Production of organic phosphorescent layers with addition of heavy main group metal complexes

Patent metadata

Field	Value
Publication number	US-10707422-B2
Application number	US-201414909996-A
Country	US
Kind code	B2
Filing date	May 8, 2014
Priority date	Aug 5, 2013
Publication date	Jul 7, 2020
Grant date	Jul 7, 2020

Abstract

A method is provided for producing organic electrical layers having organic emitters that are phosphorescent at room temperature. Organic fluorescent emitters, together with organic complex ligands containing metal complexes, and at least one heavy main group metal, selected from the group comprising In, Tl, Sn, Pb, Sb and Bi, are deposited jointly inside a layer, and the heavy main group metal changes its coordination sphere by receiving the organic fluorescent emitter.

First claim

What is claimed is:

1. A process for producing organic electronic layers including organic emitters that are phosphorescent at room temperature, the process comprising:
providing organic fluorescent emitters comprising organic molecules having either a partial or overall aromatic character with delocalized π electrons,
providing metal complexes containing organic complex ligands and at least one heavy main group metal selected from the group consisting of In, Tl, Sn, Pb, Sb and Bi, and
codepositing, in a single layer on a substrate, (a) the organic fluorescent emitters together with (b) the metal complexes containing organic complex ligands and the at least one heavy main group metal,
wherein combining the metal complexes containing the organic complex ligands and the at least one heavy main group metal with the organic fluorescent emitters via the codepositing step causes an alteration of the coordination sphere of the heavy main group metal including at least one of (a) an increase in a number of pairs of coordinated ligands and emitters or (b) a replacement of one or more of the organic complex ligands of the metal complexes by the organic fluorescent emitters.

2. The process of claim 1 , wherein the heavy main group metal comprises Bi.

3. The process of claim 1 , wherein the organic electronic layers exhibit a proportion of phosphorescent emission caused by electronic inter- and intra-ligand transfers with purely electronic excitation of not less than 20% and not more than 100%.

4. The process of claim 1 , wherein the organic fluorescent emitters comprise substituted or unsubstituted C6-C60 aromatics or heteroaromatics.

5. The process of claim 1 , wherein the organic fluorescent emitter is 4,7-di(9H-carbazol-9-yl)-1,10-phenanthroline (BUPH1).

6. The process of claim 1 , wherein the ligands of the metal complex are independently selected from the group consisting of (a) halides and (b) fluorinated or nonfluorinated C2-C20 alkyl or aryl carboxylates, alkoxides, thiolates, cyanates, isocyanates, thiocyanates, acetylacetonates, or sulfonates.

7. The process of claim 1 , wherein the metal complex comprises one or more compounds selected from the group consisting of Bi(III) fluorobenzoate, Bi(III) fluoroalkyl-benzoate, Bi(III) fluorodialkylbenzoate, Bi(III) fluorotri-alkylbenzoate, Bi(III) pentafluorobenzoate, and Bi(III) 3,5-trifluoromethylbenzoate.

8. The process of claim 1 , wherein the metal complex comprises one or more triarylbismuth(V) carboxylates.

9. The process of claim 1 , wherein the metal complex comprises Bi(III) triscarboxylate, Bi(III) fluoroacetate, or Bi(III) trifluoroacetate.

10. The process of claim 1 , comprising depositing the metal complex and the organic fluorescent emitter on a carrier substrate by coevaporation, rotary or curtain coating, bar coating, or printing.

11. The process of claim 10 , wherein the organic electronic layers have a molar ratio of metal complex to organic fluorescent emitter F of not less than 1:10 and not more than 10:1.

12. The process of claim 10 , comprising depositing the metal complex and the organic fluorescent emitter using a coevaporation process with a deposition rate of the organic electronic layer of not less than 0.1 Å/s and not more than 200 Å/s.

13. The process of claim 1 , wherein combining the metal complexes containing the organic complex ligands and the at least one heavy main group metal with the organic fluorescent emitters via the codepositing step further causes an alteration in a HOMO/LUMO energy level of at least some organic fluorescent emitters.

14. The process of claim 1 , wherein the metal complexes comprise organic complex ligands having terminal, bidentate, tridentate or heterobimetallic bridging to respective heavy metal atoms.

15. The process of claim 1 , wherein the metal complexes comprise organic complex ligands bonded to heavy metal atoms via oxygen atoms.

Assignees

• Siemens Ag

Inventors

• Kessler Florian
• Krestel Ana-Maria
• Maltenberger Anna
• Schmid Guenter
• Taroata Dan

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K71/00

  Manufacture or treatment specially adapted for the organic devices covered by this subclass · CPC title

• H10K85/611

  Charge transfer complexes · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title