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DE3731638A1 - Liquid-crystalline phenylpyrimidine derivatives, process for their preparation, and their use in liquid-crystalline mixtures - Google Patents

Liquid-crystalline phenylpyrimidine derivatives, process for their preparation, and their use in liquid-crystalline mixtures

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Publication number
DE3731638A1
DE3731638A1 DE19873731638 DE3731638A DE3731638A1 DE 3731638 A1 DE3731638 A1 DE 3731638A1 DE 19873731638 DE19873731638 DE 19873731638 DE 3731638 A DE3731638 A DE 3731638A DE 3731638 A1 DE3731638 A1 DE 3731638A1
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Prior art keywords
oxyphenyl
pyrimidine
undecen
alkyloxy
formula
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DE19873731638
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German (de)
Inventor
Rainer Dr Wingen
Hans-Rolf Dr Duebal
Claus Dr Escher
Wolfgang Dr Hemmerling
Ingrid Dr Mueller
Dieter Dr Ohlendorf
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Hoechst AG
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Hoechst AG
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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
    • 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
    • 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*-

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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)

Abstract

The novel phenylpyrimidine derivatives of the formula <IMAGE> where R<1> is alkyl having 7 to 16 carbon atoms or alkoxy having 6 to 16 carbon atoms, and n is from 4 to 14, form Sc phases and cause a pronounced melting point depression in mixtures with one another or with structurally closely related phenylpyrimidine derivatives substituted to saturation. Neither are the properties affected by this.

Description

Ferroelektrische Flüssigkristallsysteme haben in jüngerer Zeit zunehmende Aufmerksamkeit als Anzeigemedium in elektrooptischen Bauteilen gewonnen. Eine Voraussetzung für die praktische Verwendbarkeit solcher Systeme ist vielfach die Ausbildung einer smektisch-C-Phase bzw. einer chiralen smektisch-C-Phase (S c - bzw. S c *-Phase) in einem breiten Temperaturband, insbesondere auch bei Temperaturen um und unterhalb Raumtemperatur. Bei den meisten bekannten Verbindungen, die eine S c -Phase bilden, entsteht diese bei einer Temperatur, die erheblich über der Raumtemperatur liegt. Es ist also nötig, den Schmelzpunkt und insbesondere den unteren Phasenumwandlungspunkt der S c -Phase zu senken.Ferroelectric liquid crystal systems have recently received increasing attention as a display medium in electro-optical components. A prerequisite for the practical usability of such systems is often the formation of a smectic C phase or a chiral smectic C phase (S c or S c * phase) in a wide temperature range, in particular also at temperatures around and below room temperature. For most known compounds that form an S c phase, this occurs at a temperature that is significantly above room temperature. It is therefore necessary to lower the melting point and in particular the lower phase transition point of the S c phase.

Es ist bekannt, daß die Schmelzpunktdepression in Mischungen um so ausgeprägter ausfällt, je größer der strukturelle Unterschied der Gemischkomponenten ist (J. Chem. Soc. 1955, 4305). Dies gilt auch für die Schmelzpunktdepression in Systemen, die die für die Herstellung elektrooptischer Bauelemente ideale Phasenfolge K↔S c ↔S A ↔N↔I aufweisen. Hier bleiben aber andere wesentliche Kenngrößen eher dann erhalten, wenn die Komponenten der Mischung strukturell ähnlich sind. Die beiden Aufgaben - Schmelzpunktserniedrigung und Verschiebung der unteren Temperaturgrenze der S c -Phase zu tieferer Temperatur einerseits und weitestgehende Erhaltung der anderen Kenngrößen andererseits - stehen also in einem gewissen Widerspruch.It is known that the melting point depression in mixtures is more pronounced the greater the structural difference of the mixture components (J. Chem. Soc. 1955, 4305). This also applies to the melting point depression in systems that have the ideal phase sequence K ↔ S c ↔ S A ↔ N ↔ I for the manufacture of electro-optical components. However, other essential parameters are retained here if the components of the mixture are structurally similar. The two tasks - lowering the melting point and shifting the lower temperature limit of the S c phase to a lower temperature on the one hand and largely maintaining the other parameters on the other - are therefore somewhat contradictory.

