WO2018141759A1 - Composés cristaux liquides - Google Patents

Composés cristaux liquides Download PDF

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Publication number
WO2018141759A1
WO2018141759A1 PCT/EP2018/052322 EP2018052322W WO2018141759A1 WO 2018141759 A1 WO2018141759 A1 WO 2018141759A1 EP 2018052322 W EP2018052322 W EP 2018052322W WO 2018141759 A1 WO2018141759 A1 WO 2018141759A1
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WO
WIPO (PCT)
Prior art keywords
compounds
formula
liquid
atoms
crystalline
Prior art date
Application number
PCT/EP2018/052322
Other languages
German (de)
English (en)
Inventor
Constanze Brocke
Achim Goetz
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 CN201880009876.9A priority Critical patent/CN110325522B/zh
Publication of WO2018141759A1 publication Critical patent/WO2018141759A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • 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
    • C09K19/3402—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 invention relates to compounds of the formula I as defined below, a process for their preparation, liquid-crystalline media comprising at least one compound of the formula I and their use as component (s) in liquid-crystalline media. Moreover, the present invention relates to liquid crystal and electro-optical
  • Display elements which contain the liquid-crystalline media according to the invention.
  • the compounds according to the invention have as structural element a characteristically substituted 2- (4-phenyl-cyclohex-3-enyl) - [1,3] -dioxane group.
  • the nematic liquid-crystal mixtures have hitherto found the widest application in flat display devices. They were especially in passive TN or
  • the liquid-crystalline compounds according to the invention can be used as component (s) of liquid-crystalline media, in particular for displays based on the principle of the twisted cell, the guest-host effect, the effect of deformation of upright phases DAP or ECB (electrically controlled birefringence), based on the IPS effect (in-plane switching) or the effect of dynamic dispersion.
  • DAP or ECB electrically controlled birefringence
  • IPS effect in-plane switching
  • dynamic dispersion The use of polar dioxane compounds having three rings as liquid-crystalline substances is not unknown to the person skilled in the art.
  • Various compounds have been described with a dioxane ring as a liquid crystalline or mesogenic material and its preparation, such as. In document CN 105038816 A. The compounds proposed therein have no cyclohexene ring.
  • the compounds contain z.
  • -OCF 3 or fluorine it is an object of the present invention to find novel stable compounds which are suitable as component (s) of liquid-crystalline media.
  • the compounds should simultaneously have a comparatively low viscosity, as well as a high dielectric
  • the invention was thus an object of new stable
  • the compounds of the invention should be thermally and photochemically stable under the conditions prevailing in the fields of application. As mesogens they should have a broad
  • Solubility a broad liquid crystalline phase and a low tendency for spontaneous crystallization in mixtures at low temperatures.
  • the compounds according to the invention are outstandingly suitable as components of liquid-crystalline media.
  • liquid-crystalline media can be obtained for displays that require particularly high dielectric anisotropies, in particular for IPS or FFS displays, but also for TN or STN displays.
  • the compounds of the invention are sufficiently stable and colorless. In particular, they are distinguished by high dielectric anisotropies ⁇ , as a result of which, in the application in optical switching elements, lower layer thicknesses and thus
  • the compounds have relatively low melting points. Surprisingly, it is possible with the compounds according to the invention to prepare liquid-crystalline mixtures having high values for the elastic constants (K 11 / K 22 / K 33 ) without adversely affecting the other application parameters.
  • the compounds of the invention have a broad spectrum
  • these compounds may serve as base materials from which liquid crystalline media are predominantly composed. But it can also be the compounds of the invention.
