IP Library › Granted Patent US 11,787,822
Granted Patent B2
US 11,787,822 · App. 17/013,405 · Granted Oct 17, 2023

Aromatic compound and organic electroluminescence device including the same

Inventors: Heechoon Ahn (Suwon-si, KR); Soo-byung Ko (Yongin-si, KR); Mieun Jun (Hwaseong-si, KR); Sungbum Kim (Yongin-si, KR); Mina Jeon (Suwon-si, KR); Youngkook Kim (Suwon-si, KR); Seokhwan Hwang (Suwon-si, KR)
Assignee: Samsung Display Co., Ltd.
C07F7/0816C09K11/06H10K50/12H10K50/15H10K50/16H10K85/40H10K85/657C09K2211/104C09K2211/107C09K2211/1055C09K2211/1096H10K50/11
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Quick Facts
Patent No.
US 11,787,822
App. No.
17/013,405
Granted
Oct 17, 2023
Kind
B2
Abstract

An aromatic compound which improves emission efficiency and an organic electroluminescence device including the same are provided. The organic electroluminescence device includes: a first electrode; a second electrode opposite to the first electrode; and a plurality of organic layers between the first electrode and the second electrode, where at least one organic layer among the plurality of organic layers includes the aromatic compound. The aromatic compound is represented by Formula 1 below.

Claims (68)

1. An aromatic compound represented by Formula 1:

wherein in Formula 1,

R a to R d are each independently a hydrogen atom, a deuterium atom, a halogen atom, 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 5 to 30 ring-forming carbon atoms,

R 1 to R 3 are each independently represented by Formula 2, or a hydrogen atom, wherein at least one of R 1 to R 3 is represented by Formula 2,

X is O or S,

n a , n c , and n d are each independently an integer of 0 to 4, and

n b is an integer of 0 to 3:

wherein in Formula 2,

Y 1 to Y 3 are each independently CR 4 or N,

L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 5 to 11 carbon atoms for forming a ring,

R 4 is a hydrogen atom, a deuterium atom, a halogen atom, 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 5 to 30 ring-forming carbon atoms,

Ar 1 and Ar 2 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming carbon atoms, or represented by Formula 4, wherein at least one of Ar 1 or Ar 2 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, or represented by Formula 4:

wherein in Formula 4,

R e to R h are each independently a hydrogen atom, a deuterium atom, a halogen atom, 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 5 to 30 ring-forming carbon atoms,

R 5 to R 7 are each independently a position to be connected to Formula 2, or a hydrogen atom, wherein at least one of R 5 to R 7 is a position to be connected to Formula 2,

Z 4 is O or S,

n e , n g , and n h are each independently an integer of 0 to 4, and

n f is an integer of 0 to 3.

2. The aromatic compound of claim 1 , wherein R a to R d are each independently a hydrogen atom.

3. The aromatic compound of claim 1 , wherein R e to R h are each independently a hydrogen atom.

4. The aromatic compound of claim 1 , wherein L is a direct linkage, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted heteroarylene group containing N as a heteroatom.

5. The aromatic compound of claim 1 , wherein the aromatic compound represented by Formula 1 is represented by Formula 1-1 or Formula 1-2:

wherein in Formula 1-1 and Formula 1-2,

X, L, Y 1 to Y 3 , Ar 1 , Ar 2 , R a to R d , n a to n d are the same as respectively defined in Formulae 1 and 2.

6. The aromatic compound of claim 1 , wherein a moiety represented by Formula 4 is represented by Formula 4-1:

wherein in Formula 4,

—* is a position to be connected to Formula 2,

Z 4 , R e to R h , n e to n h are the same as respectively defined in Formula 4.

7. The aromatic compound of claim 1 , wherein the aromatic compound represented by Formula 1 is one selected from compounds represented in Compound Group 1:

8. An aromatic compound represented by Formula 1:

wherein in Formula 1,

R a to R d are each independently a hydrogen atom, a deuterium atom, a halogen atom, 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 5 to 30 ring-forming carbon atoms,

R 1 to R 3 are each independently represented by Formula 2, or a hydrogen atom, wherein at least one of R 1 to R 3 is represented by Formula 2,

X is O or S,

n a , n c , and n d are each independently an integer of 0 to 4, and

n b is an integer of 0 to 3:

wherein in Formula 2,

Y 1 to Y 3 are each independently CR 4 or N,

L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 5 to 11 carbon atoms for forming a ring,

R 4 is a hydrogen atom, a deuterium atom, a halogen atom, 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 5 to 30 ring-forming carbon atoms,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, or represented by Formula 4:

wherein in Formula 4,

R e to R h are each independently a hydrogen atom, a deuterium atom, a halogen atom, 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 5 to 30 ring-forming carbon atoms,

R 5 to R 7 are each independently a position to be connected to Formula 2, or a hydrogen atom, wherein at least one of R 5 to R 7 is a position to be connected to Formula 2,

Z 4 is O or S,

n e , n g , and n h are each independently an integer of 0 to 4, and

n f is an integer of 0 to 3.

9. An organic electroluminescence device, comprising:

a first electrode;

a second electrode opposite to the first electrode; and

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

wherein at least one organic layer from among the plurality of organic layers comprises an aromatic compound represented by Formula 1:

wherein in Formula 1,

R a to R d are each independently a hydrogen atom, a deuterium atom, a halogen atom, 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 5 to 30 ring-forming carbon atoms,

R 1 to R 3 are each independently represented by Formula 2, or a hydrogen atom, wherein at least one of R 1 to R 3 is represented by Formula 2,

X is O or S,

n a , n c , and n d are each independently an integer of 0 to 4, and

n b is an integer of 0 to 3:

wherein in Formula 2,

Y 1 to Y 3 are each independently CR 4 or N,

L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 5 to 11 carbon atoms for forming a ring,

R 4 is a hydrogen atom, a deuterium atom, a halogen atom, 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 5 to 30 ring-forming carbon atoms,

Ar 1 and Ar 2 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming carbon atoms, or represented by Formula 4, wherein at least one of Ar 1 or Ar 2 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, or represented by Formula 4:

wherein in Formula 4,

R e to R h are each independently a hydrogen atom, a deuterium atom, a halogen atom, 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 5 to 30 ring-forming carbon atoms,

R 5 to R 7 are each independently a position to be connected to Formula 2, or a hydrogen atom, wherein at least one of R 5 to R 7 is a position to be connected to Formula 2,

Z 4 is O or S,

n e , n g , and n h are each independently an integer of 0 to 4, and n f is an integer of 0 to 3.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 16, 2020
From: AHN, HEECHOON; KO, SOO-BYUNG; JUN, MIEUN; KIM, SUNGBUM; JEON, MINA; KIM, YOUNGKOOK; HWANG, SEOKHWAN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 054379/0349 →
Priority Claims (1)
KR 10-2017-0122057 · Sep 21, 2017 · national
Continuity (2)
Continuation 15958642 · Apr 20, 2018
Related Publication 20200399289A1 · Dec 24, 2020