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US4650600A
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Liquid crystal phase
Assignee: Merck Patent GmbH
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Filing: 1984-09-17
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Granted: 1987-03-17
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Expires: 2004-09-17
Abstract
Abstract Liquid crystal phases containing at least one chiral, compound with at least two chiral centers in the molecule which are adjacent or separated from one another by an acyclic chain, preferably at least one optically active compound of the formula I R.sup.1 --CHCH.sub.3 --CHCH.sub.3 --R.sup.2 I wherein R 1 and R 2 independently of one another are each a group --Z 1 --(A 1 ) m --Z 2 --(A 2 ) n --Y, wherein A 1 and A 2 in each case independently of one another are a 1,4-phenylene, pyrimidine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene group, it also being possible for these to be mono-substituted or poly-substituted by F, Cl, Br, CN and/or alkyl groups with up to 12 C atoms, it being possible for 1 or 2 CH 2 groups in the alkyl groups to be replaced by O atoms, Z 1 is --O--CO--, --CO--O--, --O-- or a single bond, Z 2 is --CO--O--, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --CH═N--, --N═CH--, --N═N--, --N(O)═N-- or a single bond, m and n in each case independently of one another are 0, 1 or 2 and Y is a straight-chain or branched alkyl group with up to 12 C atoms, it being possible for 1 or 2 CH 2 groups to be replaced by O atoms, or, if n is 1 or 2, Y is also F, Cl, Br or CN, exhibit electro-optical properties, which are independent of temperature over a wide range.
Inventors
- 👤 Gerd Heppke
- 👤 Feodor Oestreicher
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 12:24
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/30; C09K19/3001; C09K19/3066; C09K19/10; C09K19/14; C09K19/20; C09K19/2007; C09K19/2021; C09K19/2028; C09K19/22; C09K19/24; C09K19/26; C09K19/3003; C09K19/32; C09K19/321; C09K19/34; C09K19/3402; C09K19/3441; C09K19/345; C09K19/3458; C09K19/3463; C09K19/3491; C09K19/52; C09K19/58; C09K19/586; C09K2019/3422
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
235 words
In a liquid crystal phase comprising at least two components, the improvement wherein at least one component is an optically active compound of the formula R.sup.1 --CHCH.sub.3 --CHCH.sub.3 --R.sup.2 wherein R 1 and R 2 independently of one another are each --Z 1 --(A 1 ) m --Z 2 --(A 2 ) n --Y, wherein A 1 and A 2 in each case independently of one another are 1,4-phenylene, pyrimidine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene, or one of said groups mono-substituted or poly-substituted by F, Cl, Br, CN, alkyl of up to 12 C atoms, or C 1-12 alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, Z 1 is --O--CO--, --CO--O--, --O-- or a single bond, Z 2 is --CO--O--, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --CH═N--, --N═CH--, --N═N--, --N(O)═N-- or a single bond, m and n in each case independently of one another are 0, 1 or 2 with the proviso that in each of R 1 and R 2 , one of m and n is not zero when Z 1 and Z 2 are both single bonds, and Y is alkyl of up to 12 C atoms, or C 1-12 -alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, or, if n is 1 or 2, Y can also be F, Cl, Br or CN.
Claim 2
Dependent Claim
235 words
In a liquid crystal phase comprising at least two components, the improvement wherein at least one component is an optically active compound of the formula R.sup.1 --CHCH.sub.3 --CHCH.sub.3 --R.sup.2 wherein R 1 and R 2 independently of one another are each --Z 1 --(A 1 ) m --Z 2 --(A 2 ) n --Y, wherein A 1 and A 2 in each case independently of one another are 1,4-phenylene, pyrimidine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene, or one of said groups mono-substituted or poly-substituted by F, Cl, Br, CN, alkyl of up to 12 C atoms, or C 1-12 alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, Z 1 is --O--CO--, --CO--O--, --O-- or a single bond, Z 2 is --CO--O--, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --CH═N--, --N═CH--, --N═N--, --N(O)═N-- or a single bond, m and n in each case independently of one another are 0, 1 or 2 with the proviso that in each of R 1 and R 2 , one of m and n is not zero when Z 1 and Z 2 are both single bonds, and Y is alkyl of up to 12 C atoms, or C 1-12 -alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, or, if n is 1 or 2, Y can also be F, Cl, Br or CN.
Claim 3
Dependent Claim
17 words
A liquid crystal phase of claim 1 wherein the amount of said compound is 0.05-3% by weight.
Claim 4
Dependent Claim
20 words
A liquid crystal phase of claim 2 comprising only one chiral compound having at least two of said chiral centers.
