US 11,807,654 B2
Organometallic compound, organic light-emitting device including organometallic compound, and diagnostic composition including organometallic compound
Hyejin Bae, Suwon-si (KR); Wataru Sotoyama, Kanagawa (JP); Sangmo Kim, Hwaseong-si (KR); Wook Kim, Suwon-si (KR); Jongsoo Kim, Seoul (KR); Joonghyuk Kim, Seoul (KR); Minsik Min, 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 Jan. 16, 2020, as Appl. No. 16/744,481.
Claims priority of application No. 10-2019-0055166 (KR), filed on May 10, 2019.
Prior Publication US 2020/0354393 A1, Nov. 12, 2020
Int. Cl. H01L 51/54 (2006.01); C07F 15/00 (2006.01); H10K 85/30 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC C07F 15/0086 (2013.01) [H10K 85/346 (2023.02); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 15 Claims
 
1. An organometallic compound represented by Formula 1:
M11(L11)n11(L12)n12  Formula 1
wherein, in Formula 1,
M11 is a first-row transition metal, a second-row transition metal, or a third-row transition metal,
L11 is a ligand represented by Formula 1-1,
L12 is a monodentate ligand or a bidentate ligand,
n11 is 1, and
n12 is 0, 1, or 2:

OG Complex Work Unit Chemistry
wherein, in Formula 1-1,
Y11 is C or N,
A11 is of Formulae 2-2 to 2-20, 2-22 to 2-36 and 2-38 to 2-47:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein, in Formulae 2-2 to 2-20, 2-22 to 2-36 and 2-38 to 2-47,
X24 is N or C(R24), X25 is N or C(R25), X26 is N or C(R26), X27 is N or C(R27),
b21 is an integer from 1 to 8,
*4 indicates a binding site to M11, and
* indicates a binding site to an adjacent atom,
T11 is C(R16)(R17), Si(R16)(R17), O, S, B(R16), or N(R16),
k11 is 0, 1, 2, or 3,
k12 is 0, 1, or 2,
k13 is 0, 1, 2, 3, or 4,
the sum of k11 to k13 is 1 or greater,
E11 to E13 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 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 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2), wherein two adjacent groups of E11 to E13 are optionally bound to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
R11 to R17, R21, and R24 to R27 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 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 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2), wherein two adjacent groups R12 to R15 are optionally bound to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
R22 and R23 are each independently hydrogen,
b11 is 1, 2, 3, 4, 5, 6, 7, or 8,
wherein Q1 to Q3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, or a C6-C60 aryl group, or a C6-C60 aryl group substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, or a C6-C60 aryl group, and
*1 to *4 each independently indicate a binding site to M11.