US5273680A
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Fluorinated oligophenyls and their use in liquid crystal materials
Assignee: Merck KGaA
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Filing: 1988-08-13
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Granted: 1993-12-28
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Expires: 2008-08-13
Abstract
Abstract PCT No. PCT/EP88/00724 Sec. 371 Date Mar. 8, 1989 Sec. 102(e) Date Mar. 8, 1989 PCT Filed Aug. 13, 1988 PCT Pub. No. WO89/02425 PCT Pub. Date Mar. 23, 1989.This invention relates to fluorinated oligophenyls of formula (I), in which a is 0 or 1 and in which the terminal substituents R1, R2 and R3 are each independently an alkyl or alkenyl residue each with up to 15 C atoms, optionally substituted by CN or by at least one halogen atom, and wherein one or more non adjacent CH2 groups of these residues may be replaced by -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O- or -C 3BOND C-, one of the residues R1 and R2 may also denote a group of formula (II), any one of the following pairs of lateral substituents are both fluorine: (A, B), (C, D), (D, E), (C, E), (B, C), (D, J), (D, K), (A, C), (C, J), (C', D'), (D', E), (D', A), (C', E), (C', A), (D', J'), (D', K'), (C', J'), (B, G), (A, G), all of the other lateral substituents being hydrogen or fluorine, and to their use as components of liquid crystalline compositions.
Inventors
- 👤 George W. Gray
- 👤 Michael Hird
- 👤 David Lacey
- 👤 Kenneth J. Toyne
- 👤 Volker Reiffenrath
- 👤 Andreas Wachtler
- 👤 Joachim Krause
- 👤 Ulrich Finkenzeller
- 👤 Thomas Geelhaar
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 13:06
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/10; C09K19/12; C09K19/126; C09K19/42; C09K19/46; C09K2019/121; C09K2019/123
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
134 words
A chiral tilted smectic liquid crystalline composition comprising at least two liquid crystalline compounds, wherein at least one compound is a terphenyl of formula I: ##STR24## in which the terminal substituents R 1 , R 2 and R 3 are each independently an alkyl or alkenyl residue each with up to 15 C atoms, optionally substituted by CN or by at least one halogen atom, and wherein one or more non-adjacent CH 2 groups of these residues may be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O--, --O--CO--O or --C.tbd.C--, one of the residues R 1 and R 2 may also denote a group of the formula ##STR25## any one of the following pairs of lateral substitutents are both fluorine: (C", D') are both fluorine, all of the other lateral substituents being hydrogen or fluorine.
Claim 2
Dependent Claim
134 words
A chiral tilted smectic liquid crystalline composition comprising at least two liquid crystalline compounds, wherein at least one compound is a terphenyl of formula I: ##STR24## in which the terminal substituents R 1 , R 2 and R 3 are each independently an alkyl or alkenyl residue each with up to 15 C atoms, optionally substituted by CN or by at least one halogen atom, and wherein one or more non-adjacent CH 2 groups of these residues may be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O--, --O--CO--O or --C.tbd.C--, one of the residues R 1 and R 2 may also denote a group of the formula ##STR25## any one of the following pairs of lateral substitutents are both fluorine: (C", D') are both fluorine, all of the other lateral substituents being hydrogen or fluorine.
Claim 3
Dependent Claim
42 words
A composition of claim 1 wherein the terminal substituents R 1 and R 2 or R 3 and one of the residues of R 1 and R 2 are independently alkoxy, alkyl, perfluoroalkyl or perfluoroalkoxy each with up to 15 C atoms.
Claim 4
Dependent Claim
90 words
A liquid crystalline composition according to claim 1 comprising at least one compound of formula I and at least one compound of formula: ##STR26## wherein R A is C 5-12 -alkyl or C 5-12 -alkoxy, R B is C 1 -C 4 n-alkyl, cyclohexyl or a branched or chiral alkyl of the formula ##STR27## where a is 0 or 1-6, and each of b and c are independently 1-6, and (F) indicates that the ring may carry a lateral fluoro-substituent, n is 1 or 2, m is 0 or 1.
Claim 5
Dependent Claim
14 words
A liquid crystalline display element, comprising a liquid crystalline phase according to claim 1.
Claim 6
Dependent Claim
13 words
An electro-optical display element, comprising a liquid crystalline phase according to claim 1.
Claim 7
Dependent Claim
105 words
A composition containing a compound of formula I' ##STR28## wherein A 1 and A 2 are each independently a 1,4-phenylene group optionally substituted by one to four fluorines, R 1 and R 2 are each independently an alkyl or alkenyl residue each with up to 15 C atoms, optionally substituted by CN or by at lease one halogen atom, and wherein one or more non-adjacent CH 2 groups of these residues may be replaced by --O, --S--, --CO--, --O--CO--, --CO--O--, --O--CO--O-- or --C.tbd.C--, m is 0 or 1, n is 1, 2 or 3, and the sum of m and n is 2 or 3.
Claim 8
Dependent Claim
105 words
A composition containing a compound of formula I' ##STR28## wherein A 1 and A 2 are each independently a 1,4-phenylene group optionally substituted by one to four fluorines, R 1 and R 2 are each independently an alkyl or alkenyl residue each with up to 15 C atoms, optionally substituted by CN or by at lease one halogen atom, and wherein one or more non-adjacent CH 2 groups of these residues may be replaced by --O, --S--, --CO--, --O--CO--, --CO--O--, --O--CO--O-- or --C.tbd.C--, m is 0 or 1, n is 1, 2 or 3, and the sum of m and n is 2 or 3.
