JPWO2018139507A1 - Liquid crystal display device, liquid crystal composition and compound - Google Patents

Abstract

Provided is a liquid crystal composition in which the alignment of liquid crystal molecules of a liquid crystal display element having no alignment film is controlled by using an alignment monomer that is not colored, and the alignment monomer that is not colored exhibits good compatibility. It is to be. A liquid crystal display element and a liquid crystal composition using a liquid crystal composition containing an alignment control layer-forming monomer having a vinylene group in a partial structure and having negative dielectric anisotropy are used.

Description

  The present invention relates to a liquid crystal display element, a liquid crystal composition and a compound containing a liquid crystal composition having a negative dielectric anisotropy. In particular, the present invention relates to a liquid crystal display element using a liquid crystal composition containing an alignment monomer having a vinylene group in a partial structure and capable of achieving alignment of liquid crystal molecules by the action of this compound.

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

  The liquid crystal display element contains a liquid crystal composition having a nematic phase. This composition has suitable properties. By improving the characteristics of the composition, an AM device having good characteristics can be obtained. The relationship between the two characteristics is summarized in Table 1 below. The characteristics of the composition will be further described based on a commercially available AM device. The temperature range of the nematic phase is related to the temperature range in which the device can be used. A preferred maximum temperature of the nematic phase is about 70 ° C. or more, and a preferred minimum temperature of the nematic phase is about −10 ° C. or less. The viscosity of the composition is related to the response time of the device. A short response time is preferred for displaying moving images on the device. A shorter response time is desirable even at 1 millisecond. Therefore, a small viscosity in the composition is preferred. A small viscosity at low temperatures is even more preferred.

  The optical anisotropy of the composition is related to the contrast ratio of the device. Depending on the mode of the device, a large optical anisotropy or a small optical anisotropy, ie 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 device is designed to maximize the contrast ratio. The appropriate product value depends on the type of operation mode. This value is in the range of about 0.30 μm to about 0.40 μm for the VA mode element and in the range of about 0.20 μm to about 0.30 μm for the IPS mode or FFS mode element. In these cases, a composition having a large optical anisotropy is preferable for a device having a small cell gap. A large dielectric anisotropy in the composition contributes to a low threshold voltage, a small power consumption and a large contrast ratio in the device. Therefore, a large dielectric anisotropy is preferable. A large specific resistance in the composition contributes to a large voltage holding ratio and a large contrast ratio in the device. Therefore, a composition having a large specific resistance in the initial stage is preferable. A composition having a large specific resistance after being used for a long time is preferred. The stability of the composition to ultraviolet light and heat is related to the lifetime of the device. When this stability is high, the lifetime of the device is long. Such characteristics are preferable for an AM device used for a liquid crystal monitor, a liquid crystal television and the like.

In an AM device having a TN mode, a composition having a positive dielectric anisotropy is used. A composition having a negative dielectric anisotropy is used in an AM device having a VA mode. In an AM device having an IPS mode or an FFS mode, a composition having a positive or negative dielectric anisotropy is used.
In a polymer sustained alignment (PSA) type liquid crystal display element, a liquid crystal composition containing a polymer is used. First, a composition to which a small amount of a polymerizable compound is added is injected into the device. Next, the composition is irradiated with ultraviolet rays while applying a voltage between the substrates of the device. The polymerizable compound polymerizes to form a polymer network in the composition. In this composition, since the alignment of liquid crystal molecules can be controlled by the polymer, the response time of the device is shortened, and image burn-in is improved. Such an effect of the polymer can be expected for a device having modes such as TN, ECB, OCB, IPS, VA, FFS, and FPA.
In the IPS mode, the FFS mode, and the ECB mode, it is necessary to align liquid crystal molecules in a substantially horizontal direction with respect to the main surface of the substrate when no voltage is applied. In order to realize such alignment control of liquid crystal molecules, an alignment film such as polyimide has been used. In recent years, the narrowing of the frame of a liquid crystal panel has progressed, and the bonding width between the alignment film and the sealing agent has been narrowed, so that the adhesive strength has weakened, and peeling has progressed from the interface between the alignment film and the sealing agent. In order to prevent such a problem, a method that does not use an alignment film such as a conventional polyimide has been proposed. (Patent Documents 1 to 3).

There is a method for controlling the alignment of liquid crystals using a low molecular compound having a cinnamate group or polyvinyl cinnamate, a low molecular compound having a chalcone structure, a low molecular compound having an azobenzene structure, or a dendrimer instead of an alignment film such as polyimide. It has been reported (Patent Document 1). In the method of Patent Document 1, first, the low molecular compound or polymer is dissolved in the liquid crystal composition as an additive. Next, the additive is phase-separated to form a thin film made of the low molecular weight compound or polymer 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 a low molecular compound or polymer is dimerized or isomerized by this linearly polarized light, the molecules are arranged in a certain direction. In this method, by selecting the kind of low molecular compound or polymer, a device in a horizontal alignment mode such as IPS or FFS and a device in a vertical alignment mode such as VA can be manufactured. In this 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 is easily phase-separated from the liquid crystal composition when it is returned to room temperature. However, it has been difficult to ensure the compatibility between the low molecular weight compound or polymer and the liquid crystal composition.
In the methods of Patent Documents 2 and 3, a dendrimer having azobenzene as a partial structure is dissolved in a liquid crystal composition as an additive. Next, a thin film of the compound is formed on the substrate by phase-separating the compound. At this time, the liquid crystal composition is aligned perpendicular to the substrate. Next, linearly polarized light is irradiated without heating the substrate. When the dendrimer is dimerized or isomerized by this linearly polarized light, the molecules are arranged in a direction horizontal to the substrate. A device in a horizontal alignment mode such as IPS or FFS can be manufactured. In this method as well, the dendrimer and the liquid crystal composition must be appropriately combined so that the dendrimer can be easily dissolved and phase-separated. When a dendrimer having azobenzene as a partial structure is used, there is a problem that there is coloring derived from azobenzene.
Patent Document 4 discloses a polymer dispersion type liquid crystal optical element including a polymer resin obtained by photopolymerizing a chiral nematic liquid crystal and a (meth) acrylate compound having a stilbene skeleton. The liquid crystal optical element here reduces the drive voltage and hysteresis. A chiral nematic liquid crystal is an essential component, and is a polymer-dispersed liquid crystal optical element that is in a transparent state or a selective reflection state when no voltage is applied and is in a scattering state when a voltage is applied. There is no suggestion or description that the (meth) acrylate compound having a stilbene skeleton induces the horizontal alignment of the liquid crystal compound by polarized light irradiation.

International Publication No. 2015/146369 JP2015-64465A Japanese Patent Laying-Open No. 2015-125151 JP 08-92561 A

The subject of this invention is providing the liquid crystal display element which does not require the conventional alignment film formed with a polyimide etc., and its formation process by using the liquid crystal composition containing an orientation monomer. Furthermore, in order to realize a liquid crystal display device excellent in transmittance characteristics and contrast ratio, it is to provide an alignment monomer that exhibits good compatibility with the liquid crystal composition and has no coloring.

  The present invention uses a liquid crystal display element, a liquid crystal composition and a compound which contain an alignment monomer having a vinylene group in a partial structure and which uses a liquid crystal composition having negative dielectric anisotropy.

According to the present invention, by using a liquid crystal composition containing an alignment monomer, it is possible to produce a liquid crystal display element that is difficult to peel even with a narrow frame.
In addition, a liquid crystal display element having excellent transmittance characteristics and contrast ratio can be realized by using an alignment monomer that is excellent in solubility in a liquid crystal composition and is not colored.
Further, the manufacturing process of the alignment film is not required in the manufacture of the liquid crystal display element, and the manufacturing cost of the liquid crystal display element can be reduced.

  Terms used in this specification are 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 liquid crystal display panels and liquid crystal display modules. “Liquid crystal compound” is a compound having a liquid crystal phase such as a nematic phase and a smectic phase, and a liquid crystal phase, but has a composition for the purpose of adjusting characteristics such as temperature range, viscosity, and dielectric anisotropy of the nematic phase. It is a general term for compounds mixed with products. This compound has a six-membered ring such as 1,4-cyclohexylene and 1,4-phenylene, and its molecular structure is rod-like. The “polymerizable compound” is a compound added for the purpose of forming a polymer in the composition. A liquid crystalline compound having alkenyl is not polymerizable in that sense.

  The liquid crystal composition is prepared by mixing a plurality of liquid crystal compounds. Additives such as optically active compounds, antioxidants, ultraviolet absorbers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, and polar compounds are added to this composition as necessary. . The ratio of the liquid crystal compound is expressed as a weight percentage (% by weight) based on the weight of the liquid crystal composition not containing the additive even when the additive is added. The ratio of the additive is expressed as a percentage by weight (% by weight) based on the weight of the liquid crystal composition not containing the additive. That is, the ratio of the liquid crystal compound or additive is calculated based on the total weight of the liquid crystal compound. Weight parts per million (ppm) may be used. The ratio of the polymerization initiator and the polymerization inhibitor is exceptionally expressed based on the weight of the polymerizable compound.

  “Maximum temperature of nematic phase” may be abbreviated as “maximum temperature”. “Lower limit temperature of nematic phase” may be abbreviated as “lower limit temperature”. “High specific resistance” means that the composition has a large specific resistance in the initial stage and a large specific resistance after long-term use. "High voltage holding ratio" means that the device has a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature in the initial stage, and a large voltage not only at room temperature but also at a temperature close to the upper limit temperature after long-term use. It means having a retention rate. An aging test may be used to examine the properties of the composition or device. The expression “increasing dielectric anisotropy” means that when the composition has a positive dielectric anisotropy, the value increases positively, and the composition having a negative dielectric anisotropy When it is a thing, it means that the value increases negatively.

  The compound represented by the formula (1) may be abbreviated as “compound (1)”. At least one compound selected from the group of compounds represented by formula (1) may be abbreviated as “compound (1)”. “Compound (1)” means one compound represented by formula (1), a mixture of two compounds, or a mixture of three or more compounds. The same applies to compounds represented by other formulas. The expression “at least one‘ A ’” means that the number of ‘A’ is arbitrary. The expression “at least one 'A' may be replaced by 'B'” means that when the number of 'A' is one, the position of 'A' is arbitrary and the number of 'A' is 2 Even when there are more than two, their positions can be selected without restriction. This rule also applies to the expression “at least one 'A' is replaced by 'B'".

Expressions such as “at least one —CH ₂ — may be replaced by —O—” are used herein. In this case, —CH ₂ —CH ₂ —CH ₂ — may be converted to —O—CH ₂ —O— by replacing non-adjacent —CH ₂ — with —O—. However, adjacent —CH ₂ — is not replaced by —O—. This replacement is -O-O-CH ₂ - is because (peroxide) is produced. That is, the expression includes both “one —CH ₂ — may be replaced with —O—” and “at least two non-adjacent —CH ₂ — may be replaced with —O—”. means. This rule applies not only to replacement with —O— but also to replacement with a divalent group such as —CH═CH— or —COO—.

In the chemical formulas of the component compounds, the symbol of the terminal group R ¹ is used for a plurality of compounds. In these compounds, two groups represented by any two R ¹ may be the same or different. For example, there is a case where R ^{1 of} the compound (1-1) is ethyl and R ¹ of the compound (1-2) is ethyl. In some cases, R ^{1 of} compound (1-1) is ethyl and R ¹ of compound (1-2) is propyl. This rule also applies to symbols such as other end groups. In the formula (1), when the subscript 'a' is 2, there are two rings A. In this compound, the two rings represented by the two rings A may be the same or different. This rule also applies to any two rings A when the subscript 'a' is greater than 2. This rule also applies to symbols such as Z ¹ and ring D.

Symbols such as A, B, C, and D surrounded by hexagons correspond to rings such as ring A, ring B, ring C, and ring D, respectively, and represent rings such as six-membered rings and condensed rings. In formula (3), a diagonal line across one side of the hexagon represents that any hydrogen on the ring may be replaced with a group such as -Sp ¹ -P ¹ . A subscript such as 'e' indicates the number of groups replaced. When the subscript 'e' is 0 (zero), there is no such replacement. When the subscript 'e' is 2 or more, a plurality of -Sp ¹ -P ¹ exists on the ring F. The plurality of groups represented by -Sp ¹ -P ¹ may be the same or different.

2-Fluoro-1,4-phenylene means the following two divalent groups. In the chemical formula, fluorine may be leftward (L) or rightward (R). This rule also applies to asymmetric divalent groups generated by removing two hydrogens from the ring, such as tetrahydropyran-2,5-diyl. This rule also applies to divalent linking groups such as carbonyloxy (—COO— or —OCO—).

  The alkyl of the liquid crystal compound is linear or branched and does not include cyclic alkyl. Linear alkyl is preferred over branched alkyl. The same applies to terminal groups such as alkoxy and alkenyl. The configuration of 1,4-cyclohexylene is preferably trans rather than cis for increasing the maximum temperature.

  The present invention includes the following items.

式（Ａ）から式（Ｄ）において、Ｐ^１０、Ｐ^２０、Ｐ^３０およびＰ^４０は独立して、式（Ｑ−１）から式（Ｑ−５）で表される基から選択された基であり；

式（Ｑ−１）から式（Ｑ−５）において、Ｍ^１０、Ｍ^２０、およびＭ^３０は独立して、水素、フッ素、炭素数１から５のアルキル、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から５のアルキルであり；
Ｓｐ^１０、Ｓｐ^２０、およびＳｐ^４０は独立して、単結合または炭素数１から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素、塩素または式（Ｑ−６）で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく、少なくとも１つの−ＣＨ_２ＣＨ_２−は−ＣＨ＝ＣＨ−で置き換えられてもよく；
Ｓｐ^３０は独立して、単結合または炭素数１から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素、塩素または式（Ｑ−６）で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく；

式（Ｑ−６）において、Ｍ^１０、Ｍ^２０、およびＭ^３０は独立して、水素、フッ素、炭素数１から５のアルキル、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から５のアルキルであり；
Ｓｐ^４１は独立して、単結合または炭素数１から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素または塩素で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく；
環Ａ^１０および環Ａ^２０は独立して、フェニル、４−ビフェニル、１−ナフチル、２−ナフチル、ピリミジン−２−イル、ピリミジン−５−イル、ピリジン−２−イル、ピリジン−５−イル、フルオレン−２−イル、フルオレン−３−イル、フェナントレン−２−イル、アントラセン−２−イルであり、これらの環において、少なくとも１つの水素は、フッ素、塩素、炭素数１から１２のアルキル、炭素数２から１２のアルケニル、炭素数１から１１のアルコキシ、または炭素数２から１１のアルケニルオキシで置き換えられてもよく、これらの基において、少なくとも１つの水素は、フッ素または塩素で置き換えられてもよく；
環Ａ^１１、環Ａ^２１、環Ａ^１２、環Ａ^２２および環Ａ^３０は独立して、１，４−シクロへキシレン、１，４−シクロヘキセニレン、１，４−フェニレン、４，４’−ビフェニレン、ナフタレン−２，６−ジイル、デカヒドロナフタレン−２，６−ジイル、１，２，３，４−テトラヒドロナフタレン−２，６−ジイル、テトラヒドロピラン−２，５−ジイル、１，３−ジオキサン−２，５−ジイル、ピリミジン−２，５−ジイル、ピリジン−２，５−ジイル、フルオレン−２，７−ジイル、フェナントレン−２，７−ジイル、アントラセン−２，６−ジイル、ペルヒドロシクロペンタ［ａ］フェナントレン−３，１７−ジイル、または２，３，４，７，８，９，１０，１１，１２，１３，１４，１５，１６，１７−テトラデカヒドロシクロペンタ［ａ］フェナントレン−３，１７−ジイルであるが、隣接する結合が、−ＣＨ＝ＣＨ−、−ＣＲ^１０＝ＣＲ^２０−、−ＣＯ−ＣＨ＝ＣＨ−、−ＣＨ＝ＣＨ−ＣＯ−、−ＯＣＯ−ＣＨ＝ＣＨ−、または−ＣＨ＝ＣＨ−ＣＯＯ−であり、Ｒ^１０およびＲ^２０は独立して、水素、フッ素、シアノ、炭素数１から１０のアルキル、または少なくとも１つの水素がフッ素に置き換えられた炭素数１から１０のアルキルであるときは、１，４−フェニレン、４，４’−ビフェニレン、ナフタレン−２，６−ジイル、ピリミジン−２，５−ジイル、ピリジン−２，５−ジイル、フルオレン−２，７−ジイル、フェナントレン−２，７−ジイル、アントラセン−２，６−ジイルであり、これらの環において、少なくとも１つの水素は、フッ素、塩素、炭素数１から１２のアルキル、炭素数２から１２のアルケニル、炭素数１から１１のアルコキシ、または炭素数２から１１のアルケニルオキシで置き換えられてもよく、これらの基において、少なくとも１つの水素は、フッ素または塩素で置き換えられてもよく；
環Ａ^４０は、１，４−シクロへキシレン、１，４−シクロヘキセニレン、１，４−フェニレン、４，４’−ビフェニレン、ナフタレン−２，６−ジイル、デカヒドロナフタレン−２，６−ジイル、１，２，３，４−テトラヒドロナフタレン−２，６−ジイル、テトラヒドロピラン−２，５−ジイル、１，３−ジオキサン−２，５−ジイル、ピリミジン−２，５−ジイル、ピリジン−２，５−ジイル、フルオレン−２，７−ジイル、フェナントレン−２，７−ジイル、アントラセン−２，６−ジイル、ペルヒドロシクロペンタ［ａ］フェナントレン−３，１７−ジイル、または２，３，４，７，８，９，１０，１１，１２，１３，１４，１５，１６，１７−テトラデカヒドロシクロペンタ［ａ］フェナントレン−３，１７−ジイルであるが、隣接する結合が、−ＣＨ＝ＣＨ−、−ＣＯ−ＣＨ＝ＣＨ−、−ＣＨ＝ＣＨ−ＣＯ−、−ＯＣＯ−ＣＨ＝ＣＨ−、または−ＣＨ＝ＣＨ−ＣＯＯ−であるときは、１，４−フェニレン、４，４’−ビフェニレン、ナフタレン−２，６−ジイル、ピリミジン−２，５−ジイル、ピリジン−２，５−ジイル、フルオレン−２，７−ジイル、フェナントレン−２，７−ジイル、アントラセン−２，６−ジイルであり、これらの環において、少なくとも１つの水素は、Ｐ^２０−Ｓｐ^２０−、フッ素、塩素、炭素数１から１２のアルキル、炭素数２から１２のアルケニル、炭素数１から１１のアルコキシ、または炭素数２から１１のアルケニルオキシで置き換えられてもよく、これらの基において、少なくとも１つの水素は、フッ素または塩素で置き換えられてもよく；
Ｚ^１０は独立して、−ＣＨ＝ＣＨ−、−ＣＲ^１０＝ＣＲ^２０−、−ＣＯ−ＣＨ＝ＣＨ−、−ＣＨ＝ＣＨ−ＣＯ−、−ＯＣＯ−ＣＨ＝ＣＨ−、または−ＣＨ＝ＣＨ−ＣＯＯ−であり、Ｒ^１０およびＲ^２０は独立して、水素、フッ素、シアノ、炭素数１から１０のアルキル、または少なくとも１つの水素がフッ素に置き換えられた炭素数１から１０のアルキルであり；
Ｚ^１１は独立して、単結合または炭素数１から６のアルキレンであり、このアルキレンにおいて、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、−ＯＣＯ−、または−ＯＣＯＯ−で置き換えられてもよく、少なくとも１つの−（ＣＨ_２）_２−は、−ＣＨ＝ＣＨ−または−Ｃ≡Ｃ−で置き換えられてもよく、これらの基において、少なくとも１つの水素は、フッ素または塩素で置き換えられてもよく；
Ｚ^２０およびＺ^２１は独立して、単結合、炭素数１から６のアルキレンまたは炭素数２から６のアルケニレンであるが、少なくとも一方は、炭素数２から６のアルケニレンである。これらのアルキレン、アルケニレンにおいて、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、−ＯＣＯ−、または−ＯＣＯＯ−で置き換えられてもよく、その他の少なくとも１つの−（ＣＨ_２）_２−は、−ＣＨ＝ＣＨ−または−Ｃ≡Ｃ−で置き換えられてもよく、これらの基において、少なくとも１つの水素は、フッ素または塩素で置き換えられてもよく；
ｋ^１０およびｎ^１０は独立して０から３の整数であり、ｋ^１０とｎ^１０の和が１から６の整数であり；
ｎ^２０は１または２であり；
ｎ^３０は１または２である。Item 1.
A liquid crystal layer is sandwiched between a pair of substrates that are arranged facing each other and bonded together via a sealant,
Between the pair of substrates and the liquid crystal layer, an alignment control layer for controlling alignment of liquid crystal molecules,
The liquid crystal layer is made of a liquid crystal composition having negative dielectric anisotropy,
The liquid crystal composition contains at least one compound selected from the group of compounds represented by formulas (A) to (D) as an alignment monomer as a first additive, and a liquid crystal compound,
The said alignment control layer is a liquid crystal display element which consists of a polymer produced | generated by polymerizing the said orientation monomer.

In formulas (A) to (D), P ¹⁰ , P ²⁰ , P ³⁰ and P ⁴⁰ are each independently a group selected from the groups represented by formula (Q-1) to formula (Q-5) Is;

In formulas (Q-1) to (Q-5), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or at least one hydrogen is fluorine or chlorine 1 to 5 carbon alkyls replaced by
Sp ¹⁰ , Sp ²⁰ , and Sp ⁴⁰ are each independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene is replaced by fluorine, chlorine or the formula (Q-6) And at least one —CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—, and at least one —CH ₂ CH ₂ — may be —CH═CH—. May be replaced by;
Sp ³⁰ is independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine, chlorine or formula (Q-6), and at least one — CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—;

In Formula (Q-6), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or 1 carbon in which at least one hydrogen is replaced by fluorine or chlorine. To alkyl of 5;
Sp ⁴¹ is independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or chlorine, and at least one —CH ₂ — is —O ₂ May be replaced by-, -CO-, -COO-, or -OCO-;
Ring A ¹⁰ and Ring A ²⁰ are independently phenyl, 4-biphenyl, 1-naphthyl, 2-naphthyl, pyrimidin-2-yl, pyrimidin-5-yl, pyridin-2-yl, pyridin-5-yl, Fluoren-2-yl, fluoren-3-yl, phenanthren-2-yl, anthracen-2-yl, and in these rings, at least one hydrogen is fluorine, chlorine, alkyl having 1 to 12 carbons, carbon May be replaced by alkenyl having 2 to 12 carbon atoms, alkoxy having 1 to 11 carbon atoms, or alkenyloxy having 2 to 11 carbon atoms, and in these groups, at least one hydrogen may be replaced by fluorine or chlorine. Often;
Ring A ¹¹ , Ring A ²¹ , Ring A ¹² , Ring A ²² and Ring A ³⁰ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 4,4 ′. -Biphenylene, 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, per Hydrocyclopenta [a] phenanthrene-3,17-diyl or 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclo Is a pointer [a] phenanthrene-3,17-diyl, adjacent ^{bond, -CH = CH -, - CR} 10 = CR 20 -, - CO-CH = CH -, - CH = CH-CO-, —OCO—CH═CH—, or —CH═CH—COO—, wherein R ¹⁰ and R ²⁰ are independently hydrogen, fluorine, cyano, alkyl having 1 to 10 carbons, or at least one hydrogen is fluorine. 1, 4-phenylene, 4,4′-biphenylene, 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 which at least one hydrogen is fluorine, chlorine, Alkyl having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkoxy having 1 to 11 carbon atoms, or alkenyloxy having 2 to 11 carbon atoms may be substituted, and in these groups, at least one hydrogen is May be replaced by fluorine or chlorine;
Ring A ⁴⁰ includes 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 4,4′-biphenylene, 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, or 2,3 4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta [a] phenanthrene-3,17-diyl, but next When the bond to be —CH═CH—, —CO—CH═CH—, —CH═CH—CO—, —OCO—CH═CH—, or —CH═CH—COO— is 1, 4 -Phenylene, 4,4'-biphenylene, naphthalene-2,6-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, and in these rings, at least one of ^hydrogen, P 20 ^{-Sp 20} -, fluorine, chlorine, alkyl of from 1 to 12 carbons, alkenyl having 2 to 12 carbons, carbon atoms May be substituted with 1 to 11 alkoxy, or alkenyloxy with 2 to 11 carbons, in which at least one hydrogen is replaced with fluorine or chlorine It may be;
Z ¹⁰ is independently —CH═CH—, —CR ¹⁰ = CR ²⁰ —, —CO—CH═CH—, —CH═CH—CO—, —OCO—CH═CH—, or —CH═CH. -COO- and R ¹⁰ and R ²⁰ are independently hydrogen, fluorine, cyano, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine. ;
Z ¹¹ is independently a single bond or an alkylene having 1 to 6 carbon atoms, in which at least one —CH ₂ — is —O—, —CO—, —COO—, —OCO—, or may be replaced by -OCOO-, at least one - _{(CH 2) 2} - may be replaced by -CH = CH- or -C≡C-, and in the groups, at least one hydrogen May be replaced by fluorine or chlorine;
Z ²⁰ and Z ²¹ are independently a single bond, alkylene having 1 to 6 carbons or alkenylene having 2 to 6 carbons, but at least one is alkenylene having 2 to 6 carbons. In these alkylene and alkenylene, at least one —CH ₂ — may be replaced by —O—, —CO—, —COO—, —OCO—, or —OCOO—, and at least one other — ( CH ₂ ) ₂ — may be replaced by —CH═CH— or —C≡C—, in which at least one hydrogen may be replaced by fluorine or chlorine;
k ¹⁰ and n ¹⁰ are each independently an integer from 0 to 3, and the sum of k ¹⁰ and n ¹⁰ is an integer from 1 to 6;
n ²⁰ is 1 or 2;
n ³⁰ is 1 or 2.

式（Ａ−１）、式（Ａ−２）、式（Ｂ−１）、式（Ｃ−１）および式（Ｄ−１）において、Ｐ^１０、Ｐ^２０、Ｐ^３０、Ｐ^４０、Ｐ^５０およびＰ^６０は独立して、式（Ｑ−１）で表される基から選択された基であり；
式（Ｑ−１）において、Ｍ^１０、Ｍ^２０、およびＭ^３０は独立して、水素、フッ素、メチル、または少なくとも１つの水素がフッ素で置き換えられた炭素数１から５のアルキルであり；
Ｓｐ^１０、Ｓｐ^２０、およびＳｐ^４０は独立して、単結合または炭素数１から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素または式（Ｑ−６）で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく、少なくとも１つの−ＣＨ_２ＣＨ_２−は−ＣＨ＝ＣＨ−で置き換えられてもよく；
Ｓｐ^３０は独立して、単結合または炭素数１から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素、塩素または式（Ｑ−６）で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく；
式（Ｑ−６）において、Ｍ^１０、Ｍ^２０、およびＭ^３０は独立して、水素、フッ素、メチル、または少なくとも１つの水素がフッ素で置き換えられた炭素数１から５のアルキルであり；
Ｓｐ^４１は独立して、単結合または炭素数１から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素または塩素で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく；
Ｓｐ^５０およびＳｐ^６０は独立して、炭素数２から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素、塩素または式（Ｑ−６）で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく；
Ｒ^１０およびＲ^２０は独立して、水素、フッ素、シアノ、炭素数１から１０のアルキル、または少なくとも１つの水素がフッ素に置き換えられた炭素数１から１０のアルキルであり；
Ｒ^３０、Ｒ^４０、Ｒ^４１およびＲ^５０は独立して、水素、フッ素、塩素、炭素数１から１０のアルキル、または少なくとも１つの水素がフッ素に置き換えられた炭素数１から１０のアルキルであり；
環Ａ^１１および環Ａ^２１は独立して１，４−フェニレン、ナフタレン−２，６−ジイルであり、これらにおいて、少なくとも１つの水素は、フッ素、塩素、炭素数１から１２のアルキル、または少なくとも１つの水素がフッ素で置き換えられた炭素数１から１２のアルキルで置き換えられてもよく；
Ｚ^１１は単結合、エチレン、メチレンオキシ、−ＣＯＯ−、−ＯＣＯ−、−ＯＣＯＯ−、または−ＣＨ＝ＣＨ−ＣＯＯ−であり；
Ｚ^１２は−ＣＯ−、または−ＯＣＯ−であり；
ｋ^１０およびｎ^１０は独立して０から３の整数であり、ｋ^１０とｎ^１０の和が１から４の整数であり；
ｎ^２０は１または２であり；
ｎ^３０は１または２であり；
Ｚ^２０およびＺ^２１は独立して、単結合、−ＣＯ−ＣＨ＝ＣＨ−、−ＣＨ＝ＣＨ−ＣＯ−、−ＯＣＯ−ＣＨ＝ＣＨ−、−ＣＨ＝ＣＨ−ＣＯＯ−または−ＣＨ＝ＣＨ−であるが、同時に単結合となることはない。Item 2. Item 2. The alignment monomer in the liquid crystal composition is represented by Formula (A-1), Formula (A-2), Formula (B-1), Formula (C-1), or Formula (D-1). Liquid crystal display element.

In Formula (A-1), Formula (A-2), Formula (B-1), Formula (C-1), and Formula (D-1), P ¹⁰ , P ²⁰ , P ³⁰ , P ⁴⁰ , P ⁵⁰ And P ⁶⁰ is independently a group selected from the groups represented by formula (Q-1);
In formula (Q-1), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, methyl, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine;
Sp ¹⁰ , Sp ²⁰ , and Sp ⁴⁰ are each independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or formula (Q-6) , At least one —CH ₂ — may be replaced with —O—, —CO—, —COO—, or —OCO—, and at least one —CH ₂ CH ₂ — is replaced with —CH═CH—. May be
Sp ³⁰ is independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine, chlorine or formula (Q-6), and at least one — CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—;
In formula (Q-6), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, methyl, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine;
Sp ⁴¹ is independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or chlorine, and at least one —CH ₂ — is —O ₂ May be replaced by-, -CO-, -COO-, or -OCO-;
Sp ⁵⁰ and Sp ⁶⁰ are independently alkylene having 2 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine, chlorine or formula (Q-6), and at least one — CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—;
R ¹⁰ and R ²⁰ are independently hydrogen, fluorine, cyano, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine;
R ³⁰ , R ⁴⁰ , R ⁴¹ and R ⁵⁰ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine. ;
Ring A ¹¹ and Ring A ²¹ are independently 1,4-phenylene, naphthalene-2,6-diyl, in which at least one hydrogen is fluorine, chlorine, alkyl having 1 to 12 carbons, or at least One hydrogen may be replaced by alkyl of 1 to 12 carbons replaced by fluorine;
Z ¹¹ is a single bond, ethylene, methyleneoxy, —COO—, —OCO—, —OCOO—, or —CH═CH—COO—;
Z ¹² is —CO— or —OCO—;
k ¹⁰ and n ¹⁰ are each independently an integer from 0 to 3, and the sum of k ¹⁰ and n ¹⁰ is an integer from 1 to 4;
n ²⁰ is 1 or 2;
n ³⁰ is 1 or 2;
Z ²⁰ and Z ²¹ independently represent a single bond, —CO—CH═CH—, —CH═CH—CO—, —OCO—CH═CH—, —CH═CH—COO— or —CH═CH—. However, it does not become a single bond at the same time.

Item 3. The alignment monomer in the liquid crystal composition is formula (A-1), formula (A-2), or formula (B-1), and P ¹⁰ , P ²⁰ , P ³⁰ , P ⁴⁰ , P ^50, and P ⁶⁰ are Independently a group selected from the groups represented by formula (Q-1);
In formula (Q-1), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, methyl, or trifluoromethyl;
Sp ¹⁰ and Sp ²⁰ are independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or formula (Q-6), and at least one of —CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—;
In formula (Q-6), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, methyl, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine;
Sp ⁴¹ is independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or chlorine, and at least one —CH ₂ — is —O ₂ May be replaced by-, -CO-, -COO-, or -OCO-;
Sp ³⁰ is a single bond or alkylene having 1 to 12 carbon atoms, and at least one hydrogen of the alkylene may be replaced by fluorine, and at least one —CH ₂ — may be —O—, —CO—, May be replaced by -COO-, or -OCO-;
Sp ⁴⁰ is a single bond;
Sp ⁵⁰ and Sp ⁶⁰ are independently alkylene having 2 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine, chlorine or formula (Q-6), and at least one — CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—;
R ¹⁰ and R ²⁰ are independently hydrogen, fluorine, cyano, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine;
R ³⁰ , R ⁴⁰ and R ⁵⁰ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine;
Ring A ¹¹ and Ring A ²¹ are independently 1,4-phenylene, naphthalene-2,6-diyl, in which at least one hydrogen may be replaced by fluorine, methyl, ethyl or trifluoromethyl. Often;
Z ¹¹ is a single bond, —COO— or —OCO—;
Z ¹² is —CO— or —OCO—;
k ¹⁰ and n ¹⁰ are each independently an integer from 0 to 3, and the sum of k ¹⁰ and n ¹⁰ is an integer from 1 to 4;
n ²⁰ is 1 or 2;
n ³⁰ is 1 or 2,
Item 3. A liquid crystal display device according to item 2.

Item 4. Item 4. The ratio according to any one of Items 1 to 3, wherein the proportion of the alignment monomer in the liquid crystal composition is in the range of 0.1 to 10 parts by weight when the total amount of the liquid crystal compounds is 100 parts by weight. Liquid crystal display element.

式（１）において、Ｒ^１およびＲ^２は独立して、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、炭素数２から１２のアルケニル、または炭素数２から１２のアルケニルオキシであり；環Ａおよび環Ｃは独立して、１，４−シクロヘキシレン、１，４−シクロヘキセニレン、１，４−フェニレン、少なくとも１つの水素がフッ素または塩素で置き換えられた１，４−フェニレン、またはテトラヒドロピラン−２，５−ジイルであり；環Ｂは、２，３−ジフルオロ−１，４−フェニレン、２−クロロ−３−フルオロ−１，４−フェニレン、２，３−ジフルオロ−５−メチル−１，４−フェニレン、３，４，５−トリフルオロナフタレン−２，６−ジイル、または７，８−ジフルオロクロマン−２，６−ジイルであり；Ｚ^１およびＺ^２は独立して、単結合、エチレン、カルボニルオキシ、またはメチレンオキシであり；ａは、１、２、または３であり、ｂは０または１であり、そしてａとｂとの和は３以下である。Item 5. Item 5. The liquid crystal display element according to any one of items 1 to 4, wherein the liquid crystal composition contains at least one compound selected from the group of compounds represented by formula (1) as a first component.

In Formula (1), R ¹ and R ² are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyloxy having 2 to 12 carbons. Yes; Ring A and Ring C are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine Or tetrahydropyran-2,5-diyl; ring B is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5 - methyl-1,4-phenylene, it is a 3,4,5-trifluoro-2,6-diyl or 7,8-difluoro-chroman-2,6-diyl,; ^{Z 1} Oyo Z ² is independently a single bond, ethylene, carbonyloxy or methyleneoxy,; a is 1, 2, or 3,, b is 0 or 1, and the sum is 3 of a and b It is as follows.

式（１−１）から式（１−２２）において、Ｒ^１およびＲ^２は独立して、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、炭素数２から１２のアルケニル、または炭素数２から１２のアルケニルオキシである。Item 6. Item 5. The item according to any one of Items 1 to 5, comprising at least one compound selected from the group of compounds represented by Formula (1-1) to Formula (1-22) as the first component in the liquid crystal composition. A liquid crystal display element according to 1.

In the formula (1-1) to the formula (1-22), R ¹ and R ² are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or It is alkenyloxy having 2 to 12 carbon atoms.

Item 7. Item 7. The liquid crystal display device according to item 5 or 6, wherein the ratio of the first component in the liquid crystal composition is in the range of 10% by weight to 90% by weight.

式（２）において、Ｒ^３およびＲ^４は独立して、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、炭素数２から１２のアルケニル、少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から１２のアルキル、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数２から１２のアルケニルであり；環Ｄおよび環Ｅは独立して、１，４−シクロヘキシレン、１，４−フェニレン、２−フルオロ−１，４−フェニレン、または２，５−ジフルオロ−１，４−フェニレンであり；Ｚ^３は、単結合、エチレン、カルボニルオキシ、またはメチレンオキシであり；ｃは、１、２、または３である。Item 8. Item 8. The liquid crystal display device according to any one of items 1 to 7, wherein the liquid crystal composition further contains at least one compound selected from the group of compounds represented by formula (2) as the second component.

In Formula (2), R ³ and R ⁴ are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, and at least one hydrogen is replaced by fluorine or chlorine Substituted alkyl having 1 to 12 carbon atoms or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine; Ring D and Ring E are each independently 1,4-cyclohexylene; 1,4-phenylene, 2-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene; Z ³ is a single bond, ethylene, carbonyloxy, or methyleneoxy; c Is 1, 2 or 3.

式（２−１）から式（２−１３）において、Ｒ^３およびＲ^４は独立して、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、炭素数２から１２のアルケニル、少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から１２のアルキル、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数２から１２のアルケニルである。Item 9. Any one of Items 1 to 8, further comprising at least one compound selected from the group of compounds represented by Formula (2-1) to Formula (2-13) as the second component in the liquid crystal composition. A liquid crystal display element according to item.

In formulas (2-1) to (2-13), R ³ and R ⁴ are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, It is alkyl having 1 to 12 carbons in which one hydrogen is replaced with fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced with fluorine or chlorine.

Item 10. Item 10. The liquid crystal display device according to item 8 or 9, wherein the ratio of the second component in the liquid crystal composition is in the range of 10% by weight to 90% by weight.

