IP Library Granted Patent US 12,588,353
Granted Patent B2
US 12,588,353 · App. 17/825,399 · Granted Mar 24, 2026

Plurality of host materials, organic electroluminescent compound and organic electroluminescent device comprising the same

Inventors: Sang-Hee Cho (Gyeonggi-do, KR); Bitnari Kim (Gyeonggi-do, KR); Young-Jae Kim (Gyeonggi-do, KR); So-Young Jung (Gyeonggi-do, KR); Mi-Ja Lee (Gyeonggi-do, KR); Su-Hyun Lee (Gyeonggi-do, KR); Tae-Jun Han (Gyeonggi-do, KR); HaeYeon Kim (Gyeonggi-do, KR)
Assignee: DuPont Specialty Materials Korea Ltd.
H10K50/11C07D209/94C07D403/10C07D405/10C07D409/10C07D487/04H10K85/00H10K85/636H10K85/6572H10K85/6574H10K85/6576H10K2101/90
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Quick Facts
Patent No.
US 12,588,353
App. No.
17/825,399
Granted
Mar 24, 2026
Kind
B2
Abstract

The present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same. By comprising the specific combination of compounds according to the present disclosure as a plurality of host materials according to the present disclosure, it is possible to provide an organic electroluminescent device having improved driving voltage, luminous efficiency, and/or lifetime property compared to the conventional organic electroluminescent devices.

Claims (52)

1 . A plurality of host materials comprising a first host material comprising the compound represented by formula 1, and a second host material comprising the compound represented by formula 2:

in formula 1,

L represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C3-C30)cycloalkylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-to 30-membered)heteroarylene;

Ar represents deuterium, a halogen, a cyano, 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, a substituted or unsubstituted (3-to 30-membered) heteroaryl, —NR 11 R 12 , or —SiR 13 R 14 R 15 ;

R 11 to R 15 , 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; and

 is represented by the following formula 1-1 or 1-2:

in formulas 1-1 and 1-2,

X 1 to X 25 , each independently, represent —N═ or —C(R a )═;

R a , 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-(C2-C30) alkenylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3-to 30-membered)heteroarylamino, a substituted or unsubstituted (C1-C30)alkyl(C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl (3-to 30-membered)heteroarylamino, a substituted or unsubstituted (C2-C30) alkenyl (C6-C30)arylamino, a substituted or unsubstituted (C2-C30) alkenyl (3-to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl (3-to 30-membered)heteroarylamino, or the adjacent R a 's may be linked to each other to form a ring(s), and where if there is a plurality of R a , each of R a may be the same or different from each other; with the provisos that:

R a in X 5 is not linked to the adjacent R a in X 6 to form a ring(s);

R a in X 9 is not linked to the adjacent R a in X 10 to form a ring(s);

R a in X 18 is not linked to the adjacent R a in X 19 to form a ring(s); and

R a in X 22 is not linked to the adjacent R a in X 23 to form a ring(s); and

in formula 2,

X′ represents O, S, or CR 5 R 6 ;

R 1 to R 4 , each independently, represent hydrogen, deuterium, a cyano, 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, a substituted or unsubstituted (3-to 30-membered)heteroaryl, -L 3 -NR 16 R 17 , or —SiR 18 R 19 R 20 ; or may be linked to adjacent substituent(s) to form a ring(s);

wherein, at least one of R 1 to R 4 represents a cyano, 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, a substituted or unsubstituted (3-to 30-membered)heteroaryl, -L 3 -NR 16 R 17 , or —SiR 18 R 19 R 20 ;

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

R 5 and R 6 , 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, or R 5 and R 6 may be linked to each other to form a ring(s);

R 16 to R 20 , 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; and

a′ and d′, each independently, represent an integer of 1 to 4, b′ and c′, each independently, represent an integer of 1 or 2, and where if each of a′ to d′ is an integer of 2 or more, each of R 1 to each of R 4 may be the same or different from each other.

