WO2010022891A1 - Milieu cristallin liquide et écran à cristaux liquides - Google Patents

Milieu cristallin liquide et écran à cristaux liquides Download PDF

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WO2010022891A1
WO2010022891A1 PCT/EP2009/006045 EP2009006045W WO2010022891A1 WO 2010022891 A1 WO2010022891 A1 WO 2010022891A1 EP 2009006045 W EP2009006045 W EP 2009006045W WO 2010022891 A1 WO2010022891 A1 WO 2010022891A1
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compounds
liquid crystal
independently
formula
medium according
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PCT/EP2009/006045
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Seung-Eun Lee
Eun Young Kim
Dong-Mee Song
Byun-Ha Yoo
Sun-Mi Park
Karl Skjonnemand
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Merck Patent Gmbh
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Priority to KR1020117007227A priority Critical patent/KR101770833B1/ko
Priority to KR1020167026948A priority patent/KR20160118375A/ko
Publication of WO2010022891A1 publication Critical patent/WO2010022891A1/fr

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    • C09K19/588—Heterocyclic compounds
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    • 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
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    • C09K2019/0466—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 linking chain being a -CF2O- chain
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C09K2019/2035—Ph-COO-Ph
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    • 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
    • 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
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    • 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
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    • 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
    • C09K2019/343—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a seven-membered ring
    • C09K2019/3433—Seven-membered ring with oxygen(s) in fused, bridged or spiro ring systems
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    • 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
    • C09K2019/3438—Crown ethers

Definitions

  • the present invention relates to liquid crystalline media, preferably to dielecthcally positive, nematic media, comprising one or more dielectrically positive compounds and one or more dielectrically neutral compounds, preferably are comprising on or more chiral dopants and preferably are encapsulated in a polymer matrix and to liquid crystal displays comprising these media, especially to displays operating in reflective mode and preferably addressed by an active matrix.
  • LCDs Liquid Crystal Displays
  • LCDs are widely used to display information. LCDs are used for direct view displays, as well as for projection type displays.
  • the electro-optical mode which is employed for most displays still is the twisted nematic (TN)-mode with its various modifications. Besides this mode, the super twisted nematic (STN)-mode and more recently the optically compensated bend (OCB)-mode and the electrically controlled birefringence (ECB)-mode with their various modifications, as e. g.
  • TN twisted nematic
  • STN super twisted nematic
  • OCB optically compensated bend
  • ECB electrically controlled birefringence
  • VAN vertically aligned nematic
  • PVA patterned ITO vertically aligned nematic
  • PSVA p_olymer stabilized vertically aligned nematic
  • MVA multi domain vertically aligned nematic
  • All these modes use an electrical field, which is substantially perpendicular to the substrates, respectively to the liquid crystal layer.
  • electro-optical modes employing an electrical field substantially parallel to the substrates, respectively the liquid crystal layer, like e.g. the
  • the liquid crystals (LCs) according to the present invention are preferably used in improved LCDs using cholesteric liquid crystals, which are also known as chiral nematic liquid crystals, with short helical pitch and with high dielectric anisotropy especially for advanced applications. They are particularly useful for operation in reflected mode, as cholesteric liquid crystals having an appropriate cholesteric pitch selectively reflect light they may be coloured and allow to avoid the use of colour filters in LCDs.
  • cholesteric liquid crystals in a polymer matrix e.g. as a PDLC or a NCAP.
  • liquid crystalline media with improved properties are required.
  • Their rotational viscosity should be as low as possible.
  • the media have to exhibit a suitably wide range of the nematic phase, an appropriate birefringence ( ⁇ n), preferably in the range from 0.100 to 0.300 and a suitably high dielectric anisotropy ( ⁇ ).
  • ⁇ has to be sufficiently high to allow a reasonably low operation voltage.
  • ⁇ should be 10 or more, in order to allow use easy accessible drivers with reasonably low operation voltages.
  • ⁇ should preferably 40 or less and in particular not higher than 35, as this would be detrimental for an at least reasonably high specific resistivity, which in turn is another requirement, especially for active matrix addressing.
  • Most preferably ⁇ should be in the range of 20 to 30.
  • the displays according to the present invention are preferably active matrix LCDs, short AMDs, addressed by an active matrix, preferably by a matrix of thin film transistors (TFTs).
  • TFTs thin film transistors
  • inventive liquid crystals can also beneficially be used in displays with other known addressing means.
  • Liquid crystal compositions suitable for LCDs and in particular for TN- displays are already widely known. These compositions, however, do have significant drawbacks. Most of them, besides having other deficiencies, lead to unfavourably high response times and/or to contrast ratios, which are too low for many applications. They also most generally have - -
  • liquid crystalline media with improved suitable properties for practical applications such as a wide nematic phase range, appropriate optical anisotropy ⁇ n, according to the display mode used, a high value of ⁇ , low viscosities, in particular low rotational viscosities ( ⁇ i), high contrast ratios in displays and especially fast response times and a good reliability.
  • liquid crystalline media with a suitable phase range suitably high values of ⁇ and ⁇ n and suitably low viscosities can be realized, which do not exhibit the drawbacks of the materials of the prior art or at least do exhibit them to a significantly lesser degree.
