Metal-ligand coordination compounds

Patent metadata

Field	Value
Publication number	US-9843004-B2
Application number	US-201514850518-A
Country	US
Kind code	B2
Filing date	Sep 10, 2015
Priority date	Sep 23, 2010
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

The present invention relates to novel metal-ligand coordination compounds of the general formula T1-(A-T2)i, where T1 and T2 represent metal-ligand coordination compounds, to the use thereof in a device, and to a formulation and a device which comprise the novel compounds.

First claim

The invention claimed is:

1. A compound of the following formula

where
A is a divalent unit which contains a conjugation-interrupting unit;
M 1 and M 2 are, independently of one another and identically or differently on each occurrence, selected from the group consisting of the main-group metals, transition metals, lanthanoids and actinoids;
L 1 and L 2 are, independently of one another, and with the metal form a cyclometallated five-membered ring or six-membered ring having at least one metal-carbon bond.

2. The compound according to claim 1 , wherein M 1 and M 2 are selected, independently of one another and identically or differently on each occurrence, from the group consisting of Ir, Ru, Os, Eu, Pt, Zn, Mo, W, Rh and Pd.

3. The compound according to claim 1 , wherein A is a divalent unit selected from the group consisting of the following:
linear or branched C 1-12 -alkylene,
C 3-8 -cycloalkylene,
linear or branched mono(C 1-12 -alkyl)silylene,
linear or branched di(C 1-12 -alkyl)silylene,
linear or branched tri(C 1-12 -alkyl)silylene,
a silylene group which is substituted by one, two or three mono- or polycyclic aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms,
linear or branched Si1-5-silylene,
linear or branched C1-12-alkyloxy-C1-12-alkylene,
linear or branched aryl-C1-12-alkyloxy-C1-12-alkylene, where aryl is a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms,
linear or branched C1-12-alkylthio-C1-12-alkylene,
sulfone,
linear or branched C1-12-alkylene sulfone,
sulfone oxide and
linear or branched C 1-12 -alkylene sulfone oxide,
where one or more H atoms of the said groups which represent A is optionally replaced by F, Cl, Br, I, a further C 1-12 -alkyl or C 3-8 -cycloalkyl, where one or more CH 2 groups of the alkyl or cycloalkyl is optionally replaced by heteroatoms, or a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, and
where one or more CH 2 groups of the said groups which represent A is optionally replaced by a divalent mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, and
with the proviso that the divalent unit A can bond to the ligands L 1 or L 2 via any conceivable atom of the unit.

4. The compound according to claim 1 , wherein in each case L 1 and L 2 is a bidentate ligand independently selected from phenylpyridine, naphthylpyridine, phenylquinoline, or phenylisoquinoline, wherein each of which is optionally substituted by one or more radicals R
wherein R is alkyl(ene), cycloalkyl(ene), alkylsilyl(ene), silyl(ene), arylsilyl(ene), alkylalkoxyalkyl(ene), arylalkoxyalkyl(ene), alkylthioalkyl(ene), phosphine, phosphine oxide, sulfone, alkylene sulfone, sulfone oxide, alkylene sulfone oxide, where the alkylene group in each case, independently of one another, has 1 to 12 carbon atoms and where one or more H atoms may be replaced by F, Cl, Br, I, alkyl or cycloalkyl, where one or more CH 2 may be replaced by a heteroatom, such as NH, O or S, or an aromatic or heteroaromatic hydrocarbon radical having 5 to 20 aromatic ring atoms.

5. The compound according to claim 1 , wherein

are phosphorescent compounds.

6. An electronic device comprising the compound according to claim 1 .

7. An organic electroluminescent device containing a the compound according to claim 1 , wherein the device is an organic light-emitting diode, an organic light-emitting electrochemical cell or an organic light-emitting transistor.

8. The organic electroluminescent device according to claim 7 , wherein the device has a planar shape and/or is in the form of a fibre.

9. An electronic device comprising the compound according to claim 1 , wherein the device is selected from the group consisting of an organic integrated circuit, an organic field-effect transistor, an organic thin-film transistor, an organic solar cell, a dye-sensitised organic solar cell, an organic optical detector, an organic photoreceptor, an organic field-quench device, an organic laser diode and an organic plasmon emitting device.

10. A formulation comprising at least one compound according to claim 1 and at least one solvent.

11. The formulation according to claim 10 , wherein the formulation is a solution, dispersion or emulsion.

12. A compound according to claim 1 for the therapy, prophylaxis and/or diagnosis of diseases and/or cosmetic conditions.

13. The compound according to claim 1 , wherein A is a divalent unit selected from the group consisting of the following:
linear or branched C 1-12 -alkylene,
C 3-8 -cycloalkylene,
linear or branched C1-12-alkyloxy-C1-12-alkylene,
linear or branched aryl-C1-12-alkyloxy-C1-12-alkylene,
where aryl is a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms,
linear or branched C1-12-alkylthio-C1-12-alkylene,
sulfone,
linear or branched C1-12-alkylene sulfone,
and one or more H atoms of the said groups which represent A is optionally replaced by F, Cl, Br, I, or a further C 1-12 -alkyl or C 3-8 -cycloalkyl,
where one or more CH 2 groups of the alkyl or cycloalkyl is optionally replaced by heteroatoms, or a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, and
where one or more CH 2 groups of the said groups which represent A is optionally replaced by a divalent mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms.

14. The compound according to claim 1 , wherein A is of formula (18)

wherein R 1 and R 2 are independently selected from alkylene, cycloalkylene, alkylsilylene, silylene, arylsilylene, alkylalkoxyalkylene, arylalkoxyalkylene, alkylthioalkylene, phosphine, phosphine oxide, sulfone, alkylene sulfone, sulfone oxide, alkylene sulfone oxide, where the alkylene group in each case, independently of one another, has 1 to 12 carbon atoms and where one or more H atoms may be replaced by F, Cl, Br, I, alkyl or cycloalkyl, where one or more CH 2 may be replaced by a heteroatom, such as NH, O or S, or an aromatic or heteroaromatic hydrocarbon radical having 5 to 20 aromatic ring atoms.

15. The compound according to claim 14 , wherein R 1 and R 2 are both phenylene.

16. The compound according to claim 14 , wherein in each case L 1 and L 2 is a bidentate ligand independently selected from phenylpyridine, naphthylpyridine, phenylquinoline, or phenylisoquinoline.

17. A compound of the following formula

where
A is a divalent unit which contains a conjugation-interrupting unit;
T 2 is a monovalent unit of the formula M 2 L′ 2 ;
M 1 and M 2 are independently selected from the group consisting of the main-group metals, transition metals, lanthanoids and actinoids;
L′, L 1 and L 2 are, independently of one another, and together with M 1 and M 2 , respectively, have a cyclometallated five-membered ring or six-membered ring having at least one metal-carbon bond.

18. The compound according to claim 17 , wherein in each case L 1 and L 2 is a b

Assignees

• Merck Patent Gmbh

Inventors

• Pan Junyou
• Anémian Rémi Manouk
• Buchholz Herwig

Classifications

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• H01L51/0085

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/5016

  Electricity · mapped topic

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title