. This composition can also be used in NCAP (nematic curvilinear aligned phase) type devices prepared by microencapsulating the composition and in PD (polymer dispersed) type devices in which a three-dimensional network polymer is formed in the composition.

Examples

[0095] The present invention will be described in more detail by way of 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 obtained by mixing 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.

[0096] NMR analysis: For the measurement, a DRX-500 manufactured by Bruker BioSpin was used. 1 In the measurement of 1H-NMR, the sample was dissolved in a deuterated solvent such as CDCl3, and the measurement was carried out at room temperature under the conditions of 500 MHz and 16 integration times. Tetramethylsilane was used as an internal standard. 19 In the measurement of 19F-NMR, CFCl3 was used as an internal standard and the measurement was carried out with 24 integration times. In the description of the nuclear magnetic resonance spectrum, 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.

[0097] Gas chromatographic analysis: For the measurement, a GC-14B type gas chromatograph manufactured by Shimadzu Corporation was used. The carrier gas was helium (2 mL / min). The sample vaporization chamber was set at 280 °C and the detector (FID) was set at 300 °C. For the separation of the component compounds, a capillary column DB-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm; stationary liquid phase is dimethylpolysiloxane; non-polar) manufactured by Agilent Technologies Inc. was used. This column was held at 200 °C for 2 minutes and then heated to 280 °C at a rate of 5 °C / min. The sample was prepared in an acetone solution (0.1 mass%) and then 1 μL of it was injected into the sample vaporization chamber. The recorder was a C-R5A type Chromatopac manufactured by Shimadzu Corporation or its equivalent. The obtained gas chromatogram showed the retention time and the area of the peaks corresponding to the component compounds.

[0098] Solvents for diluting the sample may include chloroform, hexane, etc. For separating the component compounds, the following capillary columns may be used: HP-1 manufactured by Agilent Technologies Inc. (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm), Rtx-1 manufactured by Restek Corporation (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm), BP-1 manufactured by SGE International Pty. Ltd (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm). For the purpose of preventing overlap of compound peaks, a capillary column CBP1-M50-025 (length 50 m, inner diameter 0.25 mm, film thickness 0.25 μm) manufactured by Shimadzu Corporation may be used.

[0099] The ratio of the liquid crystalline compound contained in the composition may be calculated by the following method. Analyze a mixture of liquid crystalline compounds by gas chromatography (FID). The area ratio of the peaks in the gas chromatogram corresponds to the ratio of the liquid crystalline compounds. When using the capillary columns described above, the correction factor for each liquid crystalline compound may be regarded as 1. Therefore, the ratio (mass %) of the liquid crystalline compound can be calculated from the area ratio of the peaks.

[0100] Measurement sample: When measuring the properties of the composition or device, the composition was used as the sample as it was. When measuring the properties of the compound, a measurement sample was prepared by mixing this compound (15 mass %) with a host liquid crystal (85 mass %). The characteristic values of the compound were calculated by extrapolation from the values obtained by measurement. (Extrapolated value) = {(Measured value of the sample) - 0.85×(Measured value of the host liquid crystal)} / 0.15. When the smectic phase (or crystal) precipitates at 25°C at this ratio, the ratio of the compound to the host liquid crystal was changed in the order of 10 mass %:90 mass %, 5 mass %:95 mass %, 1 mass %:99 mass %. The values of the upper limit temperature, optical anisotropy, viscosity, and dielectric anisotropy of the compound were determined by this extrapolation method.

[0101] The following host liquid crystals were used. The ratios of the component compounds are shown in mass %. TIFF2025113213000034.tif84155

[0102] Measurement method: The characteristics were measured by the following methods. Many of these were the methods described in the JEITA standard (JEITA·ED-2521B) deliberated and established by the Japan Electronics and Information Technology Industries Association (JEITA), or modified methods thereof. The TN element used for measurement was not attached with a thin film transistor (TFT).

[0103] (1) Upper limit temperature of nematic phase (NI; °C): The sample was placed on the hot plate of a melting point measuring device 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 phase to an isotropic liquid was measured. The upper limit temperature of the nematic phase may be abbreviated as the "upper limit temperature".

[0104] (2) Lower limit temperature of nematic phase (T C ; °C): The sample having a nematic phase was put into a glass bottle and stored in freezers at 0 °C, -10 °C, -20 °C, -30 °C, and -40 °C for 10 days, and then the liquid crystal phase was observed. For example, when the sample remained in the nematic phase at -20 °C and changed to a crystal or smectic phase at -30 °C, T C was described as <-20 °C. The lower limit temperature of the nematic phase may be abbreviated as the "lower limit temperature".

[0105] (3) Viscosity (bulk viscosity; η; measured at 20 °C; mPa·s): An E-type rotational viscometer manufactured by Tokyo Keiki Co., Ltd. was used for the measurement.

[0106] (4) Viscosity (rotational viscosity; γ1; measured at 25 °C; mPa·s): For the measurement, a rotational viscosity measurement system LCM-2 type manufactured by Toyo Technica Co., Ltd. was used. The sample was injected into a VA element with a cell gap of 10 μm between two glass substrates. A rectangular wave (55 V, 1 ms) was applied to this element. The peak current and peak time of the transient current generated by this application were measured. Using these measured values and the dielectric anisotropy, the value of the rotational viscosity was obtained. The dielectric anisotropy was measured by the method described in measurement (6).

[0107] (5) Optical anisotropy (refractive index anisotropy; Δn; measured at 25 °C): The measurement was carried out using light with a wavelength of 589 nm and an Abbe refractometer with a polarizing plate attached to the eyepiece. After rubbing the surface of the main prism in one direction, the sample was dropped onto the main prism. The refractive index n∥ was measured when the direction of polarization was parallel to the rubbing direction. The refractive index n⊥ was measured when the direction of polarization was perpendicular to the rubbing direction. The value of the optical anisotropy was calculated from the formula Δn = n∥ - n⊥.

