US 12,404,290 B2
Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device
Jeoungin Yi, Seoul (KR); Seungyeon Kwak, Suwon-si (KR); Juhyun Kim, Seoul (KR); Sangho Park, Anyang-si (KR); Sunyoung Lee, Seoul (KR); Jiyoun Lee, Anyang-si (KR); Yoonhyun Kwak, Seoul (KR); Hyun Koo, Seongnam-si (KR); Sunghun Lee, Hwaseong-si (KR); and Hyeonho Choi, Seoul (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR)
Filed on Jan. 8, 2024, as Appl. No. 18/406,353.
Application 18/406,353 is a continuation of application No. 17/060,677, filed on Oct. 1, 2020, granted, now 11,950,494.
Claims priority of application No. 10-2020-0018566 (KR), filed on Feb. 14, 2020.
Prior Publication US 2024/0237507 A1, Jul. 11, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 85/30 (2023.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 50/18 (2023.01)
CPC C07F 15/0033 (2013.01) [C09K 11/06 (2013.01); H10K 85/342 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1033 (2013.01); C09K 2211/1044 (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)] 16 Claims
 
1. An organometallic compound which is represented by Formula 1 and capable of emitting phosphorescent light:
M(L1)n1(L2)n2  <Formula 1>
wherein, in Formula 1,
M is Ir, Os, or Pt,
L1 is a ligand represented by Formula 2A or 2B,
n1 is 1, 2, or 3, wherein, when n1 is 2 or more, two or more of L(s) are identical to or different from each other,
L2 is a ligand represented by Formula 3D,
n2 is 1, or 2, wherein, when n2 is 2, two of L2 (s) are identical to or different from each other, and
L1 and L2 are different from each other,
wherein, when M is Ir or Os, the sum of n1 and n2 is 3 or 4, and when M is Pt, the sum of n1 and n2 is 2,

OG Complex Work Unit Chemistry
X3 is Se, B(R2), N(R2), P(R2), C(R2)(R3), Si(R2)(R3), Ge(R2)(R3), N, C(R2), or Si(R2),
ring CY1 and ring CY21 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
ring CY2 is a 5-membered ring,

OG Complex Work Unit Chemistry
wherein, in Formulae 3D,
T21 is a single bond, a double bond, O, S, C(Z11)(Z12), Si(Z11)(Z12), or N(Z11),
ring CY11 and ring CY12 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
Z1 and Z2 are the same as described in R21,
d1 and d2 are each independently an integer from 0 to 20, and
* and *′ each indicate a binding site to M in Formula 1,
provided that:
(I) when L1 is a ligand represented by Formula 2A, X2, X4, and X5 are each C, X21 is C, CY1 is a benzene group, CY21 is a benzene group or a pyridine group, and X3 is N(R2), then (i) n1 is 2 or 3, or (ii) R2 is a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C1-C60 heteroaryl group, or (iii) any combination thereof,
(II) when L1 is a ligand represented by Formula 2A, X2, X4, and X5 are each C, X21 is C, CY1 is a benzene group, CY21 is a benzene group or a pyridine group, X3 is N(R2), n1 is 1, n2 is 2, Y11 is N, and Y12 is C, then (i) d1 is 1 and Z1 is not hydrogen or carboxylic group, (ii) d1 is 2 or more and Z1 are each independently not hydrogen or amino group, (iii) d2 is 1 and Z2 is not hydrogen or methyl group, (iv) d2 is 2 or more and Z2 are each independently not hydrogen or halogen, or (v) any combination thereof,
Ra, Rb, R1 to R3, and R21 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 C1-C60 heteroaryl 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),
a1 and a21 are each independently an integer from 0 to 20,
two or more of a plurality of R1(s) are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of a plurality of R21(s) are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of Ra, Rb, R1 to R3, and R21 are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
R10a is the same as described in connection with R21,
* and *′ each indicate a binding site to M in Formula 1, and
at least one substituent of each 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 C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and 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 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or any combination thereof;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or any combination thereof, each substituted with at least one deuterium, —F, —Cl, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, 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 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, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or any combination 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 C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, 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 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, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or any combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), —P(Q38)(Q39), or any combination thereof; or
any combination thereof,
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 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 C1-C60 alkyl group which is unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; 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 which is unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; 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.