JPWO2020095499A1 - Liquid crystal composition and liquid crystal display element - Google Patents

Abstract

Provided are a liquid crystal composition having a large dielectric constant (ε⊥) in the minor axis direction of a liquid crystal molecule, and a liquid crystal display element containing the composition, having a high transmittance and a large contrast ratio. It contains at least one compound selected from the compound represented by the formula (1) as the first component and at least one compound selected from the compound represented by the formula (2) as the second component, and is positive. A liquid crystal composition having dielectric anisotropy and a liquid crystal display element containing the same.

Description

The present invention relates to a liquid crystal composition, a liquid crystal display element containing the composition, and the like. In particular, it relates to a liquid crystal composition having a positive dielectric anisotropy, and an AM (active matrix) device containing the composition and having a mode of TN, ECB, OCB, IPS, FFS, or FPA.

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

The liquid crystal display element contains a liquid crystal composition having a nematic phase. This composition has suitable properties. By improving the characteristics of this composition, an AM element having good characteristics can be obtained. The relationships in these properties are summarized in Table 1 below. The 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 temperature range in which the device can be used. The preferred upper limit temperature of the nematic phase is about 70 ° C. or higher, and the preferred lower limit temperature of the nematic phase is about −10 ° C. or lower. The viscosity of the composition is related to the response time of the device. A short response time is preferred for displaying moving images on the device. A shorter response time of even 1 millisecond is desirable. Therefore, a small viscosity in the composition is preferred. Small viscosities at low temperatures are even more preferred. The elastic constant of the composition is related to the contrast of the device. In order to increase the contrast in the device, a large elastic constant in the composition is more preferable.

The optical anisotropy of the composition is related to the contrast ratio of the device. Depending on the mode of the device, a large optical anisotropy or a small optical anisotropy, that is, an appropriate optical anisotropy is required. The product (Δn × d) of the optical anisotropy (Δn) of the composition and the cell gap (d) of the device is designed to maximize the contrast ratio. The appropriate value of the product depends on the type of operation mode. For devices in modes such as TN, a suitable value is about 0.45 μm. In this case, a composition having a large optical anisotropy is preferable for a device having a small cell gap. The large permittivity anisotropy in the composition contributes to the low threshold voltage, low power consumption and large contrast ratio in the device. Therefore, large dielectric anisotropy is preferred. A large resistivity in the composition contributes to a large voltage retention and a large contrast ratio in the device. Therefore, a composition having a large resistivity at an initial stage not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase is preferable. After long-term use, a composition having a large resistivity not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase is preferable. The stability of the composition against ultraviolet light and heat is related to the life of the liquid crystal display device. When these stability is high, the life of this device is long. Such characteristics are preferable for AM elements used in liquid crystal monitors, liquid crystal televisions, and the like.

In the AM device having the TN mode, a composition having a positive dielectric anisotropy is used. In the AM device having the VA mode, a composition having a negative dielectric anisotropy is used. In an AM device having an IPS mode or an FFS mode, a composition having positive or negative dielectric anisotropy is used. In a polymer sustained alignment (PSA) type AM element, a composition having positive or negative dielectric anisotropy is used.

Especially in the FFS mode, the arrangement of some liquid crystal molecules is not parallel to the panel substrate due to the oblique electric field. Therefore, in order to suppress the tilt-up of these liquid crystal molecules, the permittivity (ε) of the liquid crystal molecules in the minor axis direction. Larger ⊥) is preferable. By suppressing the tilt-up of the liquid crystal molecules, the transmittance of the FFS mode element can be increased, which contributes to a large contrast ratio (see, for example, Non-Patent Document 1).

International Publication No. 2014/045905 International Bulletin No. 1999/021816

S.-W.Kang, I.W.Jang, D.H.Kim, Y.J.Lim, and S.H.Lee, Japanese Journal of Applied Physics, 53, 010304 (2014).

An object of the present invention is to provide a liquid crystal composition having a large dielectric constant (ε⊥) in the minor axis direction of a liquid crystal molecule. Another challenge is the high upper limit temperature of the nematic phase, the lower lower limit temperature of the nematic phase, small viscosity, proper optical anisotropy, large dielectric anisotropy, large specific resistance, high stability to heat, high stability to ultraviolet rays. It is an object of the present invention to provide a liquid crystal composition that satisfies at least one of properties such as anisotropy and a large elastic constant. Another challenge is to provide a liquid crystal composition having an appropriate balance between at least two of these properties. Another object is to provide a liquid crystal display device containing such a composition. Another object is to provide a liquid crystal display element having a high transmittance and a large contrast ratio. Another challenge is to provide an AM device with characteristics such as short response time, high voltage retention, low threshold voltage, and long lifetime.

式（１）および式（２）において、Ｒ^１は、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、または炭素数２から１２のアルケニルであり；Ｒ^２およびＲ^３は、水素、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、炭素数２から１２のアルケニル、または炭素数２から１２のアルケニルオキシであり；環Ａおよび環Ｂは、１，４−シクロヘキシレン、１，４−フェニレン、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、ピリミジン−２，５−ジイル、１，３−ジオキサン−２，５−ジイル、またはテトラヒドロピラン−２，５−ジイルであり；環Ｃおよび環Ｅは、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、１，４−フェニレン、少なくとも１つの水素がフッ素または塩素で置き換えられた１，４−フェニレン、ナフタレン−２，６−ジイル、少なくとも１つの水素がフッ素または塩素で置き換えられたナフタレン−２，６−ジイル、クロマン−２，６−ジイル、または少なくとも１つの水素がフッ素または塩素で置き換えられたクロマン−２，６−ジイルであるが、環Ｃおよび環Ｅのうち少なくとも１つは、少なくとも１つの水素がフッ素で置き換えられた１，４−フェニレンであり；環Ｄは、２，３−ジフルオロ−１，４−フェニレン、２−クロロ−３−フルオロ−１，４−フェニレン、２，３−ジフルオロ−５−メチル−１，４−フェニレン、３，４，５−トリフルオロナフタレン−２，６−ジイル、７，８−ジフルオロクロマン−２，６−ジイル、３，４，５，６−テトラフルオロフルオレン−２，７−ジイル、４，６−ジフルオロジベンゾフラン−３，７−ジイル、４，６−ジフルオロジベンゾチオフェン−３，７−ジイル、または１，１，６，７−テトラフルオロインダン−２，５−ジイルであり；Ｚ^１およびＺ^２は、単結合、エチレン、ビニレン、メチレンオキシ、カルボニルオキシ、またはジフルオロメチレンオキシであり；Ｚ^３およびＺ^４は、単結合、エチレン、ビニレン、メチレンオキシ、またはカルボニルオキシであり；Ｘ^１およびＸ^２は、水素またはフッ素であり；Ｙ^１は、フッ素、塩素、少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から１２のアルキル、少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から１２のアルコキシ、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数２から１２のアルケニルオキシであり；ａは、１、２、３、または４であり；ｂおよびｃは、０、１、２、または３であり；ｄは、０または１であり；そしてａとｂとの和は４以下であり；ｃとｄの和は、１、２、または３である。The present invention contains at least one compound selected from the compound represented by the formula (1) as the first component and at least one compound selected from the compound represented by the formula (2) as the second component. However, it is a liquid crystal composition having positive dielectric anisotropy.

In formulas (1) and (2), R ¹ is an alkyl having 1 to 12 carbon atoms, an alkoxy having 1 to 12 carbon atoms, or an alkenyl having 2 to 12 carbon atoms; R ² and R ³ are hydrogens. , Alkyl with 1 to 12 carbon atoms, alkoxy with 1 to 12 carbon atoms, alkenyl with 2 to 12 carbon atoms, or alkenyloxy with 2 to 12 carbon atoms; rings A and B are 1,4-cyclohexylene. , 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced with fluorine, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl, or tetrahydropyran-2,5 -Diyl; rings C and E are 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, and at least one hydrogen is fluorine or chlorine. 1,4-phenylene, naphthalene-2,6-diyl replaced with, naphthalene-2,6-diyl, chroman-2,6-diyl, or at least one hydrogen in which at least one hydrogen has been replaced with fluorine or chlorine. Chroman-2,6-diyl in which hydrogen has been replaced with fluorine or chlorine, but at least one of rings C and E is 1,4-phenylene in which at least one hydrogen has been replaced with fluorine; Ring D is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4. 5-Trifluoronaphthalene-2,6-diyl, 7,8-difluorochroman-2,6-diyl, 3,4,5,6-tetrafluorofluorene-2,7-diyl, 4,6-difluorodibenzofuran- 3,7-diyl, 4,6-difluorodibenzothiophene-3,7-diyl, or 1,1,6,7-tetrafluoroindan-2,5-diyl; Z ¹ and Z ² are single-bonded , ethylene, vinylene, methyleneoxy, carbonyloxy or difluoromethyleneoxy,; ^{Z 3} and ^{Z 4} is a single bond, ethylene, vinylene, methyleneoxy or carbonyloxy,; ^{X 1} and ^{X 2} is hydrogen or Fluorine; Y ¹ is fluorine, chlorine, an alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, and 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. Alkoxy, or an alkenyloxy having 2 to 12 carbon atoms in which at least one hydrogen is replaced with fluorine or chlorine; a is 1, 2, 3, or 4; b and c are 0, 1, 2 , Or 3; d is 0 or 1; and the sum of a and b is 4 or less; the sum of c and d is 1, 2, or 3.

An advantage of the present invention is a liquid crystal composition having a large dielectric constant (ε⊥) in the minor axis direction of the liquid crystal molecule. Other advantages are high upper temperature limit of nematic phase, lower lower limit temperature of nematic phase, small viscosity, proper optical anisotropy, large dielectric anisotropy, large specific resistance, high stability against heat, high stability against ultraviolet rays. A liquid crystal composition that satisfies at least one of properties such as anisotropy and a large elastic constant. Another advantage is a liquid crystal composition that has an appropriate balance between at least two of these properties. Another advantage is a liquid crystal display device containing such a composition. Another advantage is a liquid crystal display element having high transmittance and a large contrast ratio. Another advantage is an AM device that has characteristics such as short response time, high voltage retention, low threshold voltage, and long life.

The usage of terms in this specification is as follows. The terms "liquid crystal composition" and "liquid crystal display element" may be abbreviated as "composition" and "element", respectively. "Liquid crystal display element" is a general term for a liquid crystal display panel and a liquid crystal display module. A "liquid crystal compound" is a compound having a liquid crystal phase such as a nematic phase or a smectic phase and a compound having no liquid crystal phase, but for the purpose of adjusting properties such as temperature range, viscosity, and dielectric constant anisotropy of the nematic phase. It is a general term for compounds mixed in a composition. This compound has a six-membered ring such as 1,4-cyclohexylene and 1,4-phenylene, and its molecule (liquid crystal molecule) is rod-like. The "polymerizable compound" is a compound added for the purpose of forming a polymer in the composition. Liquid crystal compounds having alkenyl are not classified as polymerizable compounds in that sense.

The liquid crystal composition is prepared by mixing a plurality of liquid crystal compounds. Additives such as optically active compounds and polymerizable compounds are added to the liquid crystal composition as needed. The proportion of the liquid crystal compound is expressed as a mass percentage (mass%) based on the mass of the liquid crystal composition containing no additive even when the additive is added. The ratio of the additive is expressed as a mass percentage (mass%) based on the mass of the liquid crystal composition containing no additive. That is, the ratio of the liquid crystal compound or the additive is calculated based on the total mass of the liquid crystal compound. The ratio of the polymerization initiator and the polymerization inhibitor is exceptionally expressed based on the mass of the polymerizable compound.

The "upper limit temperature of the nematic phase" 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 when the composition has a positive dielectric anisotropy, its value increases positively, and the composition has a negative dielectric anisotropy. When it is a thing, it means that its value increases negatively. "Large voltage retention" means that the element has a large voltage retention not only at room temperature but also at a temperature close to the upper limit temperature at the initial stage, and after long-term use, it has a large voltage not only at room temperature but also at a temperature close to the upper limit temperature. It means having a retention rate. The properties of the composition or device may be examined by aging tests.

上記の化合物（１ｚ）を例にして説明する。式（１ｚ）において、六角形で囲んだαおよびβの記号はそれぞれ環αおよび環βに対応し、六員環、縮合環のような環を表す。添え字‘ｘ’が２のとき、２つの環αが存在する。２つの環αが表す２つの基は、同一であってもよく、または異なってもよい。このルールは、添え字‘ｘ’が２より大きいとき、任意の２つの環αに適用される。このルールは、結合基Ｚのような、他の記号にも適用される。環βの一辺を横切る斜線は、環β上の任意の水素が置換基（−Ｓｐ−Ｐ）で置き換えられてもよいことを表す。添え字‘ｙ’は置き換えられた置換基の数を示す。添え字‘ｙ’が０のとき、そのような置き換えはない。添え字‘ｙ’が２以上のとき、環β上には複数の置換基（−Ｓｐ−Ｐ）が存在する。この場合にも、「同一であってもよく、または異なってもよい」のルールが適用される。なお、このルールは、Ｒａの記号を複数の化合物に用いた場合にも適用される。

The above compound (1z) will be described as an example. In formula (1z), the symbols α and β enclosed in hexagons correspond to rings α and ring β, respectively, and represent rings such as a six-membered ring and a condensed ring. When the subscript'x' is 2, there are two rings α. The two groups represented by the two rings α may be the same or different. This rule applies to any two rings α when the subscript'x' is greater than 2. This rule also applies to other symbols, such as binding group Z. A diagonal line across one side of the ring β indicates that any hydrogen on the ring β may be replaced by a substituent (-Sp-P). The subscript'y'indicates the number of substituents replaced. When the subscript'y'is 0, there is no such replacement. When the subscript'y'is 2 or more, a plurality of substituents (-Sp-P) are present on the ring β. In this case as well, the rule of "may be the same or different" applies. This rule also applies when the Ra symbol is used for a plurality of compounds.

