ORGANOMETALLIC COMPOUND, LIGHT-EMITTING DEVICE INCLUDING THE ORGANOMETALLIC COMPOUND AND ELECTRONIC APPARATUS INCLUDING THE LIGHT-EMITTING DEVICE
20230118772 · 2023-04-20
Assignee
Inventors
- Eunyoung Lee (Yongin-si, KR)
- Soobyung Ko (Yongin-si, KR)
- Sungbum Kim (Yongin-si, KR)
- Sujin Shin (Yongin-si, KR)
- Mina Jeon (Yongin-si, KR)
- Jinhee JU (Yongin-si, KR)
Cpc classification
H10K85/6572
ELECTRICITY
C07B2200/05
CHEMISTRY; METALLURGY
H10K85/341
ELECTRICITY
International classification
Abstract
An electronic apparatus includes a light-emitting device that includes an organometallic compound represented by Formula 1:
##STR00001##
Claims
1. A light-emitting device comprising: a first electrode; a second electrode facing the first electrode; an interlayer located between the first electrode and the second electrode and comprising an emission layer; and an organometallic compound represented by Formula 1: ##STR00272## wherein in Formula 1, 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), ring CY.sub.1, ring CY.sub.2, ring CY.sub.4, ring CY.sub.32, and ring CY.sub.33 are each independently a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group, X.sub.1, X.sub.2, and X.sub.4 are each independently C or N, X.sub.31 and X.sub.32 are each independently C or N, X.sub.33 is C(Z.sub.3) or N, X.sub.34 is C(Z.sub.4) or N, L.sub.1 to L.sub.3 are each independently a single bond, *—C(R.sub.1a)(R.sub.1b)—*′, *—C(R.sub.1a)═*′, *═C(R.sub.1a)—*′, *—C(R.sub.1a)═C(R.sub.1b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R.sub.1a)—*′, *—N(R.sub.1a)—*′, *—O—*′, *—P(R.sub.1a)—*′, *—Si(R.sub.1a)(R.sub.1b)—*′, *—P(═O)(R.sub.1a)—*′, *—S—*′, *—S(═O)—*′, *—S(═O).sub.2—*′, or *—Ge(R.sub.1a)(R.sub.1b)—*′, wherein * and *′ each indicate a binding site to a neighboring atom, n1 to n3 are each independently an integer from 1 to 5, R.sub.1, R.sub.2, R.sub.4, R.sub.32, and R.sub.33 are each independently deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2), R.sub.1a, R.sub.1b, Z.sub.3, and Z.sub.4 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2), a1, a2, a4, a32, and a33 are each independently an integer from 0 to 10, a moiety represented by ##STR00273## in Formula 1 does not include a group represented by Formula CY1(1)-1, ##STR00274## R.sub.10a is: deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; a C.sub.1-C.sub.6 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, or a C.sub.1-C.sub.60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.11)(Q.sub.12), —B(Q.sub.11)(Q.sub.12), —C(═O)(Q.sub.11), —S(═O).sub.2(Q.sub.11), —P(═O)(Q.sub.11)(Q.sub.12), or a combination thereof; a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, or a C.sub.6-C.sub.60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, —Si(Q.sub.21)(Q.sub.22)(Q.sub.23), —N(Q.sub.21)(Q.sub.22), —B(Q.sub.21)(Q.sub.22), —C(═O)(Q.sub.21), —S(═O).sub.2(Q.sub.21), —P(═O)(Q.sub.21)(Q.sub.22), or a combination thereof; or —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), or —P(═O)(Q.sub.31)(Q.sub.32), and Q.sub.1 to Q.sub.3, Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23, and Q.sub.31 to Q.sub.33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxy group; or a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C.sub.1-C.sub.60 alkyl group, a C.sub.1-C.sub.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 located between the first electrode and the emission layer; and an electron transport region located 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 hole blocking 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 organometallic compound represented by Formula 1.
4. The light-emitting device of claim 1, wherein the emission layer emits light having a maximum emission wavelength in a range of about 430 nm to about 480 nm.
5. 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.
6. The light-emitting device of claim 1, wherein the interlayer comprises: a first compound which is the organometallic compound represented by Formula 1; and a second compound including at least one π electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or a combination of the second, third, and fourth compounds, and the first compound, the second compound, the third compound, and the fourth compound are different from each other: ##STR00275## wherein in Formula 3, ring CY.sub.71 and ring CY.sub.72 are each independently a π electron-rich C.sub.3-C.sub.60 cyclic group or a pyridine group, X.sub.71 in Formula 3 is a single bond, or a linking group including O, S, N, B, C, Si, or a combination thereof, * in Formula 3 indicates a binding site to a neighboring atom of the third compound, and the following compounds are excluded from the third compound: ##STR00276##
7. An electronic apparatus comprising the light-emitting device of claim 1.
8. The electronic apparatus of claim 7, 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.
9. The electronic apparatus of claim 7, further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or a combination thereof.
