WO1990013611A3 - Optically active compounds and liquid crystal phase - Google Patents

Optically active compounds and liquid crystal phase Download PDF

Info

Publication number
WO1990013611A3
WO1990013611A3 PCT/EP1990/000679 EP9000679W WO9013611A3 WO 1990013611 A3 WO1990013611 A3 WO 1990013611A3 EP 9000679 W EP9000679 W EP 9000679W WO 9013611 A3 WO9013611 A3 WO 9013611A3
Authority
WO
WIPO (PCT)
Prior art keywords
residue
diyl
liquid crystal
optically active
active compounds
Prior art date
Application number
PCT/EP1990/000679
Other languages
German (de)
French (fr)
Other versions
WO1990013611A2 (en
Inventor
Andreas Waechtler
Thomas Geelhaar
Reinhard Hittich
Ekkehard Bartmann
Joachim Krause
Eike Poetsch
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 DE3915698A external-priority patent/DE3915698A1/en
Priority claimed from DE3920571A external-priority patent/DE3920571A1/en
Priority claimed from DE3922307A external-priority patent/DE3922307A1/en
Priority claimed from DE3922308A external-priority patent/DE3922308A1/en
Priority claimed from DE3922416A external-priority patent/DE3922416A1/en
Priority claimed from DE3923324A external-priority patent/DE3923324A1/en
Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh
Priority to DE59008760T priority Critical patent/DE59008760D1/en
Priority to EP90915943A priority patent/EP0428720B1/en
Publication of WO1990013611A2 publication Critical patent/WO1990013611A2/en
Publication of WO1990013611A3 publication Critical patent/WO1990013611A3/en

Links

Classifications

    • 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
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed 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
    • 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
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • 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
    • 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
    • C07D239/28—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • 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
    • C09K19/34—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
    • C09K19/3463—Pyrimidine with a carbon chain containing at least one asymmetric carbon atom, i.e. optically active pyrimidines
    • 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
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur 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
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
    • C09K19/3497—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom the heterocyclic ring containing sulfur and nitrogen atoms
    • 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
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/58—Dopants or charge transfer agents
    • C09K19/586—Optically active dopants; chiral dopants
    • C09K19/588—Heterocyclic compounds
    • 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

Abstract

The invention relates to optically active compounds of formula (I) in which R denotes an alkyl or alkenyl residue with up to 15 carbon atoms which is unsubstituted or substituted once by -CN or substituted at least once with fluorine or chlorine, whereby a CH2 group in this residue can be replaced by -O-, -CO-, -O-CO-, -CO-O- or -O-CO-O-, A?1 and A2¿ independently of each other denote an unsubstituted 1,4-phenylene residue, pyridine-2,5-diyl residue, pyrimidin-2,5-diyl residue, pyrazin-2,5-diyl residue, pyridazin-3,6-diyl residue, 1,3,4-thiadiazol-2,5-diyl residue, 1,2,4-thiadiazol-3,5-diyl residue, trans-1,4-cyclohexylene residue or one of said residues substituted by one or two fluorine atoms, where one or two non-neighbouring CH¿2? groups can be replaced by -O- and/or -S- and/or a CH group, Z?1, Z2 and Z3¿ independently of each other denote -CO-O-, -O-CO-, -CH¿2?O-, -OCH2, -CH2CH2-, -CH=CH-, -C=C- or a single bond, Q?1¿ denotes -CH¿2?CH2-, -CH2CH2CH2-, -OCH2-, -CH2OCH2-, -OCH2CH2-, -O-CO-, -CO-OCH2-, Q?2¿ denotes -O-, -O-CO-, -(CH¿2?)3-O- or a single bond, m = 0, 1, 2 or 3, n = 0 or 1 and o is a number between 1 and 9. Also described is their use as components of liquid crystal phases.
PCT/EP1990/000679 1989-05-11 1990-05-10 Optically active compounds and liquid crystal phase WO1990013611A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE59008760T DE59008760D1 (en) 1989-05-11 1990-05-10 OPTICALLY ACTIVE CONNECTIONS AND LIQUID CRYSTALLINE PHASE.
EP90915943A EP0428720B1 (en) 1989-05-11 1990-05-10 Optically active compounds and liquid crystal phase

Applications Claiming Priority (14)

Application Number Priority Date Filing Date Title
DEP3915378.9 1989-05-11
DE3915378 1989-05-11
DE3915698A DE3915698A1 (en) 1989-05-13 1989-05-13 Novel fluorine-contg. phenylene cyclohexylene optically active cpds. - useful as components of chiral smectic liq. crystals
DEP3915698.2 1989-05-13
DEP3920571.1 1989-06-23
DE3920571A DE3920571A1 (en) 1989-06-23 1989-06-23 New optically active cpds. with fluoro-substd. asymmetrical carbon
DEP3922308.6 1989-07-07
DE3922307A DE3922307A1 (en) 1989-07-07 1989-07-07 New optically active cpds. with fluoro-substd. asymmetrical carbon
DE3922308A DE3922308A1 (en) 1989-07-07 1989-07-07 New optically active cpds. with fluoro-substd. asymmetrical carbon
DEP3922307.8 1989-07-07
DEP3922416.3 1989-07-07
DE3922416A DE3922416A1 (en) 1989-07-07 1989-07-07 New optically active cpds. with fluoro-substd. asymmetrical carbon
DE3923324A DE3923324A1 (en) 1989-05-11 1989-07-14 New optically active cpds. with fluoro-substd. asymmetrical carbon
DEP3923324.3 1989-07-14

Publications (2)

