Organometallic compound, organic light-emitting device including organometallic compound, and electronic apparatus including organic light-emitting device
An organometallic compound represented by Formula 1, an organic light-emitting device including the organometallic compound, and an electronic apparatus including the organic light-emitting device: M(L 1 ) n1 (L 2 ) n2 Formula 1 wherein, in Formula 1, M is a transition metal, L 1 is a ligand represented by Formula 2-1, L 2 is a ligand represented by Formula 2-2, n1 and n2 are each independently 1 or 2, with the proviso that when n1 is 2, the L 1 ligands are identical to or different from each other, and when n2 is 2, the L 2 ligands are identical to or different from each other, and L 1 is different from L 2 .
1. An organometallic compound represented by Formula 1:
M(L 1 ) n1 (L 2 ) n2 Formula 1
wherein, in Formula 1,
M is iridium,
L 1 is a ligand represented by Formula 2-1,
L 2 is a ligand represented by Formula 2-2,
n1 and n2 are each independently 1 or 2, with the proviso that when n1 is 2, the L 1 ligands are identical to or different from each other, and when n2 is 2, the L 2 ligands are identical to or different from each other, and
L 1 is different from L 2 :
wherein, in Formulae 2-1 and 2-2,
Y 2 is C, and Y 3 is N,
ring CY 2 is a benzene group, a naphthalene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, or a dibenzofuran group,
ring CY 3 is a pyrimidine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a naphthoquinoline group, a naphthoisoquinoline group, a naphthoquinoxaline group, a pyridoquinoline group, a pyridoisoquinoline group, a pyridoquinoxaline group, a pyridine group condensed with a cyclohexane group, an imidazole group, a benzimidazole group, a naphthoimidazole group, a phenanthrenoimidazole group, or a pyridoimidazole group,
ring CY 41 , ring CY 42 and ring CY 43 are each independently i) A group, ii) a polycyclic group in which at least two A groups are condensed, or iii) a polycyclic group in which at least one A group and at least one B group are condensed,
wherein A group is a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group and B group is a norbornane group, a furan group, a thiophene group, a selenophene group, a pyrrole group, or a silole group,
wherein a carbon atom in ring CY 41 in Formula 2-2 is bound to M in Formula 1 via a covalent bond, X 11 is Si or Ge,
T 3 is a single bond, a C 1 -C 20 alkylene group unsubstituted or substituted with at least one R 10a , a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
X 4 is O, S, Se, N(R 48 ), C(R 48 )(R 49 ), or Si(R 48 )(R 49 ),
R 1 to R 3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro 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 1 -C 60 alkylthio 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —Ge(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), or —P(Q 8 )(Q 9 ),
R 4 , R 14 , R 15 , R 16 , R 48 , and R 49 are each independently hydrogen, deuterium, —F, —SF 5 , 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 1 -C 60 alkylthio 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 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, or a substituted or unsubstituted C 1 -C 60 heteroaryl group,
a1 is an integer from 0 to 3,
a2 is an integer from 0 to 8,
a3 and a4 are each independently an integer from 0 to 10,
when a1 is 2 or 3, at least two of the R 1 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
when a2 is 2 to 8, at least two of the R 2 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
when a3 is 2 to 10, at least two of the R 3 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
when a4 is 2 to 10, at least two of the R 4 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
R 10a has a same definition as R 2 ,
* and *′ each indicate a binding site to M in Formula 1, and
a substituent of 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 1 -C 60 alkylthio 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 monovalent non-aromatic condensed polycyclic group, or the substituted monovalent non-aromatic condensed heteropolycyclic group is:
deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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, or a C 1 -C 60 alkylthio 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, or a C 1 -C 60 alkylthio group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro 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, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —Ge(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), —P(═O)(Q 18 )(Q 19 ), —P(Q 18 )(Q 19 ), or any combination thereof,
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, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 1 -C 60 alkylthio 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, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), —Ge(Q 23 )(Q 24 )(Q 25 ), —B(Q 26 )(Q 27 ), —P(═O)(Q 28 )(Q 29 ), P(Q 28 )(Q 29 ), or any combination thereof;
—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), —Ge(Q 33 )(Q 34 )(Q 35 ), —B(Q 36 )(Q 37 ), —P(═O)(Q 38 )(Q 39 ), or —P(Q 38 )(Q 39 ); or
any combination thereof,
wherein Q 1 to Q 9 , Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; or a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl 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, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, a C 1 -C 60 alkyl 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, or any combination thereof.
2. The organometallic compound of claim 1 , wherein ring CY 2 is a benzene group a naphthalene group.
3. The organometallic compound of claim 1 , wherein ring CY 3 is a pyrimidine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, group, a pyridine group condensed with a cyclohexane group, an imidazole group, a benzimidazole group, a naphthoimidazole group, group, or a pyridoimidazole group.
4. The organometallic compound of claim 1 , wherein ring CY 41 and ring CY 42 are each independently a benzene group, a naphthalene group, or a benzene group condensed with a norbornane group, and
ring CY 43 is:
a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, or a chrysene group; or
a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, or a chrysene group, each condensed with a norbornane group.
5. The organometallic compound of claim 1 , wherein T 3 is:
a single bond; or
a C 1 -C 20 alkylene group, a benzene group, a naphthalene group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a deuterated C 3 -C 10 cycloalkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a (C 1 -C 20 alkyl)C 3 -C 10 cycloalkyl group, a phenyl group, a deuterated a phenyl group, a fluorinated phenyl group, (C 1 -C 20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof.
6. The organometallic compound of claim 1 , wherein R 1 to R 4 , R 48 , and R 49 are each independently:
hydrogen, deuterium, —F, or a cyano group; or
a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a deuterated C 3 -C 10 cycloalkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a (C 1 -C 20 alkyl)C 3 -C 10 cycloalkyl group, a phenyl group, a deuterated a phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —Si(Q 33 )(Q 34 )(Q 35 ), —Ge(Q 33 )(Q 34 )(Q 35 ), or any combination thereof, and
R 14 to R 16 are each independently a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a deuterated C 3 -C 10 cycloalkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a (C 1 -C 20 alkyl)C 3 -C 10 cycloalkyl group, a phenyl group, a deuterated a phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof.
7. The organometallic compound of claim 1 , wherein the organometallic compound comprises deuterium, a fluoro group, or any combination thereof and at least one of Conditions 3 to 8 is satisfied:
Condition 1
at least one of the R 1 moieties, the number a1 representing a count of the R 1 moieties, may not be hydrogen and may include at least one deuterium,
Condition 2
at least one of the R 2 moieties, the number a2 representing a count of the R 2 moieties, may not be hydrogen and may include at least one deuterium,
Condition 3
at least one of the *-T 3 -R 3 moieties, the number a3 representing a count of the *-T 3 -R 3 moieties, may not be hydrogen and may include at least one deuterium,
Condition 4
at least one of the R 4 moieties, the number a4 representing a count of the R 4 moieties, may not be hydrogen and may include at least one deuterium,
Condition 5
at least one of the R 1 moieties (the number a1 representing a count of the R 1 moieties) may not be hydrogen and may include at least one fluoro group,
Condition 6
at least one of the R 2 moieties, the number a2 representing a count of the R 2 moieties, may not be hydrogen and may include at least one fluoro group,
Condition 7
at least one of the *-T 3 -R 3 moieties, the number a3 representing a count of the *-T 3 -R 3 moieties, may not be hydrogen and may include at least one fluoro group, and
Condition 8
at least one of R 4 moieties, the number a4 representing a count of the R 4 moieties, may not be hydrogen and may include at least one fluoro group.
8. The organometallic compound of claim 1 , wherein a group represented by
in Formula 2-1 is represented by one of Formulae CY1-1 or CY1-2:
wherein, in Formulae CY1-1 and CY1-2,
X 11 , R 14 to R 16 , and R 10a are respectively understood by referring to the descriptions of X 11 , R 14 to R 16 , and R 10a in claim 1 ,
R 11 to R 13 each has a same definition as R 1 ,
a14 is an integer from 0 to 4,
*′ indicates a binding site to M in Formula 1, and
*″ indicates a binding site to an adjacent atom in Formula 2-1.
