JP7597021B2 - Compound, liquid crystal composition, and liquid crystal display device - Google Patents

Description

The present invention relates to a compound, a liquid crystal composition, and a liquid crystal display element. More specifically, the present invention relates to a compound having both a polymerizable group such as methoxymethacryloyloxy and a polar group such as an -OH group, a liquid crystal composition containing this compound and having positive or negative dielectric anisotropy, and a liquid crystal display element containing this composition or a cured product of a portion thereof.

Liquid crystal display elements can be classified into 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), FPA (field-induced photo-reactive alignment), etc., based on the operation mode of the liquid crystal molecules. In addition, they can be classified into PM (passive matrix) and AM (active matrix) based on the driving method of the element. PM is classified into static, multiplex, etc., and AM is classified into TFT (thin film transistor), MIM (metal insulator metal), etc. Furthermore, TFT can be classified into amorphous silicon and polycrystal silicon. The latter is 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.

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.

The properties of the composition will be further explained based on a commercially available AM element. 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 element 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 even 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.

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.

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 has been 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 orientation of the liquid crystal molecules by the polymer, thereby shortening the response time of the element and improving image sticking. Such effects of the polymer can be expected in elements having modes such as TN, ECB, OCB, IPS, VA, FFS, and FPA.

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, a mode has been proposed in which a polar compound is added to a liquid crystal composition to align the liquid crystal molecules as a liquid crystal display element without an alignment film. First, a composition to which a small amount of a polar compound and a small amount of a polymerizable compound have been added is injected into the element. A polymerizable compound having multiple polymerizable groups is generally used as the polymerizable compound. 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 that sandwich the element. Here, the polymerizable compound polymerizes and stabilizes 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, the process of forming an alignment film is not necessary. Since there is no alignment film, the electrical resistance of the element does not decrease due to the interaction between the alignment film and the composition. Such an effect achieved by the combination of a polar compound and a polymer can be expected in elements having modes such as TN, ECB, OCB, IPS, VA, FFS, and FPA.

Up until now, polymerizable polar compounds have been synthesized as compounds that combine 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) that has multiple polar groups and multiple polymerizable groups.

International Publication No. 2016/129490 International Publication No. 2017/209161

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 large voltage holding ratio when used in a liquid crystal display element, and having high solubility in a liquid crystal composition. The second object is to provide a liquid crystal composition containing this compound and satisfying at least one of the following characteristics: a high upper limit temperature of the nematic phase, a low lower limit temperature of the 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 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.

The present invention relates to a compound represented by formula (1), a liquid crystal composition containing this compound, and a liquid crystal display element containing this composition and/or a polymer in which at least a portion of this composition is polymerized.

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 ^A1 and ring ^A2 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; In ² , at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 10 carbon atoms, alkenyl having 2 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms, 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;
^P1 and ^P2 are independently a group selected from the group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) and formula (1-p5);

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;
^R2 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 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);

^X1 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).

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 large 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 this compound and satisfying at least one of the following characteristics: a high upper limit temperature of the nematic phase, a low lower limit temperature of the 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.

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.
The term "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.

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 proportion (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 proportion (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. In other words, the proportion 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 proportion of the polymerization initiator and the polymerization inhibitor in the liquid crystal composition is exceptionally expressed based on the weight of the polymerizable compound.

The "clearing point" is the transition temperature of a liquid crystal compound between the liquid crystal phase and the isotropic phase. The "lower limit temperature of the liquid crystal phase" is the transition temperature of a solid-liquid crystal phase (such as a smectic phase or a nematic phase) in a liquid crystal compound. The "upper limit temperature of the nematic phase" is the transition temperature of a 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 becomes large. The "large voltage holding ratio" means that the element has a large voltage holding ratio not only at room temperature but also at temperatures 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 temperatures close to the upper limit temperature. The characteristics of compositions and elements may be examined before and after aging tests (including accelerated aging tests). 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.

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).
Symbols A ¹ , B ¹ , C ¹ , etc. enclosed in a hexagon correspond to ring A ¹ , ring B ¹ , ring C ¹ , etc. The hexagon represents a six-membered ring such as a cyclohexane ring or a benzene ring, or a fused ring such as a naphthalene ring. A line crossing one side of the hexagon represents that any hydrogen on the ring may be replaced with a group such as -Sp ¹ -P ¹ .
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.

In the chemical formula of a compound, the symbol of the terminal group R ¹¹ is used for a plurality of compounds, and the groups represented by R ¹¹ in these compounds may be the same or different. For example, when R ¹¹ in compound (2) is ethyl, R ¹¹ in compound (3) may be ethyl or other groups such as propyl. This rule also applies to other symbols. In compound (8), when i is 2, there are two rings D ^1. In this compound, the two groups represented by the two rings D ¹ may be the same or different. When i is greater than 2, any two rings D ¹ may be used. This rule also applies to other symbols.

The expression "at least one 'A'" means that the number of 'A' is arbitrary. The expression "at least one 'A' may be replaced with 'B'" 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 arbitrary. The rule that the replacement position is arbitrary 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 that it includes the case where A is not replaced, the case where at least one A is replaced with B, the case where at least one A is replaced with C, and the case where at least one A is replaced with D, and further the case where multiple A are replaced with at least two of B, C, and D. For example, alkyl in which at least one -CH ₂ - (or -(CH ₂ ) ₂ -) may be replaced by -O- (or -CH═CH-) includes alkyl, alkenyl, alkoxy, alkoxyalkyl, alkoxyalkenyl, and alkenyloxyalkyl. It is not preferred that two consecutive -CH ₂ - are replaced by -O- to give -O-O-. It is also not preferred that -CH ₂ - in the methyl portion (-CH ₂ -H) in alkyl, etc. is replaced by -O- to give -O-H.

The expression "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 -CH ₂ - may be replaced by -O-, and in which at least one hydrogen may be replaced by fluorine" is sometimes used. 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.

