IP Library › Granted Patent US 12,284,905
Granted Patent B2
US 12,284,905 · App. 17/449,220 · Granted Apr 22, 2025

Light emitting device

Inventors: Junha Park (Gwacheon-si, KR); Taeil Kim (Hwaseong-si, KR); Sun Young Pak (Suwon-si, KR); Jang Yeol Baek (Yongin-si, KR); Kyoung Sunwoo (Hwaseong-si, KR); Mun-Ki Sim (Seoul, KR); Chanseok Oh (Seoul, KR); Minjung Jung (Siheung-si, KR)
Assignee: Samsung Display Co., Ltd.
H10K85/322C07F5/027C09K11/06C09K2211/1018H10K50/11H10K2101/10
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 12,284,905
App. No.
17/449,220
Granted
Apr 22, 2025
Kind
B2
Abstract

Provided is a light emitting device including a first electrode, a second electrode, and an emission layer between the first electrode and the second electrode, and the emission layer may include a condensed cyclic compound represented by Formula 1 below, thereby exhibiting high luminous efficiency and improved service life characteristics.

Claims (70)

1. A light emitting device comprising:

a first electrode;

a second electrode on the first electrode; and

an emission layer which is between the first electrode and the second electrode and comprises a condensed cyclic compound represented by Formula 1 below,

wherein the first electrode and the second electrode each independently comprises any one selected from among Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/AI, Mo, Ti, W, In, Sn, Zn, a compound of two or more thereof, a mixture of two or more thereof, and an oxide thereof:

wherein, in Formula 1,

X 1 to X 4 are each independently O, S, CR 5 R 6 , or NR 7 ,

m and n are each independently an integer of 0 to 3,

and p are each independently an integer of 0 to 4,

R 0 to R 7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring-forming carbon atoms, and

at least one selected from among R 1 to R 7 comprises a substituent represented by Formula 2 or Formula 3 below:

wherein, in Formula 2 and Formula 3,

Y 1 to Y 3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocycle having 2 to 30 ring-forming carbon atoms, and

R 8 to R 14 are independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or a unsubstituted silyl group, or a substituted or unsubstituted alkyl group having 1 to 10 carbons atoms

“*”indicates a bonding point to another atom in the R 1 to R 7 group or the condensed cyclic compound represented by Formula 1.

2. The light emitting device of claim 1 , wherein Formula 1 above is represented by any one selected from among Formula 1-1 to Formula 1-6 below:

wherein, in Formula 1-1 to Formula 1-6 above,

R 71 to R 74 each independently correspond to R 7 defined in Formula 1 above, X 1 to X 4 , R 0 to R 4 , and m to p are the same as defined with respect to Formula 1.

3. The light emitting device of claim 1 , wherein at least two selected from among X 1 to X 4 are NR 7 , and the rest are each independently O, S, or CR 5 R 6 , and R 5 to R 7 are the same as defined with respect to Formula 1.

4. The light emitting device of claim 1 , wherein Formula 2 above is represented by Formula 2-1 below:

wherein, in Formula 2-1 above,

R Y1 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and

R 8 to R 11 are the same as defined with respect to Formula 2.

5. The light emitting device of claim 1 , wherein Formula 3 is represented by Formula 3-1 below:

wherein, in Formula 3-1,

R Y2 and R Y3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and

R 12 to R 14 are the same as defined with respect to Formula 3.

6. The light emitting device of claim 1 , wherein Y1 to Y3 are each independently an unsubstituted phenyl group, or a phenyl group substituted with an alkyl group having 1 to 10 carbon atoms.

7. The light emitting device of claim 1 , wherein at least one selected from among R 1 to R 7 comprises any one selected from among S-1 to S-3 below:

8. The light emitting device of claim 1 ,

wherein m and n are 1,

R 1 and R 2 are each independently NR a R b , and

at least one selected from among R a , R b , and R 7 is represented by Formula 2 or Formula 3, and the rest are substituted or unsubstituted aryl groups having 6 to 30 ring-forming carbon atoms.

9. The light emitting device of claim 1 , wherein m and n are 1, and

R 1 and R 2 are represented by any one selected from among AM-1 to AM-11 below:

10. The light emitting device of claim 1 , further comprising a capping layer on the second electrode, wherein the capping layer has a refractive index of about 1.6 or more.

11. The light emitting device of claim 1 , wherein the emission layer is a delayed fluorescence emission layer containing a host and a dopant, and

the dopant comprises the condensed cyclic compound.

12. The light emitting device of claim 1 , wherein the emission layer emits blue light having a center wavelength of about 450 nm to about 470 nm.

13. The light emitting device of claim 1 , wherein the emission layer comprises at least one selected from among the condensed cyclic compounds of Compound Group 1 below:

14. A light emitting device comprising:

a first electrode;

a second electrode on the first electrode;

an emission layer which is between the first electrode and the second electrode and comprises a condensed cyclic compound represented by Formula A below; and

a capping layer which is on the second electrode and has a refractive index of about 1.6 or more:

wherein, in Formula A above,

X 1 to X 4 are each independently O, S, CR 5 R 6 , or NR 7 ,

and p are each independently an integer of 0 to 4,

R a1 , R b1 , R a2 , and R b2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring-forming carbon atoms, or Rai and Rb1 are bonded to each other to form a ring, or R a2 and R b2 combine with each other to form a ring,

R 0 , and R 3 to R 7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring-forming carbon atoms, and

at least one selected from among R a1 , R b1 , R a2 , R b2 , and R 7 comprises a substituent represented by Formula 2 or Formula 3 below:

wherein, in Formula 2 and Formula 3,

Y 1 to Y 3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted amine group, or a substituted or unsubstituted heterocycle having 2 to 30 ring-forming carbon atoms, and

R 8 to R 14 are independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or a unsubstituted silyl group, or a substituted or unsubstituted alkyl group having 1 to 10 carbons atoms

“*”indicates a bonding point to another atom in the R a1 , R b1 , R a1 , R b2 or R 7 group or the condensed cyclic compound represented by Formula A.