Es wurde nun überraschend gefunden, daß Phenylpyrimidinderviate der allgemeinen Formel (I)It has now surprisingly been found that Phenylpyrimidine derivatives of the general formula (I)

in der R¹ ein geradkettiger oder verzweigter Alkylrest mit 7 bis 16 C-Atomen oder ein geradkettiger oder verzweigter Alkyloxyrest mit 6 bis 16 C-Atomen und n eine Zahl von 4 bis 14 ist, selbst S c -Phasen ausbilden und in Mischungen miteinander oder mit anderen Verbindungen, die S c -Phasen ausbilden, zu einer erheblichen Schmelzpunktdepression mit gleichzeitiger Verlagerung der unteren S c -Phasenumwandlungstemperatur zu tieferen Temperaturen führen, wobei aufgrund der strukturellen Ähnlichkeit andere Kenngrößen kaum beeinflußt werden (vgl. Beispiel 17 und Vergleich 17a).in which R¹ is a straight-chain or branched alkyl radical having 7 to 16 carbon atoms or a straight-chain or branched alkyloxy radical having 6 to 16 carbon atoms and n is a number from 4 to 14, itself form S c phases and in mixtures with one another or with other compounds that form S c phases lead to a significant melting point depression with simultaneous shifting of the lower S c phase transition temperature to lower temperatures, whereby other parameters are hardly influenced due to the structural similarity (cf. Example 17 and comparison 17a).

Als andere Verbindungen, die S c -Phasen ausbilden, kommen insbesondere die strukturell nahe verwandten 2-(4-Alkoxy-phenyl)-5-alkyl- pyrimidine und 2-(4-Alkoxy-phenyl)-5-alkyloxypyrimidine in Frage.Other compounds which form S c phases are, in particular, the structurally closely related 2- (4-alkoxyphenyl) -5-alkylpyrimidines and 2- (4-alkoxyphenyl) -5-alkyloxypyrimidines.

Die Verbindungen der Formel (I) sind neu. Sie sind chemisch, thermisch und photochemisch stabil und verfügen über sehr gute Mischungskompatibilität.The compounds of formula (I) are new. you are chemically, thermally and photochemically stable and available about very good mixture compatibility.

Als Komponenten nematischer Flüssigkristallmischungen sind in den EP-A 01 22 389, 01 67 912 und 01 68 683 sehr allgemein Phenylpyrimidinderivate beschrieben, die einen Alkenylsubstituenten enthalten. Hier handelt es sich aber um Verbindungen, bei denen die Doppelbindung nicht terminal ist, oder bei denen eine terminale Doppelbindung Bestandteil einer Alkenylgruppe mit maximal sechs C-Atomen ist. Das Auftreten einer S c -Phase in den erfindungsgemäßen Verbindungen und ihre Eigenschaft, in Mischung mit strukturell nahe verwandten Verbindungen eine ausgeprägte Schmelzpunktserniedrigung zu bewirken, war nicht zu erwarten.Phenylpyrimidine derivatives which contain an alkenyl substituent are very generally described as components of nematic liquid crystal mixtures in EP-A 01 22 389, 01 67 912 and 01 68 683. However, these are compounds in which the double bond is not terminal, or in which a terminal double bond is part of an alkenyl group with a maximum of six carbon atoms. The occurrence of an S c phase in the compounds according to the invention and their property of causing a pronounced lowering of the melting point in a mixture with structurally closely related compounds was not to be expected.

Ein Gegenstand der Erfindung sind demnach Verbindungen der Formel (I). The invention accordingly relates to compounds of Formula (I).  

Ein weiterer Gegenstand der Erfindung ist ein Verfahren zum Herstellen der Verbindungen der Formel (I).Another object of the invention is a method for the preparation of the compounds of formula (I).

Die Herstellung der Verbindungen der Formel (I) erfolgt vorteilhafterweise so, daß Phenole der Formel (II) mit Verbindungen der Formel (IIIa) in Gegenwart von Säurefängern wie Alkali- oder Erdalkalicarbonaten oder -hydrogencarbonaten, Alkali- oder Erdalkalihydroxiden oder organischen Basen wie Pyridin oder Diethylamin, zu (I) umgesetzt werden.The compounds of the formula (I) are prepared advantageously so that phenols of formula (II) with Compounds of formula (IIIa) in the presence of acid scavengers such as alkali or alkaline earth carbonates or -hydrogen carbonates, alkali or alkaline earth metal hydroxides or organic bases such as pyridine or diethylamine, to (I) be implemented.

Bevorzugt werden die Alkali- oder Erdalkalisalze von (II) mit (IIIa), bevorzugt den Bromiden (Y = Br) zu (I)The alkali or alkaline earth metal salts of (II) are preferred with (IIIa), preferably the bromides (Y = Br) to (I)

umgesetzt. Bevorzugt wird auch die Umsetzung von (II) mit (IIIb) unter Zuhilfenahme von Triphenylphosphin und Azodicarbonsäureester, wie sie als Mitsunobu-Reaktion, z. B. in J. Chem. Soc. Perkin Trans. 1975, 461, beschrieben ist.implemented. The reaction of (II) with is also preferred (IIIb) with the help of triphenylphosphine and Azodicarboxylic acid esters as used as a Mitsunobu reaction, e.g. B. in J. Chem. Soc. Perkin Trans. 1975, 461.

Beispiel 1example 1

2-[4-(7-Octen-1-yl)oxyphenyl]-5-octyl-pyrimidin (I, R¹ = H₁₇C₈, n = 6)2- [4- (7-octen-1-yl) oxyphenyl] -5-octyl-pyrimidine (I, R¹ = H₁₇C₈, n = 6)

Eine Lösung von 4,3 g 4-(5-Octyl-pyrimidin-2-yl)phenyl in 20 ml Dimethylformamid wird mit 0,45 g Natriumhydrid (80%) versetzt. Nach Abklingen der H₂-Entwicklung werden 2,9 g 8-Brom-1-octan zugegeben und 4 h bei 35°C gerührt. Nach Zugabe von 200 ml H₂O wird mit Dichlormethan extrahiert und der Extrakt chromatographiert (SiO₂, Dichlormethan/Hexan 1 : 1). Nach Umkristallisation aus Methanol werden 3,3 g farblose Kristalle erhalten.
Phasenfolge K 19,2 S c 33,3 S A 56,1 N 60,2 I A solution of 4.3 g of 4- (5-octyl-pyrimidin-2-yl) phenyl in 20 ml of dimethylformamide is mixed with 0.45 g of sodium hydride (80%). After the H₂ evolution has subsided, 2.9 g of 8-bromo-1-octane are added and the mixture is stirred at 35 ° C. for 4 h. After adding 200 ml of H₂O, the mixture is extracted with dichloromethane and the extract is chromatographed (SiO₂, dichloromethane / hexane 1: 1). After recrystallization from methanol, 3.3 g of colorless crystals are obtained.
Phase sequence K 19.2 S c 33.3 S A 56.1 N 60.2 I

Analog werden hergestellt:The following are produced analogously:

Beispiel 2Example 2

2-[4-(7-Octen-1-yl)oxyphenyl]-5-decyl-pyrimidin (I, R¹ = H₂₁C₁₀, n = 6)
Phasenfolge K 38,2 S c 49,6 S A 67,9 I 2- [4- (7-octen-1-yl) oxyphenyl] -5-decyl-pyrimidine (I, R¹ = H₂₁C₁₀, n = 6)
Phase sequence K 38.2 S c 49.6 S A 67.9 I

Beispiel 3Example 3

2-[4-(7-Octen-1-yl)oxyphenyl]-5-octyloxy-pyrimidin (I, R¹ = H₁₇C₈O, n = 6)
Phasenfolge K 48,5 S c 76,3 S A 92 N 92,6 I 2- [4- (7-octen-1-yl) oxyphenyl] -5-octyloxypyrimidine (I, R¹ = H₁₇C₈O, n = 6)
Phase sequence K 48.5 S c 76.3 S A 92 N 92.6 I

