Phosphorescent emitters containing dibenzo[1,4]azaborinine structure

Patent metadata

Field	Value
Publication number	US-9231218-B2
Application number	US-201313798935-A
Country	US
Kind code	B2
Filing date	Mar 13, 2013
Priority date	Jul 10, 2012
Publication date	Jan 5, 2016
Grant date	Jan 5, 2016

Abstract

A dibenzo[1,4]azaborine 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 B; and R 3 and R 4 represent mono, di, tri, tetra substitutions or no substitution;
wherein R 1 , R 2 , R 3 and R 4 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 any two adjacent R 1 , R 2 , R 3 , and R 4 are optionally joined to form a ring, which may be further substituted;
wherein L 1 is coordinated to a metal M, provided that the metal M does not form bond with E 1 and E 2 ; and
wherein L 1 may be linked with other ligands to comprise a bidentate, tridentate, tetradentate, pentadentate or hexadentate ligand.

First claim

We claim:

1. A compound comprising a first ligand L 1 ;
wherein L 1 comprises the following formula:

wherein E 1 is N;
wherein E 2 is B;
wherein R 3 and R 4 represent mono, di, tri, tetra substitutions or no substitution;
wherein R 1 , R 2 , R 3 and R 4 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 any two adjacent R 1 , R 2 , R 3 , and R 4 are optionally joined to form a ring, which may be further substituted;
wherein (i) at least one R 1 , R 2 , R 3 , or R 4 is a 5-or 6-membered heteroaryl ring A containing a nitrogen, (ii) at least one pair of adjacent substituents R 1 , R 2 , R 3 , and R 4 form a fused ring B that includes E 1 or E 2 , or (iii) both (i) and (ii);
wherein ring A, ring B, or both ring A and ring B are coordinated to metal M;
wherein ring A and ring B can be further substituted;
wherein L 1 is coordinated to a metal M, provided that the metal M does not form bond with E 1 and E 2 ; and
wherein L 1 may be linked with other ligands to comprise a bidentate, tridentate, tetradentate, pentadentate or hexadentate ligand.

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 and R 2 is aryl or substituted aryl.

6. The compound of claim 5 , wherein at least one of R 1 and R 2 is phenyl, or 2,6-disubstituted 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 the compound comprises a second ligand L 2 ;
wherein the ligand L 2 or part of the ligand L 2 if the ligand 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, sulfinyl, 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 the compound having the formula:

wherein L 2 is a second ligand coordinated to the metal M;
wherein each L 2 can be same or different;
wherein m is a value from 1 to the maximum number of ligands that may be attached to the metal M;
wherein m+n is the maximum number of ligands that may be attached to the metal M; and
wherein any of R 1 , R 2 , and R 3 are optionally linked to L 2 to comprise a bidentate, tridentate, tetradentate, pentadentate or hexadentate ligand.

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

12. The compound of claim 10 , 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 5 represents mono, di, tri, tetra substitutions or no substitution;
wherein R 5 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 , and R 5 are optionally joined to form a ring, which may be further substituted.

13. The compound of claim 12 , 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, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein R, R′ are optionally joined to form a ring with any adjacent substituent.

14. The compound of claim 10 , wherein the compound is selected from the group consisting of:

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

16. The compound of claim 14 , wherein m is 1, and n is 2.

17. The compound of claim 14 , wherein L 2 is selected from the group consisting of:

18. The compound of claim 10 , wherein the compound is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Lin Chun
• Xia Chuanjun

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K85/346

  comprising platinum · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title