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, the fluorine may be left-facing (L) or right-facing (R). This rule also applies to asymmetric divalent groups generated by removing two hydrogens from a ring, such as tetrahydropyran-2,5-diyl.

The present invention includes the following items, etc.

Item 1. A compound represented by formula (1).

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 ^A1 and ring ^A2 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; In ² , at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 10 carbon atoms, alkenyl having 2 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms, 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;
^P1 and ^P2 are independently a group selected from the group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) and formula (1-p5);

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;
^R2 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 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);

^X1 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).

Item 2. The compound described in item 1, wherein the polar group is represented by any one of formulas (X-1) to (X-27).

In formulas (X-1) to (X-27),
J ¹ and J ² are independently hydrogen, or linear alkyl having 1 to 5 carbon atoms or branched alkyl having ³ to ⁵ carbon atoms, in which at least one -CH ₂ - may be replaced by -O-;
J ³ is hydrogen, or a linear alkyl having 1 to 20 carbon atoms or a branched alkyl having ³ to 20 carbon atoms, in which at least one -CH ₂ - 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 methine or nitrogen, where the hydrogen of the methine may be replaced by alkyl having 1 to 6 carbon atoms; U ¹ and U ² are independently -CH ₂ -, -O-, -CO- or -S-;
V ¹ , V ² and V ³ are independently methine or nitrogen, and at least one of V ¹ , V ² and V ³ contains nitrogen;
W ¹ is -O- or -S-;
^W2 is carbon, sulfur or silicon.
However, when Q ¹ in formula (X-14) is a methine group, at least one of U ¹ and U ² is —O—, —CO— or —S—.

Item 3. A compound according to item 1 or 2, represented by any one of formulas (1-1) to (1-8).

In formulas (1-1) to (1-8),
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 ^A1 to Ring ^A5 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, 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 to Z ⁴ are independently a single bond, -(CH ₂ ) ₂ -, -CH=CH-, -C≡C-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -CH ₂ O-, -OCH ₂ -, or -CF=CF-;
^P1 and ^P2 are independently a group selected from the group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) and formula (1-p5);

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 an alkylene having 1 to 7 carbon atoms, in which at least one -CH ₂ - may be replaced by -O-, -CO- or -COO-, at least one -(CH ² ) ₂ - may be replaced by -CH═CH-, and at least one hydrogen may be replaced _by fluorine or chlorine;
^R2 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 is 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, in which at least one -CH ₂ ^- may be replaced by -O-, -CO-, -COO- or a group represented by formula (1-a), at least one -(CH ₂ ) 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);

^X1 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 7 carbon atoms, in which at least one -CH ² _- may be replaced by -O-, -CO-, -COO-, or a group represented by formula (1-a), at least one -(CH ₂ ) 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);
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 ⁷ 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-, or -COO-, at least one -(CH ₂ ) 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).

Item 4. A compound according to any one of items 1 to 3, represented by any one of formulas (1-9) to (1-16).

In the formulas (1-9) to (1-16),
R ¹ is hydrogen or alkyl having 1 to 10 carbon atoms, in ^which at least one -CH ₂ - may be replaced by -O-, at least one -(CH ₂ ) ₂ - may be replaced by -CH═CH-, and at least one hydrogen may be replaced by fluorine or chlorine;
Ring ^A1 to ring ^A5 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 in these rings ^A1 to ^A5 , 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 to Z ⁴ are independently a single bond, -(CH ₂ ) ₂ -, -CH=CH-, -C≡C-, -CH ₂ O-, or -OCH ₂ -;
^P1 and ^P2 are independently a group selected from the group represented by formula (1-p1), formula (1-p2) and formula (1-p3);

In formula (1-p1), formula (1-p2) and formula (1-p3),
Sp ¹ is independently a single bond or an alkylene having 1 to 5 carbon atoms, in ^which at least one -CH ₂ - may be replaced by -O-, at least one -(CH ₂ ) ₂ - may be replaced by -CH═CH-, and at least one hydrogen may be replaced by fluorine or chlorine;
^R2 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 is 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, in ^which 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 or chlorine;

^X1 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) each have at least one group selected from the groups represented by formulas (1-p1), (1-p2), and (1-p3).

Item 5. A compound according to any one of items 1 to 4, represented by any one of formulas (1-17) to (1-145).

In formulas (1-17) to (1-145),
R ¹ is an alkyl group having 1 to 10 carbon atoms;
Z ¹ to Z ³ are independently a single bond or -(CH ₂ ) ₂ -;
Sp ¹ is independently a single bond or alkylene having 1 to 5 carbon atoms, in ^which at least one -CH ₂ - may be replaced by -O-;
^R2 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 is independently chlorine, fluorine, or bromine;
Y ¹¹ to 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, in ^which 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), formula (1-p2), formula (1-p3) or formula (1-p4);

Sp ³ and Sp ⁴ are independently a ^single bond or an alkylene having 1 to ⁵ carbon atoms, in which at least one -CH ₂ - may be replaced by -O-;
^X1 is a polar group having a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, phosphorus and silicon.

Item 6. A liquid crystal composition containing at least one of the compounds described in any one of items 1 to 5.

Item 7. A liquid crystal composition according to item 6, containing at least one compound selected from the group of compounds represented by formulas (2) to (4).

In the formulas (2) to (4),
R ¹¹ and R ¹² are independently alkyl having 1 to 10 carbons or alkenyl having 2 to ^{10 carbons} , in which 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 are 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—.

Item 8. A liquid crystal composition according to item 6 or 7, containing at least one compound selected from the group of compounds represented by formulas (5) to (7).

In the formulas (5) to (7),
R ¹³ is alkyl having 1 to 10 carbons or alkenyl having 2 to ¹⁰ carbons, in which at least one -CH ₂ - may be replaced by -O-, and at least one hydrogen may be replaced by fluorine;
^X11 is 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-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₂ -, -CH═CH-, -C≡C- or -(CH ₂ ) ₄ -;
L ¹¹ and L ¹² are independently hydrogen or fluorine.

