US 11,999,891 B2
Liquid-crystal medium comprising polymerisable compounds and the use thereof in liquid-crystal displays
Helmut Haensel, Muehltal (DE); Qiong Tong, Darmstadt (DE); Edward Plummer, Frankfurt am Main (DE); Rocco Fortte, Frankfurt am Main (DE); and Thomas Eichhorn, Darmstadt (DE)
Assigned to MERCK PATENT GMBH, Darmstadt (DE)
Appl. No. 17/299,982
Filed by MERCK PATENT GMBH, Darmstadt (DE)
PCT Filed Dec. 4, 2019, PCT No. PCT/EP2019/083586
§ 371(c)(1), (2) Date Jun. 4, 2021,
PCT Pub. No. WO2020/115089, PCT Pub. Date Jun. 11, 2020.
Claims priority of application No. 18210994 (EP), filed on Dec. 7, 2018.
Prior Publication US 2023/0007940 A1, Jan. 12, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. G02F 1/1333 (2006.01); C09K 19/12 (2006.01); C09K 19/32 (2006.01); C09K 19/56 (2006.01); C09K 19/04 (2006.01)
CPC C09K 19/12 (2013.01) [C09K 19/322 (2013.01); C09K 19/56 (2013.01); C09K 2019/0448 (2013.01); C09K 2019/122 (2013.01); C09K 2019/123 (2013.01); C09K 2323/06 (2020.08)] 27 Claims
 
1. 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.