+

WO1991008184A3 - Composes de 2,6-difluorobenzol 1,4-disubstitues et milieux a cristaux liquides - Google Patents

Composes de 2,6-difluorobenzol 1,4-disubstitues et milieux a cristaux liquides 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)
English (en)
Other versions
WO1991008184A2 (fr
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 DE4000534A external-priority patent/DE4000534C2/de
Priority claimed from DE4000535A external-priority patent/DE4000535B4/de
Priority to JP3500951A priority Critical patent/JP2935746B2/ja
Priority to KR1019910700836A priority patent/KR0184869B1/ko
Priority to EP91900202A priority patent/EP0462237B1/fr
Priority to DE4092096A priority patent/DE4092096C1/de
Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh
Priority to FI913726A priority patent/FI913726A7/fi
Priority to DE90EP9002109D priority patent/DE4092096D2/de
Priority to BR909007097A priority patent/BR9007097A/pt
Priority to DE59010675T priority patent/DE59010675D1/de
Publication of WO1991008184A2 publication Critical patent/WO1991008184A2/fr
Priority to NO91913036A priority patent/NO913036L/no
Publication of WO1991008184A3 publication Critical patent/WO1991008184A3/fr
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

Des composés de 2,6-difluorobenzol 1,4-disubstitués ont la formule (I), dans laquelle R est un résidu alkyle ou alkényle non substitué ou au moins à substitution simple par un halogène, ayant entre 1 et 15 atomes de carbone, alors que dans ces résidus un ou plusieurs groupes CH2 peuvent être indépendamment substitués par -O-, -S-, des liaisons des types (α) ou (β), du -CO-, -CO-O-, -O-CO- ou -O-CO-O-, de telle sorte que les atomes d'O ne soient pas directement liés les uns aux autres; A1 et A2 représentent indépendamment l'un de l'autre: (a) un résidu trans-1,4-cyclohexylène, dans lequel un ou plusieurs groupes CH¿2? non adjacents peuvent être également remplacés par -O- et/ou -S-; (b) un résidu 1,4-phénylène, dans lequel un ou deux groupes CH peuvent également être remplacés par N; (c) un résidu sélectionné dans le groupe formé de 1,4-cyclohexénylène, 1,4-bicyclo(2,2,2)-octylène, pipéridin'1,4-diyl, naphtalin'2,6-diyl, décahydronaphtalin-2,6-diyl et 1,2,3,4-tétrahydronaphtalin-2,6diyl, alors que les résidus (a) et (b) peuvent être remplacés par CN ou substitués de manière simple ou double par du fluor; Z?1 et Z2¿ représentent indépendamment l'un de l'autre -CO-O-, -O-CO-, -CH¿2?O-, -OCH2-, -CH2CH2-, -CH=CH-, -C=C- ou une liaison simple; m et n sont égaux à 0, 1, 2 ou 3, indépendamment l'un de l'autre, (m+n) étant égal à 1, 2 ou 3; et X a une des notations de R ou représente F, Cl, -CF3, OCF3-, -OCF2H, -OC2F5, -CN ou -NCS, à condition qu'au moins un des résidus Z1 et Z?2¿ contenus dans la molécule représente -CO-O-, -O-CO-, -CH¿2?-O-, -OCH2-, -CH2CH2-, -CH=CH- ou -C=C- et/ou au moins un des résidus A?1 et A2¿ contenus dans la molécule représente un des groupes (γ) ou (δ), et/ou n soit égal à 1 ou 2, alors que dans le cas où -(Z2-A2)n est égal au groupe (ε), X représente F, Cl, -CF3, -OCF3, -OCF2H, -OC2F5, -CN ou -NCS. Ces composés sont utiles comme composants de milieux à cristaux liquides.
PCT/EP1990/002109 1989-12-06 1990-12-06 Composes de 2,6-difluorobenzol 1,4-disubstitues et milieux a cristaux liquides WO1991008184A2 (fr)

Priority Applications (10)

