阅读说明：本技术 一种液晶化合物及其制备方法与应用 (Liquid crystal compound and preparation method and application thereof ) 是由 苏学辉 于海龙 刘俊 田会强 储士红 王新颖 姜天孟 陈海光 于 2018-06-15 设计创作，主要内容包括：本发明涉及一种液晶化合物及其制备方法与应用。所述液晶化合物中,R<Sub>1</Sub>表示1～15个碳原子的烷基、烷氧基,或2～15个碳原子的链烯基；其中,任意H原子可以被F或Cl取代；任意一个或多个CH<Sub>2</Sub>可以被环戊基、环丁基或环丙基替代；X表示R<Sub>2</Sub>、F、CF<Sub>3</Sub>或OCF<Sub>3</Sub>,R<Sub>2</Sub>表示1～15个碳原子的烷基、烷氧基,2～15个碳原子的链烯基；其中,任意H原子可以被F或Cl取代,任意一个或多个CH<Sub>2</Sub>可以被环戊基、环丁基或环丙基替代；L表示H、CH<Sub>3</Sub>或OCH<Sub>3</Sub>；m、n彼此独立地表示0或1。含有该化合物的液晶组合物具有较低的旋转粘度,较大的Δε⊥。且该化合物价格低廉、性能稳定,可广泛用于液晶显示领域,具有重要的应用价值。<Image he="242" wi="700" file="DDA0001698124170000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(The invention relates to a liquid crystal compound and a preparation method and application thereof. In the liquid crystal compound, R 1 Represents an alkyl group having 1 to 15 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 15 carbon atoms; wherein any H atom may be substituted by F or Cl; any one or more CH 2 May be replaced by cyclopentyl, cyclobutyl or cyclopropyl; x represents R 2 、F、CF 3 Or OCF 3 ，R 2 Represents an alkyl group having 1 to 15 carbon atoms, an alkoxy group, an alkenyl group having 2 to 15 carbon atoms; wherein any H atom may be substituted by F or Cl, any one or more CH 2 May be replaced by cyclopentyl, cyclobutyl or cyclopropyl; l denotes H, CH 3 Or OCH 3 (ii) a m and n independently represent 0 or 1. The liquid crystal composition containing the compound has lower rotary viscosity and larger delta epsilon. And the compound has low price and stable performance, can be widely applied to the field of liquid crystal display and has important application value.)

1. A liquid crystal compound characterized by having a structure represented by the following general formula i:

in the general formula I, the compound has the following structure,

R₁represents an alkyl group having 1 to 15 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 15 carbon atoms; wherein any one or more H atoms may be substituted by F or Cl; any one or more CH₂Can be surrounded byPentyl, cyclobutyl or cyclopropyl substitution;

x represents R₂、F、CF₃Or OCF₃，R₂Represents an alkyl group having 1 to 15 carbon atoms, an alkoxy group, an alkenyl group having 2 to 15 carbon atoms; wherein any one or more H atoms may be substituted by F or Cl, any one or more CH₂May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;

each independently represent

L denotes H, CH₃Or OCH₃；

m and n independently represent 0 or 1.

2. The liquid crystal compound according to claim 1, wherein R in the formula I₁Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 10 carbon atoms; wherein any one or more H atoms may be substituted by F or Cl, any one or more CH₂May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;

x represents R₂、F、CF₃Or OCF₃，R₂Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkenyl group having 2 to 10 carbon atoms, wherein any one or more H atoms may be substituted by F or Cl, and any one or more CH₂May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;

each independently represent

L denotes H, CH₃Or OCH₃；

m and n independently represent 0 or 1.

3. The liquid crystal composition according to claim 1 or 2, wherein R in the formula I₁Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 10 carbon atoms; wherein any one or more H atoms may be substituted by F, any one or more CH₂May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;

x represents R₂、F、CF₃Or OCF₃，R₂Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkenyl group having 2 to 10 carbon atoms, wherein any one or more H atoms may be substituted by F, and any one or more CH₂May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;

each independently represent

L denotes H, CH₃Or OCH₃；

m and n independently represent 0 or 1.

4. The liquid crystal compound according to any one of claims 1 to 3, wherein the liquid crystal compound is one selected from the group consisting of compounds represented by the following formulae I-1 to I-12:

5. the liquid crystal compound according to any one of claims 1 to 4, wherein the liquid crystal compound is selected from one of the following compounds:

wherein R is₁₁、R₂₁Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 10 carbon atoms; wherein any one or more H atoms may be substituted by F.

6. A process for producing a liquid crystal compound according to any one of claims 1 to 5, wherein when n is 1,is composed ofOr when n is 0, m is 1,is composed of The synthesis route is specifically as follows:

preferably:

the preparation method specifically comprises the following steps:

(1) to be provided withThe raw material is subjected to metalation reaction with an organic lithium reagent and then is subjected to reaction with boric acid ester to obtain

(2) Obtained by the step (1)Andreaction to obtain

(3) Obtained by the step (2)Firstly carrying out metalation reaction with n-butyl lithium, and then reacting with difluorodibromomethane to synthesize the compound

(4)Firstly reacting with magnesium chips to form a Grignard reagent, and then reacting with trimethyl borate to obtain the compound

(5) Obtained by the step (4)By reaction with hydrogen peroxide to give

(6) Obtained by the step (3)And the one obtained by the step (5)Williamson synthesis methodCompound (I)

More preferably:

in the step (1), the step (c),the feeding molar ratio of the organic lithium reagent to the organic lithium reagent is 1: 1.0-2.0;the feeding molar ratio of the boric acid ester to the boric acid ester is 1: 1.0-3.0; the reaction temperature is-50 to-100 ℃; preferably, the organic lithium reagent is selected from one or more of sec-butyl lithium, tert-butyl lithium or n-butyl lithium; the boric acid ester is selected from one or more of trimethyl borate, triisopropyl borate, tributyl borate or triisobutyl borate;

and/or the presence of a gas in the gas,

in the step (2), the step (c),andthe feeding molar ratio of (A) to (B) is 1.0: 1.0 to 1.5; the reaction temperature is 50-150 ℃;

and/or the presence of a gas in the gas,

in the step (3), the step (c),the feeding molar ratio of n-butyllithium to dibromodifluoromethane is 1: 1.0-1.5: 1.6-2.0, the reaction temperature is-80-0 ℃, and the reaction time is 1-6 h;

and/or the presence of a gas in the gas,

in the step (4), the step of (C),the feeding molar ratio of the magnesium chips to the trimethyl borate is as follows: 1: 1.5-2.5: 16-2.5; the temperature for dropping trimethyl borate is-20 ℃ to 0 ℃;

and/or the presence of a gas in the gas,

in the step (5), the step (c),the feeding molar ratio of the hydrogen peroxide to the hydrogen peroxide is as follows: 1: 2.5 to 3.5; the reaction time is 2 h;

and/or the presence of a gas in the gas,

in the step (6), the step (c),andthe feeding molar ratio of (A) to (B) is 1: 1.0-2.0, the reaction temperature is 50-120 ℃, and the reaction time is 3-8 h.

7. A process for producing a liquid crystal compound according to any one of claims 1 to 5, wherein when n is 0 and m is 1,is composed ofThe synthesis route is specifically as follows:

preferably, the preparation method specifically comprises the following steps:

(1) to be provided withAs a raw material, withObtained by dehydration reaction

(2) Obtained by the step (1)Firstly carrying out metalation reaction with n-butyl lithium, and then reacting with difluorodibromomethane to synthesize the compound

(3)Firstly reacting with magnesium chips to form a Grignard reagent, and then reacting with trimethyl borate to obtain the compound

(4) Obtained by the step (3)By reaction with hydrogen peroxide to give

(5) Obtained by the step (2)And the one obtained by the step (4)Reactive synthesis of compounds by Williamson synthesis

