TW202208600A - Compound, liquid crystal composition, and liquid crystal display element - Google Patents

Abstract

The present invention provides a compound having at least one characteristic: high chemical stability, high ability to align liquid crystal molecules horizontally, high alignment in a wide range of addition concentrations, appropriate reactivity, and high solubility in liquid crystal compositions. The present invention provides a compound having the following formula (1). In formula (1), a and b are independently 0, 1, or 2, and the sum of a and b is 0, 1, 2, or 3. Ring A1, ring A2, ring A3, and ring A4 are independently, for example, 1, 4 -cyclohexylene. Z1, Z2, Z3, Z4 and Z5 are independently a single bond or an alkylene group having 1 to 10 carbons. Sp1 and Sp2 are independently a single bond or an alkylene group having 1 to 10 carbons. P1 and P2 are independently a specific polymerizable group.

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. Furthermore, in detail, it relates to a polymerizable polar compound having a 9,10-dihydrophenanthrene-type condensed ring in the molecule, a liquid crystal composition comprising the compound and having positive or negative dielectric anisotropy, and a liquid crystal composition comprising the compound. The liquid crystal display element of the composition.

In liquid crystal display elements, the classification based on the operation mode of liquid crystal molecules is phase change (PC), twisted nematic (TN), super twisted nematic (STN), electronically controlled birefringence ( 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. Component-based driving methods are classified into passive matrix (PM) and active matrix (AM). PM is classified into static type (static), multiplex type (multiplex), etc., AM is classified into thin film transistor (TFT), metal insulator metal (MIM), and the like. TFTs are classified into amorphous silicon and polycrystal silicon. The latter are classified into high temperature type and low temperature type according to the manufacturing steps. The light source is classified into a reflective type using natural light, a transmissive type using a backlight, and a transflective type using both natural light and backlight.

The liquid crystal display element contains a liquid crystal composition having a nematic phase. The composition has suitable properties. By improving the properties of the composition, an AM device having good properties can be obtained. The associations between the two properties are summarized in Table 1 below. The properties of the composition will be further described based on a commercially available AM device. The temperature range of the nematic phase correlates to the temperature range over which the element can be used. The preferable upper limit temperature of the nematic phase is about 70°C or more, and the preferable lower limit temperature of the nematic phase is about -10°C or less. The viscosity of the composition correlates with the response time of the component. In order to display a moving image using an element, it is preferable that the response time is short. The ideal is a response time of less than 1 millisecond. Therefore, the viscosity of the composition is preferably small. More preferably, the viscosity at low temperature is small.

Table 1. Properties of composition and AM device Numbering Properties of the composition Characteristics of AM Components 1 Wide temperature range for nematic phase Wide temperature range available 2 Low viscosity ^{1 )} short response time 3 Optical anisotropy is appropriate high contrast ratio 4 Positive or negative dielectric anisotropy Low threshold voltage and low power consumption high contrast ratio 5 larger than resistance High voltage holding ratio and high contrast ratio 6 UV and heat stable long life 7 high elastic constant High contrast ratio and short response time 1) The time for injecting the composition into the liquid crystal display element can be shortened

The optical anisotropy of the composition is related to the contrast ratio of the element. Depending on the mode of the element, a large optical anisotropy or a small optical anisotropy, that is, an appropriate optical anisotropy, is required. The product (Δn×d) of the optical anisotropy (Δn) of the composition and the cell gap (d) of the element is designed to maximize the contrast ratio. The appropriate value of the product depends on the type of operation mode. In elements of a mode such as TN, the value is about 0.45 μm. In the element of the VA mode, the value is in the range of about 0.30 μm to about 0.40 μm, and in the element of the IPS mode or the FFS mode, 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 of the composition contributes to the low threshold voltage, low power consumption and high contrast ratio of the device. Therefore, a large positive or negative dielectric anisotropy is preferred. The large specific resistance of the composition contributes to the high voltage holding ratio and the high contrast ratio of the element. Therefore, it is preferable to use 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 preferable to use 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 UV light and heat correlates with the life of the element. 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.

A composition having positive dielectric anisotropy is used in an AM element having a TN mode. A composition having negative dielectric anisotropy is used in an AM element having a VA mode. A composition having positive or negative dielectric anisotropy is used in an AM element having an IPS mode or an FFS mode. A polymer sustained alignment (PSA) type AM device uses a composition having positive or negative dielectric anisotropy. A liquid crystal composition containing a polymer is used for a polymer sustained alignment (PSA) type liquid crystal display element. First, a composition to which a small amount of a polymerizable compound is added is injected into the element. Next, the composition was irradiated with ultraviolet rays while applying a voltage between the substrates of the element. The polymerizable compound is polymerized to form a polymer network structure in the composition. In the composition, the alignment of the liquid crystal molecules can be controlled by the polymer, so the response time of the element is shortened and the burn marks of the image are improved. This effect of polymers can be expected for elements with modes such as TN, ECB, OCB, IPS, VA, FFS, FPA.

The following methods are reported: instead of an alignment film such as polyimide, a low molecular weight compound having a cinnamate group or a low molecular weight compound having a polyvinyl cinnamate (polyvinyl cinnamate) and a chalcone structure, a low molecular weight compound having an azo A low molecular weight compound or a dendrimer of a benzene structure controls the alignment of the liquid crystal (Patent Document 1, Patent Document 2, or Patent Document 3). In the method of Patent Document 1, Patent Document 2 or Patent Document 3, first, the low molecular weight compound or polymer is dissolved in the liquid crystal composition as an additive. Then, by phase-separating the additive, a thin film containing the low-molecular-weight compound or polymer is formed on the substrate. Finally, the substrate is irradiated with linearly polarized light at a temperature higher than the upper limit temperature of the liquid crystal composition. When the low molecular compound or polymer undergoes dimerization or isomerization through the linearly polarized light, its molecules are arranged in a certain direction. In this method, by selecting the type of the low molecular weight compound or polymer, a device of a horizontal alignment mode such as IPS or FFS and a device of a vertical alignment mode such as VA can be produced. In the method, it is important that the low molecular weight compound or polymer is easily dissolved at a temperature higher than the upper limit temperature of the liquid crystal composition, and when returned to room temperature, the compound is easily phase-separated from the liquid crystal composition. Among them, it is difficult to secure the compatibility of the low molecular weight compound or polymer with the liquid crystal composition.

In a liquid crystal display element without an alignment film so far, as a compound capable of aligning liquid crystal molecules horizontally, the compound (S-1) is described in Patent Document 2 ([Chem. 2] in paragraph 0034 of the specification), and Patent Document 3 Compound (S-2) (compound [14] of P176 in the specification) and the like are described in . However, the characteristics of the liquid crystal display element produced using these compounds are insufficient, and improvement is desired.

[現有技術文獻] [專利文獻]

[Prior Art Document] [Patent Document]

[Patent Document 1] International Publication No. 2015/146369 [Patent Document 2] International Publication No. 2017/057162 [Patent Document 3] International Publication No. 2017/102068

[Problems to be Solved by Invention] The first object of the present invention is to provide a compound having high chemical stability, high ability to align liquid crystal molecules horizontally, high alignment in a wide range of addition concentrations, appropriate reactivity, and high solubility in liquid crystal compositions. At least one characteristic, and it can be expected to have a high voltage holding ratio when used in a liquid crystal display element. The second problem is to provide a liquid crystal composition including the compound, which satisfies the requirements of high upper limit temperature of nematic phase, low minimum temperature of nematic phase, low viscosity, suitable optical anisotropy, and positive or negative dielectric properties. At least one of the characteristics of large anisotropy, large specific resistance, high stability to ultraviolet rays, high stability to heat, and large elastic constant. The third problem is to provide a liquid crystal display element including the composition, wherein when a polar compound is formed into a film in the element by irradiating the composition with ultraviolet rays, the film has appropriate hardness and low permeability of contact components , At least one characteristic of high weather resistance and appropriate volume resistance value, and the liquid crystal display element has a wide temperature range of usable elements, a short response time, high voltage retention rate, low threshold voltage, large contrast ratio, long life, AC At least one characteristic of low afterimage. [Technical means to solve the problem]

（式中的記號的說明將在下文敘述） 本發明包含下述項等。 一種化合物，由式（1）表示。

式（1）中， a及b獨立地為0、1或2，a及b的和為0、1、2或3； 環A¹ 、環A² 、環A³ 及環A⁴ 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、十氫萘-2,6-二基、1,2,3,4-四氫萘-2,6-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、吡啶-2,5-二基、芴-2,7-二基、菲-2,7-二基、蒽-2,6-二基、全氫環戊并[a]菲-3,17-二基、2,3,4,7,8,9,10,11,12,13,14,15,16,17-十四氫環戊并[a]菲-3,17-二基、式（A-1）或式（A-2）所表示的基，這些環A¹ 、環A² 、環A³ 及環A⁴ 中，至少一個氫可經氟、氯、碳數1至12的烷基、碳數2至12的烯基、碳數1至11的烷氧基、碳數2至11的烯氧基、-Sp¹ -P¹ 或-Sp² -P² 取代，這些烷基、烯基、烷氧基、烯氧基、-Sp¹ -P¹ 或-Sp² -P² 中，至少一個氫可經氟或氯取代，其中，環A¹ 、環A² 、環A³ 或環A⁴ 的至少一個為式（A-1）或式（A-2）所表示的基，式（A-1）及式（A-2）中，Q¹ 及Q² 獨立地為-CH₂ -、-O-、-N(-R⁸ )-或-S-，此處，R⁸ 為氫或碳數1至15的烷基，所述R⁸ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁸ 為氟或氯的情況；

當a為2時，兩個環A¹ 可不同，當b為2時，兩個環A⁴ 可不同； Z¹ 、Z² 、Z³ 、Z⁴ 及Z⁵ 獨立地為單鍵或碳數1至10的伸烷基，所述Z¹ 、Z² 、Z³ 、Z⁴ 及Z⁵ 中，至少一個-CH₂ -可經-O-、-S-、-CO-、-COO-、-OCO-或-OCOO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但Z² 、Z³ 或Z⁴ 中的至少一個為-COS-、-SCO-、-CH=CHCOS-、-SCOCH=CH-、-COO-、-OCO-、-CH=CH-、-CH=CHCO-或-COCH=CH-，當a為2時，兩個Z¹ 可不同，當b為2時，兩個Z⁵ 可不同； Sp¹ 及Sp² 獨立地為單鍵或碳數1至10的伸烷基，所述Sp¹ 及Sp² 中，至少一個-CH₂ -可經-O-、-CO-、-COO-、-OCO-或-OCOO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟、氯或-Sp¹ -P¹ 或-Sp² -P² 取代； 在存在多個Sp¹ 或Sp² 的情況下，任意兩個可不同； P¹ 及P² 獨立地為式（1b）至式（1h）的任一者所表示的基，在存在多個P¹ 或P² 的情況下，任意兩個可不同；

式（1b）至式（1h）中， M¹ 、M² 、M³ 及M⁴ 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基；X¹ 為-N(-R⁹ )-、-O-或-S-，此處，R⁹ 為氫或碳數1至15的烷基，所述R⁹ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁹ 為氟或氯的情況； R² 及R⁶ 獨立地為氫、氟、氯或碳數1至5的烷基，所述R² 及R⁶ 中，至少一個氫可經氟或氯取代，至少一個-CH₂ -可經-O-取代； R³ 、R⁴ 、R⁵ 及R⁷ 獨立地為氫或碳數1至15的烷基，所述R³ 、R⁴ 、R⁵ 及R⁷ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁵ 及R⁷ 為氟或氯的情況。 一種液晶組成物，含有至少一種所述的化合物。 一種液晶顯示元件，含有所述的液晶組成物。 [發明的效果]The present inventors discovered that the compound represented by the following formula (1) can solve the above-mentioned problem, and completed the invention.

(The description of the symbols in the formula will be described later.) The present invention includes the following items and the like. A compound represented by formula (1).

In formula (1), a and b are independently 0, 1 or 2, and the sum of a and b is 0, 1, 2 or 3; Ring A ¹ , Ring A ² , Ring A ³ and Ring A ⁴ are independently 1,4-cyclohexylene, 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 , pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocyclopenta[a]phenanthrene-3,17 -diyl, 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecylhydrocyclopenta[a]phenanthrene-3,17-diyl, In the group represented by the formula (A-1) or the formula (A-2), among these ring A ¹ , ring A ² , ring A ³ and ring A ⁴ , at least one hydrogen may be replaced by fluorine, chlorine, carbon number of 1 to 12 Alkyl, alkenyl with 2 to 12 carbons, alkoxy with 1 to 11 carbons, alkenyl with 2 to 11 carbons, -Sp ¹ -P ¹ or -Sp ² -P ² are substituted, these alkanes In the radical, alkenyl, alkoxy, alkenyloxy, -Sp ¹ -P ¹ or -Sp ² -P ² , at least one hydrogen may be substituted by fluorine or chlorine, wherein ring A ¹ , ring A ² , ring A At least one of ³ or ring A ⁴ is a group represented by formula (A-1) or formula (A-2), and in formula (A-1) and formula (A-2), Q ¹ and Q ² are independently -CH ₂ -, -O-, -N(-R ⁸ )- or -S-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R ⁸ , 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, but no R is present ⁸ is the case of fluorine or chlorine;

When a is 2, the two rings A ¹ may be different, and when b is 2, the two rings A ⁴ may be different; Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are independently single bonds or carbon numbers 1 to 10 alkylene groups, in said Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ , at least one -CH ₂ - may be through -O-, -S-, -CO-, -COO-, -OCO- or -OCOO- substituted, 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, but Z ² , Z ³ or At least one of Z ⁴ is -COS-, -SCO-, -CH=CHCOS-, -SCOCH=CH-, -COO-, -OCO-, -CH=CH-, -CH=CHCO-, or -COCH= CH-, when a is 2, the two Z ¹ can be different, when b is 2, the two Z ⁵ can be different; Sp ¹ and Sp ² are independently a single bond or an alkylene group having 1 to 10 carbons, In the Sp ¹ and Sp ² , at least one -CH ₂ - can be substituted by -O-, -CO-, -COO-, -OCO- or -OCOO-, and at least one -(CH ₂ ) ₂ - can be substituted by - CH=CH- or -C≡C- substituted, at least one hydrogen can be substituted by fluorine, chlorine or -Sp ¹ -P ¹ or -Sp ² -P ² ; In the presence of multiple Sp ¹ or Sp ² , any Two may be different; P ¹ and P ² are independently a group represented by any one of formulas (1b) to (1h), and when there are multiple P ¹ or P ² , any two may be different;

In formula (1b) to formula (1h), M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 5 carbon atoms, or at least one hydrogen substituted by fluorine or chlorine Alkyl having 1 to 5 carbons; X ¹ is -N(-R ⁹ )-, -O- or -S-, where R ⁹ is hydrogen or alkyl having 1 to 15 carbons, and R ⁹ Among them, at least one -CH ₂ - can be substituted by -O- or -S-, 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 substitution, but there is no case where R ⁹ is fluorine or chlorine; R ² and R ⁶ are independently hydrogen, fluorine, chlorine or an alkyl group with 1 to 5 carbons, and in said R ² and R ⁶ , at least one hydrogen Can be substituted by fluorine or chlorine, at least one -CH ₂ - can be substituted by -O-; R ³ , R ⁴ , R ⁵ and R ⁷ are independently hydrogen or an alkyl group having 1 to 15 carbons, the R ³ , Among R ⁴ , R ⁵ and R ⁷ , 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 can be replaced by fluorine or chlorine, but there is no case where R ⁵ and R ⁷ are fluorine or chlorine. A liquid crystal composition containing at least one of the compounds. A liquid crystal display element containing the liquid crystal composition. [Effect of invention]

The first advantage of the present invention is to provide a compound with high chemical stability, high ability to align liquid crystal molecules horizontally, high alignment in a wide range of addition concentrations, appropriate reactivity, and high composition in liquid crystals At least one of the solubility in substances is expected to have a high voltage holding ratio when used in a liquid crystal display element. The second advantage is to provide a liquid crystal composition, which contains the compound, and satisfies the requirements of high upper limit temperature of nematic phase, low lower limit temperature of nematic phase, low viscosity, suitable optical anisotropy, and positive or negative dielectric properties. At least one of the characteristics of large anisotropy, large specific resistance, high stability to ultraviolet rays, high stability to heat, and large elastic constant. The third advantage is to provide a liquid crystal display element including the composition, which has suitable hardness and low permeability of contact components when a polar compound is formed into a film in the element by irradiating the composition with ultraviolet rays , At least one characteristic of high weather resistance and appropriate volume resistance value, and the liquid crystal display element has a wide temperature range of usable elements, a short response time, high voltage retention rate, low threshold voltage, large contrast ratio, long life, AC At least one characteristic of low afterimage. By using the liquid crystal composition containing the compound of the present invention, the formation step of the alignment film is not required, and therefore, a liquid crystal display element with a reduced manufacturing cost can be obtained.

How to use the terms in this specification is as follows. The terms "liquid crystal composition" and "liquid crystal display element" may be abbreviated as "composition" and "element", respectively. "Liquid crystal display element" is a general term for a liquid crystal display panel and a liquid crystal display module. "Liquid crystal compound" is a compound having a liquid crystal phase such as a nematic phase and a smectic phase, and it does not have a liquid crystal phase, but is used for the purpose of adjusting the temperature range, viscosity, and dielectric anisotropy of the nematic phase. On the other hand, a general term for compounds mixed into the composition. The compound 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 generating a polymer in the composition. "Polar compounds" help the liquid crystal molecules to align through the interaction of polar groups with the surface of the substrate.

The liquid crystal composition is prepared by mixing a plurality of liquid crystal compounds. The ratio (content) of the liquid crystal compound is represented by the weight percentage (% by weight) based on the weight of the liquid crystal composition. Additives such as optically active compounds, antioxidants, ultraviolet absorbers, pigments, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, and polar compounds are optionally added to the liquid crystal composition. Like the ratio of the liquid crystal compound, the ratio (addition amount) of the additive is represented by the weight percentage (% by weight) based on the weight of the liquid crystal composition. Parts per million (ppm) by weight are also sometimes used. The ratios of the polymerization initiator and the polymerization inhibitor are expressed based on the weight of the polymerizable compound exceptionally.

The compound represented by formula (1) may be abbreviated as "compound (1)" in some cases. Compound (1) refers to one compound represented by formula (1), a mixture of two compounds, or a mixture of three or more compounds. The rule also applies to at least one compound selected from the group of compounds represented by formula (2), and the like. The symbols B ¹ , C ¹ , F, etc. surrounded by hexagons correspond to ring B ¹ , ring C ¹ , ring F, etc., respectively. The hexagon represents a six-membered ring such as a cyclohexane ring or a benzene ring, or a condensed ring such as a naphthalene ring. The oblique line across the hexagon indicates that any hydrogen on the ring can be substituted by groups such as -Sp ¹ -P ¹ . Subscripts such as e indicate the number of substituted groups. When the subscript is 0, there is no such substitution.

As will be described later, the notation of the terminal group R ¹¹ is used in various component compounds. In these compounds, the two groups represented by any two R ¹¹ may be the same or different. For example, R ¹¹ of the compound (2) may be an ethyl group, and R ¹¹ of the compound (3) may be an ethyl group. In some cases, R ¹¹ of the compound (2) is an ethyl group, and R ¹¹ of the compound (3) is a propyl group. The rules also apply to other end groups, rings, linkage groups, etc. notation. In formula (8) described later, when i is 2, two rings D ¹ exist. In the compound, the two groups represented by the two rings D ¹ may be the same or different. The rules also apply to any two rings D ¹ when i is greater than 2. The rules also apply to other notations of rings, bonding groups, and the like.

The expression "at least one 'A'" means that the number of 'A's is arbitrary. Regarding the expression "at least one 'A' can be replaced by 'B'", when the number of 'A' is one, the position of 'A' is arbitrary, and when the number of 'A' is two or more, the The positions of these 'A's can be selected indefinitely. The rules also apply to the expression "at least one 'A' is substituted with 'B'". The expression "at least one A may be substituted by B, C, or D" is meant to include at least one case where A is substituted by B, where at least one A is substituted by C, and where at least one A is substituted by D, and multiple A's are substituted by D. The case of at least two substitutions of B, C, and D. For example, among the alkyl groups in which at least one -CH ₂ - (or -(CH ₂ ) ₂ -) can be substituted by -O- (or -CH=CH-), including alkyl, alkenyl, alkoxy, alkoxy Alkyl, alkoxyalkenyl, alkenyloxyalkyl. Furthermore, it is not preferable that two consecutive -CH ₂ - are substituted by -O- to become -OO-.

Halogen means fluorine, chlorine, bromine or iodine. Preferred halogens are fluorine or chlorine. A further preferred halogen is fluorine. The alkyl group is linear or branched, and does not include cyclic alkyl groups. In general, straight chain alkyl groups are preferred over branched alkyl groups. The same applies to terminal groups such as an alkoxy group and an alkenyl group. Regarding the stereo configuration related to 1,4-cyclohexylene, in order to increase the upper temperature limit of the nematic phase, the trans configuration is preferred to the cis configuration. The 2-fluoro-1,4-phenylene group refers to the following two divalent groups. In the chemical formula, fluorine can be left (L) or right (R). The rules also apply to asymmetric divalent radicals such as tetrahydropyran-2,5-diyl, which are formed by removing two hydrogens from the ring.

The present invention includes the following items and the like.

式（1）中， a及b獨立地為0、1或2，a及b的和為0、1、2或3； 環A¹ 、環A² 、環A³ 及環A⁴ 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、十氫萘-2,6-二基、1,2,3,4-四氫萘-2,6-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、吡啶-2,5-二基、芴-2,7-二基、菲-2,7-二基、蒽-2,6-二基、全氫環戊并[a]菲-3,17-二基、2,3,4,7,8,9,10,11,12,13,14,15,16,17-十四氫環戊并[a]菲-3,17-二基、式（A-1）或式（A-2）所表示的基，這些環A¹ 、環A² 、環A³ 及環A⁴ 中，至少一個氫可經氟、氯、碳數1至12的烷基、碳數2至12的烯基、碳數1至11的烷氧基、碳數2至11的烯氧基、-Sp¹ -P¹ 或-Sp² -P² 取代，這些烷基、烯基、烷氧基、烯氧基、-Sp¹ -P¹ 或-Sp² -P² 中，至少一個氫可經氟或氯取代，其中，環A¹ 、環A² 、環A³ 或環A⁴ 的至少一個為式（A-1）或式（A-2）所表示的基，式（A-1）及式（A-2）中，Q¹ 及Q² 獨立地為-CH₂ -、-O-、-N(-R⁸ )-或-S-，此處，R⁸ 為氫或碳數1至15的烷基，所述R⁸ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁸ 為氟或氯的情況；

當a為2時，兩個環A¹ 可不同，當b為2時，兩個環A⁴ 可不同； Z¹ 、Z² 、Z³ 、Z⁴ 及Z⁵ 獨立地為單鍵或碳數1至10的伸烷基，所述Z¹ 、Z² 、Z³ 、Z⁴ 及Z⁵ 中，至少一個-CH₂ -可經-O-、-S-、-CO-、-COO-、-OCO-或-OCOO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但Z² 、Z³ 或Z⁴ 中的至少一個為-COS-、-SCO-、-CH=CHCOS-、-SCOCH=CH-、-COO-、-OCO-、-CH=CH-、-CH=CHCO-或-COCH=CH-，當a為2時，兩個Z¹ 可不同，當b為2時，兩個Z⁵ 可不同； Sp¹ 及Sp² 獨立地為單鍵或碳數1至10的伸烷基，所述Sp¹ 及Sp² 中，至少一個-CH₂ -可經-O-、-CO-、-COO-、-OCO-或-OCOO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟、氯或-Sp¹ -P¹ 或-Sp² -P² 取代； 在存在多個Sp¹ 或Sp² 的情況下，任意兩個可不同； P¹ 及P² 獨立地為式（1b）至式（1h）的任一者所表示的基，在存在多個P¹ 或P² 的情況下，任意兩個可不同；

式（1b）至式（1h）中， M¹ 、M² 、M³ 及M⁴ 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基；X¹ 為-N(-R⁹ )-、-O-或-S-，此處，R⁹ 為氫或碳數1至15的烷基，所述R⁹ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁹ 為氟或氯的情況； R² 及R⁶ 獨立地為氫、氟、氯或碳數1至5的烷基，所述R² 及R⁶ 中，至少一個氫可經氟或氯取代，至少一個-CH₂ -可經-O-取代； R³ 、R⁴ 、R⁵ 及R⁷ 獨立地為氫或碳數1至15的烷基，所述R³ 、R⁴ 、R⁵ 及R⁷ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁵ 及R⁷ 為氟或氯的情況。Item 1 A compound represented by formula (1).