10. An organometallic compound represented by Formula 1: ##STR00277## wherein in Formula 1, 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), ring CY.sub.1, ring CY.sub.2, ring CY.sub.4, ring CY.sub.32, and ring CY.sub.33 are each independently a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group, X.sub.1, X.sub.2, and X.sub.4 are each independently C or N, X.sub.31 and X.sub.32 are each independently C or N, X.sub.33 is C(Z.sub.3) or N, X.sub.34 is C(Z.sub.4) or N, L.sub.1 to L.sub.3 are each independently a single bond, *—C(R.sub.1a)(R.sub.1b)—*′, *—C(R.sub.1a)═*′, *═C(R.sub.1a)—*′, *—C(R.sub.1a)═C(R.sub.1b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R.sub.1a)—*′, *—N(R.sub.1a)—*′, *—O—*′, *—P(R.sub.1a)—*′, *—Si(R.sub.1a)(R.sub.1b)—*′, *—P(═O)(R.sub.1a)—*′, *—S—*′, *—S(═O)—*′, *—S(═O).sub.2—*′, or *—Ge(R.sub.1a)(R.sub.1b)—*′, wherein * and *′ each indicate a binding site to a neighboring atom, n1 to n3 are each independently an integer from 1 to 5, R.sub.1, R.sub.2, R.sub.4, R.sub.32, and R.sub.33 are each independently deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2), R.sub.1a, R.sub.1b, Z.sub.3, and Z.sub.4 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2), a1, a2, a4, a32, and a33 are each independently an integer from 0 to 10, a moiety represented by ##STR00278## in Formula 1 does not include a group represented by Formula CY1(1)-1, ##STR00279## R.sub.10a is: deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; a C.sub.1-C.sub.6 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, or a C.sub.1-C.sub.60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.11)(Q.sub.12), —B(Q.sub.11)(Q.sub.12), —C(═O)(Q.sub.11), —S(═O).sub.2(Q.sub.11), —P(═O)(Q.sub.11)(Q.sub.12), or a combination thereof; a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, or a C.sub.6-C.sub.60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, —Si(Q.sub.21)(Q.sub.22)(Q.sub.23), —N(Q.sub.21)(Q.sub.22), —B(Q.sub.21)(Q.sub.22), —C(═O)(Q.sub.21), —S(═O).sub.2(Q.sub.21), —P(═O)(Q.sub.21)(Q.sub.22), or a combination thereof; or —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), or —P(═O)(Q.sub.31)(Q.sub.32), and Q.sub.1 to Q.sub.3, Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23, and Q.sub.31 to Q.sub.33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxy group; or a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C.sub.1-C.sub.60 alkyl group, a C.sub.1-C.sub.60 alkoxy group, a phenyl group, a biphenyl group, or a combination thereof.
11. The organometallic compound of claim 10, wherein ring CY.sub.1 is a C.sub.1-C.sub.30 heterocyclic group containing two or more nitrogen atoms.
12. The organometallic compound of claim 10, wherein ring CY.sub.4 is pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, phenanthroline, pyrrole, pyrazole, imidazole, triazole, benzopyrazole, benzimidazole, or benzothiazole.
13. The organometallic compound of claim 10, wherein a moiety represented by ##STR00280## in Formula 1 is one of groups represented by Formulae CY1(1) to CY1(18): ##STR00281## ##STR00282## ##STR00283## wherein in Formulae CY1(1) to CY1(18), R.sub.11 to R.sub.17 are each independently deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2), R.sub.11 is not a methyl group (—CH.sub.3), a14 is an integer from 0 to 4, a15 is an integer from 0 to 3, a16 is an integer from 0 to 6, a17 is an integer from 0 to 5, * and *′ each indicate a binding site to a neighboring atom, and X.sub.1, R.sub.10a, and Q.sub.1 to Q.sub.3 are the same as described in Formula 1.
14. The organometallic compound of claim 10, wherein a moiety represented by ##STR00284## in Formula 1 is one of groups represented by Formulae CY2(1) to CY2(20): ##STR00285## ##STR00286## ##STR00287## wherein in Formulae CY2(1) to CY2(20), X.sub.2 is C or N, R.sub.21 to R.sub.23 are each independently deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2), *, *′, and *″ each indicate a binding site to a neighboring atom, and R.sub.10a and Q.sub.1 to Q.sub.3 are the same as described in Formula 1.
15. The organometallic compound of claim 10, wherein a moiety represented by ##STR00288## in Formula 1 is one of groups represented by Formulae CY4(1) to CY4(14): ##STR00289## ##STR00290## wherein in Formulae CY4(1) to CY4(14), R.sub.41 to R.sub.44 are each independently deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2), * and *′ each indicate a binding site to a neighboring atom, and R.sub.10a and Q.sub.1 to Q.sub.3 are the same as described in Formula 1.
16. The organometallic compound of claim 10, wherein ring CY.sub.32 and ring CY.sub.33 are each independently a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, or a quinoxaline group.
17. The organometallic compound of claim 10, wherein L.sub.1 and L.sub.3 are each a single bond, L.sub.2 is *—O—*′ or *—S—*′, and * and *′ each indicate a binding site to a neighboring atom.
18. The organometallic compound of claim 10, wherein R.sub.1, R.sub.2, R.sub.4, R.sub.32, and R.sub.33 are each independently: deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, or a C.sub.1-C.sub.20 alkoxy group; a C.sub.1-C.sub.20 alkyl group or a C.sub.1-C.sub.20 alkoxy group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.10 alkyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group; or a phenyl group, a biphenyl group, a terphenyl group, a C.sub.1-C.sub.10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, or a chrysenyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group.
19. The organometallic compound of claim 10, wherein the organometallic compound is represented by Formula 1-1: ##STR00291## wherein in Formula 1-1, Y.sub.31 is C(Z.sub.31) or N, Y.sub.32 is C(Z.sub.32) or N, Y.sub.33 is C(Z.sub.33) or N, Y.sub.34 is C(Z.sub.34) or N, Y.sub.35 is C(Z.sub.35) or N, Y.sub.36 is C(Z.sub.36) or N, Y.sub.37 is C(Z.sub.37) or N, Y.sub.38 is C(Z.sub.38) or N, Z.sub.31 to Z.sub.38 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2), a moiety represented by ##STR00292## in Formula 1-1 does not include a group represented by Formula CY1(1)-1, and ##STR00293## M, ring CY.sub.1, ring CY.sub.2, ring CY.sub.4, X.sub.1, X.sub.2, X.sub.4, X.sub.31 to X.sub.34, L.sub.1 to L.sub.3, n1 to n3, R.sub.1, R.sub.2, R.sub.4, a1, a2, a4, R.sub.10a, and Q.sub.1 to Q.sub.3 are the same as described in Formula 1.
20. The organometallic compound of claim 19, wherein i) Y.sub.35 is C(Z.sub.35), Y.sub.36 is C(Z.sub.36), Y.sub.37 is C(Z.sub.37), and Y.sub.38 is C(Z.sub.38), ii) Y.sub.35 is C(Z.sub.35), Y.sub.36 is C(Z.sub.36), Y.sub.37 is C(Z.sub.37), and Y.sub.38 is N, iii) Y.sub.35 is C(Z.sub.35), Y.sub.36 is C(Z.sub.36), Y.sub.37 is N, and Y.sub.38 is C(Z.sub.38), iv) Y.sub.35 is C(Z.sub.35), Y.sub.36 is N, Y.sub.37 is C(Z.sub.37), and Y.sub.38 is C(Z.sub.38), or v) Y.sub.35 is N, Y.sub.36 is C(Z.sub.36), Y.sub.37 is C(Z.sub.37), and Y.sub.38 is C(Z.sub.38), and Z.sub.35 to Z.sub.38 are the same as described in Formula 1-1.
Description
BRIEF DESCRIPTION OF THE DRAWINGS
[0057] The above and other aspects, features, and advantages of embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
[0058]
[0059]
[0060]
DETAILED DESCRIPTION OF THE EMBODIMENTS
[0061] Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are described below, with the accompanied drawings, to explain various aspects of the invention. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression “at least one of a, b or c” indicates only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.
[0062] A light-emitting device according to an embodiment may include: a first electrode; a second electrode facing the first electrode; an interlayer located between the first electrode and the second electrode and including an emission layer; and an organometallic compound represented by Formula 1:
##STR00022##
[0063] wherein in Formula 1, M may be 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).
[0064] In an embodiment, M may be platinum (Pt) or palladium (Pd).
[0065] Ring CY.sub.1, ring CY.sub.2, ring CY.sub.4, ring CY.sub.32, and ring CY.sub.33 in Formula 1 may each independently be a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group.
[0066] For example, ring CY.sub.1, ring CY.sub.2, ring CY.sub.4, ring CY.sub.32, and ring CY.sub.33 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, 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, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
[0067] In an embodiment, ring CY.sub.1 may be a C.sub.1-C.sub.30 heterocyclic group.
[0068] In an embodiment, ring CY.sub.1 may be a C.sub.1-C.sub.30 heterocyclic group containing two or more nitrogen atoms.
[0069] In an embodiment, ring CY.sub.2 may be a C.sub.5-C.sub.30 carbocyclic group.
[0070] For example, ring CY.sub.2 may be benzene or naphthalene.
[0071] In an embodiment, ring CY.sub.4 may be a C.sub.1-C.sub.30 heterocyclic group.
[0072] In an embodiment, ring CY.sub.4 may be pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, phenanthroline, pyrrole, pyrazole, imidazole, triazole, benzopyrazole, benzimidazole, or benzothiazole.
[0073] For example, ring CY.sub.4 may be pyridine.
[0074] In an embodiment, ring CY.sub.32 and ring CY.sub.33 may each independently be a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, or a quinoxaline group.
[0075] In one or more embodiments, ring CY.sub.32 may be a benzene group or a naphthalene group, and ring CY.sub.33 may be a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a quinoline group, or an isoquinoline group.
[0076] X.sub.1, X.sub.2, and X.sub.4 in Formula 1 may each independently be C or N.
[0077] In an embodiment, X.sub.1 may be C, X.sub.2 may be C, and X.sub.4 may be N.
[0078] In an embodiment, a moiety represented by
##STR00023##
in Formula 1 may be one of groups represented by Formulae CY1(1) to CY1(18):
##STR00024## ##STR00025## ##STR00026##
[0079] wherein in Formulae CY1(1) to CY1(18),
[0080] R.sub.11 to R.sub.17 may each independently be deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2),
[0081] R.sub.11 may not be a methyl group (—CH.sub.3),
[0082] a14 may be an integer from 0 to 4,
[0083] a15 may be an integer from 0 to 3,
[0084] a16 may be an integer from 0 to 6,
[0085] a17 may be an integer from 0 to 5,
[0086] * and *′ each indicate a binding site to a neighboring atom, and
[0087] X.sub.1, R.sub.10a, and Q.sub.1 to Q.sub.3 are the same as described in the disclosure.
[0088] In an embodiment, R.sub.11 may be:
[0089] —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CH.sub.2CH.sub.3, —CH.sub.2CD.sub.3, —CH.sub.2CD.sub.2H, —CH.sub.2CDH.sub.2, —CHDCH.sub.3, —CHDCD.sub.2H, —CHDCDH.sub.2, —CHDCD.sub.3, —CD.sub.2CD.sub.3, —CD.sub.2CD.sub.2H, or —CD.sub.2CDH.sub.2;
[0090] an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group, each unsubstituted or substituted with deuterium; or
[0091] a phenyl group, a biphenyl group, a terphenyl group, or a naphthalene group, each unsubstituted or substituted with at least one of deuterium, —CH.sub.3, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CH.sub.2CH.sub.3, —CH.sub.2CD.sub.3, —CH.sub.2CD.sub.2H, —CH.sub.2CDH.sub.2, —CHDCH.sub.3, —CHDCD.sub.2H, —CHDCDH.sub.2, —CHDCD.sub.3, —CD.sub.2CD.sub.3, —CD.sub.2CD.sub.2H, —CD.sub.2CDH.sub.2, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group; and a tert-butyl group.
[0092] In an embodiment, R.sub.12 to R.sub.17 may each independently be:
[0093] deuterium, —CH.sub.3, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CH.sub.2CH.sub.3, —CH.sub.2CD.sub.3, —CH.sub.2CD.sub.2H, —CH.sub.2CDH.sub.2, —CHDCH.sub.3, —CHDCD.sub.2H, —CHDCDH.sub.2, —CHDCD.sub.3, —CD.sub.2CD.sub.3, —CD.sub.2CD.sub.2H, or —CD.sub.2CDH.sub.2; or
[0094] an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group, each unsubstituted or substituted with deuterium.
[0095] In an embodiment, a moiety represented by
##STR00027##
in Formula 1 may not include a group represented by Formula CY1(1)-1:
##STR00028##
[0096] wherein in Formula CY1(1)-1, * and *′ each indicate a binding site to a neighboring atom.
[0097] In an embodiment, a moiety represented by
##STR00029##
in Formula 1 may not be a group represented by Formula CY1(1)-1, CY1(5)-1, CY1(6)-1, or CY1(9)-1:
##STR00030##
[0098] In an embodiment, a moiety represented by
##STR00031##
in Formula 1 may be one of groups represented by Formulae CY2(1) to CY2(20):
##STR00032## ##STR00033## ##STR00034##
[0099] wherein in Formulae CY2(1) to CY2(20),
[0100] X.sub.2 may be C or N,
[0101] R.sub.21 to R.sub.23 may each independently be deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2),
[0102] *, *′, and *″ each indicate a binding site to a neighboring atom, and
[0103] R.sub.10a and Q.sub.1 to Q.sub.3 are the same as described in the disclosure.
[0104] In an embodiment, a moiety represented by
##STR00035##
in Formula 1 may be one of groups represented by Formulae CY4(1) to CY4(14):
##STR00036## ##STR00037##
[0105] wherein in Formulae CY4(1) to CY4(14),
[0106] R.sub.41 to R.sub.44 may each independently be deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2),
[0107] R.sub.10a and Q.sub.1 to Q.sub.3 are the same as described in the disclosure, and
[0108] * and *′ each indicate a binding site to a neighboring atom.
[0109] In an embodiment, R.sub.41 to R.sub.44 may each independently be:
[0110] —CH.sub.3, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CH.sub.2CH.sub.3, —CH.sub.2CD.sub.3, —CH.sub.2CD.sub.2H, —CH.sub.2CDH.sub.2, —CHDCH.sub.3, —CHDCD.sub.2H, —CHDCDH.sub.2, —CHDCD.sub.3, —CD.sub.2CD.sub.3, —CD.sub.2CD.sub.2H, or —CD.sub.2CDH.sub.2;
[0111] an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group, each unsubstituted or substituted with deuterium; or
[0112] a phenyl group, a biphenyl group, a terphenyl group, or a naphthalene group, each unsubstituted or substituted with at least one of deuterium, —CH.sub.3, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CH.sub.2CH.sub.3, —CH.sub.2CD.sub.3, —CH.sub.2CD.sub.2H, —CH.sub.2CDH.sub.2, —CHDCH.sub.3, —CHDCD.sub.2H, —CHDCDH.sub.2, —CHDCD.sub.3, —CD.sub.2CD.sub.3, —CD.sub.2CD.sub.2H, —CD.sub.2CDH.sub.2, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group; and a tert-butyl group.
[0113] X.sub.31 and X.sub.32 in Formula 1 may each independently be C or N.
[0114] In an embodiment, X.sub.31 and X.sub.32 may each be C.
[0115] X.sub.33 in Formula 1 may be C(Z.sub.3) or N.
[0116] X.sub.34 in Formula 1 may be C(Z.sub.4) or N.
[0117] Z.sub.3 and Z.sub.4 are the same as described in the disclosure.
[0118] L.sub.1 to L.sub.3 in Formula 1 may each independently be a single bond, *—C(R.sub.1a)(R.sub.1b)—*, *—C(R.sub.1a)═*′, *═C(R.sub.1a)—*′, *—C(R.sub.1a)═C(R.sub.1b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R.sub.1a)—*, *—N(R.sub.1a)—*′, *—O—*′, *—P(R.sub.1a)—*′, *—Si(R.sub.1a)(R.sub.1b)—*′, *—P(═O)(R.sub.1a)—*′, *—S—*′, *—S(═O)—*′, *—S(═O).sub.2—*′, or *—Ge(R.sub.1a)(R.sub.1b)—*. * and *′ each indicate a binding site to a neighboring atom.