  • R 1 is alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy, alkenyl, alkenyloxy, alkoxyalkyl, fluorinated alkenyl or fluorinated alkenyloxy, preferably alkyl or alkoxyalkyl and most preferably n-alkyl, - -
  • L 11 and 12 are independently of each other H or F, preferably L 11 is
  • X 1 is CN or NCS, preferably CN, and
  • dielectrically positive compounds preferably having a dielectric anisotropy of more than 3, selected from the group of compounds of formulae Il and III, preferably one or more compounds of each of them,
  • R 2 and R 3 are independently of each other alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy with 1 to 7 C- atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl with 2 to 7 C-atoms and R 2 and R 3 preferably are alkyl or alkenyl,
  • L 21 , L 22 , L 31 and L 32 are independently of each other H or F, preferably L 21 and/or L 31 is F 1
  • X 2 and X 3 are independently of each other halogen, halogenated alkyl or alkoxy with 1 to 3 C-atoms or halogenated alkenyl or alkenyloxy with 2 or 3 C-atoms, preferably F, Cl, -OCF 3 or -CF 3 , most preferably F, Cl or -OCF 3 ,
  • I, m, n and o are independently of each other O or 1 and optionally
  • dielectrically neutral compounds selected from the group of formulae IV and V, preferably one or more compounds of each of them,
  • R 41 to R 52 independently of each other have the meaning given for R 2 under formula Il above, preferably R 41 is alkyl and R 42 is alkyl or alkoxy or R 41 is alkenyl and R 42 is alkyl, preferably R 51 is alkyl and R 52 is alkyl or alkenyl, or R 51 is alkenyl and R 52 is alkyl or alkenyl, preferably alkyl,
  • the media comprise one or more compounds selected from the group of compounds of formula III, wherein n and o both are 1 , Z 3 preferably is a single bond, and all rings are 1 ,4-phenylene, which independently of each other optionally are fluorinated once or twice, and of compounds of formula V, wherein q is 2 and Z 51 and Z 51 preferably are both a single bond.
  • the media according to the present invention may comprise one or more dielectrically positive compounds of formula Vl
  • R b is alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy with 1 to 7 C-atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl with 2 to 7 C-atoms and preferably is alkyl or alkenyl,
  • L 61 and L 62 are independently of each other H or F, preferably L 61 : i,s F,
  • X b is halogen, halogenated alkyl or alkoxy with 1 to 3 C- atoms or halogenated alkenyl or alkenyloxy with 2 or 3 C-atoms, preferably F, Cl, -OCF 3 or -CF 3 , most preferably F, Cl or -OCF 3 ,
  • r is O or 1.
  • the liquid crystalline media according to the instant application comprise one or more polymerisable compounds.
  • These polymerisable compounds may be non- mesogenic compounds, like e.g. the well known EHA, resp. 2EHA, or mesogenic compounds. These polymerisable mesogenic compounds are called here "reactive mesogens " (short RMs).
  • These polymerisable compounds, whether mesogenic or non-mesogenic, may be mono-reactive or multi-reactive, preferably di-reactive.
  • the media comprise both one or more mono-reactive compounds and one or more multi- reactive, preferably di-reactive compounds.
  • the media comprise one or more RMs, while non-mesogenic compounds may be present additionally.
  • the RMs can be chiral or achiral, and can comprise an acrylate/methacrylate group or another polymerisable group.
  • the RM are chiral compounds, as this allows the simple adjustment of the wavelength of the selective reflection by polymerising a certain amount of the chiral RM, which thus is no longer available to twist the liquid crystal material, leading to an increased cholesteric pitch and consequently to selective reflection at longer wavelengths.
  • the resultant cholesteric pitch may be beneficially stabilized against further change e.g. by use of an appropriate filter (e.g. UV filter) protecting the liquid crystal from ambient radiation.
  • Chiral reactive mesogens may be used in the liquid crystalline media according to the present invention as the only chiral compounds present in the media.
  • the chiral reactive mesogens are used together with conventional (non reactive) chiral dopant(s).
  • the desired starting value of the cholesteric pitch or alternatively a value already rather close to that desirable value, may be fixed by one or more conventional chiral dopant(s).
  • the additional use of one or more chiral reactive mesogen(s) then allows to further adjust the cholesteric pitch by exposure of the medium to UV radiation and the subsequent depletion of the chiral reactive mesogen(s).
  • the conventional chiral dopant(s) having signs of the HTP mutually opposite to those of the chiral reactive mesogen(s).
  • a central wavelength of the selective reflection may be fixed by the conventional chiral dopant(s). This central wavelength may then be shifted towards longer wavelengths by the chiral reactive mesogen(s) used. This effect may then be reversed by exposure of the media to UV radiation.
  • this last preferred embodiment leads to the lowest requirements for protection of the media against further change of the wavelength of selective reflection after the desired value has been achieved by irradiation with UV.
  • the HTP of a mixture of chiral compounds i.e. of conventional chiral dopants as well as of chiral reactive mesogens, may be approximated by the addition of their individual HTP values weighted by their respective concentrations in the medium.
  • the RMs can be mono-reactive or di- or multi-reactive. Especially preferred is a material comprising at least one di-reactive compound
  • cross-linking agent which is also preferably liquid crystalline or at least mesogenic with a functional group at each end; for instance it can be based on diacrylate type RMs.
  • the media comprise one or more polymerisable compounds they preferably additionally comprise one or more polymerisation initiators, e.g. photo initiators and/or thermal initiators.
  • polymerisation initiators e.g. photo initiators and/or thermal initiators.
  • the liquid crystalline media according to the present invention may be and in a preferred embodiment are stabilized by polymerisation of respective polymer precursors are consisting of said one or more polymerisable compounds and optionally one or more of said initiators.
