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WO2019030153A1 - Milieu cristal liquide et dispositif à cristaux liquides - Google Patents

Milieu cristal liquide et dispositif à cristaux liquides Download PDF

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WO2019030153A1
WO2019030153A1 PCT/EP2018/071225 EP2018071225W WO2019030153A1 WO 2019030153 A1 WO2019030153 A1 WO 2019030153A1 EP 2018071225 W EP2018071225 W EP 2018071225W WO 2019030153 A1 WO2019030153 A1 WO 2019030153A1
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phe
phel
chex
cyc
compounds
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PCT/EP2018/071225
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Simon SIEMIANOWSKI
Matthias Bremer
Jana JEHN
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Merck Patent Gmbh
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Priority to CN201880050921.5A priority Critical patent/CN110997870B/zh
Publication of WO2019030153A1 publication Critical patent/WO2019030153A1/fr

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    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
    • C09K2019/123—Ph-Ph-Ph
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    • 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
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3009—Cy-Ph
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    • 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
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/301—Cy-Cy-Ph
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    • 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
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3016—Cy-Ph-Ph
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    • 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
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3027—Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene
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    • 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
    • C09K19/3059—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds
    • C09K2019/3063—Cy-Ph-C≡C-Ph
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    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
    • C09K2019/3075—Cy-COO-Ph

Definitions

  • the invention relates to a compound of formula I, R 11 -A 11 -(Z 11 -A 12 )p-X 11 -Sp 11 -X 12 -(A 13 -Z 13 ) q -A 14 -R 12 I wherein R 11 , R 12 , A 11 to A 14 , Z 1 1 , Z 13 , X 11 , X 12 , Sp 11 , p and q have one of the meanings as given herein below.
  • the invention further relates to method of production of a compound of formula I, to the use of said compounds in LC media and to LC media comprising one or more compounds of formula I.
  • the invention relates to a method of production of such LC media, to the use of such media in LC devices, in particular, in flexoelectric LC devices and to a flexoelectric LC device comprising a LC medium according to the present invention.
  • Flexoelectric devices utilizing the flexoelectric effect for example ULH devices and liquid crystal media that are especially suitable for flexoelectric devices and are known from EP 0 971 016, GB 2 356 629 and Coles, H.J., Musgrave, B., Coles, M.J. and Willmott, J., J. Mater. Chem., 11 , p. 2709-2716 (2001 ).
  • the Uniform Lying Helix has high potential as a fast switching liquid crystal display mode. It is capable of sub millisecond switching at 35°C and possesses an intrinsically high aperture ratio, resulting in an energy efficient display mode.
  • the materials commonly used in media suitable for the ULH mode are typically bimesogens. Due to the size of these materials and the presence of polar groups, such as, for example terminal cyano groups, they normally have high rotational viscosities ( ⁇ ) in the order of many thousands mPa.s at 35°C. The high values for ⁇ - ⁇ are not problematically at increased temperatures of, for example, 35°C, since the switching speed is directly proportional to ⁇ . On the other hand, the values for ⁇ 1 are also proportional to the chiral pitch squared. Since the chiral pitch is normally in the region of 300nm this means that, the switching speeds are still very fast, in the region of 1 millisecond or a few milliseconds.
  • the corresponding LC media should exhibit favourable low values while preferably at the same time exhibiting:
  • liquid crystal means a compound that under suitable conditions of temperature, pressure and concentration can exist as a mesophase (nematic, smectic, etc.) or in particular as a LC phase.
  • mesophase nematic, smectic, etc.
  • Non-amphiphilic mesogenic compounds comprise for example one or more calamitic, banana-shaped or discotic mesogenic groups.
  • mesogenic group means in this context, a group with the ability to induce liquid crystal (LC) phase behaviour.
  • the compounds comprising mesogenic groups do not necessarily have to exhibit an LC phase themselves. It is also possible that they show LC phase behaviour only in mixtures with other compounds.
  • liquid crystal is used hereinafter for both mesogenic and LC materials.
  • aryl and heteroaryl groups encompass groups, which can be
  • monocyclic or polycyclic i.e. they can have one ring (such as, for example, phenyl) or two or more rings, which may also be fused (such as, for example, naphthyl) or covalently linked (such as, for example, biphenyl) or contain a combination of fused and linked rings.
  • one ring such as, for example, phenyl
  • two or more rings which may also be fused (such as, for example, naphthyl) or covalently linked (such as, for example, biphenyl) or contain a combination of fused and linked rings.
  • Heteroaryl groups contain one or more heteroatoms, preferably selected from O, N, S and Se. Particular preference is given to mono-, bi- or tricyclic aryl groups having 6 to 25 C atoms and mono-, bi- or tricyclic heteroaryl groups having 2 to 25 C atoms, which optionally contain fused rings and which are optionally substituted. Preference is furthermore given to 5 , 6 or 7-membered aryl and heteroaryl groups, in which, in addition, one or more CH groups may be replaced by N, S or O in such a way that O atoms and/or S atoms are not linked directly to one another.
  • Preferred aryl groups are, for example, phenyl, biphenyl, terphenyl,
  • phenanthrene pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzopyrene, fluorene, indene, indenofluorene,
  • spirobifluorene more preferably 1 ,4- phenylene, 4,4'-biphenylene, 1 , 4- tephenylene.
  • Preferred heteroaryl groups are, for example, 5 membered rings, such as pyrrole, pyrazole, imidazole, 1 ,2,3-triazole, 1 ,2,4-triazole, tetrazole, furan, thiophene, selenophene, oxazole, isoxazole, 1 ,2 thiazole, 1 ,3-thiazole, 1 ,2,3-oxadiazole, 1 ,2,4 oxadiazole, 1 ,2,5-oxadiazole, 1 ,3,4-oxadiazole, 1 ,2,3-thiadiazole, 1 ,2,4-thiadiazole, 1 ,2,5-thiadiazole, 1 ,3,4-thiadiazole, 6 membered rings, such as pyridine
  • non-aromatic alicyclic groups encompass saturated rings and “heterocyclic groups”.
  • Heterocyclic rings contain one or more heteroatoms, preferably selected from Si, O, N, S and Se.
  • the (non-aromatic) alicyclic and heterocyclic groups can be monocyclic, i.e. contain only one ring (such as, for example, cyclohexane) or polycyclic, i.e. contain a plurality of rings (such as, for example, decahydro-naphthalene or bicyclooctane).
  • Preferred alicyclic and heterocyclic groups are, for example, 5-membered groups, such as cyclopentane, tetrahydrofuran, tetrahydrothiofuran, pyrrolidine, 6-membered groups, such as
  • cycloheptane and fused groups such as tetrahydronaphthalene, decahydronaphthalene, indane, bicyclo[1 .1 .1 ]->pentane-1 ,3-diyl, bicyclo[2.2.2]octane-1 ,4-diyl, spiro[3.3]heptane-2,6-diyl, octahydro-4,7- methanoindane-2,5-diyl, more preferably 1 ,4-cyclohexylene 4,4'- bicyclohexylene, 3,17-hexadecahydro-cyclopenta[a]phenanthrene, optionally being substituted by one or more identical or different groups L.
