IP Library Granted Patent US 12,453,282
Granted Patent B2
US 12,453,282 · App. 17/374,908 · Granted Oct 21, 2025

Plurality of host materials and organic electroluminescent device comprising the same

Inventors: Hyun-Ju Kang (Gyeonggi-do, KR); So-Young Jung (Gyeonggi-do, KR); Eun-Joung Choi (Gyeonggi-do, KR); Hong-Yeop Na (Gyeonggi-do, KR); Sang-Hee Cho (Gyeonggi-do, KR); Su-Hyun Lee (Gyeonggi-do, KR); Jin-Ri Hong (Gyeonggi-do, KR)
Assignee: DuPont Specialty Materials Korea Ltd.
H10K85/636C07D413/12C07D413/14C07D487/04H10K85/6572H10K50/11H10K85/657H10K85/6574H10K85/6576H10K2101/90
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,453,282
App. No.
17/374,908
Granted
Oct 21, 2025
Kind
B2
Abstract

The present disclosure relates to a plurality of host materials comprising at least one first host compound represented by formula 1 and at least one second host compound represented by formula 2, and an organic electroluminescent device comprising the same. By comprising the host materials according to the present disclosure, an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long lifespan can be provided.

Claims (51)

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

wherein,

L 1 represents a single bond,

L 2 and L 3 each independently represent a single bond or a substituted or unsubstituted phenylene;

Ar 1 represents pyridyl substituted with deuterium or (C6-C30)aryl;

Ar 2 and Ar 3 each independently represent (C6-C30)aryl unsubstituted or substituted with deuterium or (C6-C30)aryl;

a and b each independently represent an integer of 1 or 2; and

when a and b are an integer of 2, each of Ar 2 and each of Ar 3 may be the same or different;

wherein,

X 21 and Y 21 each independently represent —N═, —NR 25 —, —O—, or —S—, provided that one of X 21 and Y 21 is —N═, and the other of X 21 and Y 21 is —NR 25 —, —O—, or —S—;

R 21 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl;

R 22 to R 25 each independently represent hydrogen, deuterium, halogen, 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 of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, 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 mono- or di- (C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl (C6-C30)arylamino, a substituted or unsubstituted mono- or di- (3- to 30-membered)heteroarylamino, 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 may be linked to the adjacent substituents to form a ring(s);

provided that at least one of R 22 to R 24 is —L 21 -Ar 21 ;

L 21 represents a single bond or a substituted or unsubstituted (C6-C30)arylene;

Ar 21 represents a substituted or unsubstituted fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or —NR 31 R 32 ;

R 31 and R 32 each independently represent 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;

e and f each independently represent an integer of 1 or 2, and g represents an integer of 1 to 4; and

when e to g are an integer of 2 or more, each of R 22 , each of R 23 , and each of R 24 may be the same or different.

2. A plurality of host materials comprising a first host material and a second host material, wherein the first host material comprises a compound selected from the following compounds:

and the second host material comprises a compound represented by the following formula 2:

wherein,

X 21 and Y 21 each independently represent —N═, —NR 25 —, —O—, or —S—, provided that one of X 21 and Y 21 is —N═, and the other of X 21 and Y 21 is —NR 25 —, —O—, or —S—;

R 21 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl;

R 22 to R 25 each independently represent hydrogen, deuterium, halogen, 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 of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, 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 mono-or di-(C6-C30) arylamino, a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, a substituted or unsubstituted mono-or di-(3- to 30-membered) heteroarylamino, 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 may be linked to the adjacent substituents to form a ring(s);

provided that at least one of R 22 to R 24 is-L 21 -Ar 21 ;

L 21 represents a single bond or a substituted or unsubstituted (C6-C30) arylene;

Ar 21 represents a substituted or unsubstituted fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, or —NR 31 R 32 ;

R 31 and R 32 each independently represent 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;

e and f each independently represent an integer of 1 or 2, and g represents an integer of 1 to 4; and

when e to g are an integer of 2 or more, each of R 22, each of R 23, and each of R 24 may be the same or different.

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

wherein,

X 21, Y 21, L 21, Ar 21, R 21 to R 24, e, f, and g are as defined in claim 1 ;

g′ represents an integer of 1 to 3; and

when g′ represents an integer of 2 or more, each of R 24 may be the same or different.

4. The host materials according to claim 3 , wherein Ar 21 represents a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted fluoranthenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted spiro [cyclopentane-fluoren]yl, a substituted or unsubstituted spiro [dihydroindene-fluoren]yl, a substituted or unsubstituted spiro [benzofluoren-fluoren]yl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzocarbazolyl, a substituted or unsubstituted dibenzocarbazolyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzothiophenyl, a substituted or unsubstituted benzonaphthothiophenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzofuranyl, or a substituted or unsubstituted benzonaphthofuranyl; or amino substituted with at least one selected from the group consisting of phenyl; naphthyl; naphthylphenyl;

phenylnaphthyl; o-biphenyl, m-biphenyl; p-biphenyl; o-terphenyl; m-terphenyl; p -terphenyl; fluorenyl; benzofluorenyl; phenanthrenyl; dibenzothiophenyl;

benzonaphthofuranyl; and dibenzofuranyl.

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

wherein,

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

Ar 1 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl; and

R 1 to R 8 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, a (C6-C30) aryl that is either unsubstituted or substituted with one selected from the group consisting of deuterium, a (C6-C30) aryl, a dibenzofuranyl or a dibenzothiophenyl,

a dibenzofuranyl that is either unsubstituted or substituted with deuterium,

a dibenzothiophenyl that is either unsubstituted or substituted with deuterium, 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 of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, 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 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 (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 may be linked to the adjacent substituents to form a ring(s);

and the second host material comprises a compound is selected from the following compounds:

6. An organic electroluminescent device comprising an anode; a cathode; and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer comprise a plurality of host materials according to claim 1 .

7. An organic electroluminescent device comprising an anode; a cathode; and

at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer comprise a plurality of host materials according to claim 2 .

8. An organic electroluminescent device comprising an anode; a cathode; and

at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer comprise a plurality of host materials according to claim 5 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 21, 2025
From: KANG, HYUN-JU; JUNG, SO-YOUNG; CHOI, EUN-JOUNG; NA, HONG-YEOP; CHO, SANG-HEE; LEE, SU-HYUN; HONG, JIN-RI
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 072612/0574 →
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 →
Priority Claims (1)
KR 10-2020-0086701 · Jul 14, 2020 · national
Continuity (1)
Related Publication 20220020931A1 · Jan 20, 2022
References Cited (12)
US 20110303901A1 · Cheng et al. · 2011 [cited by applicant]
US 20140225088A1 · Hwang et al. · 2014 [cited by applicant]
US 20180208837A1 · Ahn · 2018 [cited by applicant]
US 20210336153A1 · Kim et al. · 2021 [cited by applicant]
CN 106478672A · 2017 [cited by applicant]
CN 107602568A · 2018 [cited by applicant]
CN 110964019A · 2020 [cited by examiner]
KR 20130104451A · 2013 [cited by examiner]
WO WO2010114264A2 · 2010 [cited by examiner]
WO WO2019245164A1 · 2019 [cited by examiner]
Computer-generated English-language translation of CN-110964019-A. [cited by examiner]
Search Report from China National Intellectual Property Administration for China patent application No. 202110658149.9; Application Date: Jun. 15, 2021. [cited by applicant]