Complex compounds having tetradentate ligands and the use thereof in the opto-electronic field

Patent metadata

Field	Value
Publication number	US-9553276-B2
Application number	US-201214234809-A
Country	US
Kind code	B2
Filing date	Jul 18, 2012
Priority date	Jul 26, 2011
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

The invention describes electronic devices comprising a metal complex compound having at least one tetradentate ligand having N and/or P donors, in particular a ligand having a PPPP, NNNN, PNNP or NPPN structure, and uses of a complex of this type in the electronic field and for the generation of light.

First claim

The invention claimed is:

1. An electronic device comprising a metal complex having at least one tetradentate ligand having N and/or P donors wherein the ligand has a PPPP, NNNN, PNNP or NPPN structure wherein the ligand has the general formula I

in which
A, B, C and D are, independently of one another, P or N, where the valences of N or P may be at least partially saturated by one or two atom(s) and/or radical(s),
E is a bridge atom from the group with oxygen, sulfur, carbon, silicon or boron, to which one or two atom(s) and/or radical(s), and
F 1 and F 2 are ring systems of an aromatic or non-aromatic nature, where two adjacent ring atoms form the bridge between A and B and between C and D.

2. The device according to claim 1 , wherein the ligand has the formula II

in which
A, B, C and D are, independently of one another, P or N, where the valences of N or P may be at least partially saturated by one or two atom(s) and/or radical(s),
F 1 and F 2 are ring systems of an aromatic or non-aromatic nature, where two adjacent ring atoms form the bridge between A and B and between C and D,
R 1 to R 6 are, if they are bonded to a P, independently of one another, an atom or radical from the group comprising hydrogen, a halogen, R—, RO—, RS—, RCO—, RCOO—, RNH—, R 2 N—, RCONR— and —Si(R) x (OR) 3-x , where R=the C 1 -C 40 -hydrocarbon and X=1, 2 or 3,
R 1 to R 6 are, if they are bonded to an N, independently of one another, an atom or radical from the group with H, the C 1 -C 40 -hydrocarbon R and the silyl radical —Si(R) x (OR) 3-x ,
E is a bridge atom from the group with oxygen, sulfur, carbon, silicon or boron, where
one or two atoms and/or radicals from the group with hydrogen, halogen, —CN, R—, RO—, RS—, RCO—, RCOO—, RNH—, R 2 N—, RCONR— and —Si(R) x (OR) 3-x , where R=the C 1 -C 40 -hydrocarbon and X=1, 2 or 3, are optionally bonded to the carbon,
two radicals R— and/or RO—, where R=the C 1 -C 40 -hydrocarbon, are optionally bonded to the silicon or
one or two atoms and/or radicals from the group with halogen, R—, RO—, RS—, RCO—, RCOO—, RNH—, R 2 N—, RCONR— and —Si(R) x (OR) 3-x , where R=the C 1 -C 40 -hydrocarbon and X=1, 2 or 3, are optionally bonded to the boron.

3. The device according to claim 1 , wherein F1 and/or F2 are a cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl, aralkyl and/or heteroaralkyl radical.

4. The device according to claim 1 , wherein A and/or D are ring atoms of a ring system of an aromatic or non-aromatic nature.

5. An electronic device comprising a metal complex having at least one tetradentate ligand having N and/or P donors wherein the ligand has a PPPP, PNNP or NPPN structure and has the formula III

in which
A, B, C and D are, independently of one another, P or N, where the valences of N or P may be at least partially saturated by one or two atom(s) and/or radical(s),
R 1 to R 4 are, if they are bonded to a P, independently of one another, an atom or radical from the group comprising hydrogen, a halogen, R—, RO—, RS—, RCO—, RCOO—, RNH—, R 2 N—, RCONR— and —Si(R) x (OR) 3-x , where R=the C 1 -C 40 -hydrocarbon and X=1, 2 or 3,
R 1 to R 4 are, if they are bonded to an N, independently of one another, an atom or radical from the group with H, the C 1 -C 40 -hydrocarbon R and the silyl radical —Si(R) x (OR) 3-x ,
F 1 and F 2 are ring systems of an aromatic or non-aromatic nature, where two adjacent ring atoms form the bridge between A and B and between C and D,

and E is a carbon atom, where an atom or radical from the group with hydrogen, halogen, —CN, R—, RO—, RS—, RCO—, RCOO—, RNH—, R 2 N—, RCONR— and —Si(R) x (OR) 3-x , where R=the C 1 -C 40 -hydrocarbon and X=1, 2 or 3, is optionally bonded to the carbon.

