IP Library › Granted Patent US 11,839,150
Granted Patent B2
US 11,839,150 · App. 17/029,987 · Granted Dec 5, 2023

Organic electroluminescence device and condensed cyclic compound for organic electroluminescence device

Inventor: Yuji Suzaki (Yokohama, JP)
Assignee: Samsung Display Co., Ltd.
H10K85/631C07F5/027C09K11/06H10K85/636C09K2211/1007C09K2211/1018H10K50/11H10K85/657H10K85/6572H10K85/6574H10K2101/10
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Quick Facts
Patent No.
US 11,839,150
App. No.
17/029,987
Granted
Dec 5, 2023
Kind
B2
Abstract

An organic electroluminescence device includes a first electrode, a second electrode, and an emission layer disposed between the first electrode and the second electrode, wherein the emission layer includes a condensed cyclic compound represented by Formula 1, and the organic electroluminescence device exhibits high efficiency characteristics.

Claims (56)

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 and comprising a condensed cyclic compound represented by Formula 1,

wherein the first electrode and the second electrode each independently comprise any one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF Mo, Ti, In, Zn, Sn, and Yb, a compound of two or more thereof, a mixture of two or more thereof, or an oxide thereof:

and

wherein in Formula 1,

X 1 to X 6 are each independently a direct linkage, BAr 3 , NAr 4 , O, or S,

Ar 1 to Ar 4 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,

l, m, and n are each independently 0 or 1, at least one of l, m, or n is 1,

a to g are each independently an integer of 0 to 4, and

R 1 to R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or are bonded to an adjacent group to form a ring.

2. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by any one among Formula 1-1 to Formula 1-3:

and

wherein in Formula 1-1 to Formula 1-3, X 1 to X 6 , Ar 1 , Ar 2 , l, m, n, a to g, and R 1 to R 8 are each independently the same as defined in Formula 1.

3. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by any one among Formula 1-A to Formula 1-E:

and

wherein in Formula 1-A to Formula 1-E, X 1 to X 6 , Ar 1 , Ar 2 , a to g, and R 1 to R 8 are each independently the same as defined in Formula 1.

4. The organic electroluminescence device of claim 1 , wherein Ar 1 to Ar 4 are each independently an unsubstituted phenyl group, a phenyl group substituted with a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a phenyl group substituted with a deuterium atom.

5. The organic electroluminescence device of claim 1 , wherein R 1 to R 8 are each a deuterium atom.

6. The organic electroluminescence device of claim 1 , wherein the emission layer is to emit delayed fluorescence.

7. The organic electroluminescence device of claim 1 , wherein the emission layer comprises a host and a dopant, and the dopant comprises the condensed cyclic compound.

8. The organic electroluminescence device of claim 1 , wherein the emission layer to emit light having a center wavelength of about 460 nm to about 490 nm.

9. The organic electroluminescence device of claim 1 , wherein the emission layer comprises at least one selected from the condensed cyclic compounds represented by Compound Group 1:

10. A condensed cyclic compound represented by Formula 1:

wherein in Formula 1,

X 1 to X 6 are each independently a direct linkage, BAr 3 , NAr 4 , O, or S,

Ar 1 to Ar 4 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,

l, m, and n are each independently 0 or 1, at least one of l, m, or n is 1,

a to g are each independently an integer of 0 to 4, and

R 1 to R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or are bonded to an adjacent group to form a ring.

11. The condensed cyclic compound of claim 10 , wherein Formula 1 is represented by any one selected from Formula 1-1 to Formula 1-3:

and

wherein in Formula 1-1 to Formula 1-3, X 1 to X 6 , Ar 1 , Ar 2 , l, m, n, a to g, and R 1 to R 8 are each independently the same as defined in Formula 1.

12. The condensed cyclic compound of claim 10 , wherein Formula 1 is represented by any one selected from Formula 1-A to Formula 1-E:

and

wherein in Formula 1-A to Formula 1-E, X 1 to X 6 , Ar 1 , Ar 2 , a to g, and R 1 to R 8 are each independently the same as defined in Formula 1.

13. The condensed cyclic compound of claim 10 , wherein Ar 1 to Ar 4 are each independently an unsubstituted phenyl group, a phenyl group substituted with a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a phenyl group substituted with a deuterium atom.

14. The condensed cyclic compound of claim 10 , wherein R 1 to R 8 are each a deuterium atom.

15. The condensed cyclic compound of claim 10 , wherein Formula 1 is any one selected from the compounds represented by Compound Group 1:

16. A condensed cyclic compound represented by Formula 1A:

wherein in Formula 1A,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,

l, m, and n are each independently 0 or 1, at least one of l, m, or n is 1,

d to g are each independently an integer of 0 to 4,

R 1 to R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or are bonded to an adjacent group to form a ring, and

HAr 1 to HAr 3 are each independently represented by any one selected from 2-A to 2-J:

Ar 3 and Ar 4 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,

r is an integer of 0 to 4,

R a is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring, and

“—*” is a part bonded to Formula 1.

17. The condensed cyclic compound of claim 16 , wherein Formula 1A is represented by any one selected from Formula 1A-1 to Formula 1A-5:

and

wherein in Formulae 1A-1 to 1A-5,

Ar 1 , Ar 2 , d to g, and R 4 to R 8 are each independently the same as defined in Formula 1A, and HAr 1 to HAr 3 are each independently the same as defined in 2-A to 2-J.

18. The condensed cyclic compound of claim 16 , wherein Ar 1 to Ar 4 are each independently an unsubstituted phenyl group, a phenyl group substituted with a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a phenyl group substituted with a deuterium atom.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 23, 2020
From: SUZAKI, YUJI
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 053863/0149 →
Priority Claims (1)
KR 10-2020-0034066 · Mar 19, 2020 · national
Continuity (1)
Related Publication 20210305512A1 · Sep 30, 2021