In formula (1z), for example, the expression "Ra and Rb are alkyl, alkoxy, or alkenyl" means that Ra and Rb are independently selected from the group of alkyl, alkoxy, and alkenyl. do. That is, the group represented by Ra and the group represented by Rb may be the same or different.

At least one compound selected from the compounds represented by the formula (1z) may be abbreviated as "compound (1z)". "Compound (1z)" means one compound represented by the formula (1z), a mixture of two compounds, or a mixture of three or more compounds. The same applies to compounds represented by other formulas. The expression "at least one compound selected from the compounds of formula (1z) and formula (2z)" means at least one compound selected from the group of compounds (1z) and compound (2z). ..

The expression "at least one'A'" means that the number of'A's is arbitrary. The expression "at least one'A'may be replaced by'B'" is that when the number of'A's is 1, the position of the'A'is arbitrary and the number of'A's is 2. When there is more than one, their positions can be selected without limitation. The expression "at least one -CH _2- may be replaced by -O-" may be used. In this case, −CH ₂ −CH ₂ −CH ₂₋ may be converted to −O−CH ₂₋ O− by replacing the non-adjacent −CH _{2− with −O−.} However, the adjacent −CH ₂₋ is not replaced by −O−. This is because -O-O-CH _2- (peroxide) is produced by this replacement.

For example, in Ra and Rb of formula (1z), the alkyl is linear or branched and does not contain cyclic alkyl. Linear alkyl is preferred over branched alkyl. The same applies to terminal groups such as alkoxy and alkenyl.

テトラヒドロピラン−２，５−ジイルのような二価基においても同様である。カルボニルオキシのような結合基（−ＣＯＯ−または−ＯＣＯ−）も同様である。The configuration for 1,4-cyclohexylene is preferably trans over cis in order to raise the upper temperature limit. Since 2-fluoro-1,4-phenylene is asymmetrical, there are leftward (L) and rightward (R).

The same is true for divalent groups such as tetrahydropyran-2,5-diyl. The same is true for binding groups such as carbonyloxy (-COO- or -OCO-).

The present invention includes the following items.

式（１）および式（２）において、Ｒ^１は、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、または炭素数２から１２のアルケニルであり；Ｒ^２およびＲ^３は、水素、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、炭素数２から１２のアルケニル、または炭素数２から１２のアルケニルオキシであり；環Ａおよび環Ｂは、１，４−シクロヘキシレン、１，４−フェニレン、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、ピリミジン−２，５−ジイル、１，３−ジオキサン−２，５−ジイル、またはテトラヒドロピラン−２，５−ジイルであり；環Ｃおよび環Ｅは、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、１，４−フェニレン、少なくとも１つの水素がフッ素または塩素で置き換えられた１，４−フェニレン、ナフタレン−２，６−ジイル、少なくとも１つの水素がフッ素または塩素で置き換えられたナフタレン−２，６−ジイル、クロマン−２，６−ジイル、または少なくとも１つの水素がフッ素または塩素で置き換えられたクロマン−２，６−ジイルであるが、環Ｃおよび環Ｅのうち少なくとも１つは、少なくとも１つの水素がフッ素で置き換えられた１，４−フェニレンであり；環Ｄは、２，３−ジフルオロ−１，４−フェニレン、２−クロロ−３−フルオロ−１，４−フェニレン、２，３−ジフルオロ−５−メチル−１，４−フェニレン、３，４，５−トリフルオロナフタレン−２，６−ジイル、７，８−ジフルオロクロマン−２，６−ジイル、３，４，５，６−テトラフルオロフルオレン−２，７−ジイル、４，６−ジフルオロジベンゾフラン−３，７−ジイル、４，６−ジフルオロジベンゾチオフェン−３，７−ジイル、または１，１，６，７−テトラフルオロインダン−２，５−ジイルであり；Ｚ^１およびＺ^２は、単結合、エチレン、ビニレン、メチレンオキシ、カルボニルオキシ、またはジフルオロメチレンオキシであり；Ｚ^３およびＺ^４は、単結合、エチレン、ビニレン、メチレンオキシ、またはカルボニルオキシであり；Ｘ^１およびＸ^２は、水素またはフッ素であり；Ｙ^１は、フッ素、塩素、少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から１２のアルキル、少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から１２のアルコキシ、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数２から１２のアルケニルオキシであり；ａは、１、２、３、または４であり；ｂおよびｃは、０、１、２、または３であり；ｄは、０または１であり；そしてａとｂとの和は４以下であり；ｃとｄの和は、１、２、または３である。Item 1. Positive dielectric containing at least one compound selected from the compounds represented by the formula (1) as the first component and at least one compound selected from the compounds represented by the formula (2) as the second component. A liquid crystal composition having rate anisotropy.

In formulas (1) and (2), R ¹ is an alkyl having 1 to 12 carbon atoms, an alkoxy having 1 to 12 carbon atoms, or an alkenyl having 2 to 12 carbon atoms; R ² and R ³ are hydrogens. , Alkyl with 1 to 12 carbon atoms, alkoxy with 1 to 12 carbon atoms, alkenyl with 2 to 12 carbon atoms, or alkenyloxy with 2 to 12 carbon atoms; rings A and B are 1,4-cyclohexylene. , 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced with fluorine, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl, or tetrahydropyran-2,5 -Diyl; rings C and E are 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, and at least one hydrogen is fluorine or chlorine. 1,4-phenylene, naphthalene-2,6-diyl replaced with, naphthalene-2,6-diyl, chroman-2,6-diyl, or at least one hydrogen in which at least one hydrogen has been replaced with fluorine or chlorine. Chroman-2,6-diyl in which hydrogen has been replaced with fluorine or chlorine, but at least one of rings C and E is 1,4-phenylene in which at least one hydrogen has been replaced with fluorine; Ring D is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4. 5-Trifluoronaphthalene-2,6-diyl, 7,8-difluorochroman-2,6-diyl, 3,4,5,6-tetrafluorofluorene-2,7-diyl, 4,6-difluorodibenzofuran- 3,7-diyl, 4,6-difluorodibenzothiophene-3,7-diyl, or 1,1,6,7-tetrafluoroindan-2,5-diyl; Z ¹ and Z ² are single-bonded , ethylene, vinylene, methyleneoxy, carbonyloxy or difluoromethyleneoxy,; ^{Z 3} and ^{Z 4} is a single bond, ethylene, vinylene, methyleneoxy or carbonyloxy,; ^{X 1} and ^{X 2} is hydrogen or Fluorine; Y ¹ is fluorine, chlorine, an alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, and 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. Alkoxy, or an alkenyloxy having 2 to 12 carbon atoms in which at least one hydrogen is replaced with fluorine or chlorine; a is 1, 2, 3, or 4; b and c are 0, 1, 2 , Or 3; d is 0 or 1; and the sum of a and b is 4 or less; the sum of c and d is 1, 2, or 3.

式（１−１）から式（１−１４）において、Ｒ^１は、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、または炭素数２から１４のアルケニルであり；Ｘ^１、Ｘ^２、Ｘ^３、Ｘ^４、Ｘ^５、Ｘ^６、Ｘ^７、Ｘ^８、Ｘ^９、Ｘ^１０、Ｘ^１１、Ｘ^１２、Ｘ^１３、およびＸ^１４は、水素またはフッ素であり；Ｙ^１は、フッ素、塩素、少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から１２のアルキル、少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から１２のアルコキシ、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数２から１２のアルケニルオキシである。Item 2. Item 2. The liquid crystal composition according to Item 1, which contains at least one compound selected from the compounds represented by the formulas (1-1) to (1-14) as the first component.

In formulas (1-1) to (1-14), R ¹ is an alkyl having 1 to 12 carbon atoms, an alkoxy having 1 to 12 carbon atoms, or an alkenyl having 2 to 14 carbon atoms; X ¹ , X. ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ , X ⁸ , X ⁹ , X ¹⁰ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ are hydrogen or fluorine; Y ¹ is Fluorine, chlorine, alkyl with 1 to 12 carbon atoms in which at least one hydrogen is replaced with fluorine or chlorine, alkoxy with 1 to 12 carbon atoms in which at least one hydrogen is replaced with fluorine or chlorine, or at least one hydrogen An alkenyloxy having 2 to 12 carbon atoms replaced with fluorine or chlorine.

式（２−１）から式（２−３８）において、Ｒ^２およびＲ^３は、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、炭素数２から１２のアルケニル、または炭素数２から１２のアルケニルオキシである。Item 3. Item 2. The liquid crystal composition according to Item 1 or 2, which contains at least one compound selected from the compounds represented by the formulas (2-1) to (2-38) as the second component.

In formulas (2-1) to (2-38), R ² and R ³ are alkyls having 1 to 12 carbon atoms, alkoxys having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, or 2 carbon atoms. To 12 alkoxyoxy.

Item 4. Item 2. The liquid crystal display according to any one of Items 1 to 3, wherein the ratio of the first component is in the range of 5% by mass to 50% by mass, and the ratio of the second component is in the range of 2% by mass to 50% by mass. Composition.

式（３）において、Ｒ^４およびＲ^５は、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、炭素数２から１２のアルケニル、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数２から１２のアルケニルであり；環Ｆおよび環Ｇは、１，４−シクロヘキシレン、１，４−フェニレン、２−フルオロ−１，４−フェニレン、または２，５−ジフルオロ−１，４−フェニレンであり；Ｚ^５は、単結合、エチレン、ビニレン、メチレンオキシ、またはカルボニルオキシであり；ｅは、１、２、または３である。Item 5. Item 6. The liquid crystal composition according to any one of Items 1 to 4, which contains at least one compound selected from the compounds represented by the formula (3) as the third component.

In formula (3), R ⁴ and R ⁵ are alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, or at least one hydrogen being replaced with fluorine or chlorine. It is an alkenyl having 2 to 12 carbon atoms; ring F and ring G are 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 2,5-difluoro-1,4. -Phenylene; Z ⁵ is single bond, ethylene, vinylene, methyleneoxy, or carbonyloxy; e is 1, 2, or 3.

式（３−１）から式（３−１３）において、Ｒ^４およびＲ^５は、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、炭素数２から１２のアルケニル、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数２から１２のアルケニルである。Item 6. Item 6. The liquid crystal composition according to any one of Items 1 to 5, which contains at least one compound selected from the compounds represented by the formulas (3-1) to (3-13) as the third component.

In the formula (3-13) from equation (3-1), ^{R 4} and ^{R 5} are alkyl of from 1 to 12 carbons, alkoxy having 1 to 12 carbons, from 2 to 12 carbons, alkenyl or at least one, An alkenyl having 2 to 12 carbon atoms in which hydrogen is replaced with fluorine or chlorine.

Item 7. Item 5. The liquid crystal composition according to Item 5 or 6, wherein the proportion of the third component is in the range of 10% by mass to 90% by mass.

式（４）において、Ｒ^６は炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、または炭素数２から１２のアルケニルであり；環Ｊは、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、２，３−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、ピリミジン−２，５−ジイル、１，３−ジオキサン−２，５−ジイル、またはテトラヒドロピラン−２，５−ジイルであり；Ｚ^６は、単結合、エチレン、またはカルボニルオキシであり；Ｘ^１５およびＸ^１６は、水素またはフッ素であり；Ｙ^２は、フッ素、塩素、少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から１２のアルキル、少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数１から１２のアルコキシ、または少なくとも１つの水素がフッ素または塩素で置き換えられた炭素数２から１２のアルケニルオキシであり；ｆは、１、２、３、または４である。Item 8. Item 6. The liquid crystal composition according to any one of Items 1 to 7, which contains at least one compound selected from the compounds represented by the formula (4) as the fourth component.

In formula (4), R ⁶ is an alkyl with 1 to 12 carbons, an alkoxy with 1 to 12 carbons, or an alkenyl with 2 to 12 carbons; ring J is 1,4-cyclohexylene, 1,4. -Phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3-dioxane -2,5-diyl, or tetrahydropyran-2,5-diyl; Z ⁶ is a single bond, ethylene, or carbonyloxy; X ¹⁵ and X ¹⁶ are hydrogen or fluorine; Y ² is , Fluorine, chlorine, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, alkoxy having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or at least one hydrogen. Is an alkenyloxy having 2 to 12 carbon atoms replaced with fluorine or chlorine; f is 1, 2, 3, or 4.

式（４−１）から式（４−１６）において、Ｒ^６は、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、または炭素数２から１２のアルケニルである。Item 9. Item 6. The liquid crystal composition according to any one of Items 1 to 8, which contains at least one compound selected from the compounds represented by the formulas (4-1) to (4-16) as the fourth component.

In formulas (4-1) to (4-16), R ⁶ is an alkyl having 1 to 12 carbon atoms, an alkoxy having 1 to 12 carbon atoms, or an alkenyl having 2 to 12 carbon atoms.

