Organometallic compound and organic light-emitting device including the same
An organometallic compound and an organic light-emitting device including the same. The organometallic compound is represented by Formula 1. In Formula 1, the substituents are the same as described in the detailed description of the current disclosure.
1. An organic light-emitting device comprising:
a first electrode;
a second electrode;
an organic layer between the first electrode and the second electrode, the organic layer comprising an emission layer; and
at least one organometallic compound represented by Formula 1:
wherein, in Formula 1,
M is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),
Y 1 to Y 3 are each independently N or C,
T 1 to T 4 are each independently a chemical bond, O, S, B(R′), N(R′), P(R′), C(R′)(R″), Si(R′)(R″), Ge(R′)(R″), C(═O), B(R′)(R″), N(R′)(R″), or P(R′)(R″), wherein when T 1 is the chemical bond, Y 1 and M are directly bonded, when T 2 is the chemical bond, Y 2 and M are directly bonded, when T 3 is the chemical bond, Y 3 and M are directly bonded, and when T 4 is the chemical bond, A 4 and M are directly bonded, from among a bond between M and Y 1 or T 1 , a bond between M and Y 2 or T 2 , a bond between M and Y 3 or T 3 , and a bond between M and A 4 or T 4 , two bonds are coordinate bonds, and an other two bonds are covalent bonds,
A 1 to A 3 and A 11 to A 12 are each independently selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group,
c11 is 0 or 1, and when c11 is 0, A 11 is absent,
c12 is 0 or 1, and when c12 is 0, A 12 is absent,
L 1 to L 4 are each independently selected from a single bond, a double bond, *—N(R 5 )—*′, *—B(R 5 )—*′, *—P(R 5 )—*′, *—C(R 5 )(R 6 )—*′, *—Si(R 5 )(R 6 )—*′, *—Ge(R 5 )(R 6 )—*′, *—S—*I, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 5 )═*′, *═C(R 5 )—*′, *—C(R 5 )═C(R 6 )—*′, *—C(═S)—*′, and *—C≡C—*′,
a1 to a4 are each independently an integer from 0 to 3, wherein when a1 is 0, A 1 and A 2 are not linked to each other, when a2 is 0, A 2 and A 3 are not linked to each other, when a3 is 0, A 3 and A 4 are not linked to each other, and when a4 is 0, A 4 and A 1 are not linked to each other,
R′, R″, R 1 to R 6 , R 11 , and R 12 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), —P(═S)(Q 1 )(Q 2 ), ═O, ═S, ═N(Q 1 ), and ═C(Q 1 )(Q 2 ),
b1 to b3, b11, and b12 are each independently an integer from 0 to 20,
b4 is an integer from 0 to 7,
from among R′, R″, R 1 (s) in a number of b1, R 2 (s) in a number of b2, R 3 (s) in a number of b3, R 4 (s) in a number of b4, R 5 , R 6 , R 11 (s) in a number of b11, and R 12 (s) in a number of b12, neighboring groups are each optionally linked to each other to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
and *′ each indicate a binding site to a neighboring atom, and
at least one substituent of the substituted C 5 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio 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 C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 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 C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 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 C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), and —P(═O)(Q 21 )(Q 22 ); and
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ), and
wherein Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 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 C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C 1 -C 60 alkyl group substituted with at least one selected from deuterium, —F, and a cyano group, a C 6 -C 60 aryl group substituted with at least one selected from deuterium, —F, and a cyano group, a biphenyl group, and a terphenyl group.
2. The organic light-emitting device of claim 1 , wherein an energy level (E 3MC ) of a triplet metal-centered ( 3 MC) state of the at least one organometallic compound is about 0.26 kcal/mol or more.
3. The organic light-emitting device of claim 1 , wherein the emission layer comprises the at least one organometallic compound.
4. The organic light-emitting device of claim 3 , wherein the emission layer further comprises a host, and an amount of the at least one organometallic compound is about 0.1 parts by weight to about 50 parts by weight based on 100 parts by weight of the emission layer.
5. The organic light-emitting device of claim 3 , wherein the emission layer is to emit blue light having a maximum emission wavelength of about 450 nm to about 510 nm.
6. The organic light-emitting device of claim 1 , wherein
the first electrode is an anode,
the second electrode is a cathode,
the organic layer comprises the at least one organometallic compound,
the organic layer further comprises a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,
the hole transport region comprises at least one selected from a hole injection layer, a hole transport layer, a buffer layer, an emission auxiliary layer, and an electron blocking layer, and
the electron transport region comprises at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.
