Light-emitting device including organometallic compound, electronic apparatus including the light-emitting device, and organometallic compound
A light-emitting device may include an organometallic compound represented by Formula 1, and an electronic apparatus may include the light-emitting device including the organometallic compound represented by Formula 1. The light-emitting device may further include: a first electrode; a second electrode facing the first electrode; and an interlayer between the first electrode and the second electrode, the interlayer comprising an emission layer: wherein the detailed description of Formula 1 is the same as described in the present specification.
1 . A light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an interlayer between the first electrode and the second electrode, the interlayer comprising an emission layer; and
an organometallic compound represented by Formula 1:
wherein, in Formulae 1 and 1A,
M is platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm),
X 1 is C(Z 1 ) or N,
X 2 is C(Z 2 ) or N,
X 3 is C(Z 3 ) or N,
X 4 is C(Z 4 ) or N,
i) X 1 is C(Z 1 ), X 2 is C(Z 2 ), and Z 1 and Z 2 are linked to each other to form ring CY 5 represented by Formula 1A, ii) X 2 is C(Z 2 ), X 3 is C(Z 3 ), and Z 2 and Z 3 are linked to each other to form ring CY 5 represented by Formula 1A, or iii) X 3 is C(Z 3 ), X 4 is C(Z 4 ), and Z 3 and Z 4 are linked to each other to form ring CY 5 represented by Formula 1A,
ring CY 1 in Formula 1 and ring CY 5 represented by Formula 1A are condensed with each other,
in Formula 1A indicates a single bond or a double bond,
ring CY 5 is a C 1 -C 30 heterocyclic group,
Y 1 is Te, O, S, or Se,
ring CY 2 to ring CY 4 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
X 12 and X 13 are each independently C or N,
X 14 is C,
L 1 to L 3 are each independently a single bond, *—C(R 1a )(R 1b )—*′, *—C(R 1b )═*′, *═C(R 1a )—*′, *—C(R 1a )═C(R 1b )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R 1a )—*′, *—N(R 1a )—*′, *—O—*′, *—P(R 1a )—*′, *—Si(R 1a )(R 1b )—*′, *—P(═O)(R 1a )—*′, *—S—*′, *—S(═O)—*′, *—S(═O) 2 —*′, or *—Ge(R 1a )(R 1b )—*′, wherein * and *′ each indicate a binding site to a neighboring atom,
n1 to n3 are each independently an integer from 1 to 5,
Z 1 to Z 4 , R 2 to R 5 , R 1a , and R 1b 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 that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group that is unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group that is unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group that is 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 ),
a2 to a5 are each independently an integer from 0 to 10,
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 6 -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; 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 any combination thereof,
wherein X 1 is C(Z 1 ), X 2 is C(Z 2 ), X 3 is C(Z 3 ), and X 4 is C(Z 4 ),
i) Z 1 and Z 2 are linked to each other to form ring CY 5 represented by Formula 1A, and at least one selected from Z 3 and Z 4 is not hydrogen,
ii) Z 2 and Z 3 are linked to each other to form ring CY 5 represented by Formula 1A, and at least one selected from Z 1 and Z 4 is not hydrogen, or
iii) Z 3 and Z 4 are linked to each other to form ring CY 5 represented by Formula 1A, and at least one selected from Z 1 and Z 2 is not hydrogen.
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 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.
3 . The light-emitting device of claim 1 , wherein the organometallic compound represented by Formula 1 has a 3 MLCT value of about 10% or more.
4 . The light-emitting device of claim 1 , wherein the organometallic compound represented by Formula 1 has an energy value in a 3 MC state of about 0.3 kcal/mol or more.
5 . The light-emitting device of claim 1 , wherein the emission layer is to emit blue light.
6 . The light-emitting device of claim 1 , wherein the emission layer comprises a host and a dopant, and
the dopant comprises the organometallic compound represented by Formula 1.
7 . The light-emitting device of claim 1 , wherein the interlayer further comprises:
i) a first compound being the organometallic compound represented by Formula 1; and
ii) a second compound comprising at least one π electron-deficient nitrogen-containing C 1 -C 60 cyclic group, a third compound comprising a group represented by Formula 3, a fourth compound to emit delayed fluorescence, or any combination thereof, and
the first compound, the second compound, the third compound, and the fourth compound are different from each other
and
wherein ring CY 71 and ring CY 72 in Formula 3 are each independently a π electron-rich C 3 -C 60 cyclic group or a pyridine group,
X 71 in Formula 3 is a single bond, or a linking group comprising O, S, N, B, C, Si, or any combination thereof,
* in Formula 3 indicates a binding site to a neighboring atom in the third compound, and
the third compound does not comprise the following compounds:
8 . An electronic apparatus comprising the light-emitting device of claim 1 .
9 . The electronic apparatus of claim 8 , 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 selected from the source electrode and the drain electrode of the thin-film transistor.