Item 9. A liquid crystal composition according to any one of items 6 to 8, containing at least one compound selected from the group of compounds represented by formula (8).

In formula (8),
R ¹⁴ is alkyl having 1 to 10 carbons or alkenyl having 2 to ¹⁰ carbons, in which at least one -CH ₂ - may be replaced by -O-, and at least one hydrogen may be replaced by fluorine;
^X12 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 is replaced by fluorine;
Z ¹⁷ is 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.

Item 10. A liquid crystal composition according to any one of items 6 to 9, containing at least one compound selected from the group of compounds represented by formulas (11) to (19).

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, in which 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 is replaced by fluorine;
Ring ^E5 and Ring ^E6 are 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-, -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 -;
L ¹⁵ and L ¹⁶ are independently fluorine or chlorine;
S ¹¹ is hydrogen or methyl;
X is -CHF- or -CF ₂ -;
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.

Item 11. A liquid crystal composition according to any one of items 6 to 10, containing at least one polymerizable compound represented by formula (20) other than the compound represented by formula (1).

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, in which at least one -CH ₂ - may be replaced by -O-, -CO-, -COO-, or -OCO-, at least one -(CH ² ) ₂ - may be replaced by -CH═CH-, -C(CH ₃ )═CH-, -CH═C(CH ³ ) _{═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, in which at least one -CH ₂ ^- may be replaced by -O-, -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;
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.

Item 12. In formula (20),
Item 12. The liquid crystal composition according to item 11, wherein 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).

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.

Item 13. A 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 of polymerizable compounds represented by formulas (20-1) to (20-7).

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, and in these Sp ¹¹ , Sp ¹² , and Sp ¹³ , at least one -CH ₂ - may be replaced by -O-, -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 ¹¹ , P ¹² , and P ¹³ are independently a group selected from the group of polymerizable groups represented by formulae (P-1) to (P-3),

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.

Item 14. A liquid crystal composition according to any one of items 6 to 13, containing 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.

Item 15. A liquid crystal display element 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 polymerizing at least a portion of the liquid crystal composition according to any one of items 6 to 14.

The present invention also includes the following items.
(a) The above liquid crystal composition further containing 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 the compound (1) or the 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 prepared 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.

Below, the aspects of compound (1), the synthesis of compound (1), the liquid crystal composition, and the liquid crystal display element are described in order.

1. Aspects of Compound (1) 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 an -OH group. 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 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. Compound (1) satisfies these characteristics to a considerable extent, and has an extremely high solubility in a liquid crystal composition that could not be achieved with conventional compounds, and by using 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.

Preferred examples of compound (1) will be explained. Preferred examples of symbols such as R ¹ , A ¹ , and Sp ² in compound (1) also apply to sub-formulas of compound (1), such as formula (1-1). In compound (1), the properties can be adjusted as desired by appropriately combining the types of these groups. Compound (1) may contain isotopes such as ² H (deuterium) and ¹³ C in amounts greater than the natural abundance ratio, since there is no significant difference in the properties of the compound.

R ¹ is hydrogen or alkyl having 1 to 15 carbon atoms, and in this R ¹ , 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.

Preferred R ¹ is hydrogen or alkyl having 1 to 10 carbon atoms, in which at least one -CH ₂ ^- may be replaced by -O-, at least one -(CH ₂ ) ₂ - may be replaced by -CH═CH-, and at least one hydrogen may be replaced by fluorine or chlorine.
More preferably, R ¹ is alkyl having 1 to 10 carbon atoms.

A compound in which R ¹ is an alkyl group having 1 to 15 carbon atoms has high chemical stability. A compound in which R ¹ is an alkyl group having 1 to 15 carbon atoms has high solubility in a liquid crystal composition. A compound in which R ¹ is an alkyl group having 1 to 15 carbon atoms has a high ability to align liquid crystal molecules.

Ring ^A1 and ring ^A2 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; In ² , at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 10 carbon atoms, alkenyl having 2 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms, and in these substituents, at least one hydrogen may be replaced by fluorine or chlorine.

Preferred ring ^A1 and ring ^A2 are 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4 ^- phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5-diyl, 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.

More preferred ring ^A1 and ring ^A2 are 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5-diyl, in which 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.

Particularly preferred ring ^A1 and ring ^A2 are 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.

A compound in which ring A ¹ and ring A ² 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 has high chemical stability. A compound in which ring A ¹ and ring A ² 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 has high solubility in a liquid crystal composition. A compound in which ring ^A1 and ring ^A2 are independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is replaced by alkyl having 1 to 2 carbon atoms has a high ability to align liquid crystal molecules. A compound in which ring ^A1 and ring ^A2 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 a high polymerization reactivity when irradiated with ultraviolet light.

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.

Compounds in which a is 0 have high solubility in liquid crystal compositions. Compounds in which a is 3 or 4 have a high ability to align liquid crystal molecules. Compounds in which a is 1 or 2 have high solubility in liquid crystal compositions, a high ability to align liquid crystal molecules, and high polymerization reactivity when exposed to ultraviolet light.

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.

A compound in which the sum of b and c is 1 or more has a polymerizable group in ring A ¹ or ring A ^2. In this case, the compound has high polymerization reactivity when irradiated with ultraviolet light.

Z ¹ is independently a single bond or an alkylene having 1 to 6 carbon atoms, and in this Z ¹ , 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.

Preferred Z ¹ is a single bond, -(CH ₂ ) ₂ -, -CH=CH-, -C≡C-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -CH ₂ O-, -OCH ₂ - or -CF=CF-.
Z ¹ is more preferably a single bond, —(CH ₂ ) ₂ —, —CH═CH—, —C≡C—, —CH ₂ O—, or —OCH ₂ —, still more preferably ^a single bond or —(CH ₂ ) ₂ —, and particularly ^preferably a single bond.