7. The organic light-emitting device of claim 6 , wherein the hole transport region comprises a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level of less than about −3.5 eV.
8. An organometallic compound represented by Formula 1:
wherein, in Formula 1,
M is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),
Y 1 to Y 3 are each independently N or C,
T 1 to T 4 are each independently a chemical bond, O, S, B(R′), N(R′), P(R′), C(R′)(R″), Si(R′)(R″), Ge(R′)(R″), C(═O), B(R′)(R″), N(R′)(R″), or P(R′)(R″), wherein when T 1 is the chemical bond, Y 1 and M are directly bonded, when T 2 is the chemical bond, Y 2 and M are directly bonded, when T 3 is the chemical bond, Y 3 and M are directly bonded, and when T 4 is the chemical bond, A 4 and M are directly bonded,
from among a bond between M and Y 1 or T 1 , a bond between M and Y 2 or T 2 , a bond between M and Y 3 or T 3 , and a bond between M and A 4 or T 4 , two bonds are coordinate bonds, and an other two bonds are covalent bonds,
A 1 to A 3 and A 11 to A 12 are each independently selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group,
c11 is 0 or 1, and when c11 is 0, A 11 is absent,
c12 is 0 or 1, and when c12 is 0, A 12 is absent,
L 1 to L 4 are each independently selected from a single bond, a double bond, *—N(R 5 )—*′, *—B(R 5 )—′, *—P(R 5 )—′, *—C(R 5 )(R 6 )—′, *—Si(R 5 )(R 6 )—′, *—Ge(R 5 )(R 6 )—′, *—S—*I, *—Se—*′, *—O—′, *—C(═O)—′, *—S(═O)—′, *—S(═O) 2 —′, *—C(R 5 )═′, *═C(R 5 )—′, *—C(R 5 )═C(R 6 )—*′, *—C(═S)—′, and *—C≡C—′,
a1 to a4 are each independently an integer from 0 to 3, wherein when a1 is 0, A 1 and A 2 are not linked to each other, when a2 is 0, A 2 and A 3 are not linked to each other, when a3 is 0, A 3 and A 4 are not linked to each other, and when a4 is 0, A 4 and A 1 are not linked to each other,
R′, R″, R 1 to R 6 , R 11 , and R 12 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), —P(═S)(Q 1 )(Q 2 ), ═O, ═S, ═N(Q 1 ), and ═C(Q 1 )(Q 2 ),
b1 to b3, b11, and b12 are each independently an integer from 0 to 20,
b4 is an integer from 0 to 7,
from among R′, R″, R 1 (s) in a number of b1, R 2 (s) in a number of b2, R 3 (s) in a number of b3, R 4 (s) in a number of b4, R 5 , R 6 , R 11 (s) in a number of b11, and R 12 (s) in a number of b12, neighboring groups are each optionally linked to each other to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
and *′ each indicate a binding site to a neighboring atom, and
at least one substituent of the substituted C 5 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio 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 C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 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 C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 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, —C 1 , —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), and —P(═O)(Q 21 )(Q 22 ); and
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ), and
wherein Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 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 C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C 1 -C 60 alkyl group substituted with at least one selected from deuterium, —F, and a cyano group, a C 6 -C 60 aryl group substituted with at least one selected from deuterium, —F, and a cyano group, a biphenyl group, and a terphenyl group.
9. The organometallic compound of claim 8 , wherein M is selected from Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, and Os.
10. The organometallic compound of claim 8 , wherein T 1 to T 4 are each a chemical bond, at least one of a bond between Y 1 and M and a bond between Y 2 and M is a coordinate bond, Y 1 is N, and Y 2 is C.
11. The organometallic compound of claim 8 , wherein A 1 to A 3 and A 11 to A 12 are each independently selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentane group, a cyclopentadiene group, a cyclohexane group, a cyclohexene group, a 1,2,3,4-tetrahydronaphthalene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an indenopyridine group, an indolopyridine group, a benzofuropyridine group, a benzothienopyridine group, a benzosilolopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuropyrimidine group, a benzothienopyrimidine group, a benzosilolopyrimidine group, a dihydropyridine 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, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a 2,3-dihydroimidazole group, a triazole group, a 1,2,4-triazole group, a tetrazole group, a 2,3-dihydrotriazole group, an azasilole group, a diazasilole group, a triazasilole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a 2,3-dihydrobenzimidazole group, an imidazopyridine group, a 2,3-dihydroimidazopyridine group, an imidazopyrimidine group, a 2,3-dihydroimidazopyrimidine group, an imidazopyrazine group, a 2,3-dihydroimidazopyrazine group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group.
