WO2000031211A1 - Compose a base de cristaux liquides - Google Patents

Compose a base de cristaux liquides Download PDF

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Publication number
WO2000031211A1
WO2000031211A1 PCT/IB1999/001831 IB9901831W WO0031211A1 WO 2000031211 A1 WO2000031211 A1 WO 2000031211A1 IB 9901831 W IB9901831 W IB 9901831W WO 0031211 A1 WO0031211 A1 WO 0031211A1
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WIPO (PCT)
Prior art keywords
coo
chiral
formula
group
groups
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Application number
PCT/IB1999/001831
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English (en)
Inventor
Angela Ohlemacher
Jürg FÜNFSCHILLING
Original Assignee
Rolic Ag
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Publication date
Application filed by Rolic Ag filed Critical Rolic Ag
Priority to JP2000584028A priority Critical patent/JP2002530434A/ja
Priority to EP99954281A priority patent/EP1137737A1/fr
Priority to KR1020017006431A priority patent/KR20010089493A/ko
Priority to AU10690/00A priority patent/AU1069000A/en
Publication of WO2000031211A1 publication Critical patent/WO2000031211A1/fr

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    • 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
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
    • C09K19/3458—Uncondensed pyrimidines
    • C09K19/3466—Pyrimidine with at least another heterocycle in the chain
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring

Definitions

  • the present invention relates to liquid crystal compounds, particularly ferroelectric liquid crystal compounds or compounds for use in the preparation of liquid crystal mixtures having ferroelectric properties.
  • ferroelectric liquid crystal phases in the preparation of ferroelectric liquid crystal devices is known. See, for example, Clark and Largerwall, Appl. Phys. Lett. 1980, 36, 899.
  • Ferroelectric liquid crystal devices FLCDs have been found to overcome the limitations associated with devices based on nematic liquid crystal (LC) compounds and mixtures. These limitations include a limited range of viewing angles and relatively slow switching times.
  • Ferroelectric liquid crystal (FLC) phases comprise chiral smectic liquid crystal compounds.
  • the LC molecules are arranged in layers.
  • the director can be either orthogonal to the layer (e.g. smectic-A or S ⁇ ) or tilted (smectic-C or Sc).
  • smectic-C or Sc tilted
  • at least one component comprising the liquid crystal phase has to be chiral.
  • the chiral Sc-phase is denoted by Sc*.
  • a FLC-mixture usually comprises one or more non-chiral components and one or more chiral dopants.
  • the non-chiral component is generally not required for the preparation of FLCs.
  • pyrimidinyl compounds in liquid crystal applications are well known.
  • US 4,774,020 discloses liquid crystal materials, which include a pyrimidinyldioxane derivative. These compounds have been used in nematic liquid crystal applications. Examples of known pyrimidinyl compounds that have found application in ferroelectric liquid crystal applications can be found in WO 96/30344. These include halogen substituted pyrimidinyldioxane derivatives.
  • a first aspect of the invention provides a compound of formula (I)
  • R 1 represents a chiral or non-chiral, branched or straight chain C ⁇ -2 ⁇ alkyl or
  • a and B are each independently a 1.4-phenylene or 1 ,4-cyclohexylene group, which may each be optionally substituted by halogen, cyano or nitro or a group of formula R 1 and in which one or two non-adjacent -CH- or -CH 2 - groups may be optionally replaced by nitrogen or oxygen respectively;
  • n are each independently 0 or 1 ;
  • MG represents a 1,4 phenylene group which may be optionally substituted by hhaallooggeenn,, ccyyaannoo oorr nniittrroo oorr aa ggrroouupp ooff ffoorrmmuullaa RR 11 and in which one or two non-adjacent -CH- groups is replaced by nitrogen.
  • the dioxane-pyridine and -pyrimidine derivatives of the present invention may be included in ferroelectric LC mixtures. This allows a skilled person to selectively optimize certain mixture parameters.
  • the parameters that can be optimized include:
  • a large tilt angle This is important in applications such as DHF-LCDs because it facilitates the preparation of devices having a high brightness.
  • the suppression of the S A -phase This is important in applications such as APD-LCDs which require an N-Sc* transition without an intervening S ⁇ -phase.
  • a low birefringence ⁇ n The dioxane-phenyl-pyrimidine compounds of the present invention have lower birefringence than other common wide temperature range
  • the group R 1 is preferably a branched or straight chain C 5- i 6 alkyl group.
  • the group R ⁇ is preferably a branched or straight chain alkoxy or C 5- i 6 alk- enyloxy group.
  • the groups R and R may, independently of each other, be chiral.
  • the group MG 1 is preferably a 1 ,4-phenylene group, which is optionally substituted by halogen, cyano, nitro, an alkyl or alkoxy group.
  • Z 1 , Z 2 and Z 3 are each preferably a single bond.
  • alkyl should be understood to include groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl.
  • alkenyl should be understood to include groups such as E or Z alkenyl as well as alkenyl groups with a terminal double bond.
  • Examples of such groups include allyl, 2-butenyl, 2-pentenyl, 2-hexenyl, 2-heptenyl, 2-octenyl, 2-nonenyl, 2-decenyl, 3-but- enyl, 3-pentenyl, 3-hexenyl, 3-heptenyl, 3-octenyl, 3-nonenyl, 3-decenyl, 4-pentenyl, 4-hexenyl, 4-heptenyl, 4-octenyl, 4-nonenyl, 4-decenyl, 5-hexenyl, 6-heptenyl, 7-octenyl, 8-nonenyl, 9-decenyl, 10-undecyl, 1 1-dodecenyl and the like.
  • alkoxy should be understood to include groups such as methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy and dodecyloxy.
  • alkenyloxy should be understood to include groups such as 2E-alk- enyloxy, 3Z-alkenyloxy, 4E-alkenyloxy and alkenyloxys with a terminal double bond.
  • the terms "2E-alkenyloxy”, “3Z-alkenyloxy” and “4E-alkenyloxy” embrace straight chain alkenyloxy groups with 3 or more, 4 or more and 5 or more carbon atoms respectively in which the double bond is present in the 2. 3 and 4 positions respectively, with E and Z denoting the configuration of the double bond.
  • Such groups include 2E-butenyloxy.
