EP2181175A1 - Affichage à cristaux liquides - Google Patents

Affichage à cristaux liquides

Info

Publication number
EP2181175A1
EP2181175A1 EP08785213A EP08785213A EP2181175A1 EP 2181175 A1 EP2181175 A1 EP 2181175A1 EP 08785213 A EP08785213 A EP 08785213A EP 08785213 A EP08785213 A EP 08785213A EP 2181175 A1 EP2181175 A1 EP 2181175A1
Authority
EP
European Patent Office
Prior art keywords
compounds
formula
alkyl
atoms
independently
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP08785213A
Other languages
German (de)
English (en)
Inventor
Georg Bernatz
Melanie Klasen-Memmer
Matthias Bremer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP2181175A1 publication Critical patent/EP2181175A1/fr
Withdrawn legal-status Critical Current

Links

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
    • C09K19/06—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
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • 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
    • C09K2019/0451—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 CH3CH=CHCH2CH2- chain
    • 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
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3004—Cy-Cy
    • 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
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3009—Cy-Ph
    • 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
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/301—Cy-Cy-Ph
    • 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
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3016—Cy-Ph-Ph
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/542—Macromolecular compounds
    • C09K2019/548—Macromolecular compounds stabilizing the alignment; Polymer stabilized alignment
    • 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
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • 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
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/02—Alignment layer characterised by chemical composition

Definitions

  • the present invention relates to liquid crystal (FK) displays of the PS (polymer stabilized) or PSA (polymer sustained alignment) type, as well as novel polymerizable compounds and novel FK media for
  • the currently used liquid crystal displays are usually those of the TN type (twisted nematic). However, these have the disadvantage of a strong viewing angle dependence of the contrast.
  • VA vertical alignment
  • the FK cell of a VA display contains a layer of FK medium between two transparent electrodes, the FK medium usually having a negative value of dielectric (DK) anisotropy.
  • DK dielectric
  • the molecules of the FK layer are orientated in the off state perpendicular to the electrode surfaces (homeotropic) or tilted homeotropic (English, "tilted”). When an electrical voltage is applied to the electrodes, a reorientation of the FK molecules takes place parallel to the electrode surfaces.
  • OCB displays optical compensated bend
  • OCB displays which are based on a birefringence effect and have an FK layer with a so-called "bend” orientation and usually positive (DK) anisotropy.
  • DK positive
  • OCB displays typically contain one or more birefringent optical retardation films to avoid unwanted transmittance of the "bend" cell in the dark state.
  • OCB displays have a wider viewing angle and shorter switching times than TN displays.
  • IPS displays in-plane switching
  • FK layer between two substrates, of which only one has an electrode layer with a usually comb-shaped structure.
  • Substrate include, however, in contrast to IPS displays, only one is formed as a structured (comb-shaped) electrode, and the other electrode is unstructured. This creates a strong "fringe field", a strong electric field near the edge of the electrodes and an electric field throughout the cell that has both a strong vertical and a strong horizontal component, both IPS and FFS Displays show a low viewing angle dependence of the contrast.
  • VA displays In more recent VA displays, the uniform alignment of the FK molecules is confined to several smaller domains within the FK cell. Between these domains, also called tilt domains, there may be disclinations. VA displays with tilt domains have greater viewing angle independence of contrast and grayscale compared to traditional VA displays. In addition, such displays are easier to manufacture, since additional treatment of the electrode surface for uniform orientation of the molecules in the on state, such as, e.g. by rubbing, is no longer necessary. Instead, the preferred direction of the tilt or tilt angle (English, "pretilt") by a special
  • the distances between the slits and protrusions can be increased, which in turn leads to an extension of the switching times.
  • the so-called PVA Pattemed VA
  • PVA can be done without any protrusions by structuring both electrodes on the opposite sides through slots, which leads to increased contrast and improved light transmission, but is technologically difficult and makes the display more sensitive to mechanical influences (knocking , English, "tapping", etc.)
  • a shortening of the switching times and an improvement of the contrast and the luminance (transmission) of the display is required.
  • PSA displays polymer sustained alignment
  • FK medium a small amount (for example 0.3% by weight, typically ⁇ 1% by weight) of a polymerizable compound is added, which after filling in the FK - ZeIIe is polymerized or crosslinked in situ with applied electrical voltage between the electrodes, usually by UV photopolymerization.
  • RM reactive mesogens
  • PSA-VA, PSA-OCB, PS-IPS and PS-TN displays are known.
  • the PSA method leads to a pretilt in the cell.
  • PSA OCB displays it is therefore possible to stabilize the bend structure so that it can do without offset voltage or reduce it.
  • this pretilt has a positive effect on the switching times.
  • a standard MVA or PVA pixel and electrode layout can be used become.
  • PSA-VA displays are described, for example, in JP 10-036847 A, EP 1 170 626 A2, EP 1 378 557 A1, EP 1 498 468 A1, US 2004/0191428 A1, US 2006/0066793 A1 and US 2006/0103804 A1 , PSA-OCB displays are described, for example, in T.J. Chen et al., Jpn. J. Appl. Phys. 45, 2006, 2702-2704 and S.H. Kim, L.-C-Chien, Jpn. J. Appl. Phys. 43
  • PS-I PS displays are described, for example, in US 6,177,972 and Appl. Phys. Lett. 1999, 75 (21), 3264.
  • PS-TN displays are described, for example, in Optics Express 2004, 12 (7), 1221.
  • Photoinitiators is desired, which may be advantageous for certain applications.
  • the selected “material system” FK mixture (hereinafter also referred to as “FK host mixture”) + polymerizable component as low a rotational viscosity as possible and as possible
  • FK host mixture FK host mixture
  • the so-called “Voltage Holding Ratio” (HR or VHR) should be emphasized
  • HR or VHR Voltage Holding Ratio
  • PS (A) displays especially of the VA and OCB type, as well as LC media and polymerizable compounds for use in such displays, which do not or only slightly show the disadvantages described above and have improved properties.
  • PS (A) displays with high resistivity coupled with a large operating temperature range, short switching times even at low temperatures and low threshold voltages, which allow for a variety of gray levels, high contrast, and wide viewing angles , as well as high values of the "voltage holding ratio" (HR) after UV exposure.
  • HR voltage holding ratio
  • the invention had the object of providing PS (A) displays, which have the disadvantages mentioned above not or only to a lesser extent, allow the setting of a pretilt angle and preferably at the same time have very high resistivities, low threshold spans and low switching times.
  • the invention thus relates to a liquid crystal (FK) display of the PS (polymer stabilized) or PSA (polymer-sustained alignment) type, preferably comprising an FK cell consisting of two substrates, wherein at least one substrate is translucent and at least one substrate an electrode layer, as well as an interposed between the substrates of a FK medium containing a polymerized component and a low molecular weight component, wherein the polymerized component is obtainable by polymerization of one or more polymerizable compounds between the substrates of FK ZeIIe in FK medium under application an electrical voltage, characterized in that the low molecular weight component contains one or more compounds of the formula A.
  • FK liquid crystal
  • L 1 and L 2 are each independently H, F or Cl,
  • R 1 is the same or different at each occurrence - (CH 2 ) m -
  • n is the same or different 0, 1, 2, 3, 4 or 5 at each occurrence
  • n is identical or different at each instance and is 1, 2, 3, 4, 5 or 6, where n + m ⁇ 6.
  • Another object of the invention is an LC medium containing one or more polymerizable compounds and one or more low molecular weight compounds as described above and below.
  • FK-host mixture containing one or more, preferably two or more low molecular weight (ie monomeric or unpolymerized) compounds, of which at least a compound of Formula A is selected, as well
  • a polymerizable component B containing one or more polymerizable compounds as described above and below.
  • the invention further provides an LC display comprising one or more compounds of the formula A or an LC medium according to the invention, in particular a PS or PSA display, particularly preferably a PSA-VA, PSA-OCB, PS-IPS , PS-FFS or PS-TN
  • R 2 is preferably straight-chain alkyl or alkoxy having 1 to 8 C atoms, more preferably methoxy, ethoxy, n-propoxy or n-butoxy, or has one of the meanings given for R 1 .
  • Further preferred compounds of the formula A are those in which L 1 and L 2 are F, those in which L 1 and L 2 are H, and those in which L 1 is Cl and L 2 is F or L 1 is Fl and L 2 is Cl.
  • the compounds of the formula A are preferably selected from the following formulas:
  • R 1 is the same or different at each occurrence as defined above, o is 0 or 1
  • LC media in which component A) is an FK compound or an LC mixture having a nematic liquid crystal phase. Further preferred are LC media containing one, two or three polymerizable compounds as described above and below.
  • Containing media preferably exclusively consisting of, achiral compounds.
  • the polymerizable compounds can be added individually to the LC media, but it is also possible to use mixtures containing two or more polymerizable compounds according to the invention. Upon polymerization of such mixtures, copolymers are formed.
  • the polymerizable mixtures mentioned above and below are a further subject of the invention.
  • the polymerizable compounds are mesogenic or non-mesogenic, preferably mesogenic or liquid crystalline.
  • the polymerisable compounds are selected from formula I.
  • R a and R b are each independently P-Sp-, H, halogen, SF 5 ,
  • a 1 and A 2 each independently represent an aromatic, heteroaromatic, alicyclic or heterocyclic group, preferably of 4 to 25 carbon atoms, which may also contain fused rings, and which is optionally monosubstituted or polysubstituted by L,
  • L is P-Sp-, H, OH, CH 2 OH, halogen, SF 5 , NO 2 , a carbon group or hydrocarbon group,
  • R 0 and R 00 are each independently H or alkyl of 1 to 12 C atoms
  • n1 1, 2, 3 or 4.
  • Particularly preferred compounds of the formula I are those in which A 1 and A 2 are each independently 1, 4-phenylene, naphthalene-1, 4-diyl or naphthalene-2,6-diyl, wherein in these groups one or more CH groups may be replaced by N, cyclohexane-1 , 4-diyl, in which also one or more non-adjacent CH 2 groups may be replaced by O and / or S, 1, 4-cyclohexenylene, bicyclo [1.1.1] pentane-1, 3-diyl, bicyclo [2.2 .2] octane-1, 4-diyl, spiro [3.3] heptane-2,6-diyl, piperidine-1,4-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2 , 6-diyl, indan-2,5-diyl or octa
  • Groups can be unsubstituted or monosubstituted or polysubstituted by L,
  • Y 1 is halogen
  • R has one of the meanings given for R x , and preferably P-Sp or straight-chain or branched
  • Alkyl or alkoxy having 1 to 12 C atoms, m 2 and m 3 are each independently an integer from 1 to 8, r 0, 1, 2, 3 or 4, s 0, 1, 2 or 3,
  • R y and R z are each independently H or CH 3 ,
  • L is F or CH 3
  • Z 1 is preferably -COO-, -OCO- or a single bond, mean.
  • polymerisable compounds are chiral compounds selected from formula II:
  • R * has the same or different meanings for each occurrence as one of the meanings given for R a in formula I,
  • Q denotes a k-valent chiral group which is optionally monosubstituted or polysubstituted by L,
  • k 1, 2, 3, 4, 5 or 6,
  • Particularly preferred compounds of the formula II contain a monovalent group Q of the formula III
  • a * and B * are each independently fused benzene, cyclohexane or cyclohexene,
  • Q 1 is alkylene or alkyleneoxy having 1 to 9 C atoms or a single bond
  • Q 3 is F, Cl, CN or alkyl or alkoxy as defined for Q 2 but different from Q 2
  • Examples of preferred groups of the formula IV are 2-butyl (1-methylpropyl), 2-methylbutyl, 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, in particular 2-methylbutyl, 2-methylbutoxy, 2-methylpentoxy, 3-methylpentoxy, 2-ethylhexoxy, 1-methylhexoxy, 2-octyloxy, 2-oxa-3-methylbutyl, 3-oxa-4-methylpentyl, 4-methylhexyl, 2-hexyl, 2-octyl, 2-nonyl, 2- decyl, 2-dodecyl, 6-methoxyoctoxy, 6-methyloctoxy, 6-methyloctanoyloxy, 5-methylheptyloxycarbonyl, 2-methylbutyryloxy, 3-methylvaleroyloxy, 4-methylhexanoyloxy, 2-chloropropionyloxy, 2-chloro-3-methylbutyly
  • Phe is phenyl, which is optionally mono- or polysubstituted by L, and R x is F or optionally fluorinated alkyl having 1 to 4 carbon atoms.
  • Particularly preferred compounds of the formula II are selected from the following sub-formulas
  • L, P, Sp, m1, r and t have the abovementioned meaning
  • Z and A have the same or different meanings for Z 1 and A 1, respectively
  • t 1 is the same or different at each occurrence or 1 means.
  • PSA PS displays and PSA displays unless otherwise specified.
  • meogenic group is known to the person skilled in the art and described in the literature, and means a group which, due to the anisotropy of its attractive and repulsive interactions, contributes substantially to low molecular weight or polymeric
  • Substances cause a liquid crystal (FK) phase.
  • Compounds containing mesogenic groups may not necessarily have an FK phase themselves. It is also possible that mesogenic compounds show FK phase behavior only after mixing with other compounds and / or after polymerization.
  • Typical mesogenic groups are, for example, rigid rod-shaped or disc-shaped units.
  • spacer group or “spacer” above and below a flexible group which connects the mesogenic group and the polymerizable group (s) in a polymerizable mesogenic compound (“RM").
  • reactive mesogen refers to a compound containing a mesogenic group and one or more functional groups suitable for polymerization (also referred to as polymerizable group or group P).
  • low molecular weight compound and "unpolymerizable compound” mean, usually monomeric, compounds which do not have a functional group suitable for polymerization under the usual conditions known to those skilled in the art, especially under the conditions used to polymerize the RMs.
  • organic group means a carbon or hydrocarbon group.
  • carbon group means a monovalent or polyvalent organic group containing at least one carbon atom, which either contains no further atoms (such as -C ⁇ C-), or optionally one or more further atoms such as N, O, S, Contains P, Si, Se, As, Te or Ge (eg carbonyl, etc.).
  • hydrocarbon group means a carbon group which additionally contains one or more H atoms and optionally one or more heteroatoms such as, for example, N, O, S, P, Si, Se, As, Te or Ge.
  • Halogen means F, Cl, Br or I.
  • a carbon or hydrocarbon group may be a saturated or unsaturated group. Unsaturated groups are, for example, aryl, alkenyl or alkynyl groups.
  • a carbon or hydrocarbon radical having more than 3 C atoms may be straight-chain, branched and / or cyclic, and may also have spiro-linkages or fused rings.
  • alkyl also include polyvalent groups, for example alkylene, arylene, heteroarylene, etc.
  • aryl means an aromatic carbon group or a group derived therefrom.
  • heteroaryl means "aryl” as defined above containing one or more heteroatoms.
  • Preferred carbon and hydrocarbon groups are optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy and alkoxycarbonyloxy having from 1 to 40, preferably 1 to 25, more preferably 1 to 18 carbon atoms, optionally substituted aryl or aryloxy having 6 to 40, preferably 6 to 25 C-atoms, or optionally substituted alkylaryl, arylalkyl, alkylaryloxy, arylalkyloxy, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy and aryloxycarbonyloxy having 6 to 40, preferably 6 to 25 C-atoms.
  • carbon and hydrocarbon groups are C r C 40 alkyl, C 2 -C 40 alkenyl, C 2 -C 40 alkynyl, C 3 -C 40 allyl, C 4 -C 40 alkyl dienyl, C 4 -C 40 polyenyl, C 6 -C 40 aryl, C 6 -C 40 alkylaryl, C 6 -C 40 arylalkyl, C 6 -C 40 alkylaryloxy, C 6 -C 40 arylalkyloxy, C 2 -C 40 heteroaryl, C 4 -C 40 cycloalkyl, C 4 - C 40 cycloalkenyl, etc.
  • C 1 -C 22 alkyl Particularly preferred are C 1 -C 22 alkyl, C 2 -C 22 alkenyl, C 2 -C 22 alkynyl, C 3 -C 22 allyl, C 4 -C 22 alkyldienyl, C 6 -C 12 aryl, C 6 - C 20 arylalkyl and C 2 -C 20 heteroaryl.
  • R x is preferably H, halogen, a straight-chain, branched or cyclic alkyl chain having 1 to 25 C atoms, in which one or more nonadjacent C atoms are represented by -O-, -S-, -CO-, -CO- O-, -O-CO-, -O-CO- O- may be replaced, wherein also one or more H atoms may be replaced by fluorine, an optionally substituted aryl or aryloxy group having 6 to 40 carbon atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 to 40 carbon atoms.
  • alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, n-hexyl, cyclohexyl, 2- Ethylhexyl, n-heptyl,
  • Preferred alkenyl groups are, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, etc.
  • Preferred alkynyl groups are, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, octynyl, etc.
  • Preferred alkoxy groups are, for example, methoxy, ethoxy, 2-methoxyethoxy, 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, etc.
  • Preferred amino groups are, for example, dimethylamino, methylamino, methylphenylamino, phenylamino, etc.
  • Aryl and heteroaryl groups may be mononuclear or polynuclear, ie they may be one ring (such as phenyl) or two or more rings which may also be fused (such as naphthyl) or covalently linked (such as biphenyl), or a combination of fused and linked rings.
  • Heteroaryl groups contain one or more heteroatoms, preferably selected from O, N, S and Se.
  • Aryl and heteroaryl groups, wherein also one or more CH groups can be replaced by N, S or O so that O atoms and / or S atoms are not directly linked.
  • Preferred aryl groups are, for example, phenyl, biphenyl, terphenyl, [i.r1''r'lTerphenyl'-yl, naphthyl, anthracene, binaphthyl, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzpyrene, fluorene, indene , Indenofluoren, spirobifluoren, etc.
  • 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, pyridazine, pyrimidine, pyrazine, 1, 3,5-triazine, 1, 2,4-triazine, 1, 2,3-triazine, 1, 2,4,5-tetrazine, 1, 2,3,4-tetrazine, 1, 2,3,
  • heteroaryl groups may also be substituted by alkyl, alkoxy, thioalkyl, fluorine, fluoroalkyl or other aryl or heteroaryl groups.
  • the (non-aromatic) alicyclic and heterocyclic groups include both saturated rings, ie those containing only single bonds, and partially unsaturated rings, ie those which may also contain multiple bonds.
  • Heterocyclic rings contain one or more heteroatoms, preferably selected from Si 1 O, N, S and Se.
  • the (non-aromatic) alicyclic and heterocyclic groups may be mononuclear, i. contain only one ring (such as cyclohexane), or polynuclear, i. contain several rings (such as decahydronaphthalene or bicyclooctane). Particularly preferred are saturated groups. Also preferred are mono-, di- or trinuclear groups having 3 to 25 carbon atoms, which optionally contain fused rings and are optionally substituted. Also preferred are 5-, 6-, 7- or 8-membered carbocyclic groups in which also one or more C atoms may be replaced by Si and / or one or more CH atoms.
  • Groups may be replaced by N and / or one or more non-adjacent CH 2 groups may be replaced by -O- and / or -S-.
  • Preferred alicyclic and heterocyclic groups are, for example, 5-membered groups such as cyclopentane, tetrahydrofuran,
  • the aryl, heteroaryl, carbon and hydrocarbon radicals optionally have one or more substituents which are preferably selected from the group comprising silyl, sulfo, sulfonyl, formyl, amine, imine, nitrile, mercapto, nitro, halogen, C ⁇ 2 alkyl, C ⁇ -1 2 aryl, Ci-i 2 alkoxy, hydroxy, or combinations of these groups.
  • Preferred substituents are, for example, solubility-promoting groups such as alkyl or alkoxy, electron-withdrawing groups such as fluorine, nitro or nitrile, or substituents for increasing the glass transition temperature (Tg) in the polymer, in particular bulky groups such as e.g. t-butyl or optionally substituted aryl groups.
  • Preferred substituents are, for example, F, Cl, Br, I, -CN, -NO 2 , -NCO, -NCS, -OCN, -SCN, -
  • R x has the meaning given above and Y 1 is halogen represents optionally substituted SiIyI or aryl having 6 to 40, preferably 6 to 20 C atoms, and straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, wherein one or more H atoms optionally may be replaced by F or Cl.
  • Substituted SiIyI or aryl is preferably substituted by halogen, - CN, R 0 , -OR 0 , -CO-R 0 , -CO-OR 0 , -O-CO-R 0 or -O-CO-OR 0 , wherein R 0 has the meaning given above.
  • substituents L are, for example, F, Cl, CN, NO 2 , CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , COCH 3 , COC 2 H 5 , COOCH 3 , COOC 2 H 5 , CF 3 , OCF 3 , OCHF 2 , OC 2 F 5 , furthermore phenyl.
  • the polymerizable group P is a group suitable for a polymerization reaction, such as free-radical or ionic chain polymerization, polyaddition or polycondensation, or for a polymer-analogous reaction, for example the addition or
  • Condensation to a polymer backbone is suitable.
  • Substituted L is as defined above, ki, k 2 and k 3 are each independently O or 1, k 3 is preferably 1.
  • the polymerizable compounds of the formula I and their sub-formulas contain one or more branched radicals having two or more polymerizable groups P (multifunctional polymerizable radicals) instead of one or more radicals P-Sp.
  • Suitable radicals of this type, as well as polymerizable compounds containing them, are described, for example, in US Pat. No. 7,060,200 B1 or US 2006/0172090 A1.
  • alkyl is a single bond or straight or branched one
  • aa and bb are each independently 0, 1, 2, 3, 4, 5 or 6,
  • X has one of the meanings given for X ', and
  • pP1 1 - " 5 5 each independently have one of the meanings given above for P.
  • Preferred spacer groups Sp are selected from the formula Sp'-X 1 , so that the radical "P-Sp-" corresponds to the formula "P-Sp'-X 1 -", where
  • Sp 1 is alkylene of 1 to 20, preferably 1 to 12, C atoms, which is optionally mono- or polysubstituted by F, Cl, Br, I or CN, and wherein one or more non-adjacent CH 2 groups are each independently from each other by -O-, -S-, -
  • R 0 and R 00 are each independently H or alkyl of 1 to 12 carbon atoms
  • Y 2 and Y 3 are each independently H, F, Cl or CN.
  • X 1 is preferably -O-, -S-CO-, -COO-, -OCO-, -O-COO-, -CO-NR 0 -, -NR ° -CO-, -NR ° -CO-NR ° - or a single bond.
  • Typical spacer groups Sp ' are for example - (CH 2 ) p i-, - (CH 2 CH 2 O) q1 - CH 2 CH 2 -, -CH 2 CH 2 -S-CH 2 CH 2 -, -CH 2 CH 2 -NH-CH 2 CH 2 - or - (SiR ° R 00 -O) p1 -, wherein p1 is an integer from 1 to 12, q1 is an integer from 1 to 3, and R 0 and R 00 are as above have given meanings.
  • Particularly preferred groups -X Sp'- are - (CH 2) p i-, -O- (CH 2) p r, -OCO- (CH 2) p1 -, -OCOO- (CH 2) P1 -.
  • Particularly preferred groups Sp 1 are, for example, in each case straight-chain ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylene thioethylene, ethylene-N-methyl-iminoethylene, 1-methylalkylene , Ethenylene, propenylene and butenylene.
  • the synthesis is carried out by esterification or etherification of commercially available diols of the general formula HO-A 1 - (Z 1 -A 2 ) m rOH, where A 1 , A 2 , Z 1 and m are those indicated above
  • Polymerization methods are, for example, thermal or photopolymerization, preferably photopolymerization, in particular UV photopolymerization. If appropriate, one or more initiators can also be added. Suitable conditions for the polymerization, as well as suitable types and amounts of initiators, are known in the art and described in the literature.
  • the radical polymerization e.g. the commercially available photoinitiators Irgacure651®, Irgacure184®, Irgacure907®, Irgacure369®, or Darocurei 173® (Ciba AG).
  • the proportion in the total mixture is preferably 0.001 to 5 wt .-%, particularly preferably 0.001 to 1 wt .-%.
  • the polymerization can also be carried out without addition of an initiator.
  • the LC medium contains no polymerization initiator.
  • the polymerizable component or LC medium may also contain one or more stabilizers to prevent undesired spontaneous polymerization of the RMs, for example during storage or transportation.
  • stabilizers Suitable types and amounts of stabilizers are known to those skilled in the art and described in the literature. Particularly suitable are e.g. the commercially available stabilizers of the series Irganox ® (Ciba AG). If stabilizers are used, their proportion, based on the total amount of RMs or polymerisable component A), is preferably 10 to 5000 ppm, more preferably 50 to 500 ppm.
  • the polymerizable compounds according to the invention are also suitable for polymerization without initiator, which brings considerable advantages, such as lower material costs and in particular a lower contamination of the LC medium by possible residual amounts of the initiator or its degradation products.
  • the LC media according to the invention preferably comprise ⁇ 5%, more preferably ⁇ 1%, very preferably ⁇ 0.5% of polymerisable compounds, in particular polymerisable compounds of the abovementioned formulas.
  • the polymerizable compounds according to the invention can be added individually to the LC media, but it is also possible to use mixtures containing two or more polymerizable compounds. Upon polymerization of such mixtures, copolymers are formed.
  • the polymerizable mixtures mentioned above and below are a further subject of the invention.
  • the LC media for use in the LC displays according to the invention contain, in addition to the polymerizable described above
  • an FK blend (“host blend”) containing one or more, preferably two or more, low molecular weight (i.e., monomeric or unpolymerized) compounds.
  • the latter are stable or unreactive to a polymerization reaction under the conditions used for the polymerization of the polymerizable compounds.
  • the host mixture can be any FK mixture suitable for use in conventional VA and OCB displays.
  • Suitable LC mixtures are known to the person skilled in the art and described in the literature, for example mixtures in VA displays in EP 1 378 557 A1, and mixtures for OCB displays in EP 1 306 418 A1 and DE 102 24 046 A1.
  • FK medium containing one or more compounds selected from the following formulas:
  • L 1 "4 each independently of one another F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F, CHF 2 .
  • both radicals L 1 and L 2 are F, or one of the radicals L 1 and L 2 F and the other Cl, or both radicals L 3 and L 4 F, or one of the radicals L 3 and L 4 F and the other Cl.
  • the compounds of the formula CY are preferably selected from the following sub-formulas
  • alkyl and alkyl * each independently represent a straight-chain alkyl radical having 1-6 C atoms.
  • the compounds of formula PY are preferably selected from the following sub-formulas:
  • alkyl and alkyl * each independently represent a straight-chain alkyl radical having 1-6 C atoms.
  • the compounds of the formula ZK are preferably selected from the following sub-formulas:
  • alkyl and alkyl * each independently represent a straight-chain alkyl radical having 1-6 C atoms.
  • R 5 and R 6 are each independently one of the meanings given above for R 1 ,
  • the compounds of the formula DK are preferably selected from the following sub-formulas:
  • LC medium which additionally contains one or more compounds of the following formula:
  • L 1 and L 2 are each independently F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F, CHF 2 .
  • both radicals L 1 and L 2 are F or one of
  • the compounds of the formula LY are preferably selected from the following sub-formulas
  • R 1 has the meaning given above and v is an integer from 1 to 6.
  • R 1 is preferably straight-chain alkyl, in particular CH 3 , C 2 H 5 , nC 3 H 7> nC 4 H 9 , nC 5 Hn
  • FK medium which additionally contains one or more compounds selected from the following formulas:
  • X is F.
  • FK medium which additionally contains one or more compounds selected from the following formulas:
  • R 5 has one of the meanings given above for R 1 , alkyl Ci- ⁇ -alkyl, d is 0 or 1, and z and m are each independently an integer from 1 to 6.
  • R 5 is particularly preferably C 1 -C 6 -alkyl or -alkoxy in these compounds, d is preferably 1.
  • the LC according to the invention comprises
  • Biphenyl compounds of the following formula contains:
  • alkyl and alkyl * each independently represent a straight-chain alkyl radical having 1-6 C atoms.
  • the proportion of biphenyls of the formula B1 in the LC mixture is preferably at least 3% by weight, in particular> 5% by weight.
  • the compounds of formula B1 are preferably selected from the following sub-formula
  • alkyl * is an alkyl radical having 1-6 C atoms.
  • the medium according to the invention contains one or more compounds of the formulas B1a.
  • FK medium which additionally contains one or more terphenyl compounds of the following formula:
  • R 5 and R 6 each independently have one of the meanings given above for R 1 , and
  • L 5 is F or Cl, preferably F
  • L 6 is F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F or CHF 2, preferably F.
  • the compounds of the formula T are preferably selected from the following sub-formulas
  • R is a straight-chain alkyl or alkoxy radical having 1-7 C atoms and m is an integer from 1 to 6.
  • R is methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy or pentoxy.
  • the LC medium according to the invention contains the terphenyls of the formulas T and their preferred sub-formulas preferably in an amount of 2-30% by weight, in particular of 5-20% by weight.
  • R preferably denotes alkyl, furthermore alkoxy in each case with 1-5 C atoms.
  • the terphenyls are preferably used in mixtures according to the invention if the ⁇ n value of the mixture is to be> 0.1.
  • Preferred mixtures contain 2-20% by weight of one or more terphenyl compounds of the formula T, preferably selected from the group of the compounds T1 to T21.
  • FK medium which additionally contains one or more compounds of the following formulas:
  • R 1 and R 2 have the meanings given above, and preferably each independently represent straight-chain alkyl.
  • Preferred media contain one or more compounds selected from the formulas 01, 03 and 04.
  • LC medium which additionally contains one or more compounds of the following formula:
  • R 9 is H, CH 3 , C 2 H 5 or nC 3 H 7 and q is 1, 2 or 3, and R 7 has one of the meanings given for R 1 , preferably in amounts of> 3% by weight, in particular> 5 % By weight, and most preferably from 5-30% by weight.
  • R 7 is preferably straight-chain alkyl and R 9 is CH 3 , C 2 H 5 or nC 3 H 7 .
  • Particularly preferred are the compounds of the formula FM, FI2 and FI3.
  • FK medium which additionally contains one or more compounds of the following formulas:
  • R 8 has the meaning given for R 1 and alkyl is a straight-chain alkyl radical having 1-6 C atoms.
  • FK medium additionally containing one or more compounds having a tetrahydronaphthyl or naphthyl moiety, e.g. the compounds selected from the following formulas:
  • R 10 and R 11 each, independently of one another, have one of the meanings given for R 1 , preferably straight-chain alkyl or straight-chain alkoxy
  • FK medium which additionally contains one or more difluorodibenzochromans and / or chromans of the following formulas:
  • R 11 and R 12 each independently have the abovementioned meaning, and c is 0 or 1, preferably in amounts of 3 to 20 wt.%, In particular in amounts of 3 to 15 wt.%.
  • Particularly preferred compounds of the formulas BC and CR are selected from the following sub-formulas:
  • alkyl and alkyl * each independently represent a straight-chain alkyl radical having 1-6 C atoms.
  • FK medium which additionally contains one or more fluorinated ones
  • R 11 and R 12 each independently have the meanings given above, b is 0 or 1, LF and r is 1, 2 or 3.
  • Particularly preferred compounds of the formulas PH and BF are selected from the following sub-formulas:
  • R and R 1 each independently represent a straight-chain alkyl or alkoxy radical having 1-7 C atoms.
  • FK medium preferably for use in PSA-OCB displays, which contains one or more compounds of the following formulas:
  • R 0 is the same or different n-alkyl at each occurrence
  • Y 1'6 are each independently H or F
  • the compounds of the formula AA are preferably selected from the following formulas:
  • R 0 and X 0 have the abovementioned meaning, and X 0 is preferably F. Particular preference is given to compounds of the formulas AA2 and AA6.