[0119] In an embodiment, L.sub.1 and L.sub.3 may each be a single bond.
[0120] In an embodiment, L.sub.2 may be *—O—*′ or *—S—*′.
[0121] n1 to n3 in Formula 1 may each independently be an integer from 1 to 5.
[0122] In an embodiment, L.sub.2 may be *—O—*′ or *—S—*′, and n2 may be 1.
[0123] R.sub.1, R.sub.2, R.sub.4, R.sub.32, and R.sub.33 in Formula 1 may each independently be deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2).
[0124] For example, R.sub.1, R.sub.2, R.sub.4, R.sub.32, and R.sub.33 may each independently be:
[0125] deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, or a C.sub.1-C.sub.20 alkoxy group;
[0126] a C.sub.1-C.sub.20 alkyl group or a C.sub.1-C.sub.20 alkoxy group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;
[0127] a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a C.sub.1-C.sub.10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzosilolyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —P(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), and —P(═O)(Q.sub.31)(Q.sub.32); or
[0128] —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2), and
[0129] Q.sub.1 to Q.sub.3 and Q.sub.31 to Q.sub.33 may each independently be:
[0130] —CH.sub.3, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CH.sub.2CH.sub.3, —CH.sub.2CD.sub.3, —CH.sub.2CD.sub.2H, —CH.sub.2CDH.sub.2, —CHDCH.sub.3, —CHDCD.sub.2H, —CHDCDH.sub.2, —CHDCD.sub.3, —CD.sub.2CD.sub.3, —CD.sub.2CD.sub.2H, or —CD.sub.2CDH.sub.2;
[0131] an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each unsubstituted or substituted with at least one of deuterium, a C.sub.1-C.sub.10 alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group.
[0132] In an embodiment, R.sub.1, R.sub.2, R.sub.4, R.sub.32, and R.sub.33 may each independently be:
[0133] deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, or a C.sub.1-C.sub.20 alkoxy group;
[0134] a C.sub.1-C.sub.20 alkyl group or a C.sub.1-C.sub.20 alkoxy group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.10 alkyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group; or
[0135] a phenyl group, a biphenyl group, a terphenyl group, a C.sub.1-C.sub.10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, or a chrysenyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group.
[0136] In one or more embodiments, R.sub.1, R.sub.2, R.sub.4, R.sub.32, and R.sub.33 may each independently be:
[0137] deuterium, —F, —Cl, —Br, —I, or a C.sub.1-C.sub.20 alkyl group;
[0138] a C.sub.1-C.sub.20 alkyl group substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.10 alkyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group; or
[0139] a phenyl group, a biphenyl group, a terphenyl group, a C.sub.1-C.sub.10 alkylphenyl group, or a naphthyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a C.sub.1-C.sub.20 alkyl group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.10 alkylphenyl group, and a naphthyl group.
[0140] R.sub.1a, R.sub.1b, Z.sub.3, and Z.sub.4 in Formula 1 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2).
[0141] For example, R.sub.1a, R.sub.1b, Z.sub.3, and Z.sub.4 may each independently be:
[0142] hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, or a C.sub.1-C.sub.20 alkoxy group;
[0143] a C.sub.1-C.sub.20 alkyl group or a C.sub.1-C.sub.20 alkoxy group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;
[0144] a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzosilolyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —P(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), and —P(═O)(Q.sub.31)(Q.sub.32); or
[0145] —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2), and
[0146] Q.sub.1 to Q.sub.3 and Q.sub.31 to Q.sub.33 may each independently be:
[0147] —CH.sub.3, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CH.sub.2CH.sub.3, —CH.sub.2CD.sub.3, —CH.sub.2CD.sub.2H, —CH.sub.2CDH.sub.2, —CHDCH.sub.3, —CHDCD.sub.2H, —CHDCDH.sub.2, —CHDCD.sub.3, —CD.sub.2CD.sub.3, —CD.sub.2CD.sub.2H, or —CD.sub.2CDH.sub.2; or
[0148] an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each unsubstituted or substituted with at least one of deuterium, a C.sub.1-C.sub.10 alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group.
[0149] a1, a2, a4, a32, and a33 in Formula 1 may each independently be an integer from 0 to 10.
[0150] In one or more embodiments, the organometallic compound may be represented by Formula 1-1:
##STR00038##
[0151] wherein in Formula 1-1,
[0152] Y.sub.31 may be C(Z.sub.31) or N,
[0153] Y.sub.32 may be C(Z.sub.32) or N,
[0154] Y.sub.33 may be C(Z.sub.33) or N,
[0155] Y.sub.34 may be C(Z.sub.34) or N,
[0156] Y.sub.35 may be C(Z.sub.35) or N,
[0157] Y.sub.36 may be C(Z.sub.36) or N,
[0158] Y.sub.37 may be C(Z.sub.37) or N,
[0159] Y.sub.38 may be C(Z.sub.38) or N,
[0160] Z.sub.31 to Z.sub.38 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2),
[0161] a moiety represented by
##STR00039##
in Formula 1-1 may not include a group represented by Formula CY1(1)-1, and
##STR00040##
[0162] M, ring CY.sub.1, ring CY.sub.2, ring CY.sub.4, X.sub.1, X.sub.2, X.sub.4, X.sub.31 to X.sub.34, L.sub.1 to L.sub.3, n1 to n3, R.sub.1, R.sub.2, R.sub.4, a1, a2, a4, R.sub.10a, and Q.sub.1 to Q.sub.3 are the same as described in the disclosure.
