US5116527A
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Display element based on the electroclinic effect
Assignee: Merck Patent GmbH
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Filing: 1989-05-12
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Granted: 1992-05-26
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Expires: 2009-05-12
Abstract
Abstract The invenion relates to a display element based on the electroclinic effect containing a liquid crystal medium being a mixture of at least two chiral components and at least one non-chiral component, characterized in that said medium has a pitch compensated cholesteric phase above the optically active smectic A phase.
Inventors
- 👤 David Coates
- 👤 Ian C. Sage
- 👤 Thomas Geelhaar
- 👤 Andreas Wachtler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 21:44
CPC Classifications
G; G02; G02F; G02F1/00; G02F1/01; G02F1/13; G02F1/137; G02F1/139; G02F1/141; G02F1/1418; C; C09; C09K; C09K19/00; C09K19/04; C09K19/42; C09K19/46
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
376 words
In an electroclinic effect display element containing a liquid crystal medium, the improvement wherein: said medium is a mixture of at least two chiral components and at least one non-chiral component, said medium has a compensated cholesteric phase above an optically active smectic A phase, wherein said medium is capable of exhibiting an electroclinic effect, and wherein said at least one non-chiral component is a compound of formula I ##STR12## wherein R 1 and R 2 are each independently an alkyl group with 5 to 15 C atoms wherein one or two non-adjacent CH 2 groups can also be replaced by --O--, --S--, --CO--O--, --O--CO-- and/or --CH═CH, ##STR13## is a 1,4-phenylene group optionally substituted by fluorine wherein in Formula I, at least one group ##STR14## is a 1,4-phenylene group which is substituted by fluorine, and n and m are each independently 1 or 2, and at least one of said chiral components is a compound of formula II ##STR15## wherein R 3 is an alkyl or alkenyl group each with 5 to 15 C atoms, optionally substituted by CN or at least one halogen atom wherein one or two non-adjacent CH 2 groups can be replaced by --O--, --CO--, --CO--O--, --O--CO--, --S-- and/or --C═C--, R 4 is an alkyl group with up to 8 C atoms wherein one CH 2 group can be replaced by --O--, --CO--O-- or --O--CO--, A 1 and A 2 are independently each an unsubstituted or mono- or polysubstituted 1,4-cyclohexylene group wherein one or two non-adjacent CH 2 groups may be replaced by --O--and/or --S--, a 1,4-bicyclo[2,2,2]octylene group, or a 1,4-phenylene group optionally substituted by fluorine, and wherein one or two CH groups may be replaced by N, X is CN, Cl, F, Br, CH 3 or CF 3 , Y is H or CH 3 , Z 1 is --CO--O--, --O--CO--, --CH 2 CH 2 --, --CHCN--CH 2 --, --CH 2 --CHCN--, --CH═CH--, --C═C--, --OCH 2 --, --CH 2 O--, --CH═N--, --N═CH--, --N═N--, --N═NO-- or a single bond, is 1, 2, or 3, and is an alkylene or alkenylene group with 1 to 7 C atoms wherein one CH 2 group can be replaced by --O--, --CO--O-- or --O--CO--, with the proviso that X, Y and R 4 are different groups.
Claim 2
Dependent Claim
376 words
In an electroclinic effect display element containing a liquid crystal medium, the improvement wherein: said medium is a mixture of at least two chiral components and at least one non-chiral component, said medium has a compensated cholesteric phase above an optically active smectic A phase, wherein said medium is capable of exhibiting an electroclinic effect, and wherein said at least one non-chiral component is a compound of formula I ##STR12## wherein R 1 and R 2 are each independently an alkyl group with 5 to 15 C atoms wherein one or two non-adjacent CH 2 groups can also be replaced by --O--, --S--, --CO--O--, --O--CO-- and/or --CH═CH, ##STR13## is a 1,4-phenylene group optionally substituted by fluorine wherein in Formula I, at least one group ##STR14## is a 1,4-phenylene group which is substituted by fluorine, and n and m are each independently 1 or 2, and at least one of said chiral components is a compound of formula II ##STR15## wherein R 3 is an alkyl or alkenyl group each with 5 to 15 C atoms, optionally substituted by CN or at least one halogen atom wherein one or two non-adjacent CH 2 groups can be replaced by --O--, --CO--, --CO--O--, --O--CO--, --S-- and/or --C═C--, R 4 is an alkyl group with up to 8 C atoms wherein one CH 2 group can be replaced by --O--, --CO--O-- or --O--CO--, A 1 and A 2 are independently each an unsubstituted or mono- or polysubstituted 1,4-cyclohexylene group wherein one or two non-adjacent CH 2 groups may be replaced by --O--and/or --S--, a 1,4-bicyclo[2,2,2]octylene group, or a 1,4-phenylene group optionally substituted by fluorine, and wherein one or two CH groups may be replaced by N, X is CN, Cl, F, Br, CH 3 or CF 3 , Y is H or CH 3 , Z 1 is --CO--O--, --O--CO--, --CH 2 CH 2 --, --CHCN--CH 2 --, --CH 2 --CHCN--, --CH═CH--, --C═C--, --OCH 2 --, --CH 2 O--, --CH═N--, --N═CH--, --N═N--, --N═NO-- or a single bond, is 1, 2, or 3, and is an alkylene or alkenylene group with 1 to 7 C atoms wherein one CH 2 group can be replaced by --O--, --CO--O-- or --O--CO--, with the proviso that X, Y and R 4 are different groups.
