Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9590194-B2
Application number	US-201414181118-A
Country	US
Kind code	B2
Filing date	Feb 14, 2014
Priority date	Feb 14, 2014
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

The present invention relates to metal complexes having novel ligands. The compounds are useful in organic light emitting devices (OLEDs), particularly as emitting dopants. The incorporation of these novel ligands provides red phosphorescent materials with good external quantum efficiency, good color, and long lifetime.

First claim

What is claimed is:

1. A compound comprising a ligand L A of formula I:

wherein ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein R is fused to ring B and has the formula II:

wherein the wave lines indicate bonds to ring B;
wherein R 1 and R 3 each independently represent mono, di, tri, or tetra substitution, or no substitution;
wherein R 2 represents mono or di substitution, or no substitution;
wherein X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are each independently carbon or nitrogen;
wherein at least one of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 is nitrogen;
wherein Y 1 is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R 1 , R 2 , R 3 , R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or wherein any two adjacent substituents are optionally joined to form a ring, which can be further substituted;
wherein L A is coordinated to a metal M;
wherein L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein M is optionally coordinated to other ligands.

2. The compound of claim 1 , wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

3. The compound of claim 1 , wherein M is Ir.

4. The compound of claim 1 , wherein Y 1 is selected from the group consisting of NR′, O, S, and CR′R″.

5. The compound of claim 1 , wherein Y 1 is O.

6. The compound of claim 1 , wherein one of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 is nitrogen.

7. The compound of claim 1 , wherein two of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are nitrogen.

8. The compound of claim 1 , wherein one of X 1 , X 2 , X 3 , and X 4 is nitrogen; and one of X 5 , X 6 , X 7 , and X 8 is nitrogen.

9. The compound of claim 1 , wherein one of X 1 , X 2 , X 3 , X 4 is nitrogen; and X 5 , X 6 , X 7 , and X 8 are carbon.

10. The compound of claim 1 , wherein X 2 is nitrogen; and X 1 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are carbon.

11. The compound of claim 1 , wherein ring A is phenyl.

12. The compound of claim 1 , wherein L A is selected from the group consisting of:

13. The compound of claim 1 , wherein the compound has formula III-A:
(L A ) n Ir(L B ) 3-n   (III-A);

wherein L B is a bidentate ligand; and n is 1, 2, or 3.

14. The compound of claim 13 , wherein L A is selected from the group consisting of L A1 to L A960 as shown below:

15. The compound of claim 14 , wherein L B is selected from the group consisting of:

16. The compound of claim 15 , wherein the compound has formula V:
(L A ) 1 Ir(L B ) 2   (V);

and the compound is selected from the group consisting of compound 961 to compound 5760 listed in the table below, where L A and L R each compound

Assignees

• Universal Display Corp

Inventors

• Boudreault Pierre-Luc T
• Dyatkin Alexey Borisovich
• Xia Chuanjun
• Joseph Scott
• Li David Zenan
• Yamamoto Hitoshi
• Weaver Michael S

Classifications

• H01L51/0085 Primary

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic

• H10K50/00

  Organic light-emitting devices (integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36) · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C07D491/12

  in which the condensed system contains three hetero rings · CPC title