JP2020079215A - Liquid crystal compound - Google Patents

Abstract

（式中、Ｒ^ｉ１及びＲ^ｉ２はそれぞれ独立して、炭素原子数１から１５のアルキル基等を表し、Ａ^ｉ１及びＡ^ｉ２はそれぞれ独立して、１，４−シクロへキシレン基等を表し、Ｚ^ｉ１及びＺ^ｉ２はそれぞれ独立して、−ＣＨ_２Ｏ−等を表し、ｎ^ｉ１及びｍ^ｉ１はそれぞれ独立して０、１又は２を表し、Ｘ^ｉはフッ素原子等を表し、Ｙ^ｉは−Ｏ−等を表す。）で表される化合物。
【選択図】なしPROBLEM TO BE SOLVED: To provide a liquid crystal compound having a low viscosity and a negative dielectric anisotropy (Δε).
SOLUTION: General formula (I):

(In the formula, R ⁱ¹ and R ⁱ² each independently represent an alkyl group having 1 to 15 carbon atoms, etc., and A ⁱ¹ and A ⁱ² each independently represent a 1,4-cyclohexylene group or the like. , Z ⁱ¹ and Z ⁱ² each independently represent —CH ₂ O—, etc., n ⁱ¹ and m ⁱ¹ each independently represent 0, 1 or 2, X ⁱ represents a fluorine atom or the like, and Y ⁱ Represents -O-, etc.).
[Selection diagram] None

Description

  The present invention relates to a liquid crystal compound and a liquid crystal composition containing the same.

  Liquid crystal display devices are used in various electrical appliances for home use, measuring instruments, automobile panels, word processors, electronic notebooks, printers, computers, televisions, etc., including clocks and calculators. Typical liquid crystal display methods are TN (twisted nematic) type, STN (super twisted nematic) type, DS (dynamic light scattering) type, GH (guest host) type, IPS (in-plane switching) type. Type, OCB (optical compensation birefringence) type, ECB (voltage controlled birefringence) type, VA (vertical alignment) type, CSH (color super homeotropic) type, FLC (ferroelectric liquid crystal) and the like. Further, examples of the liquid crystal display drive system include static drive, multiplex drive, simple matrix system, and active matrix (AM) system driven by TFT (thin film transistor) or TFD (thin film diode).

Among them, in the display system such as IPS type, ECB type, VA type, or CSH type, a liquid crystal composition having a negative dielectric anisotropy (Δε) is used. These liquid crystal compositions have a low voltage drive, a fast response, and a wide operating temperature range, that is, a large absolute value of Δε, a low viscosity, and a high nematic phase-isotropic liquid phase transition temperature (T _ni ). In particular, in a VA type display system driven by AM, which is applied to a television or the like, high-speed response is important, so that the liquid crystal composition is particularly required to have low viscosity.

（式中、Ｒ^１及びＲ^２は各々独立して炭素原子数１から１５のアルキル基、炭素原子数２から１５のアルケニル基又は炭素原子数２から１５のアルキニル基を表し、ｍ及びｎは各々独立して０又は１を表す。） So far, the following compounds having a dibenzofuran ring substituted with two fluorine atoms have been reported, but a compound having a dibenzofuran ring substituted with one fluorine atom has not been disclosed (Patent Document 1 and Patent Document 2).

(In the formula, R ¹ and R ² each independently represent an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms or an alkynyl group having 2 to 15 carbon atoms, and m and n are Each independently represents 0 or 1.)

German Patent Application Publication No. 102015002298 Patent No. 4379857

  The problem to be solved by the present invention is to provide a liquid crystal compound having low viscosity and negative dielectric anisotropy (Δε), and at the same time to provide a liquid crystal composition and a liquid crystal display device using the compound as a constituent member. Especially.

  In order to solve the above problems, the present inventors have studied various compounds, as a result, found that a compound having a condensed ring substituted with the following one fluorine atom can effectively solve the problem, The invention was completed.

（式中、Ｒ^ｉ１及びＲ^ｉ２はそれぞれ独立して、塩素原子、臭素原子、ヨウ素原子、水酸基、−ＢＲ^１Ｒ^２（式中、Ｒ^１及びＲ^２はそれぞれ独立して、水酸基、炭素原子数１から４のアルコキシ基を表すか、Ｒ^１及びＲ^２は互いに結合して環状の構造となり−Ｏ−（ＣＲ^３Ｒ^４）_ｎ−Ｏ−（式中、Ｒ^３及びＲ^４はそれぞれ独立して、水素原子又は炭素原子数１から４のアルキル基を表し、ｎは２又は３を表し、複数存在するＣＲ^３Ｒ^４は同一であっても異なっていてもよい）を表す）、炭素原子数１から１５のアルキル基又は炭素原子数２から１５のアルケニル基を表し、該アルキル基又はアルケニル基中に存在する１個の−ＣＨ_２−又は隣接していない２個以上の−ＣＨ_２−はそれぞれ独立して−Ｏ−、−Ｓ−、−ＣＯ−、−ＣＯＯ−、−ＯＣＯ−、−ＳＯＯ−Ｏ−又は−Ｃ≡Ｃ−により置き換えられても良く、また、該アルキル基又はアルケニル基中に存在する水素原子はフッ素原子に置換されても良く、
Ａ^ｉ１及びＡ^ｉ２はそれぞれ独立して
（ａ）１，４−シクロへキシレン基（この基中に存在する１個の−ＣＨ_２−又は隣接していない２個以上の−ＣＨ_２−は−Ｏ−又は−Ｓ−に置き換えられても良い。）、
（ｂ）１，４−フェニレン基（この基中に存在する１個の−ＣＨ＝又は隣接していない２個以上の−ＣＨ＝は−Ｎ＝に置き換えられても良く、この基中に存在する１つの水素原子はフッ素原子に置換されても良い。）、及び
（ｃ）１，４−シクロヘキセニレン基、ナフタレン−２，６−ジイル基、１，２，３，４−テトラヒドロナフタレン−２，６−ジイル基又はデカヒドロナフタレン−２，６−ジイル基（これらの基中に存在する水素原子はフッ素原子に置換されても良く、また、ナフタレン−２，６−ジイル基又は１，２，３，４−テトラヒドロナフタレン−２，６−ジイル基中に存在する１個の−ＣＨ＝又は隣接していない２個以上の−ＣＨ＝は−Ｎ＝に置き換えられても良い。）
からなる群より選ばれる基を表し、
Ｚ^ｉ１及びＺ^ｉ２はそれぞれ独立して、−ＣＨ_２Ｏ−、−ＯＣＨ_２−、−ＣＦ_２Ｏ−、−ＯＣＦ_２−、−ＣＯＯ−、−ＯＣＯ−、−ＣＨ_２ＣＨ_２−、−ＣＦ_２ＣＦ_２−、−ＣＨ＝ＣＨ−、−ＣＦ＝ＣＦ−、−Ｃ≡Ｃ−又は単結合を表し、
ｎ^ｉ１及びｍ^ｉ１はそれぞれ独立して０、１又は２を表すが、ｎ^ｉ１が２を表しＡ^ｉ１及びＺ^ｉ１が複数存在する場合、それらは同一であっても異なっていてもよく、また、ｍ^ｉ１が２を表しＡ^ｉ２及びＺ^ｉ２が複数存在する場合、それらは同一であっても異なっていてもよく、
Ｘ^ｉはフッ素原子、塩素原子、シアノ基、トリフルオロメチル基又はトリフルオロメトキシ基を表し、
Ｙ^ｉは−Ｏ−、−Ｓ−、−ＳＯ−、−ＳＯＯ−、−ＣＦ_２−、−ＣＯ−又は−ＣＨ_２−を表す。）
で表される化合物を提供する。 One aspect of the present invention is represented by the general formula (I):

(In the formula, R ⁱ¹ and R ⁱ² are each independently a chlorine atom, a bromine atom, an iodine atom, a hydroxyl group, -BR ¹ R ² (In the formula, R ¹ and R ² are each independently a hydroxyl group, a carbon atom. Represents an alkoxy group of the formulas 1 to 4, or R ¹ and R ² are bonded to each other to form a cyclic structure —O—(CR ³ R ⁴ ) _n —O— (wherein R ³ and R ⁴ are each independently Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, n represents 2 or 3, and a plurality of CR ³ R ^{4 s} may be the same or different)), carbon It represents an alkyl group having 1 to 15 atoms or an alkenyl group having 2 to 15 carbon atoms, and one —CH ₂ — present in the alkyl group or alkenyl group or two or more —CH ₂ which are not adjacent to each other. Each -may be independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -SOO-O- or -C≡C-, and the alkyl group or The hydrogen atom present in the alkenyl group may be replaced by a fluorine atom,
A ⁱ¹ and A ⁱ² are each independently (a) a 1,4-cyclohexylene group (one —CH ₂ — present in this group or two or more —CH ₂ — not adjacent to each other is — It may be replaced with O- or -S-).
(B) 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ which are not adjacent to each other may be replaced by —N═, which is present in this group) May be substituted with a fluorine atom), and (c) 1,4-cyclohexenylene group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene- 2,6-diyl group or decahydronaphthalene-2,6-diyl group (the hydrogen atom present in these groups may be replaced by a fluorine atom, and the naphthalene-2,6-diyl group or 1, (One -CH= present in the 2,3,4-tetrahydronaphthalene-2,6-diyl group or two or more non-adjacent -CH= may be replaced by -N=.)
Represents a group selected from the group consisting of
Z ⁱ¹ and Z ⁱ² are each independently —CH ₂ O—, —OCH ₂ —, —CF ₂ O—, —OCF ₂ —, —COO—, —OCO—, —CH ₂ CH ₂ —, —CF. _{2 CF 2 -, - CH =} CH -, - CF = CF -, - C≡C- or a single bond,
n ⁱ¹ and m ⁱ¹ each independently represent 0, 1 or 2, but when n ⁱ¹ represents 2 and a plurality of A ⁱ¹ and Z ⁱ¹ are present, they may be the same or different, and , M ⁱ¹ represents 2 and a plurality of A ⁱ² and Z ⁱ² are present, they may be the same or different,
X ⁱ represents a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group or a trifluoromethoxy group,
Y ⁱ is -O -, - S -, - SO -, - SOO -, - CF 2 -, - CO- or -CH ₂ - represents a. )
A compound represented by:

  Another aspect of the present invention provides a composition containing one or more compounds represented by general formula (I), and a liquid crystal display device using the composition.

  The compound of the present invention is a liquid crystal compound having a low viscosity and a negative dielectric anisotropy (Δε). Therefore, the compound of the present invention is useful as a constituent component of a liquid crystal composition for a liquid crystal display device that requires a high-speed response.

  Hereinafter, preferred embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments.

In order to lower γ ₁ , it is preferable that R ⁱ¹ and R ⁱ² each independently represent an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms. It is more preferable to represent an alkyl group having 5 or an alkenyl group having 2 to 5 carbon atoms. Further, the alkyl group and alkenyl group are preferably linear. In order to increase the absolute value of Δε, it is preferable that R ⁱ¹ and R ⁱ² each independently represent an alkoxy group having 1 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, and It is more preferably an alkoxy group having 1 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms. In order to increase the miscibility with other liquid crystal components, R ⁱ¹ and R ⁱ² are preferably different, and the alkoxy group is preferably either R ⁱ¹ or R ⁱ² . The hydrogen atom present in R ⁱ¹ and R ⁱ² may be substituted with a fluorine atom, but is preferably not substituted with a fluorine atom.
When the general formula (I) represents an intermediate, at least one of R ⁱ¹ and R ⁱ² is a chlorine atom, a bromine atom, an iodine atom, a hydroxyl group, a methanesulfonyloxy group, a p-toluenesulfonyloxy group, trifluoromethane. Sulfonyloxy group or -BR ¹ R ² (In the formula, R ¹ and R ² each independently represent a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, or R ¹ and R ² are bonded to each other to form a ring. structure and become _{^{-O- (CR 3 R 4) n}} -O- ( wherein the, ^{R 3} and ^{R 4} each independently represent a hydrogen atom or an alkyl group having a carbon number of 1 to 4, n is 2 or 3 and a plurality of CR ³ R ^{4 present} may be the same or different)).