[0163] In an embodiment, in Formula 1-1, Y.sub.31 may be C(Z.sub.31), Y.sub.32 may be C(Z.sub.32), Y.sub.33 may be C(Z.sub.33), and Y.sub.34 may be C(Z.sub.34).
[0164] In an embodiment, in Formula 1-1,
[0165] i) Y.sub.35 may be C(Z.sub.35), Y.sub.36 may be C(Z.sub.36), Y.sub.37 may be C(Z.sub.37), and Y.sub.38 may be C(Z.sub.38),
[0166] ii) Y.sub.35 may be C(Z.sub.35), Y.sub.36 may be C(Z.sub.36), Y.sub.37 may be C(Z.sub.37), and Y.sub.38 may be N,
[0167] iii) Y.sub.35 may be C(Z.sub.35), Y.sub.36 may be C(Z.sub.36), Y.sub.37 may be N, and Y.sub.38 may be C(Z.sub.38),
[0168] iv) Y.sub.35 may be C(Z.sub.35), Y.sub.36 may be N, Y.sub.37 may be C(Z.sub.37), and Y.sub.38 may be C(Z.sub.38), or
[0169] v) Y.sub.35 may be N, Y.sub.36 may be C(Z.sub.36), Y.sub.37 may be C(Z.sub.37), and Y.sub.38 may be C(Z.sub.38).
[0170] In an embodiment, the organometallic compound represented by Formula 1 may be one of Compounds 1 to 176:
##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083## ##STR00084##
[0171] When the organometallic compound represented by Formula 1 is applied to the emission layer of the light-emitting device, luminescence efficiency characteristics and device stability may be improved. Accordingly, due to the use of the organometallic compound, an electronic device (for example, an organic light-emitting device) having low driving voltage, high efficiency, and long lifespan characteristics may be implemented.
[0172] Methods of synthesizing the organometallic compound represented by Formula 1 may be easily understood to those of ordinary skill in the art by referring to Synthesis Examples and/or Examples described herein.
[0173] In an embodiment,
[0174] the first electrode of the light-emitting device may be an anode,
[0175] the second electrode of the light-emitting device may be a cathode,
[0176] the interlayer may further include a hole transport region located between the first electrode and the emission layer and an electron transport region located between the emission layer and the second electrode,
[0177] the hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and
[0178] the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0179] In one or more embodiments, the interlayer of the light-emitting device may include the organometallic compound represented by Formula 1.
[0180] In one or more embodiments, the emission layer of the light-emitting device may include the organometallic compound represented by Formula 1.
[0181] In one or more embodiments, the emission layer may emit blue light. For example, the emission layer may emit blue light having a maximum emission wavelength in a range of about 410 nm to about 500 nm, about 420 nm to about 490 nm, about 430 nm to about 480 nm, or about 430 nm to about 470 nm.
[0182] In one or more embodiments, the emission layer of the light-emitting device may include a dopant and a host, and the organometallic compound represented by Formula 1 may be included in the dopant. That is, the organometallic compound may serve as a dopant. For example, the emission layer may emit blue light. The blue light may have a maximum emission wavelength in a range of, for example, about 430 nm to about 470 nm.
[0183] In one or more embodiments, the electron transport region of the light-emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. For example, the hole blocking layer may directly contact the emission layer.
[0184] In one or more embodiments, the light-emitting device may further include at least one of a first capping layer located outside the first electrode and a second capping layer located outside the second electrode, and the organometallic compound represented by Formula 1 may be included in at least one of the first capping layer and the second capping layer. More details for the first capping layer and/or the second capping layer are the same as described in the disclosure.
[0185] In an embodiment, the light-emitting device may include:
[0186] a first capping layer located outside the first electrode and including the organometallic compound represented by Formula 1;
[0187] a second capping layer located outside the second electrode and including the organometallic compound represented by Formula 1; or
[0188] the first capping layer and the second capping layer.
[0189] The wording “(interlayer and/or capping layer) includes an organometallic compound” as used herein may be understood as “(interlayer and/or capping layer) may include one kind of organometallic compound represented by Formula 1 or two different kinds of organometallic compounds, each represented by Formula 1”.
[0190] For example, the interlayer and/or the capping layer may include Compound 1 only as the organometallic compound. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In one or more embodiments, the interlayer may include, as the organometallic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be present in the same layer (for example, both Compound 1 and Compound 2 may be present in an emission layer), or may be present in different layers (for example, Compound 1 may be present in an emission layer, and Compound 2 may be present in an electron transport region).
[0191] The term “interlayer” as used herein refers to a single layer and/or all of a plurality of layers located between the first electrode and the second electrode of the light-emitting device.
