# US 5,702,639 A · Use of complex ligands for ions in ferroelectric liquid-crystal mixtures

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- Number: US 5,702,639 A
- Document ID: US5702639A
- Status: Granted
- Kind: A
- Application number: 08/455,668
- Filed: 1995-05-31
- Granted: 1997-12-30
- Earliest claimed: 1989-12-01
- Assignees: Hoechst Aktiengesellschaft
- Inventors: Claus Escher; Takamasa Harada; Gerhard Illian; Norbert Rosch; Rainer Wingen
- Web page: https://patentgrep.com/patent/US5702639A

## CPC

- C09K 19/584: {having a condensed ring system; macrocyclic compounds}
- C09K 19/0225: {Ferroelectric}
- C09K 2323/00: Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K 2323/023: Organic silicon compound, e.g. organosilicon
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A ferroelectric liquid crystal mixture containing two or more components, at least one of which is a complex ligand for ions, in particular for cations, is particularly suitable for use in ferroelectric liquid crystal displays.

## Claims

### Claim 1

A ferroelectric liquid-crystal mixture comprising at least two components, wherein one component is at least one electrically neutral complex ligand for cations comprising at least two donor atoms which are nitrogen, nitrogen and oxygen, nitrogen and sulfur, sulfur or sulfur and oxygen.

### Claim 2 (depends on 1)

An FLC mixture as claimed in claim 1, wherein the complex ligands are mediocyclic or macrocyclic compounds.

### Claim 3 (depends on 1)

An FLC mixture as claimed in claim 1, wherein the complex ligands are cryptands.

### Claim 4 (depends on 1)

An FLC mixture as claimed in claim 1, wherein the complex ligands are coronands.

### Claim 5 (depends on 1)

An FLC mixture as claimed in claim 1, wherein the complex ligands are podands.

### Claim 6 (depends on 1)

An FLC mixture as claimed in claim 1, wherein the complex ligands are bicyclic compounds which contain at least two nitrogen atoms.

### Claim 7 (depends on 1)

An FLC mixture as claimed in claim 1, wherein the complex ligands are bicyclic or tricyclic compounds.

### Claim 8 (depends on 1)

An FLC mixture as claimed in claim 1, wherein the complex ligands are bicyclic or tricyclic compounds which contain at least two nitrogen atoms and at least four oxygen atoms.

### Claim 9 (depends on 1)

An FLC mixture as claimed in claim 1, containing at least two different complex ligands for ions.

### Claim 10 (depends on 1)

An FLC mixture as claimed in claim 1, containing at least one complex ligand for alkali metal and/or alkaline earth metal ions.

### Claim 11 (depends on 1)

An FLC mixture as claimed in claim 1, containing at least two different complex ligands for different cations.

### Claim 12 (depends on 1)

An FLC mixture as claimed in claim 1, wherein the complex ligand is a compound of the general formula (I), ##STR15## in which
--Z-- is --O-- or --S--,
m and n are integers greater than zero, where m+n=2 to 6,
--X.sup.1 -- and --X.sup.2 -- are identical or different and are ##STR16## or --X.sup.1 -- and --X.sup.2 -- together are
N--CH.sub.2 (--CH.sub.2 --Z--CH.sub.2).sub.l --CH.sub.2 --N or
N--CO(--CH.sub.2 --Z--CH.sub.2).sub.l --CO--N or
H--C--CH.sub.2 (--CH.sub.2 --Z--CH.sub.2).sub.2 --CH.sub.2 --C--H,
where
R is alkyl or alkoxy having from 1 to 15 carbon atoms, phenyl, benzyl or benzoyl and
l is 1 or 2.

### Claim 13 (depends on 1)

An FLC mixture as claimed in claim 1, wherein the complex ligand is a compound of the general formula ##STR17## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4, independently of one another, are --H, --(C.sub.1 -C.sub.12)alkyl, ##STR18## and p, q, r and s, independently of one another, are an integer from 2 to 4, and where p+q+r+s=8 to 16.

### Claim 14 (depends on 1)

An FLC mixture as claimed in claim 1, containing from 0.01 to 10 mol-% of at least one complex ligand.

### Claim 15 (depends on 1)

An FLC mixture as claimed in claim 1, which has a spontaneous polarization of at least 35 nC.multidot.cm.sup.-2.

### Claim 16 (depends on 1)

A liquid-crystal switching or display device containing a ferroelectric liquid-crystalline medium, outer plates, electrodes, at least one alignment layer and optionally, additional auxiliary layers, wherein the ferroelectric liquid-crystalline medium is an FLC mixture as claimed in claim 1.

### Claim 17 (depends on 16)

A liquid-crystal switching or display device as claimed in claim 16, which is an SSFLC cell having an FLC layer thickness of from 1 to 20 .mu.m and wherein the FLC mixture contains, as complex ligand, at least one mediocyclic or macrocyclic compound.

### Claim 18 (depends on 16)

A liquid-crystal switching or display device as claimed in claim 16, which is an SSFLC cell having an FLC layer thickness of from 1 to 10 .mu.m and wherein the FLC mixture contains, as complex ligand, at least one cryptand and/or coronand.

### Claim 19 (depends on 16)

A liquid-crystal switching or display device as claimed in claim 16, wherein the alignment layer comprises an SiO.sub.2 -containing material.

### Claim 20

A ferroelectric liquid-crystal mixture comprising at least two compounds, wherein one component is at least one complex ligand of the formula (I), ##STR19## in which
--Z-- is --O-- or --S--,
m and n are integers greater than zero, where m+n equals 2 to 6,
--X.sup.1 -- and --X.sup.2 -- are identical or different and are ##STR20## or --X.sup.1 -- and --X.sup.2 -- together are ##STR21## where R is alkyl or alkoxy having from 1 to 15 carbon atoms, phenyl, benzyl or benzoyl and
1is 1 or 2,
with the proviso that X.sup.1, X.sup.2 and Z are not all simultaneously oxygen or all simultaneously sulfur.