Publication Number Publication Date
WO1990013611A2 WO1990013611A2 (en) 1990-11-15
WO1990013611A3 true WO1990013611A3 (en) 1990-12-27

Family

ID=27561518

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1990/000679 WO1990013611A2 (en) 1989-05-11 1990-05-10 Optically active compounds and liquid crystal phase

Country Status (4)

Country Link
EP (1) EP0428720B1 (en)
JP (1) JPH04500079A (en)
DE (1) DE59008760D1 (en)
WO (1) WO1990013611A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2901717B2 (en) * 1990-07-31 1999-06-07 高砂香料工業株式会社 Fluorine-containing optically active compound and liquid crystal composition containing the compound
JP3095927B2 (en) * 1993-02-10 2000-10-10 キヤノン株式会社 Optically active compound, liquid crystal composition containing the same, method of using the same, liquid crystal element and display device using the same
GB2316077B (en) * 1995-03-28 1999-09-08 Secr Defence Pyrimidine Compounds
GB9506309D0 (en) * 1995-03-28 1995-05-17 Secr Defence Pyrimidine compounds
US6121448A (en) * 1995-03-28 2000-09-19 The Secretary Of State For Defence In Her Brittanic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland Pyrimidine compounds

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0237007A2 (en) * 1986-03-10 1987-09-16 Canon Kabushiki Kaisha Fluoroalkane derivative and liquid crystal composition
EP0278665A2 (en) * 1987-02-02 1988-08-17 Chisso Corporation 2-Substituted-alkyl ether and liquid crystal composition
EP0289270A1 (en) * 1987-04-27 1988-11-02 Chisso Corporation Optically active 2-biphenylpyrimidine derivatives and liquid crystal compositions containing them

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0629259B2 (en) * 1987-03-31 1994-04-20 キヤノン株式会社 Liquid crystalline compound and liquid crystal composition containing the same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0237007A2 (en) * 1986-03-10 1987-09-16 Canon Kabushiki Kaisha Fluoroalkane derivative and liquid crystal composition
EP0278665A2 (en) * 1987-02-02 1988-08-17 Chisso Corporation 2-Substituted-alkyl ether and liquid crystal composition
EP0289270A1 (en) * 1987-04-27 1988-11-02 Chisso Corporation Optically active 2-biphenylpyrimidine derivatives and liquid crystal compositions containing them

Also Published As

Publication number Publication date
WO1990013611A2 (en) 1990-11-15
JPH04500079A (en) 1992-01-09
EP0428720A1 (en) 1991-05-29
EP0428720B1 (en) 1995-03-22
DE59008760D1 (en) 1995-04-27

Similar Documents

Publication Publication Date Title
DE3476207D1 (en) Thienothiophene derivatives
AU3188889A (en) Derivatives of 2,3-difluorohydroquinone
JP2001081466A5 (en)
HK27194A (en) Trifluorobenzene derivatives and liquid crystal compositions containing the same
KR880700044A (en) Smectic liquid crystal phase
KR960701848A (en) Novel compounds for use in liquid gorystal compositions
ATE188959T1 (en) FLUOROBENZENE DERIVATIVES AND LIQUID CRYSTALLINE MEDIUM
ATE60603T1 (en) CHIRAL ARYL-2,3-EPOXYALKYL ETHERS AND THEIR CORRESPONDING THIIUM COMPOUNDS AND THEIR USE AS DOPANTS IN LIQUID CRYSTAL PHASES.
KR900003180A (en) Organosilylalkyl or organosilylalkenyl compounds, preparation method thereof and use of liquid crystal mixture
EP1081123A3 (en) 2,3-Difluorophenyl derivative having negative dielectric anisotropy, liquid crystal composition, and liquid crystal display device
KR940005587A (en) 6-membered ring-containing meta-substituted aromatic compounds for use in liquid crystal mixtures
KR930010017A (en) Compounds for Use in Liquid Crystal Mixtures
DE59109263D1 (en) 2-fluoropyridines, process for their preparation and their use in liquid crystal mixtures
KR880006345A (en) Liquid crystal mixture
WO1990013611A3 (en) Optically active compounds and liquid crystal phase
KR940005573A (en) 3-fluoropyridine, preparation method thereof and use thereof in liquid crystal mixture
ATE108445T1 (en) HETEROCYCLIC DERIVATIVES OF 1,2-DIFLUOROBENZENE.
EP0328330A3 (en) Ferroelectric liquid crystal composition
WO1991009026A3 (en) Phenyldioxanes
EP0284008A3 (en) Use of derivatives of 5-phenyl pyrimidine as components of smectic liquid-crystalline mixtures
KR940011410A (en) Conjugated Enine Derivatives and Liquid Crystal Compositions
KR890700121A (en) Chiral or Achiral Ring Compounds
EP0308794A3 (en) Liquid crystal phenyl pyrimidine ester of cyclohexane-carboxylic acid with a smectic phase, process for its preparation and its use in liquid crystal mixtures
KR900701722A (en) Fluorinated biphenyldiol derivatives
KR920006479A (en) Use of 4-fluoropyrimidine derivatives as ferroelectric liquid crystal mixture components

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): JP US

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): AT BE CH DE DK ES FR GB IT LU NL SE

WWE Wipo information: entry into national phase

Ref document number: 1990915943

Country of ref document: EP

AK Designated states

Kind code of ref document: A3

Designated state(s): JP US

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): AT BE CH DE DK ES FR GB IT LU NL SE

WWP Wipo information: published in national office

Ref document number: 1990915943

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 1990915943

Country of ref document: EP