IP Library Granted Patent US 11,725,138
Granted Patent B2
US 11,725,138 · App. 17/111,339 · Granted Aug 15, 2023

Organic electroluminescent compound and organic electroluminescent device comprising the same

Inventors: Hyun Kim (Gyeonggi-do, KR); Ji-Won Um (Gyeonggi-do, KR); Kyoung-Jin Park (Gyeonggi-do, KR); Mi-Ja Lee (Gyeonggi-do, KR); Chi-Sik Kim (Gyeonggi-do, KR)
C09K11/06C07D413/14C09K2211/1018
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 11,725,138
App. No.
17/111,339
Granted
Aug 15, 2023
Kind
B2
Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound according to the present disclosure, it is possible to provide an organic electroluminescent device having improved driving voltage, luminous efficiency, lifetime and/or power efficiency properties.

Claims (23)

1. An organic electroluminescent compound represented by the following formula 1:

wherein

X and X 1 , each independently, represent O or S;

HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl;

L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroaryene;

R 1 represents a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl;

R 2 and R 3 , each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl, or may be linked to adjacent one(s) of R 2 and R 3 to form a ring(s); and

n and m represent an integer of 1 to 3; in which if n and m, each independently, are an integer of 2 or more, each of R 2 or each of R 3 may be the same or different.

2. The organic electroluminescent compound according to claim 1 , wherein the formula 1 is represented by at least one of the following formulas 1-1 to 1-8:

wherein, X, X 1 , HAr, L 1 , R 1 to R 3 , n, and m are as defined in claim 1 .

3. The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted alkyl, the substituted aryl(ene), the substituted heteroaryl(ene), and the substituted cycloalkyl, each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl(s); a (C6-C30)aryl unsubstituted or substituted with a (3- to 30-membered)heteroaryl(s); a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di-(C1-C30)alkylamino; a mono- or di-(C6-C30)arylamino unsubstituted or substituted with a (C1-C30)alkyl(s); a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl.

4. The organic electroluminescent compound according to claim 1 , wherein HAr is any one selected from the following group 1:

5. The organic electroluminescent compound according to claim 1 , wherein the compound represented by formula 1 is selected from the group consisting of the following compounds:

6. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1 .

7. A plurality of host materials comprising the organic electroluminescent material according to claim 6 as a first host material, and at least one organic electroluminescent compound as a second host material, wherein the first host material and the second host material are different from each other.

8. The plurality of host materials according to claim 7 , wherein the at least one organic electroluminescent compound is at least one of the compounds represented by the following formula 11:

wherein

A 1 and A 2 , each independently, represent a substituted or unsubstituted (C6-C30)aryl;

L 1 represents a single bond, or a substituted or unsubstituted (C6-C30)aryene; and

X 11 to X 26 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arysilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arysilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or may be linked to adjacent one(s) of X 11 to X 26 to form a ring(s).

9. The plurality of host materials according to claim 8 , wherein the compound represented by formula 11 is selected from the group consisting of the following compounds:

10. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 .

11. An organic electroluminescent device comprising the plurality of host materials according to claim 7 .

Assignments (2)
CHANGE OF NAME Recorded Oct 17, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS KOREA LTD
To: DUPONT SPECIALTY MATERIALS KOREA LTD
Reel/Frame 069185/0438 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2023
From: KIM, HYUN; UM, JI-WON; PARK, KYOUNG-JIN; LEE, MI-JA; KIM, CHI-SIK
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 064752/0082 →