Light-emitting device, electronic apparatus including the same, and organometallic compound
Provided are an organometallic compound represented by Formula 1, a light-emitting device including the same, and an electronic apparatus including the light-emitting device. The light-emitting device includes: a first electrode; a second electrode facing the first electrode; and interlayer between the first electrode and the second electrode and including an emission layer, wherein the emission layer includes an organometallic compound represented by Formula 1.
1. A light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
an interlayer between the first electrode and the second electrode and comprising an emission layer,
wherein the emission layer comprises an organometallic compound represented by Formula 1:
wherein, in Formula 1, M is platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
in Formula 1, X 1 to X 4 are each independently C or N,
in Formula 1, i) a bond between X 1 and M is a coordinate bond, and ii) one bond selected from a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a coordinate bond, and the remaining two bonds are covalent bonds,
in Formula 1, ring CY 1 is i) an X 1 -containing 5-membered ring, ii) an X 1 -containing 5-membered ring condensed with at least one 6-membered ring, or iii) an X 1 -containing 6-membered ring,
in Formula 1, ring CY 2 is a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
in Formula 1, X 31 to X 36 and X 41 to X 44 are each independently C or N,
in Formula 1, X 51 is *—N(R 5 )—*′, *—B(R 5 )—*′, *—P(R 5 )—*′, *—C(R 5a )(R 5b )—*′, *—Si(R 5a )(R 5b )—*′, *—Ge(R 5a )(R 5b )*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)*′, *—S(═O)—*′*—S(═O) 2 —*′*—C(R 5 )═*′, *═C(R 5 )—*′, *—C(R 5a )═C(R 5b )—*′, *—C(═S)—*′, or *—C≡C*′, wherein * and *′ each indicate a binding site to a neighboring atom,
in Formula 1, L 1 is a single bond, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
in Formula 1, b1 is an integer in a range from 1 to 5,
in Formula 1, R 1 to R 5 , R 5a , and R 5b are each independently a group represented by Formula 1-1, a group represented by Formula 1-2, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —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 ), or —P(═O)(Q 1 )(Q 2 ),
in Formula 1, c1 is an integer in a range from 0 to 5, a1 and a4 are each independently an integer in a range from 0 to 4, a2 is an integer in a range from 0 to 10, a3 is an integer in a range from 0 to 6, the sum of a1 to a4 is 1 or more, at least one of a group(s) represented by *-(L 1 ) b1 -(R 1 ) c1 in the number of a1, at least one of R 2 (s) in the number of a2, at least one of R 3 (s) in the number of a3, at least one of R 4 (s) in the number of a4, or any combination thereof is each independently a group represented by Formula 1-1 or a group represented by Formula 1-2,
in Formulae 1-1 and 1-2, L 7 is a single bond, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
in Formulae 1-1 and 1-2, b7 is an integer in a range from 1 to 5,
in Formulae 1-1 and 1-2, ring CY 7 is a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
in Formulae 1-1 and 1-2, n7 is an integer in a range from 1 to 5,
in Formula 1-1, ring CY 8 is a non-aromatic C 3 -C 60 carbocyclic group or a non-aromatic C 1 -C 60 heterocyclic group,
in Formulae 1-1 and 1-2, R 7 to R 9 are each the same as described in connection with R 1 , provided that, at least one of R 8 and R 9 is not hydrogen,
in Formulae 1-1 and 1-2, a7 and a8 are each independently an integer in a range from 0 to 20,
two or more selected from a group(s) represented by *-(L 1 ) b1 -(R 1 ) c1 in the number of a1 are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more selected from R 2 (s) in the number of a2 are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more selected from R 3 (s) in the number of a3 are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more selected from R 4 (s) in the number of a4 are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a , two or more selected from R 1 to R 5 , R 5a , and R 5b are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
R 10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio 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 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio 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 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or
—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 ), or —P(═O)(Q 31 )(Q 32 ), and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof.