More preferably:

in the step (1), the step (c),andthe feeding molar ratio of (A) to (B) is 1: 1.5-2; the reaction time is 3-10 h;

and/or the presence of a gas in the gas,

in the step (2), the step (c),the feeding molar ratio of n-butyllithium to dibromodifluoromethane is 1: 1.0-1.5: 1.6-2.0, the reaction temperature is-80-0 ℃, and the reaction time is 1-6 h;

and/or the presence of a gas in the gas,

in the step (3), the step (c),the feeding molar ratio of the magnesium chips to the trimethyl borate is as follows: 1: 1.5-2.5: 1.6-2.5; the temperature for dropping trimethyl borate is-20 ℃ to 0 ℃;

and/or the presence of a gas in the gas,

in the step (4), the step of (C),the feeding molar ratio of the hydrogen peroxide to the hydrogen peroxide is as follows: 1: 2.5 to 3.5; the reaction time is 2 h;

and/or the presence of a gas in the gas,

in the step (5), the step (c),andthe feeding molar ratio of (A) to (B) is 1: 1.0-2.0, the reaction temperature is 50-120 ℃, and the reaction time is 3-8 h.

8. The method for producing a liquid crystal composition according to any one of claims 1 to 5, wherein when n-0, m-1,is composed ofWhen the temperature of the water is higher than the set temperature,

the synthetic route is specifically as follows:

preferably, the first and second electrodes are formed of a metal,

the preparation method specifically comprises the following steps:

(1) to be provided withAs a raw material, withReaction to obtain

(2) Reacting the obtained product in the step (1) with boron trifluoride diethyl etherate and triethylsilane to obtain

(3) Obtained through the step (2)Firstly carrying out metalation reaction with n-butyl lithium, and then reacting with difluorodibromomethane to synthesize the compound

(4)Firstly react with magnesium chipsShould form a Grignard reagent, and then react with trimethyl borate to obtain

(5) Obtained by the step (4)By reaction with hydrogen peroxide to give

(6) Obtained by the step (3)And the one obtained by the step (5)Reactive synthesis of compounds by Williamson synthesis

More preferably, it is a mixture of more preferably,

in the step (1), the step (c),andthe feeding molar ratio of (A) to (B) is 1: 0.8-1.5;

and/or the presence of a gas in the gas,

in the step (2), the step (c),the feeding molar ratio of the boron trifluoride diethyl etherate to the boron trifluoride diethyl etherate is 1: 1.0-3.0;with triethylsilaneThe molar ratio is 1: 1.0-3.0;

and/or the presence of a gas in the gas,

in the step (3), the step (c),the feeding molar ratio of n-butyllithium to dibromodifluoromethane is 1: 1.0-1.5: 1.6-2.0, the reaction temperature is-80-0 ℃, and the reaction time is 1-6 h;

and/or the presence of a gas in the gas,

in the step (4), the step of (C),the feeding molar ratio of the magnesium chips to the trimethyl borate is as follows: 1: 1.5-2.5: 1.6-2.5; the temperature for dropping trimethyl borate is-20 ℃ to 0 ℃;

and/or the presence of a gas in the gas,

in the step (5), the step (c),the feeding molar ratio of the hydrogen peroxide to the hydrogen peroxide is as follows: 1: 2.5 to 3.5; the reaction time is 2 h;

and/or the presence of a gas in the gas,

in the step (6), the step (c),andthe feeding molar ratio of (A) to (B) is 1: 1.0-2.0, the reaction temperature is 50-120 ℃, and the reaction time is 3-8 h.

9. A liquid crystal composition comprising the liquid crystal compound according to any one of claims 1 to 5;

preferably, the liquid crystal compound accounts for 0.01-99% of the liquid crystal composition by mass; more preferably 0.01 to 60%, and still more preferably 0.1 to 40%.

10. Use of the liquid crystal compound according to any one of claims 1 to 5 or the liquid crystal composition according to claim 9 for liquid crystal display; preferably in liquid crystal display devices; more preferably in TN, ADS, VA, PSVA, FFS or IPS liquid crystal displays.

Technical Field

The invention belongs to the technical field of liquid crystal materials, and particularly relates to a liquid crystal compound and a preparation method and application thereof.

Background

In recent years, liquid crystal display devices have been developed more and more rapidly, and various types such as a small liquid crystal display device for vehicles, a portable liquid crystal display device, an ultra-thin liquid crystal display device, and the like have been developed. Developments in the field are progressing, and in the case of a television, for example, it is characterized by light weight, small space occupation, convenience in movement, and also a notebook-type personal computer, a mobile phone, and the like.

