Organometallic compound and light-emitting device including organometallic compound
Provided are an organometallic compound represented, a light-emitting device including the organometallic compound, and an electronic apparatus including the light-emitting device. The organometallic compound is represented by Formula 1, which is defined in the specification:
1. A light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an interlayer disposed between the first electrode and the second electrode, wherein
the interlayer comprises an emission layer and at least one organometallic compound represented by Formula 1:
wherein in Formula 1,
M is 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), or thulium (Tm),
X 1 to X 3 are each independently C or N,
X 4 is a carbon atom of a carbene moiety,
X 5 is C,
A 1 to A 3 are each independently a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
A 4 is an X 4 -containing imidazole group or an X 4 -containing imidazole group to which at least one 5-membered ring is condensed,
A 5 is an X 5 -containing 5-membered heterocyclic group,
T 1 to T 3 are each independently a single bond, a double bond, *—N(Z 11 )—*′, *—B (Z 11 )—*′, *—P (Z 11 )—*′, *—C(Z 11 ) (Z 12 )—*′, *—Si (Z 11 ) (Z 12 )—*′, *—Ge (Z 11 ) (Z 12 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 -*′, *—C(Z 11 )=*′, *=C (Z 11 )—*′, *—C(Z 11 )—C(Z 12 )—*′, *—C(═S)—*′, or *—C═C—*′, and * and *′ each indicate a binding site to an adjacent atom,
a1 to a3 are each independently an integer from 1 to 3,
R 1 to R 5 , Z 11 , and Z 12 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 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 , —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 ),
b1 to b5 are each independently an integer from 0 to 10,
when b4 is 2 or greater, at least two R 4 (s) of R 4 (s) in the number of b4 are optionally combined to form 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 ,
when b5 is 2 or greater, at least two R 5 (s) of Rs(s) in the number of b5 are optionally combined to form 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 , and
R 10a is:
deuterium, —F, —C 1 , —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, —C 1 , —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 a combination thereof;
a C 3 —C 60 carbocyclic group, a C 1 —C 60 heterocyclic group, a Co—C 60 aryloxy group, or a C 6 —C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —C 1 , —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 a 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 ),
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: hydrogen; deuterium;—F;—C 1 ;—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; 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, or a combination thereof.
2. 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 comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof, and
the electron transport region comprises a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or a combination thereof.
3. The light-emitting device of claim 1 , wherein the emission layer comprises the at least one organometallic compound represented by Formula 1.
4. The light-emitting device of claim 3 , wherein
the at least one organometallic compound represented by Formula 1 comprised in the emission layer serves as a phosphorescent dopant that emits phosphorescence from the emission layer, or
the at least one organometallic compound represented by Formula 1 comprised in the emission layer serves as a delayed fluorescence dopant that emits delayed fluorescence from the emission layer.
5. The light-emitting device of claim 1 , wherein
the emission layer comprises a host and a dopant, and
the dopant comprises the at least one organometallic compound represented by Formula 1.
6. An electronic apparatus comprising the light-emitting device of claim 1 .
7. The electronic apparatus of claim 6 , further comprising a thin-film transistor, wherein
the thin-film transistor comprises a source electrode and a drain electrode, and
the first electrode of the light-emitting device is electrically connected to at least one of the source electrode and the drain electrode of the thin-film transistor.
8. The electronic apparatus of claim 6 , further comprising a color filter, a color-conversion layer, a touchscreen layer, a polarization layer, or a combination thereof.
9. An organometallic compound represented by Formula 1:
wherein in Formula 1,
M is 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), or thulium (Tm),
X 1 to X 3 are each independently C or N,
X 4 is a carbon atom of a carbene moiety,
X 5 is C,
A 1 to A 3 are each independently a C 3 —C 60 carbocyclic group or a C 1 —C 60 heterocyclic group,
A 4 is an X 4 -containing imidazole group or an X 4 -containing imidazole group to which at least one 5-membered ring is condensed,
A 5 is an X 5 -containing 5-membered heterocyclic group,
T 1 to T 3 are each independently a single bond, a double bond, *—N(Z 11 )—*′, *—B (Z 11 )—*′, *—P (Z 11 )—*′, *—C(Z 11 ) (Z 12 )—*′, *—Si (Z 11 ) (Z 12 )—*′, *—Ge (Z 11 ) (Z 12 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(Z 11 )=*′, *=C (Z 11 )—*′, *—C(Z 11 )=C (Z 12 )—*′, *—C(═S)—*′, or *—C═C—*′, and * and *′ each indicate a binding site to an adjacent atom,
a1 to a3 are each independently an integer from 1 to 3,
R 1 to R 5 , Z 11 , and Z 12 are each independently hydrogen, deuterium, —F, —C 1 , —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 , —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 ),
b1 to b5 are each independently an integer from 0 to 10,
when b4 is 2 or greater, at least two R 4 (s) of R 4 (s) in the number of b4 are optionally combined to form 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 ,
when b5 is 2 or greater, at least two Rs(s) of R 5 (s) in the number of b5 are optionally combined to form 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 , and
R 10a is:
deuterium, —F, —C 1 , —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, —C 1 , —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 a 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, —C 1 , —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 a 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 ),
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 hydrogen;
deuterium;—F;—C 1 ;—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; 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, or a combination thereof.