A compound in which Z ¹ is a single bond has high chemical stability. A compound in which Z ¹ is a single bond, -(CH ₂ ) ₂ -, -CF ₂ O-, or -OCF ₂ - has high solubility in a liquid crystal composition. A compound in which ^{Z 1} is a single bond or -(CH ₂ ) ₂ - has a high ability to align liquid crystal molecules. A compound in which ^{Z 1} is a single bond, -CH=CH-, -C≡C-, -COO-, -OCO-, -CH ₂ O-, or -OCH ₂ - has high polymerization reactivity when irradiated with ultraviolet light.

^P1 and ^P2 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), and preferably, at least one of ^P1 and ^P2 has at least one group selected from the groups represented by formula (1-p1), formula (1-p2) and formula (1-p3).
Preferred ^P1 and ^P2 are groups selected from the groups represented by formula (1-p1), formula (1-p2) and formula (1-p3).

Compounds in which at least one of ^P1 and ^P2 is a group represented by formula (1-p1), formula (1-p2), or formula (1-p3) have high solubility.

Sp ¹ is independently a single bond or an alkylene having 1 to 15 carbon atoms, and in this Sp ¹ , 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.

Preferred Sp ¹ is a single bond or an alkylene having 1 to 7 carbon atoms, in ^which at least one -CH ₂ - may be replaced by -O-, -CO- or -COO-, at least one -(CH ₂ ) ₂ - may be replaced by -CH═CH-, and at least one hydrogen may be replaced by fluorine or chlorine.

More preferably, Sp ¹ is a single bond or an alkylene having 1 to 5 carbon atoms, in ^which at least one -CH ₂ - may be replaced by -O-, at least one -(CH ₂ ) ₂ - may be replaced by -CH═CH-, and at least one hydrogen may be replaced by fluorine or chlorine.
More preferably, Sp ¹ is a single bond or alkylene having 1 to 5 carbon atoms, in ^which at least one -CH ₂ - may be replaced by -O-.

A compound in which Sp ¹ is independently a single bond or an alkylene having 1 to 7 carbon atoms has high chemical stability. A compound in which Sp ¹ is independently an alkylene having 1 to 7 carbon atoms or a group in which at least one —CH ₂ — in an alkylene having 1 to 7 carbon atoms is replaced with —O— has high solubility in a liquid crystal composition.

^R2 is independently an alkyl group having 1 to 5 carbon atoms. ^R2 preferably has 1 to 3 carbon atoms. More preferably, ^R2 has 1 carbon atom. In this case, the reactivity is high, and the ability to align liquid crystal molecules and the voltage holding ratio can be maintained when used in a liquid crystal display element.

^R3 is independently a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, or a cyclic alkyl group having 3 to 8 carbon atoms. ^R3 preferably has 1 to 5 carbon atoms. More preferably, ^R3 has 1 carbon atom, in which case the reactivity is high, and the ability to align liquid crystal molecules and the voltage holding ratio can be maintained when used in a liquid crystal display element.

Y ¹ is independently chlorine, fluorine or bromine. Preferred Y ¹ is fluorine. When Y ¹ is fluorine, the solubility is high.

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) or formula (1-p4).
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).
However, 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).

Preferred Sp ² is a single bond or an alkylene having 1 to 7 carbon atoms, in which at least one -CH ₂ ^- may be replaced by -O-, -CO-, -COO- or a group represented by formula (1-a), at least one -(CH ₂ ) 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).

More preferably, Sp ² is a single bond or an alkylene having 1 to 7 carbon atoms, in ^which 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 or chlorine.
More preferably, Sp ² is a single bond or alkylene having 1 to 7 carbon atoms, in ^which at least one -CH ₂ - may be replaced by -O- or a group represented by formula (1-a).

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

^X1 is a polar group having a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, phosphorus and silicon.

Preferred ^X1 is a polar group represented by any one of formulas (X-1) to (X-27).

In formulas (X-1) to (X-27),
J ¹ and J ² are independently hydrogen, or linear alkyl having 1 to 5 carbon atoms or branched alkyl having 3 to 5 carbon atoms, and in J ¹ and J ² , at least one -CH ₂ - may be replaced by -O-.
J ³ is hydrogen, or linear alkyl having 1 to 20 carbon atoms or branched alkyl having 3 to 20 carbon atoms, and in this J ³ , at least one -CH ₂ - may be replaced by -O-, -COO- or -OCO-.
J ⁴ and J ⁵ are independently hydrogen or alkyl having 1 to 8 carbon atoms;
^Q1 is a methine or nitrogen, where the hydrogen of the methine may be replaced by alkyl having 1 to 6 carbon atoms.
U ¹ and U ² are independently —CH ₂ —, —O—, —CO— or —S—.
V ¹ , V ² and V ³ are independently methine or nitrogen, and at least one of V ¹ , V ² and V ³ contains nitrogen.
W ¹ is —O— or —S—.
^W2 is carbon, sulfur or silicon.
However, when Q ¹ in formula (X-14) is a methine group, at least one of U ¹ and U ² is —O—, —CO— or —S—.

More preferably, X ¹ is -OH, -NH ₂ , -OR ⁴ , -N(R ⁴ ) ₂ , -COOH, -SH, or -Si(R ⁴ ) ₃ .
From the viewpoint of obtaining a compound having superior solubility in a liquid crystal composition, X ¹ is more preferably --OH, --NH ₂ or --SH, and particularly preferably ^--OH .
Here, R ⁴ is hydrogen or alkyl having 1 to 10 carbon atoms, and in this R ⁴ , at least one -CH ₂ - may be replaced by -O-, at least one -(CH ₂ ) ₂ - may be replaced by -CH═CH-, and at least one hydrogen may be replaced by fluorine or chlorine.

A compound in which ^X1 is -OH, _-NH2 , or -SH has a high ability to align liquid crystal molecules. A compound in which ^X1 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 element, and a high solubility in a liquid crystal composition.

In addition, preferred compound (1) has at least one group represented by formula (1-p1), formula (1-p2), and formula (1-p3).