  • the stabilising polymer has the morphology of a polymer network, i.e. the liquid crystalline material having a low molecular weight, i.e. the non- polymerisable liquid crystalline material / mesogenic material is present in a more or less continuous form interspersed with more or less smoth strands of polymeric material.
  • Polymer network stabilised liquid crystals are disclosed e.g. in Dierking, I., Adv. Mater. 12, No. 3, pp. 167-181 (2000).
  • the liquid crystalline media according to the instant application comprise one or more polymerisable compounds and preferably RMs.
  • the host mixture contains liquid crystalline compounds having a low molar mass and preferably an amount of one or more chiral dopants sufficient to lead to selective reflection in the visible range of the electromagnetic spectrum.
  • These cholesteric phases with a relatively short cholesteric pitch preferably are stabilised by a polymer.
  • the stabilisation of the (cholesteric) phase is carried out by adding to the chiral liquid crystalline host mixture one or more polymerisable compounds, preferably RMs, preferably a mixture comprising mono-reactive and di-reactive RMs, plus a suitable photo-initiator, and polymerising the polymerisable compounds, for example by exposure to UV irradiation, for a short time.
  • the polymerisation is carried out in electro-optical cells maintained at a temperature in the cholesteric phase of the chiral liquid crystalline host mixture.
  • the mesogenic mono-reactive compounds used according to the present invention preferably comprise one or more ring elements, linked together by a direct bond or via a linking group and, where two of these ring elements optionally may be linked to each other, either directly or via a linking group, which may be identical to or different from the linking group mentioned.
  • the ring elements are preferably selected from the group of four-, five-, six- or seven-, preferably of five- or six-, membered rings.
  • the RMs used according to the present invention are preferably selected from the group of formulae VIIA and VIIB
  • R 71 is H, F, Cl, Br, I, CN, NO 2 , NCS 1 SF 5 , SO 2 CF 3 or alkyl which is straight chain or branched, preferably has 1 to 20 C-atoms, is unsubstituted, mono- or poly-substituted by F, Cl, Br, I or CN, and in which one or more non- adjacent CH 2 groups are optionally replaced, in each case independently from one another, by -O-, -S-, -NH-,
  • -NR 01 -, -SiR 01 R 02 -, -CO-, -COO-, -OCO-, -OCO-O-, -S- CO-, -CO-S-, -CY 01 CY 02 or -C ⁇ C- in such a manner that O and/or S atoms are not linked directly to one another, preferably H, Halogen, n-alkyl, n-alkoxy with 1 to 7 C-atoms preferably 2 to 5 C-atoms, alkenyl, alkenyloxy or alkoxyalkyl with 2 to 7 C-atoms, preferably with 2 to 5 C-atoms or CN, NCS, halogen, preferably F, Cl, halogenated alkyl, alkenyl or alkoxy, preferably mono-, di- or oligo-fluorinated alkyl, alkenyl or alkoxy, especially preferred CF 3 , OCF 2 H or OCF 3 ,
  • R 01 and R 02 are, independently of each other, H or alkyl with 1 to 12 C-atoms,
  • R 72 , 771 74 are, independently of each other, an aromatic and/or alicyclic ring, or a group comprising two or more fused aromatic or alicyclic rings, wherein these rings optionally contain one or more hetero atoms selected from N, O and/or S, and are optionally mono- or poly-substituted by R 72 , 771 74
  • Z" to Z are, independently of each other, -O-, -S-, -CO-, -CO-O-, -O-CO-, -S-CO-, -CO-S-, -
  • Y 01 and Y 02 are, independently of each other, F, Cl or CN, and alternatively one of them may be H,
  • R 72 is H or alkyl, preferably H or alkyl with 1 to 10 C-atoms,
  • PG 71 is a polymerisable or reactive group
  • SP 71 is a spacer group or a single bond
  • X 71 has one of the meanings given for Z 71 and preferably is -O-, -CO-O-, -O-CO-, -CF 2 O-, -OCF 2 -, -CH 2 O-, -OCH 2 - or a single bond.
  • SP i72 and SP ,73 independently of each other have one of the meanings given for SP 11 above, and
  • the precursor of the polymer comprises, besides the compound(s) of formula VIIA one or more di-reactive mesogenic monomers, preferably of formula VIIB.
  • the compounds of formulae VIIA and VIIB according to the present invention may be chiral compounds.
  • polymer precursors comprising one or more compounds of formula VIIA and/or of formula VIIB, wherein
  • Z 71 is different from a single bond and/or ring A 71 is phenylene that is optionally substituted by one or more groups R and/or
  • R 71 is alkyl or alkoxy with 1 to 12, preferably 1 to 8 C-atoms, or alkenyl, alkenyloxy or alkynyl with 2 to 12, preferably 2 to 7 C-atoms and/or
  • SP 71 is alkylene with 1 to 12 C atoms which is optionally mono- or polysubstituted by F and wherein one or more non-adjacent CH 2 may be replaced, in each case independently from one another, by
  • -O-, -CH CH- or -C ⁇ C-, and that is linked to a ring, preferably to ring 71
  • a via a group selected from -O-, -CO-O-, -O-CO-, -O-CO-O- and a single bond and/or SP 71 is a single bond.
  • Preferences for MG 72 to X 73 are the same as for MG 71 to X 71 .
