IP Library Granted Patent US 12,207,547
Granted Patent B2
US 12,207,547 · App. 16/757,844 · Granted Jan 21, 2025

Organic electroluminescent compound, organic electroluminescent material comprising the same, and organic electroluminescent device

Inventors: Hyo-Jung Lee (Gyeonggi-do, KR); Dominea Rathwell (Gyeonggi-do, KR); Sang-Hee Cho (Gyeonggi-do, KR); Hyun-Ju Kang (Gyeonggi-do, KR)
Assignee: Rohm and Haas Electronic Materials Korea Ltd.
H10K85/654C07D487/04C09K11/06H10K85/6572C09K2211/1007C09K2211/1011C09K2211/1018H10K50/11H10K2101/10
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Quick Facts
Patent No.
US 12,207,547
App. No.
16/757,844
Granted
Jan 21, 2025
Kind
B2
Abstract

The present disclosure relates to an organic electroluminescent compound, an organic electroluminescent material, and an organic electroluminescent device comprising the same. The organic electroluminescent compound of the present disclosure can provide an organic electroluminescent device having improved lifespan properties compared to the organic electroluminescent device comprising a conventional organic electroluminescent compound.

Claims (19)

1. An organic electroluminescent compound represented by formula 2, 3, 4, 5 or 7:

wherein,

X 1 to X 3 each independently represent CR 12 or N;

at least one of X 1 to X 3 represents N;

Ar 1 to Ar 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;

R 1 to R 3 , and R 12 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or R 1 and R 3 may be linked to an adjacent substituent to form a substituted or unsubstituted (C3-C30) mono- or polycyclic, alicyclic or aromatic ring or a combination thereof;

a and b each independently represent an integer from 0 to 4; c represents an integer from 0 to 2; when a or b is an integer of 2 or more or c is 2, each of R 1 , each of R 2 , or each of R 3 may be the same or different;

L 1 is represented by the following formula R-1:

wherein,

R 4 represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl;

d represents an integer from 0 to 6, when d is an integer of 2 or more, each of R 4 may be the same or different;

* represents a linkage position with an adjacent ring in formula 1.

2. The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted (C1-C30)alkyl, the substituted (C3-C30)cycloalkyl, the substituted (C3-C30)cycloalkenyl, the substituted (3- to 7-b membered)heterocycloalkyl, the substituted (C6-C30)aryl, the substituted (3- to 30-membered)heteroaryl, and the substituted (C3-C30) mono- or polycyclic, alicyclic, or aromatic ring, or a combination thereof in Ar 1 to Ar 3 , R 1 to R 4 , and R 12 , each independently, are at least one selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3- to 7-membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, unsubstituted (5- to 30-membered)heteroaryl, (5- to 30-membered)heteroaryl substituted with (C6-C30)aryl, unsubstituted (C6-C30)aryl, (C6-C30)aryl substituted with (5- to 30-membered)heteroaryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, amino, mono- or di-(C1-C30)alkylamino, unsubstituted mono- or di-(C6-C30)arylamino, mono- or di-(C6-C30)arylamino substituted with (C1-C30)alkyl, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)aryl(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl.

3. The organic electroluminescent compound according to claim 1 , wherein at least two of X 1 to X 3 represent N;

Ar 1 to Ar 3 each independently represent a substituted or unsubstituted (C6-C25)aryl;

R 1 to R 4 , and R 12 each independently represent hydrogen or deuterium.

4. The organic electroluminescent compound according to claim 1 , wherein the compound represented by formula 2 to 5 or 7 is 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 .

Assignments (3)
CHANGE OF NAME Recorded Oct 22, 2024
From: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
To: DUPONT SPECIALTY MATERIALS KOREA LTD.
Reel/Frame 069211/0582 →
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 23, 2024
From: LEE, HYO-JUNG; RATHWELL, DOMINEA; CHO, SANG-HEE; KANG, HYUNG-JU
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 068381/0578 →