CN111170827A

CN111170827A - Compound, composition and liquid crystal display element

Info

Publication number: CN111170827A
Application number: CN201911030626.6A
Authority: CN
Inventors: 门本丰; 岩楯展行; 林正直
Original assignee: DIC Corp
Current assignee: DIC Corp
Priority date: 2018-11-13
Filing date: 2019-10-28
Publication date: 2020-05-19
Also published as: JP2020079215A

Abstract

The invention relates toA compound, a composition and a liquid crystal display element. The present invention addresses the problem of providing a liquid crystal compound having low viscosity and negative dielectric anisotropy (Δ ∈). The compound is represented by the general formula (I) (wherein R isⁱ¹And Rⁱ²Each independently represents an alkyl group having 1 to 15 carbon atoms or the like, Aⁱ¹And Aⁱ²Each independently represents 1, 4-cyclohexylene or the like, Zⁱ¹And Zⁱ²Each independently represents-CH₂O-, etc., nⁱ¹And mⁱ¹Each independently represents 0, 1 or 2, XⁱRepresents a fluorine atom or the like, Yⁱrepresents-O-, etc. ).

Description

Compound, composition and liquid crystal display element

Technical Field

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

Background

Liquid crystal display elements are used in various household appliances such as clocks and calculators, measuring instruments, panels for automobiles, word processors, electronic notebooks, printers, computers, televisions, and the like. Representative examples of liquid crystal display systems include TN (twisted nematic) type, STN (super twisted nematic) type, DS (dynamic light scattering) type, GH (guest host) type, IPS (in-plane switching) type, OCB (optically compensated birefringence) type, ECB (voltage controlled birefringence) type, VA (vertically aligned) type, CSH (color super vertical) type, and FLC (ferroelectric liquid crystal). As a driving method of the liquid crystal display, a static driving method, a multiplex driving method, a simple matrix method, and an Active Matrix (AM) method using a driving method such as a TFT (thin film transistor) or a TFD (thin film diode) can be cited.

Among them, in display systems such as IPS mode, ECB mode, VA mode, and CSH mode, a liquid crystal composition having a negative dielectric anisotropy (Δ ∈) is used. These liquid crystal compositions are required to be driven at a low voltage, respond at a high speed and have a wide operating temperature range, i.e., to have a large absolute value of Δ ∈, to have low viscosity, and to have a high nematic phase-isotropic liquid phase transition temperature (T)_ni) Among them, in the VA display system using AM driving applied to a television or the like, high-speed response is important, and therefore, a liquid crystal composition is particularly required to have low viscosity.

Although the following compounds having a dibenzofuran ring substituted with 2 fluorine atoms have been reported, compounds having a dibenzofuran ring substituted with 1 fluorine atom have not been disclosed (patent documents 1 and 2).

[ solution 1]

(in the formula, R¹And R²Each independently represents 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 each independently represent 0 or 1. )

Documents of the prior art

Patent document

Patent document 1: german patent application publication No. 102015002298

Patent document 2: japanese patent No. 4379857

Disclosure of Invention

Problems to be solved by the invention

The present invention addresses the problem of providing a liquid crystal compound having low viscosity and negative dielectric anisotropy (Δ ∈), and also providing a liquid crystal composition and a liquid crystal display element each of which comprises the compound as a constituent member.

Means for solving the problems

The present inventors have conducted various studies on compounds in order to solve the above problems, and as a result, have found that the following compounds having a condensed ring substituted with 1 fluorine atom or the like can effectively solve the problems, and have completed the present invention.

One aspect of the present invention provides a compound represented by the general formula (I): [ solution 2]

(in the formula, Rⁱ¹And Rⁱ²Each independently represents a chlorine atom, a bromine atom, an iodine atom, a hydroxyl group, -BR¹R²(in the formula, R¹And R²Each independently represents a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, or R¹And R²Are bonded to each other to form a cyclic structure to represent-O- (CR)³R⁴)_n-O- (wherein R is³And R⁴Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atomsN represents 2 or 3, a plurality of CR's being present³R⁴The same or different), an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms, wherein 1-CH is present in the alkyl group or the alkenyl group₂-or non-adjacent 2 or more-CH₂Each independently of the others may be substituted by-O-, -S-, -CO-, -COO-, -OCO-, -SOO-O-or-C.ident.C-, and furthermore, the hydrogen atoms present in the alkyl or alkenyl groups may be substituted by fluorine atoms,

Aⁱ¹and Aⁱ²Each independently represents a group selected from the group consisting of,

(a)1, 4-cyclohexylene (1-CH present in the radical)₂-or non-adjacent 2 or more-CH₂-may be substituted by-O-or-S-. ) A

(b)1, 4-phenylene (1-CH ═ or non-adjacent 2 or more-CH ═ present in the group may be substituted with-N ═ and 1 hydrogen atom present in the group may be substituted with a fluorine atom), and

(c)1, 4-cyclohexenylene, naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (the hydrogen atoms present in these groups may be substituted by fluorine atoms, and further, 1-CH ═ or not adjacent 2 or more-CH ═ present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted by-N ═ to.)

Zⁱ¹And Zⁱ²Each independently represents-CH₂O-、-OCH₂-、-CF₂O-、-OCF₂-、-COO-、-OCO-、-CH₂CH₂-、-CF₂CF₂-, -CH-, -CF-, -C.ident.C-or a single bond,

nⁱ¹and mⁱ¹Each independently represents 0, 1 or 2, when nⁱ¹Represents 2 and a plurality of A existⁱ¹And Zⁱ¹In the case of (3), they may be the same or different; furthermore, when mⁱ¹Represents 2 and a plurality of A existⁱ²And Zⁱ²In the case of (2), they may be the same or different,

Xⁱrepresents a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group or a trifluoromethoxy group,

Yⁱrepresents-O-, -S-,-SO-、-SOO-、-CF₂-, -CO-or-CH₂-。)。

Another aspect of the present invention provides a composition containing 1 or 2 or more compounds represented by the general formula (I), and a liquid crystal display element using the composition.

ADVANTAGEOUS EFFECTS OF INVENTION

The compound of the present invention is a liquid crystal compound having low viscosity and negative dielectric anisotropy (. DELTA.. di-elect cons.). Therefore, the compound of the present invention is useful as a component of a liquid crystal composition for a liquid crystal display element which requires a high-speed response.

Detailed Description

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

To make gamma₁Decrease Rⁱ¹And Rⁱ²Each independently preferably represents an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, more preferably represents an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms. The alkyl group and the alkenyl group are preferably linear. In order to increase the absolute value of Δ ε, Rⁱ¹And Rⁱ²Each independently is preferably an alkoxy group having 1 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, more preferably an alkoxy group having 1 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms. In order to improve the miscibility with other liquid crystal components, R is preferablyⁱ¹And Rⁱ²Is different, preferably alkoxy is Rⁱ¹Or Rⁱ²Any one of the above. Rⁱ¹And Rⁱ²The hydrogen atoms present in (a) may be substituted by fluorine atoms, but are preferably not substituted by fluorine atoms.

When the intermediate is represented by the general formula (I), R is preferablyⁱ¹And Rⁱ²At least one of them represents a chlorine atom, a bromine atom, an iodine atom, a hydroxyl group, a methanesulfonyloxy group, a p-toluenesulfonyloxy group, a trifluoromethanesulfonyloxy group or-BR¹R²(in the formula, R¹And R²Each independently represents a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, or R¹And R²Are bonded to each other to form a cyclic structure to represent-O- (CR)³R⁴)_n-O- (wherein R is³And R⁴Each 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's are present³R⁴May be the same or different). ).

Aⁱ¹And Aⁱ²Each independently preferably represents a group selected from the following.

[ solution 3]

In particular, in order to make γ₁Decrease of Aⁱ¹And Aⁱ²Each independently is preferably trans-1, 4-cyclohexylene, unsubstituted 1, 4-phenylene, 2-fluoro-1, 4-phenylene or 3-fluoro-1, 4-phenylene, and further preferably trans-1, 4-cyclohexylene. To improve the miscibility with other liquid crystal components, Aⁱ¹And Aⁱ²Each independently preferably being trans-1, 4-cyclohexylene, 2-fluoro-1, 4-phenylene or 3-fluoro-1, 4-phenylene. To increase T_ni，Aⁱ¹And Aⁱ²Each independently of the others is preferably unsubstituted 1, 4-phenylene, unsubstituted 1, 4-cyclohexenylene, 1, 4-cyclohexenylene or unsubstituted naphthalene-2, 6-diyl. To show a large Δ ε in the negative direction, Aⁱ¹And Aⁱ²Each independently preferably being 2-fluoro-1, 4-phenylene, 3-fluoro-1, 4-phenylene or 2, 3-difluoro-1, 4-phenylene. To exhibit a large Δ ∈ while simultaneously satisfying miscibility with other liquid crystal components, aⁱ¹And Aⁱ²The total number of fluorine atoms present in (A) is preferably 1 to 4, more preferably 1 to 3.

To make gamma₁Decrease of Zⁱ¹And Zⁱ²Each independently is preferably a single bond, -CH₂CH₂-、-CH₂O-or-OCH₂-, more preferably a single bond or-CH₂CH₂-. To increase T_ni，Zⁱ¹And Zⁱ²Each independently is preferably a single bond, -COO-, -OCO-, -CH ≡ CH-or-C ≡ C-, and is more preferably a single bond, -CH ═ CH-or-C ≡ C-. To improve the miscibility with other liquid crystal components, Zⁱ¹And Zⁱ²Each independently is preferably a single bond, -CH₂CH₂-、-CH₂O-or-OCH₂-. In order to improve long-term reliability in the production of a liquid crystal display element, a single bond is preferable.

nⁱ¹And mⁱ¹Each independently preferably represents 0 or 1, more preferably nⁱ¹And mⁱ¹Both represent 0.

XⁱPreferably represents a fluorine atom.

YⁱPreferably represents-O-, -S-or-CH₂-more preferably-O-or-S, still more preferably-O-. In the general formula (I), preferred are compounds represented by the following general formulae (I-1) to (I-18).

[ solution 4]

(in the formula, Rⁱ¹And Rⁱ²Respectively represent R in the general formula (I)ⁱ¹And Rⁱ²The same meaning is used. )

Among the compounds represented by the above general formulae (I-1) to (I-18), the compounds represented by the following formulae are preferable.

[ solution 5]

[ solution 6]

[ solution 7]

[ solution 8]

[ solution 9]

[ solution 10]

[ solution 11]

[ solution 12]

[ solution 13]

[ solution 14]

[ solution 15]

[ solution 16]

[ solution 17]

[ solution 18]

[ solution 19]

[ solution 20]

[ solution 21]

[ solution 22]

[ solution 23]

[ solution 24]

[ solution 25]

[ solution 26]

(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 to these manufacturing methods.

(production method 1)

[ solution 27]

(in the formula, Rⁱ¹、Rⁱ²、Aⁱ¹、Aⁱ²、Zⁱ¹、Zⁱ²、nⁱ¹、mⁱ¹And XⁱRespectively represent R in the general formula (I)ⁱ¹、Rⁱ²、Aⁱ¹、Aⁱ²、Zⁱ¹、Zⁱ²、nⁱ¹、mⁱ¹And XⁱIn the same sense, the term "a" or "an" means,

R^im1and R^im2Each independently represents a hydrogen atom, a methyl, ethyl or propyl group, or R^im1And R^im2Are bonded to each other to form a cyclic structure to represent-CH₂-CH₂-、-CH₂-CH₂-CH₂-or-CH₂-C(CH₃)₂-CH₂-，

X^im1Represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom,

X^im2represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a p-toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group,

Y^im1represents-O-or-S-. )

The compound represented by the general formula (S-3) can be obtained by reacting the compound represented by the general formula (S-1) with the compound represented by the general formula (S-2) in the presence of a transition metal catalyst and a base.

The transition metal catalyst used may be any catalyst as long as the reaction is appropriately carried out, and is preferably tetrakis (triphenylphosphine) palladium (0), palladium (II) acetate, bis (triphenylphosphine) palladium (II) dichloride, [1,1 '-bis (diphenylphosphino) ferrocene ] palladium (II) dichloride or bis [ di-tert-butyl (4-dimethylaminophenyl) phosphine ] palladium (II) dichloride, and more preferably tetrakis (triphenylphosphine) palladium (0), [1, 1' -bis (diphenylphosphino) ferrocene ] palladium (II) dichloride or bis [ di-tert-butyl (4-dimethylaminophenyl) phosphine ] palladium (II) dichloride. In order to properly proceed the reaction, a phosphine ligand such as triphenylphosphine may be added as necessary.

The reaction solvent to be used may be any solvent as long as the reaction is appropriately carried out, and is preferably an ether solvent such as tetrahydrofuran, diethyl ether or tert-butyl methyl ether, an alcohol solvent such as methanol, ethanol or propanol, an aromatic solvent such as benzene, toluene or xylene, and more preferably tetrahydrofuran, ethanol or toluene. In order to properly proceed the reaction, water may be used as necessary.

The base to be used may be any base as long as the reaction is appropriately carried out, and is preferably a carbonate such as potassium carbonate, sodium carbonate or cesium carbonate, a phosphate such as tripotassium phosphate or monopotassium phosphate, and more preferably potassium carbonate, cesium carbonate or tripotassium phosphate.

The reaction temperature may be any temperature as long as the reaction is properly carried out, and is preferably from room temperature to the reflux temperature of the solvent used, more preferably from 40 ℃ to the reflux temperature of the solvent, and particularly preferably from 60 ℃ to the reflux temperature of the solvent.

Y in the compound represented by the general formula (I) can be obtained by subjecting the compound represented by the general formula (S-3) to intramolecular reactionⁱA compound represented by the general formula (S-4) which is-O-or-S-. The intramolecular reaction can be carried out by using a base with-Y of the general formula (S-3)^im1-H deprotonation to generate an anion.

The base used in this case includes metal hydrides, metal carbonates, metal phosphates, metal hydroxides, metal carboxylates, metal amides, metals, and the like, and among them, alkali metal hydrides, alkali metal phosphates, alkali metal carbonates, alkali metal hydroxides, alkali metal amides, and alkali metals are preferable, and alkali metal phosphates, alkali metal hydrides, and alkali metal carbonates are more preferable. As the alkali metal hydride, lithium hydride, sodium hydride and potassium hydride; as the alkali metal phosphate, there may be preferably mentioned tripotassium phosphate; as the alkali metal carbonate, sodium hydrogen carbonate, cesium carbonate, potassium carbonate and potassium hydrogen carbonate can be preferably cited.

The reaction solvent may be any solvent as long as the reaction is appropriately carried out, and an ether solvent, a chlorine solvent, a hydrocarbon solvent, an aromatic solvent, a polar solvent, or the like can be preferably used. Preferred examples of the ether solvent include 1, 4-dioxane, 1, 3-dioxane, tetrahydrofuran, diethyl ether, and tert-butyl methyl ether; preferred examples of the chlorine-based solvent include dichloromethane, 1, 2-dichloroethane, and carbon tetrachloride; preferred examples of the hydrocarbon solvent include pentane, hexane, cyclohexane, heptane, octane, and the like; preferred examples of the aromatic solvent include benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and the like; preferable examples of the polar solvent include N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, and sulfolane. Among these, 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 2 or more solvents may be used in combination.

As for the reaction temperature, it may be carried out in a range from the freezing point to the reflux temperature of the solvent, preferably 0 ℃ to 180 ℃.

(production method 2)

[ solution 28]

R^im3and R^im4Each independently represents a hydrogen atom, a methyl, ethyl or propyl group, or R^im1And R^im2Are bonded to each other to form a cyclic structure to represent-CH₂-CH₂-、-CH₂-CH₂-CH₂-or-CH₂-C(CH₃)₂-CH₂-，

X^im3Represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom,

X^im4represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a p-toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group,

Y^im2represents-O-or-S-. )

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

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

Y in the compound represented by the general formula (I) can be obtained by subjecting the compound represented by the general formula (S-7) to intramolecular reactionⁱA compound represented by the general formula (S-8) which is-O-or-S-. The intramolecular reaction can be carried out by using a base with-Y of the general formula (S-7)^im2-H deprotonation to generate an anion.

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

(production method 3)

[ solution 29]

(in the formula, Rⁱ¹、Rⁱ²、Aⁱ¹、Aⁱ²、Zⁱ¹、Zⁱ²、nⁱ¹、mⁱ¹、XⁱAnd YⁱRespectively represent R in the general formula (I)ⁱ¹、Rⁱ²、Aⁱ¹、Aⁱ²、Zⁱ¹、Zⁱ²、nⁱ¹、mⁱ¹、XⁱAnd YⁱIn the same sense, the term "a" or "an" means,

R^iaand R^ibEach independently represents a chlorine atom, a bromine atom, an iodine atom, a hydroxyl group, a methanesulfonyloxy group, a p-toluenesulfonyloxy group, a trifluoromethanesulfonyloxy group or-BR¹R²(in the formula, R¹And R²Each independently represents a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, or R¹And R²Are bonded to each other to form a cyclic structure to represent-O- (CR)³R⁴)_n-O- (wherein R is³And R⁴Each 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's are present³R⁴May be the same or different). ),

R^icand R^idEach independently represents a chlorine atom, a bromine atom, an iodine atom, a hydroxyl group, a methanesulfonyloxy group, a p-toluenesulfonyloxy group, a trifluoromethanesulfonyloxy group, -BR⁵R⁶(in the formula, R⁵And R⁶Each independently represents a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, or R⁵And R⁶Are bonded to each other to form a cyclic structure to represent-O- (CR)⁷R⁸)_n1-O- (wherein R is⁷And R⁸Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, n1 represents 2 or 3, and a plurality of CR's are present⁷R⁸May be the same or different). ) or-ZnX^im5(in the formula, X^im5Represents a chlorine atom, a bromine atom or an iodine atom. ). )

For example, R^iaAnd R^ibR is a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a p-toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group^icAnd R^idis-BR⁵R⁶or-ZnX^im5In the case of (b), the compound represented by the general formula (I) can be obtained 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. Further, by reacting the compound represented by the general formula (Ib) with the compound represented by the formula (S-10) in the presence of a transition metal catalyst and/or a base, it is possible to obtain a compound represented by the general formula (I)The compounds shown are shown. The reaction solvent, transition metal catalyst and base used are the same as those used in the step of obtaining the compound represented by the general formula (S-3). The reaction temperature is the same as that in the step of obtaining the compound represented by the general formula (S-3).

Further, for example, R^iaAnd R^ibIs hydroxy and R^icAnd R^idIn the case of a chlorine atom, a bromine atom or an iodine atom, the compound represented by the general formula (I) can be obtained by reacting the compound represented by the general formula (Ia) with the compound represented by the general formula (S-9) in the presence of a base. Further, 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 formula (S-10) in the presence of a base.

(composition)

Since the compound represented by the general formula (I) exhibits negative dielectric anisotropy (Δ ∈), the composition of the present invention containing the compound represented by the general formula (I) preferably has negative dielectric anisotropy.

In the composition of the present invention, since the effect is not exhibited if the content of the compound represented by the general formula (I) is small, the lower limit of the content is preferably 1% by mass or more (hereinafter, the% in the composition means% by mass), preferably 2% or more, preferably 5% or more, and 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, still more preferably 50% or less, and particularly preferably 40% or less. The compound represented by the general formula (I) may be used alone in 1 kind, or 2 or more kinds may be used simultaneously. In order to adjust the physical property values of the liquid crystal composition, compounds other than the compound represented by the general formula (I) may be used, and a compound having no liquid crystal phase may be added as necessary in addition to the compound having a liquid crystal phase.

The composition of the present invention contains at least 1 compound represented by the general formula (I) as a first component thereof, and particularly preferably contains at least 1 component selected from the group consisting of the following second component and third component as another component.

The second component preferably contains 1 or 2 or more compounds selected from the group of compounds represented by the general formulae (N-1), (N-2) and (N-3). These compounds correspond to compounds with negative dielectricity (Δ ∈ negative in sign and greater than 2 ° absolute).

[ solution 30]

(in the formula, wherein,

R^N11、R^N12、R^N21、R^N22、R^N31and R^N32Each independently represents an alkyl group having 1 to 8 carbon atoms, 1 or 2 or more-CH groups which are not adjacent to each other in the alkyl group₂-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,

A^N11、A^N12、A^N21、A^N22、A^N31and A^N32Each independently represents a group selected from the group consisting of,

(a11)1, 4-cyclohexylene (1-CH present in the radical)₂-or non-adjacent 2 or more-CH₂-may be substituted by-O-. )

(b11)1, 4-phenylene (1-CH-present in the radical or not adjacent 2 or more-CH-may be substituted by-N) -) and

(c11) naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-CH ═ present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or 2 or more-CH ═ which are not adjacent may be substituted by-N ═ can be used.)

The above-mentioned group (a11), group (b11) and 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^N31and Z^N32Each independently represents a single bond, -CH₂CH₂-、-(CH₂)₄-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCF₂-、-CF₂O-, -CH-N-CH-, -CH-, -CF-or-C ≡ C-,

X^N21represents a hydrogen atom or a fluorine atom,

T^N31represents-CH₂-or an oxygen atom,

n^N11、n^N12、n^N21、n^N22、n^N31and n^N32Each independently represents an integer of 0 to 3, n^N11+n^N12、n^N21+n^N22And n^N31+n^N32Each independently is 1,2 or 3, when a plurality of A's are present^N11～A^N32、Z^N11～Z^N32In the case of (2), they may be the same or different. However, the compound represented by the general formula (N-1) is not included in the general formula (N-2) and the general formula (N-3), and the compound represented by the general formula (N-2) is not included in the general formula (N-3). )

The compounds represented by the general formulae (N-1), (N-2) and (N-3) correspond to compounds having negative dielectric properties (Δ ε has a negative sign and an absolute value of more than 2.), and preferably compounds having negative Δ ε and an absolute value of more than 3.

In the general formulae (N-1), (N-2) and (N-3), R^N11、R^N12、R^N21、R^N22、R^N31And R^N32Independently of each other, the alkyl group has 1 to 8 carbon atoms, the alkoxy group has 1 to 8 carbon atoms, the alkenyl group has 2 to 8 carbon atoms or the alkenyloxy group has 2 to 8 carbon atoms, preferably the alkyl group has 1 to 5 carbon atoms, the alkoxy group has 1 to 5 carbon atoms, the alkenyl group has 2 to 5 carbon atoms or the alkenyloxy group has 2 to 5 carbon atoms, more preferably the alkyl group has 1 to 5 carbon atoms or the alkenyl group has 2 to 5 carbon atoms, more preferably the alkyl group has 2 to 5 carbon atoms or the alkenyl group has 2 to 3 carbon atoms, and particularly preferably the alkenyl group has 3 carbon atoms (propenyl). Wherein R is used in combination^N11And R^N12At least 1 or more of the compounds represented by the general formula (I) and the compound represented by the general formula (I) can significantly suppress a decrease in the Voltage Holding Ratio (VHR). Likewise, by using R in combination^N21And R^N22At least 1 or more of the compounds represented by the general formula (I) and the compound represented by the general formula (I) can remarkably inhibit the reduction of the Voltage Holding Ratio (VHR); further, by using R in combination^N31And R^N32At least 1 or more of the compounds represented by the general formula (I) and the compound represented by the general formula (I) can significantly suppress a decrease in the Voltage Holding Ratio (VHR).

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

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

[ solution 31]

In the case of a requirement to increase Δ n, A^N11、A^N12、A^N21、A^N22、A^N31And A^N32Each independently preferably aromatic; for improving the response speed, aliphatic is preferable; preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2 ] phenylene]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl; more preferably, it means a structure described below,

[ solution 32]

More preferably, it represents trans-1, 4-cyclohexylene or 1, 4-phenylene.

Z^N11、Z^N12、Z^N21、Z^N22、Z^N31And Z^N32Each independently preferably represents-CH₂O-、-CF₂O-、-CH₂CH₂-、-CF₂CF₂-or a single bond, more preferably-CH₂O-、-CH₂CH₂-or a single bond, particularly preferably-CH₂O-or a single bond.

X^N21Preferably a fluorine atom.

T^N31Preferably an oxygen atom.

n^N11+n^N12、n^N21+n^N22And n^N31+n^N32Preferably 1 or 2, preferably n^N11Is 1 and n^N12A combination of 0, n^N11Is 2 and n^N12A combination of 0, n^N11Is 1 and n^N12Is a combination of 1, n^N11Is 2 and n^N12Is a combination of 1, n^N21Is 1 and n^N22A combination of 0, n^N21Is 2 and n^N22A combination of 0, n^N31Is 1 and n^N32A combination of 0, n^N31Is 2 and n^N32Is a combination of 0.

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

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

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

When the viscosity of the composition of the present invention is kept low and a composition having a high response speed is required, the lower limit value and the upper limit value are preferably low. Further, T of the composition of the present invention is maintained_niWhen the composition has a high level and requires good temperature stability, the lower limit value and the upper limit value are preferably low. In order 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.

The composition of the present invention preferably contains 1 or 2 or more compounds represented by the general formula (i-1) as the general formula (N-1).

[ solution 33]

(in the formula, A)ⁱ¹¹、Aⁱ¹²And Aⁱ¹³Each independently represents 1, 4-cyclohexylene or 1, 4-phenylene, 1-CH present in 1, 4-cyclohexylene₂-or non-adjacent 2 or more-CH₂May be substituted by-O-or-S-, 1 hydrogen atom present in the 1, 4-phenylene group may each independently be substituted by a fluorine atom or a chlorine atom, Zⁱ¹represents-OCH₂-、-CH₂O-、-CF₂O-、-OCF₂-、-CH₂CH₂-or-CF₂CF₂-，mⁱ¹¹And mⁱ¹²Each independently represents 0 or 1, R^N11、R^N12And Z^N12Each independently represents R in the general formula (N-1)^N11、R^N12And Z^N12The same meaning is used. )

The compound represented by the general formula (i-1) is preferably a compound represented by the general formula (i-1A), the general formula (i-1B) or the general formula (i-1C).

[ chemical 34]

(in the formula, R^N11、R^N12、Aⁱ¹¹And Zⁱ¹Each independently represents R in the general formula (i-1)^N11、R^N12、Aⁱ¹¹And Zⁱ¹The same meaning is used. )

[ solution 35]

(in the formula, R^N11、R^N12、Aⁱ¹¹、Aⁱ¹²And Zⁱ¹Each independently represents R in the general formula (i-1)^N11、R^N12、Aⁱ¹¹、Aⁱ¹²And Zⁱ¹The same meaning is used. )

[ solution 36]

(in the formula, mⁱ¹³Represents 1, R^N11、R^N12、Aⁱ¹¹、Aⁱ¹²、Aⁱ¹³、Zⁱ¹、Zⁱ²And mⁱ¹¹Each independently represents R in the general formula (i-1)^N11、R^N12、Aⁱ¹¹、Aⁱ¹²、Aⁱ¹³、Zⁱ¹、Zⁱ²And mⁱ¹¹The same meaning is used. )

The compound represented by the general formula (i-1A) is preferably a compound represented by the following general formula (i-1A-1) to general formula (i-1A-4).

[ solution 37]

(in the formula, R^N11And R^N12Each independently representAnd R in the general formula (i-1)^N11And R^N12The same meaning is used. )

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).

[ solution 38]

(in the formula, R^N11And R^N12Each independently represents R in the general formula (i-1)^N11And R^N12The same meaning is used. )

As the compound represented by the general formula (i-1C), compounds represented by the following general formula (i-1C-1) and general formula (i-1C-2) are preferable.

[ solution 39]

The composition of the present invention preferably contains 1 or 2 or more compounds represented by the general formula (i-1), may contain 1 or 2 or more compounds selected from the group of compounds represented by the general formula (i-1A), the general formula (i-1B) or the general formula (i-1C), and may contain 1 or more compounds each represented by the general formula (i-1A), the general formula (i-1B) or the general formula (i-1C). It preferably contains 1 or 2 or more compounds represented by the general formula (i-1A) and the general formula (i-1B), and more preferably 2 to 10.

More specifically, the general formula (i-1A), the general formula (i-1B) and the general formula (i-1C) preferably contain 1 or 2 or more compounds selected from the group consisting of the compounds represented by the general formula (i-1A-1), the general formula (i-1B-1) and the general formula (i-1C-1), and more preferably a combination of the compound represented by the general formula (i-1A-1) and the compound represented by the general formula (i-1B-1).

Further, the composition of the present invention preferably contains 1 or 2 or more compounds represented by the general formula (ii).

[ solution 40]

(in the formula, A)ⁱⁱ¹、Aⁱⁱ²Each independently represents 1, 4-cyclohexylene or 1, 4-phenylene, 1-CH present in 1, 4-cyclohexylene₂-or non-adjacent 2 or more-CH₂May be substituted by-O-or-S-, 1 hydrogen atom present in the 1, 4-phenylene group may each independently be substituted by a fluorine atom or a chlorine atom, mⁱⁱ¹And mⁱⁱ²Each independently represents 1 or 2, R^N11And R^N12Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

The general formula (ii-1) preferably contains 1 or 2 or more compounds represented by the general formula (ii-1).

[ solution 41]

(in the formula, R^N11、R^N12、Aⁱⁱ¹And mⁱⁱ¹Represents R in the general formula (ii)^N11、R^N12、Aⁱⁱ¹And mⁱⁱ¹The same meaning is used. )

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).

[ solution 42]

(in the formula, R^N11、R^N12And Aⁱⁱ¹Represents R in the general formula (ii)^N11、R^N12And Aⁱⁱ¹The same meaning is used. )

[ solution 43]

(in the formula, A)ⁱⁱ¹¹And Aⁱⁱ¹¹Each independently represents 1, 4-cyclohexylene or 1, 4-phenylene, 1-CH present in 1, 4-cyclohexylene₂-or non-adjacent 2 or more-CH₂-may be substituted by-O-or-S-, 1 hydrogen atom present in the 1, 4-phenylene group may each independently be substituted by a fluorine atom or a chlorine atom, R^N11And R^N12Represents R in the general formula (ii)^N11And R^N12The same meaning is used. )

As the compound represented by the general formula (ii-1A), preferred are compounds represented by the following general formula (ii-1A-1) and general formula (ii-1A-2).

[ solution 44]

(in the formula, R^N11And R^N12Represents R in the general formula (ii)^N11And R^N12The same meaning is used. )

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).

[ solution 45]

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

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

Further, the general formula (N-1) preferably contains 1 or 2 or more compounds represented by the following general formula (LC 3-b).

[ solution 46]

(in the formula, R^N11、R^N12、A^N11、A^N12And Z^N11Each independently represents R in the general formula (N-1)^N11、R^N12、A^N11、A^N12And Z^N11Same meaning as X^LC3b1～X^LC3b4Represents a hydrogen atom or a fluorine atom, X^LC3b1And X^LC3b2Or X^LC3b3And X^LC3b4At least one combination of (a) and (b) each represents a fluorine atom, m^LC3b1Represents 0 or 1. However, the compounds represented by the general formula (i-1) and the general formula (ii) are not included in the general formula (LC 3-b). )

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-b 10).

[ solution 47]

(in the formula, R^N11And R^N12Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N11And R^N12The combination of (A) and (B) is not particularly limited, but it is preferably a combination of two members each representing an alkyl group, a combination of two members each representing an alkenyl group, a combination of one member each representing an alkyl group and the other representing an alkoxy group, a combination of one member each representing an alkyl group and the other representing an alkenyloxy group, and a combination of two members each representing an alkyl group and a combination of two members each representing an alkenyl groupThe method is described.

The compound represented by the general formula (LC3-b) is preferably a compound represented by the following general formula (LC 3-c).

[ solution 48]

The compound represented by the general formula (N-2) is preferably a compound selected from the group consisting of compounds represented by the general formulae (N-2-1) to (N-2-3).

[ solution 49]

(in the formula, R^N211And R^N22Each independently represents R in the general formula (N-2)^N211And R^N22The same meaning is used. )

The compound represented by the general formula (N-3) is preferably a compound selected from the group of compounds represented by the general formulae (N-3-1) and (N-3-2).

[ solution 50]

(in the formula, R^N31And R^N32Each independently represents R in the general formula (N-3)^N31And R^N32The same meaning is used. )

The third component preferably contains 1 or 2 or more compounds represented by the general formula (L). The compound represented by the general formula (L) corresponds to a compound having a substantially neutral dielectric property (Δ ε has a value of-2 to 2).

[ solution 51]

(in the formula，R^L1And R^L2Each independently represents an alkyl group having 1 to 8 carbon atoms, 1 or 2 or more-CH groups which are not adjacent to each other in the alkyl group₂-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,

n^L1represents 0, 1,2 or 3,

A^L1、A^L2and A^L3Each independently represents a group selected from the group consisting of,

(a12)1, 4-cyclohexylene (1-CH present in the radical)₂-or non-adjacent 2 or more-CH₂-may be substituted by-O-. )

(b12)1, 4-phenylene (1-CH-present in the radical or not adjacent 2 or more-CH-may be substituted by-N) -) and

(c12) naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-CH ═ present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or 2 or more-CH ═ which are not adjacent may be substituted by-N ═ can be used.)

The above-mentioned group (a12), group (b12) and group (c12) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,

Z^L1and Z^L2Each independently represents a single bond, -CH₂CH₂-、-(CH₂)₄-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCF₂-、-CF₂O-, -CH-N-CH-, -CH-, -CF-or-C ≡ C-,

when n is^L1A plurality of A's being present for 2 or 3^L2In the case of (3), they may be the same or different; when n is^L1A plurality of Z s being 2 or 3^L3In the case of (3), they may be the same or different; but does not include compounds represented by the general formula (N-1), the general formula (N-2) and the general formula (N-3). )

The compounds represented by the general formula (L) may be used alone or in combination. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with desired performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 as one embodiment of the present invention. Alternatively, in other embodiments of the present invention, 2,3,4, 5, 6, 7, 8, 9, or 10 or more species are used.

In the composition of the present invention, the content of the compound represented by the general formula (L) needs to be appropriately adjusted depending on the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, dropping marks, burn-in, dielectric anisotropy, and the like.

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

When the viscosity of the composition of the present invention is kept low and a composition having a high response speed is required, the lower limit value is preferably high and the upper limit value is preferably high. Further, T of the composition of the present invention is maintained_niWhen the composition has a high level and requires good temperature stability, the lower limit value is preferably high and the upper limit value is preferably high. In order to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable to lower the lower limit and lower the upper limit.

In the case where reliability is important, R is preferably selected^L1And R^L2Are all alkyl; when importance is attached to reduction of the volatility of the compound, an alkoxy group is preferable; when importance is attached to the reduction of viscosity, at least one of the alkenyl groups is preferably used.

With respect to R^L1And R^L2When the ring structure to which the compound is bonded is a phenyl group (aromatic group), the compound is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms; when the ring structure to be bonded is a saturated ring structure such as cyclohexane, pyran, dioxane, or the like, a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms is preferable.In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms when oxygen atoms are present is preferably 5 or less, and is preferably linear.

[ solution 52]

Wherein R is used in combination^L1And R^L2At least 1 or more of the compounds represented by the general formula (i) and the compound represented by the general formula (i) can significantly suppress a decrease in the Voltage Holding Ratio (VHR).

With respect to n^L1When importance is attached to the response speed, 0 is preferable; for improving the upper limit temperature of the nematic phase, it is preferably 2 or 3; to achieve their balance, 1 is preferred. Further, in order to satisfy the characteristics required as a composition, it is preferable to combine compounds of different values.

With respect to A^L1、A^L2And A^L3In the case where an increase Δ n is required, it is preferably aromatic; for improving the response speed, aliphatic is preferable; each independently preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2 ] benzene]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, more preferably represents the following structure,

[ Hua 53]

More preferably, it represents trans-1, 4-cyclohexylene or 1, 4-phenylene.

Z^L1And Z^L2When importance is attached to the response speed, a single key is preferable.

The number of halogen atoms in the molecule of the compound represented by the general formula (L) is preferably 0 or 1.

The compound represented by the general formula (L) is preferably a compound selected from the compounds represented by the general formula (L-1).

[ solution 54]

(in the formula, R^L1And R^L2Each independently represents R in the general formula (L)^L1And R^L2The same meaning is used. )

R^L11And R^L12Preferably, the alkyl group has 1 to 5 linear carbon atoms, the alkoxy group has 1 to 4 linear carbon atoms, and the alkenyl group has 2 to 5 linear carbon atoms. The compounds represented by the general formula (L-1) may be used alone or in combination of 2 or more. The kind of the compound that can be combined is not particularly limited, and it is suitably combined and used in accordance with the required performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.

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

When the viscosity of the composition of the present invention is kept low and a composition having a high response speed is required, the lower limit value is preferably high and the upper limit value is preferably high. Further, T of the composition of the present invention is maintained_niWhen the composition has a high level and requires good temperature stability, the lower limit value is preferably medium and the upper limit value is preferably medium. In addition, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, the lower limit is preferably set as described aboveThe value is low and the upper limit value is low.

The compound represented by the general formula (L-1) is preferably a compound represented by the general formula (L-1-1).

[ solution 55]

(in the formula, R^L11Represents a hydrogen atom or a methyl group, R^L2Represents R in the general formula (L)^L2The same meaning is used. )

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

[ solution 56]

Further, the compound represented by the general formula (L-1-1) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-1-1.21) to (L-1-1.24), and is preferably a compound represented by the formulae (L-1-1.22) to (L-1-1.24). In particular, the compounds represented by the formula (L-1-1.22) are particularly preferable because they improve the response speed of the composition of the present invention. In addition, high T is more desirable than response speed_niIn this case, it is preferable to use a compound represented by the formula (L-1-1.23) or the formula (L-1-1.24).

[ solution 57]

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

[ solution 58]

The compound represented by the general formula (L-1) is preferably a compound represented by the general formula (L-1-2).

[ chemical 59]

(in the formula, R^L121And R^L122Each independently represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms. )

The compound represented by the general formula (L-1-2) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-1-2.1) to (L-1-2.12), and is preferably a compound represented by the formula (L-1-2.1), the formula (L-1-2.3) or the formula (L-1-2.4). In particular, the compound represented by the formula (L-1-2.1) is particularly preferable because it improves the response speed of the composition of the present invention. In addition, high T is more desirable than response speed_niIn this case, it is preferable to use compounds represented by the formula (L-1-2.3), the formula (L-1-2.4), the formula (L-1-2.11) and the formula (L-1-2.12). In order to improve the solubility at low temperatures, the total content of the compounds represented by the formulae (L-1-2.3), (L-1-2.4), (L-1-2.11) and (L-1-2.12) is not preferably 20% or more.

[ solution 60]

Further, the compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formulae (L-1-3) and/or (L-1-4).

[ solution 61]

(in the formula, R^L2Represents R in the general formula (L)^L2The same meaning is used. )

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 preferably contains 1 or 2 or more compounds represented by the general formulae (L-2) to (L-11) as the compound represented by the general formula (L).

[ solution 62]

(in the formula, R^L31And R^L32Represents an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, R^L32Represents an alkyl group having 1 to 5 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. )

The compound represented by the general formula (L) is preferably a compound selected from the group consisting of the general formula (L-4), the general formula (L-6), the general formula (L-7) and the general formula (L-8), more preferably a compound selected from the group consisting of the general formula (L-7) and the general formula (L-8), and also preferably a compound selected from the group consisting of the general formula (L-6) and the general formula (L-8). More specifically, when a large Δ n is required, it is preferable that the Δ n is a compound selected from the group consisting of the compounds represented by the general formula (L-6), the general formula (L-8) and the general formula (L-11).

Among the compounds represented by the general formula (L-4), the general formula (L-7) and the general formula (L-8), R is preferably R^L31Is alkyl of 1 to 5 carbon atoms or alkenyl of 2 to 5 carbon atoms, R^L32Is alkyl of 1 to 5 carbon atoms or alkoxy of 1 to 5 carbon atoms, R^L31More preferably an alkenyl group having 2 to 5 carbon atoms, still more preferably an alkenyl group having 2 or 3 carbon atoms, and R in the compound represented by the general formula (L-6)^L31And R^L32Each independently is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms.

Furthermore, it is also preferable to contain 1 or 2 or more compounds represented by the general formula (L-12), the general formula (L-13) or the general formula (L-14) as the compound represented by the general formula (L).

[ solution 63]

(in the formula, R^L51And R^L52Each independently represents 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, X^L51And X^L52Each independently represents a fluorine atom or a hydrogen atom, X^L51And X^L52One of them is a fluorine atom and the other is a hydrogen atom. )

Further, 1 or 2 or more compounds represented by the general formulae (L-16.1) to (L-16.3) may be contained as the compound represented by the general formula (L).

[ solution 64]

Further, 1 or 2 or more compounds represented by the general formula (N-001) may be contained as the compound represented by the general formula (L).

[ solution 65]

(in the formula, R^N1And R^N2Each independently represents 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, L¹And L²Each independently represents a hydrogen atom, a fluorine atom, CH₃Or CF₃. But does not include L¹And L²Both represent the case of fluorine atoms. )

R^N1And R^N2Preferably represents an alkyl group having 1 to 5 carbon atoms.

The dielectric anisotropy (. DELTA.. di-elect cons.) of the composition of the present invention has a negative value at 25 ℃. The dielectric anisotropy (. DELTA.. di-elect cons.) of the composition of the present invention at 25 ℃ is from-2.0 to-8.0, preferably from-2.0 to-6.0, more preferably from-2.0 to-5.0, and particularly preferably from-2.5 to-4.5.

The composition having a negative value of dielectric anisotropy (. DELTA.. di-elect cons.) preferably contains a compound represented by general formulae (N-1) to (N-3) and a compound represented by general formula (L). 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 preferably contains a compound represented by the general formula (N-1) and a compound represented by the general formula (L-1-1).

In the composition of the present invention, the total content of the compound represented by the general formula (I), the compounds represented by the general formulae (N-1) to (N-3), and the compound represented by the general formula (L) is preferably 5% or more, preferably 80% or more, preferably 85% or more, preferably 88% or more, preferably 90% or more, preferably 92% or more, preferably 95% or more, preferably 97% or more, preferably 98% or more, preferably 99% or more, and preferably substantially no other compound, as a lower limit in the composition. The upper limit is preferably 90% or less, preferably 95% or less, preferably 98% or less, preferably 99% or less, and preferably substantially free of other compounds.

The refractive index anisotropy (. DELTA.n) of the composition of the present invention at 25 ℃ is 0.08 to 0.14, more preferably 0.09 to 0.13, and particularly preferably 0.09 to 0.12. More specifically, in the case of a thin cell gap, it is preferably 0.10 to 0.13; in the case of a cell gap corresponding to a thickness, it is preferably 0.08 to 0.10. In the present specification, 0.09 or more is expressed as Δ n being large.

Rotational tack (. gamma.) at 25 ℃ of the compositions of the invention₁) Is from 50 to 160 mPas, preferably from 55 to 160 mPas, preferably from 60 to 160 mPas, preferably from 80 to 130 mPas.

Nematic phase-isotropic liquid phase transition temperature (T) of the composition of the invention_NI) From 60 ℃ to 120 ℃, more preferably from 70 ℃ to 100 ℃, and particularly preferably from 70 ℃ to 85 ℃. Wherein, in the present specification, 60 ℃ or higher is expressed as T_NIHigh. In the case of liquid crystal television applications, T_NIPreferably 70 ℃ to 80 ℃; in the case of mobile phone use, T_NIPreferably from 80 ℃ to 90 ℃; in the case of outdoor Display such as PID (Public Information Display), T_NIPreferably from 90 ℃ to 110 ℃.

In addition to the above compounds, the composition of the present invention may contain a conventional nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, antioxidant, ultraviolet absorber, infrared absorber, polymerizable monomer, or light stabilizer (HALS) other than the compound of the present invention.

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, ECB mode, and the like.

Examples

The present invention will be described in further detail below with reference to examples, but the present invention is not limited to these examples. In the compositions containing the compounds of the following examples and comparative examples, "%" means "% by mass". The phase transition temperature was measured by using a polarizing microscope equipped with a temperature control stage and a Differential Scanning Calorimeter (DSC) in combination.

Hereinafter, the following abbreviations are used.

an amphos: di-tert-butyl (4-dimethylaminophenyl) phosphine

Bu: n-butyl

DMF: n, N-dimethylformamide

dppf: 1, 1' -bis (diphenylphosphino) ferrocene

Et: ethyl radical

NMP: n-methyl-2-pyrrolidone

Pent: n-pentyl group

Pr: n-propyl radical

Tf: trifluoromethanesulfonyl radical

THF: tetrahydrofuran (THF)

Example 1 Synthesis of Compound G-1-5

[ solution 66]

(Synthesis of Compound G-1-2)

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

(Synthesis of Compound G-1-3)

Compound G-1-2(34.1G) and NMP (270mL) were charged and stirred in a reaction vessel equipped with a stirrer, a thermometer, and a cooling tube under a nitrogen atmosphere. To this was added potassium carbonate (35.4g) and the solution was heated to 160 ℃ over 1 and a half hour. After stirring at 160 ℃ for 4 hours, it was cooled to room temperature, and 10% hydrochloric acid (150mL), water (150mL) and ethyl acetate (200mL) were added. The organic layer was separated and the aqueous layer was further extracted again with ethyl acetate (200 mL). The obtained organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The resulting solution was concentrated, methylene chloride (300mL) was added, and the solution obtained by dissolution was passed through a column packed with silica gel (19g) and alumina (19g), followed by passing methylene chloride (400 mL). The obtained column-passing solution was concentrated and then dried in vacuo to obtain Compound G-1-3 (33.28G).

[ solution 67]

(Synthesis of Compound G-1-4)

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

(Synthesis of Compound G-1-5)

Under a nitrogen atmosphere, compound G-1-4(10.0G), [1, 1' -bis (diphenylphosphino) ferrocene ] palladium (II) dichloride (1.08G), THF (80mL) were added to a reaction vessel equipped with a stirrer and a thermometer, followed by stirring and cooling to 0 ℃. A0.61M solution of zinc propylchloride in THF (65mL) was added dropwise over 30 minutes at 0 ℃. After stirring at 0 ℃ for 30 minutes, the temperature was raised to 45 ℃ and the mixture was stirred for 1 hour. Then, after cooling to 20 ℃ a saturated aqueous ammonium chloride solution (50mL) was added dropwise at 20 ℃ to 30 ℃ and stirred for 30 minutes. The organic layer was separated and the aqueous layer was further extracted with ethyl acetate (100 mL). The obtained organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The resulting solution was concentrated, hexane (70mL) was added, and the solution thus dissolved was passed through a column at 55 ℃ containing silica gel (7g) and alumina (7g), followed by further passage of hexane (120 mL). The obtained column-passing solution was concentrated and then dried in vacuo to obtain Compound G-1-5 (1.66G).

Phase transition temperature: cr 69.3 Iso

MS m/z：271[M⁺]

Example 2 Synthesis of Compound G-1-6

[ solution 68]

(Synthesis of Compound G-1-6)

Compound G-1-3(4.98G), potassium carbonate (5.63G), bromoethane (2.57G), and NMP (20mL) were charged into a reaction vessel equipped with a stirrer, a thermometer, and a cooling tube under a nitrogen atmosphere, and stirred. The solution temperature was heated to 100 ℃ over 1 hour. After stirring at 100 ℃ for 8 hours, the mixture was cooled to room temperature, 10% hydrochloric acid (25mL) and water (20mL) were added to the mixture, the precipitated solid was filtered, and the residue was washed with water (45 mL). The resulting compound was azeotroped in toluene (75 mL). To the resulting solid were added methylene chloride (20mL) and silica gel (7.5g), and the mixture was concentrated, dried and solidified. The resulting powder was applied to a column packed with silica gel (55g), and ethyl acetate (10mL) and hexane (500mL) were further passed therethrough. The obtained column-passing solution was concentrated and then dried in vacuo to obtain Compound G-1-6 (1.37G).

Phase transition temperature: cr 92.6 Iso

MS m/z：273[M⁺]

Example 3 Synthesis of Compound G-1-7

[ solution 69]

(Synthesis of Compound G-1-7)

Compound G-1-3(5.40G), potassium carbonate (6.08G), bromopentane (3.48G), and NMP (40mL) were charged into a reaction vessel equipped with a stirrer, a thermometer, and a cooling tube under a nitrogen atmosphere, and stirred. The solution temperature was heated to 100 ℃ over 1 hour. After stirring at 100 ℃ for 1.5 hours, the mixture was cooled to room temperature, 10% hydrochloric acid (30mL), water (30mL) and toluene (70mL) were added to separate an organic layer, and the aqueous layer was further extracted with toluene (70 mL). The obtained organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The resulting solution was concentrated and recrystallized from an acetone/ethanol mixed solution. Then, the obtained solid was dissolved in toluene (5mL) and hexane (25mL), the obtained solution was passed through a silica gel column, and the obtained column-passed solution was concentrated, dried and solidified to obtain compound G-1-7 (3.54G).

Phase transition temperature: cr 57.0 Iso

MS m/z：315[M⁺]

Example 4 Synthesis of Compound G-1-10

[ solution 70]

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

(Synthesis of Compound G-1-10)

Compound G-1-9(6.32G), potassium carbonate (4.05G) and NMP (50mL) were charged into a reaction vessel equipped with a stirrer, a thermometer and a cooling tube under a nitrogen atmosphere and stirred. The solution temperature was heated to 160 ℃ over 1 hour. After stirring at 160 ℃ for 12 hours, the mixture was cooled to room temperature, 10% hydrochloric acid (20mL) and toluene (50mL) were added to separate an organic layer, and the aqueous layer was further extracted with toluene (50 mL). The obtained organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The resulting solution was concentrated and recrystallized from an acetone/ethanol mixed solution. Then, the obtained solid was dissolved in methylene chloride (30mL), the obtained solution was passed through a silica gel column, and the obtained column-passed solution was concentrated, dried and solidified to obtain compound G-1-10 (2.61G).

Phase transition temperature: cr 84.7N 133.5 Iso

MS m/z：381[M⁺]

Example 5 Synthesis of Compound G-1-16

[ solution 71]

(Synthesis of Compound G-1-12)

Diisopropylamine (28.33g) and THF (350mL) were charged into a reaction vessel equipped with a stirrer and a thermometer under a nitrogen atmosphere, followed by stirring and cooling to-78 ℃. A2.76M butyllithium/hexane solution (94mL) was added dropwise over 1 hour at-78 ℃. After stirring at-78 ℃ for 30 minutes, Compound G-1-11(43.8G) was added dropwise at-78 ℃ over 1 hour. After stirring at-78 ℃ for 3 hours, DMF (45g) was added dropwise at-78 ℃ over 30 minutes. After stirring at-78 ℃ for 1 hour, the temperature was raised to-20 ℃ and the reaction mixture was added dropwise to 10% hydrochloric acid (100 mL). The organic layer was separated and the aqueous layer was further extracted with toluene (200 mL). The organic layers were combined, washed with water, an aqueous sodium hydrogencarbonate solution and brine, and dried over anhydrous sodium sulfate. The resulting solution was concentrated, toluene (50mL) was added thereto, the dissolved solution was passed through a silica gel column, and the obtained column-passed solution was concentrated, dried and solidified to obtain compound G-1-12 (20G).

