IP Library Granted Patent US 9,130,178
Granted Patent B2
US 9,130,178 · App. 12/306,957 · Granted Sep 8, 2015

Oligomers of isonitrile-metal complexes as triplet emitters for OLED applications

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Quick Facts
Patent No.
US 9,130,178
App. No.
12/306,957
Granted
Sep 8, 2015
Kind
B2
Abstract

The present invention relates to light-emitting devices and in particular organic light-emitting devices (OLEDs). In particular, the invention relates to the use of luminescent isonitrile/metal complexes as oligomer emitters in devices of this type.

Claims (52)

1. A light emitting device comprising

(i) an anode,

(ii) a cathode and

(iii) an emitter layer, arranged between and in direct or indirect contact with the anode and cathode, comprising at least one complex of-formula (I)

(NC) n M(CNR) m   (I)

wherein

M is (Pt(II), Pd(II), Rh(I), Ir(I), or Au(III);

R is an alkyl, alkenyl, alkynyl, heteroaryl or —SO 2 R′ group, which optionally contains one or more functional groups wherein R′ is a hydrocarbon group, which optionally contains heteroatoms; and

n =m =2;

wherein the proportion of complexes of formula (I) in the emitter layer is more than 10% by weight, based on the total weight of the emitter layer and

wherein said device is insulated from the environment, so that ingress of gas from the environment into the emitter layer cannot occur;

wherein two radicals CNR together form a radical CN—R″—NC, wherein R″ is selected from alkylene, alkenylene, alkynylene, arylene, heteroarylene, wherein R″ optionally contains one or more heteroatoms.

2. The light emitting device of claim 1 , wherein it is an organic light-emitting device (OLED).

3. The light emitting device of claim 1 , further comprising a hole-conductor layer and/or an electron-conductor layer.

4. The light emitting device of claim 1 , further comprising a CsF or LiF interlayer.

5. The light emitting device of claim 1 , wherein it is arranged on a substrate.

6. The light emitting device of claim 1 , wherein M in formula (I) is Pt(II) or Pd(II).

7. The light emitting device of claim 1 , wherein the proportion of complexes of formula (I) in the emitter layer is more than 30% by weight, based on the total weight of the emitter layer.

8. The light emitting device of claim 1 , wherein the proportion of complexes of formula (I) in the emitter layer is more than 80% by weight, based on the total weight of the emitter layer.

9. The light emitting device of claim 1 , wherein the complex of formula (I) in the emitter layer is bonded to a polymer.

10. The light emitting device of claim 9 , wherein the bonding to the polymer takes place via polymerisable groups of the radicals R.

11. The light emitting device of claim 9 , wherein an emitter layer is applied which comprises a polymer to which complexes of formula (I) are bonded, and the complexes are present in a concentration at which metal-metal interactions are able to form.

12. The light emitting device of claim 1 , wherein it comprises, as emitter, the compound

dicyanobis(1,3-diisocyanopropane)platinum(II), Pt(CN) 2 (CNCH 2 CH 2 CH 2 NC).

13. The light emitting device of claim 1 , wherein it is a display and/or a light device.

14. A process for producing the light-emitting device of claim 1 , wherein at least one complex of the formula (I) is introduced into the emitter layer by means of vacuum sublimation.

15. A process for producing the light-emitting device of claim 1 , wherein at least one complex of the formula (I) is introduced into the emitter layer by wet-chemical methods.

16. A process for producing the light-emitting device of claim 1 , wherein at least one complex of the formula (I) is applied as a colloidal suspension.

17. A light emitting device comprising

(i) an anode,

(ii) a cathode and

(iii) an emitter layer, arranged between and in direct or indirect contact with the anode and cathode, comprising at least two different complexes of formula (I)

(NC) n M(CNR) m   (I)

wherein

M is (Pt(II), Pd(II), Rh(I), Ir(I), or Au(III);

R is an alkyl, alkenyl, alkynyl, heteroaryl or —SO 2 R′ group, which optionally contains one or more functional groups wherein R′ is a hydrocarbon group, which optionally contains heteroatoms; and

n =m =2;

wherein the proportion of complexes of formula (I) in the emitter layer is more than 10% by weight, based on the total weight of the emitter layer and

wherein said device is insulated from the environment, so that ingress of gas from the environment into the emitter layer cannot occur.

18. The light emitting device of claim 17 , wherein the emitter layer comprises at least one complex of the formul (I) where M=Pt and at least one complex of the formula (I) where M=Pd.

19. The light emitting device of claim 17 , wherein the at least two different complexes of the formula (I) are present in a columnar structure in the emitter layer.

20. A light emitting device comprising

(i) an anode,

(ii) a cathode and

(iii) an emitter layer, arranged between and in direct or indirect contact with the anode and cathode, comprising at least one complex of-formula (I)

(NC) n M(CNR) m   (I)

wherein

M is (Pt(II), Pd(II), Rh(I), Ir(I), or Au(III);

R is an alkenyl, alkynyl, heteroaryl or —SO 2 R′ group, which optionally contains one or more functional groups wherein R′ is a hydrocarbon group, which optionally contains heteroatoms; and

n =m =2;

wherein the proportion of complexes of formula (I) in the emitter layer is more than 10% by weight, based on the total weight of the emitter layer and

wherein said device is insulated from the environment, so that ingress of gas from the environment into the emitter layer cannot occur.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2023
From: MERCK PATENT GMBH
To: UDC IRELAND LIMITED
Reel/Frame 064004/0725 →
CORRECTED ASSIGNMENT TO CORRECT THE DOC. DATE PREIOUSLY RECORD AT REEL 024229 FRAME 0124. Recorded May 27, 2011
From: NOVALED AG
To: MERCK PATENT GMBH
Reel/Frame 026366/0200 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 14, 2010
From: NOVALED AG
To: MERCK PATENT GMBH
Reel/Frame 024229/0124 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2009
From: YERSIN, HARTMUT; MONKOWIUS, UWE; FISCHER, TOBIAS; FINKENZELLER, WALTER; CZERWIENIEC, RAFAL
To: NOVALED AG
Reel/Frame 022424/0336 →