9. The organometallic compound of claim 1 , wherein a group represented by
in Formula 2-1 is represented by one of Formulae CY2-1, CY2-11, CY2-14, CY2-17, and CY2-20 to CY2-25:
wherein, in Formulae CY2-1, CY2-11, CY2-13, CY2-14, CY2-16, CY2-17, CY2-19, and CY2-20 to CY2-25,
Y 2 is understood by referring to the description of Y 2 in claim 1 ,
X 2 is O, S, Se, N(R 28 ), C(R 28 )(R 29 ), or Si(R 28 )(R 29 ),
R 28 and R 29 are each understood by referring to the description of R 2 claim 1 ,
*″ indicates a binding site to an adjacent atom in Formula 2-1, and
*indicates a binding site to M in Formula 1.
10. The organometallic compound of claim 1 , wherein a group represented by
in Formula 2-2 is represented by one of Formulae CY3-3, CY3-5 to CY3-11, CY3-14, CY-17, CY-20 to CY3-34, CY3-37, CY3-38, CY3-40 to CY3-42, CY3-44 to CY3-46 and CY3-48:
wherein, in Formulae CY3-3, CY3-5 to CY3-11, CY3-13, CY3-14, CY3-16 to CY3-34, CY3-37, CY3-38, CY3-40 to CY3-42, CY3-44 to CY3-46 and CY3-48,
X 3 is N(T 3 -R 3 ),
Y 3 , T 3 , and R 3 are respectively understood by referring to the descriptions of Y 3 , T 3 , and R 3 in claim 1 ,
*′ indicates a binding site to M in Formula 1, and
*″ indicates a binding site to an adjacent atom in Formula 2-2.
11. The organometallic compound of claim 1 , wherein a group represented by
in Formula 2-2 is represented by one of Formulae CY4-1 to CY4-6:
wherein, in Formulae CY4-1 to CY4-6,
X 4 , ring CY 42 , and ring CY 43 are respectively understood by referring to the descriptions of X 4 , ring CY 42 , and ring CY 43 in claim 1 ,
Z 1 to Z 4 are each independently N or C,
* indicates a binding site to M in Formula 1, and
*″ indicates a binding site to ring CY 3 in Formula 2-2.
12. The organometallic compound of claim 1 , wherein a group represented by
in Formula 2-2 is represented by one of Formulae CY401 to CY412:
wherein, in Formulae CY401 to CY412,
X 4 is understood by referring to the description of X 4 in claim 1 ,
Z 5 to Z 8 and Z 11 to Z 18 are each independently N or C, and
an X 4 -containing 5-membered ring is condensed to an adjacent ring CY 41 .
13. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode and comprising an emission layer,
wherein the organic layer comprises the organometallic compound of claim 1 .
14. The organic light-emitting device of claim 13 , wherein
the first electrode is an anode,
the second electrode is a cathode,
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 a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and
the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
15. The organic light-emitting device of claim 13 , wherein the emission layer comprises the organometallic compound.
16. The organic light-emitting device of claim 15 , wherein the emission layer is configured to emit green light.
17. The organic light-emitting device of claim 15 , wherein the emission layer further comprises a host in an amount greater than an amount of the organometallic compound.
