NO872039L - Nitrogenholdige heterocykliske forbindelser. - Google Patents

Nitrogenholdige heterocykliske forbindelser.

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Publication number
NO872039L
NO872039L NO872039A NO872039A NO872039L NO 872039 L NO872039 L NO 872039L NO 872039 A NO872039 A NO 872039A NO 872039 A NO872039 A NO 872039A NO 872039 L NO872039 L NO 872039L
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Prior art keywords
cyano
cis
cyclohexane
phenyl
ester
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NO872039A
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English (en)
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NO872039D0 (no
Inventor
Andreas Waechtler
Rudolf Eidenschink
Joachim Krause
Bernhard Scheuble
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Merck Patent Gmbh
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Publication of NO872039D0 publication Critical patent/NO872039D0/no
Publication of NO872039L publication Critical patent/NO872039L/no

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    • 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
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    • 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
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    • 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
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
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    • C09K19/00—Liquid crystal materials
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
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    • C09K19/00—Liquid crystal materials
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    • 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
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    • C09K19/00—Liquid crystal materials
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    • 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
    • C09K19/3452—Pyrazine
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C09K19/3455—Pyridazine
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
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    • 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
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
    • C09K2019/325—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a tetrahydronaphthalene, e.g. -2,6-diyl (tetralin)
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    • 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
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
    • C09K2019/326—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a decahydronaphthalene, e.g. -2,6-diyl (decalin)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Liquid Crystal Substances (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

Foreliggende oppfinnelse angår nitrogenholdige, heterocykliske forbindelser av formel II
hvori
1 2
R og R betegner en alkylgruppe med 1 til 15 C-atomer,
hvori også én eller flere CE^-grupper kan være erstattet med en gruppering valgt fra gruppen -0-, -S-, -CO-, -0-CO-, -0-COO-, -CO-0-, -CH=CH-, -CH-halogen og -CHCN-, eller også av en kombinasjon av to egnede grupperinger, hvorved to heteroatomer ikke direkte er forbundet med hverandre,
m er 0 eller 1,
Ar betegner 1,4-fenylen, 4,4'-bifenylyl eller 2,6-nafthylen,
hvorved én eller flere CH-grupper kan være erstattet med
N,
Z betegner -CO-0-, -0-CO-, -CH20-, -OCH2~, -CH2CH2-,
-CH2CHCN-, -CHCNCH2-, -CH=CH eller en enkeltbinding, og A betegner usubstituert eller i 1- eller 4-stilling CN-sub-
stituert 1,4-cyclohexylen,
med det forbehold at i det tilfellet A = usubstituert 1,4-cyclohexylen, betegner Z -CHCNCH„- eller -CH-CHCN-, og/eller
12
i det minste en CH2-gruppe i mxnst en av restene R og R er erstattet med -CHCN-,
deres anvendelse som komponenter av smektiske, flytende-krystallinske faser, såvel som smektiske, flytendekrystallinske faser, i særdeleshet chirale, skråttstilte, smektiske faser inneholdende forbindelsene av formel I.
Chirale, skråttstilte, smektiske, flytendekrystallinske
faser med ferroelektriske egenskaper kan fremstilles ved at basisblandinger med én eller flere skråttstilte, smektiske faser tilsettes et egnet, chiralt dopestoff (L.A. Beresnev et al., Mol. Cryst. Liq. Cryst. 8_9, 327 (1982);
H.R. Brand et al., J. Physique 4_4, (lett.), L-771 (1983).
Slike faser kan benyttes som dielektrika for hurtig omkoblede displayer som er basert på det av Clark og Lagerwall- be-skrevne prinsipp for SSFLC-teknologi (N.A. Clark og S.T. Lagerwall, Appl. Phys. Lett. 36.'899 (1980); USP 4 367 924) på grunn-lag av de ferroelektriske egenskaper til den chiralt skråttstilte fase. I denne fase er de langstrakte molekyler anordnet i skikt, idet molekylene oppviser en skråstillings- eller vippevinkel i forhold til skiktnormalen. Ved fremadskridende bevegelse fra skikt til skikt endres skråstillingsretningen med en liten vinkel i forhold til en loddrett, på skiktene stående akse slik at det utvikler seg en helix- eller skrue-linjestruktur. I displayer som er basert på prinsippet for SSFLC-teknologi, er de smektiske skikt anordnet loddrett på cellens plater. Den skruelinjelignende anordning av molekylenes skråstillingsretninger undertrykkes på grunn av en meget liten avstand mellom platene (ca. 1-2 um). Derved tvinges molekylenes lengdeakser til å anordne seg i et plan parallelt med cellens plater slik at det oppstår to utmerkede skråstill-ingsorienteringer. Ved hjelp av påtrykning av et passende, elektrisk vekselfelt kan det i den flytende-krystallinske fase som oppviser en spontan polarisasjon, koples frem og tilbake mellom disse tilstander. Dette koplingsforløp er vesentlig raskere enn ved tradisjonelle, skrudde celler (TN-LCD-enheter) som er basert på nematiske flytende krystaller.
En stor ulempe for flere anvendelser av de nåværende tilgjengelige materialer med chiralt skråstilte, smektiske faser (slik som f.eks. Sc<*>) er at den dielektriske anisotropi-verdi er større enn null, eller så fremt den er negativ, bare utviser en verdi som er litt forskjellig fra null. Negativ verdi for den dielektriske anisotropi er nødvendig såfremt den nødvendige planare orientering bevirkes ved overlagring av styrefeltet med et AC-holdefelt med liten amplitude
(J.M. Geary, SID-Tagung, Orlando/Florida, april/mai 1985, foredrag 8.3). Anvendelse av materialer med sterk negativ dielektrisk anisoptropi fører for det meste til en sterk ned-settelse av spontanpolarisasjonen og/eller ugunstige verdier for helningsvinkelen (pitch) og/eller skråstillingen (tilt).
Enn videre innsnevres for det meste temperaturområdet for
de ferroelektriske faser på ugunstig måte.
