Iridium complexes and organic light-emitting diodes using the same

Patent metadata

Field	Value
Publication number	US-9553277-B2
Application number	US-201615155634-A
Country	US
Kind code	B2
Filing date	May 16, 2016
Priority date	Jun 5, 2015
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

An iridium complex represented by formula (1) and an OLED using the same are shown. In Formula (1), l, m, n, p, b, R 1 -R 6 , X 1 -X 6 , A 1 , A 2 and B are the same as defined in the specification. The iridium complex is able to emit a range of visible light with high color purity and high efficiency as neat sample.

First claim

What is claimed is:

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

wherein
each of l and n is an integer of 1 to 2;
each of m and p is an integer of 1 to 3;
b is an integer of 0 or 1;
R 1 is substituted or unsubstituted C 1-12 alkyl;
each of R 2 's is independently hydrogen or substituted or unsubstituted C 1-12 alkyl, provided that when l=2, two R 2 's may join to form a C 3-8 N-heteroaromatic or aromatic ring;
each of R 3 's is independently hydrogen, fluorine or —C x F 2x+1 (x=1, 2 or 3), substituted or unsubstituted C 1-12 alkyl, or substituted or unsubstituted C 6-12 aryl, provided that when m≧2, two or more R 3 's may join to form a C 3-8 aromatic ring;
each of R 4 's is independently hydrogen or substituted or unsubstituted C 1-12 alkyl, provided that when n=2, two R 4 's may join to form a C 3-8 N-heteroaromatic or aromatic ring;
R 5 is substituted or unsubstituted C 1-12 alkyl;
each of R 6 's is independently hydrogen, fluorine or —C x F 2x+1 (x=1, 2 or 3), substituted or unsubstituted C 1-12 alkyl, or substituted or unsubstituted C 6-12 aryl, provided that when p≧2, two or more R 6 's may join to form a C 3-8 N-heteroaromatic or aromatic ring;
each of X 1 , X 2 , X 3 , X 4 and X 5 is independently nitrogen or carbon;
each of A 1 and A 2 is independently a 5-membered or 6-membered unsaturated ring containing 0, 1, 2, 3 or 4 nitrogen atoms and 0 oxygen or sulphur atom; and
B is —O—, —CH 2 —, —CR 2 — or —NR— (R=methyl, ethyl or propyl), provided that when b=1.

2. The iridium complex of claim 1 , wherein A 1 is a 5-membered ring and A 2 is a 6-membered ring, the iridium complex being represented by formula (1a):

wherein
q is an integer of 1 to 2;
r is an integer of 1 to 4;
each of R 7 's is independently hydrogen, fluorinated alkyl —C x F 2x+1 (x=1, 2 or 3) or substituted or unsubstituted C 1-12 alkyl;
each of R 8 's is independently hydrogen, fluorinated alkyl —C x F 2x+1 (x=1, 2 or 3) or substituted or unsubstituted C 1-12 alkyl, provided that when r≧2, two or more R 7 's may join to form a C 3-8 N-heteroaromatic or aromatic ring;
each of X 6 , X 7 , X 8 , X 9 and X 10 is independently nitrogen or carbon; and
l, m, n, p, b, R 1 -R 6 , X 1 -X 5 , A 1 , A 2 and B are defined as in claim 1 .

3. The iridium complex of claim 2 , having a structure selected from one of formulae (1a-1) to (1a-33):

4. The iridium complex of claim 1 , wherein A 1 is a 5-membered ring and A 2 is a 5-membered ring, the iridium complex being represented by formula (1b):

wherein
each of q and s is an integer of 1 to 2;
each of R 7 's is independently hydrogen, fluorinated alkyl —C x F 2x+1 (x=1, 2 or 3) or substituted or unsubstituted C 1-12 alkyl;
each of R 9 's is independently hydrogen, fluorinated alkyl —C x F 2x+1 (x=1, 2 or 3) or substituted or unsubstituted C 1-12 alkyl;
each of X 6 and X 15 is nitrogen or carbon; and
l, m, n, p, b, R 1 -R 6 , X 1 -X 5 , A 1 , A 2 and B are defined as in claim 1 .

5. The iridium complex of claim 4 , having a structure selected from one of formulae (1b-1) to (1b-2):

6. The iridium complex of claim 1 , wherein A 1 is a 6-membered ring and A 2 is a 6-membered ring, the iridium complex being represented by formula (1c):

wherein
each of t and r is an integer of 1 to 4;
each of R 8 's is independently hydrogen, fluorinated alkyl —C x F 2x+1 (x=1, 2 or 3) or substituted or unsubstituted C 1-12 alkyl, provided that when r≧2, two or more R 8 's may join to form a C 3-8 aromatic ring;
each of R 10 's is independently hydrogen, fluorinated alkyl —C x F 2x+1 (x=1, 2 or 3) or substituted or unsubstituted C 1-12 alkyl, provided that when t≧2, two or more R 10 's may join to form a C 3-8 aromatic ring;
each of X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 and X 14 is independently nitrogen or carbon; and
l, m, n, p, b, R 1 -R 6 , X 1 -X 5 , A 1 , A 2 and B are defined as in claim 1 .

7. The iridium complex of claim 6 , having a structure selected from one of formulae (1c-1) to (1c-2):

8. 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 .

9. The organic light-emitting diode of claim 8 , wherein the iridium complex functions as a dopant in a host material of the light-emitting layer.

10. 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 2 .

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

12. 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 4 .

13. The organic light-emitting diode of claim 12 , wherein the iridium complex functions as a dopant in a host material of the light-emitting layer.

14. 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 6 .

15. The organic light-emitting diode of claim 14 , wherein the iridium complex functions as a dopant in a host material of the light-emitting layer.

Assignees

• Nat Univ Tsing Hua

Inventors

• Chi Yun
• Kuei Chu-Yun

Classifications

• H01L51/0085

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/185

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

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H01L51/5016 Primary

  Electricity · mapped topic