TW202104557A - Compound, liquid-crystal composition, and liquid-crystal display element - Google Patents

Abstract

A compound represented by formula (1). R1 is, for example, an alkyl having 1-15 carbon atoms; ring A1 and ring A2 are 1,4-phenylene, etc.; a is 2, etc.; b and c are 0, 1, or 2; Z1 is a single bond, etc.; P1 and P2 are polymerizable groups; and Sp2 is, for example, an alkylene having 1-10 carbon atoms; and X1 is a group selected from among groups represented by formula (1-x1) to formula (1-x10).

Description

Compound, liquid crystal composition and liquid crystal display element

The present invention relates to a compound, a liquid crystal composition and a liquid crystal display element. In more detail, the present invention relates to a compound having both a polymerizable group and a specific polar group having a cyclic structure, a liquid crystal composition containing the compound and having a positive or negative dielectric anisotropy, and a composition containing the same Or a part of hardened liquid crystal display element.

If liquid crystal display elements are classified based on the operation mode of liquid crystal molecules, they can be classified into phase change (PC), twisted nematic (TN), super twisted nematic (STN), Electrically controlled birefringence (ECB), optically compensated bend (OCB), in-plane switching (IPS), vertical alignment (VA), fringe field switching, FFS), field-induced photo-reactive alignment (FPA) and other modes. In addition, based on the driving method of the element, it can be classified into a passive matrix (PM) and an active matrix (AM). PM is classified into static, multiplexed, etc., and AM is classified into thin film transistor (TFT), metal insulator metal (MIM), etc. Furthermore, TFTs can be classified into amorphous silicon and polycrystal silicon. The latter is classified into a high-temperature type and a low-temperature type according to the manufacturing steps. If it is classified based on the light source, it can be classified into a reflective type using natural light, a transmissive type using backlight, and a semi-transmissive type using both natural light and backlight.

The liquid crystal composition having a nematic phase has appropriate characteristics. By improving the characteristics of the composition, an AM device with good characteristics can be obtained. The correlation between the characteristics of the composition and the characteristics of the AM device is summarized in Table 1 below.

Table 1. Characteristics of composition and AM device To serial number Characteristics of the composition Characteristics of AM components 1 Wide temperature range of nematic phase Wide range of usable temperature 2 Low viscosity ^{1 )} Short response time 3 Appropriate optical anisotropy High contrast 4 Large positive or negative dielectric anisotropy Low threshold voltage, low power consumption High contrast 5 Specific resistance High voltage retention rate and high contrast ratio 6 Stable to UV and heat long life 7 Large elastic constant High contrast and short response time 1) The time to inject the composition into the liquid crystal display element can be shortened

The characteristics of the composition will be further described based on commercially available AM devices. The temperature range of the nematic phase (the temperature range in which the nematic phase is present) is related to the usable temperature range of the element. The preferable upper limit temperature of the nematic phase is about 70°C or higher, and the preferable lower limit temperature of the nematic phase is about -10°C or lower. The viscosity of the composition is related to the response time of the device. In order to display dynamic images with components, it is preferable that the response time be short. Ideally, the response time is shorter than 1 millisecond. Therefore, it is preferable that the viscosity of the composition is low, and furthermore, it is more preferable that the viscosity of the composition is low even at a low temperature.

The optical anisotropy of the composition is related to the contrast of the device. Depending on the mode of the element, it is necessary that the optical anisotropy is large or small, that is, the optical anisotropy is appropriate. 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. The appropriate value of the product depends on the type of operation mode. In TN and other mode devices, the value is about 0.45 μm. In the VA mode device, the value is in the range of about 0.30 μm to about 0.40 μm, and in the IPS mode or FFS mode device, the value is in the range of about 0.20 μm to about 0.30 μm. In these cases, a composition having a large optical anisotropy is preferable for an element with a small cell gap. The large dielectric anisotropy in the composition contributes to low threshold voltage, small power consumption, and large contrast ratio in the device. Therefore, a large positive or negative dielectric anisotropy is preferable. The large specific resistance in the composition contributes to a large voltage holding ratio and a large contrast ratio in the element. Therefore, it is preferably a composition having a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase in the initial stage. It is preferably a composition having a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase after long-term use. The stability of the composition to ultraviolet rays and heat is related to the life of the device. When the 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, and the like.

In a polymer sustained alignment (PSA) type liquid crystal display element, a liquid crystal composition containing a polymer is used. First, a composition containing a small amount of polymerizable compound is injected into the device. Here, a polymerizable compound having a plurality of polymerizable groups is usually used. Then, while applying a voltage between the substrates sandwiching the element, the composition was irradiated with ultraviolet rays. The polymerizable compound is polymerized to form a polymer network structure in the composition. If this composition is used, the alignment of the liquid crystal molecules can be controlled by the polymer, so the response time of the device is shortened, and the burn mark of the image is improved. Devices with modes such as TN, ECB, OCB, IPS, VA, FFS, FPA, etc. can expect this effect of polymers.

In general liquid crystal display devices, the vertical alignment of liquid crystal molecules can be achieved by polyimide alignment films. On the other hand, as a liquid crystal display element without an alignment film, a mode in which a polar compound is added to a liquid crystal composition to align liquid crystal molecules has been proposed. First, a composition containing a small amount of a polar compound and a small amount of a polymerizable compound is injected into the device. As the polymerizable compound, a polymerizable compound having a plurality of polymerizable groups is usually used. Here, the liquid crystal molecules are aligned by the action of the polar compound. Then, while applying a voltage between the substrates sandwiching the element, the composition was irradiated with ultraviolet rays. Here, the polymerizable compound is polymerized and stabilizes the alignment of liquid crystal molecules. If this composition is used, the alignment of liquid crystal molecules can be controlled by polar compounds and polymers, so the response time of the device is shortened, and the burn mark of the image can be improved. Furthermore, an element without an alignment film does not require a step of forming an alignment film. Since there is no alignment film, the resistance of the device does not decrease due to the interaction between the alignment film and the composition. Devices with modes such as TN, ECB, OCB, IPS, VA, FFS, FPA, etc. can be expected to utilize this effect of the combination of polar compounds and polymers.

Hitherto, in liquid crystal display elements without an alignment film, as a compound having both the function of a polar compound and the function of a polymerizable compound, a polymerizable polar compound has been synthesized (for example, Patent Document 1 and Patent Document 2). Patent Document 1 includes a polymerizable polar compound (S-1).

[現有技術文獻] [專利文獻]

[Prior Art Document] [Patent Document]

[Patent Document 1] International Publication No. 2016/129490 [Patent Document 2] International Publication No. 2017/209161

[The problem to be solved by the invention] The first subject of the present invention is to provide a compound that has high thermal stability, high chemical stability, high ability to align liquid crystal molecules, high polymerization reactivity caused by ultraviolet radiation, and large It is at least one of the voltage holding ratio when used in a liquid crystal display element, and has high solubility in the liquid crystal composition. The second problem is to provide a liquid crystal composition that contains the compound and satisfies the requirements of high nematic phase upper limit temperature, low nematic phase lower limit temperature, low viscosity, appropriate optical anisotropy, and positive or negative dielectric properties. At least one of the characteristics of high anisotropy, high specific resistance, high stability to ultraviolet rays, and large elastic constant. The third issue is to provide a liquid crystal display element that has the characteristics of a wide temperature range of usable elements, short response time, high transmittance, high voltage retention, low threshold voltage, high contrast, long life, and good vertical alignment. At least one of. [Means to solve the problem]

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

In formula (1), R ¹ is hydrogen or an alkyl group having 1 to 15 carbons. In R ¹ , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one -(CH ₂ ) ₂ -May be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; ring A ¹ and ring A ^{2 are} independently 1,2-cyclopropylidene, 1,3-idene Cyclobutyl, 1,3-cyclopentyl, 1,4-cyclohexylene, 1,4-cycloheptyl, 1,4-cyclohexenyl, 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 the ring A ¹ and ring A ² , at least one hydrogen can be fluorine, chlorine , Alkyl with 1 to 10 carbons, alkenyl with 2 to 10 carbons, alkoxy with 1 to 9 carbons or alkenyloxy with 2 to 9 carbons, at least one hydrogen may be substituted with fluorine or chlorine; a is 3 or 4; b and c are independently 0, 1 or 2; Z ¹ is independently a single bond or alkylene group having a carbon number 1 to 6, in which Z ^1, at least one - CH ₂ -can be substituted by -O-, -CO-, -COO-, -OCO- or -OCOO-, at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, At least one hydrogen may be substituted by fluorine or chlorine; P ¹ and P ^{2 are} independently groups selected from the groups represented by formula (1-p1) and formula (1-p2);

In formula (1-p1) and formula (1-p2), Sp ^{1 is} independently a single bond or an alkylene group having 1 to 15 carbon atoms, and in this Sp ¹ , at least one -CH ₂ -may be -O-, -CO-, -COO-, -OCO- or -OCOO- substituted, at least one -(CH ₂ ) ₂ -can be replaced by -CH=CH- or -C≡C-, at least one hydrogen can be replaced by fluorine or chlorine ; M ¹ and M ^{2 are} independently hydrogen, fluorine, chlorine, an alkyl group of 1 to 5 carbons, or an alkyl group of 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine; Y ^{1 is} independently hydrogen, C1-C10 alkyl group, C1-C9 alkoxy group, C2-C9 alkoxyalkyl group, C1-C9 alkylthio group or C2-C9 alkylthio group Alkyl group, in the Y ¹ , at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by bromine, fluorine or chlorine; R ^{2 is} independently carbon A straight chain alkyl group having a number of 1 to 10 or a branched chain alkyl group having a carbon number of 3 to 10, or a cyclic alkyl group having a carbon number of 3 to 8; in formula (1), Sp ² is a single bond or a carbon number of 1 to 10 At least one -CH ₂ -in the Sp ² may be substituted by -O-, -CO-, -COO-, -OCO-, -OCOO- or a group represented by formula (1-a), At least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine, chlorine, or a group represented by formula (1-p1) or formula (1-p2) replace;

X ¹ is a group selected from groups represented by formula (1-x1) to formula (1-x10);

In formulas (1-x1) to (1-x10), W ¹ is a methine group or nitrogen, where the hydrogen of the methine group may be substituted with an alkyl group having 1 to 6 carbon atoms; m1 is independently 0, 1 or 2, in the -(CH ₂ ) _m1 -, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; W ² Is a methine group or nitrogen, where the hydrogen of the methine group can be substituted by an alkyl group having 1 to 6 carbons; K ¹ is an alkylene group having 1 or 2 carbons, and in this K ¹ , at least one -CH ₂ -May be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; K ² is carbon In the alkylene group of 1 or 2, in the K ² , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; n1 is 2 or 3, the -( Among CH ₂ ) _n1 -, at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine or chlorine; K ^{3 is} independently a carbon number 1. Alkylene, in the K ³ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; K ⁴ is -S- or -CO- ; K ⁵ independently an alkylene group of carbon number 1 or 2, K ⁵ in which at least one -CH ₂ - may be -O -, - CO- or -S-, at least one - (CH _{2) 2} -May be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; p1 is independently 0 or 1, in the -(CH ₂ ) _p1 -, at least one hydrogen may be substituted by fluorine or chlorine; K ⁶ alkylene group having a carbon number of 1's, in which K ^6, at least one -CH ₂ - may be substituted with -O- or -S-, may be at least one hydrogen replaced by fluorine or chlorine; K ⁷ is independently The ground is a single bond or an alkylene having 1 to 3 carbon atoms. In the K ⁷ , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; K ⁸ is Hydrogen or an alkyl group having 1 to 4 carbon atoms, in the K ⁸ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one -(CH ₂ ) ₂ -may be -CH =CH- or -C≡C- substitution, at least one hydrogen can be replaced by fluorine or chlorine; when p1 is all 0, a is 1, 2, 3 or 4. [Effects of the invention]

The first advantage of the present invention is to provide a compound that has high thermal stability, high chemical stability, high ability to align liquid crystal molecules, high polymerization reactivity caused by ultraviolet radiation, and large It is at least one of the voltage holding ratio when used in a liquid crystal display element, and has high solubility in the liquid crystal composition. The second advantage is to provide a liquid crystal composition that contains the compound, and satisfies the requirements of high nematic phase upper limit temperature, low nematic phase lower limit temperature, low viscosity, appropriate optical anisotropy, and positive or negative dielectric properties. At least one of the characteristics of high anisotropy, high specific resistance, high stability to ultraviolet rays, and large elastic constant. The third advantage is to provide a liquid crystal display element, which has the characteristics of a wide temperature range of the usable element, short response time, high transmittance, high voltage retention, low threshold voltage, large contrast, long life, and good vertical alignment. At least one of.

The usage of the terms in this manual is as follows. The terms "liquid crystal compound", "liquid crystal composition" and "liquid crystal display element" are sometimes abbreviated as "compound", "composition" and "device", respectively. A "liquid crystal compound" is a compound having a liquid crystal phase such as a nematic phase and a smectic phase. Although it does not have a liquid crystal phase, it is for the purpose of adjusting the physical properties of the composition such as the upper limit temperature, the lower limit temperature, the viscosity, and the dielectric anisotropy. The general term for the added compounds. 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 the composition. The liquid crystal compound having an alkenyl group is not a polymerizable compound in its significance. "Polar compounds" help the alignment of liquid crystal molecules through the interaction of polar groups with the surface of the substrate. "Liquid crystal display element" is the general term for liquid crystal display panels and liquid crystal display modules.

The liquid crystal composition is usually prepared by mixing a plurality of liquid crystal compounds. In this composition, for the purpose of further adjusting physical properties, a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, Additives such as pigments and defoamers. Regarding the ratio (content) of the liquid crystal compound in the liquid crystal composition, even when an additive is added, it is expressed as a weight percentage (weight %) based on the weight of the liquid crystal composition not containing the additive. The ratio (addition amount) of the additive in the liquid crystal composition is expressed as a weight percentage (weight %) based on the weight of the liquid crystal composition that does not contain the additive. That is, the ratio of the liquid crystal compound or the additive is calculated based on the total weight of the liquid crystal compound. Sometimes parts per million by weight (ppm) are also used. The ratio of the polymerization initiator and the polymerization inhibitor in the liquid crystal composition is exceptionally expressed based on the weight of the polymerizable compound.

The "clear point" is the transition temperature from the liquid crystal phase to the isotropic phase in the liquid crystal compound. The "lower limit temperature of the liquid crystal phase" is the transition temperature of the solid-liquid crystal phase (equal to smectic phase and nematic phase) in the liquid crystal compound. The "upper limit temperature of the nematic phase" is the transition temperature of the nematic-isotropic phase in the mixture of the liquid crystal compound and the mother liquid crystal or the liquid crystal composition, and may be simply referred to as the "upper limit temperature". Sometimes the "lower limit temperature of the nematic phase" is simply referred to as the "lower limit temperature". The expression "increased dielectric anisotropy" or "large dielectric anisotropy" means that the absolute value of its value increases or becomes larger. "High voltage holding rate" means that the device has a large voltage holding rate not only at room temperature but also at a temperature close to the upper limit temperature in the initial stage. Moreover, after the device is used for a long time, it is not only at room temperature, but also at room temperature. It also has a large voltage holding rate at a temperature close to the upper limit temperature. In the composition or element, the characteristics may be studied before and after the time-dependent change test (including the accelerated deterioration test). The expression "high solubility in a liquid crystal composition" means that the solubility is high relative to any composition containing a liquid crystal compound at room temperature, but as the composition, it can be used in the following examples The composition evaluated for solubility was used as a reference.

The compound represented by formula (1) may be abbreviated as "compound (1)". The compound (1) refers to one compound, a mixture of two compounds, or a mixture of three or more compounds represented by the formula (1). This rule also applies to at least one compound selected from the group of compounds represented by formula (2), etc. ^{Symbols such as A 1} , B ¹ , and C ¹ surrounded by hexagons correspond to ring A ¹ , ring B ¹ , and ring C ^1, etc., respectively. Hexagon represents a six-membered ring such as a cyclohexane ring or a benzene ring or a condensed ring such as a naphthalene ring. A straight line crossing one side of the hexagon indicates that any hydrogen on the ring may be substituted by a group such as ^{-Sp 1} -P ^1. Subscripts such as f, g, and h indicate the number of substituted groups. When the subscript is 0, there is no such substitution. In the expression "ring A and ring C are independently X, Y or Z", since there are multiple subjects, "independently" is used. When the subject is "Ring A is", since the subject is single, "independently" is not used.

In the chemical formula of the ^{compound, the symbol of the terminal group R 11} is used in a variety of compounds, but the ^{groups represented by R 11} in these compounds may be the same or different. For example, R in the compound (2) in the case where ¹¹ is ethyl, R compound (3) ¹¹ can be ethyl, propyl and the like may also be other groups. This rule also applies to other marks. 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, it is also applicable to any two rings D ¹ . This rule also applies to other marks.