In formula (1), a and b are independently 0, 1 or 2, and the sum of a and b is 0, 1, 2 or 3; Ring A ¹ , Ring A ² , Ring A ³ and Ring A ⁴ are independently 1,4-cyclohexylene, 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 , pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocyclopenta[a]phenanthrene-3,17 -diyl, 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecylhydrocyclopenta[a]phenanthrene-3,17-diyl, In the group represented by the formula (A-1) or the formula (A-2), among these ring A ¹ , ring A ² , ring A ³ and ring A ⁴ , at least one hydrogen may be replaced by fluorine, chlorine, carbon number of 1 to 12 Alkyl, alkenyl with 2 to 12 carbons, alkoxy with 1 to 11 carbons, alkenyl with 2 to 11 carbons, -Sp ¹ -P ¹ or -Sp ² -P ² are substituted, these alkanes In the radical, alkenyl, alkoxy, alkenyloxy, -Sp ¹ -P ¹ or -Sp ² -P ² , at least one hydrogen may be substituted by fluorine or chlorine, wherein ring A ¹ , ring A ² , ring A At least one of ³ or ring A ⁴ is a group represented by formula (A-1) or formula (A-2), and in formula (A-1) and formula (A-2), Q ¹ and Q ² are independently -CH ₂ -, -O-, -N(-R ⁸ )- or -S-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R ⁸ , 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, but no R is present ⁸ is the case of fluorine or chlorine;

When a is 2, the two rings A ¹ may be different, and when b is 2, the two rings A ⁴ may be different; Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are independently single bonds or carbon numbers 1 to 10 alkylene groups, in said Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ , at least one -CH ₂ - may be through -O-, -S-, -CO-, -COO-, -OCO- or -OCOO- substituted, 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, but Z ² , Z ³ or At least one of Z ⁴ is -COS-, -SCO-, -CH=CHCOS-, -SCOCH=CH-, -COO-, -OCO-, -CH=CH-, -CH=CHCO-, or -COCH= CH-, when a is 2, the two Z ¹ can be different, when b is 2, the two Z ⁵ can be different; Sp ¹ and Sp ² are independently a single bond or an alkylene group having 1 to 10 carbons, In the Sp ¹ and Sp ² , at least one -CH ₂ - can be substituted by -O-, -CO-, -COO-, -OCO- or -OCOO-, and at least one -(CH ₂ ) ₂ - can be substituted by - CH=CH- or -C≡C- substituted, at least one hydrogen can be substituted by fluorine, chlorine or -Sp ¹ -P ¹ or -Sp ² -P ² ; In the presence of multiple Sp ¹ or Sp ² , any Two may be different; P ¹ and P ² are independently a base represented by any one of formulas (1b) to (1h), and when there are multiple P ¹ or P ² , any two may be different;

In formula (1b) to formula (1h), M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 5 carbon atoms, or at least one hydrogen substituted by fluorine or chlorine Alkyl having 1 to 5 carbons; X ¹ is -N(-R ⁹ )-, -O- or -S-, where R ⁹ is hydrogen or alkyl having 1 to 15 carbons, and said R ⁹ Among them, at least one -CH ₂ - can be substituted by -O- or -S-, 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 substitution, but there is no case where R ⁹ is fluorine or chlorine; R ² and R ⁶ are independently hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and among the R ² and R ⁶ , at least one hydrogen Can be substituted by fluorine or chlorine, at least one -CH ₂ - can be substituted by -O-; R ³ , R ⁴ , R ⁵ and R ⁷ are independently hydrogen or an alkyl group having 1 to 15 carbons, the R ³ , Among R ⁴ , R ⁵ and R ⁷ , 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 can be replaced by fluorine or chlorine, but there is no case where R ⁵ and R ⁷ are fluorine or chlorine.

當a為2時，兩個環A¹ 可不同，當b為2時，兩個環A⁴ 可不同； Z¹ 、Z² 、Z³ 、Z⁴ 及Z⁵ 獨立地為單鍵、-(CH₂ )₂ -、-C≡C-、-C≡C-C≡C-、-COO-、-OCO-、-CF₂ O-、-OCF₂ -、-CH₂ O-、-OCH₂ -、-CF=CF-、-CH=CHCOO-、-OCOCH=CH-、-CH=CH-、-CH=CHCO-、-COCH=CH-、-COS-、-SCO-、-CH=CHCOS-或-SCOCH=CH-；當a為2時，兩個Z¹ 可不同，當b為2時，兩個Z⁵ 可不同； Sp¹ 及Sp² 獨立地為單鍵或碳數1至10的伸烷基，所述Sp¹ 及Sp² 中，至少一個-CH₂ -可經-O-、-COO-或-OCO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-取代，至少一個氫可經氟、氯或-Sp¹ -P¹ 或-Sp² -P² 取代，在存在多個Sp¹ 或Sp² 的情況下，分別可不同； P¹ 及P² 獨立地為式（1b）至式（1h）的任一者所表示的基，在存在多個P¹ 或P² 的情況下，任意兩個可不同；

式（1b）至式（1h）中， M¹ 、M² 、M³ 及M⁴ 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基，X¹ 為-N(-R⁹ )-、-O-或-S-，此處，R⁹ 為氫或碳數1至15的烷基，所述R⁹ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁹ 為氟或氯的情況； R² 及R⁶ 為氫、氟、氯或碳數1至5的烷基，所述R² 及R⁶ 中，至少一個氫可經氟或氯取代，至少一個-CH₂ -可經-O-取代； R³ 、R⁴ 、R⁵ 及R⁷ 獨立地為氫或碳數1至15的烷基，所述R³ 、R⁴ 、R⁵ 及R⁷ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁵ 及R⁷ 為氟或氯的情況。Item 2 The compound according to Item 1, wherein, in formula (1), a and b are independently 0, 1, or 2, and the sum of a and b is 0, 1, or 2; ring A ¹ , ring A ² , Ring A ³ and Ring A ⁴ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decalin-2 ,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl base, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocycle Pento[a]phenanthrene-3,17-diyl, 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a ] phenanthrene-3,17-diyl, a group represented by the formula (A-1) or the formula (A-2), at least one hydrogen may be among these ring A ¹ , ring A ² , ring A ³ and ring A ⁴ Via fluorine, chlorine, alkyl group having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11 carbons, alkenyloxy having 2 to 11 carbons, -Sp ¹ -P ¹ or -Sp ² -P ² substituted, in these alkyl, alkenyl, alkoxy, alkenyloxy, -Sp ¹ -P ¹ or -Sp ² -P ² , at least one hydrogen may be substituted by fluorine or chlorine, wherein, At least one of ring A ¹ , ring A ² , ring A ³ or ring A ⁴ is a group represented by formula (A-1) or formula (A-2), and Q ¹ and Q ² are independently -CH ₂ -, -O-, -N(R ⁸ )- or -S-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R ⁸ , at least one -CH ₂ - may be via -O- Or -S-substituted, 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, but no R ⁸ is fluorine or chlorine Condition,

When a is 2, the two rings A ¹ may be different, and when b is 2, the two rings A ⁴ may be different; Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are independently single bonds, -( CH ₂ ) ₂ -, -C≡C-, -C≡CC≡C-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -CH ₂ O-, -OCH ₂ -, -CF=CF-, -CH=CHCOO-, -OCOCH=CH-, -CH=CH-, -CH=CHCO-, -COCH=CH-, -COS-, -SCO-, -CH=CHCOS- or -SCOCH=CH-; when a is 2, the two Z ¹ can be different, when b is 2, the two Z ⁵ can be different; Sp ¹ and Sp ² are independently a single bond or an extension of carbon number 1 to 10 Alkyl, among the Sp ¹ and Sp ² , at least one -CH ₂ - can be substituted by -O-, -COO- or -OCO-, and at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH- , at least one hydrogen can be substituted by fluorine, chlorine or -Sp ¹ -P ¹ or -Sp ² -P ² , in the presence of multiple Sp ¹ or Sp ² , they can be different respectively; P ¹ and P ² are independently The group represented by any one of formula (1b) to formula (1h), when there are multiple P ¹ or P ² , any two may be different;

In formula (1b) to formula (1h), M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 5 carbon atoms, or at least one hydrogen substituted by fluorine or chlorine an alkyl group having 1 to 5 carbon atoms, X ¹ is -N(-R ⁹ )-, -O- or -S-, where R ⁹ is hydrogen or an alkyl group having 1 to 15 carbon atoms, and the R ⁹ Among them, at least one -CH ₂ - can be substituted by -O- or -S-, 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 substitution, but there is no case where R ⁹ is fluorine or chlorine; R ² and R ⁶ are hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and among the R ² and R ⁶ , at least one hydrogen can be Fluorine or chlorine substitution, at least one -CH ₂ - may be substituted by -O-; R ³ , R ⁴ , R ⁵ and R ⁷ are independently hydrogen or an alkyl group having 1 to 15 carbons, the R ³ , R ⁴ , R ⁵ and R ⁷ , at least one -CH ₂ - can be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH- or -C≡C-, at least one One hydrogen can be replaced by fluorine or chlorine, but there is no case where ^R5 and ^R7 are fluorine or chlorine.

式（1-1）至式（1-3）中， 環A¹ 、環A² 、環A³ 及環A⁴ 獨立地為1,4-伸環己基、1,4-伸苯基、萘-2,6-二基、嘧啶-2,5-二基、吡啶-2,5-二基、芴-2,7-二基、菲-2,7-二基、蒽-2,6-二基、式（A-1）或式（A-2）所表示的基，這些環A¹ 、環A² 、環A³ 及環A⁴ 中，至少一個氫可經氟、氯、碳數1至12的烷基、碳數2至12的烯基、碳數1至11的烷氧基、碳數2至11的烯氧基、-Sp¹ -P¹ 或-Sp² -P² 取代，這些烷基、烯基、烷氧基、烯氧基、-Sp¹ -P¹ 或-Sp² -P² 中，至少一個氫可經氟或氯取代，其中，環A¹ 、環A² 、環A³ 或環A⁴ 的至少一個為式（A-1）或式（A-2），Q¹ 及Q² 獨立地為-CH₂ -、-O-、-N(R⁸ )-或-S-，此處，R⁸ 為氫或碳數1至15的烷基，所述R⁸ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁸ 為氟或氯的情況，

Z² 、Z³ 及Z⁴ 獨立地為單鍵、-(CH₂ )₂ -、-C≡C-、-C≡C-C≡C-、-COO-、-OCO-、-CF₂ O-、-OCF₂ -、-CH₂ O-、-OCH₂ -、-CF=CF-、-CH=CHCOO-、-OCOCH=CH-、-CH=CH-、-CH=CHCO-、-COCH=CH-、-COS-、-SCO-、-CH=CHCOS-或-SCOCH=CH-； Sp¹ 及Sp² 獨立地為單鍵或碳數1至10的伸烷基，所述Sp¹ 及Sp² 中，至少一個-CH₂ -可經-O-、-COO-、-OCOO-或-OCO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-取代，至少一個氫可經氟、氯或-Sp¹ -P¹ 或-Sp² -P² 取代，在存在多個Sp¹ 或Sp² 的情況下，分別可不同； P¹ 及P² 獨立地為式（1b）至式（1h）的任一者所表示的基，在存在多個P¹ 或P² 的情況下，任意兩個可不同；

式（1b）至式（1h）中， M¹ 、M² 、M³ 及M⁴ 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基；X¹ 為-N(-R⁹ )-、-O-或-S-，此處，R⁹ 為氫或碳數1至15的烷基，所述R⁹ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁹ 為氟或氯的情況； R² 及R⁶ 為氫、氟、氯或碳數1至5的烷基，所述R² 及R⁶ 中，至少一個氫可經氟或氯取代，至少一個-CH₂ -可經-O-取代； R³ 、R⁴ 、R⁵ 及R⁷ 獨立地為氫或碳數1至15的烷基，所述R³ 、R⁴ 、R⁵ 及R⁷ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁵ 及R⁷ 為氟或氯的情況。Item 3 The compound according to Item 1 or Item 2, which is represented by any one of Formula (1-1) to Formula (1-3).

In formula (1-1) to formula (1-3), ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are independently 1,4-cyclohexylene, 1,4-phenylene, naphthalene -2,6-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl In a diradical, a radical represented by formula (A-1) or formula (A-2), among these ring A ¹ , ring A ² , ring A ³ and ring A ⁴ , at least one hydrogen may be replaced by fluorine, chlorine, carbon number Alkyl of 1 to 12, alkenyl of carbon number 2 to 12, alkoxy of carbon number of 1 to 11, alkenyloxy of carbon number of 2 to 11, -Sp ¹ -P ¹ or -Sp ² -P ² substituted , in these alkyl, alkenyl, alkoxy, alkenyloxy, -Sp ¹ -P ¹ or -Sp ² -P ² , at least one hydrogen may be substituted by fluorine or chlorine, wherein ring A ¹ , ring A ² , at least one of ring A ³ or ring A ⁴ is formula (A-1) or formula (A-2), and Q ¹ and Q ² are independently -CH ₂ -, -O-, -N(R ⁸ )- or -S-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, in said R ⁸ , at least one -CH ₂ - may be substituted by -O- or -S-, 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, but there is no case where R ⁸ is fluorine or chlorine,

Z ² , Z ³ and Z ⁴ are independently a single bond, -(CH ₂ ) ₂ -, -C≡C-, -C≡CC≡C-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -CH ₂ O-, -OCH ₂ -, -CF=CF-, -CH=CHCOO-, -OCOCH=CH-, -CH=CH-, -CH=CHCO-, -COCH=CH -, -COS-, -SCO-, -CH=CHCOS- or -SCOCH=CH-; Sp ¹ and Sp ² are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and the Sp ¹ and Sp ² Among them, at least one -CH ₂ - can be substituted by -O-, -COO-, -OCOO- or -OCO-, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH-, and at least one hydrogen can be substituted by -CH=CH- Fluorine, chlorine or -Sp ¹ -P ¹ or -Sp ² -P ² substituted, in the presence of multiple Sp ¹ or Sp ² , they may be different respectively; P ¹ and P ² are independently formula (1b) to formula (1h), when there are a plurality of P ¹ or P ² , any two of them may be different;

In formula (1b) to formula (1h), M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 5 carbon atoms, or at least one hydrogen substituted by fluorine or chlorine Alkyl having 1 to 5 carbons; X ¹ is -N(-R ⁹ )-, -O- or -S-, where R ⁹ is hydrogen or alkyl having 1 to 15 carbons, and R ⁹ Among them, at least one -CH ₂ - can be substituted by -O- or -S-, 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 substitution, but there is no case where R ⁹ is fluorine or chlorine; R ² and R ⁶ are hydrogen, fluorine, chlorine or an alkyl group with 1 to 5 carbon atoms, and among the R ² and R ⁶ , at least one hydrogen can be Fluorine or chlorine substitution, at least one -CH ₂ - may be substituted by -O-; R ³ , R ⁴ , R ⁵ and R ⁷ are independently hydrogen or an alkyl group having 1 to 15 carbons, and said R ³ , R ⁴ , R ⁵ and R ⁷ , at least one -CH ₂ - can be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH- or -C≡C-, at least one One hydrogen can be replaced by fluorine or chlorine, but there is no case where ^R5 and ^R7 are fluorine or chlorine.

Z² 、Z³ 及Z⁴ 獨立地為單鍵、-(CH₂ )₂ -、-C≡C-C≡C-、-C≡C-、-COO-、-OCO-、-CH=CHCOO-、-OCOCH=CH-、-CH=CH-、-CH=CHCO-、-COCH=CH-、-COS-、-SCO-、-CH=CHCOS-或-SCOCH=CH-； Sp¹ 及Sp² 獨立地為單鍵或碳數1至10的伸烷基，所述Sp¹ 及Sp² 中，至少一個-CH₂ -可經-O-、-COO-、-OCOO-或-OCO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-取代，至少一個氫可經-Sp¹ -P¹ 或-Sp² -P² 取代，在存在多個Sp¹ 或Sp² 的情況下，分別可不同； P¹ 及P² 獨立地為式（1b）、式（1c）、式（1d）或式（1e）的任一者所表示的基，在存在多個P¹ 或P² 的情況下，任意兩個可不同；

式（1b）至式（1e）中， M¹ 、M² 、M³ 及M⁴ 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基，X¹ 為-N(-R⁹ )-、-O-或-S-，此處，R⁹ 為氫或碳數1至15的烷基，所述R⁹ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁹ 為氟或氯的情況； R² 及R⁶ 為氫、氟、氯或碳數1至5的烷基，所述R² 及R⁶ 中，至少一個氫可經氟或氯取代，至少一個-CH₂ -可經-O-取代； R³ 、R⁴ 及R⁵ 獨立地為氫或碳數1至15的烷基，所述R³ 、R⁴ 及R⁵ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁵ 為氟或氯的情況。Item 4 The compound according to Item 3, wherein, in formulas (1-1) to (1-3), ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are independently 1,4-extended Cyclohexyl, 1,4-phenylene, naphthalene-2,6-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, formula (A-1) or formula (A-2 ) represented by ), among these ring A ¹ , ring A ² , ring A ³ and ring A ⁴ , at least one hydrogen may be fluorine, chlorine, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons , alkoxy with 1 to 11 carbons, alkenyloxy with 2 to 11 carbons, -Sp ¹ -P ¹ or -Sp ² -P ² substituted, wherein, ring A ¹ , ring A ² , ring A ³ or At least one of ring A ⁴ is a group represented by formula (A-1) or formula (A-2), and Q ¹ and Q ² are independently -CH ₂ -, -O-, -N(R ⁸ )- or -S-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, in said R ⁸ , at least one -CH ₂ - may be substituted by -O- 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, but there is no case where R ⁸ is fluorine or chlorine,

Z ² , Z ³ and Z ⁴ are independently a single bond, -(CH ₂ ) ₂ -, -C≡CC≡C-, -C≡C-, -COO-, -OCO-, -CH=CHCOO-, -OCOCH=CH-, -CH=CH-, -CH=CHCO-, -COCH=CH-, -COS-, -SCO-, -CH=CHCOS- or -SCOCH=CH-; Sp ¹ and Sp ² independent is a single bond or an alkylene group having 1 to 10 carbon atoms, in the Sp ¹ and Sp ² , at least one -CH ₂ - may be substituted by -O-, -COO-, -OCOO- or -OCO-, at least One -(CH ₂ ) ₂ - can be substituted by -CH=CH-, at least one hydrogen can be substituted by -Sp ¹ -P ¹ or -Sp ² -P ² , in the presence of multiple Sp ¹ or Sp ² , may be different; P ¹ and P ² are independently a group represented by any one of formula (1b), formula (1c), formula (1d) or formula (1e), and in the presence of a plurality of P ¹ or P ² case, any two can be different;

In formula (1b) to formula (1e), M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 5 carbon atoms, or at least one hydrogen substituted by fluorine or chlorine an alkyl group having 1 to 5 carbon atoms, X ¹ is -N(-R ⁹ )-, -O- or -S-, where R ⁹ is hydrogen or an alkyl group having 1 to 15 carbon atoms, and the R ⁹ Among them, at least one -CH ₂ - can be substituted by -O- or -S-, 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 substitution, but there is no case where R ⁹ is fluorine or chlorine; R ² and R ⁶ are hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and among the R ² and R ⁶ , at least one hydrogen can be Fluorine or chlorine substitution, at least one -CH ₂ - may be substituted by -O-; R ³ , R ⁴ and R ⁵ are independently hydrogen or an alkyl group having 1 to 15 carbon atoms, and said R ³ , R ⁴ and R ⁵ Among them, at least one -CH ₂ - can be substituted by -O- or -S-, 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 is substituted, but there is no case where ^R5 is fluorine or chlorine.

Z² 、Z³ 及Z⁴ 獨立地為單鍵、-(CH₂ )₂ -、-C≡C-C≡C-、-C≡C-、-COO-、-OCO-、-CH=CHCOO-、-OCOCH=CH-、-CH=CH-、-CH=CHCO-、-COCH=CH-、-COS-、-SCO-、-CH=CHCOS-或-SCOCH=CH-； Sp¹ 及Sp² 獨立地為單鍵或碳數1至10的伸烷基，所述Sp¹ 及Sp² 中，至少一個-CH₂ -可經-O-、-COO-、-OCOO-或-OCO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-取代，至少一個氫可經-Sp¹ -P¹ 或-Sp² -P² 取代，在存在多個Sp¹ 或Sp² 的情況下，任意兩個可不同； P¹ 及P² 獨立地為式（1b-1）、式（1b-2）、式（1b-3）、式（1b-4）、式（1b-5）、式（1c-1）、式（1d-1）、式（1d-2）或式（1e-1）所表示的基，

式（1b-1）、式（1b-2）、式（1b-3）、式（1b-4）、式（1b-5）、式（1c-1）、式（1d-1）、式（1d-2）及式（1e-1）中， X² 、X³ 、X⁴ 、X⁵ 及X⁶ 獨立地為-N(-R⁹ )-、-O-或-S-，此處，R⁹ 為氫或碳數1至15的烷基，所述R⁹ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁹ 為氟或氯的情況。Item 5 The compound according to Item 3, wherein, in formulas (1-1) to (1-3), ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are independently 1,4-extended Cyclohexyl, 1,4-phenylene, naphthalene-2,6-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, formula (A-1) or formula (A-2 ), among these ring A ¹ , ring A ² , ring A ³ and ring A ⁴ , at least one hydrogen may be substituted by fluorine, chlorine, methyl or ethyl, wherein ring A ¹ , ring A ² , ring A ³ or At least one of ring A ⁴ is of formula (A-1) or formula (A-2), Q ¹ and Q ² are independently -CH ₂ -, -O-, -N(R ⁸ )- or -S-, Here, R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R ⁸ , at least one -CH ₂ - may be substituted by -O- or -S-, and at least one -(CH ₂ ) ₂ - may be substituted by -O- or -S- Substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine, but there is no case where R ⁸ is fluorine or chlorine,

Z ² , Z ³ and Z ⁴ are independently a single bond, -(CH ₂ ) ₂ -, -C≡CC≡C-, -C≡C-, -COO-, -OCO-, -CH=CHCOO-, -OCOCH=CH-, -CH=CH-, -CH=CHCO-, -COCH=CH-, -COS-, -SCO-, -CH=CHCOS- or -SCOCH=CH-; Sp ¹ and Sp ² independent is a single bond or an alkylene group having 1 to 10 carbon atoms, in the Sp ¹ and Sp ² , at least one -CH ₂ - may be substituted by -O-, -COO-, -OCOO- or -OCO-, at least One -(CH ₂ ) ₂ - can be substituted by -CH=CH-, at least one hydrogen can be substituted by -Sp ¹ -P ¹ or -Sp ² -P ² , in the presence of multiple Sp ¹ or Sp ² , Any two can be different; P ¹ and P ² are independently formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), the base represented by the formula (1d-1), the formula (1d-2) or the formula (1e-1),

Equation (1b-1), Equation (1b-2), Equation (1b-3), Equation (1b-4), Equation (1b-5), Equation (1c-1), Equation (1d-1), Equation In (1d-2) and formula (1e-1), X ² , X ³ , X ⁴ , X ⁵ and X ⁶ are independently -N(-R ⁹ )-, -O- or -S-, where , R ⁹ is hydrogen or an alkyl group with 1 to 15 carbon atoms, in said R ⁹ , at least one -CH ₂ - can be substituted by -O- or -S-, and at least one -(CH ₂ ) ₂ - can be substituted by - CH=CH- or -C≡C- substituted, at least one hydrogen can be substituted by fluorine or chlorine, but there is no case where R ⁹ is fluorine or chlorine.

