IP Library › Granted Patent US 12,441,684
Granted Patent B2
US 12,441,684 · App. 17/385,218 · Granted Oct 14, 2025

Organic compound for capping layer and organic light emitting diode comprising the same

Inventors: Ho Wan Ham (Hwaseong-si, KR); Hyun Cheol An (Hwaseong-si, KR); Hee Joo Kim (Hwaseong-si, KR); Dong Jun Kim (Hwaseong-si, KR); Jeong Woo Han (Hwaseong-si, KR); Ja Eun Ann (Hwaseong-si, KR); Dong Yuel Kwon (Hwaseong-si, KR); Sung Kyu Lee (Hwaseong-si, KR); Tae Min Kim (Hwaseong-si, KR)
Assignee: Dongjin Semichem Co., Ltd.
C07D209/86C07D493/00C07D495/00H10K50/858H10K85/622H10K85/626H10K85/636H10K85/6572H10K85/6574H10K50/80H10K71/00H10K2101/00
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Quick Facts
Patent No.
US 12,441,684
App. No.
17/385,218
Granted
Oct 14, 2025
Kind
B2
Abstract

As a compound for a capping layer for an organic light emitting device, disclosed is a capping layer compound represented by Formula 1 below. In addition, an organic light emitting device including the capping layer compound is also disclosed.

Claims (47)

1. A capping layer that is disposed on an outer surface of a first electrode or a second electrode of an organic light emitting device,

wherein the capping layer comprises a compound represented by Formula 3 below:

wherein X is O, S, Se, Te, or CRR′,

R and R′ are each independently hydrogen, deuterium, halogen, a nitro group, a nitrile group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 sulfide, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group, wherein R and R′ that are adjacent to each other form or do not form a ring by combining with each other,

Y 1 to Y 4 are each independently C, CR 1 , or N,

R 1 s are each independently hydrogen, deuterium, halogen, a nitro group, a nitrile group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 sulfide group, or a substituted or unsubstituted C6-C50 aryl group, wherein the R 1 s adjacent to each other form or do not form a ring by combining with each other,

Ar 1 and Ar 2 are each independently selected from the group consisting of an unsubstituted C6-C50 aryl group, a C6-C50 aryl group that is substituted with either an unsubstituted C6-C50 aryl group or an unsubstituted C2-C50 heteroaryl group, and an unsubstituted C2-C50 heteroaryl group,

R 2 s are each independently hydrogen, deuterium, halogen, a nitro group, a nitrile group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 sulfide group, a substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted heteroaryl group,

L is a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted terphenylene,

L 1 , and L 2 are each independently a directly-linked, substituted or unsubstituted C6-C50 arylene group, or a substituted or unsubstituted C2-C50 heteroarylene group, and

p is 0 or 1.

2. The capping layer of claim 1 , wherein Formula 3 is a compound represented by Formula 2-1 below:

wherein R 3 is defined in the same way as R 2 in Formula 3, provided that the number of carbon atoms in R 3 satisfies the carbon number range defined for L,

q is an integer in a range of from 0 to 4, and

m is an integer in a range of from 2 to 3.

3. The capping layer of claim 1 , wherein Formula 3 is a compound represented by Formula 4-1 below:

wherein R 3 is defined in the same way as R 2 in Formula 3, provided that the number of carbon atoms in R 3 satisfies the carbon number range defined for L,

q is an integer in a range of from 0 to 4, and

m is an integer in a range of from 2 to 3.

4. The capping layer of claim 1 , wherein Formula 3 is a compound represented by Formula 5-1 below:

wherein R 3 s are each independently defined in the same way as R 2 in Formula 3, provided that the number of carbon atoms in R 3 satisfies the carbon number range defined for L,

R 4 s are each independently defined in the same way as R 1 in Formula 3,

p is 0 or 1,

q is an integer in a range of from 0 to 4,

m is an integer in a range of from 2 to 3, and

n is an integer in a range of from 0 to 4.

5. The capping layer of claim 1 , wherein Formula 3 is a compound represented by Formula 6-1 below:

wherein L 3 is defined in the same way as L 2 in Formula 3,

X 2 is defined in the same way as X in Formula 3, and

Y 5 to Y 8 are each independently defined in the same way as Y 1 to Y 4 in Formula 3, provided that the number of carbon atoms in Y 5 to Y 8 satisfies the carbon number range defined for Ar 2 .

6. The capping layer of claim 1 , wherein Formula 3 is a compound represented by Formula 7-1 below:

wherein L 3 and L 4 are each independently defined in the same way as L 1 and L 2 in Formula 3,

X 2 and X 3 are each independently defined in the same way as X in Formula 3, and

Y 5 to Y 12 are each independently defined in the same way as Y 1 to Y 4 in Formula 3, provided that the number of carbon atoms in Y 5 to Y 12 satisfies the carbon number range defined for Ar 1 or Ar 2 .

7. The capping layer of claim 1 , wherein the X is O or S.

8. The capping layer of claim 1 , wherein the R 1 and R 2 are each independently selected from the group consisting of hydrogen, deuterium, a methyl group, a methoxy group, a phenyl group, and combinations thereof.

9. The capping layer of claim 8 , wherein the R 1 and R 2 are each independently selected from the group consisting of hydrogen, a phenyl group, a biphenyl group, and combinations thereof.

10. The capping layer of claim 1 , wherein the L 1 , and L 2 of the compound are not directly-linked.

11. The capping layer of claim 1 , wherein the Ar 1 and Ar 2 are each independently selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, a benzofuran group, a benzothiophene group, and combinations thereof.

12. The capping layer of claim 1 , wherein the compound is any one selected from the following compounds:

13. An organic light emitting device comprising:

a first electrode;

a second electrode;

an organic light material layer interposed between the first electrode and the second electrode; and

the capping layer of claim 1 disposed on an outer surface of either the first electrode or the second electrode.

14. The organic light emitting device of claim 13 , wherein the capping layer has a thickness in a range of from 300 Å to 1000 Å.

15. The organic light emitting device of claim 13 , wherein the capping layer has a refractive index of 2.23 or more for a wavelength of 450 nm.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2021
From: HAM, HO WAN; AN, HYUN CHEOL; KIM, HEE JOO; KIM, DONG JUN; HAN, JEONG WOO; ANN, JA EUN; KWON, DONG YUEL; LEE, SUNG KYU; KIM, TAE MIN
To: DONGJIN SEMICHEM CO., LTD.
Reel/Frame 056979/0836 →
Priority Claims (1)
KR 10-2020-0141337 · Oct 28, 2020 · national
Continuity (1)
Related Publication 20220127277A1 · Apr 28, 2022
References Cited (6)
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WO WO2011043083A1 · 2011 [cited by examiner]
Machine English translation of Fujishita et al. (JP 2001-354668 A). Mar. 27, 2024. [cited by examiner]
Machine English translation of Ham et al. (KR-10-2017-0031614). Jan. 9, 2025. [cited by examiner]