  • groups L such as tetrahydronaphthalene, decahydronaphthalene, indane, bicyclo[1 .1 .1 ]->pentane-1 ,3-diyl
  • aryl-, heteroaryl-, alicyclic- and heterocyclic groups are 1 ,4-phenylene, 4,4'-biphenylene, 1 , 4-terphenylene, 1 ,4- cyclohexylene, 4,4'- bicyclohexylene and 3,17-hexadecahydro- cyclopenta[a]-phenanthrene, optionally being substituted by one or more identical or different groups L.
  • Preferred substituents of the above-mentioned aryl-, heteroaryl-, alicyclic- and heterocyclic groups (L) are, for example, solubility-promoting groups, such as alkyl or alkoxy and electron-withdrawing groups, such as fluorine, nitro or nitrile.
  • substituents are, for example, halogen, CN, NO2, CH 3 , C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF 3 , OCF3, OCHF2 or OC2F5.
  • halogen denotes F, CI, Br or I.
  • alkyl also encompass polyvalent groups, for example alkylene, arylene,
  • aryl denotes an aromatic carbon group or a group derived there from.
  • heteroaryl denotes “aryl” in accordance with the above definition containing one or more heteroatoms.
  • Preferred alkyl groups are, for example, methyl, ethyl, n propyl, isopropyl, n butyl, isobutyl, s butyl, t butyl, 2 methylbutyl, n pentyl, s pentyl, cyclo- pentyl, n hexyl, cyclohexyl, 2 ethylhexyl, n heptyl, cycloheptyl, n octyl, cyclooctyl, n nonyl, n decyl, n undecyl, n dodecyl, dodecanyl, trifluoro- methyl, perfluoro-n-butyl, 2,2,2-trifluoroethyl, perfluorooctyl, perfluoro- hexyl, etc.
  • Preferred alkoxy groups are, for example, methoxy, ethoxy, 2-methoxy- ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, 2- methylbutoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n- decoxy, n-undecoxy, n-dodecoxy.
  • Preferred alkenyl groups are, for example, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, and octenyl.
  • Preferred alkynyl groups are, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, octynyl.
  • Preferred amino groups are, for example, dimethylamino, methylamino, methylphenylamino, phenylamino.
  • the term "chiral" in general is used to describe an object that is non- superimposable on its mirror image
  • Achiral (non- chiral) objects are objects that are identical to their mirror image.
  • bimesogenic compound relates to compounds comprising two mesogenic groups in the molecule. Just like normal mesogens, they can form many mesophases, depending on their structure. In particular, bimesogenic compound may induce a second nematic phase, when added to a nematic liquid crystal medium. Bimesogenic compounds are also known as "dimeric liquid crystals".
  • director is known in prior art and means the preferred orientation direction of the long molecular axes (in case of calamitic compounds) or short molecular axes (in case of discotic compounds) of the liquid-crystalline molecules. In case of uniaxial ordering of such anisotropic molecules, the director is the axis of anisotropy.
  • alignment relates to alignment (orientation ordering) of anisotropic units of material such as small molecules or fragments of big molecules in a common direction named "alignment direction".
  • the liquid- crystalline director coincides with the alignment direction so that the alignment direction corresponds to the direction of the anisotropy axis of the material.
  • plane orientation/alignment for example in a layer of an liquid-crystalline material, means that the long molecular axes (in case of calamitic compounds) or the short molecular axes (in case of discotic compounds) of a proportion of the liquid-crystalline molecules are oriented substantially parallel (about 180°) to the plane of the layer.
  • homeotropic orientation/alignment for example in a layer of a liquid-crystalline material, means that the long molecular axes (in case of calamitic compounds) or the short molecular axes (in case of discotic compounds) of a proportion of the liquid-crystalline molecules are oriented at an angle ⁇ ("tilt angle") between about 80° to 90° relative to the plane of the layer.
  • uniform orientation or “uniform alignment” of an liquid- crystalline material, for example in a layer of the material, mean that the long molecular axes (in case of calamitic compounds) or the short molecular axes (in case of discotic compounds) of the liquid-crystalline molecules are oriented substantially in the same direction. In other words, the lines of liquid-crystalline director are parallel.
  • the wavelength of light generally referred to in this application is 550 nm, unless explicitly specified otherwise.
  • the extraordinary refractive index n e and the ordinary refractive index n 0 can be measured using an Abbe refractometer.
  • dielectrically positive is used for compounds or components with ⁇ > 3.0, "dielectrically neutral” with -1 .5 ⁇ ⁇ 3.0 and “dielectrically negative” with ⁇ ⁇ -1 .5.
  • ⁇ is determined at a frequency of 1 kHz and at 20°C.
  • the dielectric anisotropy of the respective compound is determined from the results of a solution of 10 % of the respective individual compound in a nematic host mixture. In case the solubility of the respective compound in the host medium is less than 10 % its concentration is reduced by a factor of 2 until the resultant medium is stable enough at least to allow the determination of its properties.
  • the concentration is kept at least at 5 %, however, in order to keep the significance of the results a high as possible.
  • the capacitance of the test mixtures are determined both in a cell with homeotropic and with homogeneous alignment.
  • the cell gap of both types of cells is approximately 20 ⁇ .
  • the voltage applied is a
  • ⁇ is defined as ( ⁇
  • the dielectric permittivity of the compounds is determined from the change of the respective values of a host medium upon addition of the compounds of interest. The values are extrapolated to a concentration of the
  • a typical host medium is ZLI-4792 or BL-087 both commercially available from Merck, Darmstadt.
  • trans-1 ,4-cyclohexylene denote 1 ,4-phenylene.
  • the definitions as given in C. Tschierske, G. Pelzl and S. Diele, Angew. Chem. 2004, 1 16, 6340-6368 shall apply to non-defined terms related to liquid crystal materials in the instant application. Detailed description
  • the invention relates to a compound of formula I,
  • R 11 denotes a straight-chain or branched alkyl group, in which one or more non-adjacent and non-terminal Ch groups may be replaced, in each occurrence
  • F, CN or OCF3 denotes each independently in each occurrence denote, 1 ,4- phenylene, wherein in addition one or more CH groups may be replaced by N, trans-1 ,4-cyclo- hexylene in which, in addition, one or two non- adjacent Ch groups may be replaced by O and/or S, 1 ,4-cyclohexylene, naphthalene-2,6-diyl, decahydro- naphthalene-2,6-diyl, 1 ,2,3,4-tetrahydro-naphthalene- 2,6-diyl, it being possible for all these groups to be unsubstituted, mono-, di-, tri- or tetrasubstituted with F, CI, CN or alkyl, alkoxy, alkylcarbonyl or
  • alkoxycarbonyl groups wherein one or more H atoms may be substituted by F or CI,
  • p and q is each and independently 0, 1 , 2, 3 or 4, preferably 0,
  • X 11 and X 12 are independently from one another selected from a single bond, -CO-O-, -O-CO-, -O-COO-, -O-,
  • R 11 or R 12 is an alkyl or alkoxy radical, this may be straight chain or branched. It is preferably straight-chain, has 2, 3, 4, 5, 6, 7 or 8 carbon atoms and accordingly is preferably ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy or octoxy, furthermore methyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, nonoxy, decoxy, undecoxy, dodecoxy, tridecoxy or tetradecoxy, for example.
  • R 11 or R 12 is an alkenyl group are, this may be straight-chain or branched, preferably straight-chain, with up to 15 C atoms and more preferably, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, and corresponding isomers.
