IP Library Granted Patent US 12,612,418
Granted Patent B2
US 12,612,418 · App. 17/516,947 · Granted Apr 28, 2026

Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same

Inventors: Hyun-Ju Kang (Gyeonggi-do, KR); Eun-Joung Choi (Gyeonggi-do, KR); Hyo-Jung Lee (Gyeonggi-do, KR); Su-Hyun Lee (Gyeonggi-do, KR); Kyoung-Jin Park (Gyeonggi-do, KR); Sang-Hee Cho (Gyeonggi-do, KR); Hong-Yeop Na (Gyeonggi-do, KR)
Assignee: DuPont Specialty Materials Korea Ltd.
C07D519/00C07D498/04C07D513/04H10K85/40H10K85/622H10K85/623H10K85/625H10K85/626H10K85/633H10K85/636H10K85/654H10K85/6572H10K85/6574H10K85/6576H10K50/11H10K2101/10H10K2101/30H10K2101/40H10K2101/90
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Quick Facts
Patent No.
US 12,612,418
App. No.
17/516,947
Granted
Apr 28, 2026
Kind
B2
Abstract

The present disclosure relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound according to the present disclosure as a single host material, or the specific combination of compounds according to the present disclosure as a plurality of host materials, it is possible to provide an organic electroluminescent device having improved luminous efficiency.

Claims (29)

1 . An organic electroluminescent compound represented by the following formulas 1-1 or 1-2:

wherein

X 1 and X 2 , each independently, represents NR 1 , CR 2 R 3 , O, S, P, or P═O;

L 1 and L 2 , each independently, represent a single bond, a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), or a substituted or unsubstituted (C6-C30) arylene;

Ar 1 represents hydrogen, or a substituted or unsubstituted triazinyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl or pyrazinoindolyl;

Ar 2 represents hydrogen, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), a substituted or unsubstituted (3-to 30-membered)heteroaryl, or —N—(Ar 3 )(Ar 4 ); with the proviso that the case where both Ar 1 and Ar 2 are hydrogen is excluded;

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, or 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, or a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), and R 2 and R 3 may be linked to each other to form a spiro ring;

R 4 represents 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, 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 fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), or —N—(Ar 3 )(Ar 4 ); or may be linked to adjacent R 4 to form a ring(s);

R 5 represents hydrogen or deuterium;

Ar 3 and Ar 4 , each independently, represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-to 30-membered) heteroaryl;

c and d, each independently, represent an integer of 1 to 3; in which when R 4 and R 5 are each present in plural, each of R 4 and each of R 5 may be the same as or different from each other; and

e represents an integer of 1 or 2; in which when two Ar 1 are present, each of Ar 1 may be the same as or different from each other.

2 . The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted alkyl, the substituted alkenyl, the substituted aryl, the substituted arene, the substituted arylene, the substituted heteroaryl, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the substituted fused ring group of a aliphatic ring(s) and a aromatic ring(s), 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 at least one of deuterium and a (C6-C30)aryl(s); a (C6-C30)aryl unsubstituted or substituted with at least one of deuterium and 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; a fused ring group of a (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s); an amino; a mono- or di-(C1-C30)alkylamino; a mono- or di-(C2-C30)alkenylamino; a (C1-C30)alkyl(C2-C30)alkenylamino; a mono- or di-(C6-C30)arylamino; a (C1-C30)alkyl(C6-C30)arylamino; a mono- or di-(3- to 30-membered)heteroarylamino; a (C1-C30)alkyl(3- to 30-membered)heteroarylamino; a (C2-C30)alkenyl(C6-C30)arylamino; a (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; a (C6-C30)aryl(3- to 30-membered)heteroarylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a (C6-C30)arylphosphinyl; 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 . An organic electroluminescent compound selected from the following compounds:

4 . A plurality of host materials comprising a first host material(s) and a second host material(s), wherein the first host material comprises at least one of the compound represented by formulas 1-1 or 1-2 according to claim 1 , and the second host material comprises at least one of the compounds represented by the following formula 2 or at least one of the compounds represented by the following formula 3:

in formula 2,

X and Y, each independently, represent —N═, —NR 16 —, —O—, or —S—; with the proviso that any one of X and Y represents —N═, and the other represents —NR 16 —, —O—, or —S—;

R 6 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;

R 7 to R 11 , and R 16 , 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 (C1-C30)alkyl(C2-C30)alkenylamino, 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, 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 (C6-C30)aryl(3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or may be linked to an adjacent substituent(s) to form a ring(s);

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

m and f, each independently, represent an integer of 1 or 2, g represents an integer of 1 to 4; in which when R 7 to R 9 are each present in plural, each of R 7 to each of R 9 may be the same as or different from each other; and

in formula 3,

T 1 represents a single bond, O, or S;

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

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

R 12 to R 15 , 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 50-membered)heteroaryl, 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 fused ring group of an (C3-C30) aliphatic ring(s) and a (C6-C30) aromatic ring(s), a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C2-C30)alkenylamino, 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, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino, or may be linked to an adjacent substituent(s) to form a ring(s); and

h and k, each independently, represent an integer of 1 to 4, and i and j, each independently, represent an integer of 1 to 3; in which when R 12 to R 15 are each present in plural, each of R 12 to each of R 15 may be the same as or different from each other.

5 . The plurality of host materials according to claim 4 , wherein the compound represented by formula 2 or 3 is selected from the following compounds:

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

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 12, 2026
From: KANG, HYUN-JU; NA, HONG-YEOP; CHOI, EUN-JOUNG; LEE, HYO-JUNG; LEE, SU-HYUN; PARK, KYOUNG-JIN; CHO, SANG-HEE
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 074054/0397 →
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 →