WO2020116380A1 - Compound, liquid crystal composition and liquid crystal display element - Google Patents

Abstract

The present invention provides a polar compound which exhibits high chemical stability, high ability to align liquid crystal molecules, high solubility in a liquid crystal composition and a high voltage retention rate in a liquid crystal display element. The compound is represented by formula (1). For example, R1, R2 and R3 are each hydrogen, -Sp-P or an alkyl group having 1-15 carbon atoms; ring A1, ring A2, ring A3 and ring A4 are each independently 1,4-cyclohexylene or 1,4-phenylene; a and b are each independently 0, 1, 2 or 3, and c is 1, 2, 3 or 4; Z1, Z2 and Z3 are each independently a single bond or an alkylene group having 1-6 carbon atoms; Sp is a single bond or an alkylene group having 1-10 carbon atoms; and P is a group represented by any one of formula (1b) to formula (1h).

Description

Compound, liquid crystal composition, and liquid crystal display device

The present invention relates to a compound, a liquid crystal composition and a liquid crystal display device. More specifically, a compound having a plurality of polymerizable groups such as methacryloyloxy and having a substituent lateral to the mesogenic structure, a liquid crystal composition containing this compound and having a positive or negative dielectric anisotropy, and The present invention relates to a liquid crystal display device containing a composition or a cured product of a part thereof.

When liquid crystal display elements are classified based on the operation mode of liquid crystal molecules, PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS ( In-plane switching, VA (vertical alignment), FFS (fringe field switching), FPA (field-induced photo-reactive alignment) and other modes can be classified. Further, based on the driving method of the element, it can be classified into 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. Furthermore, TFTs can be classified into amorphous silicon and polycrystal silicon. The latter is classified into a high temperature type and a low temperature type according to the manufacturing process. Classification based on a light source can be classified into a reflective type that uses natural light, a transmissive type that uses a backlight, and a transflective type that uses both natural light and a backlight.

A liquid crystal composition having a nematic phase has appropriate properties. By improving the properties of this composition, an AM device having good properties can be obtained. The relationship between the characteristics of the composition and the characteristics of the AM device 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 (the temperature range in which the nematic phase is exhibited) is related to the temperature range in which the device can be used. The preferred maximum temperature of the nematic phase is about 70° C. or higher, and the preferred minimum temperature of the nematic phase is about −10° C. or lower.
The viscosity of the composition is related to the response time of the device. A short response time is preferable for displaying a moving image on the device. Response times as short as 1 millisecond are desirable. Therefore, the viscosity of the composition is preferably low, and more preferably low even at low temperature.

The optical anisotropy of the composition is related to the contrast ratio of the device. Depending on the mode of the device, large optical anisotropy or small optical anisotropy, that is, 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 mode of operation. This value is about 0.45 μm in a device having a mode such as TN. This value is in the range of about 0.30 μm to about 0.40 μm for the VA mode device and about 0.20 μm to about 0.30 μm for the IPS mode or FFS mode device. In these cases, a composition having a large optical anisotropy is preferable for a device having a small cell gap.
The 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, positive or negative large dielectric anisotropy is preferable. The large specific resistance in the composition contributes to a large voltage holding ratio and a large contrast ratio in the device. Therefore, in the initial stage, a composition having a large specific resistance at room temperature as well as at a temperature close to the maximum temperature of the nematic phase is preferable. A composition having a large specific resistance not only at room temperature but also at a temperature close to the maximum temperature of the nematic phase after being used for a long time is preferable.
The stability of the composition against UV and heat is related to the lifetime of the device. When this stability is high, the life of the device is long. Such characteristics are preferable for an AM element used in a liquid crystal projector, a liquid crystal television, or the like.

In a polymer-sustained alignment (PSA) type liquid crystal display device, a liquid crystal composition containing a polymer is used. First, a composition containing a small amount of a polymerizable compound is injected into the device. Here, a polymerizable compound having a plurality of polymerizable groups is generally used. Next, the composition is irradiated with ultraviolet rays while applying a voltage between the substrates sandwiching this element. The polymerizable compound polymerizes to form a polymer network in the composition. When this composition is used, the orientation of liquid crystal molecules can be controlled by the polymer, so that the response time of the device is shortened and image sticking is improved. Such effects of the polymer can be expected in devices having modes such as TN, ECB, OCB, IPS, VA, FFS, and FPA.

In a general-purpose liquid crystal display element, vertical alignment of liquid crystal molecules is achieved by a polyimide alignment film. On the other hand, as a liquid crystal display device having no alignment film, a mode has been proposed in which a polar compound is added to a liquid crystal composition to align liquid crystal molecules. First, a device containing a small amount of a polar compound and a small amount of a polymerizable compound is injected into the device. As the polymerizable compound, a polymerizable compound having a plurality of polymerizable groups is generally used. Here, the liquid crystal molecules are aligned by the action of the polar compound. Next, the composition is irradiated with ultraviolet rays while applying a voltage between the substrates sandwiching this element. Here, the polymerizable compound is polymerized to stabilize the alignment of liquid crystal molecules. By using this composition, it becomes possible to control the alignment of the liquid crystal molecules by the polar compound and the polymer, so that the response time of the device is shortened and the image sticking is improved. Further, in an element having no alignment film, the step of forming the alignment film is unnecessary. Since there is no alignment film, the electrical resistance of the device does not decrease due to the interaction between the alignment film and the composition. Such an effect of the combination of the polar compound and the polymer can be expected in a device having a mode such as TN, ECB, OCB, IPS, VA, FFS, and FPA.

Heretofore, in a liquid crystal display device having no alignment film, a polar compound having polymerizability has been synthesized as a compound having both the action of a polar compound and the action of a polymerizable compound (for example, Patent Documents 1 and 2). .. Patent Document 1 describes a polymerizable compound (S-1) having a plurality of polar groups and a plurality of polymerizable groups.

International Publication No. 2017/047177 International Publication No. 2016/129490

The first object of the present invention is to provide high chemical stability, high ability to align liquid crystal molecules, high polymerization reactivity by UV irradiation, large voltage holding ratio when used in a liquid crystal display device, suppression of afterimage, stable stability. It is to provide compounds having at least one of the formation of pretilt angles and having high solubility in liquid crystal compositions. The second problem includes this compound, and includes a high upper temperature limit of the nematic phase, a low lower limit temperature of the nematic phase, a low viscosity, a suitable optical anisotropy, a large positive or negative dielectric anisotropy, and a large specific resistance. And a liquid crystal composition satisfying at least one of properties such as high stability against ultraviolet rays, high stability against heat, and large elastic constant. The third problem is that at least one of characteristics such as a wide temperature range in which the device can be used, a short response time, a high transmittance, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, a long lifetime, and a good orientation property. It is to provide a liquid crystal display device having two.

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

式（１ｂ）～式（１ｈ）において、
　Ｍ^１、Ｍ^２、Ｍ^３およびＭ^４は独立して、水素、ハロゲン、炭素数１から５のアルキル、または少なくとも１つの水素がハロゲンで置き換えられた炭素数１から５のアルキルであり；
　Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^７、Ｒ^８およびＲ^９は独立して、水素または炭素数１から１５のアルキルであり、このＲ^４、Ｒ^５、Ｒ^６、Ｒ^７、Ｒ^８およびＲ^９において、少なくとも１つの－ＣＨ_２－は、－Ｏ－または－Ｓ－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、少なくとも１つの水素はハロゲンで置き換えられてもよい。
In equation (1),
R ¹ , R ² and R ³ are independently hydrogen, —Sp—P, or alkyl having 1 to 15 carbons, and in this R ¹ , R ² and R ³ , at least one —CH ₂ — is , —O— or —S—, at least one —(CH ₂ ) ₂ — may be replaced with —CH═CH— or —C≡C—, and at least one hydrogen is , May be replaced by fluorine or chlorine;
Ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are independently 1,2-cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,4-cyclohexylene, 1 ,4-cycloheptylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2, 6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, ring A ¹ , ring A ² , in ring A ³ and ring A ⁴ , at least one hydrogen is fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or 2 to 9 carbons. Alkenyloxy, or -Sp-P, at least one hydrogen may be replaced by fluorine or chlorine, and a plurality of ring A ¹ , ring A ² and ring A ³ are present in the structure. Each may be different, if
a and b are independently 0, 1, 2 or 3 and c is 1, 2, 3 or 4;
Z ¹ , Z ² and Z ³ are independently a single bond or alkylene having 1 to 6 carbon atoms, and in this Z ¹ , Z ² and Z ³ , at least one —CH ₂ — is —O—, May be replaced by —CO—, —COO—, —OCO—, or —OCOO—, where at least one —(CH ₂ ) ₂ — is replaced by —CH═CH— or —C≡C—. Or at least one hydrogen may be replaced by fluorine or chlorine, and when there are multiple Z ¹ , Z ² and Z ³ in the structure, each may be different;
In —Sp—P, Sp is a single bond or alkylene having 1 to 10 carbon atoms, and in this Sp, at least one —CH ₂ — is —O—, —CO—, —COO—, —OCO—, Or —OCOO—, at least one —(CH ₂ ) ₂ — may be replaced by —CH═CH— or —C≡C—, and at least one hydrogen is fluorine or chlorine. Each may be different when there are multiple Sp in the structure;
In -Sp-P, P is a group represented by any one of formula (1b) to formula (1h), and when a plurality of P are present in the structure, each may be different, but at least One P is a group in which R ⁴ in formula (1b) is —CH ₂ OCH ₃ or —CH ₂ OH;

In formulas (1b) to (1h),
M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, halogen, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen has been replaced by halogen;
R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are independently hydrogen or alkyl having 1 to 15 carbons, and R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁸ In R ⁹ , at least one —CH ₂ — may be replaced by —O— or —S—, and at least one —(CH ₂ ) ₂ — is —CH═CH— or —C≡C—. May be replaced by and at least one hydrogen may be replaced by halogen.

The first advantage of the present invention is chemically high stability, high ability to align liquid crystal molecules, high polymerization reactivity by ultraviolet irradiation, large voltage holding ratio when used in a liquid crystal display device, suppression of afterimage, stable stability. It is to provide compounds having at least one of the formation of pretilt angles and having high solubility in liquid crystal compositions. The second advantage is that it contains this compound, and has a high maximum temperature of the nematic phase, a low minimum temperature of the nematic phase, a low viscosity, a suitable optical anisotropy, a large positive or negative dielectric anisotropy, a large specific resistance. And a liquid crystal composition satisfying at least one of properties such as high stability against ultraviolet rays, high stability against heat, and large elastic constant. The third advantage is that at least one of characteristics such as a wide temperature range in which the device can be used, a short response time, a high transmittance, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, a long lifetime, and a good orientation property. It is to provide a liquid crystal display device having two.

The usage of terms in this specification is as follows. The terms "liquid crystal compound", "liquid crystal composition", and "liquid crystal display device" may be abbreviated as "compound", "composition", and "device", respectively.
The “liquid crystalline compound” is a compound having a liquid crystal phase such as a nematic phase or a smectic phase, and has no liquid crystal phase, but controls the physical properties of the composition such as the maximum temperature, the minimum temperature, the viscosity, and the dielectric anisotropy. It is a general term for compounds added for the purpose. This compound usually has a 6-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 crystal compound having an alkenyl is not a polymerizable compound in that sense.
The “polar compound” assists the alignment of liquid crystal molecules by the interaction of polar groups with the surface of the substrate.
“Liquid crystal display element” is a generic term for liquid crystal display panels, liquid crystal display modules, and the like.

The liquid crystal composition is usually prepared by mixing a plurality of liquid crystal compounds. This composition contains a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, a dye, and a depolymerizing agent for the purpose of further adjusting physical properties. Additives such as foaming agents are added as needed. The proportion (content) of the liquid crystal compound in the liquid crystal composition is expressed as a percentage by weight (% by weight) based on the weight of the liquid crystal composition containing no additive even when the additive is added. The ratio (addition amount) of the additive in the liquid crystal composition is expressed as a weight percentage (% by weight) based on the weight of the liquid crystal composition containing no additive. That is, the ratio of the liquid crystal compound or the additive is calculated based on the total weight of the liquid crystal compound. Weight parts per million (ppm) may be used. The ratio of the polymerization initiator and the polymerization inhibitor in the liquid crystal composition is exceptionally expressed based on the weight of the polymerizable compound.

“Clearing point” is the transition temperature between the liquid crystal phase and the isotropic phase in a liquid crystal compound. The "minimum temperature of the liquid crystal phase" is the transition temperature of the solid-liquid crystal phase (smectic phase, nematic phase, etc.) in the liquid crystal compound. The "maximum temperature of the nematic phase" is a transition temperature of a nematic phase-isotropic phase in a mixture of a liquid crystal compound and a mother liquid crystal or a liquid crystal composition, and may be abbreviated as "maximum temperature". The "minimum temperature of the nematic phase" may be abbreviated as "minimum temperature". The expressions “increase dielectric anisotropy” and “large dielectric anisotropy” mean that the absolute value of the value increases or increases. “High voltage holding ratio” means that the device has a large voltage holding ratio not only at room temperature in the initial stage but also at a temperature close to the upper limit temperature, and even after using the device for a long time, not only at room temperature but also at the upper limit temperature. It means having a large voltage holding ratio even at a temperature close to. The characteristics of the composition or device may be examined before and after the aging test (including the accelerated deterioration test). The expression “highly soluble in a liquid crystal composition” means that it has a high solubility in any of the compositions containing a liquid crystalline compound at room temperature. The composition used to evaluate the solubility can be the standard.

The compound represented by the formula (1) may be abbreviated as “compound (1)”. The compound (1) means one compound represented by the formula (1), a mixture of two compounds, or a mixture of three or more compounds. This rule also applies to at least one compound selected from the group of compounds represented by formula (2).
Symbols such as A ¹ , B ¹ and C ¹ surrounded by hexagons correspond to ring A ¹ , ring B ¹ and ring C ¹ , respectively. The hexagon represents a 6-membered ring such as a cyclohexane ring or a benzene ring or a condensed ring such as a naphthalene ring. A straight line across one side of this hexagon represents that any hydrogen on the ring may be replaced with a group such as -Sp ¹ -P ¹ .
Subscripts such as f, g, and h indicate the number of replaced groups. When the subscript is 0, there is no such replacement.
In the expression "ring A and ring C are independently X, Y, or Z,""independently" is used because the subject is plural. When the subject is "ring A is", "independently" is not used because the subject is singular.

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

The expression "at least one'A'" means that the number of'A's is arbitrary. The expression "at least one'A' may be replaced by'B'" means that if'A' itself is not replaced by'B', then one'A' is replaced by'B'. In this case, two or more'A's are replaced with'B', and in these, the position of'A' replaced with'B' is arbitrary. The rule that the substitution position is arbitrary also applies to the expression "at least one'A' is replaced by'B'". The expression "at least one A may be replaced by B, C, or D" means that when A is not replaced, when at least one A is replaced by B, at least one A is replaced by C. And the case where at least one A is replaced by D, and the case where a plurality of A are replaced by at least two of B, C, and D are included. For example, alkyl in which at least one —CH ₂ — (or —CH ₂ CH ₂ —) may be replaced by —O— (or —CH═CH—) includes alkyl, alkenyl, alkoxy, alkoxyalkyl. , Alkoxyalkenyl, and alkenyloxyalkyl. In addition, it is not preferable that two consecutive —CH ₂ — be replaced with —O— to form —O—O—. In alkyl and the like, it is not preferable that —CH ₂ — of the methyl moiety (—CH ₂ —H) is replaced with —O— to give —O—H.

“R ¹¹ and R ¹² are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, in which at least one —CH ₂ — is replaced with —O— Of course, in these groups, at least one hydrogen may be replaced by fluorine". In this phrase, "in these groups" may be interpreted literally. In this expression, "these groups" means alkyl, alkenyl, alkoxy, alkenyloxy and the like. That is, "these groups" refers to all of the groups listed before the term "in these groups". This common sense interpretation applies to other terms as well.

Halogen means fluorine, chlorine, bromine, or iodine. The preferred halogen is fluorine or chlorine. A more preferred halogen is fluorine. In the liquid crystal compound, alkyl is linear or branched and does not include cyclic alkyl. Straight chain alkyls are generally preferred over branched alkyls. The same applies to terminal groups such as alkoxy and alkenyl. Regarding the configuration of 1,4-cyclohexylene, trans is preferable to cis for increasing the maximum temperature of the nematic phase. 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 bivalent groups formed by removing two hydrogens from a ring, such as tetrahydropyran-2,5-diyl.

The present invention includes the following items.

式（１）において、
　Ｒ^１、Ｒ^２およびＲ^３は独立して、水素、－Ｓｐ－Ｐ、または炭素数１から１５のアルキルであり、このＲ^１、Ｒ^２およびＲ^３において、少なくとも１つの－ＣＨ_２－は、－Ｏ－または－Ｓ－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、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^１、環Ａ^２、環Ａ^３および環Ａ^４は独立して、１，２－シクロプロピレン、１，３－シクロブチレン、１，３－シクロペンチレン、１，４－シクロヘキシレン、１，４－シクロヘプチレン、１，４－シクロヘキセニレン、１，４－フェニレン、ナフタレン－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、またはピリジン－２，５－ジイルであり、環Ａ^１、環Ａ^２、環Ａ^３および環Ａ^４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１０のアルキル、炭素数２から１０のアルケニル、炭素数１から９のアルコキシ、炭素数２から９のアルケニルオキシ、または－Ｓｐ－Ｐで置き換えられてもよく、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、構造内に複数の環Ａ^１、環Ａ^２および環Ａ^３が存在する場合、それぞれが異なっていてもよく、；
　ａおよびｂは独立して、０、１、２、または３であり、ｃは１、２、３または４であり；
　Ｚ^１、Ｚ^２およびＺ^３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Ｚ^１、Ｚ^２およびＺ^３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、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、構造内に複数のＺ^１、Ｚ^２およびＺ^３が存在する場合、それぞれが異なっていてもよく、；
　－Ｓｐ－Ｐにおいて、Ｓｐは単結合または炭素数１から１０のアルキレンであり、このＳｐ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、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、構造内に複数のＳｐが存在する場合、それぞれが異なっていてもよく；
　－Ｓｐ－Ｐにおいて、Ｐは、式（１ｂ）～式（１ｈ）のいずれかで表される基であり、構造内に複数のＰが存在する場合、それぞれが異なっていてもよく、ただし少なくとも一つのＰは式（１ｂ）中のＲ^４が－ＣＨ_２ＯＣＨ_３または－ＣＨ_２ＯＨである基であり；

式（１ｂ）～式（１ｈ）において、
　Ｍ^１、Ｍ^２、Ｍ^３およびＭ^４は独立して、水素、ハロゲン、炭素数１から５のアルキル、または少なくとも１つの水素がハロゲンで置き換えられた炭素数１から５のアルキルであり；
　Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^７、Ｒ^８およびＲ^９は独立して、水素または炭素数１から１５のアルキルであり、このＲ^４、Ｒ^５、Ｒ^６、Ｒ^７、Ｒ^８およびＲ^９において、少なくとも１つの－ＣＨ_２－は、－Ｏ－または－Ｓ－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、少なくとも１つの水素はハロゲンで置き換えられてもよい。 [1] A compound represented by the formula (1).

In equation (1),
R ¹ , R ² and R ³ are independently hydrogen, —Sp—P, or alkyl having 1 to 15 carbons, and in this R ¹ , R ² and R ³ , at least one —CH ₂ — is , —O— or —S—, at least one —(CH ₂ ) ₂ — may be replaced with —CH═CH— or —C≡C—, and at least one hydrogen is , May be replaced by fluorine or chlorine;
Ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are independently 1,2-cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,4-cyclohexylene, 1 ,4-cycloheptylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2, 6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, ring A ¹ , ring A ² , in ring A ³ and ring A ⁴ , at least one hydrogen is fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or 2 to 9 carbons. Alkenyloxy, or -Sp-P, at least one hydrogen may be replaced by fluorine or chlorine, and a plurality of ring A ¹ , ring A ² and ring A ³ are present in the structure. Each may be different, if
a and b are independently 0, 1, 2 or 3 and c is 1, 2, 3 or 4;
Z ¹ , Z ² and Z ³ are independently a single bond or alkylene having 1 to 6 carbon atoms, and in this Z ¹ , Z ² and Z ³ , at least one —CH ₂ — is —O—, May be replaced by —CO—, —COO—, —OCO—, or —OCOO—, where at least one —(CH ₂ ) ₂ — is replaced by —CH═CH— or —C≡C—. Or at least one hydrogen may be replaced by fluorine or chlorine, and when there are multiple Z ¹ , Z ² and Z ³ in the structure, each may be different;
In —Sp—P, Sp is a single bond or alkylene having 1 to 10 carbon atoms, and in this Sp, at least one —CH ₂ — is —O—, —CO—, —COO—, —OCO—, Or —OCOO—, at least one —(CH ₂ ) ₂ — may be replaced by —CH═CH— or —C≡C—, and at least one hydrogen is fluorine or chlorine. Each may be different when there are multiple Sp in the structure;
In -Sp-P, P is a group represented by any one of formula (1b) to formula (1h), and when a plurality of P are present in the structure, each may be different, but at least One P is a group in which R ⁴ in formula (1b) is —CH ₂ OCH ₃ or —CH ₂ OH;

In formulas (1b) to (1h),
M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, halogen, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen has been replaced by halogen;
R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are independently hydrogen or alkyl having 1 to 15 carbons, and R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁸ In R ⁹ , at least one —CH ₂ — may be replaced by —O— or —S—, and at least one —(CH ₂ ) ₂ — is —CH═CH— or —C≡C—. May be replaced by and at least one hydrogen may be replaced by halogen.