  • one of R 11 or R 12 is preferably alkenyl or alkinyl, preferably alkenyl, with up to 15 C atoms and the other is preferably alkyl, alkenyl or alkinyl, most preferably alky or alkenyl with 2 to 15 C atoms or alkoxy with 1 to 15, preferably 2 to 15, C atoms.
  • achiral branched group R 11 and/or R 12 may occasionally be of importance, for example, due to a reduction in the tendency towards crystallisation.
  • Branched groups of this type generally do not contain more than one chain branch.
  • R 12 is selected from CN, NO 2 , halogen, OCH 3 , OCN, SCN, COR x , COOR x or a mono- oligo- or polyfluorinated alkyl or alkoxy group with 1 to 4 C atoms.
  • R x is optionally fluorinated alkyl with 1 to 4, preferably 1 to 3 C atoms.
  • Halogen is preferably F or CI.
  • R 12 in formula I is selected of H, alkenyl, F, CI, CN, NO 2 , OCHs, COCHs, COC2H5, COOCH3, COOC2H5, CF 3 , C2F5, OCF 3 , OCHF2 and OC2F5, in particular, of ethenyl, propenyl, butenyl, F, CI, CN, CF3, OCH3 and OCF3, especially of propenyl, butenyl, F, CN and OCF3.
  • a smaller group of preferred groups -A 11 (-Z 11 -A 12 -) p or MG-1 1 comprising only 6-membered rings is listed below.
  • Phe in these groups is 1 ,4-phenylene
  • PheL is a 1 ,4-phenylene group which is substituted by 1 to 4 groups L, with L being preferably F, CI, CN, OH, NO2 or an optionally fluorinated alkyl, alkoxy or alkanoyl group with 1 to 7 C atoms, very preferably F, CI, CN, OH, NO 2 , CH 3 , C2H5, OCH 3 , OC2H5, COCHs, COC2H5, COOCH3, COOC2H5, CF 3 , OCF3, OCHF2, OC2F5, in particular F, CI, CN, CH 3 , C 2 H 5 , OCH 3 , COCH 3 and OCF 3 , most
  • This list comprises the subformulae shown below ;
  • Phe is 1 ,4-phenylene
  • PheL is 1 ,4-phenylene, which is substituted by one, two or three fluorine atoms, by one or two CI atoms or by one CI atom and one F atom and
  • Z in each case independently has one of the meanings of Z 11 as given under formula I and if present twice, preferably one of Z is -COO-, -OCO-, -CH2-O-, -O- CH 2 -, -CF2-O- or -O-CF2-.
  • MG-1 1 is selected from the sub-formulae not containing two groups Z, more preferably from MG-1 1 -2 to MG-1 1 -13, more preferably from MG-1 1 -2 or MG-1 1 -3.
  • Phe in these groups is 1 ,4-phenylene
  • PheL is a 1 ,4-phenylene group which is substituted by 1 to 4 groups L, with L being preferably F, CI, CN, OH, NO2 or an optionally fluorinated alkyl, alkoxy or alkanoyl group with 1 to 7 C atoms, very preferably F, CI, CN, OH, NO2, CH3, C2H5, OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF 3 , OCF3, OCHF2, OC2F5, in particular F, CI, CN, CH 3 , C2H5, OCH 3 , COCH 3 and OCF3, most preferably F, CI, CH 3 , OCH 3 and COCH 3 and CHex is 1 ,4- cyclohexylene.
  • This list comprises the subformulae shown below,
  • CHex is 1 ,4-cyclohexylene, preferably trans-1 ,4- cyclohexylene,
  • Phe is 1 ,4-phenylene
  • PheL is 1 ,4-phenylene, which is substituted by one, two or three fluorine atoms, by one or two CI atoms or by one CI atom and one F atom and
  • Particularly preferred are the sub-formulae, wherein Z in each case independently has one of the meanings of Z 11 as given under formula I and if present twice, preferably one of Z is -COO-, -OCO-, -CH2-O-, -O- CH 2 -, -CF2-O- or -O-CF2-.
  • PheL preferably denotes the group
  • L is preferably F, CI, CH 3 , OCH 3 and COCH 3 .
  • MG-12 is selected from the sub-formulae not containing two groups Z, more preferably from MG-12-1 to MG-12-38, even more preferably from MG-12-4 or MG-12-38, in particular, from MG-12-9 to MG-12-12 or MG-12-32 to MG-12-38.
  • MG-1 1 and MG-12 each comprise two or three six-atomic rings, more preferably MG-1 1 and MG-12 each comprise two six-atomic rings or MG-1 1 comprises two six-atomic rings and MG-12 comprises three six-atomic rings or MG-1 1 comprises three six-atomic rings and MG-12 comprises two six-atomic rings.
  • compounds of formula I wherein
  • Sp 11 denotes -(CH 2 ) n - with n an integer from 1 to 15, wherein one or more -CH2- groups may be replaced by -CO-, preferably an uneven integer, more preferably 3, 5, 7, 9, 1 1 or 13,
  • CH 3 , OCHs and COCH 3 preferably F, denotes an integer between 0 and 4, preferably 0, 1 or 2,
  • R 1 1 denotes an alkyl or alkoxy radical, which may be straight chain or branched having 2, 3, 4, 5, 6, 7 or 8 carbon atoms
  • R 12 denotes CN, NO 2 , F, OCH 3 , OCN, SCN, COR x , COOR x or a mono- oligo- or polyfluorinated alkyl or alkoxy group with 1 to 4 C atoms,
  • R x is optionally fluorinated alkyl with 1 to 4, preferably 1 to 3 C atoms, and denotes 3, 5, 7, 9, 1 1 or 13.
  • R 11 denotes alkyl, which may be straight chain or branched having 2, 3, 4, 5, 6, 7 or 8 carbon atoms, preferably straight chain alkyl having 3, 4, or 5 carbon atoms,
  • R 12 denotes CN, F, CF3 or OCF3, preferably CN or F, and n denotes 3, 5, 7, 9, 1 1 or 13, preferably 7, 9 or 1 1
  • the compounds of formula I can be synthesized according to or in analogy to methods which are known per se and which are described in standard works of organic chemistry such as, for example, Houben-Weyl, Methoden der organischen Chemie, Thieme-Verlag, Stuttgart.
  • the compounds of formula I and subformulae thereof can be synthesized according to or in analogy to the following synthesis schemes 1 or 2:
  • L, r, R 11 and R 12 have one of the meanings as given above and n denotes an integer between 1 and 1 1 .
  • one of the main advantages of using compounds of formula I in LC media for flexoelecthc applications is improving the switching speed in the ULH (uniform lying helix) geometry, particularly at
  • the invention also relates to the use of compounds of formula I in LC media and to a LC media comprising one or more compounds of formula I, as such.
  • the LC media in accordance with the present invention comprise one or more compounds of formula II,
  • R 21 and R 22 denote independently H, F, CI, CN, NCS or a straight- chain or branched alkyl group, which may be
  • F preferably F, CI, CN, a straight-chain or branched alkyl or alkoxy group which may be unsubstituted, mono- or polysubstituted by halogen or CN,
  • a 21 to A 24 denote independently in each occurrence a aryl-
  • alkoxycarbonyl groups wherein one or more H atoms may be substituted by F or CI, a denotes an integer from 1 to 15, preferably an odd (i.e.
