Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9670404-B2
Application number	US-201213542868-A
Country	US
Kind code	B2
Filing date	Jul 6, 2012
Priority date	Jun 6, 2012
Publication date	Jun 6, 2017
Grant date	Jun 6, 2017

Abstract

Compounds comprising the formula L 1 L 2 MX wherein L 1 , L 2 , and X are distinct bidentate ligands that form an octahedral complex on the metal M, wherein M is a metal with an atomic weight greater than 40. Compounds of this formula are sublimated more facilely than octahedral metal complexes where L 1 , L 2 , and X are not distinct bidentate ligands. Organic light emitting devices are also described wherein the emissive layer may comprise a host material containing an emissive molecule of formula L 1 L 2 MX, which molecule is adapted to luminesce when a voltage is applied across the heterostructure, and the emissive molecule is selected from the group of phosphorescent organometallic complexes, including iridium complexes of the formula L 1 L 2 IrX wherein L 1 , L 2 , and X are distinct bidentate ligands.

First claim

The invention claimed is:

1. A compound having the Formula:
L 1 L 2 MX,  Formula I;

wherein M is a metal having an atomic weight higher than 40;
wherein L 1 is a ligand selected from the group consisting of Formula II, Formula III, and Formula IV:

wherein L 2 has a structure of Formula VII:

wherein R 13 is 2,6-diisopropylphenyl;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 12 , and R 14 may represent no substitution, or up to the maximum possible substitutions;
wherein each R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 12 , and R 14 is 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;
wherein two adjacent substitutions are optionally joined to form a ring that can be further substituted;
wherein X is a monoanionic bidentate ligand; and
wherein L 1 , L 2 , and X are different.

2. The compound of claim 1 , wherein the compound is selected from the group consisting of:

3. A compound selected from the group consisting of:

4. A first device comprising a first organic light emitting device, comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound selected from the group consisting of:

and Formula I,
wherein Formula I has the structure L 1 L 2 MX;
wherein M is a metal having an atomic weight higher than 40;
wherein L 1 is a ligand selected from the group consisting of Formula II, Formula III, and Formula IV:

wherein L 2 has a structure of Formula VII:

wherein R 13 is 2,6-diisopropylphenyl;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 12 , and R 14 may represent no substitution, or up to the maximum possible substitutions;
wherein each R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 12 , and R 14 is 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, sulfonyl, sulfonyl, phosphino, and combinations thereof;
wherein two adjacent substitutions are optionally joined to form a ring that can be further substituted;
wherein X is a monoanionic bidentate ligand; and
wherein L 1 , L 2 , and X are different.

5. The first device of claim 4 , wherein the organic layer further comprises a host.

6. The first device of claim 5 , wherein the host comprises a metal 8-hydroxyquinolate complex.

7. The first device of claim 5 , wherein the host is selected from the group consisting of:

and combinations thereof.

8. The first device of claim 4 , wherein the first device is selected from the group consisting of a consumer product, an organic light-emitting device, a lighting panel, and a combination thereof.

9. The first device of claim 4 , wherein the compound is selected from the group consisting of:

10. The first device of claim 4 , wherein the compound is selected from the group consisting of:

11. The first device of claim 4 , wherein the compound has the structure of Formula I.

Assignees

• Xia Chuanjun
• Ma Bin
• Deangelis Alan
• Universal Display Corp

Inventors

• Xia Chuanjun
• Ma Bin
• Deangelis Alan

Classifications

• H01L51/0085

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title