Claim 5
Dependent Claim
13 words
A liquid crystal phase of claim 1 comprising only one of said compounds.
Claim 6
Dependent Claim
40 words
A liquid crystal phase of claim 1 wherein the amount of said compound is effective to render the threshold voltage of said liquid crystal phase when used in a liquid crystalline electrooptical cell essentially constant as a function of temperature.
Claim 7
Dependent Claim
239 words
A liquid crystal phase of claim 1 wherein the optically active compound is of the formula Y--CHCH 3 --CHCH 3 --Z 1 --A 1 --Z 2 --(A 1 ) 2 --Y YCOO--CHCH 3 --CHCH 3 --OCOY YCOO--CHCH 3 --CHCH 3 --Z 1 --A 1 --Y YCOO--CHCH 3 --CHCH 3 --Z 1 --A 1 --A 2 --Y YCOO--CHCH 3 --CHCH 3 --Z 1 --A 1 --Z 2 --A 2 --Y YCOO--CHCH 3 --CHCH 3 --Z 1 --(A 1 ) 2 --Z 2 --A 2 --Y YCOO--CHCH 3 --CHCH 3 --Z 1 --A 1 --Z 2 --(A 2 ) 2 --Y Y--A 1 --Z 1 --CHCH 3 --CHCH 3 --Z 1 --A 1 --Y Y--A 1 --Z 1 --CHCH 3 --CHCH 3 --Z 1 --A 1 --A 2 --Y Y--A 1 --Z 1 --CHCH 3 --CHCH 3 --Z 1 --A 1 --Z 2 --A 2 --Y Y--A 1 --Z 1 --CHCH 3 --CHCH 3 --Z 1 --(A 1 ) 2 --Z 2 --A 2 --Y Y--A 1 --Z 1 --CHCH 3 --CHCH 3 --Z 1 --A 1 --Z 2 --(A 2 ) 2 --Y Y--A 1 --A 2 --Z 1 --CHCH 3 --CHCH 3 --Z 1 --A 1 --A 2 --Y Y--A 1 --A 2 --Z 1 --CHCH 3 --CHCH 3 --Z 1 --A 1 --Z 2 --A 2 --Y Y--A 2 --Z 2 --A 1 --Z 1 --CHCH 3 --CHCH 3 --Z 1 --A 1 --Z 2 --A 2 --Y.
Claim 8
Dependent Claim
25 words
A liquid crystal phase of claim 6 wherein the amount of chiral compound having at least two of said chiral centers is 0.05-3% by weight.
Claim 9
Dependent Claim
70 words
A liquid crystal phase of claim 1 wherein in the optically active compound, R 1 and R 2 are independently each --Cy--Phe--Y --Phe--Cy--Y --Phe--Phe--Y --Cy--Cy--Y --Phe--Phe--Phe--Y --Cy--Phe--Phe--Y --Cy--Cy--Phe--Y --Dio--Phe--Phe--Y --Dio--Cy--Y --Dio--Phe--Y --Pyr--Phe--Y --Pyr--Cy--Y --A 1 --CH 2 CH 2 --A 2 --Y --A 1 --OCO--A 2 --Y --Cy--Ph--CH 2 CH 2 --Cy--Y --Cy--COO--Cy--Y --Cy--COO--Ph--Y, or --Ph--COO--Ph--Y wherein "Phe" is 1,4-phenylene, "Cy" is 1,4-cyclohexylene, "Dio" is 1,3-dioxane-2,5-diyl, and "Pyr" is pyrimidine-2,5-diyl.
Claim 10
Dependent Claim
21 words
In an electro-optical cell comprising a liquid crystal phase, the improvement wherein the liquid crystal phase is one of claim 6.
Claim 11
Dependent Claim
21 words
In an electro-optical cell comprising a liquid crystal phase, the improvement wherein the liquid crystal phase is one of claim 1.
Claim 12
Dependent Claim
21 words
In an electro-optical cell comprising a liquid crystal phase, the improvement wherein the liquid crystal phase is one of claim 5.
Claim 13
Independent Claim
267 words
A method for achieving temperature compensation in a liquid crystal display element containing a liquid crystal phase, comprising including in said phase at least 0.05% of at least one chiral compound having at least two chiral centers which are adjacent or separated from one another by an acyclic chain, wherein said chiral compound is of the formula R.sup.1 --CHCH.sub.3 --CHCH.sub.3 --R.sup.2 wherein R 1 and R 2 independently of one another are each --Z 1 --(A 1 ) m --Z 2 --(A 2 ) n --Y, wherein A 1 and A 2 in each case independently of one another are 1,4-phenylene, pyrimidine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene, or one of said groups mono-substituted or poly-substituted by F, Cl, Br, CN, alkyl of up to 12 C. atoms, or C 1-12 alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, Z 1 is --O--CO--, --CO--O--, --O-- or a single bond, Z 2 is --CO--O--, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --CH═N--, --N═CH--, --N═N--, --N(O)═N-- or a single bond, m and n in each case independently of one another are 0, 1 or 2 with the proviso that in each of R 1 and R 2 , one of m and n is not zero when Z 1 and Z 2 are both single bonds, and Y is alkyl of up to 12 C atoms, or C 1-12 -alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, or, if n is 1 or 2, Y can also be F, Cl, Br or CN.