  • Preferred compounds of formula II are selected from compounds in which the groups (-A 21 -A 22 -) and (-A 23 -A 24 -) are each and independently selected from the following groups
  • Phe in these groups is 1 ,4-phenylene
  • PheL is a 1 ,4-phenylene group which is substituted by 1 to 4 groups L, with L being preferably F, CI, CN, OH, NO2 or an optionally fluorinated alkyl, alkoxy or alkanoyl group with 1 to 7 C atoms, very preferably F, CI, CN, OH, NO 2 , CH 3 , C 2 H 5 , OCH3, OC2H5, COCH3, COC2H5, COOCH3, COOC2H5, CF 3 , OCF3, OCHF2, OC2F5, in particular F, CI, CN, CH3, C2H5, OCH3, COCH3 and OCF 3 , most preferably F, CI, CH 3 , OCH3 and COCH 3 and
  • Cyc is 1 ,4-cyclohexylene.
  • n denotes an integer from 1 to 15, preferably an odd (i.e.
  • the compounds of formula II can be synthesized according to or in analogy to methods which are known per se and which are described in standard works of organic chemistry such as, for example, Houben-Weyl, Methoden der organischen Chemie, Thieme-Verlag, Stuttgart. A preferred method of preparation can be taken from WO 2013/004333 A1 .
  • the utilization of compounds of formula II beside compounds of formula I is especially useful in order to further improve the switching speeds whilst maintaining a good phase range and a favorable value for e/K.
  • the LC media in accordance with the present invention comprise one or more compounds of formula III, R31.
  • R 31 and R 32 have each and independently from another one of the meanings as given for R 21 and R 22 under formula II,
  • a 31 to A 36 have each and independently from another one of the meanings as given for A 21 to A 24 under formula II,
  • Z 31 and Z 32 are each independently in each occurrence
  • -CH CH-COO-
  • b denotes an integer from 1 to 15, preferably an odd (i.e.
  • Preferred compounds of formula III are selected from compounds in which c denotes 0 and the group (-A 31 -A 32 -) is selected from the groups MG1 to MG4 as given above.
  • Phe, PheL an L have one of the meanings given above for the groups MG-1 to MG-4.
  • Especially preferred compounds of formula III are selected from the group of compounds of the following formulae,
  • the compounds of formula III can be synthesized according to or in analogy to methods which are known per se and which are described in standard works of organic chemistry such as, for example, Houben-Weyl, Methoden der organischen Chemie, Thieme-Verlag, Stuttgart.
  • the utilization of compounds of formula III beside compounds of formula I is especially useful in order to achieve high stabilities, favourable high clearing points and broad phase ranges, as well as, low appearances of the nematic twist-bend phase.
  • the LC medium in accordance with the present invention comprises one or more compounds of formula IV,
  • R 41 and R 42 have each and independently one of the meanings as given above for R 21 under formula II,
  • a 41 to A 44 have each and independently one of the meanings as given above for A 21 under formula II,
  • Z 41 and Z 42 are each independently in each occurrence
  • -CH CH-COO-
  • d denotes an integer from 1 to 15, preferably an odd (i.e.
  • Preferred compounds of formula IV are selected from compounds in which the groups (-A 41 -A 42 -) and (-A 43 -A 44 -) are each and independently selected from the groups of MG1 to MG4 as given above.
  • Especially preferred compounds of formula IV are selected from the group of compounds of the following formulae: - symmetrical ones (IVa and IVb):
  • the compounds of formula IV are either known or can be synthesized according to or in analogy to methods which are known per se and which are described in standard works of organic chemistry such as, for example, Houben-Weyl, Methoden der organischen Chemie, Thieme- Verlag, Stuttgart.
  • the LC medium in accordance with the present invention additionally comprises one or more compounds of formula V,
  • R 51 and R 52 have each and independently one of the meanings as given above for R 21 under formula II,
  • a 51 to A 53 have each and independently one of the meanings as given above for A 21 under formula II, Z 51 and Z 52 are each independently in each occurrence,
  • -CH CH-COO-
  • e denotes an integer from 1 to 15, preferably an odd (i.e.
  • a 51 is selected from the following group of formulae Va' to Vf and the mirror images of formulae Vd' and Ve'
  • R 51 and R 52 in formula V are selected of H, F, CI, CN, NO 2 , OCHs, COCHs, COC2H5, COOCH3, COOC2H5, CF 3 , C2F5, OCF 3 , OCHF 2 and OC2F5, in particular of H, F, CI, CN, OCH3 and OCF3, especially of H, F, CN and OCF 3 .
  • Preferred compounds of formula V are selected from the group of compounds of formulae VA to VD, preferably of formulae VA and/or VC, most preferably of formula VC,
  • LG 51 is Z 51 -(CH 2 )z-Z 52 ,
  • (F)i denotes F. and the other parameters have the respective meanings given above including the preferred meanings.
  • Z 51 -(CH 2 ) Z -Z 52 denotes -O-CO-(CH 2 ) n -CO-O-, -O-(CH 2 ) n -O- or -(CH2) n -, more preferably -O-CO-(CH2) n -CO-O-, wherein n denotes 3, 5, 7 or 9,
  • Particularly preferred compounds of formula VA are selected from the group of compounds of formulae VA-1 to VA-3
  • Particularly preferred compounds of formula VB are selected from the group of compounds of formulae VB-1 to VB-3
  • Compounds of formula VC are very much preferred. And of these particularly preferred compounds are selected from the group of compounds of formulae VC-1 to VC-3
  • the LC medium in accordance with the present invention additionally comprises one or more compounds of formula VI,
  • R 61 and R 62 have each and independently one of the meanings as given above for R 21 under formula II,
  • a 61 to A 64 have each and independently one of the meanings as given above for A 21 under formula II,
  • 761 denotes -O-, -COO-, -OCO-, -O-CO-O-, -OCH 2 -, -CH 2 O,
  • -O-, -COO- or -OCO- more preferably -O-, -COO- or -OCO-, most preferably -COO- or -OCO-, denotes 0 or 1 and denotes an integer from 1 to 15, preferably an odd (i.e. uneven) integer and, more preferably 3, 5, 7 or 9.
  • Preferred compounds of formula VI are selected from compounds in which the groups (-A 61 -A 62 -) and (-A 63 -A 64 -) are each and independently selected from the groups of MG1 to MG4 as given above. Further preferred are compounds of formula VI wherein h denotes 0 and the groups (-A 61 -A 62 -) and (-A 63 -A 64 -(A 65 ) h ) in formula VI are not identical or not mirror images or wherein h denotes 1
  • the compounds of formula VI can be synthesized according to or in analogy to methods which are known per se and which are described in standard works of organic chemistry such as, for example, Houben-Weyl, Methoden der organischen Chemie, Thieme-Verlag, Stuttgart.
  • the compounds of formula VI are synthesized according to or in analogy to methods which are disclosed for example in WO 2014/005672 A1 .
  • the LC medium in accordance with the present invention additionally comprises one, two, three or more compounds of formula VII, ⁇ 1. ⁇ 71. ⁇ 71. ⁇ 72. ( ⁇ 72. ⁇ 7 3) .. ( ⁇ 2) .. ( ⁇ 74. ⁇ 73. ) . ⁇ 75. ⁇ 74. ⁇ 76. ⁇ 72 V
  • R 71 and R 72 have each and independently one of the meanings as given above for R 21 under formula II,
  • a 71 to A 76 have each and independently one of the meanings as given above for A 21 under formula II,
  • Z 71 to Z 74 each and independently denotes -COO-, -OCO-,
  • Z 71 to Z 74 is not a single bond, denotes an integer from 1 to 15, preferably an odd (i.e. uneven) integer and, more preferably 3, 5, 7 or 9 and i and k each and independently denotes 0 or 1 .
  • Preferred compounds of formula VII are selected from compounds in which at least one of the groups - ⁇ 71 - ⁇ 71 - ⁇ 72 -( ⁇ 72 - ⁇ 73 ),-,
  • L is in each occurrence independently of each other preferably F, CI, CN or an optionally fluorinated alkyl, alkoxy or alkanoyi group with 1 to 7 C atoms, very preferably F, CI, CN, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , COCHs, COC2H5, COOCH3, COOC2H5, CF 3 , OCF3, OCHF2, OC2F5, in particular F, CI, CN, CH 3 , C2H5, OCH 3 , COCH 3 and OCF 3 , most preferably F, CI, CH3, OCH3 and COCH3 and r is in each occurrence independently of each other 0, 1 , 2, 3 or 4, preferably 0, 1 or 2.
  • L is preferably F, CI, CH 3 , OCH 3 and COCH 3 .
  • L is preferably F, CI, CH 3 , OCH 3 and COCH 3 .
  • compounds of formula VII wherein the groups -A 71 - Z 71 -A 72 -(Z 72 -A 73 )i- and -(A 74 -Z 73 -) k -A 75 -Z 74 -A 76 - in formula VII are identical or mirror images with the proviso that at least one of Z 71 to Z 74 is not a single bond.
  • R 71 and R 72 each and independently denote F or CN.
  • the compounds of formula VII can be synthesized according to or in analogy to methods which are known per se and which are described in standard works of organic chemistry such as, for example, Houben-Weyl, Methoden der organischen Chemie, Thieme-Verlag, Stuttgart.
  • the compounds of formula VII are synthesized according to or in analogy to methods which are disclosed for example in WO 2013/174478 A1 .
  • the medium in accordance with the present invention optionally comprises one or more chiral dopants, especially when utilized in a flexoelectric device.
  • the chiral compounds induce a chiral nematic texture with a pitch (Po), which is in a first approximation inversely proportional to the
  • HTP helical twisting power
  • a uniform lying helix texture is realized using a chiral nematic liquid crystal with a short pitch, typically in the range from 0.2 ⁇ to 1 ⁇ , preferably of 1 .0 ⁇ or less, in particular of 0.5 ⁇ or less, which is unidirectional aligned with its helical axis parallel to the substrates, e. g. glass plates, of a liquid crystal cell.
  • the helical axis of the chiral nematic liquid crystal is equivalent to the optical axis of a birefringent plate.
  • chiral dopants with a high helical twisting power in particular those disclosed in WO 98/00428.
  • used chiral dopants are e.g. the commercially available R/S-501 1 , CD-1 , R/S-81 1 and CB-15 (from Merck KGaA, Darmstadt, Germany).
  • the chiral dopants are preferably selected from formula VIII,
  • the liquid crystalline medium preferably comprises preferably 1 to 5, in particular 1 to 3, very preferably 1 or 2 chiral dopants, preferably selected from the above formula VIII, and/or formula IX and/or
  • the chiral compound is R-501 1 , S- 501 1 .
  • the amount of chiral compounds in the liquid crystalline medium is preferably from 0.1 to 15 %, in particular from 0.5 to 10 %, very preferably 1 to 5 % by weight of the total mixture.
  • the LC medium comprises one or more nematic LC
  • L 1 and L 2 each, independently of one another, denote F, CI, CF3 or CHF2, preferably each denote F,
  • (O)C v H2v+1 denotes OCvF v+i or CvF v+i and denotes 1 to 6.
  • the liquid crystal media may contain further additives like for example stabilizers, inhibitors, surface-active compounds, lubricating agents, wetting agents, dispersing agents, hydrophobing agents, adhesive agents, flow improvers, defoaming agents, deaerators, diluents, reactive diluents, auxiliaries, colourants, dyes, pigments or nanoparticles in usual concentrations.
  • the total concentration of these further constituents is in the range of 0.1 % to 10 %, preferably 0.1 % to 6 %, based on the total mixture.
  • concentrations of the individual compounds used each are preferably in the range of 0.1 % to 3 %.
  • concentration of these and of similar additives is not taken into consideration for the values and ranges of the concentrations of the liquid crystal components and compounds of the liquid crystal media in this application. This also holds for the concentration of the dichroic dyes used in the mixtures, which are not counted when the concentrations of the compounds respectively the components of the host medium are specified.
  • concentration of the respective additives is always given relative to the final doped mixture. In general, the total concentration of all compounds in the media according to this application is 100 %.
  • the liquid crystal media according to the present invention consists of several compounds, preferably of 2 to 40, more preferably of 3 to 30 and most preferably of 4 to 25 compounds.
  • the media in accordance with the present invention exhibit high values of the elastic constant kn and a high flexoelectric coefficient e.
  • the liquid crystal media preferably exhibit a kn ⁇ 100 pN, preferably ⁇ 20 pN.
  • the liquid crystal media preferably exhibit a k33 ⁇ 100 pN, preferably ⁇ 15 pN.
  • the liquid crystal media preferably exhibit a flexoelectric coefficient I en I > 0.2 pC/m, preferably > 1 pC/m.
  • the liquid crystal media preferably exhibit a flexoelectric coefficient I ess I ⁇ 0.2 pC/m, preferably > 2 pC/m.
  • the liquid crystal media preferably exhibit a flexo-elastic ratio (e / K) in the range from 1 to 10 V “1 , preferably in the range from 1 to 7 V "1 , more preferably in the range from 1 to 5 V "1 .
  • the media in accordance with the present invention exhibit high clearing points up to 60°C and higher, preferably up 65°C and higher and more preferably up to 70°C and higher.
  • the media in accordance with the present invention exhibit broad nematic phases of 30°C and more, preferably 35°C and more or even 40°C or more.
  • the media in accordance with the present invention exhibit NTB phases below 20°C or less, preferably below 15°C or less and more preferably below 0°C or less.
  • the media in accordance with the present invention exhibit high stabilities against crystallization at room temperature of more than 100 h, preferably more than 250 h or more than 1000 h.
  • the media in accordance with the present invention exhibit high stabilities against crystallization even at low temperatures (LTS).
  • the media do not crystallize even at temperatures down to 0°C, preferably down to -10°C, more preferably down to -20°C.
  • the LC medium comprises:
  • the amount of compounds of formula I in the liquid crystalline medium as a whole is preferably in the range from 5 to 50 %, in particular in the range from 6 to 30 %, especially in the range from 7 to 20 % by weight of the total mixture, and optionally 1 to 10, preferably 1 to 5, more preferably 1 or 3, most preferably 1 or 2 compounds of formula II, preferably selected from compounds compounds of formula II wherein (-A 21 -A 22 -) and (-A 23 -A 24 -) in formula II are identical or mirror images, more preferably of compounds of formulae ll'a-5 and/or ll'a-6.
  • the amount of compounds of formula II in the liquid crystalline medium is preferably in the range from 0 to 30 %, more preferably in the range from 1 to 20 %, even more preferably in the range from 2 to 10 % by weight of the total mixture, and/or optionally 1 to 10, preferably 1 to 5, more preferably 1 or 3, most preferably 1 or 2 compounds of formula III, preferably selected from symmetrical compounds of the above formulae lllc-2 and/or lllc-3.
