IP Library › Granted Patent US 12,258,353
Granted Patent B2
US 12,258,353 · App. 17/299,376 · Granted Mar 25, 2025

Heterocyclic compound and organic light-emitting element including same

Inventors: Hyun-Ju La (Osan-si, KR); Hye-Su Ji (Hwaseong-si, KR); Won-Jang Jeong (Hwaseong-si, KR)
Assignee: LT MATERIALS CO., LTD.
C07D498/04C07D471/04C07D519/00C07F9/5325H10K85/622H10K85/654H10K85/6572H10K50/11H10K50/13H10K50/18H10K2101/30H10K2101/40
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Quick Facts
Patent No.
US 12,258,353
App. No.
17/299,376
Granted
Mar 25, 2025
Kind
B2
Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1, and an organic light emitting device including the same.

Claims (33)

1. A heterocyclic compound represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1,

L 1 to L 3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;

Z 1 to Z 3 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group;

R 1 and R 2 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or heteroring;

m, p, x, n, q and y are each an integer of 1 to 5;

a is an integer of 1 to 3;

b is an integer of 1 to 4; and

when m, p, x, n, q, y, a and b are an integer of 2 or greater, substituents in the parentheses are the same as or different from each other.

2. The heterocyclic compound of claim 1 , wherein Chemical Formula 1 is represented by one of the following Chemical Formula 2 to Chemical Formula 4:

in Chemical Formula 2 to Chemical Formula 4,

R 1 , R 2 , m, p, x, n, q, y, a and b have the same definitions as in Chemical Formula 1;

L 11 to L 13 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; and

Z 11 to Z 13 are the same as or different from each other, and each independently selected from the group consisting of a cyano group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a substituted or unsubstituted phosphine oxide group.

3. The heterocyclic compound of claim 1 , wherein R 1 and R 2 are hydrogen.

4. The heterocyclic compound of claim 1 , wherein Z 1 to Z 3 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or a substituted or unsubstituted phosphine oxide group.

5. The heterocyclic compound of claim 1 , wherein Chemical Formula 1 is represented by any one of the following compounds:

6. An organic light emitting device comprising:

a first electrode;

a second electrode; and

one or more organic material layers provided between the first electrode and the second electrode,

wherein one or more layers of the organic material layers include the heterocyclic compound of claim 1 .

7. The organic light emitting device of claim 6 , wherein the organic material layer includes an electron transfer layer, and the electron transfer layer includes the heterocyclic compound.

8. The organic light emitting device of claim 6 , wherein the organic material layer includes a hole blocking layer, and the hole blocking layer includes the heterocyclic compound.

9. The organic light emitting device of claim 6 , further comprising one, two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transfer layer, an electron injection layer, an electron transfer layer, an electron blocking layer and a hole blocking layer.

10. The organic light emitting device of claim 6 , comprising:

a first electrode;

a first stack provided on the first electrode and including a first light emitting layer;

a charge generation layer provided on the first stack;

a second stack provided on the charge generation layer and including a second light emitting layer; and

a second electrode provided on the second stack.

11. The organic light emitting device of claim 10 , wherein the charge generation layer includes the heterocyclic compound.

12. The organic light emitting device of claim 10 , wherein the charge generation layer is an N-type charge generation layer, and the charge generation layer includes the heterocyclic compound.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 3, 2021
From: LA, HYUN-JU; JI, HYE-SU; JEONG, WON-JANG
To: LT MATERIALS CO., LTD.
Reel/Frame 056475/0690 →
Priority Claims (1)
KR 10-2018-0156184 · Dec 6, 2018 · national
Continuity (1)
Related Publication 20220033415A1 · Feb 3, 2022
References Cited (19)
US 20080278072A1 · Noh et al. · 2008 [cited by applicant]
US 20120313091A1 · Kang et al. · 2012 [cited by applicant]
US 20180047914A1 · Cha et al. · 2018 [cited by applicant]
US 20180208837A1 · Ahn · 2018 [cited by applicant]
US 20180323379A1 · Kim et al. · 2018 [cited by applicant]
US 20180323397A1 · Ahn et al. · 2018 [cited by applicant]
US 20200066996A1 · La et al. · 2020 [cited by applicant]
CN 107428769A · 2017 [cited by applicant]
CN 197848399A · 2018 [cited by applicant]
CN 108884090A · 2018 [cited by applicant]
JP 2005255992A · 2005 [cited by applicant]
JP 2005259687A · 2005 [cited by applicant]
KR 1020080097153A · 2008 [cited by applicant]
KR 1020110096453A · 2011 [cited by applicant]
KR 1020170022865A · 2017 [cited by applicant]
KR 1020170051198A · 2017 [cited by applicant]
KR 1020180075398A · 2018 [cited by applicant]
1 Page brochure for Benzoquinoline, CAS Reg. No. 230-27-3, by NIST Chemistry Webbook, SRD 69, Downloaded on Nov. 7, 2024. [cited by examiner]
International Search Report (PCT/ISA/210) issued in PCT/KR2019/017203 mailed on Mar. 16, 2020. [cited by applicant]