IP Library › Granted Patent US 12,252,485
Granted Patent B2
US 12,252,485 · App. 17/606,553 · Granted Mar 18, 2025

Heterocyclic compound and organic light emitting device comprising same

Inventors: Hye-Su Ji (Yongin, KR); Hyun-Ju La (Yongin, KR); Won-Jang Jeong (Yongin, KR); Dong-Jun Kim (Yongin, KR)
Assignee: LT MATERIALS CO., LTD.
C07D471/04C07D519/00C07F9/28H10K85/622H10K85/624H10K85/626H10K85/654H10K85/6572H10K50/13H10K50/16H10K50/171H10K50/18
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Quick Facts
Patent No.
US 12,252,485
App. No.
17/606,553
Granted
Mar 18, 2025
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 (42)

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

wherein, in Chemical Formula 1,

L 1 and L 2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and a and b are an integer of 0 to 4;

R 1 is selected from the group consisting of a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C 2 to C60 heteroaryl group; —SiRR′R″; —P(═O)RR′; and an amine group unsubstituted or substituted with a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group;

R 2 is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —SiRR′R″; —P(═O)RR′; and an amine group unsubstituted or substituted with a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group;

p and q are an integer of 1 to 5;

R 3 to R 9 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —SiRR′R″; —P(═O)RR′; and an amine group unsubstituted or substituted with a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heteroring;

R, R′ and R″ are a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; and

m is an integer of 0 or 1.

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

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

3. The heterocyclic compound of claim 1 , wherein Chemical Formula 1 is represented by any one of the following Chemical Formula 2 to Chemical Formula 5:

in Chemical Formulae 2 to 5,

R 1 to R 9 , L 1 , L 2 , m, a, b, p and q have the same definitions as in Chemical Formula 1.

4. The heterocyclic compound of claim 1 , wherein Chemical Formula 1 is represented by any one of the following Chemical Formulae 6 to 8:

in Chemical Formulae 6 to 8,

R 1 , R 2 , L 1 , L 2 , a, b, p, q, R 3 , R 4 , R 9 and m have the same definitions as in Chemical Formula 1;

R 15 to R 18 are hydrogen;

L 3 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;

Z 3 is selected from the group consisting of a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —SiRR′R″; —P(═O)RR′; and an amine group unsubstituted or substituted with a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group;

r is an integer of 0 to 4;

s is an integer of 1 to 5; and

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

5. The heterocyclic compound of claim 1 , wherein R 1 is a substituted or unsubstituted C6 to C60 aryl group.

6. The heterocyclic compound of claim 1 , wherein R 3 , R 4 and R 9 are hydrogen.

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 a light emitting layer, and the light emitting 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 , 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.

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

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

the second electrode provided on the second stack.

14. The organic light emitting device of claim 13 , wherein the charge generation layer comprises the heterocyclic compound.

15. 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 comprises the heterocyclic compound.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 26, 2021
From: JI, HYE-SU; LA, HYUN-JU; JEONG, WON-JANG; KIM, DONG-JUN
To: LT MATERIALS CO., LTD.
Reel/Frame 057917/0669 →
Priority Claims (1)
KR 10-2019-0084457 · Jul 12, 2019 · national
Continuity (1)
Related Publication 20220213098A1 · Jul 7, 2022
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