15. The light emitting device of claim 14 , wherein Formula A is represented by any one selected from among Formula A-1 to Formula A-6 below:

wherein, in Formula A-1 to Formula A-6,

R 71 to R 74 each independently correspond to R7 defined in Formula A,

X 1 to X 4 , R 0 , R a1 , R b1 , R a2 , R b2 , R 3 , R 4 , o, and p are the same as defined with respect to Formula A.

16. The light emitting device of claim 14 , wherein at least two selected from among X 1 to X 4 are NR 7 , and the rest are each independently O, S, or CR 5 R 6 , and R 5 to R 7 are the same as defined with respect to Formula A.

17. The light emitting device of claim 14 , wherein Formula 2 is represented by Formula 2-1 below:

wherein, in Formula 2-1,

R Y1 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and

R 8 to R 11 are the same as defined with respect to Formula 2.

18. The light emitting device of claim 14 , wherein Formula 3 is represented by Formula 3-1 below:

wherein, in Formula 3-1,

R Y2 and R Y3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and

R 12 to R 14 are the same as defined with respect to Formula 3.

19. The light emitting device of claim 14 , wherein Y 1 to Y 3 are each independently an unsubstituted phenyl group, or a phenyl group substituted with an alkyl group having 1 to 10 carbon atoms.

20. The light emitting device of claim 14 , wherein the emission layer comprises at least one selected from among the condensed cyclic compounds of Compound Group 1 below:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 28, 2021
From: PARK, JUNHA; KIM, TAEIL; PAK, SUN YOUNG; BAEK, JANG YEOL; SUNWOO, KYOUNG; SIM, MUN-KI; OH, CHANSEOK; JUNG, MINJUNG
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 057636/0923 →
Priority Claims (2)
KR 10-2020-0128803 · Oct 6, 2020 · national
KR 10-2021-0119307 · Sep 7, 2021 · national
Continuity (1)
Related Publication 20220115595A1 · Apr 14, 2022
References Cited (46)
US 5645948A · Shi et al. · 1997 [cited by applicant]
US 7700201B2 · Seo et al. · 2010 [cited by applicant]
US 9818985B2 · Cho et al. · 2017 [cited by applicant]
US 10374166B2 · Hatakeyama et al. · 2019 [cited by applicant]
US 20040053069A1 · Sotoyama et al. · 2004 [cited by applicant]
US 20050287393A1 · Lee et al. · 2005 [cited by applicant]
US 20190115538A1 · Lim et al. · 2019 [cited by applicant]
US 20190119312A1 · Chen et al. · 2019 [cited by applicant]
US 20200020859A1 · Hatakeyama et al. · 2020 [cited by applicant]
US 20200044159A1 · Yamatani · 2020 [cited by applicant]
US 20200058885A1 · Hong et al. · 2020 [cited by applicant]
US 20200119289A1 · Lin et al. · 2020 [cited by applicant]
US 20200144503A1 · Hayano · 2020 [cited by applicant]
US 20200144513A1 · Hatakeyama et al. · 2020 [cited by applicant]
US 20200176679A1 · Jeong et al. · 2020 [cited by applicant]
US 20200190115A1 · Hatakeyama et al. · 2020 [cited by applicant]
US 20200283463A1 · Lee et al. · 2020 [cited by applicant]
US 20210277026A1 · Geum et al. · 2021 [cited by applicant]
US 20220112221A1 · Lee · 2022 [cited by examiner]
US 20220407021A1 · Shin · 2022 [cited by examiner]
EP 3109253A1 · 2016 [cited by applicant]
JP 4060669B2 · 2008 [cited by applicant]
JP 2019119680A · 2019 [cited by applicant]
KR 100525408B1 · 2005 [cited by applicant]
KR 1020160119683A · 2016 [cited by applicant]
KR 1020160125583A · 2016 [cited by applicant]
KR 1020160139101A · 2016 [cited by applicant]
KR 101876763B1 · 2018 [cited by applicant]
KR 1020180122298A · 2018 [cited by applicant]
KR 101955648B1 · 2019 [cited by applicant]
KR 1020190042791A · 2019 [cited by applicant]
KR 1020190096944A · 2019 [cited by applicant]
KR 1020190129509A · 2019 [cited by applicant]
KR 102058028B1 · 2019 [cited by applicant]
KR 1020200004248A · 2020 [cited by applicant]
KR 1020200006965A · 2020 [cited by applicant]
KR 1020200011383A · 2020 [cited by applicant]
KR 1020200014451A · 2020 [cited by applicant]
KR 1020200052513A · 2020 [cited by applicant]
KR 1020200107848A · 2020 [cited by applicant]
KR 1020200108147A · 2020 [cited by applicant]
WO WO2018212169A1 · 2018 [cited by applicant]
WO 2020040298A1 · 2020 [cited by applicant]
Kondo, et al., “Narrowband Deep-Blue Organic Light-Emitting Diode Featuring an Organoboron-Based Emitter”, Nature Photonics, Jul. 15, 2019, , vol. 13, pp. 678-682. [cited by applicant]
Office Action for U.S. Appl. No. 17/223,937 dated Oct. 25, 2023, 19 pages. [cited by applicant]
Pershin, et al., “Highly Emissive Excitons with Reduced Exchange Energy In Thermally Activated Delayed Fluorescent Molecules”, Nature Communications, Feb. 5, 2019, vol. 10, No. 597, 5 pages. [cited by applicant]
Cited By (2)
US 12,588,354 US 12,680,017