2. The light-emitting device of claim 1 , wherein:
in ring CY 1 of Formula 1, the X 1 -containing 5-membered ring is a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, or a thiadiazole group, and
in ring CY 1 of Formula 1, the 6-membered ring condensed with the X 1 -containing 5-membered ring, or the X 1 -containing 6-membered ring, is a benzene group, a pyridine group, or a pyrimidine group.
3. The light-emitting device of claim 1 , wherein a4 in Formula 1 is an integer in a range from 1 to 4, and at least one of R 4 (s) in the number of a4 is each independently a group represented by Formula 1-1 or a group represented by Formula 1-2.
4. The light-emitting device of claim 1 , wherein:
in Formulae 1-1 and 1-2, ring CY 7 is i) a first ring, ii) a second ring, iii) a condensed cyclic group in which two or more first rings are condensed with each other, iv) a condensed cyclic group in which two or more second rings are condensed with each other, or v) a condensed cyclic group in which at least one first ring is condensed with at least one second ring,
the first ring is a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norbornane group, a bicyclo[1.1.1] pentane group, a bicyclo[2.1.1] hexane group, a bicyclo[2.2.2] octane group, or a benzene group, and
the second ring is a pyrrole group, a furan group, a thiophene group, a silole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a 1,2-azaborinine group, a 1,3-azaborinine group, a 1,4-azaborinine group, a 1,2-dihydro-1,2-azaborinine group, a 1,4-oxaborinine group, a 1,4-thiaborinine group, or a 1,4-dihydroborinine group.
5. The light-emitting device of claim 1 , wherein ring CY 8 in Formula 1-1 is a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norbornane group, a bicyclo[1.1.1] pentane group, a bicyclo[2.1.1] hexane group, or a bicyclo[2.2.2] octane group.
6. The light-emitting device of claim 1 , wherein ring CY 8 in Formula 1-1 is a group represented by one of Formulae CY8-1 to CY8-8:
wherein, in Formulae CY8-1 to CY8-8, * indicates a binding site to a neighboring atom in Formula 1, and * indicates a binding site to a neighboring atom in Formula 1-1.
7. The light-emitting device of claim 1 , wherein:
the first electrode is an anode,
the second electrode is a cathode,
the interlayer 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 includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and
the electron transport region further includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
8. The light-emitting device of claim 1 , further comprising a capping layer outside the second electrode, the capping layer comprising a material having a refractive index of equal to or greater than 1.6.
9. The light-emitting device of claim 1 , wherein the emission layer emits blue light having a maximum emission wavelength in a range of 410 nm to 500 nm.
10. The light-emitting device of claim 1 , wherein:
the emission layer comprises a host and a dopant, and
the dopant comprises the organometallic compound.
11. A light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
an interlayer between the first electrode and the second electrode and comprising an emission layer,
wherein the emission layer comprises an organometallic compound represented by Formula 1:
wherein, in Formula 1, M is platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
in Formula 1, X 1 to X 4 are each independently C or N,
in Formula 1, i) a bond between X 1 and M is a coordinate bond, and ii) one bond selected from a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a coordinate bond, and the remaining two bonds are covalent bonds,
in Formula 1, ring CY 1 is i) an X 1 -containing 5-membered ring, ii) an X 1 -containing 5-membered ring condensed with at least one 6-membered ring, or iii) an X 1 -containing 6-membered ring,
in Formula 1, ring CY 2 is a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
in Formula 1, X 31 to X 36 and X 41 to X 44 are each independently C or N,
in Formula 1, X 51 is *—N(R 5 )—*′, *—B(R 5 )—*′, *—P(R 5 )—*′, *—C(R 5a )(R 5b )—*′, *—Si(R 5a )(R 5b )—*′, *—Ge(R 5a )(R 5b )*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)*′, *—S(═O)—*′*—S(═O) 2 —*′, *—C(R 5 )═*′, *═C(R 5 )—*′, *—C(R 5a )═C(R 5b )—*′, *—C(═S)—*′, or *—C≡C*′, wherein * and *′ each indicate a binding site to a neighboring atom,
in Formula 1, L 1 is a single bond, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
in Formula 1, b1 is an integer in a range from 1 to 5,
in Formula 1, R 1 to R 5 , R 5a , and R 5b are each independently a group represented by Formula 1-1, a group represented by Formula 1-2, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —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 ), or —P(═O)(Q 1 )(Q 2 ),
