Heterocyclic compound and organic electroluminescence device including the same

Patent metadata

Field	Value
Publication number	US-10741774-B2
Application number	US-201715839740-A
Country	US
Kind code	B2
Filing date	Dec 12, 2017
Priority date	Jul 4, 2017
Publication date	Aug 11, 2020
Grant date	Aug 11, 2020

Abstract

A heterocyclic compound represented by Formula 1 and an organic electroluminescence device including the same in an emission layer.

In Formula 1, Z is represented by Formula 2-1 or 2-2.

In Formula 2-2, X 1 to X 3 are each independently CR 10 or N, and at least one of X 1 to X 3 is N.

First claim

What is claimed is:

1. A heterocyclic compound represented by Formula 1,
wherein an absolute value of a difference between a singlet energy level and a triplet energy level of the heterocyclic compound is about 0.2 eV or less:

wherein, in Formula 1,
R 1 to R 6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 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,
L is 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,
a, b, c, d and e are each independently an integer of 0 to 4,
f is an integer of 0 to 3,
n is 0 or 1, and
Z is represented by Formula 2-1 or Formula 2-2:

wherein, in Formula 2-1,
g is 1 or 2, when g is 1, h is an integer of 0 to 4, and when g is 2, h is an integer of 0 to 3, and
R 7 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 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,
wherein, in Formula 2-2,
X 1 to X 3 are each independently CR 10 or N,
at least one of X 1 to X 3 is N, and
R 8 to R 10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 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,
wherein when Z is represented by Formula 2-1, n is 1.

2. The heterocyclic compound of claim 1 , wherein Z is represented by one of Formulae 3-1 to 3-9:

3. A heterocyclic compound represented by Formula 1,
wherein an absolute value of a difference between a singlet energy level and a triplet energy level of the heterocyclic compound is about 0.2 eV or less:

wherein, in Formula 1,
R 1 to R 6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 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,
L is 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,
a, b, c, d and e are each independently an integer of 0 to 4,
f is an integer of 0 to 3,
n is 0 or 1, and
Z is represented by Formula 2-1 or Formula 2-2:

wherein, in Formula 2-1,
p is 1 or 2, when g is 1, h is an integer of 0 to 4, and when g is 2, h is an integer of 0 to 3, and
R 7 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 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,
wherein, in Formula 2-2,
X 1 to X 3 are each independently CR 10 or N,
at least one of X 1 to X 3 is N, and

R 8 to R 10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 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, wherein Z is represented by Formula 2-2-1:

wherein, in Formula 2-2-1,
W 1 to W 5 are each independently CH or N, and
X 1 to X 3 are the same as defined above.

4. The heterocyclic compound of claim 3 , wherein a total number of N in W 1 to W 5 is 0 or 1.

5. The heterocyclic compound of claim 1 , wherein L is a substituted or unsubstituted phenylene group.

6. The heterocyclic compound of claim 1 , wherein at least one of R 1 , R 2 , R 4 , and R 5 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.

7. The heterocyclic compound of claim 6 , wherein at least one of R 1 , R 2 , R 4 , and R 5 is represented by one of following structures:

8. The heterocyclic compound of claim 1 , wherein a+b+d+e is 0, 1 or 2.

9. The heterocyclic compound of claim 1 , wherein the heterocyclic compound represented by Formula 1 is one selected from compounds represented in Compound Group 1:

10. An organic electroluminescence device, comprising:
a first electrode;
a hole transport region on the first electrode;
an emission layer on the hole transport region;
an electron transport region on the emission layer; and
a second electrode on the electron transport region,
wherein the emission layer comprises a heterocyclic compound represented by Formula 1, an absolute value of a difference between a singlet energy level and a tri

Assignees

• Samsung Display Co Ltd

Inventors

• Itoi Hiroaki

Classifications

• C07D403/14

  containing three or more hetero rings · CPC title

• C07D401/14 Primary

  containing three or more hetero rings · CPC title

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• H10K85/6572 Primary

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title