式（３）において、環Ｆおよび環Ｉは独立して、シクロヘキシル、シクロヘキセニル、フェニル、１−ナフチル、２−ナフチル、テトラヒドロピラン−２−イル、１，３−ジオキサン−２−イル、ピリミジン−２−イル、またはピリジン−２−イルであり、これらの環において、少なくとも１つの水素は、フッ素、塩素、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から１２のアルキルで置き換えられてもよく；環Ｇは、１，４−シクロヘキシレン、１，４−シクロヘキセニレン、１，４−フェニレン、ナフタレン−１，２−ジイル、ナフタレン−１，３−ジイル、ナフタレン−１，４−ジイル、ナフタレン−１，５−ジイル、ナフタレン−１，６−ジイル、ナフタレン−１，７−ジイル、ナフタレン−１，８−ジイル、ナフタレン−２，３−ジイル、ナフタレン−２，６−ジイル、ナフタレン−２，７−ジイル、テトラヒドロピラン−２，５−ジイル、１，３−ジオキサン−２，５−ジイル、ピリミジン−２，５−ジイル、またはピリジン−２，５−ジイルであり、これらの環において、少なくとも１つの水素は、フッ素、塩素、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から１２のアルキルで置き換えられてもよく；Ｚ^４およびＺ^５は独立して、単結合または炭素数１から１０のアルキレンであり、このアルキレンにおいて、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく、そして少なくとも１つの−ＣＨ_２ＣＨ_２−は、−ＣＨ＝ＣＨ−、−Ｃ（ＣＨ_３）＝ＣＨ−、−ＣＨ＝Ｃ（ＣＨ_３）−、または−Ｃ（ＣＨ_３）＝Ｃ（ＣＨ_３）−で置き換えられてもよく、これらの基において、少なくとも１つの水素は、フッ素または塩素で置き換えられてもよく；Ｐ^１、Ｐ^２、およびＰ^３は、重合性基であり；Ｓｐ^１、Ｓｐ^２、およびＳｐ^３は独立して、単結合または炭素数１から１０のアルキレンであり、このアルキレンにおいて、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯＯ−、−ＯＣＯ−、または−ＯＣＯＯ−で置き換えられてもよく、そして少なくとも１つの−ＣＨ_２ＣＨ_２−は、−ＣＨ＝ＣＨ−または−Ｃ≡Ｃ−で置き換えられてもよく、これらの基において、少なくとも１つの水素は、フッ素または塩素で置き換えられてもよく；ｄは０、１、または２であり；ｅ、ｆ、およびｇは独立して、０、１、２、３、または４であり、そしてｅ、ｆ、およびｇの和は、１以上である。Item 11. Item 11. The liquid crystal display according to any one of items 1 to 10, wherein the liquid crystal composition further contains at least one compound selected from the group of polymerizable compounds represented by formula (3) as the second additive. element.

In Formula (3), Ring F and Ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidine- 2-yl or pyridin-2-yl, and in these rings, at least one hydrogen is fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or at least one hydrogen. C 1-12 alkyl substituted with fluorine or chlorine may be substituted; ring G may be 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, -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 which at least one hydrogen is fluorine, chlorine, carbon number 1 to 12 alkyl, 1 to 12 carbon alkoxy, or at least one hydrogen may be replaced by 1 to 12 alkyl substituted with fluorine or chlorine; Z ⁴ and Z ⁵ are independently is a single bond or alkylene having 1 to 10 carbon atoms, in the alkylene, at least one of _-CH 2 -, -O -, - CO -, - OO-, or may be replaced by -OCO-, and at least one _-CH 2 CH ₂ - _{is, -CH = CH -, - C} (CH 3) = CH -, - CH = C (CH 3) -, or _{-C (CH 3) = C (} CH 3) - may be replaced by, in these groups, at least one hydrogen may be replaced by fluorine or ^chlorine; P ^{1, P} 2, And P ³ are polymerizable groups; Sp ¹ , Sp ² , and Sp ³ are each independently a single bond or alkylene having 1 to 10 carbons, in which at least one —CH ₂ — is , —O—, —COO—, —OCO—, or —OCOO—, and at least one —CH ₂ CH ₂ — is replaced with —CH═CH— or —C≡C—. Even In these groups, at least one hydrogen may be replaced by fluorine or chlorine; d is 0, 1, or 2; e, f, and g are independently 0, 1, 2, 3 or 4, and the sum of e, f and g is 1 or greater.

式（Ｐ−１）から式（Ｐ−５）において、Ｍ^１、Ｍ^２、およびＭ^３は独立して、水素、フッ素、炭素数１から５のアルキル、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から５のアルキルである。Item 12. In formula (3) in the liquid crystal composition, P ¹ , P ² , and P ³ were independently selected from the group of polymerizable groups represented by formula (P-1) to formula (P-5). Item 12. The liquid crystal display element according to Item 11, which is a group.

In formulas (P-1) to (P-5), M ¹ , M ² , and M ³ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or at least one hydrogen is fluorine or chlorine 1-5 alkyl substituted with

式（３−１）から式（３−２７）において、Ｐ^４、Ｐ^５、およびＰ^６は独立して、式（Ｐ−１）から式（Ｐ−３）で表される重合性基の群から選択された基であり、

ここで、Ｍ^１、Ｍ^２、およびＭ^３は独立して、水素、フッ素、炭素数１から５のアルキル、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から５のアルキルであり；Ｓｐ^１、Ｓｐ^２、およびＳｐ^３は独立して、単結合または炭素数１から１０のアルキレンであり、このアルキレンにおいて、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯＯ−、−ＯＣＯ−、または−ＯＣＯＯ−で置き換えられてもよく、少なくとも１つの−ＣＨ_２ＣＨ_２−は、−ＣＨ＝ＣＨ−または−Ｃ≡Ｃ−で置き換えられてもよく、これらの基において、少なくとも１つの水素は、フッ素または塩素で置き換えられてもよい。Item 13. Any one of Items 1 to 12 containing at least one compound selected from the group of polymerizable compounds represented by Formula (3-1) to Formula (3-27) as the second additive in the liquid crystal composition 2. A liquid crystal display device according to item 1.

In Formula (3-1) to Formula (3-27), P ⁴ , P ⁵ , and P ⁶ are independently a polymerizable group represented by Formula (P-1) to Formula (P-3). A group selected from the group;

Here, M ¹ , M ² , and M ³ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine. Yes; Sp ¹ , Sp ² , and Sp ³ are each independently a single bond or alkylene having 1 to 10 carbons, in which at least one —CH ₂ — is —O—, —COO—, -OCO-, or -OCOO- in may be replaced, at least one _-CH 2 CH ₂ - may be replaced by -CH = CH- or -C≡C-, and in the groups, at least One hydrogen may be replaced with fluorine or chlorine.

Item 14. The ratio of the second additive in the liquid crystal composition is in the range of 0.03 parts by weight to 10 parts by weight when the total amount of liquid crystal compounds is 100 parts by weight. The liquid crystal display element as described.

Item 15. Item 15. The liquid crystal composition according to any one of items 1 to 14 and an electrode between a pair of substrates, and the alignment monomer in the liquid crystal composition reacted by irradiating linearly polarized light. Liquid crystal display element.

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

Item 17. Item 16. The liquid crystal display element according to item 15, wherein the operation mode of the liquid crystal display element is an IPS mode or an FFS mode, and the driving method of the liquid crystal display element is an active matrix method.

Item 18. Item 15. A polymer-supported alignment type liquid crystal display device comprising the liquid crystal composition according to any one of items 1 to 14, wherein a polymerizable compound in the liquid crystal composition is polymerized.

Item 19. Item 15. Use of the liquid crystal composition according to any one of items 1 to 14 in a liquid crystal display device.

Item 20. Item 15. Use of the liquid crystal composition according to any one of items 1 to 14 in a polymer supported alignment type liquid crystal display device.

式（Ａ−１）において、Ｐ^１０およびＰ^２０は独立して、式（Ｑ−１）で表される基から選択された基であり；
式（Ｑ−１）において、Ｍ^１０、Ｍ^２０、およびＭ^３０は独立して、水素、フッ素、メチル、または少なくとも１つの水素がフッ素で置き換えられた炭素数１から５のアルキルであり；
Ｓｐ^１０およびＳｐ^２０は独立して、単結合または炭素数１から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素または式（Q−６）で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく、少なくとも１つの−ＣＨ_２ＣＨ_２−は、−ＣＨ＝ＣＨ−で置き換えられてもよく；
ｋ^１０およびｎ^１０は独立して０から３の整数であり、ｋ^１０とｎ^１０の和が１から４の整数であり；
Ｒ^１０、Ｒ^２０、Ｒ^３０、およびＲ^４０は独立して、水素、フッ素、炭素数１から１０のアルキル、または少なくとも１つの水素がフッ素に置き換えられた炭素数１から１０のアルキルであり；
式（Ｑ−６）において、Ｍ^１０、Ｍ^２０、およびＭ^３０は独立して、水素、フッ素、メチル、または少なくとも１つの水素がフッ素で置き換えられた炭素数１から５のアルキルであり；Ｓｐ^４１は独立して、単結合または炭素数１から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素または塩素で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく；
Ｓｐ^１０とＳｐ^２０が共に炭素数３、６または１１のアルキレンであるとき、Ｒ^１０が水素、炭素数２から１０のアルキルまたは少なくとも１つの水素がフッ素に置き換えられた炭素数１から１０のアルキルであり、Ｒ^２０が水素であり；
Ｓｐ^１０とＳｐ^２０が共に炭素数６または８のアルキレンであるとき、Ｒ^１０およびＲ^２０が水素であり、Ｒ^３０は水素、フッ素、炭素数２から１０のアルキル、または少なくとも１つの水素がフッ素に置き換えられた炭素数１から１０のアルキルであり、Ｒ^４０は水素である。Item 21. A compound represented by formula (A-1).

In formula (A-1), P ¹⁰ and P ²⁰ are independently a group selected from the group represented by formula (Q-1);
In formula (Q-1), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, methyl, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine;
Sp ¹⁰ and Sp ²⁰ are independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or formula (Q-6), and at least one of —CH ₂ — may be replaced with —O—, —CO—, —COO—, or —OCO—, and at least one —CH ₂ CH ₂ — may be replaced with —CH═CH—. Often;
k ¹⁰ and n ¹⁰ are each independently an integer from 0 to 3, and the sum of k ¹⁰ and n ¹⁰ is an integer from 1 to 4;
R ¹⁰ , R ²⁰ , R ³⁰ , and R ⁴⁰ are independently hydrogen, fluorine, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine;
In formula (Q-6), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, methyl, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine; Sp ⁴¹ is independently a single bond or alkylene having 1 to 12 carbons, wherein at least one hydrogen of the alkylene may be replaced by fluorine or chlorine, and at least one —CH ₂ — is —O— , -CO-, -COO-, or -OCO-;
When Sp ¹⁰ and Sp ²⁰ are both alkylene having 3, 6 or 11 carbon atoms, R ¹⁰ is hydrogen, alkyl having 2 to 10 carbon atoms or alkyl having 1 to 10 carbon atoms in which at least one hydrogen is replaced by fluorine. And R ²⁰ is hydrogen;
When both Sp ¹⁰ and Sp ²⁰ are alkylene having 6 or 8 carbon atoms, R ¹⁰ and R ²⁰ are hydrogen, R ³⁰ is hydrogen, fluorine, alkyl having 2 to 10 carbon atoms, or at least one hydrogen is fluorine. R 1 is alkyl having 1 to 10 carbon atoms replaced by R ⁴⁰ .

Item 22. Item 20. Use of the compound according to Item 21 as a monomer for forming an orientation control layer.

Item 23. Item 15. The liquid crystal composition according to any one of items 1 to 14.

  The present invention also includes the following items. (A) The above composition further containing at least one additive such as an optically active compound, an antioxidant, an ultraviolet absorber, a dye, an antifoaming agent, a polymerizable compound, a polymerization initiator, a polymerization inhibitor, and a polar compound. object. (B) An AM device containing the above composition. (C) A polymer-supported orientation (PSA) type AM device containing the above composition further containing a polymerizable compound. (D) A polymer-supported orientation (PSA) type AM device comprising the above-described composition, wherein the polymerizable compound in the composition is polymerized. (E) A device containing the above composition and having a mode of PC, TN, STN, ECB, OCB, IPS, VA, FFS, or FPA. (F) A transmissive device containing the above composition. (G) Use of the above composition as a composition having a nematic phase. (H) Use as an optically active composition by adding an optically active compound to the above composition.

  The alignment monomer contained in the liquid crystal composition used in the liquid crystal display element of the present invention will be described. The orientation monomer means a compound that absorbs polarized light and causes a reaction such as dimerization or isomerization. In the present invention, the formula (A), the formula (B), the formula (C), the formula (D), A compound selected from the group consisting of compounds represented by formula (A-1), formula (A-2), formula (B-1), formula (C-1), and formula (D-1) is used.

式（Ａ）から式（Ｄ）において、Ｐ^１０、Ｐ^２０、Ｐ^３０およびＰ^４０は独立して、式（Ｑ−１）から式（Ｑ−５）で表される基から選択された基であり；

式（Ｑ−１）から式（Ｑ−５）において、Ｍ^１０、Ｍ^２０、およびＭ^３０は独立して、水素、フッ素、炭素数１から５のアルキル、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から５のアルキルであり；
Ｓｐ^１０、Ｓｐ^２０、およびＳｐ^４０は独立して、単結合または炭素数１から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素、塩素または式（Ｑ−６）で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく、少なくとも１つの−ＣＨ_２ＣＨ_２−は−ＣＨ＝ＣＨ−で置き換えられてもよく；
Ｓｐ^３０は独立して、単結合または炭素数１から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素、塩素または式（Ｑ−６）で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく；

式（Ｑ−６）において、Ｍ^１０、Ｍ^２０、およびＭ^３０は独立して、水素、フッ素、炭素数１から５のアルキル、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から５のアルキルであり；
Ｓｐ^４１は独立して、単結合または炭素数１から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素または塩素で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく；
環Ａ^１０および環Ａ^２０は独立して、フェニル、４−ビフェニル、１−ナフチル、２−ナフチル、ピリミジン−２−イル、ピリミジン−５−イル、ピリジン−２−イル、ピリジン−５−イル、フルオレン−２−イル、フルオレン−３−イル、フェナントレン−２−イル、アントラセン−２−イルであり、これらの環において、少なくとも１つの水素は、フッ素、塩素、炭素数１から１２のアルキル、炭素数２から１２のアルケニル、炭素数１から１１のアルコキシ、または炭素数２から１１のアルケニルオキシで置き換えられてもよく、これらの基において、少なくとも１つの水素は、フッ素または塩素で置き換えられてもよく；
環Ａ^１１、環Ａ^２１、環Ａ^１２、環Ａ^２２および環Ａ^３０は独立して、１，４−シクロへキシレン、１，４−シクロヘキセニレン、１，４−フェニレン、４，４’−ビフェニレン、ナフタレン−２，６−ジイル、デカヒドロナフタレン−２，６−ジイル、１，２，３，４−テトラヒドロナフタレン−２，６−ジイル、テトラヒドロピラン−２，５−ジイル、１，３−ジオキサン−２，５−ジイル、ピリミジン−２，５−ジイル、ピリジン−２，５−ジイル、フルオレン−２，７−ジイル、フェナントレン−２，７−ジイル、アントラセン−２，６−ジイル、ペルヒドロシクロペンタ［ａ］フェナントレン−３，１７−ジイル、または２，３，４，７，８，９，１０，１１，１２，１３，１４，１５，１６，１７−テトラデカヒドロシクロペンタ［ａ］フェナントレン−３，１７−ジイルであるが、隣接する結合が、−ＣＨ＝ＣＨ−、−ＣＲ^１０＝ＣＲ^２０−、−ＣＯ−ＣＨ＝ＣＨ−、−ＣＨ＝ＣＨ−ＣＯ−、−ＯＣＯ−ＣＨ＝ＣＨ−、または−ＣＨ＝ＣＨ−ＣＯＯ−であり、Ｒ^１０およびＲ^２０は独立して、水素、フッ素、シアノ、炭素数１から１０のアルキル、または少なくとも１つの水素がフッ素に置き換えられた炭素数１から１０のアルキルであるときは、１，４−フェニレン、４，４’−ビフェニレン、ナフタレン−２，６−ジイル、ピリミジン−２，５−ジイル、ピリジン−２，５−ジイル、フルオレン−２，７−ジイル、フェナントレン−２，７−ジイル、アントラセン−２，６−ジイルであり、これらの環において、少なくとも１つの水素は、フッ素、塩素、炭素数１から１２のアルキル、炭素数２から１２のアルケニル、炭素数１から１１のアルコキシ、または炭素数２から１１のアルケニルオキシで置き換えられてもよく、これらの基において、少なくとも１つの水素は、フッ素または塩素で置き換えられてもよく；
環Ａ^４０は、１，４−シクロへキシレン、１，４−シクロヘキセニレン、１，４−フェニレン、４，４’−ビフェニレン、ナフタレン−２，６−ジイル、デカヒドロナフタレン−２，６−ジイル、１，２，３，４−テトラヒドロナフタレン−２，６−ジイル、テトラヒドロピラン−２，５−ジイル、１，３−ジオキサン−２，５−ジイル、ピリミジン−２，５−ジイル、ピリジン−２，５−ジイル、フルオレン−２，７−ジイル、フェナントレン−２，７−ジイル、アントラセン−２，６−ジイル、ペルヒドロシクロペンタ［ａ］フェナントレン−３，１７−ジイル、または２，３，４，７，８，９，１０，１１，１２，１３，１４，１５，１６，１７−テトラデカヒドロシクロペンタ［ａ］フェナントレン−３，１７−ジイルであるが、隣接する結合が、−ＣＨ＝ＣＨ−、−ＣＯ−ＣＨ＝ＣＨ−、−ＣＨ＝ＣＨ−ＣＯ−、−ＯＣＯ−ＣＨ＝ＣＨ−、または−ＣＨ＝ＣＨ−ＣＯＯ−であるときは、１，４−フェニレン、４，４’−ビフェニレン、ナフタレン−２，６−ジイル、ピリミジン−２，５−ジイル、ピリジン−２，５−ジイル、フルオレン−２，７−ジイル、フェナントレン−２，７−ジイル、アントラセン−２，６−ジイルであり、これらの環において、少なくとも１つの水素は、Ｐ^２０−Ｓｐ^２０−、フッ素、塩素、炭素数１から１２のアルキル、炭素数２から１２のアルケニル、炭素数１から１１のアルコキシ、または炭素数２から１１のアルケニルオキシで置き換えられてもよく、これらの基において、少なくとも１つの水素は、フッ素または塩素で置き換えられてもよく；
Ｚ^１０は独立して、−ＣＨ＝ＣＨ−、−ＣＲ^１０＝ＣＲ^２０−、−ＣＯ−ＣＨ＝ＣＨ−、−ＣＨ＝ＣＨ−ＣＯ−、−ＯＣＯ−ＣＨ＝ＣＨ−、または−ＣＨ＝ＣＨ−ＣＯＯ−であり、Ｒ^１０およびＲ^２０は独立して、水素、フッ素、シアノ、炭素数１から１０のアルキル、または少なくとも１つの水素がフッ素に置き換えられた炭素数１から１０のアルキルであり；
Ｚ^１１は独立して、単結合または炭素数１から６のアルキレンであり、このアルキレンにおいて、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、−ＯＣＯ−、または−ＯＣＯＯ−で置き換えられてもよく、少なくとも１つの−（ＣＨ_２）_２−は、−ＣＨ＝ＣＨ−または−Ｃ≡Ｃ−で置き換えられてもよく、これらの基において、少なくとも１つの水素は、フッ素または塩素で置き換えられてもよく；
Ｚ^２０およびＺ^２１は独立して、単結合、炭素数１から６のアルキレンまたは炭素数２から６のアルケニレンであるが、少なくとも一方は、炭素数２から６のアルケニレンである。これらのアルキレン、アルケニレンにおいて、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、−ＯＣＯ−、または−ＯＣＯＯ−で置き換えられてもよく、その他の少なくとも１つの−（ＣＨ_２）_２−は、−ＣＨ＝ＣＨ−または−Ｃ≡Ｃ−で置き換えられてもよく、これらの基において、少なくとも１つの水素は、フッ素または塩素で置き換えられてもよく；
ｋ^１０およびｎ^１０は独立して０から３の整数であり、ｋ^１０とｎ^１０の和が１から６の整数であり；
ｎ^２０は１または２であり；
ｎ^３０は１または２である。