2 . The plurality of host materials according to claim 1 , wherein formula 1-1 is represented by the following formula 1-1-1:

in formula 1-1-1,

R 31 to R 33 , each independently, are the same as the definition of R a , with the provisos that:

R 31 is not linked to the adjacent R 32 to form a ring(s); and

R 32 is not linked to the adjacent R 33 to form a ring(s); and

aa represents an integer of 1 to 5, ab represents an integer of 1 to 4, ac represents an integer of 1 to 3, and where if aa, ab, and ac are an integer of 2 or more, each of R 31 , each of R 32 , and each of R 33 may be the same or different from each other.

3 . The plurality of host materials according to claim 1 , wherein formula 1-2 is represented by the following formula 1-2-1:

in formula 1-2-1,

R 41 to R 44 , each independently, are the same as the definition of R a , with the provisos that:

R 42 is not linked to the adjacent R 43 to form a ring(s); and

R 43 is not linked to the adjacent R 44 to form a ring(s); and

ba represents an integer of 1 or 2, bb and bc, each independently, represent an integer of 1 to 4, bd represents an integer of 1 to 3, and where if ba, bb, bc, and bd are an integer of 2 or more, each of R 41 , each of R 42 , each of R 43 , and each of R 44 may be the same or different from each other.

4 . The plurality of host materials according to claim 1 , in formula 2,

at least one of R 1 to R 4 is-L 2 -HAr or -L 3 -NR 16 R 17 ;

L 2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-to 30-membered)heteroarylene;

HAr represents a substituted or unsubstituted (3-to 30-membered)heteroaryl comprising at least one of N, O and S; and

L 3 , R 16 , and R 17 , each independently, are as defined in claim 1 .

5 . The plurality of host materials according to claim 1 , wherein the compound represented by formula 2 is represented by any one of the following formulas 2-1 to 2-4:

in formulas 2-1 to 2-4,

X′, R 1 to R 4 , and a′ to d′ are as defined in claim 1 ;

L 2 , each independently, represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-to 30-membered)heteroarylene;

Z 1 to Z 3 , each independently, represent N or CH, provided that at least one of Z 1 to Z 3 is N;

Ar 2 and Ar 3 , each independently, represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-to 30-membered)heteroaryl; and

e′, each independently, represents an integer of 1 to 3, and where if each of e′ is an integer of 2 or more, each of R 1 and each of R 4 may be the same or different from each other.

6 . The plurality of host materials according to claim 1 , wherein the compound represented by formula 2 is represented by any one of the following formulas 2-5 to 2-8:

in formulas 2-5 to 2-8,

X′, L 3 , R 1 to R 4 , R 16 , R 17 , and a′ to d′ are as defined in claim 1 ; and

e′, each independently, represents an integer of 1 to 3, and where if each of e′ is an integer of 2 or more, each of R 1 and each of R 4 may be the same or different from each other.

7 . The plurality of host materials according to claim 1 , wherein the compound represented by formula 1 is at least one selected from the group consisting of the following compounds:

8 . The plurality of host materials according to claim 1 , wherein the compound represented by formula 2 is at least one selected from the group consisting of the following compounds:

9 . An organic electroluminescent device comprising anode; cathode; and at least one light-emitting layer between the anode and the cathode in which at least one of the light-emitting layers comprises the plurality of host materials according to claim 1 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2026
From: CHO, SANG-HEE; KIM, BITNARI; KIM, YOUNG-JAE; JUNG, SO-YOUNG; LEE, MI-JA; LEE, SU-HYUN; HAN, TAE-JUN; KIM, HAEYEON
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 073574/0728 →
CHANGE OF NAME Recorded Nov 11, 2024
From: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
To: DUPONT SPECIALTY MATERIALS KOREA LTD.
Reel/Frame 069316/0857 →
CHANGE OF NAME Recorded Oct 17, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS KOREA LTD
To: DUPONT SPECIALTY MATERIALS KOREA LTD
Reel/Frame 069185/0438 →