Liquid-crystalline medium

Patent metadata

Field	Value
Publication number	US-9376622-B2
Application number	US-201314654069-A
Country	US
Kind code	B2
Filing date	Dec 9, 2013
Priority date	Dec 20, 2012
Publication date	Jun 28, 2016
Grant date	Jun 28, 2016

Abstract

The invention relates to compounds of the formula I and to a liquid-crystalline medium which comprises one or more compounds of the formula I,

in which R 1 , X 1 , X, Y 1 and Y 2 have the meanings indicated in Claim 1 , and to the use thereof for electro-optical purposes, in particular for shutter glasses, 3D applications, in TN, PS-TN, STN, TN-TFT, OCB, IPS, PS-IPS, FFS, PS-FFS and PS-VA-IPS displays.

First claim

The invention claimed is:

1. A liquid-crystalline medium, comprising one or more compounds of formula I,

in which
R 1 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more CH 2 groups are optionally replaced, independently of one another, 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,
X 1 denotes F, Cl, CN, SF 5 , SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms,
X is C—H or N, and
Y 1 and Y 2 each, independently of one another, denote H or F.

2. The liquid-crystalline medium according to claim 1 , wherein the one or more compounds of formula I are selected from the compounds of formulae I-1 to I-15,

in which
alkyl denotes a straight-chain alkyl radical having 1-6 C atoms,
alkenyl denotes a straight-chain alkenyl radical having 2-6 C atoms, and
alkoxy denotes a straight-chain alkoxy radical having 1-6 C atoms.

3. The liquid-crystalline medium according to claim 1 , wherein the one or more compounds of formula I are compounds of formula I-4

in which
alkyl denotes a straight-chain alkyl radical having 1-6 C atom.

4. The liquid-crystalline medium according to claim 1 , which additionally comprises one or more compounds of formulae II and/or III,

in which
R 0 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more CH 2 groups are optionally replaced, independently of one another, 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,
X 0 denotes F, Cl, CN, SF 5 , SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms,
Y 1-6 each, independently of one another, denote H or F, and

 each, independently of one another, denote

5. The liquid-crystalline medium according to claim 1 , which additionally comprises one or more compounds of formulae IV to VIII,

in which
R 0 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more CH 2 groups are optionally replaced, independently of one another, 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,
X 0 denotes F, Cl, CN, SF 5 , SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms,
Y 1-4 each, independently of one another, denote H or F,
Z 0 denotes —C 2 H 4 —, —(CH 2 ) 4 —, —CH═CH—, —CF═CF—, —C 2 F 4 —, —CH 2 CF 2 —, —CF 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO—, —CF 2 O— or —OCF 2 —, in formulae V and VI also a single bond,
r denotes 0 or 1, and
s denotes 0 or 1.

6. The liquid-crystalline medium according to claim 1 , which additionally comprises one or more compounds of formulae IX to XII,

in which
X 0 denotes F, Cl, CN, SF 5 , SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms,
L denotes H or F,
“alkyl” denotes C 1-6 -alkyl,
R′ denotes C 1-6 -alkyl, C 1-6 -alkoxy or C 2-6 -alkenyl, and
“alkenyl” and “alkenyl*” each, independently of one another, denote C 2-6 -alkenyl.

7. The liquid-crystalline medium according to claim 1 , which additionally comprises one or more compounds of formula XIII,

in which R 1 and R 2 each, independently of one another, denote n-alkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl, each having up to 6 C atoms.

8. The liquid-crystalline medium according to claim 1 , which additionally comprises one or more compounds of formula XVII,

in which R 1 and R 2 each, independently of one another, denote n-alkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl, each having up to 8 C atoms, and L denotes H or F.

9. The liquid-crystalline medium according to claim 1 , which additionally comprises one or more compounds of formulae XXVII, XXVIII and/or XXIX,

in which
R 0 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more CH 2 groups are optionally replaced, independently of one another, 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
X 0 denotes F, Cl, CN, SF 5 , SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms.

10. The liquid-crystalline medium according to claim 1 , which additionally comprises one or more compounds of formulae XIX, XX, XXI, XXII, XXIII and/or XXIV,

in which
R 0 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more CH 2 groups are optionally replaced, independently of one another, 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,
X 0 denotes F, Cl, CN, SF 5 , SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms, and
Y 1-4 each, independently of one another, denote H or F.

11. The liquid-crystalline medium according to claim 1 , which additionally it comprises ≧20% by weig

Assignees

• Merck Patent Gmbh

Inventors

• Hirschmann Harald
• Pohle Andreas
• Czanta Markus
• Schoenefeld Christian
• Montenegro Elvira
• Reiffenrath Volker

Classifications

• C09K19/0208

  Twisted Nematic (T.N.); Super Twisted Nematic (S.T.N.); Optical Mode Interference (O.M.I.) · CPC title

• C09K19/3466

  Pyrimidine with at least another heterocycle in the chain · CPC title

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C09K19/3444 Primary

  the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine · CPC title

• C09K2019/0448

  the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate · CPC title