Item 10. Item 8. The liquid crystal composition according to Item 8 or 9, wherein the proportion of the fourth component is in the range of 5% by mass to 40% by mass.

式（５）において、Ｒ^７およびＲ^８は、水素、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、炭素数２から１２のアルケニル、または炭素数２から１２のアルケニルオキシであり；環Ｋおよび環Ｍは、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、１，４−フェニレン、ナフタレン−２，６−ジイル、少なくとも１つの水素がフッ素または塩素で置き換えられたナフタレン−２，６−ジイル、クロマン−２，６−ジイル、または少なくとも１つの水素がフッ素または塩素で置き換えられたクロマン−２，６−ジイルであり；環Ｌは、２，３−ジフルオロ−１，４−フェニレン、２−クロロ−３−フルオロ−１，４−フェニレン、２，３−ジフルオロ−５−メチル−１，４−フェニレン、３，４，５−トリフルオロナフタレン−２，６−ジイル、７，８−ジフルオロクロマン−２，６−ジイル、３，４，５，６−テトラフルオロフルオレン−２，７−ジイル、４，６−ジフルオロジベンゾフラン−３，７−ジイル、４，６−ジフルオロジベンゾチオフェン−３，７−ジイル、または１，１，６，７−テトラフルオロインダン−２，５−ジイルであり；Ｚ^７およびＺ^８は、単結合、エチレン、ビニレン、メチレンオキシ、またはカルボニルオキシであり；ｇは、０、１、２、または３であり；ｈは、０または１であり；そしてｇとｈとの和は３以下である。Item 11. Item 6. The liquid crystal composition according to any one of Items 1 to 10, which contains at least one compound selected from the compounds represented by the formula (5) as the fifth component.

In formula (5), R ⁷ and R ⁸ are hydrogen, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, or alkenyloxy having 2 to 12 carbon atoms. Ring K and Ring M are 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, naphthalene-2,6-diyl, at least one hydrogen. Is naphthalene-2,6-diyl, chroman-2,6-diyl replaced with fluorine or chlorine, or chroman-2,6-diyl in which at least one hydrogen is replaced with fluorine or chlorine; ring L , 2,3-Difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4,5-tri Fluoronaphthalene-2,6-diyl, 7,8-difluorochroman-2,6-diyl, 3,4,5,6-tetrafluorofluorene-2,7-diyl, 4,6-difluorodibenzofuran-3,7 - diyl, 4,6-difluoro-dibenzothiophene-3,7-diyl, or 1,1,6,7- be tetrafluoro indane-2,5-diyl; ^{Z 7} and ^{Z 8} are a single bond, ethylene, It is vinylene, methyleneoxy, or carbonyloxy; g is 0, 1, 2, or 3; h is 0 or 1; and the sum of g and h is less than or equal to 3.

式（５−１）から式（５−３１）において、Ｒ^７およびＲ^８は、水素、炭素数１から１２のアルキル、炭素数１から１２のアルコキシ、炭素数２から１２のアルケニル、または炭素数２から１２のアルケニルオキシである。Item 12. Item 6. The liquid crystal composition according to any one of Items 1 to 11, which contains at least one compound selected from the compounds represented by the formulas (5-1) to (5-31) as the fifth component.

In formulas (5-1) to (5-31), R ⁷ and R ⁸ are hydrogen, alkyl with 1 to 12 carbon atoms, alkoxy with 1 to 12 carbon atoms, alkenyl with 2 to 12 carbon atoms, or carbon. Numbers 2 to 12 of alkoxyoxy.

Item 13. Item 2. The liquid crystal composition according to Item 11 or 12, wherein the proportion of the fifth component is in the range of 2% by mass to 50% by mass.

Item 14. The upper limit temperature of the nematic phase is 70 ° C. or higher, the optical anisotropy at a wavelength of 589 nm (measured at 25 ° C.) is 0.07 or higher, and the dielectric anisotropy at a frequency of 1 kHz (measured at 25 ° C.) is 2. Item 2. The liquid crystal composition according to any one of Items 1 to 13.

Item 15. A liquid crystal display element containing the liquid crystal composition according to any one of Items 1 to 13.

Item 16. Item 15. The liquid crystal display element according to Item 15, wherein the operation mode of the liquid crystal display element is the FFS mode, and the drive method of the liquid crystal display element is the active matrix method.

Item 17. Item 15. The liquid crystal display element according to Item 15, wherein the operation mode of the liquid crystal display element is a TN mode, an ECB mode, an OCB mode, an IPS mode, or an FPA mode, and the drive method of the liquid crystal display element is an active matrix method.

Item 18. Use of the liquid crystal composition according to any one of Items 1 to 14 in a liquid crystal display element.

The present invention also includes the following sections. (A) One compound selected from additives such as optically active compounds, antioxidants, ultraviolet absorbers, quenchers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, two The above composition containing a compound, or three or more compounds. (B) AM device containing the above composition. (C) The above composition further containing a polymerizable compound, and a polymer-supported orientation (PSA) type AM device containing this composition. (D) A polymer-supported orientation (PSA) type AM device containing the above composition and in which the polymerizable compound in the composition is polymerized. (E) A device containing the above composition and having a mode of PC, TN, STN, ECB, OCB, IPS, VA, FFS, or FPA. (F) A transmissive device containing the above composition. (G) Use of the above composition as a composition having a nematic phase. (H) Use of an optically active composition obtained by adding an optically active compound to the above composition.

The composition of the present invention will be described in the following order. First, the composition of the constituent compounds in the composition will be described. Secondly, the main properties of the constituent compounds and the main effects of this compound on the composition will be described. Thirdly, the combination of the components in the composition, the preferable ratio of the components, and the rationale thereof will be described. Fourth, preferred forms of the component compounds will be described. Fifth, preferred component compounds are shown. Sixth, additives that may be added to the composition will be described. Seventh, a method for synthesizing a component compound will be described. Finally, the use of the composition will be described.

First, the composition of the composition will be described. This composition contains a plurality of liquid crystal compounds. This composition may contain additives. Additives include optically active compounds, antioxidants, UV absorbers, quenchers, dyes, defoamers, polymerizable compounds, polymerization initiators, polymerization inhibitors, polar compounds and the like. This composition is classified into composition A and composition B from the viewpoint of liquid crystal compounds. The composition A includes a liquid crystal compound selected from the compound (1), the compound (2), the compound (3), the compound (4), and the compound (5), as well as other liquid crystal compounds, additives, and the like. May be further contained. The "other liquid crystal compound" is a liquid crystal compound different from the compound (1), the compound (2), the compound (3), the compound (4), and the compound (5). Such compounds are mixed into the composition for the purpose of further adjusting the properties.

The composition B is substantially composed of only a liquid crystal compound selected from the compound (1), the compound (2), the compound (3), the compound (4), and the compound (5). "Substantially" means that composition B may contain additives but does not contain other liquid crystal compounds. The composition B has a smaller number of components than the composition A. The composition B is preferable to the composition A from the viewpoint of reducing the cost. Composition A is preferable to composition B from the viewpoint that the characteristics can be further adjusted by mixing other liquid crystal compounds.

Secondly, the main properties of the component compound and the main effect of this compound on the composition and the device will be described. The main properties of the component compounds are summarized in Table 2 based on the effects of the present invention. In the symbols in Table 2, L means large or high, M means medium, and S means small or low. The symbols L, M and S are classifications based on qualitative comparisons between the constituent compounds, with 0 (zero) meaning less than S.

The main effects of the component compounds are as follows. Compound (1) increases the dielectric anisotropy and lowers the lower limit temperature. Compound (2) increases the dielectric constant of the liquid crystal in the minor axis direction and lowers the lower limit temperature. Compound (3) lowers the viscosity or raises the upper limit temperature. Compound (4) increases the dielectric anisotropy and lowers the lower limit temperature. Compound (5) increases the dielectric constant in the minor axis direction and lowers the lower limit temperature.

Thirdly, the combination of the component compounds in the composition, the preferable ratio, and the rationale thereof will be described. Preferred combinations of the constituent compounds in the composition are compound (1) + compound (2), compound (1) + compound (2) + compound (3), compound (1) + compound (2) + compound (4), Compound (1) + Compound (2) + Compound (5), Compound (1) + Compound (2) + Compound (3) + Compound (4), Compound (1) + Compound (2) + Compound (3) + Compound (5) or compound (1) + compound (2) + compound (3) + compound (4) + compound (5). More preferred combinations are compound (1) + compound (2), compound (1) + compound (2) + compound (3), compound (1) + compound (2) + compound (3) + compound (4), Compound (1) + compound (2) + compound (3) + compound (5), or compound (1) + compound (2) + compound (3) + compound (4) + compound (5).

The preferable ratio of the compound (1) is about 5% by mass or more in order to increase the dielectric anisotropy, and about 50% by mass or less in order to lower the lower limit temperature. A more preferable ratio is in the range of about 10% by mass to about 45% by mass. A particularly preferable ratio is in the range of about 10% by mass to about 40% by mass.

The preferable ratio of the compound (2) is about 2% by mass or more in order to increase the dielectric constant of the liquid crystal molecule in the minor axis direction, and about 50% by mass or less in order to lower the lower limit temperature. A more preferable ratio is in the range of about 2% by mass to about 30% by mass. A particularly preferable ratio is in the range of about 2% by mass to about 20% by mass.

The preferable ratio of the compound (3) is about 10% by mass or more for lowering the viscosity or raising the upper limit temperature, and about 90% by mass or less for increasing the dielectric anisotropy. A more preferable ratio is in the range of about 15% by mass to about 80% by mass. A particularly preferable ratio is in the range of about 20% by mass to about 70% by mass.

The preferable ratio of compound (4) is about 5% by mass or more in order to increase the dielectric anisotropy, and about 40% by mass or less in order to lower the lower limit temperature. A more preferable ratio is in the range of about 5% by mass to about 35% by mass. A particularly preferable ratio is in the range of about 10% by mass to about 30% by mass.

The preferable ratio of the compound (5) is about 2% by mass or more in order to increase the dielectric constant in the minor axis direction, and about 50% by mass or less in order to lower the lower limit temperature. A more preferable ratio is in the range of about 4% by mass to about 40% by mass. A particularly preferable ratio is in the range of about 4% by mass to about 30% by mass.

Fourth, preferred forms of the component compounds will be described. Equation (1), equation (2), (3), (4), and in formula (5), ^{R 1} and ^{R 6,} from 1 to 12 carbons alkyl, from 1 to 12 carbons alkoxy, Alternatively, it is an alkenyl having 2 to 12 carbon atoms. Preferred R ¹ and R ⁶ are alkyl having 1 to 12 carbon atoms for increased stability to light or heat. R ^{2, R} 3, ^{R 7,} and ^{R 8} is hydrogen, alkyl of 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkenyl having 2 to 12 carbons or alkenyloxy having 2 to 12 carbons, Is. Preferred R ^2, R 3, ^R 7 and R ^8, in order to increase the stability to light or heat, alkyl of 1 to 12 carbons, increasing the maximum temperature, in order to increase the refractive index anisotropy It is an alkenyl having 2 to 12 carbon atoms, and an alkoxy having 1 to 12 carbon atoms in order to increase the dielectric anisotropy. R ⁴ and R ⁵ are alkyls with 1 to 12 carbon atoms, alkoxys with 1 to 12 carbon atoms, alkenyl with 2 to 12 carbon atoms, or 2 to 12 carbon atoms in which at least one hydrogen is replaced with fluorine or chlorine. It is alkenyl. Preferred R ⁴ and R ⁵ are alkenyl with 2 to 12 carbon atoms to reduce viscosity and alkyl with 1 to 12 carbon atoms to increase stability to light or heat.

Preferred alkyls are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, or octyl. More preferred alkyls are methyl, ethyl, propyl, butyl, or pentyl to reduce viscosity.

Preferred alkoxys are methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, or heptyloxy. More preferred alkoxys for reducing viscosity are methoxy or ethoxy.

Preferred alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, It is 3-hexenyl, 4-hexenyl, or 5-hexenyl. More preferred alkenyl is vinyl, 1-propenyl, 3-butenyl, or 3-pentenyl to reduce viscosity. The preferred configuration of -CH = CH- in these alkenyl depends on the position of the double bond. Trans is preferable in alkenyl such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyl, 3-hexenyl for the purpose of lowering the viscosity. Sith is preferred for alkenyl such as 2-butenyl, 2-pentenyl, 2-hexenyl.

Preferred alkenyloxys are vinyloxy, allyloxy, 3-butenyloxy, 3-pentenyloxy, or 4-pentenyloxy. More preferred alkenyloxy to reduce viscosity are allyloxy or 3-butenyloxy.

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

Preferred examples of alkenyl in which at least one hydrogen is replaced with fluorine or chlorine are 2,2-difluorovinyl, 3,3-difluoro-2-propenyl, 4,4-difluoro-3-butenyl, 5,5-difluoro. -4-pentenyl, or 6,6-difluoro-5-hexenyl. A more preferred example is 2,2-difluorovinyl or 4,4-difluoro-3-butenyl to reduce the viscosity.

または

であり、好ましくは

である。Rings A and B are 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced with fluorine, pyrimidine-2,5-diyl, 1,3-dioxane- 2,5-diyl, or tetrahydropyran-2,5-diyl. Preferred rings A and B are 1,4-phenylene or 2-fluoro-1,4-phenylene to increase optical anisotropy. Ring J is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,6-difluoro-1,4- Phenylene, pyrimidin-2,5-diyl, 1,3-dioxane-2,5-diyl, or tetrahydropyran-2,5-diyl. The preferred ring J is 1,4-phenylene or 2-fluoro-1,4-phenylene to increase the optical anisotropy. Tetrahydropyran-2,5-diyl is

or

And preferably

Is.

