| CPC C07F 15/0086 (2013.01) [H10K 85/346 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/171 (2023.02); H10K 50/18 (2023.02)] | 19 Claims |
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1. An organometallic compound represented by Formula 1:
 wherein, in Formula 1,
M is a transition metal,
X1 to X4 in Formula 1 are each independently C or N,
X5 in Formula 1 is O, S, N(R′), or C(R′)(R″),
wherein,
a bond between X5 and M in Formula 1 is a covalent bond, and
one of a bond between X2 and M in Formula 1, a bond between X3 and M in Formula 1, and a bond between X4 and M in Formula 1 is a covalent bond, and the other two are each a coordinate bond,
ring CY1 to ring CY4 in Formula 1 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
T1 to T4 in Formula 1 are each independently a single bond, a double bond, *—N(R5a)—*′, *—B(R5a)—*′, *—P(R5a)—*′, *—C(R5a)(R5b)—*′, *—Si(R5a)(R5b)—*′, *—Ge(R5a)(R5b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R5a)═*′, *═C(R5a)—*′, *—C(R5a)—C(R5b)—*′, *—C(═S)—*′, *—C═C—*′, 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,
each of n1 and n2 in Formula 1 is 1,
n3 and n4 in Formula 1 are each independently 0 or 1, wherein at least three of n1 to n4 are each 1,
when n3 in Formula 1 is 0, T3 is not present, and when n4 in Formula 1 is 0, T4 is not present,
Z1 to Z4 in Formula 1 are each independently a group represented by Formula 51,
 d1 to d4 in Formula 1 are each independently an integer from 0 to 20,
L1 to L4 and L51 in Formulae 1 and 51 are each independently a single bond, 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,
b1 to b4 and b51 in Formulae 1 and 51 are each independently an integer from 1 to 10,
R1 to R4, R5a, R5b, R′, R″, and Q51 to Q53 in Formulae 1 and 51 each independently a group represented by Formula 51, hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 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 C7-C60 alkyl aryl group, a substituted or unsubstituted C7-C60 aryl alkyl 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 C2-C60 heteroaryl alkyl 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, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
provided that none of Q51 to Q53 is a group represented by Formula 51,
at least one of Q51 to Q53 in Formula 51 is independently a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
c1 to c4 and a1 to a4 in Formula 1 are each independently an integer from 0 to 20,
c51 in Formula 51 is an integer from 1 to 20,
Formula 1 satisfies at least one of Condition 1 and Condition 2,
Condition 1
a sum of d1 to d4 in Formula 1 is 1 or more,
Condition 2
at least one of T1 to T4 in Formula 1 is *—N(R5a)—*′, *—B(R5a)—*′, *—P(R5a)—*′, *—C(R5a)(R5b)—*′, *—Si(R5a)(R5b)—*′, *—Ge(R5a)(R5b)—*′, *—C(R5a)═*′, *═C(R5a)—*′, or *—C(R5a)═C(R5b)—*′, and
at least one of R5a and R5b is a group represented by Formula 51,
provided that, when i) ring CY2 is a benzimidazole group, ii) d1, d3 and d4 are 0, and iii) d2 is 1 or more, then each Z2 is independently a group represented by Formula 51, wherein each L51 is independently a single bond, a monocyclic C5-C8 carbocyclic group that is unsubstituted or substituted with at least one R10b, or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10b, and the R10b is i) deuterium; ii) —F; iii) a cyano group; or iv) a C1-C20 alkyl group that is unsubstituted or substituted with deuterium, —F, a cyano group, or a combination thereof,
two or more of a plurality of R1(s) in Formula 1 are optionally bonded together 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 R2(s) in Formula 1 are optionally bonded together 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 R3(s) in Formula 1 are optionally bonded together 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 R4(s) in Formula 1 are optionally bonded together 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 R4, R5a and one or more of R1 to R4, Rob and one or more of R1 to R4, or R5a and R5b are each optionally bonded together 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 R1,
* and *′ each indicate a binding site to a neighboring atom, and
the 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 C7-C60 alkyl aryl group, the substituted C7-C60 aryl alkyl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkyl heteroaryl group, the substituted C2-C60 heteroaryl alkyl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio 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 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 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 C2-C60 heteroaryl alkyl 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, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or a 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 C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio 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 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 C1-C60 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, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or a 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
a 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 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 a combination thereof; 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 deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 heteroaryl group; a C1-C60 heteroaryloxy group; a C1-C60 heteroarylthio group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group, and
wherein a group represented by
 is a group represented by one of Formulae CY2-1 to CY2-16 or ZCY2-1 to ZCY2-19:
     wherein, in Formulae CY2-1 to CY2-16 and ZCY2-1 to ZCY2-19,
X29 is O, S, N-[(L2)b2-(R2)c2], C(R29a)(R29b), or Si(R29a)(R29b),
Z21 to Z24 are each independently as defined in connection with Z2,
R21 to R23, R29a, and R29 are each independently as defined in connection with R2, provided that each of R21 to R23 is not hydrogen, and
*′ indicates a binding site to T1 in Formula 1, * indicates a binding site to M in Formula 1, and *″ indicates a binding site to T2 in Formula 1.
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