In formulas (A) to (D), P ¹⁰ , P ²⁰ , P ³⁰ and P ⁴⁰ are each independently a group selected from the groups represented by formula (Q-1) to formula (Q-5) Is;

In formulas (Q-1) to (Q-5), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or at least one hydrogen is fluorine or chlorine 1 to 5 carbon alkyls replaced by
Sp ¹⁰ , Sp ²⁰ , and Sp ⁴⁰ are each independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene is replaced by fluorine, chlorine or the formula (Q-6) And at least one —CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—, and at least one —CH ₂ CH ₂ — may be —CH═CH—. May be replaced by;
Sp ³⁰ is independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine, chlorine or formula (Q-6), and at least one — CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—;

In Formula (Q-6), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or 1 carbon in which at least one hydrogen is replaced by fluorine or chlorine. To alkyl of 5;
Sp ⁴¹ is independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or chlorine, and at least one —CH ₂ — is —O ₂ May be replaced by-, -CO-, -COO-, or -OCO-;
Ring A ¹⁰ and Ring A ²⁰ are independently phenyl, 4-biphenyl, 1-naphthyl, 2-naphthyl, pyrimidin-2-yl, pyrimidin-5-yl, pyridin-2-yl, pyridin-5-yl, Fluoren-2-yl, fluoren-3-yl, phenanthren-2-yl, anthracen-2-yl, and in these rings, at least one hydrogen is fluorine, chlorine, alkyl having 1 to 12 carbons, carbon May be replaced by alkenyl having 2 to 12 carbon atoms, alkoxy having 1 to 11 carbon atoms, or alkenyloxy having 2 to 11 carbon atoms, and in these groups, at least one hydrogen may be replaced by fluorine or chlorine. Often;
Ring A ¹¹ , Ring A ²¹ , Ring A ¹² , Ring A ²² and Ring A ³⁰ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 4,4 ′. -Biphenylene, 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, per Hydrocyclopenta [a] phenanthrene-3,17-diyl or 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclo Is a pointer [a] phenanthrene-3,17-diyl, adjacent ^{bond, -CH = CH -, - CR} 10 = CR 20 -, - CO-CH = CH -, - CH = CH-CO-, —OCO—CH═CH—, or —CH═CH—COO—, wherein R ¹⁰ and R ²⁰ are independently hydrogen, fluorine, cyano, alkyl having 1 to 10 carbons, or at least one hydrogen is fluorine. 1, 4-phenylene, 4,4′-biphenylene, 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 which at least one hydrogen is fluorine, chlorine, Alkyl having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkoxy having 1 to 11 carbon atoms, or alkenyloxy having 2 to 11 carbon atoms may be substituted, and in these groups, at least one hydrogen is May be replaced by fluorine or chlorine;
Ring A ⁴⁰ includes 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 4,4′-biphenylene, 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, or 2,3 4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta [a] phenanthrene-3,17-diyl, but next When the bond to be —CH═CH—, —CO—CH═CH—, —CH═CH—CO—, —OCO—CH═CH—, or —CH═CH—COO— is 1, 4 -Phenylene, 4,4'-biphenylene, naphthalene-2,6-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, and in these rings, at least one of ^hydrogen, P 20 ^{-Sp 20} -, fluorine, chlorine, alkyl of from 1 to 12 carbons, alkenyl having 2 to 12 carbons, carbon atoms May be substituted with 1 to 11 alkoxy, or alkenyloxy with 2 to 11 carbons, in which at least one hydrogen is replaced with fluorine or chlorine It may be;
Z ¹⁰ is independently —CH═CH—, —CR ¹⁰ = CR ²⁰ —, —CO—CH═CH—, —CH═CH—CO—, —OCO—CH═CH—, or —CH═CH. -COO- and R ¹⁰ and R ²⁰ are independently hydrogen, fluorine, cyano, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine. ;
Z ¹¹ is independently a single bond or an alkylene having 1 to 6 carbon atoms, in which at least one —CH ₂ — is —O—, —CO—, —COO—, —OCO—, or may be replaced by -OCOO-, at least one - _{(CH 2) 2} - may be replaced by -CH = CH- or -C≡C-, and in the groups, at least one hydrogen May be replaced by fluorine or chlorine;
Z ²⁰ and Z ²¹ are independently a single bond, alkylene having 1 to 6 carbons or alkenylene having 2 to 6 carbons, but at least one is alkenylene having 2 to 6 carbons. In these alkylene and alkenylene, at least one —CH ₂ — may be replaced by —O—, —CO—, —COO—, —OCO—, or —OCOO—, and at least one other — ( CH ₂ ) ₂ — may be replaced by —CH═CH— or —C≡C—, in which at least one hydrogen may be replaced by fluorine or chlorine;
k ¹⁰ and n ¹⁰ are each independently an integer from 0 to 3, and the sum of k ¹⁰ and n ¹⁰ is an integer from 1 to 6;
n ²⁰ is 1 or 2;
n ³⁰ is 1 or 2.

式（Ａ−１）、式（Ａ−２）、式（Ｂ−１）、式（Ｃ−１）および式（Ｄ−１）において、Ｐ^１０、Ｐ^２０、Ｐ^３０、Ｐ^４０、Ｐ^５０およびＰ^６０は独立して、式（Ｑ−１）で表される基から選択された基であり；
式（Ｑ−１）において、Ｍ^１０、Ｍ^２０、およびＭ^３０は独立して、水素、フッ素、メチル、または少なくとも１つの水素がフッ素で置き換えられた炭素数１から５のアルキルであり；
Ｓｐ^１０、Ｓｐ^２０、およびＳｐ^４０は独立して、単結合または炭素数１から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素または式（Ｑ−６）で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく、少なくとも１つの−ＣＨ_２ＣＨ_２−は−ＣＨ＝ＣＨ−で置き換えられてもよく；
Ｓｐ^３０は独立して、単結合または炭素数１から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素、塩素または式（Ｑ−６）で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく；
式（Ｑ−６）において、Ｍ^１０、Ｍ^２０、およびＭ^３０は独立して、水素、フッ素、メチル、または少なくとも１つの水素がフッ素で置き換えられた炭素数１から５のアルキルであり；
Ｓｐ^４１は独立して、単結合または炭素数１から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素または塩素で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく；
Ｓｐ^５０およびＳｐ^６０は独立して、炭素数２から１２のアルキレンであり、このアルキレンの少なくとも１つの水素はフッ素、塩素または式（Ｑ−６）で置き換えられていてもよく、少なくとも１つの−ＣＨ_２−は、−Ｏ−、−ＣＯ−、−ＣＯＯ−、または−ＯＣＯ−で置き換えられてもよく；
Ｒ^１０およびＲ^２０は独立して、水素、フッ素、シアノ、炭素数１から１０のアルキル、または少なくとも１つの水素がフッ素に置き換えられた炭素数１から１０のアルキルであり；
Ｒ^３０、Ｒ^４０、Ｒ^４１およびＲ^５０は独立して、水素、フッ素、塩素、炭素数１から１０のアルキル、または少なくとも１つの水素がフッ素に置き換えられた炭素数１から１０のアルキルであり；
環Ａ^１１および環Ａ^２１は独立して１，４−フェニレン、ナフタレン−２，６−ジイルであり、これらにおいて、少なくとも１つの水素は、フッ素、塩素、炭素数１から１２のアルキル、または少なくとも１つの水素がフッ素で置き換えられた炭素数１から１２のアルキルで置き換えられてもよく；
Ｚ^１１は単結合、エチレン、メチレンオキシ、−ＣＯＯ−、−ＯＣＯ−、−ＯＣＯＯ−、または−ＣＨ＝ＣＨ−ＣＯＯ−であり；
Ｚ^１２は−ＣＯ−、または−ＯＣＯ−であり；
ｋ^１０およびｎ^１０は独立して０から３の整数であり、ｋ^１０とｎ^１０の和が１から４の整数であり；
ｎ^２０は１または２であり；
ｎ^３０は１または２であり；
Ｚ^２０およびＺ^２１は独立して、単結合、−ＣＯ−ＣＨ＝ＣＨ−、−ＣＨ＝ＣＨ−ＣＯ−、−ＯＣＯ−ＣＨ＝ＣＨ−、−ＣＨ＝ＣＨ−ＣＯＯ−または−ＣＨ＝ＣＨ−であるが、同時に単結合となることはない。

In Formula (A-1), Formula (A-2), Formula (B-1), Formula (C-1), and Formula (D-1), P ¹⁰ , P ²⁰ , P ³⁰ , P ⁴⁰ , P ⁵⁰ And P ⁶⁰ is independently a group selected from the groups represented by formula (Q-1);
In formula (Q-1), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, methyl, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine;
Sp ¹⁰ , Sp ²⁰ , and Sp ⁴⁰ are each independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or formula (Q-6) , At least one —CH ₂ — may be replaced with —O—, —CO—, —COO—, or —OCO—, and at least one —CH ₂ CH ₂ — is replaced with —CH═CH—. May be
Sp ³⁰ is independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine, chlorine or formula (Q-6), and at least one — CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—;
In formula (Q-6), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, methyl, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine;
Sp ⁴¹ is independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or chlorine, and at least one —CH ₂ — is —O ₂ May be replaced by-, -CO-, -COO-, or -OCO-;
Sp ⁵⁰ and Sp ⁶⁰ are independently alkylene having 2 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine, chlorine or formula (Q-6), and at least one — CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—;
R ¹⁰ and R ²⁰ are independently hydrogen, fluorine, cyano, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine;
R ³⁰ , R ⁴⁰ , R ⁴¹ and R ⁵⁰ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine. ;
Ring A ¹¹ and Ring A ²¹ are independently 1,4-phenylene, naphthalene-2,6-diyl, in which at least one hydrogen is fluorine, chlorine, alkyl having 1 to 12 carbons, or at least One hydrogen may be replaced by alkyl of 1 to 12 carbons replaced by fluorine;
Z ¹¹ is a single bond, ethylene, methyleneoxy, —COO—, —OCO—, —OCOO—, or —CH═CH—COO—;
Z ¹² is —CO— or —OCO—;
k ¹⁰ and n ¹⁰ are each independently an integer from 0 to 3, and the sum of k ¹⁰ and n ¹⁰ is an integer from 1 to 4;
n ²⁰ is 1 or 2;
n ³⁰ is 1 or 2;
Z ²⁰ and Z ²¹ independently represent a single bond, —CO—CH═CH—, —CH═CH—CO—, —OCO—CH═CH—, —CH═CH—COO— or —CH═CH—. However, it does not become a single bond at the same time.

The alignment monomer having a vinylene group is considered to undergo photoisomerization from a trans isomer to a cis isomer and formation of a cyclobutane ring by dimerization when irradiated with ultraviolet light. Using this property, a thin film capable of aligning liquid crystal molecules can be prepared.
In order to prepare this thin film, linearly polarized light is suitable for the ultraviolet rays to be irradiated.
First, an alignment monomer is added to the liquid crystal composition in a range of 0.1 to 10 parts by weight when the total amount of liquid crystal compounds is 100 parts by weight, and the composition is dissolved to dissolve the alignment monomer. Warm up. This composition is injected into a device having no alignment film. Next, photoisomerization and dimerization of the alignment monomer are promoted by irradiating the linearly polarized light while heating the device at a temperature higher than the upper limit temperature of the nematic phase. The photoisomerized compound and the dimerized compound are arranged in a certain direction. At the same time, photopolymerization occurs and a thin film is formed on the substrate. The formed thin film has a function as a liquid crystal alignment film.

  The composition used in the present invention will be described in the following order. First, the composition of the composition will be described. Second, the main characteristics of the component compounds and the main effects of the compounds on the composition and the device will be described. Third, the combination of components in the composition, the preferred ratio of the components, and the basis thereof will be described. Fourth, a preferred form of the component compound will be described. Fifth, preferred component compounds are shown. Sixth, additives that may be added to the composition will be described. Seventh, a method for synthesizing the component compounds will be described. Eighth, the use of the composition will be described. Ninth, a method for manufacturing an element will be described.

  First, the composition of the composition will be described. This composition contains a plurality of liquid crystal compounds. The composition may contain additives. Additives include optically active compounds, antioxidants, ultraviolet absorbers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, polar compounds and the like. This composition is classified into a composition A and a composition B from the viewpoint of a liquid crystal compound. The composition A may further contain other liquid crystal compounds in addition to the liquid crystal compound selected from the compound (1) and the compound (2). The “other liquid crystal compound” is a liquid crystal compound different from the compound (1) and the compound (2). Such compounds are mixed into the composition for the purpose of further adjusting the properties.

  Composition B consists essentially of a liquid crystalline compound selected from compound (1) and compound (2). The term “substantially” means that the composition may contain an additive but no other liquid crystal compound. Composition B has fewer components than composition A. From the viewpoint of reducing the cost, the composition B is preferable to the composition A. The composition A is preferable to the composition B from the viewpoint that the characteristics can be further adjusted by mixing other liquid crystal compounds.

  Second, the main characteristics of the component compounds and the main effects of the compounds on the composition and the device will be described. The main characteristics of the component compounds are summarized in Table 2 based on the effects of the present invention. In the symbols in Table 2, L means large or high, M means moderate, and S means small or low. The symbols L, M, and S are classifications based on qualitative comparison among the component compounds, and the symbol 0 (zero) means that the dielectric anisotropy is extremely small.

  When component compounds are mixed into the composition, the main effects of the component compounds on the properties of the composition are as follows. The alignment monomer is the first additive. This compound is arranged in a certain direction at the molecular level when dimerization or isomerization is performed by polarized light. Therefore, a thin film prepared from an alignment monomer aligns liquid crystal molecules in the same manner as an alignment film such as polyimide. Compound (1) as the first component increases the dielectric anisotropy and decreases the minimum temperature. Compound (2) as the second component increases the maximum temperature or decreases the viscosity. Compound (3), the second additive, gives a polymer by polymerization, which shortens the response time of the device and improves image burn-in.

  Third, the combination of components in the composition, the preferred ratio of the components, and the basis thereof will be described. Preferred combinations of the components in the composition are: first additive + first component, first additive + second component, first additive + first component + second component, first additive + first component + first Two additives, first additive + second component + second additive or first additive + first component + second component + second additive. Further preferred combinations are: first additive + first component + second component or first additive + first component + second component + second additive.

  A desirable ratio of the alignment monomer as the first additive is about 0.1 parts by weight or more when the total amount of the liquid crystal compounds is 100 parts by weight in order to align liquid crystal molecules. About 10 parts by weight or less to prevent. A more desirable ratio is in the range of approximately 0.3 part by weight to approximately 6 parts by weight. A particularly preferred ratio is in the range of approximately 0.5 parts by weight to approximately 4 parts by weight.

  A desirable ratio of the first component is approximately 10% by weight or more for increasing the dielectric anisotropy, and approximately 90% by weight or less for decreasing the minimum temperature. A more desirable ratio is in the range of approximately 20% by weight to approximately 85% by weight. A particularly preferred ratio is in the range of approximately 30% by weight to approximately 85% by weight.

  A desirable ratio of the second component is approximately 10% by weight or more for decreasing the viscosity, and approximately 90% by weight or less for increasing the dielectric anisotropy. A more desirable ratio is in the range of approximately 15% by weight to approximately 65% by weight. A particularly preferred ratio is in the range of approximately 20% by weight to approximately 60% by weight.

  The second additive is added to the composition for the purpose of adapting to the polymer-supported orientation type device. A desirable ratio of the additive is about 0.03 part by weight or more when the total amount of the liquid crystal compounds is 100 parts by weight for aligning liquid crystal molecules, and about 10 parts by weight for preventing display defects of the device. It is as follows. A more desirable ratio is in the range of approximately 0.1 parts by weight to approximately 2 parts by weight. A particularly preferred ratio is in the range of approximately 0.2 parts by weight to approximately 1.0 parts by weight.

Fourth, a preferred form of the component compound will be described. In Formula (1) and Formula (2), R ¹ and R ² are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or 2 to C 12 alkenyloxy. Desirable R ¹ or R ² is alkyl having 1 to 12 carbons for increasing the stability to ultraviolet light or heat, and alkoxy having 1 to 12 carbons for increasing the dielectric anisotropy. R ³ and R ⁴ are independently an alkyl having 1 to 12 carbons, an alkoxy having 1 to 12 carbons, an alkenyl having 2 to 12 carbons, an alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine 12 alkyls or alkenyls having 2 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine. Desirable R ³ or R ⁴ is alkenyl having 2 to 12 carbons for decreasing the viscosity, and alkyl having 1 to 12 carbons for increasing the stability to ultraviolet light or heat. Alkyl is linear or branched and does not include cyclic alkyl. Linear alkyl is preferred over branched alkyl. The same applies to terminal groups such as alkoxy and alkenyl.

  Preferred alkyl is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, or octyl. More desirable alkyl is methyl, ethyl, propyl, butyl or pentyl for decreasing the viscosity.

  Preferred alkoxy is methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, or heptyloxy. More desirable alkoxy is methoxy or ethoxy for decreasing the viscosity.

  Preferred alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl. More desirable alkenyl is vinyl, 1-propenyl, 3-butenyl, or 3-pentenyl for decreasing the viscosity. The preferred configuration of —CH═CH— in these alkenyls depends on the position of the double bond. Trans is preferable in alkenyl such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyl and 3-hexenyl for decreasing the viscosity. Cis is preferable in alkenyl such as 2-butenyl, 2-pentenyl and 2-hexenyl.

  Preferred examples of alkyl in which at least one hydrogen is replaced by fluorine or chlorine are fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl, 7-fluoroheptyl. Or 8-fluorooctyl. Further preferred examples are 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl or 5-fluoropentyl for increasing the dielectric anisotropy.

  Preferred examples of alkenyl in which at least one hydrogen is replaced by fluorine or chlorine are 2,2-difluorovinyl, 3,3-difluoro-2-propenyl, 4,4-difluoro-3-butenyl, 5,5-difluoro. -4-pentenyl, or 6,6-difluoro-5-hexenyl. Further preferred examples are 2,2-difluorovinyl or 4,4-difluoro-3-butenyl for decreasing the viscosity.

または

であり、好ましくは

である。Ring A and Ring C are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine, or Tetrahydropyran-2,5-diyl. Preferred ring A or ring C is 1,4-cyclohexylene for decreasing the viscosity, tetrahydropyran-2,5-diyl for increasing the dielectric anisotropy, and increasing the optical anisotropy. 1,4-phenylene. Tetrahydropyran-2,5-diyl is

Or

And preferably

It is.

  Ring B is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4, 5-trifluoronaphthalene-2,6-diyl or 7,8-difluorochroman-2,6-diyl. Preferred ring B is 2,3-difluoro-1,4-phenylene for decreasing the viscosity, and 2-chloro-3-fluoro-1,4-phenylene for decreasing the optical anisotropy. In order to increase anisotropy, it is 7,8-difluorochroman-2,6-diyl.

  Ring D and ring E are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene. Preferred ring D or ring E is 1,4-cyclohexylene for decreasing the viscosity or increasing the maximum temperature, and 1,4-phenylene for decreasing the minimum temperature. The configuration of 1,4-cyclohexylene is preferably trans rather than cis for increasing the maximum temperature.

Z ¹ and Z ² are independently a single bond, ethylene, carbonyloxy, or methyleneoxy. Desirable Z ¹ or Z ² is a single bond for decreasing the viscosity, ethylene for decreasing the minimum temperature, and methyleneoxy for increasing the dielectric anisotropy. Z ³ is a single bond, ethylene, carbonyloxy, or methyleneoxy. Desirable Z ³ is a single bond for decreasing the viscosity, ethylene for decreasing the minimum temperature, and carbonyloxy for increasing the maximum temperature.

  a is 1, 2, or 3, b is 0 or 1, and the sum of a and b is 3 or less. Preferred a is 1 for decreasing the viscosity, and 2 or 3 for increasing the maximum temperature. Preferred b is 0 for decreasing the viscosity, and 1 for decreasing the minimum temperature. c is 1, 2 or 3. Preferred c is 1 for decreasing the viscosity, and 2 or 3 for increasing the maximum temperature.

In formula (3), P ¹ , P ² , and P ³ are independently a polymerizable group. Preferred P ¹ , P ² , or P ³ is a polymerizable group selected from the group of groups represented by formula (P-1) to formula (P-5). Further preferred P ¹ , P ² , or P ³ is a group represented by the formula (P-1), the formula (P-2), or the formula (P-3). Particularly preferred P ¹ , P ² , or P ³ is a group represented by the formula (P-1) or the formula (P-2). Most preferred P ¹ , P ² or P ³ is a group represented by the formula (P-1). A preferred group represented by formula (P-1) is —OCO—CH═CH ₂ or —OCO—C (CH ₃ ) ═CH ₂ . The wavy line from Formula (P-1) to Formula (P-5) indicates the site to be bound.

In formulas (P-1) to (P-5), M ¹ , M ² , and M ³ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or at least one hydrogen is fluorine or chlorine 1-5 alkyl substituted with Preferred M ¹ , M ² or M ³ is hydrogen or methyl for increasing the reactivity. More preferred M ¹ is hydrogen or methyl, and more preferred M ² or M ³ is hydrogen.

Sp ¹ , Sp ² , and Sp ³ are each independently a single bond or alkylene having 1 to 10 carbon atoms, and in this alkylene, at least one —CH ₂ — is —O—, —COO—, —OCO. -, or it may be replaced by -OCOO-, at least one _-CH 2 -CH ₂ - may be replaced by -CH = CH- or -C≡C-, and in the groups, at least 1 One hydrogen may be replaced with fluorine or chlorine. Preferred Sp ¹ , Sp ² , or Sp ³ is a single bond, —CH ₂ —CH ₂ —, —CH ₂ O—, —OCH ₂ —, —COO—, —OCO—, —CO—CH═CH—, Or -CH = CH-CO-. Further preferred Sp ¹ , Sp ² , or Sp ³ is a single bond.

  Ring F and Ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxan-2-yl, pyrimidin-2-yl, or pyridine -2-yl, and in these rings, at least one hydrogen is fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or at least one hydrogen is replaced by fluorine or chlorine. Further, it may be substituted with alkyl having 1 to 12 carbons. Preferred ring F or ring I is 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, At least one hydrogen is fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or at least one hydrogen is fluorine or chlorine. From the obtained 1 carbon atoms may be replaced by alkyl of 12. Preferred ring G is 1,4-phenylene or 2-fluoro-1,4-phenylene.

Z ⁴ and Z ⁵ are each independently a single bond or alkylene having 1 to 10 carbons, in which at least one —CH ₂ — is —O—, —CO—, —COO—, or — may be replaced by OCO-, at least one _-CH 2 -CH ₂ - _{is, -CH = CH -, - C} (CH 3) = CH -, - CH = C (CH 3) -, or -C (CH ₃ ) ═C (CH ₃ ) — may be replaced, and in these groups at least one hydrogen may be replaced with fluorine or chlorine. Preferred Z ⁴ or Z ⁵ is a single bond, —CH ₂ —CH ₂ —, —CH ₂ O—, —OCH ₂ —, —COO—, or —OCO—. Further preferred Z ⁴ or Z ⁵ is a single bond.

  d is 0, 1, or 2. Preferred d is 0 or 1. e, f, and g are each independently 0, 1, 2, 3, or 4, and the sum of e, f, and g is 1 or more. Preferred e, f, or g is 1 or 2.

Fifth, preferred component compounds are shown. A preferred orientation monomer will be described. The orientation monomer preferably has at least two polymerizable groups. In the case where there is one polymerizable group, the orientation control layer obtained after polymerization is considered to be a flexible film. Therefore, the orientation control layer is likely to be deformed in a temperature environment for driving the liquid crystal display element, and the orientation control power is also likely to be reduced. Become. In the case where there are at least two polymerizable groups, it is considered that the crosslink density of the orientation control layer obtained after polymerization is increased and a strong film is formed. Therefore, the orientation control layer is hardly deformed even in a high temperature environment. In the case where fluorine is contained in the polymerizable group, it is considered that the polymerization reactivity is also increased. Therefore, it is preferable when the mechanical strength of the orientation control layer obtained after polymerization is controlled. A site that causes dimerization or isomerization by polarized light is a vinylene group. Even in the case of having a chalcone structure or a cinnamate structure containing a vinylene group, the same effect is preferable. In order to control the solubility in the liquid crystal compound, a spacer may be introduced between the polymerizable group and the central structure in order to increase the compatibility with the terminal chain of the liquid crystal compound. The spacer is preferably linear or branched. The length of the spacer is preferably 2 or more carbon atoms. Two or more kinds of orientation monomers may be used in combination. Specific examples of preferred orientation monomers are given below. Compound (A-1-1) to Compound (A-1-8), Compound (AA-1) to Compound (AA-15), Compound (A-2-1) to Compound (A-2) -12), compound (B-1-1) to compound (B-1-17), compound (C-1-1) to compound (C-1-10) and compound (D-1-1) to compound (D-1-9). From compound (A-1-4) to compound (A-1-7), compound (AA-5), compound (AA-7), compound (A-2-1) to compound (A-2) -2), n in the compound (A-2-7) to the compound (A-2-12) is independently 2 to 12. From the viewpoint of improving the compatibility with the liquid crystal compound in the compound (A-2-1) to the compound (A-2-2) and the compound (A-2-7) to the compound (A-2-12), More preferably n is 2 to 10.
Other than the above, preferred orientation monomers having a cinnamate structure include compounds (I-1) to (I-34) and compounds (I-36) described in paragraphs 0029 to 0033 of JP2011-202168A. To Compound (I-39), Compound (I-1) to Compound (I-52), Compound (I-56) to Compound (I-59) described in JP-A 2010-285499, paragraphs 0031 to 0042. ), Compound (I-60) to compound (I-62).

  Desirable compound (1) is the compound (1-1) to the compound (1-22) according to item 6. In these compounds, at least one of the first components is compound (1-1), compound (1-3), compound (1-4), compound (1-6), compound (1-8), or compound (1-10) is preferred. At least two of the first components are compound (1-1) and compound (1-6), compound (1-1) and compound (1-10), compound (1-3) and compound (1-6), The compound (1-3) and the compound (1-10), the compound (1-4) and the compound (1-6), or a combination of the compound (1-4) and the compound (1-8) is preferable.

  Desirable compound (2) is the compound (2-1) to the compound (2-13) according to item 9. In these compounds, at least one of the second components is compound (2-1), compound (2-3), compound (2-5), compound (2-6), compound (2-8), or compound (2-9) is preferred. At least two of the second components are the compound (2-1) and the compound (2-3), the compound (2-1) and the compound (2-5), or the compound (2-1) and the compound (2-6). A combination is preferred.

  Desirable compound (3) is the compound (3-1) to the compound (3-27) according to item 13. In these compounds, at least one of the additives is compound (3-1), compound (3-2), compound (3-3), compound (3-18), compound (3-24), or compound ( 3-25) is preferred. At least two of the additives are compound (3-1) and compound (3-2), compound (3-1) and compound (3-18), compound (3-1) and compound (3-25), compound (3-2) and compound (3-25), compound (3-2) and compound (3-26), compound (3-18) and compound (3-24), or compound (3-25) and compound A combination of (3-26) is preferable.

  Sixth, additives that may be added to the composition will be described. Such additives are optically active compounds, antioxidants, ultraviolet absorbers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, polar compounds and the like. An optically active compound is added to the composition for the purpose of inducing a helical structure of liquid crystal molecules to give a twist angle. Examples of such compounds are compounds (4-1) to (4-5). A desirable ratio of the optically active compound is approximately 5 parts by weight or less. A more desirable ratio is in the range of approximately 0.01 parts by weight to approximately 2 parts by weight.

An antioxidant is used to prevent a decrease in specific resistance due to heating in the atmosphere, or to maintain a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature after using the device for a long time. Added to the product. A preferred example of the antioxidant is a compound (5) wherein n is an integer of 1 to 9.

  In the compound (5), preferable n is 1, 3, 5, 7, or 9. Further preferred n is 7. Since the compound (5) in which n is 7 has low volatility, it is effective for maintaining a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature after the device has been used for a long time. A desirable ratio of the antioxidant is approximately 50 ppm or more for achieving its effect, and is approximately 600 ppm or less for avoiding a decrease in the maximum temperature or avoiding an increase in the minimum temperature. A more desirable ratio is in the range of approximately 100 ppm to approximately 300 ppm.

  Preferred examples of the ultraviolet absorber include benzophenone derivatives, benzoate derivatives, triazole derivatives and the like. Also preferred are light stabilizers such as sterically hindered amines. A desirable ratio of these absorbers and stabilizers is approximately 50 ppm or more for achieving the effect thereof, and approximately 10,000 ppm or less for avoiding a decrease in the maximum temperature or avoiding an increase in the minimum temperature. A more desirable ratio is in the range of approximately 100 ppm to approximately 10,000 ppm.

  A dichroic dye such as an azo dye or an anthraquinone dye is added to the composition in order to adapt to a GH (guest host) mode device. A preferred ratio of the dye is in the range of approximately 0.01 part by weight to approximately 10 parts by weight. In order to prevent foaming, an antifoaming agent such as dimethyl silicone oil or methylphenyl silicone oil is added to the composition. A desirable ratio of the antifoaming agent is approximately 1 ppm or more for obtaining the effect thereof, and approximately 1000 ppm or less for preventing a display defect. A more desirable ratio is in the range of approximately 1 ppm to approximately 500 ppm.

  A polymerizable compound is used to adapt to a polymer support alignment (PSA) type device. Compound (3) is suitable for this purpose. A polymerizable compound different from the compound (3) may be added to the composition together with the compound (3). Instead of the compound (3), a polymerizable compound different from the compound (3) may be added to the composition. Preferable examples of such a polymerizable compound are compounds such as acrylate, methacrylate, vinyl compound, vinyloxy compound, propenyl ether, epoxy compound (oxirane, oxetane), vinyl ketone and the like. Further preferred examples are acrylate or methacrylate derivatives. The reactivity of the polymerizable compound and the pretilt angle of the liquid crystal molecules can be adjusted by changing the type of the compound (3) or combining a polymerizable compound different from the compound (3) in an appropriate ratio. . By optimizing the pretilt angle, a short response time of the element can be achieved. Since the alignment of the liquid crystal molecules is stabilized, a large contrast ratio and a long lifetime can be achieved.

  A polymerizable compound such as compound (3) or an orientation monomer is polymerized by irradiation with ultraviolet rays. The polymerization may be performed in the presence of a suitable initiator such as a photopolymerization initiator. Appropriate conditions for polymerization, the appropriate type of initiator, and the appropriate amount are known to those skilled in the art and are described in the literature. For example, Irgacure 651 (registered trademark; BASF), Irgacure 184 (registered trademark; BASF), or Darocur 1173 (registered trademark; BASF), which are photoinitiators, are suitable for radical polymerization. A desirable ratio of the photopolymerization initiator is in the range of approximately 0.1% by weight to approximately 5% by weight based on the total amount of the polymerizable compound. A more desirable ratio is in the range of approximately 1% by weight to approximately 3% by weight.

  When storing a polymerizable compound such as compound (3) or an orientation monomer, a polymerization inhibitor may be added to prevent polymerization. The polymerizable compound is usually added to the composition without removing the polymerization inhibitor. Examples of the polymerization inhibitor include hydroquinone, hydroquinone derivatives such as methylhydroquinone, 4-t-butylcatechol, 4-methoxyphenol, phenothiazine and the like.

A polar compound is an organic compound having polarity. Here, a compound having an ionic bond is not included. Atoms such as oxygen, sulfur, and nitrogen are more electrically negative and tend to have partial negative charges. Carbon and hydrogen tend to be neutral or have a partial positive charge. Polarity arises from the fact that partial charges are not evenly distributed among different types of atoms in a compound. For example, the polar compound has at least one of partial structures such as —OH, —COOH, —SH, —NH ₂ ,> NH, and> N—.

  Seventh, a method for synthesizing the component compounds will be described. These compounds can be synthesized by known methods. The synthesis method is illustrated. Compound (1-1) is synthesized by the method described in JP-T-2-503441. Compound (2-5) is synthesized by the method described in JP-A-57-165328. Compound (3-18) is synthesized by the method described in JP-A-7-101900. Antioxidants are commercially available. Compounds of formula (5) where n is 1 are available from Sigma-Aldrich Corporation. Compound (5) etc. in which n is 7 are synthesized by the method described in US Pat. No. 3,660,505. The orientation monomer having a vinylene group is synthesized by a method described in International Publication No. 2013/077343, International Publication No. 2002/048821, International Publication No. 2015/004947, or US 2013-0277609. An alignment monomer having an α-fluoroacrylate group is synthesized by the method described in JP-A-2005-112850.

  Compounds that have not been described as synthetic methods are Organic Syntheses (John Wiley & Sons, Inc.), Organic Reactions (Organic Reactions, John Wiley & Sons, Inc.), Comprehensive Organic Synthesis ( Comprehensive Organic Synthesis, Pergamon Press), New Experimental Chemistry Course (Maruzen), etc. The composition is prepared from the compound thus obtained by known methods. For example, the component compounds are mixed and dissolved in each other by heating.

  Eighth, the use of the composition will be described. Most compositions have a minimum temperature of about −10 ° C. or lower, a maximum temperature of about 70 ° C. or higher, and an optical anisotropy in the range of about 0.07 to about 0.20. A composition having an optical anisotropy in the range of about 0.08 to about 0.25 may be prepared by controlling the ratio of the component compounds or by mixing other liquid crystal compounds. Furthermore, compositions having optical anisotropy in the range of about 0.10 to about 0.30 may be prepared by this method. A device containing this composition has a large voltage holding ratio. This composition is suitable for an AM device. This composition is particularly suitable for a transmissive AM device. This composition can be used as a composition having a nematic phase, or can be used as an optically active composition by adding an optically active compound.

  This composition can be used for an AM device. Further, it can be used for PM elements. This composition can be used for an AM device and a PM device having modes such as PC, TN, STN, ECB, OCB, IPS, FFS, VA, and FPA. Use for an AM device having a VA, OCB, IPS mode or FFS mode is particularly preferable. In the AM device having the IPS mode or the FFS mode, when no voltage is applied, the alignment of the liquid crystal molecules may be parallel to the glass substrate or may be vertical. These elements may be reflective, transmissive, or transflective. Use in a transmissive element is preferred. It can also be used for an amorphous silicon-TFT device or a polycrystalline silicon-TFT device. It can also be used for an NCAP (nematic curvilinear aligned phase) type device produced by microencapsulating this composition, or a PD (polymer dispersed) type device in which a three-dimensional network polymer is formed in the composition.

  Ninth, a method for manufacturing an element will be described. The first is a step of adding an alignment monomer to the liquid crystal composition, and heating and dissolving the composition at a temperature higher than the upper limit temperature. The second is a step of injecting this composition into a liquid crystal display element. In this step, when the liquid crystal composition is heated and injected at a temperature higher than the upper limit temperature, the shear stress when the liquid crystal composition flows in the cell can be reduced, and the occurrence of alignment defects can be easily prevented. . The third is a step of irradiating linearly polarized ultraviolet light while heating the liquid crystal composition to a temperature higher than the upper limit temperature. The alignment monomer is dimerized or isomerized by linearly polarized ultraviolet rays, and polymerization proceeds at the same time. Since the polymer composed of the alignment monomer is arranged in a certain direction at the molecular level and fixed on the substrate, the thin film has a function as a liquid crystal alignment film. By this method, a liquid crystal display element having no alignment film such as polyimide can be manufactured.

  The invention is explained in more detail by means of examples. The invention is not limited by these examples. The present invention includes a mixture of the composition of Example 1 and the composition of Example 2. The invention also includes a mixture of at least two of the example compositions. The synthesized compound was identified by a method such as NMR analysis. The characteristics of the compound, composition and device were measured by the methods described below.

