Compound, liquid crystal composition, and liquid crystal display device

Abstract

[Problem] To provide a compound which has high stability with respect to heat, high voltage holding ratio if used in a liquid crystal display element, and the like. [Solution] A compound which is represented by formula (1). In the formula, R1 represents an alkyl group having 1-15 carbon atoms, or the like; each of ring A1 and ring A2 represents a 1, 4-phenylene group or the like; a represents 2 or the like; each of b and c represents 0, 1 or 2; Z1 represents a single bond or the like; each of P1 and P2 represents a group of formula (1-p1), formula (1-p2) or formula (1-p3), or the like; Sp1 represents an alkylene group having 1-15 carbon atoms, or the like; R2 represents an alkyl group having 1-5 carbon atoms; R3 represents an alkyl group having 1-10 carbon atoms, or the like; Y1 represents a fluorine atom or the like; Sp2 represents an alkylene group having 1-10 carbon atoms, or the like; and X1 represents a polar group.

Description

[Technical field]

[0001] The present invention relates to a compound, a liquid crystal composition, and a liquid crystal display device. More specifically, the present invention relates to a compound having both a polymerizable group such as methoxymethacryloyloxy and a polar group such as -OH, a liquid crystal composition containing this compound and having positive or negative dielectric anisotropy, and a liquid crystal display device containing this composition or a cured product of a part of it. [Background technology]

[0002] LCD devices can be classified according to the operating mode of the liquid crystal molecules into 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). Also, according to the driving method of the device, they can be classified into PM (passive matrix) and AM (active matrix). PM can be classified into static, multiplex, etc., and AM can be classified into TFT (thin film transistor), MIM (metal insulator metal), etc. Furthermore, TFT can be classified into amorphous silicon and polycrystal silicon. The latter can be classified into high temperature type and low temperature type depending on the manufacturing process. When classified based on the light source, they can be divided into reflective types that use natural light, transmissive types that use backlight, and semi-transmissive types that use both natural light and backlight.

[0003] A liquid crystal composition having a nematic phase has suitable characteristics. By improving the characteristics of this composition, an AM element having good characteristics can be obtained. The relationship between the characteristics of the composition and the characteristics of the AM element is summarized in Table 1 below.

[0004] [Table 1]

[0005] The properties of the composition are further explained based on a commercially available AM ​​device. The temperature range of the nematic phase (the temperature range in which the nematic phase is exhibited) is related to the temperature range in which the device can be used. The preferred upper limit temperature of the nematic phase is about 70°C or more, and the preferred lower limit temperature of the nematic phase is about -10°C or less. The viscosity of the composition is related to the response time of the element. A short response time is preferable for displaying moving images with the element. A response time shorter than 1 millisecond is desirable. Therefore, it is preferable that the viscosity of the composition is low, and it is even more preferable that the viscosity is low even at low temperatures.

[0006] The optical anisotropy of the composition is related to the contrast ratio of the element. Depending on the mode of the element, large or small optical anisotropy, i.e., 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 product value depends on the type of operation mode. This value is about 0.45 μm for elements in modes such as TN. This value ranges from about 0.30 μm to about 0.40 μm for elements in VA mode, and from about 0.20 μm to about 0.30 μm for elements in IPS mode or FFS mode. In these cases, compositions with large optical anisotropy are preferred for elements with small cell gaps. A large dielectric anisotropy in the composition contributes to a low threshold voltage, small power consumption, and a large contrast ratio in the element. Therefore, a large positive or negative dielectric anisotropy is preferred. A large resistivity in the composition contributes to a large voltage holding ratio and a large contrast ratio in the element. Therefore, a composition having a large resistivity not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase in the initial stage is preferred. A composition having a large resistivity not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase after long-term use is preferred. The stability of the composition against ultraviolet light and heat is related to the life of the element. When this stability is high, the life of the element is long. Such characteristics are preferable for AM elements used in liquid crystal projectors, liquid crystal televisions, etc.

[0007] In a polymer sustained alignment (PSA) type liquid crystal display element, a liquid crystal composition containing a polymer is used. First, a composition to which a small amount of a polymerizable compound is added is injected into the element. A polymerizable compound having multiple polymerizable groups is generally used here. Next, the composition is irradiated with ultraviolet light while a voltage is applied between the substrates that sandwich the element. The polymerizable compound polymerizes to generate a polymer network structure in the composition. When this composition is used, it becomes possible to control the alignment of the liquid crystal molecules by the polymer, so that the response time of the element is shortened and image sticking is improved. Such effects of the polymer can be expected in elements having modes such as TN, ECB, OCB, IPS, VA, FFS, and FPA.

[0008] In a general-purpose liquid crystal display element, the vertical alignment of liquid crystal molecules is achieved by a polyimide alignment film. On the other hand, as a liquid crystal display element without an alignment film, a mode has been proposed in which a polar compound is added to a liquid crystal composition to align the liquid crystal molecules. First, a composition to which a small amount of a polar compound and a small amount of a polymerizable compound are added is injected into the element. As the polymerizable compound, a polymerizable compound having a plurality of polymerizable groups is generally used. Here, the liquid crystal molecules are aligned by the action of the polar compound. Next, the composition is irradiated with ultraviolet light while applying a voltage between the substrates sandwiching the element. Here, the polymerizable compound is polymerized, stabilizing the alignment of the liquid crystal molecules. When this composition is used, it becomes possible to control the alignment of the liquid crystal molecules by the polar compound and the polymer, so that the response time of the element is shortened and image sticking is improved. Furthermore, in an element without an alignment film, a process of forming an alignment film is not necessary. Since there is no alignment film, the electrical resistance of the element is not reduced by the interaction between the alignment film and the composition. Such effects due to the combination of polar compounds and polymers can be expected in elements having modes such as TN, ECB, OCB, IPS, VA, FFS, and FPA.

[0009] So far, polymerizable polar compounds have been synthesized as compounds having both the functions of a polar compound and a polymerizable compound in liquid crystal display elements that do not have an alignment film (for example, Patent Documents 1 and 2). Patent Document 2 describes a polymerizable compound (S-1) having a plurality of polar groups and a plurality of polymerizable groups.

[0010] [ka] [Prior art documents] [Patent documents]

[0011] [Patent Document 1] International Publication No. 2016 / 129490 [Patent Document 2] International Publication No. 2017 / 209161 Summary of the Invention [Problem to be solved by the invention]

[0012] The first object of the present invention is to provide a compound having at least one of high thermal stability, high chemical stability, high ability to align liquid crystal molecules, high polymerization reactivity by ultraviolet irradiation, fast consumption rate of monomers, and high voltage holding ratio when used in a liquid crystal display element, and having high solubility in a liquid crystal composition. The second object of the present invention is to provide a liquid crystal composition containing the compound and satisfying at least one of the following characteristics: a high upper limit temperature of a nematic phase, a low lower limit temperature of a nematic phase, low viscosity, appropriate optical anisotropy, large positive or negative dielectric anisotropy, large resistivity, high stability against ultraviolet rays, and large elastic constant. The third object of the present invention is to provide a liquid crystal display element having at least one of the following characteristics: a wide temperature range in which the element can be used, a short response time, a high transmittance, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, a long life, good vertical alignment, and little change in pretilt angle or brightness over time. [Means for solving the problem]

[0013] The present invention relates to a compound represented by formula (1), a liquid crystal composition containing this compound, and a liquid crystal display device containing this composition and / or a polymer formed by polymerizing at least a part of this composition.

[0014] [ka]

[0015] In formula (1), R 1 is hydrogen or alkyl having 1 to 15 carbon atoms, 1in which at least one -CH2- may be replaced by -O- or -S-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine; Ring A 1 and Ring A 2 are independently 1,2-cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,4-cyclohexylene, 1,4-cycloheptylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, and the ring A 1 and Ring A 2 in which at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or alkenyloxy having 2 to 9 carbons, and in these substituents, at least one hydrogen may be replaced by fluorine or chlorine; a is 0, 1, 2, 3, or 4; b and c are independently 0, 1, or 2; Z 1 are independently a single bond or an alkylene having 1 to 6 carbon atoms, 1 in which at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine; P 1 and P 2 are independently a group selected from groups represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) and formula (1-p5);

[0016] [ka]

[0017] In formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) and formula (1-p5), Sp 1 are independently a single bond or an alkylene having 1 to 15 carbon atoms, 1 in which at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine; R 2 is independently alkyl having 1 to 5 carbon atoms; R 3 is independently a linear alkyl having 1 to 10 carbon atoms, a branched alkyl having 3 to 10 carbon atoms, or a cyclic alkyl having 3 to 8 carbon atoms; Y 1 are independently chlorine, fluorine, or bromine; In formula (1), Sp 2 is a single bond or an alkylene having 1 to 10 carbon atoms, and Sp 2 in which at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, -OCOO- or a group represented by formula (1-a), at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) or formula (1-p5);

[0018] [ka]

[0019] X 1is a polar group having a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, phosphorus and silicon; P 1 and P 2 has at least one group selected from the groups represented by formula (1-p1), formula (1-p2), and formula (1-p3), Sp 2 is a single bond or an alkylene having 1 to 10 carbon atoms, and Sp 2 in which at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, -OCOO- or a group represented by formula (1-a), at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) or formula (1-p5); P 1 and P 2 When none of the groups represented by formula (1-p1), formula (1-p2), and formula (1-p3) is present, Sp 2 is an alkylene having 1 to 10 carbon atoms, and this Sp 2 In the formula (1-a), at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) or formula (1-p5). Effect of the Invention

[0020] The first advantage of the present invention is to provide a compound having at least one of high thermal stability, high chemical stability, high ability to align liquid crystal molecules, high polymerization reactivity by ultraviolet irradiation, fast consumption rate of monomers, and high voltage holding ratio when used in a liquid crystal display element, and having high solubility in a liquid crystal composition. The second advantage is to provide a liquid crystal composition containing the compound and satisfying at least one of the following characteristics: a high upper limit temperature of a nematic phase, a low lower limit temperature of a nematic phase, low viscosity, appropriate optical anisotropy, large positive or negative dielectric anisotropy, large resistivity, high stability against ultraviolet rays, and large elastic constant. The third advantage is to provide a liquid crystal display element having at least one of the following characteristics: a wide temperature range in which the element can be used, a short response time, a high transmittance, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, a long life, good vertical alignment, and little change in pretilt angle or brightness over time. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0021] The terms used in this specification are as follows: The terms "liquid crystal compound", "liquid crystal composition" and "liquid crystal display element" may be abbreviated to "compound", "composition" and "element", respectively. "Liquid crystal compound" is a general term for compounds having a liquid crystal phase such as a nematic phase or a smectic phase, and compounds not having a liquid crystal phase but added for the purpose of adjusting the physical properties of the composition such as the maximum temperature, the minimum temperature, the viscosity, the dielectric anisotropy, etc. This compound usually has a six-membered ring such as 1,4-cyclohexylene or 1,4-phenylene, and its molecular structure is rod-like. The "polymerizable compound" is a compound added for the purpose of forming a polymer in a composition. In this sense, the liquid crystal compound having an alkenyl group is not a polymerizable compound. The "polar compound" aids in aligning the liquid crystal molecules by interacting with the substrate surface or the like through the polar group. "Liquid crystal display element" is a general term for liquid crystal display panels and liquid crystal display modules.

[0022] A liquid crystal composition is usually prepared by mixing a plurality of liquid crystal compounds. To this composition, additives such as a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, a dye, and an antifoaming agent are added as necessary for the purpose of further adjusting the physical properties. The ratio (content) of the liquid crystal compound in the liquid crystal composition is expressed as a weight percentage (wt%) based on the weight of the liquid crystal composition not containing the additive, even when an additive is added. The ratio (addition amount) of the additive in the liquid crystal composition is expressed as a weight percentage (wt%) based on the weight of the liquid crystal composition not containing the additive. That is, the ratio of the liquid crystal compound or the additive is calculated based on the total weight of the liquid crystal compound. Parts per million (ppm) by weight may also be used. The ratio of the polymerization initiator and the polymerization inhibitor in the liquid crystal composition is exceptionally expressed based on the weight of the polymerizable compound.

[0023] The "clearing point" is the transition temperature of the liquid crystal phase to the isotropic phase in a liquid crystal compound. The "lower limit temperature of the liquid crystal phase" is the transition temperature of the solid-liquid crystal phase (smectic phase, nematic phase, etc.) in a liquid crystal compound. The "upper limit temperature of the nematic phase" is the transition temperature of the nematic phase to the isotropic phase in a mixture of a liquid crystal compound and a mother liquid crystal or in a liquid crystal composition, and is sometimes abbreviated as "upper limit temperature". The "lower limit temperature of the nematic phase" is sometimes abbreviated as "lower limit temperature". The expressions "increase the dielectric anisotropy" and "large dielectric anisotropy" mean that the absolute value of the value increases or is large. The "large voltage holding ratio" means that the element has a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature in the initial stage, and that even after the element has been used for a long time, it has a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature. The characteristics of the composition or element may be examined before and after an aging test (including an accelerated aging test). The expression "high solubility in liquid crystal compositions" means high solubility in any composition containing a liquid crystal compound at room temperature, and the composition used to evaluate the solubility in the examples below can be used as the standard for such a composition.

[0024] The compound represented by formula (1) may be abbreviated as "compound (1)". Compound (1) means one compound represented by formula (1), a mixture of two compounds, or a mixture of three or more compounds. This rule also applies to at least one compound selected from the group of compounds represented by formula (2). A in a hexagon 1 , B 1 , C 1 The symbols are ring A 1 , ring B 1 , ring C 1 The hexagon represents a six-membered ring such as a cyclohexane ring or a benzene ring, or a condensed ring such as a naphthalene ring. A line crossing one side of the hexagon indicates that any hydrogen on the ring is -Sp 1 -P 1 It means that the group may be substituted with a group such as The subscripts f, g, h, etc. indicate the number of groups replaced. When the subscript is 0, there is no such replacement. In the expression "Ring A and Ring C are independently X, Y, or Z," the subject is plural, so "independently" is used. When the subject is "Ring A is," the subject is singular, so "independently" is not used.

[0025] In the chemical formula of the compound, the terminal group R 11 The symbol R is used for several compounds. 11 The groups represented by may be the same or different. For example, R 11 is ethyl, R 11 may be ethyl or other groups such as propyl. This rule also applies to other symbols. In compound (8), when i is 2, the two rings D 1 In this compound, there are two rings D 1 The two groups represented by may be the same or different. When i is greater than 2, any two rings D 1 This rule also applies to other symbols.

[0026] The expression "at least one 'A'" means that the number of 'A' is optional. The expression "at least one 'A' may be replaced with 'B'" includes the case of 'A' itself that is not replaced with 'B', the case of one 'A' being replaced with 'B', and the case of two or more 'A' being replaced with 'B', and in these cases, the position of 'A' that is replaced with 'B' is optional. The rule that the replacement position is optional also applies to the expression "at least one 'A' is replaced with 'B'". The expression "at least one A may be replaced with B, C, or D" means the case of not replacing A, the case of at least one A being replaced with B, the case of at least one A being replaced with C, and the case of at least one A being replaced with D, and the case of multiple A being replaced with at least two of B, C, and D. For example, an alkyl in which at least one -CH2- (or -(CH2)2-) may be replaced with -O- (or -CH=CH-) includes alkyl, alkenyl, alkoxy, alkoxyalkyl, alkoxyalkenyl, and alkenyloxyalkyl. Note that it is not preferred that two consecutive -CH2- are replaced with -O- to give -OO-. In an alkyl, etc., it is also not preferred that the -CH2- of the methyl portion (-CH2-H) is replaced with -O- to give -OH.

[0027] "R 11 and R 12 are independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, in which at least one -CH2- may be replaced by -O-, and in which at least one hydrogen may be replaced by fluorine. In this expression, "in these groups" may be interpreted literally. In this expression, "these groups" means alkyl, alkenyl, alkoxy, alkenyloxy, etc. In other words, "these groups" represents all of the groups described before the term "in these groups". This common sense interpretation also applies to other terms.

