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US 12,735,641 B2Granted
Liquid-crystal medium
AssigneeMerck Patent GmbH
InventorsEun-Kyu Lee, Jin-Soon Park, Myung-Hee Kim
Life of this patent
Estimating the term…
Abstract
A liquid-crystal (LC) medium comprising polymerizable compounds, its use for optical, electro-optical and electronic purposes, in particular in LC displays, especially in LC displays of the PSA (polymer sustained alignment) or SA (self-aligning) mode, an LC display of the PSA or SA mode comprising the LC medium, and a process of manufacturing the LC display.
Claims20
An LC medium comprising:
- (i) a polymerizable component A) comprising one or more polymerizable compounds selected from formula M13:
- in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
- P1, P2 an acrylate or methacrylate group,
- Sp1, Sp2 a single bond,
- L F, Cl, CN or straight-chain, optionally mono- or polyfluorinated alkyl or alkoxy 1 to 12 C atoms, straight-chain, optionally mono- or polyfluorinated alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy having 2 to 12 C atoms, or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 3 to 12 C atoms, and
- r 0, 1, 2, 3 or 4;
- (ii) a liquid-crystalline component B), comprising one or more mesogenic or liquid-crystalline compounds, wherein component B) comprises
- one or more compounds of formula IIB2
- in which alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, and
- at least two compounds of formula IA, one or more compounds of formula IB, and at least one compound of formula IC-1 and/or IC-2 as defined below
- in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
- R1, R2 straight chain alkyl having 1 to 25 C atoms, branched or cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR0═CR00—, —C≡C—,
- in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F or Cl,
- R0, R00 H or alkyl having 1 to 12 C atoms,
- L1, L2 F,
- alkyl an alkyl radical having 1 to 7 C atoms, and
- alkenyl an alkenyl radical having 2 to 5 C atoms,
- wherein the proportion of compounds of formula IA in the component B) of the LC medium is >8% by weight, and wherein the total proportion of compounds of formulae IC-1 and/or IC-2 in the LC medium is from 20 to 45% by weight;
- and
- (iii) one or more compounds of formula III2-2:
- in which
- L11 and L12 each, independently of one another, denote F, Cl, CF3 or CHF2,
- (O) denotes O or a single bond,
- RIIIA denotes an alkyl having 1-7 C atoms, an alkenyl having 2-7 C atoms or a group Cy-CmH2m+1—,
- m and n are, identically or differently, 0, 1, 2, 3, 4, 5 or 6, and
- Cy denotes a cycloaliphatic group having 3, 4 or 5 ring atoms, wherein the cycloaliphatic group is optionally substituted with an alkyl having 1-3 carbon atoms, an alkenyl having 2-3 C atoms or with halogen or CN.
23 more elements
A process of preparing an LC medium, comprising the steps of:
- mixing one or more polymerizable compounds selected from formula M13:
- in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
- P1, P2 an acrylate or methacrylate group,
- Sp1, Sp2 a single bond,
- L F, Cl, CN or straight-chain, optionally mono- or polyfluorinated alkyl or alkoxy having 1 to 12 C atoms, straight-chain, optionally mono- or polyfluorinated alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy having 2 to 12 C atoms, or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 3 to 12 C atoms, and
- r 0, 1, 2, 3 or 4,
- with one or more compounds of formula IIB2
- in which alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, and at least two compounds of formula IA, one or more compounds of formula IB, and at least one compound of formula IC-1 and/or IC-2
- in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
- R1, R2 straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR0═CR00—, —C≡C—,
- in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F or Cl,
- R0, R00 H or alkyl having 1 to 12 C atoms,
- L1, L2 F,
- alkyl an alkyl radical having 1 to 7 C atoms, and
- alkenyl an alkenyl radical having 2 to 5 C atoms,
- wherein the proportion of compounds of formula IA of the LC medium is >8% by weight based on the total weight of compounds of formulae IA, IB, and IC present, and wherein the total proportion of compounds of formulae IC-1 and/or IC-2 in the LC medium is from 20 to 45% by weight, and
- one or more compounds of formula III2-2:
- in which
- L11 and L 12 each, independently of one another, denote F, Cl, CF3 or CHF2,
- (O) denotes O or a single bond,
- RIIIA denotes an alkyl having 1-7 C atoms, an alkenyl having 2-7 C atoms or a group Cy-CmH2m+1—,
- m and n are, identically or differently, 0, 1, 2, 3, 4, 5 or 6, and
- Cy denotes a cycloaliphatic group having 3, 4 or 5 ring atoms, wherein the cycloaliphatic group is optionally substituted with an alkyl having 1-3 carbon atoms, an alkenyl having 2-3 C atoms or with halogen or CN,
- and optionally with one or more compounds of formula II, III, IV and/or V
- wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
- R1 and R2 straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR0═CR00—, —C≡C—,
- in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F or Cl, H or alkyl having 1 to 12 C atoms,
- R0, R00 H or alkyl having 1 to 12 C atoms,
- A1 and A2 a group selected from the following formulae
- Z1 and Z2—CH2CH2—, —CH═CH—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —CO—O—, —O—CO—, —C2F4—, —CF═CF—, —CH═CH—CH2O— or a single bond,
- L1, L2, L3 and L4 F, Cl, OCF3, CF3, CH3, CH2F or CHF2,
- Y H, F, Cl, CF3, CHF2 or CH3,
- LC CH3 or OCH3,
- a1 1 or 2, and
- a2 0 or 1,
- in which
- R11 and R 12 each, independently of one another, denote H, an alkyl or alkoxy radical having 1 to 15 C atoms, where one or more CH2 groups in these radicals may each be replaced, independently of one another, by
- —C≡C—, —CF2O—, —OCF2—, —CH═CH—, by —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by halogen,
- A3 on each occurrence, independently of one another, denotes
- a) 1,4-cyclohexenylene or 1,4-cyclohexylene radical, in which one or two non-adjacent CH2 groups may be replaced by —O— or —S—,
- b) a 1,4-phenylene radical, in which one or two CH groups may be replaced by N, or
- c) a radical selected from the group consisting of spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, phenanthrene-2,7-diyl and fluorene-2,7-diyl, wherein the radicals a), b) and c) may be mono- or polysubstituted by halogen atoms, denotes 0, 1 or 2,
- n denotes 0, 1 or 2,
- Z1 on each occurrence independently of one another denotes-CO—O—, —O—CO—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —CH2—, —CH2CH2—, —(CH2)4—, —CH═CH—CH2O—, —C2F4—, —CH2CF2—, —CF2CH2—, —CF═CF—, —CH═CF—, —CF═CH—, —CH═CH—, —C≡C— or a single bond, and
- L11 and L12 each, independently of one another, denote F, Cl, CF3 or CHF2, and
- W denotes O or S, and if n is 0 then Wis not S, wherein the one or more compounds of formula III2-2 are excluded from the one or more compounds of formula III,
- in which
- R41 denotes an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkenyl radical having 2 to 7 C atoms, and
- R42 denotes an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkoxy radical having 1 to 6 C atoms, an unsubstituted alkenyl radical having 2 to 7 C atoms,
- in which
- R51 and R52 independently of one another, have one of the meanings given for R41 and R42,
- identically or differently, denote
- Z51, Z52 each, independently of one another, denote —CH2—CH2—, —CH2—O—, —CH═CH—, —C≡C—, —COO— or a single bond, and
- n is 1 or 2,
- optionally with further liquid-crystalline compounds and/or additives, and optionally polymerizing the polymerizable compounds.
52 more elements
Dependencies are inferred from the claim text.