Det er nå funnet at anvendelse av forbindelsene av formel II som komponenter av chirale, skråttstilte, smektiske blandinger kan redusere de omtalte ulemper vesentlig. Forbindelsene av formel II er således ypperlig egnet som komponenter av chirale, skråttstilte, smektiske, flytende-krystallinske faser. I særdeleshet kan det med deres hjelp fremstilles kjemisk særlig stabile, chirale, skråttstilte, smektiske, flytende-krystallinske faser med gunstig ferroelektrisk faseområde, i særdeleshet med bredt Sc<*>faseområde, negativ dielektrisk anisotropi, gunstig pitchhøyde og høye verdier for den spontane polarisasjon for slike faser. P er den spontane
2
polarisasjon i nC/cm .
Forbindelsene av formel II utviser et bredt anvend-elsesområde. Avhengig av valget av substituentene kan disse forbindelser tjene som basismaterialer av hvilke flytende-krystallinske, smektiske faser i overveiende grad er sammen-satt av, men forbindelsene av formel II kan imidlertid også tilsettes flytende-krystallinske basismaterialer av andre for-bindelsesklasser for eksempelvis å variere den dielektriske og/eller optiske anisotropi og/eller viskositeten og/eller den spontane polarisasjon og/eller faseområde og/eller skrå-stillingsvinkel og/eller hellingsvinkel av et slikt dielektrikum. Gjenstand for oppfinnelsen er således forbindelsene av formel II såvel som deres anvendelse som komponenter (chirale, skråttstilte) smektiske, flytende-krystallinske faser. Gjenstand for oppfinnelsen er enn videre smektiske, flytende-krystallinske faser, i særdeleshet chirale, skråttstilte, smektiske faser, med et innhold av minst én forbindelse av formel II, såvel som flytende-krystallinske tegnelementer, i særdeleshet elektrooptiske tegnelementer som inneholder slike faser.
Forbindelsene av formel II kan ha rettkjedede eller forgrenede vingegrupper R 1 og/eller R 2. Forbindelser med forgrenede vingegrupper kan anvendes i form av racematet eller som optisk aktive forbindelser. Achirale basisblandinger fra forbindelsene av formel II og eventuelt ytterligere achirale komponenter kan dopes med chirale forbindelser av formel II eller også med andre chirale forbindelser for å oppnå chirale, skråttstilte, smektiske faser.
Forbindelsene av formel II inneholder fortrinnsvis en gruppe av formel (A)
eller dens speilbilde i den angitte konfigurasjon med aksial nitrilgruppe og trans-stilling av substituenten. I forbindelsene av de foregående og etterfølgende formler betegner R 1 og R 2 fortrinnsvis R-, R-0-, R-0-CO-, R-O-COO- eller R-CO-0. R er fortrinnsvis en alkylgruppe med fortrinnsvis 5 til 12 C-atomer hvori også en eller to ikke endestående CB^-grupper kan være erstattet med -0-, -0-CO-, -CHCN-, -CH-halogen, -CHCH3"0-, -CHhalogen-COO-, -CHCN-COO-og/eller -CH=CH-. R betegner eksempelvis fortrinnsvis pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl eller dodecyl, men også methyl, ethyl, propyl, butyl, 2-, 3- eller 4-oxapentyl, 2-, 3-, 4- eller 5-oxahexyl, 2-, 3-, 4-, 5-eller 6-oxaheptyl, 2-, 3-, 4-, 5-, 6- eller 7-oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- eller 8-oxanonyl, 2-, 3-, 4-, 5-, 6-, 7-, 8- eller 9-oxadecyl, 1,3-dioxabuty1 (= methoxymethoxy), 1,3-, 1,4- eller 2,4-dioxapentyl, 1,3-, 1,4-, 1,5-, 2,4-, 2,5-eller 3,5-dioxahexy1, 1,3-, 1,4-, 1,5-, 1,6-, 2,4-, 2,5-, 2,6-, 3,5-, 3,6- eller 4,6-dioxahepty1, 1,4-dioxaocty1, 1,4,7-trioxaoctyl, 1,4-dioxanony1, 1,4-dioxadecyl.
Forbindelsene av formel II såvel som de foregående og etterfølgende delformler med forgrenede vingegrupper R"<*>" hhv. R 2 kan leilighetsvis på grunn av en bedre løselighet i de vanlige flytende-krystallinske basismaterialer være av betyd-ning, i særdeleshet imidlertid som chirale dopestoffer for chirale, skråttstilte, smektiske faser, når de er optisk aktive. Slike forbindelser egner seg imidlertid også som komponenter av nematiske flytende-krystallinske faser, i sær deleshet for å nedsette motsatt dreining. Forgrenede grupper av denne type inneholder som regel en eller to kjedeforgren-inger. Fortrinnsvis er det asymmetriske carbonatom forbundet med to forskjellige substituerte C-atomer, et H-atom og en substituent valgt fra gruppen halogen (i særdeleshet F, Cl eller Br), alkyl eller alkoxy med 1-5 C-atomer og CN. Den
1 2 optisk aktive organiske rest R hhv. R har fortrinnsvis formelen
hvori
X betegner -CO-0-, -0-CO-, -0-CO-O-, -CO-, -0-, -S-, -CH=CH-,
-CH=CH-C00- eller en enkeltbinding,
Q betegner alkylen med 1 til 5 C-atomer, hvori også en ikke med X forbundet Cl^-gruppe kan være erstattet med -0-, -CO-,
-0-CO-, -CO-0- eller -CH=CH-, eller en enkeltbinding,
Y betegner CN, halogen, methyl eller methoxy, og
R betegner en fra Y forskjellig alkylgruppe med 1 til 18 C-atomer, hvori også en eller to ikke-tilstøtende Cf^-grupper kan være erstattet med -0-, -CO-, -0-CO-, -CO-0- og/eller
-CH=CH-.
X er fortrinnsvis -CO-0-, -0-CO-, -CH=CH-C00- (trans) eller en enkeltbinding. Særlig foretrukket er -CO-0- og -0-C0-.
Q er fortrinnsvis - CU.^-, -Cf^Cf^- eller en enkeltbinding, og særlig foretrukket en enkeltbinding.
Y er fortrinnsvis CH^, -CN eller Cl, i særdeleshet -CN.
