Organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-12279519-B2
Application number	US-202016997715-A
Country	US
Kind code	B2
Filing date	Aug 19, 2020
Priority date	Oct 1, 2019
Publication date	Apr 15, 2025
Grant date	Apr 15, 2025

Abstract

An organic electroluminescence device of an embodiment includes a first electrode, a second electrode on the first electrode, and an emission layer between the first electrode and the second electrode, wherein the emission layer includes a first host and a second host which are different from each other, a first dopant including an organic metal complex containing Ir, Ru, Rh, Pt, Pd, Cu, or Os as a central metal atom, and a second dopant represented by Formula D-2 below, and thereby the organic electroluminescence device may exhibit high luminous efficiency and long service life characteristics.

First claim

What is claimed is:

1. An organic electroluminescence device comprising:
a first electrode;
a second electrode on the first electrode; and
an emission layer between the first electrode and the second electrode,
wherein the emission layer comprises:
a first host;
a second host different from the first host;
a first dopant represented by Formula D-1a or Formula D-1b; and
a second dopant represented by Formula D-2:

wherein, in Formula D-1a,
M1 is Pt, Pd, Cu, or Os,
Q 1 to Q 4 are each independently C or N,
C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms for forming a ring,
L 21 to L 24 are each independently a direct linkage, *—O— *, * —S—* ,

a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring,
e1 to e4 are each independently 0 or 1,
R 31 to R 36 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms for forming a ring, and any of R 31 to R 36 are optionally combined with an adjacent group to form a ring, and
d1 to d4 are each independently an integer of 0 to 4,
in Formula D-lb,
M2 is Ir, Ru, or Rh,
n is 1 or 2,
X 1 to X 4 , Y 1 to Y 4 and Z 1 to Z 4 are each independently CR n or N, and R p , R q , and R n are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted amine group, and any of R p , R q , and R n are optionally combined with an adjacent group to form a ring,

and
wherein in Formula D-2,
A 1 and A 2 are each independently NR m or O,
R m is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring, and
R 1 to R 11 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boryl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and any of R 1 to R 11 are optionally combined with an adjacent group to form a ring.

2. The organic electroluminescence device of claim 1 , wherein the first host is represented by Formula H-1:

and
wherein in Formula H-1,
L 1 is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring,
Ar 1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring,
a and b are each independently an integer of 0 to 4, and
R a and R b are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring.

3. The organic electroluminescence device of claim 1 ,
wherein the second host is represented by Formula H-2:

and
wherein in Formula H-2,
Z 1 to Z 3 are each independently CR y or N, and
R y and R 21 to R 23 are each independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring.

4. The organic electroluminescence device of claim 3 ,
wherein Formula H-2 is represented by Formula H-2a:

and
wherein, in Formula H-2a, R 21 to R 23 are the same as those defined in Formula H-2.

5. The organic electroluminescence device of claim 3 ,
wherein Formula H-2 is represented by Formula H-2b:

and
wherein in Formula H-2b,
R 21 to R 23 and R y1 to R y3 are each independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and
at least one selected from R 21 to R 23 and R y1 to R y3 is a cyano group, an aryl group having 6 to 30 carbon atoms for forming a ring and comprising at least one cyano group as a substituent, or a heteroaryl group having 2 to 30 carbon atoms for forming a ring and comprising at least one cyano group as a substituent.

6. The organic electroluminescence device of claim 1 ,
wherein Formula D-2 is represented by any one of Formulae D-2a to D-2d:

and
wherein in Formula D-2a to Formula D-2d,
R m1 to R m4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and
R 1 to R 18 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boryl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and any of R 1 to R 18 are optionally combined with an adjacent group to form a ring.

7. The organic electroluminescence device of claim 1 ,
wherein the weight ratio o

Assignees

• Samsung Display Co Ltd

Inventors

• Jung Hyejin
• Kim Minje
• Kim Eung Do
• Kim Hyunyoung
• Kim Hyojeong
• Shin Hyosup
• Yoon Seokgyu
• Lee Youngki
• Lee Jungsub
• Lee Jiyoung
• Cho Kunwook
• Cho Hyeon Gu
• Choi Minsoo
• Choi Youngeun
• Jeong Hyein

Classifications

• H10K85/322

  comprising boron · CPC title

• H10K85/658

  Organoboranes · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/12 Primary

  comprising dopants · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title