Beispiel 4Example 4

2-[4-(10-Undecen-1-yl)oxyphenyl]-5-octyl-pyrimidin (I, R¹ = H₁₇C₈, n = 9)2- [4- (10-Undecen-1-yl) oxyphenyl] -5-octyl-pyrimidine (I, R¹ = H₁₇C₈, n = 9)

Eine Lösung von 2,6 g Triphenylphosphin, 1,7 g Azodicarbonsäurediethylester, 1,74 g 10-Undecen-1-ol und 2,8 g 4-(5-Octyl-pyrimidin-2-yl)phenol in 15 ml Tetrahydrofuran wird 24 h bei 20°C belassen. Das Lösungsmittel wird abdestilliert und der Rückstand chromatographiert (SiO₂, Dichlormethan). Nach Umkristallisation aus Methanol werden 2,1 g farblose Kristalle erhalten.
Phasenfolge K 33,9 S c 53,0 S A 64,4 N 66,2 I A solution of 2.6 g of triphenylphosphine, 1.7 g of diethyl azodicarboxylate, 1.74 g of 10-undecen-1-ol and 2.8 g of 4- (5-octyl-pyrimidin-2-yl) phenol in 15 ml of tetrahydrofuran Leave for 24 h at 20 ° C. The solvent is distilled off and the residue is chromatographed (SiO₂, dichloromethane). After recrystallization from methanol, 2.1 g of colorless crystals are obtained.
Phase sequence K 33.9 S c 53.0 S A 64.4 N 66.2 I

Analog werden erhalten:The following are obtained analogously:

Beispiel 5Example 5

2-[4-(10-Undecen-1-yl)oxyphenyl]-5-octyloxy-pyrimidin (I, R¹ = H₂₁C₈O, n = 9)
Phasenfolge K 44,1 S c 78,5 S A 94,5 I 2- [4- (10-Undecen-1-yl) oxyphenyl] -5-octyloxypyrimidine (I, R¹ = H₂₁C₈O, n = 9)
Phase sequence K 44.1 S c 78.5 S A 94.5 I

Beispiel 6Example 6

2-[4-(10-Undecen-1-yl)oxyphenyl]-5-nonyl-pyrimidin (I, R¹ = H₁₉C₉, n = 9)
Phasenfolge K 31,3 S c 52,8 S A 71,7 I 2- [4- (10-Undecen-1-yl) oxyphenyl] -5-nonyl-pyrimidine (I, R¹ = H₁₉C₉, n = 9)
Phase sequence K 31.3 S c 52.8 S A 71.7 I

Beispiel 7Example 7

2-[4-(10-Undecen-1-yl)oxyphenyl]-5-decyl-pyrimidin (I, R¹ = H₂₁C₁₀, n = 9)
Phasenfolge K 39,9 S c 65,2 S A 72,5 I 2- [4- (10-Undecen-1-yl) oxyphenyl] -5-decyl-pyrimidine (I, R¹ = H₂₁C₁₀, n = 9)
Phase sequence K 39.9 S c 65.2 S A 72.5 I

Beispiel 8Example 8

2-[4-(10-Undecen-1-yl)oxyphenyl]-5-dodecyl-pyrimidin (I, R¹ = H₂₅C₁₂, n = 9)
Phasenfolge K 45,9 S c 75,5 S A 76,5 I 2- [4- (10-Undecen-1-yl) oxyphenyl] -5-dodecyl-pyrimidine (I, R¹ = H₂₅C₁₂, n = 9)
Phase sequence K 45.9 S c 75.5 S A 76.5 I

Gegenstand der Erfindung sind schließlich die Verwendung der Verbindungen nach Formel (I) als Bestandteil von flüssigkristallinen, insbesondere ferroelektrischen flüssigkristallinen Mischungen, diese Verbindungen enthaltende Flüssigkristallmischungen und elektrooptische Bauteile, die solche Mischungen enthalten.Finally, the subject of the invention is the use of the compounds of formula (I) as part of liquid crystalline, especially ferroelectric liquid crystalline mixtures, these compounds containing liquid crystal mixtures and electro-optical Components that contain such mixtures.

Beispiel 9Example 9

Eine Mischung, bestehend aus
2-[4-(10-Undecen-1-yl)oxyphenyl]-5-octyl-pyrimidin, 50 Mol-%, und
2-[4-(10-Undecen-1-yl)oxyphenyl]-5-decyl-pyrimidin, 50 Mol-%,
hat die Phasenfolge K 18,9 S c 55,2 S A 68,3 I.A mixture consisting of
2- [4- (10-Undecen-1-yl) oxyphenyl] -5-octyl-pyrimidine, 50 mol%, and
2- [4- (10-Undecen-1-yl) oxyphenyl] -5-decyl-pyrimidine, 50 mol%,
has the phase sequence K 18.9 S c 55.2 S A 68.3 I.

Beispiel 10Example 10

Eine Mischung, bestehend aus
2-[4-(10-Undecen-1-yl)oxyphenyl]-5-octyloxy-pyrimidin, 45 Mol-%, und
2-[4-(7-Undecen-1-yl)oxyphenyl]-5-octyloxy-pyrimidin, 55 Mol-%,
hat die Phasenfolge K 20 S c 68 S A 93 N 93,1 I.A mixture consisting of
2- [4- (10-Undecen-1-yl) oxyphenyl] -5-octyloxypyrimidine, 45 mol%, and
2- [4- (7-undecen-1-yl) oxyphenyl] -5-octyloxypyrimidine, 55 mol%,
has the phase sequence K 20 S c 68 S A 93 N 93.1 I.

Beispiel 11Example 11

Eine Mischung, bestehend aus
2-[4-(10-Undecen-1-yl)oxyphenyl]-5-octyl-pyrimidin, 40 Mol-%,
2-[4-(10-Undecen-1-yl)oxyphenyl]-5-decyl-pyrimidin, 40 Mol-%, und
2-[4-(10-Undecen-1-yl)oxyphenyl]-5-dodecyl-pyrimidin, 20 Mol-%,
hat die Phasenfolge K 16 S c 58 S A 70 I.A mixture consisting of
2- [4- (10-Undecen-1-yl) oxyphenyl] -5-octyl-pyrimidine, 40 mol%,
2- [4- (10-Undecen-1-yl) oxyphenyl] -5-decyl-pyrimidine, 40 mol%, and
2- [4- (10-Undecen-1-yl) oxyphenyl] -5-dodecyl-pyrimidine, 20 mol%,
has the phase sequence K 16 S c 58 S A 70 I.

Beispiel 12Example 12

Eine Mischung, bestehend aus
2-(4-Octyloxy-phenyl)-5-octyl-pyrimidin, 60 Mol-%, und
2-[4-(10-Undecen-1-yl)oxyphenyl]-5-octyl-pyrimidin, 40 Mol-%,
hat die Phasenfolge K 13,2 S c 51,1 S A 61,3 N 66,7 I.A mixture consisting of
2- (4-octyloxy-phenyl) -5-octyl-pyrimidine, 60 mol%, and
2- [4- (10-Undecen-1-yl) oxyphenyl] -5-octyl-pyrimidine, 40 mol%,
has the phase sequence K 13.2 S c 51.1 S A 61.3 N 66.7 I.

Beispiel 13Example 13

Eine Mischung, bestehend aus
2-(4-Octyloxy-phenyl)-5-octyloxy-pyrimidin, 50 Mol-%, und
2-[4-(10-Undecen-1-yl)oxyphenyl]-5-octyloxy-pyrimidin, 50 Mol-%,
hat die Phasenfolge K 27 S c 80 S A 96 N 96,1 I.A mixture consisting of
2- (4-octyloxy-phenyl) -5-octyloxypyrimidine, 50 mol%, and
2- [4- (10-Undecen-1-yl) oxyphenyl] -5-octyloxypyrimidine, 50 mol%,
has the phase sequence K 27 S c 80 S A 96 N 96.1 I.

