US 5,514,296 AGranted

Glassy low molar mass chiral nematic liquid crystalline compositions and optical articles formed therefrom

AssigneeUniversity of Rochester

InventorsShaw H. Chen, Hongqin Shi

Life of this patent

Estimating the term…

Abstract

A glassy thermotropic chiral nematic liquid crystalline composition comprises a glassy chiral nematic compound of low molar mass that includes a cycloaliphatic radical, a nematogenic moiety, and a chiral moiety, or a mixture of a nematic liquid crystalline compound of low molar mass that includes a cycloaliphatic radical and a nematogenic moiety and a chiral compound of low molar mass that includes a chiral moiety. Each cycloaliphatic radical contains 4 to about 18 carbon atoms. An optical device is formed from the described glassy thermotropic chiral nematic liquid crystalline composition.

Claims42

Dependent claims

A glassy thermotropic chiral nematic liquid crystalline composition comprising a glassy chiral nematic compound of low molar mass having the formula:

##STR63## or a mixture of a nematic liquid crystalline compound of low molar mass having the formula:
##STR64## and a chiral compound of low molar mass having the formula:
##STR65## where ##STR66## each independently represents a cycloaliphatic radical containing about 4 to 18 carbon atoms;
##STR67## represents a nematogenic moiety having the formula:
##STR68## where --Q-- is an alkylene radical containing 1 to about 8 carbon atoms, --X-- is --O--, --S--, or --CH.sub.2 --, --Y-- is ##STR69## --D-- and --E-- are each independently ##STR70## --Z is --CN, --NO.sub.2, --N.dbd.C.dbd.S, or an alkoxy, an alkylsulfonyl, or an arylsulfonyl radical containing up to about 8 carbon atoms, and q and r are each independently 0 or 1;
##STR71## represents a chiral moiety having the formula:
##STR72## where Q' is an alkylene radical containing 1 to about 8 carbon atoms, --X' is --O--, --S--, or --CH.sub.2 --,
--D'-- and --E'-- are each independently ##STR73## --G-- is --C.tbd.C--, --COO--, or --OOC--, Z' is an alkoxy, aralkoxy, alkylamino, or aralkylamino radical containing about 4 to 20 carbon atoms and containing at least one asymmetric carbon atom, and q', r', and s' are each independently 0 or 1;
CHI!'
represents a chiral compound having the formula:
M--E'--G--D'--CO--Z'
where --D'-- and --E'-- are each independently ##STR74## --G-- is
--C.tbd.C--, --COO--, or --OOC--,
--M is --H, --CN, --NO.sub.2, --N.dbd.C.dbd.S, --OH, or an alkoxy, an alkylsulfonyl, or an arylsulfonyl radical containing up to about 8 carbon atoms, and Z' is an alkoxy, aralkoxy, alkylamino, or aralkylamino radical containing about 4 to 20 carbon atoms and containing at least one asymmetric carbon atom;
--L.sub.N -- and --L.sub.C -- each individually represents a connecting group having the formula:
##STR75## where R is hydrogen or alkyl containing up to 4 carbon atoms, or forms a portion of a cycloaliphatic radical containing about 4 to 18 carbon atoms;
and x is 1 to 6, and y is at least 1, with the proviso that when ##STR76## is chiral, y can be zero.

14 more elements

An optical device comprising an optically transparent substrate and a film formed from a glassy thermotropic chiral nematic liquid crystalline composition comprising a glassy chiral nematic compound of low molar mass having the formula:

##STR95## or a mixture of a nematic liquid crystalline compound of low molar mass having the formula:
##STR96## and a chiral compound of low molar mass having the formula:
##STR97## each independently represents a cycloaliphatic radical containing about 4 to 18 carbon atoms;
##STR98## represents a nematogenic moiety having the formula:
##STR99## where --Q-- is an alkylene radical containing 1 to about 8 carbon atoms, --X-- is --O--, --S--, or --CH.sub.2 --, --Y-- is ##STR100## --D-- and --E-- are each independently ##STR101## --Z is --CN, --NO.sub.2, --N.dbd.C.dbd.S, or an alkoxy, an alkylsulfonyl, or an arylsulfonyl radical containing up to about 8 carbon atoms, and q and r are each independently 0 or 1;
##STR102## represents a chiral moiety having the formula:
##STR103## where Q' is an alkylene radical containing 1 to about 8 carbon atoms, --X' is --O--, --S--, or --CH.sub.2 --,
--D'-- and --E'-- are each independently ##STR104## --G-- is --C.tbd.C--, --COO--, or --OOC--, Z' is an alkoxy, aralkoxy, alkylamino, or aralkylamino radical containing about 4 to 20 carbon atoms and containing at least one asymmetric carbon atom, and q', r', and s' are each independently 0 or 1;
CHI!'
represents a chiral compound having the formula:
M--E'--G--D'--CO--Z'
where --D'-- and --E'-- are each independently ##STR105## --G-- is
--C.tbd.C--, --COO--, or --OOC--,
--M is --H, --CN, --NO.sub.2, --N.dbd.C.dbd.S, --OH, or an alkoxy, an alkylsulfonyl, or an arylsulfonyl radical containing up to about 8 carbon atoms, and Z' is an alkoxy, aralkoxy, alkylamino, or aralkylamino radical containing about 4 to 20 carbon atoms and containing at least one asymmetric carbon atom;
--L.sub.N -- and --L.sub.C -- each individually represents a connecting group having the formula:
##STR106## where R is hydrogen or alkyl containing up to 4 carbon atoms, or forms a portion of a cycloaliphatic radical containing about 4 to 18 carbon atoms;
and x is 1 to 6, and y is at least 1, with the proviso that when ##STR107## is chiral, y can be zero.