  • the amount of compounds of formula III in the liquid crystalline medium is preferably in the range from 1 to 50 %, more preferably in the range from 5 to 30 %, even more preferably in the range from 10 to 20 % by weight of the total mixture, and/or
  • the amount of compounds of formula IV in the liquid crystalline medium is preferably in the range from 1 to 98 %, more preferably in the range from 20 to 80 %, even more preferably in the range from 30 to 60 % by weight of the total mixture, and/or optionally, 1 to 6, in particular 2 to 5, very preferably 3 or 4 compounds of formula V, preferably selected from the above formulae VA-1 , VC-2 and/or VC-3.
  • the amount of compounds of formula V in the liquid crystalline medium is preferably in the range from 1 to 70 %, more preferably in the range from 10 to 60 %, even more preferably in the range from 20 to 50 % by weight of the total mixture, and/or optionally 1 to 10, preferably 1 to 5, more preferably 1 or 3, most preferably 1 or 2 compounds from the above formulae VI, preferably form compounds of formula VI-4, VI-5, VI-7 and/or VI-8.
  • the amount of compounds of formula VI in the liquid crystalline medium is preferably from 1 to 40 %, in particular from 5 to 25 %, very preferably 10 to 15 % by weight of the total mixture, and/or optionally 1 to 10, preferably 1 to 5, more preferably 1 or 3, most preferably 1 or 2 compounds from the above formulae VII, preferably form compounds of formula VII-4, VII-5 and/or VI I-8.
  • the amount of compounds of formula VII in the liquid crystalline medium, if present, is preferably from 1 to 35 %, in particular from 5 to 25 %, very preferably 10 to 15 % by weight of the total mixture,
  • the amount of chiral compounds in the liquid crystalline medium is preferably from 1 to 15 %, in particular from 0.5 to 10 %, very preferably 0.1 to 5 % by weight of the total mixture, and/or • optionally up to 25, in particular up to 20, very preferably up to 15, different compounds selected from compounds of formula X. If present, the amount of compounds of formula X in the liquid crystalline medium as a whole, is preferably from 1 to 50 %, in particular from 5 to 30 %, very preferably 10 to 25 % by weight of the total mixture, and/or
  • additives such as for example stabilizers,
  • antioxidants etc. in usual concentrations.
  • the total concentration of these further constituents, if present, is in the range of 0.1 to 10 %, preferably 0.1 to 6 %, based on the total mixture.
  • concentrations of the individual compounds used each are preferably in the range of 0.1 to 3 %.
  • the LC medium of the present invention consists only of compounds selected from formula I to X, very preferably the LC medium consists only of compounds selected from formula I to IX.
  • the LC medium of the present invention consists only of compounds selected from formula I to X wherein none of the compounds contains a CN group. It is well know that cyano-containing materials have issues when active driving is
  • the compounds forming the LC medium in accordance with the present invention are mixed in conventional way.
  • the required amount of the compound used in the smaller amount is dissolved in the compound used in the greater amount.
  • the temperature is above the clearing point of the compound used in the higher concentration, it is particularly easy to observe completion of the process of dissolution.
  • the media by other conventional ways, e.g. using so-called pre-mixtures, which can be e.g. homologous or eutectic media of compounds or using so-called multi-bottle-systems, the constituents of which are ready to use media themselves.
  • the invention also relates to a process for the production of an LC medium as described above and below.
  • the invention relates to a process for the production of an LC medium comprising the steps of mixing one or more compounds of formula I, with at least one compound selected from compounds of formulae II to X.
  • the liquid crystalline media in accordance with the present invention can be used in electro optic devices, for example liquid crystal devices, such as STN, TN, AMD-TN, temperature compensation, guest-host, phase change or surface stabilized or polymer stabilized cholesteric texture (SSCT, PSCT) displays, in active and passive optical elements like polarizers, compensators, reflectors, alignment layers, colour filters or holographic elements, in adhesives, synthetic resins with anisotropic mechanical properties, cosmetics, diagnostics, liquid crystal pigments, for decorative and security applications, in nonlinear optics, optical information storage or as chiral dopants.
  • another aspect of the present invention is the use of a LC medium, comprising at least one compound of formula I in electro optic devices.
  • the media in accordance with the present invention are particularly beneficially for flexoelectric liquid crystal display applications, such as, for example, devices of the ULH or USH mode.
  • another object of the present invention is a liquid crystal device, preferably a flexoelectric device, comprising a medium, which comprises one or more compounds of formula I.
  • a flexoelectric display according to a preferred embodiment of the present invention comprises two plane parallel substrates, preferably glass plates covered with a transparent conductive layer such as indium tin oxide (ITO) on their inner surfaces, optionally alignment layers and a medium comprising one or more compounds of formula I and a chiral dopant as described above and below.
  • ITO indium tin oxide
  • the optical axis is rotated in the plane of the cell, similar as the director of a ferroelectric liquid crystal rotate as in a surface stabilized ferroelectric liquid crystal display.
  • the field induces a splay bend structure in the director, which is accommodated by a tilt in the optical axis.
  • the angle of the rotation of the axis is in first approximation directly and linearly proportional to the strength of the electrical field.
  • the optical effect is best seen when the liquid crystal cell is placed between crossed polarizers with the optical axis in the unpowered state at an angle of 22.5° to the absorption axis of one of the polarizers.
  • This angle of 22.5° is also the ideal angle of rotation of the electric field, as thus, by the inversion the electrical field, the optical axis is rotated by 45° and by appropriate selection of the relative orientations of the preferred direction of the axis of the helix, the absorption axis of the polarizer and the direction of the electric field, the optical axis can be switched from parallel to one polarizer to the centre angle between both polarizers. The optimum contrast is then achieved when the total angle of the switching of the optical axis is 45°.
  • the arrangement can be used as a switchable quarter wave plate, provided the optical retardation, i. e. the product of the effective birefringence of the liquid crystal and the cell gap, is selected to be the quarter of the wavelength.
  • the wavelength referred to is 550 nm, the wavelength for which the sensitivity of the human eye is highest, unless explicitly stated otherwise.
  • Po is the undisturbed pitch of the cholesteric liquid crystal
  • e / K is called the flexo-elastic ratio.
  • This angle of rotation is half the switching angle in a flexoelectric switching element.
  • ⁇ is the effective viscosity coefficient associated with the distortion of the helix.
  • the flexoelectric effect is characterized by fast response times (T on +T 0 ff at 35°C) typically ranging from 1 ms to 10 ms, preferably ⁇ 5ms and even more preferably ⁇ 3ms. It further features excellent grey scale capability.
  • ⁇ is the permittivity of vacuum
  • ⁇ is the dielectric anisotropy of the liquid crystal.
  • inventive media in accordance with the present invention can be aligned in their cholesteric phase into different states of orientation by methods that are known to the expert, such as surface treatment or electric fields. For example, they can be aligned into the planar
  • planar alignment or orientation of a liquid crystal
  • mesogenic material in a display cell or on a substrate means that the mesogenic groups in the liquid crystal or mesogenic material are oriented substantially parallel to the plane of the cell or substrate, respectively.
