IP Library Granted Patent US 9,435,021
Granted Patent B2
US 9,435,021 · App. 13/193,036 · Granted Sep 6, 2016

Co-deposition methods for the fabrication of organic optoelectronic devices

Inventors: Mark E. Thompson (Ewing, NJ); Zhiwei Liu (Ewing, NJ); Chao Wu (Ewing, NJ)
Assignee: UNIVERSITY OF SOUTHERN CALIFORNIA
C23C14/12C07F1/005H01L51/001H01L51/0091C09K11/06C09K2211/1007C09K2211/1029C09K2211/1048C09K2211/188H01L51/5016
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Quick Facts
Patent No.
US 9,435,021
App. No.
13/193,036
Granted
Sep 6, 2016
Kind
B2
Abstract

A method for fabricating an OLED by preparing phosphorescent metal complexes in situ is provided. In particular, the method simultaneously synthesizes and deposits copper (I) complexes in an organic light emitting device. Devices comprising such complexes may provide improved photoluminescent and electroluminescent properties.

Claims (45)

1. A method, comprising:

co-depositing one or more metal complexes having the formula MX n and one or more ligands by thermal vacuum depositing from two different heating sources to form a film comprising a phosphorescent complex over a substrate,

wherein M is a transition metal or lanthanide;

wherein X is alkyl, aryl, F, Cl, Br, I, SCN, OCN, CN, OR, and SR or combinations thereof;

wherein ft is alkyl or aryl;

wherein n is 1-10;

wherein each ligand is independently a mono-, di-, tri- or polydentate ligand; and

wherein the co-depositing step forms in-situ a phosphorescent complex comprising two to six of the metal complexes having the formula MX n and the one or more ligands.

2. The method of claim 1 , wherein at least one ligand is a neutral ligand that is coordinated to the M through a C, N, O, P or S atom.

3. The method of claim 2 , wherein at least one ligand is a neutral ligand that is coordinated to the M through a N atom.

4. The method of claim 1 , wherein the phosphorescent complex is selected from the group consisting of:

5. The method of claim 1 , wherein the phosphorescent complex is homoleptic.

6. The method of claim 1 , wherein the phosphorescent complex is heteroleptic.

7. A method, comprising:

co-depositing one or more metal complexes having the formula MX n and one or more ligand by thermal vacuum depositing from two different heating sources to form a film comprising a phosphorescent complex over a substrate,

wherein M is copper (I);

wherein X is alkyl, aryl, F, Cl, Br, I, SCN, OCN, CN, OR, and SR or combinations thereof;

wherein R is alkyl or aryl;

wherein n is 1-10;

wherein each ligand is independently a mono-, di-, tri- or polydentate ligand;

wherein one to six of the metal complexes having the formula MX n and the more than one ligands react in situ during the co-depositing step and form the phosphorescent complex.

8. The method of claim 7 , wherein the metal complex is CuI.

9. The method of claim 7 , wherein n is 1-3.

10. The method of claim 7 , wherein the phosphorescent complex includes 2 of the metal complexes.

11. The method of claim 7 , wherein each ligand is a neutral ligand that is coordinated to the copper (I) through a C, N, O, P or S atom.

12. The method of claim 11 , wherein each ligand is a neutral ligand that is coordinated to the copper (I) through a N atom.

13. The method of claim 7 , wherein at least one ligand is selected from the group consisting of:

wherein X is S, O, NR;

wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

wherein the ligand is coordinated to the copper (I) via at least one atom of the ligand.

14. The method of claim 13 , wherein at least one ligand is selected from the group consisting of:

wherein R′ and R″ are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

15. The method of claim 7 , wherein at least one ligand is a charged ligand having the formula:

wherein Y and X are independently selected from the group consisting of C, N, O, P and S.

16. The method of claim 15 , wherein

wherein A and B are each independently a 5 or 6-membered aromatic or heteroaromatic ring;

wherein A-B represents a bonded pair of aromatic or heteroaromatic rings coordinated to the metal via a nitrogen atom on ring A and an sp 2 hybridized carbon atom on ring B;

wherein each of R A and R B may represent mono, di, tri, or tetra substituents;

wherein each of R A and R B substituents are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

17. The method of claim 7 , further comprising:

providing a first electrode disposed over the substrate before the co-depositing step; and

depositing a second electrode over the co-deposited film of phosphorescent complex.

18. The method of claim 17 , wherein the first electrode is an anode and the second electrode is a cathode.

19. The method of claim 7 , wherein the phosphorescent complex is homoleptic.

20. The method of claim 7 , wherein the phosphorescent complex is heteroleptic.

Assignments (2)
CONFIRMATORY LICENSE Recorded Nov 30, 2023
From: UNIVERSITY OF SOUTHERN CALIFORNIA
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 065734/0058 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2011
From: THOMPSON, MARK E.; LIU, ZHIWEI; WU, CHAO
To: THE UNIVERSITY OF SOURTHERN CALIFORNIA
Reel/Frame 027138/0653 →
Continuity (2)
Provisional Application 61400505 · Jul 29, 2010
Related Publication 20120045862A1 · Feb 23, 2012