Beispiel 14Example 14

Eine Mischung aus 2-(4-Butyloxy-phenyl)-5-octyloxy-pyrimidin, 2-(4-Hexyloxy-phenyl)-5-octyloxy-pyrimidin, 2-(4-Oxtyloxy- phenyl)-5-octyloxy-pyrimidin, 2-(4-Decyloxy-phenyl)-5- octyloxy-pyrimidin und 20 Mol-% der Verbindung aus Beispiel 5 hat die Phasenfolge K 13 S c 79 S A 94 N 97 I.A mixture of 2- (4-butyloxy-phenyl) -5-octyloxypyrimidine, 2- (4-hexyloxyphenyl) -5-octyloxypyrimidine, 2- (4-oxyloxyphenyl) -5-octyloxypyrimidine , 2- (4-Decyloxy-phenyl) -5-octyloxy-pyrimidine and 20 mol% of the compound from Example 5 has the phase sequence K 13 S c 79 S A 94 N 97 I.

Beispiel 15Example 15

Eine Mischung, bestehend aus 2-(4-Octyloxy-phenyl)-5-octyl-pyrimidin, 2-(4-Octyloxy-phenyl)-5-decyl-pyrimidin, 2-(4-Octyloxy- phenyl)-5-dodecyl-pyrimidin und 28 Mol-% der Verbindung aus Beispiel 4 hat die Phasenfolge K 10 S c 54 S A 66 N 68,5 I.A mixture consisting of 2- (4-octyloxy-phenyl) -5-octyl-pyrimidine, 2- (4-octyloxy-phenyl) -5-decyl-pyrimidine, 2- (4-octyloxy-phenyl) -5-dodecyl -pyrimidine and 28 mol% of the compound from Example 4 has the phase sequence K 10 S c 54 S A 66 N 68.5 I.

Beispiel 16Example 16

Eine Mischung aus 2-(4-Octyloxy-phenyl)-5-octyl-pyrimidin, 2-(4-Decyloxy-phenyl)-5-octyl-pyrimidin, 2-(4-Dodecyloxy- phenyl)-5-decyl-pyrimidin und 16 Mol-% der Verbindung aus Beispiel 4 hat die Phasenfolge K 15.5 S c 58 S A 61.5 N 64 I.A mixture of 2- (4-octyloxy-phenyl) -5-octyl-pyrimidine, 2- (4-decyloxy-phenyl) -5-octyl-pyrimidine, 2- (4-dodecyloxy-phenyl) -5-decyl-pyrimidine and 16 mol% of the compound from Example 4 has the phase sequence K 15.5 S c 58 S A 61.5 N 64 I.

Beispiel 17Example 17

Eine Mischung, bestehend aus
2-(4-Ethyloxy-phenyl)-5-octyloxy-pyrimidin,
2-(4-Butyloxy-phenyl)-5-octyloxy-pyrimidin,
2-(4-Hexyloxy-phenyl)-5-octyloxy-pyrimidin,
2-(4-Octyloxy-phenyl)-5-octyloxy-pyrimidin,
2-(4-Decyloxy-phenyl)-5-octyloxy-pyrimidin und
trans-4-Pentyl-cyclohexancarbonsäure-[4- (5-octyloxy-pyrimidin-2-yl]phenyl-ester
mit der Phasenfolge K 12,2 S c 79,4 S A 91,1 N 102,5 I wird mit 27,5% der Verbindung nach Beispiel 4 versetzt;
die resultierende Mischung hat die Phasenfolge K 7,8 S c 69 S A 83,5 N 93 I.A mixture consisting of
2- (4-ethyloxyphenyl) -5-octyloxypyrimidine,
2- (4-butyloxyphenyl) -5-octyloxypyrimidine,
2- (4-hexyloxyphenyl) -5-octyloxypyrimidine,
2- (4-octyloxy-phenyl) -5-octyloxy-pyrimidine,
2- (4-decyloxy-phenyl) -5-octyloxypyrimidine and
trans-4-pentylcyclohexane carboxylic acid [4- (5-octyloxypyrimidin-2-yl] phenyl ester
with the phase sequence K 12.2 S c 79.4 S A 91.1 N 102.5 I , 27.5% of the compound according to Example 4 is added;
the resulting mixture has the phase sequence K 7.8 S c 69 S A 83.5 N 93 I.