Claim 3
Dependent Claim
325 words
A display element according to claim 1, wherein at least one component is a compound of the formula III ##STR16## wherein R 5 and R 6 are each independently an alkyl group with 5 to 15 C atoms wherein one or two CH 2 groups can also be replaced by --O--, --S--, --CO--O--, --O--CO-- and/or --CH═CH--, ##STR17## denotes a 1,4-phenylene group optionally substituted by fluorine, ##STR18## denotes a 1,4-phenylene group optionally substituted by fluorine or a trans-1,4-cyclohexylene group, q is 0 or 1, and r is 1 or 2, and said at least one chiral component is a compound of the formula II wherein ##STR19## R 3 is an alkyl or alkenyl group each with 5 to 15 C atoms, optionally substituted by CN or at least one halogen atom wherein one or two nonadjacent CH 2 groups can be replaced by --O--, --CO--, --CO--O--, --O--CO--, --S-- and/or --C═C--, R 4 is an alkyl group with up to 8 C atoms wherein one CH 2 group can be replaced by --O--, --CO--O--or --O--CO, A 1 and A 2 independently are an unsubstituted or mono--or polysubstituted 1,4-cyclohexylene group, wherein one or two non-adjacent CH 2 groups may be replaced by --O-- and/or --S--, or denote a 1,4-bicyclo octylene group, or a 1,4-phenylene group optionally substituted by fluorine, and wherein one or two CH groups may be replaced by N, X is CN, Cl, F, Br, CH 3 or CF 3 , Y is H or CH 3 , Z 1 denotes --CO--O--, --O--CO--, --CH 2 CH 2 --, --CHCN--CH 2 --, --CH 2 --CHCN--, --CH═CH--, --C═C--, --OCH 2 --, --CH 2 O, --CH═N--, --N═CH--, --N═N, --NO═N--, --═NO-- or a single bond, o is 1, 2, or 3, and O is an alkylene or alkenylene group with 1 to 7 C atoms wherein one CH 2 group can be replaced by --O--, --CO--O or --O--CO--, with the proviso that X, Y and R 4 are different groups.
Claim 4
Dependent Claim
27 words
A display element according to claim 1 wherein R 1 and R 2 in formula I are each alkyl or alkoxy with 5 to 15 C atoms.
Claim 5
Dependent Claim
27 words
A display element according to claim 2, wherein R 5 and R 6 in formula III are each alkyl or alkoxy with 5 to 15 C atoms.
Claim 6
Dependent Claim
21 words
A display element according to claim 1, wherein both said at least two chiral components are compounds according to Formula II.
Claim 7
Dependent Claim
21 words
A display element according to claim 2, wherein both said at least two chiral components are compounds according to Formula II.
Claim 8
Dependent Claim
68 words
A display element according to claim 1, wherein said chiral compound according to Formula II is of Formulae IIa-IIf ##STR20## wherein R 7 is alkyl or alkoxy with 5 to 15 C atoms, R 8 is alkyl with 1 to 8 C atoms, o is 1 or 2, s is 0 or an integer value between 1 and 6, and is preferably 1,4-phenylene, pyridine-2,5-diyl pyrimidine-2,5-diyl, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene.
Claim 9
Dependent Claim
68 words
A display element according to claim 2, wherein said chiral compound according to Formula II is of Formulae IIa-IIf ##STR21## wherein R 7 is alkyl or alkoxy with 5 to 15 C atoms, R 8 is alkyl with 1 to 8 C atoms, o is 1 or 2, s is 0 or an integer value between 1 and 6, and is preferably 1,4-phenylene, pyridine-2,5-diyl pyrimidine-2,5-diyl, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene.
Claim 10
Dependent Claim
75 words
A display element according to claim 1, wherein said liquid crystal mixture further contains at least one ##STR22## wherein R 9 and R 10 are each alkyl or alkoxy with 5 or 15 C atoms, L is hydrogen or fluorine, A 3 and A 4 each independently are 1,4-phenylene or trans-1,4-cyclohexylene, u and v are each independently 0, 1 or 2, the sum of u+v being 1 or 2, and t is 1 or 2.
Claim 11
Dependent Claim
68 words
A display element according to claim 2, wherein said liquid crystal mixture further contains at least one ##STR23## wherein R 9 and R 10 are each alkyl or alkoxy with 5 or 15 C atoms, L is hydrogen or fluorine, A 3 and A 4 each independently are 1,4-phenylene or trans-1,4-cyclohexylene, u and v are each independently 0, 1, or 2, the sum of is 1 or 2.
Claim 12
Dependent Claim
17 words
A display element according to claim 1, wherein said liquid crystal medium contains 4-pentyl-2-fluorophenyl-4-octyloxybiphenyl-4-yl-carboxylate; 1-cyano-3-methylpropyl-4'-octyloxy-3'-fluorobiphenyl-4-ylcarboxylate; and 2-p-hexyloxyphenyl-5-heptylpyrimidine.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-05-26 | 1995-11-25 | 1996-05-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-05-26 | 1999-11-25 | 2000-05-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-05-26 | 2003-11-25 | 2004-05-26 | $7700.00 | Window Closed / Lapsed |