Metal complex for phosphorescent OLED

Patent metadata

Field	Value
Publication number	US-10355227-B2
Application number	US-201414450865-A
Country	US
Kind code	B2
Filing date	Aug 4, 2014
Priority date	Dec 16, 2013
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

Abstract

The present disclosure relates to novel iridium complexes that can be used in organic light emitting devices (OLEDs). The present disclosure also relates to devices and formulations that incorporate the iridium complexes. The iridium complex can be a compound having the formula (L A ) m Ir(L B ) 3-m (I);
wherein L A is

 and
wherein L B can be one of:

First claim

What is claimed is:

1. A compound having the formula
(L A ) m Ir(L B ) 3-m   (I);

wherein L A is

wherein L B is

wherein R E represents mono or di-substitution, or no substitution;
wherein R 2 represents mono, di, or tri-substitution, or no substitution;
wherein R 1 , R B , and R F are each independently mono, di, tri, or tetra-substitution, or no substitution;
wherein X 1 , X 2 , X 3 , and X 4 are each independently CH or nitrogen, wherein the H in CH can be substituted by R F ;
wherein X is selected from the group consisting of O, S, and Se;
wherein R 1 , R 2 , R E , and R F 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, carboxyl, alkoxycarbonyl, cycloalkoxycarbonyl, heteroalkyloxycarbonyl, arylalkyloxycarbonyl, alkenyloxycarbonyl, cycloalkenyloxycarbonyl, heteroalkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, cyano, carbylamino, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein R 3 is selected from the group consisting of alkyl, cycloalkyl, and combinations thereof;
wherein R 3 is optionally partially or fully deuterated; and
wherein m is 1 or 2.

2. The compound of claim 1 , wherein m is 2.

3. The compound of claim 1 , wherein X is O.

4. The compound of claim 1 , wherein R 3 is an alkyl having at least 2 carbons.

5. The compound of claim 1 , wherein R 3 is an alkyl having at least 3 carbons.

6. The compound of claim 1 , wherein R 3 is a cycloalkyl.

7. The compound of claim 1 , wherein R 3 is selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, and cyclohexyl, wherein each is optionally partially or fully deuterated.

8. The compound of claim 1 , wherein R 1 is selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof.

9. The compound of claim 1 , wherein R 2 represents no substitution.

10. The compound of claim 1 , wherein R F is selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halogen, and combinations thereof.

11. The compound of claim 1 , wherein R F is fluorine.

12. The compound of claim 1 , wherein R E represents no substitution.

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

14. The compound of claim 1 , wherein L B is:

wherein R G represents mono, di, tri, or tetra-substitution, or no substitution; and
wherein R G is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxyl, alkoxycarbonyl, cycloalkoxycarbonyl, heteroalkyloxycarbonyl, arylalkyloxycarbonyl, alkenyloxycarbonyl, cycloalkenyloxycarbonyl, heteroalkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, cyano, carbylamino, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

15. The compound of claim 14 ,
wherein R B and R E represent no substitution; and
wherein R F and R G are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halogen, and combinations thereof.

16. The compound of claim 15 , wherein R G is fluorine.

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

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

Assignees

• Universal Display Corp

Inventors

• Ma Bin
• Barron Edward
• Deangelis Alan
• Yeager Walter
• Elshenawy Zeinab
• Wendt Harvey
• Wang Ting-Chih
• Cheon Kwang-Ohk
• Xia Chuanjun

Classifications

• H01L51/0085 Primary

  Electricity · mapped topic

• H01L51/5088

  Electricity · mapped topic

• H01L51/0081

  Electricity · mapped topic

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H01L51/0054

  Electricity · mapped topic