NMR analysis: For measurement, DRX-500 manufactured by Bruker BioSpin Corporation was used. ^In the measurement of ¹ H-NMR, the sample was dissolved in a deuterated solvent such as CDCl _3, and the measurement was performed at room temperature under conditions of 500 MHz and 16 integrations. Tetramethylsilane was used as an internal standard. ^{For 19} F-NMR measurement, CFCl ₃ was used as an internal standard, and the number of integrations was 24. In the description of the nuclear magnetic resonance spectrum, s is a singlet, d is a doublet, t is a triplet, q is a quartet, quint is a quintet, sex is a sextet, m is a multiplet, and br is broad.

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

  As a solvent for diluting the sample, chloroform, hexane or the like may be used. In order to separate the component compounds, the following capillary column may be used. HP-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm) manufactured by Agilent Technologies Inc., Rtx-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm) manufactured by Restek Corporation, BP-1 made by SGE International Pty. Ltd (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm). In order to prevent compound peaks from overlapping, a capillary column CBP1-M50-025 (length 50 m, inner diameter 0.25 mm, film thickness 0.25 μm) manufactured by Shimadzu Corporation may be used.

  The ratio of the liquid crystal compound contained in the composition may be calculated by the following method. A mixture of liquid crystal compounds is detected by a gas chromatograph (FID). The area ratio of peaks in the gas chromatogram corresponds to the ratio (weight ratio) of liquid crystal compounds. When the capillary column described above is used, the correction coefficient of each liquid crystal compound may be regarded as 1. Therefore, the ratio (% by weight) of the liquid crystal compound can be calculated from the peak area ratio.

  Measurement sample: When measuring the characteristics of the composition and the device, the composition was used as it was as a sample. When measuring the characteristics of the compound, a sample for measurement was prepared by mixing this compound (15% by weight) with mother liquid crystals (85% by weight). The characteristic value of the compound was calculated from the value obtained by the measurement by extrapolation. (Extrapolated value) = {(Measured value of sample) −0.85 × (Measured value of mother liquid crystal)} / 0.15. When the smectic phase (or crystal) is precipitated at 25 ° C. at this ratio, the ratio of the compound and the mother liquid crystal is 10% by weight: 90% by weight, 5% by weight: 95% by weight, 1% by weight: 99% by weight in this order. changed. By this extrapolation method, the maximum temperature, optical anisotropy, viscosity, and dielectric anisotropy values for the compound were determined.

The following mother liquid crystals were used. The ratio of the component compound is shown by weight%.

  Measuring method: The characteristics were measured by the following method. Many of these methods are modified by a method described in the JEITA standard (JEITA ED-2521B) established by the Japan Electronics and Information Technology Industries Association (JEITA), or a modification thereof. Was the way. No thin film transistor (TFT) was attached to the TN device used for the measurement.

(1) Maximum temperature of nematic phase (NI; ° C.): A sample was placed on a hot plate of a melting point measuring apparatus equipped with a polarizing microscope and heated at a rate of 1 ° C./min. The temperature was measured when a part of the sample changed from a nematic phase to an isotropic liquid. The upper limit temperature of the nematic phase may be abbreviated as “upper limit temperature”.

(2) Minimum Temperature of a Nematic Phase _{(T C;} ° C.): A sample having a nematic phase was put in a glass bottle, 0 ℃, -10 ℃, -20 ℃, -30 ℃, and -40 ℃ for 10 days in a freezer After storage, the liquid crystal phase was observed. For example, when the sample remained in the nematic phase at −20 ° C. and changed to a crystalline or smectic phase at −30 ° C., the _TC was described as <−20 ° C. The lower limit temperature of the nematic phase may be abbreviated as “lower limit temperature”.

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

(4) Viscosity (rotational viscosity; γ1; measured at 25 ° C .; mPa · s): The measurement was performed according to the method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). I followed. A sample was put in a VA device having a distance (cell gap) between two glass substrates of 20 μm. This element was applied stepwise in increments of 1 volt within a range of 39 to 50 volts. After no application for 0.2 seconds, the application was repeated under the condition of only one rectangular wave (rectangular pulse; 0.2 seconds) and no application (2 seconds). The peak current and peak time of the transient current generated by this application were measured. These measurements and M.I. The value of rotational viscosity was obtained from the paper by Imai et al., Calculation formula (8) on page 40. The dielectric anisotropy necessary for this calculation was measured in the item (6).

(5) Optical anisotropy (refractive index anisotropy; Δn; measured at 25 ° C.): Measurement was performed with an Abbe refractometer using a light having a wavelength of 589 nm and a polarizing plate attached to an eyepiece. After rubbing the surface of the main prism in one direction, the sample was dropped on the main prism. The refractive index n‖ was measured when the polarization direction was parallel to the rubbing direction. The refractive index n⊥ was measured when the polarization direction was perpendicular to the rubbing direction. The value of optical anisotropy was calculated from the equation: Δn = n∥−n⊥.

(6) Dielectric anisotropy (Δε; measured at 25 ° C.): The value of dielectric anisotropy was calculated from the equation: Δε = ε∥−ε⊥. The dielectric constants (ε‖ and ε⊥) were measured as follows.
1) Measurement of dielectric constant (ε‖): A solution of octadecyltriethoxysilane (0.16 mL) in ethanol (20 mL) was applied to a well-cleaned glass substrate. The glass substrate was rotated with a spinner and then heated at 150 ° C. for 1 hour. A sample was put in a VA device in which the distance between two glass substrates (cell gap) was 4 μm, and the device was sealed with an adhesive that was cured with ultraviolet rays. Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2 seconds, the dielectric constant (ε‖) in the major axis direction of the liquid crystal molecules was measured.

2) Measurement of dielectric constant (ε⊥): A polyimide solution was applied to a well-cleaned glass substrate. After baking this glass substrate, the obtained alignment film was rubbed. A sample was put in a TN device in which the distance between two glass substrates (cell gap) was 9 μm and the twist angle was 80 degrees. Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2 seconds, the dielectric constant (ε⊥) in the minor axis direction of the liquid crystal molecules was measured.

(7) Threshold voltage (Vth; measured at 25 ° C .; V): An LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source was a halogen lamp. A sample is placed in a normally black mode VA element in which the distance between two glass substrates (cell gap) is 4 μm and the rubbing direction is anti-parallel, and an adhesive that cures the element with ultraviolet rays is used. And sealed. The voltage (60 Hz, rectangular wave) applied to this element was increased stepwise from 0V to 20V by 0.02V. At this time, the device was irradiated with light from the vertical direction, and the amount of light transmitted through the device 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 minimum. The threshold voltage was expressed as a voltage when the transmittance reached 10%.

(8) Voltage holding ratio (VHR-1; measured at 25 ° C .;%): The TN device used for the measurement had a polyimide alignment film, and the distance between two glass substrates (cell gap) was 5 μm. . This element was sealed with an adhesive that was cured with ultraviolet rays after the sample was placed. The TN device was charged by applying a pulse voltage (60 microseconds at 5 V). The decaying voltage was measured for 16.7 milliseconds with a high-speed voltmeter, and the area A between the voltage curve and the horizontal axis in a unit cycle was determined. Area B was the area when it was not attenuated. The voltage holding ratio was expressed as a percentage of area A with respect to area B.

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

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

(11) Voltage holding ratio (VHR-4; measured at 25 ° C .;%): The TN device into which the sample was injected was heated in a thermostatic bath at 80 ° C. for 500 hours, and then the voltage holding ratio was measured and stability against heat. Evaluated. In the measurement of VHR-4, a decaying voltage was measured for 16.7 milliseconds. A composition having a large VHR-4 has a large stability to heat.

(12) Response time (τ; measured at 25 ° C .; ms): An LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for measurement. The light source was a halogen lamp. The low-pass filter was set to 5 kHz. A sample was put in a normally black mode VA device in which the distance between two glass substrates (cell gap) was 4 μm and the rubbing direction was anti-parallel. The device was sealed using an adhesive that was cured with ultraviolet light. A rectangular wave (60 Hz, 10 V, 0.5 seconds) was applied to this element. At this time, the device was irradiated with light from the vertical direction, and the amount of light transmitted through the device was measured. It was considered that the transmittance was 100% when the light amount was the maximum, and the transmittance was 0% when the light amount was the minimum. The response time was expressed as the time required to change the transmittance from 90% to 10% (fall time; millisecond).

(13) Specific resistance (ρ; measured at 25 ° C .; Ωcm): A sample (1.0 mL) was injected into a container equipped with electrodes. A DC voltage (10 V) was applied to the container, and the DC current after 10 seconds was measured. The specific resistance was calculated from the following equation. (Resistivity) = {(Voltage) × (Capacity of container)} / {(DC current) × (Dielectric constant of vacuum)}.

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

Example 1 of device Raw material A composition to which an alignment monomer was added was injected into an element having no alignment film. After irradiation with linearly polarized ultraviolet rays, the orientation of liquid crystal molecules in this device was confirmed. First, the raw materials will be explained. The raw material is a composition such as the composition (M1) to the composition (M22), and the alignment monomer is a compound (A-1-1), a compound (A-2-1-1), or a compound (A-2). 2-1), compound (A-2-3), compound (A-2-4), compound (AA-1), compound (AA-2), compound (AA-4) , Compound (AA-11), Compound (AA-13), Compound (AA-14), Compound (AA-15), Compound (B-1-1), Compound (C- 1-1), the compound (D-1-5), the compound (D-1-7), and the compound (D-1-8) were appropriately selected.
The composition is as follows.

[Composition (M1)]
3-HB (2F, 3F) -O2 (1-1) 10%
5-HB (2F, 3F) -O2 (1-1) 7%
2-BB (2F, 3F) -O2 (1-4) 7%
3-BB (2F, 3F) -O2 (1-4) 7%
3-B (2F, 3F) B (2F, 3F) -O2 (1-5) 3%
2-HHB (2F, 3F) -O2 (1-6) 5%
3-HHB (2F, 3F) -O2 (1-6) 10%
2-HBB (2F, 3F) -O2 (1-10) 8%
3-HBB (2F, 3F) -O2 (1-10) 10%
2-HH-3 (2-1) 14%
3-HB-O1 (2-2) 5%
3-HHB-1 (2-5) 3%
3-HHB-O1 (2-5) 3%
3-HHB-3 (2-5) 4%
2-BB (F) B-3 (2-8) 4%
NI = 73.2 ° C .; Tc <−20 ° C .; Δn = 0.113; Δε = −4.0; Vth = 2.18 V; η = 22.6 mPa · s.

[Composition (M2)]
3-HB (2F, 3F) -O4 (1-1) 6%
3-H2B (2F, 3F) -O2 (1-2) 8%
3-H1OB (2F, 3F) -O2 (1-3) 4%
3-BB (2F, 3F) -O2 (1-4) 7%
2-HHB (2F, 3F) -O2 (1-6) 7%
3-HHB (2F, 3F) -O2 (1-6) 7%
3-HH2B (2F, 3F) -O2 (1-7) 7%
5-HH2B (2F, 3F) -O2 (1-7) 4%
2-HBB (2F, 3F) -O2 (1-10) 5%
3-HBB (2F, 3F) -O2 (1-10) 5%
4-HBB (2F, 3F) -O2 (1-10) 6%
2-HH-3 (2-1) 12%
1-BB-5 (2-3) 12%
3-HHB-1 (2-5) 4%
3-HHB-O1 (2-5) 3%
3-HBB-2 (2-6) 3%
NI = 82.8 ° C .; Tc <−30 ° C .; Δn = 0.118; Δε = −4.4; Vth = 2.13 V; η = 22.5 mPa · s.

[Composition (M3)]
3-HB (2F, 3F) -O2 (1-1) 7%
5-HB (2F, 3F) -O2 (1-1) 7%
3-BB (2F, 3F) -O2 (1-4) 8%
3-HHB (2F, 3F) -O2 (1-6) 5%
5-HHB (2F, 3F) -O2 (1-6) 4%
3-HH1OB (2F, 3F) -O2 (1-8) 4%
2-BB (2F, 3F) B-3 (1-9) 5%
2-HBB (2F, 3F) -O2 (1-10) 3%
3-HBB (2F, 3F) -O2 (1-10) 8%
4-HBB (2F, 3F) -O2 (1-10) 5%
5-HBB (2F, 3F) -O2 (1-10) 8%
3-HH-V (2-1) 27%
3-HH-V1 (2-1) 6%
V-HHB-1 (2-5) 3%
NI = 78.1 ° C .; Tc <−30 ° C .; Δn = 0.107; Δε = −3.2; Vth = 2.02 V; η = 15.9 mPa · s.

[Composition (M4)]
3-HB (2F, 3F) -O2 (1-1) 10%
5-HB (2F, 3F) -O2 (1-1) 10%
3-H2B (2F, 3F) -O2 (1-2) 8%
5-H2B (2F, 3F) -O2 (1-2) 8%
2-HBB (2F, 3F) -O2 (1-10) 6%
3-HBB (2F, 3F) -O2 (1-10) 8%
4-HBB (2F, 3F) -O2 (1-10) 7%
5-HBB (2F, 3F) -O2 (1-10) 7%
3-HDhB (2F, 3F) -O2 (1-16) 5%
3-HH-4 (2-1) 14%
V-HHB-1 (2-5) 10%
3-HBB-2 (2-6) 7%
NI = 88.5 ° C .; Tc <−30 ° C .; Δn = 0.108; Δε = −3.8; Vth = 2.25 V; η = 24.6 mPa · s; VHR-1 = 99.1%; VHR -2 = 98.2%; VHR-3 = 97.8%.

[Composition (M5)]
3-HB (2F, 3F) -O2 (1-1) 7%
3-HB (2F, 3F) -O4 (1-1) 8%
3-H2B (2F, 3F) -O2 (1-2) 8%
3-BB (2F, 3F) -O2 (1-4) 10%
2-HHB (2F, 3F) -O2 (1-6) 4%
3-HHB (2F, 3F) -O2 (1-6) 7%
3-HHB (2F, 3F) -1 (1-6) 6%
2-HBB (2F, 3F) -O2 (1-10) 6%
3-HBB (2F, 3F) -O2 (1-10) 6%
4-HBB (2F, 3F) -O2 (1-10) 5%
5-HBB (2F, 3F) -O2 (1-10) 4%
3-HEB (2F, 3F) B (2F, 3F) -O2
(1-11) 3%
3-H1OCro (7F, 8F) -5 (1-14) 3%
3-HDhB (2F, 3F) -O2 (1-16) 5%
3-HH-O1 (2-1) 5%
1-BB-5 (2-3) 4%
V-HHB-1 (2-5) 4%
5-HB (F) BH-3 (2-12) 5%
NI = 81.1 ° C .; Tc <−30 ° C .; Δn = 0.119; Δε = −4.5; Vth = 1.69 V; η = 31.4 mPa · s.

[Composition (M6)]
3-HB (2F, 3F) -O4 (1-1) 15%
3-HBB (2F, 3F) -O2 (1-10) 8%
4-HBB (2F, 3F) -O2 (1-10) 5%
5-HBB (2F, 3F) -O2 (1-10) 7%
3-dhBB (2F, 3F) -O2 (1-17) 5%
3-chB (2F, 3F) -O2 (1-18) 7%
2-HchB (2F, 3F) -O2 (1-19) 8%
5-HH-V (2-1) 18%
7-HB-1 (2-2) 5%
V-HHB-1 (2-5) 7%
V2-HHB-1 (2-5) 7%
3-HBB (F) B-3 (2-13) 8%
NI = 98.8 ° C .; Tc <−30 ° C .; Δn = 0.111; Δε = −3.2; Vth = 2.47 V; η = 23.9 mPa · s.

[Composition (M7)]
3-H2B (2F, 3F) -O2 (1-2) 18%
5-H2B (2F, 3F) -O2 (1-2) 17%
3-HHB (2F, 3Cl) -O2 (1-12) 5%
3-HBB (2F, 3Cl) -O2 (1-13) 8%
5-HBB (2F, 3Cl) -O2 (1-13) 7%
3-HDhB (2F, 3F) -O2 (1-16) 5%
3-HH-V (2-1) 11%
3-HH-VFF (2-1) 7%
F3-HH-V (2-1) 10%
3-HHEH-3 (2-4) 4%
3-HB (F) HH-2 (2-10) 4%
3-HHEBH-3 (2-11) 4%
NI = 77.5 ° C .; Tc <−30 ° C .; Δn = 0.084; Δε = −2.6; Vth = 2.43 V; η = 22.8 mPa · s.

[Composition (M8)]
3-HB (2F, 3F) -O2 (1-1) 8%
3-H2B (2F, 3F) -O2 (1-2) 10%
3-BB (2F, 3F) -O2 (1-4) 10%
2O-BB (2F, 3F) -O2 (1-4) 3%
2-HHB (2F, 3F) -O2 (1-6) 4%
3-HHB (2F, 3F) -O2 (1-6) 7%
2-HHB (2F, 3F) -1 (1-6) 5%
2-BB (2F, 3F) B-3 (1-9) 6%
2-BB (2F, 3F) B-4 (1-9) 6%
2-HBB (2F, 3F) -O2 (1-10) 4%
3-HBB (2F, 3F) -O2 (1-10) 7%
3-HH1OCro (7F, 8F) -5 (1-15) 4%
3-HDhB (2F, 3F) -O2 (1-16) 6%
3-dhBB (2F, 3F) -O2 (1-17) 4%
3-HH-V (2-1) 11%
1-BB-5 (2-3) 5%
NI = 70.6 ° C .; Tc <−20 ° C .; Δn = 0.129; Δε = −4.3; Vth = 1.69 V; η = 27.0 mPa · s.

[Composition (M9)]
3-HB (2F, 3F) -O4 (1-1) 14%
3-H1OB (2F, 3F) -O2 (1-3) 3%
3-BB (2F, 3F) -O2 (1-4) 10%
2-HHB (2F, 3F) -O2 (1-6) 7%
3-HHB (2F, 3F) -O2 (1-6) 7%
3-HH1OB (2F, 3F) -O2 (1-8) 6%
2-HBB (2F, 3F) -O2 (1-10) 4%
3-HBB (2F, 3F) -O2 (1-10) 6%
4-HBB (2F, 3F) -O2 (1-10) 4%
3-HH-V (2-1) 14%
1-BB-3 (2-3) 3%
3-HHB-1 (2-5) 4%
3-HHB-O1 (2-5) 4%
V-HBB-2 (2-6) 4%
1-BB (F) B-2V (2-8) 6%
5-HBBH-1O1 (-) 4%
NI = 93.0 ° C .; Tc <−30 ° C .; Δn = 0.123; Δε = −4.0; Vth = 2.27 V; η = 29.6 mPa · s.

[Composition (M10)]
3-HB (2F, 3F) -O4 (1-1) 6%
3-H2B (2F, 3F) -O2 (1-2) 8%
3-H1OB (2F, 3F) -O2 (1-3) 5%
3-BB (2F, 3F) -O2 (1-4) 10%
2-HHB (2F, 3F) -O2 (1-6) 7%
3-HHB (2F, 3F) -O2 (1-6) 7%
5-HHB (2F, 3F) -O2 (1-6) 7%
2-HBB (2F, 3F) -O2 (1-10) 4%
3-HBB (2F, 3F) -O2 (1-10) 7%
5-HBB (2F, 3F) -O2 (1-10) 6%
3-HH-V (2-1) 11%
1-BB-3 (2-3) 6%
3-HHB-1 (2-5) 4%
3-HHB-O1 (2-5) 4%
3-HBB-2 (2-6) 4%
3-B (F) BB-2 (2-7) 4%
NI = 87.6 ° C .; Tc <−30 ° C .; Δn = 0.126; Δε = −4.5; Vth = 2.21 V; η = 25.3 mPa · s.