から選ばれる基を表すことが好ましい。具体的には、γ_１を低下させるためには、Ａ^ｉ１及びＡ^ｉ２は各々独立して、トランス−１，４−シクロヘキシレン基、無置換の１，４−フェニレン基、２−フルオロ−１，４−フェニレン基又は３−フルオロ−１，４−フェニレン基であることが好ましく、トランス−１，４−シクロヘキシレン基であることが更に好ましい。他の液晶成分との混和性を向上させるためには、Ａ^ｉ１及びＡ^ｉ２は各々独立して、トランス−１，４−シクロヘキシレン基、２−フルオロ−１，４−フェニレン基又は３−フルオロ−１，４−フェニレン基であることが好ましい。Ｔ_ｎｉを上昇させるためには、Ａ^ｉ１及びＡ^ｉ２は各々独立して、無置換の１，４−フェニレン基、無置換の１，４−シクロヘキセニレン基、１，４−シクロヘキセニレン基又は無置換のナフタレン−２，６−ジイル基であることが好ましい。負に大きなΔεを示すためには、Ａ^ｉ１及びＡ^ｉ２は各々独立して、２−フルオロ−１，４−フェニレン基、３−フルオロ−１，４−フェニレン基又は２，３−ジフルオロ−１，４−フェニレン基であることが好ましい。大きなΔεを示しながら、他の液晶成分との混和性を両立させるためには、Ａ^ｉ１及びＡ^ｉ２中に存在するフッ素原子の数の合計は、１〜４であることが好ましく、１〜３であることが好ましい。 A ⁱ¹ and A ⁱ² are each independently

It is preferable to represent a group selected from Specifically, in order to reduce γ ₁ , A ⁱ¹ and A ⁱ² are each independently a trans-1,4-cyclohexylene group, an unsubstituted 1,4-phenylene group, and 2-fluoro-1. , 4-phenylene group or 3-fluoro-1,4-phenylene group is preferable, and trans-1,4-cyclohexylene group is more preferable. In order to improve miscibility with other liquid crystal components, A ⁱ¹ and A ⁱ² are each independently a trans-1,4-cyclohexylene group, a 2-fluoro-1,4-phenylene group or a 3-fluoro group. It is preferably a -1,4-phenylene group. In order to increase T _ni , A ⁱ¹ and A ⁱ² are each independently an unsubstituted 1,4-phenylene group, an unsubstituted 1,4-cyclohexenylene group or a 1,4-cyclohexenylene group. Alternatively, it is preferably an unsubstituted naphthalene-2,6-diyl group. In order to exhibit a large negative Δε, A ⁱ¹ and A ⁱ² are each independently a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group or a 2,3-difluoro-1 group. , 4-phenylene group is preferred. The total number of fluorine atoms present in A ⁱ¹ and A ⁱ² is preferably 1 to 4 in order to achieve compatibility with other liquid crystal components while exhibiting a large Δε. Is preferred.

In order to reduce γ ₁ , it is preferable that Z ⁱ¹ and Z ⁱ² are each independently a single bond, —CH ₂ CH ₂ —, —CH ₂ O— or —OCH ₂ —, and a single bond or — More preferably CH ₂ CH ₂ —. In order to increase T _ni , Z ⁱ¹ and Z ⁱ² are preferably each independently a single bond, —COO—, —OCO—, —CH═CH— or —C≡C—, and a single bond is preferred. , -CH=CH- or -C≡C- is more preferred. In order to improve the miscibility with other liquid crystal components, Z ⁱ¹ and Z ⁱ² are each independently a single bond, —CH ₂ CH ₂ —, —CH ₂ O— or —OCH ₂ —. preferable. In order to improve long-term reliability of the liquid crystal display device, a single bond is preferable.

independently n ⁱ¹ and ^{m i1,} respectively, preferably represents 0 or ^{1, n i1} and ^{m i1} is more preferably both represent 0.

X ⁱ preferably represents a fluorine atom.

Y ⁱ preferably represents —O—, —S— or —CH ₂ —, more preferably —O— or —S, even more preferably —O—.

（式中、Ｒ^ｉ１及びＲ^ｉ２は一般式（Ｉ）中のＲ^ｉ１及びＲ^ｉ２とそれぞれ同じ意味を表す。）
で表される各化合物が好ましい。 Among the general formulas (I), the following general formulas (I-1) to (I-18):

^(Wherein, each represent the same meaning as ^{R i1} and ^{R i2} in ^{R i1} and ^{R i2} are the general formula (I).)
Each compound represented by is preferable.

Further, among the compounds represented by the above general formulas (I-1) to (I-18), each compound represented by the following formula is preferable.

(Production method)
In the present invention, the compound represented by the general formula (I) can be produced as follows. The spirit and scope of the present invention are not limited by these manufacturing methods.

（式中、Ｒ^ｉ１、Ｒ^ｉ２、Ａ^ｉ１、Ａ^ｉ２、Ｚ^ｉ１、Ｚ^ｉ２、ｎ^ｉ１、ｍ^ｉ１及びＸ^ｉは、一般式（Ｉ）におけるＲ^ｉ１、Ｒ^ｉ２、Ａ^ｉ１、Ａ^ｉ２、Ｚ^ｉ１、Ｚ^ｉ２、ｎ^ｉ１、ｍ^ｉ１及びＸ^ｉとそれぞれ同じ意味を表し、
Ｒ^ｉｍ１及びＲ^ｉｍ２はそれぞれ独立して、水素原子、メチル基、エチル基又はプロピル基を表すか、又はＲ^ｉｍ１及びＲ^ｉｍ２は互いに結合して環状の構造となり−ＣＨ_２−ＣＨ_２−、−ＣＨ_２−ＣＨ_２−ＣＨ_２−、若しくは−ＣＨ_２−Ｃ（ＣＨ_３）_２−ＣＨ_２−を表し、
Ｘ^ｉｍ１はフッ素原子、塩素原子、臭素原子又はヨウ素原子を表し、
Ｘ^ｉｍ２は塩素原子、臭素原子、ヨウ素原子、メタンスルホニルオキシ基、ｐ−トルエンスルホニルオキシ基又はトリフルオロメタンスルホニルオキシ基を表し、
Ｙ^ｉｍ１は−Ｏ−又は−Ｓ−を表す。） (Manufacturing method 1)

(In the formula, R ⁱ¹ , R ⁱ² , A ⁱ¹ , A ⁱ² , Z ⁱ¹ , Z ⁱ² , n ⁱ¹ , m ⁱ¹ and X ⁱ are R ⁱ¹ , R ⁱ² , A ⁱ¹ , A ⁱ² in the general formula (I), Z ⁱ¹ , Z ⁱ² , n ⁱ¹ , m ⁱ¹ and X ⁱ each have the same meaning,
R ^im1 and R ^im2 each independently represent a hydrogen atom, a methyl group, an ethyl group or a propyl group, or R ^im1 and R ^im2 are bonded to each other to form a cyclic structure —CH ₂ —CH ₂ —, — CH ₂ —CH ₂ —CH ₂ — or —CH ₂ —C(CH ₃ ) ₂ —CH ₂ —,
X ^im1 represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom,
X ^im2 represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a p-toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group,
Y ^im1 represents -O- or -S-. )

  The compound represented by the general formula (S-1) is reacted with the compound represented by the general formula (S-2) in the presence of a transition metal catalyst and a base to give the compound represented by the general formula (S-3). Obtainable.

  The transition metal catalyst to be used may be any one as long as it allows the reaction to proceed favorably, and tetrakis(triphenylphosphine)palladium(0), palladium(II) acetate, bis(triphenylphosphine)palladium dichloride. (II), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride or bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(II) dichloride is preferable, Tetrakis(triphenylphosphine)palladium(0), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride or bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloride. More preferably, it is palladium (II). In addition, in order to allow the reaction to proceed appropriately, a phosphine-based ligand such as triphenylphosphine may be added, if necessary.

  The reaction solvent to be used may be any one as long as it allows the reaction to proceed properly, but is preferably an ether solvent such as tetrahydrofuran, diethyl ether or tert-butyl methyl ether, an alcohol solvent such as methanol, ethanol or propanol. Aromatic solvents such as benzene, toluene and xylene are preferable, and tetrahydrofuran, ethanol and toluene are more preferable. Further, water may be used if necessary in order to allow the reaction to proceed appropriately.

  As the base to be used, any base may be used as long as it allows the reaction to proceed suitably, but carbonates such as potassium carbonate, sodium carbonate and cesium carbonate, and phosphates such as tripotassium phosphate and potassium dihydrogen phosphate. Are preferred, and potassium carbonate, cesium carbonate, and tripotassium phosphate are more preferred.

  The reaction temperature may be any number as long as it allows the reaction to proceed appropriately, but it is preferably from room temperature to the temperature at which the solvent used is refluxed, more preferably from 40° C. to the solvent refluxed. It is particularly preferable that the temperature is from 60° C. to the reflux of the solvent.

By intramolecularly reacting the compound represented by the general formula (S-3), in the compound represented by the general formula (I), Y ⁱ is —O— or —S—. The compound represented by 4) can be obtained. This intramolecular reaction can be carried out by deprotonating ^-Yim1- H of the general formula (S-3) with a base to generate an anion.

  Examples of the base used in this case include metal hydrides, metal carbonates, metal phosphates, metal hydroxides, metal carboxylates, metal amides and metals, among which alkali metal hydrides and alkali metals. Phosphates, alkali metal phosphates, alkali metal carbonates, alkali metal hydroxides, alkali metal amides and alkali metals are preferred, and alkali metal phosphates, alkali metal hydrides and alkali metal carbonates are more preferred. As alkali metal hydrides, lithium hydride, sodium hydride and potassium hydride, as alkali metal phosphates, tripotassium phosphate, and as alkali metal carbonates, sodium carbonate, sodium hydrogen carbonate, cesium carbonate, potassium carbonate. And potassium hydrogen carbonate can be preferably mentioned respectively.

  As the reaction solvent, any solvent may be used as long as it allows the reaction to proceed properly, but ether solvents, chlorine solvents, hydrocarbon solvents, aromatic solvents, polar solvents and the like can be preferably used. As the ether solvent, 1,4-dioxane, 1,3-dioxane, tetrahydrofuran, diethyl ether, t-butyl methyl ether, etc., and as the chlorine solvent, dichloromethane, 1,2-dichloroethane, carbon tetrachloride, etc., As the hydrocarbon solvent, pentane, hexane, cyclohexane, heptane, octane, etc., as the aromatic solvent, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc., and as the polar solvent, N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, sulfolane and the like can be mentioned as favorable examples. Among them, ether solvents such as tetrahydrofuran and diethyl ether and polar solvents such as N-methylpyrrolidone are more preferable. Further, each of the above solvents may be used alone, or two or more kinds of solvents may be mixed and used.

  The reaction temperature may be in the reflux temperature range from the freezing point of the solvent, but is preferably 0°C to 180°C.

（式中、Ｒ^ｉ１、Ｒ^ｉ２、Ａ^ｉ１、Ａ^ｉ２、Ｚ^ｉ１、Ｚ^ｉ２、ｎ^ｉ１、ｍ^ｉ１及びＸ^ｉは、一般式（Ｉ）におけるＲ^ｉ１、Ｒ^ｉ２、Ａ^ｉ１、Ａ^ｉ２、Ｚ^ｉ１、Ｚ^ｉ２、ｎ^ｉ１、ｍ^ｉ１及びＸ^ｉとそれぞれ同じ意味を表し、
Ｒ^ｉｍ３及びＲ^ｉｍ４はそれぞれ独立して、水素原子、メチル基、エチル基又はプロピル基を表すか、又はＲ^ｉｍ１及びＲ^ｉｍ２は互いに結合して環状の構造となり−ＣＨ_２−ＣＨ_２−、−ＣＨ_２−ＣＨ_２−ＣＨ_２−、若しくは−ＣＨ_２−Ｃ（ＣＨ_３）_２−ＣＨ_２−を表し、
Ｘ^ｉｍ３はフッ素原子、塩素原子、臭素原子又はヨウ素原子を表し、
Ｘ^ｉｍ４は塩素原子、臭素原子、ヨウ素原子、メタンスルホニルオキシ基、ｐ−トルエンスルホニルオキシ基又はトリフルオロメタンスルホニルオキシ基を表し、
Ｙ^ｉｍ２は−Ｏ−又は−Ｓ−を表す。） (Manufacturing method 2)

(In the formula, R ⁱ¹ , R ⁱ² , A ⁱ¹ , A ⁱ² , Z ⁱ¹ , Z ⁱ² , n ⁱ¹ , m ⁱ¹ and X ⁱ are R ⁱ¹ , R ⁱ² , A ⁱ¹ , A ⁱ² in the general formula (I), Z ⁱ¹ , Z ⁱ² , n ⁱ¹ , m ⁱ¹ and X ⁱ each have the same meaning,
R ^im3 and R ^im4 each independently represent a hydrogen atom, a methyl group, an ethyl group or a propyl group, or R ^im1 and R ^im2 are bonded to each other to form a cyclic structure —CH ₂ —CH ₂ —, — CH ₂ —CH ₂ —CH ₂ — or —CH ₂ —C(CH ₃ ) ₂ —CH ₂ —,
X ^im3 represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom,
X ^im4 represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a p-toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group,
Y ^im2 represents -O- or -S-. )

  A compound represented by the general formula (S-7) is obtained by reacting a compound represented by the general formula (S-5) with a compound represented by (S-6) in the presence of a transition metal catalyst and a base. You can

  The transition metal catalyst, reaction solvent and base used are the same as the transition metal catalyst, reaction solvent and base used in the step of obtaining the compound represented by the general formula (S-3). The reaction temperature is the same as the reaction temperature in the step of obtaining the compound represented by the general formula (S-3).

By intramolecularly reacting the compound represented by the general formula (S-7), among the compounds represented by the general formula (I), Y ⁱ is —O— or —S—. The compound represented by 8) can be obtained. This intramolecular reaction can be performed by deprotonating ^-Yim2- H of the general formula (S-7) with a base to generate an anion.

  The base and reaction solvent used are the same as the base and reaction solvent used in the step of obtaining the compound represented by the general formula (S-4). The reaction temperature is the same as the reaction temperature in the step of obtaining the compound represented by the general formula (S-4).

（式中、Ｒ^ｉ１、Ｒ^ｉ２、Ａ^ｉ１、Ａ^ｉ２、Ｚ^ｉ１、Ｚ^ｉ２、ｎ^ｉ１、ｍ^ｉ１、Ｘ^ｉ及びＹ^ｉは一般式（Ｉ）におけるＲ^ｉ１、Ｒ^ｉ２、Ａ^ｉ１、Ａ^ｉ２、Ｚ^ｉ１、Ｚ^ｉ２、ｎ^ｉ１、ｍ^ｉ１、Ｘ^ｉ及びＹ^ｉとそれぞれ同じ意味を表し、
Ｒ^ｉａ及びＲ^ｉｂはそれぞれ独立して、塩素原子、臭素原子、ヨウ素原子、水酸基、メタンスルホニルオキシ基、ｐ−トルエンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基又は−ＢＲ^１Ｒ^２（式中、Ｒ^１及びＲ^２はそれぞれ独立して、水酸基、炭素原子数１から４のアルコキシ基を表すか、Ｒ^１及びＲ^２は互いに結合して環状の構造となり−Ｏ−（ＣＲ^３Ｒ^４）_ｎ−Ｏ−（式中、Ｒ^３及びＲ^４はそれぞれ独立して、水素原子又は炭素原子数１から４のアルキル基を表し、ｎは２又は３を表し、複数存在するＣＲ^３Ｒ^４は同一であっても異なっていてもよい）を表す。）を表し、
Ｒ^ｉｃ及びＲ^ｉｄはそれぞれ独立して、塩素原子、臭素原子、ヨウ素原子、水酸基、メタンスルホニルオキシ基、ｐ−トルエンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基、−ＢＲ^５Ｒ^６（式中、Ｒ^５及びＲ^６はそれぞれ独立して、水酸基、炭素原子数１から４のアルコキシ基を表すか、Ｒ^５及びＲ^６は互いに結合して環状の構造となり−Ｏ−（ＣＲ^７Ｒ^８）_ｎ１−Ｏ−（式中、Ｒ^７及びＲ^８はそれぞれ独立して、水素原子又は炭素原子数１から４のアルキル基を表し、ｎ１は２又は３を表し、複数存在するＣＲ^７Ｒ^８は同一であっても異なっていてもよい）を表す。）又は−ＺｎＸ^ｉｍ５（式中、Ｘ^ｉｍ５は塩素原子、臭素原子又ヨウ素原子を表す。）を表す。） (Manufacturing method 3)

(In the formula, R ⁱ¹ , R ⁱ² , A ⁱ¹ , A ⁱ² , Z ⁱ¹ , Z ⁱ² , n ⁱ¹ , m ⁱ¹ , X ^i, and Y ⁱ are R ⁱ¹ , R ⁱ² , A ⁱ¹ , and A in the general formula (I). ⁱ² , Z ⁱ¹ , Z ⁱ² , n ⁱ¹ , m ⁱ¹ , X ^i, and Y ⁱ have the same meanings,
R ^ia and R ^ib are each independently a chlorine atom, a bromine atom, an iodine atom, a hydroxyl group, a methanesulfonyloxy group, a p-toluenesulfonyloxy group, a trifluoromethanesulfonyloxy group or -BR ¹ R ² (in the formula, R ¹ and R ² each independently represent a hydroxyl group or an alkoxy group having 1 to 4 carbon atoms, or R ¹ and R ² are bonded to each other to form a cyclic structure —O—(CR ³ R ⁴ ) _n —. O- (in the formula, R ³ and R ⁴ each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, n represents 2 or 3, and a plurality of CR ³ R ^{4 s} are the same; May be present or different))),
R ^ic and R ^id are each independently a chlorine atom, a bromine atom, an iodine atom, a hydroxyl group, a methanesulfonyloxy group, a p-toluenesulfonyloxy group, a trifluoromethanesulfonyloxy group, -BR ⁵ R ⁶ (in the formula, R ⁵ and R ⁶ each independently represent a hydroxyl group or an alkoxy group having 1 to 4 carbon atoms, or R ⁵ and R ⁶ are bonded to each other to form a cyclic structure —O—(CR ⁷ R ⁸ ) _{n 1} — O-(in the formula, R ⁷ and R ⁸ each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, n1 represents 2 or 3, and a plurality of CR ⁷ R ⁸ are the same. May be present or different)) or —ZnX ^im5 (in the formula, X ^im5 represents a chlorine atom, a bromine atom or an iodine atom). )

For example, R ^ia and R ^ib are chlorine atom, bromine atom, iodine atom, methanesulfonyloxy group, p-toluenesulfonyloxy group or trifluoromethanesulfonyloxy group, and R ^ic and R ^id are -BR ⁵ R ⁶ or -ZnX ^im5 is represented by the general formula (I) by reacting the compound represented by the general formula (Ia) with the compound represented by (S-9) in the presence of a transition metal catalyst and/or a base. Can be obtained. Further, the compound represented by the general formula (Ib) is reacted with the compound represented by (S-10) in the presence of a transition metal catalyst and/or a base to obtain a compound represented by the general formula (I). You can The reaction solvent, transition metal catalyst and base used are the same as the reaction solvent, transition metal catalyst and base used in the step of obtaining the compound represented by the general formula (S-3). The reaction temperature is the same as the reaction temperature in the step of obtaining the compound represented by the general formula (S-3).

Further, for example, when R ^ia and R ^ib are hydroxyl groups and R ^ic and R ^id are chlorine atom, bromine atom or iodine atom, the compound represented by the general formula (Ia) is represented by (S-9). The compound represented by the general formula (I) can be obtained by reacting with the compound represented by the presence of a base. Moreover, the compound represented by the general formula (I) can be obtained by reacting the compound represented by the general formula (Ib) with the compound represented by the (S-10) in the presence of a base.

(Composition)
Since the compound represented by the general formula (I) exhibits a negative dielectric anisotropy (Δε), the composition of the present invention containing the compound represented by the general formula (I) has a negative dielectric anisotropy. It is preferable to have a rate anisotropy.

  In the composition of the present invention, when the content of the compound represented by the general formula (I) is small, the effect does not appear. %)), preferably 2% or more, more preferably 5% or more, still more preferably 10% or more. Further, since a large content causes problems such as precipitation, the upper limit is preferably 70% or less, more preferably 60% or less, further preferably 50% or less, 40 % Or less is particularly preferable. The compound represented by the general formula (I) may be used alone or in combination of two or more. A compound other than the compound represented by formula (I) may be used to adjust the physical properties of the liquid crystal composition, and a compound having no liquid crystal phase may be used in addition to the compound having a liquid crystal phase. It can also be added.

  The composition of the present invention contains at least one compound represented by the general formula (I) as the first component, and is selected from the group consisting of the following second and third components as other components. It is preferable to contain at least one component.

（式中、
Ｒ^Ｎ１１、Ｒ^Ｎ１２、Ｒ^Ｎ２１、Ｒ^Ｎ２２、Ｒ^Ｎ３１及びＲ^Ｎ３２はそれぞれ独立して炭素原子数１〜８のアルキル基を表し、該アルキル基中の１個又は非隣接の２個以上の−ＣＨ_２−はそれぞれ独立して−ＣＨ＝ＣＨ−、−Ｃ≡Ｃ−、−Ｏ−、−ＣＯ−、−ＣＯＯ−又は−ＯＣＯ−によって置換されていてもよく、
Ａ^Ｎ１１、Ａ^Ｎ１２、Ａ^Ｎ２１、Ａ^Ｎ２２、Ａ^Ｎ３１及びＡ^Ｎ３２はそれぞれ独立して
（ａ１１）１，４−シクロヘキシレン基（この基中に存在する１個の−ＣＨ_２−又は隣接していない２個以上の−ＣＨ_２−は−Ｏ−に置き換えられてもよい。）
（ｂ１１）１，４−フェニレン基（この基中に存在する１個の−ＣＨ＝又は隣接していない２個以上の−ＣＨ＝は−Ｎ＝に置き換えられてもよい。）及び
（ｃ１１）ナフタレン−２，６−ジイル基、１，２，３，４−テトラヒドロナフタレン−２，６−ジイル基又はデカヒドロナフタレン−２，６−ジイル基（ナフタレン−２，６−ジイル基又は１，２，３，４−テトラヒドロナフタレン−２，６−ジイル基中に存在する１個の−ＣＨ＝又は隣接していない２個以上の−ＣＨ＝は−Ｎ＝に置き換えられても良い。）
からなる群より選ばれる基を表し、上記の基（ａ１１）、基（ｂ１１）及び基（ｃ１１）はそれぞれ独立してシアノ基、フッ素原子又は塩素原子で置換されていても良く、
Ｚ^Ｎ１１、Ｚ^Ｎ１２、Ｚ^Ｎ２１、Ｚ^Ｎ２２、Ｚ^Ｎ３１及びＺ^Ｎ３２はそれぞれ独立して単結合、−ＣＨ_２ＣＨ_２−、−（ＣＨ_２）_４−、−ＯＣＨ_２−、−ＣＨ_２Ｏ−、−ＣＯＯ−、−ＯＣＯ−、−ＯＣＦ_２−、−ＣＦ_２Ｏ−、−ＣＨ＝Ｎ−Ｎ＝ＣＨ−、−ＣＨ＝ＣＨ−、−ＣＦ＝ＣＦ−又は−Ｃ≡Ｃ−を表し、
Ｘ^Ｎ２１は水素原子又はフッ素原子を表し、
Ｔ^Ｎ３１は−ＣＨ_２−又は酸素原子を表し、
ｎ^Ｎ１１、ｎ^Ｎ１２、ｎ^Ｎ２１、ｎ^Ｎ２２、ｎ^Ｎ３１及びｎ^Ｎ３２はそれぞれ独立して０〜３の整数を表すが、ｎ^Ｎ１１＋ｎ^Ｎ１２、ｎ^Ｎ２１＋ｎ^Ｎ２２及びｎ^Ｎ３１＋ｎ^Ｎ３２はそれぞれ独立して１、２又は３であり、Ａ^Ｎ１１〜Ａ^Ｎ３２、Ｚ^Ｎ１１〜Ｚ^Ｎ３２が複数存在する場合は、それらは同一であっても異なっていても良い。ただし、一般式（Ｎ−２）及び一般式（Ｎ−３）において一般式（Ｎ−１）で表される化合物は除き、また、一般式（Ｎ−３）において一般式（Ｎ−２）で表される化合物は除く。） The second component preferably contains one or more compounds selected from the group of compounds represented by formulas (N-1), (N-2) and (N-3). These compounds correspond to dielectrically negative compounds (the sign of Δε is negative and the absolute value thereof is larger than 2).

