IP Library › Granted Patent US 11,450,821
Granted Patent B2
US 11,450,821 · App. 16/897,744 · Granted Sep 20, 2022

Organic electroluminescence device and polycyclic compound for organic electroluminescence device

Inventors: Yeseul Lee (Busan, KR); Soo-Byung Ko (Yongin-si, KR); Hyeongmin Kim (Suwon-si, KR); HeeChoon Ahn (Seoul, KR); Hyunah Um (Seoul, KR); Yirang Im (Daejeon, KR)
Assignee: SAMSUNG DISPLAY CO., LTD.
H01L51/0074H01L51/0072H01L51/0073H01L51/0094H01L51/5024
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Quick Facts
Patent No.
US 11,450,821
App. No.
16/897,744
Granted
Sep 20, 2022
Kind
B2
Abstract

An organic electroluminescence device comprises a first electrode, a second electrode disposed on the first electrode, and an emission layer disposed between the first electrode and the second electrode. The emission layer comprises a polycyclic compound represented by Formula 1 and achieves high efficiency and a low driving voltage. In Formula 1, at least one of Ar 1 to Ar 4 is represented by Formula 2.

Claims (69)

1. An organic electroluminescence device, comprising:

a first electrode;

a second electrode disposed on the first electrode; and

an emission layer disposed between the first electrode and the second electrode,

wherein the first electrode and the second electrode each independently comprise at least one selected from the group consisting of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, In, Sn, Zn, an oxide thereof, a compound thereof, and a mixture thereof,

wherein the emission layer comprises a polycyclic compound represented by Formula 1:

wherein in Formula 1,

X is O, S, CR 1 R 2 , NR 3 , or SiR 4 R 5 ,

R 1 to R 5 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring,

at least one of Ar 1 to Ar 4 is represented by Formula 2 and the remainder are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, and

m1 to m4 are each independently an integer from 0 to 4, where at least one of m1 to m4 is an integer from 1 to 4:

wherein in Formula 2,

R 6 and R 7 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,

L is a direct linkage, a substituted or unsubstituted divalent alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted arylene group of 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms,

n is 0 or 1,

p is an integer from 0 to 7, and

q is an integer from 0 to 8.

2. The organic electroluminescence device of claim 1 , wherein

Ar 1 to Ar 4 are each independently represented by Formula 2.

3. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by Formula 1-1 to Formula 1-5:

wherein in Formula 1-1 to Formula 1-5,

Ar 1 to Ar 4 are each independently represented by Formula 2.

4. The organic electroluminescence device of claim 1 , wherein Formula 2 is represented by Formula 2-1:

wherein in Formula 2-1,

R 7 and q are the same as defined in Formula 2.

5. The organic electroluminescence device of claim 1 , wherein R 1 to R 5 are each independently substituted or unsubstituted alkyl groups of 1 to 5 carbon atoms, or substituted or unsubstituted phenyl groups.

6. The organic electroluminescence device of claim 1 , wherein R 7 is a hydrogen atom, a t-butyl group, an aryl silyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

7. The organic electroluminescence device of claim 1 , wherein

the emission layer comprises a host and a dopant, and

the host comprises the polycyclic compound.

8. The organic electroluminescence device of claim 7 , wherein the dopant is a phosphorescence dopant, or a thermally activated delayed fluorescence dopant.

9. The organic electroluminescence device of claim 1 , wherein the emission layer emits blue light.

10. The organic electroluminescence device of claim 1 , wherein the emission layer comprises at least one among compounds represented by Compound Group 1:

11. A polycyclic compound represented by Formula 1:

wherein in Formula 1, X is O, S, CR 1 R 2 , NR 3 , or SiR 4 R 5 ,

R 1 to R 5 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring,

at least one of Ar 1 to Ar 4 is represented by Formula 2 and the remainder are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, and

m1 to m4 are each independently an integer from 0 to 4, where at least one of m1 to m4 is an integer from 1 to 4:

wherein in Formula 2,

R 6 and R 7 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,

L is a direct linkage, a substituted or unsubstituted divalent alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted arylene group of 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms,

n is 0 or 1,

p is an integer from 0 to 7, and

q is an integer from 0 to 8.

12. The polycyclic compound of claim 11 , wherein

Ar 1 to Ar 4 are each independently represented by Formula 2.

13. The polycyclic compound of claim 11 , wherein Formula 1 is represented by Formula 1-1 to Formula 1-5:

wherein in Formula 1-1 to Formula 1-5,

Ar 1 to Ar 4 are each independently represented by Formula 2 above.

14. The polycyclic compound of claim 11 , wherein Formula 2 is represented by Formula 2-1:

wherein in Formula 2-1,

R 7 and q are the same as defined in Formula 2.

15. The polycyclic compound of claim 11 , wherein R 1 to R 5 are each independently substituted or unsubstituted alkyl groups of 1 to 5 carbon atoms, or substituted or unsubstituted phenyl groups.

16. The polycyclic compound of claim 11 , wherein R 7 is a hydrogen atom, a t-butyl group, an aryl silyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

17. The polycyclic compound of claim 11 , wherein Formula 1 is any one among compounds represented by Compound Group 1:

18. A polycyclic compound represented by Formula 3:

wherein in Formula 3,

X is O, S, CR 1 R 2 , NR 3 , or SiR 4 R 5 ,

R 1 to R 5 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring,

R 11 and R 12 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,

q11 and q12 are each independently an integer from 0 to 8, and

m11 and m12 are each independently an integer from 0 to 2, where at least one of m11 or m12 is 1 or 2.

19. The polycyclic compound of claim 18 , wherein Formula 3 is represented by Formula 3-1:

wherein in Formula 3-1,

R 21 to R 24 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,

m21 to m24 are each independently 0 or 1, where at least one of m21 to m24 is 1,

q21 to q24 are each independently an integer from 0 to 8, and

X is the same as defined in Formula 3.

20. The polycyclic compound of claim 18 , wherein Formula 3 is any one among compounds represented by Compound Group 1:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 10, 2020
From: LEE, YESEUL; KO, SOO-BYUNG; KIM, HYEONGMIN; AHN, HEECHOON; UM, HYUNAH; IM, YIRANG
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 052897/0476 →
Priority Claims (1)
KR 10-2019-0108817 · Sep 3, 2019 · national
Continuity (1)
Related Publication 20210066620A1 · Mar 4, 2021