[2] In formula (1),
Z ¹ , Z ² and Z ³ are independently a single bond, —(CH ₂ ) ₂ —, —(CH ₂ ) ₄ —, —CH═CH—, —C≡C—, —COO—, —OCO. _{-, - CF 2 O -,} - OCF 2 -, - CH 2 O -, - OCH 2 -, or -CF = CF-, compounds described in [1].

[3] In formula (1),
Ring A ¹ , Ring A ² , Ring A ³ and Ring A ⁴ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydro Pyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, wherein ring A ¹ , ring A ² , ring A ³ And in ring A ⁴ , at least one hydrogen is fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or alkenyloxy having 2 to 9 carbons. The compound according to [1] or [2], which may be replaced, and at least one hydrogen may be replaced by fluorine or chlorine.

[4] In formula (1),
The compound according to any one of [1] to [3], wherein R ¹ and R ² are -Sp-P, and R ³ is alkyl having 1 to 15 carbons, hydrogen or -Sp-P.

[5] In formula (1),
P is the formula (1b-1), (1b-2), (1b-3), (1b-4), formula (1b-5), (1c-1), (1d-1), (1d-2) ) Or (1e-1), and when a plurality of Ps are present in the structure, each may be different, provided that at least one P is represented by the formula (1b-4) or (1b- The compound according to any one of [1] to [4] which is 5).

[6] In formula (1),
a and b are independently 0, 1 or 2, provided that a+b is 3 or less, c is 1, 2 or 3, and ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are independent. The compound according to any one of [1] to [5], wherein 1,4-cyclohexylene or 1,4-phenylene is present, and Z ¹ , Z ² and Z ³ are single bonds.

　式（１－１）から式（１－１０）において、Ｒ^３は、炭素数１から１０のアルキル、水素または－Ｓｐ^３－Ｐ^３であり、環Ａ^１、環Ａ^２、環Ａ^３、環Ａ^４および環Ａ^５は独立して、１，４－シクロヘキシレン、１，４－フェニレン、１，３－ジオキサン－２，５－ジイルであり、環Ａ^１、環Ａ^２、環Ａ^３、環Ａ^４および環Ａ^５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５のアルキル、炭素数２から５のアルケニル、炭素数１から５のアルコキシ、または炭素数２から５のアルケニルオキシで置き換えられてもよく、構造内に複数の環Ａ^１が存在する場合、それぞれが異なっていてもよく、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Ｓｐ^１、Ｓｐ^２およびＳｐ^３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、　Ｐ^１、Ｐ^２およびＰ^３は独立して、式（１ｂ－１）、（１ｂ－２）、（１ｂ－３）、（１ｂ－４）、式（１ｂ－５）、（１ｃ－１）、（１ｄ－１）、（１ｄ－２）または（１ｅ－１）で表される基であり、構造内に複数のＰが存在する場合、それぞれが異なっていてもよく、ただし少なくとも一つのＰは式（１ｂ－４）または（１ｂ－５）である。

[7] The compound according to any one of [1] to [6], which is represented by any one of formula (1-1) to formula (1-10).

In formulas (1-1) to (1-10), R ³ is alkyl having 1 to 10 carbons, hydrogen or —Sp ³ —P ³ , and ring A ¹ , ring A ² , ring A ³ , Ring A ⁴ and ring A ⁵ are independently 1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5-diyl, and ring A ¹ , ring A ² , ring A ³ , In ring A ⁴ and ring A ⁵ ,
At least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 5 carbons, alkenyl having 2 to 5 carbons, alkoxy having 1 to 5 carbons, or alkenyloxy having 2 to 5 carbons, When a plurality of rings A ¹ are present in the structure, each may be different, and Sp ¹ , Sp ² and Sp ³ are independently a single bond or an alkylene having 1 to 10 carbons, and Sp ¹ , Sp ² and Sp ³ , at least one —CH ₂ — may be replaced with —O—, —CO—, —COO—, —OCO—, or —OCOO—, and at least one —(CH ₂ ) ₂ — may be replaced by —CH═CH— or —C≡C—, and P ¹ , P ² and P ³ are independently of the formulas (1b-1), (1b-2), A group represented by formula (1b-3), (1b-4), formula (1b-5), (1c-1), (1d-1), (1d-2) or (1e-1), If more than one P is present in the structure, each may be different, provided that at least one P is of formula (1b-4) or (1b-5).

　式（１－１１）から式（１－３２）において、Ｒ^３は、炭素数１から１０のアルキル、水素または－Ｓｐ^３－Ｐ^３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Ｓｐ^１、Ｓｐ^２およびＳｐ^３において、少なくとも１つの－ＣＨ_２－は、－Ｏ－、－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_２）_２－は、－ＣＨ＝ＣＨ－または－Ｃ≡Ｃ－で置き換えられてもよく、　Ｐ^１、Ｐ^２およびＰ^３は独立して、式（１ｂ－１）、（１ｂ－２）、（１ｂ－３）、（１ｂ－４）、式（１ｂ－５）、（１ｃ－１）、（１ｄ－１）、（１ｄ－２）または（１ｅ－１）で表される基であり、構造内に複数のＰが存在する場合、それぞれが異なっていてもよく、ただし少なくとも一つのＰは式（１ｂ－４）または（１ｂ－５）である。

[8] The compound according to any one of [1] to [7], which is represented by any one of formula (1-11) to formula (1-32).

In formulas (1-11) to (1-32), R ³ is alkyl having 1 to 10 carbons, hydrogen or —Sp ³ —P ³ , and Sp ¹ , Sp ² and Sp ³ are independently , A single bond or alkylene having 1 to 10 carbons, wherein in Sp ¹ , Sp ² and Sp ³ , at least one —CH ₂ — is replaced with —O—, —COO—, or —OCO— Alternatively, at least one —(CH ₂ ) ₂ — may be replaced by —CH═CH— or —C≡C—, and P ¹ , P ² and P ³ are independently of the formula (1b- 1), (1b-2), (1b-3), (1b-4), formula (1b-5), (1c-1), (1d-1), (1d-2) or (1e-1) When a plurality of Ps are present in the structure, each of them may be different, provided that at least one P is the formula (1b-4) or (1b-5).

[9] A liquid crystal composition containing at least one of the compounds according to any one of [1] to [8].

式（２）から（４）において、
　Ｒ^１１およびＲ^１２は独立して、炭素数１から１０のアルキルまたは炭素数２から１０のアルケニルであり、このＲ^１１およびＲ^１２において、少なくとも１つの－ＣＨ_２－は－Ｏ－で置き換えられてもよく、少なくとも１つの水素はフッ素で置き換えられてもよく；
　環Ｂ^１、環Ｂ^２、環Ｂ^３、および環Ｂ^４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、２，５－ジフルオロ－１，４－フェニレン、またはピリミジン－２，５－ジイルであり；
　Ｚ^１１、Ｚ^１２、およびＺ^１３は独立して、単結合、－ＣＯＯ－、－ＣＨ_２ＣＨ_２－、－ＣＨ＝ＣＨ－、または－Ｃ≡Ｃ－である。 [10] The liquid crystal composition according to [9], which contains at least one compound selected from the group of compounds represented by formulas (2) to (4).

In equations (2) to (4),
R ¹¹ and R ¹² are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in this R ¹¹ and R ¹² , at least one —CH ₂ — is replaced with —O— And at least one hydrogen may be replaced by fluorine;
Ring B ¹ , Ring B ² , Ring B ³ , and Ring B ⁴ are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro- 1,4-phenylene or pyrimidine-2,5-diyl;
Z ¹¹ , Z ¹² and Z ¹³ are independently a single bond, —COO—, —CH ₂ CH ₂ —, —CH═CH—, or —C≡C—.

式（５）から（７）において、
　Ｒ^１３は炭素数１から１０のアルキルまたは炭素数２から１０のアルケニルであり、このＲ^１３において、少なくとも１つの－ＣＨ_２－は－Ｏ－で置き換えられてもよく、少なくとも１つの水素はフッ素で置き換えられてもよく；
　Ｘ^１１は、フッ素、塩素、－ＯＣＦ_３、－ＯＣＨＦ_２、－ＣＦ_３、－ＣＨＦ_２、－ＣＨ_２Ｆ、－ＯＣＦ_２ＣＨＦ_２、または－ＯＣＦ_２ＣＨＦＣＦ_３であり；
　環Ｃ^１、環Ｃ^２、および環Ｃ^３は独立して、１，４－シクロヘキシレン、１，４－フェニレン、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、または少なくとも１つの水素がフッ素で置き換えられた１，４－フェニレンであり；
　Ｚ^１４、Ｚ^１５、およびＺ^１６は独立して、単結合、－ＣＯＯ－、－ＯＣＯ－、－ＣＨ_２Ｏ－、－ＯＣＨ_２－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＨ_２ＣＨ_２－、－ＣＨ＝ＣＨ－、－Ｃ≡Ｃ－、または－（ＣＨ_２）_４－であり；
　Ｌ^１１およびＬ^１２は独立して、水素またはフッ素である。 [11] The liquid crystal composition according to [9] or [10], containing at least one compound selected from the group of compounds represented by formulas (5) to (7).

In equations (5) to (7),
R ¹³ is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in this R ¹³ , at least one —CH ₂ — may be replaced by —O—, and at least one hydrogen is fluorine. May be replaced with;
X ¹¹ is fluorine, chlorine, —OCF ₃ , —OCHF ₂ , —CF ₃ , —CHF ₂ , —CH ₂ F, —OCF ₂ CHF ₂ , or —OCF ₂ CHFCF ₃ ;
Ring C ¹ , Ring C ² , and Ring C ³ are independently 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl. , Pyrimidine-2,5-diyl, or 1,4-phenylene having at least one hydrogen replaced by fluorine;
Z ¹⁴ , Z ¹⁵ and Z ¹⁶ are independently a single bond, —COO—, —OCO—, —CH ₂ O—, —OCH ₂ —, —CF ₂ O—, —OCF ₂ —, —CH ₂ CH ₂ —, —CH═CH—, —C≡C—, or —(CH ₂ ) ₄ —;
L ¹¹ and L ¹² are independently hydrogen or fluorine.

式（８）において、
　Ｒ^１４は炭素数１から１０のアルキルまたは炭素数２から１０のアルケニルであり、このＲ^１４において、少なくとも１つの－ＣＨ_２－は－Ｏ－で置き換えられてもよく、少なくとも１つの水素はフッ素で置き換えられてもよく；
　Ｘ^１２は－Ｃ≡Ｎまたは－Ｃ≡Ｃ－Ｃ≡Ｎであり；
　環Ｄ^１は、１，４－シクロヘキシレン、１，４－フェニレン、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、または少なくとも１つの水素がフッ素で置き換えられた１，４－フェニレンであり；
　Ｚ^１７は、単結合、－ＣＯＯ－、－ＯＣＯ－、－ＣＨ_２Ｏ－、－ＯＣＨ_２－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＨ_２ＣＨ_２－、または－Ｃ≡Ｃ－であり；
　Ｌ^１３およびＬ^１４は独立して、水素またはフッ素であり；
　ｉは、１、２、３、または４である。 [12] The liquid crystal composition according to any one of [9] to [11], containing at least one compound selected from the group of compounds represented by formula (8).

In equation (8),
R ¹⁴ is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in this R ¹⁴ , at least one —CH ₂ — may be replaced by —O—, and at least one hydrogen is fluorine. May be replaced with;
X ¹² is —C≡N or —C≡C—C≡N;
Ring D ¹ is 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or at least 1 1,4-phenylene with one hydrogen replaced by fluorine;
Z ¹⁷ is a single bond, —COO—, —OCO—, —CH ₂ O—, —OCH ₂ —, —CF ₂ O—, —OCF ₂ —, —CH ₂ CH ₂ —, or —C≡C—. And
L ¹³ and L ¹⁴ are independently hydrogen or fluorine;
i is 1, 2, 3, or 4.

式（１１）から（１９）において、
　Ｒ^１５、Ｒ^１６、およびＲ^１７は独立して、炭素数１から１０のアルキルまたは炭素数２から１０のアルケニルであり、このＲ^１５、Ｒ^１６、およびＲ^１７において、少なくとも１つの－ＣＨ_２－は－Ｏ－で置き換えられてもよく、少なくとも１つの水素はフッ素で置き換えられてもよく、そしてＲ^１７は、水素またはフッ素であってもよく；
　環Ｅ^１、環Ｅ^２、環Ｅ^３、および環Ｅ^４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、テトラヒドロピラン－２，５－ジイル、デカヒドロナフタレン－２，６－ジイル、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１，４－フェニレンであり；
　環Ｅ^５および環Ｅ^６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，テトラヒドロピラン－２，５－ジイル、またはデカヒドロナフタレン－２，６－ジイルであり；
　Ｚ^１８、Ｚ^１９、Ｚ^２０、およびＺ^２１は独立して、単結合、－ＣＯＯ－、－ＯＣＯ－、－ＣＨ_２Ｏ－、－ＯＣＨ_２－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＨ_２ＣＨ_２－、－ＣＦ_２ＯＣＨ_２ＣＨ_２－、または－ＯＣＦ_２ＣＨ_２ＣＨ_２－であり；
　Ｌ^１５およびＬ^１６は独立して、フッ素または塩素であり；
　Ｓ^１１は、水素またはメチルであり；
　Ｘは、－ＣＨＦ－または－ＣＦ_２－であり；
　ｊ、ｋ、ｍ、ｎ、ｐ、ｑ、ｒ、およびｓは独立して、０または１であり、ｋ、ｍ、ｎ、およびｐの和は、１または２であり、ｑ、ｒ、およびｓの和は、０、１、２、または３であり、
　ｔは、１、２、または３である。 [13] The liquid crystal composition according to any one of [9] to [12], containing at least one compound selected from the group of compounds represented by formulas (11) to (19).

In equations (11) to (19),
R ¹⁵ , R ¹⁶ and R ¹⁷ are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in R ¹⁵ , R ¹⁶ and R ¹⁷ , at least one —CH ₂ -May be replaced by -O-, at least one hydrogen may be replaced by fluorine, and R ¹⁷ may be hydrogen or fluorine;
Ring E ¹ , ring E ² , ring E ³ and ring E ⁴ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl. , Decahydronaphthalene-2,6-diyl, or 1,4-phenylene in which at least one hydrogen has been replaced by fluorine;
Ring E ⁵ and ring E ⁶ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6. -Is Jail;
Z ¹⁸ , Z ¹⁹ , Z ²⁰ and Z ²¹ are independently a single bond, —COO—, —OCO—, —CH ₂ O—, —OCH ₂ —, —CF ₂ O—, —OCF ₂ —, —CH ₂ CH ₂ —, —CF ₂ OCH ₂ CH ₂ —, or —OCF ₂ CH ₂ CH ₂ —;
L ¹⁵ and L ¹⁶ are independently fluorine or chlorine;
S ¹¹ is hydrogen or methyl;
X is —CHF— or —CF ₂ —;
j, k, m, n, p, q, r, and s are independently 0 or 1, and the sum of k, m, n, and p is 1 or 2, q, r, and the sum of s is 0, 1, 2, or 3,
t is 1, 2, or 3.

式（２０）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、環Ｆおよび環Ｉにおいて、少なくとも１つの水素は、ハロゲン、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つの水素がハロゲン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－シクロへキシレン、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、フェナントレン－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、環Ｇにおいて、少なくとも１つの水素は、ハロゲン、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つの水素がハロゲン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^２２およびＺ^２３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Ｚ^２２およびＺ^２３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、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、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^１１、Ｐ^１２、およびＰ^１３は独立して、重合性基であり；
　Ｓｐ^１１、Ｓｐ^１２、およびＳｐ^１３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Ｓｐ^１１、Ｓｐ^１２、およびＳｐ^１３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、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；
　ｕは、０、１、または２であり；
　ｆ、ｇ、およびｈは独立して、０、１、２、３、または４であり、そしてｆ、ｇ、およびｈの和は、１以上である。 [14] The liquid crystal composition according to any one of [9] to [13], containing at least one polymerizable compound represented by formula (20).

In equation (20),
Ring F and ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxan-2-yl, pyrimidin-2-yl, or pyridine. -2-yl, and in Ring F and Ring I, at least one hydrogen is halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or carbon in which at least one hydrogen is replaced by halogen. It may be replaced by an alkyl of the numbers 1 to 12;
Ring G is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, Naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene- 2,7-diyl, phenanthrene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5- Diyl, and in ring G, at least one hydrogen is halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen. May be replaced with;
Z ²² and Z ²³ are independently a single bond or alkylene having 1 to 10 carbon atoms, and in Z ²² and Z ²³ , at least one —CH ₂ — is —O—, —CO—, —COO. Or at least one —CH ₂ CH ₂ — is —CH═CH—, —C(CH ₃ )═CH—, —CH═C(CH ₃ )—, Or may be replaced with -C(CH ₃ )=C(CH ₃ )- and at least one hydrogen may be replaced with fluorine or chlorine;
P ¹¹ , P ¹² and P ¹³ are independently a polymerizable group;
Sp ¹¹ , Sp ¹² and Sp ¹³ are independently a single bond or an alkylene having 1 to 10 carbons, and in this Sp ¹¹ , Sp ¹² and Sp ¹³ , at least one —CH ₂ — is —O. -, -COO-, -OCO-, or -OCOO-, and at least one -CH ₂ CH ₂ -may be replaced by -CH=CH- or -C≡C-, At least one hydrogen may be replaced by fluorine or chlorine;
u is 0, 1, or 2;
f, g, and h are independently 0, 1, 2, 3, or 4, and the sum of f, g, and h is 1 or more.

式（２１）、（２２）、（２３）および（２４）において、Ｒ^５０は、水素、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、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つの水素がフッ素で置き換えられた炭素数２から１２のアルケニルであり；
　Ｒ^５１は、－ＯＨ、－ＮＨ_２、－ＯＲ^５３、－Ｎ(Ｒ^５３)_２、または－Ｓｉ（Ｒ^５３）_３で表される基であり、ここで、Ｒ^５３は、水素または炭素数１から７のアルキルであり、このＲ^５３において、少なくとも１つの－ＣＨ_２－は、－Ｏ－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、少なくとも１つの水素は、フッ素で置き換えられてもよく；
　Ｒ^５２は、水素、フッ素、または炭素数１から５のアルキルであり、このＲ^５２において、少なくとも１つの－ＣＨ_２－は、－Ｏ－で置き換えられてもよく、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てもよく；
　環Ａ^５０および環Ｂ^５０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－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、またはピリジン－２，５－ジイルであり、この環Ａ^５０および環Ｂ^５０において、少なくとも１つの水素は、フッ素、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^５０は、単結合、－ＣＨ_２ＣＨ_２－、－ＣＨ＝ＣＨ－、－Ｃ≡Ｃ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＨ_２Ｏ－、－ＯＣＨ_２－、または－ＣＦ＝ＣＦ－であり；
　Ｓｐ^５１、Ｓｐ^５２、Ｓｐ^５３およびＳｐ^５４は、単結合または炭素数１から７のアルキレンであり、このＳｐ^５１、Ｓｐ^５２、Ｓｐ^５３およびＳｐ^５４において、少なくとも１つの－ＣＨ_２－は、－Ｏ－、－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、少なくとも１つの水素は、フッ素で置き換えられてもよく；
　ａ^５０は、０、１、２、３、または４であり；
ａ^５１は、１または２であり；
　ｌは、０、１、２、３、４、５、または６であり、この－（ＣＨ_２）_ｌ－の少なくとも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_２ＣＨ_２－は、－ＣＨ＝ＣＨ－または－Ｃ≡Ｃ－で置き換えられてもよく、少なくとも１つの水素は、フッ素で置き換えられてもよい。 [15] The liquid crystal composition according to any one of [9] to [14], containing at least one compound selected from compounds represented by formulas (21) to (24).

In formulas (21), (22), (23) and (24), R ⁵⁰ is hydrogen, fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or R 2 having 2 to 12 carbons. Alkenyl, alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced by fluorine;
R ⁵¹ is a group represented by —OH, —NH ₂ , —OR ⁵³ , —N(R ⁵³ ) ₂ , or —Si(R ⁵³ ) ₃ , where R ⁵³ is hydrogen or the number of carbon atoms. 1 to 7 alkyl, in which R ⁵³ , at least one —CH ₂ — may be replaced by —O—, and at least one —CH ₂ CH ₂ — may be replaced by —CH═CH—. At least one hydrogen may be replaced by fluorine;
R ⁵² is hydrogen, fluorine, or alkyl having 1 to 5 carbons, and in this R ⁵² , at least one —CH ₂ — may be replaced by —O—, and at least one hydrogen is fluorine or May be replaced by chlorine;
Ring A ⁵⁰ and ring B ⁵⁰ are 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3 -Dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, wherein in ring A ⁵⁰ and ring B ⁵⁰ , at least one hydrogen is fluorine, carbon number 1 to 12 alkyl, 1-12 alkoxy, or at least one hydrogen may be replaced by 1-12 alkyl in which fluorine is replaced;
Z ⁵⁰ represents a single bond, —CH ₂ CH ₂ —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF ₂ O—, —OCF ₂ —, —CH ₂ O—. , —OCH ₂ —, or —CF═CF—;
Sp ⁵¹ , Sp ⁵² , Sp ⁵³ and Sp ⁵⁴ are a single bond or an alkylene having 1 to 7 carbon atoms, and in this Sp ⁵¹ , Sp ⁵² , Sp ⁵³ and Sp ⁵⁴ , at least one —CH ₂ — is — May be replaced by O—, —COO—, or —OCO—, at least one —CH ₂ CH ₂ — may be replaced by —CH═CH—, and at least one hydrogen may be replaced by fluorine. May be given;
a ⁵⁰ is 0, 1, 2, 3, or 4;
a ⁵¹ is 1 or 2;
l is 0, 1, 2, 3, 4, 5, or 6, and at least one —CH ₂ — of —(CH ₂ ) _l — is —O—, —CO—, —COO—, —OCO—, or —OCOO—, at least one —CH ₂ CH ₂ — may be replaced with —CH═CH— or —C≡C—, and at least one hydrogen is It may be replaced by fluorine.