  • the compounds of formula BB are preferably selected from the following formulas:
  • R 0 and X 0 have the abovementioned meaning, and X 0 is preferably F. Particular preference is given to compounds of the formulas BB1, BB2 and BB5.
  • the compounds of the formula CC are preferably selected from the following formulas:
  • R is identical or different in each occurrence as defined above, and preferably alkyl having 1 to 6 carbon atoms.
  • FK medium containing 1 to 5, preferably 1, 2 or 3 polymerizable compounds.
  • FK medium wherein the proportion of polymerizable compounds in the total mixture 0.05 to 5%, preferably 0.1 to 1%.
  • FK medium which contains 1 to 8, preferably 1 to 5 compounds of the formula CY1, CY2, PY1 and / or PY2. The proportion of these compounds in the total mixture is preferably 5 to 60%, particularly preferably 10 to 35%. The salary of each one
  • Compounds are preferably 2 to 20% each.
  • FK medium which 1 to 8, preferably 1 to 5 compounds of
  • Formula CY9, CY10, PY9 and / or PY10 contains.
  • the proportion of these compounds in the total mixture is preferably 5 to 60%, particularly preferably 10 to 35%.
  • the content of these individual compounds is preferably 2 to 20% in each case.
  • FK medium which contains 1 to 10, preferably 1 to 8, compounds of the formula ZK, in particular compounds of the formula ZK1,
  • ZK2 and / or ZK6 The proportion of these compounds in the total mixture is preferably 3 to 25%, particularly preferably 5 to 45%.
  • the content of these individual compounds is preferably 2 to 20% in each case.
  • PS (A) displays show significantly reduced switching times compared to the prior art media, especially the gray scale switching times.
  • the liquid-crystal mixture has a nematic phase range of at least 80 K, more preferably from at least 100 K, and a rotational viscosity of not more than 250, preferably not more than 200 mPa s, at 20 0 C.
  • LC media according to the invention for use in displays of the VA type have a negative dielectric anisotropy ⁇ , preferably from about -0.5 to -7.5, in particular from about -2.5 to -5.5 at 20 0 C and 1 kHz.
  • LC media according to the invention for use in displays of the OCB type have a positive dielectric anisotropy ⁇ , preferably of approximately +7 to +17 at 20 0 C and 1 kHz.
  • the birefringence ⁇ n in FK media according to the invention for use in displays of the VA type is preferably below 0.16, more preferably between 0.06 and 0.14, in particular between 0.07 and 0.12.
  • the birefringence ⁇ n in FK media according to the invention for use in displays of the OCB type is preferably between 0.14 and 0.22, in particular between 0.16 and 0.22.
  • the dielectrics may also contain further additives known to the person skilled in the art and described in the literature.
  • 0 to 15 wt .-% pleochroic dyes may be added, also nanoparticles, conductive salts, preferably ethyl-dimethyldodecylarnmonium-4-hexoxy-benzoate, tetrabutylammonium tetraphenylborate or complex salts of crown ethers (see, for example, Haller et al., Mol. Cryst., 24, 249-258 (1973)) for improving the conductivity, or substances for changing the dielectric anisotropy, the viscosity and / or the orientation of the nematic phases.
  • Such substances are e.g. in DE-A 22 09 127, 22 40 864, 23 21 632, 23 38 281, 24 50 088, 26 37 430 and 28 53 728 described.
  • the preparation of the FK media which can be used according to the invention is carried out in a conventional manner, for example by mixing one or more of the abovementioned compounds with one or more polymerizable compounds as defined above and, if appropriate, with further liquid-crystalline compounds and / or additives.
  • the desired amount of the components used in lesser amount is dissolved in the constituent of the main component, expediently at elevated temperature.
  • an organic solvent e.g. in acetone, chloroform or methanol, and to remove the solvent again after thorough mixing, for example by distillation.
  • the process for producing the LC media according to the invention is a further subject of the invention.
  • the LC media according to the invention can also contain compounds in which, for example, H, N, O, Cl, F have been replaced by the corresponding isotopes.
  • the construction of the FK displays according to the invention corresponds to the geometry customary for PS (A) displays, as described in the cited prior art. Geometries without protrusions are preferred, especially those in which, moreover, the electrode on the color filter side is unstructured and only the
  • Electrode has slits on the TFT side. Particularly suitable and preferred electrode structures for PSA-VA displays are described, for example, in US 2006/0066793 A1.
  • the LC media according to the invention contain one or more compounds selected from the group consisting of compounds of Table A.
  • Table B lists possible dopants which can be added to the LC media according to the invention.
  • the LC media preferably contain 0 to 10% by weight, in particular 0.01 to 5% by weight and more preferably 0.1 to 3% by weight, of dopants.
  • the LC media preferably contain one or more dopants selected from the group consisting of compounds of Table B.
  • Table C lists possible stabilizers which can be added to the LC media according to the invention, (n here denotes an integer from 1 to 12)
  • the FK media preferably contain 0 to 10% by weight, in particular 0.01 to 5% by weight and particularly preferably 0.1 to 3% by weight, of stabilizers.
  • the LC media preferably contain one or several stabilizers selected from the group consisting of compounds of Table C.
  • threshold voltage for the present invention refers to the capacitive threshold (Vo), also referred to as the Freedericksz threshold, unless explicitly stated otherwise
  • the optical threshold for 10% relative contrast can also be used (as usual). Vi 0 ).
  • Display has two plane-parallel carrier plates at a distance of 4 microns and electrode layers with overlying oriented layers of rubbed polyimide on the inner sides of the carrier plates, which cause a homeotropic edge orientation of the liquid crystal molecules.
  • the polymerizable compounds are polymerized in the display by UV irradiation for a predetermined time while applying a voltage to the display (typically 10V to 30V AC, 1 kHz).
  • a voltage to the display typically 10V to 30V AC, 1 kHz.
  • a mercury vapor lamp of 28 mW / cm 2 was used, the intensity was measured with a standard UV meter (manufactured by Ushio UNI meter) equipped with a band-pass filter at 365nm.
  • the tilt angle is determined by a rotary crystal experiment (Autronic-Melcher's TBA-105). A small value (i.e., a large deviation from the 90 ° angle) corresponds to a large TiIt.
  • the basic nematic FK mixture N1 is formulated as follows
  • Mixtures M 1-7 according to the invention are prepared by addition of 0.3% of the polymerizable compound RM1 and different percentages of inventive alkenyl compounds of the formula A with non-terminal double bond, to the base mixture N1.
  • mixtures V1-6 are also prepared by addition of 0.3% of compound RM1, as well as different percentages of alkenyl compounds having a terminal double bond, to the base mixture N1.
  • the reference mixture R1 is prepared by adding 0.3% of the compound RM1 to N1 but without adding alkenyl compounds.
  • Table 1 shows that no appreciable tilt angle can be measured for any of the comparative blends V1-6 containing a double bond-containing alkenyl compound in relevant percentages (i.e., the preferred orientation of the FK long molecular axes is close to 90 °).
  • a clear TiIt can be measured for all mixtures M1-7 according to the invention which comprise an alkenyl compound according to the invention of the formula A with a non-terminal double bond. This is of the same order of magnitude as for the reference mixture R1 without alkenyl compound.