Rings C and E are 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, at least one hydrogen replaced with fluorine or chlorine 1 , 4-Phenylene, Naphthalene-2,6-diyl, Naphthalene-2,6-diyl in which at least one hydrogen is replaced with fluorine or chlorine, Chroman-2,6-diyl, or at least one hydrogen is fluorine or chlorine. Chlorman-2,6-diyl replaced by, but at least one of rings C and E is 1,4-phenylene in which at least one hydrogen has been replaced with fluorine. Preferred examples of "1,4-phenylene in which at least one hydrogen is replaced with fluorine or chlorine" are 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene or 2-chloro-. 3-Fluoro-1,4-phenylene. Preferred rings C and E are 1,4-cyclohexylene to reduce viscosity, tetrahydropyran-2,5-diyl to increase dielectric anisotropy, and to increase optical anisotropy. It is 1,4-phenylene.

Ring K and Ring M contain 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, naphthalene-2,6-diyl, and at least one hydrogen. Naphthalene-2,6-diyl, chroman-2,6-diyl replaced with fluorine or chlorine, or chroman-2,6-diyl in which at least one hydrogen is replaced with fluorine or chlorine. Preferred examples of "1,4-phenylene in which at least one hydrogen is replaced with fluorine or chlorine" are 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene or 2-chloro-. 3-Fluoro-1,4-phenylene. Preferred rings K and M are 1,4-cyclohexylene to reduce viscosity, tetrahydropyran-2,5-diyl to increase dielectric anisotropy, and to increase optical anisotropy. It is 1,4-phenylene.

好ましい環Ｄおよび環Ｌは、粘度を下げるために２，３−ジフルオロ−１，４−フェニレンであり、光学異方性を下げるために２−クロロ−３−フルオロ−１，４−フェニレンであり、誘電率異方性を上げるために７，８−ジフルオロクロマン−２，６−ジイルである。Rings D and L are 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3 , 4,5-Trifluoronaphthalene-2,6-diyl, 7,8-difluorochroman-2,6-diyl, 3,4,5,6-tetrafluorofluorene-2,7-diyl (FLF4), 4 , 6-Difluorodibenzofuran-3,7-diyl (DBFF2), 4,6-difluorodibenzothiophene-3,7-diyl (DBTF2), or 1,1,6,7-tetrafluoroindane-2,5-diyl (InF4).

Preferred rings D and L are 2,3-difluoro-1,4-phenylene to reduce viscosity and 2-chloro-3-fluoro-1,4-phenylene to reduce optical anisotropy. , 7,8-Difluorochroman-2,6-diyl to increase the dielectric anisotropy.

Rings F and G are 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene. Preferred ring F or ring G is 1,4-cyclohexylene to reduce viscosity, or 1,4-phenylene to increase optical anisotropy.

Z ¹ and Z ² are single bonds, ethylene, vinylene, methyleneoxy, carbonyloxy, or difluoromethyleneoxy. Preferred Z ² is a single bond to reduce viscosity. Z ³ , Z ⁴ , Z ⁷ and Z ⁸ are single bonds, ethylene, vinylene, methyleneoxy, or carbonyloxy. Preferred ^{Z 3, Z 4, Z 7} , and Z ⁸ is a single bond for decreasing the viscosity, an ethylene for decreasing the minimum temperature, methyleneoxy for increasing the dielectric anisotropy. Z ⁵ is a single bond, ethylene, vinylene, methyleneoxy, or carbonyloxy. Preferred Z ⁵ is a single bond to reduce viscosity.

In methyleneoxy, −CH ₂ O− is preferred over _{−OCH 2 −.} In carbonyloxy, -COO- is preferred over -OCO-.

X ¹ and X ² are hydrogen or fluorine. Preferred X ¹ or X ² is fluorine to increase the dielectric anisotropy.

Y ¹ and Y ² are fluorine, chlorine, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, and alkoxy having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. , Or an alkenyloxy having 2 to 12 carbon atoms in which at least one hydrogen is replaced with fluorine or chlorine. Preferred Y ¹ and Y ² are fluorine to lower the lower limit temperature.

A preferred example of an alkyl in which at least one hydrogen has been replaced with fluorine or chlorine is trifluoromethyl. A preferred example of an alkoxy in which at least one hydrogen has been replaced with fluorine or chlorine is trifluoromethoxy. A preferred example of alkenyloxy in which at least one hydrogen has been replaced with fluorine or chlorine is trifluorovinyloxy.

a is 1, 2, 3, or 4, b is 0, 1, 2, or 3, and the sum of a and b is 4 or less. Preferred a is 2 for lowering the lower limit temperature and 3 for raising the dielectric anisotropy. Preferred b is 0 to raise the upper limit temperature and 1 to raise the dielectric anisotropy. c and g are 0, 1, 2, or 3, d and h are 0 or 1, the sum of c and d is 1, 2, or 3, and the sum of g and h is 3. It is as follows. The preferred c or g is 1 for lowering the viscosity and 2 or 3 for raising the upper temperature limit. The preferred d or h is 0 to lower the viscosity and 1 to lower the lower limit temperature. e is 1, 2, or 3. Preferred e is 1 for lowering the viscosity and 2 or 3 for raising the upper temperature limit. f is 1, 2, 3, or 4. The preferred f is 2 for lowering the lower limit temperature and 3 for increasing the dielectric anisotropy.

Fifth, preferred component compounds are shown. Preferred compounds (1) are compounds (1-1) to compounds (1-14) according to Item 2. In these compounds, at least one of the first components is compound (1-2), compound (1-3), compound (1-4), compound (1-7), compound (1-8), compound ( 1-9), compound (1-10), or compound (1-12) is preferred.

Preferred compounds (2) are compounds (2-1) to compounds (2-38) according to Item 3. In these compounds, at least one of the second components is compound (2-1), compound (2-2), compound (2-3), compound (2-4), compound (2-7), compound ( 2-8), compound (2-14), compound (2-15), compound (2-16), compound (2-17), compound (2-22), compound (2-32), compound (2) -34), compound (2-35), compound (2-37), or compound (2-38) is preferred. It is preferable that at least two of the second components are a combination of compound (2-1) and compound (2-3).

Preferred compounds (3) are compounds (3-1) to compounds (3-13) according to Item 6. In these compounds, at least one of the third components is compound (3-1), compound (3-2), compound (3-3), compound (3-5), compound (3-6), compound ( 3-7), compound (3-8), compound (3-11), or compound (3-13) is preferred. At least two of the third components are compound (3-1) and compound (3-5), compound (3-1) and compound (3-6), compound (3-1) and compound (3-7), Compound (3-1) and compound (3-8), compound (3-1) and compound (3-13), compound (3-3) and compound (3-5), compound (3-3) and compound (3-6), compound (3-3) and compound (3-7), compound (3-3) and compound (3-8), or a combination of compound (3-3) and compound (3-13). Is preferable.

Preferred compounds (4) are compounds (4-1) to compounds (4-16) according to Item 9. In these compounds, at least one of the fourth components is compound (4-4), compound (4-7), compound (4-8), compound (4-11), compound (4-12), compound ( 4-13), compound (4-14), or compound (4-16) is preferred. At least two of the fourth components are compound (4-11) and compound (4-12), compound (4-11) and compound (4-13), compound (4-11) and compound (4-16), Alternatively, it is preferably a combination of compound (4-12) and compound (4-13).

Preferred compounds (5) are compounds (5-1) to compounds (5-31) according to Item 12. In these compounds, at least one of the fifth components is compound (5-1), compound (5-2), compound (5-3), compound (5-6), compound (5-7), compound ( 5-8), compound (5-9), compound (5-13), compound (5-15), or compound 5-17) is preferred. At least two of the fifth components are compound (5-1) and compound (5-4), compound (5-1) and compound (5-6), compound (5-1) and compound (5-7), Compound (5-1) and compound (5-9), compound (5-1) and compound (5-13), compound (5-1) and compound (5-15), compound (5-1) and compound (5-16), compound (5-7) and compound (5-8), compound (5-7) and compound (5-9), compound (5-7) and compound (5-13), compound ( 5-7) and compound (5-15), or a combination of compound (5-13) and compound (5-15) is preferred.

Sixth, additives that may be added to the composition will be described. Such additives include optically active compounds, antioxidants, UV absorbers, quenchers, dyes, defoamers, polymerizable compounds, polymerization initiators, polymerization inhibitors, polar compounds and the like. An optically active compound is added to the composition for the purpose of inducing a helical structure of liquid crystal molecules to give a helix angle. Examples of such compounds are compound (6-1) to compound (6-5). The preferred proportion of the optically active compound is about 5% by mass or less. A more preferable ratio is in the range of about 0.01% by mass to about 2% by mass.

式（７）において、Ｒ^９は炭素数１から１２のアルキルである。好ましいＲ^９はメチル、プロピル、ペンチル、またはヘプチルである。環Ｑは１，４−シクロヘキシレン、１，４−フェニレン、または１，３−ジオキサン−２，５−ジイルである。好ましい環Ｑは１，４−シクロへキシレンである。ｊは、０、１、または２である。好ましいｊは０または１である。Antioxidants are used to prevent a decrease in resistivity due to heating in the atmosphere, or to maintain a large voltage retention not only at room temperature but also at temperatures close to the upper limit temperature after long-term use of the device. Added to the composition. An example of an antioxidant is a compound represented by the formula (7).

In formula (7), R ⁹ is an alkyl having 1 to 12 carbon atoms. Preferred ^{R 9} is methyl, propyl, pentyl, or heptyl. Ring Q is 1,4-cyclohexylene, 1,4-phenylene, or 1,3-dioxane-2,5-diyl. The preferred ring Q is 1,4-cyclohexylene. j is 0, 1, or 2. The preferred j is 0 or 1.

Preferred compounds (7) are compounds (7-1) to compounds (7-3).

Preferred examples of UV absorbers are benzophenone derivatives, benzoate derivatives, triazole derivatives and the like. Light stabilizers such as sterically hindered amines are also preferred. Preferred examples of the light stabilizer are compounds (8-1) to compounds (8-16) and the like. The preferable ratio of these absorbents and stabilizers is about 50 ppm or more in order to obtain the effect, and about 10,000 ppm or less so as not to lower the upper limit temperature or raise the lower limit temperature. A more preferred ratio is in the range of about 100 ppm to about 10000 ppm.

The quencher is a compound that prevents the decomposition of the liquid crystal compound by receiving the light energy absorbed by the liquid crystal compound and converting it into heat energy. Preferred examples of the quencher are compounds (9-1) to compounds (9-7) and the like. The preferable ratio of these quenchers is about 50 ppm or more in order to obtain the effect, and about 20000 ppm or less in order not to raise the lower limit temperature. A more preferred ratio is in the range of about 100 ppm to about 10000 ppm.

Dichroic dyes such as azo dyes, anthraquinone dyes and the like are added to the composition to accommodate devices in GH (guest host) mode. The preferred proportion of dye is in the range of about 0.01% by weight to about 10% by weight. Antifoaming agents such as dimethyl silicone oil and methyl phenyl silicone oil are added to the composition to prevent foaming. The preferable ratio of the defoaming agent is about 1 ppm or more in order to obtain the effect, and about 1000 ppm or less in order to prevent display defects. A more preferred ratio is in the range of about 1 ppm to about 500 ppm.

Polymerizable compounds are used to adapt to polymer support orientation (PSA) type devices. Preferred examples of such polymerizable compounds are compounds such as acrylates, methacrylates, vinyl compounds, vinyloxy compounds, propenyl ethers, epoxy compounds (oxylane, oxetane), vinyl ketones and the like. A more preferred example is a derivative of acrylate or methacrylate. The preferred ratio is 10% by mass or more based on the total mass of the polymerizable compound. A more preferable ratio is 50% by mass or more. A particularly preferable ratio is 80% by mass or more. The most preferable ratio is 100% by mass.

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-tert-butylcatechol, 4-methoxyphenol, phenothiazine and the like.

Polar compounds are organic compounds with polarity. Here, compounds having an ionic bond are not included. Atoms such as oxygen, sulfur, and nitrogen are more electrically negative and tend to have partial negative charges. Carbon and hydrogen tend to be neutral or have a partially positive charge. Polarity arises from the uneven distribution of partial charges between different atoms in a compound. For example, polar compounds have at least one of the partial structures such as -OH, -COOH, -SH, -NH _{2,>NH,> N-.}

Seventh, a method for synthesizing a component compound will be described. These compounds can be synthesized by known methods. An example of the synthesis method. Compound (1-1) is obtained from Sigma-Aldrich Corporation or synthesized by the method described in US Pat. No. 3,660,505. Compound (2-3 is synthesized by the method described in International Publication No. 1999/021816. Compound (3-1) is synthesized by the method described in JP-A-59-176221. Compound (4). -1) is synthesized by the method described in JP-A-2000-053602.

Compounds for which synthetic methods were not described are Organic Syntheses, John Wiley & Sons, Inc, Organic Reactions, John Wiley & Sons, Inc, and Comprehensive Organic. It can be synthesized by the methods described in books such as Synthesis, Pergamon Press) and New Experimental Chemistry Course (Maruzen). The composition is prepared from the compound thus obtained by a known method. For example, the constituent compounds are mixed and dissolved by heating.

Finally, the use of the composition will be described. The composition mainly has a lower limit temperature of about −10 ° C. or lower, an upper limit temperature of about 70 ° C. or higher, and an optical anisotropy in the range of about 0.07 to about 0.20. Compositions having an optical anisotropy in the range of about 0.08 to about 0.25 may be prepared by controlling the proportions of the constituent compounds or by mixing other liquid crystal compounds. By trial and error, a composition having an optical anisotropy in the range of about 0.10 to about 0.30 may be prepared. The device containing this composition has a large voltage holding ratio. This composition is suitable for AM devices. This composition is particularly suitable for transmissive AM devices. This composition can be used as a composition having a nematic phase, or can be used as an optically active composition by adding an optically active compound.

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

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

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

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

Chloroform, hexane or the like may be used as the solvent for diluting the sample. The following capillary columns may be used to separate the constituent compounds. HP-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm) manufactured by Agilent Technologies Inc., Rtx-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm) manufactured by Restek Corporation, BP-1 manufactured by SGE International Pty. Ltd (length 30 m, inner diameter 0.32 mm, film thickness 0.25 μm). A capillary column CBP1-M50-025 (length 50 m, inner diameter 0.25 mm, film thickness 0.25 μm) manufactured by Shimadzu Corporation may be used for the purpose of preventing overlapping of compound peaks.

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

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

The following mother liquid crystal was used. The ratio of the component compounds is shown in% by mass.

Measurement method: The characteristics were measured by the following method. Many of these are methods described in the JEITA standard (JEITA ED-2521B), which is deliberated and enacted by the Japan Electronics and Information Technology Industries Association (JEITA), or a modified method. Met. A thin film transistor (TFT) was not attached to the TN element used for the measurement.

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

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

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

(4) Viscosity (rotational viscosity; γ1; measured at 25 ° C.; mPa · s): The measurement was carried out according to the method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). I obeyed. The sample was placed in a TN device having a twist angle of 0 ° and a distance (cell gap) between the two glass substrates of 5 μm. A stepwise application was applied to this device in 0.5 V increments in the range of 16 V to 19.5 V. After no application for 0.2 seconds, application was repeated under the conditions of only one square wave (square pulse; 0.2 seconds) and no application (2 seconds). The peak current and peak time of the transient current generated by this application were measured. The value of rotational viscosity was obtained from these measured values and the calculation formula (10) described on page 40 in the paper by M. Imai et al. The value of the dielectric anisotropy required for this calculation was obtained by the method described below using the device for which the rotational viscosity was measured.

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

(6) Dielectric constant anisotropy (Δε; measured at 25 ° C.): The sample was placed in a TN element having a distance (cell gap) between two glass substrates of 9 μm and a twist angle of 80 degrees. A sine wave (10 V, 1 kHz) was applied to this device, and after 2 seconds, the permittivity (ε ‖) of the liquid crystal molecule in the long axis direction was measured. A sine wave (0.5 V, 1 kHz) was applied to this element, and after 2 seconds, the permittivity (ε⊥) of the liquid crystal molecule in the minor axis direction was measured. The value of permittivity anisotropy was calculated from the formula Δε ＝ ε‖−ε⊥.

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

(8) Voltage retention rate (VHR-9; measured at 25 ° C.;%): The TN element used for the measurement had a polyimide alignment film, and the distance (cell gap) between the two glass substrates was 5 μm. .. This device was sealed with an adhesive that cures with ultraviolet light after the sample was placed. A pulse voltage (60 microseconds at 1 V) was applied to the TN element to charge it. The decaying voltage was measured with a high-speed voltmeter for 166.7 milliseconds, and the area A between the voltage curve and the horizontal axis in a unit period was determined. Area B was the area when there was no attenuation. The voltage holding ratio is expressed as a percentage of the area A with respect to the area B.

(9) Voltage retention rate (VHR-10; measured at 60 ° C.;%): The voltage retention rate was measured by the same procedure as above except that the voltage retention rate was measured at 60 ° C. instead of 25 ° C. The obtained value was represented by VHR-10.

(10) Voltage retention rate (VHR-11; measured at 60 ° C.;%): After irradiation with ultraviolet rays, the voltage retention rate was measured to evaluate the stability against ultraviolet rays. The TN device used for the measurement had a polyimide alignment film, and the cell gap was 5 μm. A sample was injected into this device and irradiated with ultraviolet rays of ^{5 mW / cm 2 for 167 minutes.} The light source was a black light manufactured by Eye Graphics Co., Ltd., F40T10 / BL (peak wavelength 369 nm), and the distance between the element and the light source was 5 mm. In the VHR-11 measurement, the decaying voltage was measured for 166.7 milliseconds. Compositions with large VHR-11 have great stability to UV light.

(11) Voltage retention rate (VHR-12; measured at 60 ° C.;%): After heating the TN element into which the sample was injected in a constant temperature bath at 120 ° C. for 20 hours, the voltage retention rate was measured and stability against heat was measured. Was evaluated. In the VHR-12 measurement, the voltage decayed for 166.7 ms was measured. Compositions with large VHR-12 have great stability to heat.

(12) Response time (τ; measured at 25 ° C.; ms): An LCD5100 type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement. The light source was a halogen lamp. The low-pass filter was set to 5 kHz. The sample was placed in a normally white mode TN element in which the distance (cell gap) between the two glass substrates was 5.0 μm and the twist angle was 80 degrees. A square wave (60 Hz, 5 V, 0.5 seconds) was applied to this device. At this time, the element was irradiated with light from the vertical direction, and the amount of light transmitted through the element was measured. It was considered that the transmittance was 100% when the amount of light was maximum, and the transmittance was 0% when the amount of light was minimum. The rise time (τr: rise time; millisecond) is the time required for the transmittance to change from 90% to 10%. The fall time (τf: fall time; millisecond) is the time required for the transmittance to change from 10% to 90%. The response time was expressed as the sum of the rise time and the fall time obtained in this way.

(13) Elastic constant (K; measured at 25 ° C.; pN): An HP4284A type LCR meter manufactured by Yokogawa Hewlett-Packard Co., Ltd. was used for the measurement. The sample was placed in a horizontally oriented element in which the distance (cell gap) between the two glass substrates was 20 μm. A charge of 0 to 20 volts was applied to this device, and the capacitance and applied voltage were measured. Fitting the measured capacitance (C) and applied voltage (V) values using the "Liquid Crystal Device Handbook" (Nikkan Kogyo Shimbun), equations (2.98) and (2.11) on page 75. Then, the values of K11 and K33 were obtained from the formula (2.99). Next, K22 was calculated using the values of K11 and K33 obtained earlier in the formula (3.18) on page 171 of the same. The elastic constant was represented by the average value of K11, K22, and K33 thus obtained.

(14) Specific resistance (ρ; measured at 25 ° C.; Ωcm): 1.0 mL of the sample was injected into a container equipped with an electrode. A DC voltage (10 V) was applied to this container, and the DC current after 10 seconds was measured. The specific resistance was calculated from the following formula. (Specific resistance) = {(voltage) x (capacitance of container)} / {(DC current) x (vacuum permittivity)}.

(15) Spiral pitch (P; measured at room temperature; μm): The spiral pitch was measured by the wedge method. See "LCD Handbook", page 196 (published in 2000, Maruzen). The sample was injected into a wedge-shaped cell, allowed to stand at room temperature for 2 hours, and then the spacing of the dispersion lines (d2-d1) was observed with a polarizing microscope (Nikon Corporation, trade name MM40 / 60 series). The spiral pitch (P) was calculated from the following equation in which the angle of the wedge cell was expressed as θ. P = 2 × (d2-d1) × tan θ.

(16) Dielectric constant in the minor axis direction (ε⊥; measured at 25 ° C.): The sample was placed in a TN element having a distance (cell gap) between two glass substrates of 9 μm and a twist angle of 80 degrees. .. A sine wave (0.5 V, 1 kHz) was applied to this element, and after 2 seconds, the permittivity (ε⊥) of the liquid crystal molecule in the minor axis direction was measured.

(17) Line image sticking parameter (LISP;%): A line afterimage was generated by applying electrical stress to the liquid crystal display element. The brightness of the area with the line afterimage and the brightness of the remaining area were measured. The rate at which the brightness decreased due to the line afterimage was calculated, and the magnitude of the line afterimage was expressed by this rate.
17a) Luminance measurement: An image of the device was taken using an imaging color luminance meter (Radiant Zemax, PM-1433F-0). The brightness of each region of the device was calculated by analyzing this image using software (Prometric 9.1, manufactured by Radiant Imaging).

17b) Stress voltage setting: A sample is placed in an FFS element (16 cells of 4 cells vertically x 4 cells horizontally) having a cell gap of 3.5 μm and having a matrix structure, and an adhesive that cures this element with ultraviolet rays is used. And sealed. Polarizing plates were arranged on the upper surface and the lower surface of this device so that the polarization axes were orthogonal to each other. This element was irradiated with light and a voltage (square wave, 60 Hz) was applied. The voltage was gradually increased in steps of 0.1 V in the range of 0 V to 7.5 V, and the brightness of the transmitted light at each voltage was measured. The voltage when the brightness became maximum was abbreviated as V255. The voltage when the brightness becomes 21.6% of V255 (that is, 127 gradations) is abbreviated as V127.

17c) Stress conditions: V255 (square wave, 30 Hz) and 0.5 V (square wave, 30 Hz) were applied to the element under the conditions of 60 ° C. and 23 hours to display a checker pattern. Next, V127 (square wave, 0.25 Hz) was applied, and the brightness was measured under the condition of an exposure time of 4000 milliseconds.

17d) Calculation of line afterimage: Of the 16 cells, 4 cells in the center (2 vertical cells x 2 horizontal cells) were used for the calculation. These 4 cells were divided into 25 areas (5 vertical cells x 5 horizontal cells). The average brightness of the four regions (2 vertical cells x 2 horizontal cells) at the four corners is abbreviated as brightness A. The region excluding the four corner regions from the 25 regions was a cruciform. In the four regions excluding the central intersection region from this cruciform region, the minimum value of luminance is abbreviated as luminance B. The line afterimage was calculated from the following formula. (Line afterimage) = (luminance A-luminance B) / luminance A × 100.

(18) Spreadability: The spreadability of the additive was qualitatively evaluated by applying a voltage to the device and measuring the brightness. The brightness was measured in the same manner as in Item 14a above. The voltage (V127) was set in the same manner as in Item 14b above. However, a VA element was used instead of the FFS element. The brightness was measured as follows. First, a DC voltage (2V) was applied to the device for 2 minutes. Next, V127 (square wave, 0.05 Hz) was applied, and the brightness was measured under the condition of an exposure time of 4000 milliseconds. From this result, the spreadability was evaluated.

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

[Example 1]
3-GB (F, F) XB (F, F) -F (1-3) 3%
4-GB (F) B (F, F) XB (F, F) -F (1-9) 3%
5-GB (F) B (F, F) XB (F, F) -F (1-9) 2%
3-BB (F) B (F, F) XB (F, F) -F (1-10) 3%
4-BB (F) B (F, F) XB (F, F) -F (1-10) 6%
3-HB (2F) B (2F, 3F) -O2 (2-3) 13%
3-HH-V (3-1) 37%
V-HH-V1 (3-1) 4%
V-HHB-1 (3-5) 6.5%
1-BB (F) B-2V (3-8) 3.5%
3-GB (F) B (F) -F (4) 9%
3-GB (F) B (F) B (F) -F (4) 4%
3-GB (F) B (F, F) -F (4-11) 5%
4-GBB (F) B (F, F) -F (4-16) 1%
NI = 80.2 ° C; Tc <-20 ° C; Δn = 0.113; Δε = 8.0; Vth = 1.50V; γ1 = 102.5mPa · s; ε⊥ = 4.90.

[Comparative Example 1]
3-GB (F, F) XB (F, F) -F (1-3) 3%
4-GB (F) B (F, F) XB (F, F) -F (1-9) 3%
5-GB (F) B (F, F) XB (F, F) -F (1-9) 2%
3-BB (F) B (F, F) XB (F, F) -F (1-10) 3%
4-BB (F) B (F, F) XB (F, F) -F (1-10) 6%
3-HH-V (3-1) 37%
V-HH-V1 (3-1) 4%
V-HHB-1 (3-5) 6.5%
3-HBB-2 (3-6) 13%
1-BB (F) B-2V (3-8) 3.5%
3-GB (F) B (F) -F (4) 9%
3-GB (F) B (F) B (F) -F (4) 4%
3-GB (F) B (F, F) -F (4-11) 5%
4-GBB (F) B (F, F) -F (4-16) 1%
NI = 83.7 ° C; Tc <-20 ° C; η = 14.9 mPa · s; Δn = 0.115; Δε = 8.6; Vth = 1.52V; γ1 = 80.6 mPa · s; ε⊥ = 3.82.

