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

Patent metadata

Field	Value
Publication number	US-11980086-B2
Application number	US-201916729812-A
Country	US
Kind code	B2
Filing date	Dec 30, 2019
Priority date	Nov 25, 2004
Publication date	May 7, 2024
Grant date	May 7, 2024

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 comprising a structure of the formula

wherein 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 0 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 carbon atoms, so that the group

forms a benzene ring, wherein said benzene ring is substituted with a CN group and can be 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 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;
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; and
the structure is coordinated to a metal M 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.

2. The uncharged transition metal-carbene complex as claimed in claim 1 , wherein M is selected from the group consisting of Ir, Rh, Ru, Pt, and Pd in any oxidation state possible for the respective metal atom.

3. The uncharged transition metal-carbene complex as claimed in claim 1 , wherein the metal M is selected from the group consisting of Ir(III), Rh(III), and Ru(III), having a coordination number of 6; or from the group consisting of Pt(II) and Pd(II), having a coordination number of 4.

4. The uncharged transition metal-carbene complex as claim in claim 1 , wherein M is Ir(III) having a coordination number of 6 or Pt(II) having a coordination number of 4.

5. The uncharged transition metal-carbene complex as claimed in claim 1 , wherein the complex consists of a ligand comprising a structure of the formula

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

7. A light-emitting layer comprising at least one transition metal-carbene complex as claimed in claim 1 .

8. An organic light-emitting diode comprising a light-emitting layer as claimed in claim 7 .

9. 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 .

10. A method of bulk coloring a polymeric material comprising adding an uncharged transition metal complex as claimed in claim 1 to said polymeric material.

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 8 .

12. The transition metal-carbene complex as claimed in claim 1 , wherein Y 3 is a hydrogen or alkyl group.

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

• H10K85/342 Primary

  comprising iridium · CPC title

• C07F15/0033

  Iridium compounds · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · 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

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title