Landscapes

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

Abstract

L'invention concerne un affichage à cristaux liquides (FK) du type PSA (alignement entretenu polymère), ainsi que des composés polymérisables et des milieux FK destinés à être utilisés dans des affichages PSA.
EP08785213A 2007-08-29 2008-07-30 Affichage à cristaux liquides Withdrawn EP2181175A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007040716 2007-08-29
PCT/EP2008/006267 WO2009030318A1 (fr) 2007-08-29 2008-07-30 Affichage à cristaux liquides

Publications (1)

Publication Number Publication Date
EP2181175A1 true EP2181175A1 (fr) 2010-05-05

Family

ID=39816674

Family Applications (1)

Application Number Title Priority Date Filing Date
EP08785213A Withdrawn EP2181175A1 (fr) 2007-08-29 2008-07-30 Affichage à cristaux liquides

Country Status (8)

Country Link
US (1) US8999459B2 (fr)
EP (1) EP2181175A1 (fr)
JP (2) JP5583579B2 (fr)
KR (1) KR101504379B1 (fr)
CN (1) CN101790574B (fr)
DE (1) DE102008035718A1 (fr)
TW (1) TWI472597B (fr)
WO (1) WO2009030318A1 (fr)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008031518A1 (de) * 2007-07-30 2009-02-05 Merck Patent Gmbh Flüssigkristallanzeige
KR20100070337A (ko) * 2007-08-30 2010-06-25 메르크 파텐트 게엠베하 액정 디스플레이
TW201011096A (en) * 2008-09-03 2010-03-16 Au Optronics Corp Vertical alignment liquid crystal display panel and liquid crystal material thereof
DE102010012900A1 (de) * 2009-04-23 2010-11-25 Merck Patent Gmbh Flüssigkristallanzeige
TWI482839B (zh) 2010-01-26 2015-05-01 Jnc Corp 液晶組成物及液晶顯示元件
DE102011009691A1 (de) * 2010-02-09 2011-08-11 Merck Patent GmbH, 64293 Flüssigkristallines Medium
TW201144412A (en) 2010-05-12 2011-12-16 Jnc Corp Liquid crystal composition and liquid crystal display device
JP5657923B2 (ja) * 2010-06-16 2015-01-21 株式会社Adeka 重合性化合物を含有する液晶組成物及び該液晶組成物を用いた液晶表示素子
WO2012055473A1 (fr) * 2010-10-26 2012-05-03 Merck Patent Gmbh Milieu à cristaux liquides, et procédé d'élaboration de dispositif à cristaux liquides
JP5928338B2 (ja) 2010-11-15 2016-06-01 Jnc株式会社 液晶組成物および液晶表示素子
CN104910922A (zh) * 2011-03-09 2015-09-16 夏普株式会社 液晶组合物和液晶显示装置
CN105441086B (zh) * 2011-03-29 2022-01-11 默克专利股份有限公司 液晶介质
JP6056234B2 (ja) 2011-07-27 2017-01-11 Jnc株式会社 液晶組成物および液晶表示素子
TWI586645B (zh) 2011-10-12 2017-06-11 Jnc Corp 聚合性化合物、液晶組成物及液晶顯示元件
US9074132B2 (en) 2011-11-28 2015-07-07 Jnc Corporation Liquid crystal composition and liquid crystal display device
CN104136576B (zh) * 2012-02-22 2020-10-16 默克专利股份有限公司 液晶介质
US20150299571A1 (en) 2012-05-23 2015-10-22 Jnc Corporation Liquid crystal composition and liquid crystal display device
CN103589437B (zh) * 2012-06-29 2018-01-12 默克专利股份有限公司 液晶介质
US9150787B2 (en) 2012-07-06 2015-10-06 Jnc Corporation Liquid crystal composition and liquid crystal display device
TWI565790B (zh) 2012-08-08 2017-01-11 捷恩智股份有限公司 液晶組成物、液晶顯示元件及液晶組成物的使用
JP6411351B2 (ja) * 2012-10-22 2018-10-24 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
TWI623609B (zh) * 2013-03-06 2018-05-11 Dainippon Ink & Chemicals Nematic liquid crystal composition and liquid crystal display element using same
JP6241058B2 (ja) * 2013-04-15 2017-12-06 ソニー株式会社 液晶表示装置
KR102116947B1 (ko) 2013-09-05 2020-06-01 삼성디스플레이 주식회사 액정 표시 장치
US10377949B2 (en) 2013-10-22 2019-08-13 Jnc Corporation Liquid crystal composition and liquid crystal display device
JP2015110741A (ja) 2013-11-11 2015-06-18 Jnc株式会社 液晶組成物および液晶表示素子
DE102013021683A1 (de) * 2013-12-19 2015-06-25 Merck Patent Gmbh Flüssigkristallines Medium
JP2015205982A (ja) 2014-04-18 2015-11-19 Jnc株式会社 液晶組成物および液晶表示素子
WO2016020033A1 (fr) * 2014-08-08 2016-02-11 Merck Patent Gmbh Milieu a cristaux liquides et affichage a cristaux liquides comportant un tel milieu
CN105652499B (zh) * 2016-03-23 2019-01-04 石家庄诚志永华显示材料有限公司 液晶组合物及液晶显示元件或显示器
KR102662829B1 (ko) 2016-09-27 2024-05-03 티씨엘 차이나 스타 옵토일렉트로닉스 테크놀로지 컴퍼니 리미티드 액정 조성물 및 이를 포함하는 표시 장치
CN108219801B (zh) * 2016-12-15 2021-05-25 江苏和成显示科技有限公司 具有负介电各向异性的液晶组合物及其应用
US11008515B2 (en) * 2017-11-24 2021-05-18 Merck Patent Gmbh Liquid-crystalline medium
CN108822871B (zh) * 2018-05-25 2020-09-04 山西义诺电子材料有限公司 一种液晶组合物及其应用
CA3113234A1 (fr) 2018-09-18 2020-03-26 Nikang Therapeutics, Inc. Derives heteroaryles tri-substitues utilises en tant qu'inhibiteurs de la phosphatase src a homologie-2
TWI767148B (zh) 2018-10-10 2022-06-11 美商弗瑪治療公司 抑制脂肪酸合成酶(fasn)