[0108] (6) Dielectric anisotropy (Δε; measured at 25 °C): The value of the dielectric anisotropy was calculated from the formula Δε = ε∥ - ε⊥. The dielectric constants (ε∥ and ε⊥) were measured as follows. 1) Measurement of dielectric constant (ε∥): A solution of octadecyltriethoxysilane (0.16 mL) in ethanol (20 mL) was applied to a well-washed glass substrate. After rotating the glass substrate with a spinner, it was heated at 150 °C for 1 hour. The sample was put into a VA element with a cell gap of 4 μm between two glass substrates, and this element was sealed with an adhesive cured by ultraviolet light. A sine wave (0.5 V, 1 kHz) was applied to this element, and 2 seconds later, the dielectric constant (ε∥) in the long axis direction of the liquid crystal molecules was measured. (2) Measurement of dielectric constant (ε⊥): A polyimide solution was applied to a well-cleaned glass substrate. After firing this glass substrate, the obtained alignment film was rubbed. The sample was placed in a TN cell with a cell gap of 9 μm and a twist angle of 80°. A sine wave (0.5 V, 1 kHz) was applied to this cell, and 2 seconds later, the dielectric constant (ε⊥) in the short-axis direction of the liquid crystal molecules was measured.

[0109] (7) Threshold voltage (Vth; measured at 25 °C; V): An LCD5200 type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source was a halogen lamp. The sample was placed in a VA cell with a cell gap of 4 μm and an anti-parallel rubbing direction in the normally black mode, and this cell was sealed using an adhesive cured by ultraviolet light. The voltage (60 Hz, rectangular wave) applied to this cell was increased stepwise from 0 V to 20 V in increments of 0.02 V. At this time, light was irradiated on the cell from the perpendicular direction, and the amount of light transmitted through the cell was measured. A voltage-transmittance curve was created where the transmittance was 100% when the light amount was maximum and 0% when the light amount was minimum. The threshold voltage was represented by the voltage when the transmittance reached 10%.

[0110] (8) Voltage holding ratio (VHR-1; measured at 25 °C; %): The TN cell used for the measurement had a polyimide alignment film, and the cell gap between the two glass substrates was 5 μm. This cell was sealed with an adhesive cured by ultraviolet light after the sample was placed in it. A pulse voltage (5 V for 60 microseconds) was applied to this TN cell for charging. The decaying voltage was measured with a high-speed voltmeter for 16.7 milliseconds, and the area A between the voltage curve in a unit period and the horizontal axis was obtained. Area B was the area when no decay occurred. The voltage holding ratio was represented by the percentage of area A with respect to area B.

[0111] (9) Voltage holding ratio (VHR-2; measured at 80 °C; %): The voltage holding ratio was measured in the same procedure as above, except that the measurement was performed at 80 °C instead of 25 °C. The obtained value was represented by VHR-2.

[0112] (10) Voltage holding ratio (VHR-3; measured at 25 °C; %): After irradiating with ultraviolet light, the voltage holding ratio was measured to evaluate the stability against ultraviolet light. The TN element used for the measurement had a polyimide alignment film and the cell gap was 5 μm. The sample was injected into this element and irradiated with light for 20 minutes. The light source was an ultra-high pressure mercury lamp USH-500D (manufactured by Ushio Inc.), and the distance between the element and the light source was 20 cm. In the measurement of VHR-3, the voltage decaying within 16.7 milliseconds was measured. A composition having a large VHR-3 has a large stability against ultraviolet light. VHR-3 is preferably 90% or more, more preferably 95% or more.

[0113] (11) Voltage holding ratio (VHR-4; measured at 25 °C; %): After heating the TN element injected with the sample in a constant temperature bath at 80 °C for 500 hours, the voltage holding ratio was measured to evaluate the stability against heat. In the measurement of VHR-4, the voltage decaying within 16.7 milliseconds was measured. A composition having a large VHR-4 has a large stability against heat.

[0114] (12) Response time (τ; measured at 25 °C; ms): An LCD5200 type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source was a halogen lamp. The low-pass filter was set to 5 kHz. The sample was put into a normally black mode VA element with a cell gap of 4 μm between two glass substrates and an anti-parallel rubbing direction. This element was sealed using an adhesive cured by ultraviolet light. A rectangular wave (60 Hz, 10 V, 0.5 seconds) was applied to this element. At this time, the element was irradiated with light from the perpendicular direction, and the amount of light transmitted through the element was measured. It was regarded that the transmittance was 100% when this light amount was maximum, and the transmittance was 0% when this light amount was minimum. The response time was expressed as the time (fall time; milliseconds) required for the change of the transmittance from 90% to 10%.

[0115] (13) Specific Resistance (ρ; measured at 25 °C; Ωcm): 1.0 mL of the sample was injected into a container equipped with electrodes. A DC voltage (10 V) was applied to this container, and the DC current after 10 seconds was measured. The specific resistance was calculated from the following formula. (Specific Resistance) = {(Voltage) × (Electrical Capacitance of the Container)} / {(DC Current) × (Permittivity of Vacuum)}.

[0116] (14) Line Image Sticking Parameter (LISP; %): Line image sticking was generated by applying an electrical stress to the liquid crystal display element. The luminance of the area with line image sticking and the luminance of the remaining area were measured. The ratio of luminance decrease due to line image sticking was calculated, and the size of line image sticking was represented by this ratio. 14a) Measurement of Luminance: An image of the element was taken using an imaging color luminance meter (PM-1433F-0, manufactured by Radiant Zemax). The luminance of each area of the element was calculated by analyzing this image using software (Prometric 9.1, manufactured by Radiant Imaging). The light source used was an LED backlight with an average luminance of 3500 cd / m 2 ².

[0117] 14b) Setting of Stress Voltage: The sample was placed in an FFS element (16 cells, 4 cells vertically × 4 cells horizontally) with a cell gap of 3.5 μm and having a matrix structure, and this element was sealed using an adhesive cured by ultraviolet light. Polarizing plates were placed on the upper and lower surfaces of this element so that the polarization axes were orthogonal. The element was irradiated with light, and a voltage (rectangular wave, 60 Hz) was applied. The voltage was increased stepwise by 0.1 V in the range from 0 V to 7.5 V, and the luminance of the transmitted light at each voltage was measured. The voltage when the luminance reached its maximum was abbreviated as V255. The voltage when the luminance reached 21.6% of V255 (i.e., 127 gradations) was abbreviated as V127.

[0118] 14c) Stress Conditions: V255 (rectangular wave, 30 Hz) and 0.5 V (rectangular wave, 30 Hz) were applied to the element under the conditions of 60 °C for 23 hours, and a checker pattern was displayed. Next, V127 (rectangular wave, 0.25 Hz) was applied, and the luminance was measured under the condition of an exposure time of 4000 milliseconds.

