Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11056658-B2
Application number	US-201815918179-A
Country	US
Kind code	B2
Filing date	Mar 12, 2018
Priority date	Mar 29, 2017
Publication date	Jul 6, 2021
Grant date	Jul 6, 2021

Abstract

A compound having the formula:

Formula I is disclosed. The compound is useful as emitters in OLEDs.

First claim

We claim:

1. A compound having the formula [L A ] 3-n Ir[L B ] n , having the structure:

wherein R 1 , R 2 , R 3 , R 4 , and R 5 each independently represents mono, to a maximum possible number of substitutions, or no substitution;
wherein X is selected from the group consisting of BR′, NR′, PR′, 0, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R′, R″, R′, R 2 , R 3 , R 4 , and R 5 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;
wherein any substitutions are optionally joined or fused into a ring;
wherein n is 1 or 2;
wherein R is selected from the group consisting of alkyl, and partially or fully deuterated variants thereof; and
wherein R has at least five carbon atoms.

2. The compound of claim 1 , wherein R has at least six carbon atoms.

3. The compound of claim 1 , wherein R has at least seven carbon atoms.

4. The compound of claim 1 , wherein n is 2.

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

6. The compound of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, and combinations thereof.

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

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.

8. The compound of claim 1 , wherein L B is selected from the group consisting of L B1 to L B1471 having a structure according to

wherein R B1 , R B2 , R B3 , and R B4 are defined as provided below:

L Bi ,

where i is
R B1
R B2
R B3
R B4

1.
H
H
H
H

2.
CH 3
H
H
H

3.
H
CH 3
H
H

4.
H
H
CH 3
H

5.
CH 3
CH 3
H
CH 3

6.
CH 3
H
CH 3
H

7.
CH 3
H
H
CH 3

8.
H
CH 3
CH 3
H

9.
H
CH 3
H
CH 3

10.
H
H
CH 3
CH 3

11.
CH 3
CH 3
CH 3
H

12.
CH 3
CH 3
H
CH 3

13.
CH 3
H
CH 3
CH 3

14.
H
CH 3
CH 3
CH 3

15.
CH 3
CH 3
CH 3
CH 3

16.
CH 2 CH 3
H
H
H

17.
CH 2 CH 3
CH 3
H
CH 3

18.
CH 2 CH 3
H
CH 3
H

19.
CH 2 CH 3
H
H
CH 3

20.
CH 2 CH 3
CH 3
CH 3
H

21.
CH 2 CH 3
CH 3
H
CH 3

22.
CH 2 CH 3
H
CH 3
CH 3

23.
CH 2 CH 3
CH 3
CH 3
CH 3

24.
H
CH 2 CH 3
H
H

25.
CH 3
CH 2 CH 3
H
CH 3

26.
H
CH 2 CH 3
CH 3
H

27.
H
CH 2 CH 3
H
CH 3

28.
CH 3
CH 2 CH 3
CH 3
H

29.
CH 3
CH 2 CH 3
H
CH 3

30.
H
CH 2 CH 3
CH 3
CH 3

31.
CH 3
CH 2 CH 3
CH 3
CH 3

32.
H
H
CH 2 CH 3
H

33.
CH 3
H

Assignees

• Universal Display Corp

Inventors

• Tsai Jui-Yi
• Zeng Lichang
• Ji Zhiqiang
• Dyatkin Alexey Borisovich
• Yeager Walter
• Barron Edward

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title