# US 5,707,545 A · Chiral oxiranylmethyl ethers, and their use as dopants in liquid-crystal mixtures

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- Number: US 5,707,545 A
- Document ID: US5707545A
- Status: Granted
- Kind: A
- Application number: 08/256,189
- Filed: 1994-06-24
- Granted: 1998-01-13
- Earliest claimed: 1991-12-28
- Assignees: Hoechst Aktiengesellschaft
- Inventors: Hubert Schlosser; Rainer Wingen; Anke Kaltbeitzel; Javier Manero
- Web page: https://patentgrep.com/patent/US5707545A

## CPC

- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 405/14: containing three or more hetero rings
- C07K 16/2893: {against CD52}
- C09K 19/3466: {Pyrimidine with at least another heterocycle in the chain}
- C09K 19/588: {Heterocyclic compounds}
- C09K 19/3405: {the heterocyclic ring being a five-membered ring}
- C09K 19/3411: {the heterocyclic ring being a three-membered ring}
- C09K 2323/031: Polarizer or dye
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

Novel oxiranylmethyl ethers can advantageously be employed in liquid-crystal mixtures since they have high spontaneous-polarization values and features in their molecular structure which make them miscible with other components of liquid-crystal systems.

## Claims

### Claim 1

A liquid-crystal mixture which contains from 0.01 to 60% by weight of at least one oxiranylmethyl ether of the formula (I) ##STR46## in which the symbols and indices have the following meanings: * is a center of chirality,
R.sup.1 is a straight-chain or branched alkyl radical having 1 to 16 carbon atoms (with or without an asymmetric carbon atom), it also being possible for one or more non-adjacent --CH.sub.2 -- groups to be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--CO--O--, --CH.dbd.CH--, --C.tbd.C-- or .DELTA., and/or for one or more H atoms of the alkyl radical to be substituted by F or is one of the following chiral groups: ##STR47## R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8, independently of one another, are H or a straight-chain or branched alkyl radical having 1 to 16 carbon atoms, or R.sup.5 and R.sup.6 together may alternatively be --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- if they are bonded as substituents to a dioxolane system,
A.sup.1, A.sup.2 and A.sup.3 are identical or different and are 1,4-phenylene, in which one or two H atoms may be replaced by F and/or CN, pyrazine-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene, in which one H atom may be replaced by CN, 1,3,4-thiadiazole-2,5-diyl, 1,3-dioxane-2,5-diyl, 1,3-thiazole-2,4-diyl, 1,3-thiazole-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl or naphthalene-2,6-diyl, where A.sup.1 and A.sup.2 and A.sup.3 cannot simultaneously be unsubstituted 1,4-phenylene if M.sup.1 or M.sup.2 is --COO--,
M.sup.1 and M.sup.2 are identical or different and are --CO--O--, --O--CO--, --O--CO--O--, --CH.sub.2 --O--, --O--CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH-- or --C.tbd.C--,
M.sup.3 is --CH.sub.2 --O--, --O--CH.sub.2 --, --CO--O--, --O--CO-- or a single bond,
a, b, c, d and e are zero or one, with the proviso that the sum a+c+e is 1, 2 or 3,
with the exception of the compounds in which the (--A.sup.1).sub.a (--M.sup.1).sub.b (--A.sup.2).sub.c (--M.sup.2).sub.d (--A.sup.3).sub.e -group has the following meanings: ##STR48## and with the exception of the compounds in which the R.sup.1 (--A.sup.1).sub.a (M.sup.1).sub.b (--A.sup.2).sub.c (--M.sup.2).sub.d (--A.sup.3).sub.e -- group has the following meanings: ##STR49## where R.sup.9 is straight-chain or branched (C.sub.3 -C.sub.12)-alkenyl containing a terminal double bond, in which one or two non-adjacent CH.sub.2 groups may be replaced by O and/or S atoms,
R.sup.10 is straight-chain or branched alkyl having 1-12 carbon atoms, in which one or two non-adjacent CH.sub.2 groups may be replaced by O and/or S atoms, and
R.sup.11 is an alkoxy group having 5-12 carbon atoms, ##STR50## where X is straight-chain or branched alkylene having 1 to 16 carbon atoms, in which one or two non-adjacent --CH.sub.2 -- groups may also be replaced by --O--, --S--, --O--CO--, --CO--O--, --CO-- or --O--CO--O--.