[0119] 14d) Calculation of afterimage: Among the 16 cells, the 4 central cells (2 cells in the vertical direction × 2 cells in the horizontal direction) were used for the calculation. These 4 cells were divided into 25 regions (5 cells in the vertical direction × 5 cells in the horizontal direction). The average luminance of the 4 corner regions (2 cells in the vertical direction × 2 cells in the horizontal direction) was abbreviated as luminance A. The region obtained by removing the corner regions from the 25 regions was in a cross shape. In the 4 regions obtained by removing the central intersection region from this cross-shaped region, the minimum luminance value was abbreviated as luminance B. The afterimage was calculated from the following formula. (Afterimage) = (Luminance A - Luminance B) / Luminance A × 100.

[0120] (15) Spreadability: The spreadability of the additive was qualitatively evaluated by applying a voltage to the element and measuring the luminance. The luminance measurement was performed in the same manner as in item 14a above. The setting of the voltage (V127) was performed in the same manner as in item 14b above. However, a VA element was used instead of the FFS element. The luminance was measured as follows. First, a DC voltage (2V) was applied to the element for 2 minutes. Next, V127 (rectangular wave, 0.05 Hz) was applied, and the luminance was measured under the condition of an exposure time of 4000 milliseconds. The spreadability was evaluated from this result.

[0121] (16) Response time (τ-2; measured at -20 °C; ms): An LCD5200 type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source was a halogen lamp. The low-pass filter was set to 5 kHz. A sample was placed in a normally black mode VA element with a cell gap of 4 μm between two glass substrates and an anti-parallel rubbing direction. This element was sealed using an adhesive cured by ultraviolet light. A rectangular wave (60 Hz, 10V, 0.5 seconds) was applied to this element. At this time, light was irradiated on the element from the vertical direction, and the amount of light transmitted through the element was measured. It was considered that the transmittance was 100% when this amount of light was maximum, and the transmittance was 0% when this amount of light was minimum. The response time was expressed as the time (fall time; milliseconds) required for the transmittance to change from 90% to 10%.

[0122] (17) Response time (τ-3; measured at -30°C; ms): An LCD5200 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source was a halogen lamp. The low-pass filter was set at 5 kHz. The sample was placed in a normally black mode VA element with a cell gap of 4 μm between two glass substrates and an anti-parallel rubbing direction. This element was sealed using an adhesive cured with ultraviolet light. A rectangular wave (60 Hz, 10 V, 0.5 s) was applied to this element. At this time, light was irradiated from a direction perpendicular to the element, and the amount of light transmitted through the element was measured. The time when this light amount was maximum was regarded as 100% transmittance, and the time when this light amount was minimum was regarded as 0% transmittance. The response time was expressed as the time (fall time; milliseconds) required for the transmittance to change from 90% to 10%.

[0123] (18) Elastic constants (K11: splay elastic constant, K33: bend elastic constant; measured at 25°C; pN): An EC-1 type elastic constant measuring instrument manufactured by Toyo Technica Co., Ltd. was used for the measurement. The sample was placed in a vertically aligned cell with a cell gap of 20 μm between two glass substrates. A charge from 20 V to 0 V was applied to this cell, and the capacitance and the applied voltage were measured. The measured values of the capacitance (C) and the applied voltage (V) were fitted using equations (2.98) and (2.101) on page 75 of the "Liquid Crystal Device Handbook" (Nikkan Kogyo Shimbun), and the value of the elastic constant was obtained from equation (2.100).

[0124] Compound (1-2-1) was synthesized by the following route. TIFF2025113213000035.tif56168

[0125] Step 1: Synthesis of compound (b) Compound (a) (3 g, 12.1 mmol) and THF (50 ml) were placed in a reaction vessel and cooled to -60 °C or lower. n-Butyllithium (1.6 M solution; 8 ml, 12.7 mmol) was added dropwise thereto, and the mixture was stirred for 1 hour. Subsequently, sulfur powder (0.47 g, 14.5 mmol) was added, and the mixture was stirred for 2 hours while returning to 25 °C. Bromoacetaldehyde diethyl acetal (3.57 g, 18.13 mmol) and DMF (50 ml) were added thereto, and the mixture was refluxed for 2 hours. The reaction solution was poured into water (100 ml), extracted with toluene (100 ml × 2), washed with water (100 ml), dehydrated with magnesium sulfate, and concentrated. The crude product was purified by column chromatography (silica gel, toluene) to obtain compound (b) as a white solid (4.3 g, yield 90%). Compound (a) is a known substance and can be easily obtained, for example, according to the method described in JP-A-2019-112607.

[0126] Step 2: Synthesis of compound (c) Compound (b) (4.3 g), polyphosphoric acid (8 g) and toluene (250 ml) were placed in a reaction vessel and heated to reflux for 5 hours. The reaction solution was poured into water (100 ml), extracted with toluene (100 ml × 2), washed with water (100 ml), dehydrated with magnesium sulfate, and concentrated. The crude product was purified by column chromatography (silica gel, toluene / heptane = 1 / 1) to obtain compound (c) as a white solid (2.1 g, yield 64%).

[0127] Step 3: Synthesis of compound (1-2-1) Compound (d) (2.1 g) and THF (100 ml) were placed in a reaction vessel and cooled to -60 °C or lower. Lithium diisopropylamide (LDA, 1.1 M; n-hexane solution; 7.53 ml, 8.28 mmol) was added dropwise thereto, and the mixture was further stirred for 2 hours. Subsequently, a solution of iodopropane (1.76 g) in THF (10 ml) was added dropwise, and the mixture was stirred for 8 hours while returning to 25 °C. The reaction solution was poured into water (100 ml), extracted with toluene (100 ml × 2), washed with water (100 ml), dehydrated with magnesium sulfate, and concentrated. The crude product was purified by column chromatography (silica gel, toluene / heptane = 1 / 1) and recrystallization (ethanol) to obtain a white solid compound (1-2-1) (1.77 g, yield 74%).

[0128] 1 1H-NMR (CDCl3) δ 7.86 (s, 1H), 7.59 (d, 1H), 7.09 (d, 1H), 7.11 (dd, 1H), 4.23 (q, 2H), 2.90 (t, 3H), 1.82 (sex, 2H), 1.50 (t, 3H), 1.05 (t, 3H).

