US 11,753,426 B2
Organometallic compound, organic light-emitting device including the organometallic compound, and organic light-emitting apparatus including the organic light-emitting device
Byeongwook Yoo, Yongin-si (KR); Myeongsuk Kim, Yongin-si (KR); Jimyoung Ye, Yongin-si (KR); Yiseul Kim, Yongin-si (KR); and Jaehoon Hwang, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-Si (KR)
Filed on Feb. 22, 2019, as Appl. No. 16/283,173.
Claims priority of application No. 10-2018-0022237 (KR), filed on Feb. 23, 2018.
Prior Publication US 2019/0263849 A1, Aug. 29, 2019
Int. Cl. C07F 15/00 (2006.01); H10K 50/11 (2023.01); H10K 85/30 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01); H10K 101/30 (2023.01)
CPC C07F 15/004 (2013.01) [H10K 50/11 (2023.02); H10K 85/342 (2023.02); H10K 50/156 (2023.02); H10K 50/166 (2023.02); H10K 85/324 (2023.02); H10K 85/631 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 2101/10 (2023.02); H10K 2101/30 (2023.02)] 17 Claims
OG exemplary drawing
 
1. An organometallic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1, M is selected from iridium (Ir), osmium (Os), cobalt (Co), platinum (Pt), palladium (Pd), copper (Cu), and gold (Au),
in Formula 1, Li is selected from groups represented by Formulae 2a and 2b, and n1 is 1, 2, or 3, wherein, when n1 is two or more, two or more Li(s) are identical to or different from each other,
in Formula 1, L2 is an organic ligand, and n2 is 0, 1, or 2, wherein, when n2 is two or more, two or more L2(s) are identical to or different from each other,
in Formula 1, the sum of n1 and n2 is 2 or 3,
in Formulae 2a and 2b, each of * and *′ indicates a binding site to M of Formula 1,
in Formulae 2a and 2b, X1 is C(R11) or N, X2 is C(R12) or N, X3 is C(R13) or N, and X4 is C(R14) or N,
each of R1a and R11 to R14 is independently selected from 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 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 C1-C60 heteroaryl 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), —N(Q1)(Q2), —B(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2), and two neighboring groups selected from R11 to R14 are optionally linked to form a condensed ring,
in Formulae 2a and 2b, a1 is an integer from 1 to 7 wherein, when a1 is two or more, two or more R1(s) are identical to or different from each other,
at least one substituent of the substituted C1-C6 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 C1-C60 heteroaryl 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, 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, 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, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
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, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl 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, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from 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 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, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32), and
each of Q1 to Q3, Q11 to Q13, Q21 to Q23, Q31 to Q33, and Q41 to Q42 is independently selected from 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 C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group,
A2a in Formula 2a and A2b in Formula 2b each independently is selected from groups represented by Formulae 4-1 and 4-2:

OG Complex Work Unit Chemistry
wherein, in Formulae 4-1 and 4-2,
each of A41 and A42 is independently a C4-C20 carbocyclic group or a C2-C20 heterocarbocyclic group,
each of R41, and R42 is independently the same as described in connection with R1a, and a41 and a42 are each independently the same as described in connection with a1, and
*′ indicates a binding site to M in Formula 1, and *″ indicates a binding site to a neighboring group.