DD248136A1 - NEMATIC CRYSTALLINE-LIQUID MIXTURES - Google Patents

NEMATIC CRYSTALLINE-LIQUID MIXTURES Download PDF

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Publication number
DD248136A1
DD248136A1 DD86289180A DD28918086A DD248136A1 DD 248136 A1 DD248136 A1 DD 248136A1 DD 86289180 A DD86289180 A DD 86289180A DD 28918086 A DD28918086 A DD 28918086A DD 248136 A1 DD248136 A1 DD 248136A1
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German Democratic Republic
Prior art keywords
crystalline
liquid
mixtures
nematic
displays
Prior art date
Application number
DD86289180A
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German (de)
Inventor
Dietrich Demus
Horst Zaschke
Reinhard Paschke
Anton Hauser
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Univ Halle Wittenberg
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Publication date
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Priority to DD86289180A priority Critical patent/DD248136A1/en
Publication of DD248136A1 publication Critical patent/DD248136A1/en

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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/34Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/34Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K2019/3422Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
    • C09K2019/3425Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/34Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K2019/3422Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
    • C09K2019/3427Six-membered ring with 3 or more oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

Die Erfindung betrifft die Anwendung von fluessigen Kristallen in optoelektronischen Displays zur Darstellung von Ziffern, Zeichen und Abbildungen. Das Ziel der Erfindung sind kristallin-fluessige nematische Gemische fuer optoelektronische Displays mit hohen Klaerpunkten. Es wurde gefunden, dass neue kristallin-fluessige 1,4-disubstituierte 2,5,7-Trioxa-bicyclo(2.2.2)octane der allgemeinen Formel I, die in 1- und/oder 4-Position vorzugsweise substituierte Phenylreste enthalten.wobeibedeuten, dass Klaerpunkte nematischer Gemische erhoehen und somit vorteilhaft in optoelektronischen Displays eingesetzt werden koennen.The invention relates to the use of liquid crystals in optoelectronic displays for displaying numbers, characters and images. The object of the invention are crystalline-liquid nematic mixtures for optoelectronic displays with high Klaerpunkten. It has been found that novel crystalline 1,4-disubstituted 2,5,7-trioxa-bicyclo (2.2.2) octanes of the general formula I which contain preferably substituted phenyl radicals in the 1- and / or 4-position that Klaerpunkte increase nematic mixtures and thus can be used advantageously in optoelectronic displays.

Description

, -0CnH2n+1 ', - 0C n H 2n + 1 '

mit η = 1 bis 8with η = 1 to 8

bedeuten, eingesetzt werden.mean to be used.

Anwendungsgebiet der ErfindungField of application of the invention

Die Erfindung betrifft die Anwendung von flüssigen Kristallen in optoelektronischen Displays zur Darstellung von Ziffern, Zeichen und Abbildungen.The invention relates to the use of liquid crystals in optoelectronic displays for displaying numbers, characters and images.

Charakteristik der bekannten LösungenCharacteristic of the known solutions

Displays auf der Basis flüssiger Kristalle werden für viele verschiedene Zwecke verwendet. Entsprechend müssen die Eigenschaften der Displays und der eingesetzten Flüssigkristallmischungen modifiziert werden B.Behadur: Liquid Crystal Displays, Mol. Cryst. Liq. Cryst. 109 (1) 1-104(1984).Displays based on liquid crystals are used for many different purposes. Accordingly, the properties of the displays and the liquid crystal mixtures used have to be modified B.Behadur: Liquid Crystal Displays, Mol. Cryst. Liq. Cryst. 109 (1) 1-104 (1984).

Um die Eigenschaften kristallin-flüssiger Gemische gezielt beeinflussen zu können, benötigt man entsprechende Mischungskomponenten mit den unterschiedlichsten Eigenschaften. Obwohl heutzutage über 13000 Flüssigkristallsubstanzen bekannt sind (D. Demus, H.Zaschke: Flüssige Kristalle in Tabellen Leipzig 1984), gibt es keine Substanzen, die alle geforderten Eigenschaften aufweisen, so daß man ständig auf der Suche nach neuen Stoffen, insbesondere solchen, die sich von neuen Stoffklassen ableiten, ist.In order to be able to influence the properties of crystalline-liquid mixtures in a targeted manner, it is necessary to have corresponding mixture components with very different properties. Although today more than 13,000 liquid crystal substances are known (D. Demus, H. Zaschke: Liquid crystals in Tables Leipzig 1984), there are no substances that have all the required properties, so that one is constantly on the lookout for new substances, especially those derive from new classes of substance is.

