Organometallic compound and organic light-emitting device including the same
An organometallic compound represented by Formula 1: wherein, in Formula 1, M, A 11 to A 13 , L 11 , R 11 to R 15 , X 11 , Y 11 to Y 17 , b13 to b15, and n11 are the same as described in the specification.
1. An organometallic compound represented by Formula 1:
wherein, in Formula 1,
M is selected from a Period I transition metal, a Period II transition metal, and a Period III transition metal,
A 11 to A 13 are each independently a C 1 -C 20 heterocyclic group,
X 11 is selected from C(R 16 )(R 17 ) and C(═O),
Y 11 to Y 17 are each a carbon atom,
Y 11 and O, Y 11 and Y 12 , Y 12 and Y 13 , Y 13 and N, Y 14 and N, Y 14 and Y 15 , Y 15 and N, Y 16 and N, Y 16 and X 11 , Y 17 and X 11 , and Y 17 and N are each independently connected to each other via a single bond or a double bond,
R 11 to R 17 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(═O)(Q 1 ), —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), and —N(Q 1 )(Q 2 ), wherein two neighboring groups selected from R 11 to R 17 are optionally connected to each other to form a condensed ring,
wherein Q 1 to Q 3 are each independently selected from a C 1 -C 60 alkyl group and a C 6 -C 60 aryl group,
b13 to b15 are each independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10,
L 11 is selected from a monodentate ligand and a bidentate ligand, and
n11 is selected from 0, 1, and 2.
2. The organometallic compound of claim 1 , wherein
M is selected from Os, Ir, and Pt.
3. The organometallic compound of claim 1 , wherein
M is Pt.
4. The organometallic compound of claim 1 , wherein
A 11 to A 13 are each independently selected from a pyrrole, an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isoxazole, an oxadiazole, a triazole, a pyridine, a pyrimidine, a pyrazine, a pyridazine, a triazine, a quinoline, an isoquinoline, a quinoxaline, a quinazoline, an indole, an isoindole, a benzimidazole, a benzoxazole, an isobenzoxazole, and an indazole.
5. The organometallic compound of claim 1 , wherein
A 11 to A 13 are each independently selected from a pyrrole, an imidazole, a pyrazole, a triazole, a pyridine, a pyrimidine, a pyrazine, a pyridazine, a triazine, a quinoline, an isoquinoline, an indole, an isoindole, a benzimidazole, and an indazole.
6. The organometallic compound of claim 1 , wherein
A 11 to A 13 are each independently selected from Formulae 2-1 to 2-6:
wherein, in Formula 2-1 to 2-6,
* indicates a binding site to M in Formula 1,
*′ indicates a binding site to a neighboring atom,
R 21 to R 25 are each independently the same as described in connection with R 11 in Formula 1.
7. The organometallic compound of claim 1 , wherein
X 11 is C(R 16 )(R 17 ), and
when R 16 and R 17 are connected to each other, X 11 is represented by one selected from Formulae 3-1 to 3-3:
wherein, in Formulae 3-1 to 3-3,
* is a carbon atom of X 11 to which R 16 and R 17 are bonded, and
R 31 to R 40 are each independently selected from
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a 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 amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof; and
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.
8. The organometallic compound of claim 7 , wherein
R 31 to R 40 are each independently selected from hydrogen, —F, a cyano group, a methyl group, an iso-propyl group, a tert-butyl group, and —CF 3 .
9. The organometallic compound of claim 7 , wherein
R 31 to R 40 are hydrogen.
10. The organometallic compound of claim 1 , wherein
R 11 to R 17 are each independently selected from
hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, —CF 3 , a methoxy group, an ethoxy group, a tert-butoxy group, a phenyl group, —C(═O)(Q 1 ), —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), and —N(Q 1 )(Q 2 ); and
a phenyl group substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, —CF 3 , a methoxy group, an ethoxy group, and a tert-butoxy group,
wherein Q 1 to Q 3 are each independently selected from a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, and a phenyl group.
11. The organometallic compound of claim 1 , wherein
R 11 to R 17 are each independently selected from
hydrogen, deuterium, —F, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, —CF 3 , —C(═O)(Q 1 ), —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), and —N(Q 1 )(Q 2 ); and
a phenyl group substituted with at least one selected from deuterium, —F, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, and —CF 3 ,
wherein Q 1 to Q 3 are each independently selected from a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, and a phenyl group.
12. The organometallic compound of claim 1 , wherein
R 11 to R 17 are each independently selected from hydrogen, —F, a cyano group, a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, —CF 3 , —Si(CH 3 ) 3 , and groups represented by Formulae 5-1 and 5-2:
wherein, in Formula 5-1 and 5-2,
* indicates a binding site to a neighboring atom.
13. The organometallic compound of claim 1 , wherein
the organometallic compound is represented by one selected from Formulae 1-1 to 1-6:
wherein, in Formulae 1-1 to 1-6,
A 11 to A 13 , X 11 , Y 11 , Y 12 , R 11 to R 15 , and b13 to b15 are the same as in Formula 1,
R 13a and R 13b are each independently the same as R 13 in Formula 1,
R 14a and R 14b are each independently the same as R 14 in Formula 1,
R 15a and R 15b are each independently the same as R 15 in Formula 1,
R 18 is the same as R 11 in Formula 1,
b13a and b13b are each independently the same as b13 in Formula 1,
b14a and b14b are each independently the same as b14 in Formula 1,
b15a and b15b are each independently the same as b15 in Formula 1,
b18 is the same as b11 in Formula 1, and
A 14 to A 17 are each independently selected from a C 5 -C 20 carbocyclic group and a C 1 -C 20 heterocyclic group.
14. The organometallic compound of claim 13 , wherein
A 14 to A 17 are each independently selected from a benzene, a naphthalene, a fluorene, an indene, a furan, a thiophene, a carbazole, a benzofuran, a benzothiophene, a dibenzofuran, and a dibenzothiophene.
15. The organometallic compound of claim 1 , wherein
the organometallic compound is represented by one selected from Formulae 1-11 to 1-19 and 1-5:
wherein, in Formulae 1-11 to 1-19 and 1-5,
A 11 to A 13 , Y 11 , Y 12 , R 11 to R 17 , and b13 to b15 are the same as in Formula 1,
R 13a and R 13b are each independently the same as R 13 in Formula 1,
R 14a and R 14b are each independently the same as R 14 in Formula 1,
R 18 is the same as R 11 in Formula 1,
b13a and b13b are each independently the same as b13 in Formula 1,
14a and b14b are each independently the same as b14 in Formula 1,
b18 is the same as b11 in Formula 1,
A 14 to A 16 are each independently selected from a C 5 -C 20 carbocyclic group and a C 1 -C 20 heterocyclic group, and
R 31 to R 38 are each independently selected from
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a 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 amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof; and
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.
16. The organometallic compound of claim 15 , wherein
A 11 to A 13 are each independently selected from a pyrrole, an imidazole, a pyrazole, a triazole, a pyridine, a pyrimidine, a pyrazine, a pyridazine, a triazine, a quinoline, an isoquinoline, an indole, an isoindole, a benzimidazole, and an indazole, and
A 14 to A 16 are each independently selected from a benzene, a naphthalene, a fluorene, an indene, a furan, a thiophene, a carbazole, a benzofuran, a benzothiophene, a dibenzofuran, and a dibenzothiophene.
17. The organometallic compound of claim 1 , wherein
the organometallic compound is selected from Compounds 1 to 50:
18. 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, wherein the organic layer comprises an emission layer and at least one organometallic compound of claim 1 .
19. The organic light-emitting device of claim 18 , wherein the emission layer comprises the organometallic compound.
20. The organic light-emitting device of claim 19 ,
wherein the emission layer further comprises a host, and
wherein the organometallic compound is a dopant.