in Formula 1, c1 is an integer in a range from 0 to 5, a1 and a4 are each independently an integer in a range from 0 to 4, a2 is an integer in a range from 0 to 10, a3 is an integer in a range from 0 to 6, the sum of a1 to a4 is 1 or more, at least one of a group(s) represented by *-(L 1 ) b1 -(R 1 ) c1 in the number of a1, at least one of R 2 (s) in the number of a2, at least one of R 3 (s) in the number of a3, at least one of R 4 (s) in the number of a4, or any combination thereof is each independently a group represented by Formula 1-1 or a group represented by Formula 1-2,
in Formulae 1-1 and 1-2, L 7 is a single bond, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
in Formulae 1-1 and 1-2, b7 is an integer in a range from 1 to 5,
in Formulae 1-1 and 1-2, ring CY 7 is a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
in Formulae 1-1 and 1-2, n7 is an integer in a range from 1 to 5,
in Formula 1-1, ring CY 8 is a non-aromatic C 3 -C 60 carbocyclic group or a non-aromatic C 1 -C 60 heterocyclic group,
in Formulae 1-1 and 1-2, R 7 to R 9 are each the same as described in connection with R 1 ,
in Formulae 1-1 and 1-2, a7 and a8 are each independently an integer in a range from 0 to 20,
two or more selected from a group(s) represented by *-(L 1 ) b1 -(R 1 ) c1 in the number of a1 are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more selected from R 2 (s) in the number of a2 are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more selected from R 3 (s) in the number of a3 are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more selected from R 4 (s) in the number of a4 are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more selected from R 1 to R 5 , R 5a , and R 5b are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
R 10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio 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 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio 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 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or
—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 ), or —P(═O)(Q 31 )(Q 32 ), and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof,
wherein:
the first electrode is an anode,
the second electrode is a cathode,
the interlayer 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 includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and the electron transport region further includes a buffer layer, a hole blocking layer,
an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof,
wherein:
the electron transport region comprises the hole blocking layer, and
the hole blocking layer comprises a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof.
12. An electronic apparatus comprising the organic light-emitting device of claim 1 .
13. The electronic apparatus of claim 12 , wherein:
the electronic apparatus further comprises a thin-film transistor,
the thin-film transistor comprises a source electrode and a drain electrode, and
the first electrode of the light-emitting device is electrically coupled with at least one selected from the source electrode and the drain electrode of the thin-film transistor.
14. The electronic apparatus of claim 12 , wherein the electronic apparatus further comprises a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof.
15. An organometallic compound represented by Formula 1:
wherein, M in Formula 1 is platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
X 1 to X 4 in Formula 1 are each independently C or N,
in Formula 1, i) a bond between X 1 and M is a coordinate bond, and ii) one bond selected from a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a coordinate bond, and the remaining two bonds are covalent bonds,
ring CY 1 in Formula 1 is i) an X 1 -containing 5-membered ring, ii) an X 1 -containing 5-membered ring condensed with at least one 6-membered ring, or iii) an X 1 -containing 6-membered ring,
ring CY 2 in Formula 1 is a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
X 31 to X 36 and X 41 to X 44 in Formula 1 are each independently C or N,
X 51 in Formula 1 is *—N(R 5 )—*′, *—B(R 5 )—*′, *—P(R 5 )—*′, *—C(R 5a )(R 5b )—*′, *—Si(R 5a )(R 5b )—*′, *—Ge(R 5a )(R 5b )*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)*′, *—S(═O)—*′*—S(═O) 2 —*′*—C(R 5 )═*′, *═C(R 5 )—*′, *—C(R 5a )═C(R 5b )—*′, *—C(═S)—*′, or *—C≡C*′, wherein * and *′ each indicate a binding site to a neighboring atom,
L 1 in Formula 1 is a single bond, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
b1 in Formula 1 is an integer in a range from 1 to 5,
