IP Library › Granted Patent US 12,404,271
Granted Patent B2
US 12,404,271 · App. 16/523,168 · Granted Sep 2, 2025

Organic electroluminescence device and polycyclic compound for organic electroluminescence device

Inventor: Akinori Yamatani (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
H10K85/631C07D471/04C07D497/14C07F5/027C07F7/10C07F9/657163C09K11/025C09K11/06H10K85/40H10K85/60H10K85/657H10K85/6572H10K85/658C09K2211/1018H10K50/11H10K50/15H10K50/16H10K50/17H10K50/171H10K50/18H10K2101/10H10K2101/20
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 12,404,271
App. No.
16/523,168
Granted
Sep 2, 2025
Kind
B2
Abstract

An organic electroluminescence device includes a first electrode, a hole transport region on the first electrode, an emission layer on the hole transport region, the emission layer including a condensed polycyclic compound of three or more six-membered rings, at least two six-membered rings among the six-membered rings including an electron donor moiety and an electron acceptor moiety at facing positions, respectively, the at least two six-membered rings not being immediately adjacent to each other, an electron transport region on the emission layer, and a second electrode on the electron transport region.

Claims (98)

1. An organic electroluminescence device, comprising:

a first electrode;

a hole transport region on the first electrode;

an emission layer on the hole transport region, the emission layer including a condensed polycyclic compound of three or more six-membered rings, at least two six-membered rings among the six-membered rings including an electron donor moiety and an electron acceptor moiety at facing positions, respectively, the at least two six-membered rings not being immediately adjacent to each other;

an electron transport region on the emission layer; and

a second electrode on the electron transport region,

wherein the first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, In, Sn, and Zn, a compound of two or more thereof, a mixture of two or more thereof, and oxides thereof,

wherein the polycyclic compound is represented by any one among Formula 1 to Formula 3:

in Formula 1 to Formula 3,

A 1 to A 7 are each independently CO, BR 1 , SiR 2 R 3 , GeR 4 R 5 , POR 6 , PSR 7 , SO, or SO 2 ,

D 1 to D 7 are each independently NR 8 , O, S, or Se,

W 1 to W 4 are each independently N or CR 9 ,

a to g are each independently 0 or 1,

rings M 1 to M 7 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

R 1 to R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

R 9 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a phosphine oxide group, a phosphine sulfide group, a carbonyl group, a boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

when D 3 is NR 8 and A 3 and A 4 are CO, D 4 is NR 8 , O, or Se,

when D 5 to D 7 are NR 8 , at least one Ra is a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

when, in Formula 1, W 1 and We are each CR 9 , A 1 and A 2 are each BR 1 , D 1 and D 2 are each NR 8 , and rings M 1 and M 2 are each a substituted or unsubstituted phenyl group, at least one selected from R 1 , R 9 , and rings M 1 and M 2 is substituted with a halogen atom, and

when M 1 and M 2 in Formula 1 are each a six-membered ring, i) D 1 and D 2 are each not NR 8 , or ii) at least one selected from A 1 and A 2 is BR 1 , SiR 2 R 3 , GeR 4 R 5 , POR 6 , or PSR 7 , and when M 3 and M 4 in Formula 2 are each a six-membered ring, iii) D 3 and D 4 are each not NR 8 , or iv) at least one selected from A 3 and A 4 is BR 1 , SiR 2 R 3 , GeR 4 R 5 , POR 6 , or PSR 7 .

2. The organic electroluminescence device as claimed in claim 1 , wherein:

the emission layer is a delayed fluorescence emission layer including a host and a dopant, and

the host or the dopant includes the polycyclic compound.

3. The organic electroluminescence device as claimed in claim 1 , wherein:

the emission layer is a phosphorescence emission layer including a host and a dopant, and

the host includes the polycyclic compound.

4. The organic electroluminescence device as claimed in claim 1 , wherein the electron donor moiety includes an amine group, an oxygen atom, a sulfur atom, or a selenium atom.

5. The organic electroluminescence device as claimed in claim 1 , wherein the electron acceptor moiety includes a carbonyl group, a boron group, a silyl group, a germyl group, a phosphine oxide group, a phosphine sulfide group, a sulfoxide group, or a sulfur dioxide group.

6. The organic electroluminescence device as claimed in claim 1 , wherein the emission layer emits blue light.

7. The organic electroluminescence device as claimed in claim 1 , wherein A 1 to A 7 are represented by the following Formula 4:

in Formula 4,

V 1 to V 5 are each independently N, CR 10 , or CR 11 , provided that at least one among V 1 to V 5 is CR 11 ,

R 10 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a phosphine oxide group, a phosphine sulfide group, a carbonyl group, a boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and

R 11 is a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

8. The organic electroluminescence device as claimed in claim 1 , wherein Formula 1 to Formula 3 are represented by the following Formula 1-1 to Formula 1-3, respectively:

in Formulae 1-1 to 1-3,

R 21 to R 34 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a phosphine oxide group, a phosphine sulfide group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and

A 1 to A 7 , D 1 to D 7 , and W 1 to W 4 are the same as defined in Formula 1 to Formula 3.