R er fortrinnsvis rettkjedet alkyl med 1 til 10, i særdeleshet 1 til 7, C-atomer.
Foretrukne, forgrenede rester er isopropyl, 2-butyl
(= 1-methylpropyl), isobutyl (= 2-methylpropyl, isobutyl (= 2-methylpropyl), 2-methylbutyl, isopentyl {- 3-methylbutyl), 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, 2-octyl, isopropoxy, 2-methylpropoxy, 2-methylbutoxy, 3-methylbutoxy, 2-methylpentoxy, 3-methylpentoxy,
2-ethylhexoxy, 1-methylhexoxy, 1-methylheptoxy, 2-oxa-3-methylbutyl, 3-oxa-4-methylpenty1, 2-octyloxy, 2-klorpro-pionyloxy, 2-klor-3-methylbutyryloxy, 2-klor-4-methylvalery1-oxy, 2-klor-3-methylvaleryloxy, 2-methyl-3-oxa-pentyl, 2-methy1-3-oxa-hexyl.
Z er fortrinnsvis -CO-0-, -0-CO-, -CH20-, -0-CH2~,
-CH2CH2~eller en enkeltbinding. A er fortrinnsvis i 1- eller 4-stilling med CN-substituert 1,4-cyclohexylen, og særlig foretrukket er Z-A-R<2>, en gruppe av formel
R 2er fortrinnsvis rettkjedet alkyl eller forgrenet alkyl, hvori en eller to CH2~grupper kan være erstattet med -CHCH^-, med fortrinnsvis 2 til 10 C-atomer. Såfremt A betegner usubstituert 1,4-cyclohexylen (fortrinnsvis trans-1,4-cyclohexylen), er Z fortrinnsvis -CH2~CHCN- eller R 2er i særdeleshet en alkylgruppe med 2 til 15 C-atomer, hvori en CH„-gruppe er erstattet med -CHCN-. I dette tilfelle er R 2 fortri.nnsvis en gruppe av formel -(CH^ „) p-CHCN-alkyl, hvori p er 0, 1 eller 2 og alkyl er en rettkjedet alkylgruppe med (14-p) C-atomer.
Blant forbindelsene av formel II såvel som de foregående og etterfølgende delformler er slike foretrukne hvori minst én av de deri inneholdte rester har en av de angitte foretrukne betydninger.
Forbindelsene av formel II utviser en høy kjemisk sta-bilitet. De er fargeløse og godt blandbare med alle anvend-bare flytende krystaller. Deres anvendelse i flytende-krystallinske faser fører til bredere mesofaseområde og for-bedrede verdier for spontanpolarisasjon i chirale, skråttstilte, smektiske faser. Fasene ifølge oppfinnelsen egner seg således meget godt til flytende-krystallinske faser for displayer som beror på prinsippet for SSFLC-teknologi. Enn videre egner de seg imidlertid også for andre elektrooptiske tegnanordninger slik som f.eks. TN-celler eller Guest-Host-celler. Her tjener de ved siden av utvidelsen av mesofaseområdet, i særdeleshet til innstilling av negative verdier for den dielektriske anisotropi, og for forbedring av de elastiske konstanter.
Ar er fortrinnsvis en gruppe av formel a til j:
Gruppene av formel a, b, c, e, f, gogher foretrukne. Særlig foretrukket er e og f.
Forbindelsene av formel II kan eksempelvis erholdes ved omsetning av de tilsvarende cyclohexancarbonitriler (formel II, R 2=H) med et halogenid av formel R 2-halogen.
Nitrilet overføres hensiktsmessig først med en sterk base slik som NaH, NaNE^, lithiumdiisopropylamid, -piperidid eller -2,5-diisopropylpiperidid eller K-tert.-butylat i det tilsvarende carbanion, fortrinnsvis i et inert løsningsmiddel, eksempelvis et hydrocarbon slik som toluen, en ether slik som THF eller dioxan, et amid slik som DMF, et sulfoxyd slik som dimethylsulfoxyd eller en blanding av slike løsningsmidler. Etter tilsetning av R 2-halogen opprettholdes reaksjonsblandingen hensiktsmessig i 1/2 til 16 timer ved temperaturer mellom 0 og 150°C.
Halogenidene kan eksempelvis erholdes fra de tilsvarende alkoholer. Halogen er fortrinnsvis brom eller jod.
Fasene ifølge oppfinnelsen inneholder fortrinnsvis minst tre, i særdeleshet minst fem forbindelser av -formel II. Særlig foretrukket er chirale, skråttstilte, smektiske, flytende-krystallinske faser ifølge oppfinnelsen hvis achirale basisblanding ved siden av forbindelsene av formel II minst inneholder én annen komponent med negativ eller forholdsvis mindre positiv dielektrisk anisotropi. Disse ytterligere komponenter av den chirale basisblanding kan utgjøre 1 til 50%, fortrinnsvis 10 til 25% av basisblandingen. Som ytterligere komponenter med forholdsvis mindre positiv eller negativ dielektrisk anisotropi egner seg forbindelser av delformel Va til Vp:
Fasene ifølge oppfinnelsen inneholder fortrinnsvis minst tre, i særdeleshet minst fem forbindelser av -formel II. Særlig foretrukket er chirale, skråttstilte, smektiske, flytende-krystallinske faser ifølge oppfinnelsen hvis achirale basisblanding ved siden av forbindelsene av formel II minst inneholder én annen komponent med negativ eller forholdsvis mindre positiv dielektrisk anisotropi. Disse ytterligere komponenter av den chirale basisblanding kan utgjøre 1 til 50%, fortrinnsvis 10 til 25% av basisblandingen. Som ytterligere komponenter med forholdsvis mindre positiv eller negativ dielektrisk anisotropi egner seg forbindelser av delformel Va til Vp:
4 5
R og R er fortrinnsvis rettkjedet alkyl, alkoxy, alkanoyloxy eller alkoxycarbony1 med 3 til 12 C-atomer.
X er fortrinnsvis 0. n er 0 eller 1.
Særlig foretrukket er forbindelsene av delformel Va,
4 5
Vb, Vd og Vf, hvori R og R betegner rettkjedet alkyl eller alkoxy med 5 til 10 C-atomer.
