# US 5,700,393 A · Liquid crystalline compounds

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- Number: US 5,700,393 A
- Document ID: US5700393A
- Status: Granted
- Kind: A
- Application number: 08/687,869
- Filed: 1996-07-26
- Granted: 1997-12-23
- Earliest claimed: 1995-07-28
- Assignees: Rolic AG
- Inventors: Stephen Kelly
- Web page: https://patentgrep.com/patent/US5700393A

## CPC

- C09K 19/588: {Heterocyclic compounds}
- C07C 69/54: Acrylic acid esters; Methacrylic acid esters
- C07C 69/92: with etherified hydroxyl groups
- C07C 69/94: of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
- C07D 239/34: One oxygen atom
- C07D 239/52: Two oxygen atoms
- C09K 19/586: {Optically active dopants; chiral dopants}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention is concerned with photo cross-linkable liquid crystalline compounds of the general formula ##STR1## wherein A.sup.1 and A.sup.2 each are a cross-linkable mesogenic residue; and A.sup.3 is (R,R)- or (S,S)-trans-1,2-cyclohexyl-diyl, liquid crystalline mixtures which contain such compounds and their use in the cross-linked state as optical components.

## Claims

### Claim 1

A compound of the general formula ##STR13## wherein A.sup.1 and A.sup.2 each are a cross-linkable mesogenic residue; and
A.sup.3 is (R,R)- or (S,S)-trans-1,2-cyclohexyl-diyl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the mesogenic residues A.sup.1 and A.sup.2 each are a residue of general formula II ##STR14## wherein rings C and D each independently are selected from the groups consisting of pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diyl, 1,4-phenylene, and 1,4-phenylene substituted with one or more halogen, methyl or cyano;
Z.sup.1 is selected from the group consisting of (CH.sub.2).sub.m --, --CO--, --(CH.sub.2).sub.m CO-- and --(CH.sub.2).sub.m OOC--;
Z.sup.2 is selected from the group consisting of a single bond, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, --COO--, --OOC--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 -- and --(CH.sub.2).sub.3 O--;
Z.sup.3 is selected from the group consisting of --(CY.sub.2).sub.m --, --O(CY.sub.2).sub.m --, --(CY.sub.2).sub.m O--, --(CY.sub.2).sub.m COO--, --(CY.sub.2).sub.m OOC--, --(Si›(CH.sub.3).sub.2 !O).sub.m --, --OCH.sub.2 (Si›(CH.sub.3).sub.2 !O).sub.m Si›(CH.sub.3).sub.2 !CH.sub.2 O-- and --NHCH.sub.2 (Si›(CH.sub.3).sub.2 !O).sub.m Si›(CH.sub.3).sub.2 !CH.sub.2 NH--;
Y is hydrogen or fluorine;
n is 0, 1 or 2;
m is a whole number of 1 to 16; and
R.sup.1 is a cross-linkable group selected from the group consisting of CH.sub.2 .dbd.CH--, CH.sub.2 .dbd.CH--COO--, CH.sub.2 .dbd.C(CH.sub.3)--COO--, CH.sub.2 .dbd.C(Cl)--COO--, CH.sub.2 .dbd.C(Ph) --COO--, CH.sub.2 .dbd.CH--COO--Ph--, CH.sub.2 .dbd.CH--CO--NH--, CH.sub.2 .dbd.C(CH.sub.3)--CONH--, CH.sub.2 .dbd.C(Cl)--CONH--, CH.sub.2 .dbd.C(Ph)--CONH--, CH.sub.2 .dbd.C(COOR')--CH.sub.2 --COO--, CH.sub.2 .dbd.CH--O--, CH.sub.2 .dbd.CH--OOC--, Ph--CH.dbd.CH--, CH.sub.3 --C(.dbd.NR')--, cis,trans HOO--CR'.dbd.CR'--COO--, ##STR15## Ph is phenyl; R' is lower alkyl; and
R" is selected from the group consisting of methyl, methoxy, cyano and halogen;
wherein R.sup.1 --Z.sup.3 -- contains no --O--O-- or --N--O-- groups.

### Claim 3 (depends on 2)

The compound of claim 2, wherein
Z.sup.1 is selected from the group consisting of --(CH.sub.2)--, --CO--, --(CH.sub.2).sub.3 -- and --(CH.sub.2).sub.2 CO--; and
n is 0 or 1.

### Claim 4 (depends on 3)

The compound of claim 3, wherein the mesogenic residues A.sup.1 and A.sup.2 are the same.

### Claim 5 (depends on 4)

The compound of claim 4, wherein the residues A.sup.1 and A.sup.2 consist of a residue of the formula ##STR16## wherein rings C.sup.1 and D.sup.1 each independently are selected from the group consisting of pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene, 1,4-phenylene, and 1-4 phenylene substituted with fluorine;
Z.sup.11 is --CH.sub.2 -- or --CO--;
Z.sup.21 is selected from the group consisting of a single bond, --CH.sub.2 O--, --COO-- and --OOC--;
Z.sup.31 is selected from the group consisting of --(CH.sub.2).sub.m' --, --(CH.sub.2).sub.m' O--, --(CH.sub.2).sub.m' COO-- and --(CH.sub.2).sub.m' OOC--;
m' is a whole number of 3 to 12; and
R.sup.11 is selected from the group consisting of CH.sub.2 .dbd.CH--COO--, CH.sub.2 .dbd.C(CH.sub.3)--COO--, CH.sub.2 .dbd.CH--O-- and ##STR17##

### Claim 6 (depends on 5)

The compound of claim 5 selected from the group consisting of the formulae ##STR18## and the enantiomers thereof, wherein Z.sup.11 is --CO--; Z.sup.21 is a single bond or --COO--; and m' is a whole number of 3 to 12.

### Claim 7 (depends on 6)

The compound of claim 6, wherein Z.sup.21 is --COO--.

### Claim 8 (depends on 1)

A mixture consisting of photo-cross-linkable liquid crystalline compounds comprising a compound of formula I, claim 1.

### Claim 9 (depends on 8)

The liquid crystalline mixture of claim 8, further comprising a compound selected from the group of formulae consisting of ##STR19## wherein X is selected from the group consisting of hydrogen, fluorine, chlorine, bromine and methyl;
m' is a whole number of 3 to 12;
t is a whole number of 2 to 12;
Z is --OCH.sub.2 -- or --OOC--;
A is 1,4-phenylene or 2-or 3-fluoro-1,4-phenylene;
S is --(CH.sub.2).sub.m' --; --(CH.sub.2).sub.m' O-- or --O(CH.sub.2).sub.m' --; and
R is selected from the group consisting of CH.sub.2 .dbd.CH--COO--, CH.sub.2 .dbd.C(CH.sub.3)--COO--, CH.sub.2 .dbd.CH--O-- and ##STR20##

### Claim 10 (depends on 2)

The compound of claim 2, selected from the group consisting of 0.1 g of (1R,2R)-trans-1,2-bis›4-(4-›8-acryloyloxyoctyloxy!phenylcarbonyloxy)phenyl carbonyloxy!cyclohexane;
(1R,2R)-trans-1,2-bis ›4-(5-›4-Acryloyloxybutyloxy!pyrimidin-2-yl)phenylcarbonyloxy!cyclohexane;
(1R,2R)-trans-1,2-bis ›2-(4-›4-acryloyloxybutyloxy!-phenyl)pyridin-5-yl)carbonyloxy!cyclohexane; and
(1R,2R)-trans-1,2-bis ›4-(4-›6-acryloyloxyhexyloxy!-phenyl)cyclohexyl-ethylcarbonyloxy!cyclohexa ne.