IP Library › Granted Patent US 11,758,801
Granted Patent B2
US 11,758,801 · App. 17/176,714 · Granted Sep 12, 2023

Organic electroluminescence device and fused polycyclic compound for organic electroluminescence device

Inventors: Hyoyoung Lee (Suwon-si, KR); Hankyu Pak (Suwon-si, KR); Taeil Kim (Asan-si, KR); Sun Young Pak (Suwon-si, KR); Jang Yeol Baek (Yongin-si, KR); Minjung Jung (Hongcheon-gun, KR)
Assignee: Samsung Display Co., Ltd.
H10K85/322C07F5/027C09K11/06C09K2211/1018H10K50/11H10K50/15H10K50/16H10K50/17H10K2101/10
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Quick Facts
Patent No.
US 11,758,801
App. No.
17/176,714
Granted
Sep 12, 2023
Kind
B2
Abstract

An organic electroluminescence device of an embodiment includes a first electrode facing a second electrode, and a plurality of organic layers between the first electrode and the second electrode, wherein at least one organic layer among the plurality of organic layers includes a fused polycyclic compound represented by Formula 1 below, thereby showing improved emission efficiency.

Claims (101)

1. An organic electroluminescence device, comprising:

a first electrode;

a second electrode facing the first electrode; and

a plurality of organic layers between the first electrode and the second electrode,

wherein at least one organic layer among the plurality of organic layers comprises a fused polycyclic compound represented by the following Formula 1, and

at least one organic layer among the plurality of organic layers comprises an amine compound represented by the following Formula a:

wherein, in Formula 1,

Cy 1 to Cy 7 are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle,

X 1 to X 4 are each independently NR a , O or S,

R a is a substituted or unsubstituted alkyl group of 1 to 20 carbon atom, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms,

Y 1 and Y 2 are each independently BAr 1 ,

Ar 1 is a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, and

m 1 and m 2 are each independently 0 or 1, where at least one selected from among m 1 and m 2 is 1,

wherein, in Formula a,

Ar a to Ar c are each independently a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms.

2. The organic electroluminescence device of claim 1 ,

wherein the plurality of organic layers comprise:

a hole transport region on the first electrode;

an emission layer on the hole transport region; and

an electron transport region on the emission layer, and

the emission layer comprises the fused polycyclic compound represented by Formula 1 above.

3. The organic electroluminescence device of claim 2 ,

wherein the emission layer emits delayed fluorescence.

4. The organic electroluminescence device of claim 2 ,

wherein the emission layer is a delayed fluorescence emission layer comprising a host and a dopant, and

the dopant comprises the fused polycyclic compound represented by Formula 1 above.

5. The organic electroluminescence device of claim 2 ,

wherein the hole transport region comprises:

a hole injection layer on the first electrode; and

a hole transport layer on the hole injection layer, and

the hole transport layer comprises the amine compound represented by Formula a above.

6. The organic electroluminescence device of claim 1 ,

wherein the emission layer is a delayed fluorescence emission layer comprising a host and a dopant, and

the host comprises the fused polycyclic compound represented by Formula 1 above.

7. The organic electroluminescence device of claim 1 , further comprising a capping layer on the second electrode, the capping layer having a refractive index of about 1.6 or more.

8. The organic electroluminescence device of claim 1 ,

wherein the fused polycyclic compound represented by Formula 1 above is represented by the following Formula 2:

wherein, in Formula 2,

R 1 to R 6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a phosphine oxide group, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, or combined with an adjacent group to form a ring,

n 1 to n 4 are each independently an integer in a range of 0 to 4,

n 5 is an integer in a range of 0 to 3,

n 6 is an integer in a range of 0 to 2, and

X 1 to X 4 , Y 1 , Y 2 , R a , Ar 1 m 1 and m 2 are the same as defined in Formula 1.

9. The organic electroluminescence device of claim 8 ,

wherein the fused polycyclic compound represented by Formula 1 above is represented by the following Formula 3-1 to Formula 3-3:

wherein, in Formula 3-1 to Formula 3-3,

R 7 and R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a phosphine oxide group, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, or combined with an adjacent group to form a ring,

n 7 and n 8 are each independently an integer in a range of 0 to 5, and

X 1 to X 4 , R a , R 1 to R 6 , and n 1 to n 6 are the same as defined in Formula 1 and Formula 2.

10. The organic electroluminescence device of claim 8 ,

wherein the fused polycyclic compound represented by Formula 1 above is represented by the following Formula 4-1 to Formula 4-6:

wherein, in Formula 4-1 to 4-6,

R 11 to R 14 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a phosphine oxide group, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, or combined with an adjacent group to form a ring,

n 11 to n 1 are each independently an integer in a range of 0 to 5, and

Y 1 , Y 2 , Ar 1 , R 1 to R 6 , m 1 , m 2 and n 1 to n 6 are the same as defined in Formula 1 and Formula 2.

11. The organic electroluminescence device of claim 8 ,

wherein the fused polycyclic compound represented by Formula 1 above is represented by the following Formula 5:

wherein, in Formula 5,

Ar 2 and Ar 3 are each independently a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, and

X 1 to X 4 , R a , Y 1 , Y 2 , Ar 1 , m 1 and m 2 are the same as defined in Formula 1 and Formula 2.

12. The organic electroluminescence device of claim 1 ,

wherein in Formula 1, when X 1 to X 4 are each independently NR a , R a is a substituted or unsubstituted phenyl group.

13. The organic electroluminescence device of claim 1 ,

wherein in Formula 1, Ar 1 is a substituted or unsubstituted phenyl group.

14. The organic electroluminescence device of claim 1 ,

wherein in Formula 1, when m 1 is 1, X 1 is O or S, and when m 2 is 1, X 2 is O or S.

15. The organic electroluminescence device of claim 1 ,

wherein the fused polycyclic compound comprises at least one selected from among compounds represented in the following Compound Group 1:

16. An organic electroluminescence device comprising:

a first electrode;

a second electrode facing the first electrode; and

a plurality of organic layers between the first electrode and the second electrode,

wherein at least one organic layer among the plurality of organic layers comprises:

a first fused polycyclic compound represented by the following Formula 1, and

a second fused polycyclic compound represented by the following Formula 1, the second fused polycyclic compound being different from the first fused polycyclic compound:

wherein, in Formula 1,

Cy 1 to Cy 7 are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle,

X 1 to X 4 are each independently NR a , O or S,

R a is a substituted or unsubstituted alkyl group of 1 to 20 carbon atom, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms,

Y 1 and Y 2 are each independently BAr 1 ,

Ar 1 is a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, and

m 1 and m 2 are each independently 0 or 1, where at least one selected from among m 1 and m 2 is 1.

17. The organic electroluminescence device of claim 16 ,

wherein the plurality of organic layers comprise:

a hole transport region on the first electrode;

an emission layer on the hole transport region; and

an electron transport region on the emission layer, and

the emission layer comprises the first fused polycyclic compound and the second fused polycyclic compound.

18. The organic electroluminescence device of claim 17 ,

wherein the emission layer is a delayed fluorescence emission layer comprising a host and a dopant,

the host comprises the first fused polycyclic compound, and the dopant comprises the second fused polycyclic compound.

19. The organic electroluminescence device of claim 16 ,

wherein the fused polycyclic compound represented by Formula 1 above is represented by the following Formula 2:

wherein, in Formula 2,

R 1 to R 6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a phosphine oxide group, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, or combined with an adjacent group to form a ring,

n 1 to n 4 are each independently an integer in a range of 0 to 4,

n 5 is an integer in a range of 0 to 3,

n 6 is an integer in a range of 0 to 2, and

X 1 to X 4 , Y 1 , Y 2 , R a , Ar 1 m 1 and m 2 are the same as defined in Formula 1.

20. The organic electroluminescence device of claim 16 ,

wherein the fused polycyclic compound represented by Formula 1 above has an absolute value of a difference between the lowest singlet excitation energy level (S1) and the lowest triplet excitation energy level (T1) of about 0.33 eV or less.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 16, 2021
From: LEE, HYOYOUNG; PAK, HANKYU; KIM, TAEIL; PAK, SUN YOUNG; BAEK, JANG YEOL; JUNG, MINJUNG
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 055274/0306 →
Priority Claims (1)
KR 10-2020-0070836 · Jun 11, 2020 · national
Continuity (1)
Related Publication 20210391540A1 · Dec 16, 2021