式（Ｐ－１）から式（Ｐ－５）において、
　Ｍ^１１、Ｍ^１２、およびＭ^１３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つの水素がハロゲンで置き換えられた炭素数１から５のアルキルである。 [16] In equation (20),
[14], wherein P ¹¹ , P ¹² , and P ¹³ are each independently a group selected from the group of polymerizable groups represented by formula (P-1) to formula (P-5). Liquid crystal composition.

In formula (P-1) to formula (P-5),
M ¹¹ , M ¹² and M ¹³ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons or alkyl having 1 to 5 carbons in which at least one hydrogen has been replaced by halogen.

式（２０－１）から式（２０－７）において、
　Ｌ^３１、Ｌ^３２、Ｌ^３３、Ｌ^３４、Ｌ^３５、Ｌ^３６、Ｌ^３７、およびＬ^３８は独立して、水素、フッ素、またはメチルであり；
　Ｓｐ^１１、Ｓｐ^１２、およびＳｐ^１３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Ｓｐ^１１、Ｓｐ^１２、およびＳｐ^１３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、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。
　Ｐ^１１、Ｐ^１２、およびＰ^１３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、

式（Ｐ－１）から式（Ｐ－３）において、
　Ｍ^１１、Ｍ^１２、およびＭ^１３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つの水素がハロゲンで置き換えられた炭素数１から５のアルキルである。 [17] The polymerizable compound represented by the formula (20) is at least one compound selected from the group of polymerizable compounds represented by the formula (20-1) to the formula (20-7), 14] The liquid crystal composition according to any one of [16].

In equation (20-1) to equation (20-7),
L ³¹ , L ³² , L ³³ , L ³⁴ , L ³⁵ , L ³⁶ , L ³⁷ , and L ³⁸ are independently hydrogen, fluorine, or methyl;
Sp ¹¹ , Sp ¹² and Sp ¹³ are independently a single bond or an alkylene having 1 to 10 carbons, and in this Sp ¹¹ , Sp ¹² and Sp ¹³ , at least one —CH ₂ — is —O. -, -COO-, -OCO-, or -OCOO-, and at least one -CH ₂ CH ₂ -may be replaced by -CH=CH- or -C≡C-, At least one hydrogen may be replaced by fluorine or chlorine.
P ¹¹ , P ¹² , and P ¹³ are independently a group selected from the group of polymerizable groups represented by formula (P-1) to formula (P-3),

In formula (P-1) to formula (P-3),
M ¹¹ , M ¹² and M ¹³ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons or alkyl having 1 to 5 carbons in which at least one hydrogen has been replaced by halogen.

[18] At least one selected from the group of polymerizable compounds, polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, dyes, and defoamers. The liquid crystal composition according to any one of [9] to [17], containing:

[19] From the liquid crystal composition according to any one of [9] to [18] and the polymerized product of at least a part of the liquid crystal composition according to any one of [9] to [18] A liquid crystal display device containing at least one selected from the group consisting of:

The present invention also includes the following items.
(A) Further, at least two additives such as a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, a dye and an antifoaming agent. The above-mentioned liquid crystal composition containing.
(B) A polymerizable composition prepared by adding a polymerizable compound different from compound (1) or compound (20) to the above liquid crystal composition.
(C) A polymerizable composition prepared by adding the compound (1) and the compound (20) to the above liquid crystal composition.
(D) A liquid crystal composite prepared by polymerizing the polymerizable composition.
(E) A polymer-supported orientation type device containing the liquid crystal composite.
(F) Use of a polymerizable composition prepared by adding the compound (1), the compound (20), and a polymerizable compound different from the compound (1) or the compound (20) to the liquid crystal composition. A polymer-supported orientation type element produced by the above.

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

1. Aspect of Compound (1) The compound (1) of the present invention is characterized by having a mesogenic moiety composed of at least one ring, at least one polar group, and one or more polymerizable groups, and in particular, a mesogen. It is characterized by having a substituent on the side of the site. The compound (1) is useful because the polar group interacts non-covalently with the substrate surface such as glass (or metal oxide). One of the uses is an additive for a liquid crystal composition used in a liquid crystal display device, and in this use, the compound (1) is added for the purpose of controlling the alignment of liquid crystal molecules. Such an additive is chemically stable under the condition of being sealed in the device, has a high ability to align liquid crystal molecules, has a large voltage holding ratio when used in a liquid crystal display device, and suppresses an afterimage, It is preferable that the pretilt angle is formed stably and the solubility in the liquid crystal composition is large. The compound (1) having a ring in the lateral direction satisfies such characteristics to a considerable extent and has extremely high solubility in a liquid crystal composition, which cannot be achieved by conventional compounds, and thus the compound (1) is used. As a result, compared with the case of using a conventional compound, a pretilt angle is formed more stably, an afterimage is suppressed, and an element with excellent long-term stability is maintained while maintaining the same degree of orientation or voltage holding ratio or higher. Can be easily obtained.

A preferred example of the compound (1) will be described. Preferred examples of symbols such as R ¹ , A ¹ and Sp in the compound (1) also apply to the subordinate formula of the compound (1). In the compound (1), the properties can be adjusted arbitrarily by appropriately combining the types of these groups. Compound (1) may contain isotopes such as ² H (deuterium) and ¹³ C in a larger amount than the natural abundance, since there is no large difference in the properties of the compounds.

R ¹ , R ² and R ³ are independently hydrogen, —Sp—P, or alkyl having 1 to 15 carbons, and in this R ¹ , R ² and R ³ , at least one —CH ₂ — is , —O— or —S—, at least one —(CH ₂ ) ₂ — may be replaced with —CH═CH— or —C≡C—, and at least one hydrogen is , May be replaced by fluorine or chlorine.

Preferred R ¹ and R ² are -Sp-P, and preferred R ³ is -Sp-P, alkyl having 1 to 15 carbons, alkenyl having 2 to 15 carbons, alkoxy having 1 to 14 carbons, or Alkenyloxy having 2 to 14 carbon atoms, in which at least one hydrogen may be replaced by fluorine.
More desirable R ³ is —Sp—P, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons.
Particularly preferred R ³ is alkyl having 1 to 10 carbons.

The compound in which R ³ is alkyl having 1 to 15 carbons or alkoxy having 1 to 14 carbons has high chemical stability. A compound in which R ³ is alkyl having 1 to 15 carbons, alkenyl having 2 to 15 carbons, or alkenyloxy having 2 to 14 carbons has high solubility in a liquid crystal composition. When R ³ is —Sp—P, the polymerization reaction rate is high. The compound in which R ¹ is alkyl having 1 to 15 carbons has high ability to align liquid crystal molecules.

Ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are independently 1,2-cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,4-cyclohexylene, 1 ,4-cycloheptylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2, 6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, wherein ring A ¹ , ring In A ² , ring A ³ and ring A ⁴ , at least one hydrogen is fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or having 2 to carbons. 9 alkenyloxy, or —Sp—P, at least one hydrogen may be replaced by fluorine or chlorine, and there may be more than one ring A ^1, ring A ² and ring A ³ within the structure. If present, each may be different.

Preferred ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran- 2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, wherein ring A ¹ , ring A ² , ring A ³ and In ring A ⁴ , at least one hydrogen is replaced with fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or alkenyloxy having 2 to 9 carbons. And at least one hydrogen may be replaced by fluorine or chlorine.

More preferred ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl and tetrahydropyran. -2,5-diyl or 1,3-dioxane-2,5-diyl, wherein at least one hydrogen in the ring A ¹ , ring A ² , ring A ³ and ring A ⁴ is fluorine, carbon number It may be replaced by 1-10 alkyl, C2-C10 alkenyl, C1-C9 alkoxy, or C2-C9 alkenyloxy and at least one hydrogen may be replaced by fluorine. Good.

More preferred ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl and tetrahydropyran. -2,5-diyl, or 1,3-dioxane-2,5-diyl, in which at least one hydrogen is fluorine, alkyl having 1 to 5 carbons or alkenyl having 2 to 5 carbons. Or may be replaced with an alkoxy having 1 to 4 carbon atoms.

Particularly preferred ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are 1,4-cyclohexylene and 1,4-phenylene.

Ring A ¹ and ring A ² are independently 1,3-cyclopentylene, 1,4-cyclohexylene, 1,4-cycloheptylene, 1,4-phenylene, at least one hydrogen being replaced by fluorine 1. , 4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by alkyl having 1 to 5 carbons, decahydronaphthalene-2,6-diyl, or tetrahydropyran-2,5-diyl is , High chemical stability. Ring A ¹ and Ring A ² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine, at least 1,4-phenylene in which one hydrogen is replaced by alkyl having 1 to 5 carbons or 1,4-phenylene in which at least one hydrogen is replaced by alkenyl having 2 to 5 carbons has a liquid crystal composition It has a high solubility in substances. A compound in which ring A ¹ and ring A ² are independently 1,4-cyclohexylene, 1,4-phenylene, and 1,4-phenylene in which at least one hydrogen is replaced by alkyl having 1 to 2 carbons are , High ability to align liquid crystal molecules. Ring A ¹ and ring A ² are independently 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by alkyl having 1 to 5 carbons, at least one hydrogen is 1 to 4 carbons The 1,4-phenylene, naphthalene-2,6-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl substituted with the above alkoxy have high polymerization reactivity upon irradiation with ultraviolet rays.

a and b are independently 0, 1, 2 or 3, c is 1, 2, 3 or 4, more preferably a and b are independently 0, 1 or 2. , A+b is 3 or less, and c is 1, 2 or 3.

A compound in which a+b is 1 has a high solubility in the liquid crystal composition. The compound in which c is 2 or 3 has a high ability to align liquid crystal molecules.

Z ¹ , Z ² and Z ³ are independently a single bond or alkylene having 1 to 6 carbon atoms, and in this Z ¹ , Z ² and Z ³ , at least one —CH ₂ — is —O—, May be replaced by —CO—, —COO—, —OCO—, or —OCOO—, where at least one —(CH ₂ ) ₂ — is replaced by —CH═CH— or —C≡C—. Alternatively, at least one hydrogen may be replaced by fluorine or chlorine.

Preferred Z ¹ is a single bond, —(CH ₂ ) ₂ —, —(CH ₂ ) ₄ —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF ₂ O—, —OCF ₂ —, —CH ₂ O—, —OCH ₂ —, or —CF═CF—.
More preferred Z ¹ is a single bond, —(CH ₂ ) ₂ —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF ₂ O—, —OCF ₂ —, —CH. ₂ O-, -OCH ₂ -, or -CF=CF-.
Further preferred ^{Z 1} is a single _{bond, - (CH 2) 2 -} , - CH = CH -, - C≡C -, - CH 2 O-, or -OCH ₂ - is a more preferred ^{Z 1} is a single A bond or —(CH ₂ ) ₂ —, and particularly preferred Z ¹ is a single bond.

The compound in which Z ¹ is a single bond has high chemical stability. A compound in which Z ¹ is a single bond, —(CH ₂ ) ₂ —, —CF ₂ O—, or —OCF ₂ — has high solubility in a liquid crystal composition. A compound in which Z ¹ is a single bond or —(CH ₂ ) ₂ — has a high ability to align liquid crystal molecules. A compound in which Z ¹ is a single bond, —CH═CH—, —C≡C—, —COO—, —OCO—, —CH ₂ O—, —OCH ₂ — has a high polymerization reactivity upon irradiation with ultraviolet rays.

Sp is independently a single bond or alkylene having 1 to 10 carbons, and in this Sp, at least one —CH ₂ — is —O—, —CO—, —COO—, —OCO—, or —. OCOO—, at least one —(CH ₂ ) ₂ — may be replaced by —CH═CH— or —C≡C—, and at least one hydrogen is replaced by fluorine or chlorine. May be

Preferred Sp is independently a single bond or alkylene having 1 to 7 carbons, and in this Sp, at least one —CH ₂ — may be replaced by —O—, —COO—, or —OCO—. Well, at least one —(CH ₂ ) ₂ — may be replaced by —CH═CH— and at least one hydrogen may be replaced by fluorine.

A compound in which Sp is independently a single bond or alkylene having 1 to 7 carbons has high chemical stability. Sp ¹ , Sp ² , Sp ³ , Sp ⁴ , and Sp ⁵ are independently alkylene having 1 to 7 carbon atoms, or at least one —CH ₂ — of alkylene having 1 to 7 carbon atoms is replaced by —O—. The compound that is the obtained group has high solubility in the liquid crystal composition.

More preferable Sp is independently a single bond or alkylene having 1 to 5 carbon atoms, and in this Sp, at least one —CH ₂ — may be replaced by —O—, and at least one —(CH ₂ ) ₂ -may be replaced by -CH=CH-.

P is independently a group represented by any one of formula (1b) to formula (1h).

Preferred P is independently a group represented by any one of formulas (1b), (1c), (1d), and (1e).

In formulas (1b) to (1h), M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, halogen, alkyl having 1 to 5 carbons, or at least one hydrogen is replaced by halogen. It is an alkyl having 1 to 5 carbon atoms.

Preferred M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, fluorine, methyl, ethyl or trifluoromethyl. More preferably, it is hydrogen.

R ⁴ is hydrogen, halogen, or alkyl having 1 to 5 carbons, and in this R ⁴ , at least one hydrogen may be replaced with halogen, and at least one —CH ₂ — is replaced with —O—. May be.

Preferred R ⁴ is hydrogen, fluorine, methyl, ethyl, methoxymethyl, or trifluoromethyl. More preferably, it is hydrogen.

R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are independently hydrogen or linear, branched or cyclic alkyl having 1 to 15 carbons, and R ⁵ , R ⁶ , R 8 ^{In 7} , R ⁸ and R ⁹ , at least one —CH ₂ — may be replaced by —O— or —S—, and at least one —(CH ₂ ) ₂ — is —CH═CH—. Or it may be replaced by —C≡C— and at least one hydrogen may be replaced by halogen.

Preferred R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are independently hydrogen, linear alkyl having 1 to 10 carbons, linear alkenyl having 2 to 10 carbons, and 1 to 10 carbons. Is a straight-chain alkoxy or a C3-C6 cyclic alkyl. More preferably, it is hydrogen, linear alkyl having 2 to 6 carbons, linear alkenyl having 2 to 6 carbons, linear alkoxy having 1 to 5 carbons, or cyclic alkyl having 4 to 6 carbons. ..

More preferred P is P ¹ and P ² , and P ¹ and P ² are represented by formulas (1b-1), (1b-2), (1b-3), (1b-4) and formula (1b-5). , (1c-1), (1d-1), (1d-2) or (1e-1).

Preferred compounds (1) are compounds (1-1) to (1-10) and compounds (1-101) to (1-141) described in item 7.

More desirable compound (1) are the following compounds (1-33) to (1-49) and compounds (1-142) to (1-309).

2. Synthesis of Compound (1) A method for synthesizing the compound (1) will be described. The compound (1) can be synthesized by appropriately combining methods of synthetic organic chemistry. Compounds for which no synthetic method is described 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), and other methods.

2-1. Generation of Bonding Groups Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ An example of the method for generating the bonding group in the compound (1) is as shown in the following scheme. In this scheme, MSG ¹ (or MSG ² ) is a monovalent organic group having at least one ring. The monovalent organic groups represented by a plurality of MSG ¹ (or MSG ² ) may be the same or different. Compounds (1A) to (1J) correspond to compound (1) or an intermediate of compound (1).

(I) Formation of Single Bond Aryl boric acid (21) and compound (22) are reacted in the presence of a carbonate and a tetrakis(triphenylphosphine)palladium catalyst to synthesize compound (1A). This compound (1A) is also synthesized by reacting the compound (23) with n-butyllithium and then with zinc chloride, and then reacting the compound (22) in the presence of a dichlorobis(triphenylphosphine)palladium catalyst.

(II) Formation of —COO— and —OCO— Compound (23) is reacted with n-butyllithium and then carbon dioxide to obtain carboxylic acid (24). The carboxylic acid (24) and the phenol (25) derived from the compound (21) are dehydrated in the presence of DCC (1,3-dicyclohexylcarbodiimide) and DMAP (4-dimethylaminopyridine) to give —COO—. The compound (1B) having is synthesized. A compound having —OCO— is also synthesized by this method.

(III) Formation of —CF ₂ O— and —OCF ₂ — Compound (1B) is sulfurized with Lawesson's reagent to obtain compound (26). The compound (26) is fluorinated with a hydrogen fluoride pyridine complex and NBS (N-bromosuccinimide) to synthesize a compound (1C) having —CF ₂ O—. See M. Kuroboshi et al., Chem. Lett., 1992, 827. Compound (1C) is also synthesized by fluorinating compound (26) with DAST ((diethylamino)sulfur trifluoride). See W. H. Bunnelle et al., J. Org. Chem. 1990, 55, 768. A compound having —OCF ₂ — is also synthesized by this method.

(IV) Formation of -CH=CH- Compound (22) is reacted with n-butyllithium and then DMF (N,N-dimethylformamide) to obtain aldehyde (27). A phosphorus ylide generated by reacting a phosphonium salt (28) with potassium tert-butoxide is reacted with an aldehyde (27) to synthesize a compound (1D). A cis isomer is produced depending on the reaction conditions, so the cis isomer is isomerized to the trans isomer by a known method, if necessary.

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

Formation of (VI)-C≡C- After reacting compound (23) with 2-methyl-3-butyn-2-ol in the presence of a catalyst of dichloropalladium and copper iodide, the compound (23) was removed under basic conditions. Protect to give compound (29). Compound (29) is reacted with compound (22) in the presence of a catalyst of dichlorobis(triphenylphosphine)palladium and copper halide to synthesize compound (1F).

(VII) Formation of —CH ₂ O— and —OCH ₂ — Compound (27) is reduced with sodium borohydride to obtain compound (30). This is brominated with hydrobromic acid to obtain compound (31). The compound (25) and the compound (31) are reacted in the presence of potassium carbonate to synthesize the compound (1G). A compound having —OCH ₂ — is also synthesized by this method.

Production of (VIII)-CF=CF- After treating the compound (23) with n-butyllithium, tetrafluoroethylene is reacted to obtain the compound (32). The compound (22) is treated with n-butyllithium and then reacted with the compound (32) to synthesize the compound (1H).

(VIV) Formation of -CH=CHCO- and -COCH=CH- Compound (40) and compound (27) are subjected to aldol condensation reaction in the presence of NaOH to synthesize compound (1I).

(X) Formation of -CH=CHCOO- and -OCOCH=CH- Cinnamic acid (41) and compound (25) were added in the presence of DCC (1,3-dicyclohexylcarbodiimide) and DMAP (4-dimethylaminopyridine). The compound (1J) is synthesized by dehydration with.

2-2. Formation of Rings A ¹ , A ² , A ³ and A ⁴ 1,4-Cyclohexylene, 1,4-Cyclohexenylene, 1,4-Phenylene, 2-Fluoro-1,4-phenylene, 2-Methyl-1 ,4-phenylene, 2-ethyl-1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, Tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, perhydrocyclopenta[a]phenanthrene-3,17- For rings such as diyl, 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl Starting materials are either commercially available or synthetic methods are well known. The group represented by (A-1) and the group represented by (A-2) can be synthesized with reference to the formation of —C≡C—.

2-3. Formation of Linking Group Sp and Polymerizable Group P Preferred examples of the polymerizable group P include acryloyloxy (1b), maleimide (1c), itaconic acid ester (1d), vinyl ester (1e), oxiranyl (1g), or It is vinyloxy (1h).

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

(1) Synthesis of Compound Having Single Bond The method for synthesizing the compound having Sp ¹ or Sp ² as a single bond is as shown in the following scheme. In this scheme, MSG ¹ is a monovalent organic group having at least one ring. Compounds (1S) to (1X) correspond to compound (1). When the polymerizable group is an acrylate derivative, it is synthesized by esterification of HO-MSG1 with the corresponding acrylic acid. Vinyloxy is synthesized by etherification of HO-MSG1 and vinyl bromide. Oxiranyl is synthesized by the oxidation of the terminal double bond. The maleimide group is synthesized by reacting an amino group with maleic anhydride. Itaconic acid esters are synthesized by esterification of the corresponding itaconic acid with HO-MSG1. Vinyl ester is synthesized by transesterification reaction between vinyl acetate and HOOC-MSG1.

The synthetic method of the compound in which the linking group Sp is a single bond has been described above. The method for producing another linking group can be synthesized with reference to the method for synthesizing the bonding groups Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ .

2-4. Synthetic Example An example of the method for synthesizing the compound (1) is as follows. In these compounds, MES is a mesogenic group having at least one ring. The definitions of P ¹ , M ¹ , M ² , Sp ¹ and Sp ² are the same as above.
(1) Introduction of SP and P-1
Compound (51A) and compound (51B) are commercially available or can be synthesized according to a general organic synthesis method using mesogen (MES) having a suitable ring structure as a starting material.
In the case of synthesizing a compound in which MES and Sp ¹ are linked by an ether bond, the compound (51A) is used as a starting material, and the compound (52) and a base such as potassium hydroxide are used for etherification to synthesize the compound. (53A) can be obtained. When synthesizing a compound in which MES and Sp ¹ are linked by a single bond, the compound (51B) is used as a starting material, the compound (52), a metal catalyst such as palladium, and a cross-coupling reaction using a base. The compound (53B) can be obtained by performing. The compound (53A) or (53B) may be derivatized to the compound (54A) or (54B) to which a protecting group such as TMS or THP is applied, if necessary. Preferred protecting groups are THP, MOM, TMS, TES, TIPS, TBS, TBDPS, Bn, t-Bu, Me, Boc, Cbz, Fmoc, CH ₃ CO-(acetyl). Further preferred protecting groups are THP, MOM, TMS, TIPS, TBS, Bn, t-Bu. When introducing different Sp, P, etc. in a molecule, it may be necessary to introduce a plurality of different protecting groups. In that case, a protecting group under different deprotection conditions is introduced, deprotection is performed for each protecting group, and Sp, P and the like are introduced one by one.
Compound (57A) or (57B) is obtained by subjecting compound (53A), (53B), (54A) or compound (54B) to etherification again in the presence of compound (55) and a base such as potassium hydroxide. Can be obtained. At this time, when the protecting group is reacted in the previous step, the protecting group is removed by a deprotection reaction.

　Ｐ^２が式（１ｂ－４）で表される基である化合物（１Ａ）は、化合物（５７）より以下の方法で合成できる。化合物（５７）から、化合物（５８）、ＤＣＣおよびＤＭＡＰの存在下でエステル化反応を行うことにより化合物（１Ａ）に誘導できる。化合物（５８）は既知物質である。

The compound (1A) in which P ² is a group represented by the formula (1b-4) can be synthesized from the compound (57) by the following method. Compound (1) can be derived from compound (57) by performing an esterification reaction in the presence of compound (58), DCC and DMAP. Compound (58) is a known substance.

　市販されている化合物（ａ－１）を出発物として、マグネシウムを作用させGrignard試薬を調整し、そこに化合物（ａ－２）を加えて化合物（ａ－３）を得ることが出来る。化合物（ａ－３）をシラン還元することで、化合物（ａ－４）を得ることが出来る。
(2) Synthesis of mesogen-1

Starting from the commercially available compound (a-1), magnesium is allowed to act on the Grignard reagent, and the compound (a-2) is added thereto to obtain the compound (a-3). The compound (a-4) can be obtained by subjecting the compound (a-3) to silane reduction.

　市販されている化合物（ｃ－１）と（ｃ－２）を出発物として、鈴木カップリングで化合物（ｃ－３）を得ることが出来る。
(3) Synthesis of mesogen-2

Starting from the commercially available compounds (c-1) and (c-2), the compound (c-3) can be obtained by Suzuki coupling.

　市販されている化合物（ｄ－１）を出発物として、水素化アルミニウムリチウムで還元することで、化合物（ｄ－２）を得ることが出来る。市販されている化合物（ｄ－３）にＴＨＰ、Ｂｎなどの適切な保護基を作用させ化合物（ｄ－４）を得ることが出来る。化合物（ｄ－２）と（ｄ－４）とを酸触媒であるｐ－トルエンスルホン酸を用いて反応させることで、化合物（ｄ－５）を得ることが出来る。
(4) Synthesis of mesogen-3

The compound (d-2) can be obtained by reducing the commercially available compound (d-1) with lithium aluminum hydride. A compound (d-4) can be obtained by reacting a commercially available compound (d-3) with an appropriate protecting group such as THP and Bn. The compound (d-5) can be obtained by reacting the compounds (d-2) and (d-4) with p-toluenesulfonic acid which is an acid catalyst.

　市販されている化合物（ｅ－１）を出発物として、ｎ－ＢｕＬｉと反応させた後、ＤＭＦを加えることで、化合物（ｅ－２）を得ることが出来る。化合物（ｄ－２）と（ｅ－２）とを酸触媒であるｐ－トルエンスルホン酸を用いて反応させることで、化合物（ｅ－３）を得ることが出来る。
(5) Synthesis of mesogen-4

The compound (e-2) can be obtained by reacting n-BuLi with a commercially available compound (e-1) as a starting material and then adding DMF. The compound (e-3) can be obtained by reacting the compounds (d-2) and (e-2) with p-toluenesulfonic acid which is an acid catalyst.

　市販されている化合物（ｆ－１）を出発物として、ＴＨＰ、Ｂｎなどの適切な保護基を作用させ化合物（ｆ－２）を得ることが出来る。化合物（ｆ－２）とｎ－ＢｕＬｉと反応させた後、ほう酸トリメチルを加えることで化合物（ｆ－３）を得ることが出来る。化合物（ｆ－４）をN-ブロモスクシンイミド等の臭素化剤で臭素化することで、化合物（ｆ－５）を得ることが出来る。化合物（ｆ－５）と化合物（ｆ－３）を鈴木カップリングすることで化合物（ｆ－６）を得ることが出来る。
(6) Mesogen synthesis-5

Starting from the commercially available compound (f-1), the compound (f-2) can be obtained by acting an appropriate protecting group such as THP and Bn. The compound (f-3) can be obtained by reacting the compound (f-2) with n-BuLi and then adding trimethyl borate. The compound (f-5) can be obtained by brominating the compound (f-4) with a brominating agent such as N-bromosuccinimide. Compound (f-6) can be obtained by Suzuki coupling of compound (f-5) and compound (f-3).

　（６）の化合物（ｆ－６）を出発物として、トリフラート化することで化合物（ｇ－１）を得ることが出来る。化合物（ｇ－１）と化合物（ｆ－３）を鈴木カップリングすることで化合物（ｇ－２）を得ることが出来る。
　 (7) Mesogen synthesis-6

A compound (g-1) can be obtained by triflating the compound (f-6) of (6) as a starting material. Compound (g-2) can be obtained by Suzuki coupling of compound (g-1) and compound (f-3).

　市販されている化合物（ｈ－１）を出発物として、水素化ホウ素ナトリウムを用いて還元し化合物（ｈ－２）を得ることが出来る。化合物（ｈ－２）にＴＨＰ、Ｂｎなどの適切な保護基を作用させ化合物（ｈ－３）を得ることが出来る。化合物（ｈ－３）のアセタールをギ酸を用いて脱保護し化合物（ｈ－４）を得ることが出来る。（６）の化合物（ｆ－５）にＴＨＰ、Ｂｎなどの適切な保護基を作用させ化合物（ｈ－５）を得ることが出来る。化合物（ｈ－５）とｎ－ＢｕＬｉと反応させた後、ほう酸トリメチルを加えると化合物（ｈ－６）を得ることが出来る。化合物（ｈ－６）とブロモヨードベンゼンを鈴木カップリングすることで化合物（ｈ－７）を得ることが出来る。化合物（ｈ－７）とｎ－ＢｕＬｉと反応させた後、化合物（ｈ－４）を加えると化合物（ｈ－８）を得ることが出来る。化合物（ｈ－８）をシラン還元することで、化合物（ｈ－９）を得ることが出来る。
(8) Mesogen synthesis-7

Starting from the commercially available compound (h-1), the compound (h-2) can be obtained by reduction with sodium borohydride. Compound (h-3) can be obtained by reacting compound (h-2) with an appropriate protecting group such as THP and Bn. The acetal of compound (h-3) can be deprotected with formic acid to obtain compound (h-4). A compound (h-5) can be obtained by reacting the compound (f-5) of (6) with a suitable protecting group such as THP and Bn. After reacting the compound (h-5) with n-BuLi and then adding trimethyl borate, the compound (h-6) can be obtained. Compound (h-7) can be obtained by Suzuki coupling of compound (h-6) and bromoiodobenzene. After reacting compound (h-7) with n-BuLi and then adding compound (h-4), compound (h-8) can be obtained. The compound (h-9) can be obtained by subjecting the compound (h-8) to silane reduction.

　市販されている化合物（ｉ－１）を出発物として、ＴＨＰ、Ｂｎなどの適切な保護基を作用させ化合物（ｉ－２）を得ることが出来る。化合物（ｉ－２）とｎ－ＢｕＬｉと反応させた後、ほう酸トリメチルを加えると化合物（ｉ－３）を得ることが出来る。化合物（ｉ－３）と化合物（ｈ－６）を鈴木カップリングすることで化合物（ｉ－４）を得ることが出来る。
(9) Mesogen synthesis-8

Starting from commercially available compound (i-1), compound (i-2) can be obtained by acting an appropriate protecting group such as THP and Bn. After reacting the compound (i-2) with n-BuLi, trimethyl borate is added to obtain the compound (i-3). The compound (i-4) can be obtained by Suzuki coupling the compound (i-3) and the compound (h-6).

　化合物（ｆ－５）を出発物として、ｎ－ＢｕＬｉと反応させた後、（８）の化合物（ｈ－４）を加えると化合物（ｊ－１）を得ることが出来る。化合物（ｊ－１）をシラン還元することで、化合物（ｊ－２）を得ることが出来る。化合物（ｊ－２）をトリフラート化することで化合物（ｊ－３）を得ることが出来る。化合物（ｊ－３）と化合物（ｆ－３）を鈴木カップリングすることで化合物（Ｊ－４）を得ることが出来る。
(10) Mesogen synthesis-9

Compound (j-1) can be obtained by reacting n-BuLi with compound (f-5) as a starting material and then adding compound (h-4) in (8). The compound (j-2) can be obtained by subjecting the compound (j-1) to silane reduction. The compound (j-3) can be obtained by triflating the compound (j-2). The compound (J-4) can be obtained by Suzuki coupling the compound (j-3) and the compound (f-3).

　化合物（ｈ－５）を出発物として、ｎ－ＢｕＬｉと反応させた後、化合物（ｈ－１）を加えると化合物（ｋ－１）を得ることが出来る。化合物（ｋ－１）をシラン還元することで、化合物（ｋ－２）を得ることが出来る。化合物（ｋ－２）のアセタール基をギ酸で脱保護することにより化合物（ｋ－３）を得ることが出来る。ジメチルホスホノ酢酸エチルとｔ－ＢｕＯＫの中に化合物（ｋ－３）を加えることで化合物（ｋ－４）を得ることが出来る。化合物（ｋ－４）を水素雰囲気下、炭素パラジウムを用いて水素添加することにより化合物（ｋ－５）を得たのち、水素化アルミニウムリチウムにより還元することで化合物（ｋ－６）を得ることが出来る。
(11) Linker synthesis-1

The compound (h-1) can be obtained by reacting the compound (h-5) as a starting material with n-BuLi and then adding the compound (h-1). The compound (k-2) can be obtained by subjecting the compound (k-1) to silane reduction. The compound (k-3) can be obtained by deprotecting the acetal group of the compound (k-2) with formic acid. The compound (k-4) can be obtained by adding the compound (k-3) into ethyl dimethylphosphonoacetate and t-BuOK. Obtaining Compound (k-5) by Hydrogenating Compound (k-4) Using Carbon Palladium under Hydrogen Atmosphere, and then Obtaining Compound (k-6) by Reduction with Lithium Aluminum Hydride Can be done.

　(メトキシメチル)トリフェニルホスホニウムクロリドとｔ－ＢｕＯＫの中に化合物（ｋ－３）を加えることで、化合物（ｌ－１）を得ることが出来る。化合物（ｌ－１）にｐ－トルエンスルホン酸とメタノールを作用させることで、化合物（ｌ－２）を得ることが出来る。化合物（ｌ－２）にギ酸を加え脱保護することで化合物（ｌ－３）を得ることが出来る。市販されている化合物（ｌ－４）とｔ－ＢｕＯＫの中に化合物（ｌ－３）を加えることで、化合物（ｌ－５）を得ることが出来る。化合物（ｌ－５）を水素雰囲気下、水酸化パラジウムを用いて還元することで化合物（ｌ－６）を得ることが出来る。化合物（ｌ－６）のアセタールをギ酸で脱保護することで化合物（ｌ－７）を得ることが出来る。化合物（ｌ－７）を水素化ホウ素ナトリウムを用いて還元することで化合物（ｌ－８）を得ることが出来る。
(12) Linker synthesis-2

The compound (1-1) can be obtained by adding the compound (k-3) into (methoxymethyl)triphenylphosphonium chloride and t-BuOK. The compound (l-2) can be obtained by reacting the compound (l-1) with p-toluenesulfonic acid and methanol. The compound (l-3) can be obtained by adding formic acid to the compound (l-2) for deprotection. The compound (1-5) can be obtained by adding the compound (1-3) to the commercially available compound (1-4) and t-BuOK. Compound (1-6) can be obtained by reducing compound (1-5) with palladium hydroxide in a hydrogen atmosphere. The compound (1-7) can be obtained by deprotecting the acetal of the compound (1-6) with formic acid. The compound (1-8) can be obtained by reducing the compound (1-7) with sodium borohydride.

　市販されている化合物（ｍ－１）に水素化ジイソブチルアルミニウムを加え還元することで化合物（ｍ－２）を得ることが出来る。化合物（ｍ－２）をＴＨＰ、Ｂｎなどの適切な保護基を作用させることで化合物（ｍ－３）を得ることが出来る。化合物（ｍ－３）とｎ－ＢｕＬｉと反応させた後、ほう酸トリメチルを加えると化合物（ｍ－４）を得ることが出来る。化合物（ｍ－４）と化合物（ｈ－６）を鈴木カップリングすることで化合物（ｍ－５）を得ることが出来る。
(13) Linker synthesis-3

The compound (m-2) can be obtained by adding diisobutylaluminum hydride and reducing the commercially available compound (m-1). The compound (m-3) can be obtained by reacting the compound (m-2) with an appropriate protecting group such as THP and Bn. After reacting the compound (m-3) with n-BuLi, trimethyl borate is added to obtain the compound (m-4). Compound (m-5) can be obtained by Suzuki coupling of compound (m-4) and compound (h-6).

　市販されている化合物（ｎ－１）に、ＴＨＰ、Ｂｎなどの適切な保護基を作用させることで化合物（ｎ－２）を得ることが出来る。市販されている化合物（ｌ－４）とｔ－ＢｕＯＫの中に化合物（ｎ－２）を加えることで、化合物（ｎ－３）を得ることが出来る。化合物（ｎ－３）を水素雰囲気下、水酸化パラジウムを用いて還元することで化合物（ｎ－４）を得ることが出来る。化合物（ｌ－６）のアセタールをギ酸で脱保護することで化合物（ｎ－５）を得ることが出来る。化合物（ｎ－５）を水素化ホウ素ナトリウムを用いて還元することで化合物（ｎ－６）を得ることが出来る。化合物（ｎ－６）にＴＨＰ、Ｂｎなどの適切な保護基を作用させることで化合物（ｎ－７）を得ることが出来る。化合物（ｎ－７）を脱保護することで、化合物（ｎ－８）を得ることが出来る。化合物（ｎ－８）をトリフラート化することで化合物（ｎ－９）を得ることが出来る。化合物（ｎ－９）とｎ－ＢｕＬｉと反応させた後、ほう酸トリメチルを加えると化合物（ｎ－１０）を得ることが出来る。化合物（ｎ－１０）と化合物（ｈ－６）を鈴木カップリングすることで化合物（ｎ－１１）を得ることが出来る。
(14) Linker synthesis-4

The compound (n-2) can be obtained by reacting a commercially available compound (n-1) with an appropriate protecting group such as THP and Bn. The compound (n-3) can be obtained by adding the compound (n-2) to the commercially available compound (1-4) and t-BuOK. The compound (n-4) can be obtained by reducing the compound (n-3) with palladium hydroxide in a hydrogen atmosphere. The compound (n-5) can be obtained by deprotecting the acetal of the compound (1-6) with formic acid. The compound (n-6) can be obtained by reducing the compound (n-5) with sodium borohydride. Compound (n-7) can be obtained by reacting compound (n-6) with a suitable protecting group such as THP and Bn. The compound (n-8) can be obtained by deprotecting the compound (n-7). The compound (n-9) can be obtained by triflating the compound (n-8). After reacting compound (n-9) with n-BuLi, trimethyl borate is added to obtain compound (n-10). The compound (n-11) can be obtained by Suzuki coupling the compound (n-10) and the compound (h-6).

　市販されているか、もしくは上記（１）～（１０）の適切な環構造を有するメソゲン（ＭＥＳ）を出発物として一般的な有機合成法に従って合成することができる。
　ＭＥＳとＳｐがエーテル、またはエステル結合で連結している化合物を合成する場合は、化合物（６０）を出発物として、脱保護し化合物（６１）を得ることが出来る。続いて、エーテル化の場合は、化合物（６１）に化合物（６２）および水酸化カリウムなどの塩基を用いることにより、化合物（６３）を得ることができる。エステル化の場合は化合物（６１）に化合物（６２）およびDCC等の縮合剤を用いることにより化合物（６３）を得ることが出来る。他の側鎖も同様に、脱保護した後ＳｐやＰをエーテル化またはエステル化により導入することで化合物（７３）を得ることが出来る。
　Ｐが式（１ｂ－４）または式（１ｂ－５）で表される基である化合物（１Ｂ）は、化合物（７３）から、化合物（７４）、ＤＣＣおよびＤＭＡＰの存在下でエステル化反応を行うことにより化合物（１Ｂ）に誘導できる。
　 (15) Introduction of SP and P-2

It is commercially available, or can be synthesized according to a general organic synthesis method using a mesogen (MES) having an appropriate ring structure of the above (1) to (10) as a starting material.
When synthesizing a compound in which MES and Sp are linked by an ether or ester bond, compound (60) can be used as a starting material and deprotected to give compound (61). Subsequently, in the case of etherification, the compound (63) can be obtained by using the compound (62) and a base such as potassium hydroxide for the compound (61). In the case of esterification, the compound (63) can be obtained by using the compound (62) and a condensing agent such as DCC in the compound (61). Similarly, the other side chain can be deprotected, and then Sp or P can be introduced by etherification or esterification to obtain the compound (73).
The compound (1B) in which P is a group represented by the formula (1b-4) or the formula (1b-5) is obtained by subjecting the compound (73) to an esterification reaction in the presence of the compound (74), DCC and DMAP. The compound (1B) can be derived by carrying out.

　ＭＥＳとＳｐ^２が単結合で連結している化合物を合成する場合は、化合物（７５）を出発物として、化合物（７６）、パラジウムなどの金属触媒、および塩基を使用してクロスカップリング反応を行うことによって、化合物（７７）を得ることができる。その後ＳｐやＰをエーテル化またはエステル化により導入することで化合物（８４）を得ることが出来る。Ｐが式（１ｂ－４）または式（１ｂ－５）で表される基である化合物（１Ｃ）は、化合物（８４）から、化合物（７４）、ＤＣＣおよびＤＭＡＰの存在下でエステル化反応を行うことにより化合物（１Ｃ）に誘導できる。
(16) Introduction of Sp and P-3

When synthesizing a compound in which MES and Sp ² are linked by a single bond, a cross-coupling reaction is performed using compound (75) as a starting material, compound (76), a metal catalyst such as palladium, and a base. Compound (77) can be obtained by carrying out. Then, Compound (84) can be obtained by introducing Sp or P by etherification or esterification. The compound (1C) in which P is a group represented by the formula (1b-4) or the formula (1b-5) is obtained by subjecting the compound (84) to an esterification reaction in the presence of the compound (74), DCC and DMAP. The compound (1C) can be derived by carrying out.

3. Liquid crystal composition 3-1. Component Compound The liquid crystal composition of the present invention contains the compound (1) as the component A. The compound (1) can control the alignment of liquid crystal molecules by the non-covalent interaction with the substrate of the device. This composition preferably contains the compound (1) as the component A, and further contains at least one liquid crystal compound selected from the following components B, C, D and E. Ingredient B is compounds (2) to (4). Component C is compounds (5) to (7) other than compounds (2) to (4). Ingredient D is compound (8). Ingredient E is compounds (11) to (19). This composition may contain other liquid crystal compounds different from the compounds (2) to (8) and (11) to (19). When preparing this composition, it is preferable to select the components B, C, D, and E in consideration of the magnitude of positive or negative dielectric anisotropy. A composition with properly selected components has a high maximum temperature, a low minimum temperature, a low viscosity, an appropriate optical anisotropy (that is, large optical anisotropy or small optical anisotropy), and a large positive or negative dielectric constant. It has anisotropy, large resistivity, stability to heat or ultraviolet light, and a suitable elastic constant (ie, large elastic constant or small elastic constant).

Compound (1) is added to the composition for the purpose of controlling the alignment of liquid crystal molecules. The preferable ratio of the compound (1) to 100% by weight of the liquid crystal composition is 0.05% by weight or more from the viewpoint that liquid crystal molecules can be easily aligned, etc., and it is possible to further prevent defective display of the device. From the viewpoint of the above, it is preferably 10% by weight or less. A more desirable ratio is in the range of 0.1 wt% to 7 wt %, a more desirable ratio is in the range of 0.4 wt% to 5 wt %, and a particularly desirable ratio is in the range of 0.5 wt% to 5 wt %. It is in the range of% by weight. These ratios also apply to compositions containing compound (20).

Component B is a compound in which the two end groups are alkyl and the like. The component B has a small dielectric anisotropy. Preferred examples of the component B include compounds (2-1) to (2-11), compounds (3-1) to (3-19), and compounds (4-1) to (4-7). it can. In these compounds, R ¹¹ and R ¹² are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, wherein at least one —CH ₂ — is —O— May be replaced with and at least one hydrogen may be replaced with fluorine.

Component B has a small absolute value of dielectric anisotropy, so it is a compound close to neutrality. The compound (2) is mainly effective in decreasing the viscosity or adjusting the optical anisotropy. The compounds (3) and (4) are effective in increasing the temperature range of the nematic phase by increasing the maximum temperature or in adjusting the optical anisotropy.

