US4752414A
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Nitrogen-containing heterocyclic compounds
Assignee: Merck Patent GmbH
•
Filing: 1986-07-11
•
Granted: 1988-06-21
•
Expires: 2006-07-11
Abstract
Abstract Nitrogen-containing heterocyclic compounds of the formula I R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --[Z.sup.2 --A.sup.3 ].sub.n --R 2 wherein R 1 and R 2 in each case independently of one another are an alkyl group with 1-15 C atoms, it also being possible for one or two non-adjacent CH 2 groups to be replaced by O atoms and/or --CO-- groups and/or --O--CO-- groups and/or --CO--O-- groups, and one of the radicals R 1 and R 2 is also H, F, Cl, Br or CN, A 1 is a 1,4-cyclohexylene group, it also being possible for one or two non-adjacent CH 2 groups to be replaced by O atoms, a 1,4-bicyclo-(2,2,2)-octylene group or a 1,3-dithiane-2,5-diyl group, Z 1 and Z 2 in each case independently of one another are --CO--O--, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O-- or a single bond, A 2 and A 3 in each case independently of one another are a 1,4-phenylene group, pyrimidine-2,5-diyl group, 1,4-cyclohexylene group, it also being possible for one or two non-adjacent CH 2 groups to be replaced by O atoms, 1,3-dithiane-2,5-diyl group or a 1,4-bicyclo(2,2,2)-octylene group and n is 0 or 1, with the provisos that (a) at least one of the groups A 2 and A 3 is a pyrimidine-2,5-diyl group, (b) at least one of the groups Z 1 and Z 2 is not a single bond if A 2 is pyrimidine-2,5-diyl and R 2 is alkyl or CN, (c) Z 1 is not --CO--O-- if A 3 is pyrimidine-2,5-diyl and A 1 is 1,4-cyclohexylene, (d) n is not 0 if A 1 is 1,4-cyclohexylene and Z 1 is --CH 2 CH 2 --, and (e) Z 1 is not --CH 2 CH 2 -- if R 2 is CN, and (f) Z 1 is --CH 2 CH 2 --, --OCH 2 -- or --CH 2 O--, if A 1 is 1,4-cyclohexylene and --A 2 --[Z 2 --A 3 ] n -- is ##STR1## and acid addition salts thereof, can be used as components of liquid crystal phases.
Inventors
- 👤 Rudolf Eidenschink
- 👤 Joachim Krause
- 👤 Reinhard Hittich
- 👤 Eike Poetsch
- 👤 Bernhard Scheuble
- 👤 Georg Weber
- 👤 Ludwig Pohl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 08:10
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C07D239/28; C07D239/32; C07D239/34; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/34; C09K19/3441
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
174 words
In a liquid crystalline phase comprising at least two liquid crystalline compounds, the improvement wherein at least one compound is of the formula R.sup.1 -A.sup.1 -Z.sup.1 -A.sup.2 -Z.sup.2 -A.sup.3 -R.sup.2 wherein R 1 is alkyl of 1-15 C atoms, R 2 is alkyl or alkoxy of 1-10 C atoms, F or CN, A 1 is 1,4-cyclohexylene, each of Z 1 and Z 2 independently is --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--or a single bond, each of A 2 and A 3 independently is 1,4-phenylene, pyrimidine-2,5-diyl or 1,4-cyclohexylene, with the provisos that (a) at least one of A 2 and A 3 is pyrimidine-2,5-diyl, and (b) at least one of Z 1 and Z 2 is not a single bond and/or A 2 is 1,4-cyclohexylene, or of the formula Alkyl-Cy-Pyr-Phe-Alkoxy wherein Alkyl is a straight-chain alkyl group of 2 to 7 C-atoms, Alkoxy is a straight-chain alkoxy group of 1 to 12 C atoms, Cy is a 1,4-cyclohexylene group, Pyr is a pyrimidine-2,5-diyl group and Phe is a 1,4-phenylene group.
Claim 2
Dependent Claim
174 words
In a liquid crystalline phase comprising at least two liquid crystalline compounds, the improvement wherein at least one compound is of the formula R.sup.1 -A.sup.1 -Z.sup.1 -A.sup.2 -Z.sup.2 -A.sup.3 -R.sup.2 wherein R 1 is alkyl of 1-15 C atoms, R 2 is alkyl or alkoxy of 1-10 C atoms, F or CN, A 1 is 1,4-cyclohexylene, each of Z 1 and Z 2 independently is --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--or a single bond, each of A 2 and A 3 independently is 1,4-phenylene, pyrimidine-2,5-diyl or 1,4-cyclohexylene, with the provisos that (a) at least one of A 2 and A 3 is pyrimidine-2,5-diyl, and (b) at least one of Z 1 and Z 2 is not a single bond and/or A 2 is 1,4-cyclohexylene, or of the formula Alkyl-Cy-Pyr-Phe-Alkoxy wherein Alkyl is a straight-chain alkyl group of 2 to 7 C-atoms, Alkoxy is a straight-chain alkoxy group of 1 to 12 C atoms, Cy is a 1,4-cyclohexylene group, Pyr is a pyrimidine-2,5-diyl group and Phe is a 1,4-phenylene group.