[Example 2]
3-HBB (F, F) XB (F, F) -F (1-7) 7%
4-GB (F) B (F, F) XB (F, F) -F (1-9) 3%
3-BB (F) B (F, F) XB (F, F) -F (1-10) 3%
4-BB (F) B (F, F) XB (F, F) -F (1-10) 7%
3-HB (2F) B (2F, 3F) -O2 (2-3) 12%
3-HH-V (3-1) 30%
3-HH-V1 (3-1) 6%
3-HB-O2 (3-2) 5%
1-BB-3 (3-3) 6%
5-B (F) BB-2 (3-7) 4%
1-BB (F) B-2V (3-8) 5%
3-BB (F) B (F, F) -F (4-12) 6%
3-BB (F) B (F, F) -CF3 (4-13) 6%
NI = 73.3 ° C; Tc <-20 ° C; η = 17.8 mPa · s; Δn = 0.134; Δε = 6.6; Vth = 1.79 V; γ1 = 88.7 mPa · s; ε⊥ = 4.11.

[Comparative Example 2]
3-HBB (F, F) XB (F, F) -F (1-7) 7%
4-GB (F) B (F, F) XB (F, F) -F (1-9) 3%
3-BB (F) B (F, F) XB (F, F) -F (1-10) 3%
4-BB (F) B (F, F) XB (F, F) -F (1-10) 7%
3-HH-V (3-1) 30%
3-HH-V1 (3-1) 6%
3-HB-O2 (3-2) 5%
1-BB-3 (3-3) 6%
5-B (F) BB-2 (3-7) 4%
1-BB (F) B-2V (3-8) 5%
3-BB (F) B (F, F) -F (4-12) 6%
3-BB (F) B (F, F) -CF3 (4-13) 6%
3-HHB (2F, 3F) -O2 (5-7) 6%
5-HHB (2F, 3F) -O2 (5-7) 6%
NI = 77.9 ° C; Tc <-20 ° C; η = 15.2 mPa · s; Δn = 0.126; Δε = 6.9; Vth = 1.79V; ε⊥ = 3.80.

[Example 3]
3-GB (F, F) XB (F, F) -F (1-3) 8%
4-GB (F) B (F, F) XB (F, F) -F (1-9) 2%
4-BB (F) B (F, F) XB (F, F) -F (1-10) 3%
3-HB (2F) B (2F, 3F) -O2 (2-3) 4%
3-HH-V (3-1) 35%
3-HH-V1 (3-1) 2%
V-HHB-1 (3-5) 11%
1-BB (F) B-2V (3-8) 3%
2-BB (F) B-2V (3-8) 3%
3-BB (F) B-2V (3-8) 1%
3-GB (F) B (F) -F (4) 12%
3-GB (F) B (F) B (F) -F (4) 4%
3-GB (F) B (F, F) -F (4-11) 5%
4-GBB (F) B (F, F) -F (4-16) 3%
3-dhBB (2F, 3F) -O2 (5-15) 4%
NI = 80.7 ° C; Tc <-20 ° C; Δn = 0.113; Δε = 8.0; Vth = 1.50V; γ1 = 93.1mPa · s; ε⊥ = 4.63.

[Example 4]
3-BB (F, F) XB (F, F) -F (1-4) 16%
3-BB (F) B (F, F) XB (F, F) -F (1-10) 4%
4-BB (F) B (F, F) XB (F, F) -F (1-10) 5%
3-HB (2F) B (2F, 3F) -O2 (2-3) 10%
3-HH-V (3-1) 33%
3-HH-V1 (3-1) 6%
1-BB-3 (3-3) 2%
V-HHB-1 (3-5) 2%
1-BB (F) B-2V (3-8) 5%
2-BB (F) B-2V (3-8) 7%
3-dhBB (2F, 3F) -O2 (5-15) 10%
NI = 75.3 ° C; Tc <-20 ° C; η = 15.6 mPa · s; Δn = 0.130; Δε = 4.5; Vth = 1.95 V; γ1 = 64.0 mPa · s; ε⊥ = 4.45.

[Example 5]
3-GB (F, F) XB (F, F) -F (1-3) 7%
4-GB (F) B (F, F) XB (F, F) -F (1-9) 2%
3-HB (2F) B (2F, 3F) -O2 (2-3) 6%
3-HH-V (3-1) 36%
V-HHB-1 (3-5) 11%
V2-HHB-1 (3-5) 8%
3-HHB-O1 (3-5) 2%
1-BB (F) B-2V (3-8) 3%
2-BB (F) B-2V (3-8) 2%
3-GB (F) B (F) -F (4) 11%
3-GB (F) B (F, F) -F (4-11) 8%
3-GBB (F) B (F, F) -F (4-16) 2%
4-GBB (F) B (F, F) -F (4-16) 2%
NI = 78.7 ° C; Tc <-20 ° C; η = 15.7 mPa · s; Δn = 0.103; Δε = 7.0; Vth = 1.48V; γ1 = 89.4 mPa · s; ε⊥ = 4.37.

[Example 6]
3-GB (F, F) XB (F, F) -F (1-3) 7%
3-BB (2F, 3F) XB (F, F) -F (1-4) 12%
3-GB (F) B (F, F) XB (F, F) -F (1-9) 4%
3-HB (2F) B (2F, 3F) -O2 (2-3) 2%
3-HH-V (3-1) 28%
V-HHB-1 (3-5) 12%
V2-HHB-1 (3-5) 9%
3-HHB-1 (3-5) 4%
3-HHB-O1 (3-5) 2%
V-HBB-2 (3-6) 2%
2-BB (F) B-3 (3-8) 3%
3-GB (F) B (F) -F (4) 11%
3-GB (F) B (F, F) -F (4-11) 4%
NI = 83.8 ° C; Tc <-20 ° C; η = 14.8 mPa · s; Δn = 0.104; Δε = 7.6; Vth = 1.58 V; γ1 = 91.0 mPa · s; ε⊥ = 4.37.

[Example 7]
3-BB (F, F) XB (F, F) -F (1-4) 16%
3-HBBXB (F, F) -F (1-7) 6%
3-HBB (F, F) XB (F, F) -F (1-7) 5%
3-GB (F) B (F, F) XB (F, F) -F (1-9) 2%
4-GB (F) B (F, F) XB (F, F) -F (1-9) 3%
3-H1OB (2F) B (2F, 3F) -O2 (2-22) 5%
3-HH-V (3-1) 38.5%
V-HHB-1 (3-5) 3.5%
3-HBB-2 (3-6) 6%
3-HHB (2F, 3F) -O2 (5-7) 5%
5-HHB (2F, 3F) -O2 (5-7) 5%
3-HBB (2F, 3F) -O2 (5-13) 5%
NI = 84.4 ° C; Tc <-20 ° C; η = 14.1 mPa · s; Δn = 0.106; Δε = 5.8; Vth = 1.72 V; γ1 = 100.6 mPa · s; ε⊥ = 4.52.

[Example 8]
4-GB (F) B (F, F) XB (F, F) -F (1-9) 4%
3-BB (F) B (F, F) XB (F, F) -F (1-10) 3%
4-BB (F) B (F, F) XB (F, F) -F (1-10) 8%
3-HB (2F) B (2F, 3F) -O2 (2-3) 5%
3-HH-V (3-1) 46%
1-BB (F) B-2V (3-8) 6%
2-BB (F) B-2V (3-8) 4%
3-BB (F) B (F, F) -F (4-12) 9%
3-HB (2F, 3F) -O2 (5-1) 4%
3-HHB (2F, 3F) -O2 (5-7) 4%
3-HBB (2F, 3F) -O2 (5-13) 4%
3-dhBB (2F, 3F) -O2 (5-15) 3%
NI = 77.0 ° C; Tc <-20 ° C; η = 13.5mPa · s; Δn = 0.121; Δε = 4.4; Vth = 1.96V; γ1 = 80.5mPa · s; ε⊥ = 4.55.

[Example 9]
3-HHXB (F, F) -F (1-2) 1%
3-GB (F, F) XB (F, F) -F (1-3) 5%
V-HB (2F) B (2F, 3F) -O2 (2-3) 3%
3-HH-V (3-1) 36%
3-HH-V1 (3-1) 8%
V-HHB-1 (3-5) 7%
1-BB (F) B-2V (3-8) 6%
2-BB (F) B-2V (3-8) 7%
3-GB (F) B (F) -F (4) 7%
3-GB (F) B (F, F) -F (4-11) 8%
3-BB (F) B (F, F) -CF3 (4-13) 5%
2-HBB (2F, 3F) -O2 (5-13) 2%
3-HBB (2F, 3F) -O2 (5-13) 5%
NI = 74.6 ° C; Tc <-20 ° C; η = 13.1 mPa · s; Δn = 0.113; Δε = 4.9; Vth = 1.81 V; γ1 = 72.6 mPa · s; ε⊥ = 4.23.

[Example 10]
3-HHXB (F, F) -F (1-2) 1%
3-GB (F, F) XB (F, F) -F (1-3) 3%
3-BB (F, F) XB (F) B (F, F) -F (1-12) 4%
3-HB (2F) B (2F, 3F) -O2 (2-3) 4%
3-HH-V (3-1) 34%
3-HH-V1 (3-1) 3.5%
3-HB-O2 (3-2) 2%
V-HHB-1 (3-5) 7%
5-HBB (F) B-3 (3-13) 5%
3-GB (F) B (F) -F (4) 2%
3-GB (F) B (F) B (F) -F (4) 2%
3-GB (F) B (F, F) -F (4-11) 4.5%
3-BB (F) B (F, F) -CF3 (4-13) 3%
3-GBB (F) B (F, F) -F (4-16) 2%
4-GBB (F) B (F, F) -F (4-16) 2%
3-HHB (2F, 3F) -O2 (5-7) 5%
V-HHB (2F, 3F) -O2 (5-7) 6%
2-HBB (2F, 3F) -O2 (5-13) 2%
3-HBB (2F, 3F) -O2 (5-13) 5%
5-HBB (2F, 3F) -O2 (5-13) 3%
NI = 99.8 ° C; Tc <-20 ° C; η = 17.9 mPa · s; Δn = 0.113; Δε = 4.0; Vth = 2.20 V; γ1 = 161.7 mPa · s; ε⊥ = 4.91.

[Example 11]
1-HHXB (F, F) -F (1-2) 5%
3-GB (F, F) XB (F, F) -F (1-3) 6%
4-GB (F) B (F, F) XB (F, F) -F (1-9) 3%
2O-B (2F) B (2F, 3F) -O4 (2-1) 3%
3-HH2B (2F) B (2F, 3F) -O2 (2-34) 3%
3-HH-V (3-1) 18%
1V2-HH-3 (3-1) 7%
2-HH-3 (3-1) 10%
3-HH-VFF (3-1) 6%
1-BB-5 (3-3) 6%
V2-HHB-1 (3-5) 8%
3-HHB-O1 (3-5) 2%
2-BB (F) B-5 (3-8) 3%
3-BB (F) B-5 (3-8) 2%
3-GB (F) B (F) B (F) -F (4) 6%
3-GB (F) B (F, F) -F (4-11) 7%
3-GBB (F) B (F, F) -F (4-16) 3%
4-GBB (F) B (F, F) -F (4-16) 2%
NI = 76.7 ° C; Tc <-20 ° C; Δn = 0.104; Δε = 6.7; Vth = 1.64V; γ1 = 82.0mPa · s; ε⊥ = 4.04.

[Example 12]
3-GB (F, F) XB (F, F) -F (1-3) 5%
3-BB (F, F) XB (F, F) -F (1-4) 5%
3-BB (2F, 3F) XB (F, F) -F (1-4) 5%
3-GB (F) B (F, F) XB (F, F) -F (1-9) 7%
5-BB (F) B (F, F) XB (F, F) -F (1-10) 5%
2O-B (2F) B (2F, 3F) -O4 (2-1) 2%
3-HH-V (3-1) 30%
1-BB-5 (3-3) 6%
3-HHEH-3 (3-4) 6%
V-HHB-1 (3-5) 6%
V2-HHB-1 (3-5) 9%
3-HHB-1 (3-5) 3%
V-HBB-2 (3-6) 2%
2-BB (F) B-3 (3-8) 3%
2-HGB (F, F) -F (4-6) 3%
3-HGB (F, F) -F (4-6) 3%
NI = 74.7 ° C; Tc <-20 ° C; Δn = 0.101; Δε = 6.9; Vth = 1.56V; γ1 = 73.5mPa · s; ε⊥ = 3.90.

[Example 13]
3-GB (F, F) XB (F, F) -F (1-3) 7%
5-GB (F) B (F, F) XB (F, F) -F (1-9) 3%
3-BB (F) B (F, F) XB (F, F) -F (1-10) 3%
2O-B (2F) B (2F, 3F) -O4 (2-1) 6%
3-HH-V (3-1) 33%
V-HHB-1 (3-5) 11%
V2-HHB-1 (3-5) 8%
3-HHB-O1 (3-5) 2%
1-BB (F) B-2V (3-8) 3%
2-BB (F) B-2V (3-8) 2%
3-BB (F) B-2V (3-8) 3%
3-HHB-OCF3 (4-3) 4%
3-GHB (F, F) -F (4-7) 5%
4-GHB (F, F) -F (4-7) 5%
5-GHB (F, F) -F (4-7) 5%
NI = 79.0 ° C; Tc <-20 ° C; Δn = 0.098; Δε = 5.8; Vth = 1.65V; γ1 = 72.0mPa · s; ε⊥ = 4.08.