10 . The electronic apparatus of claim 8 , further comprising:
a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
11 . An organometallic compound represented by Formula 1:
wherein, in Formulae 1 and 1A,
M is platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm),
X 1 is C(Z 1 ) or N,
X 2 is C(Z 2 ) or N,
X 3 is C(Z 3 ) or N,
X 4 is C(Z 4 ) or N,
i) X 1 is C(Z 1 ), X 2 is C(Z 2 ), and Z 1 and Z 2 are linked to each other to form ring CY 5 represented by Formula 1A, ii) X 2 is C(Z 2 ), X 3 is C(Z 3 ), and Z 2 and Z 3 are linked to each other to form ring CY 5 represented by Formula 1A, or iii) X 3 is C(Z 3 ), X 4 is C(Z 4 ), and Z 3 and Z 4 are linked to each other to form ring CY 5 represented by Formula 1A,
ring CY 1 in Formula 1 and ring CY 5 represented by Formula 1A are condensed with each other,
in Formula 1A indicates a single bond or a double bond,
ring CY 5 is a C 1 -C 30 heterocyclic group,
Y 1 is Te, O, S, or Se,
ring CY 2 to ring CY 4 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
X 12 and X 13 are each independently C or N,
X 14 is C,
L 1 to L 3 are each independently a single bond, *—C(R 1a )(R 1b )—*′, *—C(R 1a )═*′, *═C(R 1a )—*′, *—C(R 1a )═C(R 1b )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R 1a )—*′, *—N(R 1a )—*′, *—O—*′, *—P(R 1a )—*′, *—Si(R 1a )(R 1b )—*′, *—P(═O)(R 1a )—*′, *—S—*′, *—S(═O)—*′, *—S(═O) 2 —*′, or *—Ge(R 1a )(R 1b )—*′, wherein * and *′ each indicate a binding site to a neighboring atom,
n1 to n3 are each independently an integer from 1 to 5,
Z 1 to Z 4 , R 2 to R 5 , R 1a , and R 1b 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 that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group that is unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group that is unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group that is 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 ),
a2 to a5 are each independently an integer from 0 to 10,
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; 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 any combination thereof,
wherein X 1 is C(Z 1 ), X 2 is C(Z 2 ), X 3 is C(Z 3 ), and X 4 is C(Z 4 ),
i) Z 1 and Z 2 are linked to each other to form ring CY 5 represented by Formula 1A, and at least one selected from Z 3 and Z 4 is not hydrogen,
ii) Z 2 and Z 3 are linked to each other to form ring CY 5 represented by Formula 1A, and at least one selected from Z 1 and Z 4 is not hydrogen, or
iii) Z 3 and Z 4 are linked to each other to form ring CY 5 represented by Formula 1A, and at least one selected from Z 1 and Z 2 is not hydrogen.
12 . The organometallic compound of claim 11 , wherein ring CY 5 is a Y 1 -containing pentagonal ring.
13 . The organometallic compound of claim 11 , wherein a group represented by
in Formula 1 is one of groups represented by Formulae CY1(4) to CY1(12), CY(16) to CY(24), and CY(28) to CY1(36):
wherein, in Formulae CY1(1) to CY1(36),
R 11 to R 14 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 , —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 ),
Y 1 , R 10a , and Q 1 to Q 3 are respectively as described in Formulae 1 and 1A, and
* and *′ each indicate a binding site to a neighboring atom.
14 . The organometallic compound of claim 11 , wherein ring CY 2 and ring CY 4 are each independently a C 1 -C 30 heterocyclic group, and
ring CY 3 is a C 5 -C 30 carbocyclic group.
15 . The organometallic compound of claim 11 , wherein a group represented by
in Formula 1 is one of groups represented by Formulae CY2(1) to CY2(7):
and
wherein, in Formulae CY2(1) to CY2(7),
b1 is an integer from 0 to 6,
b2 is an integer from 0 to 5,
X 12 and R 2 are respectively as described in Formulae 1 and 1A, and
* , *′, and *″ each indicate a binding site to a neighboring atom.
16 . The organometallic compound of claim 11 , wherein a group represented by
in Formula 1 is one of groups represented by Formulae CY3(1) to CY3(8):
and
wherein, in Formulae CY3(1) to CY3(8),
R 31 to R 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 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 ),
X 13 , R 10a , and Q 1 to Q 3 are respectively as described in Formulae 1 and 1A, and
* , *′, and *″ each indicate a binding site to a neighboring atom.
17 . The organometallic compound of claim 11 , wherein a group represented by
in Formula 1 is one of groups represented by Formulae CY4(1) to CY4(8):
and
wherein, in Formulae CY4(1) to CY4(8),
R 41 to R 44 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 , —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 ),
b3 is an integer from 0 to 4,
b4 is an integer from 0 to 6,
X 14 , R 10a , and Q 1 to Q 3 are respectively as described in Formulae 1 and 1A, and
* and *′ each indicate a binding site to a neighboring atom.
18 . The organometallic compound of claim 11 , wherein L 1 and L 3 are each a single bond,
L 2 is *—C(R 1a )(R 1b )—*′, *—C(R 1a )═*′, *═C(R 1a )—*′, *—C(R 1a )═C(R 1b )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R 1a )—*′, *—O—*′, *—P(R 1a )—*′, *—Si(R 1a )(R 1b )—*′, *—P(═O)(R 1a )—*′, *—S—*′, *—S(═O)—*′, *—S(═O) 2 —*′, or *—Ge(R 1a )(R 1b )—*′, and
* and *′ each indicate a binding site to a neighboring atom.
19 . The organometallic compound of claim 11 , wherein the organometallic compound is selected from among Compounds 1 to 54: