WO2004087835A1 - Composes polymerisables chiraux - Google Patents

Composes polymerisables chiraux Download PDF

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Publication number
WO2004087835A1
WO2004087835A1 PCT/EP2004/002157 EP2004002157W WO2004087835A1 WO 2004087835 A1 WO2004087835 A1 WO 2004087835A1 EP 2004002157 W EP2004002157 W EP 2004002157W WO 2004087835 A1 WO2004087835 A1 WO 2004087835A1
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
liquid crystal
atoms
chiral
compound
Prior art date
Application number
PCT/EP2004/002157
Other languages
English (en)
Inventor
Ian Victor Edward Hassall
Alison Linda May
Original Assignee
Merck Patent Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh
Priority to JP2006504526A priority Critical patent/JP2006526669A/ja
Publication of WO2004087835A1 publication Critical patent/WO2004087835A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/58—Dopants or charge transfer agents
    • C09K19/586—Optically active dopants; chiral dopants
    • C09K19/588—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • 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
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K2019/3095—Cyclohexane rings in which the end group is the monoterpene menthyl
    • 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
    • C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
    • C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems

Definitions

  • the invention relates to compounds of formula I
  • Sp is a spacer group or a single bond
  • the compounds of formula I are especially suitable for use in polymerizable mixtures for the preparation of patterned chiral LC films which can be used as optical films, like colour filters in an LCD, or as decorative or security images.
  • R is straight chain alkyl or alkoxy with 1 to 12, preferably 1 to 8 C- atoms or alkenyl with 2 to 12, preferably 2 to 7 C-atoms,
  • L is selected from F, CI, CN, N0 2 or straight chain or branched aikyl, alkoxy or alkylcarbonyl with 1 to 4 C atoms, wherein the alkyl groups are optionally perfluorinated.
  • Halogen is preferably F or CI.
  • OCF 3 OCHF 2 , OCH 2 F, C 2 F 5 and OC 2 F 5 , in particular F, CI, CN, CF 3 , OCHF 2 and OCF 3 .
  • a non-polar group it is preferably alkyl with up to 15 C atoms or alkoxy with 2 to 15 C atoms.
  • achiral branched group R may occasionally be of importance, for example, due to a reduction in the tendency towards crystallization.
  • Branched groups of this type generally do not contain more than one chain branch.
  • inventive compounds, mixtures and polymers are especially suitable for cholesteric displays, like for example surface stabilized or polymer stabilized cholesteric texture displays (SSCT, PSCT) as described in WO 92/19695, WO 93/23496, US 5,453,863 or US 5,493,430, in particular for liquid crystal devices with variable pitch, like multi-domain liquid crystal displays as described for example in WO 98/57223, or multicolour cholesteric displays as described for example in US 5,668,614.
  • SSCT surface stabilized or polymer stabilized cholesteric texture displays
  • the polymerizable liquid crystal mixture comprises at least one polymerizable mesogenic compound having one polymerizable functional group and at least one polymerizable mesogenic compound having two or more polymerizable functional groups.
  • a photoinitiator for radical polymerization for example the commercially available Irgacure 651 , Irgacure 184, Darocure 1173 or Darocure 4205 (all from Ciba Geigy AG) can be used, whereas in case of cationic photopolymerization the commercially available UVI 6974 (Union Carbide) can be used.
  • polymerization is carried out under an atmosphere of inert gas, preferably under a nitrogen atmosphere.
  • At least one substrate is a plastic substrate such as for example a film of polyester such as polyethyleneterephthalate (PET) or polyethylenenaphthalate (PEN), of polyvinyialcohol (PVA), polycarbonate (PC) or triacetylcellulose (TAG), especially preferably a PET film or a TAG film.
  • PET polyethyleneterephthalate
  • PEN polyethylenenaphthalate
  • PVA polyvinyialcohol
  • PC polycarbonate
  • TAG triacetylcellulose
  • PET films are commercially available from ICI Corp. under the trade name Melinex.
  • the polymerizable mixture is preferably coated as a thin layer on a substrate or between substrate, and aligned in its chiral mesophase, e.g. the cholesteric or chiral smectic phase, to give a planar orientation, i.e. wherein the axis of the molecular helix extends transversely to the layer.
  • Planar orientation can be achieved for example by shearing the mixture, e.g. by means of a doctor blade.
  • an alignment layer for example a layer of rubbed polyimide or sputtered SiO x , on top of at least one of the substrates.
  • a second substrate is put on top of the coated material. In this case, the shearing caused by putting together the two substrates is sufficient to give good alignment.
  • an electric or magnetic field to the coated mixture.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Liquid Crystal Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cleaning In Electrography (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Cette invention concerne des composés polymérisables et photo-isomérisables chiraux et concerne également leur utilisation dans des milieux à cristaux liquides, des dispositifs à cristaux liquides, des polymères anisotropiques, des applications optiques, électro-optiques, de décoration, de sécurité, cosmétiques, diagnostiques, électriques, électroniques, de transport de charge, de semi-conducteurs, d'enregistrement optique, électroluminescentes, de photoconducteurs, électrophotographiques et lasers. Cette invention concerne également des milieux à cristaux liquides, des polymères, des composants optiques, des affichages et des marquages de décoration ou de sécurité renfermant ces composés polymérisables chiraux.
PCT/EP2004/002157 2003-04-01 2004-03-04 Composes polymerisables chiraux WO2004087835A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2006504526A JP2006526669A (ja) 2003-04-01 2004-03-04 重合可能なキラル化合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP03007236 2003-04-01
EP03007236.7 2003-04-01

Publications (1)

Publication Number Publication Date
WO2004087835A1 true WO2004087835A1 (fr) 2004-10-14

Family

ID=33104042

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2004/002157 WO2004087835A1 (fr) 2003-04-01 2004-03-04 Composes polymerisables chiraux

Country Status (2)

Country Link
JP (1) JP2006526669A (fr)
WO (1) WO2004087835A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007269639A (ja) * 2006-03-30 2007-10-18 Dainippon Ink & Chem Inc 重合性キラル化合物
US8481129B2 (en) 2011-11-25 2013-07-09 Industrial Technology Research Institute Liquid crystal compounds, and liquid crystal displays and photochromic materials comprising the liquid crystal compounds
US8540896B2 (en) 2009-11-12 2013-09-24 Industrial Technology Research Institute Chiral compound and liquid crystal composition containing the same
US9663486B2 (en) 2013-10-14 2017-05-30 Eisai R&D Management Co., Ltd. Selectively substituted quinoline compounds
US10087174B2 (en) 2013-10-14 2018-10-02 Eisai R&D Management Co., Ltd. Selectively substituted quinoline compounds
CN111171202A (zh) * 2020-01-12 2020-05-19 湘潭大学 一种侧链型手性发光液晶聚合物及其制备方法
CN111187374A (zh) * 2020-01-12 2020-05-22 湘潭大学 一种含薄荷醇手性结构的发光液晶聚合物及其制备方法
CN113429982A (zh) * 2021-06-10 2021-09-24 江苏集萃智能液晶科技有限公司 一种温度自适应液晶组合物及应用其的液晶调光器件

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5245118B2 (ja) * 2008-03-07 2013-07-24 和歌山県 新規な重合性化合物およびその製造方法
US8507699B2 (en) * 2010-12-10 2013-08-13 Sabic Innovative Plastics Ip B.V. Bisphenol polymer structural units and method of making the same
US9581924B2 (en) * 2014-11-14 2017-02-28 Xerox Corporation Bio-based acrylate and (meth)acrylate resins

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998000428A1 (fr) * 1996-07-01 1998-01-08 Merck Patent Gmbh Dopants chiraux
GB2314839A (en) * 1996-07-01 1998-01-14 Merck Patent Gmbh Chiral reactive mesogens
US20030026922A1 (en) * 2001-07-02 2003-02-06 Merck Patent Gmbh Chiral compounds

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998000428A1 (fr) * 1996-07-01 1998-01-08 Merck Patent Gmbh Dopants chiraux
GB2314839A (en) * 1996-07-01 1998-01-14 Merck Patent Gmbh Chiral reactive mesogens
US20030026922A1 (en) * 2001-07-02 2003-02-06 Merck Patent Gmbh Chiral compounds

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007269639A (ja) * 2006-03-30 2007-10-18 Dainippon Ink & Chem Inc 重合性キラル化合物
US8540896B2 (en) 2009-11-12 2013-09-24 Industrial Technology Research Institute Chiral compound and liquid crystal composition containing the same
US8481129B2 (en) 2011-11-25 2013-07-09 Industrial Technology Research Institute Liquid crystal compounds, and liquid crystal displays and photochromic materials comprising the liquid crystal compounds
US9663486B2 (en) 2013-10-14 2017-05-30 Eisai R&D Management Co., Ltd. Selectively substituted quinoline compounds
US10087174B2 (en) 2013-10-14 2018-10-02 Eisai R&D Management Co., Ltd. Selectively substituted quinoline compounds
USRE47193E1 (en) 2013-10-14 2019-01-08 Eisai R&D Management Co., Ltd. Selectively substituted quinoline compounds
CN111171202A (zh) * 2020-01-12 2020-05-19 湘潭大学 一种侧链型手性发光液晶聚合物及其制备方法
CN111187374A (zh) * 2020-01-12 2020-05-22 湘潭大学 一种含薄荷醇手性结构的发光液晶聚合物及其制备方法
CN111187374B (zh) * 2020-01-12 2022-02-08 湘潭大学 一种含薄荷醇手性结构的发光液晶聚合物及其制备方法
CN111171202B (zh) * 2020-01-12 2022-02-11 湘潭大学 一种侧链型手性发光液晶聚合物及其制备方法
CN113429982A (zh) * 2021-06-10 2021-09-24 江苏集萃智能液晶科技有限公司 一种温度自适应液晶组合物及应用其的液晶调光器件

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Publication number Publication date
JP2006526669A (ja) 2006-11-24

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