[0192] In an embodiment,
[0193] the interlayer of the light-emitting device may include:
[0194] i) a first compound which is the organometallic compound represented by Formula 1; and
[0195] ii) a second compound including at least one π electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, and
[0196] the first compound, the second compound, the third compound, and the fourth compound may be different from each other:
##STR00085##
[0197] wherein in Formula 3, ring CY.sub.71 and ring CY.sub.72 may each independently be a n electron-rich C.sub.3-C.sub.60 cyclic group or a pyridine group,
[0198] X.sub.71 in Formula 3 may be a single bond, or a linking group including O, S, N, B, C, Si, or any combination thereof,
[0199] * in Formula 3 indicates a binding site to a neighboring atom in the third compound, and
[0200] the following compounds may be excluded from the third compound:
##STR00086##
[0201] In an embodiment, in the light-emitting device,
[0202] the emission layer may include: i) the first compound; and ii) the second compound, the third compound, the fourth compound, or any combination thereof, and
[0203] the emission layer may emit phosphorescence or fluorescence emitted from the first compound.
[0204] Description of Second Compound to Fourth Compound
[0205] The second compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.
[0206] For example, the light-emitting device may further include at least one of the second compound and the third compound, in addition to the first compound.
[0207] In one or more embodiments, the light-emitting device may further include the fourth compound, in addition to the first compound.
[0208] In one or more embodiments, the light-emitting device may include all of the first compound to the fourth compound.
[0209] In one or more embodiments, the interlayer may include the second compound. The interlayer may further include the third compound, the fourth compound, or a combination thereof, in addition to the first compound and the second compound.
[0210] In an embodiment, a difference between a triplet energy level (eV) and a singlet energy level (eV) of the fourth compound may be about 0 eV or higher and about 0.5 eV or lower (or about 0 eV or higher and about 0.3 eV or lower).
[0211] For example, the fourth compound may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
[0212] In one or more embodiments, the fourth compound may be a C.sub.8-C.sub.60 polycyclic group-containing compound including at least two condensed cyclic groups that share B.
[0213] In an embodiment, the fourth compound may include a condensed cyclic ring in which at least one third ring is condensed with at least one fourth ring,
[0214] the third ring may be 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 norobornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and
[0215] the fourth ring may be 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.
[0216] In one or more embodiments, the interlayer may include the fourth compound. The interlayer may further include the second compound, the third compound, or any combination thereof, in addition to the first compound and the fourth compound.
[0217] In one or more embodiments, the interlayer may include the third compound. For example, the third compound may not include a compound represented by CBP and mCBP described herein.
[0218] The emission layer in the interlayer may include: i) the first compound; and ii) the second compound, the third compound, the fourth compound, or any combination thereof.
[0219] The emission layer may emit phosphorescence or fluorescence emitted from the first compound. For example, the phosphorescence or the fluorescence emitted from the first compound may be blue light.
[0220] For example, the emission layer in the light-emitting device may include the first compound and the second compound, and the first compound and the second compound may form an exciplex.
[0221] In one or more embodiments, the emission layer in the light-emitting device may include the first compound, the second compound, and the third compound, and the first compound and the second compound may form an exciplex.
[0222] In one or more embodiments, the emission layer in the light-emitting device may include the first compound and the fourth compound, and the fourth compound may serve to improve color purity, luminescence efficiency, and lifespan characteristics of the light-emitting device.
[0223] In an embodiment, the second compound may include a compound represented by Formula 2:
##STR00087##
[0224] wherein in Formula 2,
[0225] L.sub.61 to L.sub.63 may each independently be a single bond, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0226] b61 to b63 may each independently be an integer from 1 to 5,
[0227] X.sub.64 may be N or C(R.sub.64), X.sub.65 may be N or C(R.sub.65), X.sub.66 may be N or C(R.sub.66), and at least one of X.sub.64 to X.sub.66 may be N,
[0228] R.sub.61 to R.sub.66 are the same as described in the disclosure, and
[0229] R.sub.10a is the same as described in the disclosure.
[0230] In one or more embodiments, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:
##STR00088##
[0231] wherein in Formulae 3-1 to 3-5,
[0232] ring CY.sub.71 to ring CY.sub.74 may each independently be a π electron-rich C.sub.3-C.sub.60 cyclic group or a pyridine group,
[0233] X.sub.82 may be a single bond, O, S, N-[(L.sub.82).sub.b82-R.sub.82], C(R.sub.82a)(R.sub.82b), or Si(R.sub.82a)(R.sub.82b),
[0234] X.sub.83 may be a single bond, O, S, N[(L.sub.83).sub.b83-R.sub.83], C(R.sub.83a)(R.sub.83b), or Si(R.sub.83a)(R.sub.83b),
[0235] X.sub.84 may be O, S, N[(L.sub.84).sub.b84-R.sub.84], C(R.sub.84a)(R.sub.84b), or Si(R.sub.84a)(R.sub.84b),
[0236] X.sub.85 may be C or Si,
[0237] L.sub.81 to L.sub.85 may each independently be a single bond, *—C(Q.sub.4)(Q.sub.5)-*′, *—Si(Q.sub.4)(Q.sub.5)-*′, a π electron-rich C.sub.3-C.sub.60 cyclic group unsubstituted or substituted with at least one R.sub.10a, or a pyridine group unsubstituted or substituted with at least one R.sub.10a, wherein Q.sub.4 and Q.sub.5 are the same as described in connection with Q.sub.1 in the disclosure,
[0238] b81 to b85 may each independently be an integer from 1 to 5,
[0239] R.sub.71 to R.sub.74, R.sub.81 to R.sub.85, R.sub.82a, R.sub.82b, R.sub.83a, R.sub.83b, R.sub.84a, and R.sub.84b are the same as described in the disclosure,
[0240] a71 to a74 may each independently be an integer from 0 to 20, and
[0241] R.sub.10a is the same as described in the disclosure.
