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WO1991008184A3 - 1,2-disubstituted 2,6-difluorobenzene compounds and liquid crystal media - Google Patents

1,2-disubstituted 2,6-difluorobenzene compounds and liquid crystal media Download PDF

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Publication number
WO1991008184A3
WO1991008184A3 PCT/EP1990/002109 EP9002109W WO9108184A3 WO 1991008184 A3 WO1991008184 A3 WO 1991008184A3 EP 9002109 W EP9002109 W EP 9002109W WO 9108184 A3 WO9108184 A3 WO 9108184A3
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WIPO (PCT)
Prior art keywords
residue
independently
atoms
residues
diyl
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PCT/EP1990/002109
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German (de)
French (fr)
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WO1991008184A2 (en
Inventor
Eike Poetsch
Volker Meyer
Volker Reiffenrath
Andreas Waechtler
Ulrich Finkenzeller
Hans-Adolf Kurmeier
Reinhard Hittich
Bernhard Rieger
David Coates
Simon Greenfield
Robert William Clemitson
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Merck Patent Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
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Priority claimed from DE4000534A external-priority patent/DE4000534C2/en
Priority claimed from DE4000535A external-priority patent/DE4000535B4/en
Priority to JP3500951A priority Critical patent/JP2935746B2/en
Priority to KR1019910700836A priority patent/KR0184869B1/en
Priority to EP91900202A priority patent/EP0462237B1/en
Priority to DE4092096A priority patent/DE4092096C1/en
Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh
Priority to FI913726A priority patent/FI913726A7/en
Priority to DE90EP9002109D priority patent/DE4092096D2/en
Priority to BR909007097A priority patent/BR9007097A/en
Priority to DE59010675T priority patent/DE59010675D1/en
Publication of WO1991008184A2 publication Critical patent/WO1991008184A2/en
Priority to NO91913036A priority patent/NO913036L/en
Publication of WO1991008184A3 publication Critical patent/WO1991008184A3/en
Priority to US08/917,167 priority patent/US6200654B1/en

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    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Abstract

Disclosed are 1,4-disubstituted 2,6-difluorobenzene compounds of the formula (I), in which R is an unsubstituted alkyl or alkenyl residue with 1-15 C-atoms or an alkyl or alkenyl group with 1-15 C-atoms substituted with at least one halogen residue, whereby one or more CH2 groups can be replaced, independently of each other, by -O-, -S-, (α), (β) -CO-, -CO-O-, -O-CO- or -O-CO-O in such a way that O-atoms are not directly bound to each other, A?1 and A2¿, independently of each other, are (a) a trans-1,4-cyclohexylene residue in which one or more non-adjacent CH¿2? groups can be replaced by -O- and/or -S-, (b) a 1,4-phenylene residue in which one or two CH groups can be replaced by N, (c) a 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)-octylene, piperidine-1,4-diyl, naphthalene-2,6-dyil, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl residue, whereby residues (a) and (b) can be substituted with CN or one or two fluorine atoms, Z?1 and Z2¿, independently of each other, are -CO-O, -O-CO-, -CH¿2?O-, -OCH2-, -CH2CH2-, -CH=CH-, -C=C- or a single bond, m and n, independently of each other, are 0,1,2 or 3, (m + n) being 1,2 or 3, and X has the same meaning as R, or is F, Cl, -CF3, -OCF3, -OCF2H, -OC2F5, -CN or -NCS, with the provision that at least one of the residues Z1 and Z2 in the molecule is -CO-O-, -O-CO-, -CH2-O-, -OCH2-, -CH2CH2-, -CH=CH- or -C=C- and/or at least one of the residues A?1 and A2¿ in the molecule is (γ) or (δ), and/or n is 1 or 2, whereby when -(Z2-A2)n=(ε). X is F, Cl, -CF3, -OCF3, -OCF2H, -OC2F5, -CN or -NCS. Such compounds are suitable for use as components of liquid-crystal media.
PCT/EP1990/002109 1989-12-06 1990-12-06 1,2-disubstituted 2,6-difluorobenzene compounds and liquid crystal media WO1991008184A2 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
DE59010675T DE59010675D1 (en) 1989-12-06 1990-12-06 1,4-DISUBSTITUTED 2,6-DIFLUORBENZENE COMPOUNDS AND LIQUID CRYSTALLINE MEDIUM
BR909007097A BR9007097A (en) 1989-12-06 1990-12-06 2,6-DIFLUORBENZENE 1,4-DISSUBSTITUTED COMPOUNDS AND LIQUID CRYSTALLINE MEDIA
KR1019910700836A KR0184869B1 (en) 1989-12-06 1990-12-06 1,4-disubstituted 2,6-difluorobenzene compound and liquid crystal medium
EP91900202A EP0462237B1 (en) 1989-12-06 1990-12-06 1,2-disubstituted 2,6-difluorobenzene compounds and liquid crystal media
DE4092096A DE4092096C1 (en) 1989-12-06 1990-12-06 1,4-disubstituted 2,6-difluorobenzene compounds and liquid-crystalline medium
JP3500951A JP2935746B2 (en) 1989-12-06 1990-12-06 1,4-disubstituted 2,6-difluorobenzene compound and liquid crystal phase
FI913726A FI913726A7 (en) 1989-12-06 1990-12-06 1,4-disubstituted 2,6-difluorobenzene compounds and liquid crystalline medium
DE90EP9002109D DE4092096D2 (en) 1989-12-06 1990-12-06 1,4-disubstituierte 2,6-difluorbenzolverbindungen und fluessigkristallines medium
NO91913036A NO913036L (en) 1989-12-06 1991-08-05 1,4-DISUBSTITUTED 2,6-DIFLUOROBENZENE COMPOUNDS AND LIQUID CRYSTALLINE MEDIUM.
US08/917,167 US6200654B1 (en) 1989-12-06 1997-08-25 1,4-disubstituted 2,6-difluorobenzene compounds, and a liquid-crystalline medium