[0028] Halogen means fluorine, chlorine, bromine, or iodine. Preferred halogens are fluorine or chlorine. More preferred halogen is fluorine. In liquid crystal compounds, alkyl is linear or branched, and does not include cyclic alkyl. Linear alkyl is generally preferred to branched alkyl. The same applies to terminal groups such as alkoxy and alkenyl. The configuration of 1,4-cyclohexylene is preferably trans rather than cis in order to increase the upper limit temperature of the nematic phase. 2-Fluoro-1,4-phenylene means the following two divalent groups. In the chemical formula, fluorine may face left (L) or right (R). This rule also applies to asymmetric divalent groups generated by removing two hydrogens from a ring, such as tetrahydropyran-2,5-diyl.

[0029] [ka]

[0030] The present invention includes the following items.

[0031] Item 1. A compound represented by formula (1). [ka]

[0032] In formula (1), R 1 is hydrogen or alkyl having 1 to 15 carbon atoms, 1 in which at least one -CH2- may be replaced by -O- or -S-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine; Ring A 1 and Ring A 2are independently 1,2-cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,4-cyclohexylene, 1,4-cycloheptylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, and the ring A 1 and Ring A 2 in which at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or alkenyloxy having 2 to 9 carbons, and in these substituents, at least one hydrogen may be replaced by fluorine or chlorine; a is 0, 1, 2, 3, or 4; b and c are independently 0, 1, or 2; Z 1 are independently a single bond or an alkylene having 1 to 6 carbon atoms, 1 in which at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine; P 1 and P 2 are independently a group selected from groups represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) and formula (1-p5);

[0033] [ka]

[0034] In formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) and formula (1-p5), Sp 1are independently a single bond or an alkylene having 1 to 15 carbon atoms, 1 in which at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine; R 2 is independently alkyl having 1 to 5 carbon atoms; R 3 is independently a linear alkyl having 1 to 10 carbon atoms, a branched alkyl having 3 to 10 carbon atoms, or a cyclic alkyl having 3 to 8 carbon atoms; Y 1 are independently chlorine, fluorine, or bromine; In formula (1), Sp 2 is a single bond or an alkylene having 1 to 10 carbon atoms, and Sp 2 in which at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, -OCOO- or a group represented by formula (1-a), at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) or formula (1-p5);

[0035] [ka]

[0036] X 1 is a polar group having a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, phosphorus and silicon; P 1 and P 2 has at least one group selected from the groups represented by formula (1-p1), formula (1-p2), and formula (1-p3), Sp 2is a single bond or an alkylene having 1 to 10 carbon atoms, and Sp 2 in which at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, -OCOO- or a group represented by formula (1-a), at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) or formula (1-p5); P 1 and P 2 When none of the groups represented by formula (1-p1), formula (1-p2), and formula (1-p3) is present, Sp 2 is an alkylene having 1 to 10 carbon atoms, and this Sp 2 In the formula (1-a), at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) or formula (1-p5).

[0037] Item 2. The compound according to item 1, wherein the polar group is represented by any one of formulas (X-1) to (X-27):

[0038] [ka]

[0039] In formulas (X-1) to (X-27), J 1 and J. 2 are independently hydrogen, or a linear alkyl having 1 to 5 carbon atoms or a branched alkyl having 3 to 5 carbon atoms; 1 and J. 2wherein at least one -CH2- may be replaced by -O-; J 3 is hydrogen, a linear alkyl having 1 to 20 carbon atoms, or a branched alkyl having 3 to 20 carbon atoms, 3 wherein at least one -CH2- may be replaced by -O-, -COO- or -OCO-; J 4 and J. 5 are independently hydrogen or alkyl having 1 to 8 carbon atoms; Q 1 is a methine or nitrogen, where the hydrogen of the methine may be replaced by an alkyl having 1 to 6 carbon atoms; U 1 and U 2 are independently -CH2-, -O-, -CO- or -S-; V 1 , V 2 and V 3 are independently methine or nitrogen, V 1 , V 2 and V 3 at least one of which contains nitrogen; W 1 is -O- or -S-; W 2 is carbon, sulfur or silicon. However, in formula (X-14), Q 1 If is methine, U 1 and U 2 At least one of is -O-, -CO- or -S-.

[0040] Item 3. The compound according to item 1 or 2, which is represented by any one of formulas (1-1) to (1-8):

[0041] [ka]

[0042] [ka]

[0043] In formulas (1-1) to (1-8), R 1 is hydrogen or alkyl having 1 to 15 carbon atoms, 1 in which at least one -CH2- may be replaced by -O- or -S-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine; Ring A 1 From Ring A 5 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5-diyl, and the ring A 1 From Ring A 5 in which at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or alkenyloxy having 2 to 9 carbons, and in these substituents, at least one hydrogen may be replaced by fluorine or chlorine; b and c are independently 0, 1, or 2; Z 1 From Z 4 are independently a single bond, -(CH2)2-, -CH=CH-, -C≡C-, -COO-, -OCO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, or -CF=CF-; P 1 and P 2 are independently a group selected from groups represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) and formula (1-p5);

[0044] [ka]

[0045] In formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) and formula (1-p5), Sp 1 are independently a single bond or an alkylene having 1 to 7 carbon atoms, 1 in which at least one -CH2- may be replaced by -O-, -CO- or -COO-, at least one -(CH2)2- may be replaced by -CH=CH-, and at least one hydrogen may be replaced by fluorine or chlorine; R 2 is independently alkyl having 1 to 5 carbon atoms; R 3 is independently a linear alkyl having 1 to 10 carbon atoms, a branched alkyl having 3 to 10 carbon atoms, or a cyclic alkyl having 3 to 8 carbon atoms; Y 1 are independently chlorine, fluorine, or bromine; In formulas (1-1) to (1-8), Sp 2 is a single bond or an alkylene having 1 to 7 carbon atoms, and Sp 2 in which at least one -CH2- may be replaced by -O-, -CO-, -COO- or a group represented by formula (1-a), at least one -(CH2)2- may be replaced by -CH=CH-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) or formula (1-p5);

[0046] [ka]

[0047] X 1 is a polar group having a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, phosphorus and silicon; P 1 and P 2has at least one group selected from the groups represented by formula (1-p1), formula (1-p2), and formula (1-p3), Sp 2 is a single bond or an alkylene having 1 to 7 carbon atoms, and Sp 2 in which at least one -CH2- may be replaced by -O-, -CO-, -COO- or a group represented by formula (1-a), at least one -(CH2)2- may be replaced by -CH=CH-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) or formula (1-p5); P 1 and P 2 When none of the groups represented by formula (1-p1), formula (1-p2), and formula (1-p3) is present, Sp 2 is an alkylene having 1 to 7 carbon atoms, and this Sp 2 In the formula (1-a), at least one -CH2- may be replaced by -O-, -CO-, or -COO-, at least one -(CH2)2- may be replaced by -CH=CH-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) or formula (1-p5).

[0048] Item 4. The compound according to any one of items 1 to 3, which is represented by any one of formulas (1-9) to (1-16):

[0049] [ka]

[0050] [ka]

[0051] In the formulas (1-9) to (1-16), R1 is hydrogen or alkyl having 1 to 10 carbon atoms, 1 in which at least one -CH2- may be replaced by -O-, at least one -(CH2)2- may be replaced by -CH=CH-, and at least one hydrogen may be replaced by fluorine or chlorine; Ring A 1 From Ring A 5 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5-diyl, and the ring A 1 From Ring A 5 wherein at least one hydrogen may be replaced by fluorine, alkyl having 1 to 5 carbons, alkenyl having 2 to 5 carbons, or alkoxy having 1 to 4 carbons; b and c are independently 0, 1, or 2; Z 1 From Z 4 are independently a single bond, -(CH2)2-, -CH=CH-, -C≡C-, -CH2O-, or -OCH2-; P 1 and P 2 are independently a group selected from the groups represented by formula (1-p1), formula (1-p2), and formula (1-p3);

[0052] [ka]

[0053] In formula (1-p1), formula (1-p2) and formula (1-p3), Sp 1 are independently a single bond or an alkylene having 1 to 5 carbon atoms, 1 in which at least one -CH2- may be replaced by -O-, at least one -(CH2)2- may be replaced by -CH=CH-, and at least one hydrogen may be replaced by fluorine or chlorine; R 2is independently alkyl having 1 to 5 carbon atoms; R 3 is independently a linear alkyl having 1 to 10 carbon atoms, a branched alkyl having 3 to 10 carbon atoms, or a cyclic alkyl having 3 to 8 carbon atoms; Y 1 are independently chlorine, fluorine, or bromine; In the formulas (1-9) to (1-16), Sp 2 is a single bond or an alkylene having 1 to 7 carbon atoms, and Sp 2 In the formula (1-a), at least one -CH2- may be replaced by -O- or a group represented by formula (1-a), and at least one hydrogen may be replaced by fluorine or chlorine;

[0054] [ka]

[0055] X 1 is a polar group having a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, phosphorus and silicon; The compounds represented by formulas (1-9) to (1-16) have at least one group selected from the groups represented by formulas (1-p1), (1-p2), and (1-p3).

[0056] Item 5. The compound according to any one of items 1 to 4, which is represented by any one of formulas (1-17) to (1-145):

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060]

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[0061]

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[0062]

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[0063]

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[0064]

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[0065]

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[0066]

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[0067]

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[0068]

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[0069]

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[0070]

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[0071]

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[0072]

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[0073]

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[0074]

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[0075]

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[0076]

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[0077]

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[0080]

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[0081] [ka]

[0082] [ka]

[0083] [ka]

[0084] [ka]

[0085] [ka]

[0086] [ka]

[0087] In equations (1-17) to (1-145), R 1 is alkyl having 1 to 10 carbon atoms; Z 1 From Z 3 are independently a single bond or -(CH2)2-; Sp 1 are independently a single bond or an alkylene having 1 to 5 carbon atoms, 1 wherein at least one -CH2- may be replaced by -O-; R 2 is independently alkyl having 1 to 5 carbon atoms; R 3 is independently a linear alkyl having 1 to 10 carbon atoms, a branched alkyl having 3 to 10 carbon atoms, or a cyclic alkyl having 3 to 8 carbon atoms; Y 1are independently chlorine, fluorine, or bromine; Y 11 From Y 21 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, alkenyl having 2 to 5 carbons, or alkoxy having 1 to 4 carbons; Sp 2 is a single bond or an alkylene having 1 to 7 carbon atoms, and Sp 2 In the formula (1-a), at least one -CH2- may be replaced by -O- or a group represented by formula (1-a), and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), or formula (1-p4);

[0088] [ka]

[0089] [ka]

[0090] Sp 3 and Sp 4 are independently a single bond or an alkylene having 1 to 5 carbon atoms, 3 and Sp 4 wherein at least one -CH2- may be replaced by -O-; X 1 is a polar group having a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, phosphorus and silicon.

[0091] Item 6. A liquid crystal composition comprising at least one compound according to any one of items 1 to 5.

[0092] Item 7. The liquid crystal composition according to item 6, comprising at least one compound selected from the group of compounds represented by formulas (2) to (4):

[0093] [ka]

[0094] In equations (2) to (4), R 11 and R 12 are independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, 11 and R 12 In the formula (I), at least one -CH2- may be replaced by -O-, and at least one hydrogen may be replaced by fluorine; Ring B 1 , ring B 2 , ring B 3 , and ring B 4 is independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, or pyrimidine-2,5-diyl; Z 11 , Z 12 , and Z 13 are independently a single bond, -COO-, -(CH2)2-, -CH=CH-, or -C≡C-.

[0095] Item 8. The liquid crystal composition according to item 6 or 7, which contains at least one compound selected from the group of compounds represented by formulas (5) to (7):

[0096] [ka]

[0097] In equations (5) to (7), R 13 is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, 13 In the formula (I), at least one -CH2- may be replaced by -O-, and at least one hydrogen may be replaced by fluorine; X 11is fluorine, chlorine, -OCF3, -OCHF2, -CF3, -CHF2, -CH2F, -OCF2CHF2, or -OCF2CHFCF3; Ring C 1 , ring C 2 , and ring C 3 are independently 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or 1,4-phenylene in which at least one hydrogen is replaced by fluorine; Z 14 , Z 15 , and Z 16 are independently a single bond, -COO-, -OCO-, -CHO-, -OCH-, -CFO-, -OCF-, -(CH)-, -CH=CH-, -C≡C-, or -(CH)-; L 11 and L 12 are independently hydrogen or fluorine.

[0098] Item 9. The liquid crystal composition according to any one of items 6 to 8, comprising at least one compound selected from the group of compounds represented by formula (8):

[0099] [ka]

[0100] In the formula (8), R 14 is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, 14 In the formula (I), at least one -CH2- may be replaced by -O-, and at least one hydrogen may be replaced by fluorine; X 12 is -C≡N or -C≡CC≡N; Ring D 1is 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or 1,4-phenylene in which at least one hydrogen is replaced by fluorine; Z 17 is a single bond, -COO-, -OCO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, -(CH2)2-, or -C≡C-; L 13 and L 14 are independently hydrogen or fluorine; i is 1, 2, 3, or 4.

[0101] Item 10. The liquid crystal composition according to any one of items 6 to 9, comprising at least one compound selected from the group of compounds represented by formulas (11) to (19):

[0102] [ka]

[0103] In equations (11) to (19), R 15 , R 16 , and R 17 are independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, 15 , R 16 , and R 17 In the formula (I), at least one -CH2- may be replaced by -O-, at least one hydrogen may be replaced by fluorine, and R 17 may be hydrogen or fluorine; Ring E 1 , Ring E 2 , Ring E 3 , and ring E 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, decahydronaphthalene-2,6-diyl, or 1,4-phenylene in which at least one hydrogen is replaced by fluorine; Ring E 5 and ring E 6 is independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl; Z 18 , Z 19 , Z 20 , and Z 21 are independently a single bond, -COO-, -OCO-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, -(CH2)2-, -CF2O-(CH2)2-, or -OCF2-(CH2)2-; L 15 and L 16 is independently fluorine or chlorine; S 11 is hydrogen or methyl; X is -CHF- or -CF2-; j, k, m, n, p, q, r, and s are independently 0 or 1; the sum of k, m, n, and p is 1 or 2; and the sum of q, r, and s is 0, 1, 2, or 3; t is 1, 2, or 3.

[0104] Item 11. The liquid crystal composition according to any one of items 6 to 10, which contains at least one polymerizable compound represented by formula (20) other than the compound represented by formula (1).

[0105] [ka]

[0106] In the formula (20), Ring F and ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxan-2-yl, pyrimidin-2-yl, or pyridin-2-yl, in which at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen; Ring G 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, phenanthrene, cyclohexyl, ... Z 22 and Z 23 are independently a single bond or an alkylene having 1 to 10 carbon atoms, 22 and Z 23 in which at least one -CH2- may be replaced by -O-, -CO-, -COO-, or -OCO-, at least one -(CH2)2- may be replaced by -CH=CH-, -C(CH3)=CH-, -CH=C(CH3)-, or -C(CH3)=C(CH3)-, and at least one hydrogen may be replaced by fluorine or chlorine; P 11 , P 12 , and P 13 are independently a polymerizable group; Sp 11 , Sp 12 , and Sp13 are independently a single bond or an alkylene having 1 to 10 carbon atoms, 11 , Sp 12 , and Sp 13 in which at least one -CH2- may be replaced by -O-, -COO-, -OCO-, or -OCOO-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine; u is 0, 1, or 2; f, g, and h are independently 0, 1, 2, 3, or 4, and the sum of f, g, and h is 1 or greater.

[0107] Item 12. In equation (20), P 11 , P 12 , and P 13 are independently a group selected from the group of polymerizable groups represented by formulae (P-1) to (P-5).

[0108] [ka]

[0109] In formulas (P-1) to (P-5), M 11 , M 12 , and M. 13 are independently 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 halogen.

