US 11,787,829 B2
Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound
Sangdong Kim, Seongnam-si (KR); Seoungtae Kim, Daejeon (KR); Wooyoun Kim, Daejeon (KR); Jinwoo Kim, Daejeon (KR); Muhyun Baik, Daejeon (KR); Seungyeol Baek, Daejeon (KR); Seungyeon Kwak, Suwon-si (KR); Won-joon Son, Yongin-si (KR); Yongsuk Cho, Hwaseong-si (KR); Jongwon Choi, Yongin-si (KR); Hyeonho Choi, Seoul (KR); and Byoungki Choi, Hwaseong-si (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-do (KR); and KOREA ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY, Daejeon (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR); and Korea Advanced Institute of Science and Technology, Daejeon (KR)
Filed on Jan. 10, 2020, as Appl. No. 16/739,199.
Claims priority of application No. 10-2019-0033724 (KR), filed on Mar. 25, 2019.
Prior Publication US 2020/0308207 A1, Oct. 1, 2020
Int. Cl. C07F 15/00 (2006.01); H01L 51/00 (2006.01); C09K 11/06 (2006.01); H10K 85/30 (2023.01); H10K 30/30 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01)
CPC C07F 15/0086 (2013.01) [C09K 11/06 (2013.01); H10K 85/346 (2023.02); C09K 2211/185 (2013.01); C09K 2211/186 (2013.01); C09K 2211/188 (2013.01); H10K 30/353 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/171 (2023.02)] 20 Claims
OG exemplary drawing
 
1. An organometallic compound represented by Formula 1:

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wherein, in Formula 1,
M1 is beryllium, magnesium, aluminum, calcium, titanium, manganese, cobalt, copper, zinc, gallium, germanium, zirconium, rhutenium, rhodium, palladium, silver, rhenium, platinum, or gold,
X1 is N, O, or S,
ring A1 and ring A3 are each independently a C5-C30 carbocyclic group or a C2-C30 heterocyclic group,
ring A2 and ring A4 are each independently a N-containing C2-C30 heterocyclic group,
T1 is *—N[(L1)a1-(R1)b1]—*′, *—B(R1)—*′, *—P(R1)—*′, *—C(R1)(R2)—*′, *—Si(R1)(R2)—*′, *—Ge(R1)(R2)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R1)═C(R2)—*′, *—C(═S)—*′, or *—C≡C—*′,
L1 is a single bond, a substituted or unsubstituted C5-C30 carbocyclic group, or a substituted or unsubstituted C2-C30 heterocyclic group,
a1 is an integer from 1 to 3, wherein, when a1 is 2 or more, two or more L1 are identical to or different from each other,
R1 and R2 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro 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 C2-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, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —B(Q6)(Q7), or —P(═O)(Q8)(Q9),
R10, R20, R30, and R40 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro 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 C3-C10 cycloalkyl group, a substituted or unsubstituted C2-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 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,- or —P(═O)(Q8)(Q9),
provided that when R10, R20, R30, or R40 is a substituted or unsubstituted C1-C60 heteroaryl group, then the substituted or unsubstituted C1-C60 heteroaryl group is selected from Formulae 10-76 to 10-78, 10-86 to 10-128, 10-131 to 10-139, 10-148 to 10-154, 10-157 to 10-161, and 10-183 to 10-194,

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two neighboring groups among R1, R2, R10, R20, R30, and R40 are optionally linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C2-C30 heterocyclic group,
b1 is an integer from 1 to 5, wherein, when b1 is 2 or more, two or more R1 are identical to or different from each other,
b10 and b40 are each independently an integer from 1 to 4,
b20 and b30 are each independently an integer from 1 to 3,
when b10 is 2 or more, two or more R10 are identical to or different from each other, when b20 is 2 or more, two or more R20 are identical to or different from each other, when b30 is 2 or more, two or more R30 are identical to or different from each other, and when b40 is 2 or more, two or more R40 are identical to or different from each other,
a substituent of the substituted C5-C30 carbocyclic group, the substituted C2-C30 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 C2-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, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro 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, or a combination thereof;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a combination thereof, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro 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 C2-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, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), or a combination thereof;
a C3-C10 cycloalkyl group, a C2-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, or a combination thereof;
a C3-C10 cycloalkyl group, a C2-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, or a combination thereof, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro 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 C2-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, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), or a combination thereof; and
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or a combination thereof, and
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group substituted with a C1-C60 alkyl group, and 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, or a combination thereof, a C6-C60 aryl group, or a combination thereof.