Vergleichsbeispiel 17aComparative Example 17a

Eine Mischung wie in Beispiel 17 wird anstelle der Verbindung aus Beispiel 4 mit 27,5% 2-(4-Dodecyloxy- phenyl)-5-octyl-pyrimidin versetzt; es resultiert die Phasenfolge K 11,6 S c 69,9 S A 85,3 N 93,4 I.27.5% of 2- (4-dodecyloxyphenyl) -5-octyl-pyrimidine is added to a mixture as in Example 17 instead of the compound from Example 4; this results in the phase sequence K 11.6 S c 69.9 S A 85.3 N 93.4 I.

Claims (10)

1. Neue Phenylpyrimidine der allgemeinen Formel (I), in der R¹ geradkettiges oder verzweigtes Alkyl mit 7 bis 16 C-Atomen oder geradkettiges oder verzweigtes Alkyloxy mit 6 bis 16 C-Atomen
n 4 bis 14.1. New phenylpyrimidines of the general formula (I) in which R¹ straight-chain or branched alkyl having 7 to 16 carbon atoms or straight-chain or branched alkyloxy having 6 to 16 carbon atoms
n 4 to 14. 2. Neue Phenylpyrimidine nach Anspruch 1, nämlich
2-[4-(7-Octen-1-yl)oxyphenyl]-5-octyl-pyrimidin,
2-[4-(7-Octen-1-yl)oxyphenyl]-5-decyl-pyrimidin,
2-[4-(7-Octen-1-yl)oxyphenyl]-5-octyloxy-pyrimidin,
2-[4-(10-Undecen-1-yl)oxyphenyl]-5-octyl-pyrimidin,
2-[4-(10-Undecen-1-yl)oxyphenyl]-5-octyloxy-pyrimidin,
2-[4-(10-Undecen-1-yl)oxyphenyl]-5-nonyl-pyrimidin,
2-[4-(10-Undecen-1-yl)oxyphenyl]-5-decyl-pyrimidin,
2-[4-(10-Undecen-1-yl)oxyphenyl]-5-dodecyl-pyrimidin.2. New phenylpyrimidines according to claim 1, namely
2- [4- (7-octen-1-yl) oxyphenyl] -5-octyl-pyrimidine,
2- [4- (7-octen-1-yl) oxyphenyl] -5-decyl-pyrimidine,
2- [4- (7-octen-1-yl) oxyphenyl] -5-octyloxypyrimidine,
2- [4- (10-undecen-1-yl) oxyphenyl] -5-octyl-pyrimidine,
2- [4- (10-undecen-1-yl) oxyphenyl] -5-octyloxypyrimidine,
2- [4- (10-undecen-1-yl) oxyphenyl] -5-nonyl-pyrimidine,
2- [4- (10-undecen-1-yl) oxyphenyl] -5-decyl-pyrimidine,
2- [4- (10-Undecen-1-yl) oxyphenyl] -5-dodecyl pyrimidine. 3. Verfahren zur Herstellung der Verbindungen nach Anspruch 1 und 2, dadurch gekennzeichnet, daß 2-(4-Hydroxyphenyl)- 5-alkyl- bzw. -5-alkyloxy-pyrimidine der Formel (II) nach Überführung in ihre Alkali- oder Erdalkalisalze mit Halogen-Verbindungen der Formel (IIIa) umgesetzt werden, die über eine Alkylkette mit endständiger Doppelbindung verfügen.3. A process for the preparation of the compounds according to claim 1 and 2, characterized in that 2- (4-hydroxyphenyl) - 5-alkyl- or -5-alkyloxypyrimidines of the formula (II) after conversion to their alkali or alkaline earth salts reacted with halogen compounds of the formula (IIIa) that have an alkyl chain with terminal Double bond. 4. Verfahren zur Herstellung der Verbindungen nach Anspruch 1 und 2, dadurch gekennzeichnet, daß 2-(4-Hydroxy-phenyl)-5-alkyl- bzw. -5-alkyloxy-pyrimidine der Formel II mit Hydroxyverbindungen der Formel (IIIb), die über eine Alkylkette mit endständiger Doppelbindung verfügen, unter Zuhilfenahme von Triphenylphosphin und Azodicarbonsäureester umgesetzt werden.4. Process for the preparation of the compounds according to Claims 1 and 2, characterized in that 2- (4-hydroxyphenyl) -5-alkyl- or -5-alkyloxypyrimidines of the formula II with hydroxy compounds of the formula (IIIb),  via an alkyl chain with a terminal double bond have, with the help of triphenylphosphine and Azodicarboxylic acid esters are implemented. 5. Verwendung von Verbindungen (I) als Komponenten von Flüssigkristallmischungen.5. Use of compounds (I) as components of Liquid crystal mixtures. 