The expression "at least one "A"" means that the number of "A"s is arbitrary. The expression "at least one'A' can be replaced by'B'" includes the case of'A' itself that is not replaced by'B', the case of one'A' being replaced by'B', and the case of two or more'A's being replaced by'B'. In the case of'B' substitution, in these cases, the position of'A' substituted with'B' is arbitrary. The rule that the substitution position is arbitrary also applies to the expression "at least one'A' is replaced by a'B'". The expression "at least one A can be substituted by B, C or D" refers to the case where A is not substituted, the case where at least one A is substituted by B, the case where at least one A is substituted by C, and the case where at least one A is substituted by D Cases, and cases where multiple A is replaced by at least two of B, C, and D. For example, at least one -CH _2- (or -(CH ₂ ) ₂ -) may be substituted with -O- (or -CH=CH-) in the alkyl group, including alkyl, alkenyl, alkoxy, alkoxy Alkyl, alkoxyalkenyl, alkenoxyalkyl. Furthermore, it is not good that two consecutive -CH ₂ -are replaced by -O- to become -OO-. -CH alkyl group, a methyl moiety (-CH ₂ -H) of ₂ - substituted -O- -OH case also becomes poor.

Sometimes it is used "R ¹¹ and R ^{12 are} independently an alkyl group having 1 to 10 carbons or an alkenyl group having 2 to 10 carbons, in which at least one -CH ₂ -may be substituted by -O- , In these groups, at least one hydrogen can be replaced by fluorine". In this expression, "these bases" can be interpreted as textually. In this expression, "these groups" refer to alkyl groups, alkenyl groups, alkoxy groups, alkenyloxy groups and the like. That is, "these bases" means all the bases described before the term "these bases". This common-sense explanation also applies to other terms.

Halogen refers to fluorine, chlorine, bromine or iodine. The preferred halogen is fluorine or chlorine. A particularly preferred halogen is fluorine. In the liquid crystal compound, the alkyl group is a straight-chain alkyl group or a branched-chain alkyl group, and does not include a cyclic alkyl group. Generally speaking, straight chain alkyl groups are preferred to branched chain alkyl groups. These conditions are also the same for terminal groups such as alkoxy and alkenyl. Regarding the three-dimensional configuration related to 1,4-cyclohexylene, in order to increase the upper limit temperature of the nematic phase, the trans configuration is better than the cis configuration. 2-Fluoro-1,4-phenylene refers to the following two divalent groups. In the chemical formula, fluorine can be left (L) or right (R). This rule also applies to tetrahydropyran-2,5-diyl and other divalent groups that are left and right asymmetrically generated by removing two hydrogens from the ring.

The present invention includes the following items and the like.

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

In formula (1), R ¹ is hydrogen or an alkyl group having 1 to 15 carbons. In R ¹ , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one -(CH ₂ ) ₂ -May be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; ring A ¹ and ring A ^{2 are} independently 1,2-cyclopropylidene, 1,3-idene Cyclobutyl, 1,3-cyclopentyl, 1,4-cyclohexylene, 1,4-cycloheptyl, 1,4-cyclohexenyl, 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 the ring A ¹ and ring A ² , at least one hydrogen can be fluorine, chlorine , Alkyl with 1 to 10 carbons, alkenyl with 2 to 10 carbons, alkoxy with 1 to 9 carbons or alkenyloxy with 2 to 9 carbons, at least one hydrogen may be substituted with fluorine or chlorine; a is 3 or 4; b and c are independently 0, 1 or 2; Z ¹ is independently a single bond or alkylene group having a carbon number 1 to 6, in which Z ^1, at least one - CH ₂ -can be substituted by -O-, -CO-, -COO-, -OCO- or -OCOO-, at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, At least one hydrogen may be substituted by fluorine or chlorine; P ¹ and P ^{2 are} independently groups selected from the groups represented by formula (1-p1) and formula (1-p2);

In formula (1-p1) and formula (1-p2), Sp ^{1 is} independently a single bond or an alkylene group having 1 to 15 carbon atoms, and in this Sp ¹ , at least one -CH ₂ -may be -O-, -CO-, -COO-, -OCO- or -OCOO- substituted, at least one -(CH ₂ ) ₂ -can be replaced by -CH=CH- or -C≡C-, at least one hydrogen can be replaced by fluorine or chlorine ; M ¹ and M ^{2 are} independently hydrogen, fluorine, chlorine, an alkyl group of 1 to 5 carbons, or an alkyl group of 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine; Y ^{1 is} independently hydrogen, C1-C10 alkyl group, C1-C9 alkoxy group, C2-C9 alkoxyalkyl group, C1-C9 alkylthio group or C2-C9 alkylthio group Alkyl group, in the Y ¹ , at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by bromine, fluorine or chlorine; R ^{2 is} independently carbon A straight chain alkyl group having a number of 1 to 10 or a branched chain alkyl group having a carbon number of 3 to 10, or a cyclic alkyl group having a carbon number of 3 to 8; in formula (1), Sp ² is a single bond or a carbon number of 1 to 10 At least one -CH ₂ -in the Sp ² may be substituted by -O-, -CO-, -COO-, -OCO-, -OCOO- or a group represented by formula (1-a), At least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine, chlorine, or a group represented by formula (1-p1) or formula (1-p2) replace;

X ¹ is a group selected from groups represented by formula (1-x1) to formula (1-x10);

In formulas (1-x1) to (1-x10), W ¹ is a methine group or nitrogen, where the hydrogen of the methine group may be substituted with an alkyl group having 1 to 6 carbon atoms; m1 is independently 0, 1 or 2, in the -(CH ₂ ) _m1 -, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; W ² Is a methine group or nitrogen, where the hydrogen of the methine group can be substituted by an alkyl group having 1 to 6 carbons; K ¹ is an alkylene group having 1 or 2 carbons, and in this K ¹ , at least one -CH ₂ -May be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; K ² is carbon In the alkylene group of 1 or 2, in the K ² , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; n1 is 2 or 3, the -( Among CH ₂ ) _n1 -, at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine or chlorine; K ^{3 is} independently a carbon number 1. Alkylene, in the K ³ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; K ⁴ is -S- or -CO- ; K ⁵ independently an alkylene group of carbon number 1 or 2, K ⁵ in which at least one -CH ₂ - may be -O -, - CO- or -S-, at least one - (CH _{2) 2} -May be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; p1 is independently 0 or 1, in the -(CH ₂ ) _p1 -, at least one hydrogen may be substituted by fluorine or chlorine; K ⁶ alkylene group having a carbon number of 1's, in which K ^6, at least one -CH ₂ - may be substituted with -O- or -S-, may be at least one hydrogen replaced by fluorine or chlorine; K ⁷ is independently The ground is a single bond or an alkylene having 1 to 3 carbon atoms. In the K ⁷ , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; K ⁸ is Hydrogen or an alkyl group having 1 to 4 carbon atoms, in the K ⁸ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one -(CH ₂ ) ₂ -may be -CH =CH- or -C≡C- substitution, at least one hydrogen can be replaced by fluorine or chlorine; when p1 is all 0, a is 1, 2, 3 or 4.

Item 2. The compound according to Item 1, which is represented by any one of formula (1-1) to formula (1-8).

In formulas (1-1) to (1-8), R ¹ is hydrogen or an alkyl group having 1 to 15 carbons, and in R ¹ at least one -CH ₂ -may be substituted with -O- or -S- , At least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; ring A ¹ to ring A ^{5 are} independently 1,4-extension Cyclohexyl, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane- 2,5-diyl, in the ring A ¹ to ring A ⁵ , at least one hydrogen can be fluorine, chlorine, C 1-10 alkyl, C 2-10 alkenyl, C 1-9 Alkoxy or alkenyloxy having 2 to 9 carbon atoms, at least one hydrogen may be substituted by fluorine or chlorine; b and c are independently 0, 1 or 2; Z ¹ to Z ^{4 are} independently single bonds, -( CH ₂ ) ₂ -, -CH=CH-, -C≡C-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -CH ₂ O-, -OCH ₂ -or -CF =CF-; P ¹ and P ^{2 are} independently groups selected from groups represented by formula (1-p1) and formula (1-p2);

In formula (1-p1) and formula (1-p2), Sp ^{1 is} independently a single bond or an alkylene having 1 to 7 carbon atoms, and in this Sp ¹ , at least one -CH ₂ -may be through -O-, -CO- or -COO- substitution, at least one -(CH ₂ ) ₂ -can be replaced by -CH=CH-, at least one hydrogen can be replaced by fluorine or chlorine; M ¹ and M ^{2 are} independently hydrogen, fluorine, chlorine , An alkyl group having 1 to 5 carbons, or an alkyl group having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine; Y ^{1 is} independently hydrogen, an alkyl group having 1 to 10 carbons, and a carbon number of 1 to 9 alkoxy, alkoxyalkyl having 2 to 9 carbons, an alkoxy group or alkylthio group having a carbon number of 2 to 9 carbon number of 1 to 9, in which Y ^1, at least one - (CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by bromine, fluorine or chlorine; R ^{2 is} independently a linear alkyl group having 1 to 10 carbons or a carbon number of 3 to A branched chain alkyl group of 10 or a cyclic alkyl group having 3 to 8 carbons; In formula (1-1) to formula (1-8), Sp ² is a single bond or an alkylene group having 1 to 7 carbons, In this Sp ² , at least one -CH ₂ -may be substituted by -O-, -CO-, -COO- or a group represented by formula (1-a), and at least one -(CH ₂ ) ₂ -may be -CH =CH- or -C≡C- substitution, at least one hydrogen may be substituted by fluorine, chlorine, or a group represented by formula (1-p1) or formula (1-p2);

X ¹ is a group selected from groups represented by formula (1-x1) to formula (1-x10);

In formulas (1-x1) to (1-x10), W ¹ is a methine group or nitrogen, where the hydrogen of the methine group may be substituted with an alkyl group having 1 to 6 carbon atoms; m1 is independently 0, 1 or 2, in the -(CH ₂ ) _m1 -, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; W ² Is a methine group or nitrogen, where the hydrogen of the methine group can be substituted by an alkyl group having 1 to 6 carbons; K ¹ is an alkylene group having 1 or 2 carbons, and in this K ¹ , at least one -CH ₂ -May be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; K ² is carbon In the alkylene group of 1 or 2, in the K ² , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; n1 is 2 or 3, the -( Among CH ₂ ) _n1 -, at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine or chlorine; K ^{3 is} independently a carbon number 1. Alkylene, in the K ³ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; K ⁴ is -S- or -CO- ; K ⁵ independently an alkylene group of carbon number 1 or 2, K ⁵ in which at least one -CH ₂ - may be -O -, - CO- or -S-, at least one - (CH _{2) 2} -May be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; p1 is independently 0 or 1, in the -(CH ₂ ) _p1 -, at least one hydrogen may be substituted by fluorine or chlorine; K ⁶ alkylene group having a carbon number of 1's, in which K ^6, at least one -CH ₂ - may be substituted with -O- or -S-, may be at least one hydrogen replaced by fluorine or chlorine; K ⁷ is independently The ground is a single bond or an alkylene having 1 to 3 carbon atoms. In the K ⁷ , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; K ⁸ is Hydrogen or an alkyl group having 1 to 4 carbon atoms, in the K ⁸ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one -(CH ₂ ) ₂ -may be -CH =CH- or -C≡C- substitution, at least one hydrogen can be replaced by fluorine or chlorine; In formula (1-1), there is no case where p1 in formula (1-x7) is 0.

Item 3. The compound according to Item 1 or Item 2, which is represented by any one of formula (1-9) to formula (1-16).

In formulas (1-9) to (1-16), R ¹ is hydrogen or an alkyl group having 1 to 10 carbons. In R ¹ , at least one -CH ₂ -may be substituted by -O-, and at least one- (CH ₂ ) ₂ -may be substituted by -CH=CH-, at least one hydrogen may be substituted by fluorine or chlorine; Ring A ¹ to Ring A ^{5 are} independently 1,4-cyclohexylene, 1,4-cyclohexylene Alkenyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl, the ring A ¹ to a ⁵ are, at least one hydrogen may be fluorine, an alkyl group of 1 to 5 carbon atoms, alkoxy or alkenyl having 2 to 5 carbon atoms, 1 to 4 substituents; B and c are independently 0 , 1 or 2; Z ¹ to Z ^{4 are} independently single bonds, -(CH ₂ ) ₂ -, -CH=CH-, -C≡C-, -CH ₂ O- or -OCH ₂ -; P ¹ and P ^{2 is} independently a group selected from groups represented by formula (1-p1) and formula (1-p2);

In formula (1-p1) and formula (1-p2), Sp ^{1 is} independently a single bond or an alkylene having 1 to 5 carbon atoms, and in this Sp ¹ , at least one -CH ₂ -may be substituted by -O- , At least one -(CH ₂ ) ₂ -can be replaced by -CH=CH-, at least one hydrogen can be replaced by fluorine or chlorine; M ¹ and M ^{2 are} independently hydrogen, fluorine, chlorine, and alkane with carbon numbers of 1 to 5 Group, or an alkyl group having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine; Y ^{1 is} independently hydrogen, an alkyl group having 1 to 10 carbons, an alkoxy group having 1 to 9 carbons, and a carbon number of 2 The alkoxyalkyl group with the carbon number of 1 to 9, or the alkylthio group with the carbon number of 2-9, in this Y ¹ , at least one -(CH ₂ ) ₂ -may be controlled by -CH= CH- or -C≡C- substituted, at least one hydrogen may be substituted by bromine, fluorine or chlorine; R ^{2 is} independently a linear alkyl group with 1 to 10 carbons or a branched chain alkyl group with 3 to 10 carbons, or Cyclic alkyl having 3 to 8 carbons; In formulas (1-9) to (1-16), Sp ² is a single bond or an alkylene having 1 to 7 carbons, in which at least one of ^{Sp 2 is-} CH ₂ -may be substituted by -O- or a group represented by formula (1-a), at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by Fluorine, chlorine, the group represented by formula (1-p1) or formula (1-p2) is substituted;

X ¹ is a group selected from groups represented by formula (1-x1) to formula (1-x10);

In formulas (1-x1) to (1-x10), W ¹ is a methine group or nitrogen, where the hydrogen of the methine group may be substituted with an alkyl group having 1 to 6 carbon atoms; m1 is independently 0, 1 or 2, in the -(CH ₂ ) _m1 -, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; W ² Is a methine group or nitrogen, where the hydrogen of the methine group can be substituted by an alkyl group having 1 to 6 carbons; K ¹ is an alkylene group having 1 or 2 carbons, and in this K ¹ , at least one -CH ₂ -May be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; K ² is carbon In the alkylene group of 1 or 2, in the K ² , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; n1 is 2 or 3, the -( Among CH ₂ ) _n1 -, at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine or chlorine; K ^{3 is} independently a carbon number 1. Alkylene, in the K ³ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; K ⁴ is -S- or -CO- ; K ⁵ independently an alkylene group of carbon number 1 or 2, K ⁵ in which at least one -CH ₂ - may be -O -, - CO- or -S-, at least one - (CH _{2) 2} -May be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; p1 is independently 0 or 1, in the -(CH ₂ ) _p1 -, at least one hydrogen may be substituted by fluorine or chlorine; K ⁶ alkylene group having a carbon number of 1's, in which K ^6, at least one -CH ₂ - may be substituted with -O- or -S-, may be at least one hydrogen replaced by fluorine or chlorine; K ⁷ is independently The ground is a single bond or an alkylene having 1 to 3 carbon atoms. In the K ⁷ , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; K ⁸ is Hydrogen or an alkyl group having 1 to 4 carbon atoms, in the K ⁸ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one -(CH ₂ ) ₂ -may be -CH =CH- or -C≡C- substitution, at least one hydrogen can be replaced by fluorine or chlorine; In formula (1-9), there is no case where p1 in formula (1-x7) is 0.

Item 4. The compound according to any one of items 1 to 3, which is represented by any one of formula (1-17) to formula (1-94).