[Composition (M11)]
3-HB (2F, 3F) -O4 (1-1) 6%
3-H2B (2F, 3F) -O2 (1-2) 8%
3-H1OB (2F, 3F) -O2 (1-3) 4%
3-BB (2F, 3F) -O2 (1-4) 7%
2-HHB (2F, 3F) -O2 (1-6) 6%
3-HHB (2F, 3F) -O2 (1-6) 10%
5-HHB (2F, 3F) -O2 (1-6) 8%
2-HBB (2F, 3F) -O2 (1-10) 5%
3-HBB (2F, 3F) -O2 (1-10) 7%
5-HBB (2F, 3F) -O2 (1-10) 5%
2-HH-3 (2-1) 12%
1-BB-3 (2-3) 6%
3-HHB-1 (2-5) 3%
3-HHB-O1 (2-5) 4%
3-HBB-2 (2-6) 6%
3-B (F) BB-2 (2-7) 3%
NI = 93.0 ° C .; Tc <−20 ° C .; Δn = 0.124; Δε = −4.5; Vth = 2.22 V; η = 25.0 mPa · s.

[Composition (M12)]
3-HB (2F, 3F) -O2 (1-1) 7%
5-HB (2F, 3F) -O2 (1-1) 7%
3-BB (2F, 3F) -O2 (1-4) 8%
3-HHB (2F, 3F) -O2 (1-6) 4%
5-HHB (2F, 3F) -O2 (1-6) 5%
3-HH1OB (2F, 3F) -O2 (1-8) 5%
2-BB (2F, 3F) B-3 (1-9) 4%
2-HBB (2F, 3F) -O2 (1-10) 3%
3-HBB (2F, 3F) -O2 (1-10) 8%
4-HBB (2F, 3F) -O2 (1-10) 5%
5-HBB (2F, 3F) -O2 (1-10) 8%
3-HH-V (2-1) 33%
V-HHB-1 (2-5) 3%
NI = 76.4 ° C .; Tc <−30 ° C .; Δn = 0.104; Δε = −3.2; Vth = 2.06 V; η = 15.6 mPa · s.

[Composition (M13)]
2-H1OB (2F, 3F) -O2 (1-3) 6%
3-H1OB (2F, 3F) -O2 (1-3) 4%
3-BB (2F, 3F) -O2 (1-4) 3%
2-HH1OB (2F, 3F) -O2 (1-8) 14%
2-HBB (2F, 3F) -O2 (1-10) 7%
3-HBB (2F, 3F) -O2 (1-10) 11%
5-HBB (2F, 3F) -O2 (1-10) 9%
2-HH-3 (2-1) 5%
3-HH-VFF (2-1) 30%
1-BB-3 (2-3) 5%
3-HHB-1 (2-5) 3%
3-HBB-2 (2-6) 3%
NI = 78.3 ° C .; Tc <−20 ° C .; Δn = 0.103; Δε = −3.2; Vth = 2.17 V; η = 17.7 mPa · s.

[Composition (M14)]
3-HB (2F, 3F) -O2 (1-1) 5%
5-HB (2F, 3F) -O2 (1-1) 7%
3-BB (2F, 3F) -O2 (1-4) 8%
3-HHB (2F, 3F) -O2 (1-6) 5%
5-HHB (2F, 3F) -O2 (1-6) 4%
3-HH1OB (2F, 3F) -O2 (1-8) 5%
2-BB (2F, 3F) B-3 (1-9) 4%
2-HBB (2F, 3F) -O2 (1-10) 3%
3-HBB (2F, 3F) -O2 (1-10) 9%
4-HBB (2F, 3F) -O2 (1-10) 4%
5-HBB (2F, 3F) -O2 (1-10) 8%
3-HH-V (2-1) 27%
3-HH-V1 (2-1) 6%
V-HHB-1 (2-5) 5%
NI = 81.2 ° C .; Tc <−20 ° C .; Δn = 0.107; Δε = −3.2; Vth = 2.11 V; η = 15.5 mPa · s.

[Composition (M15)]
3-H2B (2F, 3F) -O2 (1-2) 7%
3-HHB (2F, 3F) -O2 (1-6) 8%
3-HH1OB (2F, 3F) -O2 (1-8) 5%
2-BB (2F, 3F) B-3 (1-9) 7%
2-BB (2F, 3F) B-4 (1-9) 7%
3-HDhB (2F, 3F) -O2 (1-16) 3%
5-HDhB (2F, 3F) -O2 (1-16) 4%
2-HchB (2F, 3F) -O2 (1-19) 8%
4-HH-V (2-1) 15%
3-HH-V1 (2-1) 6%
1-HH-2V1 (2-1) 6%
3-HH-2V1 (2-1) 4%
V2-BB-1 (2-3) 5%
1V2-BB-1 (2-3) 5%
3-HHB-1 (2-5) 6%
3-HB (F) BH-3 (2-12) 4%
NI = 88.7 ° C .; Tc <−30 ° C .; Δn = 0.115; Δε = −1.9; Vth = 2.82 V; η = 17.3 mPa · s.

[Composition (M16)]
V2-H2B (2F, 3F) -O2 (1-2) 8%
V2-H1OB (2F, 3F) -O4 (1-3) 4%
3-BB (2F, 3F) -O2 (1-4) 7%
2-HHB (2F, 3F) -O2 (1-6) 7%
3-HHB (2F, 3F) -O2 (1-6) 7%
3-HH2B (2F, 3F) -O2 (1-7) 7%
5-HH2B (2F, 3F) -O2 (1-7) 4%
V-HH2B (2F, 3F) -O2 (1-7) 6%
V2-HBB (2F, 3F) -O2 (1-10) 5%
V-HBB (2F, 3F) -O2 (1-10) 5%
V-HBB (2F, 3F) -O4 (1-10) 6%
2-HH-3 (2-1) 12%
1-BB-5 (2-3) 12%
3-HHB-1 (2-5) 4%
3-HHB-O1 (2-5) 3%
3-HBB-2 (2-6) 3%
NI = 89.9 ° C .; Tc <−20 ° C .; Δn = 0.122; Δε = −4.2; Vth = 2.16 V; η = 23.4 mPa · s.

[Composition (M17)]
3-HB (2F, 3F) -O2 (1-1) 3%
V-HB (2F, 3F) -O2 (1-1) 3%
V2-HB (2F, 3F) -O2 (1-1) 5%
5-H2B (2F, 3F) -O2 (1-2) 5%
V2-BB (2F, 3F) -O2 (1-4) 3%
1V2-BB (2F, 3F) -O2 (1-4) 3%
3-HHB (2F, 3F) -O2 (1-6) 6%
V-HHB (2F, 3F) -O2 (1-6) 6%
V-HHB (2F, 3F) -O4 (1-6) 5%
V2-HHB (2F, 3F) -O2 (1-6) 4%
V2-BB (2F, 3F) B-1 (1-9) 4%
V2-HBB (2F, 3F) -O2 (1-10) 5%
V-HBB (2F, 3F) -O2 (1-10) 4%
V-HBB (2F, 3F) -O4 (1-10) 5%
V-HHB (2F, 3Cl) -O2 (1-12) 3%
3-HH-V (2-1) 27%
3-HH-V1 (2-1) 6%
V-HHB-1 (2-5) 3%
NI = 77.1 ° C .; Tc <−20 ° C .; Δn = 0.101; Δε = −3.0; Vth = 2.04 V; η = 13.9 mPa · s.

[Composition (M18)]
V-HB (2F, 3F) -O2 (1-1) 10%
V2-HB (2F, 3F) -O2 (1-1) 10%
2-H1OB (2F, 3F) -O2 (1-3) 3%
3-H1OB (2F, 3F) -O2 (1-3) 3%
2O-BB (2F, 3F) -O2 (1-4) 3%
V2-BB (2F, 3F) -O2 (1-4) 8%
V2-HHB (2F, 3F) -O2 (1-6) 5%
2-HBB (2F, 3F) -O2 (1-10) 3%
3-HBB (2F, 3F) -O2 (1-10) 3%
V-HBB (2F, 3F) -O2 (1-10) 6%
V-HBB (2F, 3F) -O4 (1-10) 8%
V-HHB (2F, 3Cl) -O2 (1-12) 7%
3-HH-4 (2-1) 14%
V-HHB-1 (2-5) 10%
3-HBB-2 (2-6) 7%
NI = 75.9 ° C .; Tc <−20 ° C .; Δn = 0.114; Δε = −3.9; Vth = 2.20 V; η = 24.7 mPa · s.

[Composition (M19)]
3-HB (2F, 3F) -O2 (1-1) 12%
2-HH1OB (2F, 3F) -O2 (1-8) 10%
3-HH1OB (2F, 3F) -O2 (1-8) 9%
2O-B (2F) B (2F, 3F) -O2 (1-22) 4%
2O-B (2F) B (2F, 3F) -O4 (1-22) 5%
2-HH-3 (2-1) 25%
3-HH-4 (2-1) 6%
1-BB-3 (2-3) 4%
3-HHB-1 (2-5) 9%
3-HBB-2 (2-6) 7%
5-B (F) BB-2 (2-7) 9%
NI = 74.2 ° C .; Tc <−20 ° C .; Δn = 0.103; Δε = −2.5; Vth = 2.36 V; η = 18.4 mPa · s.

[Composition (M20)]
3-H1OB (2F, 3F) -O2 (1-3) 10%
V-HHB (2F, 3F) -O2 (1-6) 5%
2-HH1OB (2F, 3F) -O2 (1-8) 4%
3-HBB (2F, 3F) -O2 (1-10) 5%
V-HBB (2F, 3F) -O2 (1-10) 9%
2O-B (2F) B (2F, 3F) -O2 (1-22) 5%
2O-B (2F) B (2F, 3F) -O4 (1-22) 5%
2-HH-3 (2-1) 22%
3-HH-4 (1-1) 5%
3-HH-5 (1-1) 3%
3-HB-O2 (1-2) 10%
3-HHB-1 (1-5) 8%
3-HHB-3 (1-5) 4%
5-B (F) BB-2 (1-7) 5%
NI = 74.9 ° C .; Tc <−20 ° C .; Δn = 0.102; Δε = −2.8; Vth = 2.30 V; η = 19.2 mPa · s.

[Composition (M21)]
3-HB (2F, 3F) -O2 (1-1) 12%
5-HB (2F, 3F) -O2 (1-1) 8%
3-HH2B (2F, 3F) -O2 (1-7) 9%
3-HDhB (2F, 3F) -O2 (1-16) 9%
3-dhBB (2F, 3F) -O2 (1-17) 7%
2O-B (2F) B (2F, 3F) -O2 (1-22) 5%
3-HH-V (2-1) 29%
2-HH-3 (2-1) 2%
V-HHB-1 (2-5) 5%
V-HBB-2 (2-6) 14%
NI = 76.5 ° C .; Tc <−20 ° C .; Δn = 0.098; Δε = −3.0; Vth = 2.15 V; η = 16.2 mPa · s.

[Composition (M22)]
2-HHB (2F, 3F) -O2 (1-6) 3%
3-HHB (2F, 3F) -O2 (1-6) 6%
V-HHB (2F, 3F) -O1 (1-6) 4%
V-HHB (2F, 3F) -O2 (1-6) 10%
3-HH2B (2F, 3F) -O2 (1-7) 9%
2O-B (2F) B (2F, 3F) -O2 (1-22) 7%
2O-B (2F) B (2F, 3F) -O4 (1-22) 7%
3-HH-V (2-1) 20%
2-HH-3 (2-1) 10%
3-HH-4 (2-1) 6%
3-HB-O2 (2-2) 7%
1-BB-3 (2-3) 4%
5-B (F) BB-2 (2-7) 7%
NI = 75.3 ° C .; Tc <−20 ° C .; Δn = 0.102; Δε = −2.6; Vth = 2.41 V; η = 17.5 mPa · s.

The first additive is the following compound.

2. Alignment evaluation of liquid crystal molecules <Polarized exposure conditions>
Ultra-high pressure mercury lamp of 250W using (Ushio multiwrite Co., Ltd.) and a wire grid polarizer (Moxtek Inc. ProFlux (UVT-260A)), 3mW / cm 2 ( illuminance Ushio Co. ultraviolet irradiance wavelength 313nm (Measured using a total of UIT-150 and UVD-S313).

Example 1
The orientation monomer (A-1-1) was added to the composition (M1) at a ratio of 0.3 part by weight. This mixture was injected into an IPS device having no alignment film at 90 ° C. (above the upper limit temperature). While heating the IPS element at 90 ° C. (above the upper limit temperature), the element was irradiated with ultraviolet light (313 nm, 5.0 J / cm ² ) linearly polarized from the normal direction to form an element on which the orientation control layer was formed. Obtained. The irradiated ultraviolet rays are linearly polarized by passing through a polarizer. Next, the element on which the alignment control layer was formed was set on a polarizing microscope, and the alignment state of the liquid crystal was observed. The polarizer and analyzer of the polarizing microscope were arranged so that their transmission axes were orthogonal to each other. First, the alignment direction of the liquid crystal molecules and the transmission axis of the polarizer of the polarizing microscope are parallel, that is, the angle formed by the alignment direction of the liquid crystal molecules and the transmission axis of the polarizer of the polarization microscope is 0 degree. The device was placed on a horizontal rotation stage of a polarizing microscope. Light was irradiated from the lower side of the element, that is, from the polarizer side, and the presence or absence of light passing through the analyzer was observed. Since no light transmitted through the analyzer was observed, the orientation was determined to be “good”. In addition, when the light which permeate | transmits an analyzer was observed in the same observation, it determined with orientation being "bad". Next, the element was rotated on the horizontal rotation stage of the polarizing microscope, and the angle formed by the transmission axis of the polarizer of the polarizing microscope and the alignment direction of the liquid crystal molecules was changed from 0 degree. The intensity of the light transmitted through the analyzer increases as the angle formed by the transmission axis of the polarizer of the polarizing microscope and the alignment direction of the liquid crystal molecules increases, and is almost maximized when the angle is 45 degrees. confirmed. In the device obtained as described above, the liquid crystal molecules were aligned in a substantially horizontal direction with respect to the main surface of the substrate of the device, and determined to be “horizontal alignment”.

Examples 2 to 9
The compound (A-1-1) or the compound (B-1-1) was added from the composition (M2) to the composition (M9). Using this mixture, an element was prepared in the same manner as in Example 1 except that the liquid crystal injection temperature and the polarization exposure temperature were set to the temperatures shown in Table 4, and the same method as in Example 1 was used. The presence or absence of light leakage was observed.

Example 10
The compound (C-1-1) was added to the composition (M10) at a ratio of 1 part by weight. This mixture was injected at 95 ° C. (above the upper limit temperature) into an IPS device having no alignment film. The device was irradiated with linearly polarized light (313 nm, 2.0 J / cm ² ) from the normal direction at 100 ° C. (above the upper limit temperature). The presence or absence of light leakage was observed in the same manner as in Example 1.

Examples 11 to 18
The compound (C-1-1) or the compound (D-1-5) was added from the composition (M11) to the composition (M18). Using this mixture, an element was produced in the same manner as in Example 10 except that the liquid crystal injection temperature and the polarization exposure temperature were set to the temperatures shown in Table 4, and the same method as in Example 1 was used. The presence or absence of light leakage was observed.

Examples 19 to 22
Compound (A-1-1), compound (B-1-1), compound (C-1-1) or compound (D-1-5) is added from composition (M19) to composition (M22). did. Using this mixture, an element was prepared in the same manner as in Example 1 except that the liquid crystal injection temperature and the polarization exposure temperature were set to the temperatures shown in Table 4, and the same method as in Example 1 was used. The presence or absence of light leakage was observed.

Examples 23 to 27
The compound (AA-1), the compound (AA-2) or the compound (AA-11) was added from the composition (M1) to the composition (M3). Using this mixture, an element was prepared in the same manner as in Example 1 except that the liquid crystal injection temperature and the polarization exposure temperature were set to the temperatures shown in Table 4, and the same method as in Example 1 was used. The presence or absence of light leakage was observed.

Comparative Example 1
Except not adding an orientation monomer to a composition (M1), it injected into the IPS element which does not have an orientation film by the method similar to Example 1, and performed the heating polarization exposure process. The presence or absence of light leakage was observed in the same manner as in Example 1. The results of Examples 1 to 26 and Comparative Example 1 are summarized in Table 4.

Table 4. Alignment of liquid crystal molecules

Comparative Example 2
In the composition (M1), the following compound (R-1) having no polymerizable group but having a vinylene moiety was added and injected into an IPS device having no alignment film in the same manner as in Example 1. A heated polarized light exposure treatment was performed. The alignment state of the liquid crystal was observed in the same manner as in Example 1. A region in which light did not pass through the analyzer was confirmed in the device, but a region in which light passed through the analyzer was also confirmed. The orientation was determined to be poor overall.

3. Compatibility of alignment monomer and liquid crystal composition Stability at room temperature of the mixture of liquid crystal composition and alignment monomer obtained in the above examples and the mixture of liquid crystal composition and polymerizable compound obtained in the above comparative examples Was evaluated. After mixing, the liquid was changed to an isotropic liquid at 100 ° C. and allowed to cool to 25 ° C. When the presence or absence of precipitation was confirmed after half a day at room temperature, no precipitation was confirmed in the mixtures of Examples 1 to 27 and Comparative Example 2, and the compatibility of any of the orientation monomers was good.

As can be seen from Table 4, in Examples 1 to 27, the type of the composition and the orientation monomer was changed, but no light leakage was observed. The same tendency was observed when a plurality of orientation monomers were used. This result shows that the alignment is good even if the device does not have an alignment film such as polyimide, and all the liquid crystal molecules are aligned in a certain direction. On the other hand, light leakage was observed in Comparative Example 1 containing no alignment monomer. Moreover, sufficient orientation is not acquired with the orientation control layer forming compound which does not have a polymeric group.
From the above results, it can be seen that a thin film formed from an alignment monomer having two or more polymerizable groups plays an important role in uniform alignment of liquid crystal molecules. It can also be seen that the compatibility with the liquid crystal composition is also good.
Similar effects can be obtained by using other orientation monomers (for example, compound (A-2-1-1), compound (A-2-2-1), compound (A-2-3), compound (A-2-1)). 4), Compound (D-1-7), Compound (D-1-8), Compound (AA-4), Compound (AA-13), Compound (AA-14), Compound ( Even in the case of AA-15)), it can be expected.
Therefore, by using the liquid crystal composition of the present invention, a liquid crystal display device having characteristics such as a wide temperature range in which the device can be used, a short response time, a high voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long lifetime. Can also be expected.
In addition, the high maximum temperature of the nematic phase, the low minimum temperature of the nematic phase, small viscosity, suitable optical anisotropy, negatively large dielectric anisotropy, large specific resistance, high stability against ultraviolet rays, high stability against heat It can be expected that a liquid crystal display element having a liquid crystal composition satisfying at least one of the above characteristics can be obtained.