The liquid crystal material is used as an environmental material and has great research value and good application prospect in the fields of information display materials, organic optoelectronic materials and the like. At present, the TFT-LCD product technology has matured, and successfully solves the technical problems of viewing angle, resolution, color saturation, brightness, etc., and large-size and medium-and small-size TFT-LCD displays have gradually occupied the mainstream status of flat panel displays in respective fields. However, the requirements for display technology are continuously increasing, and liquid crystal displays are required to achieve faster response, reduce driving voltage to reduce power consumption, and the like, and liquid crystal materials are also required to have low voltage driving, fast response, wide temperature range and good low temperature stability.

The liquid crystal material plays an important role in improving the performance of the liquid crystal display, especially reducing the rotational viscosity of the liquid crystal material and improving the dielectric anisotropy delta epsilon of the liquid crystal material. In order to improve the properties of materials and enable the materials to meet new requirements, the synthesis of novel structure liquid crystal compounds and the research of structure-property relationship become important work in the field of liquid crystal.

Disclosure of Invention

The first object of the present invention is to provide a novel liquid crystal compound. The liquid crystal composition containing the compound has lower rotary viscosity and larger delta epsilon_⊥. And the compound has low price and stable performance, can be widely applied to the field of liquid crystal display and has important application value.

The liquid crystal compound has a structure represented by the following general formula I:

in the general formula I, the compound has the following structure,

R₁represents an alkyl group having 1 to 15 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 15 carbon atoms; wherein any one or more H atoms may be substituted by F or Cl; any one or more CH₂May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;

x represents R₂、F、CF₃Or OCF₃，R₂Represents an alkyl group having 1 to 15 carbon atoms, an alkoxy group, an alkenyl group having 2 to 15 carbon atoms; wherein any one or more H atoms may be substituted by F or Cl, any one or more CH₂May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;

each independently represent

L denotes H, CH₃Or OCH₃；

m and n independently represent 0 or 1.

Preferably, in said formula I, R₁Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 10 carbon atoms; wherein any one or more H atoms may be substituted by F or Cl, any one or more CH₂May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;

x represents R₂、F、CF₃Or OCF₃，R₂Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkenyl group having 2 to 10 carbon atoms, wherein any one or more H atoms may be substituted by F or Cl, and any one or more CH₂May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;

each independently represent

L denotes H, CH₃Or OCH₃；

m, n independently of one another represent 0 or 1;

more preferably, in said formula I, R₁Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 10 carbon atoms; wherein any one or more H atoms may be substituted by F, any one or more CH₂May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;

x represents R₂、F、CF₃Or OCF₃，R₂Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkenyl group having 2 to 10 carbon atoms, wherein any one or more thereofH atoms being optionally substituted by F, any one or more CH₂May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;

each independently represent

L denotes H, CH₃Or OCH₃；

m, n independently of one another represent 0 or 1;

in the general formula I of the invention:

the R is₁Represents an alkyl group having 1 to 15 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 15 carbon atoms; preferably R₁Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 10 carbon atoms; wherein any one or more H atoms may be substituted by F, any one or more CH₂May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;

the R is₂Represents an alkyl group having 1 to 15 carbon atoms, an alkoxy group, an alkenyl group having 2 to 15 carbon atoms; preferably R₂Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, an alkenyl group having 2 to 10 carbon atoms;

wherein any one or more H atoms may be substituted by F or Cl, any one or more CH₂May be replaced by cyclopentyl, cyclobutyl or cyclopropyl;

the above-mentionedEach independently represent

Preferably, it isEach independently represent

More preferablyEach independently represent

Said L represents H, CH₃Or OCH₃；

M and n independently of one another represent 0 or 1

The present invention further preferably:

the liquid crystal compound is one selected from the group consisting of compounds represented by the following formulae I-1 to I-12:

further preferably:

the liquid crystal compound is selected from one of the following compounds:

further preferably:

the liquid crystal compound is selected from one of the following compounds:

wherein R is₁₁、R₂₁Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group, or an alkenyl group having 2 to 10 carbon atoms; wherein any one or more H atoms may be substituted by F.

Wherein R is₁₁Is R₁Further preferred is，R₂₁Is R₂Further preferred is (1).

The second object of the present invention is to provide a method for producing the above liquid crystal compound.