Item 6 The compound according to Item 3, wherein, in the compounds represented by the formulae (1-1) to (1-3), any one of Z ² , Z ³ or Z ⁴ is -COO- or -OCO- , Q ¹ is -CH ₂ - or -N(R ⁸ )-, Q ² is -N(R ⁸ )-, here, R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in the R ⁸ , at least one -CH ₂ - can be substituted by -O- or -S-, 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 substituted, but in the absence of ^R8 being fluoro or chloro.

這些式中， Sp¹ 及Sp² 獨立地為單鍵或碳數1至10的伸烷基，所述Sp¹ 及Sp² 中，至少一個-CH₂ -可經-O-、-COO-、-OCOO-或-OCO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-取代，至少一個氫可經-Sp¹ -P¹ 或-Sp² -P² 取代； P¹ 、P² 、Sp¹ 及Sp² 以外的部分結構中，至少一個氫可經氟、氯、甲基或乙基取代； Q¹ 為-CH₂ -或-N(R⁸ )-，Q² 為-N(R⁸ )-，此處，R⁸ 為氫或碳數1至15的烷基，所述R⁸ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁸ 為氟或氯的情況， P¹ 及P² 獨立地為式（1b-1）、式（1b-2）、式（1b-3）、式（1b-4）、式（1b-5）、式（1c-1）、式（1d-1）、式（1d-2）或式（1e-1）所表示的基，

式（1b-1）、式（1b-2）、式（1b-3）、式（1b-4）、式（1b-5）、式（1c-1）、式（1d-1）、式（1d-2）或式（1e-1）中，X² 、X³ 、X⁴ 、X⁵ 及X⁶ 獨立地為-N(-R⁹ )-、-O-或-S-，此處，R⁹ 為氫或碳數1至15的烷基，所述R⁹ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁹ 為氟或氯的情況。Item 7 The compound according to any one of Items 1 to 6, which is represented by any one of the following formulae.

In these formulas, Sp ¹ and Sp ² are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in the Sp ¹ and Sp ² , at least one -CH ₂ - may be through -O-, -COO-, -OCOO- or -OCO- substituted, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH-, at least one hydrogen can be substituted by -Sp ¹ -P ¹ or -Sp ² -P ² ; P ¹ , In partial structures other than P ² , Sp ¹ and Sp ² , at least one hydrogen may be substituted by fluorine, chlorine, methyl or ethyl; Q ¹ is -CH ₂ - or -N(R ⁸ )-, Q ² is - N(R ⁸ )-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, in said R ⁸ , at least one -CH ₂ - may be substituted by -O- 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, but there is no case where R ⁸ is fluorine or chlorine, P ¹ and P ² are independently is formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), formula (1d-1), The base represented by formula (1d-2) or formula (1e-1),

Equation (1b-1), Equation (1b-2), Equation (1b-3), Equation (1b-4), Equation (1b-5), Equation (1c-1), Equation (1d-1), Equation In (1d-2) or formula (1e-1), X ² , X ³ , X ⁴ , X ⁵ and X ⁶ are independently -N(-R ⁹ )-, -O- or -S-, where , R ⁹ is hydrogen or an alkyl group with 1 to 15 carbon atoms, in said R ⁹ , at least one -CH ₂ - can be substituted by -O- or -S-, and at least one -(CH ₂ ) ₂ - can be substituted by - CH=CH- or -C≡C- substituted, at least one hydrogen can be substituted by fluorine or chlorine, but there is no case where R ⁹ is fluorine or chlorine.

Item 8 The compound according to Item 7, wherein formula (1-1-11-1) to formula (1-1-11-2), formula (1-2-11-1) to formula (1-2) -11-4), formula (1-1-12-1) to formula (1-1-12-2), formula (1-2-12-1) to formula (1-2-12-4), Equation (1-1-21-1) to Equation (1-1-21-2), Equation (1-2-21-1) to Equation (1-2-21-4), Equation (1-1- In the compounds represented by 22-1) to formula (1-1-22-2) or formula (1-2-22-1) to formula (1-2-22-4), Sp ¹ and Sp ² are independently is an alkylene group having 1 to 10 carbon atoms, among the Sp ¹ and Sp ² , at least one -CH ₂ - can be substituted by -O-, and at least one hydrogen can be substituted by fluorine, chlorine or -Sp ¹ -P ¹ or - Sp ² -P ² substituted.

Item 9 A liquid crystal composition containing at least one compound according to any one of Items 1 to 8.

式（2）至式（4）中， R¹¹ 及R¹² 獨立地為碳數1至10的烷基或碳數2至10的烯基，所述R¹¹ 及R¹² 中，至少一個-CH₂ -可經-O-取代，至少一個氫可經氟取代； 環B¹ 、環B² 、環B³ 及環B⁴ 獨立地為1,4-伸環己基、1,4-伸苯基、2-氟-1,4-伸苯基、2,5-二氟-1,4-伸苯基或嘧啶-2,5-二基； Z¹¹ 、Z¹² 及Z¹³ 獨立地為單鍵、-(CH₂ )₂ -、-CH=CH-、-C≡C-或-COO-。Item 10 The liquid crystal composition according to Item 9, which further 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 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹¹ and R ¹² , at least one -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, 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 , -(CH ₂ ) ₂ -, -CH=CH-, -C≡C- or -COO-.

式（5）至式（7）中， R¹³ 為碳數1至10的烷基或碳數2至10的烯基，所述R¹³ 中，至少一個-CH₂ -可經-O-取代，至少一個氫可經氟取代； X¹¹ 為氟、氯、-OCF₃ 、-OCHF₂ 、-CF₃ 、-CHF₂ 、-CH₂ F、-OCF₂ CHF₂ 或-OCF₂ CHFCF₃ ； 環C¹ 、環C² 及環C³ 獨立地為1,4-伸環己基、至少一個氫可經氟取代的1,4-伸苯基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基或嘧啶-2,5-二基； Z¹⁴ 、Z¹⁵ 及Z¹⁶ 獨立地為單鍵、-(CH₂ )₂ -、-CH=CH-、-CH=CF-、-CF=CF-、-C≡C-、-COO-、-CF₂ O-、-OCF₂ -、-CH₂ O-、-CH=CF-CF₂ O-、-CF=CF-CF₂ O-或-(CH₂ )₄ -； L¹¹ 及L¹² 獨立地為氫或氟。Item 11 The liquid crystal composition according to Item 9 or Item 10, which further 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 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹³ , at least one -CH ₂ - may be substituted by -O- , at least one hydrogen can be substituted 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 in which at least one hydrogen may be substituted with fluorine, tetrahydropyran-2,5-diyl, 1 ,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; Z ¹⁴ , Z ¹⁵ and Z ¹⁶ are independently a single bond, -(CH ₂ ) ₂ -, -CH=CH- , -CH=CF-, -CF=CF-, -C≡C-, -COO-, -CF ₂ O-, -OCF ₂ -, -CH ₂ O-, -CH=CF-CF ₂ O-, -CF=CF-CF ₂ O- or -(CH ₂ ) ₄ -; L ¹¹ and L ¹² are independently hydrogen or fluorine.

式（8）中， R¹⁴ 為碳數1至10的烷基或碳數2至10的烯基，所述R¹⁴ 中，至少一個-CH₂ -可經-O-取代，至少一個氫可經氟取代； X¹² 為-C≡N或-C≡C-C≡N； 環D¹ 獨立地為1,4-伸環己基、至少一個氫可經氟取代的1,4-伸苯基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基或嘧啶-2,5-二基； Z¹⁷ 獨立地為單鍵、-(CH₂ )₂ -、-C≡C-、-COO-、-CF₂ O-、-OCF₂ -或-CH₂ O-； L¹³ 及L¹⁴ 獨立地為氫或氟； i為1、2、3或4。Item 12 The liquid crystal composition according to any one of Items 9 to 11, which further 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 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹⁴ , at least one -CH ₂ - may be substituted by -O-, and at least one hydrogen may be substituted by -O-. Substituted by fluorine; X ¹² is -C≡N or -C≡CC≡N; Ring D ¹ is independently 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen can be substituted by fluorine, tetrakis Hydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; Z ¹⁷ is independently a single bond, -(CH ₂ ) ₂ - , -C≡C-, -COO-, -CF ₂ O-, -OCF ₂ - or -CH ₂ O-; L ¹³ and L ¹⁴ are independently hydrogen or fluorine; i is 1, 2, 3 or 4.

式（9）至式（15）中， R¹⁵ 及R¹⁶ 獨立地為碳數1至10的烷基或碳數2至10的烯基，所述R¹⁵ 及R¹⁶ 中，至少一個-CH₂ -可經-O-取代，至少一個氫可經氟取代； R¹⁷ 為氫、氟、碳數1至10的烷基或碳數2至10的烯基，所述R¹⁷ 中，至少一個-CH₂ -可經-O-取代，至少一個氫可經氟取代，但不存在R¹⁷ 為氟的情況； 環E¹ 、環E² 、環E³ 及環E⁴ 獨立地為1,4-伸環己基、1,4-伸環己烯基、至少一個氫可經氟取代的1,4-伸苯基、四氫吡喃-2,5-二基或十氫萘-2,6-二基； 環E⁵ 及環E⁶ 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、四氫吡喃-2,5-二基或十氫萘-2,6-二基； Z¹⁸ 、Z¹⁹ 、Z²⁰ 及Z²¹ 獨立地為單鍵、-(CH₂ )₂ -、-COO-、-CH₂ O-、-OCF₂ -或-OCF₂ -(CH₂ )₂ -； L¹⁵ 及L¹⁶ 獨立地為氟或氯； S¹¹ 為氫或甲基； X獨立地為-CHF-或-CF₂ -； j、k、m、n、p、q、r及s獨立地為0或1，k、m、n及p的和為0、1、2或3，q、r及s的和為0、1、2或3，t為1、2或3； 式（DB-1）及式（DB-2）中， X¹⁰⁰ 獨立地為-S-、-O-或-CH₂ -； a¹⁰⁰ 及a²⁰⁰ 獨立地為0、1或2，a¹⁰⁰ 及a²⁰⁰ 的和為0、1、2或3； R¹⁰⁰ 及R²⁰⁰ 獨立地為氫、碳數1至15的烷基或碳數2至10的烯基，所述R¹⁰⁰ 及R²⁰⁰ 中，至少一個-CH₂ -可經-O-取代，至少一個氫可經氟取代，但不存在R¹⁰⁰ 及R²⁰⁰ 為氟的情況； A¹⁰⁰ 及A²⁰⁰ 獨立地為1,2-伸環丙基、1,3-伸環丁基、1,3-伸環戊基、1,3-伸環戊烯基、1,4-伸環己基、1,4-伸環己烯基、1,4-伸環庚基、十氫萘-2,6-二基、1,2,3,4-四氫萘-2,6-二基、2,6,7-三氧雜雙環[2.2.2]辛烷-1,4-二基、1,4-伸苯基、萘-2,6-二基、四氫吡喃-2,5-二基、二氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、吡啶-2,5-二基、嘧啶-2,5-二基、9,10-二氫菲-2,7-二基、9H-氧雜蒽-2,6-二基或9H-芴-2,7-二基，所述A¹⁰⁰ 及A²⁰⁰ 中，至少一個氫可經氟、氯、-CF₃ 、-CHF₂ 、-CH₂ F、-OCF₃ 、-OCHF₂ 、-OCH₂ F或-C≡N取代； Z¹⁰⁰ 及Z²⁰⁰ 獨立地為單鍵或碳數1至6的伸烷基，所述Z¹⁰⁰ 及Z²⁰⁰ 中，至少一個-CH₂ -可經-O-、-S-、-CO-、-COO-、-OCO-、-CF₂ O-、-OCF₂ -、-(CH₂ )₃ O-、-O(CH₂ )₃ -、-CH=CH-CH₂ O-、-OCH₂ -CH=CH-或-SiH₂ -取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； L¹⁰⁰ 及L¹⁰¹ 獨立地為氟、氯、-CF₃ 或-CHF₂ ； L¹⁰² 、L¹⁰³ 、L¹⁰⁴ 及L¹⁰⁵ 獨立地為氫、氟、氯、-CF₃ 、-CHF₂ 、-CH₂ F、-OCF₃ 、-OCHF₂ 或-OCH₂ F，不存在L¹⁰² 、L¹⁰³ 、L¹⁰⁴ 及L¹⁰⁵ 全部為氫的情況，但L¹⁰² 、L¹⁰³ 、L¹⁰⁴ 及L¹⁰⁵ 的任意一個或兩個可為氫。Item 13 The liquid crystal composition according to any one of Items 9 to 12, which further contains a compound selected from the group consisting of formula (9) to formula (15), formula (DB-1), and formula (DB-2) At least one compound of the group of compounds.

In formulas (9) to (15), R ¹⁵ and R ¹⁶ are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹⁵ and R ¹⁶ , at least one -CH ₂ - can be substituted by -O-, at least one hydrogen can be substituted by fluorine; R ¹⁷ is hydrogen, fluorine, alkyl with 1 to 10 carbons or alkenyl with 2 to 10 carbons, among the R ¹⁷ , at least one -CH ₂ - can be substituted by -O-, at least one hydrogen can be substituted by fluorine, but there is no case where R ¹⁷ is fluorine; ring E ¹ , ring E ² , ring E ³ and ring E ⁴ are independently 1,4 - cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6 -diyl; Ring E ⁵ and Ring E ⁶ are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, tetrahydropyran-2,5-di or decahydronaphthalene-2,6-diyl; Z ¹⁸ , Z ¹⁹ , Z ²⁰ and Z ²¹ are independently a single bond, -(CH ₂ ) ₂ -, -COO-, -CH ₂ O-, -OCF 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 0 or 1, the sum of k, m, n, and p is 0, 1, 2, or 3, and the sum of q, r, and s is 0, 1, 2 or 3, t is 1, 2 or 3; In formula (DB-1) and formula (DB-2), X ¹⁰⁰ is independently -S-, -O- or -CH ₂ -; a ¹⁰⁰ and a ²⁰⁰ are independently R ¹⁰⁰ and R ²⁰⁰ are independently hydrogen, alkyl having ¹ to 15 carbons or alkene having ² to 10 carbons group, in the R ¹⁰⁰ and R ²⁰⁰ , at least one -CH ₂ - can be substituted by -O-, and at least one hydrogen can be substituted by fluorine, but there is no case where R ¹⁰⁰ and R ²⁰⁰ are fluorine; A ¹⁰⁰ and A ²⁰⁰ independently 1,2-cyclopentylene, 1,3-cyclobutyl, 1,3-cyclopentylene, 1,3-cyclopentenyl, 1,4-cyclohexylene, 1, 4-cyclohexenyl, 1,4-cycloheptide, decalin-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6 ,7-Trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl , dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 9,10-diyl Dihydrophenanthrene-2,7-diyl, 9H-oxanthene-2,6-diyl or 9H-fluorene-2,7-diyl, in A ¹⁰⁰ and A ²⁰⁰ , at least one hydrogen may be fluorine , chlorine, -C F ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F or -C≡N substituted; Z ¹⁰⁰ and Z ²⁰⁰ are independently a single bond or an alkylene having 1 to 6 carbon atoms Base, in the Z ¹⁰⁰ and Z ²⁰⁰ , at least one -CH ₂ - can be via -O-, -S-, -CO-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-CH ₂ O-, -OCH ₂ -CH=CH- or -SiH ₂ - substituted, 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; L ¹⁰⁰ and L ¹⁰¹ are independently fluorine, chlorine, -CF ₃ or -CHF ₂ ; L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ and L ¹⁰⁵ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ or -OCH ₂ F, L ¹⁰² , L ¹⁰³ absent , L ¹⁰⁴ and L ¹⁰⁵ are all hydrogen, but any one or both of L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ and L ¹⁰⁵ may be hydrogen.

式（16）中， 環F及環I獨立地為環己基、環己烯基、苯基、1-萘基、2-萘基、四氫吡喃-2-基、1,3-二噁烷-2-基、嘧啶-2-基或吡啶-2-基，這些環F及環I中，至少一個氫可經氟、氯、碳數1至12的烷基、或者至少一個氫經氟或氯取代的碳數1至12的烷基取代； 環G為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-1,2-二基、萘-1,3-二基、萘-1,4-二基、萘-1,5-二基、萘-1,6-二基、萘-1,7-二基、萘-1,8-二基、萘-2,3-二基、萘-2,6-二基、萘-2,7-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基或吡啶-2,5-二基，這些環G中，至少一個氫可經氟、氯、碳數1至12的烷基、碳數1至12的烷氧基、或者至少一個氫經氟或氯取代的碳數1至12的烷基取代； Z²² 及Z²³ 獨立地為單鍵或碳數1至10的伸烷基，所述Z²² 及Z²³ 中，至少一個-CH₂ -可經-O-、-CO-、-COO-或-OCO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-、-C(CH₃ )=CH-、-CH=C(CH₃ )-或-C(CH₃ )=C(CH₃ )-取代，至少一個氫可經氟或氯取代； P¹¹ 、P¹² 及P¹³ 獨立地為選自式（P-1）至式（P-5）所表示的基的群組中的聚合性基；

M¹¹ 為氫、氟、氯或碳數1至5的烷基，所述M¹¹ 中，至少一個氫可經氟或氯取代，至少一個-CH₂ -可經-O-取代；M¹² 及M¹³ 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基； Sp¹¹ 、Sp¹² 及Sp¹³ 獨立地為單鍵或碳數1至10的伸烷基，所述Sp¹¹ 、Sp¹² 及Sp¹³ 中，至少一個-CH₂ -可經-O-、-COO-、-OCO-或-OCOO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； u為0、1或2； f、g及h獨立地為0、1、2、3或4，而且f、g及h的和為2以上。Item 14 The liquid crystal composition according to any one of Items 9 to 13, which contains at least one polymerizable compound selected from the group of compounds represented by formula (16).

In formula (16), ring F and ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxyl Alkyl-2-yl, pyrimidin-2-yl or pyridin-2-yl, in these ring F and ring I, at least one hydrogen can be fluorine, chlorine, alkyl having 1 to 12 carbon atoms, or at least one hydrogen can be fluorine Or chlorine-substituted alkyl group with 1 to 12 carbon atoms; Ring G is 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-1,2-di base, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1 ,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-diyl Oxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, in these rings G, at least one hydrogen can be through fluorine, chlorine, alkyl having 1 to 12 carbons , an alkoxy group having 1 to 12 carbon atoms, or at least one hydrogen is substituted by an alkyl group having 1 to 12 carbon atoms substituted by fluorine or chlorine; Z ²² and Z ²³ are independently a single bond or an alkylene having 1 to 10 carbon atoms Base, in said Z ²² and Z ²³ , at least one -CH ₂ - can be substituted by -O-, -CO-, -COO- or -OCO-, and at least one -(CH ₂ ) ₂ - can be substituted by -CH= CH-, -C(CH ₃ )=CH-, -CH=C(CH ₃ )- or -C(CH ₃ )=C(CH ₃ )- substituted, at least one hydrogen may be substituted by fluorine or chlorine; P ¹¹ , P ¹² and P ¹³ are independently polymerizable groups selected from the group of groups represented by formula (P-1) to formula (P-5);

M ¹¹ is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, in the M ¹¹ , at least one hydrogen can be substituted by fluorine or chlorine, and at least one -CH ₂ - can be substituted by -O-; M ¹² and M ¹³ is independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is substituted by fluorine or chlorine; Sp ¹¹ , Sp ¹² and Sp ¹³ are independently A single bond or an alkylene group having 1 to 10 carbon atoms, in said Sp ¹¹ , Sp ¹² and Sp ¹³ , at least one -CH ₂ - may be substituted by -O-, -COO-, -OCO- or -OCOO-, 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; 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 2 or more.

式（16-1）至式（16-28）中， Sp¹¹ 、Sp¹² 及Sp¹³ 獨立地為單鍵或碳數1至10的伸烷基，所述Sp¹¹ 、Sp¹² 及Sp¹³ 中，至少一個-CH₂ -可經-O-、-COO-、-OCO-或-OCOO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，u為0、1或2，g及h獨立地為0、1、2、3或4， Z²³ 為單鍵或碳數1至10的伸烷基，所述Z²³ 中，至少一個-CH₂ -可經-O-、-CO-、-COO-或-OCO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-、-C(CH₃ )=CH-、-CH=C(CH₃ )-或-C(CH₃ )=C(CH₃ )-取代，至少一個氫可經氟或氯取代， P¹¹ 、P¹² 及P¹³ 獨立地為選自式（P-1）至式（P-3）所表示的基的群組中的聚合性基；

式（P-1）至式（P-3）中， M¹¹ 為氫、氟、氯或碳數1至5的烷基，所述M¹¹ 中，至少一個氫可經氟或氯取代，至少一個-CH₂ -可經-O-取代；M¹² 及M¹³ 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基。Item 15 The liquid crystal composition according to any one of Items 9 to 14, which contains at least one polymerizable compound selected from the group of compounds represented by Formula (16-1) to Formula (16-28) .