[0110] Item 13. The liquid crystal composition according to item 11 or 12, wherein the polymerizable compound represented by formula (20) is at least one compound selected from the group consisting of polymerizable compounds represented by formulas (20-1) to (20-7):

[0111] [ka]

[0112] In equations (20-1) to (20-7), L 31 , L 32 , L 33 , L 34 , L 35 , L 36 , L 37 , and L 38 are independently hydrogen, fluorine, or methyl; Sp 11 , Sp 12 , and Sp 13 are independently a single bond or an alkylene having 1 to 10 carbon atoms, 11 , Sp 12 , and Sp 13 In the above, at least one -CH2- may be replaced by -O-, -COO-, -OCO-, or -OCOO-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine. P 11 , P 12 , and P 13 are independently a group selected from the group of polymerizable groups represented by formulas (P-1) to (P-3),

[0113] [ka]

[0114] In formulas (P-1) to (P-3), M 11 , M 12 , and M. 13 are independently 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 halogen.

[0115] Item 14. The liquid crystal composition according to any one of items 6 to 13, further comprising at least one selected from the group consisting of a polymerizable compound other than the compound represented by formula (1) or formula (20), a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, a dye, and an antifoaming agent.

[0116] Item 15. A liquid crystal display device comprising at least one selected from the group consisting of the liquid crystal composition according to any one of items 6 to 14 and a liquid crystal composition obtained by at least partially polymerizing the liquid crystal composition according to any one of items 6 to 14.

[0117] The present invention also includes the following items. (a) The liquid crystal composition described above, further comprising at least two of additives such as a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, a dye, and an antifoaming agent. (b) A polymerizable composition prepared by adding a polymerizable compound other than compound (1) or compound (20) to the above liquid crystal composition. (c) A polymerizable composition prepared by adding compound (1) and compound (20) to the above liquid crystal composition. (d) A liquid crystal composite prepared by polymerizing the polymerizable composition. (e) A polymer-supported alignment type element containing this liquid crystal composite. (f) A polymer supported alignment type element produced by using a polymerizable composition prepared by adding compound (1), compound (20), and a polymerizable compound different from compound (1) or compound (20) to the above liquid crystal composition.

[0118] The following will explain the embodiment of compound (1), the synthesis of compound (1), the liquid crystal composition, and the liquid crystal display device in this order.

[0119] 1. Aspects of compound (1) The compound (1) of the present invention is characterized by having a mesogen moiety composed of at least one ring, a polymerizable group such as methoxymethacryloyloxy, and a polar group such as -OH. The compound (1) is useful because the polar group interacts with the substrate surface such as glass (or metal oxide) in a non-covalent manner. One of its uses is as an additive for a liquid crystal composition used in a liquid crystal display device, in which the compound (1) is added for the purpose of controlling the alignment of liquid crystal molecules. It is preferable that such an additive is chemically stable under the condition of being sealed in the device, has high stability against heat, has a high ability to align liquid crystal molecules, has a high voltage holding ratio when used in a liquid crystal display device, and has a high solubility in the liquid crystal composition. The compound (1) satisfies these characteristics to a considerable extent, and has an extremely high solubility in the liquid crystal composition that could not be achieved by conventional compounds, and by using the compound (1), a device excellent in long-term stability can be easily obtained while maintaining the same or higher alignment and voltage holding ratio compared to the case of using conventional compounds.

[0120] A preferred example of compound (1) will be described. R in compound (1) 1 , A 1 , Sp 2 Preferred examples of symbols such as are also applicable to sub-formulas of compound (1), such as formula (1-1). In compound (1), by appropriately combining the types of these groups, it is possible to arbitrarily adjust the properties. Since there is no significant difference in the properties of the compound, compound (1) is 2 H (deuterium), 13 Isotopes such as C may be included in amounts greater than the natural abundance.

[0121] [ka]

[0122] R 1 is hydrogen or alkyl having 1 to 15 carbon atoms, 1In the above, at least one -CH2- may be replaced with -O- or -S-, at least one -(CH2)2- may be replaced with -CH=CH- or -C≡C-, and at least one hydrogen may be replaced with fluorine or chlorine.

[0123] Preferred R 1 is hydrogen or alkyl having 1 to 10 carbon atoms, 1 In the formula, at least one -CH2- may be replaced with -O-, at least one -(CH2)2- may be replaced with -CH=CH-, and at least one hydrogen may be replaced with fluorine or chlorine. More preferred R 1 is alkyl having 1 to 10 carbon atoms.

[0124] R 1 Compounds in which R is an alkyl group having 1 to 15 carbon atoms have high chemical stability. 1 Compounds in which R is an alkyl group having 1 to 15 carbon atoms have high solubility in liquid crystal compositions. 1 Compounds in which is an alkyl group having 1 to 15 carbon atoms have a high ability to align liquid crystal molecules.

[0125] Ring A 1 and Ring A 2 are independently 1,2-cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,4-cyclohexylene, 1,4-cycloheptylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, and the ring A 1 and Ring A 2In the above-listed groups, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or alkenyloxy having 2 to 9 carbons, and in these substituents, at least one hydrogen may be replaced by fluorine or chlorine.

[0126] Preferred Ring A 1 and Ring A 2 is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5-diyl, and the ring A 1 and Ring A 2 In the above-listed groups, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or alkenyloxy having 2 to 9 carbons, and in these substituents, at least one hydrogen may be replaced by fluorine or chlorine.

[0127] More preferred ring A 1 and Ring A 2 is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5-diyl, and the ring A 1 and Ring A 2 In the above, at least one hydrogen may be replaced by fluorine, alkyl having 1 to 5 carbons, alkenyl having 2 to 5 carbons, or alkoxy having 1 to 4 carbons.

[0128] Particularly preferred ring A 1 and Ring A 2is 1,4-cyclohexylene, 1,4-phenylene, 2-position-substituted, 3-position-substituted, or 2- and 3-position-substituted 1,4-phenylene, and the substituent is preferably hydrogen, fluorine, alkyl having 1 to 5 carbon atoms, alkenyl having 2 to 5 carbon atoms, or alkoxy having 1 to 4 carbon atoms, and more preferably hydrogen, fluorine, methyl, or ethyl.

[0129] Ring A 1 and Ring A 2 Compounds in which are independently 1,3-cyclopentylene, 1,4-cyclohexylene, 1,4-cycloheptylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine, 1,4-phenylene in which at least one hydrogen is replaced by alkyl having 1 to 5 carbon atoms, decahydronaphthalene-2,6-diyl, or tetrahydropyran-2,5-diyl have high chemical stability. 1 and Ring A 2 Compounds in which are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine, 1,4-phenylene in which at least one hydrogen is replaced by alkyl having 1 to 5 carbon atoms, or 1,4-phenylene in which at least one hydrogen is replaced by alkenyl having 2 to 5 carbon atoms have high solubility in liquid crystal compositions. 1 and Ring A 2 Compounds in which are independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is replaced by an alkyl having 1 to 2 carbon atoms have a high ability to align liquid crystal molecules. 1 and Ring A 2 A compound in which are independently 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by alkyl having 1 to 5 carbon atoms, 1,4-phenylene in which at least one hydrogen is replaced by alkoxy having 1 to 4 carbon atoms, naphthalene-2,6-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl has high polymerization reactivity when irradiated with ultraviolet light.

[0130] a is 0, 1, 2, 3, or 4, preferably 0, 1, 2, or 3, more preferably 1, 2, or 3, and particularly preferably 1 or 2.

[0131] A compound in which a is 0 has high solubility in a liquid crystal composition. A compound in which a is 3 or 4 has a high ability to align liquid crystal molecules. A compound in which a is 1 or 2 has high solubility in a liquid crystal composition, a high ability to align liquid crystal molecules, and high polymerization reactivity when irradiated with ultraviolet light.

[0132] b and c are independently 0, 1, or 2. Preferably, the sum of b and c is 1 or more. More preferably, the sum of b and c is 1, 2, 3, or 4. When the sum of b and c is 1 or 2, the solubility is high.

[0133] Compounds in which the sum of b and c is 1 or more are ring A 1 or Ring A 2 In this case, the polymerization reactivity by ultraviolet irradiation is high.

[0134] Z 1 are independently a single bond or an alkylene having 1 to 6 carbon atoms, 1 In the above, at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine.

[0135] Preferred Z 1 is a single bond, -(CH2)2-, -CH=CH-, -C≡C-, -COO-, -OCO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, or -CF=CF-. More preferred Z 1 is a single bond, -(CH2)2-, -CH=CH-, -C≡C-, -CH2O-, or -OCH2-, and more preferably Z 1is a single bond or -(CH2)2-, and particularly preferred Z 1 is a single bond.

[0136] Z 1 Compounds in which Z is a single bond have high chemical stability. 1 Compounds in which Z is a single bond, -(CH2)2-, -CF2O-, or -OCF2- have high solubility in liquid crystal compositions. 1 Compounds in which Z is a single bond or -(CH2)2- have a high ability to align liquid crystal molecules. 1 Compounds in which is a single bond, -CH=CH-, -C≡C-, -COO-, -OCO-, -CHO-, or -OCH- have high polymerization reactivity when exposed to ultraviolet light.

[0137] P 1 and P 2 are independently selected from the groups represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) and formula (1-p5), and preferably, P 1 and P 2 At least one of the formulas (1-p1), (1-p2), and (1-p3) has one or more groups selected from the group represented by formula (1-p1), (1-p2), and (1-p3). Preferred P 1 and P 2 is a group selected from the groups represented by formula (1-p1), formula (1-p2), and formula (1-p3).

[0138] [ka]

[0139] P 1 and P 2 A compound in which at least one of is a group represented by formula (1-p1), formula (1-p2), or formula (1-p3) has high solubility.

[0140] Sp 1 are independently a single bond or an alkylene having 1 to 15 carbon atoms, 1In the above, at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine.

[0141] Preferred Sp 1 is a single bond or an alkylene having 1 to 7 carbon atoms, and Sp 1 In the above, at least one -CH2- may be replaced with -O-, -CO- or -COO-, at least one -(CH2)2- may be replaced with -CH=CH-, and at least one hydrogen may be replaced with fluorine or chlorine.

[0142] More preferred Sp 1 is a single bond or an alkylene having 1 to 5 carbon atoms, and Sp 1 In the formula, at least one -CH2- may be replaced with -O-, at least one -(CH2)2- may be replaced with -CH=CH-, and at least one hydrogen may be replaced with fluorine or chlorine. More preferred Sp 1 is a single bond or an alkylene having 1 to 5 carbon atoms, and Sp 1 In the above formula, at least one -CH2- may be replaced by -O-.

[0143] Sp 1 Compounds in which are independently a single bond or an alkylene having 1 to 7 carbon atoms have high chemical stability. 1 A compound in which are independently alkylene having 1 to 7 carbon atoms or a group in which at least one -CH2- of alkylene having 1 to 7 carbon atoms is replaced with -O- has high solubility in a liquid crystal composition.

[0144] R 2 are independently alkyl having 1 to 5 carbon atoms. 2 has 1 to 3 carbon atoms. 2has one carbon atom, and in this case, it has high reactivity, and can maintain the ability to align liquid crystal molecules and the voltage holding ratio when used in a liquid crystal display element.

[0145] R 3 are independently a linear alkyl having 1 to 10 carbon atoms, a branched alkyl having 3 to 10 carbon atoms, or a cyclic alkyl having 3 to 8 carbon atoms. 3 has 1 to 5 carbon atoms. 3 has one carbon atom, and in this case, it has high reactivity, and can maintain the ability to align liquid crystal molecules and the voltage holding ratio when used in a liquid crystal display element.

[0146] Y 1 is independently chlorine, fluorine, or bromine. 1 is fluorine. 1 When is fluorine, the solubility is high.

[0147] Sp 2 is a single bond or an alkylene having 1 to 10 carbon atoms, and Sp 2 In the formula (1-a), at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, -OCOO- or a group represented by formula (1-a), at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3) or formula (1-p4). P 1 and P 2 has at least one group selected from the groups represented by formula (1-p1), formula (1-p2), and formula (1-p3), Sp 2 is a single bond or an alkylene having 1 to 10 carbon atoms, and Sp 2In the formula (1-a), at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, -OCOO- or a group represented by formula (1-a), at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) or formula (1-p5). However, P 1 and P 2 When none of the groups represented by formula (1-p1), formula (1-p2), and formula (1-p3) is present, Sp 2 is an alkylene having 1 to 10 carbon atoms, and this Sp 2 In the formula (1-a), at least one -CH2- may be replaced by -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) or formula (1-p5).

[0148] [ka]

[0149] Preferred Sp 2 is a single bond or an alkylene having 1 to 7 carbon atoms, and Sp 2 In the formula (1-a), at least one -CH2- may be replaced by -O-, -CO-, -COO- or a group represented by formula (1-a), at least one -(CH2)2- may be replaced by -CH=CH-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3) or formula (1-p4).

[0150] More preferred Sp 2is a single bond or an alkylene having 1 to 7 carbon atoms, and Sp 2 In the above formula, at least one -CH2- may be replaced by -O- or a group represented by formula (1-a), and at least one hydrogen may be replaced by fluorine or chlorine. More preferred Sp 2 is a single bond or an alkylene having 1 to 7 carbon atoms, and Sp 2 In the formula (1-a), at least one -CH2- may be replaced by -O- or a group represented by formula (1-a).

[0151] Sp 2 Compounds in which is a single bond or an alkylene having 1 to 7 carbon atoms have high chemical stability. 2 A compound in which is an alkylene having 1 to 7 carbon atoms, or an alkylene having 1 to 7 carbon atoms in which at least one -CH2- is replaced with -O- or a group represented by formula (1-a) has high solubility in a liquid crystal composition.

[0152] X 1 is a polar group having a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, phosphorus and silicon.

[0153] Preferred X 1 is a polar group represented by any one of formulas (X-1) to (X-27).

[0154] [ka]

[0155] In formulas (X-1) to (X-27), J 1 and J. 2 are independently hydrogen, or a linear alkyl having 1 to 5 carbon atoms or a branched alkyl having 3 to 5 carbon atoms; 1 and J. 2 In the above formula, at least one -CH2- may be replaced by -O-. J 3is hydrogen, a linear alkyl having 1 to 20 carbon atoms, or a branched alkyl having 3 to 20 carbon atoms, 3 In the above formula, at least one -CH2- may be replaced by -O-, -COO- or -OCO-. J 4 and J. 5 are independently hydrogen or alkyl having 1 to 8 carbon atoms; Q 1 is a methine or nitrogen, where the hydrogen of the methine may be replaced with an alkyl of 1 to 6 carbon atoms. U 1 and U 2 are independently -CH2-, -O-, -CO- or -S-. V 1 , V 2 and V 3 are independently methine or nitrogen, V 1 , V 2 and V 3 At least one of them contains nitrogen. W 1 is -O- or -S-. W 2 is carbon, sulfur or silicon. However, in formula (X-14), Q 1 If is methine, U 1 and U 2 At least one of is -O-, -CO- or -S-.

[0156] More preferred X 1 -OH, -NH2, -OR 4 , -N(R 4 )2, -COOH, -SH, or -Si(R 4 )3. More preferable X is a compound having excellent solubility in a liquid crystal composition. 1 is -OH, -NH2, or -SH, and particularly preferred X 1 is -OH. Here, R 4 is hydrogen or alkyl having 1 to 10 carbon atoms, 4In the formula, at least one -CH2- may be replaced with -O-, at least one -(CH2)2- may be replaced with -CH=CH-, and at least one hydrogen may be replaced with fluorine or chlorine.

[0157] X 1 Compounds in which X is -OH, -NH2, or -SH have a high ability to align liquid crystal molecules. 1 The compound in which is --OH has high chemical stability, a high ability to align liquid crystal molecules, a high voltage holding ratio when used in a liquid crystal display device, and a high solubility in a liquid crystal composition.

[0158] Desirable compound (1) has at least one group selected from the groups represented by formula (1-p1), formula (1-p2), and formula (1-p3).

[0159] Preferred examples of compound (1) include compounds (1-1) to (1-8) described in item 3. More preferred examples of compound (1) include compounds (1-9) to (1-16) described in item 4. Further preferred examples of compound (1) include compounds (1-17) to (1-145) described in item 5.

[0160] 2. Synthesis of compound (1) The synthesis method of compound (1) is explained below. Compound (1) can be synthesized by appropriately combining organic synthetic chemistry methods. Compounds for which no synthesis method is described can be synthesized by methods described in books such as "Organic Synthesis" (John Wiley & Sons, Inc.), "Organic Reactions" (John Wiley & Sons, Inc.), "Comprehensive Organic Synthesis" (Pergamon Press), and "New Experimental Chemistry Lectures" (Maruzen).

