Heterocyclic compound, and organic electroluminescence device and organic electroluminescence display device including the same

Patent metadata

Field	Value
Publication number	US-10844065-B2
Application number	US-201815963036-A
Country	US
Kind code	B2
Filing date	Apr 25, 2018
Priority date	Sep 21, 2017
Publication date	Nov 24, 2020
Grant date	Nov 24, 2020

Abstract

Provided are a heterocyclic compound represented by Formula 1 and an organic electroluminescence device and an organic electroluminescence display device including the heterocyclic compound represented by Formula 1 in an emission layer. In Formula 1, A is represented by Formula 2, D 1 is represented by Formula 3, and D 2 is represented by Formula 4.

First claim

What is claimed is:

1. A heterocyclic compound represented by the following Formula 1:
D 1 -A-D 2   Formula 1

wherein in Formula 1, A is represented by the following Formula 2, D 1 is represented by the following Formula 3, and D 2 is represented by the following Formula 4:

wherein in Formulae 2 to 4,
q and r are each independently an integer of 0 to 3,
p is 0 or 1,
X 1 and X 2 are each independently CR′ or N,
R′ and R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,
L 1 and L 2 are each independently 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,
Y 1 and Y 2 are each independently a substituted or unsubstituted arylamine 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 of Y 1 or Y 2 is an electron-donating group,
in case p is 0, Y 1 and Y 2 are each independently represented by the following Formula 5:

wherein in Formula 5,
R 5 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, and
m is an integer of 0 to 6, and
wherein the heterocyclic compound emits near-infrared rays in a wavelength region of about 750 nm to about 1,000 nm.

2. The heterocyclic compound of claim 1 , wherein p is 1, and X 1 and X 2 are N.

3. The heterocyclic compound of claim 1 , wherein at least one of Y 1 or Y 2 is represented by one of the above Formula 5, the following Formula 6 or the following Formula 7:

wherein in Formula 6,
Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,
wherein in Formula 7,
Z is a direct linkage, O, S, or NR 8 ,
R 6 to R 8 are each independently a hydrogen atom, a deuterium 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, and
a and b are each independently an integer of 0 to 4.

4. The heterocyclic compound of claim 1 , wherein at least one chosen from R 1 to R 4 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring.

5. The heterocyclic compound of claim 4 , wherein at least one chosen from R 1 to R 4 is a substituted or unsubstituted methyl group or a substituted or unsubstituted phenyl group.

6. The heterocyclic compound of claim 1 , wherein D 1 and D 2 are symmetric about A.

7. The heterocyclic compound of claim 6 , wherein X 1 and X 2 are the same.

8. The heterocyclic compound of claim 1 , wherein L 1 and L 2 are each independently represented by one of the following Formulae 8-1 to 8-4:

wherein in Formulae 8-2 and 8-3,
W 1 and W 2 are each independently NR 9 , S, or O, and
R 9 is a hydrogen atom, a deuterium 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.

9. The heterocyclic compound of claim 1 , wherein Y 1 and Y 2 are different from each other.

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

11. An organic electroluminescence device, comprising:
a first electrode;
a hole transport region provided on the first electrode;
an emission layer provided on the hole transport region;
an electron transport region provided on the emission layer; and
a second electrode provided on the electron transport region,
wherein the emission layer comprises a heterocyclic compound represented by the following Formula 1:
D 1 -A-D 2   Formula 1

wherein in Formula 1, A is represented by the following Formula 2, D 1 is represented by the following Formula 3, and D 2 is represented by the following Formula 4:

wherein in Formulae 2 to 4,
q and r are each independently an integer of 0 to 3,
p is 0 or 1,
X 1 and X 2 are each independently CR′ or N,
R′ and R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring,
L 1 and L 2 are each independently 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,
Y 1 and Y 2 are each independently a substituted or unsubstituted arylamine 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 of Y 1 or Y 2 is an electron-donating group,
in case p is 0, Y 1 and Y 2 are each independently represented by the following Formula 5:

wherein in Formula 5,
R 5 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, and
m is an integer of 0 to 6,
wherein the emission layer comprises a host and a dopant and emits near-infrared rays in a wavelength region of about 750 nm to about 1,000 nm, and
wherein the dopant comprises the heterocyclic compound.

12. The organic electroluminescence device of claim 11 , wherein p is 1, and X 1 and X 2 are N.

13. The organic electroluminescence device of claim 11 , wherein a

Assignees

• Samsung Display Co Ltd

Inventors

• Ye Jimyoung
• Kim Myeongsuk
• Kim Seulong
• Yoo Byeongwook
• Hwang Jaehoon
• Ko Soo-Byung
• Yoon Jihwan

Classifications

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• C07D279/18

  [b, e]-condensed with two six-membered rings · CPC title

• C07D265/38

  [b, e]-condensed with two six-membered rings · CPC title

• C07D487/02

  in which the condensed system contains two hetero rings · CPC title

• H10K85/656

  comprising two or more different heteroatoms per ring (H10K85/652 takes precedence) · CPC title