(In the formula,
^RN11 , ^RN12 , ^RN21 , ^RN22 , ^RN31 and ^RN32 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent-in the alkyl group- CH ₂ — may be each independently substituted by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—,
A ^N11 , A ^N12 , A ^N21 , A ^N22 , A ^N31 and A ^N32 are each independently (a11) 1,4-cyclohexylene group (one —CH ₂ — present in this group or adjacent to each other). no more than one -CH ₂ - may be replaced by -O-).
(B11) 1,4-phenylene group (one -CH= present in this group or two or more -CH= which are not adjacent to each other may be replaced with -N=) and (c11). Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or 1,2 , 3,4-tetrahydronaphthalene-2,6-diyl group may have one -CH= or two or more non-adjacent -CH=, which may be replaced by -N=.)
Represents a group selected from the group consisting of, the group (a11), the group (b11) and the group (c11) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,
Z ^N11 , Z ^N12 , Z ^N21 , Z ^N22 , Z ^N31 and Z ^N32 are each independently a single bond, —CH ₂ CH ₂ —, —(CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—. _{, -COO -, - OCO -,} - OCF 2 -, - CF 2 O -, - CH = N-N = CH -, - CH = CH -, - represents CF = CF- or -C≡C-,
X ^N21 represents a hydrogen atom or a fluorine atom,
T ^N31 is -CH ₂ - represents an or an oxygen atom,
n ^N11 , n ^N12 , n ^N21 , n ^N22 , n ^N31 and n ^N32 each independently represent an integer of 0 to 3, and n ^N11 +n ^N12 , n ^N21 +n ^N22 and n ^N31 +n ^N32 are each independently. When there are a plurality of A ^{N11 to} A ^N32 and Z ^{N11 to} Z ^N32 , they may be the same or different. However, in general formula (N-2) and general formula (N-3), the compound represented by general formula (N-1) is excluded, and in general formula (N-3), general formula (N-2) The compounds represented by are excluded. )

  The compounds represented by the general formulas (N-1), (N-2) and (N-3) are dielectrically negative compounds (the sign of Δε is negative and the absolute value thereof is larger than 2). Although applicable, compounds having a negative Δε and an absolute value larger than 3 are preferable.

In formulas (N-1), (N-2) and (N-3), R ^N11 , R ^N12 , R ^N21 , R ^N22 , R ^N31 and R ^N32 each independently have 1 to 8 carbon atoms. Preferred is an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms, and an alkyl group having 1 to 5 carbon atoms and the number of carbon atoms. An alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms is preferable, and an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is More preferably, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is more preferable, and an alkenyl group having 3 carbon atoms (propenyl group) is particularly preferable. Among them, by using a compound in which at least one of R ^N11 and R ^N12 represents an alkenyl group and a compound represented by the general formula (I) in combination, the decrease in voltage holding ratio (VHR) is significantly suppressed. be able to. Similarly, by using a compound in which at least one of R ^N21 and R ^N22 represents an alkenyl group and a compound represented by the general formula (I) in combination, the decrease in voltage holding ratio (VHR) is significantly suppressed. It is possible to reduce the voltage holding ratio (VHR) by using a compound in which at least one of R ^N31 and R ^N32 represents an alkenyl group in combination with a compound represented by the general formula (I). Can be significantly suppressed.

  When the ring structure to which it is bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and carbon An alkenyl group having 4 to 5 atoms is preferable, and when the ring structure to which it is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane, a linear alkyl group having 1 to 5 carbon atoms, a straight chain Preferred are an alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms. In order to stabilize the nematic phase, the total number of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear.

Ａ^Ｎ１１、Ａ^Ｎ１２、Ａ^Ｎ２１、Ａ^Ｎ２２、Ａ^Ｎ３１及びＡ^Ｎ３２はそれぞれ独立してΔｎを大きくすることが求められる場合には芳香族であることが好ましく、応答速度を改善するためには脂肪族であることが好ましく、トランス−１，４−シクロへキシレン基、１，４−フェニレン基、２−フルオロ−１，４−フェニレン基、３−フルオロ−１，４−フェニレン基、３，５−ジフルオロ−１，４−フェニレン基、２，３−ジフルオロ−１，４−フェニレン基、１，４−シクロヘキセニレン基、１，４−ビシクロ［２．２．２］オクチレン基、ピペリジン−１，４−ジイル基、ナフタレン−２，６−ジイル基、デカヒドロナフタレン−２，６−ジイル基又は１，２，３，４−テトラヒドロナフタレン−２，６−ジイル基を表すことが好ましく、下記の構造を表すことがより好ましく、

トランス−１，４−シクロへキシレン基又は１，４−フェニレン基を表すことがより好ましい。 The alkenyl group is preferably selected from the groups represented by any of the formulas (R1) to (R5). (The black dots in each formula represent carbon atoms in the ring structure.)

A ^N11 , A ^N12 , A ^N21 , A ^N22 , A ^N31 and A ^N32 are preferably aromatic when it is required to independently increase Δn, and fat is used to improve the response speed. Group 1, preferably, trans-1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5 -Difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo[2.2.2]octylene group, piperidine-1 , 4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group is preferable, and More preferably, the structure of

It is more preferable to represent a trans-1,4-cyclohexylene group or a 1,4-phenylene group.

^{Z N11, Z N12, Z N21} , Z N22, Z N31 and ^{Z N32} _-CH 2 each _{independently O -, - CF 2 O -} , - CH 2 CH 2 -, - CF 2 CF 2 - or a single bond preferably represents _{an, -CH 2 O -, - CH} 2 CH 2 - or a single bond is more preferable, _-CH 2 O-or a single bond is particularly preferred.

X ^N21 is preferably a fluorine atom.

T ^N31 is preferably an oxygen atom.

1 or 2 is preferable for n ^N11 +n ^N12 , n ^N21 +n ^N22 and n ^N31 +n ^N32 , a combination in which n ^N11 is 1 and n ^N12 is 0, a combination in which n ^N11 is 2 and n ^N12 is 0, n ^A combination in which ^N11 is 1 and n ^N12 is 1, a combination in which n ^N11 is 2, and n ^N12 is 1, a combination in which n ^N21 is 1 and n ^N22 is 0, n ^N21 is 2 and n ^N22 is A combination of 0, a combination of n ^N31 of 1 and n ^N32 of 0, and a combination of n ^N31 of 2 and n ^N32 of 0 are preferable.

  The lower limit of the preferred content of the compound represented by formula (N-1) based on the total amount of the composition of the present invention is 0%, 1%, 10%, and 20%. , 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The preferable upper limit of the content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%. Is.

  The lower limit of the preferred content of the compound represented by formula (N-2) based on the total amount of the composition of the present invention is 0%, 1%, 10%, and 20%. , 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The preferable upper limit of the content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%. Is.

  The lower limit of the preferred content of the compound represented by formula (N-3) based on the total amount of the composition of the present invention is 0%, 1%, 10%, and 20%. , 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The preferable upper limit of the content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%. Is.

When a composition having a low viscosity and a high response speed is required for the composition of the present invention, it is preferable that the lower limit value is low and the upper limit value is low. Furthermore, when the composition of the present invention is required to have a high T _ni and a composition having good temperature stability, it is preferable that the lower limit value is low and the upper limit value is low. Further, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable that the lower limit value is high and the upper limit value is high.

（式中、Ａ^ｉ１１、Ａ^ｉ１２及びＡ^ｉ１３はそれぞれ独立して１，４−シクロへキシレン基又は１，４−フェニレン基を表すが、１，４−シクロへキシレン基中に存在する１個の−ＣＨ_２−又は隣接していない２個以上の−ＣＨ_２−は−Ｏ−又は−Ｓ−に置き換えられてもよく、１，４−フェニレン基中に存在する１個の水素原子はそれぞれ独立してフッ素原子又は塩素原子に置換されてもよく、Ｚ^ｉ１は−ＯＣＨ_２−、−ＣＨ_２Ｏ−、−ＣＦ_２Ｏ−、−ＯＣＦ_２−、−ＣＨ_２ＣＨ_２−又は−ＣＦ_２ＣＦ_２−を表し、ｍ^ｉ１１及びｍ^ｉ１２はそれぞれ独立して０又は１を表し、Ｒ^Ｎ１１、Ｒ^Ｎ１２及びＺ^Ｎ１２は、それぞれ独立して一般式（Ｎ−１）におけるＲ^Ｎ１１、Ｒ^Ｎ１２及びＺ^Ｎ１２と同じ意味を表す。） The composition of the present invention preferably contains, as the general formula (N-1), one or more compounds represented by the general formula (i-1).

(In the formula, A ⁱ¹¹ , A ^i12, and A ⁱ¹³ each independently represent a 1,4-cyclohexylene group or a 1,4-phenylene group, but one present in the 1,4-cyclohexylene group. of -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O- or -S-, is one of the hydrogen atoms present in the 1,4-phenylene group, respectively It may be independently substituted with a fluorine atom or a chlorine atom, and Z ⁱ¹ is —OCH ₂ —, —CH ₂ O—, —CF ₂ O—, —OCF ₂ —, —CH ₂ CH ₂ — or —CF ₂ CF ₂ - ^{represents, m i11} and ^{m i12} are each independently 0 or ^{1, R N11,} R ^N12 and ^{Z N12 is, R} N11, ^{R N12} and in the general formula (N-1) each independently It has the same meaning as Z ^N12 .)

（式中、Ｒ^Ｎ１１、Ｒ^Ｎ１２、Ａ^ｉ１１及びＺ^ｉ１は、それぞれ独立して一般式（ｉ−１）におけるＲ^Ｎ１１、Ｒ^Ｎ１２、Ａ^ｉ１１及びＺ^ｉ１と同じ意味を表す。）

（式中、Ｒ^Ｎ１１、Ｒ^Ｎ１２、Ａ^ｉ１１、Ａ^ｉ１２及びＺ^ｉ１は、それぞれ独立して一般式（ｉ−１）におけるＲ^Ｎ１１、Ｒ^Ｎ１２、Ａ^ｉ１１、Ａ^ｉ１２及びＺ^ｉ１と同じ意味を表す。）

（式中、ｍ^ｉ１３は１を表し、Ｒ^Ｎ１１、Ｒ^Ｎ１２、Ａ^ｉ１１、Ａ^ｉ１２、Ａ^ｉ１３、Ｚ^ｉ１、Ｚ^ｉ２及びｍ^ｉ１１は、それぞれ独立して一般式（ｉ−１）におけるＲ^Ｎ１１、Ｒ^Ｎ１２、Ａ^ｉ１１、Ａ^ｉ１２、Ａ^ｉ１３、Ｚ^ｉ１、Ｚ^ｉ２及びｍ^ｉ１１と同じ意味を表す。） The compound represented by general formula (i-1) is preferably a compound represented by general formula (i-1A), general formula (i-1B) or general formula (i-1C).

(In the formula, R ^N11 , R ^N12 , A ⁱ¹¹ and Z ⁱ¹ each independently represent the same meaning as R ^N11 , R ^N12 , A ⁱ¹¹ and Z ⁱ¹ in the general formula (i-1).)

^{(Wherein, R N11, R N12, A i11} , A i12 and ^{Z i1} are the same meaning as ^{R N11, R N12, A i11} , A i12 and ^{Z i1} in the general formula (i1) independently Represents.)

(In the formula, m ⁱ¹³ represents 1, and R ^N11 , R ^N12 , A ⁱ¹¹ , A ⁱ¹² , A ⁱ¹³ , Z ⁱ¹ , Z ^i2, and m ⁱ¹¹ are each independently R ^N11 in the general formula (i-1). , R ^N12 , A ⁱ¹¹ , A ⁱ¹² , A ⁱ¹³ , Z ⁱ¹ , Z ⁱ² and m ⁱ¹¹ have the same meanings.)

（式中、Ｒ^Ｎ１１及びＲ^Ｎ１２は、それぞれ独立して一般式（ｉ−１）におけるＲ^Ｎ１１及びＲ^Ｎ１２と同じ意味を表す。） As the compound represented by the general formula (i-1A), compounds represented by the following general formulas (i-1A-1) to (i-1A-4) are preferable.

(In the formula, R ^N11 and R ^N12 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (i-1).)

（式中、Ｒ^Ｎ１１及びＲ^Ｎ１２は、それぞれ独立して一般式（ｉ−１）におけるＲ^Ｎ１１及びＲ^Ｎ１２と同じ意味を表す。） The compound represented by the general formula (i-1B) is preferably a compound represented by the following general formula (i-1B-1) to general formula (i-1B-7).

(In the formula, R ^N11 and R ^N12 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (i-1).)

（式中、Ｒ^Ｎ１１及びＲ^Ｎ１２は、それぞれ独立して一般式（ｉ−１）におけるＲ^Ｎ１１及びＲ^Ｎ１２と同じ意味を表す。） The compound represented by the general formula (i-1C) is preferably a compound represented by the following general formula (i-1C-1) and general formula (i-1C-2).

(In the formula, R ^N11 and R ^N12 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (i-1).)

  The composition of the present invention preferably contains one or more compounds represented by the general formula (i-1), but the general formula (i-1A), the general formula (i-1B) or the general formula (i-1B) One or more compounds selected from the group of compounds represented by formula (i-1C) may be contained, and general formula (i-1A), general formula (i-1B) or general formula (i One or more compounds represented by i-1C) may be contained. The compound represented by the general formula (i-1A) and the general formula (i-1B) is preferably contained in one kind or in two or more kinds, and more preferably in 2 kinds to 10 kinds.

  More specifically, the general formula (i-1A), the general formula (i-1B) and the general formula (i-1C) are the general formula (i-1A-1), the general formula (i-1B-1) and the general formula (i-1B-1). It is preferable to contain one or more compounds selected from the group of compounds represented by formula (i-1C-1), and the compound represented by formula (i-1A-1) and the general formula (i More preferably, it is a combination of compounds represented by 1B-1).

（式中、Ａ^ｉｉ１、Ａ^ｉｉ２はそれぞれ独立して１，４−シクロへキシレン基又は１，４−フェニレン基を表すが、１，４−シクロへキシレン基中に存在する１個の−ＣＨ_２−又は隣接していない２個以上の−ＣＨ_２−は−Ｏ−又は−Ｓ−に置き換えられてもよく、１，４−フェニレン基中に存在する１個の水素原子はそれぞれ独立してフッ素原子又は塩素原子に置換されてもよく、ｍ^ｉｉ１及びｍ^ｉｉ２はそれぞれ独立して１又は２を表し、Ｒ^Ｎ１１及びＲ^Ｎ１２は、それぞれ独立して一般式（Ｎ−１）におけるＲ^Ｎ１１及びＲ^Ｎ１２と同じ意味を表す。） Further, the composition of the present invention preferably contains one or more compounds represented by the general formula (ii).

(In the formula, A ⁱⁱ¹ and A ⁱⁱ² each independently represent a 1,4-cyclohexylene group or a 1,4-phenylene group, but one -CH present in the 1,4-cyclohexylene group is present. ₂ - or nonadjacent two or more -CH 2 _- is -O- or -S- to may be replaced, is one of the hydrogen atoms present in the 1,4-phenylene group independently It may be substituted by a fluorine atom or a chlorine ^{atom, m ii1} and ^{m ii2} independently represents 1 or ^{2, R N11} and ^{R N12} is, ^{R N11} and in the general formula (N-1) each independently It has the same meaning as R ^N12 .)

（式中、Ｒ^Ｎ１１、Ｒ^Ｎ１２、Ａ^ｉｉ１及びｍ^ｉｉ１は一般式（ｉｉ）におけるＲ^Ｎ１１、Ｒ^Ｎ１２、Ａ^ｉｉ１及びｍ^ｉｉ１と同じ意味を表す。） As the general formula (ii-1), it is preferable to contain one or more compounds represented by the general formula (ii-1).

^(Wherein, it represents the same meaning as R ^N11, R ^{N12, A ii1} and ^{m ii1} is ^R N11 in the general formula ^{(ii), R N12, A} ii1 and ^{m ii1.)}

（式中、Ｒ^Ｎ１１、Ｒ^Ｎ１２及びＡ^ｉｉ１は一般式（ｉｉ）におけるＲ^Ｎ１１、Ｒ^Ｎ１２及びＡ^ｉｉ１と同じ意味を表す。）

（式中、Ａ^ｉｉ１１及びＡ^ｉｉ１１はそれぞれ独立して１，４−シクロへキシレン基又は１，４−フェニレン基を表すが、１，４−シクロへキシレン基中に存在する１個の−ＣＨ_２−又は隣接していない２個以上の−ＣＨ_２−は−Ｏ−又は−Ｓ−に置き換えられてもよく、１，４−フェニレン基中に存在する１個の水素原子はそれぞれ独立してフッ素原子又は塩素原子に置換されてもよく、Ｒ^Ｎ１１及びＲ^Ｎ１２は一般式（ｉｉ）におけるＲ^Ｎ１１及びＲ^Ｎ１２と同じ意味を表す。） The compound represented by the general formula (ii-1) is preferably a compound represented by the general formula (ii-1A) or the general formula (ii-1B).

^{(Wherein, R N11,} R ^N12 and ^{A ii1} have the same meanings as ^{R N11, R N12} and ^{A ii1} in formula (ii).)

(In the formula, A ⁱⁱ¹¹ and A ⁱⁱ¹¹ each independently represent a 1,4-cyclohexylene group or a 1,4-phenylene group, but one -CH present in the 1,4-cyclohexylene group is present. ₂ - or nonadjacent two or more -CH 2 _- is -O- or -S- to may be replaced, is one of the hydrogen atoms present in the 1,4-phenylene group independently It may be substituted with a fluorine atom or a chlorine atom, and R ^N11 and R ^N12 have the same meanings as R ^N11 and R ^N12 in the general formula (ii).)

（式中、Ｒ^Ｎ１１及びＲ^Ｎ１２は、一般式（ｉｉ）におけるＲ^Ｎ１１及びＲ^Ｎ１２と同じ意味を表す。） As the compound represented by the general formula (ii-1A), compounds represented by the following general formulas (ii-1A-1) and (ii-1A-2) are preferable.

^{(Wherein, R N11} and ^{R N12} are the same as defined ^{R N11} and ^{R N12} in the general formula (ii).)

（式中、Ｒ^Ｎ１１及びＲ^Ｎ１２は、一般式（ｉｉ）におけるＲ^Ｎ１１及びＲ^Ｎ１２と同じ意味を表す。） The compound represented by the general formula (ii-1B) is preferably a compound represented by the following general formula (ii-1B-1) to general formula (ii-1B-3).

^{(Wherein, R N11} and ^{R N12} are the same as defined ^{R N11} and ^{R N12} in the general formula (ii).)

  The composition of the present invention preferably contains one or more compounds represented by the general formula (ii), and is represented by the general formula (ii-1A) and the general formula (ii-1B). One or more compounds selected from the compound group may be contained, or one or more compounds represented by the general formula (ii-1A) and the general formula (ii-1B) may be contained. Good. It is preferable to contain 2 to 10 types of compounds represented by the general formula (ii-1A) and the general formula (ii-1B).

  More specifically, the general formula (ii-1A) preferably contains one or more compounds selected from the group of compounds represented by the general formula (ii-1A-1), and the general formula (ii- 1B) preferably contains one or more compounds selected from the group of compounds represented by general formula (ii-1B-1) and general formula (ii-1B-2), and general formula (ii- 1A-1) and the compound represented by formula (ii-1B-1) are more preferred.

（式中、Ｒ^Ｎ１１、Ｒ^Ｎ１２、Ａ^Ｎ１１、Ａ^Ｎ１２及びＺ^Ｎ１１はそれぞれ独立して、一般式（Ｎ−１）におけるＲ^Ｎ１１、Ｒ^Ｎ１２、Ａ^Ｎ１１、Ａ^Ｎ１２及びＺ^Ｎ１１と同じ意味を表し、Ｘ^{ＬＣ３ｂ１}〜Ｘ^{ＬＣ３ｂ４}は水素原子又はフッ素原子を表すが、Ｘ^{ＬＣ３ｂ１}及びＸ^{ＬＣ３ｂ２}、又はＸ^{ＬＣ３ｂ３}及びＸ^{ＬＣ３ｂ４}のうちの少なくとも一方の組み合わせは共にフッ素原子を表し、ｍ^{ＬＣ３ｂ１}は０又は１を表す。ただし、一般式（ＬＣ３−ｂ）において、一般式（ｉ−１）及び一般式（ｉｉ）で表される化合物は除く。） In addition, as the general formula (N-1), it is preferable to contain one or more compounds represented by the following general formula (LC3-b).

(In the formula, R ^N11 , R ^N12 , A ^N11 , A ^N12 and Z ^N11 each independently have the same meaning as R ^N11 , R ^N12 , A ^N11 , A ^N12 and Z ^{N11 in} the general formula (N-1). ^represents, although ^{X LC3b1} ~X ^LC3b4 represents a hydrogen atom or a fluorine ^{atom, X LC3b1} and ^{X LC3b2,} or at least one combination of ^{X LC3b3} and ^{X LC3b4} together represents a fluorine ^{atom, m LC3b1} a is 0 or 1 However, in the general formula (LC3-b), compounds represented by the general formula (i-1) and the general formula (ii) are excluded.)

（式中、Ｒ^Ｎ１１及びＲ^Ｎ１２はそれぞれ独立して一般式（Ｎ−１）におけるＲ^Ｎ１１及びＲ^Ｎ１２と同じ意味を表す。） The compound represented by the general formula (LC3-b) is preferably a compound represented by the following general formula (LC3-b1) to general formula (LC3-b10).

(In the formula, R ^N11 and R ^N12 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (N-1).)

The combination of R ^N11 and R ^N12 is not particularly limited, but both represent an alkyl group, both represent an alkenyl group, one represents an alkyl group, the other represents an alkenyl group, and either one represents It is preferable that both represent an alkyl group, the other represents an alkoxy, and one represents an alkyl group and the other represents an alkenyloxy group, both represent an alkyl group, and both represent an alkenyl group. It is more preferable that it is represented.

（式中、Ｒ^Ｎ１１及びＲ^Ｎ１２はそれぞれ独立して一般式（Ｎ−１）におけるＲ^Ｎ１１及びＲ^Ｎ１２と同じ意味を表す。） Further, the compound represented by the general formula (LC3-b) is preferably a compound represented by the following general formula (LC3-c).

(In the formula, R ^N11 and R ^N12 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (N-1).)

（式中、Ｒ^Ｎ２１１及びＲ^Ｎ２２はそれぞれ独立して、一般式（Ｎ−２）におけるＲ^Ｎ２１１及びＲ^Ｎ２２と同じ意味を表す。） The compound represented by the general formula (N-2) is preferably a compound selected from the group of compounds represented by the general formulas (N-2-1) to (N-2-3).

(In the formula, R ^N211 and R ^N22 each independently have the same meaning as R ^N211 and R ^N22 in the general formula (N-2).)

（式中、Ｒ^Ｎ３１及びＲ^Ｎ３２はそれぞれ独立して、一般式（Ｎ−３）におけるＲ^Ｎ３１及びＲ^Ｎ３２と同じ意味を表す。） The compound represented by the general formula (N-3) is preferably a compound selected from the group of compounds represented by the general formulas (N-3-1) and (N-3-2).

(In the formula, R ^N31 and R ^N32 each independently have the same meaning as R ^N31 and R ^N32 in the general formula (N-3).)