Forbindelsene av delformel Vc, Vh og Vi egner seg som tilsetning for smeltepunktnedsettelse og tilsettes normalt basisblandingene i ikke mer enn 5%, fortrinnsvis 1 til 3%.
4 5
R og R betegner i forbindelsene av delformel Vc, Vh og Vi fortrinnsvis rettkjedet alkyl med 2 til 7, fortrinnsvis 3 til 5, C-atomer. En ytterligere forbindelsesklasse som er egnet for smeltepunktnedsettelse i fasene ifølge oppfinnelsen, er slike av formel
hvori R 4 og R 5 har de for Vc, Vh og Vi angitte foretrukne betydninger .
Som ytterligere komponenter med negativ dielektrisk anisotropi egner seg enn videre forbindelser inneholdende strukturelementet B eller C.
Foretrukne forbindelser av denne type tilsvarer formel VIb og VIc:
R' og R' ' betegner fortrinnsvis rettkjedede alkyl- eller 1 2
alkoxygrupper med 2 til 10 C-atomer. Q og Q betegner 1,4-fenylen, trans-1,4-cyclohexylen, 4,4<1->bifenylyl, 4-(trans-4-cyclohexyl)-fenyl, trans,trans-4,4<1->bicyclohexyl eller en av
1 2
gruppene Q og Q kan også betegne en enkeltbinding.
Q 3 og Q 4 betegner 1,4-fenylen, 4,4<1->bifenylyl eller
trans-1,4-cyclohexylen. En av gruppene Q 3 og Q 4 kan også betegne 1,4-fenylen hvori minst én CH-gruppe er erstattet med N. R''' er en optisk aktiv rest med et asymmetrisk carbonatom av
struktur
eller Særlig foretrukne forbindelser av formel VIc er slike av formel VIc<1>:
hvori A betegner 1,4-fenylen eller trans-1,4-cyclohexylen, og n er 0 eller 1.
Fremstilling av fasene ifølge oppfinnelsen skjer på i og for seg kjent måte. Generelt oppløses komponentene i hverandre, hensiktsmessig ved forhøyet temperatur.
Gjennom egnede tilsetninger kan de flytende-krystallinske faser ifølge oppfinnelsen modifiseres slik at de kan anvendes i alle tidligere kjente, foreliggende typer av flytende-krystallinske tegnelementer.
De etterfølgende eksempler illustrerer oppfinnelsen uten å begrense denne. I det foregående og det etterfølgende betegner prosentangivelser vektprosent; alle temperaturer er angitt i grader Celsius. Enn videre betyr: K: krystallin-fast tilstand, S: smektisk fase (indekset kjennetegner fase-typen), N: nematisk tilstand, Ch: cholestrisk fase, I: iso-trop fase. Tallene mellom to symboler angir omvandlingstemp-eraturen i grader Celsius. "Vanlig opparbeidelse" betyr: vann tilsettes, det ekstraheres med methylenklorid, separeres, den organiske fase tørkes, inndampes, og produktet renses ved krystallisasjon og/eller kromatografi.
Eksempel 1
Til 10,1 g diisopropylamin i 70 m THF ble under fuktighetsutelukkelse og nitrogenatmosfære ved -10°C suksessivt dråpevis tilsatt 62,5 ml av en 1,6 m løsning av N-butyllithium i hexan og 36,1 g trans-4-[5-(p-n-heptylfenyl)-2-pyrimidinyl]-cyclohexancarbonitril (EP-OS 00 14 885) i 50 ml THF. Reaksjonsblandingen ble deretter omrørt ved -10°C i 20 minutter.
16,6 g 1-brompentan ble deretter tilsatt, og reaksjonsblandingen ble omrørt i 20 minutter ved romtemperatur. Reaksjonsblandingen ble opparbeidet på vanlig måte, og produktet ble renset ved kromatografi og krystallisasjon. Det ble erholdt r-l-cyan-l-n-pentyl-cis-4-[5-(p-n-heptylfenyl)-2-pyrimidinyl]-cyclohexan.
Analogt ble fremstilt: r-1-cyan-1-propyl-cis-4-[5-(p-heptylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-l-butyl-cis-4-[5-(p-heptylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-hexyl-cis-4-[5-(p-heptylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[5-(p-heptylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-l-octyl-cis-4-[5-(p-heptylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-l-nonyl-cis-4-[5-(p-heptylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-decyl-cis-4-[5-(p-heptylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-propyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-butyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-pentyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-hexyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-heptyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-l-nonyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-1-decyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-propyl-cis-4-[5-(p-nonylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-butyl-cis-4-[5-(p-nonylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-hexyl-cis-4-[5-(p-nonylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-heptyl-cis-4-[5-(p-nonylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[5-(p-nonylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-nonyl-cis-4-[5-(p-nonylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-decyl—cis-4-[5-(p-nonylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-propyl-cis-4-[5-(p-decylfeny1)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-butyl-cis-4-[5-(p-decylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-hexyl-cis-4-[5-(p-decylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-heptyl-cis-4-[5-(p-decylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[5-(p-decylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-nonyl-cis-4-[5-(p-decylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-l-decyl-cis-4-[5-(p-decylfenyl)-2-pyrimidinyl]-cyclohexan
Eksempel 2
Til en løsning av 4,6 g natrium i 150 ml methanol ble tilsatt 34,7 g p-(4-n-hexyl-4-cyanocyclohexyl)-benzamidin-hydroklorid og 20,4 g 2-n-pentyl-3-ethoxyacrolein (analogt med A. Villiger, A. Boller, M. Schadt, Z. Naturforsch. 34b, 1535, 1979), reaksjonsblandingen ble omrørt i 12 timer under nitrogenatmosfære, ble surgjort med 3N HC1 og ble opparbeidet på vanlig måte. Det ble erholdt r-l-cyan-l-hexyl-cis-4-[p-(5-n-pentylpyrimidinyl-2)-fenyl]-cyclohexan.