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

2. Synthesis of Compound (1) A method for synthesizing compound (1) will be described. Compound (1) can be synthesized by appropriately combining methods of organic synthetic chemistry. 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).

2-1. Formation of a Bonding Group An example of a method for forming a bonding 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. The monovalent organic groups represented by multiple MSG ¹ (or MSG ² ) may be the same or different. Compounds (1A) to (1H) correspond to compound (1) or intermediates of compound (1).

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

(II) Formation of -COO- and -OCO- Compound (23) is reacted with n-butyllithium 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.

(III) Formation of -CF ₂ O- and -OCF ₂ - 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 -CF ₂ O-. 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 -OCF ₂ - can also be synthesized by this method.

(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 generated, and the cis isomer may be isomerized to a trans isomer by a known method, as necessary.

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

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

(VII) Formation of -CH ₂ O- and -OCH ₂ - Compound (27) is reduced with sodium borohydride to obtain compound (30), which is then brominated with hydrobromic acid to obtain compound (31). Compound (25) and compound (31) are reacted in the presence of potassium carbonate to synthesize compound (1G). Compounds having -OCH ₂ - can also be synthesized by this method.

(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).

2-2. Formation of Rings ^A1 and ^A2 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.

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

A compound (1-X51) having the formula (1), in which the polar group is the 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 obtain compound (52). Compound (52) is reacted in the presence of pyridinium p-toluenesulfonate (PPTS) and 3,4-dihydro-2H-pyran to obtain 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 lead to compound (1-X51).

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 preferably contains compound (1) as component A and further contains at least one liquid crystal compound selected from the following components B, C, D, and E. Component B is compound (2) to (4). Component C is compound (5) to (7) other than compounds (2) to (4). Component D is compound (8). Component E is compound (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 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 or small elastic constant).

Compound (1) is added to the composition for the purpose of controlling the alignment of the 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 it is easy to align the liquid crystal molecules, and is preferably 10% by weight or less, since it is possible to prevent display defects of the element. 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).

Component B is a compound in which the two terminal groups are alkyl or the like. Component B has a small dielectric anisotropy. Preferable 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, and in this R ¹¹ and R ¹² , at least one -CH ₂ - may be replaced by -O-, and at least one hydrogen may be replaced by fluorine.

Component B is a nearly neutral compound because the absolute value of the dielectric anisotropy is small. 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.

As the content of component B increases, the dielectric anisotropy of the composition decreases, but the viscosity decreases. For this reason, 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.

Component C is a compound having fluorine, chlorine or a fluorine-containing group at at least one terminal. 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 having 1 to 10 carbon atoms or an alkenyl having 2 to 10 carbon atoms, in which 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 .}

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 10% by weight to 97% by weight, and more preferably 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.

Component D is compound (8) having one terminal group of -C≡N or -C≡C-C≡N. Component D has a cyano group and therefore has a positively large dielectric anisotropy. Preferable examples of component D include compounds (8-1) to (8-64). In the compound of component D, R ¹⁴ is alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms, in which 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.

Component D has a positive, large dielectric anisotropy and is therefore primarily used when preparing compositions for modes such as TN. By adding component D, the dielectric anisotropy of the composition can be increased. Component D has the effect of broadening 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.

The content of component D 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 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 is possible to adjust the elastic constant of the composition and adjust the voltage-transmittance curve of the element.

Component E is the 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. Preferable 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, in ^which at ^least one -CH ₂ - may be replaced with -O-, at least one hydrogen may be replaced with fluorine, and R ¹⁷ may be hydrogen or ^fluorine .

Component E has a large negative dielectric anisotropy. Component E is suitable for use in preparing compositions for modes such as IPS, VA, and PSA. As the content of component E is increased, the dielectric anisotropy of the composition becomes larger in the negative direction, but the viscosity also increases. For this reason, as long as the required value of the threshold voltage of the element is satisfied, a small content is preferable. Considering that the dielectric anisotropy is about -5, in order to ensure 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.

Of component E, compound (11) is a two-ring compound, and therefore has the effect of lowering 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 therefore has the effect of increasing the maximum temperature, increasing optical anisotropy, or increasing dielectric anisotropy. Compounds (15) to (19) have the effect of increasing dielectric anisotropy.

The content of component E is preferably 40% by weight or more, and 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 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 is possible to adjust the elastic constant of the composition and adjust the voltage-transmittance curve of the element.

By appropriately combining the above-mentioned components B, C, D, and E, a liquid crystal composition can be prepared that 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.

3-2. Additives The liquid crystal composition is prepared by a known method. For example, the components are mixed and then 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.

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 orientation of the liquid crystal molecules, and an appropriate pretilt angle is obtained, thereby shortening the response time.

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.

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 carbon atoms, alkoxy having 1 to 12 carbon atoms, or alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by halogen.

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.

In 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 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.

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.

In formula (20), Z ²² and Z ²³ are independently a single bond or an alkylene having 1 to 10 carbon atoms, and in this Z ²² and Z ²³ , at least one -CH ₂ - may be replaced by -O-, -CO-, -COO-, or -OCO-, at least one -(CH ₂ ) ₂ - may be replaced by -CH=CH-, -C(CH ₃ )=CH-, -CH=C(CH 3 )=C(CH ₃ )-, or -C(CH ₃ )=C(CH ₃ )-, and at least one hydrogen may be replaced by fluorine or chlorine. Preferred Z ²² or Z ²³ is a single bond, -(CH ₂ ) ₂ -, -CH ₂ O-, -OCH ₂ -, -COO-, or -OCO-. More preferred Z ²² or Z ²³ is a single bond.