Application Number Priority Date Filing Date Title
DE59010675T DE59010675D1 (de) 1989-12-06 1990-12-06 1,4-disubstituierte 2,6-difluorbenzolverbindungen und flüssigkristallines medium
BR909007097A BR9007097A (pt) 1989-12-06 1990-12-06 Compostos de 2,6-difluorbenzeno 1,4-dissubstituidos e meio cristalino liquido
KR1019910700836A KR0184869B1 (ko) 1989-12-06 1990-12-06 1,4-이치환된 2,6-디플루오로벤젠 화합물 및 액정 매질
EP91900202A EP0462237B1 (fr) 1989-12-06 1990-12-06 Composes de 2,6-difluorobenzol 1,4-disubstitues et milieux a cristaux liquides
DE4092096A DE4092096C1 (de) 1989-12-06 1990-12-06 1,4-Disubstituierte 2,6-Difluorbenzolverbindungen und flüssigkristallines Medium
JP3500951A JP2935746B2 (ja) 1989-12-06 1990-12-06 １，４―ジ置換２，６―ジフルオロベンゼン化合物、および液晶相
FI913726A FI913726A7 (fi) 1989-12-06 1990-12-06 1,4-disubstituoituja 2,6-difluoribentseeniyhdisteitä ja nestekiteinen väliaine
DE90EP9002109D DE4092096D2 (en) 1989-12-06 1990-12-06 1,4-disubstituierte 2,6-difluorbenzolverbindungen und fluessigkristallines medium
NO91913036A NO913036L (no) 1989-12-06 1991-08-05 1,4-disubstituerte 2,6-difluorbenzenforbindelser og flytendekrystallinsk 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 (de) 1989-12-19 1990-01-10 1,4-Disubstituierte 2,6-Difluorbenzolverbindungen und flüssigkristallines Medium
DE4000535A DE4000535B4 (de) 1989-12-06 1990-01-10 1,4-Disubstituierte 2,6-Difluorbenzolverbindungen und flüssigkristallines Medium

Publications (2)

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

Family

ID=27434806

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1990/002109 WO1991008184A2 (fr) 1989-12-06 1990-12-06 Composes de 2,6-difluorobenzol 1,4-disubstitues et milieux a cristaux liquides

Country Status (7)