（式中、Ｒ^Ｌ１及びＲ^Ｌ２はそれぞれ独立して炭素原子数１〜８のアルキル基を表し、該アルキル基中の１個又は非隣接の２個以上の−ＣＨ_２−はそれぞれ独立して−ＣＨ＝ＣＨ−、−Ｃ≡Ｃ−、−Ｏ−、−ＣＯ−、−ＣＯＯ−又は−ＯＣＯ−によって置換されていてもよく、
ｎ^Ｌ１は０、１、２又は３を表し、
Ａ^Ｌ１、Ａ^Ｌ２及びＡ^Ｌ３はそれぞれ独立して
（ａ１２） １，４−シクロヘキシレン基（この基中に存在する１個の−ＣＨ_２−又は隣接していない２個以上の−ＣＨ_２−は−Ｏ−に置き換えられてもよい。）
（ｂ１２） １，４−フェニレン基（この基中に存在する１個の−ＣＨ＝又は隣接していない２個以上の−ＣＨ＝は−Ｎ＝に置き換えられてもよい。）及び
（ｃ１２） ナフタレン−２，６−ジイル基、１，２，３，４−テトラヒドロナフタレン−２，６−ジイル基又はデカヒドロナフタレン−２，６−ジイル基（ナフタレン−２，６−ジイル基又は１，２，３，４−テトラヒドロナフタレン−２，６−ジイル基中に存在する１個の−ＣＨ＝又は隣接していない２個以上の−ＣＨ＝は−Ｎ＝に置き換えられても良い。）
からなる群より選ばれる基を表し、上記の基（ａ１２）、基（ｂ１２）及び基（ｃ１２）はそれぞれ独立してシアノ基、フッ素原子又は塩素原子で置換されていても良く、
Ｚ^Ｌ１及びＺ^Ｌ２はそれぞれ独立して単結合、−ＣＨ_２ＣＨ_２−、−（ＣＨ_２）_４−、−ＯＣＨ_２−、−ＣＨ_２Ｏ−、−ＣＯＯ−、−ＯＣＯ−、−ＯＣＦ_２−、−ＣＦ_２Ｏ−、−ＣＨ＝Ｎ−Ｎ＝ＣＨ−、−ＣＨ＝ＣＨ−、−ＣＦ＝ＣＦ−又は−Ｃ≡Ｃ−を表し、
ｎ^Ｌ１が２又は３であってＡ^Ｌ２が複数存在する場合は、それらは同一であっても異なっていても良く、ｎ^Ｌ１が２又は３であってＺ^Ｌ３が複数存在する場合は、それらは同一であっても異なっていても良いが、一般式（Ｎ−１）、一般式（Ｎ−２）及び一般式（Ｎ−３）で表される化合物を除く。） The third component preferably contains one or more compounds represented by formula (L). The compound represented by the general formula (L) corresponds to a dielectrically almost neutral compound (Δε value is −2 to 2).

(In the formula, R ^L1 and R ^L2 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or non-adjacent two or more —CH ₂ — in the alkyl group are each independently. -CH=CH-, -C[identical to]C-, -O-, -CO-, -COO- or -OCO- may be substituted,
n ^L1 represents 0, 1, 2 or 3,
A ^L1 , A ^L2 and A ^L3 are each independently a (a12) 1,4-cyclohexylene group (one —CH ₂ — present in this group or two or more —CH ₂ — which are not adjacent to each other). May be replaced with -O-.)
(B12) 1,4-phenylene group (one -CH= present in this group or two or more -CH= which are not adjacent to each other may be replaced with -N=) and (c12). Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or 1,2 , 3,4-tetrahydronaphthalene-2,6-diyl group may have one -CH= or two or more non-adjacent -CH=, which may be replaced by -N=.)
Represents a group selected from the group consisting of, the group (a12), the group (b12) and the group (c12) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,
Z ^L1 and Z ^L2 are each independently a single bond, —CH ₂ CH ₂ —, —(CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —OCF _{2 -, - CF 2 O -,} - CH = N-N = CH -, - CH = CH -, - represents CF = CF- or -C≡C-,
When n ^L1 is 2 or 3 and plural A ^L2 are present, they may be the same or different, and when n ^L1 is 2 or 3 and Z ^L3 is plural, they may be the same. May be the same or different, but the compounds represented by the general formula (N-1), the general formula (N-2) and the general formula (N-3) are excluded. )

  The compounds represented by general formula (L) may be used alone or in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to desired properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The type of compound used is, for example, one type in one embodiment of the present invention. Alternatively, in another embodiment of the present invention, there are two types, three types, four types, five types, six types, seven types, eight types, nine types, and ten types. More than type.

  In the composition of the present invention, the content of the compound represented by the general formula (L) is such that the solubility at low temperature, the transition temperature, the electrical reliability, the birefringence, the process compatibility, the dripping mark, the seizure, It is necessary to appropriately adjust according to the required performance such as dielectric anisotropy.

  The lower limit of the preferred content of the compound represented by formula (L) relative to the total amount of the composition of the present invention is 0%, 1%, 10%, 20%, 30 %, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The upper limit of the preferable content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%.

When a composition which keeps the viscosity of the composition of the present invention low and has a fast response speed is required, it is preferable that the lower limit value is high and the upper limit value is high. Further, when the composition of the present invention has a high T _ni and a composition having good temperature stability is required, it is preferable that the lower limit value is high and the upper limit value is high. Further, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable that the lower limit value and the upper limit value are low.

Both R ^L1 and R ^L2 are preferably alkyl groups when the reliability is important, and alkoxy groups are preferable when the volatility of the compound is important, and reduction in viscosity is important. In that case, at least one of them is preferably an alkenyl group.

R ^L1 and R ^L2 are a linear alkyl group having 1 to 5 carbon atoms or a linear carbon number 1 to 4 when the ring structure to which it is bonded is a phenyl group (aromatic). And an alkenyl group having 4 to 5 carbon atoms are preferable, and when the ring structure to which it is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane, a straight chain having 1 to 5 carbon atoms. An alkyl group, a linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, the total number of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear.

The alkenyl group is preferably selected from the groups represented by any of the formulas (R1) to (R5). (The black dots in each formula represent carbon atoms in the ring structure.)

Among them, by using a compound in which at least one of R ^L1 and R ^L2 represents an alkenyl group and a compound represented by the general formula (i) in combination, the decrease in voltage holding ratio (VHR) is significantly suppressed. be able to.

n ^L1 is preferably 0 when importance is attached to the response speed, 2 or 3 is preferable for improving the maximum temperature of the nematic phase, and 1 is preferable for achieving a balance between them. Further, in order to satisfy the properties required for the composition, it is preferable to combine compounds having different values.

トランス−１，４−シクロへキシレン基又は１，４−フェニレン基を表すことがより好ましい。 A ^L1 , A ^L2, and A ^L3 are preferably aromatic when it is required to increase Δn, and preferably aliphatic in order to improve the response speed. 1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group , 1,4-cyclohexenylene group, 1,4-bicyclo[2.2.2]octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6 -Diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group is preferable, and the following structure is more preferable,

It is more preferable to represent a trans-1,4-cyclohexylene group or a 1,4-phenylene group.

Z ^L1 and Z ^L2 are preferably single bonds when importance is attached to the response speed.

  The compound represented by the general formula (L) preferably has 0 or 1 halogen atom in the molecule.

（式中、Ｒ^Ｌ１及びＲ^Ｌ２はそれぞれ独立して、一般式（Ｌ）におけるＲ^Ｌ１及びＲ^Ｌ２と同じ意味を表す。） The compound represented by the general formula (L) is preferably a compound selected from the compounds represented by the general formula (L-1).

(In the formula, R ^L1 and R ^L2 each independently represent the same meaning as R ^L1 and R ^L2 in the general formula (L).)

R ^L11 and R ^L12 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms. .. The compound represented by the general formula (L-1) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

  The lower limit of the preferable content is 1%, 2%, 3%, 5%, 7%, 10%, 15% with respect to the total amount of the composition of the present invention. %, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%. The preferable upper limit of the content is 95%, 90%, 85%, 80%, 75%, 70%, 65 with respect to the total amount of the composition of the present invention. %, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25%.

When a composition which keeps the viscosity of the composition of the present invention low and has a fast response speed is required, it is preferable that the lower limit value is high and the upper limit value is high. Further, when the composition of the present invention is required to have a high T _ni and a composition having good temperature stability, it is preferable that the lower limit value is moderate and the upper limit value is moderate. Further, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable that the lower limit value is low and the upper limit value is low.

（式中、Ｒ^Ｌ１１は水素原子又はメチル基を表し、Ｒ^Ｌ２は一般式（Ｌ）中のＲ^Ｌ２と同じ意味を表す。） The compound represented by General Formula (L-1) is preferably the compound represented by General Formula (L-1-1).

^{(Wherein, R L11} represents a hydrogen atom or a methyl ^{group, R L2} represents the same meaning as ^{R L2} in Formula (L).)

The compound represented by the general formula (L-1-1) is a compound selected from the group of compounds represented by the formula (L-1-1.11) to the formula (L-1-1.13). Is preferably a compound represented by the formula (L-1-1.12) or the formula (L-1-1.13), and particularly preferably a compound represented by the formula (L-1-1.13). The compound is preferably

The compound represented by the general formula (L-1-1) is a compound selected from the group of compounds represented by the formula (L-1-1.21) to the formula (L-1-1.24). It is preferable that the compound is represented by the formula (L-1-1.22) to the compound represented by the formula (L-1-1.24). In particular, the compound represented by the formula (L-1-1.22) is preferable because it improves the response speed of the composition of the present invention. Further, when obtaining T _ni higher than the response speed, it is preferable to use the compound represented by formula (L-1-1.23) or formula (L-1-1.24).

Further, the compound represented by the general formula (L-1-1) is a compound selected from the group of compounds represented by the formula (L-1-1.31) and the formula (L-1-1.41). Preferably.

（式中、Ｒ^Ｌ１２１及びＲ^Ｌ１２２はそれぞれ独立して炭素原子数１〜８のアルキル基又は炭素原子数１〜８のアルコキシ基を表す。） Further, the compound represented by General Formula (L-1) is preferably the compound represented by General Formula (L-1-2).

(In the formula, R ^L121 and R ^L122 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.)

The compound represented by General Formula (L-1-2) is a compound selected from the group of compounds represented by Formula (L-1-2.1) to Formula (L-1-2.12). Is preferred, and a compound represented by formula (L-1-2.1), formula (L-1-2.3) or formula (L-1-2.4) is preferred. In particular, the compound represented by the formula (L-1-2.1) is preferable because it improves the response speed of the composition of the present invention. Further, when obtaining T _ni higher than the response speed, equation (L-1-2.3), equation (L-1-2.4), equation (L-1-2.11), and equation (L It is preferable to use the compound represented by -1-2.12). The total of the compounds represented by formula (L-1-2.3), formula (L-1-2.4), formula (L-1-2.11) and formula (L-1-2.12). The content of is not preferably 20% or more in order to improve the solubility at low temperature.

（式中、Ｒ^Ｌ２は一般式（Ｌ）中のＲ^Ｌ２と同じ意味を表す。） Further, the compound represented by General Formula (L-1) is preferably a compound selected from the group of compounds represented by General Formula (L-1-3) and/or (L-1-4). ..

(In the formula, R ^L2 has the same meaning as R ^L2 in formula (L).)

（式中、Ｒ^Ｌ３１及びＲ^Ｌ３２は、炭素原子数１から５のアルキル基又は炭素原子数２から５のアルケニル基、Ｒ^Ｌ３２は、炭素原子数１から５のアルキル基、炭素原子数１から５のアルコキシル基、炭素原子数２から５のアルケニル基又は炭素原子数２から５のアルケニルオキシ基を表す。） Further, the compound represented by the general formula (L) is preferably a compound represented by the following general formula (L-2) to general formula (L-11). The composition of the present invention may contain, as the compound represented by the general formula (L), one or more compounds represented by the general formula (L-2) to the general formula (L-11). preferable.

(In the formula, R ^L31 and R ^L32 are an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R ^L32 is an alkyl group having 1 to 5 carbon atoms, and 1 to 5 carbon atoms. 5 represents an alkoxyl group having 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms.)

  The compound represented by the general formula (L) is a compound selected from the general formula (L-4), the general formula (L-6), the general formula (L-7) and the general formula (L-8). Is more preferable, and a compound selected from general formula (L-6), general formula (L-7) and general formula (L-8) is more preferable, and general formula (L-7) and general formula (L- The compound selected from 8) is more preferable, and the compound selected from general formula (L-6) and general formula (L-8) is also preferable. More specifically, when a large Δn is required, a compound selected from the general formula (L-6), the general formula (L-8) and the general formula (L-11) is preferable.

In the compounds represented by the general formula (L-4), the general formula (L-7) and the general formula (L-8), R ^L31 is an alkyl group having 1 to 5 carbon atoms or 2 carbon atoms. To alkenyl group, R ^L32 is preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, and R ^L31 is an alkenyl group having 2 to 5 carbon atoms. More preferably, it is more preferably an alkenyl group having 2 or 3 carbon atoms, and in the compound represented by formula (L-6), R ^L31 and R ^L32 each independently have 1 to 5 carbon atoms. And an alkenyl group having 2 to 5 carbon atoms.

