Compounds and liquid-crystalline medium

Patent metadata

Field	Value
Publication number	US-2018216005-A1
Application number	US-201815883976-A
Country	US
Kind code	A1
Filing date	Jan 30, 2018
Priority date	Jan 30, 2017
Publication date	Aug 2, 2018
Grant date	—

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.

First claim

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

in which
R 11 on each occurrence, independently of one another, denotes H, F, a straight-chain or branched alkyl chain having 1-20 C atoms, in which one —CH 2 -group or, if present, a plurality of —CH 2 -groups may be replaced by —O— or —C(═O)—, but two adjacent —CH 2 -groups cannot be replaced by —O—, and one or, if present, a plurality of —CH 2 -groups may be replaced by—CH═CH— or —C≡C—, and in which one H atom or a plurality of H atoms may be replaced by F, OR 13 , N( R 13 )(R 14 ) or R 15 ,
R 12 on each occurrence, independently of one another, denotes H, 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 be replaced by —O— or —C(═O)—, but two adjacent —CH 2 -groups cannot be replaced by —O—, 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 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 be replaced by OR 13 , N(R 13 )(R 14 ) or R 15 , or an aromatic or heteroaromatic hydrocarbon radical, in which one H atom or a plurality of H atoms may be replaced by F, OR 13 , N(R 13 )(R 14 ) or R 15 ,
R 13 on each occurrence, independently of one another, denotes H, a straight-chain or branched alkyl or acyl group having 1 to 10 C atoms or an aromatic hydrocarbon or carboxylic acid radical having 6-12 C atoms,
R 14 on each occurrence, independently of one another, denotes H, a straight-chain or branched alkyl or acyl group having 1 to 10 C atoms or an aromatic hydrocarbon or carboxylic acid radical having 6 to 12 C atoms,
R 15 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 be replaced by —O— or —C(═O)—, but two adjacent —CH 2 -groups cannot be replaced by —O—,
S 11 and S 12 on each occurrence, independently of one another, denote an alkylene group having 1 to 20 C atoms, which can be branched or straight-chain, in which one —CH 2 -group or, if present, a plurality of —CH 2 -groups may be replaced by —O— or —C(═O)—, but two adjacent —CH 2 -groups cannot be replaced by —O—, and one or, if present, a plurality of —CH 2 -groups may be replaced by —CH═CH— or —C≡C— and in which one H atom or a plurality of H atoms may be replaced by F, OR 13 , N(R 13 )(R 14 ) or R 15 , or denote a single bond,
Y 11 to Y 14 each, independently of one another, denote methyl or ethyl,
Z 11 to Z 14 on each occurrence, independently of one another, denote —O—, —(C═O)—, —O—(C═O)—, —(C═O)—O—, —O—(C═O)—O—, —(N—R 13 )—,or —N—R 13 —(C═O)— or additionally a single bond if S 11 is a single bond, provided that both Z 11 and Z 12 do not simultaneously denote —O—, and, provided that, if S 12 is a single bond, both Z 13 and Z 14 do not simultaneously denote —O—, and, provided that , if —X 11 [—R 11 ] 0 — is a single bond, both Z 12 and Z 13 do not simultaneously denote —O—,
P denotes 1 o 2,
o denotes (3-p),
n * p denotes an integer from 3 to 10,
in the case where p=1,
n denotes an integer from 3 to 10,
m denotes (10-n),
and in the case where p=2,
n denotes an integer from 2 to 4, and
m denotes (4-n),

denotes an organic radical having (m+n) bonding sites,
X 11 denotes C, and in the case where p=1, —X 11 [—R 11 ] 0 — may alternatively also denote a single bond,
and one or more further compounds selected from:
b) one or more compounds of the 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/or
c) one or more compounds selected from the group of the compounds of the formulae III-1 to III-4 and B,

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,
m, n and o each, independently of one another, denote 0 or 1,
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.

2 . A medium according to claim 1 , wherein the total concentration of the compounds of the formula I in the medium as a whole is from 1 ppm to 2500 ppm.

3 . A medium according to claim 1 , which comprises a compound of the formula II in which 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 comprises one or more compounds of the formula B.

6 . A medium according to claim 1 , which comprises one or more compounds of the formula III-4.

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

8 . A compound of the formula I

in which
R 11 on each occurrence, independently of one another, denotes H, F, a straight-chain or branched alkyl chain having 1-20 C atoms, in which one —CH 2 -group or, if present, a plurality of —CH 2 -groups may be replaced by —O— or —C(═O)—, but two adjacent —CH 2 -groups cannot be replaced by —O—, and one or, if present, a plurality of —CH 2 -groups may be replaced by—CH═CH— or —C≡C—, and in which one H atom or a plurality of H atoms may be replaced by F, OR 13 , N(R 3 )(R 14 ) or R 15 ,
R 12 on each occurrence, independently of one another, denotes H, 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 be replaced by —O— or —C(═O)—, but two adjacent —CH 2 -groups cannot be replaced by —O—, 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 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 be replaced by OR 13 , N(R 13 )(R 14 ) or R 15 , or an aromatic or heteroaromatic hydrocarbon radical, in which one H atom or a plurality of H atoms may be replaced by F, OR 13 , N(R 13 )(R 14 ) or R 15 ,
R 13 on each occurrence, independently of one another, denotes H, a straight-chain or branched alkyl or acyl group having 1 to 10 C atoms or an aromatic hydrocarbon or carboxylic acid radical having 6-12 C atoms,
R 14 on each occurrence, independently of one another, denotes H, a straight-chain or branched alkyl or acyl group having 1 to 10 C atoms or an aromatic hydroca

Assignees

• Merck Patent Gmbh

Inventors

• Engel Martin
• Maag Sabrina
• Almeroth Ingo
• Fortte Rocco
• Goetz Achim
• Kodek Thorsten
• Heppert Oliver

Classifications

• C09K19/3003

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

• C09K19/44 Primary

  containing compounds with benzene rings directly linked · CPC title

• C09K2019/3016

  Cy-Ph-Ph · CPC title

• C09K2019/123

  Ph-Ph-Ph · CPC title

• C09K19/3444 Primary

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