| CPC H10K 85/346 (2023.02) [C07F 15/0086 (2013.01); H10K 50/11 (2023.02)] | 20 Claims |
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1. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode and comprising an emission layer, wherein:
the organic layer comprises an organometallic compound represented by Formula 1:
 wherein, in Formulae 1, 1-1, 2-1, 2-26, 3-1, and 3-2,
M1 is selected from a Period 1 transition metal, a Period 2 transition metal, and a Period 3 transition metal;
*1 to *4 each indicate a binding site to M1;
L1 is a ligand represented by Formula 1-1;
L2 is selected from a monodentate ligand and a bidentate ligand;
n1 is 1,
n2 is selected from 0, 1, and 2;
A11 to A14 are each independently selected from a group represented by Formula 2-1, a group represented by Formula 2-26, a group represented by Formula 3-1, a group represented by Formula 3-2, a C5-C60 carbocyclic group, and a C1-C60 heterocyclic group;
at least one selected from A11 to A14 is selected from a group represented by Formula 2-1 and a group represented by Formula 2-26; and
at least one selected from A11 to A14 is selected from a group represented by Formula 3-1 and a group represented by Formula 3-2;
Y11 to Y14 are each independently selected from N and C;
T11 to T14 are each independently selected from a single bond, *—O—* ‘, and *—S—*’;
L11 to L14 are each independently selected from a single bond, *—O—*′, *—S—*′, *—C(R17)(R18)—*′, *—C(R17)═*′, *═C(R17)—*′, *—C(R17)═C(R18)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C═C—*′, *—B(R17)—*′, *—N(R17)—*′, *—P(R17)—*′, *—Si(R17)(R18)—*′, *—P(R17)(R18)—*′, and *—Ge(R17)(R18)—**;
a11 to a14 are each independently selected from 0, 1, 2, and 3, and at least three selected from a11 to a14 are selected from 1, 2, and 3;
when a11 is 0, A11 and A12 are not linked to each other, when a12 is 0, A12 and A13 are not linked to each other, when a13 is 0, A13 and A14 are not linked to each other, and when a14 is 0, A14 and A11 are not linked to each other,
R11 to R14, R17, and R18 are each 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 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, —Si(Q1)(Q2) (Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), and —P(═S)(Q1)(Q2);
R17 and R11, R17 and R12, R17 and R13, and/or R17 and R14 are optionally linked to each other to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
R17 and R18 are optionally linked to each other to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
b11 to b14 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8;
X21 is selected from O, S, N(R24), and C(R24)(R25);
X22 to X25 are each independently selected from N and C,
X26a is N, N—*, or C(R26a), X26b is N, N—*, or C(R26b), X26c is N, N—*, or C(R26c), X26d is N, N—*, or C(R26d), X26e is N, N—*, or C(R26e), X26f is N, N—*, or C(R26f), X26g is N, N—*, or C(R26g), X26h is N, N—*, or C(R26h),
A21 and A22 are each independently selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group;
X31 is N, N—*, or C(R31), X32 is N, N—*, or C(R32), X33 is N, N—*, or C(R33), X34 is N, N—*, or C(R34), X35 is N, N—*, or C(R35), X36 is N, N—*, or C(R36), X37 is N, N—*, or C(R37), and X38 is N, N—*, or C(R38),
two or more selected from X31 to X34 are each independently N or N—*,
one or more selected from X35 to X38 each independently N or N—*,
A31 is selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group;
A32 is a C1-C60 heterocyclic group containing at least one N,
R21 to R25, R26a to R26h, and R31 to R39 are each independently selected from a binding site, 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 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, —Si(Q1)(Q2) (Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), and —P(═S)(Q1)(Q2);
one, two, or three selected from R21 to R25 are binding sites,
one, two, or three selected from R24, R25 and R26a to R26h in Formula 2-26 are binding sites,
one, two, or three selected from R31 to R34 and R39 are binding sites,
one, two, or three selected from R35 to R39 are binding sites,
Q1 to Q3 are each 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 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, a biphenyl group, and a terphenyl group;
provided that none of A11 to A14 is a quinazoline group or a quinoxaline group, and none of A11 to A14 includes a pyridazine group, provided that: i) at least one selected from A11 to A14 is selected from a group represented by Formula 2-1 and a group represented by Formula 2-26 in which at least one selected from A21, A22, a group formed by X26a to X26e, and a group formed by X26f to X26h is selected from a naphthalene group, a phenanthrene group, a phenalene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, and a quinazoline group, or ii) A14 is selected from a group represented by Formula 2-1 and a group represented by Formula 2-26, A11 is selected from a group represented by Formula 3-1 and a group represented by Formula 3-2, and a14 is 0, and
provided that:
when one selected from A11 to A14 comprises a pyridine ring, at least another one selected from A11 to A14 comprises a pyrazine ring which is not directly fused to a 5-membered ring,
when at least one selected from A11 to A14 is selected from a group represented by Formula 3-1, i) X31 is N—*, X32 is C(R32), R32 is a binding site, ii) X31 is C(R31), X32 is N—*, R31 is a binding site, iii) X32 is N—*, X33 is C(R33), R33 is a binding site, or iv) X32 is C(R32), X33 is N—*, R32 is a binding site,
when at least one selected from A11 to A14 is selected from a group represented by Formula 3-2, i) X35 is N—*, X36 is C(R36), R36 is a binding site, ii) X35 is C(R35), X36 is N—*, R36 is a binding site, iii) X36 is N—*, X37 is C(R37), R37 is a binding site, or iv) X36 is C(R36), X37 is N—*, R37 is a binding site, and
and *′ each indicate a binding site to a neighboring atom.
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