  • alkylcarbonyloxy should be understood to include groups such as methylcarbonyloxy, ethylcarbonyloxy, propylcarbonyloxy, butylcarbonyloxy. pentylcarbonyloxy, hexylcarbonyloxy, octylcarbonyloxy. nonylcarbonyloxy. decylcarbonyloxy, undecylcarbonyloxy and dodecylcarbonyloxy.
  • alkenylcarbonyloxy should be understood to include groups such as lE-alkenylcarbonyloxy, 2Z-alkenylcarbonyloxy, 3E-alkenylcarbonyloxy, 4Z-alkenyl- carbonyloxy and alkenylcarbonyloxys with a terminal double bond.
  • alkenylcarbonyloxy should be understood to include groups such as lE-alkenylcarbonyloxy, 2Z-alkenylcarbonyloxy, 3E-alkenylcarbonyloxy, 4Z-alkenyl- carbonyloxy and alkenylcarbonyloxys with a terminal double bond.
  • alkenylcarbonyloxy should be understood to include groups such as lE-alkenylcarbonyloxy, 2Z-alkenylcarbonyloxy, 3E-alkenylcarbonyloxy, 4Z-alkenyl- carbonyloxy and alkenylcarbonyloxys with a terminal double bond.
  • "3E-alkenylcarbonyloxy” and “4Z-alk- enylcarbonyloxy” embrace straight chain alkenyl groups with 3 or more, 4 or more and 5 or more carbon atoms respectively in which the double bond is present in the 2, 3 and 4 positions respectively, with E and Z denoting the configuration of the double bond.
  • Such groups include allylcarbonyloxy, 2Z-butenylcarbonyloxy, 2Z-pentenylcarbonyloxy. 2Z-hexenylcarbonyloxy, 2Z-heptenylcarbonyloxy, 2Z-octenylcarbonyloxy, 2Z-nonenyl- carbonyloxy, 2Z-decenylcarbonyloxy. 3-butenylcarbonyloxy, 3E-pentenylcarbonyloxy.
  • halogen is understood to include groups such as fluorine, chlorine, bromine and iodine.
  • R , R " and Z are as defined above for the compound of formula (I);
  • X represents -CH- or nitrogen.
  • each of L 1 to L 5 represents hydrogen.
  • a second aspect of the invention provides a method for the preparation of the compounds of the invention which comprises the steps of reacting an ether of 4-(5-hydroxy-2-pyrimidyl)benzaldehyde with a 2-alkylpropane-
  • EDC is N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride
  • DMAP is 4-dimethylaminopyridine
  • DCM is dichloromethane
  • POCl 3 is phosphorous oxychloride Et 3 N is triethylamine
  • DIBAH is diisobutylaluminum hydride
  • the compounds of the invention may be used alone or as a component of a ferroelectric liquid crystal mixture.
  • a third aspect of the invention therefore provides a ferroelectric liquid crystal mixture comprising a compound of formula (I), the liquid crystal mixture comprising at least two components.
  • the additional component or components of the liquid crystal mixture may comprise one or more compounds of formula (I) or, alternatively, may include other suitable known mesogenic or non-mesogenic compounds.
  • the additional liquid crystal components must be miscible with the compounds of formula (I). Examples of known mesogenic materials suitable for use with the compounds of the present invention are listed below. Further examples of additional components that may be used in the mixtures of the present invention can be found in US 4,898,455. US 4,929,278, US 5.082,589, US 5.238,602, US 5,100.577 and US 5,242,619.
  • Ferroelectric liquid crystal mixtures may be readily prepared by admixing the compounds of formula (I) with one or more additional mesogenic or non-mesogenic components.
  • a fourth aspect of the invention therefore provides a method of preparing a ferroelectric liquid crystal mixture comprising admixing a compound of formula (I) with a further mesogenic or non-mesogenic compound.
  • the one or more additional components may include further compounds of formula (I) or other suitable mesogenic or non-mesogenic components such as those referred to above.
  • the compounds of the invention may be used in the preparation of ferroelectric liquid crystal devices. As indicated above, such devices have been found to exhibit superior optical and electro-optical properties.
  • a fifth aspect of the invention therefore provides the use of a compound of formula (I) in the preparation of a ferroelectric liquid crystal device.
  • the compounds of formula (I) may be used alone but are most preferably used in the form of a liquid crystal mixture as defined above.
  • the invention also includes an optic or electo-optic device comprising a compound of formula (I) in addition to an optic or electro-optic device comprising a liquid crystal mixture as defined above.
  • an optic or electo-optic device comprising a compound of formula (I) in addition to an optic or electro-optic device comprising a liquid crystal mixture as defined above.
  • a ferroelectric liquid crystal mixture, SCO-1014 having the composition shown in table
  • Table I The composition of the test mixture SCO-1014.
  • N, S A and Sc* are the upper temperature limits of the corresponding LC-phases.
  • a missing phase is denoted by "-".
  • 2 ⁇ is the observed switching angle at 25°C, measured in test cells with 1 OV pp / ⁇ m square wave field applied.
  • test cells have ITO electrodes, low-tilt, parallel-brushed polyimide orientation layers and a cell gap of 1 O ⁇ m.