12. The organometallic compound of claim 8 , wherein
i) A 1 is selected from a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group,
ii) A 2 is selected from an indole group, a carbazole group, an indolopyridine group, and an indolopyrimidine group,
iii) A 3 is selected from a benzene group, a naphthalene group, an anthracene group, and a phenanthrene group, or
any combination of i), ii), and iii) is satisfied.
13. The organometallic compound of claim 8 , wherein
ia) A 1 is a group represented by any one of Formulae 2A-1 to 2A-5,
iia) A 2 is a group represented by any one of Formulae 2B-1 to 2B-3,
iiia) A 3 is a group represented by Formula 2C-1, or
any combination of ia), iia), and iiia) is satisfied:
and
wherein, in Formulae 2A-1 to 2A-5, Formulae 2B-1 to 2B-3, and Formula 2C-1,
Y 21 is N or C(R 11a ), Y 22 is N or C(R 12a ), Y 23 is N or C(R 13a ), Y 24 is N or C(R 14a ), Y 25 is N or C(R 15a ), Y 26 is N or C(R 16a ), Y 27 is N or C(R 17a ), and Y 28 is N or C(R 18a ),
Z 21 is *′—C, C(R 21a ), or N, and Z 22 is *′—C, C(R 22a ), or N,
Z 31 is *′—N or N(R 31a ),
R 11a to R 18a , R 21a to R 22a , and R 31a are each independently the same as described in connection with R 1 of Formula 1, and
indicates a binding site to neighboring T 1 , T 2 , or T 3 , and *′ indicates a binding site to neighboring L 1 , L 2 , L 3 , or L 4 .
14. The organometallic compound of claim 13 , wherein, in Formulae 2A-1 to 2A-5 and 2C, Y 22 is C(R 12a ), and Rita is not hydrogen.
15. The organometallic compound of claim 8 , wherein a sum of c11 and c12 is 1 or 2.
16. The organometallic compound of claim 8 , wherein a1 to a3 are each 1, a4 is 0, L 1 and L 3 are each a single bond, and L 2 is *—O—*′.
17. The organometallic compound of claim 8 , wherein R′, R″, R 1 to R 6 , R 11 , and R 12 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 C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;
a C 1 -C 20 alkyl group and a C 1 -C 20 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 C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;
a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group;
a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl 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 C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ),
a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group, each substituted with at least one selected from a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl 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 C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ), and
—Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), —P(═S)(Q 1 )(Q 2 ), ═O, ═S, ═N(Q 1 ), and ═C(Q 1 )(Q 2 ), and
wherein Q 1 to Q 3 and Q 31 to Q 33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 20 aryl group, a C 1 -C 20 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.
18. The organometallic compound of claim 8 , wherein the organometallic compound represented by Formula 1 is represented by one selected from Formulae 1-1 to 1-10:
and
wherein, in Formulae 1-1 to 1-10,
M, A 1 to A 3 , A 11 to A 12 , Y 1 to Y 3 , L 1 to L 3 , a1 to a3, R 1 to R 4 , R 11 , R 12 , b1 to b3, b11, and b12 are each independently the same as respectively described in connection with Formula 1,
X 11 to X 13 are each independently selected from O, S, N(R 21 ), C(R 21 )(R 22 ), C(═O), C(═S), C(═NR 21 ), and C(═C(R 21 )(R 22 )),
X 21 to X 23 are each independently N or C(R 21 ), and
R 21 and R 22 are each independently the same as described in connection with R 1 of Formula 1.
19. The organometallic compound of claim 8 , wherein the organometallic compound represented by Formula 1 is represented by Formula 1A:
and
wherein, in Formula 1A,
M, A 1 , A 3 , A 11 to A 12 , Y 1 , Y 3 , L 2 to L 3 , R 1 , R 3 , R 4 , R 11 , R 12 , b1, b3, b4, b11, b12, c11, and c12 are each independently the same as described in connection with Formula 1,
X 31 to X 32 are each independently N or C(R 32 ),
A 31 is the same as described in connection with A 1 of Formula 1,
b31 is the same as described in connection with b2 of Formula 1, and
R 4a , R 31 , and R 32 are each independently the same as described in connection with R 1 of Formula 1.
20. The organometallic compound of claim 8 , wherein the organometallic compound represented by Formula 1 is selected from Compounds 1 to 12: