Compounds and liquid-crystalline medium

Patent metadata

Field	Value
Publication number	US-10907100-B2
Application number	US-201815883391-A
Country	US
Kind code	B2
Filing date	Jan 30, 2018
Priority date	Jan 30, 2017
Publication date	Feb 2, 2021
Grant date	Feb 2, 2021

Abstract

Compounds of formula I, and liquid-crystalline media, preferably having a nematic phase and negative dielectric anisotropy, comprising:
a) one or more compounds of formula I

and one or more other 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 B

Use thereof in electro-optical displays, particularly in active-matrix displays based on the VA, ECB, PALC, FFS or IPS effect and use of compounds of formula I for stabilisation of liquid-crystalline media which comprise one or more compounds of formula II and/or one or more compounds selected from compounds of formulae III-1 to III-4 and B.

First claim

The invention claimed is:

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 F, 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 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 6-12 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, 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 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 ] o — is a single bond, both Z 12 and Z 13 do not simultaneously denote —O—,
X 11 denotes C,
O. denotes an oxide radical,
p denotes 1 or 2,
o for formula I, denotes (3−p), and,
if p is 2,
n for formula I, denotes an integer from 2 to 4, and
m for formula I, denotes (4−n), and,
if p is 1,
n for formula I, denotes an integer from 5 to 10, and
m for formula I, denotes (10−n), and

denotes an organic radical having (m+n) bonding sites,
and where, in the case where p=1, —X 11 [—R 11 ] o — 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, for formulae III-1 to III-4, 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. 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 2000 ppm or less.

3. 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. 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. Medium according to claim 1 , which comprises one or more compounds of the formula B.

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

7. 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 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 F, 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 OR 13 , N(R 13 )(R 14 ) or R 15 ,
R 13 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 carboxylic acid radical having 6-12 C atoms,
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 c

Assignees

• Merck Patent Gmbh

Inventors

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

Classifications

• C09K19/3444 Primary

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

• C09K19/3402

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

• C09K19/30

  containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings · CPC title

• C09K19/10

  containing at least two benzene rings · CPC title

• G02F1/13

  based on liquid crystals, e.g. single liquid crystal display cells · CPC title