Negative dielectric anisotropic liquid crystal compounds containing 2,3-difluorophenyl group, and preparation method and use thereof

Patent metadata

Field	Value
Publication number	US-9517990-B2
Application number	US-201314407652-A
Country	US
Kind code	B2
Filing date	Nov 19, 2013
Priority date	Nov 23, 2012
Publication date	Dec 13, 2016
Grant date	Dec 13, 2016

Abstract

A negative dielectric anisotropic liquid crystal compound containing 2,3-difluorophenyl, and a preparation method and use thereof are disclosed. The compound has a general structural formula as shown in Formula I. The negative dielectric anisotropic liquid crystal compound has a negative dielectric anisotropy (Δ∈), and has cyclobutyl or cyclopentyl as a terminal group. Compared with conventional liquid crystal compounds with a flexible alkyl chain as a terminal group, the compound of Formula I according to the present invention has the advantage of high clearing point, and enables extension of the application range of a liquid crystal mixture because a positive correlation exists between the clearing points of the liquid crystal mixture and monomer liquid crystal compounds. In addition, the compound can increase the absolute value of the negative dielectric constant of the liquid crystal mixture, thus having an important application value.

First claim

What is claimed is:

1. A compound of Formula I:

wherein H is cyclopentyl;

is selected from 1,4-phenylene, 1,4-phenylene substituted with fluoro, 1,4-cyclohexyl, and 1,4-cyclohexyl in which one or two —CH 2 — is substituted with O;
Z is selected from a single bond, —COO—, —CH 2 O—, and —CH 2 CH 2 —;
R is selected from C1-C6 alkyl and C1-C6 alkoxy; and
m is 1 or 2.

2. The compound according to claim 1 , wherein the compound is one of Formulas I1 to I9 below:

wherein R is C1-C6 alkoxy.

3. A method of adjusting at least one of clearing point and negative dielectric constant of a liquid crystal mixture, comprising a step of adding a compound of Formula I according to claim 1 .

4. The method of claim 3 , wherein adjusting the clearing point of the liquid crystal mixture is increasing the clearing point of the liquid crystal mixture.

5. The method of claim 3 , wherein adjusting the negative dielectric constant of the liquid crystal mixture is increasing the negative dielectric constant of the liquid crystal mixture.

6. A method of preparing a liquid crystal display material or electrooptical display material, comprising a step of adding a compound of Formula I according to claim 1 .

7. A liquid crystal mixture comprising at least one compound of Formula I and a second component,

wherein the second component comprises 1) at least one compound of Formula II and at least one compound of Formula III; or 2) at least one compound of Formula II, at least one compound of Formula III, and at least one compound of Formula IV,

wherein H is cyclopentyl;

are each independently 1,4-phenylene, 1,4-phenylene substituted with fluoro, 1,4-cyclohexyl, or 1,4-cyclohexyl in which one or two —CH 2 — is substituted with O;
Z is a single bond, —COO—, —CH 2 O—, or —CH 2 CH 2 —;
R, R 1 , R 3 , R 4 and R 5 are each independently a C1-C6 alkyl or a C1-C6 alkoxy;
m and n are each independently 1 or 2;
R 2 and R 6 are each independently a C1-C6 alkyl or C2-C6 alkenyl;

are each independently 1,4-phenylene or 1,4-phenylene substituted with fluoro; and
a weight ratio of the compounds of Formula II and Formula III is 5-50:50-95, or a weight ratio the compounds of Formula II, Formula III and Formula IV is 5-50:50-95:1-5.

8. The liquid crystal mixture of claim 7 , wherein the at least one compound of Formula I is selected from the compounds below:

wherein R is C1-C6 alkoxy.

9. The liquid crystal mixture of claim 7 , wherein each of the at least one compound of Formula I is 1-30% by weight based on a total weight of the liquid crystal mixture.

10. The liquid crystal mixture of claim 7 , wherein the at least one compound of Formula I is 1-60% by weight based on a total weight of the liquid crystal mixture.

11. The liquid crystal mixture of claim 7 , wherein the second component comprises the following compounds in a weight ratio given below:

12. The liquid crystal mixture of claim 11 , wherein the at least one compound of Formula I is one of the following in a weight ratio given relative to a weight of 100 for the second component of claim 11 :

13. The liquid crystal mixture of claim 12 , wherein the at least one compound of Formula I is one of the following in a weight ratio given relative to a weight of 100 for the second component of claim 11 :

14. The liquid crystal mixture of claim 13 , wherein a weight of d1, e1, f1, or g1 is 27 relative to a weight of 100 for the second component of claim 11 .

15. A method of preparing a liquid crystal display material or electrooptical display material, comprising a step of adding the liquid crystal mixture of claim 7 .

Assignees

• Shijiazhuang Chengzhi Yonghua Display Materials Co Ltd
• Shijiazhuang Chenzhi Yonghua Display Mat Co Ltd

Inventors

• Yun Guoliang
• Hua Ruimao
• Wang Kui
• Hou Zefeng
• Zhao Lei
• Wen Gang
• Mao Lianbo

Classifications

• C09K19/30

  containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings · CPC title

• C07C43/225

  containing halogen · CPC title

• C09K19/3066

  in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers · CPC title

• C09K2019/3096

  Cyclobutane rings · CPC title

• C09K2019/3027

  Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene · CPC title