Analogt ble fremstilt: r-l-cyan-l-hexyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan, r-l-cyan-l-hexyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan, r-l-cyan-l-hexyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan, r-l-cyan-l-hexyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan, r-l-cyan-l-hexyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-1-cyan-1-pentyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-1-cyan-1-pentyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-decylpyrimidinyl-2)-feny1]-cyclohexan,
r-1-cyan-1-heptyl-cis-4-[p-(5-propylpyrimidinyl-2)-fenyl]-cyclohexan, smp. 94°, kp. 143°,
r-l-cyan-l-heptyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-1-cyan-1-heptyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan, smp. 101°, kp. 126°,
r-l-cyan-l-heptyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-1-cyan-1-octyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-1-cyan-1-octyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-1-cyan-1-decyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-1-cyan-1-decyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-decyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-decyl-cis-4-[p-(5-heptylpyrimidiny1-2)-fenyl]-cyclohexan,
r-l-cyan-l-decyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-decyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-decyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-penty l-cis-4- [ p- (5-butylpyrimidinyl-2) -f enyl ] - cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p- (5-pentylpyrimidinyl-2) -fenyl] - cyclohexan,
r-l-cyan-l-penty l-cis-4-[p- (5-hexylpyrimidinyl-2) -f enyl] - cyclohexan,
r-l-cyan-1- penty l-cis-4- [ p- (5-hepty lpyrimidinyl-2) -f enyl ] - cyclohexan,
r-1-cyan-1-penty 1-cis-4-[p- (5-oc ty lpyrimidinyl-2) - f enyl ] - cyclohexan,
r-1-cyan-1-penty l-cis-4-[p- (5-nony lpyrimidinyl-2) - f enyl ] - cyclohexan,
r-1-cyan-1-penty l-cis-4-[ p- (5-decy lpyrimidinyl-2) - f enyl ] - cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-nonylpyrimidiny1-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidiny1-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidiny1-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidiny1-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidiny1-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidiny1-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl) - pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-decylcyclohexy1)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-.pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-hexylcyclohexy1)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-heptylcyclohexy1)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan.
Eksempel 3
Det ble fremstilt en flytende-krystallinsk fase bestående av
4% 2-p-heptyloxyfenyl-5-heptylpyrimidin,
30% 2-p-undecyloxyfenyl-5-hexylpyrimidin,
30% 2-p-nonyloxyfenyl-5-nonylpyrimidin,
12% r-l-cyan-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclo-hexan- 1-carboxyl sy repen ty lester ,
14% r-l-cyan-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclo-hexan-l-carboxylsyrebutylester og
10% p-(5-hexylpyrimidinyl-2)-fenyl-2-klorpropionat (optisk
aktiv).
Eksempel 4
Det ble fremstilt en flytende-krystallinsk fase bestående av
20% 4-(5-hexylpyrimidin-2-y1)-fenyl-(p-pentylbenzyl)-ether, 20% 4-(5-heptylpyrimidin-2-yl)-fenyl-(p-hexylbenzyl)-ether, 20% 4-(5-nonylpyrimidin-2-yl)-fenyl-(p-propylbenzy1)-ether,
5% 4-(5-nonylpyrimidin-2-yl)-fenyl-(p-cyanbenzyl)-ether,
10% r-l-cyan-cis-4-[p-(5-heptylpyrimidiny1-2)-fenyl]-cyclohexan-l-carboxylsyrebutylester,
15% r-l-cyan-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclo-hexan- 1-carboxyl sy repenty le ster og
10% p-(5-hexylpyrimidinyl-2)-fenyl-2-klorpropionat (optisk
aktiv).
Eksempel 5
En flytende-krystallinsk fase bestående av
3% 2-p-hexyloxyfenyl-5-heptylpyrimidin,
3% 2-p-heptyloxyfeny1-5-heptylpyrimidin,
3% 2-p-octyloxyfenyl-5-heptylpyrimidin,
3% 2-p-nonyloxyfeny1-5-heptylpyrimidin,
8% 2-p-hexyloxyfenyl-5-nonylpyrimidin,
25% 2-p-nonyloxyfenyl-5-nonylpyrimidin,
30% r-l-cyan-cis-4-(4<1->octyloxybifenyl-4-yl)-1-octyl-cyclohexan,
15% r-l-cyan-cis-4-(4<1->nonanoyloxybifenyl-4-yl)-1-butyl-cyclohexan og
10% r-l-cyan-cis-4-[p-(5-nonylpyrimidin-2-yl)-fenyl]-l-(2-methylbutyl)-cyclohexan (optisk aktiv)
har K -8° S<*>65° og sj og P = 8 nC/cm<2>ved 20°.
Eksempel 6
Det ble fremstilt en flytende-krystallinsk fase bestående av
3% 2-p-hexyloxyfeny1-5-heptylpyrimidin,
3% 2-p-heptyloxyfenyl-5-heptylpyrimidin,
3% 2-p-octyloxyfeny1-5-heptylpyrimidin,
3% 2-p-nonyloxyfeny1-5-heptylpyrimidin,
8% 2-p-hexyloxyfenyl-5-nonylpyrimidin,
25% 2-p-nonyloxyfenyl-5-nonylpyrimidin,
20% r-l-cyan-1-(trans-4-octylcyclohexyl-ethyl)-cis-4-(p-octyloxyfenyl)-cyclohexan,
10% r-l-cyan-1-(trans-4-octylcyclohexyl-ethyl)-cis-4-(p-heptyloxyfenyl)-cyclohexan,
10% r-l-cyan-1-(trans-4-octylcyclohexy1-ethyl)-cis-4-(p-octylfenyl)-cyclohexan,
5% r-l-cyan-1-(trans-4-octylcyclohexyl-ethyl)-cis-4-(p-heptylfenyl)-cyclohexan,
10% r-l-cyan-cis-4-[p-(5-octylpyrimidin-2-yl)-fenyl]-l-(2-methylbutyl)-cyclohexan (optisk aktiv).