[0129] Upper limit temperature (NI) = 98.3 °C; dielectric anisotropy (Δε) = -10.8; optical anisotropy (Δn) = 0.237; viscosity (η) = 70.4 mPa·s.

[0130] Examples of the composition are shown below. The component compounds are represented by symbols based on the definitions in Table 3 below. In Table 3, the configuration regarding 1,4-cyclohexylene is trans. The number in parentheses after the symbol corresponds to the compound number. The (-) symbol means other liquid crystalline compounds. The ratio (percentage) of the liquid crystalline compound is the mass percentage (mass%) based on the mass of the liquid crystal composition. Finally, the characteristic values of the composition are summarized.

[0131] TIFF2025113213000036.tif254138

[0132] [Comparative Example 1] 2O-bt(7F)B(F)-O2 (-) 4% 3-HH-V (2-1) 29% V-HHB-1 (2-7) 4% V-HHBB-2 (2-12) 3% 2-BB(F,F)-O2 (3-6) 8% 3-BB(F,F)-O2 (3-6) 10% V2-BB(F,F)-O2 (3-6) 7% 3-HHB(F,F)-O2 (3-8) 8% V-HHB(F,F)-O2 (3-8) 4% 3-HBB(F,F)-O2 (3-14) 6% V-HBB(F,F)-O2 (3-14) 7% 3O-Phe(1F,8F)-O2 (3-36) 6% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 76.8 °C; Δn = 0.132; Δε = -3.8; γ1 = 95.7 mPa·s.

[0133] [Example 1] The composition in which the thiophene derivative of Comparative Example 1 was replaced with compound (1-1) was taken as Example 1. 3-FRDBTF2-O2 (1-1) 4% 3-HH-V (2-1) 29% V-HHB-1 (2-7) 4% V-HHBB-2 (2-12) 3% 2-BB(F,F)-O2 (3-6) 8% 3-BB(F,F)-O2 (3-6) 10% V2-BB(F,F)-O2 (3-6) 7% 3-HHB(F,F)-O2 (3-8) 8% V-HHB(F,F)-O2 (3-8) 4% 3-HBB(F,F)-O2 (3-14) 6% V-HBB(F,F)-O2 (3-14) 7% 3O-Phe(1F,8F)-O2 (3-36) 6% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 76.2 °C; Tc < -20 °C; Δn = 0.131; Δε = -4.2; γ1 = 93.4 mPa·s.

[0134] [Example 2] 3-TDBFRF2-O2 (1-2) 4% 4-TDBFRF2-O2 (1-2) 3% 5-TDBFRF2-O2 (1-2) 3% 3-HH-V (2-1) 41% 3-HH-V1 (2-1) 3% 3-HHH-V (2-4) 3% 3-BB(F,F)-O2 (3-6) 5% V2-BB(F,F)-O2 (3-6) 6% 3-HHB(F,F)-O2 (3-8) 9% V-HHB(F,F)-O2 (3-8) 8% V-HBB(F,F)-O2 (3-14) 6% 3O-Phe(1F,8F)-O2 (3-36) 5% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 80.0 °C; Tc < -20 °C; Δn = 0.114; Δε = -3.6; γ1 = 77.3 mPa·s.

[0135] [Example 3] 3-TDBFRF2-O2 (1-2) 3% 3-HH-V (2-1) 35% 3-HH-V1 (2-1) 2.5% V-HHB-1 (2-7) 2.5% V-HB(F,F)-O2 (3-6) 5.5% 3-BB(F,F)-O2 (3-6) 2.5% V2-BB(F,F)-O2 (3-6) 7% 2-HHB(F,F)-O2 (3-8) 4% 3-HHB(F,F)-O2 (3-8) 9% 3-HHB(F,F)-O1 (3-8) 3% V-HHB(F,F)-O2 (3-8) 8% 3-HBB(F,F)-O2 (3-14) 1% V-HBB(F,F)-O2 (3-14) 8% 3O-Phe(1F,8F)-O2 (3-36) 5% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 80.5 °C; Tc < -30 °C; Δn = 0.110; Δε = -3.8; γ1 = 86.2 mPa·s.

[0136] [Example 4] 3-FRDBTF2-O2 (1-1) 3% 3-HH-V (2-1) 35% 3-HH-V1 (2-1) 2.5% V-HHB-1 (2-7) 2.5% V-HB(F,F)-O2 (3-6) 5.5% 3-BB(F,F)-O2 (3-6) 2.5% V2-BB(F,F)-O2 (3-6) 7% 2-HHB(F,F)-O2 (3-8) 4% 3-HHB(F,F)-O2 (3-8) 9% 3-HHB(F,F)-O1 (3-8) 3% V-HHB(F,F)-O2 (3-8) 8% 3-HBB(F,F)-O2 (3-14) 1% V-HBB(F,F)-O2 (3-14) 8% 3O-Phe(1F,8F)-O2 (3-36) 5% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 80.8 °C; Tc < -30 °C; Δn = 0.114; Δε = -3.8; γ1 = 86.0 mPa·s.

[0137] [Example 5] 3-TDBFRF2-O2 (1-2) 3.5% 3-HH-V (2-1) 14% 3-HH-V1 (2-1) 13% 3-HH-4 (2-1) 4% 1V2-HH-3 (2-1) 9% 3-HB-O2 (2-2) 2% 3-HHH-V (2-4) 6% 3-HHB-1 (2-7) 8% V-HHB-1 (2-7) 3.5% V2-HHB-1 (2-7) 5% 3-HH2B(F,F)-O2 (3-9) 2% 3-HH1OB(F,F)-O2 (3-10) 20% 3O-Phe(1F,8F)-O2 (3-36) 6% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 116.4 °C; Tc < -20 °C; Δn = 0.100; Δε = -2.5; γ1 = 150.0 mPa·s.

[0138] [Example 6] 3-TDBFRF2-O2 (1-2) 4% 3-HH-V (2-1) 14% 3-HH-V1 (2-1) 13% 3-HH-4 (2-1) 4% 1V2-HH-3 (2-1) 9% 3-HB-O2 (2-2) 2% 3-HHH-V (2-4) 6% 3-HHB-1 (2-7) 8% V2-HHB-1 (2-7) 5% 3-HHB(F,F)-O2 (3-8) 7% 3-HH2B(F,F)-O2 (3-9) 2% 3-HH1OB(F,F)-O2 (3-10) 20% 3O-Phe(1F,8F)-O2 (3-36) 6% NI = 120.0 °C; Tc < -20 °C; Δn = 0.096; Δε = -2.7; γ1 = 162.7 mPa·s.