In formula (16-1) to formula (16-28), Sp ¹¹ , Sp ¹² and Sp ¹³ are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and among the Sp ¹¹ , Sp ¹² and Sp ¹³ , at least one -CH ₂ - can be substituted by -O-, -COO-, -OCO- or -OCOO-, 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, u is 0, 1 or 2, g and h are independently 0, 1, 2, 3 or 4, Z ²³ is a single bond or an alkylene group having 1 to 10 carbons, In the Z ²³ , at least one -CH ₂ - can be substituted by -O-, -CO-, -COO- or -OCO-, and at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH-, -C (CH ₃ )=CH-, -CH=C(CH ₃ )- or -C(CH ₃ )=C(CH ₃ )- substituted, at least one hydrogen may be substituted by fluorine or chlorine, P ¹¹ , P ¹² and P ¹³ is independently a polymerizable group selected from the group of groups represented by formula (P-1) to formula (P-3);

In formula (P-1) to formula (P-3), M ¹¹ is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and in said M ¹¹ , at least one hydrogen may be substituted by fluorine or chlorine, at least One -CH ₂ - may be substituted by -O-; M ¹² and M ¹³ are independently hydrogen, fluorine, chlorine, alkyl with 1 to 5 carbons, or at least one hydrogen with 1 to 5 carbons substituted with fluorine or chlorine the alkyl group.

Item 16 The liquid crystal composition according to any one of Items 9 to 15, which further contains a polymerizable compound other than the formula (1) according to Item 1 and the formula (16) according to Item 14, a polymer At least one of an initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, and an antifoaming agent.

Item 17 A liquid crystal display element containing the liquid crystal composition according to any one of Items 9 to 16.

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 defoaming agent, and the like; At least two of the additives. (b) A polymerizable composition prepared by adding a polymerizable compound different from the compound (1) or the compound (16) to the liquid crystal composition. (c) A polymerizable composition prepared by adding the compound (1) and the compound (16) to the liquid crystal composition. (d) A liquid crystal composite prepared by polymerizing a polymerizable composition. (e) A polymer-stabilized alignment-type element comprising the liquid crystal composite. (f) a polymer-stabilized alignment-type element produced by using a polymerizable composition obtained by adding Compound (1) and Compound (16), and It is prepared from a polymerizable compound different from compound (1) or compound (16). The form of the compound (1), the synthesis of the compound (1), the liquid crystal composition, and the liquid crystal display element will be described in this order.

1. Form of Compound (1) The compound (1) according to an embodiment of the present invention is a polar compound having a structure represented by at least one formula (A-1) or formula (A-2) and having a polymerizable group. . The compound (1) exhibits the above effects by having a structure such as formula (A-1) or formula (A-2) in the molecule.

One of the uses of the compound (1) is an additive for liquid crystal compositions used in liquid crystal display elements. Compound (1) is added for the purpose of horizontally controlling the alignment of liquid crystal molecules. Preferable properties to be possessed by such a compound are chemical stability under the condition of being enclosed in an element, high solubility in a liquid crystal composition, and high voltage holding ratio when used in a liquid crystal display element. Compound (1) satisfies this property to a considerable extent.

Preferred examples of compound (1) will be described. Preferred examples of R ¹ , Z ¹ to Z ⁵ , A ¹ to A ⁴ , Sp ¹ , Sp ² , P ¹ , P ² , a and b in compound (1) also apply to the following formula of compound (1). In the compound (1), properties can be arbitrarily adjusted by appropriately combining the types of these groups. Compound (1) may also contain isotopes such as ² H (deuterium), ¹³ C, and the like in greater amounts than naturally occurring ratios, since there is no large difference in the properties of the compounds.

當a為2時，兩個環A¹ 可不同，當b為2時，兩個環A⁴ 可不同。a and b are independently 0, 1 or 2, and the sum of a and b is 0, 1, 2 or 3; Ring A ¹ , Ring A ² , Ring A ³ and Ring A ⁴ are independently 1,4-ring-extended Hexyl, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-2,6-diyl, decalin-2,6-diyl, 1,2,3,4-tetrahydro Naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5 -diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl, 2, 3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, formula (A-1) Or formula (A-2), in these rings, at least one hydrogen can be through fluorine, chlorine, alkyl with 1 to 12 carbons, alkenyl with 2 to 12 carbons, alkoxy with 1 to 11 carbons, carbon Alkenyloxy, -Sp ¹ -P ¹ or -Sp ² -P ² of numbers 2 to 11 are substituted, in these groups, at least one hydrogen may be substituted by fluorine or chlorine, wherein ring A ¹ , ring A ² , ring A At least one of ³ or ring A ⁴ is a group represented by formula (A-1) or formula (A-2), and in formula (A-1) and formula (A-2), Q ¹ and Q ² are independently -CH ₂ -, -O-, -N(-R ⁸ )- or -S-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R ⁸ , 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, but no R is present ⁸ is fluorine or chlorine,

When a is 2, the two rings A ¹ may be different, and when b is 2, the two rings A ⁴ may be different.

Preferred Ring A ¹ , Ring A ² , Ring A ³ and Ring A ⁴ are independently 1,4-cyclohexylene, 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, perhydrocyclopenta[a]phenanthrene-3,17-diyl, 2,3 ,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, represented by formula (A-1) The group represented by the formula (A-2) or the group represented by the formula (A-2), preferably Q ¹ and Q ² are -CH ₂ -, -O-, -N(-R ⁸ )- or -S-, more preferably Q ¹ and Q ² is -CH ₂ - or -N(-R ⁸ )-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R ⁸ , at least one -CH ₂ - may be through - O- or -S- substituted, 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, but no R ⁸ is fluorine or the case of chlorine. In these rings, at least one hydrogen may be fluorine, chlorine, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11 carbons, or alkenyloxy having 2 to 11 carbons Substituted, in these groups, at least one hydrogen may be substituted with fluorine or chlorine. More preferably 1,4-cyclohexylene, 1,4-phenylene, perhydrocyclopenta[a]phenanthrene-3,17-diyl or 2,3,4,7,8,9,10, 11,12,13,14,15,16,17-Tetrahydrocyclopenta[a]phenanthrene-3,17-diyl, in these rings, at least one hydrogen can be through fluorine or alkane having 1 to 5 carbons base substitution. Especially preferred is 1,4-cyclohexylene, 1,4-phenylene or perhydrocyclopento[a]phenanthrene-3,17-diyl, in these rings, at least one hydrogen can be fluorine, methyl or Ethyl substitution.

Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and among the Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ , at least one -CH ₂ - can be substituted by -O-, -S-, -CO-, -COO-, -OCO- or -OCOO-, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH- or -C ≡C-substituted, at least one hydrogen may be replaced by fluorine or chlorine. Wherein, at least one of Z ² , Z ³ or Z ⁴ is -COS-, -SCO-, -CH=CHCOS-, -SCOCH=CH-, -COO-, -OCO-, -CH=CH-, - CH=CHCO- or -COCH=CH-, when a is 2, the two Z ¹ can be different, and when b is 2, the two Z ⁵ can be different. Preferred Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are independently a single bond, -(CH ₂ ) ₂ -, -CH=CH-, -C≡C-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -CH ₂ O-, -OCH ₂ -, -CF=CF-, -COS-, -SCO-, -CH=CHCOS-, -SCOCH=CH-, -CH =CHCO- or -COCH=CH-. More preferably, it is a single bond, -(CH ₂ ) ₂ -, -CH=CH-, -COO-, -OCO-, -CH=CHCO-, or -COCH=CH-. Particularly preferred is a single bond, -COO- or -OCO-.

Sp ¹ and Sp ² are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in the alkylene group, at least one -CH ₂ - may be via -O-, -CO-, -COO-, -OCO - or -OCOO- substituted, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH- or -C≡C-, in these groups, at least one hydrogen can be substituted by fluorine, chlorine or -Sp ¹ -P ¹ Or -Sp ² -P ² substituted. Preferred Sp ¹ and Sp ² are independently a single bond, an alkylene group having 1 to 6 carbon atoms or a -CH ₂ - alkylene group having 1 to 6 carbon atoms substituted with -O-, or -OCOO-. Furthermore, it is preferably an alkylene group having 1 to 6 carbon atoms or -OCOO-.

P ¹ and P ² are independently a group represented by any one of Formula (1b) to (1h).

Preferable P ¹ and P ² are independently a group represented by any one of formula (1b), formula (1c), formula (1d), and formula (1e).

M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, fluorine, chlorine, an alkyl group with 1 to 5 carbon atoms, or an alkyl group with 1 to 5 carbon atoms in which at least one hydrogen is substituted by fluorine or chlorine, preferably M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, fluoro, methyl, ethyl or trifluoromethyl. More preferably, it is hydrogen.

R ² and R ⁶ are hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbons, in the alkyl group, at least one hydrogen may be substituted by fluorine or chlorine, and at least one -CH ₂ - may be substituted by -O-.

Preferred R2 and ^R6 are ^hydrogen , fluorine, methyl, ethyl, methoxymethyl or trifluoromethyl. More preferably, it is hydrogen.

R ³ , R ⁴ , R ⁵ and R ⁷ are independently hydrogen or an alkyl group having 1 to 15 carbon atoms, and among said R ³ , R ⁴ , R ⁵ and R ⁷ , at least one -CH ₂ - may be through -O - or -S-substituted, 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, but there is no R ⁵ and R ⁷ are In the case of fluorine or chlorine.

Preferred R ³ , R ⁴ , R ⁵ and R ⁷ are independently hydrogen, straight-chain alkyl having 1 to 10 carbons, straight-chain alkenyl having 2 to 10 carbons, straight-chain having 1 to 10 carbons alkoxy or cyclic alkyl having 3 to 6 carbon atoms. Further preferred is hydrogen, a linear alkyl group having 2 to 6 carbon atoms, a linear alkenyl group having 2 to 6 carbon atoms, a linear alkoxy group having 1 to 5 carbon atoms, or a cyclic group having 4 to 6 carbon atoms. alkyl.

X ¹ is -N(-R ⁹ )-, -O- or -S-, where R ⁹ is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R ⁹ , at least one -CH ₂ - can be Substituted by -O- or -S-, 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, but no R ⁹ is present In the case of fluorine or chlorine.

式（1b）至式（1h）中，M¹ 及M² 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基，X² 、X³ 、X⁴ 、X⁵ 及X⁶ 獨立地為-N(-R⁹ )-、-O-或-S-，此處，R⁹ 為氫或碳數1至15的烷基，所述R⁹ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁹ 為氟或氯的情況。Further preferred groups are formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), formula (1d) -1), the group represented by the formula (1d-2) or the formula (1e-1).

In formulas (1b) to (1h), M ¹ and M ² are independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is substituted by fluorine or chlorine. Alkyl, X ² , X ³ , X ⁴ , X ⁵ and X ⁶ are independently -N(-R ⁹ )-, -O- or -S-, where R ⁹ is hydrogen or carbon number 1 to 15 The alkyl group, in the R ⁹ , at least one -CH ₂ - can be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH- or -C≡C- , at least one hydrogen can be replaced by fluorine or chlorine, but there is no case where R ⁹ is fluorine or chlorine.

式（1-1）至式（1-3）中， 環A¹ 、環A² 、環A³ 及環A⁴ 獨立地為1,4-伸環己基、1,4-伸苯基、萘-2,6-二基、嘧啶-2,5-二基、吡啶-2,5-二基、芴-2,7-二基、菲-2,7-二基、蒽-2,6-二基、式（A-1）或式（A-2）所表示的基，這些環A¹ 、環A² 、環A³ 及環A⁴ 中，至少一個氫可經氟、氯、碳數1至12的烷基、碳數2至12的烯基、碳數1至11的烷氧基、碳數2至11的烯氧基、-Sp¹ -P¹ 或-Sp² -P² 取代，這些烷基、烯基、烷氧基、烯氧基、-Sp¹ -P¹ 或-Sp² -P² 中，至少一個氫可經氟或氯取代，其中，環A¹ 、環A² 、環A³ 或環A⁴ 的至少一個為式（A-1）或式（A-2），Q¹ 及Q² 獨立地為-CH₂ -、-O-、-N(R⁸ )-或-S-，此處，R⁸ 為氫或碳數1至15的烷基，所述R⁸ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁸ 為氟或氯的情況；

Z² 、Z³ 及Z⁴ 獨立地為單鍵、-(CH₂ )₂ -、-C≡C-、-C≡C-C≡C-、-COO-、-OCO-、-CF₂ O-、-OCF₂ -、-CH₂ O-、-OCH₂ -、-CF=CF-、-CH=CHCOO-、-OCOCH=CH-、-CH=CH-、-CH=CHCO-、-COCH=CH-、-COS-、-SCO-、-CH=CHCOS-或-SCOCH=CH-； Sp¹ 及Sp² 獨立地為單鍵或碳數1至10的伸烷基，所述伸烷基中，至少一個-CH₂ -可經-O-、-COO-、-OCOO-或-OCO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-取代，這些基中，至少一個氫可經氟、氯或-Sp¹ -P¹ 或-Sp² -P² 取代，在存在多個Sp¹ 或Sp² 的情況下，任意兩個可不同； P¹ 及P² 獨立地為式（1b）至式（1h）的任一者所表示的基，在存在多個P¹ 或P² 的情況下，任意兩個可不同；

式（1b）至式（1h）中， M¹ 、M² 、M³ 及M⁴ 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基；X¹ 為-N(-R⁹ )-、-O-或-S-，此處，R⁹ 為氫或碳數1至15的烷基，所述R⁹ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁹ 為氟或氯的情況； R² 及R⁶ 為氫、氟、氯或碳數1至5的烷基，所述R² 及R⁶ 中，至少一個氫可經氟或氯取代，至少一個-CH₂ -可經-O-取代； R³ 、R⁴ 、R⁵ 及R⁷ 獨立地為氫或碳數1至15的烷基，所述R³ 、R⁴ 、R⁵ 及R⁷ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁵ 及R⁷ 為氟或氯的情況。Preferred examples of compound (1) are formula (1-1) to formula (1-3).

In formula (1-1) to formula (1-3), ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are independently 1,4-cyclohexylene, 1,4-phenylene, naphthalene -2,6-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl In a diradical, a radical represented by formula (A-1) or formula (A-2), among these ring A ¹ , ring A ² , ring A ³ and ring A ⁴ , at least one hydrogen may be replaced by fluorine, chlorine, carbon atoms Alkyl of 1 to 12, alkenyl of carbon number 2 to 12, alkoxy of carbon number of 1 to 11, alkenyloxy of carbon number of 2 to 11, -Sp ¹ -P ¹ or -Sp ² -P ² substituted , in these alkyl groups, alkenyl groups, alkoxy groups, alkenyloxy groups, -Sp ¹ -P ¹ or -Sp ² -P ² , at least one hydrogen may be substituted by fluorine or chlorine, wherein ring A ¹ , ring A ² , at least one of ring A ³ or ring A ⁴ is formula (A-1) or formula (A-2), and Q ¹ and Q ² are independently -CH ₂ -, -O-, -N(R ⁸ )- or -S-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, in said R ⁸ , at least one -CH ₂ - may be substituted by -O- or -S-, 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, but there is no situation that R ⁸ is fluorine or chlorine;

Z ² , Z ³ and Z ⁴ are independently a single bond, -(CH ₂ ) ₂ -, -C≡C-, -C≡CC≡C-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -CH ₂ O-, -OCH ₂ -, -CF=CF-, -CH=CHCOO-, -OCOCH=CH-, -CH=CH-, -CH=CHCO-, -COCH=CH -, -COS-, -SCO-, -CH=CHCOS- or -SCOCH=CH-; Sp ¹ and Sp ² are independently a single bond or an alkylene group having 1 to 10 carbon atoms, in the alkylene group, At least one -CH ₂ - can be substituted by -O-, -COO-, -OCOO- or -OCO-, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH-, among these groups, at least one hydrogen Can be substituted by fluorine, chlorine or -Sp ¹ -P ¹ or -Sp ² -P ² , in the presence of multiple Sp ¹ or Sp ² , any two can be different; P ¹ and P ² are independently of the formula ( 1b) to the group represented by any one of the formula (1h), in the case of a plurality of P ¹ or P ² , any two may be different;

In formula (1b) to formula (1h), M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 5 carbon atoms, or at least one hydrogen substituted by fluorine or chlorine Alkyl having 1 to 5 carbons; X ¹ is -N(-R ⁹ )-, -O- or -S-, where R ⁹ is hydrogen or alkyl having 1 to 15 carbons, and R ⁹ Among them, at least one -CH ₂ - can be substituted by -O- or -S-, 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 substitution, but there is no case where R ⁹ is fluorine or chlorine; R ² and R ⁶ are hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and among the R ² and R ⁶ , at least one hydrogen can be Fluorine or chlorine substitution, at least one -CH ₂ - may be substituted by -O-; R ³ , R ⁴ , R ⁵ and R ⁷ are independently hydrogen or an alkyl group having 1 to 15 carbons, the R ³ , R ⁴ , R ⁵ and R ⁷ , at least one -CH ₂ - can be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH- or -C≡C-, at least one One hydrogen can be replaced by fluorine or chlorine, but there is no case where ^R5 and ^R7 are fluorine or chlorine.

In the compound represented by formula (1-1), formula (1-2) or formula (1-3), any one of Z ² , Z ³ or Z ⁴ is preferably -COO- or -OCO-.

這些式中， Sp¹ 及Sp² 獨立地為單鍵或碳數1至10的伸烷基，所述Sp¹ 及Sp² 中，至少一個-CH₂ -可經-O-、-COO-、-OCOO-或-OCO-取代，至少一個-(CH₂ )₂ -可經-CH=CH-取代，至少一個氫可經-Sp¹ -P¹ 或-Sp² -P² 取代； P¹ 、P² 、Sp¹ 及Sp² 以外的部分結構中，至少一個氫可經氟、氯、甲基或乙基取代； Q¹ 為-CH₂ -或-N(-R⁸ )-，Q² 為-N(-R⁸ )-，此處，R⁸ 為氫或碳數1至15的烷基，所述R⁸ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁸ 為氟或氯的情況， P¹ 及P² 獨立地為式（1b-1）、式（1b-2）、式（1b-3）、式（1b-4）、式（1b-5）、式（1c-1）、式（1d-1）、式（1d-2）或式（1e-1）所表示的基；

式（1b-1）、式（1b-2）、式（1b-3）、式（1b-4）、式（1b-5）、式（1c-1）、式（1d-1）、式（1d-2）或式（1e-1）中，X² 、X³ 、X⁴ 、X⁵ 及X⁶ 獨立地為-N(-R⁹ )-、-O-或-S-，此處，R⁹ 為氫或碳數1至15的烷基，所述R⁹ 中，至少一個-CH₂ -可經-O-或-S-取代，至少一個-(CH₂ )₂ -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，但不存在R⁹ 為氟或氯的情況。Compound (1) is preferably a compound represented by the following formula.

In these formulas, Sp ¹ and Sp ² are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in the Sp ¹ and Sp ² , at least one -CH ₂ - may be through -O-, -COO-, -OCOO- or -OCO- substituted, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH-, at least one hydrogen can be substituted by -Sp ¹ -P ¹ or -Sp ² -P ² ; P ¹ , In partial structures other than P ² , Sp ¹ and Sp ² , at least one hydrogen may be substituted by fluorine, chlorine, methyl or ethyl; Q ¹ is -CH ₂ - or -N(-R ⁸ )-, Q ² is -N(-R ⁸ )-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, in said R ⁸ , at least one -CH ₂ - may be substituted by -O- or -S-, 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, but there is no case where R ⁸ is fluorine or chlorine, P ¹ and P ² independently formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), formula (1d-1) ), the base represented by formula (1d-2) or formula (1e-1);

Equation (1b-1), Equation (1b-2), Equation (1b-3), Equation (1b-4), Equation (1b-5), Equation (1c-1), Equation (1d-1), Equation In (1d-2) or formula (1e-1), X ² , X ³ , X ⁴ , X ⁵ and X ⁶ are independently -N(-R ⁹ )-, -O- or -S-, where , R ⁹ is hydrogen or an alkyl group with 1 to 15 carbon atoms, in said R ⁹ , at least one -CH ₂ - can be substituted by -O- or -S-, and at least one -(CH ₂ ) ₂ - can be substituted by - CH=CH- or -C≡C- substituted, at least one hydrogen can be substituted by fluorine or chlorine, but there is no case where R ⁹ is fluorine or chlorine.

In addition, specific examples of the compound (1) will be described in Examples to be described later.

Formulas (2) to (15) show component compounds of the liquid crystal composition. Compounds (2) to (4) have small dielectric anisotropy. Compounds (5) to (7) have large positive dielectric anisotropy. Compound (8) has a larger positive dielectric anisotropy because it has a cyano group. Compounds (9) to (16) have large negative dielectric anisotropy. Specific examples of these compounds will be described below.

In compound (16), P ¹¹ , P ¹² and P ¹³ are independently polymerizable groups.

Preferable P ¹¹ , P ¹² and P ¹³ are polymerizable groups selected from the group of groups represented by formula (P-1) to formula (P-5). Further preferable P ¹¹ , P ¹² and P ¹³ are formula (P-1), formula (P-2) or formula (P-3). A particularly preferred formula (P-1) is -OCO-CH=CH ₂ or -OCO-C(CH ₃ )=CH ₂ . The wavy lines in the formula (P-1) to the formula (P-5) indicate the part to be bonded.

In formula (P-1) to formula (P-5), M ¹¹ is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbons, and in said M ¹¹ , at least one hydrogen may be substituted by fluorine or chlorine, at least One -CH ₂ - may be substituted by -O-; M ¹² and M ¹³ are independently hydrogen, fluorine, chlorine, alkyl with 1 to 5 carbons, or at least one hydrogen with 1 to 5 carbons substituted with fluorine or chlorine the alkyl group. In order to improve reactivity, preferable M ¹¹ , M ¹² and M ¹³ are hydrogen or methyl. More preferable M ¹¹ is methyl, and more preferable M ¹² and M ¹³ are hydrogen.

Sp ¹¹ , Sp ¹² and Sp ¹³ are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and among the Sp ¹¹ , Sp ¹² and Sp ¹³ , at least one -CH ₂ - may be via -O-, -COO -, -OCO- or -OCOO- substituted, 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.

Preferred Sp ¹¹ , Sp ¹² and Sp ¹³ are single bonds.

Ring F and Ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxan-2-yl, Pyrimidine-2-yl or pyridin-2-yl, in these rings, at least one hydrogen can be fluorine, chlorine, alkyl with 1 to 12 carbons, alkoxy with 1 to 12 carbons, or at least one hydrogen with fluorine or chlorine-substituted alkyl group having 1 to 12 carbon atoms.

Preferred ring F and ring I are phenyl. 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, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2, 5-diyl or pyridine-2,5-diyl, in these rings, at least one hydrogen can be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or at least one hydrogen Substituted with alkyl having 1 to 12 carbons substituted with fluorine or chlorine. Particularly preferred ring G is 1,4-phenylene or 2-fluoro-1,4-phenylene.

Z ²² and Z ²³ are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in the alkylene group, at least one -CH ₂ - may be via -O-, -CO-, -COO- or -OCO -Substituted, at least one -(CH ₂ ) ₂ - may be via -CH=CH-, -C(CH ₃ )=CH-, -CH=C(CH ₃ )- or -C(CH ₃ )=C(CH ₃ )-Substituted, in these groups, at least one hydrogen may be replaced by fluorine or chlorine.

Preferred Z ⁷ and Z ⁸ are a single bond, -(CH ₂ ) ₂ -, -CH ₂ O-, -OCH ₂ -, -COO- or -OCO-. More preferable Z ²² and Z ²³ are single bonds.

u is 0, 1 or 2.

Preferably u is 0 or 1. f, g and h are independently 0, 1, 2, 3 or 4, and the sum of f, g and h is 1 or more. Preferred f, g or h are 1 or 2.

