Liquid crystal composition having negative dielectric anisotropy

Patent metadata

Field	Value
Publication number	US-9428693-B2
Application number	US-201314407753-A
Country	US
Kind code	B2
Filing date	Aug 23, 2013
Priority date	Dec 20, 2012
Publication date	Aug 30, 2016
Grant date	Aug 30, 2016

Abstract

A liquid crystal composition having a negative dielectric anisotropy is disclosed. The liquid crystal composition includes compounds of Formulas I to IV. The composition has a low threshold voltage, a low rotary viscosity, a high resistivity, a high voltage holding ratio, and a good high temperature and UV stability. The LC medium has the advantage of obviously reduced response time after polymerization under UV irradiation, thus having important application value.

First claim

What is claimed is:

1. A liquid crystal composition, comprising compounds of Formulas I to IV:

wherein
in Formula I, R 1 and R 2 are each selected from a group a or b below, in which:
a is selected from at least one of C1-C12 alkyl, C1-C12 alkyl substituted with fluoro or chloro, C1-C12 alkoxy, C1-C12 alkoxy substituted with fluoro or chloro, H and —CH═CH 2 ; and
b is a group formed by substituting at least one —CH 2 — in the group a with at least one of the groups below: —CH═CH— and —O—;

is selected from at least one of 1,4-phenylene, 1,4-phenylene monosubstituted with fluoro or chloro, 1,4-cyclohexyl, and a group formed by substituting one or two —CH 2 — in 1,4-cyclohexyl with O; and
m is 1 or 2;
in Formula II, H is cyclopentyl or cyclobutyl;

is as defined for

in Formula I;
Z is selected from at least one of a single bond, —COO—, —CH 2 —O— and —CH 2 CH 2 —;
R 3 is selected from at least one of C1-C6 alkyl or C1-C6 alkoxy; and
n is 1 or 2;
in Formula III, R 4 and R 5 are each selected from C2-C12 alkenyl, C2-C12 alkenyl substituted with halo, acrylate, methacrylate, ethenyloxy, propenyloxy, oxiranyl, oxetanyl and ketenyl, and at least one of R 4 and R 5 is acrylate, methacrylate, ethenyloxy, propenyloxy, oxiranyl, oxetanyl or ketenyl;

are each selected from a group g or h below, in which:
g is selected from at least one of 1,4-phenylene, 1,4-phenylene substituted with fluoro, 1,4-cyclohexyl, a group formed by substituting one or two —CH 2 — in 1,4-cyclohexyl with O or S, 3,7-dibenzofuranyl, 1,4-bicyclo[2,2,2]octylene, piperidin-1,4-diyl, naphthalen-2,6-diyl, decahydronaphthalen-2,6-diyl, 1,2,3,4-tetrahydronaphthalen-2,6-diyl and indan-2,5-diyl; and
h is a group formed by substituting at least one hydrogen in the group g with at least one of the groups below: F, Cl, C1-C7 alkyl, C1-C7 alkoxy, C1-C7 alkylcarbonyl, C1-C7 alkoxycarbonyl and C1-C7 alkylcarbonyloxy;
X 1 and X 3 are each selected from at least one of —O—, —S—, —OCH 2 —, —CH 2 —O—, —CO—, —COO—, —OCO—, —OCO—O—, —CH 2 CH 2 —, a single bond, C1-C12 alkylene, a group formed by substituting at least one —CH 2 — in C1-C12 alkylene with —O—, and C2-C12 alkylene substituted with halo;
X 2 is a single bond, —OCH 2 —, —CH 2 —O—, —CO—, —COO—, —OCO—, —OCO—O— or —CH 2 CH 2 —;
d and e are each an integer of 0-3; and
in Formula IV, R 6 and IC are each a group j or k, in which:
j is selected from at least one of C1-C8 alkyl, C1-C8 alkyl substituted with fluoro or chloro, C1-C8 alkoxy and C1-C8 alkoxy substituted with fluoro or chloro, H, —CH═CH 2 and —CH═CH—CH 3 ; and
k is a group formed by substituting at least one —CH 2 — in the group j with at least one of the groups below: —CH═CH—, —COO—, —OOC— or —O—;

is selected from at least one of 1,4-phenylene, 1,4-phenylene substituted with fluoro, 1,4-cyclohexyl, and a group formed by substituting one or two —CH 2 — in 1,4-cyclohexyl with O;
Z 3 is a single bond, —COO—, —CH 2 —O—, —CH 2 CH 2 — or —CH 2 —; and
f is 2 or 3.