Ziel der ErfindungObject of the invention

Das Ziel der Erfindung sind kristallin-flüssige nematische Gemische für optoelektronische Displays mit hohen Klärpunkten. Darlegung des Wesens der ErfindungThe object of the invention are crystalline liquid nematic mixtures for optoelectronic displays with high clearing points. Explanation of the essence of the invention

Aufgabe der Erfindung sind neue kristallin-flüssige Stoffe, welche die Klärpunkte nematischer Mischungen erhöhen.The object of the invention are new crystalline-liquid substances which increase the clearing points of nematic mixtures.

Es wurde gefunden, daß neue kristallin-flüssige 1,4-disubstituierte 2,6,7-Trioxa-bicyclo(2.2.2)octane der allgemeinen Formel I, die in 1- und/oder 4-Position vorzugsweise substituierte Phenylreste enthalten.It has been found that novel crystalline liquid 1,4-disubstituted 2,6,7-trioxa-bicyclo (2.2.2) octanes of the general formula I which contain preferably substituted phenyl radicals in the 1- and / or 4-position.

wobeiin which

R = CnH2n+l-' CnH2n+lö-' R = C n H 2n + l- ' C n H 2n + l ö -'

= -CnH2n+i'= - C n H 2n + i '

mit η = 1 bis 8 bedeuten,with η = 1 to 8,

die Klärpunkte nematischer Gemische, die für optoelektronische Dispjays eingesetzt werden, erhöhen und somit den Gebrauchswert solcher Mischungen wesentlich verbessern.increase the clearing points of nematic mixtures used for optoelectronic dispays and thus substantially improve the utility of such mixtures.

Die neuen Substanzen sind farblos und stabil gegenüber thermischen Einflüssen oder Bestrahlung.The new substances are colorless and stable against thermal influences or irradiation.

Die Substanzen sind im reinen Zustand smektisch, ergeben jedoch in Mischungen mit nematischen Komponenten nematischeThe substances are smectic in the pure state, but give nematic mixtures in mixtures with nematic components

Gemische. Mixtures.

Ausführungsbeispieleembodiments Beispiel 1:Example 1:

Die folgenden Tabellen zeigen die Umwandlungstemperaturen erfindungsgemäßer neuer Substanzen.The following tables show the transformation temperatures of novel substances according to the invention.

Tabelle 1Table 1

R1 R 1

^61M^ 6 1 m

CeHCeH

C5HC5H

'5n11'5 n 11

C7H1SC 7 H 1 S

7474 ( 50)(50) 4545 •64• 64 3535 •87• 87 4343 •85• 85

Tabelle 2Table 2

R1 R 1

2.1. 2.2 2.3 2.4 2.5 2.6 2.72.1. 2.2 2.3 2.4 2.5 2.6 2.7

C6H13 C 6 H 13

C6H13 C 6 H 13

C6H13 C 6 H 13

C6Hi3OC 6 Hi 3 O

C6Hi3OC 6 Hi 3 O

Brbr

Brbr

C3H7 C 3 H 7 •95• 95 CsH11 CsH 11 •96• 96 C6H13 C 6 H 13 •81• 81 C5H11C5H11 86 86 C6Hi3 C 6 Hi 3 •84• 84 CsH11 CsH 11 222 222 C6H13 C 6 H 13 •204• 204 kristallin-sfestcrystalline-sfest

•193 •194 •194 197 •182 (•203) (•198)• 193 • 194 • 194 197 • 182 (• 203) (• 198)

Tabelle 4Table 4

CH3 CH3 CH 3 CH 3

C7H15 C7H15 C7H15 C7H15 C7H15 C7H15 C7H15 C6H13O-C7H15 C7H15 C7H15 C7H15 C7H15 C7H15 C 7 H 15 C 6 H 13 O-

OC3H17 OC 3 H 17

-C6H1 -C 6 H 1

COOCOO

OC4H9 OC 4 H 9

OC5H1", OC6H13 OC7H15 OC8H17 OC 5 H 1 ", OC 6 H 13 OC 7 H 15 OC 8 H 17

CNCN

CH2-CH2-CNCH 2 -CH 2 -CN

CNCN

•68 •42 •48 •45 •44 •92 82 •169• 68 • 42 • 48 • 45 • 44 • 92 82 • 169

135 135

•86,5• 86.5

90 90

93 93

•94• 94

•72• 72

•155• 155

(•166)(• 166)

Beispiel 2:Example 2:

Es wird für den Einsatz in optoelektronischen Displays folgende Grundmischung MiA verwendet:For use in optoelectronic displays, the following basic mixture MiA is used:

61,7mol.-%5-n-Hexyl-2-(4-n-hexyloxyphenyl)-pyrimidin 38,3mol.-% 5-n-Hexyl-2-(4-n-nonyloxyphenyl)-pyrimidin61.7 mol% of 5-n-hexyl-2- (4-n-hexyloxyphenyl) -pyrimidine 38.3 mol% of 5-n-hexyl-2- (4-n-nonyloxyphenyl) -pyrimidine

Diese Mi A verändert die Klärtemperatur durch Zusatz von Substanz 2/1 folgendermaßen:This Mi A changes the clearing temperature by adding substance 2/1 as follows:

mol.-% mol.-% Klärtemperaturmol .-% mol .-% clearing temperature

MiA . MiA .

100 95 85 80100 95 85 80

5 15 205 15 20

59 62 66 7059 62 66 70

Beispiel 3: ·>Example 3: ·

Es wird folgende Grundmischung Mi B verwendet: 22mol.-% 5-n-Butyl-2-(4-cyanphenyl)-1,3-dioxan 26mol.-% 5-n-Pentyl-2-(4-cyanphenyl)-1,3-dioxan 32mol.-% 5-n-Hexyl-2-(4-cyanphenyl)-1,3-dioxan 20mol.-%5-(4-n-Hexylphenyl)-2-(4-cyanphenyl)-1,3-dioxanThe following basic mixture Mi B is used: 22 mol% of 5-n-butyl-2- (4-cyanophenyl) -1,3-dioxane 26 mol% of 5-n-pentyl-2- (4-cyanophenyl) -1 , 3-dioxane 32 mol% 5-n-hexyl-2- (4-cyanophenyl) -1,3-dioxane 20 mol% 5- (4-n-hexylphenyl) -2- (4-cyanophenyl) -1 , 3-dioxane

Diese Mi B verändert die Klärtemperatur durch Zusatz von Substanz 2/1 folgendermaßen:This Mi B changes the clearing temperature by adding substance 2/1 as follows:

Klärtemperatur [0C]Clearing temperature [ 0 C]

MiBMiB

Substanz 2/1Substance 2/1

100 95 85 80100 95 85 80

5 15 205 15 20

58 59 65 7058 59 65 70

Beispiel 4:Example 4:

Die SubstanzThe substance

besitzt im Zustand der smektischen B-Phase folgende optische Doppelbrechungen:has the following optical birefringence in the state of the smectic B phase:

Temperatur [°CJ Temperature [° CJ

45 56 6045 56 60

0,15 0,130.15 0.13

0,110.11

Claims (1)

Nematische kristallin-flüssige Gemische für optoelektronische Bauelemente, gekennzeichnet dadurch, daß als Komponenten neue kristallin-flüssige 1,4-disubstituierte 2,6,7-Trioxa-bicyclo (2.2.2) octane der allgemeinen Formel I, die in 1- und/oder 4-Position vorzugsweise substituierte Phenylreste enthalten,Nematic crystalline-liquid mixtures for optoelectronic components, characterized in that as components new crystalline liquid 1,4-disubstituted 2,6,7-trioxa-bicyclo (2.2.2) octanes of the general formula I, which in 1- and / or 4-position preferably contain substituted phenyl radicals, wobsi X =where X = -. R KO)--. R KO) - R = C E0 Λ- , CnHp •.O- , Br-R = C E 0 Λ - , C n Hp • .O-, Br-
DD86289180A 1986-04-16 1986-04-16 NEMATIC CRYSTALLINE-LIQUID MIXTURES DD248136A1 (en)

Priority Applications (1)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012132796A1 (en) 2011-03-25 2012-10-04 Jnc株式会社 Ortho ester derivative, liquid crystal composition, and liquid crystal display element
EP2532726A2 (en) 2011-06-08 2012-12-12 JNC Corporation Liquid Crystal Composition and Liquid Crystal Display Device
CN105238414B (en) * 2014-07-02 2017-10-27 达兴材料股份有限公司 Liquid crystal compound and liquid crystal composition containing same

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012132796A1 (en) 2011-03-25 2012-10-04 Jnc株式会社 Ortho ester derivative, liquid crystal composition, and liquid crystal display element
CN103443104A (en) * 2011-03-25 2013-12-11 捷恩智株式会社 Ortho ester derivative, liquid crystal composition, and liquid crystal display element
CN103443104B (en) * 2011-03-25 2016-08-10 捷恩智株式会社 There is compound, liquid-crystal composition and the liquid crystal display cells of 2,6,7-trioxa-l-phosphabicyclo [2.2.2] octane ring
US9605207B2 (en) 2011-03-25 2017-03-28 Jnc Corporation Orthoester derivative, liquid crystal composition and liquid crystal display device
EP2532726A2 (en) 2011-06-08 2012-12-12 JNC Corporation Liquid Crystal Composition and Liquid Crystal Display Device
EP2532726A3 (en) * 2011-06-08 2013-06-12 JNC Corporation Liquid Crystal Composition and Liquid Crystal Display Device
US8795795B2 (en) 2011-06-08 2014-08-05 Jnc Corporation Liquid crystal composition and liquid crystal display device
CN105238414B (en) * 2014-07-02 2017-10-27 达兴材料股份有限公司 Liquid crystal compound and liquid crystal composition containing same

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