IP Library Granted Patent US 11,926,591
Granted Patent B2
US 11,926,591 · App. 16/968,888 · Granted Mar 12, 2024

Organic electroluminescent compound and organic electroluminescent device comprising the same

Inventors: Hong-Se Oh (Gyeonggi-do, KR); Jeong-Eun Yang (Gyeonggi-do, KR); Tae-Jin Lee (Gyeonggi-do, KR); Sang-Hee Cho (Gyeonggi-do, KR)
Assignee: Rohm and Haas Electronic Materials Korea Ltd.
C07D209/82C07D307/91C07D333/76C07D401/04C07D401/10C07D401/14C07D405/14C07D409/14C07D487/04
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Quick Facts
Patent No.
US 11,926,591
App. No.
16/968,888
Granted
Mar 12, 2024
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, an organic electroluminescent device having improved driving voltage, luminous efficiency, and/or lifespan characteristics can be provided.

Claims (33)

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

wherein

Y 1 to Y 14 each independently represent N or CR 1 , in which if a plurality of R 1 's is present, each R 1 may be the same or different;

with the proviso that at least a pair of Y 1 to Y 14 wherein two of Y 1 to Y 14 are adjacent to each other are fused with the following formula 2 to form a ring:

Z represents NR 2 , O, S, CR 3 R 4 or SiR 5 R 6 ;

X 1 to X 4 each independently represent N or CR 7 , in which if a plurality of R 7 's is present, each R 7 may be the same or different;

the dotted line represents a site fused with the adjacent two of Y 1 to Y 14 of formula 1;

R 2 represents

wherein represents the bonding site of La to the nitrogen of NR 2 ;

La represents 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;

Ar 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, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino;

R 1 and R 7 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, a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or adjacent two R 1 's or adjacent two R 7 's may be linked to each other to form a ring;

R 3 to R 6 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or R 3 and R 4 , or R 5 and R 6 may be linked to each other to form a ring; and

a is an integer of 1 to 4, in which if a is 2 or more, each Ar 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, the substituted (C6-C30)aryl(3- to 30-membered)heteroarylamino, and the substituted (C1-C30)alkyl(C6-C30)arylamino in La, Ar, R 1 , and R 3 to R 7 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; 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

Z represents NR 2 , O or S;

La represents a single bond, a substituted or unsubstituted (C6-C15)arylene, or a substituted or unsubstituted (5- to 15-membered)heteroarylene;

Ar represents a substituted or unsubstituted (C6-C15)aryl, a substituted or unsubstituted (5- to 15-membered)heteroaryl, a substituted or unsubstituted di(C6-C15)arylamino, or a substituted or unsubstituted (C6-C15)aryl(5- to 15-membered)heteroarylamino;

R 1 represents hydrogen;

R 7 represents hydrogen, a substituted or unsubstituted (C6-C15)aryl, a substituted or unsubstituted (5- to 15-membered)heteroaryl, a substituted or unsubstituted di(C6-C15)arylamino, or a substituted or unsubstituted (C6-C15)aryl(5- to 15-membered)heteroarylamino; and

a is 1 or 2.

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

Z represents NR 2 , O or S;

La represents a single bond, an unsubstituted (C6-C15)arylene, or an unsubstituted (5- to 15-membered)heteroarylene;

Ar represents an unsubstituted (C6-C15)aryl, a (5- to 15-membered)heteroaryl unsubstituted or substituted with a (C6-C15)aryl, a di(C6-C15)arylamino unsubstituted or substituted with a (C1-C6)alkyl, or an unsubstituted (C6-C15)aryl(5- to 15-membered)heteroarylamino;

R 1 represents hydrogen;

R 7 represents hydrogen, an unsubstituted (C6-C15)aryl, a (5- to 15-membered)heteroaryl unsubstituted or substituted with a (C6-C15)aryl, a di(C6-C15)arylamino unsubstituted or substituted with a (C1-C6)alkyl, or an unsubstituted (C6-C15)aryl(5- to 15-membered)heteroarylamino; and

a is 1 or 2.

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

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

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

8. The organic electroluminescent device according to claim 7 , wherein the organic electroluminescent compound is comprised in a light-emitting layer, a hole transport zone, or both of them.

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 Feb 6, 2024
From: OH, HONG-SE; LEE, TAE-JIN; CHO, SANG-HEE; YANG, JEONG-EUN
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD
Reel/Frame 066389/0567 →
Priority Claims (2)
KR 10-2018-0021237 · Feb 22, 2018 · national
KR 10-2019-0000623 · Jan 3, 2019 · national
Continuity (1)
Related Publication 20210024466A1 · Jan 28, 2021