Formulations of bioreachable dopants for liquid crystals

Patent metadata

Field	Value
Publication number	US-2023203378-A1
Application number	US-202117928265-A
Country	US
Kind code	A1
Filing date	Jun 4, 2021
Priority date	Jun 5, 2020
Publication date	Jun 29, 2023
Grant date	—

Abstract

The present disclosure relates to formulations having one, two, or more chiral dopants, as well as materials and methods including such formulations. In particular instances, the formulation can include an achiral host, such as a nematic substance.

First claim

1 . A formulation comprising:
about 0.5 wt. % to about 30 wt. % of a first chiral dopant derived from betulin or glycyrrhetinic acid; and about 50 wt. % to about 99.5 wt. % of an achiral host.

2 . The formulation of claim 1 , wherein the first chiral dopant comprises a structure having formula (IA) or (IB):

or a salt thereof, wherein:
each of R 1 and R 2 is, independently, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aralkyl, optionally substituted aryl, optionally substituted alkaryl, optionally substituted alkanoyl, optionally substituted aryloyl, or optionally substituted heterocyclyloyl.

3 . The formulation of claims 1 - 2 , wherein the first chiral dopant comprises a structure having formula (IAa), (IBa), (IAb), or (IBb):

wherein:
each of R 1a , R 2a , R 1b , and R 2b is, independently, optionally substituted alkyl, optionally substituted haloalkyl, optionally substituted alkenyl, optionally substituted aralkyl, optionally substituted aryl, or optionally substituted alkaryl.

4 . The formulation of claims 1 - 3 , wherein the first chiral dopant is selected from the group consisting of:

5 . The formulation of claims 1 - 4 , further comprising at least one polymerizable mesogenic compound having at least one polymerizable functional group or wherein the achiral host comprises at least one polymerizable mesogenic compound having at least one polymerizable functional group.

6 . The formulation of claim 5 , wherein the polymerizable functional group includes an epoxy group, a vinyl group, an allyl group, an acrylate, a methacrylate, an isoprene group, an alpha-amino carboxylate, or any combination thereof.

7 . The formulations of claims 1 - 6 , wherein the achiral host further comprises a nematic or a nematogenic substance.

8 . The formulation of claim 7 , wherein the nematic or the nematogenic substance is selected from azoxybenzenes, benzylideneanilines, biphenyls, terphenyls, phenyl benzoates, cyclohexyl benzoates, phenyl esters of cyclohehexanecarboxylic acid, cyclohexyl esters of cyclohehexanecarboxylic acid, phenyl esters of cyclohexylbenzoic acid, cyclohexyl esters of cyclohexylbenzoic acid, phenyl esters of cyclohexylcyclohexanecarboxylic acid, cyclohexyl esters of cyclohexylcyclohexanecarboxylic acid, cyclohexylphenyl esters of benzoic acid, cyclohexylphenyl esters of cyclohexanecarboxylic acid, cyclohexylphenyl esters of cyclohexylcyclohexanecarboxylic acid, phenylcyclohexanes, cyclohexylbiphenyls, phenylcyclohexylcyclohexanes, cyclohexylcyclohexanes, cyclohexylcyclohexenes, cyclohexylcyclohexylcyclohexenes, 1,4-bis-cyclohexylbenzenes, 4,4′-bis-cyclohexylbiphenyls, phenylpyrimidines, cyclohexylpyrimidines, phenylpyridines, cyclohexylpyridines, phenylpyridazines, cyclohexylpyridazines, phenyldioxanes, cyclohexyldioxanes, phenyl-1,3-dithianes, cyclohexyl-1,3-dithianes, 1,2-diphenylethanes, 1,2-dicyclohexylethanes, 1-phenyl-2-cyclohexylethanes, 1-cyclohexyl-2-(4-phenylcyclohexyl) ethanes, 1-cyclohexyl-2-biphenylethanes, 1-phenyl2-cyclohexylphenylethanes, halogenated stilbenes, benzyl phenyl ether, tolanes, substituted cinnamic acids, or any combination thereof.

9 . A formulation comprising:
a first chiral dopant derived from betulin or glycyrrhetinic acid; and a second chiral dopant derived from betulin or glycyrrhetinic acid, wherein the first and second chiral dopants are different.

10 . The formulation of claim 9 , wherein the first chiral dopant comprises a structure having formula (IA) or (IB):

or a salt thereof, wherein:
each of R 1 and R 2 is, independently, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aralkyl, optionally substituted aryl, optionally substituted alkaryl, optionally substituted alkanoyl, optionally substituted aryloyl, or optionally substituted heterocyclyloyl.

11 . The formulation of claims 9 - 10 , wherein the second chiral dopant comprises a structure having formula (IIA) or (IIB):

wherein:
each of R 3 and R 4 is, independently, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aralkyl, optionally substituted aryl, optionally substituted alkaryl, optionally substituted alkanoyl, optionally substituted aryloyl, or optionally substituted heterocyclyloyl.

12 . The formulation of claims 9 - 11 , wherein the first or second chiral dopant comprises a structure having formula (IAa), (IBa), (IAb), or (IBb):

wherein:
each of R 1 , R 2a , R 1b , and R 2b is, independently, optionally substituted alkyl, optionally substituted haloalkyl, optionally substituted alkenyl, optionally substituted aralkyl, optionally substituted aryl, or optionally substituted alkaryl.

13 . The formulation of claims 9 - 12 , further comprising:
a third chiral dopant derived from betulin, wherein the first, second, and third chiral dopants are different.

14 . The formulation of claim 13 , wherein the third chiral dopant comprises a structure having formula (IA) or (IB).

15 . The formulation of claims 9 - 14 , wherein each of the first chiral dopant, the second chiral dopant, and the third chiral dopant, if present, is selected from the group consisting of:

16 . A liquid crystalline material comprising:
about 0.5 wt. % to about 20 wt. % of a first chiral dopant derived from betulin; and about 0.5 wt. % to about 20 wt. % of a second chiral dopant derived from betulin, wherein the first and second chiral dopants are different.

17 . The material of claim 16 , further comprising:
a third chiral dopant derived from betulin, wherein the first, second, and third chiral dopants are different.

18 . The material of claims 16 - 17 , wherein the first chiral dopant comprises a structure having formula (IA) or (IB):

or a salt thereof, wherein:
each of R 1 and R 2 is, independently, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aralkyl, optionally substituted aryl, optionally substituted alkaryl, optionally substituted alkanoyl, optionally substituted aryloyl, or optionally substituted heterocyclyloyl.

19 . The material of claims 16 - 18 , the second chiral dopant comprises a structure having formula (IIA) or (IIB):

wherein:
each of R 3 and R 4 is, independently, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aralkyl, optionally substituted aryl, optionally substituted alkaryl, opti

Assignees

• Zymergen Inc
• Univ Kent State Ohio

Inventors

• Raja Shilpa Naresh
• Zoombelt Arjan
• Safir Adam
• Palffy-Muhoray Peter
• Twieg Robert J
• Yokoyama Hiroshi
• Guo Tianyi
• Nepal Pawan

Classifications

• G02F1/13

  based on liquid crystals, e.g. single liquid crystal display cells · CPC title

• C09K19/0208

  Twisted Nematic (T.N.); Super Twisted Nematic (S.T.N.); Optical Mode Interference (O.M.I.) · CPC title

• C09K2219/03

  in the form of films, e.g. films after polymerisation of LC precursor · CPC title

• C09K2323/031

  Polarizer or dye · CPC title

• C09K19/586 Primary

  Optically active dopants; chiral dopants · CPC title