In formulas (1-17) to (1-94), R ¹ is an alkyl group having 1 to 10 carbons; Z ¹ to Z ^{3 are} independently single bonds or -(CH ₂ ) ₂ -; Sp ^{1 is} independently It is a single bond or an alkylene having 1 to 5 carbon atoms, in which at least one -CH ₂ -may be substituted by -O- ^{in Sp 1 ; M 1} and M ^{2 are} independently hydrogen, fluorine, chlorine, and carbon numbers 1 to 5 alkyl group, or an alkyl group having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine; Y ^{1 is} independently hydrogen, an alkyl group having 1 to 10 carbons, an alkoxy group having 1 to 9 carbons, carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkylthio group having 1 to 2 carbon atoms or alkylthio 9 to 9, in which Y ^1, at least one - (CH _{2) 2} - may be -CH=CH- or -C≡C- substituted, at least one hydrogen can be substituted by bromine, fluorine or chlorine; R ^{2 is} independently a linear alkyl group with 1 to 10 carbons or a branched alkane with 3 to 10 carbons Group, or a cyclic alkyl group having 3 to 8 carbons; Y ¹¹ to Y ^{21 are} independently hydrogen, fluorine, an alkyl group having 1 to 5 carbons, an alkenyl group having 2 to 5 carbons, or a carbon number of 1 to 4 alkoxy; Sp ² is a single bond or an alkylene group having a carbon number 1 to 7, in which Sp ^2, at least one -CH ₂ - group can by -O- or formula (1-a) represented by the substituent, at least One -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine, chlorine, or a group represented by formula (1-p1) or formula (1-p2) ；

In formula (1-p1) and formula (1-p2), Sp ^{1 is} independently a single bond or an alkylene having 1 to 5 carbon atoms, and in this Sp ¹ , at least one -CH ₂ -may be substituted by -O- , At least one -(CH ₂ ) ₂ -can be replaced by -CH=CH-, at least one hydrogen can be replaced by fluorine or chlorine; M ¹ and M ^{2 are} independently hydrogen, fluorine, chlorine, and alkane with carbon numbers of 1 to 5 Group, or an alkyl group having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine; Y ^{1 is} independently hydrogen, an alkyl group having 1 to 10 carbons, an alkoxy group having 1 to 9 carbons, and a carbon number of 2 The alkoxyalkyl group with the carbon number of 1 to 9, or the alkylthio group with the carbon number of 2-9, in this Y ¹ , at least one -(CH ₂ ) ₂ -may be controlled by -CH= CH- or -C≡C- substituted, at least one hydrogen may be substituted by bromine, fluorine or chlorine; R ^{2 is} independently a linear alkyl group with 1 to 10 carbons or a branched chain alkyl group with 3 to 10 carbons, or A cyclic alkyl group having 3 to 8 carbons; in formula (1-17) to formula (1-94), Sp ³ and Sp ^{4 are} independently a single bond or an alkylene group having 1 to 5 carbons, and the Sp ³ And Sp ⁴ , at least one -CH ₂ -may be substituted by -O-; X ¹ is a group selected from the group represented by the formula (1-x1) to the formula (1-x10);

In formulas (1-x1) to (1-x10), W ¹ is a methine group or nitrogen, where the hydrogen of the methine group may be substituted with an alkyl group having 1 to 6 carbon atoms; m1 is independently 0, 1 or 2, in the -(CH ₂ ) _m1 -, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; W ² Is a methine group or nitrogen, where the hydrogen of the methine group can be substituted by an alkyl group having 1 to 6 carbons; K ¹ is an alkylene group having 1 or 2 carbons, and in this K ¹ , at least one -CH ₂ -May be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; K ² is carbon In the alkylene group of 1 or 2, in the K ² , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; n1 is 2 or 3, the -( Among CH ₂ ) _n1 -, at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine or chlorine; K ^{3 is} independently a carbon number 1. Alkylene, in the K ³ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; K ⁴ is -S- or -CO- ; K ⁵ independently an alkylene group of carbon number 1 or 2, K ⁵ in which at least one -CH ₂ - may be -O -, - CO- or -S-, at least one - (CH _{2) 2} -May be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; p1 is independently 0 or 1, in the -(CH ₂ ) _p1 -, at least one hydrogen may be substituted by fluorine or chlorine; K ⁶ alkylene group having a carbon number of 1's, in which K ^6, at least one -CH ₂ - may be substituted with -O- or -S-, may be at least one hydrogen replaced by fluorine or chlorine; K ⁷ is independently The ground is a single bond or an alkylene having 1 to 3 carbon atoms. In the K ⁷ , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; K ⁸ is Hydrogen or an alkyl group having 1 to 4 carbon atoms, in the K ⁸ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one -(CH ₂ ) ₂ -may be -CH =CH- or -C≡C- substitution, at least one hydrogen can be replaced by fluorine or chlorine; in formula (1-17), formula (1-18), formula (1-47) and formula (1-48), There is no case where p1 in the formula (1-x7) is all 0.

Item 5. A liquid crystal composition containing at least one of the compounds described in any one of Items 1 to 4.

Item 6. The liquid crystal composition according to Item 5, which contains at least one compound selected from the group of compounds represented by formula (2) to formula (4).

In formulas (2) to (4), R ¹¹ and R ^{12 are} independently an alkyl group having 1 to 10 carbons or an alkenyl group having 2 to 10 carbons, and at least one of ^{R 11} and R ¹² _{is -CH 2} -May be substituted by -O-, at least one hydrogen may be substituted 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 single bonds, -COO-, -(CH ₂ ) ₂ -, -CH=CH- or -C≡C-.

Item 7. The liquid crystal composition according to Item 5 or Item 6, which contains at least one compound selected from the group of compounds represented by formula (5) to formula (7).

In formulas (5) to (7), R ¹³ is an alkyl group having 1 to 10 carbons or an alkenyl group having 2 to 10 carbons, and in R ¹³ at least one -CH ₂ -may be substituted with -O-, 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 ; 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 substituted by fluorine; Z ¹⁴ , Z ¹⁵ and Z ^{16 are} independently single bonds, -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 8. The liquid crystal composition according to any one of Items 5 to 7, which contains at least one compound selected from the group of compounds represented by formula (8).

In formula (8), R ¹⁴ is an alkyl group having 1 to 10 carbons or an alkenyl group having 2 to 10 carbons. In R ¹⁴ , at least one -CH ₂ -may be substituted by -O-, and at least one hydrogen may be Fluorine substitution; X ¹² is -C≡N or -C≡CC≡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 substituted 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 9. The liquid crystal composition according to any one of Items 5 to 8, which contains at least one compound selected from the group of compounds represented by formula (11) to formula (19).

In formulas (11) to (19), R ¹⁵ , R ¹⁶ and R ^{17 are} independently an alkyl group having 1 to 10 carbons or an alkenyl group having 2 to 10 carbons, and R ¹⁵ , R ¹⁶ and R ¹⁷ are , At least one -CH ₂ -can be replaced by -O-, at least one hydrogen can be replaced by fluorine, and R ¹⁷ can also 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, decalin-2,6-diyl or at least A 1,4-phenylene in which one hydrogen is substituted by fluorine; Ring E ⁵ and Ring E ^{6 are} independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, Tetrahydropyran-2,5-diyl or decalin-2,6-diyl; Z ¹⁸ , Z ¹⁹ , Z ²⁰ and Z ^{21 are} independently single bonds, -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 independently -CHF- or -CF ₂ -; j, k, m, n, p, q, r and s are independently The ground is 0 or 1, the sum of k, m, n, and p is 1 or 2, the sum of q, r, and s is 0, 1, 2, or 3, and t is 1, 2, or 3.

Item 10. The liquid crystal composition according to any one of items 5 to 9, which contains at least one polymerizable compound represented by formula (20) (except for 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-dioxyl Alk-2-yl, pyrimidin-2-yl or pyridin-2-yl, in ring F and ring I, at least one hydrogen can be halogenated, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons The group or at least one hydrogen is substituted by a halogen-substituted alkyl group having 1 to 12 carbons; 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-di Base, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, phenanthrene-2,7-diyl, tetrahydropyridine Pyridine-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, in the ring G, at least one hydrogen May be substituted 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 substituted by halogen; Z ²² and Z ^{23 are} independently single bonds Or an alkylene having 1 to 10 carbon atoms, in Z ²² and Z ²³ , at least one -CH ₂ -may be substituted with -O-, -CO-, -COO- or -OCO-, and at least one -(CH ₂ ) ₂ -can be replaced by -CH=CH-, -C(CH ₃ )=CH-, -CH=C(CH ₃ )- or -C(CH ₃ )=C(CH ₃ )-, at least one hydrogen can be Substituted by fluorine or chlorine; P ¹¹ , P ¹² and P ^{13 are} independently polymerizable groups; Sp ¹¹ , Sp ¹² and Sp ^{13 are} independently single bonds or alkylene groups having 1 to 10 carbon atoms, the Sp ¹¹ , Sp ^{In 12} and Sp ¹³ , at least one -CH ₂ -can be replaced by -O-, -COO-, -OCO- or -OCOO-, and at least one -(CH ₂ ) ₂ -can be replaced by -CH=CH- or -C ≡C-substitution, at least one hydrogen can 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 more.

Item 11. The liquid crystal composition according to Item 10, wherein in formula (20), P ¹¹ , P ¹² and P ^{13 are} independently selected from the group consisting of the polymerization represented by formula (P-1) to formula (P-5) The basis in the group of sex basis.

In formula (P-1) to formula (P-5), M ¹¹ , M ¹² and M ^{13 are} independently hydrogen, fluorine, an alkyl group having 1 to 5 carbons, or a carbon number of 1 to 1 in which at least one hydrogen is substituted by halogen 5的alkyl.

Item 12. The liquid crystal composition according to Item 10 or Item 11, wherein the polymerizable compound represented by formula (20) contains a polymer selected from the group consisting of polymerizable compounds represented by formula (20-1) to formula (20-7) At least one compound in the group.

In formula (20-1) to formula (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. Among the Sp ¹¹ , Sp ¹² and Sp ¹³ , at least one -CH ₂ -may be controlled by -O-, -COO-,- OCO- or -OCOO- substitution, at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine or chlorine. P ¹¹ , P ¹² and P ^{13 are} independently groups selected from the group of polymerizable groups represented by formula (P-1) to formula (P-3),

In formulas (P-1) to (P-3), M ¹¹ , M ¹² and M ^{13 are} independently hydrogen, fluorine, an alkyl group having 1 to 5 carbons, or a carbon number of 1 to 1 in which at least one hydrogen is substituted by halogen 5的alkyl.

Item 13. The liquid crystal composition according to any one of Item 5 to Item 12, which contains a polymerizable compound selected from the group consisting of a compound different from the compound represented by the formula (1) or the formula (20), and a polymerizer. At least one of the group of initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, pigments, and defoamers.

Item 14. A liquid crystal display element containing at least a part selected from the liquid crystal composition according to any one of items 5 to 13 and the liquid crystal composition according to any one of items 5 to 13 to be polymerized At least one of a group consisting of a member.

The present invention also includes the following items. (A) The liquid crystal composition, which further contains 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 pigment, a defoamer, etc. At least two kinds of additives. (B) A polymerizable composition prepared by adding a polymerizable compound different from the compound (1) or the compound (20) to the liquid crystal composition. (C) A polymerizable composition prepared by adding compound (1) and compound (20) to the liquid crystal composition. (D) A liquid crystal composite prepared by polymerizing the polymerizable composition. (E) A polymer stable alignment type element containing the liquid crystal composite. (F) A polymer stabilized alignment type device, which is made by using a polymerizable composition by adding compound (1) and compound (20) to the liquid crystal composition. ), and a polymerizable compound different from compound (1) or compound (20).

The aspect of the compound (1), the synthesis of the compound (1), the liquid crystal composition, and the liquid crystal display element will be described in order below.

1. The aspect of compound (1) The compound (1) of the present invention is characterized by including a mesogen moiety including at least one ring, a polymerizable group, and a specific polar group having a cyclic structure. The compound (1) is useful because the polar group interacts with the surface of the substrate such as glass (or metal oxide) in a non-covalent bonding manner. One of the applications is an additive for a liquid crystal composition used in a liquid crystal display element. In this application, the compound (1) is added for the purpose of controlling the alignment of liquid crystal molecules. Such additives are preferably chemically stable under the condition of being sealed in the device, and have high thermal stability, high ability to align liquid crystal molecules, and high voltage retention when used in liquid crystal display devices. The solubility in the liquid crystal composition is large. The compound (1) satisfies such characteristics to a considerable extent. If it is the previous compound, it cannot be achieved, and the solubility in the liquid crystal composition is extremely large. By using this compound (1), it is different from the case of using the previous compound. In contrast, a device with excellent long-term stability can be easily obtained in a state where the alignment or voltage retention is maintained at the same level or more.

Preferred examples of compound (1) will be described. Preferred examples of symbols such as R ¹ , A ¹ , and Sp ² in compound (1) are also applicable to the lower formula of compound (1), such as formula (1-1) and the like. In the compound (1), the properties can be adjusted arbitrarily by appropriately combining the types of these groups. Since there is no big difference in the characteristics of the compounds, compound (1) may also contain more ² H (deuterium) and ¹³ C isotopes than naturally occurring ratios.

In formula (1), R ¹ is hydrogen or an alkyl group having 1 to 15 carbons. In R ¹ , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one -(CH ₂ ) ₂ -May be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine.

Preferably R ¹ is hydrogen or an alkyl group having 1 to 10 carbons. In R ¹ , at least one -CH ₂ -may be substituted by -O-, and at least one -(CH ₂ ) ₂ -may be -CH=CH -Substitution, at least one hydrogen can be replaced by fluorine or chlorine. Particularly preferred R ¹ is an alkyl group having 1 to 10 carbon atoms.

The compound in which R ¹ is an alkyl group having 1 to 15 carbon atoms has high chemical stability. The compound in which R ¹ is an alkyl group having 1 to 15 carbons has high solubility in the liquid crystal composition. The 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 A ¹ and ring A ^{2 are} independently 1,2-cyclopropylene, 1,3-cyclobutyl, 1,3-cyclopentyl, 1,4-cyclohexyl, 1,4-cyclohexyl Cycloheptyl, 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 group, in the ring A ¹ and ring A ² , at least one hydrogen can be fluorine, chlorine, alkyl with 1 to 10 carbons, alkenyl with 2 to 10 carbons, and alkane with 1 to 9 carbons. An oxy group or an alkenyloxy group having 2 to 9 carbon atoms is substituted, and at least one hydrogen may be substituted by fluorine or chlorine.

Preferred ring A ¹ and ring A ² 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 the ring A ¹ and ring A ² , at least one hydrogen may be fluorine, chlorine, or alkyl with 1 to 10 carbon atoms , Alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons or alkenyloxy having 2 to 9 carbons, at least one hydrogen may be substituted with fluorine or chlorine.

More preferred ring A ¹ and ring A ² 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 the ring A ¹ and ring A ² , at least one hydrogen can be fluorine, an alkyl group with 1 to 5 carbons, and carbon Alkenyl having 2 to 5 or alkoxy having 1 to 4 carbons is substituted.

Particularly preferred ring A ¹ and ring A ² are 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene substituted at 2-position, and 1,4-phenylene substituted at 3-position Or the 1,4-phenylene group substituted at the 2- and 3-positions. As the substituent, hydrogen, fluorine, an alkyl group having 1 to 5 carbons, an alkenyl group having 2 to 5 carbons, or a carbon number of 1 to The alkoxy group of 4 is more preferably hydrogen, fluorine, methyl or ethyl.

Ring A ¹ and ring A ^{2 are} independently 1,3-cyclopentyl, 1,4-cyclohexyl, 1,4-cycloheptyl, 1,4-phenylene, and at least one hydrogen is substituted by fluorine 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is substituted with an alkyl group having 1 to 5 carbon atoms, decalin-2,6-diyl or tetrahydropyran-2,5 -The chemical stability of the dibasic compound is high. 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 substituted by fluorine , 1,4-phenylene compounds in which at least one hydrogen is substituted by an alkyl group having 1 to 5 carbons or 1,4-phenylene compounds in which at least one hydrogen is substituted by an alkenyl group having 2 to 5 carbons in the liquid crystal composition The solubility is large. Ring A ¹ and ring A ^{2 are} independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene compounds in which at least one hydrogen is substituted with an alkyl group having 1 to 2 carbon atoms The ability to align liquid crystal molecules is high. Ring A ¹ and ring A ^{2 are} independently 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is substituted by an alkyl group having 1 to 5 carbons, and one in which at least one hydrogen is substituted with 1 to 4 carbons Polymerization reaction of alkoxy-substituted 1,4-phenylene, naphthalene-2,6-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl compounds caused by ultraviolet radiation High sex.

a is 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, more preferably 1, 2 or 3, particularly preferably 1 or 2.

The compound in which a is 0 has high solubility in the liquid crystal composition. The compound whose a is 3 or 4 has a high ability to align liquid crystal molecules. The compound whose a is 1 or 2 has high solubility in the liquid crystal composition, high ability to align liquid crystal molecules, and high polymerization reactivity caused by ultraviolet irradiation.

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

The compound in which the total of b and c is 1 or more has a polymerizable group ^{in ring A 1} or ring A ^2. In this case, the polymerization reactivity caused by ultraviolet irradiation is high.

Z ^{1 is} independently a single bond or an alkylene having 1 to 6 carbon atoms. In Z ¹ , at least one -CH ₂ -may be -O-, -CO-, -COO-, -OCO- or -OCOO- Substitution, at least one -(CH ₂ ) ₂ -can be replaced by -CH=CH- or -C≡C-, and at least one hydrogen can be replaced by fluorine or chlorine.

Preferably 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-. More preferably Z ¹ is a single bond, -(CH ₂ ) ₂ -, -CH=CH-, -C≡C-, -CH ₂ O- or -OCH ₂ -, and more preferably Z ¹ is a single bond or- (CH ₂ ) ₂ -, especially Z ¹ is a single bond.

The 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 the liquid crystal composition. The compound in which Z ¹ is a single bond or -(CH ₂ ) ₂ -has a high ability to align liquid crystal molecules. Compounds in which Z ¹ is a single bond, -CH=CH-, -C≡C-, -COO-, -OCO-, -CH ₂ O-, -OCH ₂ -have high polymerization reactivity by ultraviolet irradiation.

P ¹ and P ^{2 are} independently groups selected from groups represented by formula (1-p1) and formula (1-p2).

