Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9502672-B2
Application number	US-201313798917-A
Country	US
Kind code	B2
Filing date	Mar 13, 2013
Priority date	Jun 21, 2012
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

Abstract

A phenazasiline comprising compound, and devices and formulations including the same are described. The compound includes a ligand L 1 including:

wherein E 1 is N, E 2 is Si, and R 4 and R 5 represent mono, di, tri, tetra substitutions or no substitution;

wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each 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 any two adjacent R 1 , R 2 , R 3 , R 4 , and R 5 , are optionally joined to form a ring, which may be further substituted. In Formula I, L 1 is coordinated to metal M, which has an atomic weight higher than 40, provided that the metal M does not form bond with E 1 and E 2 . L 1 may be linked with other ligands.

First claim

We claim:

1. A compound having a structure of Formula II:

wherein metal M has an atomic weight higher than 40;
wherein R 5 represents mono, di, tri, tetra substitutions or no substitution;
wherein R 4 represents mono, di, or tri substitutions;
wherein each L 2 is a ligand coordinated to the metal M;
wherein each L 2 can be the same or different;
wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each 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 one R 4 is coordinated to the metal M;
wherein any two adjacent R 2 , R 3 , R 4 , and R 5 are optionally joined to form a ring, which may be further substituted;
wherein the metal M does not form a direct bond with the N or the Si of Formula II;
wherein any of R 1 , R 2 , R 3 , and R 4 are optionally linked to L 2 to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand;
wherein m is a value from 1 to the maximum number of ligands that may be attached to the metal M; and
wherein m+n is the maximum number of ligands that may be attached to the metal M.

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

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

4. The compound of claim 1 , wherein the metal M is Pt.

5. The compound of claim 1 , wherein at least one of R 1 , R 2 , and R 3 is aryl or substituted aryl.

6. The compound of claim 5 , wherein at least one of R 1 , R 2 , and R 3 is phenyl or substituted phenyl.

7. The compound of claim 1 , wherein the compound is homoleptic.

8. The compound of claim 1 , wherein the compound is heteroleptic.

9. The compound of claim 8 , wherein L 2 or part of L 2 if L 2 is more than bidentate is selected from the group consisting of:

wherein R a , R b , R c , and R d may represent mono, di, tri, or tetra substitution, or no substitution;
wherein R a , R b , R c , and R d 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, sulfanyl, sulfonyl, phosphino, and combinations thereof; and
wherein two adjacent substituents of R a , R b , R c , and R d are optionally joined to form a fused ring or form a multidentate ligand.

10. The compound of claim 1 , wherein at least one of R 1 , R 2 , and R 3 are linked to L 2 to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.

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

wherein X 1 , X 2 is selected from the group consisting of C, N, O, P, S, and B;
wherein A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein R 6 represents mono, di, tri, tetra substitutions or no substitution;
wherein R 6 is 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 any two adjacent R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are optionally joined to form a ring, which may be further substituted.

12. The compound of claim 11 , wherein A is selected from the group consisting of:

wherein Y is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR;
wherein R, R′ 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, sulfanyl, sulfonyl, phosphino, and combinations thereof; and
wherein R, R′ are optionally joined to form a ring with any adjacent substituent.

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

14. The compound of claim 13 , wherein m is 3, and n is 0.

15. The compound of claim 13 , wherein m is 1, and n is 2.

16. The compound of claim 13 , wherein L 2 is selected from the group consisting of:

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

18. The compound of claim 1 , wherein R 1 comprises a 5-membered or 6-membered carbocyclic or heterocyclic aromatic ring; and
wherein R 1 is coordinated to the metal M.

19. The compound of claim 1 , wherein R 2 comprises a 5-membered or 6-membered carbocyclic or heterocyclic aromatic ring; and
wherein R 2 is coordinated to the metal M.

20. The compound of claim 18 , wherein R 1 comprises at least one of the chemical groups selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Lin Chun
• Xia Chuanjun
• Kottas Gregg
• Elshenawy Zeinab

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title