As the content of component B is increased, the dielectric anisotropy of the composition decreases, but the viscosity decreases. Therefore, as long as the required value of the threshold voltage of the device is satisfied, the content of the component B is preferably large. The content of the component B is preferably 30% by weight or more, more preferably 40% by weight or more based on 100% by weight of the liquid crystal composition, and the upper limit thereof is not particularly limited, but is 99.95% by weight, for example.

Component C is a compound having a fluorine, chlorine or fluorine-containing group at at least one end. The component C has a positively large dielectric anisotropy. Preferred examples of the component C include compounds (5-1) to (5-16), compounds (6-1) to (6-116), and compounds (7-1) to (7-59). .. In the compound of component C, R ¹³ is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and alkenyl, at least one —CH ₂ — may be replaced by —O—. , At least one hydrogen may be replaced by fluorine; X ¹¹ is fluorine, chlorine, —OCF ₃ , —OCHF ₂ , —CF ₃ , —CHF ₂ , —CH ₂ F, —OCF ₂ CHF ₂ , or -OCF ₂ CHFCF ₃ .

Component C has a positive dielectric anisotropy and has very good stability against heat, light and the like, and therefore is preferably used when preparing a composition for modes such as IPS, FFS and OCB. .. The content of the component C relative to 100% by weight of the liquid crystal composition is suitably in the range of 1% by weight to 99% by weight, preferably 10% by weight to 97% by weight, more preferably 40% by weight to 95% by weight. The range is. When the component C is added to the composition having a negative dielectric anisotropy, the content of the component C is preferably 30% by weight or less based on 100% by weight of the liquid crystal composition. By adding the component C, the elastic constant of the composition can be adjusted and the voltage-transmittance curve of the device can be adjusted.

The component D is a compound (8) in which one end group is —C≡N or —C≡C—C≡N. Since the component D has a cyano group, it has a larger positive dielectric anisotropy. Preferred examples of the component D include compounds (8-1) to (8-64). In the compound of component D, R ¹⁴ is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and alkenyl, at least one —CH ₂ — may be replaced by —O—. , At least one hydrogen may be replaced by fluorine; X ¹² is —C≡N or —C≡C—C≡N.

Component D has a positive dielectric anisotropy and has a large value, so it is mainly used when preparing a composition for modes such as TN. By adding this component D, the dielectric anisotropy of the composition can be increased. The component D is effective in extending the temperature range of the liquid crystal phase, adjusting the viscosity, or adjusting the optical anisotropy. Component D is also useful for adjusting the voltage-transmittance curve of the device.

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

Ingredient E is compounds (11) to (19). The component E has a large negative dielectric anisotropy. These compounds have phenylene substituted in the lateral position with two halogens (fluorine or chlorine), such as 2,3-difluoro-1,4-phenylene. Preferred examples of the component E include compounds (11-1) to (11-9), compounds (12-1) to (12-19), compounds (13-1) and (13-2), compound (14- 1) to (14-3), compounds (15-1) to (15-3), compounds (16-1) to (16-11), compounds (17-1) to (17-3), compounds ( 18-1) to (18-3) and the compound (19-1) can be mentioned. In these compounds, R ¹⁵ , R ¹⁶ , and R ¹⁷ are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, wherein at least one —CH ₂ — May be replaced by —O—, in these groups at least one hydrogen may be replaced by fluorine, and R ¹⁷ may be hydrogen or fluorine.

Component E has a large negative dielectric anisotropy. Ingredient E is suitably used when preparing a composition for modes such as IPS, VA, PSA. As the content of the component E is increased, the dielectric anisotropy of the composition increases negatively, but the viscosity increases. Therefore, it is preferable that the content is small as long as the required threshold voltage of the device is satisfied. Considering that the dielectric anisotropy is about -5, the content of the component E is preferably 40% by weight or more with respect to 100% by weight of the liquid crystal composition in order to drive the voltage sufficiently.

Since the compound (11) of the component E is a bicyclic compound, it has the effect of lowering the viscosity, adjusting the optical anisotropy, or increasing the dielectric anisotropy. Since the compounds (12) and (13) are tricyclic compounds and the compound (14) is a tetracyclic compound, they have the effects of increasing the maximum temperature, increasing the optical anisotropy, or increasing the dielectric anisotropy. is there. The compounds (15) to (19) have the effect of increasing the dielectric anisotropy.

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

By appropriately combining the components B, C, D, and E described above, a high maximum temperature, a low minimum temperature, a small viscosity, an appropriate optical anisotropy, a large positive or negative dielectric anisotropy, and a large dielectric anisotropy. A liquid crystal composition satisfying at least one of properties such as specific resistance, high stability against ultraviolet rays, high stability against heat, and large elastic constant can be prepared.

3-2. Additive The liquid crystal composition is prepared by a known method. For example, there may be mentioned a method of mixing the above components and dissolving them by heating. Additives may be added to the composition depending on the application. Examples of additives include polymerizable compounds other than compound (1), polar compounds, polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, dyes, and decolorizers. For example, a foaming agent. Such additives are well known to the person skilled in the art and are described in the literature.

The polymerizable compound is added for the purpose of forming a polymer in the liquid crystal composition. A polymer can be produced by polymerizing the compound (1) by irradiating it with ultraviolet rays while applying a voltage between the electrodes. At this time, the compound (1) is immobilized in a state where its polar group interacts non-covalently with the surface of the glass (or metal oxide) substrate. As a result, the ability to control the alignment of the liquid crystal molecules is further improved and an appropriate pretilt angle is obtained, so that the response time is shortened.

Preferred examples of the polymerizable compound are acrylate, methacrylate, vinyl compound, vinyloxy compound, propenyl ether, epoxy compound (oxirane, oxetane), and vinyl ketone. Further preferred examples are compounds with at least one acryloyloxy and compounds with at least one methacryloyloxy. Further preferred examples also include compounds having both acryloyloxy and methacryloyloxy.
A particularly preferable example of the polymerizable compound is the compound (20). The compound (20) is a compound different from the compound (1). The compound (1) has a polar group. On the other hand, the compound (20) preferably has no polar group.

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

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

In the formula (20), ring G is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene- 1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2, 6-diyl, naphthalene-2,7-diyl, phenanthrene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or Pyridine-2,5-diyl, in which at least one hydrogen is halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or at least one hydrogen is replaced by halogen. It may be replaced with alkyl having 1 to 12 carbons.

Preferred ring G is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3. -Diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl , Naphthalene-2,6-diyl and naphthalene-2,7-diyl. More preferred ring G is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, or 2-fluoro-1,4-phenylene. Particularly preferred ring G is 1,4-phenylene or 2-fluoro-1,4-phenylene. The most preferred ring G is 1,4-phenylene.

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

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

In formulas (P-1) to (P-5), M ¹¹ , M ¹² and M ¹³ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or at least one hydrogen is replaced with halogen. And is an alkyl having 1 to 5 carbons. Preferred M ¹¹ , M ¹² or M ¹³ is hydrogen or methyl for increasing the reactivity. More preferred M ¹¹ is hydrogen or methyl, and more preferred M ¹² or M ¹³ is hydrogen.

In the formula (20), Sp ¹¹ , Sp ¹² and Sp ¹³ are independently a single bond or an alkylene having 1 to 10 carbons, and in the Sp ¹¹ , Sp ¹² and Sp ¹³ , at least one —CH ₂ — may be replaced by —O—, —COO—, —OCO—, or —OCOO—, and at least one —CH ₂ CH ₂ — is —CH═CH— or —C≡C—. It may be replaced and at least one hydrogen may be replaced by fluorine or chlorine. Preferred Sp ¹¹ , Sp ¹² or Sp ¹³ is a single bond.

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

In formula (20), f, g, and h are independently 0, 1, 2, 3, or 4, and the sum of f, g, and h is 1 or more. Preferred f, g, or h is 1 or 2. The preferred sum is 2, 3 or 4. A further preferred sum is 2 or 3.

Preferred examples of the compound (20) are the compounds (20-1) to (20-7) and the following compounds (20-8) to (20-11) described in Item 15. More preferred examples are the following compounds (20-1-1) to (20-1-5), compounds (20-2-1) to (20-2-5), compound (20-4-1), A compound (20-5-1), a compound (20-6-1), and a compound (20-7-1). In these compounds, R ²⁵ to R ³¹ are independently hydrogen or methyl; v and x are independently 0 or 1; t and u are independently integers from 1 to 10. And t+v and x+u are each at most 10; L ³¹ to L ³⁶ are independently hydrogen or fluorine, and L ³⁷ and L ³⁸ are independently hydrogen, fluorine, or methyl.

Besides the compound (1), a polar compound can be mixed and used. Similar to the compound (1), the polar compound is added for the purpose of controlling the alignment of liquid crystal molecules by allowing the polar group to interact non-covalently with the substrate surface such as glass (or metal oxide). Like the compound (1), such a polar compound is chemically stable under the condition of being sealed in the device, has a high ability to align liquid crystal molecules, and has a voltage holding ratio when used in a liquid crystal display device. Is preferably high and the solubility in the liquid crystal composition is high. By mixing the polar compound, the orientation of the compound (1) and the voltage holding ratio can be further improved, an afterimage can be suppressed, and a stable pretilt angle can be formed.

式（２１）、（２２）、（２３）および（２４）において、Ｒ^５０は、水素、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、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つの水素がフッ素で置き換えられた炭素数２から１２のアルケニルであり；
　Ｒ^５１は、－ＯＨ、－ＣＨ(ＣＨ_２ＯＨ)_２、－ＮＨ_２、－ＯＲ^５３、－Ｎ(Ｒ^５３)_２、または－Ｓｉ（Ｒ^５３）_３で表される基であり、ここで、Ｒ^５３は、水素または炭素数１から７のアルキルであり、このＲ^５３において、少なくとも１つの－ＣＨ_２－は、－Ｏ－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、少なくとも１つの水素は、フッ素で置き換えられてもよく；
　Ｒ^５２は、水素、フッ素、または炭素数１から５のアルキルであり、このＲ^５２において、少なくとも１つの－ＣＨ_２－は、－Ｏ－で置き換えられてもよく、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てもよく；
　Ｒ^５４は、－ＯＨ、－ＮＨ_２、－ＯＲ^５３、－Ｎ(Ｒ^５３)_２、または－Ｓｉ（Ｒ^５３）_３で表される基であり、ここで、Ｒ^５３は、水素または炭素数１から７のアルキルであり、このＲ^５３において、少なくとも１つの－ＣＨ_２－は、－Ｏ－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、これらの基において、少なくとも１つの水素は、フッ素で置き換えられてもよく；

　環Ａ^５０および環Ｂ^５０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－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、またはピリジン－２，５－ジイルであり、この環Ａ^５０および環Ｂ^５０において、少なくとも１つの水素は、フッ素、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^５０は、単結合、－ＣＨ_２ＣＨ_２－、－ＣＨ＝ＣＨ－、－Ｃ≡Ｃ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＨ_２Ｏ－、－ＯＣＨ_２－、または－ＣＦ＝ＣＦ－であり；
　Ｓｐ^５１、Ｓｐ^５２、Ｓｐ^５３およびＳｐ^５４は、単結合または炭素数１から７のアルキレンであり、このＳｐ^５１、Ｓｐ^５２、Ｓｐ^５３およびＳｐ^５４において、少なくとも１つの－ＣＨ_２－は、－Ｏ－、－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、少なくとも１つの水素は、フッ素で置き換えられてもよく；
　ａ^５０は、０、１、２、３、または４であり；
ａ^５１は、１または２であり；
　ｌは、０、１、２、３、４、５、または６であり、このアルキレンの少なくとも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_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、フッ素で置き換えられてもよい。 Preferred examples of the polar compound include compounds (21) to (24).

In formulas (21), (22), (23) and (24), R ⁵⁰ is hydrogen, fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or R 2 having 2 to 12 carbons. Alkenyl, alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced by fluorine;
R ⁵¹ is a group represented by —OH, —CH(CH ₂ OH) ₂ , —NH ₂ , —OR ⁵³ , —N(R ⁵³ ) ₂ , or —Si(R ⁵³ ) ₃ , and here, , R ⁵³ is hydrogen or alkyl having 1 to 7 carbons, and in this R ⁵³ , at least one —CH ₂ — may be replaced by —O—, and at least one —CH ₂ CH ₂ —. May be replaced by -CH=CH- and at least one hydrogen may be replaced by fluorine;
R ⁵² is hydrogen, fluorine, or alkyl having 1 to 5 carbons, and in this R ⁵² , at least one —CH ₂ — may be replaced by —O—, and at least one hydrogen is fluorine or May be replaced by chlorine;
R ⁵⁴ is a group represented by —OH, —NH ₂ , —OR ⁵³ , —N(R ⁵³ ) ₂ , or —Si(R ⁵³ ) ₃ , where R ⁵³ is hydrogen or the number of carbon atoms. 1 to 7 alkyl, in which R ⁵³ , at least one —CH ₂ — may be replaced by —O—, and at least one —CH ₂ CH ₂ — may be replaced by —CH═CH—. And in these groups at least one hydrogen may be replaced by fluorine;

Ring A ⁵⁰ and ring B ⁵⁰ are 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3 -Dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, wherein in ring A ⁵⁰ and ring B ⁵⁰ , at least one hydrogen is fluorine, carbon number 1 to 12 alkyl, 1-12 alkoxy, or at least one hydrogen may be replaced by 1-12 alkyl in which fluorine is replaced;
Z ⁵⁰ represents a single bond, —CH ₂ CH ₂ —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF ₂ O—, —OCF ₂ —, —CH ₂ O—. , —OCH ₂ —, or —CF═CF—;
Sp ⁵¹ , Sp ⁵² , Sp ⁵³ and Sp ⁵⁴ are a single bond or an alkylene having 1 to 7 carbon atoms, and in this Sp ⁵¹ , Sp ⁵² , Sp ⁵³ and Sp ⁵⁴ , at least one —CH ₂ — is — May be replaced by O—, —COO—, or —OCO—, at least one —CH ₂ CH ₂ — may be replaced by —CH═CH—, and at least one hydrogen may be replaced by fluorine. May be given;
a ⁵⁰ is 0, 1, 2, 3, or 4;
a ⁵¹ is 1 or 2;
l is 0, 1, 2, 3, 4, 5, or 6 and at least one —CH ₂ — of this alkylene is —O—, —CO—, —COO—, —OCO—, or — OCOO—, at least one —CH ₂ CH ₂ — may be replaced with —CH═CH— or —C≡C—, and in these groups at least one hydrogen is fluorine. May be replaced with.

More preferable examples include the following compounds.

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

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

After adding a photo-radical polymerization initiator to the liquid crystal composition, polymerization can be performed by irradiating with ultraviolet rays while applying an electric field. However, the unreacted polymerization initiator or the decomposition product of the polymerization initiator may cause display failure such as image sticking on the device. In order to prevent this, photopolymerization may be carried out without adding a polymerization initiator. The preferable wavelength of the light for irradiation is in the range of 150 nm to 500 nm. More preferred wavelengths are in the range 250 nm to 450 nm, and most preferred wavelengths are in the range 300 nm to 400 nm.

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

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

The antioxidant is effective for maintaining a large voltage holding ratio. Preferred examples of the antioxidants include the following compounds (AO-1) and (AO-2); Irganox 415, Irganox 565, Irganox 1010, Irganox 1035, Irganox 3114, and Irganox 1098 (trade name; BASF Corporation).
The ultraviolet absorber is effective for preventing the lowering of the maximum temperature. Preferred examples of the ultraviolet absorber are benzophenone derivatives, benzoate derivatives, triazole derivatives, and the like, and specific examples thereof include the following compounds (AO-3) and (AO-4); Examples include Tinuvin 328, and Tinuvin 99-2 (trade name; BASF Corporation); and 1,4-diazabicyclo[2.2.2]octane (DABCO).

Light stabilizers such as sterically hindered amines are preferred for maintaining a large voltage holding ratio. Preferred examples of the light stabilizer include the following compounds (AO-5), (AO-6), and (AO-7); Tinuvin 144, Tinuvin 765, and Tinuvin 770DF (trade name; BASF); LA-77Y and LA-. 77G (trade name; ADEKA Co.).
A heat stabilizer is also effective for maintaining a large voltage holding ratio, and Irgafos 168 (trade name; BASF Corporation) can be mentioned as a preferable example.
If necessary, a dichroic dye such as an azo dye or anthraquinone dye is added to the composition in order to adapt to a GH (guest host) mode device.
The antifoaming agent is effective for preventing foaming. Preferred examples of the defoaming agent are dimethyl silicone oil, methylphenyl silicone oil and the like.

In the compound (AO-1), R ⁴⁰ is alkyl having 1 to 20 carbons, alkoxy having 1 to 20 carbons, —COOR ⁴¹ , or —CH ₂ CH ₂ COOR ⁴¹ , wherein R ⁴¹ is 1 To 20 alkyl. In the compounds (AO-2) and (AO-5), R ⁴² is alkyl having 1 to 20 carbons. In compound (AO-5), R ⁴³ is hydrogen, methyl or O.(oxygen radical); ring G ¹ is 1,4-cyclohexylene or 1,4-phenylene; in compound (AO-7) , Ring G ² is a group in which at least one hydrogen of 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene is replaced with fluorine; compounds (AO-5) and (AO-7) ), z is 1, 2, or 3.

4. Liquid crystal display device The liquid crystal composition has an operation mode such as PC, TN, STN, OCB, and PSA, and can be suitably used for a liquid crystal display device driven by an active matrix system. This composition has an operation mode such as PC, TN, STN, OCB, VA, and IPS, and can be suitably used for a liquid crystal display device driven by a passive matrix system. These elements can be applied to any of reflection type, transmission type, and semi-transmission type.

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

In a polymer-supported orientation type device, the polymer contained in the composition orients the liquid crystal molecules. The polar compound helps the liquid crystal molecules to align. That is, the polar compound can be used instead of the alignment film. An example of a method of manufacturing such an element is as follows. An element having two substrates called an array substrate and a color filter substrate is prepared. This substrate has no alignment film. At least one of the substrates has an electrode layer. A liquid crystal composition is prepared by mixing liquid crystal compounds. The compound (1) and, if necessary, other polymerizable compound and polar compound are added to the composition. You may add an additive further as needed. This composition is injected into the device. Light irradiation is performed with a voltage applied to this element. UV light is preferred. The polymerizable compound is polymerized by irradiation with light. By this polymerization, a composition containing a polymer is produced, and a device having a PSA mode is produced.

In this procedure, polar compounds are arranged on the substrate because the polar groups interact with the substrate surface. This polar compound aligns the liquid crystal molecules. When a plurality of polar groups are present, the interaction with the surface of the substrate becomes stronger and the alignment can be performed at a low concentration. When a voltage is applied, the alignment of liquid crystal molecules is further promoted by the action of the electric field. The polymerizable compound is also oriented according to this orientation. In this state, the polymerizable compound is polymerized by ultraviolet rays, so that a polymer maintaining this orientation is produced. The effect of this polymer additionally stabilizes the alignment of the liquid crystal molecules, thus shortening the response time of the device. Since image sticking is a malfunction of liquid crystal molecules, the effect of this polymer also improves the sticking. Since the compound (1) is polymerizable, it is consumed by the polymerization. The compound (1) is also consumed by copolymerizing with another polymerizable compound. Therefore, the compound (1) has a polar group but is consumed, so that a liquid crystal display device having a large voltage holding ratio can be obtained. If a polar compound having polymerizability is used, the effects of both the polar compound and the polymerisable compound can be achieved by a single compound, and thus the polymerizing compound having no polar group may be unnecessary. is there.

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

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

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

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

HPLC analysis: For measurement, Prominence (LC-20AD; SPD-20A) manufactured by Shimadzu Corporation was used. As the column, YMC-Pack ODS-A manufactured by YMC Co., Ltd. (length 150 mm, inner diameter 4.6 mm, particle diameter 5 μm) was used. As the eluent, acetonitrile and water were appropriately mixed and used. As the detector, a UV detector, an RI detector, a CORONA detector or the like was appropriately used. When a UV detector was used, the detection wavelength was 254 nm. The sample was dissolved in acetonitrile to prepare a 0.1% by weight solution, and 1 μL of this solution was introduced into the sample chamber. As a recorder, C-R7Aplus manufactured by Shimadzu Corporation was used.

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

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

Measurement method: The characteristics were measured by the following methods. Many of these are based on the method described in the JEITA standard (JEITA/ED-2521B), which is deliberated and enacted by the Japan Electronics and Information Technology Industries Association (JEITA), or a method modified from this. there were. No thin film transistor (TFT) was attached to the TN device used for the measurement.

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

(2) Transition temperature (℃)
For the measurement, a scanning calorimeter manufactured by Perkin Elmer, a Diamond DSC system or a high-sensitivity differential scanning calorimeter manufactured by Hitachi High-Tech Science Co., Ltd., X-DSC7000 was used. The sample was heated and lowered at a rate of 3° C./min, and the starting point of the endothermic peak or exothermic peak accompanying the phase change of the sample was obtained by extrapolation to determine the transition temperature. The melting point of the compound and the polymerization initiation temperature were also measured using this device. The temperature at which a compound transitions from a solid state to a liquid crystal phase such as a smectic phase or a nematic phase may be abbreviated as "lower limit temperature of liquid crystal phase". The temperature at which a compound transitions from a liquid crystal phase to a liquid is sometimes abbreviated as "clearing point".

