Liquid-crystalline media having homeotropic alignment

Patent metadata

Field	Value
Publication number	US-10513657-B2
Application number	US-201715803156-A
Country	US
Kind code	B2
Filing date	Nov 3, 2017
Priority date	Mar 10, 2014
Publication date	Dec 24, 2019
Grant date	Dec 24, 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 self-alignment additives which have a certain position of the functional groups.

First claim

The invention claimed is:

1. A liquid-crystal medium comprising a low-molecular-weight, non-polymerizable liquid-crystalline component and a polymerizable or polymerized component comprising one or more polymerizable compounds of formula I, where the polymerized component is obtainable by polymerization of the polymerizable component,
R 1 -[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 or -Sp-P,
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 each 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 —, —CH(-Sp-P)—, —CH 2 CH(-Sp-P)—, or —CH(-Sp-P)CH(-Sp-P)—,
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 —, —CH(-Sp-P)—, —CH 2 CH(-Sp-P)—, or —CH(-Sp-P)CH(-Sp-P)—,
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 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 each be replaced by —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, in addition, one or more H atoms may each be replaced by F or Cl,
or a group -Sp-P,

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,
where the compound of the formula I contains at least one polymerizable group P within the groups A 1 , A 2 , A 3 , Z 2 and Z 3 , as are present; and

wherein said liquid-crystal medium further comprises:
(a) one or more compounds selected from the compounds of formulae A, B and C,

in which
R 2A , R 2B and R 2C each, independently of one another, denote H, an alkyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF 3 or at least monosubstituted by halogen, where, in addition, one or more CH 2 groups in these radicals is each optimally replaced by —O—, —S—,

—C≡C—, —CF 2 O—, —OCF 2 —, —OC—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
L 1-4 each, independently of one another, denote F, Cl, CF 3 or CHF 2 ,
Z 2 and Z 2′ each, independently of one another, denote a single bond, —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, —C 2 F 4 —, —CF═CF—, or —CH═CHCH 2 O—,
(O) denotes —O— or a single bond,
p denotes 1 or 2,
q denotes 0 or 1, and
v denotes 1 to 6; or
(b) one or more compounds selected from the compounds of formulae II and III

in which
ring A denotes 1,4-phenylene or trans-1,4-cyclohexylene,
a is 0 or 1,
R 3 in each case, independently of one another, denotes alkyl having 1 to 9 C atoms or alkenyl having 2 to 9 C atoms, and
R 4 in each case, independently of one another, denotes an unsubstituted or halogenated alkyl radical having 1 to 12 C atoms, where, in addition, one or two non-adjacent CH 2 groups are each optionally replaced by —O—, —CH═CH—, —CH═CF—, —(CO)—, —O(CO)— or —(CO)O— in such a way that O atoms are not linked directly to one another; or
(c) one or more compounds selected from the compounds of formulae IV and V

in which
R 0 denotes an alkyl or alkoxy radical having 1 to 15 C atoms, in which, in addition, one or more CH 2 groups in these radicals are each optionally, independently of one another, replaced by —C≡C—, —CF 2 O—, —CH═CH—,

—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 are each optionally replaced by halogen,
ring A denotes

ring B, independently of one another, denotes 1,4-phenylene, optionally substituted by one or two F or Cl,

X 0 denotes F, Cl, CN, SF 5 , SCN, NCS, a halogenated alkyl group, a halogenated alkenyl group, a halogenated alkoxy group or a halogenated alkenyloxy group, each having up to 6 C atoms,
Y 1-4 each, independently of one another, denote H or F,
Z 0 denotes —CF 2 O—, —(CO)O— or a single bond, and
c denotes 0, 1 or 2.

2. The medium according to claim 1 , wherein, in formula I,
A 1 , A 2 , A 3 each, independently of one another, denote 1,4-phenylene, naphthalene-1,4-diyl or naphthalene-2,6-diyl, where, in addition, one or more CH groups in these groups may each be replaced by N, cyclohexane-1,4-diyl, in which, in addition, one or more non-adjacent CH 2 groups are each optionally replaced by O 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,
where all these groups are unsubstituted or mono- or polysubstituted by a group L or -Sp-P.

3. The medium according to claim 1 , wherein the one or more compounds o

Assignees

• Merck Patent Gmbh

Inventors

• Archetti Graziano
• Saito Izumi
• Fortte Rocco
• Kodek Thorsten

Classifications

• C09K2019/0425

  characterized by a specific unit that results in a functional effect · CPC title

• C09K19/3003

  Compounds containing at least two rings in which the different rings are directly linked (covalent bond) · CPC title

• C09K19/3402 Primary

  having oxygen as hetero atom (sugars C09K19/0422) · CPC title

• C09K2019/123

  Ph-Ph-Ph · CPC title

• C09K2019/3027

  Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene · CPC title