IP Library Granted Patent US 12,479,860
Granted Patent B2
US 12,479,860 · App. 17/675,393 · Granted Nov 25, 2025

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

Inventors: Ji-Song Jun (Gyeonggi-do, KR); Kyoung-Jin Park (Gyeonggi-do, KR); Chi-Sik Kim (Gyeonggi-do, KR); Sang-Hee Cho (Gyeonggi-do, KR); Su-Hyun Lee (Gyeonggi-do, KR)
Assignee: DuPont Specialty Materials Korea Ltd.
C07D517/00C07D519/00H10K85/622H10K85/626H10K85/633H10K85/654H10K85/6572H10K85/6574H10K2101/90
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Quick Facts
Patent No.
US 12,479,860
App. No.
17/675,393
Granted
Nov 25, 2025
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. An organic electroluminescent device having improved driving voltage, luminous efficiency, and/or lifespan properties can be provided by including the organic electroluminescent compound according to the present disclosure as a single host material or by including a specific combination of compounds according to the present disclosure as a plurality of host materials.

Claims (36)

1 . A plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1, and the second host compound is represented by the following formula 2:

in formula 1,

R 1 to R 8 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 fused ring group of a (C3-C30)aliphatic ring(s) and a (C6-C30)aromatic ring(s), or -(L) a -HAr;

at least one of R 1 to R 8 is -(L) a -HAr;

HAr represents a substituted or unsubstituted nitrogen-containing (3- to 20-membered)heteroaryl;

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

a represents 1 or 2;

in formula 2,

L 1 to L 3 each independently represent a single bond, a substituted or unsubstituted (C1-C30)alkylene, 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 1 to Ar 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 an unsubstituted fused ring group of a (C3-C30)aliphatic ring(s) and a (C6-C30)aromatic ring(s), or -L b -N(Ar c )(Ar d );

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

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

with the proviso that the case where all of L 1 to L 3 are single bonds and all of Ar1 to Ar3 are hydrogen is excluded.

2 . The plurality of host materials according to claim 1 , wherein the substituents of the substituted alkyl(ene), the substituted alkenyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl(ene), the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the substituted fused ring group of an aliphatic ring(s) and an 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 phosphine oxide; 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); 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 mono- or di-(C6-C30)arylamino; a mono- or di-(3- to 30-membered)heteroarylamino; a (C1-C30)alkyl(C2-C30)alkenylamino; a (C1-C30)alkyl(C6-C30)arylamino; 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)arylphosphine; 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 plurality of host materials according to claim 1 , wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-4:

in formulas 1-1 to 1-4,

R 1 to R 8 , L, HAr, and a are as defined in claim 1 .

4 . The plurality of host materials according to claim 1 , wherein the formula 2 is represented by any one of the following formulas 2-1 to 2-14:

in formulas 2-1 to 2-14,

Y 1 , Y 2 , Z 1 , and Z 2 each independently represent —N═, —NR 21 —, —O—, or —S—, with the proviso that any one of Y 1 and Z 1 represents —N═, and the other one of Y 1 and Z 1 represents —NR 21 —, —O—, or —S—, and with the proviso that any one of Y 2 and Z 2 represents —N═, and the other one of Y 2 and Z 2 represents —NR 21 —, —O—, or —S—;

T represents CR 22 R 23 , NR 24 , O, or S;

T 1 to T 13 and W 1 to W 12 each independently represent N or CV 1 ;

R 11 and Ar 6 each independently represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;

R 12 to R 19 , R 21 to R 28 , and V 1 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 fused ring group of a (C3-C30)aliphatic ring(s) and a (C6-C30)aromatic ring(s), or -L c -N(Ar e )(Ar f ); or may be linked to an adjacent substituent to form a substituted or unsubstituted ring(s);

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

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

b and i represent 1; c, d, j, m, and n each independently represent 1 or 2; e, f, g, f′, k, l, and o each independently represent an integer of 1 to 4; g′ represents an integer of 1 to 3; in which if c to g, f′, g′, l, m, n, and o are an integer of 2 or more, each of R 12 to each of R 19 and each of R 25 to each of R 28 may be the same as or different from each other; and

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

5 . The plurality of host materials according to claim 1 , wherein HAr of formula 1 is at least one selected from the following structures:

in formulas 1-5 to 1-7,

X 1 to X 8 each independently represent CR 25 or N;

R 25 , Ar 7 , and Ar 8 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, wherein R 25 may be linked to an adjacent substituent to form a ring(s); and

* represents a site linked to dibenzoselenophene.

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

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

8 . An organic electroluminescent device comprising an anode; a cathode; and at least one light-emitting layer between the anode and the cathode, wherein 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 Oct 20, 2025
From: JUN, JI-SONG; LEE, SU-HYUN; CHO, SANG-HEE; KIM, CHI-SIK; PARK, KYOUNG-JIN
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 072594/0730 →
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 →