（式中、Ｒ^Ｌ５１及びＲ^Ｌ５２はそれぞれ独立して炭素原子数１〜５のアルキル基、炭素原子数２〜５のアルケニル基又は炭素原子数１〜４のアルコキシ基を表し、Ｘ^Ｌ５１及びＸ^Ｌ５２はそれぞれ独立してフッ素原子又は水素原子を表し、Ｘ^Ｌ５１及びＸ^Ｌ５２のいずれか一つはフッ素原子であり、他の一つは水素原子である。） Further, as the compound represented by the general formula (L), one or more compounds represented by the general formula (L-12), the general formula (L-13) or the general formula (L-14) are contained. It is also preferable to

(In the formula, R ^L51 and R ^L52 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and X ^L51 and X ^L52 each independently represents a fluorine atom or a hydrogen atom, one of X ^L51 and X ^L52 is a fluorine atom, and the other one is a hydrogen atom.)

Moreover, as the compound represented by the general formula (L), one or more compounds represented by the general formula (L-16.1) to the general formula (L-16.3) may be contained. ..

（式中、Ｒ^Ｎ１及びＲ^Ｎ２はそれぞれ独立して炭素原子数１から８のアルキル基、炭素原子数１から８のアルコキシル基、炭素原子数２から８のアルケニル基又は炭素原子数２から８のアルケニルオキシル基を表し、Ｌ^１及びＬ^２はそれぞれ独立して水素原子、フッ素原子、ＣＨ_３又はＣＦ_３を表す。ただし、Ｌ^１及びＬ^２の両方がフッ素原子を表すものを除く。） In addition, as the compound represented by the general formula (L), one or more compounds represented by the general formula (N-001) may be contained.

(In the formula, R ^N1 and R ^N2 are each independently an alkyl group having 1 to 8 carbon atoms, an alkoxyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkyl group having 2 to 8 carbon atoms. In the formula ( ¹⁾ , L ¹ and L ² each independently represent a hydrogen atom, a fluorine atom, CH ₃ or CF _{3 (provided} that both L ¹ and L ² represent a fluorine atom).

R ^N1 and R ^N2 preferably represent an alkyl group having 1 to 5 carbon atoms.

  The composition of the present invention has a negative dielectric anisotropy (Δε) at 25°C. The composition of the present invention has a dielectric anisotropy (Δε) of −2.0 to −8.0 at 25° C., preferably −2.0 to −6.0, and −2. It is more preferably from 0 to -5.0, particularly preferably from -2.5 to -4.5.

  The composition having a negative dielectric anisotropy (Δε) includes compounds represented by general formula (N-1) to general formula (N-3) and compounds represented by general formula (L). It is preferable to contain. More specifically, it preferably contains a compound represented by the general formula (N-1) and a compound represented by the general formula (L-1), and a compound represented by the general formula (N-1) And a compound represented by the general formula (L-1-1) is preferably contained.

  The composition of the present invention comprises a compound represented by the general formula (I), a compound represented by the general formula (N-1) to a general formula (N-3) and a compound represented by the general formula (L). The lower limit of the total content of the composition is preferably 5% or more, more preferably 80% or more, preferably 85% or more, and preferably 88% or more. 90% or more is preferable, 92% or more is preferable, 95% or more is preferable, 97% or more is preferable, 98% or more is preferable, 99% or more is contained. It is preferable that it is substantially free of other compounds. As the upper limit value, the content is preferably 90% or less, more preferably 95% or less, preferably 98% or less, preferably 99% or less, and substantially contains another compound. Not preferably.

  The composition of the present invention has a refractive index anisotropy (Δn) at 25° C. of 0.08 to 0.14, preferably 0.09 to 0.13, more preferably 0.09 to 0.14. 12 is particularly preferable. More specifically, it is preferably 0.10 to 0.13 when it corresponds to a thin cell gap and 0.08 to 0.10 when it corresponds to a thick cell gap. In this specification, 0.09 or more is described as having a large Δn.

The composition of the present invention has a rotational viscosity (γ ₁ ) at 25° C. of 50 to 160 mPa·s, preferably 55 to 160 mPa·s, preferably 60 to 160 mPa·s, and 80 to It is preferably 130 mPa·s.

The composition of the present invention has a nematic phase-isotropic liquid phase transition temperature (T _NI ) of 60°C to 120°C, more preferably 70°C to 100°C, and more preferably 70°C to 85°C. Is particularly preferable. In addition, in this specification, _TNI is described as being high at 60° C. or higher. For liquid crystal television applications, T _NI is preferably 70° C. to 80° C., for mobile applications, T _NI is preferably 80° C. to 90° C., and outdoor display applications such as PID (Public Information Display). In the case of, T _NI is preferably 90° C. to 110° C.

  The composition of the present invention includes, in addition to the compounds described above, ordinary nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, antioxidants, ultraviolet absorbers, infrared absorbers, polymerizable monomers or light stabilizers other than the compounds of the present invention ( HALS) and the like may be contained.

  The display device using the composition containing the compound of the present invention can be applied to liquid crystal display devices of various modes such as VA mode, PSVA mode, PSA mode, IPS mode, FFS mode or ECB mode.

  The present invention is described in more detail below with reference to examples, but the present invention is not limited to these examples. Moreover, "%" in the composition containing the compound of the following Examples and Comparative Examples means "mass %." The phase transition temperature was measured by using a polarizing microscope equipped with a temperature control stage and a differential scanning calorimeter (DSC) together.

The following abbreviations are used below.
amphos: di-tert-butyl(4-dimethylaminophenyl)phosphine Bu:n-butyl DMF:N,N-dimethylformamide dppf:1,1′-bis(diphenylphosphino)ferrocene Et:ethyl NMP:N-methyl -2-Pyrrolidone Pent:n-Pentyl Pr:n-Propyl Tf:Trifluoromethanesulfonyl THF:Tetrahydrofuran

(Example 1) Synthesis of compound G-1-5

(Synthesis of Compound G-1-2)
In a nitrogen atmosphere, a reaction vessel equipped with a stirrer, a thermometer, a dropping funnel, and a cooling tube was charged with compound G-1-1 (28.8 g), 4-bromoresorcinol (24.5 g), bis[di-dichloride]. tert-Butyl(4-dimethylaminophenyl)phosphine]palladium(II) (0.23 g) and THF (98 mL) were added, and the temperature was raised to 60°C with stirring. A 2M aqueous sodium carbonate solution (130 mL) was added dropwise to the reaction mixture. After stirring at 60° C. for 6 hours, the heating was stopped and the solution temperature was returned to room temperature. Then, 10% hydrochloric acid (140 mL) was added. The organic layer was separated, and the aqueous layer was reextracted with ethyl acetate (100 mL). The obtained organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and dried. The obtained solution was concentrated, ethyl acetate (320 mL) and hexane (80 mL) were added and dissolved, and the solution was passed through a column packed with silica gel (23 g) and alumina (23 g), and further ethyl acetate (240 mL), A mixed solvent of toluene (60 mL) was passed through. The obtained column passing solution was concentrated and then vacuum dried to obtain compound G-1-2 (38.82 g).

(Synthesis of Compound G-1-3)
Under a nitrogen atmosphere, compound G-1-2 (34.1 g) and NMP (270 mL) were added to a reaction vessel equipped with a stirrer, a thermometer, and a condenser and stirred. Potassium carbonate (35.4 g) was added thereto, and the solution temperature was heated to 160° C. over 1 hour and a half. After stirring at 160° C. for 4 hours, the mixture was cooled to room temperature, 10% hydrochloric acid (150 mL), water (150 mL) and ethyl acetate (200 mL) were added. The organic layer was separated, and the aqueous layer was re-extracted with ethyl acetate (200 mL). The obtained organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and dried. After the obtained solution was concentrated, dichloromethane (300 mL) was added and dissolved, and the solution was passed through a column packed with silica gel (19 g) and alumina (19 g), and further passed through dichloromethane (400 mL). The obtained column passing solution was concentrated and then vacuum dried to obtain compound G-1-3 (33.28 g).

(Synthesis of Compound G-1-4)
Under a nitrogen atmosphere, to a reaction vessel equipped with a stirrer, a thermometer and a dropping funnel, compound G-1-3 (10.0 g), pyridine (11.12 g) and dichloromethane (92 mL) were added, and the mixture was stirred at 10°C. Cooled to. Then, trifluoromethanesulfonic anhydride (31.78 g) was added dropwise at 0° C. over 30 minutes. After stirring at 0°C for 30 minutes, the temperature was raised to 25°C and the mixture was stirred for 1 hour. Then, 10% hydrochloric acid (50 mL) was added dropwise at 20°C to 30°C, and the mixture was stirred for 30 minutes. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (200 mL). The obtained organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and dried. After the obtained solution was concentrated, dichloromethane (300 mL) was added and dissolved, and the solution was passed through a column packed with silica gel (19 g) and alumina (19 g), and further passed through dichloromethane (360 mL). The obtained column passing solution was concentrated and then vacuum dried to obtain compound G-1-4 (27.99 g).

(Synthesis of Compound G-1-5)
In a reaction vessel equipped with a stirrer and a thermometer under a nitrogen atmosphere, compound G-1-4 (10.0 g) and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (II)(1 0.08 g) and THF (80 mL) were added, and the mixture was stirred and cooled to 0°C. A 0.61 M propyl zinc chloride/THF solution (65 mL) was added dropwise at 0° C. over 30 minutes. After stirring at 0°C for 30 minutes, the temperature was raised to 45°C and the mixture was stirred for 1 hour. Then, after cooling to 20 degreeC, saturated ammonium chloride aqueous solution (50 mL) was dripped at 20 degreeC-30 degreeC, and it stirred for 30 minutes. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (100 mL). The obtained organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and dried. After concentrating the obtained solution, hexane (70 mL) was added and dissolved, and the solution was passed through a column at 55° C. packed with silica gel (7 g) and alumina (7 g), and then hexane (120 mL) was passed. The obtained column passing solution was concentrated and then vacuum dried to obtain compound G-1-5 (1.66 g).
Phase transition temperature: Cr 69.3 Iso
MS m/z: 271 [M ⁺ ]

(Example 2) Synthesis of compound G-1-6

(Synthesis of Compound G-1-6)
Compound G-1-3 (4.98 g), potassium carbonate (5.63 g), bromoethane (2.57 g), NMP (20 mL) in a reaction vessel equipped with a stirrer, a thermometer, and a condenser under a nitrogen atmosphere. Was added and stirred. The solution temperature was heated to 100° C. over 1 hour. After stirring at 100° C. for 8 hours, the mixture was cooled to room temperature, 10% hydrochloric acid (25 mL) and water (20 mL) were added, the precipitated solid was filtered off, and the residue was washed with water (45 mL). The obtained compound was azeotroped with toluene (75 mL). Dichloromethane (20 mL) and silica gel (7.5 g) were added to the obtained solid, and the mixture was concentrated to dryness. The obtained powder was added to a column packed with silica gel (55 g), and ethyl acetate (10 mL) and hexane (500 mL) were further passed through. The obtained column passing solution was concentrated and then vacuum dried to obtain compound G-1-6 (1.37 g).
Phase transition temperature: Cr 92.6 Iso
MS m/z: 273 [M ⁺ ].

(Example 3) Synthesis of compound G-1-7

(Synthesis of Compound G-1-7)
Under a nitrogen atmosphere, in a reaction vessel equipped with a stirrer, a thermometer, and a condenser, compound G-1-3 (5.40 g), potassium carbonate (6.08 g), bromopentane (3.48 g), NMP (40 mL). ) Was added and stirred. The solution temperature was heated to 100° C. over 1 hour. After stirring at 100°C for 1.5 hours, the mixture was cooled to room temperature, 10% hydrochloric acid (30 mL), water (30 mL) and toluene (70 mL) were added, the organic layer was separated, and the aqueous layer was extracted with toluene (70 mL). did. The obtained organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and dried. After the obtained solution was concentrated, it was recrystallized with an acetone/ethanol mixed solution. Thereafter, a solution obtained by dissolving the obtained solid in toluene (5 mL) and hexane (25 mL) is passed through a silica gel column, and the obtained column passing solution is concentrated to dryness to give compound G-1-7 (3. 54 g) was obtained.
Phase transition temperature: Cr 57.0 Iso
MS m/z: 315 [M ⁺ ].

