JP6511975B2 - Liquid crystal composition and liquid crystal display device containing dihydropyran compound - Google Patents

Description

  The present invention relates to a liquid crystal composition and a liquid crystal display device. More specifically, the present invention relates to a liquid crystal composition containing a dihydropyran compound, and a liquid crystal display device including the composition. It also relates to dihydropyran compounds.

  In liquid crystal display devices, classification based on the operation mode of liquid crystal molecules is as follows: phase change (PC), twisted nematic (TN), super twisted nematic (STN), electrically controlled birefringence (ECB), optically compensated bend (OCB), IPS These modes are modes such as (in-plane switching), VA (vertical alignment), FFS (fringe field switching), and FPA (field-induced photo-reactive alignment). The classification based on the driving system of elements is PM (passive matrix) and AM (active matrix). PM is classified into static, multiplex, etc., and AM is classified into thin film transistor (TFT), metal insulator metal (MIM), etc. The classification of TFT is amorphous silicon and polycrystal silicon. The latter are classified into high temperature type and low temperature type according to the manufacturing process. Source based classifications are reflective based on natural light, transmissive based on back light, and semi-transmissive based on both natural light and back light.

  The liquid crystal display device includes a liquid crystal composition having a nematic phase. This composition has appropriate physical properties. By improving the physical properties of this composition, an AM element having good characteristics can be obtained. The two associations are summarized in Table 1 below. The physical properties of the composition will be further described based on commercially available AM devices. The temperature range of the nematic phase is related to the usable temperature range of the device. The preferred upper temperature limit of the nematic phase is about 70 ° C. or higher, and the preferred lower temperature limit of the nematic phase is about -10 ° C. or lower. The viscosity of the composition is related to the response time of the device. Short response times are preferred for displaying motion pictures on the device. Even shorter response times of 1 millisecond are desirable. Thus, low viscosity in the composition is preferred. Small viscosities at low temperatures are more preferred.

  The optical anisotropy of the composition is related to the contrast ratio of the device. Depending on the mode of the device, a large or small optical anisotropy, ie a suitable 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 value of the product depends on the type of operating mode. A composition having large optical anisotropy is preferable for a small cell gap device. The large dielectric anisotropy in the composition contributes to low threshold voltage, low power consumption and high contrast ratio in the device. Therefore, positive or negative large dielectric anisotropy is preferred. The large resistivity in the composition contributes to a large voltage holding ratio and a large contrast ratio in the device. Therefore, compositions having high specific resistance not only at room temperature but also at high temperatures in the initial stage are preferred. After prolonged use, compositions having high specific resistance not only at room temperature but also at high temperatures are preferred. The stability of the composition to ultraviolet light or heat is related to the lifetime of the device. When this stability is high, the lifetime of the device is long. Such characteristics are preferable for an AM element used for a liquid crystal projector, a liquid crystal television or the like.

  In a liquid crystal display device of the polymer supported alignment (PSA) type, a liquid crystal composition containing a polymer is used. First, a composition to which a small amount of a polymerizable compound is added is injected into the device. Next, the composition is irradiated with ultraviolet light while applying a voltage between the substrates of the device. The polymerizable compound polymerizes to form a polymer network in the composition. In this composition, the polymer can control the alignment of liquid crystal molecules, thereby reducing the response time of the device and improving the image sticking. Such an effect of the polymer can be expected to devices having modes such as TN, ECB, OCB, IPS, VA, FFS, and FPA.

  The liquid crystal composition is prepared by mixing liquid crystal compounds. Many liquid crystal compounds have been synthesized so far. Development of new liquid crystalline compounds is still continued. This is because the novel compound is expected to have excellent physical properties which are not present in conventional compounds. By adding the novel compound to the liquid crystal composition, it is expected that an appropriate balance can be obtained between at least two physical properties in the composition.

There are few reported examples of the following physical properties of a compound having a divalent group and liquid crystal compositions containing this compound.

WO 2006/125526 A discloses the following compound (4-12b) on page 37: This compound is a synthetic intermediate.

JP-A-2011-136914 discloses the following compound in paragraph 0257. This compound is a synthetic intermediate.

  The first component of the composition of the present invention is a dihydropyran compound. This compound has positive, negative or neutral dielectric anisotropy depending on the structure. Such three compounds are similar in structure to each other and thus have excellent compatibility. Therefore, a composition having positive dielectric anisotropy can be prepared by mixing compounds having positive and negative dielectric anisotropy. A composition having negative dielectric anisotropy can be prepared by mixing compounds having negative dielectric anisotropy and neutral. While taking advantage of this advantage, we have developed liquid crystal compositions with positive or negative dielectric anisotropy.

WO 2006/125526 JP, 2011-136914, A

  The first subject of the present invention contains a dihydropyran compound, and has a high upper limit temperature of nematic phase, a lower lower limit temperature of nematic phase, small viscosity, appropriate optical anisotropy, positive or negative large dielectric constant anisotropy It is an object of the present invention to provide a liquid crystal composition satisfying at least one of physical properties such as elasticity, high specific resistance, high stability to ultraviolet light or heat, and a suitable elastic constant. The second problem is to provide a liquid crystal display device comprising the composition and having a wide temperature range in which the device can be used, a short response time, a high voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long lifetime. It is to be. The third problem is high stability against heat and light, high clearing point (or high upper limit temperature of nematic phase), lower lower limit temperature of liquid crystal phase, small viscosity, appropriate optical anisotropy, positively large dielectric constant difference It is an object of the present invention to provide a liquid crystal compound which satisfies at least one of physical properties such as linearity, an appropriate elastic constant, and excellent compatibility with other liquid crystal compounds. It is an object of the present invention to provide a compound having a significantly large dielectric anisotropy as compared with a similar compound. It is to provide a compound having excellent compatibility as compared with a similar compound.

  The present invention contains a compound represented by the formula (1) as the first component, a compound represented by the formulas (2) to (4) as the second component, and a liquid crystal composition having a nematic phase, the composition A liquid crystal display element including an object. The chemical formulas of Formula (1) and Formulas (2) to (4) will be described in the subsequent paragraphs.

  The first advantage of the present invention is that it contains a dihydropyran compound, and has a high upper limit temperature of nematic phase, a lower lower limit temperature of nematic phase, a small viscosity, a suitable optical anisotropy, a positive or negative large dielectric constant anisotropy It is an object of the present invention to provide a liquid crystal composition satisfying at least one of physical properties such as elasticity, high specific resistance, high stability to ultraviolet light or heat, and a suitable elastic constant. The second advantage is to provide a liquid crystal display device comprising the composition and having a wide temperature range in which the device can be used, a short response time, a high voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long lifetime. It is to be. The third advantage is high stability to heat and light, high clearing point (or high upper limit temperature of nematic phase), lower lower limit temperature of liquid crystal phase, small viscosity, appropriate optical anisotropy, positively large dielectric constant difference It is an object of the present invention to provide a liquid crystal compound which satisfies at least one of physical properties such as linearity, an appropriate elastic constant, and excellent compatibility with other liquid crystal compounds. It is an object of the present invention to provide a compound having a significantly large dielectric anisotropy as compared with a similar compound.

  The usage of the terms in this specification is as follows. The terms "liquid crystal compound", "liquid crystal composition" and "liquid crystal display element" may be abbreviated as "compound", "composition" and "element", respectively. "Liquid crystalline compound" is a compound having a liquid crystal phase such as a nematic phase or smectic phase, and has no liquid crystal phase, but controls physical properties of the composition such as upper limit temperature, lower limit temperature, viscosity, dielectric anisotropy Is a generic term for compounds added for the purpose of This compound has a 6-membered ring such as 1,4-cyclohexylene and 1,4-phenylene, and its molecular structure is rod like. "Liquid crystal display element" is a generic term for liquid crystal display panels and liquid crystal display modules. The "polymerizable compound" is a compound to be added for the purpose of forming a polymer in the composition.

  The liquid crystal composition is prepared by mixing a plurality of liquid crystal compounds. The proportion (content) of the liquid crystal compound is expressed as a weight percentage (% by weight) based on the weight of the liquid crystal composition. In this composition, additives such as a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, a pigment, and an antifoaming agent are required. Is added accordingly. The proportion (addition amount) of the additive is represented by a weight percentage (% by weight) based on the weight of the liquid crystal composition, similarly to the proportion of the liquid crystal compound. Parts per million by weight (ppm) may be used. The proportion of polymerization initiator or polymerization inhibitor is exceptionally expressed based on the weight of the polymerizable compound.

  The "clearing point" is the transition temperature of the liquid crystal phase-isotropic phase in the liquid crystal compound. The “lower limit temperature of the liquid crystal phase” is a transition temperature of a solid-liquid crystal phase (eg, smectic phase, nematic phase) in a liquid crystal compound. The “upper limit temperature of the nematic phase” is a transition temperature of the nematic phase-isotropic phase in the mixture of the liquid crystal compound and the base liquid crystal or the liquid crystal composition, and may be abbreviated as the “upper limit temperature”. The “lower limit temperature of the nematic phase” may be abbreviated as the “lower limit temperature”. The expression "increase the dielectric anisotropy" means that in the case of a composition having a positive dielectric anisotropy, the value increases positively, and a composition having a negative dielectric anisotropy. In the case of goods, it means that the value increases negatively.

The compound represented by Formula (1) may be abbreviated as a compound (1). At least one compound selected from the group of compounds represented by formula (1) may be abbreviated as compound (1). "Compound (1)" means one compound represented by Formula (1), a mixture of two compounds, or a mixture of three or more compounds. These rules also apply to compounds represented by other formulas. In formulas (2) to (15), symbols such as B ¹ , C ¹ and D ¹ surrounded by hexagons correspond to rings such as ring B ¹ , ring C ¹ and ring D ¹ respectively. The hexagon represents a six-membered ring such as cyclohexane or benzene. A hexagon may represent a fused ring such as naphthalene or a bridged ring such as adamantane.

In the chemical formulas of component compounds, the symbol of the terminal group R ^a is used for a plurality of compounds. In these compounds, two groups represented by any two R ^a may be identical or different. For example, there is a case where R ^{a of} the compound (1-1) is ethyl and R ^a of the compound (1-2) is ethyl. There is also a case where R ^{a of the} compound (1-1) is ethyl and R ^a of the compound (1-2) is propyl. This rule also applies to symbols such as R ¹¹ and Z ¹¹ . In compound (8), when i is 2, two rings D ¹ are present. Two groups represented by two rings D ¹ in this compound may be identical 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' is arbitrary. In the expression “at least one 'A' may be replaced by 'B'”, when the number of 'A' is one, the position of 'A' is arbitrary and the number of 'A' is two Also in the case of three or more, it means that those positions can be selected without limitation. This rule also applies to the expression "at least one 'A' has been replaced by 'B'". The expression “at least one 'A' may be replaced by 'B', 'C', or 'D'” is optional when any 'A' is replaced by 'B'. If A 'is replaced by' C ', and any' A 'is replaced by' D ', then more' A 'may be' B ',' C ', and / or' D ' It is meant to include the case where it is replaced by at least two. For example, "alkyl at least one of -CH ₂ -may be replaced by -O- or -CH = CH-" includes alkyl, alkoxy, alkoxyalkyl, alkenyl, alkoxyalkenyl and alkenyloxyalkyl. Note that two successive -CH ₂ - are replaced by the -O-, it is a -O-O- in such is not preferred. Alkyl such as in, -CH ₂ methyl moiety _(-CH 2 -H) - by is replaced by -O- is not preferred also be the -O-H.

  Halogen means fluorine, chlorine, bromine and iodine. Preferred halogens are fluorine and chlorine. A further preferred halogen is fluorine. The alkyl of the liquid crystal compound is linear or branched and does not contain cyclic alkyl. Linear alkyls are generally preferred over branched alkyls. The same is true for end groups such as alkoxy and alkenyl. The configuration of 1,4-cyclohexylene is preferably trans rather than cis in order to increase the maximum temperature. 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 generated by removing two hydrogens from the ring, such as tetrahydropyran-2,5-diyl.

  The present invention includes the following items.

式（１）において、
Ｒ^ａおよびＲ^ｂは独立して、水素または炭素数１から１０のアルキルであり、このアルキルにおいて、少なくとも１つの−ＣＨ_２−は−Ｏ−、−Ｓ−、−ＣＯ−、または−ＳｉＨ_２−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、これらの一価基において、少なくとも１つの水素はフッ素または塩素で置き換えられてもよく、そしてＲ^ｂは、フッ素、塩素、−Ｃ≡Ｎ、−ＮＣＳ、−ＳＦ_５、−ＣＦ_２ＳＦ_５、−Ｃ≡Ｃ−Ｃ≡Ｎ、または−Ｃ≡Ｃ−ＣＦ_３であってもよく；
Ａ^１、Ａ^２、およびＡ^３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、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、２，６，７−トリオキサビシクロ［２．２．２］オクタン−１，４−ジイル、１，４−フェニレン、ナフタレン−２，６−ジイル、９，１０−ジヒドロフェナントレン−２，７−ジイル、９Ｈ−キサンテン−２，６−ジイル、またはフルオレン−２，７−ジイルであり、これらの基において、少なくとも１つの−ＣＨ_２−は−Ｏ−、−Ｓ−、−ＣＯ−、または−ＳｉＨ_２−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−ＣＨ＝Ｎ−で置き換えられてもよく、これらの二価基において、少なくとも１つの水素は、フッ素、塩素、−Ｃ≡Ｎ、−ＣＦ_３、−ＣＨＦ_２、−ＣＨ_２Ｆ、−ＯＣＦ_３、−ＯＣＨＦ_２、または−ＯＣＨ_２Ｆで置き換えられてもよく；
Ｇは、式（ｐｒ−１）または（ｐｒ−２）で表される二価基であり；

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、このアルキレンにおいて、少なくとも１つの−ＣＨ_２−は−Ｏ−、−Ｓ−、−ＣＯ−、または−ＳｉＨ_２−で置き換えられてもよく、１つまたは２つの−ＣＨ_２ＣＨ_２−は、−ＣＨ＝ＣＨ−または−Ｃ≡Ｃ−で置き換えられてもよく、これらの二価基において、少なくとも１つの水素はフッ素または塩素で置き換えられてもよく；
ａおよびｂは独立して、０、１、２、または３であり、ａおよびｂの和は０から４であり；そして

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、このアルキルおよびアルケニルにおいて、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。 Item 1. At least one compound selected from the group of compounds represented by Formula (1) as a first component and at least one selected from the group of compounds represented by Formulas (2) to (4) as a second component Liquid crystal composition containing a compound and having a nematic phase.