  • liquid crystal base materials can be added from other classes of compounds, for example, to influence the dielectric and / or the optical anisotropy of such a dielectric and / or to optimize its threshold voltage and / or its viscosity.
  • the invention thus relates to compounds of the formula I
  • L 1 and L 2 independently of one another are H or F, preferably H,
  • the invention further relates to the use of the compounds of the formula I in liquid-crystalline media.
  • liquid-crystalline media having at least two liquid-crystalline components which contain at least one compound of the formula I.
  • the compounds of the formula I have a wide range of applications. Depending on the choice of substituents, these compounds may serve as base materials from which liquid crystalline media are predominantly composed; However, it is also possible to add compounds of the formula I to liquid-crystalline base materials from other classes of compounds in order, for example, to influence the dielectric and / or optical anisotropy of such a dielectric and / or to optimize its threshold voltage and / or its viscosity.
  • the compounds of the formula I are colorless in the pure state and form liquid-crystalline mesophases in their own or in mixtures in a temperature range which is favorably located for electrooptical use. With the compounds according to the invention, broad nematic phase ranges can be achieved. In liquid-crystalline mixtures, the substances according to the invention significantly increase the optical anisotropy and / or lead to an improvement in the low-temperature storage stability compared to comparable mixtures with a high dielectric content
  • the compounds are characterized by good UV stability.
  • R 1 of the formula I and its sub-formulas preferably denotes alkyl or alkenyl having up to 8 carbon atoms.
  • R 1 particularly preferably denotes a straight-chain alkyl radical having 1 to 7 C atoms or an unbranched alkenyl radical having 2 to 8 C atoms, in particular
  • the radical -CH CH-CF 3 is preferably trans-configured.
  • Wing groups R 1 may occasionally be of importance for better solubility in the usual liquid crystalline base materials.
  • the group R 1 is preferably straight-chain. Preference is given to compounds of the formulas I in which L 1 is H, in particular in which L 1 and L 2 are H.
  • the radical R 1 is particularly preferably selected from the substructures: -CH 3
  • alkyl chains are preferably unbranched (n-alkyl).
  • Particularly preferred compounds of the formula I are the compounds of the formulas 1-1 to I-6:
  • R 1 independently has the meanings given above.
  • the formulas 1-1 to I-6 the formulas 1-1, I-2, I-4 and I-5 are preferred, in particular the compounds of the formula 1-1 and I-2.
  • the invention therefore also has a process for the preparation of
  • the invention relates to compounds of the formula I which comprise a process step in which an arylmetal compound of the formula II
  • M means Li, MgBr or MgCl
  • PG is a protecting group, preferably benzyl
  • Reaction mixture can in principle be carried out as a batch reaction or in a continuous reaction mode.
  • the continuous reaction includes z.
  • a stirred tank cascade As the reaction in a continuous stirred tank reactor, a stirred tank cascade, a loop or cross-flow reactor, a flow tube or in a microreactor.
  • the work-up of the reaction mixtures is optionally carried out, as required, by filtration over solid phases, chromatography, separation between immiscible phases (eg extraction), adsorption on solid supports, distilling off solvents and / or azeotropic mixtures, selective distillation, sublimation, crystallization, cocrystallization or by nanofiltration on membranes.
  • Substituents in the preferred chair conformation are both preferably in the equatorial position.
  • the invention also relates to liquid-crystalline media containing one or more of the compounds of the formula I.
  • the liquid-crystalline media contain at least two components. They are preferably obtained by mixing the components together.
  • a process according to the invention for the preparation of a liquid-crystalline medium is therefore characterized in that at least one compound of the formula I is mixed with at least one further mesogenic compound and, if appropriate, additives are added.
