Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
  • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
  • C09K19/3001—Cyclohexane rings
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
  • C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
  • C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters

Definitions

• the invention relates to an electro-optical liquid crystal display with an electrode structure for the reorientation of the liquid crystalline medium which generates an electrical field with a component parallel to the liquid crystal layer which is sufficient to affect the switching of the liquid crystalline medium.
• the switching of the liquid crystalline medium takes place essentially in the plane of the liquid crystal layer.
• the liquid crystalline medium has a positive anisotropy of the dielectric permittivity and contains at least two mesogenic compounds of formula I
• R11 is alkyl or alkoxy with 1 to 7 C-atoms or alkoxyalkyl with 2 to 7 C-atoms, preferably alkyl,
• R12 is alkenyl or alkenyloxy with 2 to 7 C-atoms, preferably alkenyl
• Z 1 is -CH 2 -CH 2 - or a single bond, preferably a single bond and
• liquid crystal displays like in TN, STN, OMI and AMD-TN displays, as well as in some more recently interesting displays like VAN (or ECB) and OCB displays electrical fields which are substantially perpendicular to the liquid crystal layer are used to switch the orientation of the liquid crystals.
• VAN or ECB
• OCB displays electrical fields which are substantially perpendicular to the liquid crystal layer are used to switch the orientation of the liquid crystals.
• WO 91/10936 discloses a liquid crystal display using an electrical fiels with a significant component parallel to the liquid crystal layer used to switch the liquid crystals mainly in the plane of the liquid crystal layer called IPS from in Plane Switching.
• the principle of operation of liquid crystal displays with such an electrical field are described for example in R.A. Soref, Journal of Applied Physics, Vol. 45, Nr. 12, S. 5466-5468 (1974).
• Liquid crystalline media for such IPS displays are described e. g. in
• IPS displays of the state of the art have still severe shortcommings for several applications.
• One of the most severe problems is their long response times, which are significantly longer than those of e. g. TN or VAN displays.
• the operation voltages have to be improved. This means that they are too high for some applications.
• other requirements like long operational life time, stability both for storage and operation at extreme temperatures (high as well as low) and under illumination have to be fulfilled at the same time.
• One constituent of such displays with a crucial influence on these performance criteria is the liquid crystal medium used.
• R11 is alkyl or alkoxy with 1 to 7 C-atoms or alkoxyalkyl with 2 to 7 C-atoms, preferably alkyl,
• R12 is alkenyl or alkenyloxy with 2 to 7 C-atoms, preferably alkenyl
• liquid crystalline media according to the invention are characterized by their relatively high clearing points and their small rotational viscosities as well as their low threshold voltages.
• the invention resides, besides the liquid crystalline medium, in an electro- optical display with an electrode structure generating an electrical field with a significant component parallel to the liquid crystal layer containing a liquid crystalline medium having a positive anisotropy of the dielectric permittivity and containing at least two mesogenic compounds of formula I as given above.
• liquid crystal displays containing a liquid crystalline medium containing one or more compounds selected from the group of formulae la and lb
• R 11 is alkyl with 1 to 5 C-atoms or alkoxy with 1 to 5 C-atoms, preferably alkyl,
• R 12 is alkenyl or alkenyloxy with 2 to 7 C-atoms, preferably alkenyl and
• Z 1 is a single bond.
• liquid crystal displays containing a liquid crystalline medium containing one or more compounds each of formula la and of formula lb.
• liquid crystal displays containing a liquid crystalline medium containing one or more compounds selected from the group of formulae Ia1 , Ia2, Ib1 and Ib2
• liqiud crystal displays containing liquid crystalline media containing one, two or more compounds of formula lb, preferably of formula Ia1 , besides one or more, preferably two or more, compounds of formula la, preferably of formula Ia1.