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

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59108431D1 (de) * 1990-04-13 1997-02-06 Merck Patent Gmbh Flüssigkristallines 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 (de) * 1991-07-16 1993-01-21 Merck Patent Gmbh Fluessigkristallines medium
DE4220082C2 (de) * 1992-06-19 1994-09-15 Merck Patent Gmbh Verfahren zur Kreuzkopplung von Boronsäuren mit Halogenverbindungen
DE4239169A1 (de) * 1992-11-21 1994-05-26 Merck Patent Gmbh Cyclobutan - Benzol - Derivate
DE4414874A1 (de) * 1993-05-10 1994-11-17 Merck Patent Gmbh Benzolderivate und flüssigkristallines Medium
JP4090073B2 (ja) * 1994-08-06 2008-05-28 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング ベンゼン誘導体及び液晶媒体
US6117360A (en) * 1995-09-11 2000-09-12 Chisso Corporation Liquid crystal composition and liquid crystal display device
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
CN1227536A (zh) 1996-08-21 1999-09-01 智索公司 二氟苯基衍生物,液晶组合物和液晶显示装置
JP4526605B2 (ja) 1996-08-28 2010-08-18 チッソ株式会社 ラテラルハロゲン置換基を有する４環化合物および液晶組成物
JP2961650B2 (ja) * 1996-09-25 1999-10-12 チッソ株式会社 置換ベンゼン誘導体、液晶組成物および液晶表示素子
JP2903493B2 (ja) * 1996-09-25 1999-06-07 チッソ株式会社 テルフェニル誘導体、液晶組成物および液晶表示素子
US6579577B2 (en) 1996-09-25 2003-06-17 Chisso Corporation Substituted benzene derivative, liquid crystal composition, and liquid crystal display element
WO1998023564A1 (fr) 1996-11-28 1998-06-04 Chisso Corporation Derives de benzene a substitution de fluor, composition a cristaux liquides et element d'affichage a cristaux liquides
EP1054001B1 (fr) * 1999-05-19 2003-07-09 MERCK PATENT GmbH Tolanes d'isothiocyanate et mélanges de cristaux liquides les contenant
KR100745543B1 (ko) 2000-08-31 2007-08-03 다이니뽄 잉끼 가가꾸 고오교오 가부시끼가이샤 액정 표시 소자
DE10145780B4 (de) 2001-09-17 2012-10-04 Merck Patent Gmbh Fluorierte Cyclopenta[a]naphthaline und ihre Verwendung in Flüssigkristallmischungen und Displays
JP5154758B2 (ja) * 2005-02-25 2013-02-27 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 液晶媒体
JP4972889B2 (ja) 2005-07-22 2012-07-11 Ｊｎｃ株式会社 液晶組成物および液晶表示素子
JP5422898B2 (ja) * 2007-03-08 2014-02-19 Ｊｎｃ株式会社 ハロゲン化アルキル基と結合した２，２，２−ビシクロオクタンを有する新規な化合物およびこれを用いた液晶組成物
JP5263461B2 (ja) 2011-05-26 2013-08-14 Ｄｉｃ株式会社 ２−フルオロフェニルオキシメタン構造を持つ化合物
TWI518062B (zh) 2011-12-26 2016-01-21 迪愛生股份有限公司 具有２－氟苯基氧基甲烷構造之化合物
KR101488315B1 (ko) * 2012-05-15 2015-01-30 디아이씨 가부시끼가이샤 2-플루오로페닐옥시메탄 구조를 가지는 화합물
US9637466B2 (en) 2013-07-25 2017-05-02 Dic Corporation Liquid crystal compound having 2, 6-difluorophenyl ether structure and liquid crystal composition thereof
WO2015029876A1 (fr) 2013-08-30 2015-03-05 Dic株式会社 Composition de cristaux liquides nématiques
KR101649180B1 (ko) 2013-10-03 2016-08-19 디아이씨 가부시끼가이샤 2,6-디플루오로페닐에테르 구조를 갖는 액정성 화합물 및 그 액정 조성물
JP5910800B1 (ja) 2014-07-31 2016-04-27 Dic株式会社 ネマチック液晶組成物
WO2016017615A1 (fr) 2014-07-31 2016-02-04 Dic株式会社 Composition à cristaux liquides nématiques

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0090183A1 (fr) * 1982-03-13 1983-10-05 MERCK PATENT GmbH Composés aromatiques polyhalogénés
EP0117631A1 (fr) * 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 Ethanes disubstitués et leur emploi dans des matériaux et dispositifs à cristaux liquides
WO1989002425A1 (fr) * 1987-09-09 1989-03-23 MERCK Patent Gesellschaft mit beschränkter Haftung Oligophenyles fluores et leur emploi dans des materiaux a cristaux liquides
WO1989008687A1 (fr) * 1988-03-10 1989-09-21 MERCK Patent Gesellschaft mit beschränkter Haftung Difluoro-2,3 biphenyles

