Polycyclic compound and organic electroluminescence device including the same

Patent metadata

Field	Value
Publication number	US-10886476-B2
Application number	US-201816164650-A
Country	US
Kind code	B2
Filing date	Oct 18, 2018
Priority date	Oct 24, 2017
Publication date	Jan 5, 2021
Grant date	Jan 5, 2021

Abstract

A polycyclic compound may be represented by Formula 1 below. The polycyclic compound may improve the light emitting efficiency of a blue light emitting region, and an organic electroluminescence device including the polycyclic compound may have improved blue light emission, high external quantum efficiency, and long life. The polycyclic compound may be used as a thermally activated delayed fluorescence material, which emits blue light, to improve the blue light emitting efficiency of the organic electroluminescence device.

First claim

What is claimed is:

1. A polycyclic compound represented by Formula 1 below:

wherein in Formula 1,
X 1 to X 24 are each independently CR 10 or N;
at least one of X 1 to X 8 and at least one of X 9 to X 16 is N;
R 1 to R 9 are each independently selected from hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms;
R 10 is selected from hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; and
n is 0 or 1.

2. The polycyclic compound of claim 1 , wherein the polycyclic compound of Formula 1 is represented by Formula 1-1 below or Formula 1-2 below:

wherein in Formula 1-1 and Formula 1-2,
X 1 to X 24 , and R 1 to R 10 are the same as defined in Formula 1.

3. The polycyclic compound of claim 1 , wherein at least two of X 1 to X 8 and at least two of X 9 to X 16 are N.

4. The polycyclic compound of claim 1 , wherein when n is 1, at least one of X 17 to X 24 is N.

5. The polycyclic compound of claim 1 , wherein when n is 1, at least two of X 17 to X 24 are N.

6. The polycyclic compound of claim 1 , wherein at least two of X 1 , X 2 , X 9 or X 10 are N.

7. The polycyclic compound of claim 1 , wherein X 1 , X 2 , X 9 and X 10 are each N.

8. The polycyclic compound of claim 1 , wherein when n is 1, at least one of X 17 or X 18 is N.

9. The polycyclic compound of claim 1 , wherein R 1 to R 9 are each hydrogen.

10. The polycyclic compound of claim 1 , wherein R 10 is an unsubstituted methyl group or a methyl group substituted with a cyano group or a fluorine atom.

11. The polycyclic compound of claim 1 , wherein the polycyclic compound of Formula 1 is one selected from Compounds 1 to 24, collectively denoted as Compound Group 1:

12. An organic electroluminescence device comprising:
a first electrode;
a hole transport region on the first electrode;
a light emitting layer on the hole transport region;
an electron transport region on the light emitting layer; and
a second electrode on the electron transport region,
wherein the first electrode and the second electrode each independently comprise at least one selected from AQ, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/AI, Mo, Ti, In, Sn, and Zn, a compound of two or more thereof, a mixture of two or more thereof, and an oxide of one or more thereof,
wherein the light emitting layer comprises a polycyclic compound represented by Formula 1:

wherein in Formula 1,
X 1 to X 24 are each independently CR 10 or N;
at least one of X 1 to X 8 and at least one of X 9 to X 16 is N;
R 1 to R 9 are each independently selected from hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms;
R 10 is selected from hydrogen, deuterium, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; and
n is 0 or 1.

13. The organic electroluminescence device of claim 12 , wherein the light emitting layer is for emitting blue light.

14. The organic electroluminescence device of claim 12 , wherein the light emitting layer is a fluorescent light emitting layer comprising a host and a dopant, and the dopant comprises the polycyclic compound represented by Formula 1.

15. The organic electroluminescence device of claim 12 , wherein the polycyclic compound represented by Formula 1 is a thermally activated delayed fluorescence compound.

16. The organic electroluminescence device of claim 12 , wherein the polycyclic compound represented by Formula 1 is a thermally activated delayed fluorescence dopant.

17. The organic electroluminescence device of claim 12 , wherein, in the polycyclic compound represented by Formula 1, an absolute value of a difference between a singlet energy level and a triplet energy level is 0.2 eV or less.

18. The organic electroluminescence device of claim 12 , wherein at least two of X 1 to X 8 and at least two of X 9 to X 16 are N.

19. The organic electroluminescence device of claim 12 , wherein when n is 1, at least one of X 17 to X 24 is N.

20. The organic electroluminescence device of claim 12 , wherein at least two of X 1 , X 2 , X 9 or X 10 are N.

21. The organic electroluminescence device of claim 12 , wherein the light emitting layer comprises at least one of Compounds 1 to 24, collectively denoted as Compound Group 1:

Assignees

• Samsung Display Co Ltd

Inventors

• FUCHIWAKI Junta
• Akashi Nobutaka

Classifications

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K85/6572

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

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C07D471/20 Primary

  Spiro-condensed systems · CPC title