[go: up one dir, main page]

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

Info

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
Authority
WO
WIPO (PCT)
Prior art keywords
residue
independently
atoms
residues
diyl
Prior art date
Application number
PCT/EP1990/002109
Other languages
German (de)
French (fr)
Other versions
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
Original Assignee
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
Publication date
Priority claimed from DE4000535A external-priority patent/DE4000535B4/en
Priority claimed from DE4000534A external-priority patent/DE4000534C2/en
Priority to JP3500951A priority Critical patent/JP2935746B2/en
Priority to EP91900202A priority patent/EP0462237B1/en
Priority to DE90EP9002109D priority patent/DE4092096D2/en
Priority to KR1019910700836A priority patent/KR0184869B1/en
Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh
Priority to FI913726A priority patent/FI913726A7/en
Priority to DE59010675T priority patent/DE59010675D1/en
Priority to BR909007097A priority patent/BR9007097A/en
Priority to DE4092096A priority patent/DE4092096C1/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

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/16—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon double bonds, e.g. stilbenes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
    • C09K19/3458—Uncondensed pyrimidines
    • C09K19/3469—Pyrimidine with a specific end-group other than alkyl, alkoxy or -C*-
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
    • C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3021—Cy-Ph-Ph-Cy

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Crystal Substances (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

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
DE4092096A DE4092096C1 (en) 1989-12-06 1990-12-06 1,4-disubstituted 2,6-difluorobenzene 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
EP91900202A EP0462237B1 (en) 1989-12-06 1990-12-06 1,2-disubstituted 2,6-difluorobenzene compounds and liquid crystal media
DE90EP9002109D DE4092096D2 (en) 1989-12-06 1990-12-06 1,4-disubstituierte 2,6-difluorbenzolverbindungen und fluessigkristallines medium
KR1019910700836A KR0184869B1 (en) 1989-12-06 1990-12-06 1,4-disubstituted 2,6-difluorobenzene compound and liquid crystal 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
DE59010675T DE59010675D1 (en) 1989-12-06 1990-12-06 1,4-DISUBSTITUTED 2,6-DIFLUORBENZENE COMPOUNDS AND LIQUID CRYSTALLINE 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
DEP3940343.2 1989-12-06
DE3940343 1989-12-06
DEP3941881.2 1989-12-12
DE3941881 1989-12-19
DEP4000535.6 1990-01-10
DEP4000534.8 1990-01-10
DE4000535A DE4000535B4 (en) 1989-12-06 1990-01-10 1,4-disubstituted 2,6-difluorobenzene compounds and liquid-crystalline medium
DE4000534A DE4000534C2 (en) 1989-12-19 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

Family

ID=27434806

Family Applications (1)

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

Country Status (7)

Country Link
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
WO1991016392A1 (en) * 1990-04-13 1991-10-31 MERCK Patent Gesellschaft mit beschränkter Haftung Liquid crystalline medium
GB2257701A (en) * 1991-07-04 1993-01-20 Merck Patent Gmbh 1,4 - disubstituted 2,6 - difluorfobenzene compounds
DE4123539A1 (en) * 1991-07-16 1993-01-21 Merck Patent Gmbh LIQUID CRYSTAL MEDIUM
US5520846A (en) * 1991-07-16 1996-05-28 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid-crystalline 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
DE4414874A1 (en) * 1993-05-10 1994-11-17 Merck Patent Gmbh Benzene derivatives, and liquid-crystalline medium
DE59508281D1 (en) * 1994-08-06 2000-06-08 Merck Patent Gmbh BENZENE DERIVATIVES AND LIQUID CRYSTAL MEDIUM
US6013198A (en) * 1995-09-11 2000-01-11 Chisso Corporation Liquid crystalline compound replaced by fluorine containing group, liquid crystal composition, and liquid crystal display device
US5948318A (en) * 1995-09-11 1999-09-07 Chisso Corporation Liquid crystal composition and liquid crystal display device
EP0922021A1 (en) 1996-08-21 1999-06-16 Chisso Corporation Difluorophenyl derivative compound, liquid crystal composition and liquid crystal display device
JP4526605B2 (en) * 1996-08-28 2010-08-18 チッソ株式会社 Tetracyclic compound having lateral halogen substituent and liquid crystal composition
JP2961650B2 (en) * 1996-09-25 1999-10-12 チッソ株式会社 Substituted benzene derivative, liquid crystal composition and liquid crystal display device
US6579577B2 (en) 1996-09-25 2003-06-17 Chisso Corporation Substituted benzene derivative, liquid crystal composition, and liquid crystal display element
JP2903493B2 (en) * 1996-09-25 1999-06-07 チッソ株式会社 Terphenyl derivative, liquid crystal composition and liquid crystal display device
AU5191798A (en) 1996-11-28 1998-06-22 Chisso Corporation Fluorine-substituted benzene derivatives, liquid-crystal composition, and liquid-crystal display element
DE69909436T2 (en) * 1999-05-19 2004-04-15 Merck Patent Gmbh Isothione cyanate tolanes and liquid-crystalline mixtures containing them
KR100745543B1 (en) 2000-08-31 2007-08-03 다이니뽄 잉끼 가가꾸 고오교오 가부시끼가이샤 Liquid crystal display
DE10145780B4 (en) 2001-09-17 2012-10-04 Merck Patent Gmbh Fluorinated cyclopenta [a] naphthalenes and their use in liquid crystal mixtures and displays
TWI403573B (en) * 2005-02-25 2013-08-01 Merck Patent Gmbh Liquid-crystalline medium
JP4972889B2 (en) 2005-07-22 2012-07-11 Ｊｎｃ株式会社 Liquid crystal composition and liquid crystal display element
JP5422898B2 (en) * 2007-03-08 2014-02-19 Ｊｎｃ株式会社 Novel compound having 2,2,2-bicyclooctane bonded to halogenated alkyl group and liquid crystal composition using the same
KR101451205B1 (en) 2011-05-26 2014-10-15 디아이씨 가부시끼가이샤 Compound having 2-fluorophenyloxymethane structure
TWI518062B (en) 2011-12-26 2016-01-21 迪愛生股份有限公司 Compound having 2-fluorophenyloxymethane structure
US9181484B2 (en) 2012-05-15 2015-11-10 Dic Corporation Compound having 2-fluorophenyloxymethane structure
WO2015012156A1 (en) 2013-07-25 2015-01-29 Dic株式会社 Liquid crystalline compound having 2,6-difluorophenyl ether structure and liquid crystal composition thereof
JP5776864B1 (en) 2013-08-30 2015-09-09 Dic株式会社 Nematic liquid crystal composition
US9573923B2 (en) 2013-10-03 2017-02-21 Dic Corporation Liquid crystal compound having 2, 6-difluorophenylether structure, and liquid crystal composition containing the same
US10000700B2 (en) 2014-07-31 2018-06-19 Dic Corporation Nematic liquid crystal composition
WO2016017615A1 (en) 2014-07-31 2016-02-04 Dic株式会社 Nematic liquid crystal composition

