# US 11,078,420 B2 · Liquid crystal composition and liquid crystal display element

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- Number: US 11,078,420 B2
- Document ID: US11078420B2
- Status: Granted
- Kind: B2
- Application number: 16/228,435
- Filed: 2018-12-20
- Published: 2019-06-20
- Granted: 2021-08-03
- Earliest claimed: 2017-12-20
- Assignees: Shijiazhuang Chengzhi Yonghua Display Material Co., Ltd.
- Applicants: Shijiazhuang Chengzhi Yonghua Display Material Co., Ltd
- Inventors: Jinsong Meng; Ming Li; Kui Wang; Xing Zhang; Guoliang Yun; Zhian Liang; Yiping Wang; Gang Wen
- Web page: https://patentgrep.com/patent/US11078420B2

## CPC

- C09K 19/32: containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K 19/3003: {Compounds containing at least two rings in which the different rings are directly linked (covalent bond)}
- C09K 19/3028: {in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds}
- C09K 19/3066: {in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers}
- C09K 19/3098: {Unsaturated non-aromatic rings, e.g. cyclohexene rings}
- C09K 2019/0448: {the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate}
- C09K 2019/122: {Ph-Ph}
- C09K 2019/123: {Ph-Ph-Ph}
- C09K 2019/3004: {Cy-Cy}
- C09K 2019/3009: {Cy-Ph}
- C09K 2019/301: {Cy-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 2019/548: {stabilizing the alignment; Polymer stabilized alignment}
- G02F 1/1362: Active matrix addressed cells {(G02F1/134336, G02F1/134363 take precedence)}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS

## Abstract

Provided are a polymerizable compound represented by formula I and a liquid crystal composition comprising the polymerizable compound, particularly a PSVA liquid crystal composition for displays or TV applications and a PSA-IPS liquid crystal composition for an IPS mode; in particular, the polymerizable compound has a faster polymerization rate, and a “material system” formed from the selected polymerizable component and liquid crystal component has a lower rotary viscosity and better photoelectric properties, and has a high VHR after (UV) photoradiation, this avoiding the problem of the occurrence of residual images to final displays.

## Claims

### Claim 1

A polymerizable liquid crystal compound represented by formulas I-1 to I-23:
wherein
each S independently represents H, a C1-C5 alkyl group, a C1-C5 alkoxy group, a fluorine-substituted C1-C5 alkyl group, a fluorine-substituted C1-C5 alkoxy group, F or Cl, wherein any one or more unconnected CH2 may be independently replaced by —O—, —S—, —CO—, —CH2O—, —OCH2—, —COO—, —OOC— or an acrylate group or a methacrylate group;
each P independently represents
each Sp independently represents a single bond, a C1-C5 alkyl group, a C1-C5 alkenyl group, wherein any one or more unconnected CH2 may be replaced by —O—, —S—, —CO—, —CH2O—, —OCH2—, —COO—, —OOC— or an acrylate group;
and each o independently represents 0, 1, 2 or 3.

### Claim 2 (depends on 1)

The polymerizable liquid crystal compound according to claim 1, wherein the compound represented by formula I-1 to I-23 is a compound represented by formulas I-1-1 to I-23-4:

### Claim 3 (depends on 1)

A liquid crystal composition, comprising one or more compounds represented by formula I-1 to I-23 of claim 1 as a first component, one or more compounds represented by formula II as a second component, and one or more compounds represented by formula III as a third component:
wherein
R1, R2, R3, and R4 each independently represent an alkyl group having a carbon atom number of 1-10, a fluorine-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorine-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorine-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluorine-substituted alkenoxy group having a carbon atom number of 3-8, and any one or more unconnected CH2 in the groups represented by R3 and R4 may be substituted with cyclopentyl, cyclobutyl or cyclopropyl;
Z1 and Z2 each independently represent a single bond, —CH2CH2— or —CH2O—;
each independently represent
each independently represent one or more of
m represents 1 or 2; and
n represents 0, 1 or 2.

### Claim 4 (depends on 3)

The liquid crystal composition according to claim 3, wherein in said liquid crystal composition, a total mass content of the compounds represented by formula I-1 to I-23 is 0.01-1%, a total mass content of the compounds represented by formula II is 15-60%, and a total mass content of the compounds represented by formula III is 20-60%.

### Claim 5 (depends on 3)

The liquid crystal composition according to claim 3, wherein said one or more compounds represented by formula II are one or more compounds represented by formulas II-1 to II-15; and said one or more compounds represented by formula III are one or more compounds represented by formulas III-1 to III-12:
wherein
R3 and R4 each independently represent an alkyl group having a carbon atom number of 1-10, a fluorine-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorine-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorine-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluorine-substituted alkenoxy group having a carbon atom number of 3-8, and any one or more unconnected CH2 in the groups represented by R3 and R4 may be substituted with cyclopentyl, cyclobutyl or cyclopropyl.

### Claim 6 (depends on 3)

The liquid crystal composition according to claim 3, wherein said liquid crystal composition is a negative liquid crystal composition, and further comprises one or more compounds represented by formula IV:
wherein
R5 and R6 each independently represent an alkyl group having a carbon atom number of 1-10, a fluorine-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorine-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorine-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluorine-substituted alkenoxy group having a carbon atom number of 3-8, and any one or more CH2 in the groups represented by R5 and R6 may be substituted with cyclopentyl, cyclobutyl or cyclopropyl;
and W represents O, S or —CH2O—.

### Claim 7 (depends on 3)

The liquid crystal composition according to claim 3, wherein said liquid crystal composition is a negative liquid crystal composition, and further comprises one or more compounds represented by formula V:
wherein
R7 and R8 each independently represent an alkyl group having a carbon atom number of 1-10, a fluorine-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorine-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorine-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or an fluorine-substituted alkenoxy group having a carbon atom number of 3-8;
and
each independently represent 1,4-phenylene, 1,4-cyclohexylene or 1,4-cyclohexenylene.

### Claim 8 (depends on 3)

The liquid crystal composition according to claim 3, wherein said liquid crystal composition is a negative liquid crystal composition, and further comprises one or more compounds represented by formula VI,
wherein
R9 and R10 each independently represent an alkyl group having a carbon atom number of 1-10, a fluorine-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorine-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorine-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or an fluorine-substituted alkenoxy group having a carbon atom number of 3-8;
represents 1,4-phenylene, 1,4-cyclohexylene or 1,4-cyclohexenylene;
and each (F) independently represents H or F.

### Claim 9 (depends on 3)

A liquid crystal display element or liquid crystal display comprising the liquid crystal composition of claim 3, wherein said display element or display is an active matrix display element or display or a passive matrix display element or display.

### Claim 10 (depends on 9)

The liquid crystal display element or liquid crystal display according to claim 9, wherein said active matrix display element or display is a PSVA-TFT liquid crystal display element or display.