  • the term "homeotropic alignment" or orientation of a liquid crystal or mesogenic material in a display cell or on a substrate means that the mesogenic groups in the liquid crystal or mesogenic material are oriented substantially perpendicular to the plane of the cell or substrate,
  • the sample is placed into a cell comprising two plane-parallel glass plates coated with electrode layers, e.g. ITO layers and aligned in its cholesteric phase into a planar state wherein the axis of the cholesteric helix is oriented normal to the cell walls.
  • This state is also known as Grandjean state and the texture of the sample, which is observable e.g. in a polarization microscope, as Grandjean texture.
  • Planar alignment can be achieved e.g. by surface treatment of the cell walls, for example by rubbing and/or coating with an alignment layer such as polyimide.
  • a Grandjean state with a high quality of alignment and only few defects can further be achieved by heating the sample to the isotropic phase, subsequently cooling to the chiral nematic phase at a temperature close to the chiral nematic-isotropic phase transition and flow alignment by lightly pressing the cell.
  • the sample shows selective reflection of incident light, with the central wavelength of reflection depending on the helical pitch and the mean refractive index of the material.
  • the sample When an electric field is applied to the electrodes, for example with a frequency from 10 Hz to 1 kHz and an amplitude of up to 12 Vrms/ ⁇ , the sample is being switched into a homeotropic state where the helix is unwound and the molecules are oriented parallel to the field, i.e. normal to the plane of the electrodes. In the homeotropic state, the sample is transmissive when viewed in normal daylight and appears black when being put between crossed polarizers.
  • the sample Upon reduction or removal of the electric field in the homeotropic state, the sample adopts a focal conic texture, where the molecules exhibit a helically twisted structure with the helical axis being oriented
  • a focal conic state can also be achieved by applying only a weak electric field to a sample in its planar state. In the focal conic state the sample is scattering when viewed in normal daylight and appears bright between crossed polarizers.
  • a sample of a medium in accordance with the present invention in different states of orientation exhibits different transmission of light.
  • the respective state of orientation, as well as its quality of alignment can be controlled by measuring the light transmission of the sample depending on the strength of the applied electric field. Thereby it is also possible to determine the electric field strength required to achieve specific states of orientation and transitions between these different states.
  • the above-described focal conic state consists of many disordered birefringent small domains.
  • this texture is also called uniformly lying helix (ULH) texture. This texture is required to characterize the flexoelectric properties of the inventive compound.
  • the inventive media can be subjected to flexoelectric switching by application of an electric field. This causes rotation of the optic axis of the material in the plane of the cell substrates, which leads to a change in transmission when placing the material between crossed polarizers.
  • the flexoelectric switching of inventive materials is further described in detail in the introduction above and in the examples.
  • the ULH texture starting from the focal conic texture, by applying an electric field with a high frequency, of for example 10 kHz, to the sample whilst cooling slowly from the isotropic phase into the cholesteric phase and shearing the cell.
  • the field frequency may differ for different compounds.
  • the media in accordance with the present invention are also suitable for other types of displays and other optical and electro optical applications, such as optical
  • the parameter ranges indicated in this application all include the limit values including the maximum permissible errors as known by the expert.
  • the different upper and lower limit values indicated for various ranges of properties in combination with one another give rise to additional preferred ranges.
  • the LC media may also comprise compounds in which, for example, H, N, O, CI, F have been replaced by the corresponding isotopes.
  • All groups CnH n+i , CmH m+i and C1H21+1 are preferably straight chain alkyl groups with n, m and I C-atoms, respectively, all groups CnH n, CmH m and C1H21 are preferably (Ch jn, (Ch jm and (CH2)i, respectively and
  • n, m and I denote an integer between 1 and 12.
  • Table A lists the symbols used for the ring elements, table B those for the linking groups and table C those for the symbols for the left hand and the right hand end groups of the molecules.
  • n und m each are integers and three points indicate a space for other symbols of this table.
  • Test cells and methods Typically a 3 ⁇ thick cell, having an anti-parallel rubbed PI alignment layer on their mutually opposite substrate, is filled on a hotplate at a temperature at which the flexoelectric mixture in the isotropic phase.
  • phase transitions including clearing point and the crystallization behavior are determined using Differential Scanning Calorimetry (DSC) and verified by optical inspection.
  • DSC Differential Scanning Calorimetry
  • a Mettler FP90 hot-stage controller connected to a FP82 hot-stage is used to control the
  • the temperature of the cell is increased from ambient temperature at a rate of 5 degrees C per minute, until the onset of the isotropic phase is observed.
  • the texture change is observed through crossed polarizers using an Olympus BX51 microscope and the respective temperature noted. Wires are then attached to the ITO electrodes of the cell using indium metal.
  • the cell is secured in a Linkam THMS600 hot-stage connected to a Linkam TMS93 hot-stage controller.
  • the hot-stage is secured to a rotation stage in an Olympus BX51 microscope.
  • the cell is heated until the liquid crystal is completely isotropic.
  • the cell is then cooled under an applied electric field until the sample is
  • the driving waveform is supplied by a Tektronix AFG3021 B arbitrary function generator, which is sent through a
  • Newtons4th LPA400 power amplifier before being applied to the cell.
  • the cell response is monitored with a Thorlabs PDA55 photodiode. Both input waveforms and optical response are measured using a Tektronix TDS 2024B digital oscilloscope.
  • the applied field is monitored using a HP 34401A multimeter.
  • the tilt angle is measured using the aforementioned microscope and oscilloscope.
  • the undisturbed cholesteric pitch, Po is measured using an Ocean Optics USB4000 spectrometer attached to a computer.
  • the selective reflection band is obtained and the pitch determined from the spectral data.
  • the media shown in the following examples are well suitable for use in ULH-displays. To that end, an appropriate concentration of the chiral dopant or dopants used has to be applied in order to achieve a typical cholesteric pitch of 350 to 275 nm.
  • the resulting mixture is homogenized and filled into a test cell as described above. Measurements with respect to the switching performance, the TNI (clearing point), the e/K (flexo elastic constant) and the NTB (transition temperature to the second nematic phase or nematic twist bend phase) are performed and the results are summarized in the following table.
  • the resulting mixture is homogenized and filled into a test cell as described above. Measurements with respect to the switching performance, the clearing point, the flexo elastic constant and the NTB transition temperature are performed and the results are summarized in the following table.
  • the resulting mixture is homogenized and filled into a test cell as described above. Measurements with respect to the switching
  • the resulting mixture is homogenized and filled into a test cell as described above. Measurements with respect to the switching
  • the resulting mixture is homogenized and filled into a test cell as described above. Measurements with respect to the switching
  • the resulting mixture is homogenized and filled into a test cell as described above. Measurements with respect to the switching
  • the material M-3 shows an advantage in terms of switching speeds when compared to the material CM-4.
  • the flexo elastic constant and the phase range stays at an acceptable level.
  • the TNI of the mixture M-4 is significantly higher than the TNI of the mixture CM-4.

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  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

L'invention concerne un composé de formule (I), R11-A11-(Z11-A12)p-X11-Sp11-X12-(A13-Z13)q-A14-R12, dans laquelle R11, R12, A11 to A14, Z11, Z13, X11, X12, Sp11, p et q ont l'une des significations données ci-dessous. L'invention concerne en outre un procédé de production d'un composé de formule I, l'utilisation desdits composés dans des milieux critaux liquides (CL) et des milieux CL comprenant un ou plusieurs composés représentés par la formule I. En outre, l'invention concerne un procédé de production de tels milieux CL, l'utilisation de tels milieux dans des dispositifs à cristaux liquides (CL), en particulier dans des dispositifs à CL flexoélectriques, et un dispositif à CL flexoélectrique comprenant un milieu CL selon la présente invention.