Claim 3
Dependent Claim
156 words
A compound of the formula R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.2 wherein R 1 is alkyl of 1-15 C atoms, R 2 is alkyl or alkoxy of 1-10 C atoms, F or CN, A 1 is 1,4-cyclohexylene, each of Z 1 and Z 2 independently is --CH 2 CH 2 --, --OCH 2 --, --CH 2 O-- or a single bond, each of A 2 and A 3 independently is 1,4-phenylene, pyrimidine-2,5-diyl or 1,4-cyclohexylene, with the provisos that (a) at least one of A 2 and A 3 is pyrimidine-2,5-diyl, and (b) at least one of Z 1 and Z 2 is not a single bond and/or A 2 is 1,4-cyclohexylene, or of the formula Alkyl--Cy--Pyr--Phe--Alkoxy wherein Alkyl is a straight-chain alkyl group of 2 to 7 C-atoms, Alkoxy is a straight-chain alkoxy group of 1 to 12 C-atoms, Cy is a 1,4-cyclohexylene group, Pyr is a pyrimidine-2,5-diyl group and Phe is a 1,4-phenylene group.
Claim 4
Dependent Claim
156 words
A compound of the formula R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.2 wherein R 1 is alkyl of 1-15 C atoms, R 2 is alkyl or alkoxy of 1-10 C atoms, F or CN, A 1 is 1,4-cyclohexylene, each of Z 1 and Z 2 independently is --CH 2 CH 2 --, --OCH 2 --, --CH 2 O-- or a single bond, each of A 2 and A 3 independently is 1,4-phenylene, pyrimidine-2,5-diyl or 1,4-cyclohexylene, with the provisos that (a) at least one of A 2 and A 3 is pyrimidine-2,5-diyl, and (b) at least one of Z 1 and Z 2 is not a single bond and/or A 2 is 1,4-cyclohexylene, or of the formula Alkyl--Cy--Pyr--Phe--Alkoxy wherein Alkyl is a straight-chain alkyl group of 2 to 7 C-atoms, Alkoxy is a straight-chain alkoxy group of 1 to 12 C-atoms, Cy is a 1,4-cyclohexylene group, Pyr is a pyrimidine-2,5-diyl group and Phe is a 1,4-phenylene group.
Claim 5
Dependent Claim
46 words
A phase of claim 1, wherein said formula is R.sup.1 --A.sup.1 --A.sup.2 --A.sup.3 --R.sup.2 R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.2 R.sup.1 --A.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.2 R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.2 wherein each of Z 1 and Z 2 is not a single bond.
Claim 6
Dependent Claim
22 words
A phase of claim 1, wherein said formula is R.sup.1 --Cy--Cy--Pyr--R.sup.2 wherein Cy is 1,4-cyclohexylene, Phe is 1,4-phenylene and Pyr is pyrimidine-2,5-diyl.
Claim 7
Dependent Claim
32 words
A phase of claim 1, wherein said formula is R.sup.1 --Cy--Z.sup.1 --Pyr--Phe--R.sup.2 R.sup.1 --Cy--Z.sup.1 --Phe--Pyr--R.sup.2 R.sup.1 --Cy--Z.sup.1 --Pyr--Cy--R.sup.2 R.sup.1 --Cy--Z.sup.1 --Cy--Pyr--R.sup.2 wherein Cy is 1,4-cyclohexylene, Phe is 1,4-phenylene and Pyr is pyrimidine-2,5-diyl.
Claim 8
Dependent Claim
32 words
A phase of claim 1, wherein said formula is R.sup.1 --Cy--Pyr--Z.sup.2 --Phe--R.sup.2 R.sup.1 --Cy--Pyr--Z.sup.2 --Cy--R.sup.2 R.sub.1 --Cy--Phe--Z.sup.2 --Pyr--R.sup.2 R.sup.1 --Cy--Cy--Z.sup.2 --Pyr--R.sup.2 wherein Cy is 1,4-cyclohexylene, Phe is 1,4-phenylene and Pyr is pyrimidine-2,5-diyl.
Claim 9
Dependent Claim
18 words
A phase of claim 1, wherein said formula is R.sup.1 --A.sup.1 --CH.sub.2 CH.sub.2 --A.sup.2 --CH.sub.2 CH.sub.2 --A.sup.3 --R.sup.2.
