IP Library Granted Patent US 9,024,308
Granted Patent B2
US 9,024,308 · App. 14/540,838 · Granted May 5, 2015

Transition metal complexes with carbene ligands as emitters for organic light-emitting diodes (OLEDs)

Inventors: Markus Bold (Dirmstein, DE); Christian Lennartz (Neuhofen, DE); Martina Egen (Wachenheim, DE); Hans-Werner Schmidt (Bayreuth, DE); Mukundan Thelakkat (Bayreuth, DE); Markus Baete (Kulmain, DE); Christian Neuber (Bayreuth, DE); Wolfgang Kowalsky (Braunschweig, DE); Christian Schildknecht (Braunschweig, DE); Hans-Hermann Johannes (Braunschweig, DE)
Assignee: BASF SE
H01L51/0085H01L51/5096
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Quick Facts
Patent No.
US 9,024,308
App. No.
14/540,838
Granted
May 5, 2015
Kind
B2
Abstract

Use of transition metal complexes of the formula (I) in organic light-emitting diodes where: M 1 is a metal atom; carbene is a carbene ligand; L is a monoanionic or dianionic ligand; K is an uncharged monodentate or bidentate ligand selected from the group consisting of phosphines; CO; pyridines; nitriles and conjugated dienes which form a π complex with M 1 ; n is the number of carbene ligands and is at least 1; m is the number of ligands L, where m can be 0 or ≧1; o is the number of ligands K, where o can be 0 or ≧1; where the sum n+m+o is dependent on the oxidation state and coordination number of the metal atom and on the denticity of the ligands carbene, L and K and also on the charge on the ligands carbene and L, with the proviso that n is at least 1, and also an OLED comprising these transition metal complexes, a light-emitting layer comprising these transition metal complexes, OLEDs comprising this light-emitting layer, devices comprising an OLED according to the present invention, and specific transition metal complexes comprising at least two carbene ligands.

Claims (32)

1. An organic light-emitting diode comprising at least one uncharged transition metal complex of the formula (I) comprising at least one carbene ligand

wherein the symbols have the following meanings:

M 1 is Ir in any oxidation state possible for the respective metal atom;

carbene is a carbene ligand which may be uncharged or monoanionic and monodentate, bidentate or tridentate, with the carbene ligand also being able to be a biscarbene or triscarbene ligand;

L is a monoanionic or dianionic ligand, which may be monodentate or bidentate;

n is the number of carbene ligands, wherein n is at least 1 and when n>1 the carbene ligands in the complex of the formula I can be identical or different;

m is the number of ligands L, wherein m can be 0 or ≧1 and when m>1 the ligands L can be identical or different;

o is the number of ligands K, wherein o is 0;

wherein the sum n+m+o is dependent on the oxidation state and coordination number of the metal atom and on the denticity of the ligands carbene, L and also on the charge on the ligands carbene and L, with the proviso that n is at least 1,

wherein the carbene ligand or ligands has/have the formula II

wherein the symbols have the following meanings:

Do 1 is S or 0;

r is 0;

p is 0;

q is 0;

Y 1 and Y 2 together form a bridge between the donor atom Do 1 and the nitrogen atom N which has two atoms of which one is a carbon atom, and the other is a carbon or nitrogen atom;

R 1 and R 2 together form a bridge having a total of from three to five atoms of which one or two atoms may be heteroatoms and the remaining atoms are carbon atoms, so that the group

forms a five- to seven-membered, ring which may contain, in addition to the existing double bond, one further double bond or in the case of a six- or seven-membered ring two further double bonds and may be substituted by alkyl or aryl groups and may contain at least one heteroatom.

2. The organic light-emitting diode as claimed in claim 1 , wherein the uncharged transition metal complexes are employed as emitter molecules.

3. The organic light-emitting diode as claimed in claim 1 , wherein the carbene ligand or ligands is/are bidentate.

4. The organic light-emitting diode as claimed in claim 1 , wherein the carbene ligand or ligands is/are monoanionic.

5. The organic light-emitting diode as claimed in claim 1 , wherein the group

denotes the structure

wherein the symbols have the following meanings:

Z is CH or N and can be located in the o, m or p position relative to the point of linkage of the group to the carbene ligand;

R 12 is an alkyl, aryl, heteroaryl or alkenyl radical, or 2 radicals R 12 together form a fused-on ring which may contain one or more heteroatoms, or R 12 is a radical which acts as a donor or acceptor; and

t is 0 to 3 and when t>1 the radicals R 12 can be identical or different.

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

7. An OLED comprising a light-emitting layer as claimed in claim 6 .

8. A device selected from the group consisting of stationary VDUs and mobile VDUs each comprising an OLED as claimed in claim 1 .

9. A device selected from the group consisting of stationary VDUs and mobile VDUs each comprising an OLED as claimed in claim 7 .

10. The organic light-emitting diode as claimed in claim 1 , wherein the two atoms of the bridge formed by Y 1 and Y 2 are substituted, and the substituents of the groups Y 1 and Y 2 together form a bridge having a total of four atoms of which one or two may be N-heteroatoms and the remaining atoms are carbon atoms, so that the Y 1 and Y 2 together with the bridge form a six-membered aromatic ring.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE INCORRECT APPL. NO. 14/901,736 PREVIOUSLY RECORDED AT REEL: 039460 FRAME: 0615. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 8, 2017
From: BASF SE
To: UDC IRELAND LIMITED
Reel/Frame 042740/0222 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2016
From: BASF SE
To: UDC IRELAND LIMITED
Reel/Frame 039460/0615 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 23, 2015
From: BOLD, MARKUS; LENNARTZ, CHRISTIAN; EGEN, MARTINA; SCHMIDT, HANS-WERNER; THELAKKAT, MUKUNDAN; BAETE, MARKUS; NEUBER, CHRISTIAN; KOWALSKY, WOLFGANG; SCHILDKNECHT, CHRISTIAN; JOHANNES, HANS-HERMANN
To: BASF SE
Reel/Frame 035232/0668 →
Priority Claims (1)
DE 103 38 550 · Aug 19, 2003 · national
Continuity (3)
Continuation 12905112 · Oct 15, 2010
Division 10568344
Related Publication 20150073152A1 · Mar 12, 2015