In equation (1),
R ^a and R ^b are independently hydrogen or alkyl having 1 to 10 carbon atoms, and in this alkyl, at least one —CH ₂ — is —O—, —S—, —CO— or —SiH ₂ And at least one —CH ₂ CH ₂ — may be replaced by —CH = CH— or —C≡C—, and in these monovalent groups, at least one hydrogen is fluorine or It may be replaced by chlorine and R ^b may be fluorine, chlorine, -C≡N, -NCS, -SF ₅ , -CF ₂ SF ₅ , -C≡C-C≡N, or -C≡C- May be CF ₃ ;
A ¹ , A ² and A ³ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene- 2,6-diyl, 2,6,7-trioxabicyclo [2.2.2] octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, 9,10-dihydrophenanthrene -2,7-diyl, 9H-xanthene-2,6-diyl, or fluorene-2,7-diyl, in which at least one -CH ₂ -is -O-, -S-,- CO— or —SiH ₂ — may be replaced, and at least one —CH ₂ CH ₂ — may be replaced by —CH = CH— or —CH = N—, and in these divalent groups, Less At most one hydrogen may be replaced by fluorine, chlorine, -C≡N, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ or -OCH ₂ F;
G is a divalent group represented by the formula (pr-1) or (pr-2);

Z ¹ , Z ² and Z ³ independently represent a single bond or alkylene having 1 to 6 carbon atoms, and in this alkylene, at least one —CH ₂ — is —O—, —S—, —CO— Or -SiH _2- , and one or two -CH ₂ CH ₂ -may be replaced by -CH = CH- or -C≡C-, in these divalent groups , At least one hydrogen may be replaced by fluorine or chlorine;
a and b are independently 0, 1, 2, or 3, and the sum of a and b is 0 to 4; and

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 the alkyl and alkenyl, at least one —CH ₂ — may be replaced by —O— Well, at least one hydrogen may be replaced by fluorine;
Ring B ¹ , ring B ² , ring B ³ and ring B ⁴ are each 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（１ａ）から式（１ｄ）において、
Ｒ^ａおよびＲ^ｂは独立して、炭素数１から１０のアルキルであり、このアルキルにおいて、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−または−Ｃ≡Ｃ−で置き換えられてもよく、これらの一価基において、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、Ｒ^ｂはフッ素、塩素、−Ｃ≡Ｎ、−ＮＣＳ、−ＳＦ_５、−ＣＦ_２ＳＦ_５、−Ｃ≡Ｃ−Ｃ≡Ｎ、または−Ｃ≡Ｃ−ＣＦ_３であってもよく；
Ａ^１およびＡ^２は独立して、１，４−シクロヘキシレン、１，４−フェニレン、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；
Ｇは、式（ｐｒ−１）または（ｐｒ−２）で表される二価基であり；

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、このアルキレンにおいて、１つの−ＣＨ_２−は−Ｏ−または−ＣＯ−で置き換えられてもよく、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、これらの二価基において、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；
ａおよびｂは独立して、０、１、２、または３であり、ａおよびｂの和は０から３であ
る。 Item 2. Item 2. The liquid crystal composition according to item 1, wherein the first component is at least one compound selected from the group of compounds represented by formula (1a) to formula (1d).

In formulas (1a) to (1d),
R ^a and R ^b are independently alkyl having 1 to 10 carbons, and in this alkyl, at least one —CH ₂ — may be replaced by —O—, at least one —CH ₂ CH ₂ -May be replaced by -CH = CH- or -C≡C-, and in these monovalent groups, at least one hydrogen may be replaced by fluorine, and R ^b is fluorine, chlorine, -C≡ _{N, -NCS, -SF 5, -CF} 2 SF 5, may be a -C≡C-C≡N or -C≡C-CF _3,;
A ¹ and A ² are independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is replaced by fluorine;
G is a divalent group represented by the formula (pr-1) or (pr-2);

Z ¹ , Z ² and Z ³ independently represent a single bond or alkylene having 1 to 6 carbon atoms, and in this alkylene, one —CH ₂ — is replaced by —O— or —CO— Well, one —CH ₂ CH ₂ — may be replaced by —CH = CH— or —C≡C—, and in these divalent groups, at least one hydrogen may be replaced by fluorine;
a and b are independently 0, 1, 2, or 3, and the sum of a and b is 0 to 3.

式（１ａ）において、
Ｒ^ａは、炭素数１から１０のアルキル、炭素数１から１０のアルコキシ、炭素数１から１０のアルコキシアルキル、または炭素数２から１２のアルケニルであり、Ｒ^ｂは水素または少なくとも１つの水素がフッ素で置き換えられた炭素数１から１０のアルキル、フッ素、塩素、−Ｃ≡Ｎ、−ＮＣＳ、−ＳＦ_５、−ＣＦ_２ＳＦ_５、−Ｃ≡Ｃ−Ｃ≡Ｎ、または−Ｃ≡Ｃ−ＣＦ_３であり、このアルキルにおいて、少なくとも１つの−ＣＨ_２−は−Ｏ−、−Ｓ−、−ＣＯ−、または−ＳｉＨ_２−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、これらの一価基において、少なくとも１つの水素はフッ素または塩素で置き換えられてもよく；
Ａ^１およびＡ^２は独立して、１，４−シクロヘキシレン、１，４−フェニレン、または少なくとも１つの水素がフッ素または塩素で置き換えられた１，４−フェニレンであり；
Ｇは、式（ｐｒ−１）または（ｐｒ−２）で表される二価基であり；

Ｚ^１、Ｚ^２、およびＺ^３は独立して、単結合、−ＣＯＯ−、−ＣＦ_２Ｏ−、−ＯＣＦ_２−、−ＣＨ_２ＣＨ_２−、または−ＣＨ＝ＣＨ−であり；
Ｙ^１およびＹ^２は独立して、水素またはフッ素であり；
ａおよびｂは独立して、０、１、または２であり、ａおよびｂの和は０から２である。 Item 3. The liquid crystal composition according to item 1 or 2, wherein the first component is at least one compound selected from the group of compounds represented by formula (1a).

In formula (1a),
R ^a is alkyl of 1 to 10 carbons, alkoxy of 1 to 10 carbons, alkoxyalkyl of 1 to 10 carbons, or alkenyl of 2 to 12 carbons, and R ^b is hydrogen or at least one hydrogen is Fluorine-substituted alkyl having 1 to 10 carbon atoms, fluorine, chlorine, -C≡N, -NCS, -SF ₅ , -CF ₂ SF ₅ , -C≡C-C≡N, or -C≡C- CF ₃ , at least one of —CH ₂ — in this alkyl may be replaced by —O—, —S—, —CO—, or —SiH ₂ —, and at least one —CH ₂ CH ₂ — May be replaced by -CH = CH- or -C≡C-, and in these monovalent groups, at least one hydrogen may be replaced by fluorine or chlorine;
A ¹ and A ² are independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine;
G is a divalent group represented by the formula (pr-1) or (pr-2);

Z ¹ , Z ² and Z ³ are independently a single bond, -COO-, -CF ₂ O-, -OCF _2- , -CH ₂ CH _2- or -CH = CH-;
Y ¹ and Y ² are independently hydrogen or fluorine;
a and b are independently 0, 1 or 2, and the sum of a and b is 0 to 2.

式（１ｂ）において、
Ｒ^ａおよびＲ^ｂは独立して、炭素数１から１０のアルキル、炭素数１から１０のアルコキシ、炭素数１から１０のアルコキシアルキル、または炭素数２から１２のアルケニルであり；
Ａ^１およびＡ^２は独立して、１，４−シクロヘキシレン、１，４−フェニレン、または少なくとも１つの水素がフッ素または塩素で置き換えられた１，４−フェニレであり；
Ｙ^０およびＹ^１は独立して、水素またはフッ素であり；
Ｇは、式（ｐｒ−１）または（ｐｒ−２）で表される二価基であり；

Ｚ^１、Ｚ^２、およびＺ^３は独立して、単結合、−ＣＨ_２Ｏ−、−ＯＣＨ_２−、−ＣＨ_２ＣＨ_２−、または−ＣＨ＝ＣＨ−であり；
ａおよびｂは独立して、０、１、または２であり、ａおよびｂの和は０から２である。 Item 4. The liquid crystal composition according to item 1 or 2, wherein the first component is at least one compound selected from the group of compounds represented by formula (1b).

In formula (1b),
R ^a and R ^b are independently alkyl having 1 to 10 carbons, alkoxy having 1 to 10 carbons, alkoxyalkyl having 1 to 10 carbons, or alkenyl having 2 to 12 carbons;
A ¹ and A ² are independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine;
Y ⁰ and Y ¹ are independently hydrogen or fluorine;
G is a divalent group represented by the formula (pr-1) or (pr-2);

Z ¹ , Z ² and Z ³ are independently a single bond, -CH ₂ O-, -OCH _2- , -CH ₂ CH _2- , or -CH = CH-;
a and b are independently 0, 1 or 2, and the sum of a and b is 0 to 2.

式（１ｃ）および（１ｄ）において、
Ｒ^ａおよびＲ^ｂは独立して、炭素数１から１０のアルキル、炭素数１から１０のアルコキシ、炭素数１から１０のアルコキシアルキル、または炭素数２から１２のアルケニルであり；
Ａ^１およびＡ^２は独立して、１，４−シクロヘキシレン、１，４−フェニレン、または少なくとも１つの水素がフッ素または塩素で置き換えられた１，４−フェニレンであり；
Ｇは、式（ｐｒ−１）または（ｐｒ−２）で表される二価基であり；

Ｚ^１、Ｚ^２、およびＺ^３は独立して、単結合、−ＣＯＯ−、−ＣＨ_２ＣＨ_２−、−ＣＨ＝ＣＨ−、または−Ｃ≡Ｃ−であり；
Ｙ^０およびＹ^２は独立して、水素またはフッ素であり；
ａおよびｂは独立して、０、１、または２であり、ａおよびｂの和は０から２である。 Item 5. The liquid crystal composition according to item 1 or 2, wherein the first component is at least one compound selected from the group of compounds represented by formula (1c) or (1d).

In formulas (1c) and (1d),
R ^a and R ^b are independently alkyl having 1 to 10 carbons, alkoxy having 1 to 10 carbons, alkoxyalkyl having 1 to 10 carbons, or alkenyl having 2 to 12 carbons;
A ¹ and A ² are independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine;
G is a divalent group represented by the formula (pr-1) or (pr-2);

Z ¹ , Z ² and Z ³ are independently a single bond, -COO-, -CH ₂ CH _2- , -CH = CH-, or -C≡C-;
Y ⁰ and Y ² are independently hydrogen or fluorine;
a and b are independently 0, 1 or 2, and the sum of a and b is 0 to 2.

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、このアルキルおよびアルケニルにおいて、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、少なくとも１つの水素がフッ素で置き換えられてもよい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、またはピリミジン−２，５−ジイルであり；
Ｚ^１４、Ｚ^１５、およびＺ^１６は独立して、単結合、−ＣＯＯ−、−ＣＦ_２Ｏ−、−ＯＣＦ_２−、−ＣＨ_２Ｏ−、−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。 Item 6. 6. The liquid crystal composition according to any one of items 1 to 5, further 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 the alkyl and alkenyl, at least one —CH ₂ — may be replaced by —O—, and at least one hydrogen is May be replaced by fluorine;
X ¹¹ represents fluorine, chlorine, -OCF ₃ , -OCHF ₂ , -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₂ CHF ₂ , or -OCF ₂ CHFCF ₃ ;
Ring C ¹ , ring C ² and ring C ³ are independently 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl;
Z ^{14, Z 15,} and ^{Z 16} are independently a single _{bond, -COO -, - CF 2 O} -, - OCF 2 -, - CH 2 O -, - CH 2 CH 2 -, - CH = CH- , -C≡C-, or - _{(CH 2) 4} - a and;
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、このアルキルおよびアルケニルにおいて、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、少なくとも１つの水素がフッ素で置き換えられてもよい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、またはピリミジン−２，５−ジイルであり；
Ｚ^１７は、単結合、−ＣＯＯ−、−ＣＦ_２Ｏ−、−ＯＣＦ_２−、−ＣＨ_２Ｏ−、−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。 Item 7. 7. The liquid crystal composition according to any one of items 1 to 6, further 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 the alkyl and alkenyl, at least one —CH ₂ — may be replaced by —O—, and at least one hydrogen is May be replaced by fluorine;
X ¹² is —C≡N or —C≡C—C≡N;
Ring D ¹ is 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl Or pyrimidine-2,5-diyl;
Z ¹⁷ represents a single bond, -COO-, -CF ₂ O-, -OCF _2- , -CH ₂ O-, -CH ₂ CH _2- , or -C≡C-;
L ¹³ and L ¹⁴ are independently hydrogen or fluorine;
i is 1, 2, 3 or 4;

式（９）から（１５）において、
Ｒ^１５およびＲ^１６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、このアルキルおよびアルケニルにおいて、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；
Ｒ^１７は、水素、フッ素、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、このアルキルおよびアルケニルにおいて、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、少なくとも１つの水素がフッ素で置き換えられてもよい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；
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−、−ＣＨ_２Ｏ−、−ＯＣＦ_２−、−ＣＨ_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。 Item 8. 8. The liquid crystal composition according to any one of items 1 to 7, further containing at least one compound selected from the group of compounds represented by formulas (9) to (15).

In equations (9) to (15),
R ¹⁵ and R ¹⁶ are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in this alkyl and alkenyl, at least one of —CH ₂ — may be replaced by —O— Well, at least one hydrogen may be replaced by fluorine;
R ¹⁷ is hydrogen, fluorine, 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;
Ring E ¹ , ring E ² , ring E ³ , and ring E ⁴ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, or at least one hydrogen optionally substituted by fluorine 1, 4-phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl;
Ring E ⁵ and ring E ⁶ are each independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6 -Diyl;
^{Z 18, Z 19, Z 20} , and ^{Z 21} are independently a single _{bond, -COO -, - CH 2 O} -, - OCF 2 -, - CH 2 CH 2 -, or -OCF ₂ CH ₂ CH ₂ -And
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 and t is 1, 2 or 3.

Item 9. Item 9. A liquid crystal display device comprising the liquid crystal composition according to any one of items 1 to 8.

式（１）において、
Ｒ^ａは水素または炭素数１から１０のアルキルであり、このアルキルにおいて、少なくとも１つの−ＣＨ_２−は−Ｏ−、−Ｓ−、または−ＣＯ−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、これらの一価基において、少なくとも１つの水素はフッ素または塩素で置き換えられてもよく、Ｒ^ｂは水素または少なくとも１つの水素がフッ素で置き換えられた炭素数１から１０のアルキル、フッ素、塩素、−Ｃ≡Ｎ、−ＮＣＳ、−ＳＦ_５、−ＣＦ_２ＳＦ_５、−Ｃ≡Ｃ−Ｃ≡Ｎ、または−Ｃ≡Ｃ−ＣＦ_３であり、このアルキルにおいて、少なくとも１つの−ＣＨ_２−は−Ｏ−、−Ｓ−、−ＣＯ−、または−ＳｉＨ_２−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、これらの一価基において、少なくとも１つの水素はフッ素または塩素で置き換えられてもよく；
Ａ^１およびＡ^２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、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、２，６，７−トリオキサビシクロ［２．２．２］オクタン−１，４−ジイル、１，４−フェニレン、ナフタレン−２，６−ジイル、９，１０−ジヒドロフェナントレン−２，７−ジイル、９Ｈ−キサンテン−２，６−ジイル、またはフルオレン−２，７−ジイルであり、これらの基において、少なくとも１つの−ＣＨ_２−は−Ｏ−、−Ｓ−、−ＣＯ−、または−ＳｉＨ_２−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−ＣＨ＝Ｎ−で置き換えられてもよく、これらの二価基において、少なくとも１つの水素は、フッ素、塩素、−Ｃ≡Ｎ、−ＣＦ_３、−ＣＨＦ_２、−ＣＨ_２Ｆ、−ＯＣＦ_３、−ＯＣＨＦ_２、または−ＯＣＨ_２Ｆで置き換えられてもよく；
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、このアルキレンにおいて、少なくとも１つの−ＣＨ_２−は−Ｏ−、−Ｓ−、−ＣＯ−、または−ＳｉＨ_２−で置き換えられてもよく、１つまたは２つの−ＣＨ_２ＣＨ_２−は−ＣＨ＝ＣＨ−または−Ｃ≡Ｃ−で置き換えられてもよく、これらの二価基において、少なくとも１つの水素はフッ素または塩素で置き換えられてもよく；
ａおよびｂは独立して、０、１、２、または３であり、ａおよびｂの和は０から４であり；
Ｇは、式（ｐｒ−１）または（ｐｒ−２）で表される二価基であり；

Ａ^３は、式（ａｒ−１）または（ａｒ−２）で表される二価基であり；

式（ａｒ−１）および（ａｒ−２）において、Ｙ^１、Ｙ^２、およびＹ^３は独立して、水素、フッ素、塩素、−ＣＦ_３、−ＣＨＦ_２、−ＣＨ_２Ｆ、−ＯＣＦ_３、−ＯＣＨＦ_２、または−ＯＣＨ_２Ｆである。 Item 10. The compound represented by Formula (1).

In equation (1),
R ^a is hydrogen or alkyl having 1 to 10 carbons, and in this alkyl, at least one —CH ₂ — may be replaced by —O—, —S—, or —CO—, and at least one — CH ₂ CH ₂ -may be replaced by -CH = CH- or -C≡C-, and in these monovalent groups, at least one hydrogen may be replaced by fluorine or chlorine, and R ^b is hydrogen Or C 1 -C 10 alkyl in which at least one hydrogen is replaced by fluorine, fluorine, chlorine, -C≡N, -NCS, -SF ₅ , -CF ₂ SF ₅ , -C≡C-C−N, Or —C≡C—CF ₃ , in which alkyl at least one —CH ₂ — may be replaced by —O—, —S—, —CO—, or —SiH ₂ —, at least 1 And one —CH ₂ CH ₂ — may be replaced by —CH = CH— or —C≡C—, and in these monovalent groups, at least one hydrogen may be replaced by fluorine or chlorine;
A ¹ and A ² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6- Diyl, 2,6,7-trioxabicyclo [2.2.2] octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, 9,10-dihydrophenanthrene-2,7 -Diyl, 9H-xanthene-2, 6-diyl or fluorene-2, 7-diyl, in these groups at least one of -CH ₂ -is -O-, -S-, -CO-, or -SiH _2- may be replaced, and at least one -CH ₂ CH ₂ -may be replaced by -CH = CH- or -CH = N-, and at least one of these divalent groups is Is hydrogen, fluorine, _{chlorine, -C≡N, -CF 3, -CHF 2} , -CH 2 F, -OCF 3, may be replaced by -OCHF _2, or -OCH ₂ F;
Z ¹ , Z ² and Z ³ independently represent a single bond or alkylene having 1 to 6 carbon atoms, and in this alkylene, at least one —CH ₂ — is —O—, —S—, —CO— Or -SiH _2- , and one or two -CH ₂ CH ₂ -may be replaced by -CH = CH- or -C≡C-, and in these divalent groups, At least one hydrogen may be replaced by fluorine or chlorine;
a and b are independently 0, 1, 2 or 3 and the sum of a and b is 0 to 4;
G is a divalent group represented by the formula (pr-1) or (pr-2);

A ³ is a divalent group represented by the formula (ar-1) or (ar-2);

In formulas (ar-1) and (ar-2), Y ¹ , Y ² and Y ³ are independently hydrogen, fluorine, chlorine, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF _2, or -OCH ₂ F.

式（１−１）および（１−２）において、
Ｒ^ａは水素または炭素数１から１０のアルキルであり、このアルキルにおいて、少なくとも１つの−ＣＨ_２−は−Ｏ−、−Ｓ−、−ＣＯ−、または−ＳｉＨ_２−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、これらの一価基において、少なくとも１つの水素はフッ素または塩素で置き換えられてもよく、Ｒ^ｂは水素または炭素数１から１０のポリフルオロアルキル、炭素数１から１０のポリフルオロアルコキシ、炭素数１から１０のポリフルオロアルケニル、フッ素、塩素、−Ｃ≡Ｎ、−ＮＣＳ、−ＳＦ_５、−ＣＦ_２ＳＦ_５、−Ｃ≡Ｃ−Ｃ≡Ｎまたは−Ｃ≡Ｃ−ＣＦ_３であり；
Ａ^１およびＡ^２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、テトラヒドロピラン−２，５−ジイル、テトラヒドロ−２Ｈ−ピラン−２−オン−３，６−ジイル、１，３−ジオキサン−２，５−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、２，６，７−トリオキサビシクロ［２．２．２］オクタン−１，４−ジイル、１，４−フェニレン、２−フルオロ−１，４−フェニレン、２，３−ジフルオロ−１，４−フェニレン、２，５−ジフルオロ−１，４−フェニレン、２，６−ジフルオロ−１，４−フェニレン、２−クロロ−１，４−フェニレン、２−フルオロ−３−クロロ−１，４−フェニレン、２，３−ジクロロ−１，４−フェニレン、ピリジン−２，５−ジイル、ピリミジン−２，５−ジイル、またはナフタレン−２，６−ジイルであり、これらの基において、少なくとも１つの水素は、フッ素、塩素、−ＣＦ_３、−ＣＨＦ_２、−ＣＨ_２Ｆ、−ＯＣＦ_３、−ＯＣＨＦ_２、または−ＯＣＨ_２Ｆで置き換えられてもよく；
Ｇは、式（ｐｒ−１）または（ｐｒ−２）で表される二価基であり；

Ｚ^１、Ｚ^２、およびＺ^３は独立して、単結合、−ＣＯＯ−、−ＯＣＯ−、−ＣＨ_２Ｏ−、−ＯＣＨ_２−、−ＣＦ_２Ｏ−、−ＯＣＦ_２−、−ＣＨ_２ＣＨ_２−、−ＣＨ＝ＣＨ−、−ＣＦ＝ＣＨ−、−ＣＨ＝ＣＦ−、−ＣＦ＝ＣＦ−、−Ｃ≡Ｃ−、−ＣＨ_２ＣＯ−、−ＣＯＣＨ_２−、−ＣＨ_２ＳｉＨ_２−、−ＳｉＨ_２ＣＨ_２−、−（ＣＨ_２）_４−、−（ＣＨ_２）_２ＣＯＯ−、−（ＣＨ_２）_２ＯＣＯ−、−ＯＣＯ（ＣＨ_２）_２−、−ＣＯＯ（ＣＨ_２）_２−、−（ＣＨ_２）_２ＣＦ_２Ｏ−、−（ＣＨ_２）_２ＯＣＦ_２−、−ＯＣＦ_２（ＣＨ_２）_２−、−ＣＦ_２Ｏ（ＣＨ_２）_２−、−（ＣＨ_２）_３Ｏ−、または−Ｏ（ＣＨ_２）_３−であり；
Ｙ^１、Ｙ^２、およびＹ^３は独立して、水素、フッ素、塩素、−ＣＦ_３、−ＣＨＦ_２、−ＣＨ_２Ｆ、−ＯＣＦ_３、−ＯＣＨＦ_２、または−ＯＣＨ_２Ｆである。
ａおよびｂは独立して、０、１、２、または３であり、ａおよびｂの和は０から４であり； Item 11. Item 11. The compound according to item 10, which is represented by Formula (1-1) or (1-2).

In formulas (1-1) and (1-2),
R ^a is hydrogen or alkyl having 1 to 10 carbons, and in this alkyl, at least one —CH ₂ — may be replaced by —O—, —S—, —CO—, or —SiH ₂ — At least one -CH ₂ CH ₂ -may be replaced by -CH = CH- or -C≡C-, and in these monovalent groups, at least one hydrogen may be replaced by fluorine or chlorine , R ^b is hydrogen or polyfluoroalkyl having 1 to 10 carbons, polyfluoroalkoxy having 1 to 10 carbons, polyfluoroalkenyl having 1 to 10 carbons, fluorine, chlorine, -C≡N, -NCS, -SF _{5, -CF} 2 _{SF 5,} be a -C≡C-C≡N or -C≡C-CF _3;
A ¹ and A ² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, tetrahydro-2H-pyran-2-one-3,6-diyl, 1,3-dioxane-2,5-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo [2 .2.2] Octane-1,4-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4 -Phenylene, 2,6-difluoro-1,4-phenylene, 2-chloro-1,4-phenylene, 2-fluoro-3-chloro-1,4-phenylene, 2,3-dichloro-1,4-phenylene , Pili Down-2,5-diyl, pyrimidine-2,5-diyl or naphthalene-2,6-diyl, in these groups, at least one of hydrogen, fluorine, _chlorine, -CF 3, -CHF _2, -CH ₂ F, -OCF ₃ , -OCHF ₂ , or -OCH ₂ F may be substituted;
G is a divalent group represented by the formula (pr-1) or (pr-2);

Z ¹ , Z ² and Z ³ independently represent a single bond, -COO-, -OCO-, -CH ₂ O-, -OCH _2- , -CF ₂ O-, -OCF _2- , -CH _{2 CH 2 -, - CH = CH} -, - CF = CH -, - CH = CF -, - CF = CF -, - C≡C -, - CH 2 CO -, - COCH 2 -, - CH 2 SiH 2 _{-, - SiH 2 CH 2 -} , - (CH 2) 4 -, - (CH 2) 2 COO -, - (CH 2) 2 OCO -, - OCO (CH 2) 2 -, - COO (CH 2) ₂ -,-(CH ₂ ) ₂ CF ₂ O-,-(CH ₂ ) ₂ OCF _2- , -OCF ₂ (CH ₂ ) _2- , -CF ₂ O (CH ₂ ) ₂ -,-(CH ₂ ) ₃ O-, or -O (CH ₂ ) _3- ;
Y ^{1, Y 2,} and ^{Y 3} are independently hydrogen, fluorine, _{chlorine, -CF 3, -CHF 2, -CH} 2 F, -OCF 3, -OCHF 2, or -OCH ₂ F.
a and b are independently 0, 1, 2 or 3 and the sum of a and b is 0 to 4;

式（１−１１ａ）から（１−１６ａ）、式（１−１１ｂ）から（１−１６ｂ）、式（１−２１ａ）から（１−２６ａ）、および式（１−２１ｂ）から（１−２６ｂ）において、
Ｒ^ａは炭素数１から１０のアルキルであり、このアルキルにおいて、１つまたは２つの−ＣＨ_２−は−Ｏ−または−Ｓ−で置き換えられてもよく、１つまたは２つの−ＣＨ_２ＣＨ_２−は−ＣＨ＝ＣＨ−または−Ｃ≡Ｃ−で置き換えられてもよく、これらの一価基において、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、そしてＲ^ｂは水素または炭素数１から４のポリフルオロアルキル、炭素数１から４のポリフルオロアルコキシ、炭素数１から４のポリフルオロアルケニル、フッ素、塩素、−ＳＦ_５、−ＣＦ_２ＳＦ_５、または−Ｃ≡Ｃ−ＣＦ_３であり；
Ａ^１１、Ａ^１２、Ａ^２１、およびＡ^２２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、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、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、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、２，６−ジフルオロ−１，４−フェニレン、２−クロロ−１，４−フェニレン、ピリジン−２，５−ジイル、ピリミジン−２，５−ジイル、またはナフタレン−２，６−ジイルであり；
Ｚ^１１、Ｚ^１２、Ｚ^２１、Ｚ^２２、およびＺ^３１は独立して、単結合、−ＣＯＯ−、−ＯＣＯ−、−ＣＨ_２Ｏ−、−ＯＣＨ_２−、−ＣＦ_２Ｏ−、−ＯＣＦ_２−、−ＣＨ_２ＣＨ_２−、−ＣＨ＝ＣＨ−、−ＣＦ＝ＣＨ−、−ＣＨ＝ＣＦ−、−ＣＦ＝ＣＦ−、−Ｃ≡Ｃ−、−（ＣＨ_２）_４−、−（ＣＨ_２）_２ＣＯＯ−、−ＯＣＯ（ＣＨ_２）_２−、−（ＣＨ_２）_２ＣＦ_２Ｏ−、−ＯＣＦ_２（ＣＨ_２）_２−、−（ＣＨ_２）_３Ｏ−、または−Ｏ（ＣＨ_２）_３−であり；
Ｙ^１、Ｙ^２、およびＹ^３は独立して、水素、フッ素、または塩素である。 Item 12. Formulas (1-11a) to (1-16a), formulas (1-11b) to (1-16b), formulas (1-21a) to (1-26a), and formulas (1-21b) to (1- Item 12. The compound according to item 10 or 11, which is represented by any one of 26b).

Formulas (1-11a) to (1-16a), formulas (1-11b) to (1-16b), formulas (1-21a) to (1-26a), and formulas (1-21b) to (1- In 26b),
R ^a is alkyl having 1 to 10 carbons, and in this alkyl, one or two of —CH ₂ — may be replaced by —O— or —S—, one or two of —CH ₂ CH _2- may be replaced by -CH = CH- or -C≡C-, and in these monovalent groups, at least one hydrogen may be replaced by fluorine, and R ^b may be hydrogen or C 1 To 4 polyfluoroalkyl, polyfluoroalkoxy having 1 to 4 carbon atoms, polyfluoroalkenyl having 1 to 4 carbon atoms, fluorine, chlorine, -SF ₅ , -CF ₂ SF ₅ , or -C≡C-CF ₃ Yes;
A ¹¹ , A ¹² , A ²¹ and A ²² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5 -Diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5- Difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2-chloro-1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, or naphthalene-2 , 6-diyl;
^{Z 11, Z 12, Z 21} , Z 22, and ^{Z 31} are independently a single _{bond, -COO -, - OCO -,} - CH 2 O -, - OCH 2 -, - CF 2 O -, - OCF _{2 -, - CH 2 CH 2} -, - CH = CH -, - CF = CH -, - CH = CF -, - CF = CF -, - C≡C -, - (CH 2) 4 -, - ( _{CH 2) 2 COO -, -} OCO (CH 2) 2 -, - (CH 2) 2 CF 2 O -, - OCF 2 (CH 2) 2 -, - (CH 2) 3 O-, or -O ( CH ₂ ) _3- ;
Y ¹ , Y ² and Y ³ are independently hydrogen, fluorine or chlorine.

式（１−１１ａ）から（１−１６ａ）において、
Ｒ^ａは、炭素数１から１０のアルキル、炭素数１から１０のアルコキシ、または炭素数２から１０のアルケニルであり、Ｒ^ｂは、フッ素、−ＣＦ_３、または−ＯＣＦ_３であり；
Ａ^１１、Ａ^１２、Ａ^２１、およびＡ^２２は独立して、１，４−シクロヘキシレン、１，４−フェニレン、２−フルオロ−１，４−フェニレン、または２，６−ジフルオロ−１，４−フェニレンであり；
Ｚ^１１、Ｚ^１２、Ｚ^２１、Ｚ^２２、およびＺ^３１は独立して、単結合、−ＣＯＯ−、−ＯＣＨ_２−、−ＣＦ_２Ｏ−、または−ＣＨ_２ＣＨ_２−であり；
Ｙ^１およびＹ^２は独立して、水素またはフッ素である。 Item 13. Item 13. The compound according to any one of items 10 to 12, represented by any one of formulas (1-11a) to (1-16a).

In formulas (1-11a) to (1-16a),
R ^a is alkyl having 1 to 10 carbons, alkoxy having 1 to 10 carbons, or alkenyl having 2 to 10 carbons, and R ^b is fluorine, -CF ₃ or -OCF ₃ ;
A ¹¹ , A ¹² , A ²¹ and A ²² are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,6-difluoro-1,4 -Phenylene;
Z ¹¹ , Z ¹² , Z ²¹ , Z ²² and Z ³¹ are independently a single bond, -COO-, -OCH _2- , -CF ₂ O-or -CH ₂ CH _2- ;
Y ¹ and Y ² are independently hydrogen or fluorine.

式（１−２１ａ）から（１−２６ａ）において、
Ｒ^ａは、炭素数１から１０のアルキル、炭素数１から１０のアルコキシ、または炭素数２から１０のアルケニルであり、Ｒ^ｂは、フッ素、−ＣＦ_３、または−ＯＣＦ_３であり；
Ａ^１１、Ａ^１２、Ａ^２１、およびＡ^２２は独立して、１，４−シクロヘキシレン、１，４−フェニレン、２−フルオロ−１，４−フェニレン、または２，６−ジフルオロ−１，４−フェニレンであり；
Ｚ^１１、Ｚ^１２、Ｚ^２１、Ｚ^２２、およびＺ^３１は独立して、単結合、−ＣＨ_２ＣＨ_２−、−ＣＯＯ−、−ＯＣＨ_２−、または−ＣＦ_２Ｏ−であり；
Ｙ^１、Ｙ^２、およびＹ^３は独立して、水素またはフッ素である。 Item 14. 14. The compound according to any one of items 10 to 13, represented by any one of formulas (1-21a) to (1-26a).

