Co-deposition methods for the fabrication of organic optoelectronic devices

Patent metadata

Field	Value
Publication number	US-9435021-B2
Application number	US-201113193036-A
Country	US
Kind code	B2
Filing date	Jul 28, 2011
Priority date	Jul 29, 2010
Publication date	Sep 6, 2016
Grant date	Sep 6, 2016

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.

First claim

The invention claimed is:

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.

Assignees

• Thompson Mark E
• Liu Zhiwei
• Wu Chao
• Univ Southern California

Inventors

• Thompson Mark E
• Liu Zhiwei
• Wu Chao

Classifications

• C09K2211/1048

  with oxygen · CPC title

• H01L51/0091

  Electricity · mapped topic

• C07F1/005

  without C-Metal linkages · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title