Back to results
US 11,999,891 B2Granted
Liquid-crystal medium comprising polymerisable compounds and the use thereof in liquid-crystal displays
AssigneeMerck Patent GmbH
InventorsHelmut Haensel, Qiong Tong, Edward Plummer, Rocco Fortte, Thomas Eichhorn
Life of this patent
Estimating the term…
Abstract
The present invention relates to a liquid-crystal (LC) medium comprising one or more polymerisable compounds and to the use of the LC medium for optical, electro-optical and electronic purposes, in particular in LC displays, especially in LC displays of the polymer sustained alignment (PS, PSA) or self-aligning (SA) type.
Claims27
An LC medium comprising
- a polymerisable component A) comprising, one or more polymerisable compounds, wherein at least one of said polymerisable compounds is a compound of formula I,
- a liquid-crystalline component B), wherein said a liquid-crystalline component B is a LC host mixture comprising one or more mesogenic or liquid-crystalline compounds,
- optionally one or more additives selected from the group consisting of self-alignment additives for vertical alignment of formula II and stabilizers
- P-Sp—A1-(Z1—A2)z-Rb I
- MES-Ra II
- wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
- Rb P-Sp- or R,
- R is F, Cl, —CN or a straight chain alkyl having 1 to 25 C atoms, or a 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—, or —O—CO—O— 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,
- P is selected from the group consisting of vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxide,
- Sp is a spacer group which is optionally substituted by P, or a single bond,
- A1 A2 are a monocyclic or polycyclic aromatic or heteroaromatic group with 4 to 20 ring atoms, which is optionally substituted by one or more groups L, A or P-Sp-,
- wherein the compounds of formula I contain at least one group A1 or A2 that is substituted by at least one group A,
- Z1 is —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —(CH2)n1—, —CF2CH2—, —CH2CF2—, —(CF2)n1—, —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C—, —CH═CH—CO—O—, —O—CO—CH═CH—, —CH2—CH2—CO—O—, —O—CO—CH2—CH2—, —CR0R00—, or a single bond,
- R0, R00 are H or alkyl having 1 to 12 C atoms,
- A is —CH═CH2, —CH2—CH═CH2, —CH═CH—CH3, —CH═CH—CH═CH2 or —C(CH3)═CH2,
- L is F, Cl, —CN, P-Sp- or a straight chain alkyl having 3 to 25 C atoms, or a 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-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 P-Sp-, F or Cl,
- z is 0, 1, 2 or 3,
- n1 is 1, 2, 3 or 4,
- MES is a calamitic mesogenic group containing two or more rings, which are connected directly or indirectly to each other or which are condensed to each other, which are optionally substituted and which mesogenic group is optionally substituted additionally by one or more polymerizable groups, which are connected to MES directly or via a spacer, and
- Ra a polar anchor group, residing in a terminal position of the calamitic mesogenic group MES which comprises at least one carbon atom and at least one group selected from —OH, —SH, —COOH, —CHO or primary or secondary amine function, which optionally contains one or two polymerizable groups P,
- wherein —A1-(Z1—A2)z- in formula I denotes benzene, biphenylene, p-terphenylene (1,4-diphenylbenzene), m-terphenylene (1,3-diphenylbenzene), naphthylene, 2-phenyl-naphthylene, phenanthrene, anthracene, dibenzofuran or dibenzothiophene, all of which are optionally substituted by one or more groups A, L or P-Sp- and are at least monosubstituted by A.
18 more elements
An LC medium comprising
- a polymerisable component A) comprising, one or more polymerisable compounds, wherein at least one of said polymerisable compounds is a compound of the formula I5A-2:
- a liquid-crystalline component B), wherein said a liquid-crystalline component B is a LC host mixture comprising one or more mesogenic or liquid-crystalline compounds,
- optionally one or more additives selected from the group consisting of self-alignment additives for vertical alignment of formula II and stabilizers
- MES-Ra II
- wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings:
- P is a polymerisable group,
- Sp is a spacer group which is optionally substituted by P, or a single bond,
- A1, A2 are a monocyclic or polycyclic aromatic or heteroaromatic group with 4 to 20 ring atoms, which is optionally substituted by one or more groups L, A or P-Sp-,
- A is alkenyl with 2 to 7 C-atoms,
- L is F, Cl, -CN, P-Sp- or a straight chain alkyl having 1 to 25 C atoms, or a branched or cyclic alkyl having from 3 to 25 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO—O— 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 P-Sp-, F or Cl,
- MES is a calamitic mesogenic group containing two or more rings, which are connected directly or indirectly to each other or which are condensed to each other, which are optionally substituted and which mesogenic group is optionally substituted additionally by one or more polymerizable groups, which are connected to MES directly or via a spacer, and
- Ra is a polar anchor group, residing in a terminal position of the calamitic mesogenic group MES which comprises at least one carbon atom and at least one group selected from —OH, —SH, —COOH, —CHO or primary or secondary amine function, which optionally contains one or two polymerizable groups P.