Claim 9
Dependent Claim
17 words
A composition comprising a p-terphenyl of claim 6, wherein the sum of m and n is 2.
Claim 10
Dependent Claim
132 words
A chiral tilted smectic composition comprising at least two LC comopunds, wherein at least one compound is a biphenyl compound of the formula ##STR29## in which the terminal substituents R 1 , R 2 and R 3 are each independently an alkyl or alkenyl residue each with up to 15 C atoms, optionally substituted by CN or by at least one halogen atom, and wherein one or more non-adjacent CH 2 groups of these residues may be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O--, --O--CO--O or --C.tbd.C--, one of the residues R 1 and R 2 may also denote a group of the formula, ##STR30## any one of the following pairs of lateral substitutents are both fluorine: (C", D') are both fluorine, all of the other lateral substituents being hydrogen or fluorine.
Claim 11
Dependent Claim
132 words
A chiral tilted smectic composition comprising at least two LC comopunds, wherein at least one compound is a biphenyl compound of the formula ##STR29## in which the terminal substituents R 1 , R 2 and R 3 are each independently an alkyl or alkenyl residue each with up to 15 C atoms, optionally substituted by CN or by at least one halogen atom, and wherein one or more non-adjacent CH 2 groups of these residues may be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O--, --O--CO--O or --C.tbd.C--, one of the residues R 1 and R 2 may also denote a group of the formula, ##STR30## any one of the following pairs of lateral substitutents are both fluorine: (C", D') are both fluorine, all of the other lateral substituents being hydrogen or fluorine.
Claim 12
Dependent Claim
114 words
A compound of the formula: ##STR31## in which the terminal substituents R 1 , R 2 and R 3 are each independently an alkyl or alkenyl residue each with up to 15 C atoms, optionally substituted by CN or by at least one halogen atom, and wherein one or more non-adjacent CH 2 groups of these residues may be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O--, --O--CO--O or --C.tbd.C--, one of the residues R 1 and R 2 may also denote a group of the formula, ##STR32## any one of the following pairs of lateral substitutents are both fluorine: (C", D') are both fluorine, all of the other lateral substituents being hydrogen or fluorine.
Claim 13
Dependent Claim
114 words
A compound of the formula: ##STR31## in which the terminal substituents R 1 , R 2 and R 3 are each independently an alkyl or alkenyl residue each with up to 15 C atoms, optionally substituted by CN or by at least one halogen atom, and wherein one or more non-adjacent CH 2 groups of these residues may be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O--, --O--CO--O or --C.tbd.C--, one of the residues R 1 and R 2 may also denote a group of the formula, ##STR32## any one of the following pairs of lateral substitutents are both fluorine: (C", D') are both fluorine, all of the other lateral substituents being hydrogen or fluorine.
Claim 14
Dependent Claim
21 words
A compound of claim 9 wherein the terminal substituents are each independently n-alkyl or n-alkoxy with 5 to 12 carbon atoms.
Claim 15
Dependent Claim
24 words
A compound of claim 10, wherein at least one terminal substituent is a chiral alkyl or alkoxy group with 5 to 12 carbon atoms.
Claim 16
Dependent Claim
130 words
An electro-optical display element based on the ECB effect, containing a liquid crystalline phase, which has a negative dielectric anisotropy, comprising at least one liquid crystalline component is a compound of formula I' ##STR33## wherein A 1 and A 2 are each independently a 1,4-phenylene group optionally substituted by one to four fluorines, R 1 and R 2 are each independently an alkyl or alkenyl residue each with up to 15 C atoms, optionally substituted by CN or by at lease one halogen atom, and wherein one or more non-adjacent CH 2 groups of these residues may be replaced by --O, --S--, --CO--, --O--CO--, --CO--O--, --O--CO--O-- or --C.tbd.C--, m is 0 or 1, n is 1, 2 or 3, and the sum of m and n is 2 or 3.
Claim 17
Dependent Claim
130 words
An electro-optical display element based on the ECB effect, containing a liquid crystalline phase, which has a negative dielectric anisotropy, comprising at least one liquid crystalline component is a compound of formula I' ##STR33## wherein A 1 and A 2 are each independently a 1,4-phenylene group optionally substituted by one to four fluorines, R 1 and R 2 are each independently an alkyl or alkenyl residue each with up to 15 C atoms, optionally substituted by CN or by at lease one halogen atom, and wherein one or more non-adjacent CH 2 groups of these residues may be replaced by --O, --S--, --CO--, --O--CO--, --CO--O--, --O--CO--O-- or --C.tbd.C--, m is 0 or 1, n is 1, 2 or 3, and the sum of m and n is 2 or 3.
Claim 18
Dependent Claim
16 words
An electro-optical display element of claim 12, wherein the sum of m and n is 2.
Claim 19
Dependent Claim
23 words
An electro-optical display element of claim 13, wherein the terminal substituents are each independently n-alkyl or alkoxy with 1 to 7 carbon atoms.
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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) | 1996-12-27 | 1997-06-28 | 1997-12-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-12-27 | 2001-06-28 | 2001-12-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-12-27 | 2005-06-28 | 2005-12-28 | $7700.00 | Window Closed / Lapsed |