6. Ausführungsform nach Anspruch 5, dadurch gekennzeichnet, daß die Flüssigkristallmischung 5-Alkyl-2-(4-alkyloxy- phenyl)pyrimidine und/oder 5-Alkyloxy-2-(4-alkyloxy- phenyl)pyrimidine zu mehr als 25% enthält.6. Embodiment according to claim 5, characterized in that the liquid crystal mixture 5-alkyl-2- (4-alkyloxy- phenyl) pyrimidines and / or 5-alkyloxy-2- (4-alkyloxy- phenyl) pyrimidine contains more than 25%. 7. Verwendung der Verbindungen nach Anspruch 5 als Komponenten von ferroelektrischen Flüssigkristallmischungen.7. Use of the compounds according to claim 5 as Components of ferroelectric Liquid crystal mixtures. 8. Ausführungsform nach Anspruch 7, dadurch gekennzeichnet, daß die ferroelektrische Flüssigkristallmischung 5-Alkyl-2-(4-alkyloxy-phenyl)pyrimidine und/oder 5-Alkyloxy-2-(4-alkyloxy-phenyl)pyrimidine zu mehr als 25% enthält.8. Embodiment according to claim 7, characterized in that the ferroelectric liquid crystal mixture 5-alkyl-2- (4-alkyloxy-phenyl) pyrimidines and / or 5-alkyloxy-2- (4-alkyloxy-phenyl) pyrimidines to more than Contains 25%. 9. Flüssigkristalline Mischung, insbesondere ferroelektrische flüssigkristalline Mischung, enthaltend mindestens eine Verbindung der Formel (I).9. Liquid crystalline mixture, in particular Ferroelectric liquid crystalline mixture containing at least one compound of formula (I). 10. Elektrooptisches Bauteil, enthaltend eine flüssigkristalline Mischung nach Anspruch 9.10. Electro-optical component containing one Liquid-crystalline mixture according to claim 9.
DE19873731638 1987-09-19 1987-09-19 Liquid-crystalline phenylpyrimidine derivatives, process for their preparation, and their use in liquid-crystalline mixtures Withdrawn DE3731638A1 (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0518190A3 (en) * 1991-06-14 1993-03-10 F. Hoffmann-La Roche Ag Alkenyloxyphenyl pyrimidines
EP0634469A1 (en) * 1993-07-13 1995-01-18 Sumitomo Chemical Company, Limited Compound having unsaturated side-chain, process for preparing the same, liquid crystalline polymer prepared from the same, liquid crystal mixture and display element
US5662828A (en) * 1993-07-13 1997-09-02 Sumitomo Chemical Company, Limited Compound having unsaturated side chain, process for preparing the same, liquid crystalline polymer prepared from the same, liquid crystal mixture and display element

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0518190A3 (en) * 1991-06-14 1993-03-10 F. Hoffmann-La Roche Ag Alkenyloxyphenyl pyrimidines
US5234622A (en) * 1991-06-14 1993-08-10 Hoffman-La Roche Inc. Alkenyloxyphenylpyrimidine derivatives and liquid crystalline mixtures containing same
EP0634469A1 (en) * 1993-07-13 1995-01-18 Sumitomo Chemical Company, Limited Compound having unsaturated side-chain, process for preparing the same, liquid crystalline polymer prepared from the same, liquid crystal mixture and display element
US5554317A (en) * 1993-07-13 1996-09-10 Sumitomo Chemical Company, Limited Compound having unsaturated side chain, process for preparing the same, liquid crystalline polymer prepared from the same, liquid crystal mixture and display element
US5662828A (en) * 1993-07-13 1997-09-02 Sumitomo Chemical Company, Limited Compound having unsaturated side chain, process for preparing the same, liquid crystalline polymer prepared from the same, liquid crystal mixture and display element

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