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 王新颖 戴雄 王迎运 储士红 田会强 姜天孟 陈海光 于 2019-02-20 设计创作，主要内容包括：本发明属于液晶材料技术领域,具体涉及一种液晶化合物及其制备方法与应用,其结构式为：<Image he="104" wi="526" file="DDA0001973602520000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>本发明所述液晶化合物具有较大的垂直介电各项异性,具有较大的穿透率,且同时具有高清亮点,比较高的光学各向异性,适中的旋转粘度和液晶互溶性,低温工作效果表现优秀,良好的热稳定性、化学稳定性、光学稳定性及力学等方面的性能；从而有效降低驱动电压,提高了液晶显示装置的响应速度,同时具有光学各向异性数值适中、电荷保持率高等特点。(The invention belongs to the technical field of liquid crystal materials, and particularly relates to a liquid crystal compound, a preparation method and application thereof, wherein the structural formula of the liquid crystal compound is as follows:)

1. A liquid crystal compound having a formula as described in formula (I):

in the general formula I, R₁Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with F, an alkoxy group having 1 to 10 carbon atoms substituted with F, a cyclopropyl group, a cyclobutyl group or a cyclopentyl group;

Z₁、Z₂represents a single bond, -O-, -CH₂-、-CH₂CH₂-or-CH₂O-；

To represent

n represents 1 or 2; when n is equal to 2, the compound is,represent the same or different groups;

to represent

R₂Denotes CF₃Or OCF₃。

2. A compound according to claim 1, wherein in formula (I), R is₁Represents an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms.

3. The compound of claim 1, having the formula:

R₀represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with F, an alkoxy group having 1 to 10 carbon atoms substituted with F; z₁、Z₂Represents a single bond, -O-, -CH₂-、-CH₂CH₂-or-CH₂O-；R₂Denotes CF₃Or OCF₃。

4. The compound of claim 1, having the formula:

5. a process for the preparation of a compound according to any one of claims 1 to 4, characterized in that it is prepared by the following route:

6. the method of claim 5, comprising the step of

1) Will be provided withMetalating with organic lithium reagent, and reacting with boric acid ester to obtain

2)By suzuki reaction, obtaining

7. The production method according to claim 6,

in the step 1) described above, the step of,the feeding molar ratio of the organic lithium reagent to the organic lithium reagent is 1: 1.0-2.0, and the feeding molar ratio of the organic lithium reagent to the boric acid ester is 1: 1.0-3.0;

preferably, the reaction temperature can be between-50 and-100 ℃;

and/or in said step 2) of the method,the feeding molar ratio of (A) to (B) is 1.0: 1.0 to 1.5;

preferably, the reaction temperature can be 60-140 ℃.

8. A composition comprising a compound according to any one of claims 1 to 4.

9. The composition according to claim 8, wherein the compound is present in the composition in an amount of 0.01 to 60% by weight, preferably 0.1 to 50% by weight, and more preferably 0.1 to 40% by weight.

10. Use of the compound according to any one of claims 1 to 4 and a composition containing the same in the field of liquid crystal display, preferably in a liquid crystal display device.

Technical Field

The invention belongs to the technical field of liquid crystal materials, and 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, and in order to improve the performance of the material and enable the material to adapt to new requirements, the synthesis of a novel structure liquid crystal compound and the research of the structure-performance relationship become important work in the field of liquid crystal.

Disclosure of Invention

The invention aims to protect a liquid crystal compound containing a dibenzofuran structure, which has a structural formula shown in a general formula (I):

in the general formula I, R₁Indicating toolAn alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with F, an alkoxy group having 1 to 10 carbon atoms substituted with F, a cyclopropyl group, a cyclobutyl group or a cyclopentyl group;

Z₁、Z₂represents a single bond, -O-, -CH₂-、-CH₂CH₂-or-CH₂O-；

To representOr

n represents 1 or 2; when n is equal to 2, the compound is,represent the same or different groups;

to represent

R₂Denotes CF₃Or OCF₃。

Preferably, in the formula (I), R₁Represents an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms.

Preferably, R₁Represents propyl, cyclopropyl or cyclopentyl;

preferably, Z₁Represents a single bond;

preferably, the first and second liquid crystal materials are,to represent

Preferably, Z₂Represents a single bond or-CH₂O-；

Preferably, the first and second liquid crystal materials are,to represent

Preferably, R₁Represents propyl, cyclopropyl or cyclopentyl; z₁Represents a single bond;to represent Z₂Represents a single bond or-CH₂O-；To represent

Preferably, the compounds of the present invention have the structural formula:

R₀represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms substituted with F, an alkoxy group having 1 to 10 carbon atoms substituted with F; z₁、Z₂Represents a single bond, -O-, -CH₂-、-CH₂CH₂-or-CH₂O-；R₂Denotes CF₃Or OCF₃。

Further preferably, the compound of the present invention has a structural formula:

another object of the invention is to protect the preparation of the compounds according to the invention, which is prepared by the following route:

preferably, the method comprises the following preparation steps:

1) will be provided withMetalating with organic lithium reagent, and reacting with boric acid ester to obtain

2)Andby suzuki reaction, obtaining

In the step 1) of the above-mentioned method,the feeding molar ratio of the organic lithium reagent to the organic lithium reagent is 1: 1.0-2.0, and the feeding molar ratio of the organic lithium reagent to the boric acid ester is 1: 1.0-3.0;

preferably, the reaction temperature can be between-50 and-100 ℃;

wherein the content of the first and second substances,are 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 method,andthe feeding molar ratio of (A) to (B) is 1.0: 1.0 to 1.5;

preferably, the reaction temperature can be 60-140 ℃;

wherein, the raw materialsAre commercially available through the open.

The method of the invention, if necessary, involves conventional post-treatment, such as: extracting with dichloromethane, ethyl acetate or toluene, separating liquid, washing with water, drying, evaporating with vacuum rotary evaporator, and purifying the obtained product by vacuum distillation or recrystallization and/or chromatographic separation.

The compound of the invention can be stably and efficiently obtained by the preparation method.

A third object of the invention is to protect compositions containing said compounds. The mass percentage of the compound in the composition is 0.01-60%, preferably 0.1-50%, and more preferably 0.1-40%.

The fourth object of the present invention is to protect the use of said compounds and compositions containing said compounds in the field of liquid crystal displays, preferably in liquid crystal display devices. The liquid crystal display device includes, but is not limited to, a VA, TN, STN, FFS or IPS liquid crystal display.

The invention has the following beneficial effects:

the liquid crystal compound has larger vertical dielectric anisotropy, larger penetration rate, high clearing point, higher optical anisotropy, moderate rotary viscosity and liquid crystal intersolubility, excellent low-temperature working effect, good thermal stability, chemical stability, optical stability, mechanical property and the like; therefore, the driving voltage is effectively reduced, the response speed of the liquid crystal display device is improved, and the liquid crystal display device has the characteristics of moderate optical anisotropy value, high charge retention rate and the like.

Detailed Description

The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.

The starting materials are commercially available from the open literature unless otherwise specified.

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 represents the dielectric anisotropy (25 ℃, 1000 Hz); and ^ represents a dielectric constant (25 ℃, 1000Hz) in the vertical molecular axis direction.