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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 13:36
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.
References Cited (Backward Citations)
US4664840A
Cited
US4368135A
Cited
DE2939782A1
Cited
US4545922A
Cited
US4415470A
Cited
EP0051738A1
Cited
US4808333A
Cited
US4514317A
Cited
US4551264A
Cited
US4606845A
Cited
US4724097A
Cited
US4602851A
Cited
US4594465A
Cited
EP0133489A2
Cited
US4637897A
Cited
US4659502A
Cited
US4710315A
Cited
US4726911A
Cited
US4776973A
Cited
US4846998A
Cited
US4834904A
Cited
US4820839A
Cited
US4925278A
Cited
WO1988002130A2
Cited
US5037576A
Cited
GB2198743A
Cited
US5147577A
Cited
US5133896A
Cited
US4897216A
Cited
US4925590A
Cited
US5087764A
Cited
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 |