US 11,691,957 B2
Condensed cyclic compound and organic light-emitting device including the same
Yongsik Jung, Seoul (KR); Wataru Sotoyama, Kanagawa (JP); Hosuk Kang, Suwon-si (KR); Sungjun Kim, Seongnam-si (KR); Joonghyuk Kim, Seoul (KR); Youngmok Son, Hwaseong-si (KR); Won-Joon Son, Yongin-si (KR); and Yeonsook Chung, Seoul (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR)
Filed on Jun. 9, 2020, as Appl. No. 16/897,189.
Claims priority of application No. 10-2019-0176733 (KR), filed on Dec. 27, 2019.
Prior Publication US 2021/0198222 A1, Jul. 1, 2021
Int. Cl. C07D 307/79 (2006.01); C07D 407/04 (2006.01); C07D 409/04 (2006.01); C07D 407/10 (2006.01); C07D 333/54 (2006.01); C07D 409/14 (2006.01); C07D 409/10 (2006.01); C07D 405/04 (2006.01); C07D 413/10 (2006.01); C07D 471/04 (2006.01); C07F 7/08 (2006.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01); H10K 50/17 (2023.01); H10K 50/12 (2023.01); C07D 405/10 (2006.01); C07D 413/04 (2006.01); C07D 419/04 (2006.01); C07D 407/14 (2006.01); C07D 333/72 (2006.01); H01L 51/00 (2006.01); H01L 51/50 (2006.01); C07D 307/87 (2006.01); H01L 51/42 (2006.01)
CPC C07D 307/79 (2013.01) [C07D 307/87 (2013.01); C07D 333/54 (2013.01); C07D 333/72 (2013.01); C07D 405/04 (2013.01); C07D 405/10 (2013.01); C07D 407/04 (2013.01); C07D 407/10 (2013.01); C07D 407/14 (2013.01); C07D 409/04 (2013.01); C07D 409/10 (2013.01); C07D 409/14 (2013.01); C07D 413/04 (2013.01); C07D 413/10 (2013.01); C07D 419/04 (2013.01); C07D 471/04 (2013.01); C07F 7/0816 (2013.01); H01L 51/0065 (2013.01); H01L 51/0068 (2013.01); H01L 51/0069 (2013.01); H01L 51/0072 (2013.01); H01L 51/0073 (2013.01); H01L 51/0074 (2013.01); H01L 51/0094 (2013.01); H01L 51/5024 (2013.01); H01L 51/5092 (2013.01); H01L 51/4273 (2013.01); H01L 51/5056 (2013.01); H01L 51/5072 (2013.01)] 19 Claims
 
1. A condensed cyclic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
X1 is O or S,
A1 is a C5-C60 carbocyclic group or a C1-C60 heterocyclic group,
L11 is a substituted or unsubstituted C5-C60 carbocyclic group, or a substituted or unsubstituted C1-C60 heterocyclic group,
a11 is an integer 0 to 3,
Ar11 and Ar12 are each independently a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one Ra,
b11 is an integer 1 to 5,
R11, R12, and Ra are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an am idino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 C2-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 C1-C60 heteroaryl 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), or —B(Q6)(Q7),
c11 is an integer 1 to 20,
c12 is an integer 1 to 4,
when c11 is 2 or greater, two adjacent R11(s) are optionally linked to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
when c12 is 2 or greater, two adjacent R12(s) are optionally linked to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
A1 and Ar12 are optionally condensed with each other via a first linking group of a single bond, *—Ar31—*′, *—O—*′, *—S—*′, *—[C(R31)(R32)]k11—*′, *—C(R31)═*′, *═C(R31)—*′, *—C(R31)═C(R32)—′, *—C(═O)—′, *—C(═S)—*′, *—C≡C—*′, *—N(R31)—*′, *—P(R31)—*′, *—[Si(R31)(R32)]k11—*′, or *—P(R31)(R32)—*′ to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
a12 is an integer of 0 or 1,
Ar31 is a C5-C30 carbocyclic group,
R31 and R32 are each independently the same as defined in connection with R11,
k11 is 1, 2, 3, or 4,
at least one of substituents of the substituted C5-C60 carbocyclic group, the substituted C1-C60 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C2-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is: deuterium, —CD3, —CD2H, —CDH2, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with at least one deuterium, —CD3, —CD2H, —CDH2, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q14)(Q15), —B(Q16)(Q17), or any combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one deuterium, —CD3, —CD2H, —CDH2, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 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 C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q24)(Q25), —B(Q26)(Q27), or any combination thereof; or
—Si(Q31)(Q32)(Q33), —N(Q34)(Q35), or —B(Q36)(Q37), and
Q1 to Q7, Q11 to Q17, Q21 to Q27, and Q31 to Q37 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 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 C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group,
provided that the condensed cyclic compound represented by Formula 1 is not Compound A or Compound 1:

OG Complex Work Unit Chemistry