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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)
  • Plural Heterocyclic Compounds (AREA)
  • Liquid Crystal (AREA)

Abstract

L'invention concerne un composé correspondant à la formule (1): (formule 1) dans laquelle R1 représente un alkyle C1-20 ou un alcényle C1-20 chiral, non chiral, ramifié ou droit, qui peut être éventuellement substitué par un ou plusieurs atomes d'halogène et dans lequel un ou plusieurs groupes -CH2- non adjacents peuvent être éventuellement remplacés par -CH=CH-, -O-, -CO-, -COO-, -OOC-, -O-OC-O- ou -S-; R2 représente un C¿1-20? alcoxy, C1-20 alcényloxy, C1-20 alkylcarbonyloxy (alkyl-COO-) ou C1-20 alcénylcarbonyloxy (alcényl-COO-) chiral, non chiral, ramifié ou droit, qui peut être éventuellement substitué par un ou plusieurs atomes d'halogène et dans lequel un ou plusieurs groupes CH2- non adjacents peuvent être éventuellement remplacés par -CH=CH-, -O-, -CO-, -COO-, -OOC-, -O-OC-O- ou -S-; MG1 représente un groupe correspondant à la formule (1a): (formule 1a) dans laquelle A et B sont chacun indépendamment un groupe 1,4-phénylène ou 1,4-cyclohéxylène, chacun pouvant être éventuellement remplacé par halogène, cyano ou nitro ou un groupe correspondant à R?1¿ et dans lequel un ou plusieurs groupes -CH- ou -CH¿2?- non adjacents peuvent éventuellement être remplacés par azote ou oxygène, respectivement; Z?1, Z2, Z3¿ représentent indépendamment une liaison unique -COO- ou -OOC-, -CH¿2?CH2-, -CH=CH-, -C C-, -OCH2- ou -CH2O-, m et n étant chacun indépendamment 0 ou 1; et MG?2¿ représente un groupe 1,4 phénylène pouvant être éventuellement substitué par halogène, cyano ou nitro ou un groupe correspondant à R1 et dans lequel un ou plusieurs groupes -CH- non adjacents sont remplacés par azote. Le composé peut servir dans la préparation de dispositif à cristaux liquides ferroélectriques.
PCT/IB1999/001831 1998-11-23 1999-11-15 Compose a base de cristaux liquides WO2000031211A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2000584028A JP2002530434A (ja) 1998-11-23 1999-11-15 液晶化合物
EP99954281A EP1137737A1 (fr) 1998-11-23 1999-11-15 Compose a base de cristaux liquides
KR1020017006431A KR20010089493A (ko) 1998-11-23 1999-11-15 액정 화합물
AU10690/00A AU1069000A (en) 1998-11-23 1999-11-15 Liquid crystal compound

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9825628.2 1998-11-23
GBGB9825628.2A GB9825628D0 (en) 1998-11-23 1998-11-23 Liquid crystal compound

Publications (1)

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WO2000031211A1 true WO2000031211A1 (fr) 2000-06-02

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EP (1) EP1137737A1 (fr)
JP (1) JP2002530434A (fr)
KR (1) KR20010089493A (fr)
CN (1) CN1328596A (fr)
AU (1) AU1069000A (fr)
GB (1) GB9825628D0 (fr)
WO (1) WO2000031211A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0154840A2 (fr) * 1984-02-18 1985-09-18 MERCK PATENT GmbH Composés de cristaux liquides
WO1996030344A2 (fr) * 1995-03-28 1996-10-03 The Secretary Of State For Defence Composes de pyrimidine
WO1998032721A1 (fr) * 1997-01-22 1998-07-30 Chisso Corporation Composes et composition a cristaux liquides et element graphique a cristaux liquides contenant lesdits composes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0154840A2 (fr) * 1984-02-18 1985-09-18 MERCK PATENT GmbH Composés de cristaux liquides
WO1996030344A2 (fr) * 1995-03-28 1996-10-03 The Secretary Of State For Defence Composes de pyrimidine
WO1998032721A1 (fr) * 1997-01-22 1998-07-30 Chisso Corporation Composes et composition a cristaux liquides et element graphique a cristaux liquides contenant lesdits composes

Also Published As

Publication number Publication date
EP1137737A1 (fr) 2001-10-04
CN1328596A (zh) 2001-12-26
KR20010089493A (ko) 2001-10-06
GB9825628D0 (en) 1999-01-13
AU1069000A (en) 2000-06-13
JP2002530434A (ja) 2002-09-17

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