In formula (1-p1) and formula (1-p2), Sp ^{1 is} independently a single bond or an alkylene group having 1 to 15 carbon atoms, and in this Sp ¹ , at least one -CH ₂ -may be -O-, -CO-, -COO-, -OCO- or -OCOO- substituted, at least one -(CH ₂ ) ₂ -can be replaced by -CH=CH- or -C≡C-, at least one hydrogen can be replaced by fluorine or chlorine .

The preferred Sp ¹ is a single bond or an alkylene having 1 to 7 carbon atoms. In the Sp ¹ , at least one -CH ₂ -can be substituted by -O-, -CO- or -COO-, and at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH-, at least one hydrogen may be substituted by fluorine or chlorine.

Sp ¹ is a single bond better carbon atoms or alkylene of 1 to 5, in which Sp ^1, at least one -CH ₂ - may be substituted with -O-, at least one - (CH _{2) 2} - may be -CH =CH- substitution, at least one hydrogen can be replaced by fluorine or chlorine. Particularly preferred Sp ¹ is a single bond or an alkylene having 1 to 5 carbon atoms, and in this Sp ¹ , at least one -CH ₂ -may be substituted by -O-.

The compound in which Sp ^{1 is} independently a single bond or an alkylene group having 1 to 7 carbon atoms has high chemical stability. Sp ^{1 is} independently an alkylene having 1 to 7 carbons or _{a compound in which at least one -CH 2} -is substituted with -O- of an alkylene having 1 to 7 carbons. The solubility of the compound in the liquid crystal composition is high .

M ¹ and M ^{2 are} independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbons, or an alkyl group having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine.

R ^{2 is} independently a linear alkyl group having 1 to 10 carbons, a branched alkyl group having 3 to 10 carbons, or a cyclic alkyl group having 3 to 8 carbons. Preferably R ² has 1 to 5 carbon atoms. Particularly preferred R ² is carbon number 1. In this case, the reactivity is high, and the ability to align liquid crystal molecules and the voltage retention rate when used in a liquid crystal display device can be maintained.

Y ^{1 is} independently hydrogen, an alkyl group having 1 to 10 carbons, an alkoxy group having 1 to 9 carbons, an alkoxyalkyl group having 2 to 9 carbons, an alkylthio group having 1 to 9 carbons, or a carbon number 2 to 9 alkylthioalkyl groups, in the Y ¹ , at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by bromine, fluorine or chlorine .

In the formula (1), Sp ² is a single bond or an alkylene group having 1 to 10 carbons, and in the Sp ² at least one -CH ₂ -can pass through -O-, -CO-, -COO-, -OCO- , -OCOO- or the group represented by formula (1-a), at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine, chlorine, The group represented by the formula (1-p1) or the formula (1-p2) is substituted.

The preferred Sp ² is a single bond or an alkylene having 1 to 7 carbon atoms. In the Sp ² at least one -CH ₂ -can pass through -O-, -CO-, -COO- or formula (1-a) The represented group is substituted, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH-, and at least one hydrogen may be substituted by fluorine, chlorine, the group represented by the formula (1-p1) or the formula (1-p2) replace.

More preferably, Sp ² is a single bond or an alkylene group having 1 to 7 carbon atoms. In this Sp ² , at least one -CH ₂ -may be substituted by -O- or a group represented by the formula (1-a), and at least one Hydrogen can be replaced by fluorine or chlorine, at least one -(CH ₂ ) ₂ -can be replaced by -CH=CH-, at least one hydrogen can be represented by fluorine, chlorine, formula (1-p1) or formula (1-p2) The group is substituted. Particularly preferred Sp ² is a single bond or an alkylene group having 1 to 7 carbon atoms. In this Sp ² , at least one -CH ₂ -may be substituted with -O- or a group represented by the formula (1-a).

The compound in which Sp ² is a single bond or an alkylene group having 1 to 7 carbon atoms has high chemical stability. Sp ² _{is a group in which at least one -CH 2} -of an alkylene having 1 to 7 carbons or an alkylene having 1 to 7 carbons is substituted with -O- or a group represented by formula (1-a) The compound has high solubility in the liquid crystal composition.

X ¹ is a group selected from groups represented by formula (1-x1) to formula (1-x10).

In formulas (1-x1) to (1-x10), W ¹ is a methine group or nitrogen, and here, the hydrogen of the methine group may be substituted with an alkyl group having 1 to 6 carbon atoms. m1 is independently 0, 1, or 2, in the -(CH ₂ ) _m1 -, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be fluorine Or chlorine substitution. W ² is a methine group or nitrogen. Here, the hydrogen of the methine group may be substituted with an alkyl group having 1 to 6 carbon atoms.

K ¹ is an alkylene having 1 or 2 carbon atoms. In K ¹ , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one -(CH ₂ ) ₂ -may be -CH=CH -Or -C≡C- substitution, at least one hydrogen can be replaced by fluorine or chlorine. K ² is an alkylene group having 1 or 2 carbon atoms. In K ² , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine.

n1 is 2 or 3. Among the -(CH ₂ ) _n1 -, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine. K ^{3 is} independently an alkylene having a carbon number of 1. In K ³ , at least one -CH ₂ -may be substituted with -O-, -CO- or -S-, and at least one hydrogen may be substituted with fluorine or chlorine. K ⁴ is -S- or -CO-. K ^{5 is} independently an alkylene having 1 or 2 carbon atoms. In this K ⁵ , at least one -CH ₂ -may be substituted with -O-, -CO- or -S-, and at least one -(CH ₂ ) _2- It may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine.

p1 is independently 0 or 1, and in the -(CH ₂ ) _p1 -, at least one hydrogen may be replaced by fluorine or chlorine. K ⁶ is an alkylene group having a carbon number of 1. In K ⁶ , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine. K ⁷ independently a single bond or alkylene group having a carbon number of 1 to 3, the K ^7, at least one -CH ₂ - may be substituted with -O- or -S-, may be at least one hydrogen replaced by fluorine or chlorine; K ⁸ is hydrogen or an alkyl group having 1 to 4 carbons. In the K ⁸ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one -(CH ₂ ) ₂ -may be Substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine. When p1 is all 0, a is 1, 2, 3, or 4.

Preferred examples of the compound (1) are the compound (1-1) to the compound (1-8) described in Item 2. More preferable examples of the compound (1) are the compound (1-9) to the compound (1-16) described in item 3. Particularly preferable examples of the compound (1) are the compound (1-17) to the compound (1-94) described in Item 4.

2. Synthesis of compound (1) The synthesis method of compound (1) will be described. Compound (1) can be synthesized by appropriately combining organic synthetic chemistry methods. Compounds that are not described in the synthesis method can be obtained through "Organic Syntheses" (John Wiley & Sons, Inc), "Organic Reactions" (John Wiley & Sons, Inc.) Company (John Wiley & Sons, Inc), "Comprehensive Organic Synthesis" (Pergamon Press), "New Experimental Chemistry Lecture" (Maruzen) and other books synthesis.

2-1. Formation of bonding group An example of a method of generating a bonding group in compound (1) is as described in the following scheme. In this process, MSG ¹ (or MSG ² ) is a monovalent organic group with at least one ring. The monovalent organic groups represented by a plurality of MSG ¹ (or MSG ² ) may be the same or different. The compound (1A) to the compound (1H) are equivalent to the compound (1) or the intermediate of the compound (1).

(I) Generation of single key In the presence of a carbonate and a tetrakis (triphenylphosphine) palladium catalyst, the boric acid compound (21) and the compound (22) are reacted to synthesize the compound (1A). The compound (1A) can also be synthesized in the following way: the compound (23) is reacted with n-butyllithium, followed by reaction with zinc chloride, and then in the presence of dichlorobis(triphenylphosphine) palladium catalyst React with compound (22).

(II) Formation of -COO- and -OCO- The compound (23) is reacted with n-butyllithium, and then reacted with carbon dioxide to obtain the carboxylic acid (24). The carboxylic acid (24) and the alcohol (25) derived from the compound (21) are combined with 1,3-dicyclohexylcarbodiimide (DCC) and 4-dimethylamino group Dehydration in the presence of pyridine (4-dimethylamino pyridine, DMAP) to synthesize the -COO- compound (1B). Compounds with -OCO- are also 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 using hydrogen fluoride pyridine complex and N-bromosuccinimide (NBS) to synthesize compound (1C) _{with -CF 2 O-.} Refer to "Chem. Lett." Issue 827, 1992 by M. Kuroboshi and others. Compound (1C) can also be synthesized by fluorinating compound (26) with (diethylamino) sulphur trifluoride (DAST). Refer to WH Bunnelle et al., "Journal of Organic Chemistry (J. Org. Chem.)", No. 55, p. 768, 1990. Compounds with -OCF ₂ -can also be synthesized by this method.

(IV) Generation of -CH=CH- The compound (22) is reacted with n-butyllithium, and then reacted with N,N-Dimethyl Formamide (DMF) to obtain aldehyde (27). The phosphonium salt (28) is reacted with potassium tert-butoxide to generate a phosphor ylide, and the phosphorous dipole is reacted with the aldehyde (27) to synthesize the compound (1D). Since the cis isomer is generated due to the reaction conditions, the cis isomer is isomerized to the trans isomer by a known method as necessary.

The formation of (V)-(CH ₂ ) ₂ -is in the presence of a palladium-carbon catalyst, and compound (1D) is hydrogenated to synthesize compound (1E).

(VI) Generation of -C≡C- In the presence of palladium dichloride and copper iodide as a catalyst, compound (23) is reacted with 2-methyl-3-butyn-2-ol, and then deprotected under alkaline conditions to obtain compound (29) ). In the presence of a catalyst of dichlorobis(triphenylphosphine)palladium and copper halide, compound (29) and compound (22) are reacted to synthesize compound (1F).

(VII) _{Formation of -CH 2} O- and -OCH ₂ -The compound (27) is reduced with sodium borohydride to obtain the compound (30). It was brominated with hydrobromic acid to obtain compound (31). In the presence of potassium carbonate, compound (25) and compound (31) are reacted to synthesize compound (1G). Compounds with -OCH ₂ -can also be synthesized by this method.

(VIII) Generation of -CF=CF- After treating compound (23) with n-butyllithium, tetrafluoroethylene is reacted to obtain compound (32). After treating compound (22) with n-butyllithium, it reacts with compound (32) to synthesize compound (1H).

2-2. ^{The formation of ring A 1} and ring A ² is about 1,2-cyclopropylene, 1,3-cyclobutyl, 1,3-cyclopentyl, 1,4-cyclohexyl, 1 ,4-cycloheptyl, 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 , Pyridine-2,5-diyl and other rings, the starting materials are commercially available, or the synthesis method is widely known.

2-3. Synthesis Examples Examples of methods for synthesizing compound (1) are as follows. In these compounds, ^{the definitions of R 1} , A ¹ , A ² , Z ¹ , P ¹ , P ² , Sp ² , X ¹ , K ⁸ , a, b, and c are the same as those described in Item 1.

In the formula (1), the compound (1-X51) whose polar group is the formula (1-x9) can be synthesized by the following method. The compound (51) and the compound (52) are reacted in the presence of p-toluenesulfonic acid monohydrate to obtain the compound (53). The compound (54) is reacted with 2-fluoroacrylic acid, N,N-dicyclohexylcarbodiimide (DCC), and N,N-dimethyl-4-aminopyridine (DMAP) to obtain compound (56) . By reacting compound (56) with compound (53) in the presence of potassium carbonate, compound (1-X51) can be derived.

3. Liquid crystal composition 3-1. Component compounds The liquid crystal composition of the present invention contains the compound (1) as the component A. The compound (1) can control the alignment of liquid crystal molecules through the non-covalent bonding interaction with the substrate of the device. The composition preferably contains the compound (1) as the component A, and further contains at least one liquid crystal compound selected from the following component B, component C, component D, and component E. Component B is compound (2) to compound (4). Component C is compound (5) to compound (7) other than compound (2) to compound (4). Component D is compound (8). Component E is compound (11) to compound (19). The composition may also include other liquid crystal compounds different from the compound (2) to the compound (8) and the compound (11) to the compound (19). When preparing the composition, it is preferable to select Component B, Component C, Component D, and Component E in consideration of the magnitude of positive or negative dielectric anisotropy. The composition of appropriately selected components has a high upper limit temperature, a low lower limit temperature, a low viscosity, an appropriate optical anisotropy (that is, a large optical anisotropy or a small optical anisotropy), a large positive or negative Dielectric anisotropy, large specific resistance, stability to heat or ultraviolet rays, and appropriate elastic constant (ie, large or small elastic constant).

The compound (1) is added to the composition for the purpose of controlling the alignment of liquid crystal molecules. With regard to the preferred ratio of compound (1) to 100% by weight of the liquid crystal composition, it is more than 0.05% by weight in terms of easily aligning the liquid crystal molecules, etc., and in terms of further preventing poor display of the device, etc. It is preferably 10% by weight or less. A particularly preferable ratio is in the range of 0.1% by weight to 7% by weight, and a particularly preferable 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 two terminal groups are alkyl groups or the like. Component B has small dielectric anisotropy. Preferred examples of component B include compound (2-1) to compound (2-11), compound (3-1) to compound (3-19), and compound (4-1) to compound (4-7). In these compounds, R ¹¹ and R ^{12 are} independently an alkyl group having 1 to 10 carbons or an alkenyl group having 2 to 10 carbons. In R ¹¹ and R ¹² , at least one -CH ₂ -may be controlled by -O- Substitution, at least one hydrogen may be replaced by fluorine.

Component B is a near neutral compound because the absolute value of dielectric anisotropy is small. Compound (2) is mainly effective in reducing viscosity or adjusting optical anisotropy. The compound (3) and the compound (4) have the effect of increasing the temperature range of the nematic phase by increasing the upper limit temperature, or have the effect of adjusting the optical anisotropy.

As the content of component B increases, the dielectric anisotropy of the composition becomes smaller, but the viscosity becomes smaller. Therefore, as long as the required value of the threshold voltage of the element is satisfied, the content of the component B is preferably more. With respect to 100% by weight of the liquid crystal composition, the content of Component B is preferably 30% by weight or more, more preferably 40% by weight or more, and the upper limit is not particularly limited, and is, for example, 99.95% by weight.

Component C is a compound having fluorine, chlorine or a fluorine-containing group at at least one end. Component C has a large positive dielectric anisotropy. Preferred examples of component C include compound (5-1) to compound (5-16), compound (6-1) to compound (6-116), and compound (7-1) to compound (7-59). In the compound of component C, R ¹³ is an alkyl group having 1 to 10 carbons or an alkenyl group having 2 to 10 carbons. In R ¹³ , at least one -CH ₂ -may be substituted by -O-, and at least one hydrogen may be Fluorine substitution. 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 .

The dielectric anisotropy of component C is positive, and the stability to heat, light, etc. is very good, so it can be preferably used in the preparation of IPS, FFS, OCB and other mode compositions. The content of component C relative to 100% by weight of the liquid crystal composition is suitably in the range of 1% to 99% by weight, preferably in the range of 10% to 97% by weight, and particularly preferably in the range of 40% to 95% by weight. . When the component C is added to a composition having a negative dielectric anisotropy, the content of the component C is preferably 30% by weight or less with respect to 100% by weight of the liquid crystal composition. By adding component C, the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the device can be adjusted.

Component D is a compound (8) with a single end group of -C≡N or -C≡CC≡N. Since component D has a cyano group, it has a greater positive dielectric anisotropy. Preferred examples of component D include compound (8-1) to compound (8-64). In the compound of component D, R ¹⁴ is an alkyl group having 1 to 10 carbons or an alkenyl group having 2 to 10 carbons. In R ¹⁴ , at least one -CH ₂ -may be substituted by -O-, and at least one hydrogen may be Fluorine substitution. -X ¹² is -C≡N or -C≡CC≡N.

The dielectric anisotropy of component D is positive and its value is large, so it is mainly used for the preparation of TN and other mode compositions. By adding this component D, the dielectric anisotropy of the composition can be increased. Component D has the effect of expanding 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 device.

The content of component D relative to 100% by weight of the liquid crystal composition is suitably in the range of 1% to 99% by weight, preferably in the range of 10% to 97% by weight, and particularly preferably in the range of 40% to 95% by weight. . When adding the component D to a composition having a negative dielectric anisotropy, the content of the component D is preferably 30% by weight or less with respect to 100% by weight of the liquid crystal composition. By adding component D, the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the device can be adjusted.

Component E is compound (11) to compound (19). Component E has a large negative dielectric anisotropy. These compounds have 2,3-difluoro-1,4-phenylene-like phenylene substituted by two halogens (fluorine or chlorine) in the lateral position. Preferred examples of component E include compound (11-1) to compound (11-9), compound (12-1) to compound (12-19), compound (13-1) to compound (13-2), Compound (14-1) to Compound (14-3), Compound (15-1) to Compound (15-3), Compound (16-1) to Compound (16-11), Compound (17-1) to Compound (17-3), compound (18-1) to compound (18-3) and compound (19-1). In these compounds, R ¹⁵ , R ¹⁶ and R ^{17 are} independently an alkyl group having 1 to 10 carbons or an alkenyl group having 2 to 10 carbons, and at least one of ^{R 15} , R ¹⁶ and R ¹⁷ _{is -CH 2} -May be substituted by -O-, at least one hydrogen may be substituted by fluorine, and R ¹⁷ may also be hydrogen or fluorine.