PCT/EP2018/071225 2017-08-08 2018-08-06 Milieu cristal liquide et dispositif à cristaux liquides WO2019030153A1 (fr)

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Citations (18)

* 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
GB2328207A (en) 1997-08-13 1999-02-17 Merck Patent Gmbh Chiral hydrobenzoin derivatives for use as dopants in liquid crystalline mixtures
EP0971016A1 (fr) 1998-07-08 2000-01-12 MERCK PATENT GmbH Estradiols mésogènes
EP1053996A1 (fr) * 1998-01-09 2000-11-22 Chisso Corporation Composes esters, compositions de cristaux liquides et dispositifs afficheurs a cristaux liquides
EP1081123A2 (fr) * 1999-08-31 2001-03-07 Chisso Corporation Derivé de 2,3-difluorophenyle à anisotropie diélectrique negative, composition liquide cristalline et dispositif d'affichage à cristaux liquides
GB2356629A (en) 1999-10-04 2001-05-30 Merck Patent Gmbh Bimesogenic compounds and their use in flexoelectric liquid crystal devices
JP2001226675A (ja) * 2000-02-18 2001-08-21 Asahi Denka Kogyo Kk 液晶組成物
EP1900792A1 (fr) * 2006-09-13 2008-03-19 Merck Patent GmbH Composés de fluorphényle pour mélanges de cristaux liquides
US20120193577A1 (en) * 2011-01-31 2012-08-02 Jnc Petrochemical Corporation Liquid crystal compound, liquid crystal composition and liquid crystal display device
WO2013004333A1 (fr) 2011-07-05 2013-01-10 Merck Patent Gmbh Composés bimésogènes
WO2013174478A1 (fr) 2012-05-25 2013-11-28 Merck Patent Gmbh Composés bimésogènes et milieux mésogènes
WO2014005672A1 (fr) 2012-07-06 2014-01-09 Merck Patent Gmbh Composés bimésogènes et milieux mésogènes
WO2015036079A1 (fr) 2013-09-12 2015-03-19 Merck Patent Gmbh Composés mésogènes et milieux mésogènes
US20150124210A1 (en) * 2013-11-05 2015-05-07 Industrial Technology Research Institute Liquid crystal compound with negative dielectric anisotropy, liquid crystal display, and optoelectronic device
WO2016074762A1 (fr) * 2014-11-11 2016-05-19 Merck Patent Gmbh Composés bimésogènes et milieux mésogènes
WO2016143634A1 (fr) * 2015-03-12 2016-09-15 Jnc株式会社 Composé cristallin liquide, composition de cristaux liquides, matériau composite contenant des cristaux liquides et élément d'affichage à cristaux liquide utilisant le composé cristallin liquide, la composition de cristaux liquides ou le matériau composite contenant des cristaux liquides
US20160280997A1 (en) * 2015-03-25 2016-09-29 Jnc Corporation Liquid crystal compound having cyclohexene ring, liquid crystal composition and liquid crystal display device
CN106281359A (zh) * 2015-06-04 2017-01-04 江苏和成显示科技股份有限公司 液晶组合物及其显示器件

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1477547B1 (fr) * 2003-05-09 2006-06-14 MERCK PATENT GmbH Milieu liquide cristallin et dispositif d'affichage à cristaux liquides
US10190049B2 (en) * 2014-07-11 2019-01-29 Merck Patent Gmbh Mesogenic media and liquid crystal display
CN106281355B (zh) * 2015-06-04 2019-02-15 江苏和成显示科技有限公司 液晶介质及其应用

Patent Citations (18)

* 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
GB2328207A (en) 1997-08-13 1999-02-17 Merck Patent Gmbh Chiral hydrobenzoin derivatives for use as dopants in liquid crystalline mixtures
EP1053996A1 (fr) * 1998-01-09 2000-11-22 Chisso Corporation Composes esters, compositions de cristaux liquides et dispositifs afficheurs a cristaux liquides
EP0971016A1 (fr) 1998-07-08 2000-01-12 MERCK PATENT GmbH Estradiols mésogènes
EP1081123A2 (fr) * 1999-08-31 2001-03-07 Chisso Corporation Derivé de 2,3-difluorophenyle à anisotropie diélectrique negative, composition liquide cristalline et dispositif d'affichage à cristaux liquides
GB2356629A (en) 1999-10-04 2001-05-30 Merck Patent Gmbh Bimesogenic compounds and their use in flexoelectric liquid crystal devices
JP2001226675A (ja) * 2000-02-18 2001-08-21 Asahi Denka Kogyo Kk 液晶組成物
EP1900792A1 (fr) * 2006-09-13 2008-03-19 Merck Patent GmbH Composés de fluorphényle pour mélanges de cristaux liquides
US20120193577A1 (en) * 2011-01-31 2012-08-02 Jnc Petrochemical Corporation Liquid crystal compound, liquid crystal composition and liquid crystal display device
WO2013004333A1 (fr) 2011-07-05 2013-01-10 Merck Patent Gmbh Composés bimésogènes
WO2013174478A1 (fr) 2012-05-25 2013-11-28 Merck Patent Gmbh Composés bimésogènes et milieux mésogènes
WO2014005672A1 (fr) 2012-07-06 2014-01-09 Merck Patent Gmbh Composés bimésogènes et milieux mésogènes
WO2015036079A1 (fr) 2013-09-12 2015-03-19 Merck Patent Gmbh Composés mésogènes et milieux mésogènes
US20150124210A1 (en) * 2013-11-05 2015-05-07 Industrial Technology Research Institute Liquid crystal compound with negative dielectric anisotropy, liquid crystal display, and optoelectronic device
WO2016074762A1 (fr) * 2014-11-11 2016-05-19 Merck Patent Gmbh Composés bimésogènes et milieux mésogènes
WO2016143634A1 (fr) * 2015-03-12 2016-09-15 Jnc株式会社 Composé cristallin liquide, composition de cristaux liquides, matériau composite contenant des cristaux liquides et élément d'affichage à cristaux liquide utilisant le composé cristallin liquide, la composition de cristaux liquides ou le matériau composite contenant des cristaux liquides
US20160280997A1 (en) * 2015-03-25 2016-09-29 Jnc Corporation Liquid crystal compound having cyclohexene ring, liquid crystal composition and liquid crystal display device
CN106281359A (zh) * 2015-06-04 2017-01-04 江苏和成显示科技股份有限公司 液晶组合物及其显示器件

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
C. TSCHIERSKE; G. PELZL; S. DIELE, ANGEW. CHEM., vol. 116, 2004, pages 6340 - 6368
CHANDRASEKHAR: "Liquid Crystals", 1992, CAMBRIDGE UNIVERSITY PRESS
COLES, H.J.; MUSGRAVE, B.; COLES, M.J.; WILLMOTT, J., J. MATER. CHEM., vol. 11, 2001, pages 2709 - 2716
P. RUDQUIST ET AL., LIQ. CRYST., vol. 23, no. 4, 1997, pages 503
P.G. DEGENNES ET AL.: "The Physics of Liquid Crystals", 1995, OXFORD SCIENCE PUBLICATIONS

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