US 11,856,851 B2
Condensed cyclic compound and organic light-emitting device including the same
Yeonsook Chung, Seoul (KR); Sangmo Kim, Hwaseong-si (KR); Hyunjung Kim, Suwon-si (KR); Soonok Jeon, Seoul (KR); Yongsik Jung, Yongin-si (KR); Miyoung Chae, Suwon-si (KR); Dalho Huh, Suwon-si (KR); Hosuk Kang, Suwon-si (KR); and Jongsoo Kim, 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 Jan. 8, 2020, as Appl. No. 16/737,177.
Application 16/737,177 is a continuation of application No. 15/234,089, filed on Aug. 11, 2016, granted, now 10,593,891.
Claims priority of application No. 10-2015-0114548 (KR), filed on Aug. 13, 2015.
Prior Publication US 2020/0144517 A1, May 7, 2020
Int. Cl. H01L 51/54 (2006.01); H10K 85/60 (2023.01); C07D 405/14 (2006.01); C07D 405/10 (2006.01); C07D 495/04 (2006.01); C07D 491/04 (2006.01); C07D 417/14 (2006.01); C07D 493/04 (2006.01); C07D 417/10 (2006.01); H10K 85/30 (2023.01); C07D 409/10 (2006.01); C07D 491/048 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/155 (2023.01); H10K 71/00 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/6572 (2023.02) [C07D 405/10 (2013.01); C07D 405/14 (2013.01); C07D 409/10 (2013.01); C07D 417/10 (2013.01); C07D 417/14 (2013.01); C07D 491/04 (2013.01); C07D 491/048 (2013.01); C07D 493/04 (2013.01); C07D 495/04 (2013.01); C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 85/322 (2023.02); H10K 85/342 (2023.02); H10K 85/361 (2023.02); H10K 85/654 (2023.02); H10K 85/657 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1022 (2013.01); C09K 2211/1044 (2013.01); H10K 50/11 (2023.02); H10K 50/155 (2023.02); H10K 71/00 (2023.02); H10K 2101/10 (2023.02)] 15 Claims
 
1. A condensed cyclic compound represented by one of Formula 1A to 1H:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein, in Formulae 1A to 1H,
X4 is selected from O, S, N(R4c) and C(R4d)(R4e),
R4a to R4e are the same as R4,
aa4 is an integer of 0 to 3,
ab4 is an integer of 0 to 2,
X1 is selected from a single bond, O, S, N(R11) and C(R12)(R13),
X2 is O or S,
ring A1 to ring A4 are each independently a C5-C60 carbocyclic group or a C2-C60 heterocyclic group,
ring A3 is selected from a benzene, a pyridine, a pyrimidine, a pyrazine, a pyridazine, an indene, an indole, a benzofuran, a benzothiophene, a fluorene, a carbazole, a dibenzofuran and a dibenzothiophene,
ring A5 is selected from a benzene, a pyridine, a pyrimidine, a pyrazine, a pyridazine and a triazine,
ring A6 is represented by Formula 2A,
ring A7 is represented by Formula 2B,
R1 to R6 and R11 to R13 are each independently selected from a hydrogen, a 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 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-C10 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 C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted C2-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 is an integer of 1 to 4,
a2 to a6 are each independently an integer of 0 to 4,
L1 is selected from
a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group and a triazinylene group; and
a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group and a triazinylene group, each substituted with at least one selected from a 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-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group and —Si(Q8)(Q9)(Q10),
b1 is an integer of 1 to 3,
n is an integer of 0 to 3,
the number of cyano groups in Formulae 1A to 1H is 2, 3 or 4, and
i) one or more groups R5 in the number of a5, and optionally, one or more of groups R3 in the number of a3 is a cyano group, or ii) one or more of groups R3 in the number of a3, one or more groups R5 in the number of a5, or any combination thereof is a cyano group-substituted C6-C10 aryl group,
at least one substituent of the substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C1-C60 alkoxy 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 C1-C60 heteroaryloxy group, substituted C1-C60 heteroarylthio group, substituted C2-C60 heteroarylalkyl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from
a deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 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, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 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 C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-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 C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-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 C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-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, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 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 C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-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 Q10, Q11 to Q17, Q21 to Q27 and Q31 to Q37 are each independently selected from a hydrogen, a 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 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 C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted C2-C60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.