Iridium complexes and organic light-emitting diodes using the same

Patent metadata

Field	Value
Publication number	US-2016359129-A1
Application number	US-201615155634-A
Country	US
Kind code	A1
Filing date	May 16, 2016
Priority date	Jun 5, 2015
Publication date	Dec 8, 2016
Grant date	—

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 1=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 2+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 and A 2 is independently a 5-membered or 6-membered ring; 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 oft 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

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H01L51/0085

  Electricity · mapped topic

• H01L51/5016 Primary

  Electricity · mapped topic

• C09K2211/185

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

• C09K11/06

  containing organic luminescent materials · CPC title