18. An electronic apparatus comprising the organic light-emitting device of claim 13 .
19. An organometallic compound represented by Formula 1:
M(L 1 ) n1 (L 2 ) n2 Formula 1
wherein, in Formula 1,
M is iridium,
L 1 is a ligand represented by Formula 2-1,
L 2 is a ligand represented by Formula 2-2,
n1 and n2 are each independently 1 or 2, with the proviso that when n1 is 2, the L 1 ligands are identical to or different from each other, and when n2 is 2, the L 2 ligands are identical to or different from each other, and
L 1 is different from L 2 :
wherein, in Formulae 2-1 and 2-2,
Y 2 is C, and Y 3 is N,
ring CY 2 is a benzene group, a naphthalene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, or a dibenzofuran group,
ring CY3 is a pyridine group,
ring CY 41 , ring CY 42 , and ring CY 43 are each independently i) A group, ii) a polycyclic group in which at least two A groups are condensed, or iii) a polycyclic group in which at least one A group and at least one B group are condensed,
wherein A group is a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group and B group is a norbornane group, a furan group, a thiophene group, a selenophene group, a pyrrole group, or a silole group,
wherein a carbon atom in ring CY 41 in Formula 2-2 is bound to M in Formula 1 via a covalent bond,
wherein a group represented by
in Formula 2-2 is represented by one of Formulae CY4-1 to CY4-3, CY4-5 and CY4-6:
wherein, in Formulae CY4-1 to CY4-3, CY4-5 and CY4-6,
Z 1 to Z 4 are each independently N or C,
* indicates a binding site to M in Formula 1, and *″ indicates a binding site to ring CY 3 in Formula 2-2,
X 11 is Si or Ge,
T 3 is a single bond, a C 1 -C 20 alkylene group unsubstituted or substituted with at least one R 10a , a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
X 4 is O, S, Se, N(R 48 ), C(R 48 )(R 49 ), or Si(R 48 )(R 49 ),
R 1 to R 3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro 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 1 -C 60 alkylthio 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —Ge(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), or —P(Q 8 )(Q 9 ),
R 4 , R 14 , R 15 , R 16 , R 48 , and R 49 are each independently hydrogen, deuterium, —F, —SF 5 , 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 1 -C 60 alkylthio 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 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, or a substituted or unsubstituted C 1 -C 60 heteroaryl group,
a1 is an integer from 0 to 3,
a2 is an integer from 0 to 8,
a3 and a4 are each independently an integer from 0 to 10,
when a1 is 2 or 3, at least two of the R 1 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
when a2 is 2 to 8, at least two of the R 2 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
when a3 is 2 to 10, at least two of the R 3 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
when a4 is 2 to 10, at least two of the R 4 moieties are optionally bound to each other to form a C 5 -C 30 unsaturated carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
R 10a has a same definition as R 2 ,
* and *′ each indicate a binding site to M in Formula 1, and
a substituent of 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 1 -C 60 alkylthio 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 monovalent non-aromatic condensed polycyclic group, or the substituted monovalent non-aromatic condensed heteropolycyclic group is:
deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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, or a C 1 -C 60 alkylthio 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, or a C 1 -C 60 alkylthio group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro 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, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —Ge(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), —P(═O)(Q 18 )(Q 19 ), —P(Q 18 )(Q 19 ), or any combination thereof,
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, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 1 -C 60 alkylthio 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, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), —Ge(Q 23 )(Q 24 )(Q 25 ), —B(Q 26 )(Q 27 ), —P(═O)(Q 28 )(Q 29 ), P(Q 28 )(Q 29 ), or any combination thereof;
—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), —Ge(Q 33 )(Q 34 )(Q 35 ), —B(Q 36 )(Q 37 ), —P(═O)(Q 38 )(Q 39 ), or —P(Q 38 )(Q 39 ); or
any combination thereof,
wherein Q 1 to Q 9 , Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; or a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl 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, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, a C 1 -C 60 alkyl 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, or any combination thereof.
20. The organometallic compound of claim 19 , wherein a group represented by
in Formula 2-2 is represented by one of Formulae CY3(1) to CY3(16):
wherein, in Formulae CY3(1) to CY3(16),
Y 3 is understood by referring to the description of Y 3 in claim 19 ,
R 31 to R 34 each has a same definition as R 3 , with the proviso that R 31 to R 34 are each not hydrogen,
*′ indicates a binding site to M in Formula 1, and
*″ indicates a binding site to an adjacent atom in Formula 2-2.
21. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode and comprising an emission layer,
wherein the organic layer comprises the organometallic compound of claim 19 .