6. A process for the production of the electronic device according to claim 1 , which comprises printing on a substrate a metal complex compound having at least one ligand of the formula I.

7. The device according to claim 1 wherein A, B, C and D are, independently of one another, P or N, where the valences of N or P may be at least partially saturated by one or two atom(s) and/or radical(s), and is selected from the group comprising hydrogen, a halogen, R—, RO—, RS—, RCO—, RCOO—, RNH—, R 2 N—, RCONR— and —Si(R) x (OR) 3-x , where R=the C 1 -C 40 -hydrocarbon and X=1, 2 or 3, and
E is a bridge atom from the group with oxygen, sulfur, carbon, silicon or boron, to which one or two atom(s) and/or radical(s), and is selected from the group with hydrogen, halogen, —CN, R—, RO—, RS—, RCO—, RCOO—, RNH—, R 2 N—, RCONR— and —Si(R) x (OR) 3-x , where R=the C 1 -C 40 -hydrocarbon and X=1, 2 or 3, may optionally be bonded.

8. The device according to claim 5 , wherein the device comprises the metal complex as constituent of an emitter layer, where the proportion of the metal complex in the emitter layer is between 0.1 and 50% by weight.

9. The device according to claim 5 , wherein the C1- to C40-hydrocarbon R is an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkylcycloalkyl, aryl, heteroaryl, aralkyl or heteroaralkyl radical, each of which may have one or more halogen, hydroxyl, thiol, carbonyl, keto, carboxyl, cyano, sulfone, nitro, amino and/or imino functions.

10. The device according to claim 5 , wherein the metal complex is mononuclear or polynuclear.

11. The device according to claim 5 , wherein the metal complex is a Cu, Ag, Au, Pd, Pt, Rh, Ir, Re, Os, Mo, W or Zn complex or the complex contains at least one of these metals.

12. The device according to claim 5 , wherein the device is selected from the group consisting of organic electroluminescent devices (OLEDs), light-emitting electrochemical cells (LEECs), organic solar cells (OSCs), organic field-effect transistors and organic lasers.

13. The device according to claim 5 , wherein the device comprises the metal complex as constituent of an absorber layer, where the proportion of the metal complex in the absorber layer is between 30 and 100% by weight.

14. The device according to claim 5 , wherein the metal complex is mononuclear or polynuclear and has between two and six metal centres.

15. An electronic device comprising a metal complex having at least one tetradentate ligand having N and/or P donors wherein the ligand has a PPPP, PNNP or NPPN structure and wherein the metal complex has the formula IV or formula V,

in which
A, B, C and D are, independently of one another, P or N, where the valences of N or P may be at least partially saturated by one or two atom(s) and/or radical(s),
R 1 to R 6 are, if they are bonded to a P, independently of one another, an atom or radical from the group comprising hydrogen, a halogen, R—, RO—, RS—, RCO—, RCOO—, RNH—, R 2 N—, RCONR— and —Si(R) x (OR) 3-x , where R=the C 1 -C 40 -hydrocarbon and X=1, 2 or 3,
R 1 to R 6 are, if they are bonded to an N, independently of one another, an atom or radical from the group with H, the C 1 -C 40 -hydrocarbon R and the silyl radical —Si(R) x (OR) 3-x

E is a bridge atom from the group with oxygen, sulfur, carbon

Assignees

• Wesemann Lars
• Mayer Hermann August
• Schubert Hartmut
• Wernitz Sophie
• Merck Patent Gmbh

Inventors

• Wesemann Lars
• Mayer Hermann August
• Schubert Hartmut
• Wernitz Sophie

Classifications

• C09K2211/187

  of the iron group metals, i.e. Fe, Co or Ni · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C07F15/0073

  Rhodium compounds · CPC title

• C07F15/0033

  Iridium compounds · CPC title

• C07F15/0093

  without a metal-carbon linkage · CPC title