14 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/274,909Filed 14 Jul 1994 · continuation in part
Priority: 16 Nov 1993
Granted: 7 May 1996
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C09K 19/3483
Having nitrogen as hetero atom: the heterocyclic ring being a non-aromatic ring
C09K 19/30
Containing at least two non-condensed rings: containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
C09K 19/3068
In which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers: chain containing -COO- or -OCO- groups
C09K 19/32
Non-steroidal liquid crystal compounds: containing condensed ring systems, i.e. fused, bridged or spiro ring systems

Family

Serial153,570Parent of this continuation-in-part · filed 16 Nov 1993
US 5,378,393 AParent of this continuation-in-part
US 5,514,296 AThis patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

Open elsewhere

patentgrep

Loading patent…

Abstract

A glassy thermotropic chiral nematic liquid crystalline composition comprising a glassy chiral nematic compound of low molar mass having the formula:

##STR63## or a mixture of a nematic liquid crystalline compound of low molar mass having the formula:
##STR64## and a chiral compound of low molar mass having the formula:
##STR65## where ##STR66## each independently represents a cycloaliphatic radical containing about 4 to 18 carbon atoms;
##STR67## represents a nematogenic moiety having the formula:
##STR68## where --Q-- is an alkylene radical containing 1 to about 8 carbon atoms, --X-- is --O--, --S--, or --CH.sub.2 --, --Y-- is ##STR69## --D-- and --E-- are each independently ##STR70## --Z is --CN, --NO.sub.2, --N.dbd.C.dbd.S, or an alkoxy, an alkylsulfonyl, or an arylsulfonyl radical containing up to about 8 carbon atoms, and q and r are each independently 0 or 1;
##STR71## represents a chiral moiety having the formula:
##STR72## where Q' is an alkylene radical containing 1 to about 8 carbon atoms, --X' is --O--, --S--, or --CH.sub.2 --,
--D'-- and --E'-- are each independently ##STR73## --G-- is --C.tbd.C--, --COO--, or --OOC--, Z' is an alkoxy, aralkoxy, alkylamino, or aralkylamino radical containing about 4 to 20 carbon atoms and containing at least one asymmetric carbon atom, and q', r', and s' are each independently 0 or 1;
CHI!'
represents a chiral compound having the formula:
M--E'--G--D'--CO--Z'
where --D'-- and --E'-- are each independently ##STR74## --G-- is
--C.tbd.C--, --COO--, or --OOC--,
--M is --H, --CN, --NO.sub.2, --N.dbd.C.dbd.S, --OH, or an alkoxy, an alkylsulfonyl, or an arylsulfonyl radical containing up to about 8 carbon atoms, and Z' is an alkoxy, aralkoxy, alkylamino, or aralkylamino radical containing about 4 to 20 carbon atoms and containing at least one asymmetric carbon atom;
--L.sub.N -- and --L.sub.C -- each individually represents a connecting group having the formula:
##STR75## where R is hydrogen or alkyl containing up to 4 carbon atoms, or forms a portion of a cycloaliphatic radical containing about 4 to 18 carbon atoms;
and x is 1 to 6, and y is at least 1, with the proviso that when ##STR76## is chiral, y can be zero.

14 more elements

Facts

Application

08/274,909Filed 14 Jul 1994 · continuation in part

Priority

16 Nov 1993

Granted

7 May 1996

Term ends

Not estimatedThe source records don’t support an estimate.

Classification5 codes

C09K 19/3483
Having nitrogen as hetero atom: the heterocyclic ring being a non-aromatic ring
C09K 19/30
Containing at least two non-condensed rings: containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
C09K 19/3068
In which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers: chain containing -COO- or -OCO- groups
C09K 19/32
Non-steroidal liquid crystal compounds: containing condensed ring systems, i.e. fused, bridged or spiro ring systems