10. The organometallic compound of claim 9 , wherein
a bond between X 1 and M and a bond between X 4 and M are each a coordinate bond, and
a bond between X 2 and M and a bond between X 3 and M are each a covalent bond.
11. The organometallic compound of claim 9 , wherein
X 1 is N, and
X 2 and X 3 are each C.
12. The organometallic compound of claim 9 , wherein A 1 is a X 1 -containing 6-membered ring.
13. The organometallic compound of claim 12 , wherein the X 1 -containing 6-membered ring of A 1 is a benzene group, a pyridine group, or a pyrimidine group, and
the 5-membered ring which is condensed to the X 4 -containing imidazole group of A 4 , and the X 5 -containing 5-membered heterocyclic group of A 5 are each independently a pyrrole group, a pyrazole group, an imidazole group, a triazole group, a furan group, an oxazole group, a thiazole group, an isothiazole group, an oxadiazole group, or a thiadiazole group.
14. The organometallic compound of claim 9 , wherein a group represented by
in Formula 1 is a group represented by one of Formulae A1-1 to A1-3:
wherein in Formulae A1-1 to A1-3,
X 1 and R 1 are respectively the same as described in connection with X 1 and R 1 in Formula 1,
X 11 to X 15 are each independently the same as described in connection with X 1 in Formula 1,
b14 is an integer from 0 to 4,
indicates a binding site to M in Formula 1, and
′ indicates a binding site to T 1 in Formula 1.
15. The organometallic compound of claim 9 , wherein a group represented by
in Formula 1 is represented by one of Formulae A2-1 to A2-7:
wherein in Formulae A2-1 to A2-7,
X 2 and R 2 are respectively the same as described in connection with X 2 and R 2 in Formula 1,
R 21 is the same as described in connection with R 2 in Formula 1,
X 21 to X 28 are each independently the same as described in connection with X 2 in Formula 1,
b25 is an integer from 0 to 5,
b26 is an integer from 0 to 6,
indicates a binding site to M in Formula 1,
′ indicates a binding site to T 1 in Formula 1, and
″ indicates a binding site to T 2 in Formula 1.
16. The organometallic compound of claim 9 , wherein a group represented by
in Formula 1 is a group represented by one of Formulae A3-1 to A3-8:
wherein in Formulae A3-1 to A3-8,
R 3 is the same as described in connection with R 3 in Formula 1,
X 31 to X 35 are each independently the same as described in connection with X 3 in Formula 1,
b33 is an integer from 0 to 3,
indicates a binding site to M in Formula 1,
*′ indicates a binding site to T 2 in Formula 1, and
*″ indicates a binding site to T 3 in Formula 1.
17. The organometallic compound of claim 9 , wherein a group represented by
in Formula 1 is represented by one of Formulae A45-1 to A45-16:
wherein in Formulae A45-1 to A45-16,
Y 4 is O, S, N (R 4a ), C (R 4a ) (R 4b ), or Si (R 4a ) (R 4b ), Y 5 is O, S, N (R 5a ), C (R 5a ) (R 5b ), or Si (R 5a ) (R 5b ),
R 41 and R 42 are each independently the same as described in connection with R 4 in Formula 1, except that R 41 and R 42 are not each hydrogen,
R 51 is the same as described in connection with R 5 in Formula 1, except that R 51 is not hydrogen,
X 4 and X 5 are each independently the same as described in connection with X 4 and X 5 in Formula 1,
R 4a and R 4b are each independently the same as described in connection with R 4 in Formula 1,
R 5a and R 5b are each independently the same as described in connection with R 5 in Formula 1,
indicates a binding site to M in Formula 1, and
′ indicates a binding site to T 3 in Formula 1.
18. The organometallic compound of claim 17 , wherein at least one of R 41 and R 42 comprises a group represented by Formula 2:
wherein in Formula 2,
X 6 is C or N,
A 6 , A 61 , and A 62 are each independently a C 3 —C 60 carbocyclic group or a C 1 —C 60 heterocyclic group,
R 6 , R 61 , and R 62 are each independently the same as described in connection with R 4 in Formula 1,
b6, b61, and b62 are each independently the same as described in connection with b4 in Formula 1, and
indicates a binding site to an adjacent atom.
19. The organometallic compound of claim 9 , wherein the organometallic compound is selected from Compounds 1 to 30 :
20. The organometallic compound of claim 9 , wherein the organometallic compound emits blue light having a maximum emission wavelength in a range of about 400 nanometers (nm) to about 490 nm.