Use of transition metal carbene complexes in organic light-emitting diodes (OLEDs)

• US 10,522,768 B2
• Filed: 06/25/2014
• Issued: 12/31/2019
• Est. Priority Date: 11/25/2004
• Status: Active Grant

• Current Assignee: UDC Ireland Limited (Universal Display Corporation)
• Original Assignee: UDC Ireland Limited (Universal Display Corporation)
• Inventors: Egen, Martina, Kahle, Klaus, Bold, Markus, Gessner, Thomas, Lennartz, Christian, Nord, Simon, Schmidt, Hans-Werner, Thelakkat, Mukundan, Baete, Markus, Neuber, Christian, Kowalsky, Wolfgang, Schildknecht, Christian, Johannes, Hans-Hermann
• Primary Examiner(s): Yamnitzky, Marie R.
• Application Number:
  US14/314,753
• Publication Number:
  US 20140309428A1
• Time in Patent Office: 2,015 Days
• Field of Search: None
• CPC Class Codes: C07F 15/00 Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/14 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 Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 50/181 Electron blocking layers
• CPC Class Codes: H10K 85/342 comprising iridium

Abstract

The present invention relates to the use of transition metal-carbene complexes in organic light-emitting diodes (OLEDs), to a light-emitting layer, to a blocking layer for electrons or excitons, or to a blocking layer for holes, each comprising these transition metal-carbene complexes, to OLEDs comprising these transition metal-carbene complexes, to devices which comprise an inventive OLED, and to transition metal-carbene complexes.

Claims

1. An uncharged transition metal-carbene complex of the formula I

2. The complex of formula I as claimed in claim 1, wherein

M is selected from the group consisting of Rh, Ir, Pd, Pt, Ru and Os in any oxidation state possible for the particular metal atom.

3. The complex of formula I as claimed in claim 1, wherein

n is at least 2 and the carbene ligands may be the same or different;

m is 0 or ≥

1 and the ligands L, when m>

1, may be the same or different; and

q is 0 or ≥

1 and the ligands K, when q>

1, may be the same or different.

4. The complex of formula I as claimed in claim 1, wherein

n is at least 2 and the carbene ligands may be the same or different;

and

m, q are each 0.

5. The complex of formula I as claimed in claim 1, wherein

n is at least 2 and the carbene ligands are the same;

and

m and q are each 0.

6. An organic light-emitting diode comprising an uncharged transition metal-carbene complex of general formula I as claimed in claim 1.

7. A device selected from the group consisting of stationary visual display units of computers, televisions, visual display units in printers, kitchen appliances and advertising panels, illuminations, and information panels;

and mobile visual display units in mobile telephones, laptops, vehicles and destination displays in buses and trains, comprising an organic light-emitting diode as claimed in claim 6.

8. A process for preparing a transition metal-carbene complex of a formula I as claimed in claim 1 by deprotonating a ligand precursor corresponding to the particular carbene ligand and subsequently or simultaneously reacting it with a suitable metal complex comprising the desired metal.

9. A light-emitting layer comprising at least one transition metal-carbene complex of formula I as claimed in claim 1.

10. An organic light-emitting diode comprising a light-emitting layer as claimed in claim 9.

11. A device selected from the group consisting of stationary visual display units of computers, televisions, visual display units in printers, kitchen appliances and advertising panels, illuminations, and information panels;

and mobile visual display units in mobile telephones, laptops, vehicles and destination displays in buses and trains, comprising an organic light-emitting diode as claimed in claim 10.

12. A method of bulk coloring a polymeric material comprising adding an uncharged transition metal-carbene complex of formula I as claimed in claim 1 to said polymeric material.

13. The complex of formula I as claimed in claim 1, wherein Y³ is a hydrogen or alkyl group.

14. The complex of formula I as claimed in claim 1, wherein the complex is of the formula: