IP Library Granted Patent US 11,495,755
Granted Patent B2
US 11,495,755 · App. 16/784,492 · Granted Nov 8, 2022

Organic electroluminescent materials and devices

Inventors: Raymond Kwong (Plainsboro, NJ); Bin Ma (Plainsboro, NJ); Chuanjun Xia (Lawrenceville, NJ); Bert Alleyne (Ewing, NJ); Jason Brooks (Philadelphia, PA)
Assignee: UNIVERSAL DISPLAY CORPORATION
H01L51/0085C07F15/0033C09K11/06H01L51/0081H01L51/0092H05B33/14C09K2211/1007C09K2211/1029C09K2211/1037C09K2211/185C09K2211/188H01L51/5016H01L51/5056H01L51/5072H01L51/5092
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Quick Facts
Patent No.
US 11,495,755
App. No.
16/784,492
Granted
Nov 8, 2022
Kind
B2
Abstract

A compound having a structure of is disclosed. In these formulas, each R 1 , R 2 , and R 3 is independently selected from hydrogen, alkyl, and aryl; at least one of R 1 and R 2 is a branched alkyl containing at least 4 carbon atoms, where the branching occurs at a position further than the benzylic position; where R 1 and R 3 are mono-, di-, tri-, tetra-, or no substitutions; and R 2 is mono-, di-, or no substitutions. Heteroleptic iridium complexes including such compounds, and devices including such compounds are also disclosed.

Claims (37)

1. An iridium compound having the formula:

wherein:

n is 1, 2 or 3;

each of R 1 , R 2 , and R 3 is independently a hydrogen, or a mono-substitution, up to the maximum allowable substitutions of alkyl, aryl, or combinations thereof;

at least one R 1 , R 2 , or R 3 is a branched alkyl containing at least 4 carbon atoms, and wherein the branching occurs at a position further than the benzylic position; and

X—Y is a bidentate ligand,

wherein any adjacently positioned substituents can, together, form a 4- to 7-member fused cyclic group.

2. The compound of claim 1 , wherein the branched alkyl is an isobutyl group.

3. The compound of claim 1 , wherein X—Y comprises acac.

4. A compound including a ligand having the formula:

each of R 1 , R 2 , and R 3 is independently a hydrogen, or a mono-substitution, up to the maximum allowable substitutions of alkyl, aryl, or combinations thereof;

at least one R 1 , R 2 , or R 3 is a branched alkyl containing at least 4 carbon atoms, and wherein the branching occurs at a position further than the benzylic position,

wherein any adjacently positioned substituents can, together, form a 4- to 7-member fused cyclic group.

5. The compound of claim 4 , wherein the ligand is coordinated to a metal having an atomic number greater than 40.

6. The compound of claim 4 , wherein the metal is Ir.

7. An organic light emitting device comprising:

an anode;

a cathode; and

an emissive organic layer, disposed between the anode and the cathode, the organic layer further comprising an iridium compound having the formula:

wherein n is 1, 2 or 3;

each of R 1 , R 2 , and R 3 is independently a hydrogen, or a mono-substitution, up to the maximum allowable substitutions of alkyl, aryl, or combinations thereof;

at least one R 1 , R 2 , or R 3 is a branched alkyl containing at least 4 carbon atoms, and wherein the branching occurs at a position further than the benzylic position; and

X—Y is a bidentate ligand,

wherein any adjacently positioned substituents can, together, form a 4- to 7-member fused cyclic group.

8. The device of claim 7 , wherein the organic emissive layer further comprises

9. The device of claim 7 , wherein the organic emissive layer further comprises BAlq.

10. The device of compound 11, wherein the device is selected from the group consisting of computer monitors, televisions, personal digital assistants, calculators, printers, instrument panels, wireless phones, handheld computers, flat-panel displays, heads-up displays, and bill boards.

11. The device of claim 7 , wherein the organic layer further comprises a host, wherein the host is an organic compound.

12. The device of claim 7 , wherein the organic layer further comprises a host, wherein the host is an organometallic compound.

13. The compound of claim 1 , wherein at least one R 1 is a branched alkyl containing at least 4 carbon atoms, and wherein the branching occurs at a position further than the benzylic position.

14. The compound of claim 1 , wherein at least one R 2 is a branched alkyl containing at least 4 carbon atoms, and wherein the branching occurs at a position further than the benzylic position.

15. The compound of claim 1 , wherein at least one R 3 is a branched alkyl containing at least 4 carbon atoms, and wherein the branching occurs at a position further than the benzylic position.

16. The compound of claim 1 , wherein two adjacently positioned substituents together form a 4- to 7-member fused cyclic group.

17. The compound of claim 1 , wherein two adjacently positioned substituents together form a 5- to 6-member fused cyclic group.

18. The compound of claim 1 , wherein two adjacently positioned R 1 together form a 4- to 7-member fused cyclic group.

19. The compound of claim 1 , wherein two adjacently positioned R 2 together form a 4- to 7-member fused cyclic group.

20. The compound of claim 1 , wherein two adjacently positioned R 3 together form a 4- to 7-member fused cyclic group.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 11, 2020
From: KWONG, RAYMOND; MA, BIN; XIA, CHUANJUN; ALLEYNE, BERT; BROOKS, JASON
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 051785/0362 →
Continuity (8)
Continuation 16255206 · Jan 23, 2019
Continuation 15873472 · Jan 17, 2018
Continuation 15400538 · Jan 6, 2017
Continuation 14826762 · Aug 14, 2015
Continuation 13849028 · Mar 22, 2013
Continuation 12044234 · Mar 7, 2008
Provisional Application 60905758 · Mar 8, 2007
Related Publication 20200176693A1 · Jun 4, 2020
Cited By (1)
US 12,622,128