IP Library › Granted Patent US 10,913,897
Granted Patent B2
US 10,913,897 · App. 15/883,976 · Granted Feb 9, 2021

Compounds and liquid-crystalline medium

Inventors: Martin Engel (Darmstadt, DE); Sabrina Maag (Pfungstadt, DE); Ingo Almeroth (Bensheim, DE); Rocco Fortte (Frankfurt Am Main, DE); Achim Goetz (Alsbach-Haehnlein, DE); Thorsten Kodek (Moerfelden-Walldorf, DE); Oliver Heppert (Weiterstadt, DE)
Assignee: MERCK PATENT GMBH
C09K19/44C07D401/14C09K19/12C09K19/3003C09K19/3098C09K19/3405C09K19/3483G02F1/1333C09K19/0216C09K2019/122C09K2019/123C09K2019/301C09K2019/3004C09K2019/3009C09K2019/3016C09K2019/3027C09K2019/3408
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Quick Facts
Patent No.
US 10,913,897
App. No.
15/883,976
Granted
Feb 9, 2021
Kind
B2
Abstract

Compounds of the formula I, and liquid-crystalline media, preferably having a nematic phase and negative dielectric anisotropy, comprising a) one or more compounds of the formula I and one or more compounds selected from b) one or more compounds of formula II and/or c) one or more compounds selected from compounds of formulae III-1 to III-4 and formula B Methods for making and using these liquid-crystalline media in electro-optical displays, particularly in active-matrix displays based on the VA, ECB, PALC, FFS or IPS effect and the displays which contain these media. Methods for stabilizing liquid-crystalline media with compounds of formula I, where the liquid-crystalline media comprise one or more compounds of the formula II and one or more compounds selected from compounds of the formulae III-1 to III-4 and formula B.

Claims (38)

1. A liquid crystalline medium comprising

a. one or more compounds of the formulae I-9, I-10 or I-11

2. A medium according to claim 1 , wherein the total concentration of the one or more compounds of the formulae I-9, I-10 or I-11 in the medium as a whole is from 1 ppm to 2500 ppm.

3. A medium according to claim 1 , which further comprises a compound of the formula II

in which

R 22 denotes an unsubstituted alkenyl radical having 2 to 7 C atoms

and R 21 denotes n-propyl and R 22 denotes vinyl.

4. A medium according to claim 3 , wherein the total concentration of the compounds of the formula II in the medium as a whole is from 25% to 45%.

5. A medium according to claim 1 , which further comprises one or more compounds of the formula 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.

6. A medium according to claim 1 , which additionally comprises one or more chiral compounds.

7. A compound of the formulae I-9, I-10 or I-11

8. An electro-optical display electro-optical component, which contains a liquid-crystalline medium according to claim 1 .

9. A display according to claim 8 , which utilize a IPS, FFS, VA or ECB effect.

10. A display according to claim 8 , which contains an active-matrix addressing device.

11. A method which comprises including a compound of claim 7 in a liquid-crystalline medium.

12. A method which comprises including a liquid-crystalline medium according to claim 1 in an electro-optical display or in an electro-optical component.

13. A process for the preparation of a liquid-crystalline medium according to claim 1 , comprising mixing one or more compounds of the formulae I-9, I-10 or I-11 with one or more compounds of the formula B

in which

R B1 and R B2 each, independently of one another, denote an unsubstituted alkyl radical, alkoxy radical, oxaalkyl radical or alkoxyalkyl radical having 1 to 7 C atoms, or an alkenyl radical or alkenyloxy radical having 2 to 7 C atoms, and

L B1 and L B2 each, independently of one another, denote F or Cl.

14. A process for the stabilization of a liquid-crystalline medium which comprises adding to said liquid-crystalline medium one or more compounds of claim 7 , and optionally one or more compounds of the formulae OH-1 to OH-6,

15. A process for the preparation of a compound according to claim 7 , which comprises hydrogenating the corresponding 2,2,6,6-tetramethylpiperidine 1-oxyl or 1-benzyl precursor.

16. A process for the preparation of a liquid-crystalline medium according to claim 3 , comprising mixing one or more compounds of the formulae I-9, I-10 or I-11 with one or more compounds of the formula B

in which

R B1 and R B2 each, independently of one another, denote an unsubstituted alkyl radical, alkoxy radical, oxaalkyl radical or alkoxyalkyl radical having 1 to 7 C atoms, or an alkenyl radical or alkenyloxy radical having 2 to 7 C atoms, and

L B1 and L B2 each, independently of one another, denote F or Cl and one or more compounds of the formula II.

17. A process for the preparation of a liquid-crystalline medium according to claim 5 , comprising mixing one or more compounds of the Formulae I-9, I-10 or I-11 with one or more compounds of the formula B

in which

R B1 and R B2 each, independently of one another, denote an unsubstituted alkyl radical, alkoxy radical, oxaalkyl radical or alkoxyalkyl radical having 1 to 7 C atoms, or an alkenyl radical or alkenyloxy radical having 2 to 7 C atoms, and

L B1 and L B2 each, independently of one another, denote F or Cl

and one or more compounds of the formula III-4.

18. A medium according to claim 3 , which further comprises a compound of the formula II and one or more compounds of formula B,

in which

R B1 and R B2 each, independently of one another, denote an unsubstituted alkyl radical, alkoxy radical, oxaalkyl radical or alkoxyalkyl radical having 1 to 7 C atoms, or an alkenyl radical or alkenyloxy radical having 2 to 7 C atoms, and

L B1 and L B2 each, independently of one another, denote F or Cl.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 28, 2018
From: ENGEL, MARTIN; MAAG, SABRINA; ALMEROTH, INGO; GOETZ, ACHIM; FORTTE, ROCCO; KODEK, THORSTEN; HEPPERT, OLIVER
To: MERCK PATENT GMBH
Reel/Frame 045061/0855 →
Priority Claims (1)
DE 10 2017 000 812 · Jan 30, 2017 · national
Continuity (1)
Related Publication 20180216005A1 · Aug 2, 2018
Cited By (2)
US 12,187,946 US 12,325,817