Wherein R is prepared in the following preparation process₁Can be replaced by R₁₁。

1) When n is equal to 1, the compound is,is composed ofOr when n is 0, m is 1,is composed of The synthesis route is specifically as follows:

the preparation method specifically comprises the following steps:

(1) to be provided withThe raw material is subjected to metalation reaction with an organic lithium reagent and then is subjected to reaction with boric acid ester to obtain

(2) Obtained by the step (1)Andreaction to obtain

(3) Obtained by the step (2)Firstly carrying out metalation reaction with n-butyl lithium, and then reacting with difluorodibromomethane to synthesize the compound

(4)Firstly reacting with magnesium chips to form a Grignard reagent, and then reacting with trimethyl borate to obtain the compound

(5) Obtained by the step (4)By reaction with hydrogen peroxide to give

(6) Obtained by the step (3)And the one obtained by the step (5)Williamson Synthesis (Williamson Synthesis) reaction for Synthesis of compounds

R in the compound involved in the above reactions of each step₁L, X, m, n and R in the obtained liquid crystal compound product₁L, X, m, n correspond to (as above).

The above method isIn the step (1), the step (c),the feeding molar ratio of the organic lithium reagent to the organic lithium reagent is 1: 1.0-2.0;the feeding molar ratio of the boric acid ester to the boric acid ester is 1: 1.0-3.0; the reaction temperature can be between-50 and-100 ℃.

Wherein, the raw materialsAre available through public commercial routes;

the organic lithium reagent is selected from one or more of sec-butyl lithium, tert-butyl lithium or n-butyl lithium;

the boric acid ester is selected from one or more of trimethyl borate, triisopropyl borate, tributyl borate or triisobutyl borate.

In the step (2) of the above preparation method,andthe feeding molar ratio of (A) to (B) is 1.0: 1.0 to 1.5; the reaction temperature can be 50-150 ℃.

Wherein, the raw materialsAre commercially available through the open.

In the step (3) of the above production method,the feeding molar ratio of n-butyllithium to dibromodifluoromethane is 1: 1.0-1.5: 1.6-2.0, the reaction temperature is-80-0 ℃, and the reaction time is 1-6 h.

In the step (4) of the above preparation method,the feeding molar ratio of the magnesium chips to the trimethyl borate is as follows: 1: 1.5-2.5: 1.6-2.5. The temperature for dropping trimethyl borate is-20 to 0 ℃.

In the step (5) of the above production method,the feeding molar ratio of the hydrogen peroxide to the hydrogen peroxide is as follows: 1: 2.5 to 3.5; the reaction time was 2 h.

In the step (6) of the above production method,andthe feeding molar ratio of (A) to (B) is 1: 1.0-2.0, the reaction temperature is 50-120 ℃, and the reaction time is 3-8 h.

2) When n is 0, m is 1,is composed ofThe synthesis route is specifically as follows:

the preparation method specifically comprises the following steps:

(1) to be provided withAs a raw material, withObtained by dehydration reaction

(2) Through the steps of (1) ObtainedFirstly carrying out metalation reaction with n-butyl lithium, and then reacting with difluorodibromomethane to synthesize the compound

(3)Firstly reacting with magnesium chips to form a Grignard reagent, and then reacting with trimethyl borate to obtain the compound

(4) Obtained by the step (3)By reaction with hydrogen peroxide to give

(5) Obtained by the step (2)And the one obtained by the step (4)Williamson Synthesis (Williamson Synthesis) reaction for Synthesis of compounds

R in the compound involved in the above reactions of each step₁L, X and R in the resulting liquid-crystalline compound product₁L, X (same as above).

In the step (1) of the above production method,andthe feeding molar ratio of (A) to (B) is 1: 1.5-2; the reaction time is 3-10 h.

In the step (2) of the above preparation method,the feeding molar ratio of n-butyllithium to dibromodifluoromethane is 1: 1.0-1.5: 1.6-2.0, the reaction temperature is-80-0 ℃, and the reaction time is 1-6 h.

In the step (3) of the above production method,the feeding molar ratio of the magnesium chips to the trimethyl borate is as follows: 1: 1.5-2.5: 1.6-2.5. The temperature for dropping trimethyl borate is-20 to 0 ℃.