  • liquid-crystalline media according to the invention contain
  • Compounds as further constituents 2 to 40 more preferably 4 to 30 components.
  • these media include next to one or more compounds of the invention 7 to 25 components.
  • These further constituents are preferably selected from nematic or nematogenic (monotropic or isotropic) substances, in particular substances from the classes of azoxybenzenes,
  • Cyclohexylbenzoe phenyl or cyclohexyl esters of cyclohexylcyclohexanecarboxylic, Cyclohexylphenylester of benzoic acid, cyclohexanecarboxylic or Cyclohexylcyclohexancarbonklare, Phenylcyclohexane, Cyclohexylbiphenyls, Phenylcyclohexylcyclohexane, Cyclohexylcyclohexane, Cyclohexylcyclohexylcyclohexane, 1, 4-bis-cyclo-hexylbenzenes, 4,4'-bis-cyclohexylbiphenyls , Phenyl- or cyclohexylpyrimidines, phenyl- or cyclohexylpyridines, phenyl- or cyclohexyl-dioxanes, phen
  • R'-LC CE "5 In the formulas 1, 2, 3, 4 and 5, L and E, which may be the same or different, each independently represent a bivalent radical of the structural elements -Phe-, -Cyc-, -Phe- Phe-, - Phe-Cyc, -Cyc-Cyc, -Pyr, -Dio, -Py, -G-Phe, -G-Cyc and their mirror images formed group, wherein Phe is unsubstituted or substituted by fluorine 1, 4 Phenylene, Cyc trans-1, 4-cyclohexylene, Pyr pyrimidine-2,5-diyl or pyridine-2,5-diyl, diol 1, 3-dioxane-2,5-diyl, Py
  • one of L and E is Cyc, Phe or Pyr.
  • E is preferably Cyc, Phe or Phe-Cyc.
  • the media according to the invention preferably comprise one or more components selected from the compounds of the formulas 1, 2, 3, 4 and 5, in which L and E are selected from the group Cyc, Phe and Pyr and simultaneously one or more components selected from the compounds of the
  • R 'and / or R each independently represent alkyl, alkenyl, alkoxy, alkoxyalkyl, alkenyloxy or alkanoyloxy having up to 8 C atoms, -F, -Cl, -CN, -NCS or - (O) iCH 3 -kF k , where i is 0 or 1 and k is 1, 2 or 3.
  • R 'and R each independently represent alkyl, alkenyl, alkoxy, alkoxyalkyl, alkenyloxy or alkanoyloxy having up to 8 C atoms in a smaller subgroup of the compounds of the formulas 1, 2, 3, 4 and 5 Subgroup group A called and the compounds are with the subformulae 1 a, 2 a, 3 a, 4 a and 5 a
  • R 'and R "are different from each other one of these radicals is usually alkyl, alkenyl, alkoxy or alkoxyalkyl.
  • the compounds in which R "has this meaning are designated by the subformulae 1 b, 2b, 3b, 4b and 5b.
  • R has the meaning -F, -Cl, -NCS, -CF 3 , -OCHF 2 or -OCF 3 .
  • R ' has the meanings given for the compounds of the subformulae 1a to 5a and is preferably alkyl, alkenyl, alkoxy or alkoxyalkyl.
  • R denotes -CN.
  • This subgroup is referred to below as group C and the compounds of this subgroup are correspondingly reacted with partial formulas 1 c, 2c, 3c, 4c and 5c
  • R ' has the meanings given for the compounds of the subformulae 1a to 5a and is preferably alkyl, alkoxy or alkenyl.
  • the media according to the invention preferably comprise one or more compounds which are selected from the groups A, B and / or C.
  • the mass fractions of the compounds from these groups in the media according to the invention are preferably:
  • Group A 0 to 90%, preferably 20 to 90%, particularly preferably 30 to 90%;
  • Group B 0 to 80%, preferably 10 to 80%, particularly preferably 10 to 65%
  • Group C 0 to 80%, preferably 0 to 80%, particularly preferably 0 to 50%; wherein the sum of the mass fractions of the compounds of the groups A, B and / or C contained in the respective inventive media is preferably 5 to 90% and particularly preferably 10 to 90%.
  • the media according to the invention preferably contain 1 to 40%, particularly preferably 3 to 30%, of the compounds according to the invention.
  • the preparation of the liquid-crystal mixtures according to the invention is carried out in a conventional manner.
  • the desired amount of the components used in lesser amount in the main constituent components is dissolved, preferably at elevated
  • premixes e.g. Homologous mixtures or using so-called “multi-bottle” systems produce.
  • the dielectrics may also contain further additives known to the person skilled in the art and described in the literature. For example, 0 to 15%, preferably 0 to 10%, pleochroic dyes, chiral
  • Dopants, stabilizers or nanoparticles can be added.
  • the individual added compounds are used in concentrations of 0.01 to 6%, preferably from 0.1 to 3%.
  • concentration data of the other constituents of the liquid-crystal mixtures ie the liquid-crystalline or mesogenic compounds are given, without taking into account the concentration of these additives.
  • the liquid-crystal mixtures according to the invention enable a significant expansion of the available parameter space.
  • the invention also provides electro-optical displays (in particular TFT displays with two plane-parallel carrier plates which form a cell with a border, integrated non-linear elements for switching individual pixels on the carrier plates and a nematic liquid crystal mixture having positive dielectric anisotropy and in the cell high resistivity) containing such media and the use of these media for electro-optical purposes.
  • electro-optical displays in particular TFT displays with two plane-parallel carrier plates which form a cell with a border, integrated non-linear elements for switching individual pixels on the carrier plates and a nematic liquid crystal mixture having positive dielectric anisotropy and in the cell high resistivity
  • alkyl embraces unbranched and branched alkyl groups having 1-15 carbon atoms, in particular the unbranched groups methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl and n-heptyl. Groups of 2-5 carbon atoms are generally
  • alkenyl includes unbranched and branched alkenyl groups having up to 15 carbon atoms, especially the unbranched groups. Particularly preferred alkenyl groups are C 2 -C 7 -1 E-alkenyl, C 4 -C 7 -3E-alkenyl, C 5 -C 7 -4-alkenyl, C 6 -C 7 -5-alkenyl and C 7 -6 Alkenyl, in particular C 2 -C 7 -1 E-alkenyl, C 4 -C 7 3E-alkenyl and C 5 -C 7 -4-alkenyl. Examples of preferred alkenyl groups are vinyl, 1 E-propenyl,
  • Groups of up to 5 carbon atoms are generally preferred.
  • halogenated alkyl preferably includes mono- or polyfluorinated and / or chlorinated radicals. Perhalogenated radicals are included. Particularly preferred are fluorinated alkyl radicals,
  • the total amount of compounds of the formula I in the mixtures according to the invention is not critical.
  • the mixtures may therefore contain one or more other components to optimize various properties.
  • the structure of the matrix display of polarizers, electrode base plates and electrodes with surface treatment according to the invention corresponds to the usual construction for such displays.
  • the term of the usual construction is broad and includes all
  • the dielectric anisotropy ⁇ of the individual substances is determined at 20 ° C and 1 kHz. For this purpose, 5-10% by weight of the substance to be investigated is dissolved in the dielectrically positive mixture ZLI-4792 (Merck KGaA) and the measured value is brought to a concentration of 100%. extrapolated.
  • the optical anisotropy ⁇ is at 20 ° C and a
  • Wavelength of 589.3 nm determines the rotational viscosity at 20 ° C, both also by linear extrapolation.
  • the plural form of a term means both the singular form and the plural form, and vice versa.
  • the aqueous phase is separated and extracted with DCM.
  • the combined organic phases are mixed with water and Washed sodium chloride solution, dried over sodium sulfate, filtered and evaporated to dryness to the residue.
  • the crude product is then chromatographed on silica gel (DCM / EA 8: 2). 4-Hydroxy-4- (4-trifluoromethyl-phenyl) -cyclohexanecarbaldehyde 5 is obtained as a yellow oil.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des composés de formule (I) dans laquelle R1, L1, L2 et X ont les significations figurant dans la revendication 1, un procédé pour leur préparation, des milieux cristaux liquides contenant au moins un composé de formule (I) ainsi que des écrans électro-optiques contenant un tel milieu cristal liquide.
PCT/EP2018/052322 2017-02-03 2018-01-31 Composés cristaux liquides WO2018141759A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201880009876.9A CN110325522B (zh) 2017-02-03 2018-01-31 液晶化合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102017000971 2017-02-03
DE102017000971.6 2017-02-03

Publications (1)

Publication Number Publication Date
WO2018141759A1 true WO2018141759A1 (fr) 2018-08-09

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PCT/EP2018/052322 WO2018141759A1 (fr) 2017-02-03 2018-01-31 Composés cristaux liquides

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CN (1) CN110325522B (fr)
DE (1) DE102018000075A1 (fr)
TW (1) TWI761441B (fr)
WO (1) WO2018141759A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020094535A1 (fr) 2018-11-07 2020-05-14 Merck Patent Gmbh Milieu cristallin liquide et écran à cristaux liquides comprenant celui-ci
CN111170984A (zh) * 2019-03-18 2020-05-19 默克专利股份有限公司 液晶化合物
DE102021000109A1 (de) 2020-02-05 2021-08-05 MERCK Patent Gesellschaft mit beschränkter Haftung Flüssigkristalline verbindungen

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4940822A (en) 1988-11-04 1990-07-10 Warner-Lambert Company Substituted benzenemethanol compounds, intermediates thereof, and preparation thereof
WO2008019743A1 (fr) * 2006-08-16 2008-02-21 Merck Patent Gmbh Composés de cyclohexène pour mélanges liquides cristallins
CN105038816A (zh) 2015-07-13 2015-11-11 石家庄诚志永华显示材料有限公司 液晶组合物
US20150368225A1 (en) * 2014-06-18 2015-12-24 Jnc Corporation 1,3-dioxane compound having fluorine atom in axial position, liquid crystal composition and liquid crystal display device
WO2016133035A1 (fr) * 2015-02-17 2016-08-25 Jnc株式会社 Composé présentant un cycle saturé à six chaînons et un groupe alcoxy ou un groupe alcoxyalkyle, composition de cristaux liquides et élément d'affichage à cristaux liquides

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010119779A1 (fr) * 2009-04-14 2010-10-21 Dic株式会社 Composition de cristaux liquides contenant un composé polymérisable, élément d'affichage à cristaux liquides l'utilisant

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4940822A (en) 1988-11-04 1990-07-10 Warner-Lambert Company Substituted benzenemethanol compounds, intermediates thereof, and preparation thereof
WO2008019743A1 (fr) * 2006-08-16 2008-02-21 Merck Patent Gmbh Composés de cyclohexène pour mélanges liquides cristallins
US20150368225A1 (en) * 2014-06-18 2015-12-24 Jnc Corporation 1,3-dioxane compound having fluorine atom in axial position, liquid crystal composition and liquid crystal display device
WO2016133035A1 (fr) * 2015-02-17 2016-08-25 Jnc株式会社 Composé présentant un cycle saturé à six chaînons et un groupe alcoxy ou un groupe alcoxyalkyle, composition de cristaux liquides et élément d'affichage à cristaux liquides
EP3260450A1 (fr) * 2015-02-17 2017-12-27 JNC Corporation Composé présentant un cycle saturé à six chaînons et un groupe alcoxy ou un groupe alcoxyalkyle, composition de cristaux liquides et élément d'affichage à cristaux liquides
CN105038816A (zh) 2015-07-13 2015-11-11 石家庄诚志永华显示材料有限公司 液晶组合物

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020094535A1 (fr) 2018-11-07 2020-05-14 Merck Patent Gmbh Milieu cristallin liquide et écran à cristaux liquides comprenant celui-ci
CN112996882A (zh) * 2018-11-07 2021-06-18 默克专利股份有限公司 液晶介质和包含其的液晶显示器
US20230045269A1 (en) * 2018-11-07 2023-02-09 Merck Patent Gmbh Liquid-crystalline medium and liquid-crystal display comprising the same
CN112996882B (zh) * 2018-11-07 2024-07-23 默克专利股份有限公司 液晶介质和包含其的液晶显示器
CN111170984A (zh) * 2019-03-18 2020-05-19 默克专利股份有限公司 液晶化合物
EP3712230A1 (fr) 2019-03-18 2020-09-23 Merck Patent GmbH Composés à cristaux liquides
US11208595B2 (en) 2019-03-18 2021-12-28 Merck Patent Gmbh Liquid-crystalline compounds
CN111170984B (zh) * 2019-03-18 2024-09-10 默克专利股份有限公司 液晶化合物
DE102021000109A1 (de) 2020-02-05 2021-08-05 MERCK Patent Gesellschaft mit beschränkter Haftung Flüssigkristalline verbindungen
WO2021156232A1 (fr) 2020-02-05 2021-08-12 Merck Patent Gmbh Composés cristallins liquides

Also Published As

Publication number Publication date
CN110325522B (zh) 2022-07-22
CN110325522A (zh) 2019-10-11
DE102018000075A1 (de) 2018-08-09
TW201840828A (zh) 2018-11-16
TWI761441B (zh) 2022-04-21

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