IP Library Granted Patent US 11,434,228
Granted Patent B2
US 11,434,228 · App. 16/650,732 · Granted Sep 6, 2022

Heterocyclic compound and organic light emitting device comprising same

Inventors: Gi-Back Lee (Osan-si, KR); Seong-Jong Park (Osan-si, KR); Ji-Young Kim (Yongin-si, KR); Won-Jang Jeong (Hwaseong-si, KR); Jin-Seok Choi (Suwon-si, KR); Dae-Hyuk Choi (Yongin-si, KR); Joo-Dong Lee (Seongnam-si, KR)
Assignee: LT MATERIALS CO., LTD.
C07D403/14C07D403/04C07D407/14C07D409/14H01L51/0054H01L51/0067H01L51/0073H01L51/4273H01L51/5072H01L51/5092
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Quick Facts
Patent No.
US 11,434,228
App. No.
16/650,732
Granted
Sep 6, 2022
Kind
B2
Abstract

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

Claims (37)

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

wherein, in Chemical Formula 1,

R 1 is hydrogen; a C1 to C60 alkyl group; a C6 to C60 aryl group; a C2 to C60 heteroaryl group; P(═O)RR′; or SiRR′R″;

Ar is selected from the group consisting of deuterium; a halogen group; —CN; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; —SiRR′R″; —P(═O)RR′; and an amine group unsubstituted or substituted with a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;

R 2 to R 5 , R a and R b are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a halogen group; —CN; 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; —SiRR′R″; —P(═O)RR′; and an amine group unsubstituted or substituted with a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl 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;

wherein R, R′ and R″ are the same as or different from each other, and each independently hydrogen; deuterium; —CN; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; and

p and q are an integer of 0 to 5.

2. The heterocyclic compound of claim 1 , wherein the “substituted or unsubstituted” means being substituted with one or more substituents selected from the group consisting of C1 to C60 linear or branched alkyl; C2 to C60 linear or branched alkenyl; C2 to C60 linear or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; —SiRR′R″; —P(═O)RR′; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine, or being unsubstituted, or being substituted with a substituent linking two or more substituents selected from among the substituents illustrated above, or being unsubstituted; and

wherein R, R′ and R″ have the same definitions as in Chemical Formula 1.

3. The heterocyclic compound of claim 1 , wherein Ar may be represented by -(L)m-(Z)n;

L is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;

Z is deuterium; a substituted or unsubstituted alkyl group; a halogen group; —CN; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; —SiRR′R″; or —P(═O)RR′;

m is an integer of 0 to 4;

n is an integer of 1 to 5; and

r, R′ and R″ have the same definitions as in Chemical Formula 1.

4. The heterocyclic compound of claim 3 , wherein L is a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group;

wherein Z is a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or —P(═O)RR′; and

R, R′ and R″ have the same definitions as in claim 3 .

5. The heterocyclic compound of claim 1 , wherein R 2 to R 5 , R a and R b are hydrogen.

6. The heterocyclic compound of claim 1 , wherein R 1 of Chemical Formula 1 is hydrogen; or a C6 to C40 aryl group.

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

8. An organic light emitting device comprising:

a first electrode;

a second electrode provided opposite to the first 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 comprise the heterocyclic compound of claim 1 .

9. The organic light emitting device of claim 8 , wherein the organic material layer comprises an electron transfer layer, and the electron transfer layer comprises the heterocyclic compound.

10. The organic light emitting device of claim 8 , wherein the organic material layer comprises an electron injection layer or an electron transfer layer, and the electron injection layer or the electron transfer layer comprises the heterocyclic compound.

11. The organic light emitting device of claim 8 , wherein the organic material layer comprises an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the heterocyclic compound.

12. The organic light emitting device of claim 8 , comprising:

a first electrode;

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

a charge generation layer provided on the first stack;

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

a second electrode provided on the second stack.

13. The organic light emitting device of claim 12 , wherein the charge generation layer comprises the heterocyclic compound represented by Chemical Formula 1.

14. The organic light emitting device of claim 13 , wherein the charge generation layer is an N-type charge generation layer, and the charge generation layer further comprises a dopant in addition to the heterocyclic compound represented by Chemical Formula 1.

Assignments (2)
CHANGE OF NAME Recorded Jun 23, 2020
From: HEESUNG MATERIAL LTD.
To: LT MATERIALS CO., LTD.
Reel/Frame 053613/0824 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 25, 2020
From: LEE, GI-BACK; PARK, SEONG-JONG; KIM, JI-YOUNG; JEONG, WON-JANG; CHOI, JIN-SEOK; CHOI, DAE-HYUK; LEE, JOO-DONG
To: HEESUNG MATERIAL LTD.
Reel/Frame 052230/0216 →
Priority Claims (1)
KR 10-2017-0127755 · Sep 29, 2017 · national
Continuity (1)
Related Publication 20200308150A1 · Oct 1, 2020