IP Library Granted Patent US 11,653,562
Granted Patent B2
US 11,653,562 · App. 17/267,469 · Granted May 16, 2023

Organic electroluminescent compound and organic electroluminescent device comprising the same

Inventors: Jin-Ri Hong (Gyeonggi-do, KR); Doo-Hyeon Moon (Gyeonggi-do, KR); Du-Yong Park (Gyeonggi-do, KR); Young-Mook Lim (Gyeonggi-do, KR)
H10K85/633C07C211/61C09K11/06C09K2211/1014H10K50/15H10K85/626
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Quick Facts
Patent No.
US 11,653,562
App. No.
17/267,469
Granted
May 16, 2023
Kind
B2
Abstract

The present disclosure relates to an organic electroluminescent compound represented by formula 1 and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having improved driving voltage, luminous efficiency, and/or lifespan characteristics can be provided.

Claims (28)

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

wherein Ar 1 and Ar 2 each independently are selected from the following structures:

wherein

A 1 to A 3 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;

L represents a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene,

L 1 represents a single bond, an unsubstituted (C6-C30)arylene, or an unsubstituted (3- to 30-membered)heteroarylene, where if a plurality of L 1 is present, each of L 1 may be the same or different;

R 1 and R 2 each independently represent a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;

R 3 represents 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;

R 4 to R 5 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,

where if a plurality of R 3 to R 5 is present, each of R 3 , each of R 4 , and each of R 5 may be the same or different; and

a represents an integer of 1 to 4, b represents 1 or 2, c represents an integer of 1 to 3, d represents 1 or 2, and c+d is 4, where if a, b, c, and d each independently are 2 or more, each of R 3 , each of R 4 , each of R 5 , and each of -L 1 -NAr 1 Ar 2 may be the same or different.

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

L 1 represents a single bond, an unsubstituted (C6-C12)arylene, or an unsubstituted (5- to 15-membered)heteroarylene;

R 1 and R 2 each independently represent a substituted or unsubstituted (C1-C6)alkyl; and

R 3 to R 5 each independently represent hydrogen, or a substituted or unsubstituted (C6-C12)aryl.

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

L 1 represents a single bond, an unsubstituted (C6-C12)arylene, or an unsubstituted (5- to 15-membered)heteroarylene;

R 1 and R 2 each independently represent an unsubstituted (C1-C6)alkyl; and

R 3 to R 5 each independently represent hydrogen, or an unsubstituted (C6-C12)aryl.

4. An organic electroluminescent compound selected from the following compounds:

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

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

7. The organic electroluminescent device according to claim 6 , wherein the organic electroluminescent compound is comprised in a hole transport zone.

8. The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted alkyl, the substituted aryl, the substituted heteroaryl, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino, and the substituted alkylarylamino in L 1 , and R 1 to R 5 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.

9. The organic electroluminescent compound according to claim 1 , wherein formula 1 is represented by any one of the following formulas 2 to 7:

wherein

Ar 1 , Ar 2 , L 1 , R 1 to R 5 , and a to c are as defined in claim 4 , and

in formulas 6 and 7, each of L 1 , each of Ar 1 , and each of Ar 2 may be the same or different.

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 Mar 27, 2023
From: HONG, JIN-RI; MOON, DOO-HYEON; PARK, DU-YONG; LIM, YOUNG-MOOK
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 063104/0777 →
Priority Claims (2)
KR 10-2018-0093813 · Aug 10, 2018 · national
KR 10-2019-0093605 · Aug 1, 2019 · national
Continuity (1)
Related Publication 20210320252A1 · Oct 14, 2021
Cited By (1)
US 12,262,633