US 12,312,364 B2
Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound
Hyeonho Choi, Seoul (KR); Kyuyoung Hwang, Anyang-si (KR); Seungyeon Kwak, Suwon-si (KR); Youngmin Nam, Seoul (KR); Kum Hee Lee, Suwon-si (KR); Aram Jeon, Suwon-si (KR); Whail Choi, Seoul (KR); Kyungdoc Kim, Seoul (KR); Jiho Yoo, Hwaseong-si (KR); and Younsuk Choi, Seongnam-si (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR)
Filed on Aug. 29, 2019, as Appl. No. 16/555,257.
Claims priority of application No. 10-2018-0104040 (KR), filed on Aug. 31, 2018; and application No. 10-2019-0105899 (KR), filed on Aug. 28, 2019.
Prior Publication US 2020/0083464 A1, Mar. 12, 2020
Int. Cl. H10K 85/30 (2023.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); 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); H10K 101/10 (2023.01)
CPC C07F 15/0033 (2013.01) [C09K 11/06 (2013.01); H10K 85/342 (2023.02); C09K 2211/1029 (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)] 11 Claims
 
1. An organometallic compound represented by Formula 1:
M(L1)n1(L2)n2  Formula 1
wherein, in Formula 1,
M is iridium (Ir), osmium (Os), titanium (Ti), hafnium (Hf), europium (Eu), rhodium (Rh), or ruthenium (Ru),
L1 is a ligand represented by Formula 2,
n1 is 1 or 2, and when n1 is 2, the two L1 groups are identical to or different from each other,
L2 is a group represented by one of Formulae 3-1(61) to 3-1(66), 3-1(301) and 3-1(305) to 3-1(307), and 3-1(309),

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wherein, in Formulae 3-1(61) to 3-1(66), 3-1(301) and 3-1(305) to 3-1(307), and 3-1(309),
X41 is O, S, N(Z21), C(Z21)(Z22), or Si(Z21)(Z22),
Z1 to Z4, and Z11 to Z14 are each the same as defined in connection with R21,
d14 is an integer from 0 to 4,
d26 is an integer from 0 to 6,
* and *′ each indicate a binding site to M in Formula 1, and
in Formula 1,
n2 is 1 or 2, and when n2 is 2, the two L2 groups are identical to or different from each other, and
L1 and L2 are different from each other,

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wherein, in Formula 2,
X1 is N and X21 is C,
ring CY11 and ring CY12 are condensed with each other,
T1 is *—O—*′, wherein * and *′ each indicate a binding site to a neighboring atom,
a group represented by

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 in Formula 2 is a group represented by one of Formulae CY1-30 to CY1-33, CY1-35 to CY1-37, CY1-39 to CY1-42, CY1-44 to CY1-48, CY1-50 to CY1-52, CY1-54 to CY1-58 and CY1-60 to CY1-69:

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wherein, in Formulae CY1-30 to CY1-33, CY1-35 to CY1-37, CY1-39 to CY1-42, CY1-44 to CY1-48, CY1-50 to CY1-52, CY1-54 to CY1-58 and CY1-60 to CY1-69,
X11 is O, S, Se, N(R19), C(R19a)(R19b), or Si(R19a)(R19b),
R19, R19a, R19b, R1a and R1b are each the same as defined in connection with R1,
a18 is an integer from 0 to 8,
a14 is an integer from 0 to 4,
a13 is an integer from 0 to 3,
*″ indicates a binding site to Tin Formula 2, and
*′ indicates a binding site to M in Formula 1,
a group represented by

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 in Formula 2 is a group represented by one of Formulae CY21-1 to CY21-25:

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wherein, in Formulae CY21-1 to CY21-25,
X22 is C(R22)(R23), N(R22), O, S, or Si(R22)(R23),
R22 to R29 are each the same as defined in connection with R21,
a26 is an integer from 0 to 6,
a24 is an integer from 0 to 4,
a23 is an integer from 0 to 3,
a22 is an integer from 0 to 2,
*″ indicates a binding site to T1 in Formula 2, and
*′ indicates a binding site to M in Formula 1,
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 hydrazino group, a hydrazono 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 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 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),
provided that when CY21 is a benzene group, then at least one of R21 is not —F, —Cl, —Br, or —I,
a1 and a21 are each independently an integer from 0 to 20,
two or more of a plurality of groups R1 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 groups 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,
two or more of 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 defined in connection with R21,
* and *′ each indicate a binding site to M in Formula 1, and
a substituent(s) 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 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 monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is each independently:
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 hydrazino group, a hydrazono 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, or a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with 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 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 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 monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with 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 hydrazino group, a hydrazono 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 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 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)(Q19), —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), or —P(Q38)(Q39); or
any combination thereof, and
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; a guanidino group; an amidino group; a guanidino 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 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 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 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 monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.