2. Synthesis of compound (1) The synthesis method of compound (1) is demonstrated. Compound (1) can be synthesized by appropriately combining methods of synthetic organic chemistry. Compounds with undocumented syntheses were identified by Organic Syntheses (John Wiley & Sons, Inc), Organic Reactions (John Wiley & Sons) , Inc)), "Comprehensive Organic Synthesis" (Pergamon Press), "New Experimental Chemistry Lectures" (Maruzen) and other books to synthesize.

2-1. Generation of Bonding Group Z ¹ , Bonding Group Z ² , Bonding Group Z ³ , Bonding Group Z ⁴ and Bonding Group Z ⁵ Examples of the method for generating the bonding group in compound (1) are as follows described in the process. In the scheme, MSG ¹ (or MSG ² ) is a monovalent organic group having at least one ring. The monovalent organic groups represented by a plurality of MSG ¹ (or MSG ² ) may be the same, or may be different. Compound (1A) to compound (1L) correspond to compound (1) or an intermediate of compound (1).

(I) Generation of single bonds Compound (1A) is synthesized by reacting arylboronic acid (21) with compound (22) in the presence of a carbonate and a tetrakis(triphenylphosphine)palladium catalyst. The compound (1A) can also be synthesized by reacting the compound (23) with n-butyllithium, followed by a reaction with zinc chloride, and then in the presence of a dichlorobis(triphenylphosphine)palladium catalyst React with compound (22).

(II) Generation of -COO- and -OCO- The carboxylic acid (24) is obtained by reacting compound (23) with n-butyllithium and then reacting with carbon dioxide. The carboxylic acid (24) is combined with the phenol (25) derived from compound (21) in 1,3-dicyclohexylcarbodiimide (1,3-dicyclohexylcarbodiimide, DCC) with 4-dimethylamine Compound (1B) with -COO- was synthesized by dehydration in the presence of 4-dimethylamino pyridine (DMAP). Compounds with -OCO- were also synthesized using the method.

(III) Production of -CF ₂ O- and -OCF ₂ - Compound ( 26 ) is obtained by sulfurizing compound ( 1B ) with Lawesson's reagent. Compound (1C) having -CF ₂ O- was synthesized by fluorination of compound (26) with hydrogen fluoride pyridine complex and N-bromosuccinimide (NBS). See M. Kuroboshi et al., Chem. Lett., 1992, No. 827. Compound (1C) can also be synthesized by fluorination of compound (26) with (diethylamino)sulphur trifluoride (DAST). See WH Bunnelle et al., J. Org. Chem., 1990, vol. 55, p. 768. Compounds with -OCF2- _were also synthesized using the method described.

(IV) Generation of -CH=CH- The aldehyde (27) is obtained by reacting the compound (22) with n-butyllithium and then with N,N-Dimethylformamide (N,N-Dimethyl Formamide, DMF). Compound (1D) is synthesized by reacting a phosphonium salt (28) with potassium tert-butoxide to produce a phosphorus ylide, and reacting the phosphorous ylide with an aldehyde (27). Since a cis isomer is produced depending on the reaction conditions, the cis isomer is isomerized into a trans isomer by a known method if necessary.

Formation of (V)-(CH ₂ ) ₂ - Compound (1E) is synthesized by hydrogenating compound (1D) in the presence of a palladium-carbon catalyst.

(VI) Generation of -C≡C- Compound (23) is reacted with 2-methyl-3-butyn-2-ol in the presence of a catalyst of dichloropalladium and copper iodide, followed by deprotection under basic conditions to obtain compound (29) . Compound (1F) is synthesized by reacting compound (29) with compound (22) in the presence of a catalyst of dichlorobis(triphenylphosphine)palladium and copper halide.

(VII) Production of -CH ₂ O- and -OCH ₂ - Compound (30) is obtained by reducing compound (27) with sodium borohydride. It is brominated with hydrobromic acid to obtain compound (31). Compound (1G) is synthesized by reacting compound (25) with compound (31) in the presence of potassium carbonate. Compounds with -OCH ₂ - were also synthesized using the method described.

(VIII) Generation of -CF=CF- Compound (32) is obtained by treating compound (23) with n-butyllithium and then reacting tetrafluoroethylene. Compound (22) is treated with n-butyllithium and then reacted with compound (32) to synthesize compound (1H).

(IX) Generation of -CH=CHCO- and -COCH=CH- Compound (1I) is synthesized by aldol condensation of compound (40) with compound (27) in the presence of NaOH.

(X) Generation of -CH=CHCOO- and -OCOCH=CH- Compound (1J) is synthesized by dehydrating cinnamic acid (41) and compound (25) in the presence of 1,3-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP).

(X) Generation of -CH=CHCOS- and -SCOCH=CH- Compound (1K) is synthesized by dehydrating cinnamic acid (41) and compound (26) in the presence of 1,3-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP).

(XI) Generation of -COS- and -SCO- Compound (1L) is synthesized by dehydrating carboxylic acid (24) and compound (26) in the presence of 1,3-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP).

2-2. Generation of Ring A ¹ , Ring A ² , Ring A ³ and Ring A ⁴ Fluoro-1,4-phenylene, 2-methyl-1,4-phenylene, 2-ethyl-1,4-phenylene, naphthalene-2,6-diyl, decalin-2 ,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl base, pyrimidine-2,5-diyl, pyridine-2,5-diyl, perhydrocyclopento[a]phenanthrene-3,17-diyl, 2,3,4,7,8,9,10 ,11,12,13,14,15,16,17-Tetrahydrocyclopenta[a]phenanthrene-3,17-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 5, Rings such as 6-dihydrophenanthridine-3,8-diyl and 6(5H)-phenanthridinone-3,8-diyl, starting materials are commercially available or synthetic methods are widely known.

2-3. Formation of the linking group Sp ¹ or the linking group Sp ² and the polymerizable group P ¹ or the polymerizable group P ² Preferred examples of the polymerizable group P ¹ or the polymerizable group P ² are acrylate (1b), cis-butyl enediimide (1c), itaconate (1d), vinyl ester (1e), formula (1f), oxane (1g) or vinyloxy (1h).

An example of a method for synthesizing a compound in which the polymerizable group is bonded to the ring via the linking group Sp ¹ or the linking group Sp ² is as follows. First, an example in which the linking group Sp ¹ or the linking group Sp ² is a single bond is shown.

(1) Synthesis of Compounds in which Sp 1 or Sp 2 are Single Bonds The methods for synthesizing compounds in which Sp ¹ or Sp ² are single bonds are as described in the following scheme. In the scheme, MSG ¹ is a monovalent organic group having at least one ring. Compound (1S) to compound (1X) correspond to compound (1). When the polymerizable group is an acrylate or acrylamide derivative, it is synthesized by esterification or amidation of the corresponding acrylic acid with HO-MSG ¹ or HNR ⁹ -MSG ¹ . Ethyleneoxy was synthesized by etherification of HO-MSG ¹ with vinyl bromide. The oxane group is synthesized by oxidation of the terminal double bond. The maleimide group is synthesized by the reaction of the amine group with maleic anhydride. Itaconic acid esters were synthesized by esterification of the corresponding itaconic acid with HO-MSG ¹ . Vinyl esters were synthesized by transesterification of vinyl acetate with HOOC-MSG ¹ .

The synthesis method of the compound in which the linking group Sp ¹ or the linking group Sp ² is a single bond has been described above. The method for generating other linking groups can be synthesized by referring to the synthesis method of the bonding group Z ¹ , the bonding group Z ² , the bonding group Z ³ , the bonding group Z ⁴ , and the bonding group Z ⁵ .

2-4. Synthesis Examples Examples of the method for synthesizing the compound (1) are as follows. Among these compounds, MES is a mesogen group having at least one ring. The definitions of P ¹ , M ¹ , M ² , Sp ¹ and Sp ² are the same as described above. Compound (51A) and compound (51B) are commercially available or can be synthesized according to a usual organic synthesis method using mesogen (MES) having an appropriate ring structure as a starting material. When synthesizing a compound in which MES and Sp ¹ are linked by an ether bond, compound (53A) can be obtained by etherifying compound (52) and a base such as potassium hydroxide using compound (51A) as a starting material. In addition, when synthesizing a compound in which MES and Sp ¹ are linked by a single bond, a compound (51B) can be obtained by performing a cross-coupling reaction using compound (52), a metal catalyst such as palladium, and a base using compound (51B) as a starting material. (53B). The compound (53A) or the compound (53B) is sometimes derived as a compound (54A) or a compound in which a protecting group such as trimethylsilyl (TMS) and tetrahydropyranyl (THP) functions as necessary. (54B). Then, compound (57A) can be obtained by etherifying compound (53A), compound (53B), compound (54A) or compound (54B) again in the presence of compound (55) and a base such as potassium hydroxide. ) or compound (57B). At this time, when the protective group is made to function in the previous stage, the protective group is removed by a deprotection reaction.

P² 例如為式（1b-3）所表示的基的化合物（1）可由化合物（57）並利用以下方法來合成。由化合物（57）並在化合物（58）、DCC及DMAP的存在下進行酯化反應，由此可衍生為化合物（1Y）。

Compound (1) in which P ² is, for example, a group represented by formula (1b-3) can be synthesized from compound (57) by the following method. Compound (1Y) can be derived from compound (57) by performing an esterification reaction in the presence of compound (58), DCC and DMAP.

3. Liquid crystal composition The liquid crystal composition of the embodiment of the present invention contains the compound (1) as the component A. The compound (1) contributes to the control of the alignment of the liquid crystal molecules by the interaction with the substrate of the element in a non-covalent bonding manner. The composition preferably contains the compound (1) as the component A, and further contains a liquid crystal compound selected from the group consisting of the component B, the component C, the component D, and the component E shown below. Ingredient B is compound (2) to compound (4). Ingredient C is compound (5) to compound (7). Ingredient D is compound (8). Ingredient E is compound (9) to compound (16). The composition may also contain other liquid crystal compounds other than the compounds (2) to (16). 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 and the like. A composition with appropriately selected components has a high upper limit temperature, a low lower limit temperature, a small viscosity, an appropriate optical anisotropy (ie, a large optical anisotropy or a small optical anisotropy), a large positive or Negative dielectric anisotropy, large specific resistance, stability to heat or ultraviolet light, and appropriate elastic constant (ie, large elastic constant or small elastic constant).

In order to maintain high stability to ultraviolet rays, the preferred ratio of compound (1) is usually about 0.01% by weight or more based on the weight of the liquid crystal composition, and the preferred ratio of compound (1) is usually about 10% in order to dissolve in the liquid crystal composition. % by weight or less. A further preferred ratio is in the range of about 0.1% by weight to about 5% by weight based on the weight of the liquid crystal composition. The most preferred ratio is in the range of about 0.5 wt % to about 3 wt % based on the weight of the liquid crystal composition.

Component B is a compound whose two terminal groups are alkyl groups or the like. 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 the compound of component B, R ¹¹ and R ¹² are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in the alkyl or alkenyl group, at least one -CH ₂ - may be through - O-substituted, at least one hydrogen may be replaced by fluorine.

Component B is a nearly neutral compound because the absolute value of the dielectric anisotropy is small. Compound (2) is mainly effective in reducing viscosity or adjusting optical anisotropy. Compound (3) and compound (4) have the effect of expanding 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 is increased, the dielectric anisotropy of the composition decreases, but the viscosity decreases. Therefore, as long as the required value of the threshold voltage of the element is satisfied, the content should be large. When preparing compositions for modes such as IPS and VA, the content of component B is preferably 30% by weight or more, and more preferably 40% by weight or more, based on the weight of the liquid crystal composition.

Component C is compound (5) to compound (7) having fluorine, chlorine or a fluorine-containing group at the right terminal. Preferred examples of component C include compound (5-1) to compound (5-16), compound (6-1) to compound (6-120), compound (7-1) to compound (7-62) ). In the compound of component C, R ¹³ is an alkyl group having ₁ to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms. _{One hydrogen} may be substituted with fluorine _; X11 is fluorine, chlorine, _-OCF3 , _-OCHF2 , _-CF3 , _-CHF2 , ^-CH2F , _-OCF2CHF2 or _-OCF2CHFCF3 .

Component C has positive dielectric anisotropy and is very excellent in stability to heat, light, and the like, so it is used in the preparation of compositions for modes such as IPS, FFS, and OCB. The content of Component C is suitably in the range of 1 to 99% by weight, preferably in the range of 10 to 97% by weight, and more preferably in the range of 40 to 95% by weight, based on the weight of the liquid crystal composition. When Component C is added to a composition having a negative dielectric anisotropy, the content of Component C is preferably 30% by weight or less based on the 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 element can be adjusted.

Component D is a compound (8) whose right terminal group is -C≡N or -C≡CC≡N. Preferable 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 carbon atoms or an alkenyl group having 2 to 10 carbon atoms. One hydrogen may be replaced by fluorine; X ¹² is -C≡N or -C≡CC≡N.

Since the dielectric anisotropy of component D is positive and its value is large, it is mainly used when preparing a composition for modes such as TN. By adding the component D, the dielectric anisotropy of the composition can be increased. Component D brings about 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 element.

In the case of preparing a composition for modes such as TN, the content of the component D is suitably in the range of 1% by weight to 99% by weight, preferably in the range of 10% by weight to 97% by weight, based on the weight of the liquid crystal composition, and further It is preferably in the range of 40% by weight to 95% by weight. When Component D is added to a composition having a negative dielectric anisotropy, the content of Component D is preferably 30% by weight or less based on the 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 element can be adjusted.

Ingredient E is compound (9) to compound (16). These compounds have phenylene substituted with two fluorine or chlorine in the lateral position like 2,3-difluoro-1,4-phenylene.

Preferred examples of component E include compound (9-1) to compound (9-8), compound (10-1) to compound (10-17), compound (11-1), compound (12-1) ) to compound (12-3), compound (13-1) to compound (13-11), compound (14-1) to compound (14-3), compound (15-1) to compound (15-3) and compound (16-1) to compound (16-3). In the compound of component E, R ¹⁵ and R ¹⁶ are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having ₂ to 10 carbon atoms. O-substituted, at least one hydrogen can be substituted by fluorine; R ¹⁷ is hydrogen, fluorine, alkyl with 1 to 10 carbons or alkenyl with 2 to 10 carbons, among the alkyl and alkenyl, at least one -CH ₂ - may be substituted with -O-, at least one hydrogen may be substituted with fluorine.

The dielectric anisotropy of the component E is negative and large. Component E is used in the preparation of modal compositions such as IPS, VA, and PSA. As the content of the component E is increased, the dielectric anisotropy of the composition becomes negative and increases, but the viscosity increases. Therefore, as long as the required value of the threshold voltage of the element is satisfied, the content should be small. Considering that the dielectric anisotropy is about -5, the content of Component E is preferably 40% by weight or more based on the weight of the liquid crystal composition in order to perform sufficient voltage driving.

Among the components E, since the compound (9) is a bicyclic compound, it is mainly effective in reducing the viscosity, adjusting the optical anisotropy, or increasing the dielectric anisotropy. Since compound (10) and compound (11) are tricyclic compounds, they have the effect of increasing the upper limit temperature, increasing the optical anisotropy, or increasing the dielectric anisotropy. Compounds (12) to (16) have an effect of increasing the dielectric anisotropy.

Component F is compound (DB-1) and compound (DB-2). These compounds have the structure of dibenzothiophene substituted with two fluorines or chlorines on the side like 1,8-difluoro-2,7-dibenzothiophene, 1,8-difluoro-2,7-dibenzothiophene Furan structure, etc. Preferred examples of Component F include Compound (DB-1-1) to Compound (DB-1-14) and Compound (DB-2-1) to Compound (DB-2-9). Further preferable examples of Component F include compound (DB-1-1) to compound (DB-1-14). In the compound of component F, R ¹⁰⁰ is independently hydrogen, straight-chain alkyl having 1 to 10 carbons, branched alkyl having 3 to 10 carbons, or alkenyl having 2 to 10 carbons, and in said R ¹⁰⁰ , At least one -CH ₂ - can be substituted by -O-, at least one hydrogen can be substituted by fluorine, R ²⁰⁰ is independently a straight chain alkyl group with 1 to 10 carbons, a branched chain alkyl group with 3 to 10 carbons or a carbon number The alkenyl group of 2 to 10, in the R ²⁰⁰ , at least one -CH ₂ - may be substituted by -O- or -S-, and at least one hydrogen may be substituted by fluorine.

The dielectric anisotropy of Component E and Component F is negative and large. Component E and Component F can be used in the preparation of modal compositions such as IPS, FFS, VA, and PSA. As the total content of Component E and Component F is increased, the dielectric anisotropy of the composition becomes negative and increases, but the viscosity increases. Therefore, as long as the required value of the threshold voltage of the element is satisfied, the content should be small. Considering that the dielectric anisotropy is about -5, the total content of Component E and Component F is preferably 40% by weight or more based on the weight of the liquid crystal composition in order to perform sufficient voltage driving. Component F has a condensed ring structure such as dibenzothiophene, dibenzofuran, and dibenzofluorene. It mainly has the effect of increasing the upper limit temperature, increasing the optical anisotropy or increasing the dielectric anisotropy. In addition, since it is a condensed ring structure and may have a hetero atom, it is considered that the polarity tends to be higher than that of other liquid crystal compounds, so it is estimated that the compatibility with the alignment control layer-forming monomer is relatively higher. The preferable content of Component F is in the range of 1% by weight to 20% by weight based on the weight of the liquid crystal composition. A more preferable content of the component F is in the range of 3% by weight to 20% by weight based on the weight of the liquid crystal composition. A more preferable content of the component F is in the range of 3% by weight to 15% by weight.

Among the components E, since the compound (9) is a bicyclic compound, it is mainly effective in reducing the viscosity, adjusting the optical anisotropy, or increasing the dielectric anisotropy. The compound (10) and the compound (11) are tricyclic compounds, and therefore have the effect of increasing the upper limit temperature, increasing the optical anisotropy, or increasing the dielectric anisotropy. Compounds (12) to (15) have the effect of increasing the dielectric anisotropy.

When preparing compositions for modes such as IPS, VA, and PSA, the total content of component E and component F is preferably 40% by weight or more, and more preferably 50% by weight to 95% by weight, based on the weight of the liquid crystal composition. scope. When Component E and Component F are added to a composition having positive dielectric anisotropy, the total content of Component E and Component F is preferably 30% by weight or less based on the weight of the liquid crystal composition. By adding component E and component F, the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the element can be adjusted.

By properly combining the components B, C, D, and E described above, it is possible to prepare materials that satisfy the requirements of high upper limit temperature, low minimum temperature, low viscosity, appropriate optical anisotropy, large positive or negative dielectric anisotropy, A liquid crystal composition having at least one of characteristics such as high specific resistance, high stability to ultraviolet rays, high thermal stability, and high elastic constant. A liquid crystal compound different from the component B, the component C, the component D, and the component E may be added as necessary.

The liquid crystal composition can be prepared by a known method. For example, the component compounds are mixed and then heated to dissolve each other. Additives may be added to the composition according to the application. Examples of additives are polymerizable compounds other than formula (1) and formula (16), polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, antifoaming agents agent, etc. Such additives are well known to those of ordinary skill in the art and are documented in the literature.

The polymerizable compound is added for the purpose of generating a polymer in the liquid crystal composition. A polymer is formed in the liquid crystal composition by irradiating ultraviolet rays in a state where a voltage is applied between the electrodes to copolymerize the polymerizable compound and the compound (1). At this time, the compound (1) is immobilized in a state in which the polar group interacts with the substrate surface of the glass (or metal oxide) in a non-covalent bond manner. Thereby, the ability to control the alignment of the liquid crystal molecules is further improved, and the compound (1) does not leak into the liquid crystal composition. In addition, an appropriate pretilt can be obtained also on the surface of the glass (or metal oxide) substrate, so that a liquid crystal display element with a shortened response time and a large voltage holding ratio can be obtained.

Preferable examples of the polymerizable compound are acrylates, methacrylates, vinyl compounds, vinyloxy compounds, propenyl ethers, epoxy compounds (oxiranes, oxetanes), and vinyl ketones. Further preferred examples are compounds having at least one acryloxy group and compounds having at least one methacryloyloxy group. Further preferred examples include compounds having both acryloxy and methacryloyloxy groups.

Further preferred examples of the polymerizable compound are compound (M-1) to compound (M-17). In compounds (M-1) to (M-17), R ²⁵ to R ³¹ are independently hydrogen or methyl; s, v and x are independently 0 or 1; t and u are independently 1 to 10 Integer; L ²¹ to L ²⁶ are independently hydrogen or fluorine, and L ²⁷ and L ²⁸ are independently hydrogen, fluorine or methyl.

The polymerizable compound can be rapidly polymerized by adding a polymerization initiator. By optimizing the reaction temperature, the amount of the remaining polymerizable compound can be reduced. Examples of photo-radical polymerization initiators are TPO, 1173 and 4265 in the Darocure series of BASF; 184, 369, 500, 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/Michel's ketone mixture, hexaarylbiimidazole/mercaptobenzimidazole Mixture, 1-(4-Isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, Benzyldimethylketal, 2-methyl-1-[4-(methylthio ) Phenyl]-2-morpholinopropan-1-one, 2,4-diethylxanthone/p-dimethylaminobenzoic acid methyl ester mixture, benzophenone/methyltriethanolamine mixture .

Polymerization can be carried out by adding a photoradical polymerization initiator to the liquid crystal composition, and then irradiating ultraviolet rays in a state where an electric field is applied. However, the unreacted polymerization initiator or the decomposition product of the polymerization initiator may cause poor display of images such as burn marks on the element. In order to prevent such a situation, photopolymerization may be performed without adding a polymerization initiator. The preferred wavelength of the irradiated light is in the range of 150 nm to 500 nm. A further preferred wavelength is in the range of 250 nm to 450 nm, and the most preferred wavelength is in the range of 300 nm to 400 nm.

When the compound (1) having an ester (-COO-, -OCO-) as a bonding group is mixed into the composition, the main effects of the compound (1) as the component A on the properties of the composition are as follows said. When the compound (1) undergoes Fries rearrangement or photodimerization by polarized light, it is arranged in a certain direction at the molecular level. Therefore, a thin film prepared from a polar compound aligns liquid crystal molecules in the same manner as an alignment film such as polyimide.

In the case of the compound (1) having an aromatic ester and a polymerizable group, by irradiation with ultraviolet light, the aromatic ester moiety undergoes photolysis, thereby forming a radical and generating a photo-Friesian rearrangement. In the photofries rearrangement, when the polarization direction of the polarized ultraviolet light is the same as the long axis direction of the aromatic ester moiety, photodecomposition of the aromatic ester moiety occurs. After photolysis, rebonding proceeds and intramolecular hydroxyl groups are generated by tautomerization. It is considered that the interaction of the substrate interface occurs due to the hydroxyl group, and the polar compound has anisotropy and is easily adsorbed on the substrate interface side. Moreover, since it has a polymerizable group, the compound (1) which reacts in the direction of polarized light by polymerization is fixed without losing the directionality. Such properties can be exploited to prepare thin films capable of aligning liquid crystal molecules. In order to prepare the film, the irradiated ultraviolet rays are suitably linearly polarized light. First, the compound (1), which is a polar compound, is added in a range of 0.1% by weight to 10% by weight to the liquid crystal composition, and the composition is heated in order to dissolve the polar compound. The composition is injected into an element without an alignment film. Next, while heating the element, linearly polarized light is irradiated, whereby the polar compound undergoes photofrisian rearrangement and is polymerized. The polar compounds rearranged by photofries are arranged in a certain direction, and the thin film formed after polymerization has a function as a liquid crystal alignment film.