R 1 to R 5 , R 5a , and R 5b in Formula 1 are each independently a group represented by Formula 1-1, a group represented by Formula 1-2, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —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 ), or —P(═O)(Q 1 )(Q 2 ),
in Formula 1, c1 is an integer in a range from 0 to 5, a1 and a4 are each independently an integer in a range from 0 to 4, a2 is an integer in a range from 0 to 10, a3 is an integer in a range from 0 to 6, the sum of a1 to a4 is 1 or more, at least one of a group(s) represented by *-(L 1 ) b1 -(R 1 ) c1 in the number of a1, at least one of R 2 (s) in the number of a2, at least one of R 3 (s) in the number of a3, at least one of R 4 (s) in the number of a4, or any combination thereof is each independently a group represented by Formula 1-1 or a group represented by Formula 1-2,
in Formulae 1-1 and 1-2, L 7 is a single bond, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
in Formulae 1-1 and 1-2, b7 is an integer in a range from 1 to 5,
in Formulae 1-1 and 1-2, ring CY 7 is a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
in Formulae 1-1 and 1-2, n7 is an integer in a range from 1 to 5,
in Formula 1-1, ring CY 8 is a non-aromatic C 3 -C 60 carbocyclic group or a non-aromatic C 1 -C 60 heterocyclic group,
in Formulae 1-1 and 1-2, R 7 to R 9 are each the same as described in connection with R 1 , provided that, at least one of R 8 and R 9 is not hydrogen,
in Formulae 1-1 and 1-2, a7 and a8 are each independently an integer in a range from 0 to 20,
two or more selected from a group(s) represented by *-(L 1 ) b1 -(R 1 ) c1 in the number of a1 are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more selected from R 2 (s) in the number of a2 are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more selected from R 3 (s) in the number of a3 are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more selected from R 4 (s) in the number of a4 are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more selected from R 1 to R 5 , R 5a , and R 5b are optionally linked together to form a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
R 10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio 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 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio 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 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or
—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 ), or —P(═O)(Q 31 )(Q 32 ), and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof.
16. The organometallic compound of claim 15 , wherein, in ring CY 1 of Formula 1, the X 1 -containing 5-membered ring is a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, or a thiadiazole group, and
in ring CY 1 of Formula 1, the 6-membered ring condensed with the X 1 -containing 5-membered ring, or the X 1 -containing 6-membered ring, is a benzene group, a pyridine group, or a pyrimidine group.
17. The organometallic compound of claim 15 , wherein a4 in Formula 1 is an integer in a range from 1 to 4, and at least one of R 4 (s) in the number of a4 is each independently a group represented by Formula 1-1 or a group represented by Formula 1-2.
18. The organometallic compound of claim 15 , wherein:
in Formulae 1-1 and 1-2, ring CY 7 is i) a first ring, ii) a second ring, iii) a condensed cyclic group in which two or more first rings are condensed with each other, iv) a condensed cyclic group in which two or more second rings are condensed with each other, or v) a condensed cyclic group in which at least one first ring is condensed with at least one second ring,
the first ring is a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norbornane group, a bicyclo[1.1.1] pentane group, a bicyclo[2.1.1] hexane group, a bicyclo[2.2.2] octane group, or a benzene group, and
the second ring is a pyrrole group, a furan group, a thiophene group, a silole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a 1,2-azaborinine group, a 1,3-azaborinine group, a 1,4-azaborinine group, a 1,2-dihydro-1,2-azaborinine group, a 1,4-oxaborinine group, a 1,4-thiaborinine group, or a 1,4-dihydroborinine group.
19. The organometallic compound of claim 15 , wherein ring CY 8 in Formula 1-1 is a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norbornane group, a bicyclo[1.1.1] pentane group, a bicyclo[2.1.1] hexane group, or a bicyclo[2.2.2] octane group.
20. The organometallic compound of claim 15 , wherein ring CY 8 in Formula 1-1 is a group represented by one of Formulae CY8-1 to CY8-8:
wherein, in Formulae CY8-1 to CY8-8, * indicates a binding site to a neighboring atom in Formula 1, and *′ indicates a binding site to a neighboring atom in Formula 1-1.