US 12,404,271 B2
Organic electroluminescence device and polycyclic compound for organic electroluminescence device
Akinori Yamatani, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by SAMSUNG DISPLAY CO., LTD., Yongin-si (KR)
Filed on Jul. 26, 2019, as Appl. No. 16/523,168.
Claims priority of application No. 10-2018-0088926 (KR), filed on Jul. 31, 2018.
Prior Publication US 2020/0044159 A1, Feb. 6, 2020
Int. Cl. H01L 51/50 (2006.01); C07D 471/04 (2006.01); C07D 497/14 (2006.01); C07F 5/02 (2006.01); C07F 7/10 (2006.01); C07F 9/6571 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 50/18 (2023.01); H10K 101/10 (2023.01); H10K 101/20 (2023.01)
CPC H10K 85/631 (2023.02) [C07D 471/04 (2013.01); C07D 497/14 (2013.01); C07F 5/027 (2013.01); C07F 7/10 (2013.01); C07F 9/657163 (2013.01); C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 85/40 (2023.02); H10K 85/60 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); H10K 85/658 (2023.02); C09K 2211/1018 (2013.01); H10K 50/11 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/17 (2023.02); H10K 50/171 (2023.02); H10K 50/18 (2023.02); H10K 2101/10 (2023.02); H10K 2101/20 (2023.02)] 21 Claims
OG exemplary drawing
 
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:

OG Complex Work Unit Chemistry
in Formula 1 to Formula 3,
A1 to A7 are each independently CO, BR1, SiR2R3, GeR4R5, POR6, PSR7, SO, or SO2,
D1 to D7 are each independently NR8, O, S, or Se,
W1 to W4 are each independently N or CR9,
a to g are each independently 0 or 1,
rings M1 to M7 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,
R1 to R8 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,
R9 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 D3 is NR8 and A3 and A4 are CO, D4 is NR8, O, or Se,
when D5 to D7 are NR8, 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, W1 and We are each CR9, A1 and A2 are each BR1, D1 and D2 are each NR8, and rings M1 and M2 are each a substituted or unsubstituted phenyl group, at least one selected from R1, R9, and rings M1 and M2 is substituted with a halogen atom, and
when M1 and M2 in Formula 1 are each a six-membered ring, i) D1 and D2 are each not NR8, or ii) at least one selected from A1 and A2 is BR1, SiR2R3, GeR4R5, POR6, or PSR7, and when M3 and M4 in Formula 2 are each a six-membered ring, iii) D3 and D4 are each not NR8, or iv) at least one selected from A3 and A4 is BR1, SiR2R3, GeR4R5, POR6, or PSR7.
 
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:

OG Complex Work Unit Chemistry
in Formula 1 to Formula 3,
A1 to A7 are each independently CO, BR1, SiR2R3, GeR4R5, POR6, PSR7, SO, or SO2,
D1 to D7 are each independently NR8, O, S, or Se,
W1 to W4 are each independently N or CR9,
a to g are each independently 0 or 1,
rings M1 to M7 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,
R1 to R8 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,
R9 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 D3 is NR8 and A3 and A4 are CO, D4 is NR8, O, or Se,
when D5 to D7 are NR8, at least one R8 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, W1 and We are each CR9, A1 and A2 are each BR1, D1 and D2 are each NR8, and rings M1 and M2 are each a substituted or unsubstituted phenyl group, at least one selected from R1, R9, and rings M1 and M2 is substituted with a halogen atom, and
when M1 and M2 in Formula 1 are each a six-membered ring, i) D1 and D2 are each not NR8, or ii) at least one selected from A1 and A2 is BR1, SiR2R3, GeR4R5, POR6, or PSR7, and when M3 and M4 in Formula 2 are each a six-membered ring, iii) D3 and D4 are each not NR8, or iv) at least one selected from A3 and A4 is BR1, SiR2R3, GeR4R5, POR6, or PSR7.
 
15. A polycyclic compound represented by any one among Formula 1 to Formula 3:

OG Complex Work Unit Chemistry
in Formula 1 to Formula 3,
A1 to A7 are each independently CO, BR1, SiR2R3, GeR4R5, POR6, PSR7, SO, or SO2,
D1 to D7 are each independently NR8, O, S, or Se,
W1 to W4 are each independently N or CR9,
a to g are each independently 0 or 1,
rings M1 to M7 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,
R1 to R8 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,
R9 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 D3 is NR8 and A3 and A4 are CO, D4 is NR8, O, or Se,
when D5 to D7 are NR8, at least one R8 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, W1 and We are each CR9, A1 and A2 are each BR1, D1 and D2 are each NR8, and rings M1 and M2 are each a substituted or unsubstituted phenyl group, at least one selected from R1, R9, and rings M1 and M2 is substituted with a halogen atom, and
when M1 and M2 in Formula 1 are each a six-membered ring, i) D1 and D2 are each not NR8, or ii) at least one selected from A1 and A2 is BR1, SiR2R3, GeR4R5, POR6, or PSR7, and when M3 and M4 in Formula 2 are each a six-membered ring, iii) D3 and D4 are each not NR8 and A3 and A4 are not both CO, or iv) at least one selected from A3 and A4 is BR1, SiR2R3, GeR4R5, POR6, or PSR7, 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.