Complex compounds having anionic ligands containing two P donors and the use thereof in the opto-electronic field

Patent metadata

Field	Value
Publication number	US-9425398-B2
Application number	US-201214234857-A
Country	US
Kind code	B2
Filing date	Jul 18, 2012
Priority date	Jul 26, 2011
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

The invention describes electronic devices comprising a metal complex compound having at least one anionic ligand containing two P donors, having the formula (I), in which R1 to R4 are, independently of one another, an atom or radical from the group comprising hydrogen, a halogen, R, RO—, RS—, RCO—, RCOO—, RNH—, R2N—, RCONR— and —Si(R)X(OR)3-X, where R=a C1-C40-hydrocarbon and X=1, 2 or 3, and E is a bridge atom from the group with carbon or boron, where an atom or radical from the group with hydrogen, halogen, —CN, R, RO—, RS—, RCO—, RCOO—, RNH—, R2N—, RCONR— and —Si(R)X(OR)3-X, where R=the C1-C40-hydrocarbon and X=1, 2 or 3, is optionally bonded to the carbon, and two radicals from the group with halogen, R, RO—, RS—, RCO—, RCOO—, RNH—, R2N—, RCONR— and —Si(R)X(OR)3-X, where R=the C1-C40-hydrocarbon and X=1, 2 or 3, are optionally bonded to the boron. The invention furthermore describes a process for the production of an electronic device of this type and processes for the generation of light or blue emission using a metal complex compound of this type.

First claim

The invention claimed is:

1. An electronic device comprising a metal complex compound having at least one anionic ligand containing two P donors, having the formula I

in which
R 1 to R 4 are, 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=a C 1 -C 40 -hydrocarbon and X=1, 2 or 3, and
E is a carbon or a boron atom, where
if E is a carbon atom, 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, and
if E is a boron atom, two 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.

2. The device according to claim 1 , wherein the C 1 - to C 40 -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.

3. The device according to claim 1 , wherein at least one of the two P is a ring atom of a ring system of an aromatic or non-aromatic nature which includes the radicals R 1 and R 2 and/or R 3 and R 4 .

4. The device according to claim 1 , wherein the metal complex compound is mononuclear or polynuclear.

5. The device according to claim 1 , wherein the metal complex compound is mononuclear or polynuclear, and has one to six metal centers.

6. The device according to claim 1 , wherein the metal complex compound includes at least one of the metals Cu, Ag, Au, Pd, Pt, Rh, Ir, Re, Os, Mo, W or Zn.

7. The device according to claim 1 , wherein the metal complex compound includes at least one of the metals Cu, Ag, Au, Pd, Pt, Rh, Ir, Re, Os, Mo, W or Zn in ionic form.

8. The device according to claim 5 , wherein the metal complex compound includes a Cu or Ag ion and at least one further metal from the group with Cu, Ag, Au, Pd, Pt, Rh, Ir, Re, Os, Mo, W or Zn.

9. The device according to claim 1 , wherein that the metal complex compound has the formula II

in which
R 1 to R 4 and E are defined as in formula I,
[M] n represents a complex fragment where M=at least one metal from the group with Cu, Ag, Au, Pd, Pt, Rh, Ir, Re, Os, Mo, W and Zn,
n is equal to 1 or a higher integer and
y is equal to 1, 2 or 3.

10. The device according to claim 1 , wherein the metal complex compound has a ΔE separation between the lowest triplet state and the higher singlet state of between 50 cm-1 and 3000 cm-1.

11. The device according to claim 1 , wherein the device is selected from the group consisting of an organic electroluminescent device, a light-emitting electrochemical cell, an organic solar cell, an organic field-effect transistor and an organic laser.

12. The device according to claim 1 , wherein the device comprises the metal complex compound 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.

13. The device according to claim 1 , wherein the device comprises the metal complex compound 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. A process for the generation of light of a certain wavelength, comprising the step of the providing a metal complex compound having a ligand containing P donors of the formula I

in which
R 1 to R 4 are, 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=a C 1 -C 40 hydrocarbon and X=1, 2 or 3, and
E is a carbon or a boron atom, where
an atom or radical from the group of 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, and two radicals from the group of 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.

15. A process for the generation of blue emission which comprises utilizing a metal complex having a compound having a ligand containing P donors of the formula I

in which
R 1 to R 4 are, 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=a C 1 -C 40 hydrocarbon and X=1, 2 or 3, and
E is a carbon or a boron 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, and two radicals from the group of 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.

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

in which
R 1 to R 4 are, 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=a C 1 -C 40 hydrocarbon and X=1, 2 or 3, and
E is a carbon or a boron atom, where
an atom or radical from the group of 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, and two radicals from the group of 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 onto a substrate.

Assignees

• Wesemann Lars
• Schubert Hartmut
• Mayer Hermann August
• Yersin Hartmut
• Rausch Andreas
• Merck Patent Gmbh

Inventors

• Wesemann Lars
• Schubert Hartmut
• Mayer Hermann August
• Yersin Hartmut
• Rausch Andreas

Classifications

• C09K2211/183

  of the refractory metals, i.e. Ti, V, Cr, Zr, Nb, Mo, Hf, Ta or W · CPC title

• C09K2211/188

  of other metals not provided for in one of the previous groups · CPC title

• C09K2211/1096

  containing other heteroatoms · CPC title

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• Y02E10/549

  Organic PV cells · CPC title