Fluorinated dibenzofuran and dibenzothiophene derivatives

Patent metadata

Field	Value
Publication number	US-10017695-B2
Application number	US-201615095229-A
Country	US
Kind code	B2
Filing date	Apr 11, 2016
Priority date	Apr 13, 2015
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

Disclosed are dibenzofuran and dibenzothiophene derivatives of the general formula I,

in which X 1 , X 2 , W, Y, R, A, Z and m have the meaning defined in claim 1 , to a process for the preparation thereof, to the use thereof as components in liquid-crystalline media, and to electro-optical display elements which contain the liquid-crystalline media according to the invention.

First claim

The invention claimed is:

1. A compound of the formula I

in which
W denotes O or S,
Y denotes F, Cl, CF 3 , OCF 3 or OCF 2 H,
with the proviso that, if W denotes O, Y cannot be F,

X 1 , X 2 denote H or F,
with the proviso that at least one radical X 1 or X 2 denotes F,

R denotes an alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH 2 groups in these radicals may each be replaced, independently of one another, by —C≡C—, —CF 2 O—, —OCF 2 —, —CH═CH—,

—O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by halogen,
A on each occurrence, identically or differently, denotes a radical selected from the following groups:
a) 1,4-phenylene, in which, in addition, one or two CH groups may be replaced by N and in which, in addition, one or more H atoms may be replaced by a group L,
b) the group consisting of trans-1,4-cyclohexylene and 1,4-cyclohexenylene, in which, in addition, one or more non-adjacent CH 2 groups may be replaced by —O— and/or —S— and in which, in addition, one or more H atoms may be replaced by F or Cl, and
c) the group consisting of tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl and selenophene-2,5-diyl, each of which may also be mono- or polysubstituted by a group L,

L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF 5 or straight-chain or branched, and in each case optionally fluorinated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, and
Z on each occurrence, identically or differently, denotes a single bond, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —(CO)O—, —O(CO)—, —(CH 2 ) 4 —, —CH 2 CH 2 —, —CF 2 —CF 2 —, —CF 2 —CH 2 —, —CH 2 —CF 2 —, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —(CH 2 ) 3 O—, —O(CH 2 ) 3 —, —C≡C—, —O—, —CH 2 —, —(CH 2 ) 3 — or —CF 2 —,
m denotes 0, 1 or 2.

2. A compound according to claim 1 , wherein X 1 and X 2 both denote F.

3. A compound according to claim 1 , wherein m denotes 0 or 1.

4. A compound according to claim 1 , wherein Y in formula I denotes CF 3 or OCF 3 .

5. A compound according to claim 4 , wherein Y denotes OCF 3 .

6. A compound according to claim 1 , wherein the compound of the formula I is selected from the compounds of sub-formulae Ia to Id,

in which R, A, Z and Y have the meanings indicated for formula I in claim 1 .

7. A compound according to claim 1 , wherein W denotes O.

8. A compound according to claim 1 , wherein the compound is selected from the compounds of the following formulae:

9. Liquid-crystalline medium comprising at least two compounds, which comprises at least one compound according to claim 1 .

10. Electro-optical display element containing a liquid-crystalline medium according to claim 9 .

11. Process for the preparation of a compound of the formula I according to claim 1 , comprising converting a compound of the formula II into a compound of the formula I

where R, A, Z, X 1 , X 2 , W, Y and m have the meaning indicated under claim 1 and G denotes —OH or —SG′, where G′ denotes H or a protecting group.

Assignees

• Merck Patent Gmbh

Inventors

• Lietzau Lars
• Brocke Constanze
• Reiffenrath Volker
• Manabe Atsutaka

Classifications

• C09K19/3491 Primary

  having sulfur as hetero atom · CPC title

• C07D307/91 Primary

  Dibenzofurans; Hydrogenated dibenzofurans · CPC title

• C09K19/3405

  the heterocyclic ring being a five-membered ring · CPC title

• C07D333/76

  Dibenzothiophenes · CPC title

• C09K2019/3408

  Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems · CPC title