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

Patent metadata

Field	Value
Publication number	US-10522768-B2
Application number	US-201414314753-A
Country	US
Kind code	B2
Filing date	Jun 25, 2014
Priority date	Nov 25, 2004
Publication date	Dec 31, 2019
Grant date	Dec 31, 2019

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.

First claim

What is claimed is:

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

where the variables are each defined as follows:
M is a metal atom selected from the group consisting of Co, Rh, Ir, Nb, Pd, Pt, Fe, Ru, Os, Cr, Mo, W, Mn, Re, Cu, Ag and Au in any oxidation state possible for the particular metal atom;
L is a mono- or dianionic ligand which may be mono- or bidentate;
K is an uncharged mono- or bidentate ligand selected from the group consisting of phosphines; phosphonates and derivatives thereof; arsenates and derivatives thereof; phosphites; CO; pyridines; nitriles, monoolefins and conjugated dienes which form a π-complex with M;
n is the number of carbene ligands, where n is at least 1 and the carbene ligands in the complex of formula I, when n>1, may be the same or different;
m is the number of ligands L, where m may be 0 or ≥1 and the ligands L, when m>1, may be the same or different;
q is the number of ligands K, where q may be 0 or ≥1 and the ligands K, when q>1, may be the same or different,
where the sum of n+m+q depends upon the oxidation state and coordination number of the metal atom M and upon the denticity and the charge of the ligands, with the condition that n is at least 1;
Do is a donor atom selected from the group consisting of N, O and S;
r is 1 when Do is N, and r is O when Do is O or S;
Y 1 , Y 2 are each independently hydrogen, alkyl, aryl, heteroaryl or alkenyl;
or
Y 1 and Y 2 , together with the carbon atoms to which they are bonded, form a six-membered aromatic ring which may comprise one or two nitrogen atoms, and is optionally fused to a further ring which is optionally fused and optionally comprises heteroatoms;
Y 3 is hydrogen or alkyl;
or
Y 3 and Y 2 , together with the donor atom Do and the carbon atom to which Y 2 is bonded, form a five- or six-membered ring which, apart from the donor atom Do, may also comprise a further heteroatom selected from the group consisting of N, O and S;
A is a bridge having four atoms, so that the group

forms a benzene ring, wherein said benzene ring is substituted at the 4-position with a CN group and said benzene ring is optionally further substituted by substituents selected from the group consisting of alkyl, alkyloxy, alkylthio, aryl, aryloxy, arylthio, halogen, CHO, alkylcarbonyl, arylcarbonyl, carboxyl, alkyloxycarbonyl, aryloxycarbonyl, hydroxysulfonyl, alkyloxysulfonyl, aryloxysulfonyl, NO 2 and NO,
where Y 1 , together with a group selected from chemical single bond, C(Y 4 ) 2 , C(O), O, S, S(O), SO 2 and NY 5 , may optionally form a two-membered bridge B to that carbon atom of the bridge A which is in the α-position to the carbon atom which is bonded to the nitrogen atom of the carbene unit of the carbene ligand; and
Y 4 , Y 5 are each independently hydrogen, alkyl, aryl or heteroaryl, and the two Y 4 groups in the C(Y 4 ) 2 bridge may be varied independently of one another.

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 Y 3 is a hydrogen or alkyl group.

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

Assignees

• Udc Ireland Ltd

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

Classifications

• 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

• C07F15/0033

  Iridium compounds · CPC title

• C09K2211/185

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

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title