IP Library Granted Patent US 10,600,975
Granted Patent B2
US 10,600,975 · App. 16/255,206 · Granted Mar 24, 2020

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 10,600,975
App. No.
16/255,206
Granted
Mar 24, 2020
Kind
B2
Abstract

A compound including a ligand having the formula: or 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 (46)

1. An electronic display comprising an organic light emitting diode (OLED) comprising:

an anode;

a cathode; and

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

wherein n is 1, 2 or 3;

wherein each R 1 , R 2 , and R 3 is independently selected from the group consisting of hydrogen, alkyl, and aryl;

wherein at least one of R 1 and 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;

wherein R 1 and R 3 are mono-, di-, tri-, tetra-, or no substitutions;

wherein R 2 is mono-, di-, or no substitutions; and

wherein X—Y is an ancillary ligand.

2. The electronic display of claim 1 , wherein at least one R 3 is a branched alkyl containing at least 4 carbon atoms.

3. The electronic display of claim 1 , wherein the organic emissive layer further comprises BAlq or

4. The electronic display of claim 1 , wherein the branched alkyl is an isobutyl group.

5. The electronic display of claim 1 , wherein at least one R 3 is an isobutyl group.

6. The electronic display of claim 1 , wherein X—Y is acac.

7. The electronic display of claim 1 , wherein the compound is selected from the group consisting of:

and wherein the organic emissive layer further comprises BAlq or

8. The electronic display of claim 1 , wherein the electronic display is one of a computer monitor, a television, a personal digital assistant, a printer, an instrument panel, a calculator, a wireless phone, handheld computers, and a bill board.

9. An electronic display comprising an organic light emitting diode (OLED) comprising:

an anode;

a cathode; and

an emissive organic layer, disposed between the anode and the cathode, the organic layer comprising a host and a compound including a ligand having a formula:

wherein each R 1 , R 2 , and R 3 is independently selected from the group consisting of hydrogen, alkyl, and aryl;

wherein at least one of R 1 and 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;

wherein R 1 and R 3 are mono-, di-, tri-, tetra-, or no substitutions; and

wherein R 2 is mono-, di-, or no substitutions.

10. The electronic display of claim 9 , wherein the ligand is coordinated to a metal having an atomic number greater than 40.

11. The electronic display of claim 10 , wherein the metal is Ir.

12. The electronic display of claim 9 , wherein at least one R 3 is a branched alkyl containing at least 4 carbon atoms.

13. An emissive layer comprising a host material doped with a compound having a formula:

wherein n is 1, 2 or 3;

wherein each R 1 , R 2 , and R 3 is independently selected from the group consisting of hydrogen, alkyl, and aryl;

wherein at least one of R 1 and 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;

wherein R 1 and R 3 are mono-, di-, tri-, tetra-, or no substitutions;

wherein R 2 is mono-, di-, or no substitutions; and

wherein X—Y is an ancillary ligand.

14. The emissive layer of claim 13 , wherein at least one R 1 is a branched alkyl containing at least 4 carbon atoms.

15. The emissive layer of claim 13 , wherein at least one R 2 is a branched alkyl containing at least 4 carbon atoms.

16. The emissive layer of claim 13 , wherein at least one R 3 is a branched alkyl containing at least 4 carbon atoms.

17. The emissive layer of claim 13 , wherein the branched alkyl is an isobutyl group.

18. The emissive layer of claim 13 , wherein at least one R 1 is an isobutyl group.

19. The emissive layer of claim 13 , wherein at least one R 2 is an isobutyl group.

20. The emissive layer of claim 13 , wherein at least one R 3 is an isobutyl group.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 24, 2019
From: KWONG, RAYMOND; MA, BIN; XIA, CHUANJUN; ALLEYNE, BERT; BROOKS, JASON
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 048121/0477 →
Continuity (7)
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 20190157576A1 · May 23, 2019
Cited By (2)
US 12,495,662 US 12,622,128