[0161] 2-1. Formation of bonding groups An example of a method for forming the linking group in compound (1) is shown in the following scheme. In this scheme, MSG 1 (or MSG 2 ) is a monovalent organic group having at least one ring. 1 (or MSG 2 The monovalent organic groups represented by may be the same or different. Compounds (1A) to (1H) correspond to compound (1) or intermediates of compound (1).

[0162] [ka]

[0163] [ka]

[0164] [ka]

[0165] [ka]

[0166] [ka]

[0167] [ka]

[0168] (I) Formation of a single bond The boric acid compound (21) is reacted with the compound (22) in the presence of carbonate and tetrakis(triphenylphosphine)palladium catalyst to synthesize the compound (1A). The compound (1A) can also be synthesized by reacting the compound (23) with n-butyllithium and then with zinc chloride, and then reacting the compound (22) in the presence of dichlorobis(triphenylphosphine)palladium catalyst.

[0169] (II) Formation of -COO- and -OCO- Compound (23) is reacted with n-butyl lithium and then with carbon dioxide to obtain carboxylic acid (24). This carboxylic acid (24) and alcohol (25) derived from compound (21) are dehydrated in the presence of DCC (1,3-dicyclohexylcarbodiimide) and DMAP (4-dimethylaminopyridine) to synthesize compound (1B) having -COO-. Compounds having -OCO- can also be synthesized by this method.

[0170] (III) Generation of -CF2O- and -OCF2- Compound (1B) is sulfurized with Lawesson's reagent to obtain compound (26). Compound (26) is fluorinated with hydrogen fluoride pyridine complex and NBS (N-bromosuccinimide) to synthesize compound (1C) having -CF2O-. See M. Kuroboshi et al., Chem. Lett., 1992, 827. Compound (1C) can also be synthesized by fluorinating compound (26) with DAST ((diethylamino)sulfur trifluoride). See WH Bunnelle et al., J. Org. Chem. 1990, 55, 768. Compounds having -OCF2- can also be synthesized by this method.

[0171] (IV) Formation of -CH=CH- Compound (22) is reacted with n-butyllithium and then with DMF (N,N-dimethylformamide) to obtain aldehyde (27). Phosphonium salt (28) is reacted with potassium tert-butoxide to generate phosphorus ylide, which is then reacted with aldehyde (27) to synthesize compound (1D). Depending on the reaction conditions, a cis isomer may be produced, and the cis isomer may be isomerized to a trans isomer by a known method, as necessary.

[0172] Formation of (V)-(CH2)2- Compound (1D) is hydrogenated in the presence of a palladium carbon catalyst to synthesize compound (1E).

[0173] (VI) Formation of -C≡C- In the presence of dichloropalladium and copper iodide catalysts, compound (23) is reacted with 2-methyl-3-butyn-2-ol, and then deprotected under basic conditions to obtain compound (29). In the presence of dichlorobis(triphenylphosphine)palladium and copper halide catalysts, compound (29) is reacted with compound (22) to synthesize compound (1F).

[0174] (VII) Generation of -CH2O- and -OCH2- Compound (27) is reduced with sodium borohydride to obtain compound (30). This is brominated with hydrobromic acid to obtain compound (31). Compound (1G) is synthesized by reacting compound (25) with compound (31) in the presence of potassium carbonate. Compounds having -OCH2- can also be synthesized by this method.

[0175] (VIII) Formation of -CF=CF- Compound (23) is treated with n-butyllithium, and then reacted with tetrafluoroethylene to obtain compound (32). Compound (22) is treated with n-butyllithium, and then reacted with compound (32) to synthesize compound (1H).

[0176] 2-2. Ring A 1 and A 2 Generation of For rings such as 1,2-cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,4-cyclohexylene, 1,4-cycloheptylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, and pyridine-2,5-diyl, the starting materials are commercially available or the synthesis methods are well known.

[0177] 2-3. Synthesis examples An example of a method for synthesizing compound (1) is as follows. In these compounds, R 1 , A 1 , A 2 , Z 1 , P 1 , P 2 , Sp 2 , X 1 The definitions of a, b, and c are the same as those described in section 1.

[0178] The compound (1-X51) of formula (1) in which the polar group is formula (X-24) and the polymerizable group is fluoroacryloyloxy can be synthesized by the following method. Compound (51) is reacted in the presence of formaldehyde and DABCO (1,4-diazabicyclo[2.2.2]octane) to give compound (52). Compound (52) is reacted in the presence of pyridinium p-toluenesulfonate (PPTS) and 3,4-dihydro-2H-pyran to give compound (53). Compound (54) is reacted with 2-fluoroacrylic acid, N,N-dicyclohexylcarbodiimide (DCC), and N,N-dimethyl-4-aminopyridine (DMAP) to obtain compound (55). Compound (55) is reacted with tetrabutylammonium fluoride (TBAF) to obtain compound (56). Compound (56) is reacted with compound (53), N,N-dicyclohexylcarbodiimide, and N,N-dimethyl-4-aminopyridine to obtain compound (57). Compound (57) is reacted with pyridinium p-toluenesulfonate (PPTS) to obtain compound (1-X51).

[0179] [ka]

[0180] 3. Liquid crystal composition 3-1.Component compounds The liquid crystal composition of the present invention contains compound (1) as component A. Compound (1) can control the alignment of liquid crystal molecules by non-covalent interaction with the substrate of the element. This composition contains compound (1) as component A, and preferably further contains at least one liquid crystal compound selected from the following components B, C, D, and E. Component B is compounds (2) to (4). Component C is compounds (5) to (7) other than compounds (2) to (4). Component D is compound (8). Component E is compounds (11) to (19). This composition may contain other liquid crystal compounds different from compounds (2) to (8) and (11) to (19). When preparing this composition, it is preferable to select components B, C, D, and E in consideration of the magnitude of positive or negative dielectric anisotropy, etc. A composition in which the components are appropriately selected has a high upper limit temperature, a low lower limit temperature, low viscosity, suitable optical anisotropy (i.e., large optical anisotropy or small optical anisotropy), large positive or negative dielectric anisotropy, large resistivity, stability against heat or ultraviolet light, and suitable elastic constant (i.e., large elastic constant or small elastic constant).

[0181] Compound (1) is added to the composition for the purpose of controlling the alignment of liquid crystal molecules. The preferred ratio of compound (1) to 100% by weight of the liquid crystal composition is 0.05% by weight or more, since liquid crystal molecules can be easily aligned, and is preferably 10% by weight or less, since display defects of the device can be more effectively prevented. A more preferred ratio is in the range of 0.1% by weight to 7% by weight, and a particularly preferred ratio is in the range of 0.4% by weight to 5% by weight. These ratios also apply to compositions containing compound (20).

[0182] Component B is a compound in which the two terminal groups are alkyl or the like. Component B has a small dielectric anisotropy. Preferred examples of component B include compounds (2-1) to (2-11), compounds (3-1) to (3-19), and compounds (4-1) to (4-7). In these compounds, R 11 and R 12 are independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, 11 and R 12 In the above formula, at least one -CH2- may be replaced by -O-, and at least one hydrogen may be replaced by fluorine.

[0183] [ka]

[0184] Component B is a nearly neutral compound because of its small absolute value of dielectric anisotropy. Compound (2) is mainly effective in reducing viscosity or adjusting optical anisotropy. Compounds (3) and (4) are effective in expanding the temperature range of the nematic phase by increasing the upper limit temperature, or in adjusting optical anisotropy.

[0185] As the content of component B increases, the dielectric anisotropy of the composition decreases, but the viscosity decreases. Therefore, as long as the required value of the threshold voltage of the element is satisfied, a larger content of component B is preferable. The content of component B is preferably 30% by weight or more, more preferably 40% by weight or more, relative to 100% by weight of the liquid crystal composition, and the upper limit is not particularly limited, but is, for example, 99.95% by weight.

[0186] Component C is a compound having fluorine, chlorine or a fluorine-containing group at at least one end. Component C has a positively large dielectric anisotropy. Preferable examples of component C include compounds (5-1) to (5-16), compounds (6-1) to (6-116), and compounds (7-1) to (7-59). In the compound of component C, R 13 is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, 13 In the formula, at least one -CH2- may be replaced by -O-, and at least one hydrogen may be replaced by fluorine; 11 is fluorine, chlorine, -OCF3, -OCHF2, -CF3, -CHF2, -CH2F, -OCF2CHF2, or -OCF2CHFCF3.

[0187] [ka]

[0188] [ka]

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[0194] Component C has positive dielectric anisotropy and is very stable against heat, light, etc., and is therefore suitable for use in preparing compositions for modes such as IPS, FFS, and OCB. The content of component C relative to 100% by weight of the liquid crystal composition is suitably in the range of 1% by weight to 99% by weight, preferably in the range of 10% by weight to 97% by weight, and more preferably in the range of 40% by weight to 95% by weight. When component C is added to a composition having negative dielectric anisotropy, the content of component C is preferably 30% by weight or less relative to 100% by weight of the liquid crystal composition. By adding component C, it is possible to adjust the elastic constant of the composition and adjust the voltage-transmittance curve of the element.

[0195] Component D is a compound (8) having one terminal group of -C≡N or -C≡CC≡N. Component D has a cyano group and therefore has a large positive dielectric anisotropy. Preferred examples of component D include compounds (8-1) to (8-64). In the compound of component D, R 14 is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, 14 In the above, at least one -CH2- may be replaced by -O-, and at least one hydrogen may be replaced by fluorine; 12 is -C≡N or -C≡CC≡N.

[0196] [ka]

[0197] [ka]

[0198] Component D has a positive and large dielectric anisotropy, and is therefore mainly used when preparing compositions for modes such as TN. The addition of component D can increase the dielectric anisotropy of the composition. Component D has the effect of widening the temperature range of the liquid crystal phase, adjusting the viscosity, or adjusting the optical anisotropy. Component D is also useful for adjusting the voltage-transmittance curve of the element.

[0199] The content of component D relative to 100% by weight of the liquid crystal composition is suitably in the range of 1 to 99% by weight, preferably in the range of 10 to 97% by weight, and more preferably in the range of 40 to 95% by weight. When component D is added to a composition having negative dielectric anisotropy, the content of component D is preferably 30% by weight or less relative to 100% by weight of the liquid crystal composition. By adding component D, it becomes possible to adjust the elastic constant of the composition and adjust the voltage-transmittance curve of the element.

[0200] Component E is compounds (11) to (19). Component E has a large negative dielectric anisotropy. These compounds have phenylene substituted with two halogens (fluorine or chlorine) at the lateral positions, such as 2,3-difluoro-1,4-phenylene. Preferred examples of component E include compounds (11-1) to (11-9), compounds (12-1) to (12-19), compounds (13-1) and (13-2), compounds (14-1) to (14-3), compounds (15-1) to (15-3), compounds (16-1) to (16-11), compounds (17-1) to (17-3), compounds (18-1) to (18-3), and compound (19-1). In these compounds, R 15 , R 16 , and R 17 are independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, 15 , R16 , and R 17 In the formula (I), at least one -CH2- may be replaced by -O-, at least one hydrogen may be replaced by fluorine, and R 17 may be hydrogen or fluorine.

[0201] [ka]

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[0203] Component E has a large negative dielectric anisotropy. Component E is preferably used when preparing a composition for modes such as IPS, VA, and PSA. As the content of component E is increased, the dielectric anisotropy of the composition becomes larger negatively, but the viscosity also increases. For this reason, as long as the required value of the threshold voltage of the element is satisfied, a smaller content is preferable. Considering that the dielectric anisotropy is about -5, in order to achieve sufficient voltage driving, the content of component E relative to 100% by weight of the liquid crystal composition is preferably 40% by weight or more.

[0204] Of component E, compound (11) is a two-ring compound and has the effects of decreasing viscosity, adjusting optical anisotropy, or increasing dielectric anisotropy. Compounds (12) and (13) are three-ring compounds, and compound (14) is a four-ring compound and has the effects of increasing the maximum temperature, increasing optical anisotropy, or increasing dielectric anisotropy. Compounds (15) to (19) have the effect of increasing dielectric anisotropy.

[0205] The content of component E is preferably 40% by weight or more, more preferably in the range of 50 to 95% by weight, based on 100% by weight of the liquid crystal composition. When component E is added to a composition having a positive dielectric anisotropy, the content of component E is preferably 30% by weight or less, based on 100% by weight of the liquid crystal composition. By adding component E, it becomes possible to adjust the elastic constant of the composition and adjust the voltage-transmittance curve of the element.

[0206] By appropriately combining the above-mentioned components B, C, D, and E, a liquid crystal composition can be prepared which satisfies at least one of the following properties: a high upper limit temperature, a low lower limit temperature, a small viscosity, suitable optical anisotropy, a large positive or negative dielectric anisotropy, a large resistivity, high stability against ultraviolet light, high stability against heat, and a large elastic constant.

[0207] 3-2. Additives The liquid crystal composition is prepared by a known method. For example, the components are mixed and dissolved in each other by heating. Depending on the application, additives may be added to the composition. Examples of additives include polymerizable compounds other than compound (1), polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, dyes, antifoaming agents, etc. Such additives are well known to those skilled in the art and are described in the literature.

[0208] The polymerizable compound is added to the liquid crystal composition for the purpose of generating a polymer. The liquid crystal composition is injected into the element, and then irradiated with ultraviolet light while a voltage is applied between the electrodes to polymerize compound (1), thereby generating a polymer. At this time, compound (1) is fixed in a state in which its polar group interacts non-covalently with the glass (or metal oxide) substrate surface. This further improves the ability to control the alignment of the liquid crystal molecules, and an appropriate pretilt angle is obtained, thereby shortening the response time.

[0209] Preferred examples of the polymerizable compound are acrylate, methacrylate, vinyl compound, vinyloxy compound, propenyl ether, epoxy compound (oxirane, oxetane), and vinyl ketone.More preferred examples are compounds having at least one acryloyloxy and compounds having at least one methacryloyloxy.More preferred examples include compounds having both acryloyloxy and methacryloyloxy. A particularly preferred example of the polymerizable compound is compound (20). Compound (20) is a compound different from compound (1). Compound (1) has a polar group. On the other hand, compound (20) preferably does not have a polar group.

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[0211] In formula (20), ring F and ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxan-2-yl, pyrimidin-2-yl, or pyridin-2-yl, and in ring F and ring I, at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen.

[0212] Preferred ring F or ring I is cyclohexyl, cyclohexenyl, phenyl, fluorophenyl, difluorophenyl, 1-naphthyl, or 2-naphthyl. More preferred ring F or ring I is cyclohexyl, cyclohexenyl, or phenyl. Particularly preferred ring F or ring I is phenyl.

[0213] In the formula (20), ring G 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, phenanthrene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, in which at least one hydrogen in the ring G may be replaced by a halogen, an alkyl having 1 to 12 carbons, an alkoxy having 1 to 12 carbons, or an alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by a halogen.

[0214] Preferred ring G is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 2-fluoro-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.More preferred ring G is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, or 2-fluoro-1,4-phenylene.Particularly preferred ring G is 1,4-phenylene or 2-fluoro-1,4-phenylene. The most preferred ring G is 1,4-phenylene.

[0215] In formula (20), Z 22 and Z 23 are independently a single bond or an alkylene having 1 to 10 carbon atoms, 22 and Z 23In the above, at least one -CH2- may be replaced by -O-, -CO-, -COO-, or -OCO-, at least one -(CH2)2- may be replaced by -CH=CH-, -C(CH3)=CH-, -CH=C(CH3)-, or -C(CH3)=C(CH3)-, and at least one hydrogen may be replaced by fluorine or chlorine. 22 or Z 23 is a single bond, -(CH2)2-, -CH2O-, -OCH2-, -COO-, or -OCO-. 22 or Z 23 is a single bond.

[0216] In compound (20), P 11 , P 12 , and P 13 are independently polymerizable groups. 11 From P 13 is a group selected from the group of polymerizable groups represented by formulas (P-1) to (P-5). 11 From P 13 is a group represented by formula (P-1), formula (P-2), or formula (P-3). Particularly preferred P 11 From P 13 is a group represented by formula (P-1). A preferred group represented by formula (P-1) is acryloyloxy (-OCO-CH=CH2) or methacryloyloxy (-OCO-C(CH3)=CH2). The wavy lines in formulas (P-1) to (P-5) indicate the bonding site.