[0139] [Example 7] 3-FRDBFRF2-O2 (1) 5% 3-HH-V (2-1) 29% V-HHB-1 (2-7) 3% V-HBB-2 (2-8) 2% V-HHBB-2 (2-12) 3% 2-BB(F,F)-O2 (3-6) 8% 3-BB(F,F)-O2 (3-6) 10% V2-BB(F,F)-O2 (3-6) 7% 3-HHB(F,F)-O2 (3-8) 8% V-HHB(F,F)-O2 (3-8) 8% 3-HBB(F,F)-O2 (3-14) 3% 2-BB(F,F)B-3 (3-19) 4% 3O-Phe(1F,8F)-O2 (3-36) 6% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 71.0°C; Δn = 0.130; Δε = -4.2; γ1 = 90.0 mPa·s.

[0140] [Example 8] 3-FRDBFRF2-O2 (1) 3% 3-HH-V (2-1) 35% 3-HH-V1 (2-1) 2.5% V-HHB-1 (2-7) 2.5% V-HB(F,F)-O2 (3-1) 5.5% 3-BB(F,F)-O2 (3-6) 2.5% V2-BB(F,F)-O2 (3-6) 7% 2-HHB(F,F)-O2 (3-8) 4% 3-HHB(F,F)-O2 (3-8) 9% 3-HHB(F,F)-O1 (3-8) 3% V-HHB(F,F)-O2 (3-8) 8% 3-HBB(F,F)-O2 (3-14) 1% V-HBB(F,F)-O2 (3-14) 8% 3O-Phe(1F,8F)-O2 (3-36) 5% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 79.5°C; Δn = 0.111; Δε = -3.8; γ1 = 86.0 mPa·s.

[0141] [Example 9] 3-FRDBFRF2-O2 (1) 3.5% 3-HH-V (2-1) 14% 3-HH-V1 (2-1) 13% 3-HH-4 (2-1) 4% 1V2-HH-3 (2-1) 9% 3-HB-O2 (2-2) 2% 3-HHH-V (2-4) 6% 3-HHB-1 (2-7) 8% V-HHB-1 (2-7) 3.5% V2-HHB-1 (2-7) 5% 3-HH2B(F,F)-O2 (3-9) 2% 3-HH1OB(F,F)-O2 (3-10) 20% 3O-Phe(1F,8F)-O2 (3-36) 6% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 115.4°C; Δn = 0.101; Δε = -2.5; γ1 = 149.8 mPa·s.

[0142] [Example 10] 3-FRDBTF2-O2 (1-1) 3% 3-TDBFRF2-O2 (1-2) 3% 3-HH-V (2-1) 35% 3-HH-V1 (2-1) 2.5% V-HHB-1 (2-7) 4% V-HB(F,F)-O2 (3-1) 6.5% V2-BB(F,F)-O2 (3-6) 7% 2-HHB(F,F)-O2 (3-8) 4% 3-HHB(F,F)-O2 (3-8) 9% 3-HHB(F,F)-O1 (3-8) 4% V-HHB(F,F)-O2 (3-8) 8% V-HBB(F,F)-O2 (3-14) 5% 3O-Phe(1F,8F)-O2 (3-36) 5% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 82.9 °C; Tc < -20 °C; Δn = 0.110; Δε = -4.0; γ1 = 86.8 mPa·s.

[0143] [Example 11] 3-TDBFRF2-O2 (1-2) 3.5% 3-HH-V (2-1) 14% 3-HH-V1 (2-1) 13% 3-HH-4 (2-1) 4% 1V-HH-V1 (2-1) 9% 3-HB-O2 (2-2) 2% 3-HHH-V (2-4) 6% 3-HHB-1 (2-7) 8% V-HHB-1 (2-7) 3.5% V2-HHB-1 (2-7) 5% 3-HH2B(F,F)-O2 (3-9) 2% 3-HH1OB(F,F)-O2 (3-10) 20% 3O-Phe(1F,8F)-O2 (3-36) 6% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 116.3 °C; Tc < -20 °C; Δn = 0.097; Δε = -2.5; γ1 = 148.5 mPa·s.

[0144] [Example 12] 3-FRDBTF2-O2 (1-1) 3% 3-HH-V (2-1) 10% 3-HH-V1 (2-1) 6% 1V2-HH-3 (2-1) 10% 1V-HH-V1 (2-1) 10% 3-HHH-V (2-4) 5% V2-HHB-1 (2-7) 2.5% 1V2-HHB-1 (2-7) 7% 3-H2B(F,F)-O2 (3-2) 8% 3-H1OB(F,F)-O2 (3-3) 7% 3-HHB(F,F)-O2 (3-8) 2.5% 3-HH2B(F,F)-O2 (3-9) 15% 3-HH1OB(F,F)-O2 (3-10) 7% 3O-Phe(1F,8F)-O2 (3-36) 7% NI = 105.9℃; Tc < -20℃; Δn = 0.100; Δε = -3.5; γ1 = 161.4 mPa·s.

[0145] [Example 13] 3-FRDBTF2-O2 (1-1) 3% 3-HH-V (2-1) 13% 3-HH-V1 (2-1) 6% 1V2-HH-1 (2-1) 2% 1V2-HH-3 (2-1) 10.5% 1V-HH-V1 (2-1) 10% 3-HHH-V (2-4) 6% 3-HHVH-V (2-5) 5.5% 3-H1OB(F,F)-O2 (3-3) 10% 3-HH2B(F,F)-O2 (3-9) 15% 3-HH1OB(F,F)-O2 (3-10) 8% 3-HDhB(F,F)-O2 (3-13) 4% 3O-Phe(1F,8F)-O2 (3-36) 7% NI = 108.7 °C; Δn = 0.950; Δε = -3.4; γ1 = 147.6 mPa·s.