The crystal was designated as C. When the types of crystals can be distinguished, they are represented as C ₁ and C ₂ . The smectic phase was represented by S and the nematic phase was represented by N. When a smectic A phase, a smectic B phase, a smectic C phase, or a smectic F phase can be distinguished among the smectic phases, they are represented as S _A , S _B , S _C , or S _F , respectively. The liquid (isotropic) was designated as I. The transition temperature is expressed as, for example, “C 50.0 N 100.0 I”. This indicates that the transition temperature from the crystal to the nematic phase is 50.0°C and the transition temperature from the nematic phase to the liquid is 100.0°C.

(3) Maximum temperature of nematic phase (T _NI or NI; °C)
The sample was placed on a hot plate of a melting point measuring device equipped with a polarization 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 maximum temperature of the nematic phase may be abbreviated as “maximum temperature”. When the sample was a mixture of the compound (1) and the mother liquid crystal, it was indicated by the symbol T _NI . When the sample was a mixture of the compound (1) and a compound such as the components B, C and D, it was indicated by the symbol NI.

(4) Minimum Temperature of a Nematic Phase (T _C; ° C.)
After storing the sample having a nematic phase in a freezer at 0°C, -10°C, -20°C, -30°C, and -40°C for 10 days, the liquid crystal phase was observed. For example, T _C was described as ≦−20° C. when the sample remained in the nematic phase at −20° C. and changed to a crystalline or smectic phase at −30° C. The lower limit temperature of the nematic phase may be abbreviated as “lower limit temperature”.

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

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

(7) Specific resistance (ρ; measured at 25°C; Ωcm)
1.0 mL of the sample was injected into a container equipped with an electrode. A direct current voltage (10 V) was applied to this container, and the direct current after 10 seconds was measured. The specific resistance was calculated from the following formula. (Specific resistance)={(voltage)×(electric capacity of container)}/{(direct current)×(dielectric constant of vacuum)}.

ㆍThe measurement method of the characteristics may differ between the sample with positive dielectric anisotropy and the sample with negative dielectric anisotropy. The measurement method when the dielectric anisotropy is positive is described in items (8a) to (12a). When the dielectric anisotropy is negative, it is described in the items (8b) to (12b).

(8a) Viscosity (rotary viscosity; γ1; measured at 25°C; mPa·s)
Positive dielectric anisotropy: The measurement followed the method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). The sample was put in a TN device in which the twist angle was 0 degree and the distance (cell gap) between the two glass substrates was 5 μm. A voltage was applied to the device stepwise in the range of 16V to 19.5V at intervals of 0.5V. After 0.2 seconds of non-application, application was repeated under the conditions of only one rectangular wave (rectangular pulse; 0.2 seconds) and no application (2 seconds). The peak current and the peak time of the transient current generated by this application were measured. These measurements and M. The value of rotational viscosity was obtained from the paper of Imai et al., Formula (8) on page 40. The value of the dielectric anisotropy required for this calculation was determined by the method described below using the device whose rotational viscosity was measured.

(8b) Viscosity (rotational viscosity; γ1; measured at 25°C; mPa·s)
Negative dielectric anisotropy: The measurement followed the method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). The sample was put in a VA device in which the distance (cell gap) between the two glass substrates was 20 μm. A voltage was applied to the device stepwise in the range of 39 V to 50 V in steps of 1 V. After 0.2 seconds of non-application, application was repeated under the conditions of only one rectangular wave (rectangular pulse; 0.2 seconds) and no application (2 seconds). The peak current and the peak time of the transient current generated by this application were measured. These measurements and M. The value of rotational viscosity was obtained from the paper of Imai et al., Formula (8) on page 40. As the dielectric anisotropy necessary for this calculation, the value measured in the following section of dielectric anisotropy was used.

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

(9b) Dielectric anisotropy (Δε; measured at 25°C)
Negative dielectric anisotropy: The value of dielectric anisotropy was calculated from the formula: Δε=ε∥−ε⊥. Dielectric constants (ε∥ and ε⊥) were measured as follows.
1) Measurement of dielectric constant (ε∥): A well-cleaned glass substrate was coated with a solution of octadecyltriethoxysilane (0.16 mL) in ethanol (20 mL). The glass substrate was rotated with a spinner and then heated at 150° C. for 1 hour. The sample was put in a VA device having a distance (cell gap) of 4 μm between two glass substrates, and the device was sealed with an adhesive that was cured by ultraviolet rays. A sine wave (0.5 V, 1 kHz) was applied to this device, and after 2 seconds, the dielectric constant (ε∥) of the liquid crystal molecule in the major axis direction was measured.
2) Measurement of dielectric constant (ε⊥): A polyimide solution was applied to a well washed glass substrate. After firing this glass substrate, the obtained alignment film was rubbed. The sample was put in a TN device in which the distance (cell gap) between the two glass substrates was 9 μm and the twist angle was 80 degrees. A sine wave (0.5 V, 1 kHz) was applied to this device, and after 2 seconds, the dielectric constant (ε⊥) in the short axis direction of the liquid crystal molecule was measured.

(10a) Elastic constant (K; measured at 25° C.; pN)
Positive dielectric anisotropy: An HP4284A type LCR meter manufactured by Agilent Technologies was used for measurement. The sample was placed in a horizontal alignment device in which the distance (cell gap) between two glass substrates was 20 μm. A charge of 0 V to 20 V was applied to this device, and the electrostatic capacity and the applied voltage were measured. Fitting the measured capacitance (C) and applied voltage (V) values using the formula (2.98) and formula (2.101) on page 75 of "Liquid Crystal Device Handbook" (Nikkan Kogyo Shimbun). Then, the values of K ₁₁ and K ₃₃ were obtained from the formula (2.99). Next, K ₂₂ was calculated by using the values of K ₁₁ and K ₃₃ obtained above in the equation (3.18) on page 171. The elastic constant K is represented by the average value of K ₁₁ , K ₂₂ and K ₃₃ thus obtained.

(10b) Elastic constants (K ₁₁ and K ₃₃ ; measured at 25° C.; pN)
Negative dielectric anisotropy: For measurement, an EC-1 type elastic constant measuring device manufactured by Toyo Technica Co., Ltd. was used. The sample was placed in a vertical alignment device in which the distance (cell gap) between two glass substrates was 20 μm. A charge of 20 V to 0 V was applied to this device, and the electrostatic capacity and the applied voltage were measured. The values of the electrostatic capacitance (C) and the applied voltage (V) were fitted using the formula (2.98) and formula (2.101) on page 75 of "Liquid Crystal Device Handbook" (Nikkan Kogyo Shimbun). The value of the elastic constant was obtained from the equation (2.100).

(11a) Threshold voltage (Vth; measured at 25°C; V)
Positive dielectric anisotropy: LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for measurement. The light source was a halogen lamp. The sample was put in a normally white mode TN device in which the distance (cell gap) between the two glass substrates was 0.45/Δn (μm) and the twist angle was 80 degrees. The voltage (32 Hz, rectangular wave) applied to this element was increased stepwise from 0 V to 10 V by 0.02 V. 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 in which the transmittance is 100% when the amount of light is maximum and the transmittance is 0% when the amount of light is minimum was created. The threshold voltage is represented by the voltage when the transmittance reaches 90%.

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

(12a) Response time (τ; measured at 25° C.; ms)
Positive dielectric anisotropy: LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for measurement. The light source was a halogen lamp. The low-pass filter (Low-pass filter) was set to 5 kHz. The sample was put into a normally white mode TN device in which a distance (cell gap) between two glass substrates was 5.0 μm and a twist angle was 80 degrees. A rectangular wave (60 Hz, 5 V, 0.5 seconds) was applied to this device. 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 amount of light was maximum, and the transmittance was 0% when the amount of light was minimum. The rise time (τr: rise time; millisecond) is the time required for the transmittance to change from 90% to 10%. The fall time (τf: fall time; millisecond) is the time required to change the transmittance from 10% to 90%. The response time was represented by the sum of the rise time and fall time thus obtained.

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

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

(14) Alignment stability (stability of liquid crystal alignment axis): Changes in the liquid crystal alignment axis on the electrode side of the liquid crystal display element were evaluated. The liquid crystal orientation angle φ (before) on the electrode side before stress application was measured, and then a rectangular wave of 4.5 V and 60 Hz was applied to the device for 20 minutes, followed by short-circuiting for 1 second, and again after 1 and 5 minutes. The liquid crystal orientation angle φ (after) on the side was measured. From these values, the change Δφ (deg.) in the liquid crystal orientation angle after 1 second and 5 minutes was calculated using the following formula.
Δφ (deg.) = φ (after)-φ (before) (Equation 2)
These measurements were performed with reference to J. Hilfiker, B. Johs, C. Herzinger, JF Elman, E. Montbach, D. Bryant, and PJ Bos, Thin Solid Films, 455-456, (2004) 596-600. .. It can be said that the smaller the Δφ, the smaller the rate of change of the liquid crystal alignment axis and the better the stability of the liquid crystal alignment axis.

(15) Pretilt angle stability (ΔPt angle; degree): Changes in the pretilt angle of the liquid crystal display device were evaluated. The pretilt angle Pt angle (before) before stress application was measured, and after that, a rectangular wave of 7.0 V and 60 Hz was applied to the device for 24 hours, and then the pretilt angle Pt angle (after) after stress application was measured again. From these values, the change in pretilt angle ΔPt angle (deg.) was calculated using the following formula.
ΔPt angle =Pt angle (after)-Pt angle (before)
Optipro (manufactured by Shintech) was used for the measurement of the pretilt angle. It can be said that the smaller the ΔPt angle, the smaller the change in the pretilt angle and the better the pretilt angle stability. Particularly, the ΔPt angle is preferably 0.1° or less.

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

[Synthesis example 1]
Synthesis of compound (No. 13)

The compound (T-1) (4.55 g), the compound (T-2) (3.23 g), DMAP (0.3 g) and dichloromethane (50 ml) were placed in a reactor and cooled to 0°C.
DCC (5.74g) was added there, and it stirred for 24 hours, returning to room temperature. The insoluble material was filtered off, the reaction mixture was poured into water, and the aqueous layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, toluene:ethyl acetate=4:1) to obtain compound (No. 13) (3.4 g; 50%).

The NMR analysis values of the obtained compound (No. 13) are as follows.
¹ H-NMR: chemical shift δ (ppm; CDCl ₃ ): 7.57 (d, 2H), 7.47 (d, 1H), 7.39 (dd, 1H), 7.19 (d, 2H) , 7.12 (d, 1H), 6.57 (s, 2H), 6.07 (s, 2H), 4.28 (d, 4H), 3.48 (d, 6H), 3.40 ( s, 3H), 2.32 (t, J=6.7 Hz, 1H), 2.13-2.04 (m, 1H), 2.61 (tt, 1H), 1.95-0.85( m, 26H).

Physical properties of compound (No. 13) were as described below.
Transition temperature (°C): C 101 I Polymerization temperature (°C): 157

[Synthesis example 2]
Synthesis of compound (No. 1)

Using compound (T-3) (6.36 g) as a starting material, compound (No. 1) (6.80 g; 66%) was obtained by a method similar to the method of synthesizing compound (No. 13).

The NMR analysis values of the obtained compound (No. 1) are as follows.
¹ H-NMR: chemical shift δ (ppm; CDCl ₃ ): 7.58 (d, 2H), 7.49 (d, 1H), 7.40 (dd, 1H), 7.20 (d, 2H). , 7.13 (d, 1H), 6.59 (s, 2H), 6.08 (s, 2H), 4.29 (d, 4H), 3.49 (d, 6H), 3.41 ( s, 3H), 2.34 (t, J=6.7 Hz, 1H), 2.15-2.05 (m, 1H), 2.61 (tt, 1H), 1.92-0.86( m, 16H).

The physical properties of the compound (No. 1) were as follows.
Transition temperature (°C): C 64.2 I Polymerization temperature (°C): 81.3

The compounds (No. 1) to (No. 24) and the compounds (I-1) to (I) below are referred to with reference to the methods described in the synthesis examples and the section “2. Synthesis of compound (1)”. -214), compounds (II-1) to (II-172), compounds (III-1) to (III-141), compounds (IV-1) to (IV-105), compounds (V-1) to (V-152), Compounds (VI-1) to (VI-98), Compounds (VII-1) to (VII-117), Compounds (VIII-1) to (VIII-138), Compound (IX-1) ) To (IX-107), compounds (X-1) to (X-115), compounds (XI-1) to (XI-205), compounds (XII-1) to (XII-118), compound (XIII) -1) to (XIII-118), compounds (XIV-1) to (XIV-116), and compounds (XV-1) to (XV-117) can be synthesized.

2. Composition Examples The compounds in the examples are represented by symbols based on the definitions in Table 2 below. In Table 2, the configuration for 1,4-cyclohexylene is trans. The number in parentheses after the symbol corresponds to the compound number. The symbol (−) means other liquid crystal compound. 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 liquid crystal composition are summarized. The characteristics were measured according to the method described above, and the measured values were directly described (without extrapolation).

[Composition M1]
1-BB-3 (2-8) 7%
1-BB-5 (2-8) 8%
2-BTB-1 (2-10) 3%
3-HHB-1 (3-1) 8%
3-HHB-3 (3-1) 14%
3-HHB-O1 (3-1) 5%
3-HHB-F (6-1) 4%
2-HHB(F)-F (6-2) 7%
3-HHB(F)-F (6-2) 7%
5-HHB(F)-F (6-2) 7%
3-HHB(F,F)-F (6-3) 5%
3-HHEB-F (6-10) 4%
5-HHEB-F (6-10) 4%
2-HB-C (8-1) 5%
3-HB-C (8-1) 12%
NI=95.8° C.; η=16.9 mPa·s; Δn=0.108; Δε=4.8.

[Composition M2]
3-HH-4 (2-1) 12%
7-HB-1 (2-5) 3%
5-HB-O2 (2-5) 5%
5-HBB(F)B-2 (4-5) 5%
5-HBB(F)B-3 (4-5) 5%
3-HB-CL (5-2) 13%
3-HHB(F,F)-F (6-3) 3%
3-HBB(F,F)-F (6-24) 30%
5-HBB(F,F)-F (6-24) 24%
NI=70.0° C.; η=19.4 mPa·s; Δn=0.113; Δε=5.7.

[Composition M3]
1V2-HH-1 (2-1) 3%
1V2-HH-3 (2-1) 4%
7-HB(F,F)-F (5-4) 3%
2-HHB(F)-F (6-2) 10%
3-HHB(F)-F (6-2) 10%
5-HHB(F)-F (6-2) 10%
2-HBB-F (6-22) 4%
3-HBB-F (6-22) 4%
5-HBB-F (6-22) 3%
2-HBB(F)-F (6-23) 9%
3-HBB(F)-F (6-23) 9%
5-HBB(F)-F (6-23) 16%
3-HBB(F,F)-F (6-24) 5%
5-HBB(F,F)-F (6-24) 10%
NI=84.9° C.; η=25.1 mPa·s; Δn=0.111; Δε=5.7.

[Composition M4]
2-HH-3 (2-1) 4%
3-HH-4 (2-1) 12%
1O1-HBBH-5 (4-1) 3%
5-HB-CL (5-2) 16%
3-HHB-F (6-1) 4%
3-HHB-CL (6-1) 3%
4-HHB-CL (6-1) 4%
3-HHB(F)-F (6-2) 10%
4-HHB(F)-F (6-2) 9%
5-HHB(F)-F (6-2) 9%
7-HHB(F)-F (6-2) 8%
5-HBB(F)-F (6-23) 4%
3-HHBB(F,F)-F (7-6) 2%
4-HHBB(F,F)-F (7-6) 3%
5-HHBB(F,F)-F (7-6) 3%
3-HH2BB(F,F)-F (7-15) 3%
4-HH2BB(F,F)-F (7-15) 3%
NI=113.2° C.; η=18.7 mPa·s; Δn=0.090; Δε=3.7.

[Composition M5]
V-HBB-2 (3-4) 10%
1O1-HBBH-4 (4-1) 4%
1O1-HBBH-5 (4-1) 4%
3-HHB(F,F)-F (6-3) 9%
3-H2HB(F,F)-F (6-15) 8%
4-H2HB(F,F)-F (6-15) 8%
5-H2HB(F,F)-F (6-15) 8%
3-HBB(F,F)-F (6-24) 11%
5-HBB(F,F)-F (6-24) 20%
3-H2BB(F,F)-F (6-27) 10%
5-HHBB(F,F)-F (7-6) 3%
3-HH2BB(F,F)-F (7-15) 3%
5-HHEBB-F (7-17) 2%
NI=106.5° C.; η=32.5 mPa·s; Δn=0.123; Δε=8.2.

[Composition M6]
5-HBBH-3 (4-1) 3%
3-HB(F)BH-3 (4-2) 3%
5-HB-F (5-2) 12%
6-HB-F (5-2) 9%
7-HB-F (5-2) 7%
2-HHB-OCF3 (6-1) 7%
3-HHB-OCF3 (6-1) 7%
4-HHB-OCF3 (6-1) 7%
5-HHB-OCF3 (6-1) 5%
3-HHB(F,F)-OCF2H (6-3) 4%
3-HHB(F,F)-OCF3 (6-3) 5%
3-HH2B-OCF3 (6-4) 4%
5-HH2B-OCF3 (6-4) 4%
3-HH2B(F)-F (6-5) 3%
3-HBB(F)-F (6-23) 10%
5-HBB(F)-F (6-23) 10%
NI=85.3° C.; η=14.9 mPa·s; Δn=0.092; Δε=4.5.

[Composition M7]
3-HH-4 (2-1) 4%
2-HH-5 (2-1) 5%
5-B(F)BB-2 (3-8) 4%
5-HB-CL (5-2) 11%
3-HHB(F,F)-F (6-3) 8%
3-HHEB(F,F)-F (6-12) 10%
4-HHEB(F,F)-F (6-12) 3%
5-HHEB(F,F)-F (6-12) 3%
3-HBB(F,F)-F (6-24) 20%
5-HBB(F,F)-F (6-24) 15%
2-HBEB(F,F)-F (6-39) 3%
3-HBEB(F,F)-F (6-39) 5%
5-HBEB(F,F)-F (6-39) 3%
3-HHBB(F,F)-F (7-6) 6%
NI=76.6° C.; η=22.7 mPa·s; Δn=0.108; Δε=8.6.

[Composition M8]
V2-HHB-1 (3-1) 5%
3-HB-CL (5-2) 6%
5-HB-CL (5-2) 4%
3-HHB-OCF3 (6-1) 5%
5-HHB(F)-F (6-2) 5%
V-HHB(F)-F (6-2) 5%
3-H2HB-OCF3 (6-13) 5%
5-H2HB(F,F)-F (6-15) 5%
5-H4HB-OCF3 (6-19) 15%
5-H4HB(F,F)-F (6-21) 7%
3-H4HB(F,F)-CF3 (6-21) 8%
5-H4HB(F,F)-CF3 (6-21) 10%
2-H2BB(F)-F (6-26) 5%
3-H2BB(F)-F (6-26) 10%
3-HBEB(F,F)-F (6-39) 5%
NI=72.6° C.; η=24.8 mPa·s; Δn=0.099; Δε=8.1.

[Composition M9]
3-HH-4 (2-1) 10%
3-HH-5 (2-1) 5%
3-HB-O2 (2-5) 15%
3-HHB-1 (3-1) 8%
3-HHB-O1 (3-1) 5%
5-HB-CL (5-2) 17%
7-HB(F,F)-F (5-4) 3%
2-HHB(F)-F (6-2) 7%
3-HHB(F)-F (6-2) 7%
5-HHB(F)-F (6-2) 7%
3-HHB(F,F)-F (6-3) 6%
3-H2HB(F,F)-F (6-15) 5%
4-H2HB(F,F)-F (6-15) 5%
NI=71.0° C.; η=13.5 mPa·s; Δn=0.074; Δε=2.8.

[Composition M10]
3-HH-4 (2-1) 9%
3-HH-5 (2-1) 10%
3-HHB-1 (3-1) 13%
5-HB-CL (5-2) 3%
7-HB(F)-F (5-3) 7%
2-HHB(F,F)-F (6-3) 4%
3-HHB(F,F)-F (6-3) 5%
3-HHEB-F (6-10) 8%
5-HHEB-F (6-10) 8%
3-HHEB(F,F)-F (6-12) 10%
4-HHEB(F,F)-F (6-12) 5%
3-GHB(F,F)-F (6-109) 5%
4-GHB(F,F)-F (6-109) 6%
5-GHB(F,F)-F (6-109) 7%
NI=87.0° C.; η=22.2 mPa·s; Δn=0.071; Δε=6.0.

[Composition M11]
3-HH-VFF (2-1) 5%
5-HH-VFF (2-1) 25%
2-BTB-1 (2-10) 10%
3-HHB-1 (3-1) 4%
VFF-HHB-1 (3-1) 8%
VFF2-HHB-1 (3-1) 11%
3-H2BTB-2 (3-17) 5%
3-H2BTB-3 (3-17) 4%
3-H2BTB-4 (3-17) 4%
3-HB-C (8-1) 18%
1V2-BEB(F,F)-C (8-15) 6%
NI=81.0° C.; η=11.1 mPa·s; Δn=0.130; Δε=6.6.

