Organometallic complex and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-9741947-B2
Application number	US-201414231224-A
Country	US
Kind code	B2
Filing date	Mar 31, 2014
Priority date	Dec 9, 2013
Publication date	Aug 22, 2017
Grant date	Aug 22, 2017

Abstract

An organometallic complex represented by Formula 1 below and an organic light-emitting device including the same:

Formula 1 is as defined in the specification.

First claim

What is claimed is:

1. An organometallic complex represented by Formula 2 below:

wherein M is a metal selected from silver (Ag), gold (Au) and copper (Cu);
A, B, C, and D are each independently a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, or a substituted or unsubstituted C 6 -C 60 condensed polycyclic group;
each of X and Z is N and each of Y and W is P, or each of X and Z is P and each of Y and W is N;
for each of X, Y, Z and W that is N, a corresponding one of R 1 to R 4 is a lone electron pair or H, and for each of X, Y, Z and W that is P, a corresponding one of R 1 to R 4 is =O; a substituted or unsubstituted C 1 -C 60 alkyl group; a substituted or unsubstituted C 2 -C 60 alkenyl group; a substituted or unsubstituted C 2 -C 60 alkynyl group; a substituted or unsubstituted C 3 -C 60 cycloalkyl group; a substituted or unsubstituted C 3 -C 60 cycloalkenyl group; a substituted or unsubstituted C 6 -C 60 aryl group; a C 3 -C 60 alkylsilyl group; a C 6 -C 60 arylsilyl group; or a C 7 -C 60 alkylarylsilyl group.

2. The organometallic complex of claim 1 , wherein A, B, C, and D are each independently represented by one of Formulae 2a to 2f below:

wherein Z 1 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 1 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group;
p is an integer from 1 to 8; and
* is a binding site with X, Y, Z or W.

3. The organometallic complex of claim 1 , wherein for each of X, Y, Z and W that is N, a corresponding one of R 1 to R 4 is a lone pair electron, and for each of X, Y, Z and W that is P, a corresponding one of R 1 to R 4 is independently represented by one of Formulae 3a to 3f below:

wherein Z 1 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 1 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group;
wherein Z′ 1 to Z′ 3 are each independently a substituted or unsubstituted C 1 -C 20 alkyl group, or a substituted or unsubstituted C 6 -C 20 aryl group;
p is an integer from 1 to 7; and
* is a binding site.

4. The organometallic complex of claim 1 , wherein M is Cu, and the complex of Formula 2 is a delayed fluorescent material.

5. The organometallic complex of claim 1 , wherein the complex of Formula 2 is one selected from the group consisting of the following compounds:

wherein iPr represents isopropyl.

6. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode,
wherein the organic layer comprises the organometallic complex according to claim 1 .

7. The organic light-emitting device of claim 6 , wherein the organic layer comprises an emission layer.

8. The organic light-emitting device of claim 7 , wherein the emission layer comprises a compound represented by Formula 3 below:

wherein X is C, O, S, or N;
R a , R b , and R c , are each independently a hydrogen atom, a deuterium atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 arylamino group, or a substituted or unsubstituted C 6 -C 60 condensed polycyclic group; and
m and n are each independently an integer from 0 to 4, and when m or n is 2 or greater, a plurality of adjacent R a s or R b s are optionally linked to each other to form a ring;
when X is C, o is 2, when X is O or S, o is 0, and when X is N, o is 1.

9. The organic light-emitting device of claim 8 , wherein the plurality of adjacent R a s or R b s are linked to each other to form the ring.

10. The organic light-emitting device of claim 8 , wherein R a and R b are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 1 -C 30 heteroaryl group, a substituted or unsubstituted C 6 -C 30 arylamino group, or a compound represented by Formula 4a below:

wherein Z 1 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 1 -C 20 heteroaryl group, a substituted or u

Assignees

• Samsung Display Co Ltd
• Korea Advanced Inst Sci & Tech

Inventors

• Kim Youn-Sun
• Lee Yun-Ho
• Kim Seul-Ong
• Shin Dong-Woo
• Lee Jung-Sub
• Ito Naoyuki
• Chu Chang-Woong
• Kim Yeong-Eun

Classifications

• C09K2211/188

  of other metals not provided for in one of the previous groups · CPC title

• H01L51/0087

  Electricity · mapped topic

• H01L51/0085

  Electricity · mapped topic

• H01L51/0061

  Electricity · mapped topic

• H01L51/0091 Primary

  Electricity · mapped topic