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

Claims (23)

A liquid crystal layer is sandwiched between a pair of substrates that are arranged facing each other and bonded together via a sealant,
Between the pair of substrates and the liquid crystal layer, an alignment control layer for controlling alignment of liquid crystal molecules,
The liquid crystal layer is made of a liquid crystal composition having negative dielectric anisotropy,
The liquid crystal composition contains at least one compound selected from the group of compounds represented by formulas (A) to (D) as an alignment monomer as a first additive, and a liquid crystal compound,
The said alignment control layer is a liquid crystal display element which consists of a polymer produced | generated by polymerizing the said orientation monomer.

In formulas (A) to (D), P ¹⁰ , P ²⁰ , P ³⁰ and P ⁴⁰ are each independently a group selected from the groups represented by formula (Q-1) to formula (Q-5) Is;

In formulas (Q-1) to (Q-5), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or at least one hydrogen is fluorine or chlorine 1 to 5 carbon alkyls replaced by
Sp ¹⁰ , Sp ²⁰ , and Sp ⁴⁰ are each independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene is replaced by fluorine, chlorine or the formula (Q-6) And at least one —CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—, and at least one —CH ₂ CH ₂ — may be —CH═CH—. May be replaced by;
Sp ³⁰ is independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine, chlorine or formula (Q-6), and at least one — CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—;

In Formula (Q-6), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or 1 carbon in which at least one hydrogen is replaced by fluorine or chlorine. To alkyl of 5;
Sp ⁴¹ is independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or chlorine, and at least one —CH ₂ — is —O ₂ May be replaced by-, -CO-, -COO-, or -OCO-;
Ring A ¹⁰ and Ring A ²⁰ are independently phenyl, 4-biphenyl, 1-naphthyl, 2-naphthyl, pyrimidin-2-yl, pyrimidin-5-yl, pyridin-2-yl, pyridin-5-yl, Fluoren-2-yl, fluoren-3-yl, phenanthren-2-yl, anthracen-2-yl, and in these rings, at least one hydrogen is fluorine, chlorine, alkyl having 1 to 12 carbons, carbon May be replaced by alkenyl having 2 to 12 carbon atoms, alkoxy having 1 to 11 carbon atoms, or alkenyloxy having 2 to 11 carbon atoms, and in these groups, at least one hydrogen may be replaced by fluorine or chlorine. Often;
Ring A ¹¹ , Ring A ²¹ , Ring A ¹² , Ring A ²² and Ring A ³⁰ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 4,4 ′. -Biphenylene, 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, per Hydrocyclopenta [a] phenanthrene-3,17-diyl or 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclo Is a pointer [a] phenanthrene-3,17-diyl, adjacent ^{bond, -CH = CH -, - CR} 10 = CR 20 -, - CO-CH = CH -, - CH = CH-CO-, —OCO—CH═CH—, or —CH═CH—COO—, wherein R ¹⁰ and R ²⁰ are independently hydrogen, fluorine, cyano, alkyl having 1 to 10 carbons, or at least one hydrogen is fluorine. 1, 4-phenylene, 4,4′-biphenylene, 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 which at least one hydrogen is fluorine, chlorine, Alkyl having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkoxy having 1 to 11 carbon atoms, or alkenyloxy having 2 to 11 carbon atoms may be substituted, and in these groups, at least one hydrogen is May be replaced by fluorine or chlorine;
Ring A ⁴⁰ includes 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 4,4′-biphenylene, 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, or 2,3 4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta [a] phenanthrene-3,17-diyl, but next When the bond to be —CH═CH—, —CO—CH═CH—, —CH═CH—CO—, —OCO—CH═CH—, or —CH═CH—COO— is 1, 4 -Phenylene, 4,4'-biphenylene, naphthalene-2,6-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, and in these rings, at least one of ^hydrogen, P 20 ^{-Sp 20} -, fluorine, chlorine, alkyl of from 1 to 12 carbons, alkenyl having 2 to 12 carbons, carbon atoms May be substituted with 1 to 11 alkoxy, or alkenyloxy with 2 to 11 carbons, in which at least one hydrogen is replaced with fluorine or chlorine It may be;
Z ¹⁰ is independently —CH═CH—, —CR ¹⁰ = CR ²⁰ —, —CO—CH═CH—, —CH═CH—CO—, —OCO—CH═CH—, or —CH═CH. -COO- and R ¹⁰ and R ²⁰ are independently hydrogen, fluorine, cyano, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine. ;
Z ¹¹ is independently a single bond or an alkylene having 1 to 6 carbon atoms, in which at least one —CH ₂ — is —O—, —CO—, —COO—, —OCO—, or may be replaced by -OCOO-, at least one - _{(CH 2) 2} - may be replaced by -CH = CH- or -C≡C-, and in the groups, at least one hydrogen May be replaced by fluorine or chlorine;
Z ²⁰ and Z ²¹ are independently a single bond, alkylene having 1 to 6 carbons or alkenylene having 2 to 6 carbons, but at least one is alkenylene having 2 to 6 carbons. In these alkylene and alkenylene, at least one —CH ₂ — may be replaced by —O—, —CO—, —COO—, —OCO—, or —OCOO—, and at least one other — ( CH ₂ ) ₂ — may be replaced by —CH═CH— or —C≡C—, in which at least one hydrogen may be replaced by fluorine or chlorine;
k ¹⁰ and n ¹⁰ are each independently an integer from 0 to 3, and the sum of k ¹⁰ and n ¹⁰ is an integer from 1 to 6;
n ²⁰ is 1 or 2;
n ³⁰ is 1 or 2. The alignment monomer in the liquid crystal composition is represented by formula (A-1), formula (A-2), formula (B-1), formula (C-1), and formula (D-1). The liquid crystal display element as described.

In Formula (A-1), Formula (A-2), Formula (B-1), Formula (C-1), and Formula (D-1), P ¹⁰ , P ²⁰ , P ³⁰ , P ⁴⁰ , P ⁵⁰ And P ⁶⁰ is independently a group selected from the groups represented by formula (Q-1);
In formula (Q-1), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, methyl, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine;
Sp ¹⁰ , Sp ²⁰ , and Sp ⁴⁰ are each independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or formula (Q-6) , At least one —CH ₂ — may be replaced with —O—, —CO—, —COO—, or —OCO—, and at least one —CH ₂ CH ₂ — is replaced with —CH═CH—. May be
Sp ³⁰ is independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine, chlorine or formula (Q-6), and at least one — CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—;
In formula (Q-6), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, methyl, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine;
Sp ⁴¹ is independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or chlorine, and at least one —CH ₂ — is —O ₂ May be replaced by-, -CO-, -COO-, or -OCO-;
Sp ⁵⁰ and Sp ⁶⁰ are independently alkylene having 2 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine, chlorine or formula (Q-6), and at least one — CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—;
R ¹⁰ and R ²⁰ are independently hydrogen, fluorine, cyano, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine;
R ³⁰ , R ⁴⁰ , R ⁴¹ and R ⁵⁰ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine. ;
Ring A ¹¹ and Ring A ²¹ are independently 1,4-phenylene, naphthalene-2,6-diyl, in which at least one hydrogen is fluorine, chlorine, alkyl having 1 to 12 carbons, or at least One hydrogen may be replaced by alkyl of 1 to 12 carbons replaced by fluorine;
Z ¹¹ is a single bond, ethylene, methyleneoxy, —COO—, —OCO—, —OCOO—, or —CH═CH—COO—;
Z ¹² is —CO— or —OCO—;
k ¹⁰ and n ¹⁰ are each independently an integer from 0 to 3, and the sum of k ¹⁰ and n ¹⁰ is an integer from 1 to 4;
n ²⁰ is 1 or 2;
n ³⁰ is 1 or 2;
Z ²⁰ and Z ²¹ independently represent a single bond, —CO—CH═CH—, —CH═CH—CO—, —OCO—CH═CH—, —CH═CH—COO— or —CH═CH—. However, it does not become a single bond at the same time. The alignment monomer in the liquid crystal composition is formula (A-1), formula (A-2), or formula (B-1), and P ¹⁰ , P ²⁰ , P ³⁰ , P ⁴⁰ , P ^50, and P ⁶⁰ are Independently a group selected from the groups represented by formula (Q-1);
In formula (Q-1), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, methyl, or trifluoromethyl;
Sp ¹⁰ and Sp ²⁰ are independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or formula (Q-6), and at least one of —CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—;
In formula (Q-6), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, methyl, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine;
Sp ⁴¹ is independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or chlorine, and at least one —CH ₂ — is —O ₂ May be replaced by-, -CO-, -COO-, or -OCO-;
Sp ³⁰ is a single bond or alkylene having 1 to 12 carbon atoms, and at least one hydrogen of the alkylene may be replaced by fluorine, and at least one —CH ₂ — may be —O—, —CO—, May be replaced by -COO-, or -OCO-;
Sp ⁴⁰ is a single bond;
Sp ⁵⁰ and Sp ⁶⁰ are independently alkylene having 2 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine, chlorine or formula (Q-6), and at least one — CH ₂ — may be replaced by —O—, —CO—, —COO—, or —OCO—;
R ¹⁰ and R ²⁰ are independently hydrogen, fluorine, cyano, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine;
R ³⁰ , R ⁴⁰ and R ⁵⁰ are independently hydrogen, fluorine, chlorine, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine;
Ring A ¹¹ and Ring A ²¹ are independently 1,4-phenylene, naphthalene-2,6-diyl, in which at least one hydrogen may be replaced by fluorine, methyl, ethyl or trifluoromethyl. Often;
Z ¹¹ is a single bond, —COO— or —OCO—;
Z ¹² is —CO— or —OCO—;
k ¹⁰ and n ¹⁰ are each independently an integer from 0 to 3, and the sum of k ¹⁰ and n ¹⁰ is an integer from 1 to 4;
n ²⁰ is 1 or 2;
n ³⁰ is 1 or 2,
The liquid crystal display element according to claim 2.   The ratio of the alignment monomer in the liquid crystal composition is in the range of 0.1 to 10 parts by weight when the total amount of liquid crystal compounds is 100 parts by weight. The liquid crystal display element as described. The liquid crystal display element according to any one of claims 1 to 4, wherein the liquid crystal composition contains at least one compound selected from the group of compounds represented by formula (1) as a first component.

In Formula (1), R ¹ and R ² are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyloxy having 2 to 12 carbons. Yes; Ring A and Ring C are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine Or tetrahydropyran-2,5-diyl; ring B is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5 - methyl-1,4-phenylene, it is a 3,4,5-trifluoro-2,6-diyl or 7,8-difluoro-chroman-2,6-diyl,; ^{Z 1} Oyo Z ² is independently a single bond, ethylene, carbonyloxy or methyleneoxy,; a is 1, 2, or 3,, b is 0 or 1, and the sum is 3 of a and b It is as follows. 6. The liquid crystal composition according to claim 1, comprising at least one compound selected from the group of compounds represented by formula (1-1) to formula (1-22) as a first component in the liquid crystal composition. A liquid crystal display element according to item.

In the formula (1-1) to the formula (1-22), R ¹ and R ² are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or It is alkenyloxy having 2 to 12 carbon atoms.   The liquid crystal display element of Claim 5 or 6 whose ratio of the 1st component in a liquid-crystal composition is the range of 10 weight%-90 weight%. The liquid crystal display element according to claim 1, wherein the liquid crystal composition further contains at least one compound selected from the group of compounds represented by formula (2) as the second component.

In Formula (2), R ³ and R ⁴ are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, and at least one hydrogen is replaced by fluorine or chlorine Substituted alkyl having 1 to 12 carbon atoms or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine; Ring D and Ring E are each independently 1,4-cyclohexylene; 1,4-phenylene, 2-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene; Z ³ is a single bond, ethylene, carbonyloxy, or methyleneoxy; c Is 1, 2 or 3. The liquid crystal composition according to any one of claims 1 to 8, further comprising at least one compound selected from the group of compounds represented by formula (2-1) to formula (2-13) as a second component in the liquid crystal composition. 2. A liquid crystal display element according to item 1.

In formulas (2-1) to (2-13), R ³ and R ⁴ are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, It is alkyl having 1 to 12 carbons in which one hydrogen is replaced with fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced with fluorine or chlorine.   10. The liquid crystal display element according to claim 8, wherein the ratio of the second component in the liquid crystal composition is in the range of 10 wt% to 90 wt%. The liquid crystal according to any one of claims 1 to 10, wherein the liquid crystal composition further contains at least one compound selected from the group of polymerizable compounds represented by formula (3) as the second additive. Display element.

In Formula (3), Ring F and Ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidine- 2-yl or pyridin-2-yl, and in these rings, at least one hydrogen is fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or at least one hydrogen. C 1-12 alkyl substituted with fluorine or chlorine may be substituted; ring G may be 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, -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 which at least one hydrogen is fluorine, chlorine, carbon number 1 to 12 alkyl, 1 to 12 carbon alkoxy, or at least one hydrogen may be replaced by 1 to 12 alkyl substituted with fluorine or chlorine; Z ⁴ and Z ⁵ are independently is a single bond or alkylene having 1 to 10 carbon atoms, in the alkylene, at least one of _-CH 2 -, -O -, - CO -, - OO-, or may be replaced by -OCO-, and at least one _-CH 2 CH ₂ - _{is, -CH = CH -, - C} (CH 3) = CH -, - CH = C (CH 3) -, or _{-C (CH 3) = C (} CH 3) - may be replaced by, in these groups, at least one hydrogen may be replaced by fluorine or ^chlorine; P ^{1, P} 2, And P ³ are polymerizable groups; Sp ¹ , Sp ² , and Sp ³ are each independently a single bond or alkylene having 1 to 10 carbons, in which at least one —CH ₂ — is , —O—, —COO—, —OCO—, or —OCOO—, and at least one —CH ₂ CH ₂ — is replaced with —CH═CH— or —C≡C—. Even In these groups, at least one hydrogen may be replaced by fluorine or chlorine; d is 0, 1, or 2; e, f, and g are independently 0, 1, 2, 3 or 4, and the sum of e, f and g is 1 or greater. In formula (3) in the liquid crystal composition, P ¹ , P ² , and P ³ were independently selected from the group of polymerizable groups represented by formula (P-1) to formula (P-5). The liquid crystal display element according to claim 11, which is a group.

In formulas (P-1) to (P-5), M ¹ , M ² , and M ³ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or at least one hydrogen is fluorine or chlorine 1-5 alkyl substituted with The at least 1 compound selected from the group of the polymeric compound represented by Formula (3-1) to Formula (3-27) as a 2nd additive in a liquid-crystal composition of Claim 1 to 12 The liquid crystal display element according to any one of the above.

In Formula (3-1) to Formula (3-27), P ⁴ , P ⁵ , and P ⁶ are independently a polymerizable group represented by Formula (P-1) to Formula (P-3). A group selected from the group;

Here, M ¹ , M ² , and M ³ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine. Yes; Sp ¹ , Sp ² , and Sp ³ are each independently a single bond or alkylene having 1 to 10 carbons, in which at least one —CH ₂ — is —O—, —COO—, -OCO-, or -OCOO- in may be replaced, at least one _-CH 2 CH ₂ - may be replaced by -CH = CH- or -C≡C-, and in the groups, at least One hydrogen may be replaced with fluorine or chlorine.   The ratio of the second additive in the liquid crystal composition is in the range of 0.03 to 10 parts by weight when the total amount of liquid crystal compounds is 100 parts by weight. A liquid crystal display element according to 1.   The alignment monomer in the liquid crystal composition reacts by irradiating linearly polarized light between the pair of substrates and the liquid crystal composition according to any one of claims 1 to 14 and an electrode. Liquid crystal display element.   The liquid crystal display element according to claim 15, wherein an operation mode of the liquid crystal display element is an IPS mode, a VA mode, an FFS mode, or an FPA mode, and a driving method of the liquid crystal display element is an active matrix method. The liquid crystal display element according to claim 15, wherein an operation mode of the liquid crystal display element is an IPS mode or an FFS mode, and a driving system of the liquid crystal display element is an active matrix system.   15. A polymer-supported alignment type liquid crystal display element comprising the liquid crystal composition according to claim 1, wherein a polymerizable compound in the liquid crystal composition is polymerized.   Use of the liquid crystal composition according to claim 1 in a liquid crystal display device.   Use of the liquid crystal composition according to any one of claims 1 to 14 in a polymer supported alignment type liquid crystal display device. A compound represented by formula (A-1).

In formula (A-1), P ¹⁰ and P ²⁰ are independently a group selected from the group represented by formula (Q-1);
In formula (Q-1), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, methyl, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine;
Sp ¹⁰ and Sp ²⁰ are independently a single bond or alkylene having 1 to 12 carbons, and at least one hydrogen of the alkylene may be replaced by fluorine or formula (Q-6), and at least one of —CH ₂ — may be replaced with —O—, —CO—, —COO—, or —OCO—, and at least one —CH ₂ CH ₂ — may be replaced with —CH═CH—. Often;
k ¹⁰ and n ¹⁰ are each independently an integer from 0 to 3, and the sum of k ¹⁰ and n ¹⁰ is an integer from 1 to 4;
R ¹⁰ , R ²⁰ , R ³⁰ , and R ⁴⁰ are independently hydrogen, fluorine, alkyl having 1 to 10 carbons, or alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine;
In formula (Q-6), M ¹⁰ , M ²⁰ , and M ³⁰ are independently hydrogen, fluorine, methyl, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine; Sp ⁴¹ is independently a single bond or alkylene having 1 to 12 carbons, wherein at least one hydrogen of the alkylene may be replaced by fluorine or chlorine, and at least one —CH ₂ — is —O— , -CO-, -COO-, or -OCO-;
When Sp ¹⁰ and Sp ²⁰ are both alkylene having 3, 6 or 11 carbon atoms, R ¹⁰ is hydrogen, alkyl having 2 to 10 carbon atoms or alkyl having 1 to 10 carbon atoms in which at least one hydrogen is replaced by fluorine. And R ²⁰ is hydrogen;
When both Sp ¹⁰ and Sp ²⁰ are alkylene having 6 or 8 carbon atoms, R ¹⁰ and R ²⁰ are hydrogen, R ³⁰ is hydrogen, fluorine, alkyl having 2 to 10 carbon atoms, or at least one hydrogen is fluorine. R 1 is alkyl having 1 to 10 carbon atoms replaced by R ⁴⁰ . Use of the compound according to claim 21 as a monomer for forming an orientation control layer.   The liquid crystal composition according to any one of claims 1 to 14.