The dielectric anisotropy of component E is negative and large. Component E can be preferably used in the preparation of IPS, VA, PSA and other mode compositions. As the content of component E is increased, the dielectric anisotropy of the composition becomes negative and becomes larger, but the viscosity becomes larger. Therefore, as long as the required value of the threshold voltage of the element is met, the content is preferably less. Considering that the dielectric anisotropy is about -5, in order to perform sufficient voltage driving, the content of the component E relative to 100% by weight of the liquid crystal composition is preferably 40% by weight or more.

Among component E, compound (11) is a bicyclic compound, and therefore has the effect of reducing viscosity, adjusting optical anisotropy, or increasing dielectric anisotropy. The compound (12) and the compound (13) are tricyclic compounds, and the compound (14) is a tetracyclic compound, so it has the effect of increasing the upper limit temperature, increasing the optical anisotropy, or increasing the dielectric anisotropy. Compounds (15) to (19) have an effect of improving dielectric anisotropy.

Relative to 100% by weight of the liquid crystal composition, the content of Component E is preferably 40% by weight or more, and more preferably in the range of 50% by weight to 95% by weight. When the component E is added to a composition having a positive dielectric anisotropy, the content of the component E is preferably 30% by weight or less with respect to 100% by weight of the liquid crystal composition. By adding component E, the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the device can be adjusted.

By appropriately combining the above-mentioned component B, component C, component D, and component E, a liquid crystal composition that satisfies at least one of the following characteristics can be prepared: high upper limit temperature, low lower limit temperature, low viscosity, and appropriate optical anisotropy , Positive or negative dielectric anisotropy, high specific resistance, high stability to ultraviolet light, high stability to heat, large elastic constant, etc.

3-2. Additives The liquid crystal composition is prepared by a known method. For example, a method of mixing the above-mentioned components and then dissolving each other by heating is mentioned. It is also possible to add additives to the composition according to the application. Examples of additives are polymerizable compounds other than compound (1), polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, pigments, defoamers, and the like. Such additives are well known to those with ordinary knowledge in the technical field and are described in the literature.

The polymerizable compound is added for the purpose of forming a polymer in the liquid crystal composition. The liquid crystal composition is injected into the device, and ultraviolet rays are irradiated with a voltage applied between the electrodes to polymerize the compound (1), thereby producing a polymer. At this time, the compound (1) is immobilized in a state where its polar group interacts with the surface of the glass (or metal oxide) substrate in a non-covalent bonding manner. Thereby, the ability to control the alignment of liquid crystal molecules is further improved, and an appropriate pretilt angle can be obtained, so the response time can be shortened.

Preferred examples of the polymerizable compound are acrylate, methacrylate, vinyl compound, vinyloxy compound, propenyl ether, epoxy compound (oxetane, oxetane), and vinyl ketone. Particularly preferred examples are compounds having at least one acryloxy group and compounds having at least one methacryloxy group. Particularly preferred examples also include compounds having both an acryloxy group and a methacryloxy group. A particularly preferable example of the polymerizable compound includes compound (20). Compound (20) is a different compound from compound (1). Compound (1) has a polar group. On the other hand, the 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-dioxyl Alk-2-yl, pyrimidin-2-yl or pyridin-2-yl, in ring F and ring I, at least one hydrogen can be halogenated, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons The group or at least one hydrogen is substituted with a halogen-substituted alkyl group having 1 to 12 carbons.

Preferred ring F or ring I is cyclohexyl, cyclohexenyl, phenyl, fluorophenyl, difluorophenyl, 1-naphthyl or 2-naphthyl. Particularly 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 the ring G, at least one hydrogen may be halogen, an alkyl group having 1 to 12 carbons, The alkoxy group having 1 to 12 carbons or at least one hydrogen is substituted with a halogen-substituted alkyl group having 1 to 12 carbons.

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. Particularly preferred ring G is 1,4-cyclohexenylene, 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 best ring G is 1,4-phenylene.

In the formula (20), Z ²² and Z ^{23 are} independently a single bond or an alkylene group having 1 to 10 carbons. In Z ²² and Z ²³ , at least one -CH ₂ -may pass through -O-, -CO- , -COO- or -OCO- substitution, at least one -(CH ₂ ) ₂ -can be replaced by -CH=CH-, -C(CH ₃ )=CH-, -CH=C(CH ₃ )- or -C( CH ₃ )=C(CH ₃ )-substitution, at least one hydrogen can be replaced by fluorine or chlorine. Preferably Z ²² or Z ²³ is a single bond, -(CH ₂ ) ₂ -, -CH ₂ O-, -OCH ₂ -, -COO- or -OCO-. Z ²² or Z ²³ is preferably a single bond.

In the compound (20), P ¹¹ , P ¹² and P ^{13 are} independently polymerizable groups. Preferred P ¹¹ to P ¹³ are groups selected from the group of polymerizable groups represented by formula (P-1) to formula (P-5). Particularly preferred P ¹¹ to P ¹³ are groups represented by formula (P-1), formula (P-2) or formula (P-3). Particularly preferred P ¹¹ to P ¹³ are groups represented by formula (P-1). The preferred group represented by the formula (P-1) is acryloxy group (-OCO-CH=CH ₂ ) or methacryloxy group (-OCO-C(CH ₃ )=CH ₂ ). The wavy lines from formula (P-1) to formula (P-5) indicate the location where bonding is performed.

In formula (P-1) to formula (P-5), M ¹¹ , M ¹² and M ^{13 are} independently hydrogen, fluorine, an alkyl group having 1 to 5 carbons, or a carbon number of 1 to 1 in which at least one hydrogen is substituted by halogen 5的alkyl. In order to improve the reactivity, preferably M ¹¹ , M ¹² or M ¹³ is hydrogen or methyl. 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, and among the Sp ¹¹ , Sp ¹² and Sp ¹³ , at least one -CH ₂ -may be- O-, -COO-, -OCO- or -OCOO- substitution, at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine or chlorine. Preferably 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 preferred sum is 2 or 3.

Preferred examples of the compound (20) are the compound (20-1) to the compound (20-7) described in Item 12 and the compound (20-8) to the compound (20-11) described later. Particularly preferred examples are compound (20-1-1) to compound (20-1-5), compound (20-2-1) to compound (20-2-5), compound (20-4-1), Compound (20-5-1), Compound (20-6-1) and Compound (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 an alkyl group having 1 to 5 carbons, and at least ^{R 32} , R ³³ and R ^{34 are} One is an alkyl group 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 a maximum of 10; L ³¹ to L ³⁶ Each is hydrogen or fluorine, and L ³⁷ and L ^{38 are} independently hydrogen, fluorine or methyl.

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

Additional examples of photo radical polymerization initiators are 4-methoxyphenyl-2,4-bis(trichloromethyl)triazine, 2-(4-butoxystyryl)-5-trichloro Methyl-1,3,4-oxadiazole, 9-phenylacridine, 9,10-benzophenazine, benzophenone/Michelone mixture, hexaarylbiimidazole/mercaptobenzimidazole Mixture, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1-one, benzyldimethyl ketal, 2-methyl-1-[4-(methylthio) )Phenyl]-2-morpholinopropane-1-one, 2,4-diethylxanthone/methyl p-dimethylaminobenzoate mixture, benzophenone/methyltriethanolamine mixture .

After adding a photoradical polymerization initiator to the liquid crystal composition, ultraviolet rays are irradiated in a state where an electric field is applied, thereby allowing polymerization to proceed. However, unreacted polymerization initiators or decomposition products of the polymerization initiators may cause image burn marks and other display defects on the device. In order to prevent this, it is also possible to perform photopolymerization without adding a polymerization initiator. The preferred wavelength of the irradiated light is in the range of 150 nm to 500 nm. The preferred wavelength is in the range of 250 nm to 450 nm, and the optimal wavelength is in the range of 300 nm to 400 nm.

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

The optically active compound has the effect of preventing reverse twist by inducing a helical structure in the liquid crystal molecules to impart a desired twist angle. By adding optically active compounds, the spiral pitch can be adjusted. For the purpose of adjusting the temperature dependence of the spiral pitch, two or more optically active compounds may be added. Preferred examples of the optically active compound include the following compounds (Op-1) to (Op-18). In the compound (Op-18), ring J is 1,4-cyclohexylene or 1,4-phenylene, and R ²⁸ is an alkyl group having 1 to 10 carbons. The * symbol indicates asymmetric carbon.

In order to maintain a large voltage holding rate, antioxidants are effective. Preferred examples of antioxidants include: the following compounds (AO-1) and compounds (AO-2); Irganox 415, Irganox 565, Irganox 1010, Yan Irganox 1035, Irganox 3114 and Irganox 1098 (trade name; BASF company). In order to prevent a decrease in the upper limit temperature, an ultraviolet absorber is effective. Preferred examples of ultraviolet absorbers are benzophenone derivatives, benzoate derivatives, triazole derivatives, etc. Specific examples include the following compounds (AO-3) and compounds (AO-4); Tinuvin 329, Tinuvin P, Tinuvin 326, Tinuvin 234, Tinuvin 213, Tinuvin 400, and Tinuvin (Tinuvin) 328 and Dinubin (Tinuvin) 99-2 (trade name; BASF (BASF)); and 1,4-diazabicyclo[2.2.2]octane (DABCO).

In order to maintain a large voltage retention rate, a light stabilizer such as an amine having a steric hindrance is preferred. Preferred examples of light stabilizers include the following compounds (AO-5), compound (AO-6) and compound (AO-7); Tinuvin 144, Tinuvin 765 and Tinuvin 770DF (trade name; BASF); LA-77Y and LA-77G (trade name; ADEKA). In order to maintain a large voltage holding rate, a heat stabilizer is also effective. A preferred example can be Irgafos 168 (trade name; BASF). In order to be suitable for a guest host (GH) mode element, dichroic dyes such as azo dyes and anthraquinone dyes are added to the composition as needed. In order to prevent foaming, defoamers are effective. Preferable examples of the defoaming agent are dimethyl silicone oil, methyl phenyl silicone oil, and the like.

In the compound (AO-1), R ⁴⁰ is an alkyl group having 1 to 20 carbons, an alkoxy group having 1 to 20 carbons, -COOR ⁴¹ or -(CH ₂ ) ₂ -COOR ⁴¹ , where R ⁴¹ is An alkyl group having 1 to 20 carbons. In compound (AO-2) and compound (AO-5), R ⁴² is an alkyl group having 1 to 20 carbons. In compound (AO-5), R ⁴³ is hydrogen, methyl or O ^· (oxygen radical); ring G ¹ is 1,4-cyclohexylene or 1,4-phenylene; compound (AO-7) Wherein, ring G ² is a group in which at least one hydrogen of 1,4-cyclohexylene, 1,4-phenylene or 1,4-phenylene is substituted by fluorine; compound (AO-5) and compound (AO- In 7), z is 1, 2 or 3.

4. Liquid crystal display element The liquid crystal composition can be preferably used for liquid crystal display elements that have operating modes such as PC, TN, STN, OCB, PSA, etc. and are driven in an active matrix manner. The composition can also be preferably used for liquid crystal display elements with PC, TN, STN, OCB, VA, IPS and other operating modes and driven in a passive matrix manner. These elements can also be applied to any type of reflection type, transmission type, and semi-transmission type.

The composition is also suitable for nematic curvilinear aligned phase (NCAP) elements, where the composition is microencapsulated. The composition can also be used in polymer dispersed liquid crystal display (PDLCD) or polymer network liquid crystal display (PNLCD). In these compositions, a large amount of polymerizable compounds is added. On the other hand, regarding the composition for the liquid crystal display element of the PSA mode, the ratio of the polymerizable compound is preferably 10% by weight or less, and more preferably 0.1% by weight to 2% by weight relative to 100% by weight of the liquid crystal composition. % Is in the range, and a particularly preferable ratio is in the range of 0.2% by weight to 1.0% by weight. PSA mode components can be driven in active matrix mode, passive matrix mode, and other driving methods. This type of element can also be applied to any type of reflection type, transmission type, and semi-transmission type.

In a polymer stabilized alignment type device, the polymer contained in the composition aligns liquid crystal molecules. Polar compounds help the liquid crystal molecules to align. That is, the polar compound can be used instead of the alignment film. An example of a method of manufacturing such an element is as follows. An element having two substrates called an array substrate and a color filter substrate is prepared. The substrate does not have an alignment film. At least one of the substrates has an electrode layer. The liquid crystal compounds are mixed to prepare a liquid crystal composition. The compound (1) and other polymerizable compounds and polar compounds as necessary are added to the composition. If necessary, further additives can be added. The composition is injected into the device. Light irradiation is performed in a state where a voltage is applied to the element. Preferably it is ultraviolet light. The polymerizable compound is polymerized by light irradiation. By this polymerization, a composition containing a polymer is produced, and an element having a PSA mode is produced.

In this procedure, the polar compounds are arranged on the substrate due to the interaction of the polar groups with the surface of the substrate. The polar compound aligns liquid crystal molecules. When there are multiple polar groups, the interaction with the substrate surface becomes stronger, and alignment can be performed at a low concentration. When a voltage is applied, the electric field is used to further promote the alignment of the liquid crystal molecules. According to this alignment, the polymerizable compound is also aligned. In this state, the polymerizable compound is polymerized by ultraviolet rays, so that a polymer that maintains the alignment is produced. Due to the effect of the polymer, the alignment of the liquid crystal molecules is additionally stabilized, and therefore the response time of the device is shortened. Since the burn mark of the image is the poor operation of the liquid crystal molecules, the effect of the polymer can also improve the burn mark. The compound (1) is polymerizable and therefore is consumed by polymerization. Compound (1) is also consumed by copolymerization with other polymerizable compounds. Therefore, although the compound (1) has a polar group, it is consumed, and therefore a liquid crystal display element with a large voltage holding ratio can be obtained. Furthermore, if a polar compound having polymerizability is used, the effects of both the polar compound and the polymerizable compound can be achieved by one compound, and therefore, a polymerizable compound that does not have a polar group is sometimes unnecessary. [Example]

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

1. Examples of Compound (1) Unless otherwise stated, the reaction is carried out under a nitrogen atmosphere. Compound (1) was synthesized by the procedure shown in Example 1 and the like. The synthesized compound is identified by nuclear magnetic resonance (Nuclear Magnetic Resonance, NMR) analysis and other methods. The characteristics of the compound (1), the liquid crystal compound, the composition, and the device were measured by the following methods.

NMR analysis: In the measurement, DRX-500 manufactured by Bruker BioSpin was used. In the ¹ H-NMR measurement, the sample is dissolved in a _{deuterated solvent such as CDCl 3} and the measurement is performed at room temperature (25° C.) under the conditions of 500 MHz and 16 cumulative times. Tetramethylsilane is used as the internal standard. In ^{the measurement of 19} F-NMR, CFCl _{3 was} used as an internal standard, and the measurement was carried out at 24 cumulative times. In the description of NMR spectrum, s refers to singlet, d refers to doublet, t refers to triplet, q refers to quartet, and quin refers to quintet. (Quintet), sext means sextet, m means multiplet, br means broad.

Gas chromatography analysis: In the measurement, a GC-2010 gas chromatograph manufactured by Shimadzu Corporation (stock) was used. The column is a capillary column DB-1 manufactured by Agilent Technologies Inc. (length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm). As the carrier gas, helium gas (1 ml/min) is used. Set the temperature of the sample vaporization chamber to 300°C, and set the temperature of the detector (flame ionization detector (FID)) part to 300°C. The sample is prepared by dissolving in acetone and becoming a 1% by weight solution, and 1 μL of the obtained solution is injected into the sample vaporization chamber. The recorder uses the GC solution system manufactured by Shimadzu Corporation.

High Performance Liquid Chromatography (HPLC) analysis: In the measurement, Prominence (LC-20AD; SPD-20A) manufactured by Shimadzu Corporation (Stock) was used. The column is YMC-Pack (YMC-Pack) ODS-A (length 150 mm, inner diameter 4.6 mm, particle size 5 μm) manufactured by YMC. The eluate is used by appropriately mixing acetonitrile and water. As the detector, it is suitable to use an ultraviolet (Ultraviolet, UV) detector, a Reflective Index (RI) detector, a Corona (CORONA) detector, etc. In the case of using a UV detector, set the detection wavelength to 254 nm. The sample is prepared by dissolving in acetonitrile to become a 0.1% by weight solution, and 1 μL of this solution is introduced into the sample chamber. The recorder uses C-R7A plus manufactured by Shimadzu Corporation.

Ultraviolet visible spectroscopy analysis: In the measurement, PharmaSpec UV-1700 manufactured by Shimadzu Corporation (stock) was used. Set the detection wavelength to 190 nm to 700 nm. The sample was prepared by dissolving in acetonitrile and becoming a 0.01 mmol/L solution, and placed in a quartz cell (optical path length of 1 cm) for measurement.