9 more elements
A LC medium comprising
- a polymerisable component A) comprising, one or more polymerisable compounds, wherein at least one of said polymerisable compounds is a compound of formula I,
- a liquid-crystalline component B), wherein said liquid-crystalline component B is a LC host mixture comprising one or more mesogenic or liquid-crystalline compounds,
- at least one additional polymerizable compound (C) selected from formulae M1 to M32,
- in which the individual radicals have the following meanings:
- P1, P2 and P3 each, independently of one another, denote an acrylate or methacrylate group,
- Sp1, Sp2 and Sp3 each, independently of one another, denote a single bond or a spacer group having one of the meanings below for Sp, in which p1 is an integer from 1 to 12, where one or more of the radicals P1-Sp1-, P1-Sp2- and P3-Sp3- may denote Raa, with the proviso that at least one of the radicals, P1-Sp1-, P2-Sp2 and P3-Sp3- present is different from Raa,
- Raa denotes H, F, Cl, CN or a straight-chain alkyl having 1 to 25 C atoms or a branched alkyl having 3 to 25 C atoms, in which one or more non-adjacent CH2 groups may each be replaced, independently of one another, by C(R0)═C(R00)-, —C≡C—, —N(R0)—, —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO—O-in such a way that O and/or S atoms are not linked directly to one another, and in which one or more H atoms may be replaced by F, Cl, CN or P1-Sp1-, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms where the alkenyl and alkynyl radicals have at least two C atoms and any branched radicals have at least three C atoms,
- R0, R00 each, independently of one another and identically or differently on each occurrence, denote H or alkyl having 1 to 12 C atoms,
- Ry and Rz each, independently of one another, denote H, F, CH3 or CF3,
- X1, X2 and X3 each, independently of one another, denote —CO—O—, —O—CO- or a single bond,
- Z1 denotes —O—, —CO—, —C(RyRz)- or —CF2CF2—,
- Z2 and Z3 each, independently of one another, denote —CO—O—, —O—CO—, —CH2O—, —OCH2—, —CF2O—, —OCF2— or —(CH2)n-, where n is 2, 3 or 4,
- L on each occurrence, identically or differently, denotes F, Cl, CN or a straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, where the alkenyl and alkynyl radicals have at least two C atoms and any branched radicals have at least three C atoms,
- L′ and L″ each, independently of one another, denote H, F or Cl,
- k denotes 0 or 1,
- r denotes 0, 1, 2, 3 or 4,
- s denotes 0, 1, 2 or 3,
- t denotes 0, 1 or 2,
- x denotes 0 or 1
- and
- optionally one or more additives selected from the group consisting of self-alignment additives for vertical alignment of formula II and stabilizers
- P-Sp—A1-(Z1—A2)z-Rb I
- MES-Ra II
- wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
- Rb is P-Sp- or R,
- R is F, Cl, —CN or a straight chain alkyl having 1 to 25 C atoms, or a branched or cyclic alkyl having from 3 to 25 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO—O-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,
- P is a polymerisable group,
- Sp is a spacer group which is optionally substituted by P, or a single bond,
- A1, A2 are a monocyclic or polycyclic aromatic or heteroaromatic group with 4 to 20 ring atoms, which is optionally substituted by one or more groups L, A or P-Sp-,
- wherein the compounds of formula I contain at least one group A1 or A2 that is substituted by at least one group A,
- Z1 is —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —(CH2)n1-, —CF2CH2—, —CH2CF2—, —(CF2)n1-, —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C—, —CH═CH—CO—O—, —O—CO—, —CH═CH—, —CH2—CH2—CO—O—, -O—CO—CH2—CH2—, —CR0R00-, or a single bond,
- R0, R00 is H or alkyl having 1 to 12 C atoms,
- A is alkenyl with 2 to 7 C-atoms,
- L is F, Cl, -CN, P-Sp- or a straight chain alkyl having 1 to 25 C atoms, or a 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—, or —O—CO—O-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 P-Sp-, F or Cl,
- z is 0, 1, 2 or 3,
- n1 is 1, 2, 3 or 4,
- MES is a calamitic mesogenic group containing two or more rings, which are connected directly or indirectly to each other or which are condensed to each other, which are optionally substituted and which mesogenic group is optionally substituted additionally by one or more polymerizable groups, which are connected to MES directly or via a spacer, and
- Ra is a polar anchor group, residing in a terminal position of the calamitic mesogenic group MES which comprises at least one carbon atom and at least one group selected from —OH, —SH, —COOH, —CHO or primary or secondary amine function, which optionally contains one or two polymerizable groups P.
35 more elements
Dependencies are inferred from the claim text.