IP Library Granted Patent US 11,788,000
Granted Patent B2
US 11,788,000 · App. 16/962,257 · Granted Oct 17, 2023

Organic electroluminescent compound and organic electroluminescent device comprising the same

Inventors: Ga-Won Lee (Gyeonggi-do, KR); Sang-Hee Cho (Gyeonggi-do, KR); Hee-Ryong Kang (Gyeonggi-do, KR); Hong-Se Oh (Gyeonggi-do, KR); Jeong-Eun Yang (Gyeonggi-do, KR)
C09K11/06H10K85/6572H10K85/6574H10K85/6576C09K2211/1029H10K50/11
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 11,788,000
App. No.
16/962,257
Granted
Oct 17, 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 of the present disclosure, it is possible to provide an organic electroluminescent device with improved driving voltage, luminous efficiency, lifespan properties and/or power efficiency.

Claims (27)

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

wherein

X 1 represents —N(L 1 -R 5 )—, —O—, —S— or —C(R 6 )(R 7 )—;

Y 1 represents —N═, —N(R 8 )—, —O—, —S—, —C(R 9 )═ or —C(R 10 )(R 11 )—;

Y 2 represents —N— or —C═;

L 1 and L 2 , each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;

R 1 to R 3 and R 6 to R 11 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent to form a ring;

R 4 and R 5 , each independently, represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; and

a represents an integer of 1 or 2; b represents an integer of 1 to 3; c represents an integer of 1 to 4; where if a to c, each independently, are an integer of 2 or more, each of R 1 , each of R 2 , and each of R 3 may be the same or different.

2. The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted (C1-C30)alkyl, the substituted (C6-C30)aryl(ene), the substituted (3- to 30-membered)heteroaryl(ene), the substituted (C3-C30)cycloalkyl(ene), the substituted (C1-C30)alkoxy, the substituted tri(C1-C30)alkylsilyl, the substituted di(C1-C30)alkyl(C6-C30)arylsilyl, the substituted (C1-C30)alkyldi(C6-C30)arylsilyl, the substituted tri(C6-C30)arylsilyl, the substituted mono- or di-(C1-C30)alkylamino, the substituted mono- or di-(C6-C30)arylamino, and the substituted (C1-C30)alkyl(C6-C30)arylamino in L 1 , L 2 , and R 1 to R 11 , 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 (5- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl; a (C6-C30)aryl unsubstituted or substituted with a (5- to 30-membered)heteroaryl; 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; 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.

3. The organic electroluminescent compound according to claim 1 , wherein L 1 and L 2 , each independently, represent a single bond, or any one of the following R-1 to R-4:

4. The organic electroluminescent compound according to claim 1 , wherein

L 1 and L 2 , each independently, represent a single bond, a substituted or unsubstituted (C6-C15)arylene, or a substituted or unsubstituted (5- to 15-membered)heteroarylene;

R 1 to R 3 , each independently, represent hydrogen, a substituted or unsubstituted (C6-C15)aryl, or a substituted or unsubstituted (5- to 15-membered)heteroaryl; or may be linked to an adjacent substituent to form a ring;

R 4 and R 5 , each independently, represent a substituted or unsubstituted (C6-C15)aryl, a substituted or unsubstituted (5- to 15-membered)heteroaryl, or a substituted or unsubstituted mono- or di-(C6-C15)arylamino;

R 6 to R 11 , each independently, represent a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C15)aryl; and

a, b and c, each independently, represent 1 or 2.

5. The organic electroluminescent compound according to claim 1 , wherein

L 1 and L 2 , each independently, represent a single bond, or an unsubstituted (C6-C15)arylene;

R 1 to R 3 , each independently, represent hydrogen, an unsubstituted (C6-C15)aryl, or an unsubstituted (5- to 15-membered)heteroaryl; or may be linked to an adjacent substituent to form a ring;

R 4 and R 5 , each independently, represent an unsubstituted (C6-C15)aryl; a (5- to 15-membered)heteroaryl unsubstituted or substituted with a (C6-C15)aryl; a (5- to 15-membered)heteroaryl substituted with a (C6-C15)aryl and a (5- to 15-membered)heteroaryl; or a mono- or di-(C6-C15)arylamino unsubstituted or substituted with a (C1-C6)alkyl;

R 6 to R 11 , each independently, represent an unsubstituted (C1-C6)alkyl, or an unsubstituted (C6-C15)aryl; and

a, b and c, each independently, represent 1 or 2.

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

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

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

9. The organic electroluminescent device according to claim 8 , wherein the organic electroluminescent compound is comprised in a light-emitting layer.

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 28, 2023
From: LEE, GA-WON; CHO, SANG-HEE; KANG, HEE-RYONG; OH, HONG-SE; YANG, JEONG-EUN
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 064717/0282 →