[0146] [Example 14] 3-TDBFRF2-O2 (1-2) 5% 4-TDBFRF2-O2 (1-2) 4% 3-HH-V (2-1) 33.5% 3-HH-V1 (2-1) 6% V-HH-V1 (2-1) 5.5% 3-HB(F,F)-O2 (3-1) 10% V2-BB(F,F)-O2 (3-6) 3.5% 3-HHB(F,F)-O1 (3-8) 1% 3-HHB(F,F)-O2 (3-8) 8.5% V-HHB(F,F)-O2 (3-8) 9% 3-HDhB(F,F)-O2 (3-13) 8% 3O-Phe(1F,8F)-O2 (3-36) 6% NI = 74.6 °C; Tc < -20 °C; Δn = 0.100; Δε = -4.0; γ1 = 82.0 mPa·s.

[0147] [Example 15] 3-FRDBTF2-O2 (1-1) 5% 3-TDBFRF2-O2 (1-2) 5% 3-HH-V (2-1) 40% 3-HH-V1 (2-1) 7% 3-HB(F,F)-O2 (3-1) 3% 3-BB(F,F)-O2 (3-6) 5% 3-HHB(F,F)-O2 (3-8) 7% V-HHB(F,F)-O2 (3-8) 5% 3-HBB(F,F)-O2 (3-14) 8% V-HBB(F,F)-O2 (3-14) 6% 3O-Phe(1F,8F)-O2 (3-36) 5% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 81.3 °C; Δn = 0.115; Δε = -3.5; γ1 = 79.7 mPa·s.

[0148] [Example 16] 3-FRDBTF2-O2 (1-1) 5% 3-TDBFRF2-O2 (1-2) 5% 3-HH-V (2-1) 42% 3-HH-V1 (2-1) 3% 3-HB(F,F)-O2 (3-1) 6% 3-HHB(F,F)-O2 (3-8) 5% V-HHB(F,F)-O2 (3-8) 7% 3-HBB(F,F)-O2 (3-14) 4% V-HBB(F,F)-O2 (3-14) 6% 2-BB(F,F)B-3 (3-19) 8% 3O-Phe(1F,8F)-O2 (3-36) 5% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 80.3 °C; Δn = 0.120; Δε = -3.4; γ1 = 80.3 mPa·s.

[0149] [Example 17] 3-TDBFRF2-O2 (1-2) 5% 3-HH-V (2-1) 40% 3-HH-V1 (2-1) 8% 3-HB(F,F)-O2 (3-1) 7% 3-BB(F,F)-O2 (3-6) 3.5% 3-HHB(F,F)-O2 (3-8) 6% V-HHB(F,F)-O2 (3-8) 8.5% 3-HBB(F,F)-O2 (3-14) 5% 3O-Phe(1F,8F)-O2 (3-36) 5% 4O-Phe(1F,8F)-O2 (3-36) 4% 1-Tda-3 (3-37) 8% NI = 80.3 °C; Tc < -20 °C; Δn = 0.114; Δε = -3.3; γ1 = 74.6 mPa·s.

[0150] [Example 18] 3-TDBFRF2-O2 (1-2) 5% 4-TDBFRF2-O2 (1-2) 3% 3-HH-V (2-1) 42% 3-HB(F,F)-O2 (3-1) 6% V2-BB(F,F)-O2 (3-6) 2% 3-HHB(F,F)-O2 (3-8) 8% V-HHB(F,F)-O2 (3-8) 7% 3-HBB(F,F)-O2 (3-14) 2% V-HBB(F,F)-O2 (3-14) 8% 2-BB(F,F)B-3 (3-19) 8% 3O-Phe(1F,8F)-O2 (3-36) 5% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 80.0 °C; Tc < -20 °C; Δn = 0.120; Δε = -3.5; γ1 = 79.2 mPa·s.

[0151] [Example 19] 3-TDBFRF2-O2 (1-2) 5% 3-HH-V (2-1) 38% 3-HH-V1 (2-1) 2% V-HHB-1 (2-7) 1.5% V-HB(F,F)-O2 (3-1) 3% 3-BB(F,F)-O2 (3-6) 5% V2-BB(F,F)-O2 (3-6) 6% 2-HHB(F,F)-O2 (3-8) 3.5% 3-HHB(F,F)-O1 (3-8) 4% 3-HHB(F,F)-O2 (3-8) 9% V-HHB(F,F)-O2 (3-8) 8% V-HBB(F,F)-O2 (3-14) 6% 3O-Phe(1F,8F)-O2 (3-36) 5% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 78.8 °C; Tc < -20 °C; Δn = 0.110; Δε = -3.8; γ1 = 81.9 mPa·s.

[0152] [Example 20] 4-TDBFRF2-O2 (1-2) 5% 3-HH-V (2-1) 39% 3-HH-V1 (2-1) 3% 3-BB(F,F)-O2 (3-6) 5% V2-BB(F,F)-O2 (3-6) 7.5% 2-HHB(F,F)-O2 (3-8) 6% 3-HHB(F,F)-O1 (3-8) 4% 3-HHB(F,F)-O2 (3-8) 9% V-HHB(F,F)-O2 (3-8) 7% V-HBB(F,F)-O2 (3-14) 5.5% 3O-Phe(1F,8F)-O2 (3-36) 5% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 79.5 °C; Tc < -20 °C; Δn = 0.109; Δε = -3.8; γ1 = 83.2 mPa·s.

[0153] [Example 21] 5-TDBFRF2-O2 (1-2) 5% 3-HH-V (2-1) 39% 3-HH-V1 (2-1) 3% 3-BB(F,F)-O2 (3-6) 5% V2-BB(F,F)-O2 (3-6) 7.5% 2-HHB(F,F)-O2 (3-8) 6% 3-HHB(F,F)-O1 (3-8) 4% 3-HHB(F,F)-O2 (3-8) 9% V-HHB(F,F)-O2 (3-8) 7% V-HBB(F,F)-O2 (3-14) 5.5% 3O-Phe(1F,8F)-O2 (3-36) 5% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 79.7 °C; Tc < -20 °C; Δn = 0.109; Δε = -3.8; γ1 = 83.4 mPa·s.