(Example 4) Synthesis of compound G-1-10

(Synthesis of Compound G-1-9)
Under a nitrogen atmosphere, in a reaction vessel equipped with a stirrer, a thermometer, a dropping funnel, and a cooling tube, compound G-1-8 (4.26 g), 6-bromo-3-butoxy-2-fluorophenol (3.88 g). ), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(II) dichloride (0.10 g) and THF (16 mL) were added, and the temperature was raised to 60°C with stirring. A 2M sodium carbonate aqueous solution (11 mL) was added dropwise to the reaction mixture. After stirring at 60° C. for 1.5 hours, the heating was stopped and the solution temperature was returned to room temperature. Then, 10% hydrochloric acid (15 ml) was added. The organic layer was separated, and the aqueous layer was reextracted with ethyl acetate (100 mL). The obtained organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and dried. After the obtained solution was concentrated, ethyl acetate (5 mL) and hexane (45 mL) were added and dissolved, and the solution was passed through a column packed with silica gel (7 g) and alumina (7 g), and further ethyl acetate (20 mL), A mixed solvent of hexane (180 mL) was passed through. The obtained column passing solution was concentrated and then vacuum dried to obtain compound G-1-9 (6.32 g).

(Synthesis of Compound G-1-10)
Under a nitrogen atmosphere, a compound G-1-9 (6.32 g), potassium carbonate (4.05 g), and NMP (50 mL) were added to a reaction vessel equipped with a stirrer, a thermometer, and a condenser, and stirred. The solution temperature was heated to 160° C. over 1 hour. After stirring at 160° C. for 12 hours, the mixture was cooled to room temperature, 10% hydrochloric acid (20 mL) and toluene (50 mL) were added, the organic layer was separated, and the aqueous layer was extracted with toluene (50 mL). The obtained organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and dried. After the obtained solution was concentrated, it was recrystallized with an acetone/ethanol mixed solution. Then, the solution obtained by dissolving the obtained solid in dichloromethane (30 mL) was passed through a silica gel column, and the obtained column passing solution was concentrated to dryness to obtain compound G-1-10 (2.61 g). ..
Phase transition temperature: Cr 84.7 N 133.5 Iso
MS m/z: 381 [M ⁺ ]

（化合物Ｇ−１−１２の合成）
窒素雰囲気下、撹拌装置、温度計を備えた反応容器に、ジイソプロピルアミン（２８．３３ｇ）、ＴＨＦ（３５０ｍＬ）を加えて攪拌し、−７８℃に冷却した。２．７６Ｍブチルリチウム／ヘキサン溶液（９４ｍＬ）を−７８℃にて１時間かけて滴下した。−７８℃で３０分攪拌後、化合物Ｇ−１−１１（４３．８ｇ）を−７８℃にて１時間かけて滴下した。−７８℃で３時間攪拌した後、ＤＭＦ（４５ｇ）を−７８℃にて３０分かけて滴下した。−７８℃で１時間攪拌後、−２０℃まで昇温し、反応液を１０％塩酸（１００ｍＬ）に滴下した。有機層を分け取り、さらに水層をトルエン（２００ｍＬ）で抽出した。得られた有機層を合わせた後、水、炭酸水素ナトリウム水溶液、飽和食塩水で洗浄し、無水硫酸ナトリウムを加えて乾燥した。得られた溶液を濃縮後、トルエン（５０ｍＬ）を加えて溶解した溶液を、シリカゲルカラムを通過させ、得られたカラム通過溶液を濃縮乾固することで化合物Ｇ−１−１２（２０ｇ）を得た。 (Example 5) Synthesis of compound G-1-16

(Synthesis of Compound G-1-12)
Under a nitrogen atmosphere, diisopropylamine (28.33 g) and THF (350 mL) were added to a reaction vessel equipped with a stirrer and a thermometer, and the mixture was stirred and cooled to -78°C. A 2.76M butyllithium/hexane solution (94 mL) was added dropwise at -78°C over 1 hour. After stirring at -78 °C for 30 minutes, compound G-1-11 (43.8 g) was added dropwise at -78 °C over 1 hour. After stirring at −78° C. for 3 hours, DMF (45 g) was added dropwise at −78° C. over 30 minutes. After stirring at −78° C. for 1 hour, the temperature was raised to −20° C., and the reaction solution was added dropwise to 10% hydrochloric acid (100 mL). The organic layer was separated, and the aqueous layer was extracted with toluene (200 mL). The organic layers thus obtained were combined, washed with water, an aqueous solution of sodium hydrogen carbonate and saturated saline, and dried by adding anhydrous sodium sulfate. After concentrating the obtained solution, toluene (50 mL) was added and dissolved, the solution was passed through a silica gel column, and the obtained column passing solution was concentrated to dryness to obtain compound G-1-12 (20 g). It was

(Synthesis of Compound G-1-13)
Under a nitrogen atmosphere, in a reaction vessel equipped with a stirrer, a thermometer, a dropping funnel, and a cooling tube, compound G-1-12 (20 g), 4-propylphenylboric acid (14.6 g), bis[di-dichloride] tert-Butyl(4-dimethylaminophenyl)phosphine]palladium(II) (0.27 g) and THF (80 mL) were added, and the temperature was raised to 60°C with stirring. A 2M aqueous sodium carbonate solution (60 ml) was added dropwise to the reaction mixture. After stirring at 60° C. for 2 hours, heating was stopped and the solution temperature was returned to room temperature. Then, 10% hydrochloric acid (75 mL) was added. The organic layer was separated, and the aqueous layer was reextracted with toluene (200 mL). The obtained organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and dried. After concentrating the obtained solution, toluene (100 mL) was added and dissolved, and the solution was passed through a silica gel column, and the obtained column passing solution was concentrated to dryness to give compound G-1-13 (23.4 g). ) Got.

(Synthesis of Compound G-1-14)
Compound G-1-13 (23.4 g), 2-methyl-2-butene (57.4 g), butanol (240 mL), water (240 mL) were placed in a reaction vessel equipped with a stirrer, a thermometer, and a dropping funnel. After stirring with stirring, NaClO ₂ (22.1 g), NaH ₂ PO ₄ (49.07 g) and water (100 mL) were added dropwise over 1 hour. After stirring at room temperature for 30 minutes, aqueous sodium sulfite solution was added, and the mixture was extracted with ethyl acetate (1000 mL). The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The obtained solution was concentrated to obtain compound G-1-14 (28 g).

(Synthesis of Compound G-1-15)
Under a nitrogen atmosphere, to a reaction vessel equipped with a stirrer and a thermometer, compound G-1-14 (28 g) and concentrated sulfuric acid (112 g) were added and stirred, heated to 90° C. and stirred for 20 hours. The reaction solution was added to a 15% aqueous sodium carbonate solution for neutralization, and the mixture was extracted with ethyl acetate (800 mL). The obtained organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and dried. After concentrating the obtained solution, toluene (100 mL) was added and dissolved, and the solution was passed through a silica gel column, and the obtained column passing solution was concentrated to dryness to obtain compound G-1-15 (14 g). It was

(Synthesis of Compound G-1-16)
Under a nitrogen atmosphere, to a reaction vessel equipped with a stirrer, a thermometer and a dropping funnel, compound G-1-15 (14 g), hydrazine monohydrate (12 g) and diethylene glycol (500 mL) were added and stirred for 1 hour. The temperature was raised to 80°C. After stirring at 80°C for 2 hours, the mixture was cooled to room temperature, potassium hydroxide (16.5 g) and water (70 mL) were added, the temperature was raised to 80°C over 1 hour, and the mixture was refluxed for 2 hours. The reaction solution was cooled to room temperature, poured into water (500 mL), and stirred for 30 minutes. The aqueous layer was extracted with toluene (200 mL). The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. After concentrating the obtained solution, toluene was added and dissolved, and the solution was passed through a silica gel column, and the obtained column passing solution was concentrated to dryness to obtain compound G-1-16 (5 g).
Phase transition temperature: Cr 43.4 Iso
MS m/z: 269 [M ⁺ ]

(Comparative Example 1)
The compound of Comparative Example 1 below was synthesized according to the method described in Patent Document 1 above.

(Measurement of extrapolated rotational viscosity (γ ₁ ))
The host liquid crystal (H) described in Example 5 in JP2018-2670A was prepared. T _n-i (nematic phase-isotropic liquid phase transition temperature), Δε (dielectric anisotropy at 25° C.), Δn (refractive index anisotropy at 25° C.) and γ _{1 of the} host liquid crystal (H) The values of (rotational viscosity coefficient at 25° C.) (all measured values) were as follows.
Δε: -2.79
Δn: 0.101
γ ₁ : 112

A liquid crystal composition comprising 90% of the base liquid crystal (H) and 10% of the compound obtained in each of Examples and Comparative Examples was prepared. The rotational viscosity (mPa·s) value at 25° C. of this composition was measured, and extrapolation rotation of the compounds obtained in Examples and Comparative Examples was based on the amount of change from the host liquid crystal (LC-1). The viscosity (γ ₁ ) was determined. The results are shown in Table 1.

Claims (8)

General formula (I):

(In the formula, R ⁱ¹ and R ⁱ² are each independently a chlorine atom, a bromine atom, an iodine atom, a hydroxyl group, -BR ¹ R ² (In the formula, R ¹ and R ² are each independently a hydroxyl group, a carbon atom. Represents an alkoxy group of the formulas 1 to 4, or R ¹ and R ² are bonded to each other to form a cyclic structure —O—(CR ³ R ⁴ ) _n —O— (wherein R ³ and R ⁴ are each independently Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, n represents 2 or 3, and a plurality of CR ³ R ^{4 s} may be the same or different)), carbon It represents an alkyl group having 1 to 15 atoms or an alkenyl group having 2 to 15 carbon atoms, and one —CH ₂ — present in the alkyl group or alkenyl group or two or more —CH ₂ which are not adjacent to each other. Each -may be independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -SOO-O- or -C≡C-, and the alkyl group or The hydrogen atom present in the alkenyl group may be replaced by a fluorine atom,
A ⁱ¹ and A ⁱ² are each independently (a) a 1,4-cyclohexylene group (one —CH ₂ — present in this group or two or more —CH ₂ — not adjacent to each other is — It may be replaced with O- or -S-).
(B) 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ which are not adjacent to each other may be replaced by —N═, which is present in this group) May be substituted with a fluorine atom), and (c) 1,4-cyclohexenylene group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene- 2,6-diyl group or decahydronaphthalene-2,6-diyl group (the hydrogen atom present in these groups may be replaced by a fluorine atom, and the naphthalene-2,6-diyl group or 1, (One -CH= present in the 2,3,4-tetrahydronaphthalene-2,6-diyl group or two or more non-adjacent -CH= may be replaced by -N=.)
Represents a group selected from the group consisting of
Z ⁱ¹ and Z ⁱ² are each independently —CH ₂ O—, —OCH ₂ —, —CF ₂ O—, —OCF ₂ —, —COO—, —OCO—, —CH ₂ CH ₂ —, —CF. _{2 CF 2 -, - CH =} CH -, - CF = CF -, - C≡C- or a single bond,
n ⁱ¹ and m ⁱ¹ each independently represent 0, 1 or 2, but when n ⁱ¹ represents 2 and a plurality of A ⁱ¹ and Z ⁱ¹ are present, they may be the same or different, and , M ⁱ¹ represents 2 and a plurality of A ⁱ² and Z ⁱ² are present, they may be the same or different,
X ⁱ represents a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group or a trifluoromethoxy group,
Y ⁱ is -O -, - S -, - SO -, - SOO -, - CF 2 -, - CO- or -CH ₂ - represents a. )
The compound represented by. In formula (I), R ⁱ¹ and R ⁱ² are each independently an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or a carbon atom. The compound according to claim 1, which represents an alkenyloxy group of the number 2 to 8. The compound according to claim 1 or 2, wherein in the general formula (I), X ⁱ represents a fluorine atom. In the general formula (I), ^{Y i} represents -O- or -S-, the compound according to any one of claims 1 to 3. The compound according to any one of claims 1 to 4, wherein in the general formula (I), n ⁱ¹ and m ⁱ¹ both represent 0.   A composition containing one kind or two or more kinds of the compound according to any one of claims 1 to 5.   The composition according to claim 6, which exhibits a liquid crystal phase. A liquid crystal display device using the composition according to claim 6.