### Claim 2

A chiral oxiranylmethyl ether of the formula (I) ##STR51## in which the symbols and indices have the following meanings: * is a center of chirality,
R.sup.1 is a straight-chain or branched alkyl radical having 1 to 16 carbon atoms (with or without an asymmetric carbon atom), it also being possible for one or more non-adjacent --CH.sub.2 -- groups to be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--CO--O--, --CH.dbd.CH--, --C.tbd.C-- or .DELTA., and/or for one or more H atoms of the alkyl radical to be substituted by F, or is one of the following chiral groups: ##STR52## R.sup.2, R.sup.3, R.sup.5, R.sup.6, R.sup.7 and R.sup.8, independently of one another, are H or a straight-chain or branched alkyl radical having 1 to 16 carbon atoms, or R.sup.5 and R.sup.6 together may alternatively be --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- if they are bonded as substituents to a dioxolane system,
R.sup.4 is a straight-chain or branched alkyl radical having 1 to 16 carbon atoms,
A.sup.1, A.sup.2 and A.sup.3 are identical or different and are 1,4-phenylene, in which one or two H atoms may be replaced by F and/or CN, pyrazine-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene, in which one H atom may be replaced by CN, 1,3,4-thiadiazole-2,5-diyl, 1,3-dioxane-2,5-diyl, 1,3-thiazole-2,4-diyl, 1,3-thiazole-2,5-diyl, thiophene-2,4-diyl, thiophene-2,5-diyl or naphthalene-2,6-diyl, where A.sup.1 and A.sup.2 and A.sup.3 cannot simultaneously be unsubstituted 1,4-phenylene if M.sup.1 or M.sup.2 is --COO--,
M.sup.1 and M.sup.2 are identical or different and are --CO--O--, --O--CO--, --O--CO--O--, --CH.sub.2 --O--, --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH-- or --C.tbd.C--,
M.sup.3 is --CH.sub.2 --O--, --O--CH.sub.2 --, --CO--O--, --O--CO-- or a single bond,
a, b, c, d and e are zero or one, with the proviso that the sum a+c+e is 1, 2 or 3,
with the exception of the compounds in which the (--A.sup.1).sub.a (--M.sup.1).sub.b (--A.sup.2).sub.c (--M.sup.2).sub.d (--A.sup.3).sub.e -- group has the following meanings: ##STR53## and with the exception of the compounds in which the R.sup.1 (--A.sup.1).sub.a (--M.sup.1).sub.b (--A.sup.2).sub.c (M.sup.2).sub.d (--A.sup.3).sub.e -- group has the following meanings: ##STR54## where R.sup.9 is straight-chain or branched (C.sub.3 -C.sub.12)-alkenyl containing a terminal double bond, in which one or two non-adjacent CH.sub.2 groups may be replaced by O and/or S atoms,
R.sup.10 is straight-chain or branched alkyl having 1-12 carbon atoms, in which one or two non-adjacent CH.sub.2 groups may be replaced by O and/or S atoms, and
R.sup.11 is an alkoxy group having 5-12 carbon atoms, ##STR55## where X is straight-chain or branched alkylene having 1 to 16 carbon atoms in which one or two non-adjacent --CH.sub.2 -- groups may also be replaced by --O--, --S--, --O--CO--, --CO--O--, --CO-- or --O--CO--O--.