[Example 14]
3-GB (F, F) XB (F, F) -F (1-3) 7%
3-BB (2F, 3F) XB (F, F) -F (1-4) 12%
3-GB (F) B (F, F) XB (F, F) -F (1-9) 4%
2O-B (2F) B (2F, 3F) -O4 (2-1) 2%
3-HH-V (3-1) 10%
3-HH-V1 (3-1) 5%
3-HH-VFF (3-1) 8%
4-HH-V (3-1) 5%
5-HH-V (3-1) 5%
V2-HHB-1 (3-5) 4%
3-HHB-1 (3-5) 4%
3-HHB-3 (3-5) 3%
2-HHB-1 (3-5) 3%
1V2-HHB-1 (3-5) 3%
V-HBB-2 (3-6) 2%
2-BB (F) B-3 (3-8) 3%
5-HBB (F) B-2 (3-13) 5%
1-HHB (F, F) -F (4-4) 3%
2-HHB (F, F) -F (4-4) 3%
2-HBEB (F, F) -F (4-10) 4%
3-GB (F) B (F, F) -F (4-11) 3%
3-BB (F) B (F, F) -F (4-12) 2%
NI = 76.5 ° C; Tc <-20 ° C; Δn = 0.103; Δε = 7.3; Vth = 1.50V; γ1 = 84.5mPa · s; ε⊥ = 4.17.

[Example 15]
3-GB (F) B (F, F) XB (F, F) -F (1-9) 7%
4-GB (F) B (F, F) XB (F, F) -F (1-9) 2%
2O-B (2F) B (2F, 3F) -O4 (2-1) 6%
3-HH-V (3-1) 30%
7-HB-1 (3-2) 5%
5-HB-O2 (3-2) 5%
V2-BB-1 (3-3) 7%
V2-HHB-1 (3-5) 8%
3-HHB-O1 (3-5) 2%
1-BB (F) B-2V (3-8) 3%
2-BB (F) B-2V (3-8) 2%
2-HHEB (F, F) -F (4-5) 4%
3-HHEB (F, F) -F (4-5) 5%
4-HHEB (F, F) -F (4-5) 3%
3-GB (F) B (F, F) -F (4-11) 5%
3-GBB (F) B (F, F) -F (4-16) 3%
4-GBB (F) B (F, F) -F (4-16) 3%
NI = 71.2 ° C; Tc <-20 ° C; Δn = 0.105; Δε = 6.2; Vth = 1.60V; γ1 = 68.4mPa · s; ε⊥ = 4.12.

[Example 16]
3-GB (F, F) XB (F, F) -F (1-3) 6%
3-BB (2F, 3F) XB (F, F) -F (1-4) 5%
3-GB (F) B (F, F) XB (F, F) -F (1-9) 6%
4-GB (F) B (F, F) XB (F, F) -F (1-9) 6%
2O-B (2F) B (2F, 3F) -O4 (2-1) 2%
3-HH-V (3-1) 28%
V-HHB-1 (3-5) 12%
V2-HHB-1 (3-5) 9%
V-HBB-2 (3-6) 3%
2-BB (F) B-3 (3-8) 3%
3-HHEBH-3 (3-11) 2%
3-HHB-F (4) 3%
3-HB-CL (4-1) 5%
5-HB-CL (4-1) 3%
7-HB-CL (4-1) 3%
3-BB (F) B (F, F) -F (4-12) 4%
NI = 75.7 ° C; Tc <-20 ° C; Δn = 0.101; Δε = 6.8; Vth = 1.52V; γ1 = 70.9mPa · s; ε⊥ = 3.86.

[Example 17]
3-GB (F, F) XB (F, F) -F (1-3) 7%
3-HBBXB (F, F) -F (1-7) 2%
2O-B (2F) B (2F, 3F) -O4 (2-1) 6%
3-HH-V (3-1) 30%
3-HH-V1 (3-1) 6%
V-HHB-1 (3-5) 6%
V2-HHB-1 (3-5) 4%
3-HHB-O1 (3-5) 2%
V-HBB-2 (3-6) 5%
3-HHEBH-5 (3-11) 4%
2-HBB-F (4) 4%
3-HHB (F, F) -F (4-4) 4%
5-HHEB (F, F) -F (4-5) 4%
3-GB (F) B (F, F) -F (4-11) 6%
3-BB (F) B (F, F) -CF3 (4-13) 10%
NI = 80.2 ° C; Tc <-20 ° C; Δn = 0.101; Δε = 6.1; Vth = 1.66V; γ1 = 73.1mPa · s; ε⊥ = 4.04.

[Example 18]
3-GB (F, F) XB (F, F) -F (1-3) 7%
3-BB (2F, 3F) XB (F, F) -F (1-4) 6%
3-GB (F) B (F, F) XB (F, F) -F (1-9) 5%
4-GB (F) B (F, F) XB (F, F) -F (1-9) 5%
2O-B (2F) B (2F, 3F) -O4 (2-1) 2%
3-HH-V (3-1) 30%
3-HH-V1 (3-1) 6%
V-HHB-1 (3-5) 5%
V2-HHB-1 (3-5) 6%
3-HHB-1 (3-5) 3%
V-HBB-2 (3-6) 4%
2-BB (F) B-3 (3-8) 5%
2-HBB (F, F) -F (4-8) 3%
3-HBB (F, F) -F (4-8) 3%
5-HBB (F, F) -F (4-8) 3%
3-GB (F) B (F, F) -F (4-11) 4%
1O1-HBBH-5 (-) 3%
NI = 78.0 ° C; Tc <-20 ° C; Δn = 0.104; Δε = 7.6; Vth = 1.51V; γ1 = 73.7mPa · s; ε⊥ = 3.95.

[Example 19]
3-GB (F, F) XB (F, F) -F (1-3) 6%
3-BB (F, F) XB (F, F) -F (1-4) 3%
2O-B (2F) B (2F, 3F) -O4 (2-1) 6%
3-HH-V (3-1) 36%
3-HH-VFF (3-1) 7%
V-HHB-1 (3-5) 11%
V2-HHB-1 (3-5) 8%
3-GB (F) B (F) B (F) -F (4) 5%
3-BB (F) B (F, F) -CF3 (4-13) 12%
4-HHBB (F, F) -F (4-14) 6%
NI = 77.2 ° C; Tc <-20 ° C; Δn = 0.101; Δε = 5.9; Vth = 1.67V; γ1 = 67.0mPa · s; ε⊥ = 3.91.

[Example 20]
3-GB (F, F) XB (F, F) -F (1-3) 7%
3-BB (2F, 3F) XB (F, F) -F (1-4) 8%
3-GB (F) B (F, F) XB (F, F) -F (1-9) 8%
2O-B (2F) B (2F, 3F) -O4 (2-1) 2%
3-HH-V (3-1) 34%
3-HH-V1 (3-1) 6%
V-HHB-1 (3-5) 10%
V2-HHB-1 (3-5) 6%
3-HHB-3 (3-5) 5%
2-BB (F) B-3 (3-8) 3%
3-BB (F) B (F, F) -CF3 (4-13) 7%
5-HHBB (F, F) -F (4-14) 4%
NI = 77.3 ° C; Tc <-20 ° C; Δn = 0.100; Δε = 7.2; Vth = 1.53V; γ1 = 72.3mPa · s; ε⊥ = 3.85.

[Example 21]
3-dhBB (F, F) XB (F, F) -F (1-8) 5%
5-GB (F) B (F, F) XB (F, F) -F (1-9) 3%
3-BB (F) B (F, F) XB (F) -F (1-10) 3%
3-BB (F) B (F, F) XB (F, F) -F (1-10) 3%
3-HB (2F) B (2F, 3F) -O2 (2-3) 6%
3-DhB (F) B (2F, 3F) -O2 (2-17) 4%
3-HH-V (3-1) 25%
2-HH-3 (3-1) 10%
V-HHB-1 (3-5) 10%
3-HBB-2 (3-6) 8%
1-BB (F) B-2V (3-8) 3%
2-BB (F) B-2V (3-8) 2%
3-HBB-F (4) 3%
5-HBB-F (4) 3%
7-HB (F, F) -F (4-2) 3%
3-GHB (F, F) -F (4-7) 3%
4-GHB (F, F) -F (4-7) 3%
5-GHB (F, F) -F (4-7) 3%
NI = 85.9 ° C; Tc <-20 ° C; η = 17.1 mPa · s; Δn = 0.109; Δε = 4.7; Vth = 1.98 V; γ1 = 86.9 mPa · s; Δ⊥ = 3.85.

[Example 22]
3-GB (F, F) XB (F, F) -F (1-3) 7%
3-HBBXB (F, F) -F (1-7) 2%
2O-B (2F) B (2F, 3F) -O4 (2-1) 6%
3-HH-V (3-1) 20%
3-HH-V1 (3-1) 6%
1V2-HH-1 (3-1) 5%
3-HH-O1 (3-1) 5%
V-HHB-1 (3-5) 6%
V2-HHB-1 (3-5) 4%
3-HHB-O1 (3-5) 2%
V-HBB-2 (3-6) 5%
3-HHEBH-4 (3-11) 3%
2-HBB-F (4) 4%
4-HHB (F, F) -F (4-4) 4%
4-HGB (F, F) -F (4-6) 3%
5-HGB (F, F) -F (4-6) 3%
3-GB (F) B (F, F) -F (4-11) 6%
3-BB (F) B (F, F) -CF3 (4-13) 9%
NI = 73.2 ° C; Tc <-20 ° C; Δn = 0.098; Δε = 6.3; Vth = 1.58V; γ1 = 71.6mPa · s; ε⊥ = 4.25.

[Example 23]
3-GB (F) B (F, F) XB (F, F) -F (1-9) 7%
4-GB (F) B (F, F) XB (F, F) -F (1-9) 2%
2O-B (2F) B (2F, 3F) -O4 (2-1) 6%
3-HH-V (3-1) 30%
7-HB-1 (3-2) 5%
5-HB-O2 (3-2) 5%
V2-BB-1 (3-3) 7%
V2-HHB-1 (3-5) 8%
3-HHB-O1 (3-5) 2%
1-BB (F) B-2V (3-8) 3%
2-BB (F) B-2V (3-8) 2%
2-HHEB (F, F) -F (4-5) 4%
3-HHEB (F, F) -F (4-5) 4%
4-HHEB (F, F) -F (4-5) 3%
3-HBEB (F, F) -F (4-10) 3%
5-HBEB (F, F) -F (4-10) 3%
2-HHBB (F, F) -F (4-14) 3%
3-HHBB (F, F) -F (4-14) 3%
NI = 76.5 ° C; Tc <-20 ° C; Δn = 0.103; Δε = 5.2; Vth = 1.81V; γ1 = 66.6mPa · s; ε⊥ = 3.86.

[Example 24]
3-HHXB (F, F) -CF3 (1-2) 5%
3-BB (F, F) XB (F, F) -F (1-4) 12%
4-GBB (F, F) XB (F, F) -F (1-9) 2%
5-GBB (F, F) XB (F, F) -F (1-9) 3%
3-BB (F) B (F, F) XB (F) -F (1-10) 4%
3-HB (2F) B (2F, 3F) -O2 (2-3) 5%
V-HBB (F) -O2 (3) 3%
3-HH-V (3-1) 33%
V-HHB-1 (3-5) 3%
2-HHB-CL (4) 3%
3-HHB-CL (4) 3%
2-HHB (F) -F (4) 3%
3-HHB (F) -F (4) 3%
V-H2HBB (2F, 3F) -O2 (5) 3%
5-HB (2F, 3F) -O2 (5-1) 3%
V-HB (2F, 3F) -O4 (5-1) 3%
3-H2B (2F, 3F) -O2 (5-2) 3%
2-HH1OB (2F, 3F) -O2 (5-9) 3%
3-HB (2F, 3F) B-2 (5-16) 3%
NI = 75.6 ° C; Tc <-20 ° C; Δn = 0.099; Δε = 4.8; Vth = 1.80V; γ1 = 97.1mPa · s; ε⊥ = 4.92.

[Example 25]
3-HHXB (F, F) -F (1-2) 3%
3-GB (F, F) XB (F, F) -F (1-3) 3%
3-BB (F) B (F, F) XB (F, F) -F (1-10) 3%
4-BB (F) B (F, F) XB (F, F) -F (1-10) 4%
2O-B (2F) B (2F, 3F) -O2 (2-1) 3%
3-HB (2F) B (2F, 3F) -O2 (2-3) 3%
3-BB (F) B (2F, 3F) -O2 (2-8) 3%
3-HH-V (3-1) 40%
1V2-HH-3 (3-1) 2%
V-HHB-1 (3-5) 4%
5-B (F) BB-3 (3-7) 3%
3-HBB (F) -F (4) 3%
5-HBB (F) -F (4) 3%
3-GB (F) B (F, F) -F (4-11) 3%
3-BB (F) B (F, F) -F (4-12) 4%
3-BB (F) B (F, F) -CF3 (4-13) 4%
4-HBB (2F, 3F) -O2 (5-13) 3%
V-HBB (2F, 3F) -O2 (5-13) 3%
2-BB (2F, 3F) B-4 (5-17) 3%
V-HH2BB (2F, 3F) -O2 (5-20) 3%
NI = 77.9 ° C; Tc <-20 ° C; Δn = 0.123; Δε = 4.4; Vth = 2.05V; γ1 = 85.0mPa · s; ε⊥ = 4.63.