Test sample: When determining the phase structure and transition temperature (transparency point, melting point, polymerization start temperature, etc.), the compound itself is used as the sample.

Measuring method: The characteristic is measured by the following method. Most of these methods are methods described in the JEITA standard (JEITA·ED-2521B) reviewed and formulated by the Japan Electronics and Information Technology Industries Association (JEITA) or modified methods. In the TN device used for the measurement, no thin film transistor (TFT) was installed.

(1) Phase structure The sample was placed on a hot plate (manufactured by Mettler, FP-52 hot stage) equipped with a melting point measuring device with a polarizing microscope. While heating the sample at a rate of 3°C/min, the state of the phase and its change were observed with a polarizing microscope to determine the type of phase.

(2) Transition temperature (℃) In the measurement, a scanning calorimeter Diamond DSC system manufactured by Perkin Elmer or a high-sensitivity differential scanning calorimeter X-DSC7000 manufactured by Hitachi High-Tech Science (stock) is used. The temperature of the sample is raised and lowered at a rate of 3°C/min, and the starting point of the endothermic peak or exothermic peak accompanying the phase change of the sample is obtained by extrapolation, and the transition temperature is determined. The melting point of the compound and the polymerization initiation temperature are also measured using this device. The temperature at which the compound transforms from a solid into a smectic or nematic liquid crystal phase is sometimes referred to as the "lower limit temperature of the liquid crystal phase". The temperature at which a compound changes from a liquid crystal phase to a liquid is sometimes referred to as the "clear point".

Denote the crystal as C. When distinguishing the types of crystals, they are represented as C ₁ and C ₂ , respectively. The smectic phase is denoted as S, and the nematic phase is denoted as N. Smectic phase, smectic A phase in the layered region, smectic B phase, a smectic C phase or a smectic F phase of the case, are expressed as S _A, S _B, S _C or S _F. Denote liquid (isotropic) as I. The transition temperature is expressed as "C 50.0 N 100.0 I", for example. It means that the temperature for transforming from crystallization to nematic phase is 50.0°C, and the temperature for transforming from nematic phase to liquid is 100.0°C.

(3) Upper limit temperature of nematic phase (T _NI or NI; °C) Place the sample on the hot plate of a melting point measuring device equipped with a polarizing microscope and heat it at a rate of 1 °C/min. The temperature at which a part of the sample changes from a nematic phase to an isotropic liquid is measured. The upper limit temperature of the nematic phase is sometimes referred to simply as the "upper limit temperature". When the sample is a mixture of compound (1) and mother liquid crystal, it is represented by the symbol of _{T NI.} When the sample is a mixture of compound (1) and a compound such as component B, component C, and component D, it is represented by the symbol of NI.

(4) Lower limit temperature of nematic phase (T _C ; ℃) After storing the sample with nematic phase in a freezer at 0°C, -10°C, -20°C, -30°C, and -40°C for 10 days , Observe the liquid crystal phase. For example, when the sample maintains a nematic phase at -20°C and changes to a crystalline or smectic phase at -30°C, T _{C is} described as ≦-20°C. The lower limit temperature of the nematic phase is sometimes referred to simply as the "lower limit temperature".

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

(6) Optical anisotropy (refractive index anisotropy; measured at 25°C; Δn) Using light with a wavelength of 589 nm, the measurement is performed with an Abbe refractometer with a polarizing plate attached to the eyepiece. After rubbing the surface of the main shaft in one direction, drop the sample onto the main shaft. The refractive index (n∥) is measured when the direction of polarized light is parallel to the direction of rubbing. The refractive index (n⊥) is measured when the direction of polarized light is perpendicular to the direction of rubbing. The value of optical anisotropy (Δn) is calculated according to the formula of Δn=n∥-n⊥.

(7) Specific resistance (ρ; measured at 25°C; Ωcm) Inject 1.0 mL of sample into a container equipped with electrodes. A DC voltage (10 V) was applied to the container, and the DC current after 10 seconds was measured. The specific resistance is calculated according to the following formula. (Specific resistance)={(voltage)×(capacitance of container)}/{(direct current)×(dielectric constant of vacuum)}.

A sample with positive dielectric anisotropy and a sample with negative dielectric anisotropy may have different characteristic measurement methods. The method of measuring when the dielectric anisotropy is positive is described in items (8a) to (12a). When the dielectric anisotropy is negative, the measurement method is described in items (8b) to (12b).

(8a) Viscosity (rotational viscosity; γ1; measured at 25°C; mPa·s) Positive dielectric anisotropy: The measurement is based on the method described in "Molecular Crystals and Liquid Crystals" (Vol. 259, 37 (1995)) by M. Imai et al. . A sample was placed in a TN device with a torsion angle of 0 degrees and a gap between two glass substrates (cell gap) of 5 μm. A voltage was applied to the device in steps of 0.5 V in the range of 16 V to 19.5 V. After the voltage was not applied for 0.2 seconds, the voltage was repeatedly applied with only one rectangular wave (rectangular pulse; 0.2 seconds) and no voltage (2 seconds). The peak current and peak time of the transient current generated by this application are measured. Based on these measured values and the calculation formula (8) on page 40 of the paper by M. Imai et al., the value of the rotational viscosity is obtained. The value of dielectric anisotropy necessary for this calculation is obtained by the method described below using an element whose rotational viscosity has been measured.

(8b) Viscosity (rotational viscosity; γ1; measured at 25°C; mPa·s) Negative dielectric anisotropy: The measurement is based on the method described in "Molecular Crystals and Liquid Crystals" (Vol. 259, 37 (1995)) by M. Imai et al. . A sample is placed in a VA element with a distance between two glass substrates (cell gap) of 20 μm. A voltage was applied stepwise in units of 1 volt in the range of 39 volts to 50 volts to the device. After the voltage was not applied for 0.2 seconds, the voltage was repeatedly applied with only one rectangular wave (rectangular pulse; 0.2 seconds) and no voltage (2 seconds). The peak current and peak time of the transient current generated by this application are measured. Based on these measured values and the calculation formula (8) on page 40 of the paper by M. Imai et al., the value of the rotational viscosity is obtained. The dielectric anisotropy necessary for this calculation is a value measured in the item of dielectric anisotropy described below.

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

(9b) Dielectric anisotropy (Δε; measured at 25°C) Negative dielectric anisotropy: The value of dielectric anisotropy is calculated according to the formula Δε=ε∥-ε⊥. The dielectric constant (ε∥ and ε⊥) is measured as follows. 1) Measurement of dielectric constant (ε∥): Coat a fully cleaned glass substrate with a solution of octadecyltriethoxysilane (0.16 mL) in ethanol (20 mL). After the glass substrate was rotated by a rotator, it was heated at 150 degreeC for 1 hour. A sample was placed in a VA device with a distance (cell gap) of 4 μm between two glass substrates, and the device was sealed with an adhesive that was cured by ultraviolet rays. A sine wave (0.5 V, 1 kHz) was applied to the device, and after 2 seconds, the dielectric constant (ε∥) in the long axis direction of the liquid crystal molecules was measured. 2) Measurement of dielectric constant (ε⊥): Coat polyimide solution on a fully cleaned glass substrate. After sintering the glass substrate, rubbing treatment was performed on the resulting alignment film. A sample was placed in a TN device with a gap between two glass substrates (cell gap) of 9 μm and a twist angle of 80 degrees. A sine wave (0.5 V, 1 kHz) was applied to the device, and after 2 seconds, the dielectric constant (ε⊥) in the minor axis direction of the liquid crystal molecules was measured.

(10a) Elastic constant (K; measured at 25°C; pN) Positive dielectric anisotropy: In the measurement, the HP4284A LCR meter manufactured by Agilent Technologies was used. A sample is placed in a horizontal alignment element with a distance between two glass substrates (cell gap) of 20 μm. A charge of 0V to 20V is applied to the device, and the capacitance and the applied voltage are measured. Use the equations (2.98) and (2.101) on page 75 of the "Liquid Crystal Element Handbook" (Nikkan Kogyo Kogyo) to fit the measured capacitance (C) and applied voltage (V), according to the equation (2.99) The values of K ₁₁ and K _{33 are obtained.} Then, in equation (3.18) on page 171, _{K 22} is calculated using the values _{of K 11} and K ₃₃ obtained earlier. The elastic constant K is expressed as the average value _{of K 11} , K _22, and K _{33 obtained in this way.}

(10b) Elastic constants (K ₁₁ and K ₃₃ ; measured at 25°C; pN) Negative dielectric anisotropy: In the measurement, use the EC-1 elastic constant manufactured by TOYO Technica (stock) Tester. A sample is placed in a vertical alignment element with a distance (cell gap) of 20 μm between two glass substrates. A charge of 20V to 0V was applied to the device, and the capacitance and applied voltage were measured. Use the equations (2.98) and (2.101) on page 75 of the "Liquid Crystal Element Handbook" (Nikkan Kogyo Kogyo) to fit the values of electrostatic capacitance (C) and applied voltage (V), and obtain flexibility according to equation (2.100) The value of the constant.

(11a) Threshold voltage (Vth; measured at 25°C; V) Positive dielectric anisotropy: The LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source is set to a halogen lamp. A sample was placed in a normally white mode (normally white mode) TN device with a distance (cell gap) of 0.45/Δn (μm) between two glass substrates and a twist angle of 80 degrees. The voltage (32 Hz, rectangular wave) applied to the device is gradually increased from 0 V to 10 V in units of 0.02 V. At this time, the element was irradiated with light from the vertical direction, and the amount of light passing through the element was measured. A voltage-transmittance curve in which the transmittance is 100% when the amount of light reaches the maximum, and the transmittance is 0% when the amount of light is the smallest is prepared. The threshold voltage is expressed as the voltage at which the transmittance becomes 90%.

(11b) Threshold voltage (Vth; measured at 25°C; V) Negative dielectric anisotropy: In the measurement, an LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. The light source is set to a halogen lamp. Place a sample in a normally black mode (normally black mode) VA device with a distance of 4 μm between two glass substrates (cell gap) and anti-parallel rubbing directions, and seal the device with an adhesive that is cured by ultraviolet rays . The voltage (60 Hz, rectangular wave) applied to the device is increased from 0 V to 20 V in steps of 0.02 V. At this time, the element was irradiated with light from the vertical direction, and the amount of light passing through the element was measured. A voltage-transmittance curve in which the transmittance is 100% when the amount of light reaches the maximum, and the transmittance is 0% when the amount of light is the smallest is prepared. The threshold voltage is expressed as the voltage when the transmittance becomes 10%.

(12a) Response time (τ; measured at 25°C; ms) Positive dielectric anisotropy: The LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source is set to a halogen lamp. The Low-pass filter is set to 5 kHz. A sample was placed in a normally white mode (normally white mode) TN device with a distance (cell gap) of 5.0 μm between two glass substrates and a twist angle of 80 degrees. A rectangular wave (60 Hz, 5 V, 0.5 seconds) was applied to the element. At this time, the element was irradiated with light from the vertical direction, and the amount of light passing through the element was measured. When the light amount reaches the maximum, the transmittance is regarded as 100%, and when the light amount is the smallest, the transmittance is regarded as 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 is expressed as the sum of the rise time and fall time obtained in this way.

(12b) Response time (τ; measured at 25°C; ms) Negative dielectric anisotropy: In the measurement, an LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. The light source is set to a halogen lamp. The Low-pass filter is set to 5 kHz. The sample was placed in a normally black mode (normally black mode) PVA element with a distance between two glass substrates (cell gap) of 3.2 μm and an anti-parallel rubbing direction. The device is sealed with an adhesive that is cured by ultraviolet rays. A voltage slightly exceeding the threshold voltage was applied to the device for 1 minute, and then, while applying a voltage of 5.6 V, ^{ultraviolet rays of 23.5 mW/cm 2} were irradiated for 8 minutes. A rectangular wave (60 Hz, 10 V, 0.5 seconds) was applied to this element. At this time, the element was irradiated with light from the vertical direction, and the amount of light passing through the element was measured. When the light amount reaches the maximum, the transmittance is regarded as 100%, and when the light amount is the smallest, the transmittance is regarded as 0%. The response time is expressed by the time (fall time; milliseconds) required for the transmittance to change from 90% to 10%.

(13) Voltage retention rate The polymerizable compound is polymerized by irradiating ultraviolet light with black light, F40T10/BL (peak wavelength 369 nm) manufactured by Eye Graphics (stock). The device was charged by applying a pulse voltage (1 V for 60 microseconds) at 60°C. The attenuated voltage was measured during a period of 1.67 seconds with a high-speed voltmeter, and the area A between the voltage curve per unit period and the horizontal axis was obtained. Area B is the area without attenuation. The voltage retention rate is expressed as the percentage of area A to area B.

raw material Solmix (registered trademark) A-11 is a mixture of ethanol (85.5%), methanol (13.4%) and isopropanol (Isopropanol, IPA) (1.1%). It is sold from Japan Alcohol (shares) )Obtain. [Synthesis Example 1]

In the first step, compound (T-1) (5.0 g), compound (T-2) (5.9 g), p-toluenesulfonic acid monohydrate (PTSA·H ₂ O) (0.70 g) and toluene (100 ml) Put it into the reactor and heat to reflux for 5 hours. The reaction mixture was poured into water, and the water layer was extracted with toluene. The obtained organic layer was washed with water, and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, ethanol:toluene=3:1) to obtain compound (T-3) (0.5 g; 9%).

Step 2 Compound (T-4) (3.1 g), compound (T-3) (0.5 g), potassium carbonate (0.86 g) and N,N-dimethylformamide (50 ml) synthesized by a known method ) Put it into the reactor and heat to reflux 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 with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:ethyl acetate=2:1) to obtain compound (1-3-1) (0.83 g; 51%) ).

¹ H-NMR (ppm; CDCl ₃ ): 7.41-7.39 (m, 2H), 6.90-86 (m, 2H), 4.29 (t, J=6.5 Hz, 2H), 3.81-3.56 (m, 8H), 3.35 (t, J=5.9 Hz, 2H), 2.77-2.75 (m, 1H), 1.98-1.19 (m, 32H), 0.88 (t, J=7.2 Hz, 3H). [Synthesis example 2]

Step 1 The compound (T-5) (10.3 g), potassium carbonate (10.5 g) and N,N-dimethylformamide (90 ml) were put into the reactor and stirred at 50°C for 30 minutes. A solution of compound (T-6) (18.0 g) in N,N-dimethylformamide (20 ml) was added dropwise thereto, and the mixture was stirred at 50°C for 5 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 with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:ethyl acetate=2:1) to obtain compound (T-7) (18.4 g; 91%).

Step 2 Put compound (T-7) (17.3 g), tetrahydrofuran (Tetrahydrofuran, THF) (170 ml), methanol (85 ml) and pyridinium paratoluenesulfonate (PPTS) (6.8 g) into the reactor In, stirring at 50°C for 4 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 with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:ethyl acetate=1:2) to obtain compound (T-8) (10.2 g; 80%).

Step 3 The compound (T-8) (0.8 g) and THF (20 ml) were put into the reactor and cooled to 0°C. Compound (T-9) (2.0 g) and triphenylphosphine (1.1 g) were added thereto, and diethyl azodicarboxylate (1.88 ml) was added dropwise, followed by stirring at room temperature (25°C) for 12 hour. 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 with 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 (1-3-133) (0.89 g; 33%) ).

¹ H-NMR (ppm; CDCl ₃ ): 7.64 (d, J=9.5 Hz, 1H), 7.37 (d, J=8.5 Hz, 1H), 6.86-6.82 (m, 4H), 6.25 (d, J= 9.5 Hz, 1H), 6.10 (s, 2H), 5.55-5.54 (m, 2H), 4.18 (t, J=6.5 Hz, 4H), 4.10 (t, J=6.0 Hz, 2H), 3.81 (t, J=6.2 Hz, 2H), 2.70-2.67 (m, 4H), 2.37-2.32 (m, 1H), 2.07-1.96 (m, 8H), 1.94 (s, 6H), 1.88-1.72 (m, 8H) , 1.38-1.20 (m, 8H), 1.16-0.96 (m, 9H), 0.90-0.82 (m, 5H).

[Comparative Example 1] Compatibility comparison As a comparative compound, the following compound (S-1) was selected. This compound is synthesized according to a known method.

¹ H-NMR (ppm; CDCl ₃ ): 6.24 (s, 1H), 5.64 (s, 1H), 4.74-4.67 (m, 1H), 3.79-3.75 (m, 2H), 3.68-3.63 (m, 2H) ), 2.59-2.57 (m, 2H), 2.39 (d, J=7.4 Hz, 2H), 2.04-2.02 (m, 2H), 1.87-1.69 (m, 7H), 1.39-0.80 (m, 22H).

The compatibility of the compound (1-3-1) and the comparative compound (S-1) with respect to the liquid crystal composition was compared. The mother liquid crystal (i) containing the following compounds (i-1) to (i-9) was used for the evaluation.

The ratio of the components of the mother liquid crystal (i) is expressed in% by weight.

A sample in which the compound (1-3-1) or the comparative compound (S-1) is added to the mother liquid crystal (i) in a ratio of 3% by weight to 0.5% by weight is prepared. The sample was allowed to stand at 25°C and -20°C for 7 days, and then visually observed. The case where the nematic phase was maintained was represented by ○, and the case where a crystal or a smectic phase was precipitated was represented by ×. The results are shown in Table 2.

室溫 -20℃ 室溫 -20℃ 3.0 ○ ○ × × 1.0 ○ ○ × × 0.5 ○ ○ ○ × [Table 2] Table 2. Compatibility Compound (1-3-1) Compound (S-1) Addition amount (wt%)

Room temperature -20℃ Room temperature -20℃ 3.0 ○ ○ X X 1.0 ○ ○ X X 0.5 ○ ○ ○ X

As a result of comparing the solubility, even if 3% by weight of the compound (1-3-1) is added to the mother liquid crystal (i), the nematic phase is maintained at both 25°C and -20°C. In contrast, When 1% by weight of the comparative compound (S-1) was added, crystals were precipitated at 25°C. These compounds have a ring structure and are similar in terms of having a polar group, but the compatibility of the two is quite different. It can be considered that the reason is that the crystallinity of the compound (1-3-1) is lower than that of the diol compound, and therefore, the affinity for the liquid crystal composition is improved compared with the comparative compound (S-1). Therefore, the compound of the present application can be said to be an excellent compound with large compatibility.

[Comparative Example 2] Compatibility comparison As a comparative compound, the following compound (S-2) was selected. This compound is synthesized according to a known method.

¹ H-NMR (ppm; CDCl ₃ ): 7.15-7.08 (m, 3H), 7.02 (s, 2H), 6.31 (s, 1H), 6.12 (s, 2H), 5.71 (s, 1H), 5.78 ( s, 2H), 4.29 (t, J=6.0 Hz, 2H), 4.22 (t, J=6.4 Hz, 4H), 3.88-3.81 (m, 4H), 3.71-3.68 (m, 2H), 2.77-2.71 (m, 6H), 2.58 (q, J=7.5 Hz, 2H), 2.51 (tt, J=12.1 Hz, 3.1 Hz, 1H), 2.43 (d, J=7.3 Hz, 2H), 2.08-1.90 (m , 18H), 1.55-1.25 (m, 12H), 1.14-1.05 (m, 5H), 0.92 (m, J=6.9 Hz, 3H).

A sample prepared by adding the compound (1-3-133) or the comparative compound (S-2) to the mother liquid crystal (i) in a ratio of 1.5% by weight to 0.5% by weight was prepared. The sample was allowed to stand at 25°C and -20°C for 10 days, and then visually observed. The case where the nematic phase was maintained was indicated as ○, and the case where crystals or smectic phase was precipitated was indicated as ×. The results are shown in Table 3.

室溫 -20℃ 室溫 -20℃ 1.5 ○ ○ ○ × 1.0 ○ ○ ○ × 0.5 ○ ○ ○ × [Table 3] Table 3. Compatibility Compound (1-3-133) Compound (S-2) Addition amount (wt%)

Room temperature -20℃ Room temperature -20℃ 1.5 ○ ○ ○ X 1.0 ○ ○ ○ X 0.5 ○ ○ ○ X

Comparing the solubility results, even if 1.5% by weight of the compound (1-3-133) is added to the mother liquid crystal (i), the nematic phase is maintained at both 25°C and -20°C. In contrast, In any case where 1.5 wt% to 0.5 wt% of the comparative compound (S-2) was added, crystals were also precipitated at -20°C. These compounds have a ring structure and are similar in terms of having a polar group, but the compatibility of the two is quite different. It can be considered that the reason is that the crystallinity of the compound (1-3-133) is lower than that of the diol compound, and therefore the affinity for the liquid crystal composition is improved compared with the comparative compound (S-2). Therefore, the compound of the present application can be said to be an excellent compound with large compatibility.

The compound shown below can be synthesized while referring to the method described in the synthesis example or the item "2. Synthesis of compound (1)".

2. Examples of composition The compounds in the examples are represented by symbols based on the definition in Table 4 below. In Table 4, the three-dimensional configuration related to 1,4-cyclohexylene is the trans configuration. The number in parentheses after the symbol corresponds to the number of the compound. The symbol (-) refers to other liquid crystal compounds. The ratio (percentage) of the liquid crystal compound is the weight percentage (% by weight) based on the weight of the liquid crystal composition. Finally, the characteristic values of the liquid crystal composition are summarized. The characteristics are measured according to the method described above, (without extrapolation) directly record the measured value.

[Table 4]

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

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

[Use example 2] 3-HH-V 30% 3-HH-V1 5% 5-HH-V 10% 3-HHB-1 5% V-HHB-1 4% 2-BB(F)B-3 5% 3-HHEH-5 (3-13) 3% 1V2-BB-F 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% The following compound (1-3-8) was added to the composition in a ratio of 3% by weight.

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

[Use example 3] 1-BB-3 6% 1-BB-5 7% 2-BTB-1 (2-10) 3% 3-HHB-1 7% 3-HHB-3 12% 3-HHB-O1 6% 3-HHB-F 4% 2-HHB(F)-F 8% 3-HHB(F)-F 8% 5-HHB(F)-F 7% 3-HHB(F,F)-F (6-3) 5% 3-HHEB-F 4% 5-HHEB-F 4% 2-HB-C 6% 3-HB-C 13% The following compound (1-3-122) was added to the composition in a ratio of 3% by weight.

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

[Use example 4] 1V2-HH-1 3% 1V2-HH-3 4% 7-HB(F,F)-F 3% 2-HHB(F)-F 8% 3-HHB(F)-F 12% 5-HHB(F)-F 10% 2-HBB-F (6-22) 4% 3-HBB-F (6-22) 2% 5-HBB-F (6-22) 4% 2-HBB(F)-F 9% 3-HBB(F)-F 10% 5-HBB(F)-F 16% 3-HBB(F,F)-F (6-24) 5% 5-HBB(F,F)-F (6-24) 10% The following compound (1-3-131) was added to the composition in a ratio of 3.5% by weight.

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

[Use Example 5] 3-HH-4 11% 5-HB-O2 (2-5) 4% 7-HB-1 2% 5-HBB(F)B-2 5% 5-HBB(F)B-3 5% 3-HB-CL 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% The following compound (1-3-132) was added to the composition in a ratio of 3% by weight.

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

[Use Example 6] 3-HH-V 30% 3-HH-V1 8% 3-HHB-1 (3-1) 4% V-HHB-1 5% V2-BB(F)B-1 4% 3-HHEH-5 (3-13) 4% 3-HHEBH-3 (4-6) 3% 1V2-BB-F 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% The following compound (1-4-10) was added to the composition in a ratio of 3% by weight.

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

[Use Example 7] 5-HBBH-3 3% 3-HB(F)BH-3 (4-2) 3% 5-HB-F 12% 6-HB-F 9% 7-HB-F 7% 2-HHB-OCF3 7% 3-HHB-OCF3 (6-1) 4% 4-HHB-OCF3 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 5% 5-HBB(F)-F 15% The following compound (1-4-16) was added to the composition in a ratio of 2% by weight.

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

[Use example 8] 3-HH-V 25% 3-HH-V1 10% V-HH-V1 9% 3-HHB-1 (3-1) 4% V-HHB-1 5% 1-BB(F)B-2V 4% 3-HHEH-5 (3-13) 3% 1V2-BB-F 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% The following compound (1-4-20) was added to the composition in a ratio of 3% by weight.

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

[Use Example 9] V-HBB-2 10% 1O1-HBBH-4 (4-1) 3% 1O1-HBBH-5 5% 3-HHB(F,F)-F 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 21% 3-H2BB(F,F)-F (6-27) 10% 5-HHBB(F,F)-F 4% 3-HH2BB(F,F)-F (7-15) 2% 5-HHEBB-F (7-17) 2% The following compound (1-4-118) was added to the composition in a ratio of 4% by weight.

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

[Use Example 10] 2-HH-3 8% 3-HH-4 8% 1O1-HBBH-5 4% 5-HB-CL 15% 3-HHB-F 4% 3-HHB-CL (6-1) 3% 4-HHB-CL 4% 3-HHB(F)-F 10% 4-HHB(F)-F 9% 5-HHB(F)-F 9% 7-HHB(F)-F 8% 5-HBB(F)-F 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% The following compound (1-1-28) was added to the composition in a ratio of 3% by weight.

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

[Use example 11] 3-HH-4 5% 3-HH-5 10% 3-HB-O2 (2-5) 15% 3-HHB-1 5% 3-HHB-O1 8% 5-HB-CL 17% 7-HB(F,F)-F 3% 2-HHB(F)-F 8% 3-HHB(F)-F 8% 5-HHB(F)-F 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% The following compound (1-2-52) was added to the composition in a ratio of 3% by weight.

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

[Use example 12] 3-HH-V 25% 3-HH-V1 10% 3-HHB-1 5% V-HHB-1 7% V2-BB(F)B-1 5% 3-HHEH-5 (3-13) 3% 1V2-BB-F 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% The following compound (1-3-126) was added to the composition in a ratio of 2% by weight.

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

[Use example 13] V2-HHB-1 4% 3-HB-CL (5-2) 3% 5-HB-CL 7% 3-HHB-OCF3 (6-1) 5% 5-HHB(F)-F 7% V-HHB(F)-F 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% The following compound (1-3-82) was added to the composition in a ratio of 2% by weight.

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

[Use example 14] 3-HH-4 12% 3-HH-5 7% 3-HHB-1 13% 5-HB-CL 3% 7-HB(F)-F 7% 2-HHB(F,F)-F (6-3) 2% 3-HHB(F,F)-F 7% 3-HHEB-F 8% 5-HHEB-F 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% The following compound (1-3-92) was added to the composition in a ratio of 2% by weight.

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

[Use Example 15] 3-HH-V 30% 3-HH-V1 10% 3-HHB-1 5% V-HHB-1 3% 3-HBB-2 6% V2-BB(F)B-1 5% 3-HHEH-3 (3-13) 3% 3-HHEH-5 (3-13) 3% 1V2-BB-F 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% The following compound (1-3-107) was added to the composition in a ratio of 3% by weight.

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

[Use Example 16] 2-HH-5 2% 3-HH-4 7% 5-B(F)BB-2 4% 5-HB-CL 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 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% The following compound (1-4-57) was added to the composition in a ratio of 2% by weight.

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

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

no

Claims (14)

A compound represented by formula (1);

In the formula (1), R ¹ is hydrogen or an alkyl group having 1 to 15 carbons. In the R ¹ , at least one -CH ₂ -may be substituted by -O- or -S-, and at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; ring A ¹ and ring A ^{2 are} independently 1,2-cyclopropylidene, 1,3- Cyclobutyl, 1,3-cyclopentyl, 1,4-cyclohexyl, 1,4-cycloheptyl, 1,4-cyclohexenyl, 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 the ring A ¹ and ring A ² , at least one hydrogen can be fluorine , Chlorine, C1-C10 alkyl group, C2-C10 alkenyl group, C1-C9 alkoxy group or C2-C9 alkenyloxy group, at least one hydrogen may be substituted by fluorine or chlorine Substitution; 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 an alkylene having 1 to 6 carbon atoms, in the Z ¹ , At least one -CH ₂ -can be substituted by -O-, -CO-, -COO-, -OCO- or -OCOO-, and at least one -(CH ₂ ) ₂ -can be -CH=CH- or -C≡C -Substitution, at least one hydrogen may be substituted by fluorine or chlorine; P ¹ and P ^{2 are} independently selected from the group represented by formula (1-p1) and formula (1-p2);

In formula (1-p1) and formula (1-p2), Sp ^{1 is} independently a single bond or an alkylene group having 1 to 15 carbons, and in the Sp ¹ , at least one -CH ₂ -may be -O- , -CO-, -COO-, -OCO- or -OCOO- substituted, at least one -(CH ₂ ) ₂ -can be replaced by -CH=CH- or -C≡C-, at least one hydrogen can be replaced by fluorine or chlorine Substitution; M ¹ and M ^{2 are} independently hydrogen, fluorine, chlorine, an alkyl group with 1 to 5 carbons, or an alkyl group with 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine; Y ^{1 is} independently hydrogen , C1-C10 alkyl group, C1-C9 alkoxy group, C2-C9 alkoxyalkyl group, C1-C9 alkylthio group or C2-C9 alkylsulfide In the Y ¹ , at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by bromine, fluorine or chlorine; R ^{2 is} independently Is a straight chain alkyl group having 1 to 10 carbons or a branched chain alkyl group having 3 to 10 carbons, or a cyclic alkyl group having 3 to 8 carbons; in formula (1), Sp ² is a single bond or a carbon number of 1 To 10, in the Sp ² at least one -CH ₂ -may be represented by -O-, -CO-, -COO-, -OCO-, -OCOO- or formula (1-a) At least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine, chlorine, formula (1-p1) or formula (1-p2) The indicated group is substituted;

X ¹ is a group selected from groups represented by formula (1-x1) to formula (1-x10);

In formulas (1-x1) to (1-x10), W ¹ is a methine group or nitrogen, where the hydrogen of the methine group is substituted with an alkyl group having 1 to 6 carbon atoms; m1 is independently 0, 1 Or 2, in the -(CH ₂ ) _m1 -, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; W ² Is a methine group or nitrogen, where the hydrogen of the methine group can be substituted by an alkyl group having 1 to 6 carbons; K ¹ is an alkylene group having 1 or 2 carbons, and in said K ¹ , at least one -CH ₂ -may be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; K ² is Alkylene with carbon number 1 or 2, in said K ² , at least one -CH ₂ -is substituted by -O- or -S-, and at least one hydrogen can be substituted by fluorine or chlorine; n1 is 2 or 3, said -(CH ₂ ) _n1 -, at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; K ^{3 is} independently the number of carbons In the alkylene group of 1, in the K ³ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; K ⁴ is -S- or -CO-; K ^{5 is} independently an alkylene having 1 or 2 carbon atoms, in said K ⁵ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one -( CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; p1 is independently 0 or 1, in the -(CH ₂ ) _p1 -, at least one hydrogen may be substituted by fluorine or chlorine; K ⁶ is the alkylene group having a carbon number of 1, the K ^6, at least one -CH ₂ - may be substituted with -O- or -S-, may be at least one hydrogen or fluoro chloro substituent; K ⁷ independently a single bond or alkylene group having a carbon number of 1 to 3, the K ^7, at least one -CH ₂ - replaced by -O- or -S-, may be at least one hydrogen or fluoro Chlorine substitution; K ⁸ is hydrogen or an alkyl group having 1 to 4 carbons. In said K ⁸ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; when p1 is all 0, a is 1, 2, 3 or 4. The compound according to claim 1, which is represented by any one of formula (1-1) to formula (1-8);

In formulas (1-1) to (1-8), R ¹ is hydrogen or an alkyl group having 1 to 15 carbons, and in the R ¹ , at least one -CH ₂ -may be -O- or -S- Substitution, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; Ring A ¹ to Ring A ^{5 are} independently 1,4- Cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane -2,5-diyl group, in the ring A ¹ to ring A ⁵ , at least one hydrogen may be fluorine, chlorine, an alkyl group having 1 to 10 carbons, an alkenyl group having 2 to 10 carbons, or a carbon number of 1 to The alkoxy group of 9 or the alkenyloxy group of carbon number 2 to 9, 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 single bonds, -(CH ₂ ) ₂ -, -CH=CH-, -C≡C-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -CH ₂ O-, -OCH ₂ -or -CF=CF-; P ¹ and P ^{2 are} independently groups selected from groups represented by formula (1-p1) and formula (1-p2);

In the formulas (1-p1) and (1-p2), Sp ^{1 is} independently a single bond or an alkylene group having 1 to 7 carbon atoms, and in the Sp ¹ at least one -CH ₂ -may pass through -O- , -CO- or -COO-, at least one -(CH ₂ ) ₂ -can be replaced by -CH=CH-, at least one hydrogen can be replaced by fluorine or chlorine; M ¹ and M ^{2 are} independently hydrogen, fluorine, Chlorine, an alkyl group having 1 to 5 carbons, or an alkyl group having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine; Y ^{1 is} independently hydrogen, an alkyl group having 1 to 10 carbons, and an alkyl group having 1 to 10 carbons. 9 alkoxy group, carbon number 2-9 alkoxyalkyl group, carbon number 1-9 alkylthio group or carbon number 2-9 alkylthio group, in said Y ¹ , at least one -( CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by bromine, fluorine or chlorine; R ^{2 is} independently a linear alkyl group with 1 to 10 carbons or carbon number A branched chain alkyl group having 3 to 10 or a cyclic alkyl group having 3 to 8 carbons; In formula (1-1) to formula (1-8), Sp ² is a single bond or an alkylene having 1 to 7 carbons In the Sp ² , at least one -CH ₂ -may be substituted by -O-, -CO-, -COO- or a group represented by formula (1-a), and at least one -(CH ₂ ) ₂ -may Substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine, chlorine, a group represented by formula (1-p1) or formula (1-p2);

X ¹ is a group selected from groups represented by formula (1-x1) to formula (1-x10);