Eksempel 7
En flytende-krystallinsk fase bestående av
3% 2-p-hexyloxyfeny1-5-heptylpyrimidin,
3% 2-p-heptyloxyfeny1-5-heptylpyrimidin,
3% 2-p-octyloxyfeny1-5-heptylpyrimidin,
3% 2-p-heptyloxyfeny1-5-heptylpyrimidin,
3% 2-p-octyloxyfenyl-5-heptylpyrimidin,
3% 2-p-nonyloxyfenyl-5-heptylpyrimidin,
8% 2-p-hexyloxyfeny1-5-nonylpyrimidin,
2 5% 2-p-nonyloxyfeny1-5-nonylpyrimidin,
30% r-l-cyan-cis-4-(4<1->octyloxybifenyl-4-yl)-1-octyl-cyclohexan,
15% r-l-cyan-cis-4-(4'-nonanoyloxybifenyl-4-yl)-1-buty1-cyclohexan og
10% r-l-cyan-cis-4-[p-(5-nonylpyrimidin-2-yl)-fenyl]-1-(2-methylbutyl)-cyclohexan (optisk aktiv)
har K -8° S<*>65° og S<*>og P = 8 nC/cm<2>ved 20°.
Eksempel 6
Det ble fremstilt en flytende-krystallinsk fase bestående av
3% 2-p-hexyloxyfeny1-5-heptylpyrimidin,
3% 2-p-heptyloxyfenyl-5-heptylpyrimidin,
3% 2-p-octyloxyfenyl-5-heptylpyrimidin,
3% 2-p-nonyloxyfenyl-5-heptylpyrimidin,
8% 2-p-hexyloxyfeny1-5-nonylpyrimidin,
25% 2-p-nonyloxyfeny1-5-nonylpyrimidin,
20% r-l-cyan-1-(trans-4-octylcyclohexyl-ethyl)-cis-4-(p-octyloxyfenyl)-cyclohexan,
10% r-l-cyan-1-(trans-4-octylcyclohexyl-ethyl)-cis-4-(p-heptyloxyfenyl)-cyclohexan,
10% r-l-cyan-1-(trans-4-octylcyclohexyl-ethyl)-cis-4-(p-octylfenyl)-cyclohexan,
5% r-l-cyan-1-(trans-4-octylcyclohexyl-ethyl)-cis-4-(p-heptylfenyl)-cyclohexan,
10% r-l-cyan-cis-4-[p-(5-octylpyrimidin-2-yl)-fenyl]-l-(2-methylbutyl)-cyclohexan (optisk aktiv).
Eksempel 7
En flytende-krystallinsk fase bestående av
3% 2-p-hexyloxyfeny1-5-heptylpyrimidin,
3% 2-p-heptyloxyfeny1-5-heptylpyrimidin,
3% 2-p-octyloxyfeny1-5-heptylpyrimidin,
3% 2-p-nonyloxyfeny1-5-heptylpyrimidin,
8% 2-p-hexyloxyfenyl-5-nonylpyrimidin,
25% 2-p-nonyloxyfeny1-5-nonylpyrimidin,
30% r-l-cyan-cis-4-[p-(p-octyloxybenzoyloxy)-fenyl]-1-octyl-cyclohexan,
15% r-l-cyan-cis-4-[p-(p-octyloxybenzoyloxy)-fenyl]-1-penty1-cyclohexan,
10% r-l-cyan-cis-4-[p-(5-nonyloxypyrimidin-2-yl)-fenyl]-l-(2-methylbutyl)-cyclohexan (optisk aktiv)
har K -10° S<*>61° S<*>og P = 10 nC/cm<2>ved 20°.
Eksempel 8
Det ble fremstilt en flytende-krystallinsk fase bestående av
3% 2-p-hexyloxyfeny1-5-heptylpyrimidin,
3% 2-p-heptyloxyfeny1-5-heptylpyrimidin,
3% 2-p-octyloxyfenyl-5-heptylpyrimidin,
3% 2-p-nonyloxyfeny1-5-heptylpyrimidin,
8% 2-p-hexyloxy f eny.l-5-nony lpyrimidin,
25% 2-p-nonyloxyfeny1-5-nonylpyrimidin,
15% l-cyan-l-trans-4-(p-heptyloxyfenyl)-cyclohexyl-2-(trans-4-octylcyclohexyl)-ethan,
15% l-cyan-l-trans-4-(p-octyloxyfenyl)-cyclohexyl-2-(trans-4-octylcyclohexyl)-ethan,
10% l-cyan-l-trans-4-(p-octylfenyl)-cyclohexyl-2-(trans-4-butylcyclohexyl)-ethan,
5% l-cyan-l-trans-4-(p-heptylfenyl)-cyclohexyl-2-(trans-4-butylcyclohexy1)-ethan og
10% r-l-cyan-cis-4-[p-(5-octylpyrimidin-2-yl)-fenyl]-1-(2-methylbutyl)-cyclohexan.
Eksempel 9
Det ble fremstilt en flytende-krystallinsk fase bestående av
3% 2-p-hexyloxyfenyl-5-heptylpyrimidin,
3% 2-p-heptyloxyfeny1-5-heptylpyrimidin,
3% 2-p-octyloxyfenyl-5-heptylpyrimidin,
3% 2-p-nonyloxyfenyl-5-heptylpyrimidin,
8% 2-p-hexyloxyfeny1-5-nonylpyrimidin,
25% 2-p-nonyloxyfeny1-5-nonylpyrimidin,
10% r-l-cyan-cis-4-(p-octyloxyfenyl)-1-octylcyclohexan,
10% r-l-cyan-cis-4-(4<1->octyloxycarbonylbifenyl-4-yl)-1-octyl-cyclohexan ,
5% r-l-cyan-cis-4-(p-heptyloxybenzoyloxy)-1-nonylcyclohexan, 10% r-l-cyan-cis-4-[p-(p-octylfenyl)-benzoyloxy]-1-butyl-cyclohexan,
5% r-l-cyan-cis-4-[p-(p-octyloxyfenyl)-benzoyloxy]-1-butyl-cyclohexan og
15% r-l-cyan-cis-4-[p-(5-nonylpyrimidin-2-yl)-fenoxycarbonyl]-1-(2-methylbutyl)-cyclohexan (optisk aktiv).