Family Cites Families (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE795849A (fr) 1972-02-26 1973-08-23 Merck Patent Gmbh Phases nematiques modifiees
US3814700A (en) 1972-08-03 1974-06-04 Ibm Method for controllably varying the electrical properties of nematic liquids and dopants therefor
DE2450088A1 (de) 1974-10-22 1976-04-29 Merck Patent Gmbh Biphenylester
DE2637430A1 (de) 1976-08-20 1978-02-23 Merck Patent Gmbh Fluessigkristallines dielektrikum
DE2636684C3 (de) 1976-08-14 1980-06-19 Merck Patent Gmbh, 6100 Darmstadt Phenylcyclohexanderivate und ihre Verwendung in flüssigkristallinen Dielektrika
DE2853728A1 (de) 1978-12-13 1980-07-17 Merck Patent Gmbh Fluessigkristalline carbonsaeureester, verfahren zu ihrer herstellung, diese enthaltende dielektrika und elektrooptisches anzeigeelement
DE3321373A1 (de) * 1983-06-14 1984-12-20 Merck Patent Gmbh, 6100 Darmstadt Bicyclohexyle
DE3807872A1 (de) 1988-03-10 1989-09-21 Merck Patent Gmbh Difluorbenzolderivate
US5871665A (en) 1992-04-27 1999-02-16 Merck Patent Gesellschaft Mit Beschrankter Haftung Electrooptical liquid crystal system
DE4426799B4 (de) 1993-08-03 2013-07-25 Merck Patent Gmbh Benzolderivate und flüssigkristallines Medium
AU1320097A (en) * 1996-01-23 1997-08-20 Chisso Corporation Benzyl ether derivatives, liquid crystal composition, and liquid crystal display
JPH1036847A (ja) 1996-07-25 1998-02-10 Seiko Epson Corp 液晶表示素子およびその製造方法
EP0834491B1 (fr) * 1996-10-02 2001-09-05 MERCK PATENT GmbH Bisalkenyle de bicyclohexane et milieu liquide cristallin
DE19707807A1 (de) 1997-02-27 1998-09-03 Merck Patent Gmbh Elektrooptische Flüssigkristallanzeige
GB2358870B (en) 1997-02-27 2001-10-10 Merck Patent Gmbh Liquid crystalline media having 4,4'-dialk-(1E or 3E)-enyl-1,1'-bicyclohexane and 3,4,5-trifluorophenyl-terminated components, and use in IPS displays
DE19733199A1 (de) * 1997-08-01 1999-02-04 Merck Patent Gmbh Nematische Flüssigkristallzusammensetzung
EP1026142A1 (fr) * 1997-10-24 2000-08-09 Chisso Corporation Derives de 2,3-difluorophenyle presentant une valeur negative d'anisotropie de permittivite, composition a cristaux liquides et element d'affichage a cristaux liquides
JP4989815B2 (ja) * 1998-09-12 2012-08-01 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 液晶媒体およびこれを含有する液晶ディスプレイ
US6177972B1 (en) 1999-02-04 2001-01-23 International Business Machines Corporation Polymer stabilized in-plane switched LCD
US7060200B1 (en) 1999-09-03 2006-06-13 Merck Patent Gmbh Multireactive polymerizable mesogenic compounds
JP2002023199A (ja) 2000-07-07 2002-01-23 Fujitsu Ltd 液晶表示装置およびその製造方法
JP5279975B2 (ja) * 2000-12-19 2013-09-04 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 負のｄｃ異方性のアルケニル化合物と液晶性媒体
DE10224046B4 (de) 2001-06-26 2013-02-07 Merck Patent Gmbh Flüssigkristallines Medium und seine Verwendung
GB2379931B (en) 2001-08-17 2004-12-22 Merck Patent Gmbh Polymerisable dicyclohexylbenzenes
EP1306418B1 (fr) 2001-10-23 2008-06-04 MERCK PATENT GmbH Milieu liquide cristallin et dispositif d'affichage à cristaux liquides
JP4175826B2 (ja) 2002-04-16 2008-11-05 シャープ株式会社 液晶表示装置
DE50306559D1 (de) * 2002-07-06 2007-04-05 Merck Patent Gmbh Flüssigkristallines Medium
ATE368091T1 (de) * 2003-03-06 2007-08-15 Merck Patent Gmbh Elektrolumineszenz-vorrichtung sowie verfahren zu ihrer herstellung
JP2004294605A (ja) 2003-03-26 2004-10-21 Fujitsu Display Technologies Corp 液晶パネル
US7074464B2 (en) 2003-05-14 2006-07-11 Chisso Petrochemical Corporation Perfluoropropenyl-containing compound, liquid crystal composition and liquid crystal display element
JP4387276B2 (ja) 2004-09-24 2009-12-16 シャープ株式会社 液晶表示装置
JP2006139047A (ja) 2004-11-12 2006-06-01 Sharp Corp 液晶表示装置およびその製造方法
JP2006143895A (ja) * 2004-11-19 2006-06-08 Semiconductor Energy Lab Co Ltd 液晶組成物及び電気光学装置
US7527746B2 (en) 2005-01-28 2009-05-05 Chisso Corporation Liquid crystal polyfunctional acrylate derivative and polymer thereof
ATE446351T1 (de) * 2006-07-25 2009-11-15 Merck Patent Gmbh Flüssigkristallines medium
DE502007004908D1 (de) 2006-10-12 2010-10-14 Merck Patent Gmbh Flüssigkristallanzeige
US8114310B2 (en) * 2007-10-22 2012-02-14 Merck Patent Gmbh Liquid-crystal display

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2009030318A1 *

Also Published As

Publication number Publication date
WO2009030318A1 (fr) 2009-03-12
TW200920820A (en) 2009-05-16
KR101504379B1 (ko) 2015-03-19
CN101790574A (zh) 2010-07-28
JP2010537010A (ja) 2010-12-02
JP2014198851A (ja) 2014-10-23
CN101790574B (zh) 2013-09-18
US20100304049A1 (en) 2010-12-02
TWI472597B (zh) 2015-02-11
JP5583579B2 (ja) 2014-09-03
US8999459B2 (en) 2015-04-07
KR20100059916A (ko) 2010-06-04
DE102008035718A1 (de) 2009-03-05

Similar Documents

Publication Publication Date Title
EP2053113B1 (fr) Milieu liquide cristallin
EP2484743B1 (fr) Dispositif d'affichage à base de cristaux liquides
EP2361290B1 (fr) Affichage à base de cristaux liquides
EP2181173B1 (fr) Affichage à base de cristaux liquides
EP2181175A1 (fr) Affichage à cristaux liquides
EP2432851B1 (fr) Dispositif d'affichage à base de cristaux liquides
EP2340292B1 (fr) Dispositif d'affichage a base de cristaux liquides
EP3257916B1 (fr) Milieu cristallin liquide
EP1911828B1 (fr) Affichage à cristaux liquides
EP2483370B1 (fr) Composés polymérisables et leur utilisation dans des dispositifs d'affichage à base de cristaux liquides
EP2181174B1 (fr) Affichage à base de cristaux liquides
EP2585555B1 (fr) Composes polymerisables et utilisation de ceux-ci dans des ecrans a cristaux liquides
WO2010089092A1 (fr) Milieu cristal liquide et dispositif d'affichage à cristaux liquides
DE102009011652A1 (de) Flüssigkristallanzeige
WO2011160764A1 (fr) Composés polymérisables et utilisation de ceux-ci dans des écrans à cristaux liquides
DE102007043921A1 (de) Flüssigkristallanzeige

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20091223

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA MK RS

17Q First examination report despatched

Effective date: 20101104

DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20110315