### Claim 3 (depends on 2)

A chiral oxiranylmethyl ether as claimed in claim 2, wherein the symbols and indices in the formula (I) have the following meanings:
R.sup.1 is a straight-chain or branched alkyl radical having 1 to 16 carbon atoms (with or without an asymmetric carbon atom), it also being possible for one or more --CH.sub.2 -- groups to be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--CO--O, --CH.dbd.CH--, --C.tbd.C-- or .DELTA., or is one of the following chiral groups: ##STR56## R.sup.2, R.sup.3, R.sup.5, R.sup.6, R.sup.7 and R.sup.8, independently of one another, are H or a straight-chain or branched alkyl radical having 1 to 16 carbon atoms, where R.sup.5 and R.sup.6 together may alternatively be --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- if they are bonded as substituents to a dioxolane system,
R.sup.4 is a straight-chain or branched alkyl radical having 1 to 16 carbon atoms,
A.sup.1, A.sup.2 and A.sup.3 are identical or different and are 1,4-phenylene, pyrazine-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene, 1,3,4-thiadiazole-2,5-diyl, 1,3-dioxane-2,5-diyl or naphthalene-2,6-diyl, where A.sup.1 and A.sup.2 and A.sup.3 cannot simultaneously be unsubstituted 1,4-phenylene if M.sup.1 or M.sup.2 is --COO--,
M.sup.1 and M.sup.2 are identical or different and are --CO--O--, --O--CO--, --CH.sub.2 --O--, --O--CH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH-- or --C.tbd.C--, and
M.sup.3 is --CH.sub.2 --O--, --O--CH.sub.2 --, --CO--O--, --O--CO-- or a single bond.

### Claim 4 (depends on 2)

A chiral oxiranylmethyl ether as claimed in claim 2, wherein the symbols and indices in the formula (I) have the following meanings:
R.sup.1 is a straight-chain or branched alkyl radical having 1 to 16 carbon atoms (with or without an asymmetric carbon atom), it also being possible for one or two --CH.sub.2 -- groups to be replaced by --O--, --CO--, --CO--O--, --O--CO--, --CH.dbd.CH--, or .DELTA., or is one of the following chiral groups: ##STR57## R.sup.2, R.sup.3, R.sup.5, R.sup.6, R.sup.7 and R.sup.8, independently of one another, are H or a straight-chain or branched alkyl radical having 1 to 16 carbon atoms, where R.sup.5 and R.sup.6 together may alternatively be --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- if they are bonded as substituents to a dioxolane system,
R.sup.4 is a straight-chain or branched alkyl radical having 1 to 16 carbon atoms,
A.sup.1, A.sup.2 and A.sup.3 are identical or different and are 1,4-phenylene, pyrazine-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene, 1,3,4-thiadiazole-2,5-diyl or naphthalene-2,6-diyl, where A.sup.1 and A.sup.2 and A.sup.3 cannot simultaneously be unsubstituted 1,4-phenylene if M.sup.1 or M.sup.2 is --COO--,
M.sup.1 and M.sup.2 are identical or different and are --CO--O--, --O--CO--, --CH.sub.2 --O--, --O--CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH-- or --C.tbd.C--, and
M.sup.3 is --CH.sub.2 --O--, --O--CH.sub.2 --, --CO--O--, --O--CO-- or a single bond.

### Claim 5 (depends on 2)

A chiral oxiranylmethyl ether as claimed in claim 2, wherein
R.sup.1 is an alkyl radical having 1 to 16 carbon atoms, it being possible for one or two non-adjacent --CH.sub.2 -- groups to be replaced by --O--, .DELTA. or --CH.dbd.CH--, or is one of the chiral groups ##STR58## R.sup.2, R.sup.3, R.sup.5 and R.sup.6, independently of one another, are H or an alkyl radical having 1 to 16 carbon atoms,
R.sup.4 is a straight-chain or branched alkyl radical having 1 to 16 carbon atoms,
M.sup.3 is --CH.sub.2 --O-- or --CO--O--,
and the (--A.sup.1).sub.a (--M.sup.1).sub.b (--A.sup.2).sub.c (--M.sup.2).sub.d (--A.sup.3).sub.e -group has the following meanings: ##STR59##

### Claim 6 (depends on 2)

A liquid-crystal mixture which contains from 0.01 to 60% by weight of at least one oxiranylmethyl ether as claimed in claim 2.

### Claim 7 (depends on 1)

A ferroelectric liquid-crystal mixture which contains from 0.01 to 60% by weight of at least one oxiranylmethyl ether as claimed in claim 1.

### Claim 8 (depends on 4)

A ferroelectric liquid-crystal mixture which contains from 0.01 to 60% by weight of at least one oxiranylmethyl ether as claimed in claim 4.

### Claim 9 (depends on 5)

A ferroelectric liquid-crystal mixture which contains from 0.01 to 60% by weight of at least one oxiranylmethyl ether as claimed in claim 5.

### Claim 10 (depends on 1, 6, 7, 8)

An electro-optical or fully optical component containing a liquid-crystal mixture as claimed in claim 1, 6, 7 or 8.