US 11,957,044 B2
Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound
Jongwon Choi, Yongin-si (KR); Sukekazu Aratani, Hwaseong-si (KR); Kum Hee Lee, Suwon-si (KR); Banglin Lee, Suwon-si (KR); Hyeonho Choi, Seoul (KR); Seungyeon Kwak, Suwon-si (KR); Yoonhyun Kwak, Seoul (KR); Sangdong Kim, Seongnam-si (KR); Jiwhan Kim, Suwon-si (KR); Chul Baik, Seoul (KR); and Yongsuk Cho, Suwon-si (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR)
Filed on Sep. 4, 2018, as Appl. No. 16/120,916.
Claims priority of application No. 10-2017-0113560 (KR), filed on Sep. 5, 2017; and application No. 10-2018-0104722 (KR), filed on Sep. 3, 2018.
Prior Publication US 2019/0074457 A1, Mar. 7, 2019
Int. Cl. C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/12 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 50/18 (2023.01); H10K 85/30 (2023.01); H10K 101/10 (2023.01); H10K 102/00 (2023.01)
CPC H10K 85/346 (2023.02) [C07F 15/0086 (2013.01); C09K 11/06 (2013.01); C09K 2211/1033 (2013.01); C09K 2211/1037 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/1092 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); 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); H10K 2101/10 (2023.02); H10K 2102/3026 (2023.02); H10K 2102/3035 (2023.02)] 19 Claims
OG exemplary drawing
 
1. An organometallic compound represented by Formula 1:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein, M in Formula 1 is a transition metal,
X1 in Formula 1 is nitrogen (N),
X2 to X4 in Formula 1 are each independently carbon (C) or N,
in Formula 1, a bond between X1 and M is a coordinate bond, and one bond selected from a bond between X2 and M, a bond between X3 and M, and a bond between X4 and M is a coordinate bond while the remaining two bonds are each independently be a covalent bond,
n in Formula 1 is 0 or 1, wherein, when n is 0, CY1 and CY4 are not linked each other,
CY1 and CY4 are identical to each other,
in Formula 1, i) when n is 0, CY1 is a group represented by one selected from Formulae A1-1 to A1-6; and ii) when n is 1, CY1 is a group represented by one selected from Formulae A11-1 to A11-4,
in Formulae A1-1 to A1-6 and A11-1 to A11-4,
i) X11 is *—N[(L11)c11-(R11)]—*′, *—B(R11)—*′, *—P(R11)—*′, *—C(R11a)(R11b)—*′, *—Si(R11a)(R11b)—*′, *—Ge(R11a)(R11b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, or *—C(═S)—*′, X12 is C(R12) or N, X13 is C(R13) or N, X14 is C(R14) or N, and X15 is C(R15) or N;
ii) when X14 is C(R14) and X15 is C(R15), R14 and R15 are not linked each other; and
iii) R11a and R11b, are optionally linked each other via a second linking group to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
in Formulae A1-1 to A1-6 and A1l-1 to A11-4, * may indicate a binding site to M in Formula 1, *′ may indicate a binding site to T1 in Formula 1, and *” may indicate a binding site to T4 in Formula 1,
in Formula 1, CY2 to CY4are each independently selected from a C5-C30 carbocyclic group and a C1-C30 heterocyclic group,
in Formula 1, T1 to T4 are each independently selected from a single bond, a double bond, *—N[(L5)c5-(R5)]—*′, *—B(R5)—*′, *—P(R5)—*′, *—C(R5)(R6)—*′, *—Si(R5)(R6)—*′, *—Ge(R5)(R6)—*′, *—S—*′, *—Se—*′, *—O—*, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R5)═*′, *═C(R5)—*′,*—C(R5)═C(R6)—*′, *—C(═S)—*′, and *—C≡C—*′, wherein R5 and R6 are optionally be linked each other via a first linking group to form a substituted or unsubstituted C5-C30carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
L5 and L11 are each independently selected from a single bond, a substituted or unsubstituted C5-C30 carbocyclic group, and a substituted or unsubstituted C1-C30 heterocyclic group,
c5 and c11 are each independently an integer from 1 to 3, wherein, when c5 is two or more, two or more of groups L5 are identical to or different from each other, and when c 11 is two or more, two or more of groups L11 are identical to or different from each other,
R2 to R6, R11 to R15, R11a, and R11b are each independently selected from 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-C60alkyl 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 C7-C60 alkyl 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 alkyl heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted C2-C60 heteroaryl alkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or un substituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —B(Q6)(Q7), and —P(═O)(Q8)(Q9),
provided that when CY1 is a group represented by Formula A1-1, then i) X11 is O and at least one of X12 to X15 is N, or ii) X11 is *—S—*′ or *—Se—*′, a2 to a4 are each independently an integer from 0 to 20,
in Formula 1, two or more selected from groups R2 in the number of a2 are optionally linked each other to forma substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
in Formula 1, two or more selected from groups R3 in the number of a3 are optionally linked each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
in Formula 1, two or more selected from groups R4 in the number of a4 are optionally linked each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
in Formula 1, two or more of R2 to R4 are optionally linked each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
in Formula 1, one of R5 and R6 and one of R2 to R4 are optionally linked each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
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 C7-C60 alkyl aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C7-C60 aryl alkyl group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkyl heteroaryl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the C2-C60 heteroaryl alkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is 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 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 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 C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroaryl alkyl 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), and —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 C7-C60 alkylaryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C1-C60 heteroaryl group, a C1-C60heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroaryl alkyl 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 C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroaryl alkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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 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 C7-C60 alkyl aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroaryl alkyl 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), and —P(═O)(Q28)(Q29); and
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —B(Q36)(Q37), and —P(═O)(Q38)(Q39), and
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently selected from 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 C1-C10heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60aryl group, a C6-C60 aryl group substituted with at least one selected from a C1-C60 alkyl group, and a C6-C60aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroaryl alkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.