In compound (20), P ¹¹ , P ¹² and P ¹³ are independently a polymerizable group. Preferred P ¹¹ to P 13 are groups selected from the group of polymerizable groups represented by formulae (P-1) to (P-5). More preferred P ¹¹ to P ¹³ are groups represented by formulae (P-1), (P-2) or (P-3). Particularly preferred P ¹¹ to P ¹³ are groups represented by formula (P-1). Preferred groups represented by formula (P-1) are acryloyloxy ( ^-OCO -CH=CH ₂ ) or methacryloyloxy (-OCO-C(CH ₃ )=CH ₂ ). The wavy lines in formulae (P-1) to (P-5) indicate the bonding site.

In formulae (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. M ¹¹ , M ¹² or M ¹³ is preferably hydrogen or methyl for increasing reactivity. More preferably, M ¹¹ is hydrogen or methyl, and more preferably, M ¹² or M ¹³ is hydrogen.

In formula (20), Sp ¹¹ , Sp ¹² and Sp ¹³ are independently a single bond or an alkylene having 1 to ¹⁰ carbon atoms, in which at least one -CH ₂ - may be replaced by -O-, ^-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. Preferred Sp ¹¹ , Sp ¹² and Sp ¹³ are single bonds.

In formula (20), u is 0, 1, or 2. Preferably, u is 0 or 1.

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. The preferred sum is 2, 3, or 4. The more preferred sum is 2 or 3.

Preferred examples of compound (20) are compounds (20-1) to (20-7) described in item 13 and compounds (20-8) to (20-11) described later. 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 to R ³¹ are independently hydrogen or methyl; R ³² , R ³³ , and R ³⁴ are independently hydrogen or alkyl having 1 to 5 carbon atoms, and at least one of R ³² , R ³³ , and R ³⁴ is 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 to L ³⁶ are independently hydrogen or fluorine, and L ³⁷ and L ³⁸ are independently hydrogen, fluorine, or methyl.

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 remaining polymerizable compound can be reduced by optimizing the reaction conditions during polymerization. Examples of photoradical polymerization initiators include TPO, 1173, and 4265 from the Darocure series of BASF Corporation, and 184, 369, 500, 651, 784, 819, 907, 1300, 1700, 1800, 1850, and 2959 from the Irgacure series.

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, and benzophenone/methyltriethanolamine mixture.

After adding a photoradical polymerization initiator to the liquid crystal composition, polymerization can be carried out 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 burn-in on the element. To prevent this, photopolymerization may be carried out 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.

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.

The optically active compound has the effect of preventing reverse twisting by inducing a helical structure in the liquid crystal molecules and imparting a 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 represents an asymmetric carbon.

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): Irganox 415, Irganox 565, Irganox 1010, Irganox 1035, Irganox 3114, and Irganox 1098 (product names; BASF Corporation).
The ultraviolet absorber is effective in preventing a decrease in the maximum temperature. Preferred examples of the ultraviolet absorber include benzophenone derivatives, benzoate derivatives, and triazole derivatives, 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 names; BASF Corporation); and 1,4-diazabicyclo[2.2.2]octane (DABCO).

A light stabilizer such as a sterically hindered amine is preferred in order 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 Irgafos 168 (product name; BASF Corporation).
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 as necessary.
The antifoaming agent is effective in preventing foaming. Preferred examples of the antifoaming agent include dimethyl silicone oil and methyl phenyl silicone oil.

In compound (AO-1), R ⁴⁰ is alkyl having 1 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, -COOR ⁴¹ , or -(CH ₂ ) ₂ -COOR ⁴¹ , where R ⁴¹ is alkyl having 1 to 20 carbon atoms. In compounds (AO-2) and (AO-5), R ⁴² is alkyl 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 is 1,4-cyclohexylene, 1,4-phenylene, or a group in which at least one hydrogen of 1,4-phenylene is replaced by fluorine; and in compounds (AO-5) and (AO-7), z is 1, 2, or 3.

4. Liquid crystal display element The liquid crystal composition has an operation mode such as PC, TN, STN, OCB, PSA, etc., and can be suitably used in a liquid crystal display element driven by an active matrix method. The composition has an operation mode such as PC, TN, STN, OCB, VA, IPS, etc., and can be suitably used in a liquid crystal display element driven by a passive matrix method. These elements can be applied to any of the reflective, transmissive, and semi-transmissive types.

The composition is also suitable for NCAP (nematic curvilinear aligned phase) elements, where the composition is microencapsulated. The 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 type of reflection type, transmission type, or semi-transmission type.

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.

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 oriented 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. In addition, 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.

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

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

NMR analysis: A DRX-500 manufactured by Bruker Biospin was used for the measurement. In the measurement of ¹ H-NMR, the sample was dissolved in a deuterated solvent such as CDCl ₃ , and the measurement was performed under the conditions of room temperature, 500 MHz, and 16 times of accumulation. Tetramethylsilane was used as an internal standard. In the measurement of ¹⁹ F-NMR, CFCl ₃ 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.

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) part 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.

HPLC analysis: Shimadzu Corporation's Prominence (LC-20AD; SPD-20A) was used for the measurements. 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% by weight solution, and 1 μL of this solution was introduced into the sample chamber. Shimadzu Corporation's C-R7Aplus was used as the recorder.

UV-Visible Spectroscopic Analysis: Measurements were performed using a PharmaSpec UV-1700 manufactured by Shimadzu Corporation. The detection wavelengths were 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.

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

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

(1) Phase structure A sample was placed on the 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 a polarizing microscope, and the type of phase was identified.

(2) Transition temperature (°C)
For the measurements, a scanning calorimeter, Diamond DSC System, manufactured by PerkinElmer, or a high-sensitivity differential scanning calorimeter, X-DSC7000, manufactured by Hitachi High-Tech Science, Ltd., 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 obtained by extrapolation 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 a 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".

Crystals were represented as C. When the types of crystals could be distinguished, they were represented as _C1 , _C2 , etc. Smectic phases were represented as S, and nematic phases as N. When the smectic phases could be distinguished into smectic A phase, smectic B phase, smectic C phase, or smectic F phase, they were represented as S _A , S _B , S _C , or S _F, respectively. Liquids (isotropic) were represented as I. Transition temperatures were represented 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.

(3) Maximum temperature of nematic phase (T _NI or NI; ° C.)
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 was a mixture of compound (1) and mother liquid crystals, it was indicated by the symbols 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 symbols NI.

(4) Minimum temperature of nematic phase (T _C ; ° C.)
Samples having a nematic phase were stored in freezers at 0°C, -10°C, -20°C, -30°C, and -40°C for 10 days, and then the liquid crystal phase was observed. For example, when a sample remained in a nematic phase at -20°C and changed to a crystal or smectic phase at -30°C, the T _C was recorded as ≦-20°C. The lowest temperature of the nematic phase is sometimes abbreviated as "lower limit temperature".

(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.

(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⊥.

(7) Specific resistance (ρ; measured at 25° C.; Ωcm)
1.0 mL of the 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)}.

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

(8a) Viscosity (rotational viscosity; γ1; measured at 25° C.; mPa s)
Positive dielectric anisotropy: The measurement was performed according to the method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). The 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 in the range of 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 voltage application were measured. The value of the rotational viscosity was obtained from these measured values 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 obtained by the method described below using the device in which the rotational viscosity was measured.

(8b) Viscosity (rotational viscosity; γ1; measured at 25° C.; mPa s)
Negative dielectric anisotropy: The 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 VA element with a cell gap of 20 μm between two glass substrates. Voltage was applied to this element in steps of 1 volt at a time in the range of 39 to 50 volts. After 0.2 seconds of no voltage application, voltage application was repeated 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 voltage application were measured. The value of rotational viscosity was obtained from these measured values 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 measured in the section on dielectric anisotropy below.

(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⊥.

(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 with 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 washed 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 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.

(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. A sample was placed in a horizontally aligned element with a cell gap between two glass substrates of 20 μm. 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 formulas (2.98) and (2.101) on page 75 of "Liquid Crystal Device Handbook" (Nikkan Kogyo Shimbun), and the values of _K11 and _K33 were obtained from formula (2.99). Next, _K22 was calculated using the previously obtained values of _K11 and _K33 in formula (3.18) on page 171. The elastic constant K was expressed as the average value of _K11 , _K22 , and _K33 thus obtained.

(10b) Elastic constants ( _K11 and _K33 ; measured at 25°C; pN)
Negative dielectric anisotropy: An EC-1 elastic constant measuring device manufactured by Toyo Corporation was used for the measurement. A sample was placed in a vertical alignment element with a distance (cell gap) between two glass substrates of 20 μm. A charge of 20 volts to 0 volts was applied to this element, and the capacitance and applied voltage were measured. The values of capacitance (C) and applied voltage (V) were fitted using formulas (2.98) and (2.101) on page 75 of "Liquid Crystal Device Handbook" (The Nikkan Kogyo Shimbun), and the value of the elastic constant was obtained from formula (2.100).

(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. A sample was placed in a normally white mode TN element in which the distance (cell gap) between two glass substrates was 0.45/Δn (μm) and the twist angle was 80 degrees. The voltage (32 Hz, square wave) applied to this element was increased stepwise by 0.02 V from 0 V to 10 V. At this time, light was irradiated from the vertical direction to the element, 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 90%.

(11b) Threshold voltage (Vth; measured at 25° C.; V)
Negative 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. A sample was placed in a normally black mode VA element in which the distance (cell gap) between two glass substrates was 4 μm and the rubbing direction was anti-parallel, 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%.

(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 element in which the distance (cell gap) between two glass substrates was 5.0 μm and the twist angle was 80 degrees. A square wave (60 Hz, 5 V, 0.5 seconds) was applied to this element. At this time, light was irradiated from the vertical direction to measure the amount of light transmitted through the element. 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.

(12b) Response time (τ; measured at 25° C.; ms)
Negative 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 black mode PVA element in which the distance (cell gap) between two glass substrates was 3.2 μm and the rubbing direction was anti-parallel. The element was sealed using an adhesive that hardens with ultraviolet light. A voltage slightly exceeding the threshold voltage was applied to the element for 1 minute, and then ultraviolet light of 23.5 mW/cm ² was irradiated for 8 minutes while applying a voltage of 5.6 V. A square wave (60 Hz, 10 V, 0.5 seconds) was applied to the element. At this time, light was irradiated from the vertical direction to the element, and the amount of light transmitted through the element was measured. The maximum amount of light was considered to be 100% transmittance, and the minimum amount of light was considered to be 0% transmittance. The response time was expressed as the time required for the transmittance to change from 90% to 10% (fall time; milliseconds).

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

Raw Materials 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.

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

First 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%).

Second step: Put known compound (T-3) (72.1 g) and tetrahydrofuran (THF) (500 ml) into a reactor, add n-butyllithium (1.6 mol/L, hexane solution) (185.7 ml) dropwise at -70°C, and stir at -70°C for 1 hour. Add a THF solution (150 ml) of compound (T-4) (50.0 g) dropwise thereto, and stir for 5 hours while raising the temperature 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%).

Third step: 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%).

Fourth 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%).

Fifth 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. This 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%).

Sixth 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%).

Seventh Step Compound (T-10) (63.7 g), sodium hydrogen carbonate (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 resulting 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-11) (42.0 g; 65%).

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%).

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%).

Tenth 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 the mixture was 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%).

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%).

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%).

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 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=1:1) to obtain compound (1-3-30) (6.6 g; 70%).

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

First 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%).

Second Step 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 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=2:1) to obtain compound (T-20) (8.4 g; 70%).

Third step 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 the mixture was 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%).

Fourth 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 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=1:1) to obtain compound (1-3-70) (5.4 g; 70%).

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

First 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%).

Second Step 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 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=1:3) to obtain compound (T-24) (14.2 g; 78%).

Third step 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, followed by stirring for 12 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. 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%).