Eksempel 10
Til en blanding av 3,2 g 2-p-hydroxyfenyl-5-hexyl-pyrimidin, 3,15 g 4-cyan-4-heptylcyclohexancarboxylsyre (som kan erholdes fra 4-cyancyclohexancarboxylsyre ved omsetning med n-heptylbromid i nærvær av 2 ekvivalenter lithiumdiisopropylamid) og 150 mg 4-N,N'-dimethylaminopyridin i 150 ml diklormethan ble ved 5 - 10° og under fuktighetsutelukkelse tilsatt 2,8 g dicyclohexylcarbodiimid i 50 ml methylenklorid, blandingen ble omrørt en time ved romtemperatur, det utfelte ureaderivat ble fjernet, og filtratet ble opparbeidet på vanlig måte. Det ble erholdt r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-hexylpyrimidin-2-yl)-fenylester.
Analogt ble fremstilt: r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-propylpyrimidin-2-yl)-fenylester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-butylpyrimidin-2-yl)-fenylester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-pentylpyrimidin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-heptylpyrimidin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-octylpyrimidin-2-yl)-fenylester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-nonylpyrimidin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-decylpyrimidin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-propylpyrimidin-2-yl)-fenylester
r-l-cyan-l-octylcyclohexan-cis-4-carboxylsyre-p-(5-butylpyrimidin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-pentylpyrimidin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-hexylpyrimidin-2-yl)-fenylester
r-1-cyan-l-octylcyclohexan-cis-4-carboxylsyre-p-(5-heptylpyrimidin-2-yl)-fenylester
r-l-cyan-l-octylcyclohexan-cis-4-carboxylsyre-p-(5-octylpyrimidin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-nonylpyrimidin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-decylpyrimidin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-propylpyrimidin-2-y1)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-butylpyrimidin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-pentylpyrimidin-2-y1)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-hexylpyrimidin-2-yl)-fenylester
r-1-cyan-1-nonylcyclohexan-cis-4-carboxylsyre-p-(5-heptylpyrimidin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-octylpyrimidin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-nonylpyrimidin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-decylpyrimidin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-propylpyridin-2-yl)-fenylester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-butylpyridin-2-yl)-fenylester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-pentylpyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-hexylpyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-heptylpyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-octylpyridin-2-yl)-fenylester
r-1-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-nonylpyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-decylpyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-butoxypyridin-2-yl)-fenylester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-pentoxypyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-hexoxypyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-heptoxypyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-octoxypyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-nonoxypyridin-2-yl)-fenylester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-decoxypyridin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-propylpyridin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-butylpyridin-2-yl)-fenylester
r-l-cyan-l-octylcyclohexan-cis-4-carboxy1syre-p-(5-pentylpyridin-2-yl)-fenylester
r-l-cyan-l-octylcyclohexan-cis-4-carboxy1syre-p-(5-hexylpyridin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-heptylpyridin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxy1syre-p-(5-octylpyridin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxy1syre-p-(5-nonylpyridin-2-yl)-fenylester
r-1-cyan-l-octylcyclohexan-cis-4-carboxylsyre-p-(5-decylpyridin-2-yl)-fenylester
r-1-cyan-l-octylcyclohexan-cis-4-carboxylsyre-p-(5-butoxypyridin-2-yl)-fenylester r-l-cyan-l-octylcyclohexan-cis-4-carboxy1syre-p-(5-pentoxypyridin-2-yl)-fenylester
r-l-cyan-l-octylcyclohexan-cis-4-carboxylsyre-p-(5-hexoxypyridin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-heptoxypyridin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-octoxypyridin-2-yl)-fenylester
r-l-cyan-l-octylcyclohexan-cis-4-carboxylsyre-p-(5-nonoxypyridin-2-yl)-fenylester
r-l-cyan-l-octylcyclohexan-ci,s-4-carboxylsyre-p- (5-decoxypyridin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-propylpyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p- (5-butylpyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-pentylpyridin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-hexylpyridin-2-yl)-fenylester
r-1-cyån-1-nonylcyclohexan-cis-4-carboxylsyre-p-(5-heptylpyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-octylpyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-nonylpyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-decylpyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-butoxypyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-pentoxypyridin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-hexoxypyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-heptoxypyridin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-octoxypyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-nonoxypyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-decoxypyridin-2-yl)-fenylester
r-l-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-propylpyrimidin-2-yl)-fenylester
r-l-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-butylpyrimidin-2-yl)-fenylester
r-l-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-pentylpyrimidin-2-y1)-fenylester
r-l-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-hexylpyrimidin-2-yl)-fenylester
r-l-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-heptylpyrimidin-2-yl)-fenylester
r-l-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-octylpyrimidin-2-yl)-fenylester
r-1-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-nonylpyrimidin-2-yl)-fenylester
r-1-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-decylpyrimidin-2-yl)-fenylester
5-propyl-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-butyl-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-pentyl-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-hexyl-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-hepty1-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-octy1-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-nony1-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-decy1-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-butoxy-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-pentoxy-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-hexoxy-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-heptoxy-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-octoxy-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-nonoxy-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-decoxy-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-propy1-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-buty1-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-penty1-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-hexy1-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-hepty1-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-octy1-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-nonyl-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-decy1-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-butoxy-pyridin-5-carboxylsyre-(4-cyan-4-heptyl-cyclohexylester
2-pentoxy-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-hexoxy-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-heptoxy-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-octoxy-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-nonoxy-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-decoxy-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-propylpyridin-5-yl-ester
r-l-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-butylpyridin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-(2-pentylpyridin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-(2-hexylpyridin-5— yl-ester
r-l-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-heptylpyridin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-octylpyridin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-nonylpyridin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-decylpyridin-5-yl-ester