[0217] [ka]

[0218] In formulas (P-1) to (P-5), M 11 , M 12 , and M. 13 are independently 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 halogen. 11 , M12 , or M 13 is hydrogen or methyl to increase reactivity. More preferably, M 11 is hydrogen or methyl, more preferably M 12 or M 13 is hydrogen.

[0219] In equation (20), Sp 11 , Sp 12 , and Sp 13 are independently a single bond or an alkylene having 1 to 10 carbon atoms, 11 , Sp 12 , and Sp 13 In the above, at least one -CH2- may be replaced by -O-, -COO-, -OCO-, or -OCOO-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine. 11 , Sp 12 , and Sp 13 is a single bond.

[0220] In formula (20), u is 0, 1, or 2. Preferred u is 0 or 1.

[0221] In formula (20), f, g, and h are independently 0, 1, 2, 3, or 4, and the sum of f, g, and h is 1 or more. Preferably, f, g, or h is 1 or 2. Preferably, the sum is 2, 3, or 4. More preferably, the sum is 2 or 3.

[0222] Preferred examples of compound (20) are compounds (20-1) to (20-7) described in item 13 and compounds (20-8) to (20-11) described below. More preferred examples are compounds (20-1-1) to (20-1-5), compounds (20-2-1) to (20-2-5), compounds (20-4-1), compounds (20-5-1), compounds (20-6-1), and compounds (20-7-1). In these compounds, R 25 From R31 are independently hydrogen or methyl; R 32 , R 33 , and R 34 are independently hydrogen or alkyl having 1 to 5 carbon atoms; R 32 , R 33 , and R 34 at least one of is an alkyl having 1 to 5 carbon atoms; v and x are independently 0 or 1; t and u are independently integers from 1 to 10, and t+v and x+u are each up to 10; L 31 From L 36 are independently hydrogen or fluorine, and L 37 and L 38 are independently hydrogen, fluorine, or methyl.

[0223] [ka]

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[0225] The polymerizable compound in the composition can be polymerized quickly by using a polymerization initiator such as a photoradical polymerization initiator. In addition, the amount of the remaining polymerizable compound can be reduced by optimizing the reaction conditions during polymerization. Examples of the photoradical polymerization initiator include TPO, 1173, and 4265 from the Darocure series of BASF, and 184, 369, 500, 651, 784, 819, 907, 1300, 1700, 1800, 1850, and 2959 from the Irgacure series.

[0226] Additional examples of photoradical polymerization initiators are 4-methoxyphenyl-2,4-bis(trichloromethyl)triazine, 2-(4-butoxystyryl)-5-trichloromethyl-1,3,4-oxadiazole, 9-phenylacridine, 9,10-benzphenazine, benzophenone / Michler's ketone mixture, hexaarylbiimidazole / mercaptobenzimidazole mixture, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, benzyl dimethyl ketal, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2,4-diethylxanthone / methyl p-dimethylaminobenzoate mixture, benzophenone / methyltriethanolamine mixture.

[0227] After adding a photoradical polymerization initiator to the liquid crystal composition, polymerization can be performed by irradiating ultraviolet light while applying an electric field. However, unreacted polymerization initiator or decomposition products of the polymerization initiator may cause display defects such as image sticking on the device. To prevent this, photopolymerization may be performed without adding a polymerization initiator. The preferred wavelength of the irradiated light is in the range of 150 nm to 500 nm. More preferred wavelengths are in the range of 250 nm to 450 nm, and most preferred wavelengths are in the range of 300 nm to 400 nm.

[0228] When storing a polymerizable compound, a polymerization inhibitor may be added to prevent polymerization. The polymerizable compound is usually added to the composition without removing the polymerization inhibitor. Examples of polymerization inhibitors are hydroquinone, hydroquinone derivatives such as methylhydroquinone, 4-t-butylcatechol, 4-methoxyphenol, and phenothiazine.

[0229] The optically active compound has the effect of preventing reverse twisting by inducing a helical structure in the liquid crystal molecules and imparting the necessary twist angle. The helical pitch can be adjusted by adding an optically active compound. Two or more optically active compounds may be added for the purpose of adjusting the temperature dependency of the helical pitch. Preferable examples of the optically active compound include the following compounds (Op-1) to (Op-18). In compound (Op-18), ring J is 1,4-cyclohexylene or 1,4-phenylene, and R 28 is an alkyl group having 1 to 10 carbon atoms. The * symbol indicates an asymmetric carbon atom.

[0230] [ka]

[0231] The antioxidant is effective in maintaining a large voltage holding ratio. Preferable examples of the antioxidant include the following compounds (AO-1) and (AO-2): Irganox415, Irganox565, Irganox1010, Irganox1035, Irganox3114, and Irganox1098 (trade name; BASF). The ultraviolet absorber is effective in preventing the lowering of the upper limit temperature.Preferred examples of the ultraviolet absorber include benzophenone derivatives, benzoate derivatives, triazole derivatives, etc., and specific examples thereof include the following compounds (AO-3) and (AO-4); Tinuvin 329, Tinuvin P, Tinuvin 326, Tinuvin 234, Tinuvin 213, Tinuvin 400, Tinuvin 328, and Tinuvin 99-2 (trade name; BASF); and 1,4-diazabicyclo[2.2.2]octane (DABCO).

[0232] A light stabilizer such as a sterically hindered amine is preferred to maintain a large voltage holding ratio. Preferred examples of the light stabilizer include the following compounds (AO-5), (AO-6), and (AO-7); Tinuvin 144, Tinuvin 765, and Tinuvin 770DF (trade names; BASF); and LA-77Y and LA-77G (trade names; ADEKA). A thermal stabilizer is also effective in maintaining a large voltage holding ratio, and a preferred example is Irgafos168 (trade name; BASF). In order to adapt the composition to a GH (guest host) mode element, a dichroic dye such as an azo dye or an anthraquinone dye may be added to the composition, if necessary. The antifoaming agent is effective in preventing foaming. Preferred examples of the antifoaming agent include dimethyl silicone oil and methyl phenyl silicone oil.

[0233] [ka]

[0234] In compound (AO-1), R 40 is an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, -COOR 41 , or -(CH2)2-COOR 41 where R 41 is an alkyl group having 1 to 20 carbon atoms. In compounds (AO-2) and (AO-5), R 42 is an alkyl group having 1 to 20 carbon atoms. In compound (AO-5), R 43 is hydrogen, methyl or O · (oxygen radical); Ring G 1 is 1,4-cyclohexylene or 1,4-phenylene; in compound (AO-7), ring G 2 represents 1,4-cyclohexylene, 1,4-phenylene, or a group in which at least one hydrogen of 1,4-phenylene is replaced by fluorine; in compounds (AO-5) and (AO-7), z is 1, 2, or 3.

[0235] 4. Liquid crystal display element The liquid crystal composition can be suitably used in liquid crystal display elements that have operating modes such as PC, TN, STN, OCB, PSA, etc. and are driven by an active matrix system. The composition can also be suitably used in liquid crystal display elements that have operating modes such as PC, TN, STN, OCB, VA, IPS, etc. and are driven by a passive matrix system. These elements can be applied to any of the reflective, transmissive, and semi-transmissive types.

[0236] This composition is also suitable for NCAP (nematic curvilinear aligned phase) elements, where the composition is microencapsulated. This composition can also be used for polymer dispersed liquid crystal display elements (PDLCD) and polymer network liquid crystal display elements (PNLCD). In these compositions, a large amount of polymerizable compound is added. On the other hand, in the composition used for PSA mode liquid crystal display elements, the ratio of the polymerizable compound is preferably 10% by weight or less, more preferably 0.1% by weight to 2% by weight, and even more preferably 0.2% by weight to 1.0% by weight, based on 100% by weight of the liquid crystal composition. The PSA mode element can be driven by a driving method such as an active matrix method or a passive matrix method. Such elements can be applied to any of the reflective, transmissive, and semi-transmissive types.

[0237] In a polymer-supported alignment type element, the polymer contained in the composition aligns the liquid crystal molecules. The polar compound assists the liquid crystal molecules in aligning. That is, the polar compound can be used instead of an alignment film. An example of a method for manufacturing such an element is as follows. An element having two substrates called an array substrate and a color filter substrate is prepared. These substrates do not have an alignment film. At least one of these substrates has an electrode layer. A liquid crystal composition is prepared by mixing liquid crystal compounds. Compound (1) and, if necessary, other polymerizable compounds and polar compounds are added to this composition. If necessary, additives may be further added. This composition is injected into the element. The element is irradiated with light while a voltage is applied. Ultraviolet light is preferred. The polymerizable compound is polymerized by light irradiation. This polymerization produces a composition containing a polymer, and an element having a PSA mode is produced.

[0238] In this procedure, the polar compound is aligned on the substrate because the polar group interacts with the substrate surface. This polar compound aligns the liquid crystal molecules. When multiple polar groups are present, the interaction with the substrate surface becomes stronger, and alignment can be achieved at a low concentration. When a voltage is applied, the alignment of the liquid crystal molecules is further promoted by the action of the electric field. The polymerizable compound is also aligned according to this alignment. In this state, the polymerizable compound is polymerized by ultraviolet light, so a polymer that maintains this alignment is generated. The effect of this polymer additionally stabilizes the alignment of the liquid crystal molecules, so the response time of the element is shortened. Image sticking is a malfunction of the liquid crystal molecules, so the effect of this polymer also improves sticking at the same time. Since compound (1) is polymerizable, it is consumed by polymerization. Compound (1) is also consumed by copolymerization with other polymerizable compounds. Therefore, although compound (1) has a polar group, it is consumed, so a liquid crystal display element with a large voltage retention rate is obtained. Furthermore, if a polar compound having polymerizability is used, it is possible to achieve the effects of both a polar compound and a polymerizable compound with a single compound, so there may be cases where a polymerizable compound without a polar group is not required. EXAMPLES

[0239] The present invention will be described in more detail with reference to examples (including synthesis examples and use examples). The present invention is not limited by these examples. The present invention also includes a mixture prepared by mixing at least two of the compositions in the use examples.

[0240] 1. Examples of Compound (1) Unless otherwise stated, the reaction was carried out under a nitrogen atmosphere. Compound (1) was synthesized according to the procedure shown in Example 1. The synthesized compound was identified by a method such as NMR analysis. The characteristics of compound (1), liquid crystal compound, composition, and element were measured by the following methods.

[0241] NMR analysis: For the measurement, a DRX-500 manufactured by Bruker Biospin was used. 1 In the H-NMR measurement, the sample was dissolved in a deuterated solvent such as CDCl3, and the measurement was performed at room temperature, at 500 MHz, and with 16 accumulations. Tetramethylsilane was used as the internal standard. 19 In the F-NMR measurement, CFCl3 was used as an internal standard, and the number of accumulations was 24. In the explanation of the nuclear magnetic resonance spectrum, s means singlet, d means doublet, t means triplet, q means quartet, quin means quintet, sext means sextet, m means multiplet, and br means broad.

[0242] Gas chromatographic analysis: A GC-2010 gas chromatograph manufactured by Shimadzu Corporation was used for the measurements. A capillary column DB-1 manufactured by Agilent Technologies Inc. (length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm) was used as the column. Helium (1 ml / min) was used as the carrier gas. The temperature of the sample vaporizer was set to 300°C, and the temperature of the detector (FID) was set to 300°C. The sample was dissolved in acetone to prepare a 1 wt% solution, and 1 μl of the resulting solution was injected into the sample vaporizer. A GCSolution system manufactured by Shimadzu Corporation was used as the recorder.

[0243] HPLC analysis: Prominence (LC-20AD; SPD-20A) manufactured by Shimadzu Corporation was used for the measurement. YMC-Pack ODS-A (length 150 mm, inner diameter 4.6 mm, particle size 5 μm) manufactured by YMC Corporation was used as the column. A suitable mixture of acetonitrile and water was used as the eluent. UV detectors, RI detectors, CORONA detectors, etc. were used as appropriate as detectors. When a UV detector was used, the detection wavelength was 254 nm. The sample was dissolved in acetonitrile to prepare a 0.1 wt % solution, and 1 μL of this solution was introduced into the sample chamber. C-R7Aplus manufactured by Shimadzu Corporation was used as the recorder.

[0244] Ultraviolet-visible spectroscopic analysis: For the measurement, a PharmaSpec UV-1700 manufactured by Shimadzu Corporation was used. The detection wavelength was 190 nm to 700 nm. The sample was dissolved in acetonitrile to prepare a 0.01 mmol / L solution, which was then placed in a quartz cell (path length 1 cm) and measured.

[0245] Measurement sample: When measuring the phase structure and transition temperature (clearing point, melting point, polymerization initiation temperature, etc.), the compound itself was used as the sample.

[0246] Measurement method: The characteristics were measured by the following methods. Most of these were methods described in the JEITA standard (JEITA ED-2521B) established by the Japan Electronics and Information Technology Industries Association (JEITA), or modified methods. No thin film transistors (TFTs) were attached to the TN elements used for the measurements.

[0247] (1) Phase structure The sample was placed on a hot plate of a melting point measuring device equipped with a polarizing microscope (Mettler, FP-52 hot stage). The sample was heated at a rate of 3°C / min, while observing the phase state and its change under the polarizing microscope, and the type of phase was identified.

[0248] (2) Transition temperature (℃) For the measurements, a PerkinElmer scanning calorimeter, Diamond DSC system, or a high-sensitivity differential scanning calorimeter, X-DSC7000, manufactured by Hitachi High-Tech Science Corporation, was used. The temperature of the sample was raised and lowered at a rate of 3°C / min, and the onset of the endothermic or exothermic peak associated with the phase change of the sample was extrapolated to determine the transition temperature. The melting point and polymerization initiation temperature of the compound were also measured using this device. The temperature at which a compound transitions from a solid to a liquid crystal phase such as a smectic phase or nematic phase is sometimes abbreviated as the "lower limit temperature of the liquid crystal phase." The temperature at which a compound transitions from a liquid crystal phase to a liquid is sometimes abbreviated as the "clearing point."

[0249] Crystals are represented as C. When the types of crystals can be distinguished, they are represented as C1, C2, etc. Smectic phases are represented as S, and nematic phases as N. When the smectic phases can be distinguished into smectic A, smectic B, smectic C, and smectic F, they are represented as S. A , S B , S C , or S F The phase is expressed as follows: Liquid (isotropic) is expressed as I. The transition temperature is expressed as, for example, "C 50.0 N 100.0 I." This indicates that the transition temperature from crystal to nematic phase is 50.0°C, and the transition temperature from nematic phase to liquid is 100.0°C.

[0250] (3) The maximum temperature of the nematic phase (T NI or NI;℃) The sample was placed on the hot plate of a melting point measuring apparatus equipped with a polarizing microscope and heated at a rate of 1°C / min. The temperature at which a part of the sample changed from a nematic phase to an isotropic liquid was measured. The upper limit temperature of the nematic phase is sometimes abbreviated as the "upper limit temperature". When the sample is a mixture of compound (1) and mother liquid crystals, T NI When the sample was a mixture of compound (1) and compounds such as components B, C, and D, it was indicated by the symbol NI.

[0251] (4) The minimum temperature of the nematic phase (T C ;℃) The liquid crystal phase was observed after storing samples with a nematic phase in freezers at 0°C, -10°C, -20°C, -30°C, and -40°C for 10 days. For example, when a sample remained in a nematic phase at -20°C and changed to a crystalline or smectic phase at -30°C, T C The lowest temperature of the nematic phase is sometimes abbreviated as "lower limit temperature."

[0252] (5) Viscosity (bulk viscosity; η; measured at 20°C; mPa s) For the measurement, an E-type rotational viscometer manufactured by Tokyo Keiki Co., Ltd. was used.

[0253] (6) Optical anisotropy (refractive index anisotropy; measured at 25°C; Δn) Measurements were performed using light with a wavelength of 589 nm and an Abbe refractometer with a polarizing plate attached to an eyepiece. The surface of the main prism was rubbed in one direction, and then the sample was dropped onto the main prism. The refractive index (n∥) was measured when the direction of polarized light was parallel to the direction of rubbing. The refractive index (n⊥) was measured when the direction of polarized light was perpendicular to the direction of rubbing. The optical anisotropy (Δn) was calculated from the formula Δn=n∥-n⊥.

[0254] (7) Resistivity (ρ; measured at 25°C; Ωcm) 1.0 mL of sample was poured into a container equipped with electrodes. A DC voltage (10 V) was applied to the container, and the DC current was measured after 10 seconds. The resistivity was calculated from the following formula: (resistivity) = {(voltage) x (capacity of container)} / {(DC current) x (dielectric constant of vacuum)}.

[0255] The measurement methods for the properties of samples with positive and negative dielectric anisotropy may differ. The measurement methods for positive dielectric anisotropy are described in items (8a) to (12a). For negative dielectric anisotropy, the measurement methods are described in items (8b) to (12b).

[0256] (8a) Viscosity (rotational viscosity; γ1; measured at 25°C; mPa s) Positive dielectric anisotropy: Measurement was performed according to the method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). A sample was placed in a TN device with a twist angle of 0 degrees and a distance (cell gap) between two glass substrates of 5 μm. Voltage was applied to this device in steps of 0.5 V increments from 16 V to 19.5 V. After no voltage was applied for 0.2 seconds, voltage was applied repeatedly under the conditions of only one square wave (square pulse; 0.2 seconds) and no voltage application (2 seconds). The peak current and peak time of the transient current generated by this application were measured. The value of rotational viscosity was obtained from these measurements and the calculation formula (8) on page 40 of the paper by M. Imai et al. The value of dielectric anisotropy required for this calculation was obtained by the method described below using the device in which the rotational viscosity was measured.

[0257] (8b) Viscosity (rotational viscosity; γ1; measured at 25°C; mPa s) Negative dielectric anisotropy: Measurements were performed according to the method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). A sample was placed in a VA element with a cell gap of 20 μm between two glass substrates. Voltages were applied to this element in steps of 1 volt each in the range of 39 to 50 volts. After no voltage was applied for 0.2 seconds, voltages were applied repeatedly under the conditions of a single square wave (square pulse; 0.2 seconds) and no voltage application (2 seconds). The peak current and peak time of the transient current generated by this voltage application were measured. The rotational viscosity was obtained from these measurements and the calculation formula (8) on page 40 of the paper by M. Imai et al. The value of the dielectric anisotropy required for this calculation was the value measured in the section on dielectric anisotropy below.

[0258] (9a) Dielectric anisotropy (Δε; measured at 25°C) Positive dielectric anisotropy: A sample was placed in a TN device with a cell gap of 9 μm between two glass substrates and a twist angle of 80 degrees. A sine wave (10 V, 1 kHz) was applied to the device, and the dielectric constant (ε∥) in the long axis direction of the liquid crystal molecules was measured after 2 seconds. A sine wave (0.5 V, 1 kHz) was applied to the device, and the dielectric constant (ε⊥) in the short axis direction of the liquid crystal molecules was measured after 2 seconds. The value of the dielectric anisotropy was calculated from the formula Δε=ε∥-ε⊥.

[0259] (9b) Dielectric anisotropy (Δε; measured at 25°C) Negative dielectric anisotropy: 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 thoroughly cleaned glass substrate. The glass substrate was rotated on a spinner and then heated at 150°C for 1 hour. A sample was placed in a VA element with a cell gap of 4 μm between two glass substrates, and the element was sealed with an adhesive that hardens with ultraviolet light. A sine wave (0.5 V, 1 kHz) was applied to the element, and the dielectric constant (ε∥) in the long axis direction of the liquid crystal molecules was measured after 2 seconds. 2) Measurement of dielectric constant (ε⊥): A polyimide solution was applied to a thoroughly cleaned glass substrate. After baking the glass substrate, the resulting alignment film was subjected to a rubbing treatment. A sample was placed in a TN element with a cell gap of 9 μm between the two glass substrates and a twist angle of 80 degrees. A sine wave (0.5 V, 1 kHz) was applied to the element, and the dielectric constant (ε⊥) in the minor axis direction of the liquid crystal molecules was measured after 2 seconds.

[0260] (10a) Elastic constant (K; measured at 25°C; pN) Positive dielectric anisotropy: An HP4284A LCR meter manufactured by Agilent Technologies was used for the measurement. The sample was placed in a horizontally aligned element with a cell gap of 20 μm between the two glass substrates. A charge of 0 to 20 volts was applied to this element, and the capacitance and applied voltage were measured. The measured capacitance (C) and applied voltage (V) were fitted using equations (2.98) and (2.101) on page 75 of the Liquid Crystal Device Handbook (published by Nikkan Kogyo Shimbun), and K was calculated from equation (2.99). 11 and K. 33 Next, we add the value of K 11 and K. 33 Using the value of K 22 The elastic constant K was calculated as follows: 11 , K 22 and K. 33 The results are expressed as the average value.

[0261] (10b) Elastic constant (K 11 and K. 33 Measured at 25°C; pN Negative dielectric anisotropy: Measurements were performed using an EC-1 elastic constant measuring device manufactured by Toyo Corporation. The sample was placed in a vertically aligned element with a cell gap of 20 μm between two glass substrates. A charge of 20 volts to 0 volts was applied to this element, and the capacitance and applied voltage were measured. The capacitance (C) and applied voltage (V) values ​​were fitted using equations (2.98) and (2.101) on page 75 of the Liquid Crystal Device Handbook (published by Nikkan Kogyo Shimbun), and the elastic constant value was obtained from equation (2.100).

[0262] (11a) Threshold voltage (Vth; measured at 25°C; V) Positive dielectric anisotropy: An LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. A halogen lamp was used as the light source. The sample was placed in a normally white mode TN element with a cell gap of 0.45 / Δn (μm) between two glass substrates and a twist angle of 80 degrees. The voltage (32 Hz, square wave) applied to the element was increased stepwise by 0.02 V from 0 V to 10 V. At this time, light was irradiated vertically onto the element, and the amount of light transmitted through the element was measured. A voltage-transmittance curve was created in which the maximum amount of light was the transmittance of 100% and the minimum amount of light was the transmittance of 0%. The threshold voltage was expressed as the voltage at which the transmittance was 90%.

[0263] (11b) Threshold voltage (Vth; measured at 25°C; V) Negative dielectric anisotropy: For the measurement, an LCD5100-type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. A halogen lamp was used as the light source. A sample was placed in a normally black mode VA element in which the distance (cell gap) between the two glass substrates was 4 μm and the rubbing direction was antiparallel, and the element was sealed using an adhesive that hardens with ultraviolet light. The voltage (60 Hz, square wave) applied to the element was increased stepwise from 0 V to 20 V in increments of 0.02 V. At this time, the element was irradiated with light from a vertical direction, and the amount of light transmitted through the element was measured. A voltage-transmittance curve was created in which the transmittance was 100% when the amount of light was maximum and the transmittance was 0% when the amount of light was minimum. The threshold voltage was expressed as the voltage at which the transmittance was 10%.

[0264] (12a) Response time (τ; measured at 25°C; ms) Positive dielectric anisotropy: An LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. A halogen lamp was used as the light source. The low-pass filter was set to 5 kHz. A sample was placed in a normally white mode TN device with a cell gap of 5.0 μm between two glass substrates and a twist angle of 80 degrees. A square wave (60 Hz, 5 V, 0.5 seconds) was applied to this device. At this time, light was irradiated from the vertical direction to measure the amount of light transmitted through the device. The maximum amount of light was considered to be the transmittance of 100%, and the minimum amount of light was considered to be the transmittance of 0%. The rise time (τr: rise time; milliseconds) is the time required for the transmittance to change from 90% to 10%. The fall time (τf: fall time; milliseconds) is the time required for the transmittance to change from 10% to 90%. The response time was expressed as the sum of the rise time and fall time thus determined.

[0265] (12b) Response time (τ; measured at 25°C; ms) Negative dielectric anisotropy: A LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. A halogen lamp was used as the light source. The low-pass filter was set to 5 kHz. The sample was placed in a normally black mode PVA element in which the distance between the two glass substrates (cell gap) was 3.2 μm and the rubbing direction was anti-parallel. This element was sealed with an adhesive that hardens with ultraviolet light. A voltage slightly exceeding the threshold voltage was applied to this element for 1 minute, and then a voltage of 5.6 V was applied while maintaining a constant current of 23.5 mW / cm. 2 The element was irradiated with ultraviolet light of 1000 nm for 8 minutes. A square wave (60 Hz, 10 V, 0.5 seconds) was applied to the element. During this process, light was irradiated vertically onto the element, and the amount of light transmitted through the element was measured. When the amount of light was at its maximum, the transmittance was considered to be 100%, and when the amount of light was at its minimum, the transmittance was considered to be 0%. The response time was expressed as the time required for the transmittance to change from 90% to 10% (fall time; milliseconds).

[0266] (13) Voltage holding ratio The polymerizable compound was polymerized by irradiating it with ultraviolet light using a black light, F40T10 / BL (peak wavelength 369 nm) manufactured by Eye Graphics Co., Ltd. A pulse voltage (1 V for 60 microseconds) was applied to this element at 60°C to charge it. The decaying voltage was measured for 1.67 seconds using a high-speed voltmeter, and the area A between the voltage curve and the horizontal axis in a unit period was calculated. Area B is the area when there was no decay. The voltage retention rate was expressed as a percentage of area A to area B.

[0267] raw material Solmix® A-11 is a mixture of ethanol (85.5%), methanol (13.4%) and isopropanol (IPA) (1.1%) and was obtained from Japan Alcohol Sales Co., Ltd.

[0268] [Synthesis Example 1] Synthesis of compound (1-3-30)

[0269] [ka]

[0270] 1st step Compound (T-1) (100.0 g), compound (T-2) (58.6 g) synthesized by a known method, sodium carbonate (68.1 g), [1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloride, dichloromethane (9.80 g), dioxane (1000 ml), and pure water (250 ml) were placed in a reactor and stirred at 80°C for 8 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The resulting organic layer was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:toluene = 4:1) to obtain compound (T-3) (72.1 g; 77%).

[0271] 2nd process A known compound (T-3) (72.1 g) and tetrahydrofuran (THF) (500 ml) were placed in a reactor, and n-butyllithium (1.6 mol / L, hexane solution) (185.7 ml) was added dropwise at -70°C, and the mixture was stirred at -70°C for 1 hour. A THF solution (150 ml) of compound (T-4) (50.0 g) was added dropwise thereto, and the mixture was stirred for 5 hours while being heated to room temperature. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate = 19:1) to obtain compound (T-5) (84.8 g; 90%).

[0272] 3rd process Aluminum chloride (29.7 g) and toluene (400 ml) were placed in a reactor, and 1,1,3,3-tetramethyldisiloxane (14.9 g) was added dropwise at -70°C. A solution of compound (T-5) (84.8 g) in toluene (400 ml) was added dropwise thereto, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The resulting organic layer was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:ethyl acetate = 19:1) to obtain compound (T-6) (61.7 g; 76%).

[0273] 4th step Compound (T-6) (61.7 g) and dichloromethane (500 ml) were placed in a reactor, and boron tribromide (1.0 mol / L, dichloromethane solution) (220 ml) was added dropwise at 0°C, and the mixture was stirred for 6 hours while warming to room temperature. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate = 9:1) to obtain compound (T-7) (52.0 g; 87%).

[0274] 5th step Compound (T-7) (50.0 g), dichloromethane (500 ml), and methanol (500 ml) were placed in a reactor and cooled to 0°C. Benzyltrimethylammonium tribromide (116.8 g) was added thereto, and the mixture was stirred for 8 hours while returning to room temperature. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate = 9:1) to obtain compound (T-8) (59.4 g; 82%).

[0275] 6th step Compound (T-8) (59.4 g), compound (T-9) (24.7 g), potassium iodide (21.3 g), potassium carbonate (32.3 g), and N,N-dimethylformamide (DMF) (600 ml) were placed in a reactor and stirred at 80° C. for 8 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate=9:1) to obtain compound (T-10) (63.7 g; 82%).

[0276] 7th step Compound (T-10) (63.7 g), sodium bicarbonate (16.1 g), palladium acetate (4.30 g), methyl acrylate (24.7 g), and DMF (600 ml) were placed in a reactor and stirred at 90° C. for 9 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate=4:1) to obtain compound (T-11) (42.0 g; 65%).

[0277] 8th process Compound (T-11) (42.0 g), palladium catalyst (PH type) (0.70 g), toluene (500 ml), and isopropanol (IPA) (500 ml) were placed in a reactor and stirred under a hydrogen atmosphere for 24 hours. The reaction mixture was filtered, the solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate = 4:1) to obtain compound (T-12) (38.0 g; 90%).

[0278] 9th step Lithium aluminum hydride (LAH) (2.54 g) and tetrahydrofuran (THF) (500 ml) were placed in a reactor, and a solution of compound (T-12) (38.0 g) in THF (500 ml) was added at 0°C, followed by stirring at room temperature for 4 hours. Water was poured into the reaction mixture, and the aqueous layer was extracted with ethyl acetate. The resulting organic layer was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate = 1:2) to obtain compound (T-13) (24.4 g; 70%).

[0279] 10th step Compound (T-13) (24.4 g), N,N-dimethylaminopyridine (DMAP) (4.79 g), 2-fluoroacrylic acid (10.5 g), and dichloromethane (500 ml) were placed in a reactor and cooled to 0°C. N,N-dicyclohexylcarbodiimide (DCC) (20.2 g) was added thereto and stirred at room temperature for 8 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. This solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate = 4:1) to obtain compound (T-14) (19.5 g; 65%).

[0280] 11th step Compound (T-14) (19.5 g), pyridinium p-toluenesulfonate (PPTS) (3.19 g), THF (200 ml), and methanol (200 ml) were placed in a reactor and stirred at 50° C. for 12 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate=1:1) to obtain compound (T-15) (14.6 g; 75%).

[0281] 12th step Compound (T-15) (14.6 g), N,N-dimethylaminopyridine (DMAP) (1.16 g), compound (T-16) (4.25 g) synthesized by a known method, and dichloromethane (500 ml) were placed in a reactor and cooled to 0°C. N,N-dicyclohexylcarbodiimide (DCC) (4.71 g) was added thereto and stirred at room temperature for 8 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. This solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate = 4:1) to obtain compound (T-17) (10.5 g; 65%).

[0282] 13th step Compound (T-17) (10.5 g), pyridinium p-toluenesulfonate (PPTS) (1.55 g), THF (100 ml), and methanol (100 ml) were placed in a reactor and stirred at 50° C. for 12 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate=1:1) to obtain compound (1-3-30) (6.6 g; 70%).

[0283] [Synthesis Example 2] Synthesis of compound (1-3-70)

[0284] [ka]

[0285] 1st step Compound (T-13) (20.0 g), N,N-dimethylaminopyridine (DMAP) (9.80 g), compound (T-18) (11.8 g) synthesized by a known method, and dichloromethane (500 ml) were placed in a reactor and cooled to 0°C. N,N-dicyclohexylcarbodiimide (DCC) (19.8 g) was added thereto and stirred at room temperature for 12 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. This solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate = 4:1) to obtain compound (T-19) (13.4 g; 51%).

[0286] 2nd process Compound (T-19) (13.4 g), pyridinium p-toluenesulfonate (PPTS) (2.05 g), THF (100 ml), and methanol (100 ml) were placed in a reactor and stirred at 50° C. for 12 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate=2:1) ​​to obtain compound (T-20) (8.4 g; 70%).

[0287] 3rd process Compound (T-20) (8.4 g), N,N-dimethylaminopyridine (DMAP) (0.70 g), compound (T-16) (2.55 g), and dichloromethane (100 ml) were placed in a reactor and cooled to 0°C. N,N-dicyclohexylcarbodiimide (DCC) (2.82 g) was added thereto and stirred at room temperature for 12 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. This solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate = 2:1) to obtain compound (T-21) (7.74 g; 75%).

