Compounds and liquid-crystalline medium

Patent metadata

Field	Value
Publication number	US-9920248-B2
Application number	US-201514627852-A
Country	US
Kind code	B2
Filing date	Feb 20, 2015
Priority date	Apr 21, 2011
Publication date	Mar 20, 2018
Grant date	Mar 20, 2018

Abstract

The invention relates to compounds of the formula I, and to a liquid-crystalline medium, preferably having a nematic phase and negative dielectric anisotropy, which comprises one or more compounds of formula I, defined herein, for use in an electro-optical display, particularly in an active-matrix display based on the VA, ECB, PALC, FFS or IPS effect, and to the use of the compounds of the formula I for the stabilization of a liquid-crystalline medium which comprises one or more compounds of the formula II and one or more compounds of the formulae III-1 to III-4, defined herein.

First claim

The invention claimed is:

1. A liquid-crystalline medium comprising:
a) one or more compounds of formula I

in which
n denotes 3 or 4,
m denotes (4−n),

 denotes an organic radical having 4 bonding sites,
Z 11 and Z 12 , independently of one another, denote —O—, —(C═O)—, (N—R 14 )— or a single bond, but do not both simultaneously denote —O—,
r and s, independently of one another, denote 0 or 1,
Y 11 to Y 14 each, independently of one another, denote alkyl having 1 to 4 C atoms, or alternatively, independently from each other, the two pairs (Y 11 and Y 12 ) and (Y 13 and Y 14 ) may be connected by a bond to form together a divalent group having 3 to 6 C-atoms,
R 11 in each case, denotes O • ,
R 12 on each occurrence, independently of one another, denotes H, F, OR 14 , NR 14 R 15 , a straight-chain or branched alkyl chain having 1-20 C atoms, in which one —CH 2 — group or a plurality of —CH 2 — groups may each be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—, or denotes a hydrocarbon radical which contains a cycloalkyl or alkylcycloalkyl unit, and in which one —CH 2 — group or a plurality of —CH 2 — groups may each be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—, and in which one H atom or a plurality of H atoms may each be replaced by OR 14 , N(R 14 )(R 15 ) or R 16 , or denotes an aromatic or heteroaromatic hydrocarbon radical, in which one H atom or a plurality of H atoms may each be replaced by OR 14 , N(R 14 )(R 15 ) or R 16 ,
R 13 on each occurrence, independently of one another, denotes a straight-chain or branched alkyl chain having 1-20 C atoms, in which one —CH 2 — group or a plurality of —CH 2 — groups may each be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—, or denotes a hydrocarbon radical which contains a cycloalkyl or alkylcycloalkyl unit, and in which one —CH 2 — group or a plurality of —CH 2 — groups may each be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—, and in which one H atom or a plurality of H atoms may each be replaced by OR 14 , N(R 14 )(R 15 ) or R 16 , denotes an aromatic or heteroaromatic hydrocarbon radical, in which one H atom or a plurality of H atoms may each be replaced by OR 14 , N(R 14 )(R 15 ) or R 16 ,
or can be

 (1,4-cyclohexyl), in which one or more —CH 2 — groups may each be replaced by —O—, —CO— or —NR 14 —, or an acetophenyl, isopropyl or 3-heptyl radical,

R 14 on each occurrence, independently of one another, denotes a straight-chain or branched alkyl or acyl group having 1 to 10 C atoms or an aromatic hydrocarbon or carboxyl radical having 6-12 C atoms,
R 15 on each occurrence, independently of one another, denotes a straight-chain or branched alkyl or acyl group having 1 to 10 C atoms or an aromatic hydrocarbon or carboxyl radical having 6-12 C atoms,
R 16 on each occurrence, independently of one another, denotes a straight-chain or branched alkyl group having 1 to 10 C atoms, in which one —CH 2 — group or a plurality of —CH 2 — groups may each be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—,
and
b) one or more compounds of formula II

in which
R 21 denotes an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkenyl radical having 2 to 7 C atoms, and
R 22 denotes an unsubstituted alkenyl radical having 2 to 7 C atoms,
and optionally
c) one or more compounds selected from formulae III-1 to III-4,

in which
R 31 denotes an unsubstituted alkyl radical having 1 to 7 C atoms,
R 32 denotes an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkoxy radical having 1 to 6 C atoms, and
m, n and o each, independently of one another, denote 0 or 1.

2. The medium according to claim 1 , wherein said medium contains one or more compounds selected from formulae III-1 to III-4.

3. The medium according to claim 1 , wherein the total concentration of the compounds of the formula I in the medium as a whole is 1 ppm or more to 1,000 ppm or less.

4. The medium according to claim 1 , wherein said medium comprises a compound of the formula II in which R 21 denotes n-propyl and R 22 denotes vinyl.

5. The medium according to claim 4 , wherein the total concentration of the compounds of the formula II in the medium as a whole is 25% or more to 45% or less.

6. The medium according to claim 1 , wherein said medium comprises one or more compounds of formula III-2-2

in which R 31 and R 32 have the respective meanings given under formula III-2 in claim 1 .

7. The medium according to claim 1 , wherein said medium comprises one or more compounds of formula III-4.

8. The medium according to claim 1 , wherein said medium additionally comprises one or more chiral compounds.

9. An electro-optical display or electro-optical component, comprising a liquid-crystalline medium according to claim 1 .

10. The display according to claim 9 , wherein said display is based on the VA or ECB effect.

11. The display according to claim 9 , wherein said display comprises an active-matrix addressing device.

12. A method of generating an electro-optical effect comprising applying a voltage to a liquid-crystalline medium according to claim 1 .

13. A method according to claim 12 , wherein said liquid-crystalline medium is in an electro-optical display or in an electro-optical component.

14. A process for the preparation of a liquid-crystalline medium according to claim 1 , said process comprising: mixing one or more compounds of formula I, with one or more compounds of formula II, and optionally one or more compounds selected from formulae III-1 to III-4.

15. A liquid-crystalline medium according to claim 1 , wherein said medium further comprises one or more compounds selected from formulae OH-1 to OH-6

16. A liquid-crystalline medium according to claim 1 , wherein ZG denotes

17. A compound selected from formulae I-1b-1 and I-1b-2,

18. A compound selected from formulae I-1c-1 and I-1c-2,

19. A compound selected from the following formulae:

20. The liquid crystal medium according to claim 16 , wherein ZG denotes

Assignees

• Merck Patent Gmbh

Inventors

• Goebel Mark
• Fortte Rocco
• Pauluth Detlef

Classifications

• G02F1/13306

  Circuit arrangements or driving methods for the control of single liquid crystal cells (G02F1/132, G02F1/133382 take precedence) · CPC title

• C09K2019/3016

  Cy-Ph-Ph · CPC title

• C09K2019/301

  Cy-Cy-Ph · CPC title

• C07D211/94 Primary

  Oxygen atom, e.g. piperidine N-oxide · CPC title

• C09K19/3483

  the heterocyclic ring being a non-aromatic ring · CPC title