US 12,225,817 B2
Condensed cyclic compound and organic light-emitting device including the same
Sangmo Kim, Hwaseong-si (KR); Hyunjung Kim, Suwon-si (KR); Soonok Jeon, Seoul (KR); Yeonsook Chung, Seoul (KR); Miyoung Chae, Suwon-si (KR); Dalho Huh, Suwon-si (KR); Eunsuk Kwon, Suwon-si (KR); Jongsoo Kim, Suwon-si (KR); and Myungsun Sim, Suwon-si (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR); and SAMSUNG SDI CO., LTD., Gyeonggi-Do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR); and Samsung SDI Co., Ltd., Yongin-si (KR)
Filed on May 9, 2022, as Appl. No. 17/739,532.
Application 17/739,532 is a continuation of application No. 15/258,544, filed on Sep. 7, 2016, abandoned.
Claims priority of application No. 10-2015-0127715 (KR), filed on Sep. 9, 2015; and application No. 10-2016-0110092 (KR), filed on Aug. 29, 2016.
Prior Publication US 2022/0271237 A1, Aug. 25, 2022
Int. Cl. H01L 51/54 (2006.01); C07D 209/94 (2006.01); C07D 487/04 (2006.01); C07D 491/04 (2006.01); C07D 491/048 (2006.01); C07D 495/04 (2006.01); C07D 513/04 (2006.01); C07D 519/00 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 85/30 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/6572 (2023.02) [C07D 209/94 (2013.01); C07D 487/04 (2013.01); C07D 491/04 (2013.01); C07D 491/048 (2013.01); C07D 495/04 (2013.01); C07D 513/04 (2013.01); C07D 519/00 (2013.01); C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 85/657 (2023.02); H10K 50/11 (2023.02); H10K 85/342 (2023.02); H10K 85/615 (2023.02); H10K 85/631 (2023.02); H10K 85/653 (2023.02); H10K 2101/10 (2023.02)] 14 Claims
 
1. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode and comprising an emission layer,
wherein the emission layer comprises a host and a dopant, wherein the host comprises one or more of a condensed cyclic compound represented by Formula 1:

OG Complex Work Unit Chemistry
in Formulae 1 to 5,
Ar1 is a group represented by Formula 2,
Ar2 is a group represented by Formula 3,
CY1 is selected from a fluorene group, a carbazole group, and a dibenzofuran group,
CY2 and CY3 are each a benzene group,
i) L1 is a group represented by Formula 4 and L2 is a group represented by Formula 5;
ii) L1 is a group represented by Formula 5 and L2 is a group represented by Formula 4; or
iii) L1 and L2 are each independently a group represented by Formula 4,
CY4 and CY5 are each independently selected from C5-C30 carbocyclic groups,
R1 to R4, R10, R20 and R30 are each independently selected from a hydrogen, a deuterium, a cyano group (CN), a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryloxy group, a substituted or unsubstituted C2-C60 heteroarylthio group, a substituted or unsubstituted C3-C60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q4)(Q5), and —B(Q6)(Q7),
R40 and R50 are each independently selected from a hydrogen, a deuterium, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryloxy group, a substituted or unsubstituted C2-C60 heteroarylthio group, a substituted or unsubstituted C3-C60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q4)(Q5), and —B(Q6)(Q7),
a1 to a5 are each independently an integer of 0 to 10,
each of * and *′ is a binding site to a neighboring atom,
at least one substituent of the substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C3-C10 cycloalkyl group, substituted C1-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C1-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C7-C60 arylalkyl group, substituted C1-C60 heteroaryl group, substituted C2-C60 heteroaryloxy group, substituted C2-C60 heteroarylthio group, substituted C3-C60 heteroarylalkyl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
a deuterium, —CD3, —CD2H, —CDH2, a cyano group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group and a C1-C60 alkoxy group, each substituted with at least one selected from a deuterium, —CD3, —CD2H, —CDH2, a cyano group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q14)(Q15) and —B(Q16)(Q17);
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —CD3, —CD2H, —CDH2, a cyano group, a C1-Coo alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q24)(Q25) and —B(Q26)(Q27); and
—Si(Q31)(Q32)(Q33), —N(Q34)(Q35) and —B(Q36)(Q37), and
Q1 to Q7, Q11 to Q17, Q21 to Q27 and Q31 to Q37 are each independently selected from a hydrogen, a deuterium, a cyano group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryloxy group, a substituted or unsubstituted C2-C60 heteroarylthio group, a substituted or unsubstituted C3-C60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.