Liquid crystalline media having homeotropic alignment

Patent metadata

Field	Value
Publication number	US-10294426-B2
Application number	US-201515321596-A
Country	US
Kind code	B2
Filing date	Jun 25, 2015
Priority date	Jul 28, 2014
Publication date	May 21, 2019
Grant date	May 21, 2019

Abstract

The present invention relates to liquid-crystalline media (LC media) having negative or positive dielectric anisotropy, comprising a low-molecular-weight component and a polymerizable component. The polymerizable component comprises self-aligning, polymerizable mesogens (polymerizable self-alignment additives) which effect homeotropic (vertical) alignment of the LC media at a surface or the cell walls of a liquid-crystal display (LC display). The invention therefore also encompasses LC displays having homeotropic alignment of the LC medium without alignment layers. The invention discloses novel structures for polymerizable self-alignment additives which have a certain position of the functional groups.

First claim

The invention claimed is:

1. A LC medium comprising:
i) a low-molecular-weight, non polymerizable liquid-crystalline component
and
ii) one or more polymerizable compounds of the formula I,
or
a polymerized component obtainable by polymerization of the polymerisable compound of formula I,
P-Sp-[A 3 -Z 3 ] m -[A 2 ] k -[Z 2 ] n -A 1 -R a   (I)

in which
A 1 , A 2 , A 3 each, independently of one another, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, which may also contain fused rings, and which may also be mono- or polysubstituted by a group L,
L in each case, independently of one another, denotes H, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)N(R 0 ) 2 , —C(═O)R 0 , optionally substituted silyl, optionally substituted aryl or cycloalkyl having 3 to 20 C atoms, or straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl,
P denotes a polymerizable group,
Sp denotes a spacer group or a single bond,
Z 2 in each case, independently of one another, denotes —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —(CH 2 ) n1 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —(CF 2 ) n1 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, —(CR 0 R 00 ) n1 —,
Z 3 in each case, independently of one another, denotes a single bond, —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —(CH 2 ) n1 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —(CF 2 ) n1 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, —(CR 0 R 00 ) n1 —,
n1 denotes 1, 2, 3 or 4,
n denotes 0 or 1,
m denotes 0, 1, 2, 3, 4, 5 or 6,
k denotes 0 or 1,
R 0 in each case, independently of one another, denotes alkyl having 1 to 12 C atoms,
R 00 in each case, independently of one another, denotes H or alkyl having 1 to 12 C atoms,
R a denotes an anchor group of the formula

p denotes 1 or 2,
q denotes 2 or 3,
B denotes a substituted or unsubstituted ring system or condensed ring system,
Y, independently of one another, denotes —O—, —S—, —C(O)—, —C(O)O—, —OC(O)—, —NR 11 — or a single bond,
o denotes 0 or 1,
X 1 , independently of one another, denotes H, alkyl, fluoroalkyl, OH, NH 2 , NHR 11 , NR 11 2 , OR 11 , C(O)OH, —CHO,
where at least one group X 1 denotes a radical selected from —OH, —NH 2 , NHR 11 , C(O)OH and —CHO,

R 11 denotes alkyl having 1 to 12 C atoms,
Sp a , Sp c , Sp d each, independently of one another, denote a spacer group or a single bond, and
Sp b denotes a tri- or tetravalent group.

2. A Medium according to claim 1 , wherein, for formula I,
A 1 , A 2 , A 3 each, independently of one another, denote 1,4-phenylene, 1,3-phenylene, naphthalene-1,4-diyl or naphthalene-2,6-diyl, where, in addition, one or more CH groups in these groups may be replaced by N, cyclohexane-1,4-diyl, in which, in addition, one or more non-adjacent CH 2 groups may be replaced by O and/or S, 3,3′-bicyclobutylidene, 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, indane-2,5-diyl or octahydro-4,7-methanoindane-2,5-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl (in particular gonane-3,17-diyl),
where all these groups may be unsubstituted or mono- or polysubstituted by a group L.

3. A Medium according to claim 1 , wherein the compound of the formula I is a compound of the formula I1,

in which
R a , A 1 , A 2 , A 3 , Z 2 , Z 3 , L, Sp, P, k, m and n independently are as defined in claim 1 , and
r1, r2, r3 independently denote 0, 1, 2 or 3.

4. A LC medium according to claim 1 , wherein the compound of the formula I contains in total at least one group L on the groups A 1 , A 2 and A 3 , as are present.

5. A LC medium according to claim 1 , wherein the one or more compounds of the formula I are selected from compounds of the formulae IA, IB, IC, ID, IE or IF:

in which R a , Z 2 , Z 3 , L, Sp, P and n independently are as defined in claim 1 , and
r1, r2, r3 independently denote 0, 1, 2 or 3.

6. A LC medium according to claim 1 , wherein, besides one or more compounds of the formula I, the polymerizable or polymerized component comprises one or more further polymerizable or polymerized compounds, where the polymerized component is obtainable by polymerization of the polymerizable component.

7. A LC medium according to claim 1 , wherein one or more compounds of the formula I, additionally comprises one or more non-polymerizable compounds of the formula I′,
R 1 -[A 3 -Z 3 ] m -[A 2 ] k -[Z 2 ] a -A 1 -R a   I′

in which m, k, n and the group R a are as defined for formula I according to claim 1 , and
A 1 , A 2 , A 3 each, independently of one another, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, which may also contain fused rings, and which may also be mono- or polysubstituted by a group L,
Z 2 in each case, independently of one another, denotes —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —(CH 2 ) n1 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —(CF 2 ) n1 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, —(CR 0 R 00 ) n1 —,
Z 3 in each case, independently of one another, denotes a single bond, —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —(CH 2 ) n1 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —(CF 2 ) n1 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, —(CR 0 R 00 ) n1 —,
n1 denotes 1, 2, 3 or 4,
L in each case, independently of one another, denotes H, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)N(R 0 ) 2 , —C(═O)R 0 , optionally substituted silyl, optionally substituted aryl or cycloalkyl having 3 to 20 C atoms, or straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl,
R 0 in each case, independently of one another, denotes alkyl having 1 to 12 C atoms,
R 00 in each case, independently of one another, denotes H or alkyl having 1 to 12 C atoms,
and
R 1 , independently of one another, denotes H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH 2 groups may be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another and in which, in addition, one or more H atoms may be replaced by F or Cl.

8. A LC medium according to claim 7 , which comprises one or more polymerizable compounds selected from the following formulae:

in which R 1 , R a , Z 2 , Z 3 , L and n independently are as defined in claim 7 , and
r1, r2, r3 independently denote 0, 1, 2, 3 or 4.

9. A LC medium according to claim 1 , which comprises one or more compounds of the formula I selected from the following formulae:

Assignees

• Merck Patent Gmbh

Inventors

• Archetti Graziano
• Saito Izumi
• Fortte Rocco
• Heppert Oliver
• Taugerbeck Andreas
• Neumann Elena

Classifications

• C09K2019/304

  Cy-C2H4-Ph-Ph · CPC title

• C09K2019/3016

  Cy-Ph-Ph · CPC title

• C09K2019/548

  stabilizing the alignment; Polymer stabilized alignment · CPC title

• C09K19/14

  linked by a carbon chain · CPC title

• C09K2019/301

  Cy-Cy-Ph · CPC title