9. The organic electroluminescence device as claimed in claim 1 , wherein Formula 1 to Formula 3 are represented by the following Formula 2-1 to Formula 2-3, respectively:

in Formula 2-1 to Formula 2-3,

R 35 to R 62 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a phosphine oxide group, a phosphine sulfide group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and

A 1 to A 7 , D 1 to D 7 , and W 1 to W 4 are the same as defined in Formula 1 to Formula 3.

10. The organic electroluminescence device as claimed in claim 1 , wherein the condensed polycyclic compound in the emission layer includes at least one compound among compounds represented in the following Compound Group 1:

11. An organic electroluminescence device, comprising:

a first electrode;

a hole transport region on the first electrode;

an emission layer on the hole transport region;

an electron transport region on the emission layer; and

a second electrode on the electron transport region,

wherein the first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, In, Sn, and Zn, and a compound of two or more thereof, a mixture of two or more thereof, and oxides thereof, and

wherein the emission layer includes a polycyclic compound represented by any one among the following Formula 1 to Formula 3:

in Formula 1 to Formula 3,

A 1 to A 7 are each independently CO, BR 1 , SiR 2 R 3 , GeR 4 R 5 , POR 6 , PSR 7 , SO, or SO 2 ,

D 1 to D 7 are each independently NR 8 , O, S, or Se,

W 1 to W 4 are each independently N or CR 9 ,

a to g are each independently 0 or 1,

rings M 1 to M 7 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

R 1 to R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

R 9 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a phosphine oxide group, a phosphine sulfide group, a carbonyl group, a boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

when D 3 is NR 8 and A 3 and A 4 are CO, D 4 is NR 8 , O, or Se,

when D 5 to D 7 are NR 8 , at least one R 8 is a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

when, in Formula 1, W 1 and We are each CR 9 , A 1 and A 2 are each BR 1 , D 1 and D 2 are each NR 8 , and rings M 1 and M 2 are each a substituted or unsubstituted phenyl group, at least one selected from R 1 , R 9 , and rings M 1 and M 2 is substituted with a halogen atom, and

when M 1 and M 2 in Formula 1 are each a six-membered ring, i) D 1 and D 2 are each not NR 8 , or ii) at least one selected from A 1 and A 2 is BR 1 , SiR 2 R 3 , GeR 4 R 5 , POR 6 , or PSR 7 , and when M 3 and M 4 in Formula 2 are each a six-membered ring, iii) D 3 and D 4 are each not NR 8 , or iv) at least one selected from A 3 and A 4 is BR 1 , SiR 2 R 3 , GeR 4 R 5 , POR 6 , or PSR 7 .

12. The organic electroluminescence device as claimed in claim 11 , wherein:

the emission layer is a delayed fluorescence emission layer including a host and a dopant, and

the host includes the polycyclic compound represented by any one among Formula 1 to Formula 3.

13. The organic electroluminescence device as claimed in claim 11 , wherein:

the emission layer is a phosphorescence emission layer including a host and a dopant, and

the host includes the polycyclic compound represented by any one among Formula 1 to Formula 3.

14. The organic electroluminescence device as claimed in claim 12 , wherein the polycyclic compound is at least one among compounds represented in the following Compound Group 1:

15. A polycyclic compound represented by any one among Formula 1 to Formula 3:

in Formula 1 to Formula 3,

A 1 to A 7 are each independently CO, BR 1 , SiR 2 R 3 , GeR 4 R 5 , POR 6 , PSR 7 , SO, or SO 2 ,

D 1 to D 7 are each independently NR 8 , O, S, or Se,

W 1 to W 4 are each independently N or CR 9 ,

a to g are each independently 0 or 1,

rings M 1 to M 7 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

R 1 to R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

R 9 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a phosphine oxide group, a phosphine sulfide group, a carbonyl group, a boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

when D 3 is NR 8 and A 3 and A 4 are CO, D 4 is NR 8 , O, or Se,

when D 5 to D 7 are NR 8 , at least one R 8 is a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

when, in Formula 1, W 1 and We are each CR 9 , A 1 and A 2 are each BR 1 , D 1 and D 2 are each NR 8 , and rings M 1 and M 2 are each a substituted or unsubstituted phenyl group, at least one selected from R 1 , R 9 , and rings M 1 and M 2 is substituted with a halogen atom, and

when M 1 and M 2 in Formula 1 are each a six-membered ring, i) D 1 and D 2 are each not NR 8 , or ii) at least one selected from A 1 and A 2 is BR 1 , SiR 2 R 3 , GeR 4 R 5 , POR 6 , or PSR 7 , and when M 3 and M 4 in Formula 2 are each a six-membered ring, iii) D 3 and D 4 are each not NR 8 and A 3 and A 4 are not both CO, or iv) at least one selected from A 3 and A 4 is BR 1 , SiR 2 R 3 , GeR 4 R 5 , POR 6 , or PSR 7 , and

wherein the polycyclic compound represented by any one among Formula 1 to Formula 3 has a lowest triplet excitation energy of about 3.0 eV or less.

16. The polycyclic compound as claimed in claim 15 , wherein Formula 1 to Formula 3 are represented by the following Formula 1-1 to Formula 1-3, respectively:

in Formulae 1-1 to 1-3,

R 21 to R 34 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a phosphine oxide group, a phosphine sulfide group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and

A 1 to A 7 , D 1 to D 7 , and W 1 to W 4 are the same as defined in Formula 1 to Formula 3.

17. The polycyclic compound as claimed in claim 15 , wherein Formula 1 to Formula 3 are represented by the following Formula 2-1 to Formula 2-3, respectively:

in Formula 2-1 to Formula 2-3,

R 35 to R 62 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a phosphine oxide group, a phosphine sulfide group, a silyl group, a carbonyl group, a boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and

A 1 to A 7 , D 1 to D 7 , and W 1 to W 4 are the same as defined in Formula 1 to Formula 3.

18. The polycyclic compound as claimed in claim 15 , wherein:

in Formula 1, D 1 and D 2 are the same, and A 1 and A 2 are the same, and

in Formula 3, D 5 to D 7 are the same, and A 5 to A 7 are the same.

19. The polycyclic compound as claimed in claim 15 , wherein the polycyclic compound represented by any one among Formula 1 to Formula 3 is a material for emitting thermally activated delayed fluorescence.

20. The polycyclic compound as claimed in claim 15 , wherein the polycyclic compound represented by any one among Formula 1 to Formula 3 is a phosphorescence host material.

21. The polycyclic compound as claimed in claim 15 , wherein the polycyclic compound represented by any one among Formula 1 to Formula 3 is at least one among compounds represented in the following Compound Group 1:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2019
From: YAMATANI, AKINORI
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 049871/0374 →
Priority Claims (1)
KR 10-2018-0088926 · Jul 31, 2018 · national
Continuity (1)
Related Publication 20200044159A1 · Feb 6, 2020
References Cited (76)
US 6602618B2 · Watanabe et al. · 2003 [cited by applicant]
US 10374166B2 · Hatakeyama et al. · 2019 [cited by applicant]
US 10483471B2 · Ishidai et al. · 2019 [cited by applicant]
US 10804482B2 · Sakamoto · 2020 [cited by applicant]
US 20040170863A1 · Kim · 2004 [cited by examiner]
US 20070059552A1 · Takeda et al. · 2007 [cited by applicant]
US 20120319091A1 · Kato · 2012 [cited by applicant]
US 20140034926A1 · Matsubara et al. · 2014 [cited by applicant]
US 20150236274A1 · Hatakeyama et al. · 2015 [cited by applicant]
US 20160351811A1 · Lam et al. · 2016 [cited by applicant]
US 20180069182A1 · Hatakeyama et al. · 2018 [cited by applicant]
US 20180094000A1 · Hatakeyama et al. · 2018 [cited by applicant]
US 20180108857A1 · Adachi et al. · 2018 [cited by applicant]
US 20180301629A1 · Hatakeyama et al. · 2018 [cited by applicant]
US 20190058124A1 · Hatakeyama et al. · 2019 [cited by applicant]
US 20190115538A1 · Lim et al. · 2019 [cited by applicant]
US 20190207112A1 · Hatakeyama et al. · 2019 [cited by applicant]
US 20190348617A1 · Mamada · 2019 [cited by examiner]
US 20210159411A1 · Sim et al. · 2021 [cited by applicant]
US 20210273174A1 · Kuwabara et al. · 2021 [cited by applicant]
US 20210305512A1 · Suzaki · 2021 [cited by applicant]
US 20210376250A1 · Suzaki · 2021 [cited by applicant]
CA 3017002A1 · 2019 [cited by examiner]
CH 422200A · 1966 [cited by examiner]
CN 107417715A · 2017 [cited by applicant]
JP 200773891A · 2007 [cited by applicant]
JP 2012116784 · 2012 [cited by examiner]
JP 5935199B2 · 2016 [cited by applicant]
JP WO2017138526A1 · 2017 [cited by applicant]
JP 2018043984A2 · 2018 [cited by applicant]
KR 101516062B1 · 2015 [cited by applicant]
KR 101523124B1 · 2015 [cited by applicant]
KR 1020160119683A · 2016 [cited by applicant]
KR 1020170082447A · 2017 [cited by applicant]
KR 1020170130434A · 2017 [cited by applicant]
KR 1020170130435A · 2017 [cited by applicant]
KR 101876763B1 · 2018 [cited by applicant]
KR 101886773B1 · 2018 [cited by applicant]
KR 1020180108604A · 2018 [cited by applicant]
KR 1020180122298A · 2018 [cited by applicant]
KR 1020180134850A · 2018 [cited by applicant]
KR 1020190025065 · 2019 [cited by applicant]
KR 101955647B1 · 2019 [cited by applicant]
KR 101955648B1 · 2019 [cited by applicant]
KR 1020190035990A · 2019 [cited by applicant]
KR 1020190042791A · 2019 [cited by applicant]
WO WO2015102118A1 · 2015 [cited by applicant]
WO WO2016152418A1 · 2016 [cited by applicant]
WO WO2016152544A1 · 2016 [cited by applicant]
WO WO2016152605A1 · 2016 [cited by applicant]
WO WO2017188111A1 · 2017 [cited by applicant]
WO WO2018212169A1 · 2018 [cited by applicant]
WO WO2019052940 · 2019 [cited by examiner]
WO WO2019052940A1 · 2019 [cited by examiner]
WO 2021230133A1 · 2021 [cited by applicant]
WO 2022096495A1 · 2022 [cited by applicant]
Chibani et al. “Excited States of Ladder-Type π-Conjugated Dyes with a Joint SOS-CIS(D) and PCM-TD-DFT Approach” J. Phys. Chem. A. 119—pp. 5417-5425. 2015 (Year: 2015). [cited by examiner]
Wang et al. “Synthesis of Di- and Trixanthones that Display High Stability and a Visual Fluorescence Response to Strong Acid” Chem. Asian J. 9—pp. 3307-3312. 2014 (Year: 2014). [cited by examiner]
Coloquhour et al., Synthesis of Dixanthones and Poly(dixanthone)s by Cyclization of 2-Aryloxybenzonitriles in rifluoromethanesulfonic Acid; 2001; Org. Lett., vol. 3, No. 15, p. 2337-2340 (Year: 2001). [cited by examiner]
Anton Pershin, et al., “Highly emissive excitons with reduced exchange energy in thermally activated delayed fluorescent molecules,” Nature Communications, vol. 10, No. 597, (2019), pp. 1-5. [cited by applicant]
Agou, T., et al. “Syntheses, Structure, and Optical Properties of Ladder-Type Fused Azaborines,” Organic Letters 8(11), 2006, pp. 2241-2244. [cited by applicant]
Chinese Office Action dated Mar. 17, 2023 for corresponding CN Appl. No. 201910694080.8, citing JP 2012-116784 A (previously cited), 11 pages. [cited by applicant]
English abstract for JP 2012-116784 A (previously cited), 1 page. [cited by applicant]
Office Action for U.S. Appl. No. 17/002,617 dated Mar. 17, 2023, 6 pages. [cited by applicant]
Zhang, J., et al. “The Ground State Spin Multiplicity of Schlenk-type Biradicals and the Influence of Additional Linkage to Ladder Type Structures” Chemical Physics 206, 1996, pp. 339-351. [cited by applicant]
WO-2021230133-A1 machine translation (Year: 2021). [cited by applicant]
U.S. Office Action dated May 17, 2023, issued in U.S. Appl. No. 17/110,108 (35 pages). [cited by applicant]
U.S. Notice of Allowance dated Jul. 19, 2023, issued in U.S. Appl. No. 17/002,617 (8 pages). [cited by applicant]
Notice of Allowance for U.S. Appl. No. 17/110,108 dated Dec. 22, 2023, 10 pages. [cited by applicant]
Agou, et. al., “Electronic and Optical Properties of Ladder-type Heteraborins,” Chem. Eur. J. (2007), pp. 8051-8060. [cited by applicant]
Office Action for U.S. Appl. No. 16/780,744 dated Feb. 1, 2024, 8 pages. [cited by applicant]
U.S. Final Office Action dated Jun. 18, 2024, issued in U.S. Appl. No. 16/780,744 (9 pages). [cited by applicant]
U.S. Office Action dated Sep. 17, 2024, issued in U.S. Appl. No. 16/780,744 (9 pages). [cited by applicant]
Korean Notice of Allowance dated Nov. 27, 2024, issued in corresponding Korean Patent Application No. 10-2019-0042995 (7 pages). [cited by applicant]
US Final Office Action dated Feb. 24, 2025, issued in U.S. Appl. No. 16/780,744 (9 pages). [cited by applicant]
US Notice of Allowance dated Jun. 13, 2025, issued in U.S. Appl. No. 16/780,744, 8 pages. [cited by applicant]