In formulas (1-21a) to (1-26a),
R ^a is alkyl having 1 to 10 carbons, alkoxy having 1 to 10 carbons, or alkenyl having 2 to 10 carbons, and R ^b is fluorine, -CF ₃ or -OCF ₃ ;
A ¹¹ , A ¹² , A ²¹ and A ²² are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,6-difluoro-1,4 -Phenylene;
^{Z 11, Z 12, Z 21} , Z 22, and ^{Z 31} are independently a single _{bond, -CH 2 CH 2 -, -} COO -, - OCH 2 -, or _-CF 2 O-a and;
Y ¹ , Y ² and Y ³ are independently hydrogen or fluorine.

  The present invention also includes the following items. (A) at least one compound selected from the group of compounds represented by formula (1) as a first component, and selected from the group of compounds represented by formulas (2) to (4) as a second component At least one compound, at least one compound selected from the group of compounds represented by formulas (5) to (7) as the third component, and represented by formulas (9) to (15) as the fourth component A composition containing at least one compound selected from the group of compounds and having a nematic phase. (B) In item (a), the proportion of the first component is in the range of 5% by weight to 60% by weight, and the proportion of the second component is 30% by weight or more, based on the weight of the composition; In the item (a), the proportion of the component is in the range of 10% by weight to 95% by weight, the proportion of the fourth component is in the range of 0% by weight to 30% by weight, and the dielectric anisotropy is positively large. Composition as described. (C) In item (a), the proportion of the first component is in the range of 5% by weight to 60% by weight and the proportion of the second component is 30% by weight or more, based on the weight of the composition; The composition according to item (a), wherein the proportion of the component is in the range of 50% by weight to 30% by weight, the proportion of the fourth component is 40% by weight or more, and the dielectric anisotropy is negatively large.

  The present invention also includes the following items. (D) The above composition, which further contains at least one of an optically active compound, an antioxidant, an ultraviolet light absorber, a light stabilizer, a heat stabilizer, an antifoamer, a polymerizable compound, a polymerization initiator and a polymerization inhibitor object. (E) The upper limit temperature of the nematic phase is 70 ° C. or higher, the optical anisotropy (measured at 25 ° C.) at a wavelength of 589 nm is 0.07 or more, and the dielectric anisotropy (measured at 25 ° C. at a frequency of 1 kHz) The composition as described above, wherein 2) or more. (F) The upper limit temperature of the nematic phase is 70 ° C. or higher, the optical anisotropy (measured at 25 ° C.) at a wavelength of 589 nm is 0.08 or more, and the dielectric anisotropy (measured at 25 ° C. at a frequency of 1 kHz) The above composition, wherein) is -2 or less.

  The present invention also includes the following items. (G) A device comprising the above composition and having a mode of PC, TN, STN, ECB, OCB, IPS, VA, FFS, FPA, or PSA. (H) An AM device containing the above composition. (I) A transmission type element containing the above composition. (J) Use of the above composition as a composition having a nematic phase. (K) Use as an optically active composition by adding an optically active compound to the above composition.

  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 1-1 of the Compound (1) Preferred embodiment The compound (1) is characterized by having a divalent group represented by the formula (pr-1) or (pr-2).

  Compound (1) is extremely stable physically and chemically under the conditions in which the device is usually used, and the composition containing this compound is stable under the conditions in which the device is usually used. The compound (1) has a large dielectric anisotropy as compared with similar compounds, so that the threshold voltage of the device can be lowered. The compound (1) has good compatibility with other liquid crystal compounds as compared with similar compounds. Even when the composition is stored at low temperature, the compound does not precipitate as crystals (or smectic phase).

Preferred examples of the compound (1) will be described. Preferred examples of the terminal groups R ^a and R ^b , the rings A ¹ , A ² and A ³ and the linking groups Z ¹ , Z ² and Z ^{3 in} the compound (1) also apply to the subformula of the compound (1) Be done. In the compound (1), physical properties can be arbitrarily adjusted by appropriately combining these groups. Compound (1) may contain isotopes such as ² H (deuterium) and ¹³ C in an amount larger than the natural abundance ratio, because there is no large difference in the physical properties of the compounds. In addition, the definition of the symbol of compound (1) is as having described in the item 1.

In formula (1), R ^a and R ^b are independently hydrogen or alkyl having 1 to 10 carbon atoms, and in this alkyl, at least one —CH ₂ — is —O—, —S—, —CO -Or -SiH _2- may be replaced, and at least one -CH ₂ CH ₂ -may be replaced by -CH = CH- or -C≡C-, and in these R ^a and R ^b , At least one hydrogen may be replaced by fluorine or chlorine, and R ^b may be fluorine, chlorine, -C≡N, or -C≡C-C≡N.

Specific R ^a or R ^b is hydrogen, alkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, alkylthio, alkylthioalkoxy, acyl, acylalkyl, acyloxy, acyloxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkenyl, alkenyloxy, alkenyl Oxyalkyl, alkoxyalkenyl, alkynyl, alkynyloxy, silaalkyl or disilaalkyl. In these groups, at least one hydrogen may be replaced by fluorine or chlorine. At least two hydrogens may be replaced by fluorine and chlorine. In these groups, straight chain is preferable to branched chain. It is preferable when R ^a or R ^b is branched even if it is optically active. Preferred R ^a or R ^b is alkyl, alkoxy, alkoxyalkyl or alkenyl. In addition to these groups, R ^b may be polyfluoroalkyl, polyfluoroalkoxy, polyfluoroalkenyl, fluorine, chlorine, -C≡N, or -C≡C-C≡N. Examples of polyfluoroalkyl include perfluoroalkyl. This rule also applies to polyfluoroalkoxy and the like.

  The preferred configuration of -CH = CH- in alkenyl depends on the position of the double bond. The trans configuration is preferred in the alkenyl such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyl and 3-hexenyl. The cis configuration is preferred in the alkenyl such as 2-butenyl, 2-pentenyl and 2-hexenyl.

Preferred R ^a or R ^b is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, methoxymethyl, methoxyethyl, methoxypropyl, Ethoxymethyl, ethoxyethyl, ethoxypropyl, propoxymethyl, butoxymethyl, pentoxymethyl, vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3 -Pentenyl, 4-pentenyl, 2-propenyloxy, 2-butenyloxy, 2-pentenyloxy, 1-propynyl or 1-pentenyl.

Further preferable R ^a or R ^b is 2-fluoroethyl, 3-fluoropropyl, 2,2,2-trifluoroethyl, 2-fluorovinyl, 2,2-difluorovinyl, 2-fluoro-2-vinyl, 3 It is also -fluoro-1-propenyl, 3,3,3-trifluoro-1-propenyl, 4-fluoro-1-propenyl, or 4,4-difluoro-3-butenyl.

More preferable R ^a or R ^b is —CF ₃ , —CHF ₂ , —CH ₂ F, —CF ₂ CF ₃ , —CF ₂ CHF ₂ , —CF ₂ CH ₂ F, —CHFCF ₃ , —CH ₂ CF _{3 , -CF 2 CF 2 CF 3,} -CF 2 CHFCF 3, -CHFCF 2 CF 3, -OCF 3, -OCHF 2, -OCH 2 F, -OCF 2 CF 3, -OCF 2 CHF 2, -OCF 2 CH _{2 F, -OCHFCF 3, -OCH 2} CF 3, -OCF 2 CF 2 CF 3, -OCF 2 CHFCF 3, -OCHFCF 2 CF 3, is fluorine, chlorine or even C≡N,.

Particularly preferred R ^a or R ^b is ethyl, propyl, butyl, pentyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, methoxymethyl, ethoxymethyl, propoxymethyl, vinyl, 1-propenyl, 2-propenyl, 1-butenyl , 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 2-propenyloxy, 2-butenyloxy, 2-pentenyloxy, -OCF ₃ , -OCHF ₂ , -OCH _{2 F, -OCF 2 CF 3, -OCF} 2 CHF 2, -OCF 2 CH 2 F, -OCF 2 CF 2 CF 3, -OCF 2 CHFCF 3, -OCHFCF 2 CF 3, fluorine, chlorine or C≡N, is there. Most preferred R ^a or R ^b is ethyl, propyl, butyl, pentyl, methoxy, ethoxy, propoxy, methoxymethyl, vinyl, 1-propenyl, 3-butenyl, 3-pentenyl, -OCF ₃ , -OCHF ₂ , -CF _{3, -CHF 2, -CH 2 F} , -OCF 2 CHF 2, -OCF 2 CHFCF 3, fluorine or C≡N,.

In formula (1), A ¹ , A ² and A ³ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, decahydronaphthalene-2,6-diyl, 1,2,3 2,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo [2.2.2] octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-xanthene-2,6-diyl, or fluorene-2,7-diyl, in which at least one -CH ₂ -is -O- , -S-, -CO-, or -SiH _2- , and at least one -CH ₂ CH ₂ -may be replaced by -CH = CH- or -CH = N-, and these Two In monovalent group, at least one of hydrogen, fluorine, _{chlorine, -C≡N, -CF 3, -CHF 2} , -CH 2 F, -OCF 3, -OCHF 2, or be replaced by -OCH ₂ F Good.

“In these groups, at least one —CH ₂ — may be replaced by —O—, —S—, —CO—, or —SiH ₂ —, and at least one —CH ₂ CH ₂ — is —CH A preferred example of “= CH— or —CH = N—” is a divalent group represented by the following formulas (16-1) to (16-50). Further preferred examples are formulas (16-1) to (16-4), formulas (16-15), formulas (16-23), formulas (16-27) to (26-29) and formulas (16-36). And a divalent group represented by Formula (16-39) and Formula (16-45).

"In these divalent groups, at least one hydrogen is fluorine, chlorine, -C≡N, -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₃ , -OCHF ₂ or -OCH ₂ F Preferred examples of “which may be substituted” are divalent groups represented by the following formulas (17-1) to (17-77). Further preferred examples are formulas (17-1) to (17-4), formulas (17-6), formulas (17-10) to (17-15) and formulas (17-54) to (17-59). , And divalent groups represented by formulas (17-72) to (17-77).

Preferred A ¹ , A ² or A ³ is 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, 1, 4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2,3,5-trifluoro-1,4-phenylene, pyridine-2,5-diyl, 3-fluoropyridine-2,5-diyl, pyrimidine-2,5-diyl, pyridazine-2,5-diyl, Decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, or naphthalene-2,6-diyl. The configuration of 1,4-cyclohexylene and 1,3-dioxane-2,5-diyl is preferably trans rather than cis.

Further preferred A ¹ , A ² or A ³ is 1,4-cyclohexylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 2-fluoro -1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyridine-2,5-diyl Or pyrimidine-2,5-diyl. Particularly preferred A ¹ , A ² or A ³ is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene or 2 , 6-difluoro-1,4-phenylene. Most preferred A ¹ , A ² or A ³ is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,6-difluoro-1,4-phenylene . Most preferred A ¹ , A ² or A ³ is also 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,3-difluoro-1,4-phenylene .

式（ｐｒ−１）で表される二価基を有する化合物は、正に大きな誘電率異方性の観点から好ましい。式（ｐｒ−２）で表される二価基を有する化合物は、負に大きな誘電率異方性の観点から好ましい。 In Formula (1), G is a divalent group represented by Formula (pr-1) or (pr-2).

The compound having a divalent group represented by the formula (pr-1) is preferable from the viewpoint of a large dielectric anisotropy. The compound having a divalent group represented by the formula (pr-2) is preferable from the viewpoint of negatively large dielectric anisotropy.

In formula (1), Z ¹ , Z ² and Z ³ are independently a single bond or alkylene having 1 to 6 carbon atoms, and in this alkylene, at least one —CH ₂ — is —O—, — S-, -CO-, or -SiH _2- may be replaced, and one or two -CH ₂ CH ₂ -may be replaced by -CH = CH- or -C≡C-, In these divalent groups, at least one hydrogen may be replaced by fluorine or chlorine.

Preferred Z ¹ , Z ² or Z ³ is a single bond, -COO-, -OCO-, -CH ₂ O-, -OCH _2- , -CF ₂ O-, -OCF _2- , -CH ₂ CH ₂ -, - CH = CH -, - CF = CH -, - CH = CF -, - CF = CF -, - C≡C -, - CH 2 CO -, - COCH 2 -, - CH 2 SiH 2 -, _{-SiH 2 CH 2 -, - (} CH 2) 4 -, - (CH 2) 2 COO -, - (CH 2) 2 OCO -, - OCO (CH 2) 2 -, - COO (CH 2) 2 - _{, - (CH 2) 2 CF} 2 O -, - (CH 2) 2 OCF 2 -, - OCF 2 (CH 2) 2 -, - CF 2 O (CH 2) 2 -, - (CH 2) 3 O -, or -O _{(CH 2) 3} - is. -CH = CH -, - CF = CF -, - configuration about the double bond of the _CH = CH-CH 2 O-, and -OCH ₂ -CH = CH- bond group such as trans is preferable to cis .

Further preferred Z ¹ , Z ² or Z ³ is a single bond, -COO-, -OCO-, -CH ₂ O-, -OCH _2- , -CF ₂ O-, -OCF _2- , -CH ₂ CH ₂ -, - CH = CH -, - CF = CF -, - C≡C-, and - _{(CH 2) 4} - a. Particularly preferred Z ¹ , Z ² or Z ³ is a single bond, -CH ₂ CH _2- , -COO-, -OCO-, -CF ₂ O-, -OCF _2- , -CH = CH-, and- C≡C-. Most preferred Z ¹ , Z ² or Z ³ is a single bond.

  In formula (1), a and b are independently 0, 1, 2, or 3, and the sum of a and b is 0 to 4. The compound (1) has two to six rings. These rings include fused rings and bridged six-membered rings in addition to six-membered rings such as 1,4-phenylene. Such rings are also counted as one ring. When the compound (1) has two rings, the compatibility with other liquid crystal compounds is good. When the compound (1) has two or three rings, the viscosity is small. When the compound (1) has three or four rings, the upper limit temperature is high. When the compound (1) has four rings, the temperature range of the liquid crystal phase is wide.

Physical properties such as optical anisotropy and dielectric anisotropy can be arbitrarily adjusted by appropriately selecting the terminal group, ring and linking group of compound (1). The effects of the types of terminal groups R ^a and R ^b , rings A ¹ , A ² , and A ³ , linking groups Z ¹ , Z ² , and Z ^{3 on} the physical properties of compound (1) are described below.

1-2. Physical Properties Preferred examples of the compound (1) described in Item 1 are the compounds (1a) to (1d) described in Item 2.

In compound (1a), R ^a is alkyl, alkoxy or the like, and R ^b is an electron attractive group such as fluorine, -OCF ₃ , -C≡N. The compound (1a) has a large dielectric anisotropy. This compound is suitable as a component to lower the threshold voltage of a device such as FFS or TN. In compound (1b), R ^a and R ^b are alkyl, alkoxy and the like, and Y ⁰ and Y ¹ are electron withdrawing groups such as fluorine and chlorine. The compound (1b) has a large negative dielectric anisotropy. This compound is suitable as a component for lowering the threshold voltage of a device such as VA. In the compound (1c), Y ⁰ and Y ² are hydrogen, fluorine and the like. The compound (1c) or (1d) has a small dielectric anisotropy. When this compound has two rings, it is suitable as a component to lower the viscosity of the composition. When this compound has four rings, it is suitable as a component for raising the upper limit temperature. "Large" and "small" are relative expressions. An example of "small" is dielectric anisotropy ranging from about -1 to about +2.