  • rings A 71 to A 73 are, independently of each other, an aromatic or alicyclic ring, preferably a 5-, 6- or 7-membered ring, or a group comprising two or more, preferably two or three, fused aromatic or alicyclic rings, wherein these rings optionally contain one or more hetero atoms selected from N, O and/or S, and are optionally mono- or poly- substituted with L 7 , wherein L 7 is F, Cl, Br, CN, OH, NO 2 , and/or an alkyl, alkoxy, alkylcarbonyl or alkoxycarbonyl group with 1 to 12 C atoms, wherein one or more H atoms are optionally replaced by F or Cl.
  • L 7 is preferably F, Cl, CN, OH, NO 2 , CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , COCH 3 ,
  • Preferred rings A 71 to A 73 are, for example, furan, pyrrol, thiophene, oxazole, thiazole, thiadiazole, imidazole, phenylene, cyclohexylene, cyclohexenylene, pyridine, pyrimidine, pyrazine, azulene, indane, naphthalene, tetrahydronaphthalene, decahydronaphthalene, tetrahydropyrane, anthracene, phenanthrene and fluorene.
  • one or more of these rings A 71 to A 73 is selected from furane-2,5-diyl, thiophene-2,5-diyl, thienothiophene-2,5-diyl, dithienothiophene-2,6-diyl, pyrrol-2,5-diyl, 1 ,4-phenylene, azulene-2,6-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, 1 ,2,3,4- tetrahydro-naphthalene-2,6-diyl, indane-2,5-diyl, or 1 ,4-cyclohexylene wherein one or two non-adjacent CH 2 groups are optionally replaced by O and/or S, wherein these groups are unsubstituted, mono- or polysubstituted by L as
  • 71 7* ⁇ contains only monocyclic rings A to A . Very preferably this is a group with one or two 5- and/or 6-membered rings.
  • Phe in these groups is 1 ,4-phenylene
  • PheL is a 1 ,4-phenylene group which is substituted by 1 to 4 groups L as defined above
  • Cyc is 1 ,4- cyclohexylene
  • Pyd is pyridine-2,5-diyl
  • Pyr is pyrimidine-2,5-diyl.
  • the following list of preferred groups comprises the sub formulae VII-1 to VII- 20 as well as their mirror images,
  • Z has the meaning of Z 71 as given in formula VIIA.
  • Z is -COO-, -OCO-, -CH 2 CH 2 -, -C ⁇ C- or a single bond.
  • the group is selected from the following formulae Vila to VIIj and their mirror images
  • L is F, Cl 1 Br, CN 1 OH, NO 2 , and/or an alkyl, alkoxy, alkylcarbonyl or alkoxycarbonyl group with 1 to 12 C atoms, wherein one or more H atoms are optionally replaced by F or Cl and r is 0, 1 , 2, 3 or 4, preferably 0, 1 or 2.
  • Especially preferred compounds of formula I comprise at least
  • 1 ,4-phenylene rings may optionally be substituted by R, preferably by alkyl, preferably by methyl, and/or by alkoxy and/or by halogen, preferably F.
  • liquid crystalline media comprise one or more compounds of formula I selected from the compounds of its sub-formulae 1-1 to I-5, preferably selected from formulae I-2, I-4 and I-5, most preferably of formula I-2
  • R 1 has the respective meanings given under formula I above and preferably is alkyl, most preferably n-alkyl, and X 1 preferably is CN.
  • liquid crystalline media comprise one or more compounds selected from the group of compounds of formulae 11-1 and 11-2, preferably of formula 11-2
  • X /2 is preferably F or -OCF 3 .
  • the media comprise one or more compounds selected from the ggrrcoup of compounds of formulae 11-1 and II-2, wherein L 21 and L 22 both are
  • the media comprise one or more compounds of formula 11-1 , which preferably are selected from the group of compounds of formulae 11-1 a to 11-1 c, preferably of formula 11-1 c
  • L 21 and L 22 are both F and L 32 and L 24 are both H or
  • L 21 , L 22 , L 23 and L 24 are all F.
  • the media comprise one or more compounds of formula IMc, wherein L 21 , L 22 , L 23 and L 24 all are F.
  • the media comprise one or more compounds selected from the group of compounds of formulae ll-2a to ll-2c, preferably of formula ll-2c,
  • L 23 to L 27 are independently of each other and of the other parameters H or F and preferably L 21 and L 22 are both F and two or three of L 23 to L 27 , most preferably L 23 to L 25 , are F and the others of L 21 to L 27 are H or F, preferably H and X ,2 is preferably F or -OCF 3 and most preferably F.
  • Especially preferred compounds of formula II-2 are the compounds of formula ll-2c-1
  • the media comprise one or more compounds selected from the group of compounds of formulae III-1 and III-2
  • the media comprise one or more compounds of formula 111-1 , preferably selected from the group of compounds of formulae Hl-I a to lll-1f, preferably selected from the group of compounds of formulae Ml-I a, 111-1 c and ill-Id, and most preferably one or more compounds each of formulae 11-1 a and/or Hl-Ic and/or Ill-Id
  • L 33 to L 37 are independently of each other and of the other parameters H or F and preferably L 31 and L 32 are both F and two or three of L 33 to L 37 most preferably L 33 to L 35 , are F and the others of L 31 to L 37 are H or F, preferably H and X 3 is preferably F or -OCF 3 .