[0154] [Example 22] 3-TDBFRF2-O2 (1-2) 4% 4-TDBFRF2-O2 (1-2) 3% 5-TDBFRF2-O2 (1-2) 3% 3-HH-V (2-1) 41% 3-HH-V1 (2-1) 3% 3-HHH-V (2-4) 3% 3-BB(F,F)-O2 (3-6) 5% V2-BB(F,F)-O2 (3-6) 6% 3-HHB(F,F)-O2 (3-8) 9% V-HHB(F,F)-O2 (3-8) 8% V-HBB(F,F)-O2 (3-14) 6% 3O-Phe(1F,8F)-O2 (3-36) 5% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 80.0 °C; Tc < -20 °C; Δn = 0.114; Δε = -3.6; γ1 = 77.3 mPa·s.

[0155] [Example 23] 3-TDBFRF2-O2 (1-2) 6% 3-HH-V (2-1) 34% 3-HH-V1 (2-1) 6% V-HBB-2 (2-8) 6% 3-BB(F,F)-O2 (3-6) 8% V2-BB(F,F)-O2 (3-6) 8% V-HHB(F,F)-O2 (3-8) 9% 3-HH1OB(F,F)-O2 (3-10) 15% V-HBB(F,F)-O2 (3-14) 8% NI = 80.3°C; Δn = 0.111; Δε = -3.6; γ1 = 82.5 mPa·s.

[0156] [Example 24] 3-TDBFRF2-O2 (1-2) 5% 3-HH-V (2-1) 30.5% 3-HH-V1 (2-1) 10% 1V2-HH-3 (2-1) 12% 3-HHH-V (2-4) 7% V2-HHB-1 (2-7) 1% 3-H1OB(F,F)-O2 (3-3) 5% V2-BB(F,F)-O2 (3-6) 1% 3-HHB(F,F)-O2 (3-8) 12% 3-HH1OB(F,F)-O2 (3-10) 5.5% 3O-Phe(1F,8F)-O2 (3-36) 6% 4O-Phe(1F,8F)-O2 (3-36) 5% NI = 94.8°C; Tc < -20°C; Δn = 0.096; Δε = -2.6; γ1 = 72.6 mPa·s.

[0157] [Example 25] 3-TDBFRF2-O2 (1-2) 3% 3-HH-V (2-1) 25% 3-HH-V1 (2-1) 10% 1V2-HH-3 (2-1) 8.5% 3-HHH-V (2-4) 3% 3-H1OB(F,F)-O2 (3-3) 6% V2-BB(F,F)-O2 (3-6) 4% 3-HH2B(F,F)-O2 (3-9) 10% 3-HH1OB(F,F)-O2 (3-10) 18.5% 3-HBB(F,F)-O2 (3-14) 2% 3O-Phe(1F,8F)-O2 (3-36) 6% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 94.4°C; Tc < -30°C; Δn = 0.101; Δε = -4.0; γ1 = 119.3 mPa·s.

[0158] [Example 26] 3-TDBFRF2-O2 (1-2) 5% 3-HH-V (2-1) 26% 3-HH-V1 (2-1) 10% 1V2-HH-3 (2-1) 9.5% 1V-HH-V1 (2-1) 3% 3-H1OB(F,F)-O2 (3-3) 6% V2-BB(F,F)-O2 (3-6) 2% 3-HH2B(F,F)-O2 (3-9) 10% 3-HH1OB(F,F)-O2 (3-10) 18.5% 3O-Phe(1F,8F)-O2 (3-36) 6% 4O-Phe(1F,8F)-O2 (3-36) 4% NI = 90.5°C; Δn = 0.100; Δε = -3.9; γ1 = 116.5 mPa·s.

[0159] [Example 27] 3-FRDBTF2-O2 (1-1) 4% 3-TDBFRF2-O2 (1-2) 4% 3-HH-V (2-1) 41% V2-BB-1 (2-3) 10.5% 3-HBB-2 (2-8) 2.5% V-HBB-2 (2-8) 5% 2O-B(F,F)B(F)-O2 (3-7) 4% 3-HH1OB(F,F)-O2 (3-10) 7% 3-HBB(F,F)-O2 (3-14) 9% V-HBB(F,F)-O2 (3-14) 3% 3O-Phe(1F,8F)-O2 (3-36) 6% 4O-Phe(1F,8F)-O2 (3-36) 4% 0.34 mass% of the polymerizable compound represented by (4-1) was added as additive X. TIFF2025113213000037.tif25109 NI = 74.2 °C; Δn = 0.129; Δε = -2.8; γ1 = 88.0 mPa·s.

[0160] [Example 28] 3-FRDBTF2-O2 (1-1) 4% 3-TDBFRF2-O2 (1-2) 4% 3-HH-V (2-1) 41% V2-BB-1 (2-3) 10.5% 3-HBB-2 (2-8) 2.5% V-HBB-2 (2-8) 5% 2O-B(F,F)B(F)-O2 (3-7) 4% 3-HH1OB(F,F)-O2 (3-10) 7% 3-HBB(F,F)-O2 (3-14) 9% V-HBB(F,F)-O2 (3-14) 3% 3O-Phe(1F,8F)-O2 (3-36) 6% 4O-Phe(1F,8F)-O2 (3-36) 4% 0.30 mass% of the polymerizable compound represented by (4-25) was added as additive X. TIFF2025113213000038.tif37112 NI = 74.2 °C; Δn = 0.129; Δε = -2.8; γ1 = 88.0 mPa·s.

[0161] [Example 29] 3-FRDBTF2-O2 (1-1) 4% 3-TDBFRF2-O2 (1-2) 4% 3-HH-V (2-1) 41% V2-BB-1 (2-3) 10.5% 3-HBB-2 (2-8) 2.5% V-HBB-2 (2-8) 5% 2O-B(F,F)B(F)-O2 (3-7) 4% 3-HH1OB(F,F)-O2 (3-10) 7% 3-HBB(F,F)-O2 (3-14) 9% V-HBB(F,F)-O2 (3-14) 3% 3O-Phe(1F,8F)-O2 (3-36) 6% 4O-Phe(1F,8F)-O2 (3-36) 4% As additive X, 0.29% by mass of the polymerizable compound represented by (4-1) and 0.05% by mass of the polymerizable compound represented by (4-25) were added. TIFF2025113213000039.tif25109 TIFF2025113213000040.tif37112 NI = 74.2 °C; Δn = 0.129; Δε = -2.8; γ1 = 88.0 mPa·s.