In the step (4) of the above preparation method,the feeding molar ratio of the hydrogen peroxide to the hydrogen peroxide is as follows: 1: 2.5 to 3.5; the reaction time was 2 h.

In the step (5) of the above production method,andthe feeding molar ratio of (A) to (B) is 1: 1.0-2.0, the reaction temperature is 50-120 ℃, and the reaction time is 3-8 h.

3) When n is 0, m is 1,is composed ofThe synthesis route is specifically as follows:

the preparation method specifically comprises the following steps:

(1) to be provided withAs a raw material, withReaction to obtain

(2) Reacting the obtained product in the step (1) with boron trifluoride diethyl etherate and triethylsilane to obtain

(3) Obtained through the step (2)Firstly carrying out metalation reaction with n-butyl lithium, and then reacting with difluorodibromomethane to synthesize the compound

(4)Firstly reacting with magnesium chips to form a Grignard reagent, and then reacting with trimethyl borate to obtain the compound

(5) Obtained by the step (4)By reaction with hydrogen peroxide to give

(6) Obtained through the step (3)Is/are as followsAnd the one obtained by the step (5)Williamson Synthesis (Williamson Synthesis) reaction for Synthesis of compounds

R in the compound involved in the above reactions of each step₁L, X and R in the resulting liquid-crystalline compound product₁L, X (same as above).

In the step (1) of the above production method, theAnd the above-mentionedThe feeding molar ratio of (A) to (B) is 1: 0.8-1.5;

in the step (2) of the above production method, theThe feeding molar ratio of the boron trifluoride diethyl etherate to the boron trifluoride diethyl etherate is 1: 1.0-3.0; the above-mentionedThe feeding molar ratio of the triethyl silane to the triethyl silane is 1: 1.0-3.0;

in the step (3) of the above production method,the feeding molar ratio of n-butyllithium to dibromodifluoromethane is 1: 1.0-1.5: 1.6-2.0, the reaction temperature is-80-0 ℃, and the reaction time is 1-6 h.

In the step (4) of the above preparation method,the feeding molar ratio of the magnesium chips to the trimethyl borate is as follows: 1: 1.5-2.5: 1.6-2.5. The temperature for dropping trimethyl borate is-20 to 0 ℃.

In the step (5) of the above production method,the feeding molar ratio of the hydrogen peroxide to the hydrogen peroxide is as follows: 1: 2.5 to 3.5; the reaction time was 2 h.

In the step (6) of the above production method,andthe feeding molar ratio of (A) to (B) is 1: 1.0-2.0, the reaction temperature is 50-120 ℃, and the reaction time is 3-8 h.

A third object of the present invention is to provide a liquid crystal composition comprising the above liquid crystal compound.

Preferably, the liquid crystal compound accounts for 0.01-99% of the liquid crystal composition by mass; more preferably 0.01 to 60%, and still more preferably 0.1 to 40%.

A fourth object of the present invention is to provide a liquid crystal compound and a composition containing the liquid crystal compound, which are useful in the field of liquid crystal displays, preferably liquid crystal display devices. The liquid crystal display device includes, but is not limited to, TN, ADS, VA, PSVA, FFS or IPS liquid crystal display. The liquid crystal compound or the composition containing the liquid crystal compound has the performances of wide nematic phase temperature range, proper or high birefringence anisotropy A n, high resistivity, good ultraviolet resistance, high charge retention rate, low vapor pressure and the like.

Detailed Description

The following examples are intended to illustrate the present invention, but are not intended to limit the scope of the invention, which is intended to include within the scope of the appended claims all such equivalent changes and modifications as may be made without departing from the spirit of the invention disclosed herein.

The liquid crystal compounds used in the following examples can be synthesized by a known method or obtained from a publicly available commercial source, unless otherwise specified, and these synthesis techniques are conventional, and the resulting liquid crystal compounds are tested to meet the standards for electronic compounds.

According to the conventional detection method in the field, various performance parameters of the liquid crystal compound are obtained through linear fitting, wherein the specific meanings of the performance parameters are as follows:

Δ n represents optical anisotropy (25 ℃); Δ ε represents the dielectric anisotropy (25 ℃, 1000 Hz); γ 1 represents rotational viscosity (mpa.s, 25 ℃); cp stands for clearing point.