In formulas (1-x1) to (1-x10), W ¹ is a methine group or nitrogen, where the hydrogen of the methine group is substituted with an alkyl group having 1 to 6 carbon atoms; m1 is independently 0, 1 Or 2, in the -(CH ₂ ) _m1 -, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; W ² Is a methine group or nitrogen, where the hydrogen of the methine group can be substituted by an alkyl group having 1 to 6 carbons; K ¹ is an alkylene group having 1 or 2 carbons, and in said K ¹ , at least one -CH ₂ -may be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; K ² is Alkylene with carbon number 1 or 2, in said K ² , at least one -CH ₂ -is substituted by -O- or -S-, and at least one hydrogen can be substituted by fluorine or chlorine; n1 is 2 or 3, said -(CH ₂ ) _n1 -, at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; K ^{3 is} independently the number of carbons In the alkylene group of 1, in the K ³ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; K ⁴ is -S- or -CO-; K ^{5 is} independently an alkylene having 1 or 2 carbon atoms, in said K ⁵ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one -( CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; p1 is independently 0 or 1, in the -(CH ₂ ) _p1 -, at least one hydrogen may be substituted by fluorine or chlorine; K ⁶ is the alkylene group having a carbon number of 1, the K ^6, at least one -CH ₂ - may be substituted with -O- or -S-, may be at least one hydrogen or fluoro chloro substituent; K ⁷ independently a single bond or alkylene group having a carbon number of 1 to 3, the K ^7, at least one -CH ₂ - replaced by -O- or -S-, may be at least one hydrogen or fluoro Chlorine substitution; K ⁸ is hydrogen or an alkyl group having 1 to 4 carbons. In said K ⁸ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; in formula (1-1), no p1 in formula (1-x7) is 0 Case. The compound according to claim 1 or claim 2, which is represented by any one of formula (1-9) to formula (1-16);

In formulas (1-9) to (1-16), R ¹ is hydrogen or an alkyl group having 1 to 10 carbons. In the R ¹ , at least one -CH ₂ -may be substituted by -O-, and at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH-, at least one hydrogen may be substituted by fluorine or chlorine; ring A ¹ to ring A ^{5 are} independently 1,4-cyclohexyl or 1,4-ring Hexenyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl, the In ring A ¹ to ring A ⁵ , at least one hydrogen may be substituted with fluorine, an alkyl group having 1 to 5 carbons, an alkenyl group having 2 to 5 carbons, or an alkoxy group having 1 to 4 carbons; b and c are independently Is 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 -; P ¹ and P ^{2 are} independently groups selected from groups represented by formula (1-p1) and formula (1-p2);

In the formulas (1-p1) and (1-p2), Sp ^{1 is} independently a single bond or an alkylene having 1 to 5 carbons, and in the Sp ¹ at least one -CH ₂ -may pass through -O- Substitution, at least one -(CH ₂ ) ₂ -can be replaced by -CH=CH-, at least one hydrogen can be replaced by fluorine or chlorine; M ¹ and M ^{2 are} independently hydrogen, fluorine, chlorine, carbon number 1 to 5 An alkyl group or an alkyl group having 1 to 5 carbons in which at least one hydrogen is substituted by fluorine or chlorine; Y ^{1 is} independently hydrogen, an alkyl group having 1 to 10 carbons, an alkoxy group having 1 to 9 carbons, and a carbon number alkoxyalkyl group having 2 to 9 carbon atoms, alkylthio group having 1 to 2 carbon atoms or alkylthio 9 to 9, wherein Y ^1, at least one - (CH _{2) 2} - may be - CH=CH- or -C≡C- substituted, at least one hydrogen may be substituted by bromine, fluorine or chlorine; R ^{2 is} independently a straight chain alkyl group with 1 to 10 carbons or a branched chain alkyl group with 3 to 10 carbons , Or a cyclic alkyl group having 3 to 8 carbons; In formulas (1-9) to (1-16), Sp ² is a single bond or an alkylene having 1 to 7 carbons, and in Sp ² , At least one -CH ₂ -may be substituted by -O- or a group represented by formula (1-a), at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one Hydrogen may be substituted by fluorine, chlorine, a group represented by formula (1-p1) or formula (1-p2);

X ¹ is a group selected from groups represented by formula (1-x1) to formula (1-x10);

In formulas (1-x1) to (1-x10), W ¹ is a methine group or nitrogen, where the hydrogen of the methine group is substituted with an alkyl group having 1 to 6 carbon atoms; m1 is independently 0, 1 Or 2, in the -(CH ₂ ) _m1 -, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; W ² Is a methine group or nitrogen, where the hydrogen of the methine group can be substituted by an alkyl group having 1 to 6 carbons; K ¹ is an alkylene group having 1 or 2 carbons, and in the K ¹ , at least one -CH ₂ -may be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; K ² is Alkylene with carbon number 1 or 2, in said K ² , at least one -CH ₂ -is substituted by -O- or -S-, and at least one hydrogen can be substituted by fluorine or chlorine; n1 is 2 or 3, said -(CH ₂ ) _n1 -, at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; K ^{3 is} independently the number of carbons In the alkylene group of 1, in the K ³ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; K ⁴ is -S- or -CO-; K ^{5 is} independently an alkylene having 1 or 2 carbon atoms, in said K ⁵ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one -( CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; p1 is independently 0 or 1, in the -(CH ₂ ) _p1 -, at least one hydrogen may be substituted by fluorine or chlorine; K ⁶ is the alkylene group having a carbon number of 1, the K ^6, at least one -CH ₂ - may be substituted with -O- or -S-, may be at least one hydrogen or fluoro chloro substituent; K ⁷ independently a single bond or alkylene group having a carbon number of 1 to 3, the K ^7, at least one -CH ₂ - replaced by -O- or -S-, may be at least one hydrogen or fluoro Chlorine substitution; K ⁸ is hydrogen or an alkyl group having 1 to 4 carbons. In said K ⁸ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; in formula (1-9), no p1 in formula (1-x7) is 0 Case. The compound according to claim 1 or claim 2, which is represented by any one of formula (1-17) to formula (1-94);

In formulas (1-17) to (1-94), R ¹ is an alkyl group having 1 to 10 carbons; Z ¹ to Z ^{3 are} independently single bonds or -(CH ₂ ) ₂ -; Sp ^{1 is} independently It is a single bond or an alkylene having 1 to 5 carbon atoms, in the Sp ¹ at least one -CH ₂ -may be substituted by -O-; M ¹ and M ^{2 are} independently hydrogen, fluorine, chlorine, and carbon number 1. Alkyl group to 5, or an alkyl group of 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine; Y ^{1 is} independently hydrogen, an alkyl group having 1 to 10 carbons, or an alkoxy group having 1 to 9 carbons , carbon atoms, alkoxyalkyl having 2 to 9 carbon atoms, alkylthio group having 1 to 2 carbon atoms or alkylthio 9 to 9, wherein Y ^1, at least one - (CH _{2) 2} - May be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by bromine, fluorine or chlorine; R ^{2 is} independently a linear alkyl group with 1 to 10 carbons or a branch with 3 to 10 carbons Alkyl or cyclic alkyl having 3 to 8 carbons; Y ¹¹ to Y ^{21 are} independently hydrogen, fluorine, alkyl having 1 to 5 carbons, alkenyl having 2 to 5 carbons, or carbon 1 to 4 is an alkoxy group; Sp ² is a single bond or an alkylene group having 1 to 7 carbon atoms, in the Sp ² at least one -CH ₂ -may be -O- or a group represented by the formula (1-a) Substitution, at least one -(CH ₂ ) ₂ -can be replaced by -CH=CH- or -C≡C-, at least one hydrogen can be represented by fluorine, chlorine, formula (1-p1) or formula (1-p2) Substitution of the group;

In the formulas (1-p1) and (1-p2), Sp ^{1 is} independently a single bond or an alkylene having 1 to 5 carbons, and in the Sp ¹ at least one -CH ₂ -may pass through -O- Substitution, at least one -(CH ₂ ) ₂ -can be replaced by -CH=CH-, at least one hydrogen can be replaced by fluorine or chlorine; M ¹ and M ^{2 are} independently hydrogen, fluorine, chlorine, carbon number 1 to 5 An alkyl group or an alkyl group having 1 to 5 carbons in which at least one hydrogen is substituted by fluorine or chlorine; Y ^{1 is} independently hydrogen, an alkyl group having 1 to 10 carbons, an alkoxy group having 1 to 9 carbons, and a carbon number alkoxyalkyl group having 2 to 9 carbon atoms, alkylthio group having 1 to 2 carbon atoms or alkylthio 9 to 9, wherein Y ^1, at least one - (CH _{2) 2} - may be - CH=CH- or -C≡C- substituted, at least one hydrogen may be substituted by bromine, fluorine or chlorine; R ^{2 is} independently a straight chain alkyl group with 1 to 10 carbons or a branched chain alkyl group with 3 to 10 carbons , Or a cyclic alkyl group having 3 to 8 carbons; In formula (1-17) to formula (1-94), Sp ³ and Sp ^{4 are} independently a single bond or an alkylene having 1 to 5 carbons, so In the aforementioned Sp ³ and Sp ⁴ , at least one -CH ₂ -may be substituted by -O-; X ¹ is a group selected from the group represented by the formula (1-x1) to the formula (1-x10);

In formulas (1-x1) to (1-x10), W ¹ is a methine group or nitrogen, where the hydrogen of the methine group is substituted with an alkyl group having 1 to 6 carbon atoms; m1 is independently 0, 1 Or 2, in the -(CH ₂ ) _m1 -, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; W ² Is a methine group or nitrogen, where the hydrogen of the methine group can be substituted by an alkyl group having 1 to 6 carbons; K ¹ is an alkylene group having 1 or 2 carbons, and in said K ¹ , at least one -CH ₂ -may be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; K ² is Alkylene with carbon number 1 or 2, in said K ² , at least one -CH ₂ -is substituted by -O- or -S-, and at least one hydrogen can be substituted by fluorine or chlorine; n1 is 2 or 3, said -(CH ₂ ) _n1 -, at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; K ^{3 is} independently the number of carbons In the alkylene group of 1, in the K ³ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one hydrogen may be substituted by fluorine or chlorine; K ⁴ is -S- or -CO-; K ^{5 is} independently an alkylene having 1 or 2 carbon atoms, in said K ⁵ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one -( CH ₂ ) ₂ -may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine; p1 is independently 0 or 1, in the -(CH ₂ ) _p1 -, at least one hydrogen may be substituted by fluorine or chlorine; K ⁶ is the alkylene group having a carbon number of 1, the K ^6, at least one -CH ₂ - may be substituted with -O- or -S-, may be at least one hydrogen or fluoro chloro substituent; K ⁷ independently a single bond or alkylene group having a carbon number of 1 to 3, the K ^7, at least one -CH ₂ - replaced by -O- or -S-, may be at least one hydrogen or fluoro Chlorine substitution; K ⁸ is hydrogen or an alkyl group having 1 to 4 carbons. In said K ⁸ , at least one -CH ₂ -may be substituted by -O-, -CO- or -S-, and at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; formula (1-17), formula (1-18), formula (1-47) and formula In (1-48), there is no case where p1 in formula (1-x7) is all 0. A liquid crystal composition containing at least one of the compounds described in any one of Claims 1 to 4. The liquid crystal composition according to claim 5, which contains at least one compound selected from the group of compounds represented by formula (2) to formula (4);

In formulas (2) to (4), R ¹¹ and R ^{12 are} independently an alkyl group having 1 to 10 carbons or an alkenyl group having 2 to 10 carbons, and at least one of ^{R 11} and R ^{12 is -CH} ₂ -may be substituted by -O-, and at least one hydrogen may be substituted by fluorine; ring B ¹ , ring B ² , ring B ³ and ring B ^{4 are} independently 1,4-cyclohexylene and 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 single bonds , -COO-, -(CH ₂ ) ₂ -, -CH=CH- or -C≡C-. The liquid crystal composition according to claim 5 or claim 6, which contains at least one compound selected from the group of compounds represented by formula (5) to formula (7);

In formulas (5) to (7), R ¹³ is an alkyl group having 1 to 10 carbons or an alkenyl group having 2 to 10 carbons, and in the R ¹³ at least one -CH ₂ -may be substituted with -O- , 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 ; 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 substituted by fluorine; Z ¹⁴ , Z ¹⁵ and Z ^{16 are} independently single bonds, -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 5 or claim 6, which contains at least one compound selected from the group of compounds represented by formula (8);

In formula (8), R ¹⁴ is an alkyl group having 1 to 10 carbons or an alkenyl group having 2 to 10 carbons. In the R ¹⁴ , at least one -CH ₂ -may be substituted by -O-, and at least one hydrogen may be Substituted by fluorine; X ¹² is -C≡N or -C≡CC≡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 substituted 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 5 or claim 6, which contains at least one compound selected from the group of compounds represented by formula (11) to formula (19);

In formulas (11) to (19), R ¹⁵ , R ¹⁶ and R ^{17 are} independently an alkyl group having 1 to 10 carbons or an alkenyl group having 2 to 10 carbons, and R ¹⁵ , R ¹⁶ and R ¹⁷ Among them, at least one -CH ₂ -may be substituted by -O-, at least one hydrogen may be substituted by fluorine, and R ¹⁷ may also be hydrogen or fluorine; ring E ¹ , ring E ² , ring E ³ and ring E ^{4 are} independently It is 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 substituted by fluorine; ring E ⁵ and ring E ^{6 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 single bonds, -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 independently -CHF- or -CF ₂ -; j, k, m, n, p, q, r and s Independently 0 or 1, the sum of k, m, n, and p is 1 or 2, the sum of q, r, and s is 0, 1, 2, or 3, and t is 1, 2, or 3. The liquid crystal composition according to claim 5 or claim 6, which contains at least one polymerizable compound represented by formula (20) (except for 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-dioxyl Alk-2-yl, pyrimidin-2-yl or pyridin-2-yl, in the ring F and ring I, at least one hydrogen may be halogenated, alkyl having 1 to 12 carbons, or alkyl having 1 to 12 carbons. The oxy group or at least one hydrogen is substituted by a halogen-substituted alkyl group having 1 to 12 carbons; 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, tetrahydro Pyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, in the ring G, at least One hydrogen may be substituted by halogen, an alkyl group having 1 to 12 carbons, an alkoxy group having 1 to 12 carbons, or an alkyl group having 1 to 12 carbons in which at least one hydrogen is substituted by halogen; Z ²² and Z ^{23 are} independently A single bond or an alkylene having 1 to 10 carbon atoms, in Z ²² and Z ²³ , at least one -CH ₂ -may be substituted with -O-, -CO-, -COO- or -OCO-, and at least one- (CH ₂ ) ₂ -can be replaced by -CH=CH-, -C(CH ₃ )=CH-, -CH=C(CH ₃ )- or -C(CH ₃ )=C(CH ₃ )-, at least One hydrogen may be replaced by fluorine or chlorine; P ¹¹ , P ¹² and P ^{13 are} independently polymerizable groups; Sp ¹¹ , Sp ¹² and Sp ^{13 are} independently single bonds or alkylene groups having 1 to 10 carbon atoms, said Among Sp ¹¹ , Sp ¹² and Sp ¹³ , at least one -CH ₂ -may be substituted by -O-, -COO-, -OCO- or -OCOO-, and at least one -(CH ₂ ) ₂ -may be -CH=CH -Or -C≡C- substitution, at least one hydrogen can 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 f, g and The sum of h is 1 or more. The liquid crystal composition according to claim 10, wherein in formula (20), P ¹¹ , P ¹² and P ^{13 are} independently selected from the group consisting of polymerizable groups represented by formula (P-1) to formula (P-5) The base in the group;

In formula (P-1) to formula (P-5), M ¹¹ , M ¹² and M ^{13 are} independently hydrogen, fluorine, an alkyl group having 1 to 5 carbons, or a carbon number of 1 to 1 in which at least one hydrogen is substituted by halogen 5的alkyl. The liquid crystal composition according to claim 10, wherein the polymerizable compound represented by formula (20) contains at least one selected from the group of polymerizable compounds represented by formula (20-1) to formula (20-7) A compound

In formula (20-1) to formula (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. Among the Sp ¹¹ , Sp ¹² and Sp ¹³ , at least one -CH ₂ -may be -O-, -COO-, -OCO- or -OCOO- substitution, at least one -(CH ₂ ) ₂ -can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; P ¹¹ , P ¹² and P ^{13 is} independently a group selected from the group of polymerizable groups represented by formula (P-1) to formula (P-3),

In formulas (P-1) to (P-3), M ¹¹ , M ¹² and M ^{13 are} independently hydrogen, fluorine, an alkyl group having 1 to 5 carbons, or a carbon number of 1 to 1 in which at least one hydrogen is substituted by halogen 5的alkyl. The liquid crystal composition according to claim 5 or 6, which contains a polymerizable compound different from the compound represented by the formula (1) or the formula (20), a polymerization initiator, and a polymerization inhibitor. At least one of the group of agents, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, pigments, and defoamers. A liquid crystal display element containing at least a part selected from the liquid crystal composition according to any one of claims 5 to 13 and the liquid crystal composition according to any one of claims 5 to 13 At least one of the group consisting of aggregated persons.