[Composition M12]
2-HH-3 (2-1) 14%
3-HB-O1 (2-5) 5%
3-HHB-1 (3-1) 3%
3-HHB-O1 (3-1) 3%
3-HHB-3 (3-1) 4%
2-BB(F)B-3 (3-6) 4%
3-HB(2F,3F)-O2 (11-1) 10%
5-HB(2F,3F)-O2 (11-1) 7%
2-BB(2F,3F)-O2 (11-3) 7%
3-BB(2F,3F)-O2 (11-3) 7%
2-HHB(2F,3F)-O2 (12-1) 5%
3-HHB(2F,3F)-O2 (12-1) 10%
2-HBB(2F,3F)-O2 (12-7) 8%
3-HBB(2F,3F)-O2 (12-7) 10%
3-B(2F,3F) B(2F,3F)-O2
(11-7) 3%
NI=73.2° C.; Δn=0.113; Δε=−4.0;

[Composition M13]
2-HH-3 (2-1) 12%
1-BB-5 (2-8) 12%
3-HHB-1 (3-1) 4%
3-HHB-O1 (3-1) 3%
3-HBB-2 (3-4) 3%
3-HB(2F,3F)-O4 (11-1) 6%
3-BB(2F,3F)-O2 (11-3) 7%
3-H2B(2F,3F)-O2 (11-4) 8%
3-H1OB(2F,3F)-O2 (11-5) 4%
2-HHB(2F,3F)-O2 (12-1) 7%
3-HHB(2F,3F)-O2 (12-1) 7%
3-HH2B(2F,3F)-O2 (12-4) 7%
5-HH2B(2F,3F)-O2 (12-4) 4%
2-HBB(2F,3F)-O2 (12-7) 5%
3-HBB(2F,3F)-O2 (12-7) 5%
4-HBB(2F,3F)-O2 (12-7) 6%
NI=82.8° C.; Δn=0.118; Δε=−4.4;

[Composition M14]
3-HH-V (2-1) 27%
3-HH-V1 (2-1) 6%
V-HHB-1 (3-1) 3%
3-HB(2F,3F)-O2 (11-1) 7%
5-HB(2F,3F)-O2 (11-1) 7%
3-BB(2F,3F)-O2 (11-3) 8%
3-HHB(2F,3F)-O2 (12-1) 5%
5-HHB(2F,3F)-O2 (12-1) 4%
3-HH1OB(2F,3F)-O2 (12-5) 4%
2-HBB(2F,3F)-O2 (12-7) 3%
3-HBB(2F,3F)-O2 (12-7) 8%
4-HBB(2F,3F)-O2 (12-7) 5%
5-HBB(2F,3F)-O2 (12-7) 8%
2-BB (2F, 3F) B-3 (13-1) 5%
NI=78.1° C.; Δn=0.107; Δε=−3.2;

[Composition M15]
3-HH-4 (2-1) 14%
V-HHB-1 (3-1) 10%
3-HBB-2 (3-4) 7%
3-HB(2F,3F)-O2 (11-1) 10%
5-HB(2F,3F)-O2 (11-1) 10%
3-H2B(2F,3F)-O2 (11-4) 8%
5-H2B(2F,3F)-O2 (11-4) 8%
3-HDhB(2F,3F)-O2 (12-3) 5%
2-HBB(2F,3F)-O2 (12-7) 6%
3-HBB(2F,3F)-O2 (12-7) 8%
4-HBB(2F,3F)-O2 (12-7) 7%
5-HBB(2F,3F)-O2 (12-7) 7%
NI=88.5° C.; Δn=0.108; Δε=−3.8;

[Composition M16]
3-HH-O1 (2-1) 5%
1-BB-5 (2-8) 4%
V-HHB-1 (3-1) 4%
5-HB(F)BH-3 (4-2) 5%
3-HB(2F,3F)-O2 (11-1) 7%
3-HB(2F,3F)-O4 (11-1) 8%
3-H2B(2F,3F)-O2 (11-4) 8%
3-BB(2F,3F)-O2 (11-3) 10%
2-HHB(2F,3F)-O2 (12-1) 4%
3-HHB(2F,3F)-O2 (12-1) 7%
3-HHB(2F,3F)-1 (12-1) 6%
3-HDhB(2F,3F)-O2 (12-3) 5%
2-HBB(2F,3F)-O2 (12-7) 6%
3-HBB(2F,3F)-O2 (12-7) 6%
4-HBB(2F,3F)-O2 (12-7) 5%
5-HBB(2F,3F)-O2 (12-7) 4%
3-H1OCro(7F,8F)-5 (16-2) 3%
3-HEB(2F,3F)B(2F,3F)-O2 (12)
3%
NI=81.1° C.; Δn=0.119; Δε=−4.5;

[Composition M17]
5-HH-V (2-1) 18%
7-HB-1 (2-5) 5%
V-HHB-1 (3-1) 7%
V2-HHB-1 (3-1) 7%
3-HBB(F)B-3 (4-5) 8%
3-HB(2F,3F)-O4 (11-1) 15%
3-chB(2F,3F)-O2 (11) 7%
2-HchB(2F,3F)-O2 (12-18) 8%
3-HBB(2F,3F)-O2 (12-7) 8%
4-HBB(2F,3F)-O2 (12-7) 5%
5-HBB(2F,3F)-O2 (12-7) 7%
3-dhBB(2F,3F)-O2 (12-9) 5%
NI=98.8° C.; Δn=0.111; Δε=−3.2;

[Composition M18]
3-HH-V (2-1) 11%
3-HH-VFF (2-1) 7%
F3-HH-V (2-1) 10%
3-HHEH-3 (3-13) 4%
3-HHEBH-3 (4-6) 4%
3-HB(F)HH-2 (4-7) 4%
3-H2B(2F,3F)-O2 (11-4) 18%
5-H2B(2F,3F)-O2 (11-4) 17%
3-HDhB(2F,3F)-O2 (12-3) 5%
3-HHB(2F,3Cl)-O2 (12) 5%
3-HBB(2F,3Cl)-O2 (12) 8%
5-HBB(2F,3Cl)-O2 (12) 7%
NI=77.5° C.; Δn=0.084; Δε=−2.6;

[Composition M19]
3-HH-V (2-1) 11%
1-BB-5 (2-8) 5%
3-HB(2F,3F)-O2 (11-1) 8%
3-H2B(2F,3F)-O2 (11-4) 10%
3-BB(2F,3F)-O2 (11-3) 10%
2O-BB(2F,3F)-O2 (11-3) 3%
3-dhBB(2F,3F)-O2 (12-9) 4%
2-HHB(2F,3F)-O2 (12-1) 4%
3-HHB(2F,3F)-O2 (12-1) 7%
2-HHB(2F,3F)-1 (12-1) 5%
3-HDhB(2F,3F)-O2 (12-3) 6%
2-HBB(2F,3F)-O2 (12-7) 4%
3-HBB(2F,3F)-O2 (12-7) 7%
2-BB (2F, 3F) B-3 (13-1) 6%
2-BB (2F, 3F) B-4 (13-1) 6%
3-HH1OCro(7F,8F)-5
(15-3) 4%
NI=70.6° C.; Δn=0.129; Δε=-4.3;

[Composition M20]
3-HH-V (2-1) 14%
1-BB-3 (2-8) 3%
3-HHB-1 (3-1) 4%
3-HHB-O1 (3-1) 4%
V-HBB-2 (3-4) 4%
1-BB(F)B-2V (3-6) 6%
5-HBBH-1O1 (4-1) 4%
3-HB(2F,3F)-O4 (11-1) 14%
3-BB(2F,3F)-O2 (11-3) 10%
3-H1OB(2F,3F)-O2 (11-5) 3%
2-HHB(2F,3F)-O2 (12-1) 7%
3-HHB(2F,3F)-O2 (12-1) 7%
3-HH1OB(2F,3F)-O2 (12-5) 6%
2-HBB(2F,3F)-O2 (12-7) 4%
3-HBB(2F,3F)-O2 (12-7) 6%
4-HBB(2F,3F)-O2 (12-7) 4%
NI=93.0° C.; Δn=0.123; Δε=-4.0;

[Composition M21]
3-HH-V (2-1) 11%
1-BB-3 (2-8) 6%
3-HHB-1 (3-1) 4%
3-HHB-O1 (3-1) 4%
3-HBB-2 (3-4) 4%
3-B(F)BB-2 (3-6) 4%
3-HB(2F,3F)-O4 (11-1) 6%
3-BB(2F,3F)-O2 (11-3) 10%
3-H2B(2F,3F)-O2 (11-4) 8%
3-H1OB(2F,3F)-O2 (11-5) 5%
2-HHB(2F,3F)-O2 (12-1) 7%
3-HHB(2F,3F)-O2 (12-1) 7%
5-HHB(2F,3F)-O2 (12-1) 7%
2-HBB(2F,3F)-O2 (12-7) 4%
3-HBB(2F,3F)-O2 (12-7) 7%
5-HBB(2F,3F)-O2 (12-7) 6%
NI=87.6° C.; Δn=0.126; Δε=−4.5;

[Composition M22]
2-HH-3 (2-1) 12%
1-BB-3 (2-8) 6%
3-HHB-1 (3-1) 3%
3-HHB-O1 (3-1) 4%
3-HBB-2 (3-4) 6%
3-B(F)BB-2 (3-6) 3%
3-HB(2F,3F)-O4 (11-1) 6%
3-BB(2F,3F)-O2 (11-3) 7%
3-H2B(2F,3F)-O2 (11-4) 8%
3-H1OB(2F,3F)-O2 (11-5) 4%
2-HHB(2F,3F)-O2 (12-1) 6%
3-HHB(2F,3F)-O2 (12-1) 10%
5-HHB(2F,3F)-O2 (12-1) 8%
2-HBB(2F,3F)-O2 (12-7) 5%
3-HBB(2F,3F)-O2 (12-7) 7%
5-HBB(2F,3F)-O2 (12-7) 5%
NI=93.0° C.; Δn=0.124; Δε=−4.5;

[Composition M23]
3-HH-V (2-1) 33%
V-HHB-1 (3-1) 3%
3-HB(2F,3F)-O2 (11-1) 7%
5-HB(2F,3F)-O2 (11-1) 7%
3-BB(2F,3F)-O2 (11-3) 8%
3-HHB(2F,3F)-O2 (12-1) 4%
5-HHB(2F,3F)-O2 (12-1) 5%
3-HH1OB(2F,3F)-O2 (12-5) 5%
2-HBB(2F,3F)-O2 (12-7) 3%
3-HBB(2F,3F)-O2 (12-7) 8%
4-HBB(2F,3F)-O2 (12-7) 5%
5-HBB(2F,3F)-O2 (12-7) 8%
2-BB (2F, 3F) B-3 (13-1) 4%
NI=76.4° C.; Δn=0.104; Δε=−3.2;

[Composition M24]
2-HH-3 (2-1) 5%
3-HH-VFF (2-1) 30%
1-BB-3 (2-8) 5%
3-HHB-1 (3-1) 3%
3-HBB-2 (3-4) 3%
2-H1OB(2F,3F)-O2 (11-5) 6%
3-H1OB(2F,3F)-O2 (11-5) 4%
3-BB(2F,3F)-O2 (11-3) 3%
2-HH1OB(2F,3F)-O2 (12-5) 14%
2-HBB(2F,3F)-O2 (12-7) 7%
3-HBB(2F,3F)-O2 (12-7) 11%
5-HBB(2F,3F)-O2 (12-7) 9%
NI=78.3° C.; Δn=0.103; Δε=−3.2;

[Composition M25]
3-HH-V (2-1) 27%
3-HH-V1 (2-1) 6%
V-HHB-1 (3-1) 5%
3-HB(2F,3F)-O2 (11-1) 5%
5-HB(2F,3F)-O2 (11-1) 7%
3-BB(2F,3F)-O2 (11-3) 8%
3-HHB(2F,3F)-O2 (12-1) 5%
5-HHB(2F,3F)-O2 (12-1) 4%
3-HH1OB(2F,3F)-O2 (12-5) 5%
2-HBB(2F,3F)-O2 (12-7) 3%
3-HBB(2F,3F)-O2 (12-7) 9%
4-HBB(2F,3F)-O2 (12-7) 4%
5-HBB(2F,3F)-O2 (12-7) 8%
2-BB (2F, 3F) B-3 (13-1) 4%
NI=81.2° C.; Δn=0.107; Δε=−3.2;

[Composition M26]
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 (2-8) 5%
1V2-BB-1 (2-8) 5%
3-HHB-1 (3-1) 6%
3-HB(F)BH-3 (4-2) 4%
3-H2B(2F,3F)-O2 (11-4) 7%
3-HHB(2F,3F)-O2 (12-1) 8%
3-HH1OB(2F,3F)-O2 (12-5) 5%
2-HchB(2F,3F)-O2 (12) 8%
3-HDhB(2F,3F)-O2 (12-3) 3%
5-HDhB(2F,3F)-O2 (12-3) 4%
2-BB (2F, 3F) B-3 (13-1) 7%
2-BB (2F, 3F) B-4 (13-1) 7%
NI=88.7° C.; Δn=0.115; Δε=-1.9;

[Composition M27]
2-HH-3 (2-1) 12%
1-BB-5 (2-8) 12%
3-HHB-1 (3-1) 4%
3-HHB-O1 (3-1) 3%
3-HBB-2 (3-4) 3%
V2-H2B(2F,3F)-O2 (11-4) 8%
V2-H1OB(2F,3F)-O4 (11-5) 4%
3-BB(2F,3F)-O2 (11-3) 7%
2-HHB(2F,3F)-O2 (12-1) 7%
3-HHB(2F,3F)-O2 (12-1) 7%
3-HH2B(2F,3F)-O2 (12-4) 7%
5-HH2B(2F,3F)-O2 (12-4) 4%
V-HH2B(2F,3F)-O2 (12-4) 6%
V2-HBB(2F,3F)-O2 (12-7) 5%
V-HBB(2F,3F)-O2 (12-7) 5%
V-HBB(2F,3F)-O4 (12-7) 6%
NI=89.9° C.; Δn=0.122; Δε=−4.2;

[Composition M28]
3-HH-V (2-1) 27%
3-HH-V1 (2-1) 6%
V-HHB-1 (3-1) 3%
3-HB(2F,3F)-O2 (11-1) 3%
V-HB(2F,3F)-O2 (11-1) 3%
V2-HB(2F,3F)-O2 (11-1) 5%
V2-BB(2F,3F)-O2 (11-3) 3%
1V2-BB(2F,3F)-O2 (11-3) 3%
5-H2B(2F,3F)-O2 (11-4) 5%
3-HHB(2F,3F)-O2 (12-1) 6%
V-HHB(2F,3F)-O2 (12-1) 6%
V-HHB(2F,3F)-O4 (12-1) 5%
V2-HHB(2F,3F)-O2 (12-1) 4%
V-HHB(2F,3Cl)-O2 (12) 3%
V2-HBB(2F,3F)-O2 (12-7) 5%
V-HBB(2F,3F)-O2 (12-7) 4%
V-HBB(2F,3F)-O4 (12-7) 5%
V2-BB (2F, 3F) B-1 (13-1) 4%
NI=77.1° C.; Δn=0.101; Δε=−3.0;

[Composition M29]
3-HH-4 (2-1) 14%
V-HHB-1 (3-1) 10%
3-HBB-2 (3-4) 7%
V-HB(2F,3F)-O2 (11-1) 10%
V2-HB(2F,3F)-O2 (11-1) 10%
2O-BB(2F,3F)-O2 (11-3) 3%
V2-BB(2F,3F)-O2 (11-3) 8%
2-H1OB(2F,3F)-O2 (11-5) 3%
3-H1OB(2F,3F)-O2 (11-5) 3%
V2-HHB(2F,3F)-O2 (12-1) 5%
V-HHB(2F,3Cl)-O2 (12) 7%
2-HBB(2F,3F)-O2 (12-7) 3%
3-HBB(2F,3F)-O2 (12-7) 3%
V-HBB(2F,3F)-O2 (12-7) 6%
V-HBB(2F,3F)-O4 (12-7) 8%
NI=75.9° C.; Δn=0.114; Δε=-3.9;

[Composition M30]
2-HH-3 (2-1) 20%
3-HH-4 (2-1) 6%
3-HB-O2 (2-5) 3%
3-HHB-O1 (3-1) 3%
3-HHB-3 (3-1) 6%
3-HHB-1 (3-1) 6%
3-HBB-2 (3-4) 10%
3-HB(2F,3F)-O2 (11-1) 12%
5-BB(2F,3F)-O2 (11-3) 4%
3-BB(2F,3F)-O2 (11-3) 10%
3-HDhB(2F,3F)-O2 (12-3) 12%
3-dhBB(2F,3F)-O2 (12-9) 8%
NI=75.9° C.; Δn=0.101; Δε=−2.7.

[Composition M31]
2-HH-3 (2-1) 18%
3-HH-4 (2-1) 3%
3-HH-5 (2-1) 3%
2-HH-5 (2-1) 2%
3-HB-O2 (2-5) 17%
3-HBB-2 (3-4) 10%
2-H1OB(2F,3F)-O2 (11-5) 7%
3-H1OB(2F,3F)-O2 (11-5) 7%
3-HHB(2F,3F)-O2 (12-1) 4%
2-HBB(2F,3F)-O2 (12-7) 4%
3-HBB(2F,3F)-O2 (12-7) 8%
4-HBB(2F,3F)-O2 (12-7) 4%
5-HBB(2F,3F)-O2 (12-7) 9%
3-dhBB(2F,3F)-O2 (12-9) 4%
NI=78.4° C.; Δn=0.105; Δε=−2.7;

[Composition M32]
2-HH-3 (2-1) 22%
3-HH-4 (2-1) 4%
3-HB-O2 (2-5) 10%
3-HBB-2 (3-4) 14%
2-H1OB(2F,3F)-O2 (11-5) 10%
3-H1OB(2F,3F)-O2 (11-5) 10%
2-HHB(2F,3F)-O2 (12-1) 3%
3-HHB(2F,3F)-O2 (12-1) 9%
5-HHB(2F,3F)-O2 (12-1) 3%
2-HBB(2F,3F)-O2 (12-7) 3%
3-HBB(2F,3F)-O2 (12-7) 8%
4-HBB(2F,3F)-O2 (12-7) 4%
NI=76.0° C.; Δn=0.097; Δε=−3.0;

[Composition M33]
2-HH-3 (2-1) 21%
3-HH-4 (2-1) 5%
3-HH-5 (2-1) 6%
1-BB-3 (2-8) 4%
1-BB-5 (2-8) 10.5%
3-H1OB(2F,3F)-O2 (11-5) 10.5%
3-HHB(2F,3F)-O2 (12-1) 6%
V-HHB(2F,3F)-O2 (12-1) 12%
3-HBB(2F,3F)-O2 (12-7) 10%
V-HBB(2F,3F)-O2 (12-7) 8%
V-HBB(2F,3F)-O4 (12-7) 7%
NI=75.3° C.; Δn=0.109; Δε=-3.1;

[Composition M34]
2-HH-3 (2-1) 25%
1-BB-2 (2-8) 15%
1-BB-3 (2-8) 4%
3-HHB-1 (3-1) 6%
3-HBB-2 (3-4) 8%
3-H1OB(2F,3F)-O2 (11-5) 8%
3-HHB(2F,3F)-O2 (12-1) 8%
3-HH1OB(2F,3F)-O2 (12-5) 26%
NI=73.5° C.; Δn=0.100; Δε=-2.6.

[Composition M35]
3-DhB(2F,3F)-O2 (11-2) 7%
2-HHB(2F,3F)-O2 (12-1) 3%
3-HHB(2F,3F)-O2 (12-1) 9%
5-HHB(2F,3F)-O2 (12-1) 9%
3-HDhB(2F.3F)-O2 (12-3) 10%
2-HBB(2F,3F)-O2 (12-7) 3%
3-HBB(2F,3F)-O2 (12-7) 8%
5-HFLF4-3 (19-1) 3%
2-HH-3 (2-1) 22%
3-HH-4 (2-1) 4%
3-HH-5 (2-1) 4%
1-BB-3 (2-8) 4%
1-BB-5 (2-8) 12%
3-HHB-1 (3-1) 2%
NI=74.8° C.; Δn=0.099; Δε=−3.2.

[Composition M36]
2-HH-3 (2-1) 18%
V-HH-V (2-1) 8%
3-HB-O2 (2-5) 17%
3-HBB-2 (3-4) 10%
2-H1OB(2F,3F)-O2 (11-5) 7%
3-H1OB(2F,3F)-O2 (11-5) 7%
3-dhBB(2F,3F)-O2 (12-9) 4%
3-HB(2F)B(2F,3F)-O2
(12) 9%
3-HHB(2F,3F)-O2 (12-1) 4%
2-HBB(2F,3F)-O2 (12-7) 4%
3-HBB(2F,3F)-O2 (12-7) 8%
4-HBB(2F,3F)-O2 (12-7) 4%
NI=71.1° C.; Δn=0.105; Δε=−2.7.

[Composition M37]
2-HH-3 (2-1) 19%
3-HH-4 (2-1) 5%
3-HH-5 (2-1) 4%
1-BB-3 (2-8) 4%
1-BB-5 (2-8) 16%
3-HHB-1 (3-1) 2.5%
3-HBB-2 (3-4) 8%
3-dhBB(2F,3F)-O2 (12-9) 6%
3-H1OB(2F,3F)-O2 (11-5) 8%
3-HHB(2F,3F)-O2 (12-1) 7.5%
3-HH1OB(2F,3F)-O2 (12-5) 20%
NI=75.6° C.; Δn=0.104; Δε=−2.4.