r-l-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-butoxypyridin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-(2-pentoxypyridin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-(2-hexoxypyridin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-(2-heptoxypyridin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-(2-octoxypyridin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-nonoxypyridin-5-yl-ester
r-1-cyan-1-hepty lcyclohexan-cis-4-carboxy lsyre-.( 2-decoxypyridin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-propylfenyl)-pyridazin-3-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-6-(p-buty1fenyl)-pyridazin-3-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-pentylfenyl)-pyridazin-3-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-hexylfenyl)-pyridazin-3-yl-ester
r-1-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-6-(p-heptylfenyl)-pyridazin-3-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-6-(p-octylfenyl)-pyridazin-3-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-6-(p-nonylfenyl)-pyridazin-3-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-decylfenyl)-pyridazin-3-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-6-(p-butoxyfenyl)-pyridazin-3-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-pentoxyfenyl)-pyridazin-3-yl-ester
r-l-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-hexoxyfenyl)-pyridazin-3-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-6-(p-heptoxyfenyl)-pyridazin-3-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-octoxyfenyl)-pyridazin-3-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-nonoxyfenyl)-pyridazin-3-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-6-(p-decoxyfenyl)-pyridazin-3-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-5-(p-propylfenyl)-pyrazin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-butylfenyl)-pyrazin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-pentylfenyl)-pyrazin-5-yl-ester
r-l-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-octylfenyl)-pyrazin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-nonylfenyl)-pyrazin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-5-(p-decylfenyl)-pyrazin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-butoxyfenyl)-pyrazin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-5-(p-pentoxyfenyl)-pyrazin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-5-(p-hexoxyfenyl)-pyrazin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-heptoxyfenyl)-pyrazin-5-yl-ester
r-l-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-octoxyfenyl)-pyrazin-5-y1-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-nonoxyfenyl)-pyrazin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-decoxyfenyl)-pyrazin-5-yl-ester
p-(5-propylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-butylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-pentylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-hexylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-heptylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-octylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-nonylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-decylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-butoxypyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-pentoxypyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-hexoxypyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-heptoxypyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-octoxypyrimidin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-nonoxypyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-decoxypyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-propylpyridin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-butylpyridin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-pentylpyridin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-hexylpyridin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-heptylpyridin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-octylpyridin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-nonylpyridin-2-y1)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-decylpyridin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-butoxypyridin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-pentoxypyridin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-hexoxypyridin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-heptoxypyridin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-octoxypyridin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-nonoxypyridin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-decoxypyridin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
Eksempel 11
En blanding av 61,2 g 2-p-hydroxyfeny1-5-heptyl-pyridin (som kan erholdes fra 2-p-methoxyfeny1-5-heptyl-pyridin ved basisk etherspaltning med kalium-tert.-butylat i N-methylpyrrolidon ved 150°), 35 g kaliumcarbonat og 85 g 4-cyan-4-heptylcyclohexylmethyljodid (som kan erholdes ved red-uksjon av 4-cyan-4-heptylcyclohexancarboxylsyreethylester med LiBH^, overføring av carbinolen i mesylat og omsetning med NaJ/aceton etter Finkelstein) i 500 ml dimethylformamid ble omrørt under nitrogenatmosfære ved 110° i 8 timer. Etter vanlig opparbeidelse ble det erholdt r-l-cyan-l-heptyl-cis-4-[p-(5-heptylpyridin-2-yl)-fenoxy-methyl]-cyclohexan.
Analogt ble fremstilt: r-l-cyan-l-octyl-cis-4-[p-(5-propylpyridin-2-y1)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-butylpyridin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-pentylpyridin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-hexylpyridin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-heptylpyridin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-octylpyridin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-nonylpyridin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-decylpyridin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-propylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-butylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-pentylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-hexylpyrimidin-2-y1)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-heptylpyrimidin-2-y1)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-octylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-nonylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-decylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-propylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-butylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-pentylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-hexylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-heptylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-octylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-nonylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-decylpyrimidin-2-yl) - fenoxymethyl]-cyclohexan

Claims (5)

1. Nitrogenholdige, heterocykliske forbindelser av formel II
hvori
1 2 R og R betegner en alkylgruppe med 1 til 15 C-atomer, hvori også én eller flere CF^-grupper kan være erstattet med en gruppering valgt fra gruppen -0-, -S-, -CO-, -0-CO-, -0-COO-, -CO-0-, -CH=CH -, -CH-halogen og -CHCN-, eller også av en kombinasjon av to egnede grupperinger, hvorved to heteroatomer ikke kan være direkte forbundet med hverandre, m er 0 eller 1, Ar betegner 1,4-fenylen, 4,4 <1-> bifenylyl eller 2,6-nafthylen, hvorved én eller flere CH-grupper kan være erstattet med N, Z betegner -CO-0-, -0-CO-, -CH2 0-, -0CH2 -, -CH2 CH2" , -CH2 CHCN-, -CHCNCH2 -, -CH=CH eller en enkeltbinding, og A betegner usubstituert eller i 1- eller 4-stilling CN-substituert 1,4-cyclohexylen, med det forbehold at i det tilfelle A = usubstituert 1,4-cyclohexylen, betegner Z -CHCNCH-- eller -CH„CHCN, og/eller 12.^ at i minst en av restene R og R er minst en CH2~ gruppe erstattet med -CHCN-.
2. Anvendelse av forbindelsene av formel II ifølge krav 1 som komponenter av smektiske, flytende-krystallinske faser.
3. Smektisk, flytende-krystallinsk fase med minst to flytende-krystallinske komponenter, karakterisert ved at den minst inneholder en forbindelse av formel II ifølge krav 1.
4. Fase ifølge krav 3, karakterisert ved at den inneholder minst én optisk aktiv forbindelse.
5. Elektrooptisk tegnelement, karakterisert ved at det som dielektrikum inneholder en fase ifølge krav 3 eller 4.
NO872039A 1985-09-18 1987-05-15 Nitrogenholdige heterocykliske forbindelser. NO872039L (no)

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US5002694A (en) 1991-03-26
KR870700610A (ko) 1987-12-30
NO872039D0 (no) 1987-05-15
EP0238576B1 (de) 1992-05-06
EP0238576A1 (de) 1987-09-30
WO1987001701A2 (en) 1987-03-26
JPS63500948A (ja) 1988-04-07
DE3685213D1 (de) 1992-06-11
DD252197A5 (de) 1987-12-09
DE3533333A1 (de) 1987-03-26
JPS63500945A (ja) 1988-04-07
JP2777885B2 (ja) 1998-07-23
WO1987001701A3 (fr) 1987-06-18
DD252196A5 (de) 1987-12-09

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