Compound and liquid crystal composition

Patent metadata

Field	Value
Publication number	US-12480049-B2
Application number	US-202318165361-A
Country	US
Kind code	B2
Filing date	Feb 7, 2023
Priority date	Feb 7, 2022
Publication date	Nov 25, 2025
Grant date	Nov 25, 2025

Abstract

A ferroelectric liquid crystal (FLC) material for the deformed helix FLC (DHFLC) electro-optical mode devices and shows optimum electro-optical properties including high tilt angle (>38°), and short helix pitch (<120 nm), and spontaneous polarization (>100 nC/cm2) comprising at least two components, wherein at least one FLC component is a chiral compound of Formula (I):particularly:wherein W1 and W2 are chiral groups with polar substituent at chiral centre, A and B are independently N atom or CH groups providing that at least one of A or B is N atom. Other various groups are as defined herein.

First claim

The invention claimed is:

1 . A ferroelectric liquid crystal (FLC) material for deformed helix FLC (DHFLC) electro-optical mode devices comprising at least two components and shows optimum electro-optical properties, wherein at least one FLC component is a chiral compound of Formula (I):

wherein:
n is 0 or 1;
R 1 and R 4 each independently 1,4-phenylene substituted with one or more substituents selected from the group consisting of halogen and methyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, wherein the pyrimidine-2,5-diyl and the pyridine-2,5-diyl are optionally substituted with one or more substituents selected from the group consisting of halogen and methyl;
R 2 , and R 3 each independently are 1,4-phenylene, or pyrimidine-2,5-diyl, or pyridine-2,5-diyl, optionally substituted with one or more substituents selected from the group consisting of halogen and methyl;
A 1 and A 2 are independently absent, that has meaning the group W 1 or W 2 are directly attached to the rings R 1 or R 4 , or selected from the group consisting of —O—, —S—, and ester; and
W 1 and W 2 are independently chiral alkyl C m H 2m+1 or alkenyl C m H 2m , wherein m=4-14, and optionally wherein one or more hydrogens are independently replaced by F, Cl or cyano, and optionally one or more CH 2 are independently replaced with CF 2 , O, or —CO— groups provided that two O atoms are not linked together, and

wherein at least one FLC component is at least one achiral smectic C liquid crystal compound of Formula (II):

wherein:
R 5 , R 6 , R 7 , and R 8 independently are 1,4-phenylene, or pyrimidine-2,5-diyl, or pyridine-2,5-diyl, optionally substituted with at least one substituent selected from the group consisting of halogen and methyl;
k is 0 or 1;
A 3 and A 4 are independently absent or selected from the group consisting of —O—, —S—, and ester; and

W 3 and W 4 are independently alkyl C m H 2m+1 or alkenyl C m H 2m , wherein m=4-12, and optionally one or more hydrogens are independently replaced by F, furthermore, optionally one or more CH 2 are independently replaced with CF 2 , O, or —CO— groups provided that two O atoms are not linked together, wherein the FLC material exhibits a tilt angle between 35-47 degrees and a spontaneous polarization larger than 100 nC/cm 2 at 25° C. and 1 atm.

2 . The FLC material of claim 1 , wherein W 1 and W 2 are independently substituted at their chiral center/centers with at least one moiety selected from the group consisting of F, Cl, trifluoromethyl, O, and cyano.

3 . The FLC material of claim 1 , wherein W 1 and W 2 are independently selected from the group consisting of:

wherein
* for each instance represents a chiral center;
X is fluoro or chloro or cyano; and
p is an integer in the range of 2 to 10.

4 . The FLC material of claim 1 , wherein the chiral compound of Formula (I) is of Formula (Ia):

wherein
R 3 , W 1 and W 2 are as defined in claim 1 .

5 . The FLC material of claim 1 , wherein the chiral compound of Formula (I) is of Formula (Ib):

wherein
R 3 , W 1 and W 2 are as defined in claim 1 .

6 . The FLC material of claim 1 , wherein the chiral compound of Formula (I) is of Formula (Ic):

wherein
R 3 , W 1 and W 2 are as defined in claim 1 .

7 . The FLC material of claim 1 , wherein the chiral compound of Formula (I) is of Formula (Id):

wherein
R 3 , W 1 and W 2 are as defined in claim 1 .

8 . The FLC material of claim 1 , wherein the chiral compound of Formula (I) is of Formula (Ie):

wherein
R 3 , W 1 and W 2 are as defined in claim 1 .

9 . The FLC material of claim 1 , wherein the chiral compound of Formula (I) is of Formula (If):

wherein
R 3 , W 1 and W 2 are as defined in claim 1 .

10 . The FLC material of claim 1 , wherein the chiral compound of Formula (I) is selected from the group consisting of:

11 . The FLC material of claim 1 , wherein the at least one achiral smectic C liquid crystal compound of Formula (II) is of the Formula (IIa):

wherein
R 11 and R 12 independently are 1,4-phenylene, or pyrimidine-2,5-diyl, or pyridine-2,5-diyl, optionally substituted with at least one substituent selected from the group consisting of halogen and methyl; and
W 3 , A 4 and W 4 are as defined in claim 1 .

12 . The FLC material of claim 1 , wherein the at least one achiral smectic C liquid crystal compound of Formula (II) is selected from the group consisting of:

13 . The FLC material of claim 1 , wherein an average length of W 1 and W 2 is larger than an average length of W 3 and W 4 .

14 . The FLC material of claim 1 , wherein an average length of W 1 and W 2 is equal to an average length of W 3 and W 4 or larger than that by up to 2-times.

15 . The FLC material of claim 1 , wherein the total number of rings in R 1 , R 2 , R 3 and R 4 is equal to the total numbers of rings in R 5 , R 6 , R 7 and R 8 .

16 . The FLC material of claim 1 , wherein the chiral compound of Formula (I) and the at least one achiral smectic C liquid crystal compound of Formula (II) have a molar ratio in the range of 10:90 to 40:60.

17 . The FLC material of claim 1 , wherein the chiral compound of Formula (I) has a concentration of less than 20 molar % based on the total number of moles of the FLC material.

Assignees

• Univ Hong Kong Science & Tech

Inventors

• Vashchenko Valerii Vladimirovich
• Vashchenko Olena V
• Srivastava Abhishek Kumar
• Sun Zhibo
• Yuan Zhengnan
• Kwok Hoi Sing

Classifications

• C09K19/345

  the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms · CPC title

• C09K2019/323

  containing a binaphthyl · CPC title

• C09K2019/123

  Ph-Ph-Ph · CPC title

• C09K19/322

  Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring · CPC title

• C09K2019/122

  Ph-Ph · CPC title