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US5209866A Expired / Lapsed US ⏱️ 0.0 years remaining

Heterocyclic 1,2-difluorobenzene derivatives

Assignee: Merck Patent GmbH
•
Filing: 1989-05-15
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Granted: 1993-05-11
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Expires: 2009-05-15
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Abstract

Abstract Heterocyclic 1,2-difluorobenzene derivatives of the formula I ##STR1## in which R 1 and R 2 , in each case independently of one another, are an alkyl groups (sic) having 1-15 C atoms in which, in addition, one or more CH 2 groups may be replaced by a divalent radical selected from the group comprising --O--, --S--, --CO--, --O--CO--, --CO--O--, --CH═CH-- and --C.tbd.C--, where two heteroatoms are not linked directly to one another, A 1 and A 2 , in each case independently of one another, are a 1,4-phenylene group which is unsubstituted or monosubstituted or polysubstituted by fluorine, and in which, in addition, one or two CH groups may be replaced by N, or are a 1,3,4-thiadiazole-2,5-diyl group or a trans-1,4-cyclohexylene group, m and n are each 0 or 2, o is 0 or 1, and p is 0, 1 or 2, where (o+p) is 1, 2 or 3 and, in the case where p=2, the A 2 groups and n may be identical or different with the proviso that at least one of the groups A 1 and A 2 is a 1,3,4-thiadiazole-2,5-diyl group or an unsubstituted or substituted 1,4-phenylene group in which one or two CH groups have been replaced by N, are suitable as components of liquid-crystalline phases.

Inventors

  • 👤 Volker Reiffenrath
  • 👤 Joachim Krause
  • 👤 Andreas Wachtler
  • 👤 Thomas Geelhaar

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 11:23
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/30; C07D213/60; C07D213/62; C07D213/63; C07D213/65; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C07D239/28; C07D239/32; C07D239/34; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/12; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/34; C09K19/3441; C09K19/3444; C09K19/345; C09K19/3458; C09K19/3491; C09K19/3497

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 145 words
A heterocyclic 1,2-difluorobenzene derivative of the formula I2 ##STR11## in which R is a straight chain alkyl group having 1 to 15 C atoms in which, in addition, one or more CH 2 may be replaced by a divalent radical selected from --O--, --S--, --CO--, --O--CO--, --CO--O--, --CH═CH-- or --C.tbd.C--, where two heteroatoms are not linked directly to one another, P is 1 or 2, n is 0 or 2, R 2 is a straight chain alkyl group having 1-15 C atoms in which, in addition, one or more CH 2 groups may be replaced by a divalent radical selected from --O--, --S--, --CO--, --O--CO--, --CO--O, or --C.tbd.C--, where two heteroatoms are not linked directly to one another, A 2 is a 1,4-phenylene group which is unsubstituted or monosubstituted or polysubstituted by fluorine, or a trans-1,4-cyclohexylene group, and A is a 1,3,4-thiadiazole-2,5-diyl- or pyridine 2,5-diyl.
Claim 2
Dependent Claim 145 words
A heterocyclic 1,2-difluorobenzene derivative of the formula I2 ##STR11## in which R is a straight chain alkyl group having 1 to 15 C atoms in which, in addition, one or more CH 2 may be replaced by a divalent radical selected from --O--, --S--, --CO--, --O--CO--, --CO--O--, --CH═CH-- or --C.tbd.C--, where two heteroatoms are not linked directly to one another, P is 1 or 2, n is 0 or 2, R 2 is a straight chain alkyl group having 1-15 C atoms in which, in addition, one or more CH 2 groups may be replaced by a divalent radical selected from --O--, --S--, --CO--, --O--CO--, --CO--O, or --C.tbd.C--, where two heteroatoms are not linked directly to one another, A 2 is a 1,4-phenylene group which is unsubstituted or monosubstituted or polysubstituted by fluorine, or a trans-1,4-cyclohexylene group, and A is a 1,3,4-thiadiazole-2,5-diyl- or pyridine 2,5-diyl.
Claim 3
Dependent Claim 39 words
A difluorobenzene derivative of claim 1, wherein RO is a straight-chain group which is selected from methoxy, ethoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, tridecosy, tetradecoxy, 1,3-, 1,4- or 1,5-dioxahexyl and 1,3-, 1,4-, 1,5- or 1,6-dioxaheptyl.
Claim 4
Dependent Claim 23 words
A difluorobenzene derivative of claim 1, wherein R 2 is a straight-chain alkyl, alkoxy, oxaalkyl or dioxyalkyl group each of 2-12 C atoms.
Claim 5
Dependent Claim 10 words
A difluorobenzene derivative of claim 1, wherein n is 0.
Claim 6
Dependent Claim 53 words
A difluorobenzene derivative of claim 6, of the formulae having the ##STR12## wherein R is, in each case independently of one another, straight-chain or monobranched alkyl having 3 to 12 C atoms in which, in addition, one CH 2 group which is not linked to 0 may be replaced by --O-- or --CH═CH--.
Claim 7
Dependent Claim 19 words
A difluorobenzene derivative of claim 5, wherein R is alkyl, oxaalkyl or alkenyl having 3 to 12 C atoms.
Claim 8
Dependent Claim 10 words
A difluorobenzene derivative of claim 1, wherein A is ##STR13##
Claim 9
Dependent Claim 23 words
A liquid-crystalline phase having at least two liquid-crystalline components, which contains at least one compound of the formula I2 according to claim 1.
Claim 10
Dependent Claim 14 words
An electrooptical display element, which contains, as dielectric, a phase according to claim 8.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1996-05-10 1996-11-09 1997-05-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2000-05-10 2000-11-09 2001-05-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2004-05-10 2004-11-09 2005-05-11 $7700.00 Window Closed / Lapsed

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