IP Library Granted Patent US 11,997,924
Granted Patent B2
US 11,997,924 · App. 16/795,199 · Granted May 28, 2024

Organic compound and organic electroluminescent element comprising same

Inventors: Min-Sik Eum (Seoul, KR); Hojun Son (Yongin-si, KR); Woo Jae Park (Seoul, KR); Tae Hyung Kim (Yongin-si, KR); Jiyi Kim (Yongin-si, KR); Youngmi Beak (Yongin-si, KR)
Assignee: SOLUS ADVANCED MATERIALS CO., LTD.
H10K85/654C07D213/16C07D239/26C07D251/24C09K11/025C09K11/06H10K50/11H10K85/342H10K85/615H10K85/622H10K85/623H10K85/624H10K85/631H10K85/636H10K85/6572C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/185H10K50/16H10K50/166H10K50/171H10K50/80H10K2101/10H10K2101/30H10K2101/40
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,997,924
App. No.
16/795,199
Granted
May 28, 2024
Kind
B2
Abstract

Disclosed are a novel organic compound, and an organic electroluminescent element having improved characteristics, such as luminous efficiency, driving voltage, and lifespan, by containing the novel organic compound in one or more organic material layers.

Claims (36)

1. An organic electroluminescent element comprising, in the order,

an anode,

a hole injection layer,

a hole transport layer,

a light emitting layer;

an auxiliary electron transport layer;

an electron transport layer;

an electron injection layer; and

a cathode,

wherein the auxiliary electron transport layer, the electron transport layer, and the electron injection layer are different from each other, and

wherein the auxiliary electron transport layer comprises a compound of the following Formula 5:

wherein,

R a and R b are the same or different from each other and are each independently a C 1 -C 40 alkyl group or a C 6 -C 60 aryl group,

R 1 and R 2 are the same or different from each other and are each independently selected from the group consisting of a hydrogen, a deuterium, a halogen, a cyano group, a nitro group, an amino group, a C 1 -C 40 alkyl group, a C 2 -C 40 alkenyl group, a C 2 -C 40 alkynyl group, a C 3 -C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 -C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 -C 40 alkyloxy group, a C 6 -C 60 aryloxy group, a C 1 -C 40 alkylsilyl group, a C 6 -C 60 arylsilyl group, a C 1 -C 40 alkylboron group, a C 6 -C 60 arylboron group, a C 1 -C 40 phosphine group, a C 1 -C 40 phosphine oxide group, and a C 6 -C 60 arylamine group, or adjacent ones of R 1 and R 2 are optionally respectively to each other to form a fused ring,

R 3 is a hydrogen,

L is selected from the group consisting of a single bond, phenylene, and a heteroarylene group having 5 to 18 nuclear atoms,

c and e are each an integer of 0 to 4,

d is an integer of 0 to 3,

m and n are each 1, and

R 4 is selected from the group consisting of a hydrogen, a deuterium, a halogen, a cyano group, a nitro group, an amino group, a C 1 -C 40 alkyl group, a C 2 -C 40 alkenyl group, a C 2 -C 40 alkynyl group, a C 3 -C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 -C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 -C 40 alkyloxy group, a C 6 -C 60 aryloxy group, a C 1 -C 40 alkylsilyl group, a C 6 -C 60 arylsilyl group, a C 1 -C 40 alkylboron group, a C 6 -C 60 arylboron group, a C 1 -C 40 phosphine group, a C 1 -C 40 phosphine oxide group, and a C 6 -C 60 arylamine group,

wherein the alkyl and aryl groups of R a and R b , the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkyloxy, aryloxy, alkylsilyl, arylsilyl, alkylboron, arylboron, phosphine, phosphine oxide, and arylamine groups of R 1 , R 2 , and R 4 are optionally each independently unsubstituted or substituted with one or more substituents selected from the group consisting of a deuterium, a halogen, a cyano group, a nitro group, an amino group, a C 1 -C 40 alkyl group, a C 2 -C 40 alkenyl group, a C 2 -C 40 alkynyl group, a C 3 -C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 -C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 -C 40 alkyloxy group, a C 6 -C 60 aryloxy group, a C 1 -C 40 alkylsilyl group, a C 6 -C 60 arylsilyl group, a C 1 -C 40 alkylboron group, a C 6 -C 60 arylboron group, a C 1 -C 40 phosphine group, a C 1 -C 40 phosphine oxide group, and a C 6 -C 60 arylamine group, provided that when the substituents are present in a plural number, the substituents are the same or different from each other,

with the proviso that compound of the following formula is excluded:

2. The organic electroluminescent element of claim 1 , wherein L is selected from the group consisting of the structures represented by the following L-1 or L-2:

wherein * is a site where to bond.

3. The organic electroluminescent element of claim 1 , wherein the compound of Formula 5 is selected from the group consisting of the following Compounds 1 to 4, 70 to 72:

4. An organic electroluminescent element comprising, in the order,

an anode,

a hole injection layer;

a hole transport layer;

a light emitting layer;

an auxiliary electron transport layer;

an electron transport layer;

an electron injection layer; and

a cathode,

wherein the auxiliary electron transport layer, the electron transport layer, and the electron injection layer are different from each other, and

the auxiliary electron transport layer comprises a compound selected from the group consisting o the following Compounds 22, 24, 25, 27 to 28, 65, 67, 90, 92 to 96, 190, 198, 225, 235:

Assignments (2)
CHANGE OF NAME Recorded Dec 29, 2020
From: DOOSAN SOLUS CO., LTD.
To: SOLUS ADVANCED MATERIALS CO., LTD.
Reel/Frame 054867/0169 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 16, 2020
From: DOOSAN CORPORATION
To: DOOSAN SOLUS CO., LTD.
Reel/Frame 052128/0274 →