US 11,889,749 B2
Organometallic compound, organic light-emitting device including organometallic compound, and diagnostic composition including organometallic compound
Minsik Min, Suwon-si (KR); Wook Kim, Yongin-si (KR); Sangmo Kim, Hwaseong-si (KR); Jongsoo Kim, Hanam-si (KR); Joonghyuk Kim, Seoul (KR); Hyejin Bae, Suwon-si (KR); Jhunmo Son, Yongin-si (KR); Hasup Lee, Seoul (KR); and Yongsik Jung, Seoul (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 Aug. 7, 2020, as Appl. No. 16/987,950.
Claims priority of application No. 10-2019-0097638 (KR), filed on Aug. 9, 2019.
Prior Publication US 2021/0043856 A1, Feb. 11, 2021
Int. Cl. H10K 85/00 (2023.01); H10K 85/30 (2023.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 50/18 (2023.01)
CPC H10K 85/346 (2023.02) [C07F 15/0086 (2013.01); C09K 11/06 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1048 (2013.01); C09K 2211/185 (2013.01); 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)] 19 Claims
 
1. An organometallic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
M1 is beryllium, magnesium, aluminum, calcium, titanium, manganese, cobalt, copper, zinc, gallium, germanium, zirconium, ruthenium, rhodium, palladium, silver, rhenium, platinum, or gold,
A1 to A3 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
A4 is a 5-membered heterocyclic group,
A5 is represented by any one of Formulae A5-1 to A5-6,
X10, X20, X30, and X40 to X44 are each independently C or N,
T1 to T3 are each independently a single bond, *—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—*′,
* and *′ each indicate a binding site to an adjacent atom,
n1 to n3 are each independently an integer from 1 to 3,
L1 is a single bond, a substituted or unsubstituted C5-C30 carbocyclic group, or a substituted or unsubstituted C1-C30 heterocyclic group,
a1 is an integer from 1 to 3, and when a1 is 2 or greater, at least two L1 groups are identical to or different from each other,
R1, R2, R10, R20, R30, R40, and R50 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 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, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(Q8)(Q9), or —P(═O)(Q8)(Q9),
at least two adjacent R1, R2, R10, R20, R30, R40, or R50 groups are optionally bound together to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
b1 is an integer from 1 to 5, and when b1 is 2 or greater, at least two R1 groups are identical to or different from each other,
b10, b20, b30, and b50 are each independently an integer from 1 to 10,
b40 is an integer from 1 to 3,
when b10 is 2 or greater, at least two R10 groups are identical to or different from each other, when b20 is 2 or greater, at least two R20 groups are identical to or different from each other, when b30 is 2 or greater, at least two R30 groups are identical to or different from each other, when b40 is 2 or greater, at least two R40 groups are identical to or different from each other, when b50 is 2 or greater, at least two R50 groups are identical to or different from each other, and
at least one substituent of the substituted C5-C30 carbocyclic group, the substituted C1-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 C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C7-C60 arylalkyl group, the substituted C1-C60 heteroaryl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted C2-C60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, or 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 C6-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 selected from 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 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, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(Q18)(Q19), or —P(═O)(Q18)(Q19);
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 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 C1-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 of 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 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, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(Q28)(Q29), or —P(═O)(Q28)(Q29); or
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(Q38)(Q39), or —P(═O)(Q38)(Q39),
wherein Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently hydrogen; —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 C1-C10 heterocycloalkyl group; a C3-C10 cycloalkenyl group; a C1-C10 heterocycloalkenyl group; a C6-C60 aryl group; a C6-C60 aryl group substituted with a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof, 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; or a monovalent non-aromatic condensed heteropolycyclic group,

OG Complex Work Unit Chemistry
wherein, in Formulae A5-1 to A5-6,
Y51 is *—O—*′ *—S—*′ *—N(R5)—*′, *—C(R5)(R6)—*′, *—Si(R5)(R6)—*′, *—B(R5)—*′, *—P(R5)—*′, or *—P(═O)(R5)—*′, wherein * and *′ each indicate a binding site to an adjacent atom,
R5 and R6 are respectively understood by referring to R1 and R2, and
X51 is C(R51) or N, X52 is C(R52) or N, X53 is C(R53) or N, X54 is C(R54) or N, X55 is C(R55) or N, X56 is C(R56) or N, and
wherein R51 to R56 are each independently understood by referring to the description of R50.