The NMR analysis values of the obtained compound (1-3-267) are as follows.
¹ H-NMR: Chemical shift δ (ppm; CDCl ₃ ): 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), 4.29-4.26 (m, 6H), 4.1 9-4.16 (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°C)

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

¹ H-NMR (ppm; CDCl ₃ ): 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).

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

The proportions of the components of composition (i) are expressed as weight percent.

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

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) precipitated crystals 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 believed to be 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.

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), (1-2-1) to (1-2-256), (1-3-1) to (1-3-276), and (1-4-1) to (1-4-155).

2. Examples of Compositions 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 ratio (percentage) of the liquid crystal compound is the weight percentage (wt%) based on the weight of the liquid crystal composition. Finally, the property values of the liquid crystal compositions are summarized. The properties were measured according to the methods described above, and the measured values are listed as they are (without extrapolation).

[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.

NI=80.8°C; η=10.8 mPa·s; Δn=0.130; Δε=6.6.

[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-HBBXB(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.

NI=78.0°C; η=12.1 mPa·s; Δn=0.097; Δε=5.5.

[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.

NI=95.6°C; η=17.9 mPa·s; Δn=0.107; Δε=5.1.

[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.

NI=85.1°C; η=25.3 mPa·s; Δn=0.111; Δε=5.7.

[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-HBB(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.

NI=70.6°C; η=20.8 mPa·s; Δn=0.115; Δε=6.0.

[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.

NI=84.6°C; η=19.3 mPa·s; Δn=0.102; Δε=5.6.

[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.

NI=86.0°C; η=14.6 mPa·s; Δn=0.092; Δε=4.3.

[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.

NI=81.5°C; η=13.3 mPa·s; Δn=0.106; Δε=7.3.

[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-HBB(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.

NI=106.7°C; η=32.6 mPa·s; Δn=0.123; Δε=8.3.

[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.

NI=114.4°C; η=18.7 mPa·s; Δn=0.091; Δε=3.7.

[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.

NI=71.9°C; η=14.1 mPa·s; Δn=0.075; Δε=2.9.

[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.

NI=83.5°C; η=16.6 mPa·s; Δn=0.098; Δε=6.2.

[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.

NI=72.8°C; η=25.0 mPa·s; Δn=0.098; Δε=8.2.

[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.

NI=87.1°C; η=21.7 mPa·s; Δn=0.071; Δε=5.9.

[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-HBB(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.

NI=81.9°C; η=13.5 mPa·s; Δn=0.092; Δε=5.8.

[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-HBB(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.

NI=77.1°C; η=22.4 mPa·s; Δn=0.108; Δε=8.5.

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

Claims (11)

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).
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 an alkyl group having 1 to 10 carbon atoms;
Z ¹ to Z ³ are independently a single bond;
Sp ¹ is independently a single bond or alkylene having 1 to 5 carbon atoms, in ^which at least one -CH ₂ - may be replaced by -O-;
Y ¹ is independently fluorine;
Y ¹¹ to 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, in ^which 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);
Sp ³ and Sp ⁴ are independently a ^single bond or an alkylene having 1 to ⁵ carbon atoms, in which at least one -CH ₂ - may be replaced by -O-;
^X1 is a polar group represented by any one of formulas (X-20) and (X-24);
In formula (X-24),
J ⁴ is hydrogen or alkyl having 1 to 8 carbon atoms. A liquid crystal composition containing at least one of the compounds according to claim 1. 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):
In the formulas (2) to (4),
R ¹¹ and R ¹² are independently alkyl having 1 to 10 carbons or alkenyl having 2 to ^{10 carbons} , in which 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 are 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. 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):
In the formulas (5) to (7),
R ¹³ is alkyl having 1 to 10 carbons or alkenyl having 2 to ¹⁰ carbons, in which at least one -CH ₂ - may be replaced by -O-, and at least one hydrogen may be replaced by fluorine;
^X11 is 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-, -CH ₂ O-, -OCH ₂ -, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₂ -, -CH═CH-, -C≡C- or -(CH ₂ ) ₄ -;
L ¹¹ and L ¹² are independently hydrogen or fluorine. The liquid crystal composition according to claim 2 , comprising at least one compound selected from the group of compounds represented by formula (8):
In formula (8),
R ¹⁴ is alkyl having 1 to 10 carbons or alkenyl having 2 to ¹⁰ carbons, in which at least one -CH ₂ - may be replaced by -O-, and at least one hydrogen may be replaced by fluorine;
^X12 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 is replaced by fluorine;
Z ¹⁷ is 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. 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):
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, in which 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 is replaced by fluorine;
Ring ^E5 and Ring ^E6 are 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 are independently fluorine or chlorine;
S ¹¹ is hydrogen or methyl;
X is -CHF- or -CF ₂ -;
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. 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).
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, in which at least one -CH ₂ - may be replaced by -O-, -CO-, -COO-, or -OCO-, at least one -(CH ² ) ₂ - may be replaced by -CH═CH-, -C(CH ₃ )═CH-, -CH═C(CH ³ ) _{═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, in which at least one -CH ₂ ^- may be replaced by -O-, -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;
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.
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 A1 ^and ring A2 ^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 ^; In ² , at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 10 carbon atoms, alkenyl having 2 to 10 carbon atoms, alkoxy having 1 to 9 carbon atoms, or alkenyloxy having 2 to 9 carbon atoms, 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;
P1 and P2 ^are independently a group selected from the group represented by formula (1-p1), formula (1-p2), formula (1-p3), formula (1-p4) and formula (1-p5) ^;
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;
R2 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 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);
X1 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). In formula (20),
8. The liquid crystal composition according to claim 7, wherein 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).
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. 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):
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, and in these Sp ¹¹ , Sp ¹² , and Sp ¹³ , at least one -CH ₂ - may be replaced by -O-, -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 ¹¹ , P ¹² , and P ¹³ are independently a group selected from the group of polymerizable groups represented by formulae (P-1) to (P-3),
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. 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. 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 polymerizing at least a portion of the liquid crystal composition according to any one of claims 2 to 10.