Claim 10
Dependent Claim
61 words
A phase of claim 1, wherein said formula is Alkyl--Cy--Cy--Pyr--Alkyl Alkyl--Cy--Cy--Pyr--Alkoxy Alkyl--Cy--CH.sub.2 CH.sub.2 --Phe--Pyr--Alkyl Alkyl--Cy--CH.sub.2 CH.sub.2 --Phe--Pyr--Alkoxy Alkyl--Cy--CH.sub.2 CH.sub.2 --Phe--Pyr--CN Alkyl--Cy--Pyr--Phe--Alkoxy Alkyl--Cy--CH.sub.2 CH.sub.2 --Pyr--Phe--Alkyl Alkyl--Cy--CH.sub.2 CH.sub.2 --Pyr--Phe--Alkoxy Alkyl--Cy--CH.sub.2 CH.sub.2 --Pyr--Phe--CN Alkyl--Cy--Pyr--CH.sub.2 CH.sub.2 --Phe--Alkyl Alkyl--Cy--Pyr--CH.sub.2 CH.sub.2 --Phe--Alkoxy Alkyl--Cy--Pyr--CH.sub.2 CH.sub.2 --Phe--CN Alkyl--Cy--Pyr--CH.sub.2 CH.sub.2 --Cy--Alkyl Alkyl--Cy--CH.sub.2 --O--Phe--Pyr--Alkyl Alkyl--Cy--CH.sub.2 CH.sub.2 --Cy--Pyr--Alkyl Alkyl--Cy--Cy--CH.sub.2 CH.sub.2 --Pyr--Alkyl wherein Cy is 1,4-cyclohexylene, Phe is 1,4-phenylene and Pyr is pyrimidine-2,5-diyl.
Claim 11
Dependent Claim
36 words
A phase of claim 1, wherein said formula is R.sup.1 --Cy--Cy--Pyr--R.sup.2 R.sup.1 --Cy--Z.sup.1 --Pyr--Phe--R.sup.2 R.sup.1 --Cy--Z.sup.1 --Phe--Pyr--R.sup.2 R.sup.1 --Cy--Z.sup.1 --Pyr--Cy--R.sup.2 R.sup.1 --A.sup.1 --A.sup.2 --CH.sub.2 CH.sub.2 --A.sup.3 --R.sup.2 R.sup.1 --A.sup.1 --CH.sub.2 CH.sub.2 --A.sup.2 --CH.sub.2 CH.sub.2 --A.sup.3 --R.sup.2.
Claim 12
Dependent Claim
42 words
A phase of claim 1, wherein said formula is Alkyl--Cy--Cy--Pyr--Alkyl Alkyl--Cy--Cy--Pyr--Alkoxy Alkyl--Cy--CH.sub.2 CH.sub.2 --Phe--Pyr--Alkyl Alkyl--Cy--CH.sub.2 CH.sub.2 --Phe--Pyr--Alkoxy Alkyl--Cy--CH.sub.2 CH.sub.2 --Phe--Pyr--CN Alkyl--Cy--CH.sub.2 CH.sub.2 --Pyr--Phe--Alkyl Alkyl--Cy--CH.sub.2 CH.sub.2 --Pyr--Phe--Alkoxy Alkyl--Cy--CH.sub.2 CH.sub.2 --Pyr--Phe--CN Alkyl--Cy--CH.sub.2 --O--Phe--Pyr--Alkyl wherein Cy is 1,4-cyclohexylene, Phe is 1,4-phenylene and Pyr is pyrimidine-2,5-diyl.
Claim 13
Dependent Claim
36 words
A phase of claim 1, wherein in said formula one of Z 1 and Z 2 is a single bond and the other is --CH 2 CH 2 --, --OCH 2 -- or --CH 2 O--.
Claim 14
Dependent Claim
34 words
A phase of claim 1, wherein in said formula Z 1 is --CH 2 CH 2 --, --OCH 2 -- or --CH 2 O--, and --A 2 --Z 2 --A 3 -- is ##STR5##
Claim 15
Dependent Claim
18 words
A phase of claim 1, wherein in said formula --A 1 --Z 1 --A 2 -- is --Cy--Cy.
Claim 16
Dependent Claim
21 words
In a liquid crystal display element comprising a liquid crystalline phase, the improvement wherein the phase is one of claim 1.
Claim 17
Dependent Claim
21 words
In an electrooptical display element comprising a liquid crystalline dielectric, the improvement wherein the dielectric is a phase of claim 1.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1991-06-21 | 1991-12-21 | 1992-06-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-06-21 | 1995-12-21 | 1996-06-21 | $3760.00 | Window Closed / Lapsed |
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