In these compounds, when R ^a or R ^b is linear, the temperature range of the liquid crystal phase is wide and the viscosity is small. When R ^a or R ^b is a branched chain, the compatibility with other liquid crystal compounds is good. Compounds in which R ^a or R ^b is an optically active group are useful as chiral dopants. By adding this compound to the composition, it is possible to prevent the reverse twist domain generated in the device. Compounds in which R ^a or R ^b is not an optically active group are useful as components of the composition. When R ^a or R ^b is alkenyl, the preferred configuration depends on the position of the double bond. An alkenyl compound having a preferred configuration has a high upper temperature limit or a wide temperature range of liquid crystal phase. A detailed description is given in Mol. Cryst. Liq. Cryst., 1985, 131, 109 and Mol. Cryst. Liq. Cryst., 1985, 131, 327.

When A ¹ or A ² is 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine, pyridine-2,5-diyl, or 1,3-dioxane-2,5-diyl, Dielectric anisotropy is positively large. When the ring is 1,4-phenylene in which at least one hydrogen may be replaced by fluorine or chlorine, pyridine-2,5-diyl, pyrimidine-2,5-diyl, or pyridazine-3,6-diyl , Optical anisotropy is large. When the ring is 1,4-cyclohexylene, 1,4-cyclohexenylene, or 1,3-dioxane-2,5-diyl, the optical anisotropy is small.

  When at least two rings are 1,4-cyclohexylene, the upper limit temperature is high, the optical anisotropy is small, and the viscosity is small. When at least one ring is 1,4-phenylene, the optical anisotropy is relatively large, and the orientational order parameter is large. When at least two rings are 1,4-phenylene, the optical anisotropy is large, the temperature range of the liquid crystal phase is wide, and the upper limit temperature is high.

Bonding group ^Z 1, ^{Z 2} or ^{Z 3,} is a single _{bond, -CH 2 O -, - CF} 2 O -, - OCF 2 -, - CH 2 CH 2 -, - CH = CH -, - CF = CF -, or - _{(CH 2) 4} - is when the viscosity is small. Bonding group is a single _{bond, -OCF 2 -, - CF 2} O -, - CH 2 CH 2 -, or viscosity is smaller when a -CH = CH-. When the binding group is -CH = CH-, wide temperature range of liquid crystal phase, and the elastic constant ratio _{K 33 / K 11 (K 33} : bend elastic _{constant, K 11:} splay elastic constant) is large. When the bonding group is -C≡C-, the optical anisotropy is large.

In the compound (1a), preferred examples of Z ¹ , Z ² or Z ³ are a single bond, -COO-, -CF ₂ O-, -OCF _2- , -CH ₂ CH _2- , -CH = CH- , -CF = CF-, or -C≡C-. More preferred examples include a single _{bond, -COO -, - CF 2 O} -, - OCF 2 -, - CH 2 CH 2 -, or -CH = CH-. The most preferred example is a single bond.

In the compound (1b), preferred examples of Z ¹ , Z ² or Z ³ are a single bond, -CH ₂ O-, -OCH _2- , -CF ₂ O-, -OCF _2- , -CH ₂ CH ₂ -, -CH = CH-, -CF = CF-, or -C≡C-. More preferred examples include a single _{bond, -CH 2 O -, - OCH} 2 -, or _-CH 2 CH ₂ -. The most preferred example is a single bond.

In the compounds (1c) or (1d), preferred examples of Z ¹ , Z ² or Z ³ are a single bond, -COO-, -CH ₂ O-, -OCH _2- , -CH ₂ CH _2- , -CH = CH-, or -C≡C-. Further preferred examples are a single bond, -COO-, -CH ₂ CH _2- , -CH = CH-, or -C≡C-, and the most preferred example is a single bond.

When in the compound (1a) Y ¹ and Y ² are hydrogen, this compound is preferred. This compound is further preferred when Y ¹ is hydrogen and Y ² is fluorine. When Y ¹ and Y ² are fluorine, this compound is most preferred from the viewpoint of large dielectric anisotropy. When in formula ( ¹ b) Y ¹ and Y ³ are fluorine, chlorine, -CF ₃ or -CHF ₂ this compound is preferred. When Y ⁰ and Y ¹ are fluorine or chlorine, this compound is further preferred. This compound is most preferred when Y ⁰ and Y ¹ are fluorine. When Y ⁰ and Y ² in compound (1c) are hydrogen, this compound is preferred. When Y ⁰ is hydrogen and Y ² is fluorine, this compound is preferable from the viewpoint of dielectric anisotropy. When Y ⁰ is fluorine and Y ² is hydrogen, this compound is preferable from the viewpoint of compatibility with other liquid crystal compounds. When Y ⁰ and Y ² are both fluorine, this compound is also preferred.

  When the compound (1) has two or three rings, the viscosity is small. When the compound (1) has four or five rings, the upper limit temperature is high. As described above, a compound having the desired physical properties can be obtained by appropriately selecting the types of terminal groups, rings and linking groups, and the number of rings. Accordingly, the compound (1) is useful as a component of a composition used for devices such as PC, TN, STN, ECB, OCB, IPS, VA and the like.

1-3. Compounds (1-1) and (1-2)
Examples of the compound (1) having a positive dielectric anisotropy are the compounds (1-1) and (1-2). R ^b is an electron withdrawing group such as fluorine, —OCF ₃ or —C≡N. Preferred compounds (1-1) and (1-2) are compounds (1-11a) to (1-16a), liquid crystal compounds (1-11b) to (1-16b), and compounds (1-21a) (1-26a), and compounds (1-21b) to (1-26b). The compound having a divalent group represented by the formula (pr-1) is preferable to the compound having a divalent group represented by the formula (pr-2) from the viewpoint of a large dielectric anisotropy. The compound (1-11a), the compound (1-13a), and the compound (1-16a) are preferable from the viewpoint of high upper limit temperature and large dielectric anisotropy. The compound (1-12a), the compound (1-14a), and the compound (1-15a) are preferable from the viewpoint of excellent compatibility. The compound (1-21a), the compound (1-23a), and the compound (1-26a) are preferable from the viewpoint of high upper limit temperature and large dielectric anisotropy. The compound (1-22a), the compound (1-24a), and the compound (1-25a) are preferable from the viewpoint of excellent compatibility.

2. Synthesis of Compound (1) A synthesis method of compound (1) will be described. Compound (1) can be synthesized by appropriately combining the methods of synthetic organic chemistry. Methods for introducing the desired end groups, rings and linking groups into the starting material are organic synthesis (Organic Syntheses, John Wiley & Sons, Inc.), Organic Reactions (John Wiley & Sons, Inc.), Complement The book is described in books such as "Hensive Organic Synthesis (Pergamon Press)" and "New Experimental Chemistry Course (Maruzen)".

2-1. Formation of Bonding Group Z First, a scheme is shown for the method of generating the bonding groups Z ¹ to Z ³ . Next, the reactions described in the schemes in formations (1) to (11) will be described. In this scheme, MSG ¹ (or MSG ² ) is a monovalent organic group having at least one ring. Plural MSG ¹ (or MSG ² ) used in the scheme may be identical or different. Compounds (1A) to (1K) correspond to compound (1).

(1) Formation of Single Bond: Arylboric acid (21) is reacted with a compound (22) synthesized by a known method in an aqueous carbonate solution in the presence of a catalyst such as tetrakis (triphenylphosphine) palladium. Compound (1A) is synthesized. Compound (1A) is prepared by reacting compound (23) synthesized by a known method with n-butyllithium and then with zinc chloride, and reacting compound (22) in the presence of a catalyst such as dichlorobis (triphenylphosphine) palladium. It is also synthesized by reacting.

(2) Formation of -COO- and -OCO- Compound (23) is reacted with n-butyllithium and then carbon dioxide to obtain carboxylic acid (24). A compound having -COO- by dehydrating compound (24) and phenol (25) synthesized by a known method in the presence of DCC (1,3-dicyclohexylcarbodiimide) and DMAP (4-dimethylaminopyridine) Synthesize (1B). A compound having -OCO- can also be synthesized by this method.

(3) Formation of —CF ₂ O— and —OCF ₂ — Compound (1B) is treated with a sulfurizing agent such as Lawesson's reagent to give compound (26). The compound (26) is fluorinated with 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) can also be synthesized by fluorinating compound (26) with (diethylamino) sulfur trifluoride (DAST). See WH Bunnelle et al., J. Org. Chem. 1990, 55, 768. -OCF ₂ by this method - compounds having also synthesized. It is also possible to generate these linking groups by the method described in Peer. Kirsch et al., Angew. Chem. Int. Ed. 2001, 40, 1480.

(4) Formation of -CH = CH- Compound (23) is treated with n-butyllithium and then reacted with formamide such as N, N-dimethylformamide (DMF) to obtain aldehyde (28). The compound (1D) is synthesized by reacting a phosphorylide generated by treating a phosphonium salt (27) synthesized by a known method with a base such as potassium t-butoxide, with an aldehyde (28). Depending on the reaction conditions, a cis form is formed, and if necessary, the cis form is isomerized to a trans form by a known method.

(5) Formation of —CH ₂ CH ₂ — Compound (1E) is synthesized by hydrogenating compound (1D) in the presence of a catalyst such as palladium carbon.

(6) Formation of (CH ₂ ) _4-Using phosphonium salt (29) instead of phosphonium salt (27), according to the method of paragraph (IV), a compound having-(CH ₂ ) ₂ -CH = CH- obtain. The compound is catalytically hydrogenated to synthesize a compound (1F).

(7) Formation of -C≡C- After reacting compound (23) with 2-methyl-3-butyn-2-ol in the presence of a catalyst of dichloropalladium and copper halide, under basic conditions Deprotection provides compound (30). Compound (30) is reacted with compound (22) in the presence of a catalyst of dichloropalladium and copper halide to synthesize compound (1G).

(8) Formation of -CF = CF- After compound (23) is treated with n-butyllithium, tetrafluoroethylene is reacted to obtain compound (31). The compound (22) is treated with n-butyllithium and then reacted with the compound (31) to synthesize a compound (1H).

(9) Formation of -CH ₂ O- and -OCH _2- Compound (28) is reduced with a reducing agent such as sodium borohydride to give compound (32). This is halogenated with hydrobromic acid or the like to obtain a compound (33). Compound (33) is reacted with compound (25) in the presence of potassium carbonate or the like to synthesize compound (1J).

Formation of (10)-(CH ₂ ) ₃ O- and -O (CH ₂ ) _3-Using compound (34) instead of compound (32), compound (1K) is synthesized according to the method of item (9) Do.

(11) _{-CF 2} CF 2 - generation of
J. Am. Chem. Soc., 2001, 123, 5414. The diketone (-COCO-) is fluorinated with sulfur tetrafluoride in the presence of a hydrogen fluoride catalyst according to the method described in-(CF ₂ ) A compound having _2- is obtained.

2-2. Formation of ring A 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene For rings such as, pyridine-2,5-diyl, pyrimidine-2,5-diyl, starting materials are commercially available or synthetic methods are well known. Thus, compounds (64), (67) and (71) shown below will be described.

  Decahydronaphthalene-2,6-dione (64) is the starting material for compounds with decahydronaphthalene-2,6-diyl. The compound (64) is synthesized by catalytic hydrogen reduction of a diol (63) in the presence of ruthenium oxide and further oxidation with chromium oxide according to the method described in JP-A-2000-239564.

  The structural unit of 2,3- (bistrifluoromethyl) phenylene is synthesized by the method described in Org. Lett., 2000, 2 (21), 3345. Aniline (66) is synthesized by reaction of furan (65) with 1,1,1,4,4,4-hexafluoro-2-butyne at high temperature in Diels-Alder type reaction. This compound is subjected to Sand-Meier type reaction according to the method described in Org. Synth. Coll., Vol. 2, 1943, 355 to obtain iodide (67). This compound is converted to compound (1) by a general method of synthetic organic chemistry.

  The structural unit of 2-difluoromethyl-3-fluorophenylene is synthesized by the following method. The hydroxyl group of compound (68) is protected with a suitable protecting group to give compound (69). P means a protecting group. Compound (69) is reacted with s-butyllithium and subsequently reacted with N, N-dimethylformamide (DMF) to give aldehyde (70). The compound is fluorinated with diethylaminosulfur trifluoride (DAST) and subsequently deprotected to give phenol (71). This compound is converted to compound (1) by a general method of synthetic organic chemistry.

2-3. Method for Synthesizing Compound (1) The method for producing a dihydropyran ring is as follows.

  In the above scheme, the compound (1-a) is described as an example. A Grignard reagent prepared from compound (23) is reacted with glutaric anhydride to obtain compound (s-1). This is dehydrated and condensed in the presence of DCC and DMAP to derive a compound (s-2). This is reacted with DIBAL-H (hydrogenated diisobutylaluminum hydride) to obtain a compound (s-3). Compound (s-3) is dehydrated over phosphorus pentoxide to give compound (s-4). This is reacted with borane-THF complex and then treated with 30% hydrogen peroxide to derive a compound (s-5). Compound (s-5) is oxidized with Dess-Martin periodinane (DMP) to obtain Compound (s-6).

  Compound (s-6) is reacted with LDA (lithium diisopropylamide) and then reacted with trimethylsilyl chloride to obtain compound (s-7). This is reacted with palladium (II) acetate and 1,4-benzoquinone to derive a compound (s-8). Compound (s-8) is reacted with the Grignard reagent prepared from the above-mentioned compound (22) to obtain compound (s-9). This compound is reduced with triethylsilane in the presence of boron trifluoride diethyl etherate to obtain the desired compound (1-a). Compounds in which G is a divalent group represented by formula (pr-2) can also be synthesized by this method.

3. Liquid Crystal Composition 3-1. Component Compounds The liquid crystal composition of the present invention will be described. This composition contains at least one compound (1) as component A. The composition may comprise two or more compounds (1). The component of the composition may be only the compound (1). It is preferable that the composition contains at least one of the compounds (1) in the range of 1% by weight to 99% by weight in order to exhibit excellent physical properties. In the composition having a positive dielectric anisotropy, a preferable content of the compound (1) is in the range of 5% by weight to 60% by weight. In the composition having negative dielectric anisotropy, a preferable content of the compound (1) is 30% by weight or less.

  It is preferable that this composition contains the compound (1) as the component A and further contains a liquid crystal compound selected from the components B, C, D and E shown below. Component B is compounds (2) to (4). Component C is compounds (5) to (7). Component D is a compound (8). Component E is compounds (9) to (15). This composition may contain other liquid crystal compounds different from the compounds (2) to (15). The composition may not contain other liquid crystal compounds. When preparing this composition, it is preferable to select components B, C, D, and E in consideration of the positive / negative and magnitude of dielectric anisotropy. Compositions with appropriately selected components have high stability to heat and light, high upper limit temperature, low lower limit temperature, small viscosity, appropriate optical anisotropy (ie large optical anisotropy or small optical anisotropy) , Large dielectric anisotropy, large specific resistance, and appropriate elastic constant (ie, large elastic constant or small elastic constant).

The liquid crystal composition is prepared by mixing a compound having large or small dielectric anisotropy with a positive or negative large dielectric anisotropy. The compounds (1) are classified into the compounds (1a) to (1d). The magnitudes of the dielectric anisotropy of these compounds are different. Therefore, it is preferable to use these compounds properly depending on the mode of the device. In Table 2, when R ^b of the compound (1a) is fluorine, —OCF ₃ or the like, this compound is used for an element having a mode such as FFS or PSA. When R ^b of the compound (1a) is —C≡N or the like, this compound is used for a device having a mode such as TN or STN. The compound (1b) is used for devices having modes such as VA and PSA. The compounds (1c) or (1d) can be used for the device of any mode, similarly to the compounds (2) to (4).

Component B is a compound in which the two end groups are alkyl or the like. Preferred examples of 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, and in the alkyl and alkenyl, at least one —CH ₂ — is —O— And at least one hydrogen may be replaced by fluorine.

  Component B has a small dielectric anisotropy. Component B is near neutral. The compound (2) has the effect of reducing the viscosity or adjusting the optical anisotropy. Compounds (3) and (4) have the effect of extending the temperature range of the nematic phase or raising the optical anisotropy by raising the upper limit temperature.

  As the content of component B is increased, the viscosity of the composition decreases but the dielectric anisotropy decreases. Therefore, as long as the required value of the threshold voltage of the device is satisfied, it is preferable that the content be as high as possible. When preparing a composition for a mode such as IPS or VA, the content of component B is preferably 30% by weight or more, more preferably 40% by weight or more, based on the weight of the liquid crystal composition.

Component C is a compound having a halogen or fluorine-containing group at the right end. Preferred examples of component C include compounds (5-1) to (5-16), compounds (6-1) to (6-113), and compounds (7-1) to (7-57). . In these compounds, 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 is used when preparing a composition for modes such as IPS, FFS, and OCB because the dielectric anisotropy is positive and the stability to heat and light is very excellent. The content of component C is suitably in the range of 1% by weight to 99% by weight based on the weight of the liquid crystal composition, preferably in the range of 10% by weight to 97% by weight, more preferably 40% by weight to 95%. It is in the range of%. When component C is added to a composition having a negative dielectric anisotropy, the content of component C is preferably 30% by weight or less. By adding the component C, it is possible to adjust the elastic constant of the composition and adjust the voltage-transmittance curve of the device.

Component D is a compound (8) in which the right terminal group is -C≡N or -C≡C-C≡N. Preferred examples of component D include compounds (8-1) to (8-64). In these compounds, 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 is used when preparing a composition for a mode such as TN since the dielectric anisotropy is positive and the value thereof is large. By adding this component D, the dielectric anisotropy of the composition can be increased. Component D has the effect of widening 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.

  When preparing a composition for a mode such as TN, the content of component D is suitably in the range of 1% by weight to 99% by weight, preferably 10% by weight, based on the weight of the liquid crystal composition. It is in the range of 97% by weight, more preferably in the range of 40% to 95% by weight. When component D is added to a composition having a negative dielectric anisotropy, the content of component D is preferably 30% by weight or less. By adding the component D, it is possible to adjust the elastic constant of the composition and adjust the voltage-transmittance curve of the device.

Component E is compounds (9) to (15). These compounds have phenylene in which the lateral position is substituted with two halogens, such as 2,3-difluoro-1,4-phenylene. Preferred examples of component E include compounds (9-1) to (9-8), compounds (10-1) to (10-17), compounds (11-1), and compounds (12-1) to (12-). 3), compounds (13-1) to (13-11), compounds (14-1) to (14-3), and compounds (15-1) to (15-3). In these compounds, R ¹⁵ and R ¹⁶ are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and alkenyl, at least one —CH ₂ — is —O— And at least one hydrogen may be replaced by fluorine; R ¹⁷ is hydrogen, fluorine, alkyl having 1 to 10 carbons, or alkenyl having 2 to 10 carbons, and the alkyl and In alkenyl, at least one —CH ₂ — may be replaced by —O— and at least one hydrogen may be replaced by fluorine.

  Component E has a large negative dielectric anisotropy. Component E is used when preparing a composition for modes such as IPS, VA, PSA and the like. As the content of component E is increased, the dielectric anisotropy of the composition increases negatively, but the viscosity increases. Therefore, the smaller the content, the better, as long as the required value of the threshold voltage of the device is satisfied. Considering that the dielectric anisotropy is about -5, the content is preferably 40% by weight or more in order to achieve sufficient voltage driving.

  Among the component E, since the compound (9) is a bicyclic compound, it has an effect of lowering the viscosity, adjusting the optical anisotropy or increasing the dielectric anisotropy. Since the compounds (10) and (11) are tricyclic compounds, they have the effect of increasing the maximum temperature, increasing the optical anisotropy, or increasing the dielectric anisotropy. Compounds (12) to (15) have the effect of increasing the dielectric anisotropy.

  When preparing a composition for a mode such as IPS, VA, or PSA, the content of component E is preferably 40% by weight or more, more preferably 50% by weight, based on the weight of the liquid crystal composition. To 95% by weight. When component E is added to a composition having a positive dielectric anisotropy, the content of component E is preferably 30% by weight or less. By adding the component E, it is possible to adjust the elastic constant of the composition and adjust the voltage-transmittance curve of the device.

  High stability to heat and light, high upper limit temperature, low lower limit temperature, small viscosity, appropriate optical anisotropy, large dielectric constant anisotropy by appropriately combining the components B, C, D and E described above A liquid crystal composition can be prepared which satisfies at least one of physical properties such as conductivity, large specific resistance, and a suitable elastic constant. If necessary, liquid crystal compounds different from the components B, C, D, and E may be added.

3-2. Additives The liquid crystal composition is prepared by a known method. For example, the component compounds are mixed and dissolved together by heating. Depending on the application, additives may be added to the composition. Examples of the additives are a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet light absorber, a light stabilizer, a heat stabilizer, a dye, an antifoaming agent and the like. Such additives are well known to those skilled in the art and are described in the literature.

  In a liquid crystal display device having a PSA (polymer sustained alignment) mode, the composition contains a polymer. The polymerizable compound is added in order to form a polymer in the composition. A polymer is formed in the composition by polymerizing the polymerizable compound by irradiation with ultraviolet light in a state where a voltage is applied between the electrodes. By this method, an appropriate pretilt is achieved, so that the response time is shortened and an element with improved image sticking is produced.

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

Further preferred examples are compounds (M-1) to (M-17). In these compounds, R ²⁵ to R ³¹ are independently hydrogen or methyl; s, v and x are independently 0 or 1; It is an integer. L ²¹ to L ²⁶ are independently hydrogen or fluorine; L ²⁷ and L ²⁸ are independently hydrogen, fluorine or methyl.

  The polymerizable compound can be rapidly polymerized by adding a polymerization initiator. By optimizing the reaction temperature, the amount of remaining polymerizable compound can be reduced. Examples of photo radical polymerization initiators are TPO, 1173, and 4265 from Darrocure series of BASF, and 184, 369, 500, 651, 784, 819, 907, 1300, 1700, 1800, 1850 from Irgacure series. , And 2959.

  Additional examples of photo radical polymerization initiators 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 It is.

  After adding a photo radical polymerization initiator to the liquid crystal composition, polymerization can be performed by irradiating ultraviolet light in a state where an electric field is applied. However, unreacted polymerization initiator or decomposition products of the polymerization initiator may cause display defects such as image sticking to the device. In order to prevent this, photopolymerization may be carried out without adding a polymerization initiator. The preferred wavelength of the light to be irradiated is in the range of 150 nm to 500 nm. A further preferred wavelength is in the range of 250 nm to 450 nm, and the most preferred wavelength is in the range of 300 nm to 400 nm.

  When storing the 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, phenothiazine and the like.

The optically active compound has an effect of preventing reverse twist by inducing a helical structure to liquid crystal molecules to give 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 in order to adjust the temperature dependency of the helical pitch. The following compounds (Op-1) to (Op-18) can be mentioned as preferable examples of the optically active compound. 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.

  Antioxidants are effective to maintain a large voltage holding ratio. Preferred examples of the antioxidant include the following compounds (AO-1) and (AO-2); IRGANOX 415, IRGANOX 565, IRGANOX 1010, IRGANOX 1035, IRGANOX 3114, and IRGANOX 1098 (trade name; BASF Corporation) be able to. UV absorbers are effective to prevent the lowering of the upper limit temperature. Preferred examples of UV absorbers are benzophenone derivatives, benzoate derivatives, triazole derivatives and the like, and specific examples include the following compounds (AO-3) and (AO-4): TINUVIN 329, TINUVIN P, TINUVIN 326, TINUVIN 234, Mention may be made of TINUVIN 213, TINUVIN 400, 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 to maintain high voltage holding rates. The following compounds (AO-5) and (AO-6); TINUVIN 144, TINUVIN 765, and TINUVIN 770DF (brand name; BASF Corporation) can be mentioned as a preferable example of a light stabilizer. 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. In order to conform to a guest host (GH) mode device, a dichroic dye such as an azo dye or an anthraquinone dye is added to the composition. Defoamers are effective to prevent foaming. Preferred examples of the antifoaming 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 carbon To 20 alkyl. In 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 is 1,4-cyclohexylene or 1,4-phenylene; z is 1, 2 or It is three.

4. Liquid Crystal Display Device A liquid crystal composition having a positive dielectric anisotropy has an operation such as PC, TN, STN, OCB or PSA and can be used for a liquid crystal display device driven by an active matrix (AM method). This composition can be used also for a liquid crystal display device having an operation of PC, TN, STN, OCB, VA, IPS, etc. and driven by a passive matrix (PM) method. These AM type and PM type elements can be applied to any of reflective type, transmissive type, and semi-transmissive type.

  A liquid crystal composition having a large negative dielectric anisotropy has an operation mode such as VA, IPS, or PSA, and can be suitably used for a liquid crystal display element driven by an AM method. This composition can be particularly suitably used for a liquid crystal display element having a VA mode and driven by an AM mode.

  The composition is also suitable for a nematic curvilinear aligned phase (NCAP) device, in which the composition is microencapsulated. This composition can also be used for polymer dispersed liquid crystal display (PDLCD) and polymer network liquid crystal display (PNLCD). In these compositions, a large amount of polymerizable compound is added. On the other hand, when the addition amount of the polymerizable compound is 10% by weight or less based on the weight of the liquid crystal composition, a PSA mode liquid crystal display device is produced. The preferred proportion is in the range of 0.1% by weight to 2% by weight. A further preferred ratio is in the range of 0.2% by weight to 1.0% by weight. The elements in the PSA mode can be driven by a driving method such as an active matrix or passive matrix. Such an element can be applied to any of reflective, transmissive and semi-transmissive types.

  The invention will be further described in detail by way of examples (including synthesis examples and usage examples). The invention is not limited by these examples. The present invention comprises a mixture of the composition of Use Example 1 and the composition of Use Example 2. The present invention also includes a composition prepared by mixing at least two of the compositions of Use Examples.

1. Examples of Compound (1) Compound (1) was synthesized by the following procedure. The compound synthesized was identified by a method such as NMR analysis. The physical properties of the compounds and compositions and the characteristics of the devices were measured by the following methods.

NMR analysis: For measurement, DRX-500 manufactured by Bruker Biospin Ltd. was used. ^In the measurement of ¹ H-NMR, the sample was dissolved in a deuterated solvent such as CDCl ₃ , and measurement was performed under the conditions of room temperature, 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 integrations was 24 times. In the description of nuclear magnetic resonance spectrum, s is singlet, d is doublet, t is triplet, q is quartet, quin is quintet, sex is sextet, m is multiplet, br is broad.

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

  HPLC analysis: For measurement, Prominence (LC-20AD; SPD-20A) manufactured by Shimadzu Corporation was used. As a column, YMC YMC-Pack ODS-A (length 150 mm, inner diameter 4.6 mm, particle diameter 5 μm) was used. The eluate was used by appropriately mixing acetonitrile and water. As a detector, a UV detector, an RI detector, a CORONA detector, etc. were used suitably. 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 made by Shimadzu Corporation was used.

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

  Measurement sample: When measuring the phase structure and transition temperature (clearing point, melting point, polymerization initiation temperature, etc.), the compound itself was used as a sample. When physical properties such as the upper limit temperature of the nematic phase, viscosity, optical anisotropy, dielectric anisotropy and the like were measured, a mixture of the compound and the base liquid crystal was used as a sample.

  When using the sample which mixed the compound with the mother liquid crystal, it measured by the following method. A sample was prepared by mixing 15% by weight of the compound and 85% by weight of mother liquid crystals. From the measured values of this sample, extrapolated values were calculated according to the extrapolation method represented by the following equation, and this value was described. <Extrapolated value> = (100 × <measured value of sample> − <weight% of mother liquid crystal> × <measured value of mother liquid crystal>) / <weight% of compound>

  Even if the ratio between the compound and the base liquid crystal is this ratio, when crystals (or smectic phase) precipitate at 25 ° C., the ratio between the compound and the base liquid crystal is 10% by weight: 90% by weight, 5% %: 95% by weight, and 1% by weight: 99% by weight, and the physical properties of the sample were measured at a rate at which crystals (or smectic phase) did not precipitate at 25 ° C. The ratio of the compound to the mother liquid crystals is 15% by weight: 85% by weight unless otherwise specified.

When the dielectric anisotropy of the compound was positive, the following mother liquid crystals (i) were used. The proportions of the components of the mother liquid crystals are shown by weight%.
Mother LCD (i):

When the dielectric anisotropy of the compound was negative, the following mother liquid crystal (ii) was used.
Mother liquid crystal (ii):

  Measurement method: Measurement of physical properties was performed by the following method. Many of these are described in the JEITA standard (JEITA ED-2521B), which is deliberately established by the Japan Electronics and Information Technology Industries Association (JEITA). A modified method of this was also used. A thin film transistor (TFT) was not attached to the TN device used for the measurement.

(1) Phase structure: The sample was placed on a hot plate of a melting point measuring apparatus equipped with a polarization microscope (model: Model FP-52 hot stage). While heating this sample at a rate of 3 ° C./min, the phase state and its change were observed with a polarization microscope to identify the type of phase.

(2) Transition temperature (° C.): For measurement, a scanning calorimeter manufactured by Perkin Elmer, a Diamond DSC system, or a high-sensitive differential scanning calorimeter manufactured by SII Nano Technology, X-DSC7000 was used. The temperature of the sample was raised and lowered at a rate of 3 ° C./min, and the transition point was determined by extrapolating the start point of the endothermic peak or exothermic peak accompanying the phase change of the sample. The melting point of the compound and the polymerization initiation temperature were also measured using this apparatus. The temperature at which a compound transitions from a solid to a liquid crystal phase such as a smectic phase or a nematic phase may be abbreviated as "the lower limit temperature of the liquid crystal phase". The temperature at which a compound transitions from liquid crystal phase to liquid may be abbreviated as the "clearing point".

The crystal is designated C. When the type of crystal can be distinguished, each is expressed as C ₁ or C ₂ . The smectic phase is represented by S and the nematic phase is 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 crystal to nematic phase is 50.0 ° C., and the transition temperature from nematic phase to liquid is 100.0 ° C.

(3) Low temperature compatibility: A sample in which the base liquid crystal and the compound are mixed such that the proportion of the compound is 20% by weight, 15% by weight, 10% by weight, 5% by weight, 3% by weight, and 1% by weight Prepared and put the sample in a glass bottle. After storing the glass bottle in a -10 ° C or -20 ° C freezer for a certain period of time, it was observed whether crystals or a smectic phase had precipitated.

(4) Upper limit temperature of nematic phase (T _NI or NI; ° C.): The sample was placed on a hot plate of a melting point measuring apparatus equipped with a polarization microscope and heated at a rate of 1 ° C./min. The temperature was measured when part of the sample changed from the nematic phase to the isotropic liquid. When the sample is a mixture of compound (1) and mother liquid crystals, it is indicated by the symbol _TNI . When the sample is a mixture of compound (1) and a compound such as component B, C or D, it is indicated by the symbol NI. The upper limit temperature of the nematic phase may be abbreviated as "upper limit temperature".

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

(6) Viscosity (bulk viscosity; ;; measured at 20 ° C .; mPa · s): For measurement, an E-type rotational viscometer manufactured by Tokyo Keiki Co., Ltd. was used.
(7) Optical anisotropy (refractive index anisotropy; measured at 25 ° C .; Δn): Measurement was carried out with an Abbe refractometer with a polarizing plate attached to the ocular, using light of wavelength 589 nm. After rubbing the surface of the main prism in one direction, a sample was dropped on the main prism. The refractive index (n‖) was measured when the direction of polarization was parallel to the direction of rubbing. The refractive index (n⊥) was measured when the polarization direction was perpendicular to the rubbing direction. The value of optical anisotropy (Δn) was calculated from the equation of Δn = n‖-n⊥.

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

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

(10) Voltage holding ratio (VHR-2; measured at 80 ° C .;%): The voltage holding ratio was measured by the above method except that measurement was performed at 80 ° C. instead of 25 ° C. The obtained result is shown by the symbol of VHR-2.

  The measurement method of physical properties may be different between a sample with positive dielectric anisotropy and a sample with negative dielectric anisotropy. The measuring methods when the dielectric anisotropy is positive are described in the items (11a) to (15a). When the dielectric anisotropy is negative, the terms (11b) to (15b) are described.

(11a) Viscosity (rotational viscosity; γ1; measured at 25 ° C .; mPa · s)
Positive dielectric anisotropy: The measurement was according to the method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). The sample was placed in a TN device having a twist angle of 0 degree and a distance between two glass substrates (cell gap) of 5 μm. The device was applied stepwise in steps of 0.5 V in the range of 16 V to 19.5 V. After 0.2 seconds of no application, application was repeated under the condition of only one rectangular wave (rectangular pulse; 0.2 seconds) and no application (2 seconds). The peak current and peak time of transient current generated by this application were measured. These measurements and M. The rotational viscosity was obtained from the paper of Imai et al., Calculation formula (8) on page 40. The value of dielectric anisotropy required for this calculation was determined by the method described below using the device for which this rotational viscosity was measured.

(11b) Viscosity (rotational viscosity; γ1; measured at 25 ° C .; mPa · s)
Negative dielectric anisotropy: Measurement was according to the method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). A sample was placed in a VA device in which the distance between two glass substrates (cell gap) was 20 μm. The device was applied stepwise in the range of 39 to 50 volts in increments of 1 volt. After 0.2 seconds of no application, application was repeated under the condition of only one rectangular wave (rectangular pulse; 0.2 seconds) and no application (2 seconds). The peak current and peak time of transient current generated by this application were measured. These measurements and M. The rotational viscosity was obtained from the paper of Imai et al., Calculation formula (8) on page 40. The dielectric anisotropy required for this calculation was the value measured in the section of dielectric anisotropy described below.

(12a) Dielectric anisotropy (Δε; measured at 25 ° C.)
Positive dielectric anisotropy: A sample was placed in a TN device in which the distance between two glass substrates (cell gap) is 9 μm and the twist angle is 80 degrees. Sine waves (10 V, 1 kHz) were applied to this device, and after 2 seconds, the dielectric constant (‖) in the major axis direction of liquid crystal molecules was measured. Sine waves (0.5 V, 1 kHz) were applied to this device, and after 2 seconds, the dielectric constant (⊥) in the minor axis direction of liquid crystal molecules was measured. The value of dielectric anisotropy was calculated from the equation of Δε = ε‖−ε⊥.

(12b) dielectric anisotropy (Δε; measured at 25 ° C.)
Negative dielectric anisotropy: The value of dielectric anisotropy was calculated from the equation of Δε = ε‖−ε⊥. The dielectric constants (ε‖ and ε⊥) were measured as follows.
1) Measurement of dielectric constant (‖): A solution of octadecyltriethoxysilane (0.16 mL) in ethanol (20 mL) was applied to a well-cleaned glass substrate. The glass substrate was rotated by a spinner and then heated at 150 ° C. for 1 hour. A sample was placed in a VA device in which the distance between two glass substrates (cell gap) was 4 μm, and this device was sealed with an adhesive cured with ultraviolet light. Sine waves (0.5 V, 1 kHz) were applied to this device, and after 2 seconds, the dielectric constant (‖) in the major axis direction of liquid crystal molecules was measured.
2) Measurement of dielectric constant (ε⊥): A polyimide solution was applied to a well-cleaned glass substrate. After firing the glass substrate, the obtained alignment film was rubbed. The sample was placed in a TN device in which the distance between two glass substrates (cell gap) was 9 μm and the twist angle was 80 degrees. Sine waves (0.5 V, 1 kHz) were applied to this device, and after 2 seconds, the dielectric constant (⊥) in the minor axis direction of liquid crystal molecules was measured.

(13a) elastic constant (K; measured at 25 ° C .; pN)
Positive dielectric anisotropy: An HP4284A LCR meter manufactured by Yokogawa-Hewlett-Packard Co. was used for measurement. The sample was placed in a horizontal alignment device in which the distance between two glass substrates (cell gap) was 20 μm. A charge of 0 to 20 volts was applied to the device, and the capacitance and the applied voltage were measured. The values of the measured capacitance (C) and the applied voltage (V) are calculated using the formula (2.98) and formula (2.101) on page 75 of “Liquid Crystal Device Handbook” (Nippon Kogyo Shimbun) Fitting was performed to obtain values of K ₁₁ and K ₃₃ from equation (2.99). Then the equation (3.18) on page 171, to calculate the _{K 22} using the values of _{K 11} and _{K 33} was determined previously. The elastic constant K was represented by the average value of K ₁₁ , K ₂₂ and K ₃₃ thus determined.

(13b) elastic constant (K ₁₁ and K ₃₃ ; measured at 25 ° C .; pN)
Negative dielectric anisotropy: For measurement, an EC-1 elastic modulus measuring device manufactured by Toyo Corporation was used. The sample was placed in a vertical alignment device in which the distance between two glass substrates (cell gap) was 20 μm. A charge of 20 volts to 0 volts was applied to the device, and the capacitance and the applied voltage were measured. The values of capacitance (C) and applied voltage (V) are fitted using the formula (2.98) and formula (2.101) shown on page 75 of “Liquid Crystal Device Handbook” (Nippon Kogyo Shimbun Ltd.) The value of the elastic constant was obtained from the equation (2.100).

(14a) Threshold voltage (Vth; measured at 25 ° C .; V)
Positive dielectric anisotropy: For measurement, an LCD 5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. The light source was a halogen lamp. The sample was placed in a normally white mode TN device in which the distance between two glass substrates (cell gap) is 0.45 / Δn (μm) and the twist angle is 80 degrees. The voltage (32 Hz, rectangular wave) applied to this element was gradually increased by 0.02 V from 0 V to 10 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 was created in which the transmittance was 100% when the light amount was maximum, and the transmittance was 0% when the light amount was minimum. The threshold voltage was represented by the voltage at 90% transmittance.

(14b) Threshold voltage (Vth; measured at 25 ° C .; V)
Negative dielectric anisotropy: For measurement, an LCD 5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. The light source was a halogen lamp. A sample is placed in a normally black mode VA device in which the distance between two glass substrates (cell gap) is 4 μm and the rubbing direction is antiparallel, and an adhesive for curing this device with ultraviolet light is used. Used and sealed. The voltage (60 Hz, rectangular wave) applied to this element was gradually increased by 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 was created in which the transmittance was 100% when the light amount was maximum, and the transmittance was 0% when the light amount was minimum. The threshold voltage was represented by the voltage at 10% transmittance.

(15a) Response time (τ; measured at 25 ° C; ms)
Positive dielectric anisotropy: For measurement, an LCD 5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. The light source was a halogen lamp. The low pass filter (Low-pass filter) was set to 5 kHz. The sample was placed in a normally white mode TN device in which the distance between two glass substrates (cell gap) was 5.0 μm and the twist angle was 80 degrees. A rectangular wave (60 Hz, 5 V, 0.5 seconds) was applied to this element. At this time, the device was irradiated with light from the vertical direction, and the amount of light transmitted through the device was measured. It was considered that the transmittance was 100% when the light amount was maximum, and the transmittance was 0% when the light amount was minimum. The rise time (τr: millisecond) is the time taken for the transmittance to change from 90% to 10%. The fall time (τf: milliseconds) is the time taken to change from 10% transmission to 90% transmission. The response time is represented by the sum of the rise time and the fall time obtained in this manner.

(15b) Response time (τ; measured at 25 ° C; ms)
Negative dielectric anisotropy: For measurement, an LCD 5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. The light source was a halogen lamp. The low pass filter (Low-pass filter) was set to 5 kHz. The sample was placed in a normally black mode PVA element in which the distance between two glass substrates (cell gap) was 3.2 μm and the rubbing direction was antiparallel. The device was sealed using an adhesive that cures with ultraviolet light. A voltage slightly higher than the threshold voltage was applied to the device for 1 minute, and then ultraviolet light of 23.5 mW / cm ² was applied for 8 minutes while applying a voltage of 5.6 V. A rectangular wave (60 Hz, 10 V, 0.5 seconds) was applied to this element. At this time, the device was irradiated with light from the vertical direction, and the amount of light transmitted through the device was measured. It was considered that the transmittance was 100% when the light amount was maximum, and the transmittance was 0% when the light amount was minimum. The response time is represented by the time (fall time; milliseconds) taken to change from 90% transmittance to 10% transmittance.

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

Synthesis Example 1 Synthesis of Compound (1)

[First step]
5.0 g of a compound (t-1) synthesized by a known method was dissolved in 60 mL of THF, to which 26.3 mL of propylmagnesium bromide THF solution (1 M / L) was dropped at room temperature. After stirring for 30 minutes at 50 ° C., the mixture was stirred overnight at room temperature. Under ice-cooling, a saturated aqueous solution of magnesium chloride was added dropwise, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 5.9 g of a compound (t-2). Compound t-2 was used for the next reaction without purification.

[Second step]
Under a nitrogen atmosphere, 5.9 g of the compound (t-2) was dissolved in a mixed solvent of 70 mL of dichloromethane and 70 mL of acetonitrile, and 3.8 g of triethylsilane was added thereto. In this solution, 4.0 g of trifluoroborane-diethyl ether complex was dropped at -50 ° C, and the mixture was stirred at -50 ° C for 30 minutes, and then stirred at room temperature for 1 hour. The reaction mixture was quenched by the dropwise addition of saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with dichloromethane, and the combined organic phase was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure, and the residue is purified by silica gel column chromatography (heptane: toluene = 6: 4, volume ratio) and further purified by recrystallization (Solmix) to obtain compound (1) 1.0 g I got

¹ H-NMR (CDCl ₃ ): δ 6.72 (dd, 2 H), 6.02 (dd, 1 H), 5.38 (dd, 1 H), 5.26 (dd, 1 H), 3.48-3 23 (m, 2H), 2.31-2.28 (m, 1H), 1.31-1.04 (m, 4H), 0.90 (t, 3H).

  The compounds shown below can be synthesized with reference to the method described in the synthesis example and the description of “2. Synthesis of compound (1)”.

2. Composition Examples The compositions of the present invention will be described in detail by way of examples. The present invention comprises a mixture of the composition of Use Example 1 and the composition of Use Example 2. The present invention also includes a mixture of at least two of the compositions of Use Examples. The compounds in the use examples are represented by symbols based on the definition of Table 3 below. In Table 3, the configuration for 1,4-cyclohexylene is trans. The number in parenthesis after the symbol in the example of use represents the chemical formula to which the compound belongs. The symbol (-) means other liquid crystal compounds different from the compounds (2) to (15). The proportion (percentage) of the liquid crystal compound is a weight percentage (% by weight) based on the weight of the liquid crystal composition. Finally, the physical properties of the composition were summarized. Physical properties were measured according to the method described above, and the measured values were described as they were (without extrapolation).

[Composition Example 1]
3-cxOB (F) B (F, F) XB (F, F) -F (54) 5%
3-HB-O1 (2-5) 15%
3-HB (2F, 3F) -O2 (9-1) 12%
5-HB (2F, 3F) -O2 (9-1) 12%
2-HHB (2F, 3F) -1 (10-1) 12%
3-HHB (2F, 3F) -1 (10-1) 12%
3-HHB (2F, 3F) -O2 (10-1) 13%
5-HHB (2F, 3F) -O2 (10-1) 13%
3-HHB-1 (3-1) 6%

[Composition Example 2]
3-cxOB (F) B (F, F) XB (F, F) -CF3 (53) 5%
5-HB-O2 (2-5) 3%
3-H 2 B (2F, 3F) -O 2 (9-4) 22%
5-H2B (2F, 3F) -O2 (9-4) 22%
2-HHB (2F, 3CL) -O2 (10-12) 2%
3-HHB (2F, 3CL) -O2 (10-12) 3%
4-HHB (2F, 3CL) -O2 (10-12) 2%
5-HHB (2F, 3CL) -O2 (10-12) 2%
3-HBB (2F, 3F) -O2 (10-7) 9%
5-HBB (2F, 3F) -O2 (10-7) 9%
V-HHB-1 (3-1) 6%
3-HHB-3 (3-1) 6%
3-HHEBH-3 (4-6) 3%
3-HHEBH-4 (4-6) 3%
3-HHEBH-5 (4-6) 3%

Composition Example 3
3-cxOB (F, F) B (F, F) XB (F, F) -F (52) 5%
3-HB-O1 (2-5) 15%
3-HB (2F, 3F) -O2 (9-1) 12%
5-HB (2F, 3F) -O2 (9-1) 12%
2-HHB (2F, 3F) -1 (10-1) 12%
3-HHB (2F, 3F) -1 (10-1) 12%
3-HHB (2F, 3F) -O2 (10-1) 13%
5-HHB (2F, 3F) -O2 (10-1) 13%
6-HEB (2F, 3F) -O2 (9-6) 6%

[Composition Example 4]
3-HCxOB (2F, 3F)-O2 5%
3-HB-O2 (2-5) 17%
5-HB-O2 (2-5) 5%
3-H 2 B (2F, 3F) -O 2 (9-4) 18%
5-H2B (2F, 3F) -O2 (9-4) 19%
3-HHB (2F, 3CL) -O2 (10-12) 5%
2-HBB (2F, 3F) -O2 (10-7) 3%
3-HBB (2F, 3F) -O2 (10-7) 9%
5-HBB (2F, 3F) -O2 (10-7) 9%
3-HHB-1 (3-1) 3%
3-HHB-3 (3-1) 4%
3-HHB-O1 (3-1) 3%

[Composition Example 5]
3-CxOBB (2F, 3F) -O2 5%
1-BB-3 (2-8) 12%
3-HB-O2 (2-5) 7%
5-HB-O2 (2-5) 5%
3-BB (2F, 3F)-O2 (9-3) 10%
5-BB (2F, 3F) -O2 (9-3) 7%
2-HH1OB (2F, 3F)-O2 (10-5) 14%
3-HH1OB (2F, 3F) -O2 (10-5) 22%
5-HBB (2F, 3F) -O2 (10-7) 8%
3-HHB-1 (3-1) 5%
3-HHB-O1 (3-1) 3%
5-B (F) BB-2 (3-8) 2%

[Example 6]
3-HHcxO-5 5%
3-HB-O2 (2-5) 10%
5-HB-CL (5-2) 13%
3-HBB (F, F) -F (6-24) 7%
3-PyB (F) -F (5-15) 9%
5-PyB (F) -F (5-15) 9%
3-PyBB-F (6-81) 9%
4-PyBB-F (6-81) 9%
5-PyBB-F (6-81) 9%
5-HBB (F) B-2 (4-5) 10%
5-HBB (F) B-3 (4-5) 10%

[Example 7]
3-cxOB (F) B (F, F) XB (F, F) -F (54) 5%
2-HB-C (8-1) 5%
3-HB-C (8-1) 10%
3-HB-O2 (2-5) 12%
2-BTB-1 (2-10) 3%
3-HHB-F (6-1) 4%
3-HHB-1 (3-1) 8%
3-HHB-O1 (3-1) 5%
3-HHB-3 (3-1) 14%
3-HHEB-F (6-10) 4%
5-HHEB-F (6-10) 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%

[Example 8]
3-cxOB (F) B (F, F) XB (F, F) -CF3 (53) 5%
7-HB (F, F)-F (5-4) 3%
3-HB-O2 (2-5) 7%
2-HHB (F) -F (6-2) 9%
3-HHB (F) -F (6-2) 9%
5-HHB (F) -F (6-2) 10%
2-HBB (F)-F (6-23) 9%
3-HBB (F) -F (6-23) 9%
5-HBB (F)-F (6-23) 13%
2-HBB-F (6-22) 4%
3-HBB-F (6-22) 4%
5-HBB-F (6-22) 3%
3-HBB (F, F)-F (6-24) 5%
5-HBB (F, F)-F (6-24) 10%

