Iridium complex, OLED using the same, and nitrogen-containing tridentate ligand having carbene unit

Patent metadata

Field	Value
Publication number	US-10153442-B2
Application number	US-201615099290-A
Country	US
Kind code	B2
Filing date	Apr 14, 2016
Priority date	Dec 31, 2015
Publication date	Dec 11, 2018
Grant date	Dec 11, 2018

Abstract

An iridium complex and an OLED using the same are shown. The iridium complex is represented by formula (I),

wherein R 1 is substituted or unsubstituted C 1-12 alkyl, or substituted or unsubstituted C 6-12 aryl; R 2 is hydrogen, fluorine or —C m F 2m+1 (m=1, 2 or 3), substituted or unsubstituted C 1-12 alkyl, or substituted or unsubstituted C 6-12 aryl; R 3 is hydrogen, fluorine or —C m F 2m+1 (m=1, 2 or 3), substituted or unsubstituted C 1-6 alkyl or alkoxy, and n is 1, 2, 3 or 4; each of R 4 is hydrogen or substituted or unsubstituted C 1-12 alkyl, or R 4 's may join to form a C 3-8 aromatic ring, and R 4 's may be the same or different; X 1 , X 2 , X 3 and X 4 are each independently CH or nitrogen; Y 1 , Y 2 and Y 3 are each independently carbon or nitrogen, with a proviso that at least one of Y 1 , Y 2 and Y 3 is nitrogen, and the tridentate chelate Y 1 ^Y 2 ^Y 3 is dianionic.

First claim

What is claimed is:

1. An iridium complex, being represented by formula (I):

wherein R 1 is substituted or unsubstituted C 1-12 alkyl, or substituted or unsubstituted C 6-12 aryl; R 2 is hydrogen, fluorine or —C m F 2m+1 (m=1, 2 or 3), substituted or unsubstituted C 1-12 alkyl, or substituted or unsubstituted C 6-12 aryl; R 3 is hydrogen, fluorine or —C m F 2m+1 (m=1, 2 or 3), substituted or unsubstituted C 1-6 alkyl, or substituted or unsubstituted C 1-6 alkoxy, and n is 1, 2, 3 or 4; each of R 4 is hydrogen or substituted or unsubstituted C 1-12 alkyl, or R 4 's may join to form a C 3-8 N-heteroaromatic or aromatic ring, and R 4 's may be the same or different; X 1 , X 2 , X 3 and X 4 are each independently CH or nitrogen; Y 1 is nitrogen in a pyrazole ring as a part of the tridentate chelate Y 1 ^Y 2 ^Y 3 , Y 2 and Y 3 are each independently carbon or nitrogen, and the tridentate chelate Y 1 ^Y 2 ^Y 3 is dianionic.

2. The iridium complex of claim 1 , wherein the tridentate chelate Y 1 ^Y 2 ^Y 3 has at least one electron-withdrawing substituent.

3. The iridium complex of claim 1 , wherein is nitrogen and Y 3 is carbon, the iridium complex being represented by formula (I-1):

wherein R 1 , R 2 , R 3 , R 4 , n, X 1 , X 2 , X 3 and X 4 are defined as in claim 1 .

4. The iridium complex of claim 1 , wherein X 1 , X 2 , X 3 and X 4 are all CH.

5. The iridium complex of claim 4 , being represented by any one of formulae (I-1-1) to (I-1-24):

6. The iridium complex of claim 1 , wherein at least one of X 1 , X 2 , X 3 and X 4 is nitrogen.

7. The iridium complex of claim 6 , being represented by any one of formulae (I-1-25) to (I-1-31):

8. The iridium complex of claim 1 , having a structure represented by one of formulae (I-a) and (I-b):

9. An organic light-emitting diode, comprising two electrodes and a light-emitting layer disposed between the two electrodes, wherein the light-emitting layer contains the iridium complex of claim 1 .

10. The organic light-emitting diode of claim 9 , wherein the iridium complex functions as a dopant in a host material of the light-emitting layer.

11. An N-containing tridentate chelate having a carbene unit, represented by formula (1):

wherein R 1 is substituted or unsubstituted C 1-12 alkyl, or substituted or unsubstituted C 6-12 aryl; R 2 is hydrogen, fluorine or —C m F 2m+1 (m is 1, 2 or 3), substituted or unsubstituted C 1-12 alkyl, or substituted or unsubstituted C 6-12 aryl; R 3 is hydrogen, fluorine or —C m F 2m+1 (m=1, 2 or 3), substituted or unsubstituted C 1-6 alkyl, or substituted or unsubstituted C 1-6 alkoxy, and n is 1, 2, 3 or 4; each of R 4 is hydrogen or substituted or unsubstituted C 1-12 alkyl, or R 4 's may join to form a C 3-8 N-heteroaromatic or aromatic ring, and R 4 's may be the same or different; X 1 , X 2 , X 3 and X 4 are each independently CH or nitrogen, wherein at least one of X 1 , X 2 , X 3 and X 4 is nitrogen.

Assignees

• Univ Nat Tsing Hua

Inventors

• Chi Yun
• Lin Jun

Classifications

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• H01L51/0085 Primary

  Electricity · mapped topic

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H01L51/5016

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title