[0162] The rotational viscosity and dielectric anisotropy of the composition of Comparative Example 1 were 95.7 mPa·s and -3.8, respectively. On the other hand, the rotational viscosity and dielectric anisotropy of the composition of Example 1 were 93.4 mPa·s and -4.2, respectively. Therefore, it is concluded that the liquid crystal composition of the present invention has excellent properties.

Industrial Applicability

[0163] The liquid crystal composition of the present invention can be used in liquid crystal monitors, liquid crystal TVs, etc.

Claims

1. A liquid crystal composition containing at least one compound selected from the compounds represented by formula (1) as Component A and having negative dielectric anisotropy. In formula (1), R １ and R ２ are hydrogen, alkyl having 1 to 12 carbon atoms, cyclic alkyl having 3 to 5 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; X １ and X ２ are O or S; L １ and L ２ are hydrogen, fluorine, or trifluoromethyl; ring A and ring B 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, chroman - 2,6 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, fluorene - 2,7 - diyl, fluorene - 2,7 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, dibenzofuran - 3,7 - diyl, dibenzofuran - 3,7 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, dibenzothiophene - 3,7 - diyl, dibenzothiophene - 3,7 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, indane - 2,5 - diyl, indane - 2,5 - diyl in which at least one hydrogen is replaced by fluorine or chlorine, thiophene - 2,5 - diyl, or furan - 2,5 - diyl; Z １ and Z ２ are a single bond, ethylene, vinylene, ethynylene, methyleneoxy, or carbonyloxy; a and b are 0 or 1.

2. In formula (1), X １ and X ２ The liquid crystal composition according to claim 1, wherein at least one of is S.

3. The liquid crystal composition according to claim 1 or 2, containing at least one compound selected from the compounds represented by formulas (1-1) to (1-3) as Component A. In Formula (1-1) to Formula (1-3), R １ and R ２ are hydrogen, alkyl having 1 to 12 carbon atoms, cyclic alkyl having 3 to 5 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; L １ and L ２ are hydrogen, fluorine, or trifluoromethyl.

4. The liquid crystal composition according to claim 1 or 2, wherein the proportion of Component A is in the range of 3% by mass to 20% by mass.

5. The liquid crystal composition according to claim 1, containing at least one compound selected from the compounds represented by formula (2) as Component B. In formula (2), R ３ and R ４ are alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, 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 ３ is a single bond, ethylene, vinylene, methyleneoxy, or carbonyloxy; and c is 1, 2, or 3.

6. The liquid crystal composition according to claim 1, containing at least one compound selected from the compounds represented by formulas (2-1) to (2-15) as Component B. In Formula (2-1) to Formula (2-15), R ３ and R ４ are alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine.

7. The liquid crystal composition according to claim 5 or 6, wherein the proportion of Component B is in the range of 10% by mass to 90% by mass.

8. The liquid crystal composition according to claim 1 or 5, containing at least one compound selected from the compounds represented by formula (3) as Component C. In formula (3), R ５ and R ６ are 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 chroman-2,6-diyl in which at least one hydrogen is replaced by fluorine or chlorine; ring F is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 1,8-difluorophenanthrene-2,7-diyl, 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, 1,1,6,7-tetrafluoroindane-2,5-diyl, or 1,3,4-thiadiazole-2,5-diyl; Z ４ and Z ５ are 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.

9. The liquid crystal composition according to claim 1, containing at least one compound selected from the compounds represented by formulas (3-1) to (3-37) as Component C. In Formula (3-1) to Formula (3-37), R ５ and R ６ are 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.

10. The liquid crystal composition according to claim 8, wherein the proportion of Component C is in the range of 10% by mass to 85% by mass.

11. The liquid crystal composition according to claim 1, containing at least one compound selected from the polymerizable compounds represented by formula (4) as Additive X. In formula (4), 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; 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, tetrahydropyran-2,5-diyl, 1,3-dioxan-2,5-diyl, pyrimidin-2,5-diyl, or pyridin-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; Z ６ and Z ７ are a single bond or 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 - may be replaced by -CH=CH-, -C(CH ３ )=CH-, -CH=C(CH ３ )-, or -C(CH ３ )=C(CH ３ )-, and in these groups, at least one hydrogen may be replaced by fluorine or chlorine; P １ to P ３ are polymerizable groups; Sp １ to Sp ３ 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-, -COO-, -OCO-, or -OCOO-, and at least one -CH ２ CH ２ - may be replaced by -CH=CH- or -C≡C-, and in these groups, at least one hydrogen may be replaced by fluorine or chlorine; f is 0, 1, or 2; g, h, and i are 0, 1, 2, 3, or 4; and the sum of g, h, and i is 1 or more.

12. In formula (4), P １ to P ３ is a group selected from the polymerizable groups represented by formulas (P-1) to (P-5), the liquid crystal composition according to claim 11. In Formula (P-1) to Formula (P-5), M １ to M ３ is hydrogen, fluorine, an alkyl having 1 to 5 carbon atoms, or an alkyl having 1 to 5 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine.

13. The liquid crystal composition according to claim 1, containing at least one compound selected from the polymerizable compounds represented by formulas (4-1) to (4-29) as Additive X. In Formula (4-1) to Formula (4-29), Sp １ from Sp ３ 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-, -COO-, -OCO-, or -OCOO-, and at least one -CH ２ CH ２ - may be replaced by -CH=CH- or -C≡C-, and in these groups, at least one hydrogen may be replaced by fluorine or chlorine; P ４ from P ６ is a polymerizable group selected from the groups represented by Formula (P-1) to Formula (P-3); In Formula (P-1) to Formula (P-3), M １ to 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 is replaced by fluorine or chlorine.

14. The liquid crystal composition according to any one of claims 11 to 13, wherein the proportion of Additive X is in the range of 0.03% by mass to 10% by mass.

15. A liquid crystal display element containing the liquid crystal composition according to claim 1.

16. The liquid crystal display element according to claim 15, wherein the operation mode is an IPS mode, a VA mode, an FFS mode, or an FPA mode, and the driving method is an active matrix method.

17. A polymer-supported alignment type liquid crystal display element containing the liquid crystal composition according to claim 11 and in which the polymerizable compound in this liquid crystal composition has polymerized.

18. Use of the liquid crystal composition according to claim 1 in a liquid crystal display element.

19. Use of the liquid crystal composition according to claim 11 in a polymer-supported alignment type liquid crystal display element.

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