# US 9,517,990 B2 · Negative dielectric anisotropic liquid crystal compounds containing 2,3-difluorophenyl group, and preparation method and use thereof

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- Number: US 9,517,990 B2
- Document ID: US9517990B2
- Status: Granted
- Kind: B2
- Application number: 14/407,652
- Filed: 2013-11-19
- Published: 2015-06-04
- Granted: 2016-12-13
- Earliest claimed: 2012-11-23
- Assignees: Shijiazhuang Chenzhi Yonghua Display Materials Co., Ltd.
- Applicants: Shijiazhuang Chengzhi Yonghua Display Materials Co., Ltd.
- Inventors: Guoliang Yun; Ruimao Hua; Kui Wang; Zefeng Hou; Lei Zhao; Gang Wen; Lianbo Mao
- Web page: https://patentgrep.com/patent/US9517990B2

## CPC

- C07C 43/247: containing halogen
- C07C 43/225: containing halogen
- C09K 19/30: containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K 19/3066: {in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers}
- C09K 19/3068: {chain containing -COO- or -OCO- groups}
- C09K 2019/122: {Ph-Ph}
- C09K 2019/123: {Ph-Ph-Ph}
- C09K 2019/3004: {Cy-Cy}
- C09K 2019/3009: {Cy-Ph}
- C09K 2019/3016: {Cy-Ph-Ph}
- C09K 2019/3027: {Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene}
- C09K 2019/3036: {Cy-C2H4-Ph}
- C09K 2019/3075: {Cy-COO-Ph}
- C09K 2019/3096: {Cyclobutane rings}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## 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.

## Claims

### Claim 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 —CH2— is substituted with O;
Z is selected from a single bond, —COO—, —CH2O—, and —CH2CH2—;
R is selected from C1-C6 alkyl and C1-C6 alkoxy; and
m is 1 or 2.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein the compound is one of Formulas I1 to I9 below:
wherein R is C1-C6 alkoxy.

### Claim 3 (depends on 1)

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.

### Claim 4 (depends on 3)

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.

### Claim 5 (depends on 3)

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.

### Claim 6 (depends on 1)

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.

### Claim 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 —CH2— is substituted with O;
Z is a single bond, —COO—, —CH2O—, or —CH2CH2—;
R, R1, R3, R4 and R5 are each independently a C1-C6 alkyl or a C1-C6 alkoxy;
m and n are each independently 1 or 2;
R2 and R6 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.

### Claim 8 (depends on 7)

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.

### Claim 9 (depends on 7)

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.

### Claim 10 (depends on 7)

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.

### Claim 11 (depends on 7)

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

### Claim 12 (depends on 11)

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:

### Claim 13 (depends on 11, 12)

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:

### Claim 14 (depends on 11, 13)

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.

### Claim 15 (depends on 7)

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.