Binuclear compounds

• US 7,090,928 B2
• Filed: 04/01/2003
• Issued: 08/15/2006
• Est. Priority Date: 04/01/2003
• Status: Expired due to Term

• Current Assignee: University of Southern California
• Original Assignee: University of Southern California
• Inventors: Thompson, Mark E., Djurovich, Peter, Alleyne, Bert
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US10/404,785
• Publication Number:
  US 20040197600A1
• Time in Patent Office: 1,232 Days
• Field of Search: 428/690, 428/917, 313/504, 313/506, 252/301.16, 257/40, 257/88, 257/89, 257/102, 257/103, 546/2, 546/4, 546/6, 548/101, 548/103, 556/13, 556/14, 556/17, 556/28, 556/32, 556/136
• US Class Current: 428/690
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/125 specially adapted for multicolour light emission, e.g. for emitting white light
• CPC Class Codes: H10K 85/30 Coordination compounds
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: H10K 85/361 Polynuclear complexes, i.e. complexes comprising two or more metal centers
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

Devices are provided having an anode, a cathode, and an emissive layer disposed between and electrically connected to the anode and the cathode. The emissive layer includes an emissive material having more than one metal center. In one embodiment, first and second metal centers are independently selected from the group consisting of d7, d8 and d9 metals. A bridging ligand is coordinated to the first metal center and to the second metal center. In one embodiment, the first and second metal centers each have coordination numbers of at least 3, and more preferably each have coordination numbers of 4. In one embodiment, photoactive ligands are coordinated to the first and second metal centers. In one embodiment, there are no photoactive ligands. In one embodiment, a charge neutral bi-nuclear emissive material is provided. In one embodiment the first and metal centers have a co-facial configuration, and preferably a square planar co-facial configuration. In one embodiment, the metal centers are selected from metals having an atomic number greater than or equal to 40.

Claims

1. An organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer comprising an organometallic emissive material comprising;

a first metal center selected from the group consisting of d8 metals;

a second metal center selected from the group consisting of d8 metals; and

a bridging ligand coordinated to the first metal center and to the second metal center;

wherein

the distance between the first metal center and the second metal center is such that there is significant overlap between a d8 orbital of the first metal and a d8 orbital of the second metal center, and wherein the organometallic emissive material meets (a) or (b) or (c);

(a) the metal centers are held in a co-facial configuration by the bridging ligand;

or

(b) the organometallic emissive material further comprises a second bridging ligand;

or

(c) the organometallic emissive material further comprises a second bridging ligand, and the metal centers are held in a co-facial configuration by at least one of the bridging ligands.

2. An organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer comprising a organometallic emissive material, wherein the organometallic emissive material is a binuclear material that comprises;

a first metal center selected from the group consisting of d7, d8 and d9 metals;

a second metal center selected from the group consisting of d7, d8 and d9 metals;

two bridging ligands, wherein each bridging ligand is coordinated to the first metal center and to the second metal center;

a first bidentate photoactive ligand bound to the first metal center, and

a second bidentate photoactive ligand bound to the second metal center.

3. The device of claim 2, wherein the first photoactive ligand and the second photoactive ligand are held in proximity by the bridging ligands and the first and second metal centers allowing for a significant π

—

π

interaction between the first and second photoactive ligands.

4. The device of claim 3, wherein the first and second photoactive ligands have the same structure.

6. The device of claim 2, wherein the first and second photoactive ligands have the following partial structure:

5. An organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer comprising an organometallic emissive material comprising;

a first metal center selected from the group consisting of d7, d8 and d9 metals;

a second metal center selected from the group consisting of d7, d8 and d9 metals; and

a bridging ligand coordinated to the first metal center and to the second metal center,

wherein substantially all of the light emitted from the device results from emission from an excimer-like excited state in which an excited state wave function extends over the first and second metal centers; and

wherein the organometallic emissive material meets (a) or (b) or (c);

(a) the metal centers are held in a co-facial configuration by the bridging ligand;

or

(b) the organometallic emissive material further comprises a second bridging ligand;

or

(c) the organometallic emissive material further comprises a second bridging ligand, and the metal centers are held in a co-facial configuration by at least one of the bridging ligands.

7. An organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer comprising an organometallic emissive material, wherein the emissive material has the structure;

8. An organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer comprising an organometallic emissive material comprising;

a first metal center selected from the group consisting of d7, d8 and d9 metals;

a second metal center selected from the group consisting of d7, d8 and d9 metals; and

a bridging ligand coordinated to the first metal center and to the second metal center;

wherein the distance between the first metal center and the second metal center is less than about 4 Angstroms; and

wherein the organometallic emissive material meets (a) or (b) or (c);

(a) the metal centers are held in a co-facial configuration by the bridging ligand;

or

(b) the organometallic emissive material further comprises a second bridging ligand;

or

(c) the organometallic emissive material further comprises a second bridging ligand, and the metal centers are held in a co-facial configuration by at least one of the bridging ligands.

9. An organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer comprising a binuclear organometallic emissive material comprising;

a first metal center that has a coordination number of 4;

a second metal center that has a coordination number of 4; and

a bridging ligand coordinated to the first metal center and to the second metal center;

wherein the organometallic emissive material meets (a) or (b) or (c);

(a) the metal centers are held in a co-facial configuration by the bridging ligand;

or

(b) the organometallic emissive material further comprises a second bridging ligand;

or

(c) the organometallic emissive material further comprises a second bridging ligand, and the metal centers are held in a co-facial configuration by at least one of the bridging ligands.

10. An organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer comprising a binuclear organometallic emissive material comprising;

a first metal center;

a second metal center;

a bridging ligand coordinated to the first metal center and to the second metal center;

a first photoactive ligand coordinated to the first metal center;

a second photoactive ligand coordinated to the second metal center;

wherein the first and second photoactive ligands have the following partial structure;

11. An organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer comprising a binuclear organometallic emissive material comprising;

a first metal center;

a second metal center;

a bridging ligand coordinated to the first metal center and to the second metal center;

a first photoactive ligand coordinated to the first metal center;

a second photoactive ligand coordinated to the second metal center;

wherein each bridging ligand is selected from the group consisting of carboxylates (RCCO⁻

), thiocarboxyloic acids (RCSS⁻

), pyrophosphate (⁻

O₃P—

O—

PO-₃⁻

) or a compound of the formula

12. An organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer comprising a binuclear organometallic emissive material comprising;

a first metal center;

a second metal center; and

a bridging ligand coordinated to the first metal center and to the second metal center;

wherein the metal centers are held in a co-facial configuration by the bridging ligand.

13. The device of claim 12, wherein the first and second metal centers each have a square planar configuration.