[Example 26]
3-GB (F, F) XB (F, F) -F (1-3) 7%
3-GB (F) B (F, F) XB (F, F) -F (1-9) 3%
5-GB (F) B (F, F) XB (F, F) -F (1-9) 3%
5-BB (F) B (F, F) XB (F, F) -F (1-10) 4%
3-HB (2F) B (2F, 3F) -O2 (2-3) 5%
5-HB (2F) B (2F, 3F) -O2 (2-3) 3%
3-HH-V (3-1) 29%
3-HH-V1 (3-1) 5%
3-HHEBH-3 (3-11) 3%
5-HHB-CL (4) 3%
5-HHB (F) -F (4) 3%
3-GB (F) B (F) B (F) -F (4) 5%
3-BB (F) B (F, F) -F (4-12) 3%
5-H2B (2F, 3F) -O2 (5-2) 3%
3-H1OB (2F, 3F) -O2 (5-3) 3%
5-BB (2F, 3F) -O2 (5-6) 3%
V-HHB (2F, 3F) -O4 (5-7) 3%
V2-HHB (2F, 3F) -O2 (5-7) 3%
3-HDhB (2F, 3F) -O2 (5-12) 3%
2-BB (2F, 3F) B-3 (5-17) 3%
V-H2BBB (2F, 3F) -O2 (5-21) 3%
NI = 90.7 ° C; Tc <-20 ° C; Δn = 0.111; Δε = 5.1; Vth = 1.99V; γ1 = 169.8mPa · s; ε⊥ = 5.96.

[Example 27]
3-GB (F) B (F, F) XB (F, F) -F (1-9) 4%
5-GB (F) B (F, F) XB (F, F) -F (1-9) 3%
3-BB (F) B (F, F) XB (F, F) -F (1-10) 4%
3-HB (2F) B (2F, 3F) -O2 (2-3) 4%
3-HH-V (3-1) 34%
3-HH-V1 (3-1) 4%
3-HB-O2 (3-2) 2%
V-HHB-1 (3-5) 7%
5-HBB (F) B-3 (3-13) 5%
3-GB (F) B (F, F) -F (4-11) 4%
3-BB (F) B (F, F) -CF3 (4-13) 3%
3-GBB (F) B (F, F) -F (4-16) 2%
4-GBB (F) B (F, F) -F (4-16) 2%
2-H1OB (2F, 3F) -O2 (5-3) 3%
3-DhB (2F, 3F) -O2 (5-4) 3%
2-BB (2F, 3F) -O2 (5-6) 3%
V2-BB (2F, 3F) -O2 (5-6) 3%
V-HHB (2F, 3F) -O1 (5-7) 4%
3-HH2B (2F, 3F) -O2 (5-8) 3%
3-HH1OB (2F, 3F) -O2 (5-9) 3%
NI = 79.4 ° C; Tc <-20 ° C; Δn = 0.107; Δε = 4.3; Vth = 1.98V; γ1 = 116.3mPa · s; ε⊥ = 5.59.

[Example 28]
3-GB (F) B (F, F) XB (F, F) -F (1-9) 4%
5-GB (F) B (F, F) XB (F, F) -F (1-9) 3%
3-BB (F) B (F, F) XB (F, F) -F (1-10) 4%
3-HB (2F) B (2F, 3F) -O2 (2-3) 4%
3-HH-V (3-1) 34%
3-HH-V1 (3-1) 4%
3-HB-O2 (3-2) 2%
V-HHB-1 (3-5) 7%
5-HBB (F) B-3 (3-13) 5%
3-GB (F) B (F, F) -F (4-11) 4%
3-BB (F) B (F, F) -CF3 (4-13) 3%
3-GBB (F) B (F, F) -F (4-16) 2%
4-GBB (F) B (F, F) -F (4-16) 2%
V-HB (2F, 3F) -O2 (5-1) 3%
3-DhB (2F, 3F) -O2 (5-4) 3%
3-BB (2F, 3F) -O2 (5-6) 3%
V2-BB (2F, 3F) -O2 (5-6) 3%
3-HH1OB (2F, 3F) -O2 (5-9) 3%
V-HBB (2F, 3F) -O4 (5-13) 4%
5-HFLF4-3 (5-24) 3%
NI = 77.8 ° C; Tc <-20 ° C; Δn = 0.110; Δε = 4.2; Vth = 2.01V; γ1 = 118.5 mPa · s; ε⊥ = 5.69.

Comparing Example 1 and Comparative Example 1, the value of ε⊥ in Example 1 is larger, and the liquid crystal molecule has a large dielectric constant in the minor axis direction. Further, comparing Example 2 and Comparative Example 2, the value of ε⊥ in Example 2 is larger, and the liquid crystal molecule has a large dielectric constant in the minor axis direction. Therefore, it is concluded that the composition of the present invention has excellent properties.

The liquid crystal composition of the present invention can be used for liquid crystal monitors, liquid crystal televisions and the like.

Claims (18)

It contains at least one compound selected from the compound represented by the formula (1) as the first component and at least one compound selected from the compound represented by the formula (2) as the second component, and is positive. A liquid crystal composition having dielectric anisotropy.

In formulas (1) and (2), R ¹ is an alkyl having 1 to 12 carbon atoms, an alkoxy having 1 to 12 carbon atoms, or an alkenyl having 2 to 12 carbon atoms; R ² and R ³ are hydrogens. , Alkyl with 1 to 12 carbon atoms, alkoxy with 1 to 12 carbon atoms, alkenyl with 2 to 12 carbon atoms, or alkenyloxy with 2 to 12 carbon atoms; rings A and B are 1,4-cyclohexylene. , 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced with fluorine, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl, or tetrahydropyran-2,5 -Diyl; rings C and E are 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, and at least one hydrogen is fluorine or chlorine. 1,4-phenylene, naphthalene-2,6-diyl replaced with, naphthalene-2,6-diyl, chroman-2,6-diyl, or at least one hydrogen in which at least one hydrogen has been replaced with fluorine or chlorine. Chroman-2,6-diyl in which hydrogen has been replaced with fluorine or chlorine, but at least one of rings C and E is 1,4-phenylene in which at least one hydrogen has been replaced with fluorine; Ring D is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4. 5-Trifluoronaphthalene-2,6-diyl, 7,8-difluorochroman-2,6-diyl, 3,4,5,6-tetrafluorofluorene-2,7-diyl, 4,6-difluorodibenzofuran- 3,7-diyl, 4,6-difluorodibenzothiophene-3,7-diyl, or 1,1,6,7-tetrafluoroindan-2,5-diyl; Z ¹ and Z ² are single-bonded , ethylene, vinylene, methyleneoxy, carbonyloxy or difluoromethyleneoxy,; ^{Z 3} and ^{Z 4} is a single bond, ethylene, vinylene, methyleneoxy or carbonyloxy,; ^{X 1} and ^{X 2} is hydrogen or Fluorine; Y ¹ is fluorine, chlorine, an alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, and 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. Alkoxy, or an alkenyloxy having 2 to 12 carbon atoms in which at least one hydrogen is replaced with fluorine or chlorine; a is 1, 2, 3, or 4; b and c are 0, 1, 2 , Or 3; d is 0 or 1; and the sum of a and b is 4 or less; the sum of c and d is 1, 2, or 3.
The liquid crystal composition according to claim 1, which contains at least one compound selected from the compounds represented by the formulas (1-1) to (1-14) as the first component.

In formulas (1-1) to (1-14), R ¹ is an alkyl having 1 to 12 carbon atoms, an alkoxy having 1 to 12 carbon atoms, or an alkenyl having 2 to 14 carbon atoms; X ¹ , X. ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ , X ⁸ , X ⁹ , X ¹⁰ , X ¹¹ , X ¹² , X ¹³ , and X ¹⁴ are hydrogen or fluorine; Y ¹ is Fluorine, chlorine, alkyl with 1 to 12 carbon atoms in which at least one hydrogen is replaced with fluorine or chlorine, alkoxy with 1 to 12 carbon atoms in which at least one hydrogen is replaced with fluorine or chlorine, or at least one hydrogen An alkenyloxy having 2 to 12 carbon atoms replaced with fluorine or chlorine. The liquid crystal composition according to claim 1 or 2, which contains at least one compound selected from the compounds represented by the formulas (2-1) to (2-38) as the second component.

In formulas (2-1) to (2-38), R ² and R ³ are alkyls having 1 to 12 carbon atoms, alkoxys having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, or 2 carbon atoms. To 12 alkoxyoxy. The invention according to any one of claims 1 to 3, wherein the proportion of the first component is in the range of 5% by mass to 50% by mass, and the proportion of the second component is in the range of 2% by mass to 50% by mass. Liquid crystal composition. The liquid crystal composition according to any one of claims 1 to 4, which contains at least one compound selected from the compounds represented by the formula (3) as the third component.

In formula (3), R ⁴ and R ⁵ are alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, or at least one hydrogen being replaced with fluorine or chlorine. It is an alkenyl having 2 to 12 carbon atoms; ring F and ring G are 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 2,5-difluoro-1,4. -Phenylene; Z ⁵ is single bond, ethylene, vinylene, methyleneoxy, or carbonyloxy; e is 1, 2, or 3. The liquid crystal composition according to any one of claims 1 to 5, which contains at least one compound selected from the compounds represented by the formulas (3-1) to (3-13) as the third component. ..

In the formula (3-13) from equation (3-1), ^{R 4} and ^{R 5} are alkyl of from 1 to 12 carbons, alkoxy having 1 to 12 carbons, from 2 to 12 carbons, alkenyl or at least one, An alkenyl having 2 to 12 carbon atoms in which hydrogen is replaced with fluorine or chlorine. The liquid crystal composition according to claim 5 or 6, wherein the proportion of the third component is in the range of 10% by mass to 90% by mass. The liquid crystal composition according to any one of claims 1 to 7, which contains at least one compound selected from the compounds represented by the formula (4) as the fourth component.

In formula (4), R ⁶ is an alkyl with 1 to 12 carbons, an alkoxy with 1 to 12 carbons, or an alkenyl with 2 to 12 carbons; ring J is 1,4-cyclohexylene, 1,4. -Phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3-dioxane -2,5-diyl, or tetrahydropyran-2,5-diyl; Z ⁶ is a single bond, ethylene, or carbonyloxy; X ¹⁵ and X ¹⁶ are hydrogen or fluorine; Y ² is , Fluorine, chlorine, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, alkoxy having 1 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine, or at least one hydrogen. Is an alkenyloxy having 2 to 12 carbon atoms replaced with fluorine or chlorine; f is 1, 2, 3, or 4. The liquid crystal composition according to any one of claims 1 to 6, which contains at least one compound selected from the compounds represented by the formulas (4-1) to (4-16) as the fourth component. ..

In formulas (4-1) to (4-16), R ⁶ is an alkyl having 1 to 12 carbon atoms, an alkoxy having 1 to 12 carbon atoms, or an alkenyl having 2 to 12 carbon atoms. The liquid crystal composition according to claim 8 or 9, wherein the proportion of the fourth component is in the range of 5% by mass to 40% by mass. The liquid crystal composition according to any one of claims 1 to 10, which contains at least one compound selected from the compounds represented by the formula (5) as the fifth component.

In formula (5), R ⁷ and R ⁸ are hydrogen, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, or alkenyloxy having 2 to 12 carbon atoms. Ring K and Ring M are 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, naphthalene-2,6-diyl, at least one hydrogen. Is naphthalene-2,6-diyl, chroman-2,6-diyl replaced with fluorine or chlorine, or chroman-2,6-diyl in which at least one hydrogen is replaced with fluorine or chlorine; ring L , 2,3-Difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4,5-tri Fluoronaphthalene-2,6-diyl, 7,8-difluorochroman-2,6-diyl, 3,4,5,6-tetrafluorofluorene-2,7-diyl, 4,6-difluorodibenzofuran-3,7 - diyl, 4,6-difluoro-dibenzothiophene-3,7-diyl, or 1,1,6,7- be tetrafluoro indane-2,5-diyl; ^{Z 7} and ^{Z 8} are a single bond, ethylene, It is vinylene, methyleneoxy, or carbonyloxy; g is 0, 1, 2, or 3; h is 0 or 1; and the sum of g and h is less than or equal to 3. The liquid crystal composition according to any one of claims 1 to 11, which contains at least one compound selected from the compounds represented by the formulas (5-1) to (5-31) as the fifth component. ..

In formulas (5-1) to (5-31), R ⁷ and R ⁸ are hydrogen, alkyl with 1 to 12 carbon atoms, alkoxy with 1 to 12 carbon atoms, alkenyl with 2 to 12 carbon atoms, or carbon. Numbers 2 to 12 of alkoxyoxy. The liquid crystal composition according to claim 11 or 12, wherein the proportion of the fifth component is in the range of 2% by mass to 50% by mass. The upper limit temperature of the nematic phase is 70 ° C. or higher, the optical anisotropy of measurement at 25 ° C. at a wavelength of 589 nm is 0.07 or higher, and the dielectric anisotropy of measurement at 25 ° C. at a frequency of 1 kHz is 2 or higher. The liquid crystal composition according to any one of claims 1 to 13. A liquid crystal display element containing the liquid crystal composition according to any one of claims 1 to 14. The liquid crystal display element according to claim 15, wherein the operation mode of the liquid crystal display element is the FFS mode, and the drive method of the liquid crystal display element is the active matrix method. The liquid crystal display element according to claim 15, wherein the operation mode of the liquid crystal display element is a TN mode, an ECB mode, an OCB mode, an IPS mode, or an FPA mode, and the drive method of the liquid crystal display element is an active matrix method. Use of the liquid crystal composition according to any one of claims 1 to 14 in a liquid crystal display element.