  • Most preferable compounds of formula 111-1 are selected from the group of compounds of formulae lll-1a, IIMc-1 , and IIMd-1
  • the compounds of formula IV are selected from the group of compounds of formulae IV-1 to IV-7, more preferably of formulae IV-6 and/or IV-7
  • R 41 and R 42 have the respective meanings given under formula IV above and generally and in particular in formulae IV-1 and IV-5, R 41 preferably is alkyl or alkenyl, preferably alkenyl and R 42 preferably is alkyl or alkenyl, preferably alkyl and alternatively in formula IV-2 R 41 and R 42 preferably both are alkyl and in formula IV-4 R ,41 preferably is alkyl or aallkkeennyyll,, preferably alkyl and R 42 preferably is alkyl or alkoxy, preferably alkoxy.
  • the media comprise one or more compounds selected from the group of compounds of formulae IV-6 and IV-7 and, most preferably, one or more compounds each of formulae IV-6 and IV-7.
  • Preferred compounds of formula IV-6 are compounds of formulae CPTP-n-m and CPTP-n-Om, more preferably compounds of formula CPTP-n-Om, whereas preferred compounds of formula IV-7 are compounds of formula CPGP-n-m.
  • the definitions of these abbreviations are explained in tables A to C and illustrated in table D below.
  • liquid crystalline media according to the present invention comprise one or more compounds of formula V selected from the group of compounds of formulae V-1 to V-6
  • R 51 and R 52 have the respective meanings given under formula V above and R 51 preferably is alkyl, more preferably n-alkyl and in formula V-1
  • R 52 preferably is alkyl and in V-4 "F 0/ i" preferably is F.
  • Preferred compounds of formula V-1 are compounds of formulae PP-n-2V and PP-n-2Vm, more preferably compounds of formula PP-1-2V1.
  • Preferred compounds of formula V-2 are compounds of formulae PTP-n-Om, especially preferred PTP-1-02, PTP-2-O1 and PTP-3-O1.
  • Preferred compounds of formula V-3 are compounds of formulae PGP-n-m, PGP-n-2V and PGP-n-2Vm, more preferably of formulae PGP-2-m, PGP-3-m and PGP-n-2V.
  • Preferred compounds of formula V-4 are compounds of formulae PPTUI-n-m, especially preferred PPTUI-3-2, PPTUI-3-3, PPTUI-3-4 and PPTUI-4.
  • Preferred compounds of formula V-5 are compounds of formulae PGGIP-n-m.
  • Preferred compounds of formula V-6 are compounds of formulae PGIGP-n-m. The definitions of these abbreviations (acronyms) are explained in tables A to C and illustrated in table D below.
  • the compounds of formula Vl are preferably selected from the group of compounds of formulae VI-1 and VI-2, preferably of formula VI-1
  • the liquid crystalline media according to the instant invention comprise, more preferably predominantly consist of, more preferably essentially consist of and most preferably entirely consist of compounds selected from the group of compounds of formulae I to Vl and Vila and VIIb, more preferably of formulae I to V and Vila and/or VIIb.
  • compositions that the entity referred to, e.g. the medium or the component, contains the component or components or of the compound or compounds in question, preferably in a total concentration of 10 % or more and most preferably of 20 % or more unless explicitly defined otherwise.
  • the term "predominantly consisting of means that the entity referred to contains 55 % or more, preferably 60 % or more and most preferably 70 % or more of the component or components or of the compound or compounds in question unless explicitly defined otherwise.
  • the term "essentially consisting of means that the entity referred to contains 80 % or more, preferably 90 % or more and most preferably 95 % or more of the component or components or of the compound or compounds in question unless explicitly defined otherwise.
  • the term "entirely consisting of” means that the entity referred to contains 98 % or more, preferably 99 % or more and most preferably 100.0 % of the component or components or of the compound or compounds in question unless explicitly defined otherwise.
  • mesogenic compounds which are not explicitly mentioned above, can optionally and beneficially be used in the media according to the instant invention. Such compounds are known to the expert in the field.
  • the liquid crystal media according to the instant invention are characterised by a clearing point of 85 0 C or more, preferably of 90 0 C or more.
  • the ⁇ n, at 589 nm (Na D ) and 20 °C, of the liquid crystal media according to the instant invention preferably is in the range of 0.150 or more to 0.350 or less, more preferably in the range of 0.170 or more to 0.250 or less and most preferably in the range of 0.180 or more to 0.220 or less.
  • the ⁇ , at 1 kHz and 20 0 C, of the liquid crystal medium according to the invention preferably is 10 or more, preferably 15 or more, more preferably 20 or more and most preferably 25 or more, whereas it preferably is 40 or less, more preferably 35 or less and more preferably it is in the range of 10 or more, to 40 or less and most in the range of 20 to 30 (how about 10 to 40.
  • the nematic phase of the inventive media without the chiral dopants extends at least from 0 0 C or less to 80 0 C or more, more preferably at least from -20 0 C or less to 85 0 C or more, most preferably at least from -20 0 C or less to 90 0 C or more and in particular at least from -30 0 C or less to 95 0 C or more.
  • the liquid crystalline media are preferably characterized for comparison purposes in TN displays operating in the second transmission minimum according to Gooch and Tarry having an optical retardation (d • ⁇ n) in the range of 1.0 ⁇ m or more to 1.1 ⁇ m or less.
  • cholesteric liquid crystals also called chiral nematic liquid crystals, having a rather short cholesteric pitch, preferably their cholesteric pitch is selected such, that their wavelength of selective reflection is in the in the range in the visible range of the electromagnetic spectrum i.e. in the range from of 400 nm to 800 nm.