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0090183A1 (en) * 1982-03-13 1983-10-05 MERCK PATENT GmbH Polyhalogenated aromatic compounds
EP0117631A1 (en) * 1983-01-26 1984-09-05 The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Disubstituted ethanes and their use in liquid crystal materials and devices
WO1989002425A1 (en) * 1987-09-09 1989-03-23 MERCK Patent Gesellschaft mit beschränkter Haftung Fluorinated oligophenyls and their use in liquid crystal materials
WO1989008687A1 (en) * 1988-03-10 1989-09-21 MERCK Patent Gesellschaft mit beschränkter Haftung 2,3-difluorobiphenyls

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3117152A1 (en) * 1981-04-30 1982-11-18 Merck Patent Gmbh, 6100 Darmstadt "FLUORINE 4,4'-BIS (CYCLOHEXYL) BIPHENYL DERIVATIVES, THESE DIELECTRICS AND ELECTRO-OPTICAL DISPLAY ELEMENT"
JPH0730007B2 (en) * 1985-07-23 1995-04-05 旭硝子株式会社 Difluorocyano compound and liquid crystal composition containing the same
JPH0830054B2 (en) * 1987-03-06 1996-03-27 セイミケミカル株式会社 Difluorocyanophenyl cyclohexane compound and liquid crystal composition containing the same
JPH0684339B2 (en) * 1987-11-16 1994-10-26 チッソ株式会社 Cyclohexane derivative
EP0317175B1 (en) * 1987-11-17 1993-09-22 Seiko Epson Corporation Pyrimidine derivatives
JP2696557B2 (en) * 1989-03-07 1998-01-14 チッソ株式会社 Trifluorobenzene derivative
DE4027315A1 (en) * 1989-08-30 1991-03-07 Merck Patent Gmbh HALOGENATED BENZENE DERIVATIVES AND LIQUID CRYSTALLINE MEDIUM
DE59006700D1 (en) * 1989-09-05 1994-09-08 Merck Patent Gmbh DIFLUORBON ZONITRILE AND LIQUID CRYSTALLINE MEDIUM.
ATE188959T1 (en) * 1989-09-06 2000-02-15 Merck Patent Gmbh FLUOROBENZENE DERIVATIVES AND LIQUID CRYSTALLINE MEDIUM
JP2745072B2 (en) * 1989-10-16 1998-04-28 チッソ株式会社 Difluorobenzonitrile derivative

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0090183A1 (en) * 1982-03-13 1983-10-05 MERCK PATENT GmbH Polyhalogenated aromatic compounds
EP0117631A1 (en) * 1983-01-26 1984-09-05 The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Disubstituted ethanes and their use in liquid crystal materials and devices
WO1989002425A1 (en) * 1987-09-09 1989-03-23 MERCK Patent Gesellschaft mit beschränkter Haftung Fluorinated oligophenyls and their use in liquid crystal materials
WO1989008687A1 (en) * 1988-03-10 1989-09-21 MERCK Patent Gesellschaft mit beschränkter Haftung 2,3-difluorobiphenyls