(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, compounds G-1 to 12(20G), 4-propylphenylboronic acid (14.6G), bis [ di-tert-butyl (4-dimethylaminophenyl) phosphine ] palladium (II) dichloride (0.27G) and THF (80mL) were charged, and the temperature was raised to 60 ℃ while stirring. To the reaction mixture was added dropwise a 2M aqueous sodium carbonate solution (60 ml). After stirring at 60 ℃ for 2 hours, heating was stopped and the temperature of the solution was returned to room temperature. Then, 10% hydrochloric acid (75mL) was added. The organic layer was separated and the aqueous layer was further re-extracted with toluene (200 mL). The obtained organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The resulting solution was concentrated, toluene (100mL) was added thereto, the dissolved solution was passed through a silica gel column, and the obtained column-passed solution was concentrated, dried and solidified to obtain compound G-1-13 (23.4G).

[ chemical formula 72]

(Synthesis of Compound G-1-14)

Compound G-1-13(23.4G), 2-methyl-2-butene (57.4G), butanol (240mL), and water (240mL) were charged into a reaction vessel equipped with a stirrer, a thermometer, and a dropping funnel, followed by stirring, and NaClO was added dropwise over 1 hour₂(22.1g)、NaH₂PO₄(49.07g), water (100 mL). After stirring at room temperature for 30 minutes, an 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, and dried over anhydrous sodium sulfate. The resulting solution was concentrated to obtain Compound G-1-14 (28G).

(Synthesis of Compound G-1-15)

In a reaction vessel equipped with a stirrer and a thermometer under nitrogen atmosphere, the compounds G-1 to 14(28G) and concentrated sulfuric acid (112G) were charged and stirred, and the temperature was raised to 90 ℃ and stirred for 20 hours. The reaction mixture was neutralized with a 15% aqueous solution of sodium carbonate and extracted with ethyl acetate (800 mL). The obtained organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The resulting solution was concentrated, toluene (100mL) was added thereto, the dissolved solution was passed through a silica gel column, and the obtained column-passed solution was concentrated, dried and solidified to obtain compound G-1-15 (14G).

[ solution 73]

(Synthesis of Compound G-1-16)

Under a nitrogen atmosphere, compound G-1-15(14G), hydrazine 1 hydrate (12G) and diethylene glycol (500mL) were charged into a reaction vessel equipped with a stirrer, a thermometer and a dropping funnel, and stirred, and the temperature was raised to 80 ℃ over 1 hour. After stirring at 80 ℃ for 2 hours, the mixture was cooled to room temperature, and potassium hydroxide (16.5g) and water (70mL) were added thereto, and the mixture was heated to 80 ℃ over 1 hour and refluxed for 2 hours. The reaction solution was cooled to room temperature, poured into water (500mL), and stirred for 30 minutes. The aqueous layer was extracted with toluene (200 mL). The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The obtained solution was concentrated, toluene was added thereto, the dissolved solution was passed through a silica gel column, and the obtained column-passed solution was concentrated, dried and solidified to obtain compound G-1-16 (5G).

Phase transition temperature: cr 43.4 Iso

MS m/z：269[M⁺]

Comparative example 1

The compound of comparative example 1 was synthesized according to the method described in patent document 1.

[ chemical formula 74]

(extrapolated rotational viscosity (. gamma.))₁) Measurement of (2)

A host liquid crystal (H) described in example 5 of Japanese patent laid-open publication No. 2018-2670 was prepared. T of the host liquid crystal (H)_n-i(nematic phase-isotropic liquid phase transition temperature), Δ ∈ (dielectric constant anisotropy at 25 ℃), Δ n (refractive index anisotropy at 25 ℃), and γ₁The values (all measured values) of (rotational viscosity coefficient at 25 ℃) are as follows.

Δε：-2.79

Δn：0.101

γ₁：112

A liquid crystal composition was prepared which contained 90% of the mother liquid crystal (H) and 10% of the compound obtained in examples and comparative examples. The rotational viscosity (mPas) of the composition at 25 ℃ was measured, and the extrapolated rotational viscosity (. gamma.) of the compounds obtained in examples and comparative examples was determined based on the amount of change from the mother liquid crystal (LC-1)₁). The results are shown in Table 1.

[ Table 1]

Compound (I)	Y_l(mPa·s)
		Example 1	122
Example 3	191
		Comparative example 1	325

Claims

1. A compound represented by the general formula (I),

[ solution 1]

In the formula, Rⁱ¹And Rⁱ²Each independently represents a chlorine atom, a bromine atom, an iodine atom, a hydroxyl group, -BR¹R²An alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms, formula-BR¹R²In, R¹And R²Each independently represents a hydroxyl group, an alkoxy group having 1 to 4 carbon atoms, or R¹And R²Are bonded to each other to form a cyclic structure to represent-O- (CR)³R⁴)_n-O-, of the formula-O- (CR)³R⁴)_nin-O-, R³And R⁴Each 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's are present³R⁴Which may be the same or different, the carbon atom1-CH present in an alkyl group having a number of 1 to 15 or an alkenyl group having 2 to 15 carbon atoms₂-or non-adjacent 2 or more-CH₂Each independently of the other may be substituted by-O-, -S-, -CO-, -COO-, -OCO-, -SOO-O-or-C.ident.C-, and furthermore, the hydrogen atom present in the alkyl group of carbon atoms 1 to 15 or the alkenyl group of carbon atoms 2 to 15 may be substituted by a fluorine atom,

(a)1, 4-cyclohexylene radical, 1-CH present in this radical₂-or non-adjacent 2 or more-CH₂-may be substituted by-O-or-S-,

(b)1, 4-phenylene, 1-CH ═ or non-adjacent 2 or more-CH ═ present in the group may be substituted by-N ═ and 1 hydrogen atom present in the group may be substituted by a fluorine atom, and

(c)1, 4-cyclohexenylene, naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl, the hydrogen atoms present in these groups may be substituted by fluorine atoms, and furthermore, 1-CH ═ or not adjacent 2 or more-CH ═ present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted by-N ═ in the above groups,

Yⁱrepresents-O-, -S-, -SO-, -SOO-, -CF₂-, -CO-or-CH₂-。

2. A compound according to claim 1, formula (I), wherein Rⁱ¹And Rⁱ²Each independently represents 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 an alkenyloxy group having 2 to 8 carbon atoms.

3. A compound according to claim 1 or 2, formula (I) wherein XⁱRepresents a fluorine atom.

4. A compound according to any one of claims 1 to 3, formula (I) wherein Y isⁱrepresents-O-or-S-.

5. A compound according to any one of claims 1 to 4, wherein in formula (I), n isⁱ¹And mⁱ¹Both represent 0.

6. A composition comprising 1 or 2 or more compounds according to any one of claims 1 to 5.

7. The composition of claim 6, which is in a liquid crystal phase.

8. A liquid crystal display element using the composition according to claim 6 or 7.