Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11744141-B2
Application number	US-201816044583-A
Country	US
Kind code	B2
Filing date	Jul 25, 2018
Priority date	Aug 9, 2017
Publication date	Aug 29, 2023
Grant date	Aug 29, 2023

Abstract

A compound having the formula [LA]yIr[LB]x is disclosed, where LA is selected from one of the following:The compounds have at least one pyridyl dibenzo-substituted ligand that coordinates to metal center from the sterically hindered position as exemplified by LA. Because of this unique configuration, the compounds display better photo-physical and thermal properties and can be used in OLED devices to improve their performance, particularly with respect to the device's lifetime.

First claim

We claim:

1. A compound having the formula [L A ] y Ir[L B ] x ;
wherein L A is selected from the group consisting of:

wherein L B is

wherein each L A and L B can be the same or different;
wherein the compound is heteroleptic;
wherein x=1 or 2;
wherein y=1 or 2;
wherein x+y=3;
wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 are each independently selected from the group consisting of N and C;
wherein X 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 1 , R 2 , R 3 , R 4 , and R 5 each represents mono to a maximum possible number of substitutions, or no substitution;
wherein R, R′, R 1 , R 2 , R 3 , R 4 , and R 5 are each independently hydrogen or substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any two substituents may be optionally joined or fused together to form a ring;
wherein when X is NR and R is aryl or heteroaryl, R does not join with R 4 to form a ring;
wherein when R 4 is phenyl, Z 6 is C;
wherein adjacent R 3 and R 4 join to form a 5-membered ring, wherein the 5-membered ring is a cyclopentadiene, furan, or thiophene; and
wherein each L A and L B may be independently further substituted or linked together to form into a tridentate, tetradentate, pentadentate, or hexadentate ligand.

2. The compound of claim 1 , wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 are each C.

3. The compound of claim 1 , wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 is N.

4. The compound of claim 1 , wherein Z 1 is N, Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 are each C.

5. The compound of claim 1 , wherein R, R′, R 1 , R 2 , R 3 , R 4 , and R 5 are each independently hydrogen or substituents selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

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

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

8. The compound of claim 1 , where in LA is selected from the group consisting of:

wherein R 6 has the same definition as R 1 -R 5 ; and
wherein X and Y are each independently selected from the group consisting of NR, PR, O, S, Se, S═O, SO 2 , CRR′, SiRR′, and GeRR′.

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

wherein R 7 has the same definition as R 1 and R 2 .

10. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising the compound of claim 1 .

11. The OLED of claim 10 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

12. The OLED of claim 10 , wherein the organic layer further comprises a host, wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

13. The OLED of claim 12 , wherein the host is selected from the group consisting of:

and combinations thereof.

14. A consumer product comprising an organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising the compound of claim 1 .

15. The compound of claim 1 , A compound having the formula [L A ] y Ir[L B ] x ;
wherein each L A and L B can be the same or different;
wherein the compound is heteroleptic;
wherein x=1 or 2;
wherein y=1 or 2;
wherein x+y=3;
wherein L A is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

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

Classifications

• H10K85/342 Primary

  comprising iridium · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title