Claim 14
Independent Claim
267 words
A method for achieving temperature compensation in a liquid crystal display element containing a liquid crystal phase, comprising including in said phase at least 0.05% of at least one chiral compound having at least two chiral centers which are adjacent or separated from one another by an acyclic chain, wherein said chiral compound is of the formula R.sup.1 --CHCH.sub.3 --CHCH.sub.3 --R.sup.2 wherein R 1 and R 2 independently of one another are each --Z 1 --(A 1 ) m --Z 2 --(A 2 ) n --Y, wherein A 1 and A 2 in each case independently of one another are 1,4-phenylene, pyrimidine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene, or one of said groups mono-substituted or poly-substituted by F, Cl, Br, CN, alkyl of up to 12 C. atoms, or C 1-12 alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, Z 1 is --O--CO--, --CO--O--, --O-- or a single bond, Z 2 is --CO--O--, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --CH═N--, --N═CH--, --N═N--, --N(O)═N-- or a single bond, m and n in each case independently of one another are 0, 1 or 2 with the proviso that in each of R 1 and R 2 , one of m and n is not zero when Z 1 and Z 2 are both single bonds, and Y is alkyl of up to 12 C atoms, or C 1-12 -alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, or, if n is 1 or 2, Y can also be F, Cl, Br or CN.
Claim 15
Independent Claim
264 words
A method for rendering the electro-optical properties of a liquid crystal phase essentially independent of temperature comprising adding thereto at least 0.05% of at least one chiral compound having at least two chiral centers which are adjacent or separated from one another by an acyclic chain, wherein said chiral compound is of the formula R.sup.1 --CHCH.sub.3 --CHCH.sub.3 --R.sup.2 wherein R 1 and R 2 independently of one another are each --Z 1 --(A 1 ) m --Z 2 --(A 2 ) n --Y, wherein A 1 and A 2 in each case independently of one another are 1,4-phenylene, pyrimidine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene, or one of said groups mono-substituted or poly-substituted by F, Cl, Br, CN, alkyl of up to 12 C atoms, or C 1-12 alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, Z 1 is --O--CO--, --CO--O--, --O-- or a single bond, Z 2 is --CO--O--, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --CH═N--, --N═CH--, --N═N--, --N(O)═N-- or a single bond, m and n in each case independently of one another are 0, 1 or 2 with the proviso that in each of R 1 and R 2 , one of m and n is not zero when Z 1 and Z 2 are both single bonds, and Y is alkyl of up to 12 C atoms, or C 1-12 -alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, or, if n is 1 or 2, Y can also be F, Cl, Br or CN.
Claim 16
Independent Claim
264 words
A method for rendering the electro-optical properties of a liquid crystal phase essentially independent of temperature comprising adding thereto at least 0.05% of at least one chiral compound having at least two chiral centers which are adjacent or separated from one another by an acyclic chain, wherein said chiral compound is of the formula R.sup.1 --CHCH.sub.3 --CHCH.sub.3 --R.sup.2 wherein R 1 and R 2 independently of one another are each --Z 1 --(A 1 ) m --Z 2 --(A 2 ) n --Y, wherein A 1 and A 2 in each case independently of one another are 1,4-phenylene, pyrimidine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene, or one of said groups mono-substituted or poly-substituted by F, Cl, Br, CN, alkyl of up to 12 C atoms, or C 1-12 alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, Z 1 is --O--CO--, --CO--O--, --O-- or a single bond, Z 2 is --CO--O--, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --CH═N--, --N═CH--, --N═N--, --N(O)═N-- or a single bond, m and n in each case independently of one another are 0, 1 or 2 with the proviso that in each of R 1 and R 2 , one of m and n is not zero when Z 1 and Z 2 are both single bonds, and Y is alkyl of up to 12 C atoms, or C 1-12 -alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, or, if n is 1 or 2, Y can also be F, Cl, Br or CN.
Claim 17
Dependent Claim
18 words
A liquid crystal phase of claim 1, wherein for all Y groups, all alkyl portions are straight chained.
