Organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-12096683-B2
Application number	US-202017035552-A
Country	US
Kind code	B2
Filing date	Sep 28, 2020
Priority date	Oct 1, 2019
Publication date	Sep 17, 2024
Grant date	Sep 17, 2024

Abstract

An organic electroluminescence device according to an embodiment of the present disclosure includes a first electrode, a second electrode, and an emission layer. The emission layer includes host compounds and dopant compounds. The hot compounds include a first host compound represented by Formula 1, and a second host compound represented by Formula 2, and the dopant compounds include an assistant dopant compound represented by Formula 3, and a light-emitting dopant compound represented by Formula 4:

Accordingly, the organic electroluminescence device according to an embodiment may achieve high efficiency and long life.

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 host compounds and dopant compounds,
the host compounds comprise a first host compound represented by Formula 1, and a second host compound represented by Formula 2, and
the dopant compounds comprise an assistant dopant compound represented by Formula 3 and a light-emitting dopant compound represented by Formula 4:

wherein, in Formula 1,
R 1 and R 2 are each independently a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms for forming a ring,
L 1 is a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 3 to 30 carbon atoms for forming a ring,
Ar 1 is a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms for forming a ring, and
a and b are each independently an integer of 0 to 4,
in Formula 2,
Z 1 to Z 3 are each independently CR 11 or N, and
a plurality of R 11 and a plurality of R 12 are each independently a hydrogen atom, a deuterium atom, a cyano group, a substituted silyl group, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms for forming a ring,
in Formula 3,
A1 to A4 are each independently a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 1 to 30 carbon atoms for forming a ring,
X 1 to X 4 are each independently C or N,
R 21 to R 24 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 of 1 o 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 1 to 30 carbon atoms for forming a ring, and any of R 21 to R 24 are optionally combined with an adjacent group to form a ring,
d1 to d4 are each independently an integer of 0 to 4,
L 21 to L 23 are each independently a direct linkage,

a substituted or unsubstituted divalent alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring,
R 25 to R 27 are each independently a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms for forming a ring, and any of R 25 to R 27 are optionally combined with an adjacent group to form a ring,
d5 is an integer of 0 to 8,
M is platinum, palladium, copper, osmium, iridium, rubidium, or rhodium,
e1 to e3 are each independently 0 or 1, and
m is 1 or 2,
when M is platinum, palladium, copper or osmium, m is 1, and
when M is iridium, rubidium, or rhodium, m is 2 and e2 is 0, and
in Formula 4,
R 31 to R 41 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms for forming a ring.

2. The organic electroluminescence device of claim 1 , wherein L 1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted carbazolene group.

3. The organic electroluminescence device of claim 1 , wherein Ar 1 is a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted biphenyl group.

4. The organic electroluminescence device of claim 1 , wherein Formula 2 is represented by the following Formula 2-1:

wherein, in Formula 2-1,
a plurality of R 12 are each independently a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms for forming a ring.

5. The organic electroluminescence device of claim 1 , wherein Formula 2 is represented by the following Formula 2-2:

wherein, in Formula 2-2,
a plurality of R 11 and a plurality of R 12 are each independently a hydrogen atom, a deuterium atom, a cyano group, a substituted silyl group, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms for forming a ring, and
at least one selected from the plurality of R 11 and the plurality of R 12 is a cyano group, an aryl group of 6 to 30 carbon atoms, which comprises at least one cyano group as a substituent, or a heteroaryl group of 3 to 20 carbon atoms for forming a ring, which comprises at least one cyano group as a substituent.

6. The organic electroluminescence device of claim 1 , wherein Formula 3 is represented by the following Formula 3-1:

wherein, in Formula 3-1,
A1 to A4, X 1 to X 4 , R 21 to R 24 , d1 to d4, and L 22 are the same as defined in Formula 3.

7. The organic electroluminescence device of claim 6 , wherein A1 to A4 are each independently represented by any one selected from Structures 1-1 to 1-3:

wherein in Structures 1-1 to 1-3,
Y 1 is

or CR 54 , Y 2 is

or NR 61 , Y 3 is

or NR 62 ,
R 51 to R 64 are each independently a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 6 to 30 carbon atoms for forming a ring, and any of R 51 to R 64 are optionally combined with an adjacent group to form a ring.

8. The organic elect

Assignees

• Samsung Display Co Ltd

Inventors

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

Classifications

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• H10K85/371

  Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver · CPC title

• H10K85/348

  comprising osmium · CPC title

• H10K85/346

  comprising platinum · CPC title

• H10K85/344

  comprising ruthenium · CPC title