IP Library Granted Patent US 12,084,446
Granted Patent B2
US 12,084,446 · App. 17/442,469 · Granted Sep 10, 2024

Organic electroluminescent compound and organic electroluminescent device comprising the same

Inventors: Hong-Se Oh (Gyeonggi-do, KR); Sung-Woo Jang (Gyeonggi-do, KR); Joon-Hyung Kil (Gyeonggi-do, KR); Seon-Jin Hwang (Gyeonggi-do, KR); Seung-Ae Kim (Gyeonggi-do, KR); Hee-Ryong Kang (Gyeonggi-do, KR); Sang-Hee Cho (Gyeonggi-do, KR); Hyo-Soon Park (Gyeonggi-do, KR)
Assignee: Rohm and Haas Electronic Materials Korea
C07D487/00C07D519/00H10K85/626H10K85/654H10K85/6572H10K85/6574H10K85/6576H10K50/11H10K2101/30H10K2101/40
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Quick Facts
Patent No.
US 12,084,446
App. No.
17/442,469
Granted
Sep 10, 2024
Kind
B2
Abstract

The present disclosure relates to an organic electroluminescent compound, and an organic electroluminescent device comprising the same. It is possible to provide an organic electroluminescent device which can be deposited at a low deposition temperature and/or in which clogging is reduced.

Claims (32)

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

wherein

X 1 to X 12 each independently represent N or CR 1 ;

T 1 to T 4 each independently represent N or CR 2 ;

Y 1 to Y 3 each independently represent N or CR 3 , in which at least one of Y 1 to Y 3 is N;

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

Ar 1 , Ar 2 , and R 1 to R 3 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(s), where if a plurality of R 1 to R 3 is present, 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 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, 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 , Ar 1 , Ar 2 , and R 1 to R 3 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(s); a (C6-C30)aryl unsubstituted or substituted with a (5- 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.

3. The organic electroluminescent compound according to claim 1 , wherein formula 1 is represented by the following formula 2 or formula 3:

wherein

a and b each independently represent an integer of 1 to 6, in which, if a and b are an integer of 2 or more, each of R 2 may be the same or different;

Y′ represents CR 4 R 5 , O, or S;

R 4 and R 5 each independently represent a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; and

X 1 to X 12 , Y 1 to Y 3 , L 1 , Ar 1 , and Ar 2 are as defined in claim 1 .

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

X 1 to X 12 each independently represent N or CR 1 ;

T 1 to T 4 each independently represent N or CR 2 ;

Y 1 to Y 3 each independently represent N or CR 3 , in which at least one of Y 1 to Y 3 is N;

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

Ar 1 and Ar 2 each independently represent a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted (5- to 15-membered)heteroaryl; and

R 1 to R 3 each independently represent hydrogen, a substituted or unsubstituted (C6-C12)aryl, or a substituted or unsubstituted (5- to 15-membered)heteroaryl; or may be linked to an adjacent substituent to form a ring(s).

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

X 1 to X 12 each independently represent CR 1 ;

T 1 to T 4 each independently represent N or CR 2 ;

Y 1 to Y 3 each independently represent N or CR 3 , in which at least one of Y 1 to Y 3 is N;

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

Ar 1 and Ar 2 each independently represent a (C6-C18)aryl unsubstituted or substituted with one or more deuterium, or an unsubstituted (5- to 15-membered)heteroaryl; and

R 1 to R 3 each independently represent hydrogen, an unsubstituted (C6-C12)aryl, or an unsubstituted (5- to 15-membered)heteroaryl; or may be linked to an adjacent substituent to form a ring(s).

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

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. An 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 Jul 22, 2024
From: OH, HONG-SE; KIL, JOON-HYUNG; KIM, SEUNG-AE; CHO, SANG-HEE; JANG, SUNG-WOO; HWANG, SEON-JIN; KANG, HEE-RYONG; PARK, HYO-SOON
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 068041/0556 →