IP Library › Granted Patent US 11,980,091
Granted Patent B2
US 11,980,091 · App. 17/023,189 · Granted May 7, 2024

Organic electroluminescence device and compound for organic electroluminescence device

Inventors: Dongchan Lee (Sejong-si, KR); Eu-gene Oh (Seoul, KR); SeulOng Kim (Hwaseong-si, KR); Yunjee Park (Asan-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.
H10K85/657C07D498/04C07D513/04C09K11/02C09K11/06H10K85/636H10K85/6572C09K2211/1007C09K2211/1018H10K50/11H10K2101/10
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Quick Facts
Patent No.
US 11,980,091
App. No.
17/023,189
Granted
May 7, 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, and the emission layer includes a compound represented by Formula 1 below, and thus the organic electroluminescence device may exhibit high luminous efficiency characteristics and improved service life characteristics.

Claims (87)

1. An organic electroluminescence device comprising:

a first electrode;

a second electrode on the first electrode; and

an emission layer which is between the first electrode and the second electrode and includes a compound represented by the following Formula 1:

in Formula 1,

at least one selected from among X 2 to X 4 is N, the rest are CR a , or each of X 1 and X 4 among X 1 to X 4 is N, the rest are CR a ,

Y is O or S,

n is 1 or 2,

L is an unsubstituted phenylene or an unsubstituted pyridinylene,

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 having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or is combined with an adjacent group to form a ring, and

Ar is represented by the following Formula 2:

in Formula 2,

W 1 to W 8 are each independently N or CR b ,

Z is a direct linkage, O, or CR c R d , and

R b to R d 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 having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or are combined with an adjacent group to form a ring.

2. The organic electroluminescence device of claim 1 ,

wherein Formula 1 above is represented by the following Formula 1-1 or Formula 1-2 below:

in Formula 1-1 and Formula 1-2, X 1 to X 4 , L, n, Z, and W 1 to W 8 are the same as those defined with respect to Formula 1 and Formula 2.

3. The organic electroluminescence device of claim 1 ,

wherein Formula 2 is represented by any one selected from the following Formula 2-1 to Formula 2-4 below:

in Formula 2-4,

R e is a hydrogen atom, a deuterium atom, a halogen atom, 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,

W 9 to W 12 are each independently N or CR f ,

R f 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 having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or are combined with an adjacent group to form a ring, and

in Formula 2-1 to Formula 2-4, W 1 to W 8 are the same as those defined with respect to Formula 2.

4. The organic electroluminescence device of claim 1 ,

wherein Ar is represented by any one selected from the following Ar-1 to Ar-6:

in Ar-3, m1 and m2 are each independently 0 or 1, and

R b1 and R b2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring.

5. The organic electroluminescence device of claim 1 ,

wherein L is represented by any one selected from the following L-1 and L-2

6. The organic electroluminescence device of claim 1 ,

wherein the emission layer comprises a host and a dopant, and

the host comprises the compound.

7. The organic electroluminescence device of claim 1 ,

wherein the emission layer emits a delayed fluorescence, and

the compound is a delayed fluorescence dopant.

8. The organic electroluminescence device of claim 1 ,

wherein the emission layer emits light having a center wavelength of 500 nm or more and 550 nm or less, or light having a center wavelength of 450 nm or more and less than 500 nm.

9. The organic electroluminescence device of claim 1 ,

wherein the emission layer comprises at least one selected from compounds represented in the following Compound Group 1 and Compound Group 2:

Compound Group 1

Compound Group 2

10. A compound represented by the following Formula 1:

in Formula 1,

at least one selected from among X 2 to X 4 is N, the rest are CR a , or each of X 1 and X 4 among X 1 to X 4 is N, the rest are CR a ,

Y is O or S,

n is 1 or 2,

L is an unsubstituted phenylene or an unsubstituted pyridinylene,

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 having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or is combined with an adjacent group to form a ring, and

Ar is represented by Formula 2 below:

in Formula 2,

W 1 to W 8 are each independently N or CR b ,

Z is a direct linkage, O, or CR c R d , and

R b to R d 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 having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or are combined with an adjacent group to form a ring.

11. The compound of claim 10 ,

wherein Formula 1 above is represented by the following Formula 1-1 or Formula 1-2:

in Formula 1-1 and Formula 1-2, X 1 to X 4 , L, n, Z, and W 1 to W 8 are the same as those defined with respect to Formula 1 and Formula 2 above.

12. The compound of claim 10 ,

wherein any one selected from among X 1 to X 4 is N, the rest are CR a , or

each of X 1 and X 4 among X 1 to X 4 is N, the rest are CR a , and

R a is a hydrogen atom, or represented by any one selected from the following R a -1 to R a -4:

13. The compound of claim 10 ,

wherein Formula 2 is represented by any one selected from the following Formula 2-1 to Formula 2-4:

in Formula 2-4,

R e is a hydrogen atom, a deuterium atom, a halogen atom, 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,

W 9 to W 12 are each independently N or CR f ,

R f 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 having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or are combined with an adjacent group to form a ring, and

in Formula 2-1 to Formula 2-4, W 1 to W 8 are the same as those defined with respect to Formula 2 above.

14. The compound of claim 10 ,

wherein Ar is represented by any one selected from the following Ar-1 to Ar-6:

in Ar-3, m1 and m2 are each independently 0 or 1, and

R b1 and R b2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring.

15. The compound of claim 10 ,

wherein L is represented by any one selected from the following L-1 and L-2:

16. The compound of claim 10 ,

wherein the compound represented by Formula 1 is a green dopant to emit green light having a center wavelength of 500 nm or more and 550 nm or less.

17. The compound of claim 10 ,

wherein the compound represented by Formula 1 is a blue dopant to emit blue light having a center wavelength of 450 nm or more and less than 500 nm.

18. The compound of claim 10 ,

wherein the compound represented by Formula 1 is a host material.

19. The compound of claim 10 ,

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

20. The compound of claim 10 ,

wherein the compound represented by Formula 1 is represented by any one selected from compounds represented in the following Compound Group 1 or Compound Group 2:

Compound Group 1

Compound Group 2

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2020
From: LEE, DONGCHAN; OH, EU-GENE; KIM, SEULONG; PARK, YUNJEE; KIM, MUNSOO; MAENG, JUWAN; HAN, KAP-JONG
To: SAMSUNG DISPLAY CO., LTD.; LAPTO CO., LTD.
Reel/Frame 053794/0657 →
Priority Claims (1)
KR 10-2019-0121044 · Sep 30, 2019 · national
Continuity (1)
Related Publication 20210098711A1 · Apr 1, 2021