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Band 107, Nr. 20, 16. November 1987, Seite 793, Zusammenfassung Nr. 187655k, (Columbus, Ohio, US), & JP,A,62103057 (ASAHI GLASS CO., LTD) 13. Mai 1987, siehe Zusammenfassung *
CHEMICAL ABSTRACTS, Band 110, Nr. 14, 3. April 1989, Seite 760, Zusammenfassung Nr. 125648p, (Columbus, Ohio, US), & JP,A,63216858 (SEIMI CHEMICAL CO., LTD) 9. September 1988, siehe Zusammenfassung *
MOLECULAR CRYSTALS AND LIQUID CRYSTALS, Band 172, Juli 1989, (Chur, CH), G.W. GRAY et al.: "The synthesis and transition temperatures of some fluoro-substituted 4-cyanophenyl and 4-cyanobiphenyl-4'-yl 4-pentyl- and 4-butoxy-benzoates", Seiten 165-189, siehe Seite 170, Tabelle I; Seite 174, Tabelle II *

Also Published As

Publication number Publication date
AU6900391A (en) 1991-06-26
JPH06504032A (en) 1994-05-12
JP2935746B2 (en) 1999-08-16
EP0462237A1 (en) 1991-12-27
WO1991008184A2 (en) 1991-06-13
EP0462237B1 (en) 1997-03-12
DE4092096C1 (en) 2001-03-15
BR9007097A (en) 1992-02-18
CA2046590A1 (en) 1991-06-07

Similar Documents

Publication Publication Date Title
WO1991008184A3 (en) 1,2-disubstituted 2,6-difluorobenzene compounds and liquid crystal media
KR100215373B1 (en) Fluorobenzene derivatives and liquid-crystalline medium
TWI405841B (en) Nematic liquid crystal composition and liquid crystal display element using the same
US7651630B2 (en) Difluorobenzene derivative and nematic liquid crystal composition using the same
KR907001958A (en) Difluoromethyl compound
TWI560260B (en) Liquid-crystalline medium
CA2381007A1 (en) Fused ring compound
JP4947342B2 (en) Difluorobenzene derivative and liquid crystal composition using the same
KR930701564A (en) Vinyl Compound and Liquid Crystal Medium
US4830470A (en) Liquid crystalline esters
KR890701555A (en) Aryl-sulfur pentafluoride
KR900700572A (en) Smetic liquid crystal medium
JP2006233182A (en) Nematic liquid crystal composition and liquid crystal display device using the same
KR940005587A (en) 6-membered ring-containing meta-substituted aromatic compounds for use in liquid crystal mixtures
HK19396A (en) Ferroelectric liquid crystals
KR940005573A (en) 3-fluoropyridine, preparation method thereof and use thereof in liquid crystal mixture
KR0170363B1 (en) Alkoxymethylcyclohexane, alkenyloxymethylcyclohexane and preparation method thereof
KR950702612A (en) Benzene Derivatives and Liquid Crystal Medium (BENZENE DERIVATIVES, AND LIQUID-CRYSTALLINE MEDIUM)
AU2002213922A1 (en) Liquid crystalline medium
JP5077621B2 (en) Difluorobenzene derivative and liquid crystal composition using the same
KR920701098A (en) 1,4-disubstituted 2,6-difluorobenzene compound and liquid crystal medium
US5032312A (en) 3E-cyclohexylalkoxy derivatives
JP2006206887A (en) Liquid crystal composition
JPWO2005095311A1 (en) Benzene derivative, liquid crystal composition, and liquid crystal display device
JP2006206888A (en) Liquid crystal composition

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AT AU BB BG BR CA CH DE DK ES FI GB HU JP KP KR LK LU MC MG MW NL NO RO SD SE SU US

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): AT BE BF BJ CF CG CH CM DE DK ES FR GA GB GR IT LU ML MR NL SE SN TD TG

CFP Corrected version of a pamphlet front page
CR1 Correction of entry in section i

Free format text: IN PAT.BUL.13/91, UNDER INID (54) TITLE REPLACE THE EXISTING TEXT BY "1,4-DISUBSTITUTED 2,6-DIFLUOROBENZENE COMPOUNDS AND LIQUID CRYSTAL MEDIA"

WWE Wipo information: entry into national phase

Ref document number: 1991900202

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2046590

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 913726

Country of ref document: FI

Ref document number: KR

WWP Wipo information: published in national office

Ref document number: 1991900202

Country of ref document: EP

REF Corresponds to

Ref document number: 4092096

Country of ref document: DE

Date of ref document: 19920130

WWE Wipo information: entry into national phase

Ref document number: 4092096

Country of ref document: DE

AK Designated states

Kind code of ref document: A3

Designated state(s): AT AU BB BG BR CA CH DE DK ES FI GB HU JP KP KR LK LU MC MG MW NL NO RO SD SE SU US

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): AT BE BF BJ CF CG CH CM DE DK ES FR GA GB GR IT LU ML MR NL SE SN TD TG

WWG Wipo information: grant in national office

Ref document number: 1991900202

Country of ref document: EP