• liquid crystal displays contain liquid crystalline media containing one or more mesogenic compounds of the formula II
• R 21 is alkyl or alkoxy with 1 to 7 C atoms or alkenyl, alkenyloxy or alkoxyalkyl with 2 to 7 C atoms,
• R 22 is alkyl with 1 to 7 C atoms or alkenyl with 2 to 7 C atoms
• n 0, 1 or 2
• liquid crystal displays contain liquid crystalline media A Q containing one or more mesogenic compounds of the formula II selected from the group of formulae lla to lie
• liquid crystal displays containing liquid crystalline media containing compounds of formula III
• R 3 is alkyl or alkoxy with 1 to 7 C atoms or alkenyl, alkenyloxy or alkoxyalkyl with 2 bis 7 C atoms,
• 7 3 is -CH 2 -CH 2 , -COO-, -CF 2 O- or a single bond and
• X° is F, CI, CN or NCS, preferably CN.
• liqiud crystalline media containing one or more compounds of formula III wherein
• X 3 is CN
• Z 3 is a single bond. Further preferred are liqiud crystalline media containing one or more compounds of formula III wherein
• X 3 is CN
• X 3 is CN
• X 3 is CN
• Z 31 is -CH 2 -CH 2 - or a single bond.
• liquid crystal displays containing liquid crystalline media containoing one, two, three or more compounds of formula IV
• R 4 is alkyl or alkoxy with 1 to 7 C atoms or alkenyl, alkenyloxy or alkoxyalkyl with 2 to 7 C atoms,
• Y 41 and Y 42 each independently of one another H or F.
• liquid crystal dislpays containing liquid crystalline media containing compounds of formula IV, wherein at least one of
• liquid crystalline media containing at least one compound of formula I, preferably at least one compound of formula la and at least one compound of formula lb, and at least one compound of formula II and at least one compound of formula III.
• liquid crystal displays cintaining liquid crystalline media containing one or more compounds of formula III selected from the group of formulae Ilia to lilt.
• R 3 has the meaning given under formula III above.
• the liquid crystal display contains a liquid crystal medium containing one oer mora compounds selected from the group of formulae III b, III c, III i, 111 j, III m, III o bis III s, most preferrably of formulae III b, III c, 111 i, III m, III o und III s.
• k 1 , 2, 3, 4 or 5
• n and n each independently from one another are 0, 1 , 2 or 3
• o 0 or 1.
• R 4 has the meaning given above under the respective formulae formula IVa to IVd.
• the displays contain media containing one or more compounds of formula I in a concentration relative to the whole medium in a concentration in the range from 20%, preferably 27%, to 75%, preferably from 40% to 70%, more preferably from 45% to 65% and most preferred from 50% to 60%.
• the displays contain media containing one or more compounds of formula la, preferably of formula Ia1 , in a concentration relative to the whole medium in a concentration in the range from 15% to 60%, preferably from 20% to 55%, more preferably from 25% to 50% and most preferred from 29% to 45%.
• the displays contain media containing one or more compounds of formula lb, preferablay of formula Ib1 , in a concentration relative to the whole medium in a concentration in the range from 1 % to 40%, preferably from 5% to 35%, more preferably from 10% to 30% and most preferred from 15% to 30%.
• the medium contains only compounds of formula I which are compounds of formula la their concentration is 22% or more, preferrably 25% or more and most preferrably 28% or more.
• the media preferably contain two or more compounds of formula la, preferably of formula Ia1
• the media contain one or more compounds each of formulae la and lb.
• the media preferably contain two, three or more compounds of formula la, preferably of formula Ia1 and the concentration of all compounds of formula I in the medium is 37% or more preferably 43% or more.
• R21 is alkyl or alkoxy with 1 to 7 C atoms, preferably alkyl or alkoxy, especially preferred alkoxy, with 1 to 3 C atoms and
• R 2 is alkyl with 1 to 7 C atoms, preferably witt 1 to 5 C atoms and/or one or more compounds of formula Hb1
• R21 and R22 each independently of one another are alkyl or alkoxy with 1 to 7 C atoms or alkoxyalkyl with 2 to 7 C atoms, preferably R 21 is n-alkyl and R 22 is n-alkyl with 3 to 5 C atoms and
• R21 and R22 each independently of one another are alkyl or alkoxy with 1 to 7 C atoms or alkoxyalkyl with 2 to 7 C atoms, preferably R 21 and R 22 are n-alkyl with 3 to 5 C atoms and
• R 51 and R 52 each independently of one another are alkyl or alkoxy with 1 to 7 C atoms or alkoxyalkyl with 2 to 7 C atoms, and R 52 may also be F or OCF 3 ,
• R 51 and R 52 have the respective meanings given under formula V above, preferably R 51 is n-alkyl and R 52 is n- alkayl or n- alkoxy.
• one or more compounds of formula Ila1 wwhheerreeiin preferably at least one of the groups R and R is n-alkoxy and/or
• one or more compounds of formula Ilb1 wwhheerreeiin preferably at least one of the groups R 21 and R 22 is n-alkoxy and/or
• displays according to the invention which are addessed by a matrix of active electrical switching elements which have a non-linear voltage-current characteristic.
• a further topic of the invention is a liquid crystalline medium having a positive dielectric anisitropy containing two, three, four, five or more compounds of formula I and one or more compounds selected from the group of formulae lla to lie, one or more compounds selected from the group of formulae Ilia to lilt and one or more compounds selected from the group of formulae IVa to IVe, in particular a medium which contains
• the media used according to the invention generally have a birefringence ( ⁇ n) at 20°C which is in the range from 0.060 to 0.150, preferably from 0.065 to 0.140 and most preferably from 0.070 to 0.130.
• the clearing points of the media preferably are in the range from 60°C to 110°C, more preferably from 65°C to 100°C and most preferably from 67°C to 90°C.
• the rotational viscosity ( ⁇ i) of the media used according to the invention at 20°C is, as a rule 100 mPa-s or less, preferably 90 mPa-s or less, more preferably 80 mPa-s or less and most preferably 70 mPa-s or less.
• the rotational viscosity of the inventive liquid crystalline media is related to the clearing point and especially to the polarity, i.e. the dielectrical anisotropy, of the media.
• the polarity i.e. the dielectrical anisotropy
• a rotational viscosity of 85 mPa-s or less preferably of 80 mPa-s or less most preferably of 75 mPa-s or less is achieved
• a rotational viscosity of 80 mPa-s or less preferably of 75 mPa-s or less most preferably of 70 mPa-s or less is achieved
• for media with a clearing point of 70°C and a dielectrical anisotropy of 7 or less a rotational viscosity of 75 mPa-s or less preferably of 70 mPa-s or less most preferably of 60 mPa-s or less is achieved.
• the specific resistance of the media according to the invention at20°C generally is in the range from 5 x 10io to 5 x 10is ⁇ • cm, preferably from 5 x 1011 to 5 x 1012 ⁇ - cm.
• liquid crystalline media used according to the invention are stable against storage in liquid crystal display test cells at -30°C for 1000 h or more, preferably at -40°C for 500 h or more and most preferably at -40°C for 1000 h or more.
• the liquid crystalline media used according to the invention consist of 5 to 30 compounds, preferably of 6 to 20 compounds and most preferably of 7 to 16 compounds.
• alkyl in this application comprises straight chain and branched alkyl groups with 1 to 7 carbon atoms, preferably the straight chain groups methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl and n-heptyl. Groups with 2 to 5 carbon atoms are preferred, unless explicitly stated otherwise.
• alkenyl in this application comprises straight chain and branched alkenyl groups with 2 to 7 carbon atoms, preferably the straight chain groups. Particularly preferred alkenylgroups are C 2 to C 7 1 E-alkenyl, C to C 7 3E-alkenyl, C 5 to C 7 4-alkenyI, C 6 to C 7 5 alkenyl und C 7 6-alkenyl, most preferred C 2 to C 7 1 E-alkenyl, C 4 to C 7 3E-alkenyl and C 5 to C 7 4- alkenyl.
• alkenyl groups which are particularly preferred are vinyl, 1 E-propenyl, 1 E-butenyl, 1 E-pentenyl, 1 E-hexenyl, 1 E-heptenyl, 3E- butenyl, 3E-pentenyl, 3E-hexenyl, 3E-heptenyl, 4-pentenyl, 4Z-hexenyl, 4E-hexenyl, 4Z-heptenyl, 5-hexenyl and 6-heptenyl. Groups with up to 5 C atoms are preferred unless explicitly stated otherwise.
• alkoxyalkyl in this application comprises preferably straigt chain groups of the formula C n H 2n+1 -O-(CH 2 ) m , wherein n und m each are 1 to 6 and n+m is 2 to 7.
• n is 1 and n is 1 to 4.
• E-alkenyl groups, 3E-alkenyl groupd and 2E-alkenyloxy groups generally lead to shorter response times and more stable nematic phases. Shorter side chains, especially with one or two C aloms only also improve the response time significantly. The maximum concentration of compounds with such groups in the media, however is limited by the desired clearing point.
• the optimal proportions of the compounds of formulae I to V depends largely on the desired properties of the medium, on the choice of the compounds of formulae I to V and on the choice of furthe optional compounds. Appropriate mixing ratios within the ranges given in this application can be easily determined.
• the total ammount of compounds of formulae I to V in the media used according to the present invention is not very crucial.
• the media contain 80 to 100% of compounds of formolae I to V.
• the media may also contain one or more additional compounds in order to optimize various properties.
• the effect of the media used according to the invention, however, especially on the response time, generally is larger, in case the total concentration of the compounds of formulae I to V, inparticular of compounds of formula I.
• the media used according to the present invention contain one or more compounds of formula IVc.
• the liquid crystalline media which are used according to the present invention contain besides two or more compounds of formula I preferably three to 40 other compounds, particularly preferred four to 30 other compounds and most preferrably seven to 15 other compounds. These other compounds are preferrably selected from the group of nematic or nematogenic, preferably monotropic or isotropic, compounds.
• liquid crystalline media which are used according to the present invention contain besides two or more compounds of formula I preferably contain 38 to 67%, especially preferred 45 to 55% of compounds of formula I. They contain preferrably three, four, five, six or more compounds of formula I
• the consruction of the electro-optical displays according to the present invention corresponds to the characteristic construction of an I PS-display as described e. g. in WO 91/10936 or EP 0 588 568.
• the term ..characteristic construction is construed rather braodly here and encompasses all known modificatoins of the IPS display, especially IPS displays driven by an active matrix and IPS displays with electrode structures with nonlinar electrodes and/or with non-constant electrode spacing in an individual pixel.
• the liquid crystalline media used according to the present invention are prepared by conventional methods. As a rule the required amounts of the compounds are successively dissolved in the compound or compounds used as the mjor constituent of the medium. This is done preferentially at elevated temperature in order to facilitate mixing of the compounds. Further other known methods of preparation can be emplyed. E. g. the media can be prepared by mixing pre-mixtures, which may be mixtures of homologuous compounds or ready to use mixtures which can be costituents of so called ..multi bottle systems".
• the liquid crystalline media optionally contain further additives known to the expert.
• the media can contain 0% to 15%, preferably 0% to 10%, of pleochroic dyes and/or chiral dopants.
• the concentrations of the single compounds added are in the range from 0.01% to 6%, preferably from 0.1 % to 3%.
• the concentrations of these additives are, however, not considered in the concentrations and ranges of the concentration ranges of the main compounds making up the media (i. e. of formulae I to V and of the optional compounds).
• V 0 is the capacitive threshold.
• ⁇ n is the optical aisotropy (birefringence) at 589 nm.
• ⁇ is the dielektrical anisotropy at 1 kHz.
• the electro-optical properties were determined in planar cells. The cells are operated in the normally white mode.
• PGU-n-F Prefered displays contain liquid crystalline media containing, besides two or more compounds of formula I, one or more compounds selected from the group of formulae of thables A and B.
• IPS displays containing media containing
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• V 0 (1 kHz, 20 °C) 1.45 V
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties
• the display shows excellent contrast and a fast response time.
• An IPS-display is prepared containing a nematic liquid crystal mixture having the following composition and physical properties

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• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Organic Chemistry (AREA)
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• Liquid Crystal (AREA)

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• 2001
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