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
DE3940343 1989-12-06
DEP3940343.2 1989-12-06
DEP3941881.2 1989-12-12
DE3941881 1989-12-19
DEP4000535.6 1990-01-10
DEP4000534.8 1990-01-10
DE4000534A DE4000534C2 (en) 1989-12-19 1990-01-10 1,4-disubstituted 2,6-difluorobenzene compounds and liquid-crystalline medium
DE4000535A DE4000535B4 (en) 1989-12-06 1990-01-10 1,4-disubstituted 2,6-difluorobenzene compounds and liquid-crystalline medium

Publications (2)

Publication Number Publication Date
WO1991008184A2 WO1991008184A2 (en) 1991-06-13
WO1991008184A3 true WO1991008184A3 (en) 1992-09-17

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PCT/EP1990/002109 WO1991008184A2 (en) 1989-12-06 1990-12-06 1,2-disubstituted 2,6-difluorobenzene compounds and liquid crystal media

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EP (1) EP0462237B1 (en)
JP (1) JP2935746B2 (en)
AU (1) AU6900391A (en)
BR (1) BR9007097A (en)
CA (1) CA2046590A1 (en)
DE (1) DE4092096C1 (en)
WO (1) WO1991008184A2 (en)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59108431D1 (en) * 1990-04-13 1997-02-06 Merck Patent Gmbh LIQUID CRYSTAL MEDIUM
GB2257701A (en) * 1991-07-04 1993-01-20 Merck Patent Gmbh 1,4 - disubstituted 2,6 - difluorfobenzene compounds
US5520846A (en) * 1991-07-16 1996-05-28 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid-crystalline medium
DE4123539A1 (en) * 1991-07-16 1993-01-21 Merck Patent Gmbh LIQUID CRYSTAL MEDIUM
DE4220082C2 (en) * 1992-06-19 1994-09-15 Merck Patent Gmbh Process for the cross-coupling of boronic acids with halogen compounds
DE4239169A1 (en) * 1992-11-21 1994-05-26 Merck Patent Gmbh Cyclobutane - benzene derivatives
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JPH06504032A (en) 1994-05-12
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