  • the liquid crystal media contain one or more chiral dopants preferably having an absolute value of the helical twisting power (HTP) of 20 ⁇ m "1 or more, preferably of 40 ⁇ m "1 or more, more preferably in the range of 60 ⁇ m "1 or more, most preferably in the range of 80 ⁇ m "1 or more to 260 ⁇ m "1 or less.
  • HTP helical twisting power
  • the liquid crystal media contain 50 % to 100 %, more preferably 70 % to 100 % more preferably 80 % to 100 % and in particular 90 % to 100 % totally of compounds of formulae I, II, III, IV, V and Vl, preferably of formulae I, II, III, IV and V.
  • liquid crystal media comprise, more preferably predominantly consist of, more preferably essentially consist of and most preferably entirely consist of compounds of formulae I, II, III, IV, V and Vl, preferably of formulae I, II, III, IV and V.
  • Compounds of formula I preferably are used in the media in a total concentration from 1 % to 35 %, more preferably from 2 % to 30 %, more preferably from 3 % to 20 % and most preferably from 5 % to 15 % of the total mixture.
  • Compounds of formulae Il and III preferably are used together in the media in a total concentration from 40% to 80 %, more preferably from 45 % to 75 %, more preferably from 50 % to 70 % and most preferably from 55 % to 65 % of the total mixture.
  • Compounds of formula Il preferably are used in the media in a total concentration from 15 % to 35 %, more preferably from 20 % to 30 % and most preferably from 22 % to 28 % of the total mixture.
  • Compounds of formula III preferably are used in the media in a total concentration from 20 % to 45 %, more preferably from 25 % to 40 % and most preferably from 30 % to 35 % of the total mixture.
  • Compounds of formula IV preferably are used in the media in a total concentration from 10 % to 35 %, more preferably from 15 % to 30 % and most preferably from 20 % to 25 % of the total mixture.
  • Compounds of formula V preferably are used in the media in a total concentration from 10 % to 30 %, preferably from 12 % to 28 % and most preferably from 16 % to 23 % of the total mixture.
  • Compounds of formula Vl preferably are used in the media in a total concentration from 0 % to 30 %, preferably from 0 % to 15 % and most preferably from 1 % to 10 % of the total mixture.
  • Compounds of the polymerisable compounds preferably of formulae VIIA and/or VIJB, preferably are used in the media in a total concentration from 0 % to 10 %, more preferably from 0 % to 7 % and most preferably from 0.5 % to 5 % of the total mixture.
  • one or more polymerisation initiators preferably one or more photo initiators are used.
  • concentration of the initiators is from 0.1 % to 10 %, more preferably from 0.2 % to 5 % and most preferably from 0.5 % to 2 % of the total concentration of the polymerisable compounds.
  • the media according to the present invention further comprise one or more chiral compounds as chiral dopants in order to adjust their cholesteric pitch.
  • Their total concentration in the media according to the instant invention is preferably in the range 0.1 % to 15 %, more preferably from 1 % to 10 % and most preferably from 2 % to 6 %.
  • the media according to the present invention may comprise further liquid crystal compounds in order to adjust the physical properties. Such compounds are known to the expert.
  • Their concentration in the media according to the instant invention is preferably 0 % to 30 %, more preferably 0.1 % to 20 % and most preferably 1 % to 15 %.
  • the media according to the present invention comprise one or more compounds of
  • V- 1 preferably of formula PP-n-mV, and/or PP-n-mVI, and/or
  • 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 mixture is less than 10 % its concentration is reduced by a factor of 2 until the resultant mixture 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 capacities 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 ⁇ m.
  • the voltage applied is a rectangular wave with a frequency of 1 kHz and a root mean square value typically of 0.5 V to 1.0 V, however, it is always selected to be below the capacitive threshold of the respective test mixture.
  • ⁇ is defined as ( ⁇ n - ⁇ _i_), whereas ⁇ av . is ( ⁇ n + 2 ⁇ x ) / 3.
  • the mixture ZLI-4792 and for dielectrically neutral, as well as for dielectrically negative compounds are used as host mixture, respectively.
  • the dielectric permittivities of the compounds are determined from the change of the respective values of the host mixture upon addition of the compounds of interest. The values are extrapolated to a concentration of the compounds of interest of 100 %.
  • Components having a nematic phase at the measurement temperature of 20 0 C are measured as such, all others are treated like compounds.
  • threshold voltage refers in the instant application to the optical threshold and is given for 10 % relative contrast ( ⁇ o) and the term saturation voltage refers to the optical saturation and is given for 90 % relative contrast (Vg 0 ) both, if not explicitly stated otherwise.
  • the capacitive threshold voltage (V 0 ), also called Freedericks-threshold (V Fr ) is only used if explicitly mentioned.
  • the ranges of parameters given in this application are all including the limiting values, unless explicitly stated otherwise.
  • the optical anisotropy ( ⁇ n) is determined at a wavelength of 589.3 nm.
  • the dielectric anisotropy ( ⁇ ) is determined at a frequency of 1 kHz.
  • the threshold voltages, as well as all other electro- optical properties have been determined with test cells prepared at Merck KGaA, Germany. The test cells for the determination of ⁇ had a cell gap of approximately 20 ⁇ m.
  • the electrode was a circular ITO electrode with an area of 1.13 cm 2 and a guard ring.
  • the orientation layers were lecithin for homeotropic orientation ( ⁇ n) and polyimide AL-1054 from Japan Synthetic Rubber for planar homogeneous orientation ( ⁇ _ ⁇ _).
  • the capacities were determined with a frequency response analyser Solatron 1260 using a sine wave with a voltage of 0.3 V rms .
  • the test cells used have cell gap selected to have an optical retardation matching the first transmission minimum according to Gooch and Tarry or below, typically of about 0.45 ⁇ m "1 .
  • the light used in the electro-optical measurements was white light.
  • the set up used was commercially available equipment of Autronic Melchers, Düsseldorf, Germany.
  • the characteristic voltages have been determined under perpendicular observation.
  • the threshold (V 10 ) - mid grey (V 50 ) - and saturation (Vg 0 ) voltages have been determined for 10 %, 50 % and 90 % relative contrast, respectively
  • the liquid crystal media according to the present invention may contain further additives in usual concentrations.
  • the total concentration of these further constituents is in the range of 0 % to 10 %, preferably 0.1 % to 6 %, based on the total mixture.
  • the concentrations of the individual compounds used each are preferably in the range of 0.1 % to 3 %.
  • the 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 mixture are specified.
  • the concentration of the respective additives is always given relative to the final doped mixture.
  • the liquid crystal media according to the present invention consist of several compounds, preferably of 3 to 30, more preferably of 4 to 20 and most preferably of 4 to 16 compounds. These compounds are mixed in conventional way. As a rule, the required amount of the compound used in the smaller amount is dissolved in the compound used in the greater amount. In case 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. It is, however, also possible to prepare the media by other conventional ways, e.g. using so called pre-mixtures, which can be e.g. homologous or eutectic mixtures of compounds or using so called multi-bottle-systems, the constituents of which are ready to use mixtures themselves.
  • pre-mixtures which can be e.g. homologous or eutectic mixtures of compounds or using so called multi-bottle-systems, the constituents of which are ready to use mixtures themselves.
  • the liquid crystal media according to the present invention comprising one or more chiral dopants selectively reflect radiation in the visible range of the electromagnetic spectrum, i.e. in the range from 400 nm to 800 nm.
  • their band of selective reflection extends into this range of wavelengths more preferably the centre wavelength of their reflection band lies within this range and most preferably their complete reflection band lies within this range.
  • they have a selective reflection with a half bandwidth (1/2 FWHM) in the range from 15 nm to 60 nm, preferably in the range from 20 nm to 55 nm and most preferably from 25 nm to 50 nm.
  • the relative half bandwidth i.e.
  • ratio of the half bandwidth (1/2 FWHM) and the centre wavelength of the reflection band preferably is in the range from 1 % to 20 %, more preferably in the range from 2 % to 16 %, more preferably in the range from 4 % to 10 %, and most preferably in the range from 6 % to 8 %.
  • the wavelength of the centre of the resultant selective reflection at a given temperature may be calculated from the actual concentration of the chiral dopant in the host used via the approximation of the polynomial series (I):
  • ⁇ , ⁇ and ⁇ are material constants specific for the combination of a given chiral dopant in a given host mixture
  • c(dop.) is the concentration of the chiral dopant in the host mixture.
  • the parameters ⁇ , ⁇ and ⁇ do depend more strongly on the type of the chiral dopant, than on the specific liquid crystal mixture used.
  • the absolute value of the parameter ⁇ of the chiral dopant, respectively the chiral dopants, in the respective liquid crystal medium according to the present application is in the range from 5 nm to 25 nm, more preferably in the range from 10 nm to 20 nm and most preferably in the range from 12 nm to 16 nm.
  • These media may comprise more than one chiral dopant.
  • these may beneficially selected in one of the known ways to compensate e.g. against the temperature dependence of the cholesteric pitch and, hence, of the wavelength of selective reflection.
  • chiral dopants having the same sign of the parameter ⁇ may be used as well as chiral dopants having the opposite sign of this parameter, depending on the nature of the parameters for the terms of higher order of equation (I), in particular of the parameter ⁇ , the parameter of the quadratic term.
  • liquid crystal media according to the instant invention can be modified in such a way, that they are usable in all known types of liquid crystal displays, either using the liquid crystal media as such, like TN-, TN-AMD, ECB-AMD, VAN-AMD, IPS and OCB LCDs and in particular in composite systems, like PDLC, NCAP, PN LCDs and especially in ASM-PA LCDs.
  • the melting point T(C 1 N), the transition from the smectic (S) to the nematic (N) phase T(S 1 N) and the clearing point T(N 1 I) of the liquid crystals are given in degrees centigrade.
  • the structures of the liquid crystal compounds are represented by abbreviations, which are also called “acronyms".
  • abbreviations which are also called "acronyms”.
  • the transformation of the abbreviations into the corresponding structures is straight forward according to the following three tables A to C.
  • H 2 ⁇ + i are preferably straight chain alkyl groups with n, m and I C-atoms, respectively, all groups C n H 2n , C m H 2m and
  • 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.
  • Table D lists exemplary molecular structures together with their respective codes.
  • n und m each are integers and three points "" indicate a space for other symbols of this table.
  • liquid crystalline media according to the present invention comprise, besides the compound(s) of formula I one or more compounds selected from the group of compounds of the formulae of the following table.
  • Table E lists chiral dopants, which are preferably used in the liquid crystalline media according to the present invention.
  • the media according to the present invention comprise one or more compounds selected from the group of compounds of table E.
  • Table F lists stabilizers, which are preferably used in the liquid crystalline media according to the present invention.
  • n means an integer in the range from 1 to 12.
  • the media according to the present invention comprise one or more compounds selected from the group of compounds of table F.