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3117152A1 (de) * 1981-04-30 1982-11-18 Merck Patent Gmbh, 6100 Darmstadt "fluorhaltige 4,4'-bis-(cyclohexyl)-biphenylderivate, diese enthaltende dielektrika und elektrooptisches anzeigeelement"
JPH0730007B2 (ja) * 1985-07-23 1995-04-05 旭硝子株式会社 ジフルオロシアノ化合物及びそれを含有する液晶組成物
JPH0830054B2 (ja) * 1987-03-06 1996-03-27 セイミケミカル株式会社 ジフルオロシアノフエニルシクロヘキサン系化合物及びそれを含有する液晶組成物
JPH0684339B2 (ja) * 1987-11-16 1994-10-26 チッソ株式会社 シクロヘキサン誘導体
DE3884347T2 (de) * 1987-11-17 1994-04-28 Seiko Epson Corp Pyrimidinderivate.
JP2696557B2 (ja) * 1989-03-07 1998-01-14 チッソ株式会社 トリフルオロベンゼン誘導体
DE4027315A1 (de) * 1989-08-30 1991-03-07 Merck Patent Gmbh Halogenierte benzolderivate und fluessigkristallines medium
DE59006700D1 (de) * 1989-09-05 1994-09-08 Merck Patent Gmbh Difluorbenzonitrile und flüssigkristallines medium.
ATE188959T1 (de) * 1989-09-06 2000-02-15 Merck Patent Gmbh Fluorbenzolderivate und flüssigkristallines medium
JP2745072B2 (ja) * 1989-10-16 1998-04-28 チッソ株式会社 ジフルオロベンゾニトリル誘導体

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0090183A1 (fr) * 1982-03-13 1983-10-05 MERCK PATENT GmbH Composés aromatiques polyhalogénés
EP0117631A1 (fr) * 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 Ethanes disubstitués et leur emploi dans des matériaux et dispositifs à cristaux liquides
WO1989002425A1 (fr) * 1987-09-09 1989-03-23 MERCK Patent Gesellschaft mit beschränkter Haftung Oligophenyles fluores et leur emploi dans des materiaux a cristaux liquides
WO1989008687A1 (fr) * 1988-03-10 1989-09-21 MERCK Patent Gesellschaft mit beschränkter Haftung Difluoro-2,3 biphenyles

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

Similar Documents

Publication Publication Date Title
WO1991008184A3 (fr) Composes de 2,6-difluorobenzol 1,4-disubstitues et milieux a cristaux liquides
KR100215373B1 (ko) 플루오로벤젠유도체및액정매질
TWI405841B (zh) 向列液晶組成物及使用它之液晶顯示元件
US7651630B2 (en) Difluorobenzene derivative and nematic liquid crystal composition using the same
KR907001958A (ko) 디플루오로메틸 화합물
CA2381007A1 (fr) Compose de cycles accoles
JP4947342B2 (ja) ジフルオロベンゼン誘導体及びこれを用いた液晶組成物
KR930701564A (ko) 비닐 화합물 및 액정 매질
KR19980702976A (ko) 전기-광학적 액정 디스플레이
KR890701555A (ko) 아릴-황 펜타플루오라이드
JP4947339B2 (ja) ネマチック液晶組成物及びこれを用いた液晶表示素子
KR900700572A (ko) 스메틱 액정매체
KR20070118093A (ko) 디플루오로벤젠 유도체 및 이를 사용한 네마틱 액정 조성물
KR940005587A (ko) 액정 혼합물에 사용하기 위한 6원 환 함유 메타 치환된 방향족 화합물
EP0377516A3 (fr) Composés liquides cristallins à haute anisotropie optique
KR0170363B1 (ko) 알콕시메틸사이클로헥산, 알케닐옥시메틸사이클로헥산 및 이들의 제조방법
JP5488514B2 (ja) ベンゼン誘導体、液晶組成物および液晶表示素子
KR950702612A (ko) 벤젠 유도체 및 액정 매질(benzene derivatives, and liquid-crystalline medium)
KR920702849A (ko) 부분적으로 플루오르화된 화합물
AU2002213922A1 (en) Liquid crystalline medium
JP5077621B2 (ja) ジフルオロベンゼン誘導体及びこれを用いた液晶組成物
KR890700121A (ko) 키랄 또는 아키랄 링 화합물
US5032312A (en) 3E-cyclohexylalkoxy derivatives
JP2006206887A (ja) 液晶組成物
KR0177584B1 (ko) 알콕시메틸사이클로헥산 및 알케닐옥시메틸사이클로헥산을함유하는 액정 혼합물 및 액정 셀

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

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载