[0288] 4th step Compound (T-21) (7.74 g), pyridinium p-toluenesulfonate (PPTS) (1.07 g), THF (50 ml), and methanol (50 ml) were placed in a reactor and stirred at 50° C. for 8 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate=1:1) to obtain compound (1-3-70) (5.4 g; 70%).

[0289] [Synthesis Example 3] Synthesis of compound (1-3-267)

[0290] [ka]

[0291] 1st step Compound (T-15) (15.0 g), N,N-dimethylaminopyridine (DMAP) (1.34 g), and compound (T-22) (5.27 g) synthesized by the synthesis method described in International Publication No. 2019 / 220673 were placed in a reactor and cooled to 0 ° C. N,N-dicyclohexylcarbodiimide (DCC) (5.43 g) was added thereto and stirred at room temperature for 12 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane: ethyl acetate = 4: 1) to obtain compound (T-23) (19.1 g; 82%).

[0292] 2nd process Compound (T-23) (19.1 g), pyridinium p-toluenesulfonate (PPTS) (1.10 g), THF (100 ml), and methanol (100 ml) were placed in a reactor and stirred at room temperature for 6 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The organic layer obtained was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:ethyl acetate = 1:3) to obtain compound (T-24) (14.2 g; 78%).

[0293] 3rd process Compound (T-24) (14.2 g) and dichloromethane (100 ml) were placed in a reactor and cooled to 0°C. Ethyl chloroformate (3.92 g) was added thereto, and then triethylamine (7.2 ml) was added dropwise and stirred for 12 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. This solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:ethyl acetate = 1:1) to obtain compound (1-3-267) (11.8 g; 81%).

[0294] The NMR analysis values ​​of the obtained compound (1-3-267) are as follows. 1H-NMR: Chemical shift δ (ppm; CDCl3): 7.12(s,1H), 7.09-7.05(m,2H), 6.99(s,2H), 6.35(s,1H), 5.72(s,1H), 5. 70(d,J=3.2Hz,1H), 5.61(d,J=3.2Hz,1H), 5.31(dd,J=3.2Hz,13.1Hz,2H), 4.46-4.43(m,2H), 4.29-4.2 6(m,6H), 4.19-4.16(m,2H), 3.85-3.83(m,2H), 2.73(t,J=7.4Hz,4H), 2.58-2.45(m,6H), 2.08-2.02(m, 4H), 1.98-1.87(m,8H), 1.53-1.45(m,2H), 1.34-1.20(m,9H), 1.11-1.02(m,5H), 0.90(t,J=7.1Hz,3H). (Polymerization initiation temperature: 125℃)

[0295] [Comparative Example 1] Compatibility Comparison The following compound (S-1) was selected as a comparative compound and was synthesized according to a known method.

[0296] [ka]

[0297] 1 H-NMR(ppm;CDCl3):6.25(S,1H), 6.10(s,1H), 5.66(S,1H), 5.58-5.57(m,1H), 4.22-4.10(m,4H), 3.80-3.75(m,2H), 3.67-3.62(m,2H), 2.55-2 .52(m,2H), 2.37(d,J=7.4Hz,2H), 2.10-2.05(m,1H), 1.94(s,3H), 1.90 -1.86(m,1H), 1.75-1.67(m,8H), 1.48-1.37(m,2H), 1.32-0.79(m,25H).

[0298] The compatibility of the compound (1-3-30) and the comparative compound (S-1) in a liquid crystal composition was compared. For the evaluation, a composition (i) containing the following compounds (i-1) to (i-9) was used.

[0299] The proportions of the components of composition (i) are shown in % by weight.

[0300] [ka]

[0301] Compound (1-3-30) or comparative compound (S-1) was added to mother liquid crystal (i) at a ratio of 3% by weight to 0.5% by weight to prepare a sample. The sample was left to stand at 25°C and -20°C for 7 days, and then visually observed. If the sample maintained a nematic phase, it was indicated by ○, and if a crystal or smectic phase was precipitated, it was indicated by ×.

[0302] [Table 2]

[0303] As a result of comparing the solubilities, compound (1-3-30) maintained a nematic phase at both 25°C and -20°C even when added at 3% by weight to the mother liquid crystal, whereas comparative compound (S-1) crystallized at -20°C when added at 3% by weight. These compounds are similar in that they have the same ring structure and multiple polymerizable groups are bonded to them, but their compatibility is significantly different. This is because compound (1-3-30) has lower crystallinity than the diol compound, and therefore has improved affinity for the liquid crystal composition compared to comparative compound (S-1). Therefore, it can be said that the compound of the present application is an excellent compound with high compatibility.

[0304] By referring to the methods described in the synthesis examples and the section "2. Synthesis of compound (1)", it is possible to synthesize the following compounds (1-1-1) to (1-1-134), compounds (1-2-1) to (1-2-256), compounds (1-3-1) to (1-3-276), and compounds (1-4-1) to (1-4-155).

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[0338] [ka]

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[0346] [ka]

[0347] 2. Composition Examples The compounds in the examples are represented by symbols based on the definitions in Table 3 below. In Table 3, the configuration of 1,4-cyclohexylene is trans. The number in parentheses after the symbol corresponds to the compound number. The symbol (-) means other liquid crystal compounds. The proportion (percentage) of the liquid crystal compound is a weight percentage (wt%) based on the weight of the liquid crystal composition. Finally, the property values ​​of the liquid crystal composition are summarized. The properties were measured according to the methods described above, and the measured values ​​were listed as they were (without extrapolation).

[0348] [Table 3]

[0349] [Usage example 1] 3-HH-VFF (2-1) 8% 5-HH-VFF (2-1) 22% 2-BTB-1 (2-10) 10% 3-HHB-1 (3-1) 4% VFF-HHB-1 (3-1) 10% VFF2-HHB-1 (3-1) 9% 3-H2BTB-2 (3-17) 5% 3-H2BTB-3 (3-17) 5% 3-H2BTB-4 (3-17) 3% 3-HB-C (8-1) 18% 1V2-BEB(F,F)-C (8-15) 6% To the above composition, the following compound (1-3-30) was added in a proportion of 2% by weight.

[0350] [ka]

[0351] NI=80.8℃;η=10.8mPa·s;Δn=0.130;Δε=6.6.

[0352] [Usage example 2] 3-HH-V (2-1) 30% 3-HH-V1 (2-1) 5% 5-HH-V (2-1) 10% 3-HHB-1 (3-1) 5% V-HHB-1 (3-1) 4% 2-BB(F)B-3 (3-6) 5% 3-HHEH-5 (3-13) 3% 1V2-BB-F (5-1) 3% 3-BB(F,F)XB(F,F)-F (6-97) 8% 3-BB(2F,3F)XB(F,F)-F (6-114) 5% 3-HHBB(F,F)-F (7-6) 2% 3-HBBBXB(F,F)-F (7-32) 4% 5-HB(F)B(F,F)XB(F,F)-F (7-41) 5% 3-BB(F)B(F,F)XB(F,F)-F (7-47) 4% 4-BB(F)B(F,F)XB(F,F)-F (7-47) 4% 5-BB(F)B(F,F)XB(F,F)-F (7-47) 3% To the above composition, the following compound (1-3-70) was added in a proportion of 3% by weight.

[0353] [ka]

[0354] NI=78.0℃;η=12.1mPa·s;Δn=0.097;Δε=5.5.

[0355] [Usage example 3] 1-BB-3 (2-8) 6% 1-BB-5 (2-8) 7% 2-BTB-1 (2-10) 3% 3-HHB-1 (3-1) 7% 3-HHB-3 (3-1) 12% 3-HHB-O1 (3-1) 6% 3-HHB-F (6-1) 4% 2-HHB(F)-F (6-2) 8% 3-HHB(F)-F (6-2) 8% 5-HHB(F)-F (6-2) 7% 3-HHB(F,F)-F (6-3) 5% 3-HHEB-F (6-10) 4% 5-HHEB-F (6-10) 4% 2-HB-C (8-1) 6% 3-HB-C (8-1) 13% To the above composition, the following compound (1-3-68) was added in a proportion of 3% by weight.

[0356] [ka]

[0357] NI=95.6℃;η=17.9mPa·s;Δn=0.107;Δε=5.1.

[0358] [Usage example 4] 1V2-HH-1 (2-1) 3% 1V2-HH-3 (2-1) 4% 7-HB(F,F)-F (5-4) 3% 2-HHB(F)-F (6-2) 8% 3-HHB(F)-F (6-2) 12% 5-HHB(F)-F (6-2) 10% 2-HBB-F (6-22) 4% 3-HBB-F (6-22) 2% 5-HBB-F (6-22) 4% 2-HBB(F)-F (6-23) 9% 3-HBB(F)-F (6-23) 10% 5-HBB(F)-F (6-23) 16% 3-HBB(F,F)-F (6-24) 5% 5-HBB(F,F)-F (6-24) 10% To the above composition, the following compound (1-3-240) was added in a proportion of 3.5% by weight.

[0359] [ka]

[0360] NI=85.1℃;η=25.3mPa·s;Δn=0.111;Δε=5.7.

[0361] [Usage example 5] 3-HH-4 (2-1) 11% 5-HB-O2 (2-5) 4% 7-HB-1 (2-5) 2% 5-HBB(F)B-2 (4-5) 5% 5-HBB(F)B-3 (4-5) 5% 3-HB-CL (5-2) 13% 3-HHB(F,F)-F (6-3) 3% 3-HB(F,F)-F (6-24) 24% 4-HBB(F,F)-F (6-24) 16% 5-HBB(F,F)-F (6-24) 17% To the above composition, the following compound (1-3-249) was added in a proportion of 3% by weight.

[0362] [ka]

[0363] NI=70.6℃;η=20.8mPa·s;Δn=0.115;Δε=6.0.

[0364] [Usage example 6] 3-HH-V (2-1) 30% 3-HH-V1 (2-1) 8% 3-HHB-1 (3-1) 4% V-HHB-1 (3-1) 5% V2-BB(F)B-1 (3-6) 4% 3-HHEH-5 (3-13) 4% 3-HHEBH-3 (4-6 3% 1V2-BB-F (5-1) 4% 3-BB(F)B(F,F)-F (6-69) 5% 3-BB(F,F)XB(F,F)-F (6-97) 3% 3-HHBB(F,F)-F (7-6) 3% 5-HB(F)B(F,F)XB(F,F)-F (7-41) 4% 3-BB(F,F)XB(F)B(F,F)-F (7-56) 5% 4-BB(F)B(F,F)XB(F,F)-F (7-47) 3% 5-BB(F)B(F,F)XB(F,F)-F (7-47) 4% 2-dhBB(F,F)XB(F,F)-F (7-50) 3% 3-dhBB(F,F)XB(F,F)-F (7-50) 2% 3-GBB(F)B(F,F)-F (7-55) 2% 4-GBB(F)B(F,F)-F (7-55) 4% To the above composition, the following compound (1-3-257) was added in a proportion of 3% by weight.

[0365] [ka]

[0366] NI=84.6℃;η=19.3mPa·s;Δn=0.102;Δε=5.6.

[0367] [Usage example 7] 5-HBBH-3 (4-1) 3% 3-HB(F)BH-3 (4-2) 3% 5-HB-F (5-2) 12% 6-HB-F (5-2) 9% 7-HB-F (5-2) 7% 2-HHB-OCF3 (6-1) 7% 3-HHB-OCF3 (6-1) 4% 4-HHB-OCF3 (6-1) 7% 5-HHB-OCF3 (6-1) 8% 3-HHB(F,F)-OCF2H (6-3) 6% 3-HHB(F,F)-OCF3 (6-3) 3% 3-HH2B-OCF3 (6-4) 4% 5-HH2B-OCF3 (6-4) 4% 3-HH2B(F)-F (6-5) 3% 3-HBB(F)-F (6-23) 5% 5-HBB(F)-F (6-23) 15% To the above composition, the following compound (1-4-139) was added in a proportion of 2% by weight.

[0368] [ka]

[0369] NI=86.0℃;η=14.6mPa·s;Δn=0.092;Δε=4.3.

[0370] [Usage example 8] 3-HH-V (2-1) 25% 3-HH-V1 (2-1) 10% V-HH-V1 (2-1) 9% 3-HHB-1 (3-1) 4% V-HHB-1 (3-1) 5% 1-BB(F)B-2V (3-6) 4% 3-HHEH-5 (3-13) 3% 1V2-BB-F (5-1) 3% 3-BB(F,F)XB(F,F)-F (6-97) 6% 3-HHXB(F,F)-CF3 (6-100) 2% 3-GB(F,F)XB(F,F)-F (6-113) 4% 3-GB(F)B(F,F)-F (6-116) 4% 3-HHBB(F,F)-F (7-6) 3% 3-BB(F)B(F,F)XB(F,F)-F (7-47) 5% 4-BB(F)B(F,F)XB(F,F)-F (7-47) 5% 5-BB(F)B(F,F)XB(F,F)-F (7-47) 3% 3-GB(F)B(F,F)XB(F,F)-F (7-57) 5% To the above composition, the following compound (1-4-149) was added in a proportion of 3% by weight.

[0371] [ka]

[0372] NI=81.5℃;η=13.3mPa·s;Δn=0.106;Δε=7.3.

[0373] [Usage example 9] V-HBB-2 (3-4) 10% 1O1-HBBH-4 (4-1) 3% 1O1-HBBH-5 (4-1) 5% 3-HHB(F,F)-F (6-3) 9% 3-H2HB(F,F)-F (6-15) 10% 4-H2HB(F,F)-F (6-15) 6% 5-H2HB(F,F)-F (6-15) 8% 3-HB(F,F)-F (6-24) 10% 5-HBB(F,F)-F (6-24) 21% 3-H2BB(F,F)-F (6-27) 10% 5-HHBB(F,F)-F (7-6) 4% 3-HH2BB(F,F)-F (7-15) 2% 5-HHEBB-F (7-17) 2% To the above composition, the following compound (1-3-245) was added in a proportion of 4% by weight.

[0374] [ka]

[0375] NI=106.7℃;η=32.6mPa·s;Δn=0.123;Δε=8.3.

[0376] [Usage example 10] 2-HH-3 (2-1) 8% 3-HH-4 (2-1) 8% 1O1-HBBH-5 (4-1) 4% 5-HB-CL (5-2) 15% 3-HHB-F (6-1) 4% 3-HHB-CL (6-1) 3% 4-HHB-CL (6-1) 4% 3-HHB(F)-F (6-2) 10% 4-HHB(F)-F (6-2) 9% 5-HHB(F)-F (6-2) 9% 7-HHB(F)-F (6-2) 8% 5-HBB(F)-F (6-23) 4% 3-HHBB(F,F)-F (7-6) 2% 4-HHBB(F,F)-F (7-6) 3% 5-HHBB(F,F)-F (7-6) 3% 3-HH2BB(F,F)-F (7-15) 3% 4-HH2BB(F,F)-F (7-15) 3% To the above composition, the following compound (1-3-270) was added in a proportion of 3% by weight.

[0377] [ka]

[0378] NI=114.4℃;η=18.7mPa·s;Δn=0.091;Δε=3.7.

[0379] [Usage example 11] 3-HH-4 (2-1) 5% 3-HH-5 (2-1) 10% 3-HB-O2 (2-5) 15% 3-HHB-1 (3-1) 5% 3-HHB-O1 (3-1) 8% 5-HB-CL (5-2) 17% 7-HB(F,F)-F (5-4) 3% 2-HHB(F)-F (6-2) 8% 3-HHB(F)-F (6-2) 8% 5-HHB(F)-F (6-2) 5% 3-HHB(F,F)-F (6-3) 6% 3-H2HB(F,F)-F (6-15) 5% 4-H2HB(F,F)-F (6-15) 5% To the above composition, the following compound (1-3-266) was added in a proportion of 3% by weight.

[0380] [ka]

[0381] NI=71.9℃;η=14.1mPa·s;Δn=0.075;Δε=2.9.

[0382] [Usage example 12] 3-HH-V (2-1) 25% 3-HH-V1 (2-1) 10% 3-HHB-1 (3-1) 5% V-HHB-1 (3-1) 7% V2-BB(F)B-1 (3-6) 5% 3-HHEH-5 (3-13) 3% 1V2-BB-F (5-1) 5% 3-BB(F)B(F,F)-CF3 (6-69) 3% 3-BB(F,F)XB(F,F)-F (6-97) 5% 3-HHXB(F,F)-F (6-100) 5% 3-GB(F,F)XB(F,F)-F (6-113) 3% 3-GB(F)B(F)-F (6-115) 3% 3-HHBB(F,F)-F (7-6) 2% 5-HB(F)B(F,F)XB(F,F)-F (7-41) 5% 3-GB(F)B(F,F)XB(F,F)-F (7-57) 3% 3-GBB(F,F)XB(F,F)-F (7-58) 4% 4-GBB(F,F)XB(F,F)-F (7-58) 2% 5-GBB(F,F)XB(F,F)-F (7-58) 2% 3-GB(F)B(F)B(F)-F (7-59) 3% To the above composition, the following compound (1-3-223) was added in a proportion of 2% by weight.

[0383] [ka]

[0384] NI=83.5℃;η=16.6mPa·s;Δn=0.098;Δε=6.2.

[0385] [Usage example 13] V2-HHB-1 (3-1) 4% 3-HB-CL (5-2) 3% 5-HB-CL (5-2) 7% 3-HHB-OCF3 (6-1) 5% 5-HHB(F)-F (6-2) 7% V-HHB(F)-F (6-2) 4% 3-H2HB-OCF3 (6-13) 5% 5-H2HB(F,F)-F (6-15) 5% 5-H4HB-OCF3 (6-19) 15% 5-H4HB(F,F)-F (6-21) 7% 3-H4HB(F,F)-CF3 (6-21) 8% 5-H4HB(F,F)-CF3 (6-21) 10% 2-H2BB(F)-F (6-26) 5% 3-H2BB(F)-F (6-26) 10% 3-HBEB(F,F)-F (6-39) 5% To the above composition, the following compound (1-3-237) was added in a proportion of 2% by weight.

[0386] [ka]

[0387] NI=72.8℃;η=25.0mPa·s;Δn=0.098;Δε=8.2.

[0388] [Usage example 14] 3-HH-4 (2-1) 12% 3-HH-5 (2-1) 7% 3-HHB-1 (3-1) 13% 5-HB-CL (5-2) 3% 7-HB(F)-F (5-3) 7% 2-HHB(F,F)-F (6-3) 2% 3-HHB(F,F)-F (6-3) 7% 3-HHEB-F (6-10) 8% 5-HHEB-F (6-10) 8% 3-HHEB(F,F)-F (6-12) 5% 4-HHEB(F,F)-F (6-12) 10% 3-GHB(F,F)-F (6-109) 6% 4-GHB(F,F)-F (6-109) 5% 5-GHB(F,F)-F (6-109) 7% To the above composition, the following compound (1-2-202) was added in a proportion of 2% by weight.

[0389] [ka]

[0390] NI=87.1℃;η=21.7mPa·s;Δn=0.071;Δε=5.9.

[0391] [Usage example 15] 3-HH-V (2-1) 30% 3-HH-V1 (2-1) 10% 3-HHB-1 (3-1) 5% V-HHB-1 (3-1) 3% 3-HBB-2 (3-4) 6% V2-BB(F)B-1 (3-6) 5% 3-HHEH-3 (3-13) 3% 3-HHEH-5 (3-13) 3% 1V2-BB-F (5-1) 3% 3-BB(F,F)XB(F,F)-F (6-97) 4% 3-GB(F,F)XB(F,F)-F (6-113) 3% 3-HHBB(F,F)-F (7-6) 3% 3-HB(F,F)XB(F,F)-F (7-38) 3% 3-BB(F)B(F,F)XB(F)-F (7-46) 4% 4-BB(F)B(F,F)XB(F,F)-F (7-47) 2% 5-BB(F)B(F,F)XB(F,F)-F (7-47) 3% 3-GB(F)B(F,F)XB(F,F)-F (7-57) 3% 4-GB(F)B(F,F)XB(F,F)-F (7-57) 5% 5-GB(F)B(F,F)XB(F,F)-F (7-57) 2% To the above composition, the following compound (1-2-213) was added in a proportion of 3% by weight.

[0392] [ka]

[0393] NI=81.9℃;η=13.5mPa·s;Δn=0.092;Δε=5.8.

[0394] [Usage example 16] 2-HH-5 (2-1) 2% 3-HH-4 (2-1) 7% 5-B(F)BB-2 (3-8) 4% 5-HB-CL (5-2) 11% 3-HHB(F,F)-F (6-3) 8% 3-HHEB(F,F)-F (6-12) 5% 4-HHEB(F,F)-F (6-12) 8% 5-HHEB(F,F)-F (6-12) 3% 3-HB(F,F)-F (6-24) 20% 5-HBB(F,F)-F (6-24) 15% 2-HBEB(F,F)-F (6-39) 3% 3-HBEB(F,F)-F (6-39) 3% 5-HBEB(F,F)-F (6-39) 5% 3-HHBB(F,F)-F (7-6) 6% To the above composition, the following compound (1-3-8) was added in a proportion of 2% by weight.

[0395] [ka]

[0396] NI=77.1℃;η=22.4mPa·s;Δn=0.108;Δε=8.5. [Industrial Applicability]

[0397] A liquid crystal composition containing the compound (1) can be used in display devices such as liquid crystal projectors and liquid crystal televisions.

Claims

1. A compound represented by any one of formulas (1-22), (1-23), (1-25), (1-26), (1-28) to (1-30), (1-33), (1-37), (1-38), (1-40), (1-41), (1-43), and (1-44). 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 In formulas (1-22), (1-23), (1-25), (1-26), (1-28) to (1-30), (1-33), (1-37), (1-38), (1-40), (1-41), (1-43), and (1-44), R １ is alkyl having 1 to 10 carbon atoms; Z １ From Z ３ are independently a single bond; Sp １ is independently a single bond or an alkylene having 1 to 5 carbon atoms, １ In the above, at least one -CH ２ - may be replaced by -O-; Y １ is independently fluorine; Y １１ From Y ２１ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, alkenyl having 2 to 5 carbons, or alkoxy having 1 to 4 carbons; Sp ２ is a single bond or an alkylene having 1 to 7 carbon atoms, ２ In the above, at least one -CH ２ - may be replaced by -O- or a group represented by formula (1-a), and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1); 【Chemistry 43】 【Chemistry 44】 Sp ３ and Sp ４ is independently a single bond or an alkylene having 1 to 5 carbon atoms, ３ and Sp ４ In the above, at least one -CH ２ - may be replaced by -O-; X １ is a polar group represented by any one of formulas (X-20) and (X-24); 【Chemical 44A】 In formula (X-24), J ４ is hydrogen or alkyl having 1 to 8 carbon atoms.

2. A liquid crystal composition comprising at least one compound according to claim 1.

3. 3. The liquid crystal composition according to claim 2, comprising at least one compound selected from the group of compounds represented by formulas (2) to (4): 【Chemistry 45】 In the formulas (2) to (4), R １１ and R １２ are independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, １１ and R １２ In the above, at least one -CH ２ - may be replaced by -O-, and at least one hydrogen may be replaced by fluorine; Ring B １ , ring B ２ , ring B ３ , and ring B ４ is independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, or pyrimidine-2,5-diyl; Z １１ , Z １２ , and Z １３ are independently a single bond, -COO-, -(CH ２ ) ２ -, -CH=CH-, or -C≡C-.

4. 4. The liquid crystal composition according to claim 2, comprising at least one compound selected from the group of compounds represented by formulas (5) to (7): 【Chemistry 46】 In the formulas (5) to (7), R １３ is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, １３ In the above, at least one -CH ２ - may be replaced by -O-, and at least one hydrogen may be replaced by fluorine; X １１ is fluorine, chlorine, -OCF ３ , -OCHF ２ , -CF ３ , -CHF ２ , -CH ２ F, -OCF ２ CHF ２ , or -OCF ２ CHFCF ３ and Ring C １ , ring C ２ , and ring C ３ are independently 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or 1,4-phenylene in which at least one hydrogen is replaced by fluorine; Z １４ , Z １５ , and Z １６ are independently a single bond, —COO—, —OCO—, or —CH ２ O-, -OCH ２ -, -CF ２ O-, -OCF ２ -, -(CH ２ ) ２ -, -CH=CH-, -C≡C-, or -(CH ２ ) ４ - and L １１ and L １２ are independently hydrogen or fluorine.

5. The liquid crystal composition according to claim 2 , comprising at least one compound selected from the group of compounds represented by formula (8): 【Chemistry 47】 In formula (8), R １４ is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, １４ In the above, at least one -CH ２ - may be replaced by -O-, and at least one hydrogen may be replaced by fluorine; X １２ is -C≡N or -C≡C-C≡N; Ring D １ is 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or 1,4-phenylene in which at least one hydrogen has been replaced by fluorine; Z １７ represents a single bond, -COO-, -OCO-, -CH ２ O-, -OCH ２ -, -CF ２ O-, -OCF ２ -, -(CH ２ ) ２ - or -C≡C-; L １３ and L １４ are independently hydrogen or fluorine; i is 1, 2, 3, or 4.

6. The liquid crystal composition according to claim 2 , comprising at least one compound selected from the group of compounds represented by formulas (11) to (19): 【Chemistry 48】 In the formulas (11) to (19), R １５ , R １６ , and R １７ are independently alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, １５ , R １６ , and R １７ In the above, at least one -CH ２ - may be replaced by -O-, at least one hydrogen may be replaced by fluorine, and R １７ may be hydrogen or fluorine; Ring E １ , ring E ２ , ring E ３ , and ring E ４ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, decahydronaphthalene-2,6-diyl, or 1,4-phenylene in which at least one hydrogen has been replaced by fluorine; Ring E ５ and Ring E ６ is independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl; Z １８ , Z １９ , Z ２０ , and Z ２１ each independently represents a single bond, —COO—, or —OCO— , -CH ２ O-, -OCH ２ -, -CF ２ O-, -OCF ２ -, -(CH ２ ) ２ -, -CF ２ O-(CH ２ ) ２ - or -OCF ２ - (CH ２ ) ２ - and L １５ and L １６ is independently fluorine or chlorine; S １１ is hydrogen or methyl; X is -CHF- or -CF ２ - and j, k, m, n, p, q, r, and s are independently 0 or 1, the sum of k, m, n, and p is 1 or 2, and the sum of q, r, and s is 0, 1, 2, or 3; t is 1, 2, or 3.

7. The liquid crystal composition according to claim 2 , which contains at least one polymerizable compound represented by formula (20) other than the compound represented by formula (1). 【Chemistry 49】 In formula (20), Ring F and ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxan-2-yl, pyrimidin-2-yl, or pyridin-2-yl, in which at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen; Ring G 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, phenanthrene, cyclohexyl, ... Z ２２ and Z ２３ are independently a single bond or an alkylene having 1 to 10 carbon atoms; ２２ and Z ２３ In the above, at least one -CH ２ - may be replaced by -O-, -CO-, -COO-, or -OCO-, and at least one -(CH ２ ) ２ - is -CH=CH-, -C(CH ３ )=CH-, -CH=C(CH ３ ) - or -C(CH ３ )=C(CH ３ )-, and at least one hydrogen may be replaced by fluorine or chlorine; P １１ , P １２ , and P １３ are independently a polymerizable group; Sp １１ , Sp １２ , and Sp １３ are independently a single bond or an alkylene having 1 to 10 carbon atoms, １１ , Sp １２ , and Sp １３ In the above, at least one -CH ２ - may be replaced by -O-, -COO-, -OCO-, or -OCOO-, and at least one -(CH ２ ) ２ - may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine; u is 0, 1, or 2; f, g, and h are independently 0, 1, 2, 3, or 4, and the sum of f, g, and h is 1 or greater. 【Chemical 49A】 In formula (1), R 1 is hydrogen or alkyl having 1 to 15 carbon atoms, in which at least one -CH 2 - may be replaced by -O- or -S-, at least one -(CH 2 ) 2 - may be replaced by -CH═CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine; Ring A 1 and ring A 2 are independently 1,2-cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,4-cyclohexylene, 1,4-cycloheptylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, and ring A 1 and ring A 2 in which at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or alkenyloxy having 2 to 9 carbons, and in these substituents, at least one hydrogen may be replaced by fluorine or chlorine; a is 0, 1, 2, 3, or 4; b and c are independently 0, 1, or 2; Z 1 is independently a single bond or alkylene having 1 to 6 carbon atoms, in which at least one -CH 2 - may be replaced by -O-, -CO-, -COO-, -OCO- or -OCOO-, at least one -(CH 2 ) 2 - may be replaced by -CH═CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine; P 1 and P 2 are independently a group selected from the groups represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) and formula (1-p5); 【Chemistry 49B】 In formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) and formula (1-p5), Sp 1 is independently a single bond or alkylene having 1 to 15 carbon atoms, in which at least one -CH 2 - may be replaced by -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH 2 ) 2 - may be replaced by -CH═CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine; R 2 is independently alkyl having 1 to 5 carbon atoms; R 3 is independently a linear alkyl having 1 to 10 carbon atoms or a branched alkyl having 3 to 10 carbon atoms, or a cyclic alkyl having 3 to 8 carbon atoms; Y 1 is independently chlorine, fluorine, or bromine; In formula (1), Sp 2 is a single bond or an alkylene having 1 to 10 carbon atoms, in which at least one -CH 2 - may be replaced by -O-, -CO-, -COO-, -OCO-, -OCOO- or a group represented by formula (1-a), at least one -(CH 2 ) 2 - may be replaced by -CH═CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) or formula (1-p5); 【Chemistry 49C】 X 1 is a polar group having a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, phosphorus and silicon; When at least one of P 1 and P 2 has at least one group selected from the groups represented by formula (1-p1), formula (1-p2), and formula (1-p3), Sp 2 is a single bond or an alkylene having 1 to 10 carbon atoms, in which at least one -CH 2 - may be replaced by -O-, -CO-, -COO-, -OCO-, -OCOO- or a group represented by formula (1-a), at least one -(CH 2 ) 2 - may be replaced by -CH═CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) or formula (1-p5); When neither P 1 nor P 2 has a group represented by formula (1-p1), formula (1-p2), or formula (1-p3), Sp 2 is an alkylene having 1 to 10 carbon atoms, in which at least one -CH 2 - is replaced by a group represented by formula (1-a), at least one -CH 2 - may be replaced by -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH 2 ) 2 - may be replaced by -CH═CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine, chlorine, or a group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) or formula (1-p5).

8. In formula (20), P １１ , P １２ , and P １３ The liquid crystal composition according to claim 7, wherein each of the formulas (P-1) to (P-5) is independently a group selected from the group of polymerizable groups represented by the formulas (P-1) to (P-5). 【Chemistry 50】 In formulas (P-1) to (P-5), M １１ , M. １２ , and M １３ are independently 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 halogen.

9. The liquid crystal composition according to claim 7 or 8, wherein the polymerizable compound represented by formula (20) is at least one compound selected from the group of polymerizable compounds represented by formulas (20-1) to (20-7): 【Chemistry 51】 In the formulas (20-1) to (20-7), L ３１ , L ３２ , L ３３ , L ３４ , L ３５ , L ３６ , L ３７ , and L ３８ are independently hydrogen, fluorine, or methyl; Sp １１ , Sp １２ , and Sp １３ are independently a single bond or an alkylene having 1 to 10 carbon atoms, １１ , Sp １２ , and Sp １３ In the above, at least one -CH ２ - may be replaced by -O-, -COO-, -OCO-, or -OCOO-, and at least one -(CH ２ ) ２ - may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine. P １１ , P １２ , and P １３ are independently a group selected from the group of polymerizable groups represented by formulas (P-1) to (P-3), 【Chemistry 52】 In formulas (P-1) to (P-3), M １１ , M. １２ , and M １３ are independently 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 halogen.

10. 8. The liquid crystal composition according to claim 7, comprising at least one selected from the group consisting of a polymerizable compound different from the compound represented by formula (1) or formula (20), a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, a dye, and an antifoaming agent.

11. A liquid crystal display element comprising at least one selected from the group consisting of the liquid crystal composition according to any one of claims 2 to 10 and a liquid crystal composition obtained by at least partially polymerizing the liquid crystal composition according to any one of claims 2 to 10.

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