  • liquid crystalline media according to the present invention comprise preferably four or more, preferably six or more, compounds selected from the group of compounds of table D, preferably
  • Liquid crystal mixtures are realized with the compositions and properties given in the following tables. Their optical performance is investigated. Especially their reflection spectra are recorded.
  • Mixture A-1 shows a reflection in the blue range of the spectrum ranging from 377 nm to 435 nm (FWHM), as shown in figure 1
  • mixture A- 2 has a selective reflection in the green spectral region, ranging from 506 nm to 576 nm (FWHM), see also figure 1.
  • the commas in the figures on the "R"-axis of the figure are representing decimal points.
  • the concentration of the RM used is 1 %, whereas the concentration of the photo initiator is set to 1 % of the concentration of the RM.
  • the mixture B-2 of example 2.2 is stabilized by a polymer formed in the material.
  • the concentration of the RM is again changed from 1 % over 3 % to 5 % of the mixture, whereas the concentration of the photo initiator is set to 1 % of the RM in each case.
  • a basic mixture is stabilized by a polymer formed in the material.
  • the concentration of the RM is again changed from 1 % over 3 % to 5 % of the mixture, whereas the concentration of the photo initiator is set to 1 % of the RM in each case.
  • the di-reactive mesogen, RM2 is used.
  • Mixture E-1 shows a reflection in the blue range of the spectrum, ranging from 438 nm to 510 nm (FWHM)
  • mixture E-2 has a selective reflection in the green spectral region, ranging from 490 nm to 567 nm (FWHM)
  • mixture E-3 has a selective reflection in the red spectral region, ranging from 595 nm to 681 nm (FWHM).
  • the resultant mixture F- 1 has a clearing point of 86.0 0 C and a central wavelength of the selective reflection of 558 nm.
  • the band of selective reflection ranges from 524 nm to 592 nm (FWHM) and ⁇ /2 is thus 34 nm.
  • the respective concentrations are 2.73 %, 2.22 %. 3.02 % and 2.93 % for the respective mixtures G-1. H-1. 1-1 and J-1.
  • the cells for the LC are made from AF glass and have orientation layers of AL3046 (from JSR, Japan). The first one of these cells is investigated as such.
  • the parameter ⁇ is 21.2 nm here.
  • the 2 nd and 3 rd one of these cells are exposed to UV-irradiation with a different dose each.
  • a high pressure mercury lamp EXECURE-w 3000 from HOYA Schott, Japan is used. The intensity of the UV radiation is 100 mW/cm.
  • a cut-off filter with a cut-off wave length of 320 nm is placed between the lamp and the LC cell.
  • the 2 nd cell is exposed to UV radiation with an energy of 22 J, whereas the 3 rd cell is exposed to 71 J.
  • the wavelength of the selective reflection can be altered to any desired colour simply by varying the intensity/energy of the UV irradiation.
  • R-5011 and 3.00 % of the chiral reactive mesogen RM3 * are added to the liquid crystalline host mixture B-O of example 2.
  • R-5011 RM3 * both have a positive value of the HTP.
  • several cells are filled with the resultant mixture and processed and investigated as described under example 14. Here four cells are prepared. The 1 st cell is investigated as such. The 2 nd cell is exposed to UV radiation having an energy of 60 J, the 3 rd cell is exposed to 120 J and the 4 th cell is exposed to 300 J, respectively.
  • the wavelength of the selective reflection can be altered to any desired colour by variation of the intensity/energy of the UV irradiation.
  • the wavelength of the selective reflection can be adjusted to any desired colour by variation of the intensity/energy of the UV irradiation.
  • the energy of the Uv radiation needed to achieve a given shift of the wavelength of selective reflection is significantly lower when a photo initiator is used, as in the present example, compared to the situation with out presence of a photo initiator, like in the previous example, example 15.
  • a given, longer value of the wavelength of selective reflection e.g. (598 ⁇ 3) nm

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Abstract

La présente invention concerne des milieux nématiques diélectriquement positifs comprenant un ou deux composés de formule I ou plus, et un ou plusieurs composés choisis dans l'ensemble des composés de formules II et III, et, en option, un ou plusieurs composés choisis dans l'ensemble des composés de formules IV et V, dont les paramètres sont définis dans la revendication 1. Le milieu comprend en option un ou plusieurs dopants chiraux. L'invention concerne aussi des écrans à cristaux liquides comprenant ces milieux, en particulier des écrans à cristaux liquides nématiques en hélice, et plus particulièrement des écrans à matrice active.
PCT/EP2009/006045 2008-08-29 2009-08-20 Milieu cristallin liquide et écran à cristaux liquides WO2010022891A1 (fr)

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WO2015162950A1 (fr) * 2014-04-25 2015-10-29 Jnc株式会社 Composition à cristaux liquides et élément d'affichage à cristaux liquides
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WO2018036989A1 (fr) * 2016-08-24 2018-03-01 Merck Patent Gmbh Milieu cristallin liquide et écran à cristaux liquides
CN108707464A (zh) * 2018-06-05 2018-10-26 晶美晟光电材料（南京）有限公司 一种具有高光学各项异性的液晶组合物及其应用
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WO2021127949A1 (fr) * 2019-12-24 2021-07-01 北京八亿时空液晶科技股份有限公司 Composition de cristaux liquides pouvant être adaptée à des températures de fonctionnement relativement larges et son utilisation dans un dispositif
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JP2017522432A (ja) * 2014-05-09 2017-08-10 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ 液晶媒体およびそれを含む高周波数素子
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