IP Library › Granted Patent US 11,877,512
Granted Patent B2
US 11,877,512 · App. 17/028,938 · Granted Jan 16, 2024

Organic electroluminescence device and compound for organic electroluminescence device

Inventors: SeulOng Kim (Hwaseong-si, KR); Eu Gene Oh (Seoul, KR); Hyein Jeong (Suwon-si, KR); Seung-Jin Chu (Gwangmyeong-si, KR); Munsoo Kim (Seongnam-si, KR); Juwan Maeng (Seongnam-si, KR); Kap Jong Han (Gwangju-si, KR)
Assignees: Samsung Display Co., Ltd.; Lapto Co., Ltd.
H10K85/656C07D498/04C07D519/00C07F5/027C09K11/06H10K85/324H10K85/636H10K85/654C09K2211/1033H10K50/12
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Quick Facts
Patent No.
US 11,877,512
App. No.
17/028,938
Granted
Jan 16, 2024
Kind
B2
Abstract

An organic electroluminescence device of an embodiment includes a first electrode, a second electrode, and an emission layer between the first electrode and the second electrode, wherein the emission layer includes a compound represented by Formula 1, thereby showing excellent emission efficiency properties and long-life characteristics:

Claims (57)

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, the emission layer comprising a compound represented by Formula 1:

in Formula 1,

X 1 to X 4 are each independently CR a ,

L is a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring,

“n” is 1 or 2,

Ar is a substituted or unsubstituted aryl group of 6 to 15 carbon atoms for forming a ring, or represented by Formula 2:

in Formula 2,

Y is N or B,

Z is a direct linkage, O, S, NR d , or CR e R f ,

“b” and “c” are each independently an integer of 0 to 4, and

R b to R f are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, 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, and/or combined with an adjacent group to form a ring, and

R a is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, 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, and/or combined with an adjacent group to form a ring.

2. The organic electroluminescence device of claim 1 , wherein L is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted pyridylene group.

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

in Formula 2-1 and Formula 2-2, Z, R b , R c , “b”, and “c” are the same as defined in Formula 2.

4. The organic electroluminescence device of claim 3 , wherein Formula 2-2 is represented by any one selected from among Formula 2-2A to Formula 2-2E:

in Formula 2-2E,

“b1” is an integer of 0 to 3, “b2” is an integer of 0 to 4, and

R b1 and R b2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, 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, and/or combined with an adjacent group to form a ring, and

in Formula 2-2A to Formula 2-2E, R b , R c , “b”, and “c” are the same as defined in Formula 2.

5. The organic electroluminescence device of claim 1 , wherein the emission layer comprises a host and a dopant, and

the host comprises the compound.

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

the compound is a delayed fluorescence dopant.

7. The organic electroluminescence device of claim 1 , wherein the emission layer is to emit light having a central wavelength of about 500 nm to about 550 nm, or light having a central wavelength of about 420 nm to about 470 nm.

8. 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, wherein the emission layer comprises at least one selected from among compounds in Compound Group 1 as a light-emitting dopant:

9. A compound represented by Formula 1:

in Formula 1,

X 1 to X 4 are each independently CR a ,

L is a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring,

“n” is 1 or 2,

Ar is a substituted or unsubstituted aryl group of 6 to 15 carbon atoms for forming a ring, or represented by Formula 2:

in Formula 2,

Y is N or B,

Z is a direct linkage, O, S, NR d , or CR e R f ,

“b” and “c” are each independently an integer of 0 to 4, and

R b to R f are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, 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, and/or combined with an adjacent group to form a ring, and

R a is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, 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, and/or combined with an adjacent group to form a ring.

10. The compound of claim 9 , wherein Formula 1 is represented by Formula 1-1:

in Formula 1-1, L, “n”, and Ar are the same as defined in Formula 1.

11. The compound of claim 9 , wherein Formula 2 is represented by Formula 2-1 or Formula 2-2:

in Formula 2-1 and Formula 2-2, Z, R b , R c , “b”, and “c” are the same as defined in Formula 2.

12. The compound of claim 11 , wherein Formula 2-2 is represented by any one selected from among Formula 2-2A to Formula 2-2E:

in Formula 2-2E,

“b1” is an integer of 0 to 3, “b2” is an integer of 0 to 4, and

R b1 and R b2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, 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, and/or combined with an adjacent group to form a ring, and

in Formula 2-2A to Formula 2-2E, R b , R c , “b”, and “c” are the same as defined in Formula 2.

13. The compound of claim 9 , wherein the compound represented by Formula 1 is a green dopant to emit green light having a central wavelength of about 500 nm to about 550 nm.

14. The compound of claim 9 , wherein the compound represented by Formula 1 is a blue dopant to emit blue light having a central wavelength of about 420 nm to about 470 nm.

15. The compound of claim 9 , wherein the compound represented by Formula 1 has an absolute value (ΔE ST ) of a difference between a lowest excitation singlet energy level (S1) and a lowest excitation triplet energy level (T1) of about 0.2 eV or less.

16. The compound of claim 9 , wherein the compound represented by Formula 1 is represented by any one selected from among compounds in Compound Group 1:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2020
From: KIM, SEULONG; OH, EU GENE; JEONG, HYEIN; CHU, SEUNG-JIN; KIM, MUNSOO; MAENG, JUWAN; HAN, KAP JONG
To: SAMSUNG DISPLAY CO., LTD.; LAPTO CO., LTD.
Reel/Frame 053851/0261 →
Priority Claims (1)
KR 10-2019-0121047 · Sep 30, 2019 · national
Continuity (1)
Related Publication 20210098708A1 · Apr 1, 2021