Granted Patent B2

US 12,635,402 · App. 18/487,224 · Granted May 19, 2026

Inventors: Martina Egen (Dossenheim, DE); Klaus Kahle (Ludwigshafen, DE); Markus Bold (Dirmstein, DE); Thomas Gessner (Heidelberg, DE); Christian Lennartz (Schifferstadt, DE); Simon Nord (Roemerberg, DE); Hans-Werner Schmidt (Bayreuth, DE); Mukundan Thelakkat (Bayreuth, DE); Markus Baete (Bayreuth, DE); Christian Neuber (Kulmain, DE); Wolfgang Kowalsky (Bayreuth, DE); Christian Schildknecht (Braunschweig, DE); Hans-Hermann Johannes (Braunschweig, DE)

Assignee: UDC IRELAND LIMITED

H10K85/342C07F15/0033C09K11/06H05B33/14H10K50/11C09K2211/1044C09K2211/185H10K50/14H10K2101/10

Abstract

Claims (25)

1 . An uncharged transition metal-carbene complex comprising a structure of the formula

wherein Do is;

r is 1;

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 wherein the 6-membered aromatic ring is fused to a further ring which is optionally further fused and optionally comprises heteroatoms;

Y 3 and Y 2 , together with the donor atom Do and the carbon atom to which Y 2 is bonded, form a ring which, apart from the donor atom Do, may also comprise further heteroatoms;

A is a bridge having three or four atoms, of which one or two atoms may be heteroatoms and the remaining atoms are carbon atoms, so that the group

forms a five- or six-membered heteroaromatic ring or benzene ring, each of which is optionally substituted by substituents selected from the group consisting of alkyl, alkyloxy, alkylthio, aryl, aryloxy, arylthio, chlorine, bromine, iodine, CN, 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 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 light-emitting layer comprising at least one transition metal-carbene complex as claimed in claim 1 .

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

10 . 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 9 .

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

12 . The uncharged transition metal-carbene complex as claimed in claim 1 , wherein the group

is fused to a further ring that is optionally further fused and optionally comprises heteroatoms.

13 . The uncharged transition metal-carbene complex as claimed in claim 1 , wherein Y 1 , together with a group selected from a chemical single bond, C(Y 4 ) 2 , C(O), O, S, S(O), SO 2 , and NY 5 , forms a bridge to the carbon atom or heteroatom of the bridge A which is in the α-position to the carbon atom that is bonded to the nitrogen atom of the carbene unit.

14 . The uncharged transition metal-carbene complex as claimed in claim 1 , wherein the metal M is selected from the group consisting of Pt(II) and Pd(II), having a coordination number of 4.

15 . The uncharged transition metal-carbene complex as claimed in claim 1 , wherein the metal M is Ir(III).

Priority Claims (1)

Continuity (4)

References Cited (37)