[Composition M38]
3-HH-V (2-1) 29%
2-HH-3 (2-1) 2%
V-HHB-1 (3-1) 5%
V-HBB-2 (3-4) 14%
3-HB(2F,3F)-O2 (11-1) 12%
5-HB(2F,3F)-O2 (11-1) 8%
2O-B(2F)B(2F,3F)-O2
(11-9) 5%
3-HH2B(2F,3F)-O2 (12-4) 9%
3-HDhB(2F,3F)-O2 (12-3) 9%
3-dhBB(2F,3F)-O2 (12-9) 7%
NI=76.5° C.; Δn=0.098; Δε=−3.0;

[Composition M39]
3-HH-V (2-1) 20%
2-HH-3 (2-1) 10%
3-HH-4 (2-1) 6%
3-HB-O2 (2-5) 7%
1-BB-3 (2-8) 4%
5-B(F)BB-2 (3-6) 7%
2O-B(2F)B(2F,3F)-O2
(11-9) 7%
2O-B (2F) B (2F, 3F)-O4
(11-9) 7%
2-HHB(2F,3F)-O2 (12-1) 3%
3-HHB(2F,3F)-O2 (12-1) 6%
V-HHB(2F,3F)-O1 (12-1) 4%
V-HHB(2F,3F)-O2 (12-1) 10%
3-HH2B(2F,3F)-O2 (12-4) 9%
NI=75.3° C.; Δn=0.102; Δε=-2.6;

The following polymerizable compounds (RM-1) to (RM-9) were used.

2. Orientation of liquid crystal display device [Comparative Example 1]
For comparison, the polymerizable compound (RM-1) was added to the composition (M1) at a ratio of 1.0% by mass. The liquid crystal composition of the present invention to which this polar compound was added was enclosed in a VA element of a glass substrate having no alignment film, and the vertical alignment of the composition on the substrate was confirmed. As a result, no vertical alignment was exhibited. ..
[Example 1]
The compound No. 13 as the compound (1) was added to the composition (M1) at a ratio of 1.0% by mass. The liquid crystal composition of the present invention to which this compound (1) was added was enclosed in a VA element of a glass substrate having no alignment film, and the vertical alignment of the composition on the substrate was confirmed. It was

[Examples 2 to 39]
As shown in Tables 3-1 to 3-3, liquid crystal compositions were prepared by changing the type of composition and the types and concentrations of polar compounds and polymerizable compounds. In these tables, "%" is% by mass, "No. 13" means the compound of No. 13, "polar compound" means a polar compound other than the formula (1), and a polar compound. And the like, "21-1" and the like represent a preferable polar compound such as formula (21-1), and "RM-1" and the like described as the polymerizable compound include the above formula (RM- 1) and the like, and “−” means that the component is not included.
Vertical alignment was confirmed by the same method as in Example 1. The results are summarized in Tables 3-4 to 3-6, in which the case where the vertical alignment is shown is “◯”, and the case where the vertical alignment is not shown is “x”.

Table 3-1

Table 3-2

Table 3-3

Table 3-4

Table 3-5

Table 3-6

From the results of Tables 3-4 to 3-6, the device using the liquid crystal composition containing the compound (1) showed vertical alignment. On the other hand, the device using the composition to which the compound (1) was not added did not show vertical alignment. Further, in the liquid crystal compositions of Examples 15 to 30, polar compounds (21-1) to (24-6) and polymerizable compounds (RM-1) to (RM-9) were further added, but similar results were obtained. Was obtained. This result shows that the compound (1) of the present invention has a vertical alignment property in a liquid crystal display device.

[Example 40]
The compound of No. 1 as the compound (1) was added to the composition (M1) at a ratio of 1.0% by mass. The liquid crystal composition of the present invention to which this compound (1) was added was enclosed in a VA element of a glass substrate having no alignment film, and the vertical alignment of the composition on the substrate was confirmed. It was

[Examples 41 to 78]
As shown in Tables 3-7 to 3-9, liquid crystal compositions were prepared by changing the type of composition and the types and concentrations of polar compounds and polymerizable compounds. In these tables, "%" is% by mass, "No. 1" means the compound of No. 1, "polar compound" means a polar compound other than the formula (1), and a polar compound. And the like, "21-1" and the like represent a preferable polar compound such as formula (21-1), and "RM-1" and the like described as the polymerizable compound include the above formula (RM- 1) and the like, and “−” means that the component is not included.
Vertical alignment was confirmed by the same method as in Example 40. The results are summarized in Tables 3-10 to 3-12, in which the case where the vertical orientation is shown is “◯” and the case where the vertical orientation is not shown is “x”.

Table 3-7

Table 3-8

Table 3-9

Table 3-10

Table 3-11

Table 3-12

From the results of Tables 3-10 to 3-12, the device using the liquid crystal composition containing the compound (1) exhibited vertical alignment. On the other hand, the device using the composition to which the compound (1) was not added did not show vertical alignment. Further, in the liquid crystal compositions of Examples 54 to 78, polar compounds (21-1) to (24-6) and polymerizable compounds (RM-1) to (RM-9) were further added, but similar results were obtained. Was obtained. This result shows that the compound (1) of the present invention has a vertical alignment property in a liquid crystal display device.

The liquid crystal composition of the present invention can control the alignment of liquid crystal molecules in an element having no alignment film. A liquid crystal display device containing this composition has characteristics such as a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long life, so that it can be used for a liquid crystal projector, a liquid crystal television and the like. ..

Claims (19)

A compound represented by the formula (1).

In equation (1),
R ¹ , R ² and R ³ are independently hydrogen, —Sp—P, or alkyl having 1 to 15 carbons, and in this R ¹ , R ² and R ³ , at least one —CH ₂ — is , —O— or —S—, at least one —(CH ₂ ) ₂ — may be replaced with —CH═CH— or —C≡C—, and at least one hydrogen is , May be replaced by fluorine or chlorine;
Ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are independently 1,2-cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,4-cyclohexylene, 1 ,4-cycloheptylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2, 6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, ring A ¹ , ring A ² , in ring A ³ and ring A ⁴ , at least one hydrogen is fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or 2 to 9 carbons. Alkenyloxy, or -Sp-P, at least one hydrogen may be replaced by fluorine or chlorine, and a plurality of ring A ¹ , ring A ² and ring A ³ are present in the structure. Each may be different, if
a and b are independently 0, 1, 2 or 3 and c is 1, 2, 3 or 4;
Z ¹ , Z ² and Z ³ are independently a single bond or alkylene having 1 to 6 carbon atoms, and in this Z ¹ , Z ² and Z ³ , at least one —CH ₂ — is —O—, May be replaced by —CO—, —COO—, —OCO—, or —OCOO—, where at least one —(CH ₂ ) ₂ — is replaced by —CH═CH— or —C≡C—. Or at least one hydrogen may be replaced by fluorine or chlorine, and when there are multiple Z ¹ , Z ² and Z ³ in the structure, each may be different;
In —Sp—P, Sp is a single bond or alkylene having 1 to 10 carbon atoms, and in this Sp, at least one —CH ₂ — is —O—, —CO—, —COO—, —OCO—, Or —OCOO—, at least one —(CH ₂ ) ₂ — may be replaced by —CH═CH— or —C≡C—, and at least one hydrogen is fluorine or chlorine. Each may be different when there are multiple Sp in the structure;
In -Sp-P, P is a group represented by any one of formula (1b) to formula (1h), and when a plurality of P are present in the structure, each may be different, but at least One P is a group in which R ⁴ in formula (1b) is —CH ₂ OCH ₃ or —CH ₂ OH;

In formulas (1b) to (1h),
M ¹ , M ² , M ³ and M ⁴ are independently hydrogen, halogen, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen has been replaced by halogen;
R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are independently hydrogen or alkyl having 1 to 15 carbons, and R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁸ In R ⁹ , at least one —CH ₂ — may be replaced by —O— or —S—, and at least one —(CH ₂ ) ₂ — is —CH═CH— or —C≡C—. May be replaced by and at least one hydrogen may be replaced by halogen. In equation (1),
Z ¹ , Z ² and Z ³ are independently a single bond, —(CH ₂ ) ₂ —, —(CH ₂ ) ₄ —, —CH═CH—, —C≡C—, —COO—, —OCO. _{-, - CF 2 O -,} - OCF 2 -, - CH 2 O -, - OCH 2 -, or -CF = CF-, a compound of claim 1. In equation (1),
Ring A ¹ , Ring A ² , Ring A ³ and Ring A ⁴ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydro Pyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, wherein ring A ¹ , ring A ² , ring A ³ And in ring A ⁴ , at least one hydrogen is fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or alkenyloxy having 2 to 9 carbons. 3. A compound according to claim 1 or 2 which may be replaced and at least one hydrogen may be replaced by fluorine or chlorine. In equation (1),
The compound according to any one of claims 1 to 3, wherein R ¹ and R ² are -Sp-P, and R ³ is alkyl having 1 to 15 carbons, hydrogen or -Sp-P. In equation (1),
P is the formula (1b-1), (1b-2), (1b-3), (1b-4), formula (1b-5), (1c-1), (1d-1), (1d-2) ) Or (1e-1), and when a plurality of Ps are present in the structure, each may be different, provided that at least one P is represented by the formula (1b-4) or (1b- 5) The compound according to any one of claims 1 to 4, which is

In the described formula (1),
a and b are independently 0, 1 or 2, provided that a+b is 3 or less, c is 1, 2 or 3, and ring A ¹ , ring A ² , ring A ³ and ring A ⁴ are independent. And the compound is 1,4-cyclohexylene or 1,4-phenylene, and Z ¹ , Z ² and Z ³ are single bonds, and the compound according to any one of claims 1 to 5. The compound according to any one of claims 1 to 6, which is represented by any one of formulas (1-1) to (1-10).

In formulas (1-1) to (1-10), R ³ is alkyl having 1 to 10 carbons, hydrogen or —Sp ³ —P ³ , and ring A ¹ , ring A ² , ring A ³ , Ring A ⁴ and ring A ⁵ are independently 1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5-diyl, and ring A ¹ , ring A ² , ring A ³ , In ring A ⁴ and ring A ⁵ ,
At least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 5 carbons, alkenyl having 2 to 5 carbons, alkoxy having 1 to 5 carbons, or alkenyloxy having 2 to 5 carbons, When a plurality of rings A ¹ are present in the structure, each may be different, and Sp ¹ , Sp ² and Sp ³ are independently a single bond or an alkylene having 1 to 10 carbons, and Sp ¹ , Sp ² and Sp ³ , at least one —CH ₂ — may be replaced with —O—, —CO—, —COO—, —OCO—, or —OCOO—, and at least one —(CH ₂ ) ₂ — may be replaced by —CH═CH— or —C≡C—, and P ¹ , P ² and P ³ are independently of the formulas (1b-1), (1b-2), A group represented by formula (1b-3), (1b-4), formula (1b-5), (1c-1), (1d-1), (1d-2) or (1e-1), If more than one P is present in the structure, each may be different, provided that at least one P is of formula (1b-4) or (1b-5).

The compound according to any one of claims 1 to 7, which is represented by any one of formulas (1-11) to (1-32).

In formulas (1-11) to (1-32), R ³ is alkyl having 1 to 10 carbons, hydrogen or —Sp ³ —P ³ , and Sp ¹ , Sp ² and Sp ³ are independently , A single bond or alkylene having 1 to 10 carbons, wherein in Sp ¹ , Sp ² and Sp ³ , at least one —CH ₂ — is replaced with —O—, —COO—, or —OCO— Alternatively, at least one —(CH ₂ ) ₂ — may be replaced by —CH═CH— or —C≡C—, and P ¹ , P ² and P ³ are independently of the formula (1b- 1), (1b-2), (1b-3), (1b-4), formula (1b-5), (1c-1), (1d-1), (1d-2) or (1e-1) When a plurality of Ps are present in the structure, each of them may be different, provided that at least one P is the formula (1b-4) or (1b-5).

A liquid crystal composition containing at least one of the compounds according to any one of claims 1 to 8. The liquid crystal composition according to claim 9, containing at least one compound selected from the group of compounds represented by formulas (2) to (4).

In equations (2) to (4),
R ¹¹ and R ¹² are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in this R ¹¹ and R ¹² , at least one —CH ₂ — is replaced with —O— And at least one hydrogen may be replaced by fluorine;
Ring B ¹ , Ring B ² , Ring B ³ , and Ring B ⁴ are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro- 1,4-phenylene or pyrimidine-2,5-diyl;
Z ¹¹ , Z ¹² and Z ¹³ are independently a single bond, —COO—, —CH ₂ CH ₂ —, —CH═CH—, or —C≡C—. The liquid crystal composition according to claim 9 or 10, containing at least one compound selected from the group of compounds represented by formulas (5) to (7).

In equations (5) to (7),
R ¹³ is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in this R ¹³ , at least one —CH ₂ — may be replaced by —O—, and at least one hydrogen is fluorine. May be replaced with;
X ¹¹ is fluorine, chlorine, —OCF ₃ , —OCHF ₂ , —CF ₃ , —CHF ₂ , —CH ₂ F, —OCF ₂ CHF ₂ , or —OCF ₂ CHFCF ₃ ;
Ring C ¹ , Ring C ² , and Ring C ³ are independently 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl. , Pyrimidine-2,5-diyl, or 1,4-phenylene having at least one hydrogen replaced by fluorine;
Z ¹⁴ , Z ¹⁵ and Z ¹⁶ are independently a single bond, —COO—, —OCO—, —CH ₂ O—, —OCH ₂ —, —CF ₂ O—, —OCF ₂ —, —CH ₂ CH ₂ —, —CH═CH—, —C≡C—, or —(CH ₂ ) ₄ —;
L ¹¹ and L ¹² are independently hydrogen or fluorine. The liquid crystal composition according to any one of claims 9 to 11, containing at least one compound selected from the group of compounds represented by formula (8).

In equation (8),
R ¹⁴ is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in this R ¹⁴ , at least one —CH ₂ — may be replaced by —O—, and at least one hydrogen is fluorine. May be replaced with;
X ¹² is —C≡N or —C≡C—C≡N;
Ring D ¹ is 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or at least 1 1,4-phenylene with one hydrogen replaced by fluorine;
Z ¹⁷ is a single bond, —COO—, —OCO—, —CH ₂ O—, —OCH ₂ —, —CF ₂ O—, —OCF ₂ —, —CH ₂ CH ₂ —, or —C≡C—. And
L ¹³ and L ¹⁴ are independently hydrogen or fluorine;
i is 1, 2, 3, or 4. The liquid crystal composition according to any one of claims 9 to 12, containing at least one compound selected from the group of compounds represented by formulas (11) to (19).

In equations (11) to (19),
R ¹⁵ , R ¹⁶ and R ¹⁷ are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in R ¹⁵ , R ¹⁶ and R ¹⁷ , at least one —CH ₂ -May be replaced by -O-, at least one hydrogen may be replaced by fluorine, and R ¹⁷ may be hydrogen or fluorine;
Ring E ¹ , ring E ² , ring E ³ and ring E ⁴ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl. , Decahydronaphthalene-2,6-diyl, or 1,4-phenylene in which at least one hydrogen has been replaced by fluorine;
Ring E ⁵ and ring E ⁶ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6. -Is Jail;
Z ¹⁸ , Z ¹⁹ , Z ²⁰ and Z ²¹ are independently a single bond, —COO—, —OCO—, —CH ₂ O—, —OCH ₂ —, —CF ₂ O—, —OCF ₂ —, —CH ₂ CH ₂ —, —CF ₂ OCH ₂ CH ₂ —, or —OCF ₂ CH ₂ CH ₂ —;
L ¹⁵ and L ¹⁶ are independently fluorine or chlorine;
S ¹¹ is hydrogen or methyl;
X is —CHF— or —CF ₂ —;
j, k, m, n, p, q, r, and s are independently 0 or 1, and the sum of k, m, n, and p is 1 or 2, q, r, and the sum of s is 0, 1, 2, or 3,
t is 1, 2, or 3. 14. The liquid crystal composition according to claim 9, containing at least one polymerizable compound represented by formula (20).

In equation (20),
Ring F and ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxan-2-yl, pyrimidin-2-yl, or pyridine. -2-yl, and in Ring F and Ring I, at least one hydrogen is halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or carbon in which at least one hydrogen is replaced by halogen. It may be replaced by an alkyl of the numbers 1 to 12;
Ring G is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, Naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene- 2,7-diyl, phenanthrene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5- Diyl, and in ring G, at least one hydrogen is halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen. May be replaced with;
Z ²² and Z ²³ are independently a single bond or alkylene having 1 to 10 carbon atoms, and in Z ²² and Z ²³ , at least one —CH ₂ — is —O—, —CO—, —COO. Or at least one —CH ₂ CH ₂ — is —CH═CH—, —C(CH ₃ )═CH—, —CH═C(CH ₃ )—, Or may be replaced with -C(CH ₃ )=C(CH ₃ )- and at least one hydrogen may be replaced with fluorine or chlorine;
P ¹¹ , P ¹² and P ¹³ are independently a polymerizable group;
Sp ¹¹ , Sp ¹² and Sp ¹³ are independently a single bond or an alkylene having 1 to 10 carbons, and in this Sp ¹¹ , Sp ¹² and Sp ¹³ , at least one —CH ₂ — is —O. -, -COO-, -OCO-, or -OCOO-, and at least one -CH ₂ CH ₂ -may be replaced by -CH=CH- or -C≡C-, At least one hydrogen may be replaced by fluorine or chlorine;
u is 0, 1, or 2;
f, g, and h are independently 0, 1, 2, 3, or 4, and the sum of f, g, and h is 1 or more. 15. The liquid crystal composition according to claim 9, containing at least one compound selected from compounds represented by formulas (21) to (24).

In formulas (21), (22), (23) and (24), R ⁵⁰ is hydrogen, fluorine, chlorine, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or R 2 having 2 to 12 carbons. Alkenyl, alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced by fluorine;
R ⁵¹ is a group represented by —OH, —NH ₂ , —OR ⁵³ , —N(R ⁵³ ) ₂ , or —Si(R ⁵³ ) ₃ , where R ⁵³ is hydrogen or the number of carbon atoms. 1 to 7 alkyl, in which R ⁵³ , at least one —CH ₂ — may be replaced by —O—, and at least one —CH ₂ CH ₂ — may be replaced by —CH═CH—. At least one hydrogen may be replaced by fluorine;
R ⁵² is hydrogen, fluorine, or alkyl having 1 to 5 carbons, and in this R ⁵² , at least one —CH ₂ — may be replaced by —O—, and at least one hydrogen is fluorine or May be replaced by chlorine;
Ring A ⁵⁰ and ring B ⁵⁰ are 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3 -Dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, wherein in ring A ⁵⁰ and ring B ⁵⁰ , at least one hydrogen is fluorine, carbon number 1 to 12 alkyl, 1-12 alkoxy, or at least one hydrogen may be replaced by 1-12 alkyl in which fluorine is replaced;
Z ⁵⁰ represents a single bond, —CH ₂ CH ₂ —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF ₂ O—, —OCF ₂ —, —CH ₂ O—. , —OCH ₂ —, or —CF═CF—;
Sp ⁵¹ , Sp ⁵² , Sp ⁵³ and Sp ⁵⁴ are a single bond or an alkylene having 1 to 7 carbon atoms, and in this Sp ⁵¹ , Sp ⁵² , Sp ⁵³ and Sp ⁵⁴ , at least one —CH ₂ — is — May be replaced by O—, —COO—, or —OCO—, at least one —CH ₂ CH ₂ — may be replaced by —CH═CH—, and at least one hydrogen may be replaced by fluorine. May be given;
a ⁵⁰ is 0, 1, 2, 3, or 4;
a ⁵¹ is 1 or 2;
l is 0, 1, 2, 3, 4, 5, or 6, and at least one —CH ₂ — of —(CH ₂ ) _l — is —O—, —CO—, —COO—, —OCO—, or —OCOO—, at least one —CH ₂ CH ₂ — may be replaced with —CH═CH— or —C≡C—, and at least one hydrogen is It may be replaced by fluorine. In equation (20),
15. The group according to claim 14, wherein P ¹¹ , P ¹² and P ¹³ are independently a group selected from the group of polymerizable groups represented by formula (P-1) to formula (P-5). Liquid crystal composition.

In formula (P-1) to formula (P-5),
M ¹¹ , M ¹² and M ¹³ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons or alkyl having 1 to 5 carbons in which at least one hydrogen has been replaced by halogen. 15. The polymerizable compound represented by the formula (20) is at least one compound selected from the group of polymerizable compounds represented by the formula (20-1) to the formula (20-7). 17. The liquid crystal composition according to any one of 16.

In equation (20-1) to equation (20-7),
L ³¹ , L ³² , L ³³ , L ³⁴ , L ³⁵ , L ³⁶ , L ³⁷ , and L ³⁸ are independently hydrogen, fluorine, or methyl;
Sp ¹¹ , Sp ¹² and Sp ¹³ are independently a single bond or an alkylene having 1 to 10 carbons, and in this Sp ¹¹ , Sp ¹² and Sp ¹³ , at least one —CH ₂ — is —O. -, -COO-, -OCO-, or -OCOO-, and at least one -CH ₂ CH ₂ -may be replaced by -CH=CH- or -C≡C-, At least one hydrogen may be replaced by fluorine or chlorine.
P ¹¹ , P ¹² , and P ¹³ are independently a group selected from the group of polymerizable groups represented by formula (P-1) to formula (P-3),

In formula (P-1) to formula (P-3),
M ¹¹ , M ¹² and M ¹³ are independently hydrogen, fluorine, alkyl having 1 to 5 carbons or alkyl having 1 to 5 carbons in which at least one hydrogen has been replaced by halogen. It contains at least one selected from the group of polymerizable compounds, polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, dyes, and defoamers. The liquid crystal composition according to any one of claims 9 to 17. At least one selected from the group consisting of the liquid crystal composition according to any one of claims 9 to 18 and a polymer in which at least a part of the liquid crystal composition according to any one of claims 9 to 18 is polymerized. Liquid crystal display element containing one.