Claim 18
Dependent Claim
23 words
A liquid crystal phase of claim 1, wherein in R 1 and R 2 , one of n and m is not 0.
Claim 19
Dependent Claim
215 words
In a liquid crystal phase comprising at least two components, the improvement wherein at least one component is an optically active compound of the formula R.sup.1 --CHCH.sub.3 --CHCH.sub.3 --R.sup.2 wherein R 1 and R 2 independently of one another are each --Z 1 --(A 1 ) m --Z 2 --(A 2 ) n --Y, wherein A 1 and A 2 in each case independently of one another are 1,4-phenylene, pyrimidine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene, or one of said groups monosubstituted or polysubstituted by F, Cl, Br, CN, alkyl of up to 12 C atoms, or C 1-12 alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, Z 1 is --O--CO--, --CO--O--, --O-- or a single bond, Z 2 is --CO--O--, --O--CO--, --CH 2 CH 2 , --OCH 2 , --CH 2 O--, --CH═N--, --N═CH--, --N═N--, --N(O)═N-- or a single bond, m and n in each case independently of one another are 0, 1 or 2, and Y is alkyl of up to 12 C atoms, or C 1-12 alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, or, if n is 1 or 2, Y can also be F, Cl, Br or CN, wherein for all Y groups, all alkyl portions are straight chained.
Claim 20
Dependent Claim
215 words
In a liquid crystal phase comprising at least two components, the improvement wherein at least one component is an optically active compound of the formula R.sup.1 --CHCH.sub.3 --CHCH.sub.3 --R.sup.2 wherein R 1 and R 2 independently of one another are each --Z 1 --(A 1 ) m --Z 2 --(A 2 ) n --Y, wherein A 1 and A 2 in each case independently of one another are 1,4-phenylene, pyrimidine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene, or one of said groups monosubstituted or polysubstituted by F, Cl, Br, CN, alkyl of up to 12 C atoms, or C 1-12 alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, Z 1 is --O--CO--, --CO--O--, --O-- or a single bond, Z 2 is --CO--O--, --O--CO--, --CH 2 CH 2 , --OCH 2 , --CH 2 O--, --CH═N--, --N═CH--, --N═N--, --N(O)═N-- or a single bond, m and n in each case independently of one another are 0, 1 or 2, and Y is alkyl of up to 12 C atoms, or C 1-12 alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, or, if n is 1 or 2, Y can also be F, Cl, Br or CN, wherein for all Y groups, all alkyl portions are straight chained.
Claim 21
Dependent Claim
222 words
In a liquid crystal phase comprising at least two components, the improvement wherein at least one component is an optically active compound of the formula R.sup.1 --CHCH.sub.3 --CHCH.sub.3 --R.sup.2 wherein R 1 and R 2 independently of one another are each --Z 1 --(A 1 ) m --Z 2 --(A 2 ) n --Y, wherein A 1 and A 2 in each case independently of one another are 1,4-phenylene, pyrimidine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene, or one of said groups mono-substituted or poly-substituted by F, Cl, Br, CN, alkyl of up to 12 C atoms, or C 1-12 alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, Z 1 is --O--CO--, --CO--O--, --O-- or a single bond, Z 2 is --CO--O--, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --CH═N--, --N═CH--, --N═N--, --N(O)═N-- or a single bond, m and n in each case independently of one another are 0, 1, or 2, and Y is alkyl of up to 12 C atoms, or C 1-12 -alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, or, if n is 1 or 2, Y can also be F, Cl, Br or CN, wherein in each of R 1 and R 2 , one of n and m is not zero.
Claim 22
Dependent Claim
222 words
In a liquid crystal phase comprising at least two components, the improvement wherein at least one component is an optically active compound of the formula R.sup.1 --CHCH.sub.3 --CHCH.sub.3 --R.sup.2 wherein R 1 and R 2 independently of one another are each --Z 1 --(A 1 ) m --Z 2 --(A 2 ) n --Y, wherein A 1 and A 2 in each case independently of one another are 1,4-phenylene, pyrimidine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene, or one of said groups mono-substituted or poly-substituted by F, Cl, Br, CN, alkyl of up to 12 C atoms, or C 1-12 alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, Z 1 is --O--CO--, --CO--O--, --O-- or a single bond, Z 2 is --CO--O--, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --CH═N--, --N═CH--, --N═N--, --N(O)═N-- or a single bond, m and n in each case independently of one another are 0, 1, or 2, and Y is alkyl of up to 12 C atoms, or C 1-12 -alkyl wherein 1 or 2 non-adjacent CH 2 groups are replaced by 0 atoms, or, if n is 1 or 2, Y can also be F, Cl, Br or CN, wherein in each of R 1 and R 2 , one of n and m is not zero.
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