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, hydroquinone derivatives such as methyl hydroquinone, 4-tert-butylcatechol, 4-methoxyphenol, phenothiazine, and the like.

The optically active compound brings about the effect of preventing reverse twist by inducing a helical structure in the liquid crystal molecule to impart a desired twist angle. By adding optically active compounds, the pitch of the helix can be adjusted. Two or more optically active compounds may be added for the purpose of adjusting the temperature dependence of the helical pitch. Preferred examples of the optically active compound include the following compounds (Op-1) to (Op-18). In compound (Op-18), ring J is 1,4-cyclohexylene or 1,4-phenylene, and R ²⁸ is an alkyl group having 1 to 10 carbon atoms.

In order to maintain a large voltage holding ratio, antioxidants are effective. Preferable examples of antioxidants include the following compound (AO-1) and compound (AO-2); IRGANOX 415, IRGANOX 565, and IRGANOX 1010 , Yan Jianuo (IRGANOX) 1035, Yan Jianuo (IRGANOX) 3114 and Yan Jianuo (IRGANOX) 1098 (trade name: BASF (BASF) company). In order to prevent the lowering of the upper limit temperature, an ultraviolet absorber is effective. Preferable examples of the ultraviolet absorber are benzophenone derivatives, benzoate derivatives, triazole derivatives, and the like. Specific examples include the following compounds (AO-3) and compounds (AO-4); TINUVIN 329, TINUVIN P, TINUVIN 326, TINUVIN 326 TINUVIN 234, TINUVIN 213, TINUVIN 400, TINUVIN 328 and TINUVIN 99-2 (trade name: BASF); And 1,4-diazabicyclo[2.2.2]octane (1,4-Diazabicyclo[2.2.2]octane, DABCO).

In order to maintain a large voltage holding ratio, a light stabilizer such as an amine having steric hindrance is preferable. Preferred examples of light stabilizers include the following compounds (AO-5) and compounds (AO-6); TINUVIN 144, TINUVIN 765, and TINUVIN 770DF (trade name: BASF Corporation). In order to maintain a large voltage holding ratio, a thermal stabilizer is also effective, and as a preferable example, IRGAFOS 168 (trade name: BASF) can be mentioned. To prevent foaming, antifoaming agents are effective. Preferable examples of the defoaming agent are dimethyl silicone oil, methyl phenyl silicone oil, and the like.

In compound (AO-1), R ⁴⁰ is an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, -COOR ⁴¹ or -CH ₂ CH ₂ COOR ⁴¹ , where R ⁴¹ is a carbon number 1 to 20 alkyl groups. In compound (AO-2) and compound (AO-5), R ⁴² is an alkyl group having 1 to 20 carbon atoms. In compound (AO-5), R ⁴³ is hydrogen, methyl or O ⁽ oxygen radical), ring G is 1,4-cyclohexylene or 1,4-phenylene, z is 1, 2 or 3 .

4. Liquid crystal display element The liquid crystal composition can be used for liquid crystal display elements having operating modes such as PC, TN, STN, OCB, PSA, etc. and driven in an active matrix manner. The composition can also be used for liquid crystal display elements having operating modes such as PC, TN, STN, OCB, VA, IPS, etc. 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 can also be used for nematic curvilinear aligned phase (NCAP) elements prepared by microencapsulating nematic liquid crystals, and polymer-dispersed liquid crystals prepared by forming three-dimensional network polymers in liquid crystals. Display element (Polymer Dispersed Liquid Crystal Display, PDLCD), and polymer network liquid crystal display element (Polymer Network Liquid Crystal Display, PNLCD). When the addition amount of the polymerizable compound is about 10% by weight or less based on the weight of the liquid crystal composition, a PSA mode liquid crystal display element can be produced. The preferred ratio of the polymerizable compound is in the range of about 0.1% by weight to about 2% by weight based on the weight of the liquid crystal composition. A further preferable ratio is in the range of about 0.2 wt % to about 1.0 wt % based on the weight of the liquid crystal composition. The elements in the PSA mode can be driven by active matrix, passive matrix and other driving methods. This type of element can also be applied to any type of reflection type, transmission type, and semi-transmission type. By increasing the addition amount of the polymerizable compound, a device of a polymer dispersed mode can also be produced.

In the polymer-stabilized alignment element, the polymer contained in the composition aligns the liquid crystal molecules. Compound (1), which is a polar compound, helps the liquid crystal molecules to align. That is, the compound (1) can be used instead of the alignment film. An example of a method of manufacturing such an element is described below. 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 compound is mixed to prepare a liquid crystal composition. A polymerizable compound and compound (1) as a polar compound are added to the composition. Additives may be further added if necessary. The composition is injected into the element. The element is irradiated with light. Ultraviolet rays are preferred. The polymerizable compound is polymerized by light irradiation. By the polymerization, a polymer-containing composition can be produced, whereby a device having a PSA mode can be produced.

A method of manufacturing the element will be described. The first step is to add the compound (1), which is a polar compound, to the liquid crystal composition, and to heat and dissolve the composition at a temperature higher than the upper limit temperature. The second step is to inject the composition into the liquid crystal display element. The third step is to irradiate polarized ultraviolet rays in a state where the liquid crystal composition is heated to a temperature higher than the upper limit temperature. The compound (1), which is a polar compound, undergoes photofrisian rearrangement or photodimerization by linear polarization, and also polymerizes at the same time. The polymer of compound (1) is formed on the substrate in the form of a thin film and fixed. The polymers are arranged in a certain direction at the molecular level, so the thin film has a function as a liquid crystal alignment film. This method can be used to manufacture a liquid crystal display element without an alignment film such as polyimide.

In the above procedure, the compound (1), which is a polar compound, tends to exist on the substrate because the polar group interacts with the surface of the substrate. The compound (1) aligns liquid crystal molecules by irradiation with polarized ultraviolet rays, and at the same time, the polymerizable compound is polymerized by ultraviolet rays, thereby producing a polymer that maintains the alignment. By the effect of the polymer, the alignment of the liquid crystal molecules is additionally stabilized, so that the response time of the device is shortened. The burn marks of the image are caused by the poor functioning of the liquid crystal molecules, so the burn marks are also improved at the same time by the effect of the polymer. In particular, since the compound (1) according to the embodiment of the present invention is a polymerizable polar compound, it aligns liquid crystal molecules and copolymerizes with other polymerizable compounds. Thereby, since the polar compound does not leak into the liquid crystal composition, a liquid crystal display element having a large voltage holding ratio can be obtained. [Example]

The present invention will be further described in detail with reference to Examples (including synthesis examples and use examples of elements). The present invention is not limited by these examples. The present invention includes a mixture of the composition of Use Example 1 and the composition of Use Example 2. The present invention also includes mixtures prepared by mixing at least two of the compositions of the use examples. 1. Examples of compound (1)

Compound (1) was synthesized by the procedure shown in Example 1 and the like. Unless otherwise specified, the reaction is carried out in a nitrogen atmosphere. The synthesized compounds were identified by methods such as nuclear magnetic resonance (Nuclear Magnetic Resonance, NMR) analysis. The properties 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 measurement of ¹ H-NMR, the sample is dissolved in a deuterated solvent such as CDCl ₃ , and the measurement is performed at room temperature under the conditions of 500 MHz and 16 cumulative times. Tetramethylsilane was used as an internal standard. In the measurement of ¹⁹ F-NMR, CFCl ₃ was used as an internal standard, and the measurement was carried out in a cumulative number of 24 times. In the description of NMR spectra, s refers to singlet, d refers to doublet, t refers to triplet, q refers to quartet, quin refers to quintet, sex refers to sextet, and m refers to multiplet. Peak, br means broad peak.

Gas chromatographic analysis: In the measurement, a GC-2010 gas chromatograph manufactured by Shimadzu Corporation was used. As the column, a capillary column DB-1 (length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm) manufactured by Agilent Technologies Inc. was used. As carrier gas helium (1 ml/min) was used. The temperature of the sample vaporization chamber was set to 300°C, and the temperature of the detector (flame ionization detector (FID)) portion was set to 300°C. The sample was dissolved in acetone to prepare a 1 wt % solution, and 1 μl of the obtained solution was injected into the sample vaporization chamber. As the recorder, a GC solution (GC Solution) system manufactured by Shimadzu Corporation or the like was used.

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

UV-Vis Spectroscopic Analysis: PharmaSpec UV-1700 manufactured by Shimadzu Corporation was used for the measurement. Set the detection wavelength from 190 nm to 700 nm. The sample was dissolved in acetonitrile to prepare a solution of 0.01 mmol/L, and placed in a quartz cell (optical path length 1 cm) for measurement.

Measurement sample: When measuring the phase structure and transition temperature (clear point, melting point, polymerization initiation temperature, etc.), the compound itself is used as a sample.

Measurement method: The measurement of the characteristic was carried out 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 methods that have been modified. Thin film transistors (TFTs) were not mounted on the TN elements used for the measurement.

(1) Phase structure The sample was placed on a hot plate (hot stage, model FP-52 from Mettler) of a melting point determination apparatus including a polarizing microscope. The phase state and its change were observed with a polarizing microscope while heating the sample at a rate of 3°C/min, and the type of the phase was determined.

(2) Transformation temperature (℃) During the measurement, a scanning calorimeter, a Diamond Differential Scanning Calorimeter (DSC) system manufactured by Perkin Elmer, or a high-precision DSC system manufactured by SSI Nanotechnology was used. Sensitivity differential scanning calorimeter X-DSC7000. The temperature of the sample was raised and lowered at a rate of 3°C/min, and the starting point of the endothermic peak or the exothermic peak accompanying the phase change of the sample was obtained by extrapolation, and the transition temperature was determined. The melting point of the compound and the polymerization initiation temperature were also measured using the apparatus. The temperature at which the compound is transformed from a solid to a smectic phase or a nematic phase liquid crystal phase is sometimes simply referred to as "the lower limit temperature of the liquid crystal phase". The temperature at which a compound transitions from a liquid crystal phase to a liquid is sometimes simply referred to as the "clearing point".

The crystal is represented as C. When distinguishing the type of crystals, they are represented as C ₁ and C ₂ , respectively. Denote the smectic phase as S and the nematic phase as N. Among the smectic phases, when the smectic A phase, the smectic B phase, the smectic C phase, or the smectic F phase are distinguished, they are represented as S _A , S _B , S _C or _SF , respectively. Denote the liquid (isotropic) as I. The transition temperature is expressed as, for example, "C 50.0 N 100.0 I". It indicates that the temperature at which the self-crystal transitions to the nematic phase is 50.0°C, and the temperature at which the transition from the nematic phase to the liquid is 100.0°C.

(3) Upper limit temperature of nematic phase (T _NI or NI; °C) The sample was placed on a heating plate of a melting point measuring apparatus including a polarizing microscope, and heated at a rate of 1 °C/min. The temperature at which a part of the sample changes from the nematic phase to the isotropic liquid is measured. The upper limit temperature of the nematic phase is sometimes simply referred to 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 _TNI . When the sample is a mixture of compound (1) and compounds 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 ; °C) After storing the sample having a 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 a sample maintains a nematic phase at -20°C and changes to a crystalline or smectic phase at -30°C, the T _C is described as ≦-20°C. The lower limit temperature of the nematic phase is sometimes simply referred to as the "lower limit temperature".

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

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

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

The method for measuring properties may be different between a sample with positive dielectric anisotropy and a sample with negative dielectric anisotropy. The method of measuring when the dielectric anisotropy is positive is described in the items (8a) to (12a). When the dielectric anisotropy is negative, it is described in the items (8b) to (12b).

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

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

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

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

(10a) Elastic constant (K; measured at 25° C.; pN) Positive dielectric anisotropy: An LCR meter HP4284A manufactured by Yokogawa-Hewlett Packard Co., Ltd. was used for the measurement. A sample was placed in a horizontal alignment element with a gap (cell gap) between two glass substrates of 20 μm. A charge of 0 V to 20 V was applied to the element, and the electrostatic capacitance and the applied voltage were measured. Using equations (2.98) and (2.101) in the "Handbook of Liquid Crystal Devices" (Nikkan Kogyo Shimbun) on page 75, the measured electrostatic capacitance (C) and the value of the applied voltage (V) were fitted, and the equation (2.99) The values of K ₁₁ and K ₃₃ were obtained. Next, in the formula (3.18) on page 171, K ₂₂ is calculated using the values of K ₁₁ and K ₃₃ previously obtained. The elastic constant K is represented by the average value of K ₁₁ , K ₂₂ and K ₃₃ obtained as described above.

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

(11a) Threshold voltage (Vth; measured at 25°C; V) Positive dielectric anisotropy: LCD5100 type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source is a halogen lamp. A sample was placed in a normally white mode TN element with an interval (cell gap) of two glass substrates of 0.45/Δn (μm) and a twist angle of 80 degrees. The voltage (32 Hz, rectangular wave) applied to the element was increased from 0 V to 10 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 transmitted through the element was measured. A voltage-transmittance curve was created in which the transmittance was 100% when the light amount reached the maximum, and the transmittance was 0% when the light amount was the smallest. The threshold voltage is represented by the voltage at which the transmittance becomes 90%.

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

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

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

(13) AC afterimage (brightness change rate) The luminance-voltage characteristics (B-V characteristics) of the liquid crystal display element described later were measured. Let it be the luminance-voltage characteristic before stress application: B (before). In addition, the voltage at which the maximum luminance measured here can be obtained is set as Vmax. Next, after applying an alternating current of 120 Hz to the element for 20 minutes at Vmax, it was short-circuited for 1 second, and the luminance-voltage characteristic (B-V characteristic) was measured again. Let this be the luminance-voltage characteristic after stress application: B (after). Based on these values, the luminance change rate ΔB (%) is estimated using the following equation. ΔB(%)=[B(after)-B(before)]/B(before) (Formula 1) These measurements were performed with reference to International Publication No. 2000/43833. In the present invention, it can be said that the smaller the value of ΔB (%) at the voltage at which the relative luminance becomes 21.6%, the more the generation of AC afterimages can be prevented.

raw material Solmix (registered trademark) A-11 is a mixture of ethanol (85.5%), methanol (13.4%) and isopropanol (1.1%), and was obtained from Nippon Alcohol Sales Co., Ltd.

[Synthesis Example 1] Synthesis of Compound (No. 2)

first step Compound (T-1) (12.6 g), potassium carbonate (9.5 g), compound (T-2) (11.5 g) and DMF (100 ml) were put into a reactor and stirred at 60°C for 2 hours . The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The 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, ethyl acetate:toluene=1:9) to obtain Compound (T-3) (12.0 g; 65%). In addition, compound (T-1) is a known substance, and compound (T-2) is a commercial item.

The second step The compound (T-3) (12.0 g) and tetrahydrofuran (Tetrahydrofuran, THF) (150 ml) were put into the reactor and cooled to below -60°C. n-BuLi (n-BuLi) (1.6 M hexane solution) (20.5 ml) was added dropwise thereto while maintaining -60° C. or lower, followed by stirring for 1 hour. CO ₂ gas was blown into it until the temperature did not rise, and after stirring for 30 minutes, the temperature was returned to room temperature, and the mixture was further stirred for 1 hour. The reaction mixture was poured into water, the pH was adjusted to between 6 and 5 with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and washed with a toluene/heptane mixed solvent to obtain Compound (T-4) (6.5 g; 59%).

third step Compound (T-4) (1.89 g), compound (T-5) (1.5 g), DMAP (0.13 g) and dichloromethane (100 ml) were put into a reactor, and cooled to 0°C. Thereto was added DCC (1.08 g), returned to room temperature and stirred for 12 hours. After the insoluble matter was separated by filtration, the reaction mixture was poured into water, and the aqueous layer was extracted with dichloromethane. The organic layer was washed with water and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, the residue was purified by silica gel chromatography (volume ratio, ethyl acetate:toluene=1:9), and reprecipitated with heptane to obtain compound (T-6 ) (3.7 g; 112%). In addition, the compound (T-5) can be easily synthesized by a person with ordinary knowledge in the technical field.

Fourth step Compound (T-6) (3.7 g), Pyridinium p-toluenesulfonate (PPTS) (2.2 g), THF (50 ml) and methanol (50 ml) were put into the reactor, and Stir at 50°C for 2 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with toluene. The 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, ethyl acetate:toluene=1:4) to obtain Compound (T-7) (3.24 g; 100%).

Fifth step Compound (T-7) (3.24 g), compound (T-8) (0.78 g), DMAP (0.14 g) and dichloromethane (100 ml) were put into a reactor, and cooled to 0°C. Thereto was added DCC (1.08 g), returned to room temperature and stirred for 12 hours. After the insoluble matter was separated by filtration, the reaction mixture was poured into water, and the aqueous layer was extracted with dichloromethane. The 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, ethyl acetate:toluene=1:9), and reprecipitated with heptane to obtain the compound (No. 2). ) (2.83 g; 77%).

The NMR analysis value of the obtained compound (No. 2) is as follows. ¹ H-NMR: chemical shift δ (ppm; CDCl ₃ ): 8.11 (dd, 1H), 8.04 (s, 1H), 7.77 (d, 1H), 7.74 (d, 1H), 7.02 (d, 1H), 6.89 (dd, 1H), 6.83 (d, 1H), 6.79 (d, 1H), 6.76 (dd, 1H), 6.09 (s, 1H), 5.72 (dd, 1H), 5.54 (d, 1H), 5.36 (dd, 1H), 4.61 (t, 2H), 4.29 (t, 3H), 4.15 (t, 2H), 3.94 (t, 2H), 2.95-2.86 (m, 4H), 2.19 (s, 2H), 1.94 (s, 3H), 1.79 (quint, 2H), 1.70 (quint, 2H), 1.55 (quint, 2H), 1.49 (quint, 2H).

The physical properties of compound (No. 2) are as follows. Transition temperature (°C): C 63.9 I Polymerization temperature (°C): 118.8

[Synthesis Example 2] Synthesis of Compound (No. 5) Compound (No. 5) can be synthesized by substituting Compound (T-1) in Synthesis Example 1 with Compound (T-9) and performing the same operation. .

The NMR analysis value of the obtained compound (No. 5) is as follows. ¹ H-NMR: chemical shift δ (ppm; CDCl ₃ ): 8.15 (dd, 1H), 8.09 (s, 1H), 7.88 (d, 1H), 7.87 (d, 1H), 7.59 (d, 2H), 7.54 (dd, 1H), 7.47 (s, 1H), 7.04 (d, 1H), 7.01 (d, 2H), 6.81 (d, 1H), 6.77 (dd, 1H), 6.11 (s, 1H), 5.73 (dd, 1H), 5.54 (d, 1H), 5.37 (dd, 1H), 4.62 (t, 2H), 4.30 (t, 2H), 4.16 (t, 2H), 3.96 (t, 2H), 3.02- 2.96 (m, 4H), 1.79 (quint, 2H), 1.70 (quint, 2H), 1.55 (quint, 2H), 1.49 (quint, 2H).

The physical properties of compound (No. 5) are as follows. Transition temperature (°C): C 79.49 I Polymerization temperature (°C): 145.6

使化合物（T-10）（7.1 g）、4-碘苯酚（4-iodophenol）（20 g）溶解於甲苯（100 ml）中，加入水（100 ml）、乙醇（100 ml）、Pd(PPh₃ )₄ （0.54 g）、四丁基溴化銨（tetrabutylammonium bromide，TBAB）（0.76 g）及碳酸鉀（9.72 g），並加熱回流6小時。反應結束後，利用乙酸乙酯進行提取，利用水進行清洗，然後利用無水硫酸鎂進行乾燥，並進行減壓濃縮而獲得淡茶色固體。將所述固體製成溶液，實施矽膠管柱色譜法（體積比，乙酸乙酯：甲苯=9：1）及再結晶（甲醇），由此獲得化合物（T-9）（3.7 g；45%）。再者，化合物（T-10）為已知物質。Synthesis of Compound (T-9)

Compound (T-10) (7.1 g), 4-iodophenol (20 g) were dissolved in toluene (100 ml), water (100 ml), ethanol (100 ml), Pd (PPh) were added ₃ ) ₄ (0.54 g), tetrabutylammonium bromide (TBAB) (0.76 g) and potassium carbonate (9.72 g), and heated to reflux for 6 hours. After completion of the reaction, extraction was performed with ethyl acetate, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a light brown solid. The solid was made into a solution and subjected to silica gel column chromatography (volume ratio, ethyl acetate:toluene=9:1) and recrystallization (methanol) to obtain compound (T-9) (3.7 g; 45%) ). In addition, compound (T-10) is a known substance.

[Synthesis Example 3] Synthesis of Compound (No. 3) Compound (No. 3) can be synthesized by substituting Compound (T-5) in Synthesis Example 1 with Compound (T-11) and performing the same operation .

The NMR analysis value of the obtained compound (No. 3) is as follows. ¹ H-NMR: chemical shift δ (ppm; CDCl ₃ ): 8.15 (dd, 1H), 8.08 (s, 1H), 7.80 (d, 1H), 7.76 (d, 1H), 7.51 (d, 2H), 7.45 (s, 1H), 7.42 (dd, 1H), 7.18 (d, 1H), 6.96 (d, 2H), 6.90 (dd, 1H), 6.85 (d, 1H), 6.11 (s, 1H), 5.78 (dd, 1H), 5.55 (d, 1H), 5.37 (dd, 1H), 4.62 (t, 2H), 4.31 (t, 2H), 4.17 (t, 2H), 4.01 (t, 2H), 2.98- 2.89 (m, 4H), 2.30 (s, 3H), 1.95 (s, 3H), 1.83 (quint, 2H), 1.73 (quint, 2H), 1.55 (quint, 2H), 1.49 (quint, 2H).

The physical properties of compound (No. 3) are as follows. Transition temperature (°C): C 76.2 I Polymerization temperature (°C): 110.7

第一步驟 使化合物（T-12）（18 g）、4-碘酚（16.7 g）溶解於甲苯（150 ml）中，加入水（70 ml）、乙醇（70 ml）、Pd(PPh₃ )₄ （0.88 g）、TBAB（2.5 g）及碳酸鉀（21 g），並加熱回流6小時。反應結束後，利用乙酸乙酯進行提取，利用水進行清洗，然後利用無水硫酸鎂進行乾燥，並進行減壓濃縮而獲得淡茶色固體。利用甲苯對所述固體進行加熱清洗，獲得化合物（T-13）（13 g；60%）。再者，化合物（T-12）為已知物質。Synthesis of Compound (T-11)

In the first step, compound (T-12) (18 g) and 4-iodophenol (16.7 g) were dissolved in toluene (150 ml), water (70 ml), ethanol (70 ml), Pd(PPh ₃ ) were added ₄ (0.88 g), TBAB (2.5 g) and potassium carbonate (21 g) and heated to reflux for 6 hours. After completion of the reaction, extraction was performed with ethyl acetate, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a light brown solid. The solid was heated and washed with toluene to obtain Compound (T-13) (13 g; 60%). In addition, compound (T-12) is a known substance.

second step Compound (T-13) (5 g), potassium carbonate (4.9 g), compound (T-14) (5.26 g) and DMF (100 ml) were put into a reactor and stirred at 60°C for 2 hours . The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The 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, ethyl acetate:toluene=1:9) to obtain Compound (T-15) (7.5 g; 94%). In addition, compound (T-14) is a known substance.

third step Compound (T-15) (7.5 g), pyridinium p-toluenesulfonate (PPTS) (6.2 g), THF (50 ml) and methanol (50 ml) were put into a reactor and stirred at 50°C 2 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The 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, ethyl acetate:toluene=1:9) to obtain Compound (T-11) (5.6 g; 92%).

[Synthesis Example 4] Synthesis of Compound (No. 46) Compound (No. 46) can be synthesized by substituting Compound (T-5) in Synthesis Example 1 with Compound (T-16) and performing the same operation .

The NMR analysis value of the obtained compound (No. 46) is as follows. ¹ H-NMR: chemical shift δ (ppm; CDCl ₃ ): 8.14 (dd, 1H), 8.08 (s, 1H), 7.80 (d, 1H), 7.76 (d, 1H), 7.50 (d, 2H), 7.45 (s, 1H), 7.42 (dd, 1H), 7.18 (d, 1H), 6.96 (d, 2H), 6.90 (dd, 1H), 6.84 (d, 1H), 6.10 (s, 1H), 5.73 (dd, 1H), 5.55 (d, 1H), 5.37 (dd, 1H), 4.62 (t, 2H), 4.31 (t, 2H), 4.03 (t, 2H), 3.97 (d, 2H), 3.48 ( t, 2H), 3.25 (d, 2H), 2.98-2.89 (m, 4H), 2.30 (s, 3H), 1.95-1.5 (m, 10H), 1.1-0.9 (m, 4H)

The physical properties of compound (No. 46) are as follows. Transition temperature (°C): C 115.5 I Polymerization temperature (°C): 147.9

Synthesis of Compound (T-16) In the synthesis of Compound (T-11), Compound (T-16) was synthesized by using Compound (T-17) instead of Compound (T-14).

[Synthesis Example 5] Synthesis of Compound (No. 47) Compound (No. 47) can be synthesized by substituting Compound (T-5) in Synthesis Example 1 with Compound (T-18) and performing the same operation . In addition, a compound (T-18) can be easily synthesized using 2,7-dihydro-2,7-phenanthrenediol, which is a known substance, for those skilled in the art.

The NMR analysis value of the obtained compound (No. 47) is as follows. ¹ H-NMR: chemical shift δ (ppm; CDCl ₃ ): 8.11 (dd, 1H), 8.05 (s, 1H), 7.78 (d, 1H), 7.76 (d, 1H), 7.71 (d, 2H), 7.65 (d, 1H), 7.12 (dd, 1H), 7.09 (s, 1H), 6.90 (dd, 2H), 6.83 (s, 1H), 6.82 (dd, 1H), 6.78 (s, 1H), 6.10 (s, 1H), 5.73 (dd, 1H), 5.55 (d, 1H), 5.37 (dd, 1H), 4.62 (t, 2H), 4.30 (t, 2H), 4.17 (t, 2H), 4.00 ( t, 2H), 2.98-2.85 (m, 8H), 1.81 (quint, 2H), 1.73 (quint, 2H), 1.55 (quint, 2H), 1.49 (quint, 2H).

The physical properties of compound (No. 47) are as follows. Transition temperature (°C): C 105.2 I Polymerization temperature (°C): 146.8

The following compounds (No. 1) to (No. 47) can be synthesized as specific examples of the compound (1) according to the synthesis methods described in the synthesis examples.

2. Use examples of elements The compounds in the use examples are represented by symbols based on the definitions of 1) to 5) in Table 2 below. In Table 2, the steric configuration related to the 1,4-cyclohexylene group 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 composition are summarized.

1. Raw materials A composition to which a polar compound is added is injected into a device without an alignment film. After the linearly polarized light was irradiated, the alignment of the liquid crystal molecules in the element was confirmed. First, the raw material will be described. The raw material is appropriately selected from the composition such as the composition (M1) to the composition (M8) and the compound (1) such as the compound (No. 1) to the compound (No. 47). The composition is as follows.

[Composition (M1)] 2-HH-3 (2-1) 21% 3-HH-4 (2-1) 5% 3-HB-O2 (2-5) 2.5% 1-BB-3 (2-8) 4% 3-HHB-1 (3-1) 1.5% 3-HBB-2 (3-4) 9.5% 2-H1OB(2F,3F)-O2 (9-5) 7% 3-H1OB(2F,3F)-O2 (9-5) 11% 3-HDhB(2F,3F)-O2 (10-3) 3.5% 3-HH1OB(2F,3F)-O2 (10-5) 8% 2-HBB(2F,3F)-O2 (10-7) 3% 3-HBB(2F,3F)-O2 (10-7) 9% 5-HBB(2F,3F)-O2 (10-7) 7% V-HBB(2F,3F)-O2 (10-7) 8% NI=80.8℃; Tc＜-20℃; Δn=0.108; Δε=-3.8; Vth=2.02 V; η=19.8 mPa·s; γ1=115.0 mPa·s.

[Composition (M2)] 2-HH-3 (2-1) 21% 3-HH-4 (2-1) 5% 3-HBB-2 (3-4) 9% 3-HHB-3 (3-1) 8% 5-HBB(F,F)-F (6-24) 20% 3-HBB(F,F)-F (6-24) 30% 2-HHBB(F,F)-F (7-6) 3% 3-HHBB(F,F)-F (7-6) 4% NI=85.1℃; Tc＜-20℃; Δn=0.109; Δε=5.3; Vth=1.83 V; η=20.1 mPa·s; γ1=82.4 mPa·s.

[Composition (M3)] 3-HH-V (2-1) 18% 3-HH-4 (2-1) 11% 5-HB-O2 (2-5) 2% 3-HHB-1 (3-1) 5% 3-HHB-3 (3-1) 5% 3-HHB-O1 (3-1) 6% 3-HHB(F,F)-F (6-3) 10% 3-BB(F)B(F,F)-F (6-69) 7% 3-BB(F,F)XB(F,F)-F (6-97) 14% 3-HHXB(F,F)-F (6-100) 2% 3-GHB(F,F)-F (6-109) 4% 4-BB(F)B(F,F)XB(F,F)-F (7-47) 10% 5-BB(F)B(F,F)XB(F,F)-F (7-47) 6% NI=78.4℃; Tc＜-20℃; Δn=0.108; Δε=10.4; Vth=1.35 V; η=17.8 mPa·s; γ1=79.9 mPa·s.

[Composition (M4)] 3-HH-V (2-1) 34% V-HHB-1 (3-1) 12% V-HBB-2 (3-4) 5% 3-HBB-2 (3-4) 5% 3-BB(F,F)XB(F,F)-F (6-97) 15% 3-GB(F,F)XB(F,F)-F (6-113) 4% 3-HHB(F,F)XB(F,F)-F (7-29) 8% 3-HBBXB(F,F)-F (7-32) 5% 3-BB(F,F)XB(F)B(F,F)-F (7-56) 4% 4-GB(F)B(F,F)XB(F,F)-F (7-57) 4% 5-GB(F)B(F,F)XB(F,F)-F (7-57) 4% NI=77.4℃; Tc＜-20℃; Δn=0.108; Δε=10.2; Vth=1.35 V; η=13.2 mPa·s; γ1=69.0 mPa·s.

[Composition (M5)] 3-HH-V (2-1) 29% 3-HH-V1 (2-1) 2% V-HHB-1 (3-1) 5% 2-BB(2F,3F)-O2 (9-3) 3% 3-BB(2F,3F)-O2 (9-3) 10.5% 3-H2B(2F,3F)-O2 (9-4) 5% V2-HHB(2F,3F)-O2 (10-1) 12% V-HHB(2F,3F)-O2 (10-1) 11.5% 3-HH2B(2F,3F)-O2 (10-4) 9% V-HBB(2F,3F)-O2 (10-7) 11% V-HBB(2F,3F)-O4 (10-7) 2% NI=89.1℃; Tc＜-20℃; Δn=0.107; Δε=-3.7; Vth=2.32 V; γ1=129.7 mPa·s.

[Composition (M6)] 2-HH-3 (2-1) 20% 3-HH-VFF (2-1) 6% V-HBB-2 (3-4) 10% 3-HB(2F,3F)-O2 (9-1) 12% 5-HB(2F,3F)-O2 (9-1) 11% 3-HHB(2F,3F)-O2 (10-1) 9% V-HHB(2F,3F)-O1 (10-1) 3% V-HHB(2F,3F)-O2 (10-1) 8% 2-HBB(2F,3F)-O2 (10-7) 3% 3-HBB(2F,3F)-O2 (10-7) 9% 4-HBB(2F,3F)-O2 (10-7) 9% NI=85.7℃; Tc＜-20℃; Δn=0.104; Δε=-3.5; Vth=2.12 V; γ1=102 mPa·s.

[Composition (M7)] 2-HH-3 (2-1) 9% 3-HH-5 (2-1) 11% 5-HH-O1 (2-1) 5% 5-HB-3 (2-5) 12% V-HHB-1 (3-1) 4% 3-HB(2F,3F)-O4 (9-1) 4% 5-HB(2F,3F)-O4 (9-1) 5% 2-HHB(2F,3F)-1 (10-1) 9% 3-HHB(2F,3F)-1 (10-1) 10% 3-HHB(2F,3F)-O2 (10-1) 10% 5-HHB(2F,3F)-O2 (10-1) 9% 2-HBB(2F,3F)-O2 (10-7) 2% 2O-DBTF2-O4 (DB-1-1) 5% 2O-DBTF2-O5 (DB-1-1) 5% NI=81.3℃; Δn=0.091; Δε=-3.4; Vth=2.25 V.

[Composition (M8)] 3-HH-V (2-1) 29% 1-BB-3 (2-8) 5% 3-HBB-2 (3-4) 5% V-HBB-2 (3-4) 4% 3-HB(2F,3F)-O2 (9-1) 15% 5-HB(2F,3F)-O2 (9-1) 3% 3-HHB(2F,3F)-O2 (10-1) 9% 5-HHB(2F,3F)-O2 (10-1) 4% V-HHB(2F,3F)-O1 (10-1) 4% V-HHB(2F,3F)-O2 (10-1) 10% 3-HBB(2F,3F)-O2 (10-7) 6% 2O-DBTF2-O4 (DB-1-1) 2% 3-HDBTF2-O4 (DB-1-2) 4% NI=83.4℃; Δn=0.104; Δε=-3.4; Vth=2.26 V.

2. Alignment of Liquid Crystal Molecules Use Examples 1 to 7 (Preparation of Samples) In the composition (M1), 0.1 wt %, 0.3 wt %, 0.5 wt %, 1.0 wt %, 3.0 wt %, 5.0 wt % %, 10.0% by weight, as compound (1), compound (No. 2) as a compound that can align liquid crystal molecules horizontally, and as an antioxidant, a compound in which R ⁴⁰ is n-heptyl is added at a ratio of 150 ppm (AO-1). After heating and stirring at 100°C, the mixture was returned to room temperature and allowed to stand for one week. As a result, these mixtures were completely dissolved without precipitation of crystals or the like.

(Production of components) These mixtures were injected into IPS elements without alignment films at 90°C. These mixtures showed an isotropic phase at 90°C, so these mixtures were injected at temperatures above the upper temperature limit of the nematic phase. While heating the IPS element at 90°C, the element is irradiated with polarized ultraviolet rays having peaks at wavelengths of 313 nm, 335 nm, and 365 nm from the normal direction for a certain period of time, thereby performing the alignment treatment, which is continued. Irradiate until the alignment becomes good.

(Irradiation conditions of polarized ultraviolet rays) The illuminance at a wavelength of 313 nm was 3 mW/cm ² . Measured using UIT-150 and UVD-S313 manufactured by Ushio Electric Co., Ltd. As the ultraviolet irradiation lamp, USH-250BY manufactured by Ushio Electric Co., Ltd. was used. The exposure machine unit used ML-251A/B manufactured by Ushio Electric Co., Ltd. The polarized ultraviolet rays were formed using a wire grid polarizing element (ProFlux UVT260A manufactured by Polatechno Co., Ltd.).

(How to check the alignment) The elements were parallel to the polarization axis of linearly polarized light, and were installed on a polarizing microscope in which the polarizing element and the analyzer were arranged orthogonally, and the element was irradiated with light from below to observe whether there was light leakage. When light did not pass through the element, the alignment was determined to be "good". When the light passing through the element was observed, it was judged that the alignment was "defective" and the irradiation was insufficient.

(AC afterimage) AC afterimages were determined using the unit and are summarized in Table 3 below.

Use Example 8 to Use Example 42 Using the composition (M1), a compound (AO-1) in which R ⁴⁰ is an n-heptyl group as an antioxidant was added at a ratio of 150 ppm, and the compounds were mixed at a ratio shown in Table 3 below (1) As a compound that can align liquid crystal molecules horizontally. In addition, it carried out similarly to the use example 1. AC afterimages were measured in the same manner as in Use Example 1. The results are summarized in Table 3 below. The mixtures of Use Example 8 to Use Example 14 also showed an isotropic phase at 90°C. In addition, the compound which can align liquid crystal molecules horizontally may be called "the compound for horizontal alignment" etc. below.

table 3 use case composition Compounds for Horizontal Alignment (1) Additive concentration (wt%) AC afterimage (%) 1 M1 No.2 0.1 5 2 M1 No.2 0.3 6 3 M1 No.2 0.5 7 4 M1 No.2 1 6 5 M1 No.2 3 8 6 M1 No.2 5 9 7 M1 No.2 10 5 8 M1 No.3 0.1 7 9 M1 No.3 0.3 8 10 M1 No.3 0.5 3 11 M1 No.3 1 9 12 M1 No.3 3 5 13 M1 No.3 5 4 14 M1 No.3 10 6 15 M1 No.3 0.1 7 16 M1 No.3 0.3 9 17 M1 No.3 0.5 8 18 M1 No.3 1 5 19 M1 No.3 3 7 20 M1 No.3 5 7 twenty one M1 No.3 10 6 twenty two M1 No.46 0.1 5 twenty three M1 No.46 0.3 6 twenty four M1 No.46 0.5 7 25 M1 No.46 1 6 26 M1 No.46 3 8 27 M1 No.46 5 9 28 M1 No.46 10 5 29 M1 No.47 0.1 7 30 M1 No.47 0.3 8 31 M1 No.47 0.5 5 32 M1 No.47 1 9 33 M1 No.47 3 5 34 M1 No.47 5 4 35 M1 No.47 10 6 36 M1 No.47 0.1 7 37 M1 No.47 0.3 9 38 M1 No.47 0.5 8 39 M1 No.47 1 5 40 M1 No.47 3 7 41 M1 No.47 5 7 42 M1 No.47 10 6

The composition M1 used in Use Example 1 to Use Example 42 was changed to M2 to M8, and the same operations were performed, respectively. As a result, AC afterimages did not change significantly in any of them.

From the composition (M1) to the composition (M8), the compound (1) from the compound (No.1) to the compound (No.45) was appropriately selected, and the same operation was performed. As a result, in any one, AC afterimages are all below 15%.

Comparative Examples 1 to 14 The compound (S-1) described in Patent Document 3 and the compound (S-2) described in Patent Document 2 are shown in Table 4 below as compounds capable of horizontal alignment of liquid crystal molecules. The ratio of 1 was mixed in the composition (M1), and the AC afterimage was evaluated by the same operation as in the use example. The mixtures of Comparative Examples 1 to 21 also showed an isotropic phase at 90°C. As a result, compared with the compound of the embodiment of the present invention, in any compound, the value of the AC afterimage in the use example was 20% or more. In addition, when the same evaluation was performed using the composition (M2) to the composition (M8), all of the results showed the same tendency as the case where the composition (M1) was used.

Table 4 Comparative example composition Compounds for Horizontal Alignment Additive concentration (wt%) AC afterimage (%) 1 M1 S-1 0.1 25 2 M1 S-1 0.3 28 3 M1 S-1 0.5 twenty two 4 M1 S-1 1 29 5 M1 S-1 3 twenty one 6 M1 S-1 5 27 7 M1 S-1 10 26 8 M1 S-2 0.1 31 9 M1 S-2 0.3 34 10 M1 S-2 0.5 38 11 M1 S-2 1 39 12 M1 S-2 3 36 13 M1 S-2 5 33 14 M1 S-2 10 37

The irradiation time is 10 minutes to 30 minutes in the use examples and 30 minutes to 60 minutes in the comparative examples, and the sensitivity of the use examples is basically good. In the use example, although the type and amount of compound (1), which is a compound capable of horizontally aligning liquid crystal molecules, were changed in composition or polar compound, there was no residual dissolution or precipitation, and the value of AC afterimage did not change significantly. On the other hand, in the comparative example, the value of the AC afterimage was 20% or more. Therefore, it turned out that if the compound (1) of embodiment of this invention is used, AC afterimages can be suppressed low, and the horizontal alignment type liquid crystal display element excellent in reliability can be obtained. In addition, by using the liquid crystal composition according to the embodiment of the present invention, it is possible to obtain a device having at least one of the characteristics of a wide usable element temperature range, a short response time, a high voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long life. Liquid crystal display element. Furthermore, a liquid crystal display element having a liquid crystal composition having a high upper limit temperature of a nematic phase, a low lower limit temperature of a nematic phase, a small viscosity, a suitable optical anisotropy, and a negative dielectric property can be obtained. At least one of properties such as high anisotropy, high specific resistance, high stability to ultraviolet rays, and high thermal stability are satisfied. [Industrial Availability]

The liquid crystal composition of the embodiment of the present invention can be used for a liquid crystal monitor, a liquid crystal television, and the like.

without

Claims (17)

a compound represented by formula (1);

In formula (1), a and b are independently 0, 1 or 2, and the sum of a and b is 0, 1, 2 or 3; Ring A ¹ , Ring A ² , Ring A ³ and Ring A ⁴ are independently 1,4-cyclohexylene, 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 , pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocyclopenta[a]phenanthrene-3,17 -diyl, 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecylhydrocyclopenta[a]phenanthrene-3,17-diyl, In the group represented by the formula (A-1) or the group represented by the formula (A-2), among these ring A ¹ , ring A ² , ring A ³ and ring A ⁴ , at least one hydrogen may be replaced by fluorine, chlorine, carbon Alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11 carbons, alkenyloxy having 2 to 11 carbons, -Sp ¹ -P ¹ or -Sp ² -P ² Substituted, in these alkyl, alkenyl, alkoxy, alkenyloxy, -Sp ¹ -P ¹ or -Sp ² -P ² , at least one hydrogen may be substituted by fluorine or chlorine, wherein ring A ¹ , ring A ^2. At least one of ring A ³ or ring A ⁴ is a group represented by formula (A-1) or a group represented by formula (A-2), in formula (A-1) and formula (A-2), Q ¹ and Q ² are independently -CH ₂ -, -O-, -N(-R ⁸ )- or -S-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbons, the R In ⁸ , at least one -CH ₂ - can be substituted by -O- or -S-, 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 substitution, but there is no case where R ⁸ is fluorine or chlorine;

When a is 2, the two rings A ¹ may be different, and when b is 2, the two rings A ⁴ may be different; Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are independently single bonds or carbon numbers 1 to 10 alkylene groups, in said Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ , at least one -CH ₂ - may be through -O-, -S-, -CO-, -COO-, -OCO- or -OCOO- substituted, 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, but Z ² , Z ³ or At least one of Z ⁴ is -COS-, -SCO-, -CH=CHCOS-, -SCOCH=CH-, -COO-, -OCO-, -CH=CH-, -CH=CHCO-, or -COCH= CH-, when a is 2, the two Z ¹ can be different, when b is 2, the two Z ⁵ can be different; Sp ¹ and Sp ² are independently a single bond or an alkylene group having 1 to 10 carbons, In the Sp ¹ and Sp ² , at least one -CH ₂ - can be substituted by -O-, -CO-, -COO-, -OCO- or -OCOO-, and at least one -(CH ₂ ) ₂ - can be substituted by - CH=CH- or -C≡C- substituted, at least one hydrogen can be substituted by fluorine, chlorine or -Sp ¹ -P ¹ or -Sp ² -P ² ; In the presence of multiple Sp ¹ or Sp ² , any Two may be different; P ¹ and P ² are independently a base represented by any one of formulas (1b) to (1h), and when there are multiple P ¹ or P ² , any two may be different;

In formula (1b) to formula (1h), M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 5 carbon atoms, or at least one hydrogen substituted by fluorine or chlorine Alkyl having 1 to 5 carbons; X ¹ is -N(-R ⁹ )-, -O- or -S-, where R ⁹ is hydrogen or alkyl having 1 to 15 carbons, and R ⁹ Among them, at least one -CH ₂ - can be substituted by -O- or -S-, 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 substitution, but there is no case where R ⁹ is fluorine or chlorine; R ² and R ⁶ are independently hydrogen, fluorine, chlorine or an alkyl group with 1 to 5 carbons, and in said R ² and R ⁶ , at least one hydrogen Can be substituted by fluorine or chlorine, at least one -CH ₂ - can be substituted by -O-; R ³ , R ⁴ , R ⁵ and R ⁷ are independently hydrogen or an alkyl group having 1 to 15 carbons, the R ³ , Among R ⁴ , R ⁵ and R ⁷ , 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 can be replaced by fluorine or chlorine, but there is no case where R ⁵ and R ⁷ are fluorine or chlorine. The compound according to claim 1, wherein, in formula (1), a and b are independently 0, 1 or 2, and the sum of a and b is 0, 1 or 2; ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are independently 1,4-cyclohexylene, 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, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocyclopentane [a]phenanthrene-3,17-diyl, 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a] A phenanthrene-3,17-diyl group, a group represented by the formula (A-1), or a group represented by the formula (A-2), among these ring A ¹ , ring A ² , ring A ³ and ring A ⁴ , at least One hydrogen can be through fluorine, chlorine, alkyl group of carbon number 1 to 12, alkenyl group of carbon number 2 to 12, alkoxy group of carbon number 1 to 11, alkenyloxy group of carbon number 2 to 11, -Sp ¹ - P ¹ or -Sp ² -P ² is substituted, and in these alkyl, alkenyl, alkoxy, alkenyloxy, -Sp ¹ -P ¹ or -Sp ² -P ² , at least one hydrogen may be substituted by fluorine or chlorine , wherein at least one of ring A ¹ , ring A ² , ring A ³ or ring A ⁴ is a group represented by formula (A-1) or a group represented by formula (A-2), and Q ¹ and Q ² are independent is -CH ₂ -, -O-, -N(R ⁸ )- or -S-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R ⁸ , at least one -CH ₂ - can be substituted by -O- or -S-, 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, but is absent When R ⁸ is fluorine or chlorine,

When a is 2, the two rings A ¹ may be different, and when b is 2, the two rings A ⁴ may be different; Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are independently single bonds, -( CH ₂ ) ₂ -, -C≡C-, -C≡CC≡C-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -CH ₂ O-, -OCH ₂ -, -CF=CF-, -CH=CHCOO-, -OCOCH=CH-, -CH=CH-, -CH=CHCO-, -COCH=CH-, -COS-, -SCO-, -CH=CHCOS- or -SCOCH=CH-; when a is 2, the two Z ¹ can be different, when b is 2, the two Z ⁵ can be different; Sp ¹ and Sp ² are independently a single bond or an extension of carbon number 1 to 10 Alkyl, among the Sp ¹ and Sp ² , at least one -CH ₂ - can be substituted by -O-, -COO- or -OCO-, and at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH- , at least one hydrogen can be substituted by fluorine, chlorine or -Sp ¹ -P ¹ or -Sp ² -P ² , when there are multiple Sp ¹ or Sp ² , any two can be different; P ¹ and P ² are independent ground is a base represented by any one of formula (1b) to formula (1h), and in the case of a plurality of P ¹ or P ² , any two may be different;

In formula (1b) to formula (1h), M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 5 carbon atoms, or at least one hydrogen substituted by fluorine or chlorine an alkyl group having 1 to 5 carbon atoms, X ¹ is -N(-R ⁹ )-, -O- or -S-, where R ⁹ is hydrogen or an alkyl group having 1 to 15 carbon atoms, and the R ⁹ Among them, at least one -CH ₂ - can be substituted by -O- or -S-, 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 substitution, but there is no case where R ⁹ is fluorine or chlorine; R ² and R ⁶ are hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and among the R ² and R ⁶ , at least one hydrogen can be Fluorine or chlorine substitution, at least one -CH ₂ - may be substituted by -O-; R ³ , R ⁴ , R ⁵ and R ⁷ are independently hydrogen or an alkyl group having 1 to 15 carbons, the R ³ , R ⁴ , R ⁵ and R ⁷ , at least one -CH ₂ - can be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH- or -C≡C-, at least one One hydrogen can be replaced by fluorine or chlorine, but there is no case where ^R5 and ^R7 are fluorine or chlorine. The compound of claim 1 or claim 2, which is represented by any one of formula (1-1) to formula (1-3);

In formula (1-1) to formula (1-3), ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are independently 1,4-cyclohexylene, 1,4-phenylene, naphthalene -2,6-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl In a diradical, a radical represented by formula (A-1) or formula (A-2), among these ring A ¹ , ring A ² , ring A ³ and ring A ⁴ , at least one hydrogen may be replaced by fluorine, chlorine, carbon number Alkyl of 1 to 12, alkenyl of carbon number 2 to 12, alkoxy of carbon number of 1 to 11, alkenyloxy of carbon number of 2 to 11, -Sp ¹ -P ¹ or -Sp ² -P ² substituted , in these alkyl, alkenyl, alkoxy, alkenyloxy, -Sp ¹ -P ¹ or -Sp ² -P ² , at least one hydrogen may be substituted by fluorine or chlorine, wherein ring A ¹ , ring A ² , at least one of ring A ³ or ring A ⁴ is formula (A-1) or formula (A-2), and Q ¹ and Q ² are independently -CH ₂ -, -O-, -N(R ⁸ )- or -S-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, in said R ⁸ , at least one -CH ₂ - may be substituted by -O- or -S-, 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, but there is no situation that R ⁸ is fluorine or chlorine;

Z ² , Z ³ and Z ⁴ are independently a single bond, -(CH ₂ ) ₂ -, -C≡C-, -C≡CC≡C-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -CH ₂ O-, -OCH ₂ -, -CF=CF-, -CH=CHCOO-, -OCOCH=CH-, -CH=CH-, -CH=CHCO-, -COCH=CH -, -COS-, -SCO-, -CH=CHCOS- or -SCOCH=CH-; Sp ¹ and Sp ² are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and the Sp ¹ and Sp ² Among them, at least one -CH ₂ - can be substituted by -O-, -COO-, -OCOO- or -OCO-, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH-, and at least one hydrogen can be substituted by -CH=CH- Fluorine, chlorine or -Sp ¹ -P ¹ or -Sp ² -P ² substitution, in the case of multiple Sp ¹ or Sp ² , any two can be different; P ¹ and P ² are independently formula (1b) To the group represented by any one of the formula (1h), when there are multiple P ¹ or P ² , any two may be different;

In formula (1b) to formula (1h), M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 5 carbon atoms, or at least one hydrogen substituted by fluorine or chlorine Alkyl having 1 to 5 carbons; X ¹ is -N(-R ⁹ )-, -O- or -S-, where R ⁹ is hydrogen or alkyl having 1 to 15 carbons, and R ⁹ Among them, at least one -CH ₂ - can be substituted by -O- or -S-, 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 substitution, but there is no case where R ⁹ is fluorine or chlorine; R ² and R ⁶ are hydrogen, fluorine, chlorine or an alkyl group with 1 to 5 carbon atoms, and among the R ² and R ⁶ , at least one hydrogen can be Fluorine or chlorine substitution, at least one -CH ₂ - may be substituted by -O-; R ³ , R ⁴ , R ⁵ and R ⁷ are independently hydrogen or an alkyl group having 1 to 15 carbons, and said R ³ , R ⁴ , R ⁵ and R ⁷ , at least one -CH ₂ - can be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH- or -C≡C-, at least one One hydrogen can be replaced by fluorine or chlorine, but there is no case where ^R5 and ^R7 are fluorine or chlorine. The compound according to claim 3, wherein, in formula (1-1) to formula (1-3), ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are independently 1,4-ring-extended Hexyl, 1,4-phenylene, naphthalene-2,6-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, group represented by formula (A-1) or formula ( In the group represented by A-2), among these ring A ¹ , ring A ² , ring A ³ and ring A ⁴ , at least one hydrogen may be substituted by fluorine, chlorine, alkyl having 1 to 12 carbons, 2 to 12 carbons alkenyl, alkoxy with 1 to 11 carbons, alkenyl with 2 to 11 carbons, -Sp ¹ -P ¹ or -Sp ² -P ² substituted, wherein ring A ¹ , ring A ² , ring At least one of A ³ or ring A ⁴ is a group represented by formula (A-1) or a group represented by formula (A-2), and Q ¹ and Q ² are independently -CH ₂ -, -O-, - N(R ⁸ )- or -S-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R ⁸ , at least one -CH ₂ - may be substituted by -O- or -S- , 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, but there is no case where R ⁸ is fluorine or chlorine,

Z ² , Z ³ and Z ⁴ are independently a single bond, -(CH ₂ ) ₂ -, -C≡CC≡C-, -C≡C-, -COO-, -OCO-, -CH=CHCOO-, -OCOCH=CH-, -CH=CH-, -CH=CHCO-, -COCH=CH-, -COS-, -SCO-, -CH=CHCOS- or -SCOCH=CH-; Sp ¹ and Sp ² independent is a single bond or an alkylene group having 1 to 10 carbon atoms, in the Sp ¹ and Sp ² , at least one -CH ₂ - may be substituted by -O-, -COO-, -OCOO- or -OCO-, at least One -(CH ₂ ) ₂ - can be substituted by -CH=CH-, at least one hydrogen can be substituted by -Sp ¹ -P ¹ or -Sp ² -P ² , in the presence of multiple Sp ¹ or Sp ² , Any two may be different; P ¹ and P ² are independently a group represented by any one of formula (1b), formula (1c), formula (1d) or formula (1e), when there are multiple P ¹ or P In the case of ² , any two can be different;

In formula (1b) to formula (1e), M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 5 carbon atoms, or at least one hydrogen substituted by fluorine or chlorine an alkyl group having 1 to 5 carbon atoms, X ¹ is -N(-R ⁹ )-, -O- or -S-, where R ⁹ is independently hydrogen or an alkyl group having 1 to 15 carbon atoms, said In R ⁹ , at least one -CH ₂ - can be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by -CH=CH- or -C≡C- Fluorine or chlorine substitution, but there is no case where R ⁹ is fluorine or chlorine; R ² and R ⁶ are hydrogen, fluorine, chlorine or an alkyl group with 1 to 5 carbon atoms, and among the R ² and R ⁶ , at least one hydrogen Can be substituted by fluorine or chlorine, at least one -CH ₂ - can be substituted by -O-; R ³ , R ⁴ and R ⁵ are independently hydrogen or an alkyl group having 1 to 15 carbons, the R ³ , R ⁴ and In R ⁵ , at least one -CH ₂ - can be substituted by -O- or -S-, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by -CH=CH- or -C≡C- Fluorine or chlorine substitution, but not where ^R5 is fluorine or chlorine. The compound according to claim 3, wherein, in formula (1-1) to formula (1-3), ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are independently 1,4-ring-extended Hexyl, 1,4-phenylene, naphthalene-2,6-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, formula (A-1) or formula (A-2) , in these ring A ¹ , ring A ² , ring A ³ and ring A ⁴ , at least one hydrogen may be substituted by fluorine, chlorine, methyl or ethyl, wherein ring A ¹ , ring A ² , ring A ³ or ring At least one of A ⁴ is formula (A-1) or formula (A-2), Q ¹ and Q ² are independently -CH ₂ -, -O-, -N(R ⁸ )- or -S-, and this where, R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, in said R ⁸ , 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- substituted, at least one hydrogen can be substituted by fluorine or chlorine, but there is no case where R ⁸ is fluorine or chlorine,

Z ² , Z ³ and Z ⁴ are independently a single bond, -(CH ₂ ) ₂ -, -C≡CC≡C-, -C≡C-, -COO-, -OCO-, -CH=CHCOO-, -OCOCH=CH-, -CH=CH-, -CH=CHCO-, -COCH=CH-, -COS-, -SCO-, -CH=CHCOS- or -SCOCH=CH-; Sp ¹ and Sp ² independent is a single bond or an alkylene group having 1 to 10 carbon atoms, in the Sp ¹ and Sp ² , at least one -CH ₂ - may be substituted by -O-, -COO-, -OCOO- or -OCO-, at least One -(CH ₂ ) ₂ - can be substituted by -CH=CH-, at least one hydrogen can be substituted by -Sp ¹ -P ¹ or -Sp ² -P ² , in the presence of multiple Sp ¹ or Sp ² , Any two can be different; P ¹ and P ² are independently formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), the base represented by the formula (1d-1), the formula (1d-2) or the formula (1e-1),

Equation (1b-1), Equation (1b-2), Equation (1b-3), Equation (1b-4), Equation (1b-5), Equation (1c-1), Equation (1d-1), Equation In (1d-2) and formula (1e-1), X ² , X ³ , X ⁴ , X ⁵ and X ⁶ are independently -N(-R ⁹ )-, -O- or -S-, where , R ⁹ is hydrogen or an alkyl group with 1 to 15 carbon atoms, in said R ⁹ , at least one -CH ₂ - can be substituted by -O- or -S-, and at least one -(CH ₂ ) ₂ - can be substituted by - CH=CH- or -C≡C- substituted, at least one hydrogen can be substituted by fluorine or chlorine, but there is no case where R ⁹ is fluorine or chlorine. The compound according to claim 3, wherein in the compounds represented by formula (1-1) to formula (1-3), any one of Z ² , Z ³ or Z ⁴ is -COO- or -OCO-, Q ¹ is -CH ₂ - or -N(R ⁸ )-, Q ² is -N(R ⁸ )-, here, R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, in the R ⁸ , At least one -CH ₂ - can be substituted by -O- or -S-, 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 , but there is no case where R ⁸ is fluorine or chlorine. The compound according to claim 1 or claim 2, which is composed of formula (1-1-11-1) to formula (1-1-11-2), formula (1-2-11-1) to formula ( 1-2-11-4), formula (1-1-12-1) to formula (1-1-12-2), formula (1-2-12-1) to formula (1-2-12- 4), formula (1-1-21-1) to formula (1-1-21-2), formula (1-2-21-1) to formula (1-2-21-4), formula (1 -1-22-1) to formula (1-1-22-2) and any one of formula (1-2-22-1) to formula (1-2-22-4) represents;

In these formulas, Sp ¹ and Sp ² are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in the Sp ¹ and Sp ² , at least one -CH ₂ - may be through -O-, -COO-, -OCOO- or -OCO- substituted, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH-, at least one hydrogen can be substituted by -Sp ¹ -P ¹ or -Sp ² -P ² ; P ¹ , In partial structures other than P ² , Sp ¹ and Sp ² , at least one hydrogen may be substituted by fluorine, chlorine, methyl or ethyl; Q ¹ is -CH ₂ - or -N(-R ⁸ )-, Q ² is -N(-R ⁸ )-, where R ⁸ is hydrogen or an alkyl group having 1 to 15 carbon atoms, in said R ⁸ , at least one -CH ₂ - may be substituted by -O- or -S-, 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, but there is no case where R ⁸ is fluorine or chlorine, P ¹ and P ² independently formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), formula (1d-1) ), the base represented by formula (1d-2) or formula (1e-1),

Equation (1b-1), Equation (1b-2), Equation (1b-3), Equation (1b-4), Equation (1b-5), Equation (1c-1), Equation (1d-1), Equation In (1d-2) or formula (1e-1), X ² , X ³ , X ⁴ , X ⁵ and X ⁶ are independently -N(-R ⁹ )-, -O- or -S-, where , R ⁹ is hydrogen or an alkyl group with 1 to 15 carbon atoms, in said R ⁹ , at least one -CH ₂ - can be substituted by -O- or -S-, and at least one -(CH ₂ ) ₂ - can be substituted by - CH=CH- or -C≡C- substituted, at least one hydrogen can be substituted by fluorine or chlorine, but there is no case where R ⁹ is fluorine or chlorine. The compound according to claim 7, wherein formula (1-1-11-1) to formula (1-1-11-2), formula (1-2-11-1) to formula (1-2- 11-4), formula (1-1-12-1) to formula (1-1-12-2), formula (1-2-12-1) to formula (1-2-12-4), formula (1-1-21-1) to formula (1-1-21-2), formula (1-2-21-1) to formula (1-2-21-4), formula (1-1-22) -1) In the compounds represented by formula (1-1-22-2) or formula (1-2-22-1) to formula (1-2-22-4), Sp ¹ and Sp ² are independently Alkylene with 1 to 10 carbon atoms, among the Sp ¹ and Sp ² , at least one -CH ₂ - can be substituted by -O-, and at least one hydrogen can be substituted by fluorine, chlorine or -Sp ¹ -P ¹ or -Sp ² -P ² substituted. A liquid crystal composition containing at least one compound according to any one of claim 1 to claim 8. The liquid crystal composition according to claim 9, further comprising 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 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹¹ and R ¹² , at least one -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 , -(CH ₂ ) ₂ -, -CH=CH-, -C≡C- or -COO-. The liquid crystal composition according to claim 9 or claim 10, further comprising 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 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹³ , at least one -CH ₂ - may be substituted by -O- , at least one hydrogen can be substituted 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 in which at least one hydrogen may be substituted with fluorine, tetrahydropyran-2,5-diyl, 1 ,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; Z ¹⁴ , Z ¹⁵ and Z ¹⁶ are independently a single bond, -(CH ₂ ) ₂ -, -CH=CH- , -CH=CF-, -CF=CF-, -C≡C-, -COO-, -CF ₂ O-, -OCF ₂ -, -CH ₂ O-, -CH=CF-CF ₂ O-, -CF=CF-CF ₂ O- or -(CH ₂ ) ₄ -; L ¹¹ and L ¹² are independently hydrogen or fluorine. The liquid crystal composition according to claim 9 or claim 10, further comprising 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 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹⁴ , at least one -CH ₂ - may be substituted by -O-, and at least one hydrogen may be substituted by -O-. Substituted by fluorine; X ¹² is -C≡N or -C≡CC≡N; Ring D ¹ is independently 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen can be substituted by fluorine, tetrakis Hydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; Z ¹⁷ is independently a single bond, -(CH ₂ ) ₂ - , -C≡C-, -COO-, -CF ₂ O-, -OCF ₂ - or -CH ₂ O-; L ¹³ and L ¹⁴ are independently hydrogen or fluorine; i is 1, 2, 3 or 4. The liquid crystal composition according to claim 9 or claim 10, further comprising a compound selected from the group consisting of compounds represented by formula (9) to formula (15), formula (DB-1) and formula (DB-2) at least one compound in;

In formulas (9) to (15), R ¹⁵ and R ¹⁶ are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R ¹⁵ and R ¹⁶ , at least one -CH ₂ - can be substituted by -O-, at least one hydrogen can be substituted by fluorine; R ¹⁷ is hydrogen, fluorine, alkyl with 1 to 10 carbons or alkenyl with 2 to 10 carbons, among the R ¹⁷ , at least one -CH ₂ - can be substituted by -O-, at least one hydrogen can be substituted by fluorine, but there is no case where R ¹⁷ is fluorine; ring E ¹ , ring E ² , ring E ³ and ring E ⁴ are independently 1,4 - cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6 -diyl; Ring E ⁵ and Ring E ⁶ are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, tetrahydropyran-2,5-di or decahydronaphthalene-2,6-diyl; Z ¹⁸ , Z ¹⁹ , Z ²⁰ and Z ²¹ are independently a single bond, -(CH ₂ ) ₂ -, -COO-, -CH ₂ O-, -OCF 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 0 or 1, the sum of k, m, n, and p is 0, 1, 2, or 3, and the sum of q, r, and s is 0, 1, 2 or 3, t is 1, 2 or 3; In formula (DB-1) and formula (DB-2), X ¹⁰⁰ is independently -S-, -O- or -CH ₂ -; a ¹⁰⁰ and a ²⁰⁰ are independently R ¹⁰⁰ and R ²⁰⁰ are independently hydrogen, alkyl having ¹ to 15 carbons or alkene having ² to 10 carbons group, in the R ¹⁰⁰ and R ²⁰⁰ , at least one -CH ₂ - can be substituted by -O-, and at least one hydrogen can be substituted by fluorine, but there is no case where R ¹⁰⁰ and R ²⁰⁰ are fluorine; A ¹⁰⁰ and A ²⁰⁰ independently 1,2-cyclopentylene, 1,3-cyclobutyl, 1,3-cyclopentylene, 1,3-cyclopentenyl, 1,4-cyclohexylene, 1, 4-cyclohexenyl, 1,4-cycloheptide, decalin-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6 ,7-Trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl , dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 9,10-diyl Dihydrophenanthrene-2,7-diyl, 9H-oxanthene-2,6-diyl or 9H-fluorene-2,7-diyl, in A ¹⁰⁰ and A ²⁰⁰ , at least one hydrogen may be fluorine , chlorine, -C F ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ , -OCH ₂ F or -C≡N substituted; Z ¹⁰⁰ and Z ²⁰⁰ are independently a single bond or an alkylene having 1 to 6 carbon atoms base, in the Z ¹⁰⁰ and Z ²⁰⁰ , at least one -CH ₂ - can be via -O-, -S-, -CO-, -COO-, -OCO-, -CF ₂ O-, -OCF ₂ -, -(CH ₂ ) ₃ O-, -O(CH ₂ ) ₃ -, -CH=CH-CH ₂ O-, -OCH ₂ -CH=CH- or -SiH ₂ - substituted, 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; L ¹⁰⁰ and L ¹⁰¹ are independently fluorine, chlorine, -CF ₃ or -CHF ₂ ; L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ and L ¹⁰⁵ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ or -OCH ₂ F, L ¹⁰² , L ¹⁰³ absent , L ¹⁰⁴ and L ¹⁰⁵ are all hydrogen, but any one or both of L ¹⁰² , L ¹⁰³ , L ¹⁰⁴ and L ¹⁰⁵ may be hydrogen. The liquid crystal composition according to claim 9 or claim 10, comprising at least one polymerizable compound selected from the group of compounds represented by formula (16);

In formula (16), ring F and ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxyl Alkyl-2-yl, pyrimidin-2-yl or pyridin-2-yl, in these ring F and ring I, at least one hydrogen can be fluorine, chlorine, alkyl having 1 to 12 carbon atoms, or at least one hydrogen can be fluorine Or chlorine-substituted alkyl group with 1 to 12 carbon atoms; Ring G is 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-1,2-di base, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1 ,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-diyl Oxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, in these rings G, at least one hydrogen can be through fluorine, chlorine, alkyl having 1 to 12 carbons , an alkoxy group having 1 to 12 carbon atoms, or at least one hydrogen is substituted by an alkyl group having 1 to 12 carbon atoms substituted by fluorine or chlorine; Z ²² and Z ²³ are independently a single bond or an alkylene having 1 to 10 carbon atoms Base, in said Z ²² and Z ²³ , at least one -CH ₂ - can be substituted by -O-, -CO-, -COO- or -OCO-, and at least one -(CH ₂ ) ₂ - can be substituted by -CH= CH-, -C(CH ₃ )=CH-, -CH=C(CH ₃ )- or -C(CH ₃ )=C(CH ₃ )- substituted, at least one hydrogen may be substituted by fluorine or chlorine; Sp ¹¹ , Sp ¹² and Sp ¹³ are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and among the Sp ¹¹ , Sp ¹² and Sp ¹³ , at least one -CH ₂ - may be through -O-, -COO-, -OCO- or -OCOO- substituted, 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; 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 2 or more, and P ¹¹ , P ¹² and P ¹³ are independently selected from the formula (P-1) to a polymerizable group in the group of groups represented by formula (P-5);

In formula (P-1) to formula (P-5), M ¹¹ is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, in said M ¹¹ , at least one hydrogen may be substituted by fluorine or chlorine, at least One -CH ₂ - may be substituted by -O-; M ¹² and M ¹³ are independently hydrogen, fluorine, chlorine, alkyl with 1 to 5 carbons, or at least one hydrogen with 1 to 5 carbons substituted with fluorine or chlorine the alkyl group. The liquid crystal composition according to claim 9 or claim 10, comprising at least one polymerizable compound selected from the group of compounds represented by formula (16-1) to formula (16-28);

In formula (16-1) to formula (16-28), Sp ¹¹ , Sp ¹² and Sp ¹³ are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and among the Sp ¹¹ , Sp ¹² and Sp ¹³ , at least one -CH ₂ - can be substituted by -O-, -COO-, -OCO- or -OCOO-, 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, u is 0, 1 or 2, g and h are independently 0, 1, 2, 3 or 4, Z ²³ is independently a single bond or an alkylene having 1 to 10 carbons base, in said Z ²³ , at least one -CH ₂ - can be substituted by -O-, -CO-, -COO- or -OCO-, at least one -(CH ₂ ) ₂ - can be substituted by -CH=CH-, -C(CH ₃ )=CH-, -CH=C(CH ₃ )- or -C(CH ₃ )=C(CH ₃ )- substituted, at least one hydrogen can be substituted by fluorine or chlorine, P ¹¹ , P ¹² and P ¹³ is independently a polymerizable group selected from the group of groups represented by formula (P-1) to formula (P-3);

In formula (P-1) to formula (P-3), M ¹¹ is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbons, and in said M ¹¹ , at least one hydrogen may be substituted by fluorine or chlorine, at least One -CH ₂ - may be substituted by -O-; M ¹² and M ¹³ are independently hydrogen, fluorine, chlorine, alkyl with 1 to 5 carbons, or at least one hydrogen with 1 to 5 carbons substituted with fluorine or chlorine the alkyl group. The liquid crystal composition according to claim 9 or claim 10, further comprising a polymerizable compound other than formula (1) according to claim 1 and formula (16) according to claim 14, and a polymerization start At least one of an agent, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, and an antifoaming agent. A liquid crystal display element comprising the liquid crystal composition according to any one of claim 9 to claim 16.