US 12,221,454 B2
Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device
Bumwoo Park, Yongin-si (KR); Ohyun Kwon, Seoul (KR); Virendra Kumar RAI, Hwaseong-si (KR); Sungmin Kim, Incheon (KR); Sunghun Lee, Hwaseong-si (KR); Hwayoung Cho, Hwaseong-si (KR); and Byoungki Choi, Hwaseong-si (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR)
Filed on Mar. 30, 2021, as Appl. No. 17/217,638.
Claims priority of application No. 10-2020-0141569 (KR), filed on Oct. 28, 2020.
Prior Publication US 2022/0127287 A1, Apr. 28, 2022
Int. Cl. H01L 51/00 (2006.01); C07F 15/00 (2006.01); H10K 85/30 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/18 (2023.01)
CPC C07F 15/0033 (2013.01) [H10K 85/342 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/18 (2023.02)] 17 Claims
OG exemplary drawing
 
1. An organometallic compound represented by Formula 1:
M(L1)n1(L2)n2  Formula 1
wherein, in Formula 1,
M is a transition metal,
L1 is a ligand represented by Formula 2,
n1 is 1, 2, or 3, and when n1 is 2 or more, two or more of L1(s) are identical to or different from each other,
L2 is a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand,
n2 is 0, 1, 2, 3, or 4, and when n2 is 2 or more, two or more of L2(s) are identical to or different from each other, and
L1 and L2 are different from each other,

OG Complex Work Unit Chemistry
wherein, in Formula 2,
a group represented by

OG Complex Work Unit Chemistry
in Formula 2 is a group represented by one of Formulae 2-2 to 2-11:

OG Complex Work Unit Chemistry
wherein, in Formulae 2-1 to 2-11,
ring CY21 is a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
b24 is an integer from 0 to 4,
b23 is an integer from 0 to 3,
b22 is an integer from 0 to 2,
b20 is an integer from 0 to 20,
*′ indicates a binding site to M in Formula 1, and
*″ indicates a binding site to a neighboring atom,
L11 and L13 are each independently a single bond, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
R1 to R3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 C1-C60 alkylthio 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 C2-C60 alkylheteroaryl 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(═O)(Q8)(Q9), or —P(Q8)(Q9),
b1 is an integer from 0 to 20,
b2 is an integer from 0 to 4,
T1 is a carbazole group unsubstituted or substituted with at least one R10a,
c1 is an integer from 1 to 5,
two or more of a plurality of R2(s) are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or two or more of a plurality of R2(s) are optionally linked to each other to form a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of R1 to R3 are optionally linked to each other to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or two or more of R1 to R3 are optionally linked to each other to form a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
R10a is the same as described in connection with R1,
*and *′ each indicate a binding site to M in Formula 1, and
at least one substituent of 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 C1-C60 alkylthio 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 C2-C60 alkylheteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are each independently:
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 C1-C60 alkylthio group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or a C1-C60 alkylthio 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 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 C2-C60 alkylheteroaryl 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(═O)(Q18)(Q19), or —P(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, each unsubstituted or 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 C1-C60 alkylthio 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 C2-C60 alkylheteroaryl 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(═O)(Q28)(Q29), or —P(Q28)(Q29); or
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); wherein 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 which is unsubstituted or substituted with at least one of deuterium, a C1-C60 alkyl group, or a C6-C60 aryl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C1-C60 alkylthio 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 which is unsubstituted or substituted with at least one of deuterium, a C1-C60 alkyl group, or 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 C2-C60 alkylheteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group,
wherein the group represented by:

OG Complex Work Unit Chemistry
in Formula 2 is a group represented by one of Formulae CY1-11, CY1-12, CY1-17, CY1-18, CY1-23, CY1-24, CY1-29, CY1-30, CY1-35, CY1-36, CY1-41, or CY1-42:

OG Complex Work Unit Chemistry
wherein X1 is O, S, N(R18), C(R18)(R19), or Si(R18)(R19), and R18 and R19 are each the same as described in connection with R1.