[Example 9]
3-cxOB (F, F) B (F, F) XB (F, F) -F (52) 2%
5-HB-CL (5-2) 21%
3-HHB-F (6-1) 4%
3-HHB-CL (6-1) 3%
4-HHB-CL (6-1) 4%
3-HHB (F) -F (6-2) 15%
4-HHB (F) -F (6-2) 11%
5-HHB (F) -F (6-2) 11%
7-HHB (F) -F (6-2) 8%
5-HBB (F)-F (6-2) 4%
1O1-HBBH-5 (4-1) 3%
3-HBBB (F, F)-F (7-6) 2%
4-HBBB (F, F)-F (7-6) 3%
5-HBBB (F, F)-F (7-6) 3%
3-HH2BB (F, F) -F (7-15) 3%
4-HH2BB (F, F) -F (7-15) 3%

[Usage example 10]
3-HCxOB (2F, 3F)-O2 5%
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) 18%
5-HBB (F, F)-F (6-24) 18%
3-H 2 BB (F, F)-F (6-27) 10%
5-HBBB (F, F)-F (7-6) 3%
5-HHEBB-F (7-17) 2%
3-HH2BB (F, F) -F (7-15) 3%
1O1-HBBH-4 (4-1) 4%
1O1-HBBH-5 (4-1) 4%

[Example 11 of use]
3-CxOBB (2F, 3F) -O2 4%
3-HB-CL (2-5) 6%
5-HB-CL (2-5) 4%
3-HHB-OCF3 (6-1) 5%
3-H2HB-OCF3 (6-13) 5%
5-H4HB-OCF3 (6-19) 13%
V-HHB (F) -F (6-2) 5%
3-HHB (F) -F (6-2) 5%
5-HHB (F) -F (6-2) 5%
3-H4HB (F, F) -CF3 (6-21) 8%
5-H4HB (F, F) -CF3 (6-21) 8%
5-H2HB (F, F) -F (6-15) 5%
5-H4HB (F, F) -F (6-21) 7%
2-H2BB (F) -F (6-26) 5%
3-H2BB (F) -F (6-26) 10%
3-HBEB (F, F)-F (6-39) 5%

[Example 12 of use]
3-HHcxO-5 5%
7-HB-1 (2-5) 10%
3-HB-O2 (2-5) 5%
5-HB-O2 (2-5) 13%
3-HB (2F, 3F) -O2 (9-1) 18%
5-HB (2F, 3F) -O2 (9-1) 16%
3-HHB (2F, 3CL) -O2 (10-12) 3%
4-HHB (2F, 3CL) -O2 (10-12) 3%
5-HHB (2F, 3CL) -O2 (10-12) 2%
3-HH1OCro (7F, 8F) -5 (13-6) 5%
5-HBB (F) B-2 (4-5) 10%
5-HBB (F) B-3 (4-5) 10%

[Example 13 of use]
3-cxOB (F) B (F, F) XB (F, F) -F (54) 5%
1-BB-3 (2-8) 10%
3-HB-O2 (2-5) 5%
5-HB-O2 (2-5) 5%
3-BB (2F, 3F) -O2 (9-3) 18%
2-HH1OB (2F, 3F) -O2 (10-5) 20%
3-HH1OB (2F, 3F) -O2 (10-5) 14%
5-HBB (2F, 3F) -O2 (10-7) 9%
3-HHB-1 (3-1) 8%
5-B (F) BB-2 (3-8) 6%

[Example 14]
3-cxOB (F) B (F, F) XB (F, F) -CF3 (53) 5%
3-HB-O1 (2-5) 15%
3-HB (2F, 3F) -O2 (9-1) 12%
5-HB (2F, 3F) -O2 (9-1) 12%
2-HHB (2F, 3F) -1 (10-1) 12%
3-HHB (2F, 3F) -1 (10-1) 12%
3-HHB (2F, 3F) -O2 (10-1) 13%
5-HHB (2F, 3F) -O2 (10-1) 13%
3-HHB-1 (3-1) 6%

[Example 15 of use]
3-cxOB (F, F) B (F, F) XB (F, F) -F (52) 5%
5-HB-O2 (2-5) 3%
3-H 2 B (2F, 3F) -O 2 (9-4) 22%
5-H2B (2F, 3F) -O2 (9-4) 22%
2-HHB (2F, 3CL) -O2 (10-12) 2%
3-HHB (2F, 3CL) -O2 (10-12) 3%
4-HHB (2F, 3CL) -O2 (10-12) 2%
5-HHB (2F, 3CL) -O2 (10-12) 2%
3-HBB (2F, 3F) -O2 (10-7) 9%
5-HBB (2F, 3F) -O2 (10-7) 9%
V-HHB-1 (3-1) 6%
3-HHB-3 (3-1) 6%
3-HHEBH-3 (4-6) 3%
3-HHEBH-4 (4-6) 3%
3-HHEBH-5 (4-6) 3%

[Example 16]
3-HCxOB (2F, 3F)-O2 3%
3-HB-O2 (2-5) 10%
5-HB-CL (5-2) 13%
3-HBB (F, F) -F (6-24) 7%
3-PyB (F) -F (5-15) 10%
5-PyB (F) -F (5-15) 10%
3-PyBB-F (6-80) 9%
4-PyBB-F (6-80) 9%
5-PyBB-F (6-80) 9%
5-HBB (F) B-2 (4-5) 10%
5-HBB (F) B-3 (4-5) 10%

[Example 17]
3-CxOBB (2F, 3F) -O2 5%
3-HB-O1 (2-5) 15%
3-HB (2F, 3F) -O2 (9-1) 12%
5-HB (2F, 3F) -O2 (9-1) 12%
2-HHB (2F, 3F) -1 (10-1) 12%
3-HHB (2F, 3F) -1 (10-1) 12%
3-HHB (2F, 3F) -O2 (10-1) 13%
5-HHB (2F, 3F) -O2 (10-1) 13%
6-HEB (2F, 3F) -O2 (9-6) 6%

[Example 18]
3-HHcxO-5 5%
2-HB-C (8-1) 5%
3-HB-C (8-1) 10%
3-HB-O2 (2-5) 12%
2-BTB-1 (2-10) 3%
3-HHB-F (6-1) 4%
3-HHB-1 (3-1) 8%
3-HHB-O1 (3-1) 5%
3-HHB-3 (3-1) 14%
3-HHEB-F (6-10) 4%
5-HHEB-F (6-10) 4%
2-HHB (F) -F (6-2) 7%
3-HHB (F) -F (6-2) 7%
5-HHB (F) -F (6-3) 7%
3-HHB (F, F) -F (6-3) 5%

[Example 19]
3-cxOB (F) B (F, F) XB (F, F) -F (54) 5%
3-HB-O2 (2-5) 17%
5-HB-O2 (2-5) 5%
3-H 2 B (2F, 3F) -O 2 (6-4) 18%
5-H2B (2F, 3F) -O2 (6-4) 19%
3-HHB (2F, 3CL) -O2 (10-12) 5%
2-HBB (2F, 3F) -O2 (10-7) 3%
3-HBB (2F, 3F) -O2 (10-7) 9%
5-HBB (2F, 3F) -O2 (10-7) 9%
3-HHB-1 (3-1) 3%
3-HHB-3 (3-1) 4%
3-HHB-O1 (3-1) 3%

[Example 20]
3-cxOB (F) B (F, F) XB (F, F) -CF3 (53) 5%
7-HB (F, F)-F (5-4) 3%
3-HB-O2 (2-5) 7%
2-HHB (F) -F (6-2) 9%
3-HHB (F) -F (6-2) 9%
5-HHB (F) -F (6-2) 10%
2-HBB (F)-F (6-23) 9%
3-HBB (F) -F (6-23) 9%
5-HBB (F)-F (6-23) 13%
2-HBB-F (6-22) 4%
3-HBB-F (6-22) 4%
5-HBB-F (6-22) 3%
3-HBB (F, F)-F (6-24) 5%
5-HBB (F, F)-F (6-24) 10%

[Example 21]
3-cxOB (F, F) B (F, F) XB (F, F) -F (52) 5%
1-BB-3 (2-8) 12%
3-HB-O2 (2-5) 7%
5-HB-O2 (2-5) 5%
3-BB (2F, 3F)-O2 (9-3) 10%
5-BB (2F, 3F) -O2 (9-3) 7%
2-HH1OB (2F, 3F)-O2 (10-5) 14%
3-HH1OB (2F, 3F) -O2 (10-5) 21%
3-HBB (2F, 3F) -O2 (10-7) 9%
3-HHB-1 (3-1) 5%
3-HHB-O1 (3-1) 3%
5-B (F) BB-2 (3-8) 2%

[Example 22]
3-HCxOB (2F, 3F)-O2 5%
5-HB-CL (5-2) 20%
3-HHB-F (6-1) 4%
3-HHB-CL (6-1) 3%
4-HHB-CL (6-1) 4%
3-HHB (F) -F (6-2) 15%
4-HHB (F)-F (6-2) 10%
5-HHB (F) -F (6-2) 10%
7-HHB (F) -F (6-2) 8%
5-HBB (F)-F (6-23) 4%
1O1-HBBH-5 (4-1) 3%
3-HBBB (F, F)-F (7-6) 2%
4-HBBB (F, F)-F (7-6) 3%
5-HBBB (F, F)-F (7-6) 3%
3-HH2BB (F, F) -F (7-15) 3%
4-HH2BB (F, F) -F (7-15) 3%

[Example 23]
3-CxOBB (2F, 3F) -O2 5%
3-HB-O1 (2-5) 15%
3-HB (2F, 3F) -O2 (9-1) 12%
5-HB (2F, 3F) -O2 (9-1) 12%
2-HHB (2F, 3F) -1 (10-1) 12%
3-HHB (2F, 3F) -1 (10-1) 12%
3-HHB (2F, 3F) -O2 (10-1) 13%
5-HHB (2F, 3F) -O2 (10-1) 13%
3-HHB-1 (3-1) 6%

  The liquid crystal composition of the present invention has high stability to ultraviolet light and heat, high upper limit temperature of nematic phase, lower lower limit temperature of nematic phase, small viscosity, appropriate optical anisotropy, large dielectric anisotropy, appropriate At least one of the physical properties such as the elastic constant is satisfied, or an appropriate balance regarding at least two physical properties is provided. Therefore, the liquid crystal display element containing this composition can be used for a liquid crystal projector, a liquid crystal television, etc.

Claims (7)

At least one compound selected from the group of compounds represented by formula (1a) as the first component and at least one selected from the group of compounds represented by formulas (2) to (4) as the second component Liquid crystal composition containing a compound and having a nematic phase.

In formula (1a),
R ^a is alkyl having 1 to 10 carbons or alkenyl having 2 to 12 carbons, R ^b is alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine, or fluorine In the alkyl, 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 monovalent groups, At least one hydrogen may be replaced by fluorine;
A ¹ and A ² are independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is replaced by fluorine;
G is a divalent group represented by the formula (pr-1) or (pr-2);

Z ¹ , Z ² and Z ³ are independently a single bond, —CF ₂ O—, —OCF ₂ — or —CH ₂ CH ₂ —;
Y ¹ and Y ² are independently hydrogen or fluorine;
a and b are independently 0, 1 or 2, and the sum of a and b is 0 to 2.
And

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 the alkyl and alkenyl, at least one —CH ₂ — may be replaced by —O— Well, at least one hydrogen may be replaced by fluorine;
Ring B ¹ , ring B ² , ring B ³ and ring B ⁴ are each 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-. Further comprising at least one compound selected from the group of compounds represented by the formula (5) (7) The liquid crystal composition according to claim 1.

In equations (5) to (7),
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—, and at least one hydrogen is May be replaced by fluorine;
X ¹¹ represents fluorine, chlorine, -OCF ₃ , -OCHF ₂ , -CF ₃ , -CHF ₂ , -CH ₂ F, -OCF ₂ CHF ₂ , or -OCF ₂ CHFCF ₃ ;
Ring C ¹ , ring C ² and ring C ³ are independently 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl;
Z ^{14, Z 15,} and ^{Z 16} are independently a single _{bond, -COO -, - CF 2 O} -, - OCF 2 -, - CH 2 O -, - CH 2 CH 2 -, - CH = CH- , -C≡C-, or - _{(CH 2) 4} - a and;
L ¹¹ and L ¹² are independently hydrogen or fluorine. Further contains at least one compound selected from the group of compounds represented by formula (8), the liquid crystal composition according to claim 1 or 2.

In equation (8),
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—, and at least one hydrogen is May be replaced by fluorine;
X ¹² is —C≡N or —C≡C—C≡N;
Ring D ¹ is 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl Or pyrimidine-2,5-diyl;
Z ¹⁷ represents a single bond, -COO-, -CF ₂ O-, -OCF _2- , -CH ₂ O-, -CH ₂ CH _2- , or -C≡C-;
L ¹³ and L ¹⁴ are independently hydrogen or fluorine;
i is 1, 2, 3 or 4; The liquid crystal composition according to any one of claims 1 to 3 , further comprising at least one compound selected from the group of compounds represented by formulas (9) to (15).

In equations (9) to (15),
R ¹⁵ and R ¹⁶ are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in this alkyl and alkenyl, at least one of —CH ₂ — may be replaced by —O— Well, at least one hydrogen may be replaced by fluorine;
R ¹⁷ is hydrogen, fluorine, 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;
Ring E ¹ , ring E ² , ring E ³ , and ring E ⁴ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, or at least one hydrogen optionally substituted by fluorine 1, 4-phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6-diyl;
Ring E ⁵ and ring E ⁶ are each independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, or decahydronaphthalene-2,6 -Diyl;
^{Z 18, Z 19, Z 20} , and ^{Z 21} are independently a single _{bond, -COO -, - CH 2 O} -, - OCF 2 -, - CH 2 CH 2 -, or -OCF ₂ CH ₂ CH ₂ -And
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 and t is 1, 2 or 3. The liquid crystal display element containing the liquid crystal composition of any one of Claim 1 to 4 . The compound represented by any one of Formula (1-11a) to (1-16a) and Formula (1-11b) to (1-16b ) .

Oite from equation (1-11a) (1-16a), and from equation (1-11b) to (1-16B),
R ^a is alkyl of 1 to 10 carbon atoms, in the alkyl, one or two _-CH 2 CH ₂ - is -CH = CH - can be replaced by, in these monovalent group, at least 1 One of hydrogen may be replaced by fluorine, and R ^b is a polyfluoroalkyl from carbon number 1 4, polyfluoroalkoxy of 1 to 4 carbon atoms, or is an fluorine;
A ¹¹ , A ¹² , A ²¹ and A ²² are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5 - diyl, 1, 4-phenylene, 2-fluoro-1,4-phenylene, be a 2,5-difluoro-1,4-phenylene or 2,6-difluoro-1,4-phenylene;
^{Z 11, Z 12, Z 21} , Z 22, and ^{Z 31} are independently a single _{bond, - CF 2 O -, -} OCF 2 -, or is _-CH 2 CH ₂ - and are;
Y ¹ and ^{Y 2} are independently hydrogen or fluorine. The compound according to claim 6 , which is represented by any one of formulas (1-11a) to (1-16a).

In formulas (1-11a) to (1-16a),
R ^a is alkyl of 1 to 10 carbon atoms, or is alkenyl of 2 to 10 carbons, ^{R b} is fluorine, -CF ₃ or -OCF _3,;
A ¹¹ , A ¹² , A ²¹ and A ²² are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,6-difluoro-1,4 -Phenylene;
Z ¹¹ , Z ¹² , Z ²¹ , Z ²² and Z ³¹ are independently a single bond , —CF ₂ O— or —CH ₂ CH ₂ —;
Y ¹ and Y ² are independently hydrogen or fluorine.