2. The composition of claim 1 , wherein the liquid crystal composition consists of the compounds of Formulas I to IV.

3. The composition of claim 1 , wherein the weight ratio of the compounds of Formulas I, II, III and IV is 5-60:1-60:0.1-5:1-80.

4. The composition of claim 1 , wherein the compound of Formula III is any one of the compounds of Formulas III-1 to III-32:

wherein P 1 and P 2 are selected from C2-C12 alkenyl, C2-C12 alkenyl substituted with halo, acrylate, methacrylate, ethenyloxy, propenyloxy, oxiranyl, oxetanyl, and ketenyl, and at least one of P 1 and P 2 is acrylate, methacrylate, ethenyloxy, propenyloxy, oxiranyl, oxetanyl or ketenyl
and the compound of Formula IV is selected from any one of the compounds of Formulas IV-1 to IV-10:

wherein in Formulas IV-1 to IV-10, R 8 and R 9 are each selected from at least one of C1-C8 alkyl groups.

5. The composition of claim 1 , wherein the liquid crystal composition consists of 1 to 5 compounds of Formula I, 1 to 6 compounds of Formula II, 1 to 2 compounds of Formula III and 1 to 6 compounds of Formula IV.

6. The composition of claim 1 , wherein the composition further comprises at least one of the following components: a compound of Formulas V, a compound of VI, and an initiator;

wherein in Formula V, R 10 and R 11 are each selected from at least one of C1-C8 alkyl groups; and

the compound of Formula V is present in an amount of 1-40% based on the total weight of the composition;

in Formula VI, R′ is selected from at least one of C1-C8 alkyl or C1-C8 alkoxy; and g is an integer of 0-2;
the compound of Formula VI is present in an amount of 0.001-0.1% based on the total weight of the composition;
the initiator is selected from at least one of

and
the initiator is present in an amount of 0.001-0.05% based on the total weight of the composition.

7. The composition of claim 1 , wherein a difference between a maximum temperature and a minimum temperature over which the liquid crystal composition is maintained in a nematic phase is not less than 80 temperature units;
the liquid crystal composition has a rotational viscosity not higher than 250 mPa·s;
a dielectric anisotropy Δ∈ at 25° C. and 1 kHz is −0.5 to −7.5; and
a birefringence Δn lower than 0.15.

8. A method for preparing the composition of claim 1 , comprising the step of uniformly mixing each of the components of the composition according to claim 1 to obtain the composition.

9. An electro-optical display with active matrix addressing, having the composition of claim 1 as an electrolyte.

10. The electro-optical display of claim 9 , wherein the display is a VA, MVA, PVA, PSVA, PSA-VA, PS-IPS or PSA-IPS type display.

11. The composition of claim 1 , wherein the weight ratio of the compounds of Formulas I, II, III and IV is 10-40:1-40:0.1-2:10-60.

12. The composition of claim 1 , wherein the weight ratio of the compounds of Formulas I, II, III and IV is 2-20:2-20:0.1-1:10-60.

13. The composition of claim 1 , wherein the liquid crystal composition consists of 1 to 4 compounds of Formula I, 1 to 5 compounds of Formula II, 1-2 compounds of Formula III

Assignees

• Shijiazhuang Chengzhi Yonghua Display Materials Co Ltd

Inventors

• Wen Gang
• Hua Ruimao
• Yuan Guoliang
• Feng Jingyi
• Mao Lianbo
• Rong Xiaobin
• Gui Lihong
• Shi Ziqian

Classifications

• C09K19/3003

  Compounds containing at least two rings in which the different rings are directly linked (covalent bond) · CPC title

• C09K19/44

  containing compounds with benzene rings directly linked · CPC title

• C09K19/30 Primary

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

• C09K2019/0448

  the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate · CPC title

• C09K2019/301

  Cy-Cy-Ph · CPC title