[0242] In one or more embodiments, the fourth compound may include a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
##STR00089##
[0243] wherein in Formulae 502 and 503,
[0244] ring A.sub.501 to ring A.sub.504 may each independently be a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group,
[0245] Y.sub.505 may be O, S, N(R.sub.504), B(R.sub.505), C(R.sub.505a)(R.sub.505b), or Si(R.sub.505a)(R.sub.505b),
[0246] Y.sub.506 may be O, S, N(R.sub.506), B(R.sub.506), C(R.sub.506a)(R.sub.506b), or Si(R.sub.506a)(R.sub.506b),
[0247] Y.sub.507 may be O, S, N(R.sub.507), B(R.sub.507), C(R.sub.507a)(R.sub.507b), or Si(R.sub.507a)(R.sub.507b),
[0248] Y.sub.508 may be O, S, N(R.sub.508), B(R.sub.508), C(R.sub.508a)(R.sub.508b), or Si(R.sub.558a)(R.sub.508b),
[0249] Y.sub.51 and Y.sub.52 may each independently be B, P(═O), or S(═O),
[0250] R.sub.500a, R.sub.500b, R.sub.501 to R.sub.508, R.sub.505a, R.sub.505b, R.sub.506a, R.sub.506b, R.sub.507a, R.sub.507b, R.sub.508a, and R.sub.508b are the same as described in the disclosure,
[0251] a501 to a504 may each independently be an integer from 0 to 20, and
[0252] R.sub.10a is the same as described in the disclosure.
[0253] Description of Formulae 2 to 4
[0254] b61 to b63 in Formula 2 respectively indicate numbers of L.sub.61 to L.sub.63, and may each be an integer from 1 to 5. When b61 is 2 or more, two or more of L.sub.61(s) may be identical to or different from each other, when b62 is 2 or more, two or more of L.sub.62(s) may be identical to or different from each other, and when b63 is 2 or more, two or more of L.sub.63(s) may be identical to or different from each other. For example, b61 to b63 may each independently be 1 or 2.
[0255] L.sub.61 to L.sub.63 in Formula 2 may each independently be:
[0256] a single bond; or
[0257] a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, 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, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a dibenzooxasiline group, a dibenzothiasiline group, a dibenzodihydroazasiline group, a dibenzodihydrodihydrodisiline group, a dibenzodihydrosiline group, a dibenzodioxine group, a dibenzooxathiine group, a dibenzooxazine group, a dibenzopyran group, a dibenzodithiine group, a dibenzotiazine group, a dibenzothiopyran group, a dibenzocyclohexadiene group, a dibenzodihydropyridine group, or a dibenzodihydropyrazine group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a dimethyldibenzosilolyl group, a diphenyldibenzosilolyl group, —O (Q.sub.31), —S(Q.sub.31), —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —P(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), —P(═O)(Q.sub.31)(Q.sub.32), or any combination thereof, and
[0258] Q.sub.31 to Q.sub.33 may each independently be hydrogen, deuterium, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group.
[0259] In an embodiment, in Formula 2, a bond between L.sub.61 and R.sub.61, a bond between L.sub.62 and R.sub.62, a bond between L.sub.63 and R.sub.63, a bond between two or more L.sub.61(s), a bond between two or more L.sub.62(s), a bond between two or more L.sub.63(s), a bond between L.sub.61 and carbon between X.sub.64 and X.sub.65 in Formula 2, a bond between L.sub.62 and carbon between X.sub.64 and X.sub.66 in Formula 2, and a bond between L.sub.63 and carbon between X.sub.65 and X.sub.66 in Formula 2 may each be a “carbon-carbon a single bond”.
[0260] In Formula 2, X.sub.64 may be N or C(R.sub.64), X.sub.65 may be N or C(R.sub.65), X.sub.66 may be N or C(R.sub.66), and at least one of X.sub.64 to X.sub.66 may be N. R.sub.64 to R.sub.66 are the same as described in the disclosure. For example, two or three of X.sub.64 to X.sub.66 may each be N.
[0261] R.sub.61 to R.sub.66, R.sub.71 to R.sub.74, R.sub.81 to R.sub.85, R.sub.82a, R.sub.82b, R.sub.83a, R.sub.83b, R.sub.84a, R.sub.84b, R.sub.500a, R.sub.500b, R.sub.501 to R.sub.508, R.sub.505a, R.sub.505b, R.sub.506a, R.sub.506b, R.sub.507a, R.sub.507b, R.sub.508a, and R.sub.508b may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.6 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.6 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2). Q.sub.1 to Q.sub.3 are the same as described in the disclosure.
[0262] For example, i) R.sub.61 to R.sub.66, R.sub.71 to R.sub.74, R.sub.81 to R.sub.85, R.sub.82a, R.sub.82b, R.sub.83a, R.sub.83b, R.sub.84a, R.sub.84b, R.sub.500a, R.sub.500b, R.sub.501 to R.sub.508, R.sub.505a, R.sub.505b, R.sub.506a, R.sub.506b, R.sub.507a, R.sub.507b, R.sub.508a, and R.sub.508b in Formulae 2, 3-1 to 3-5, 502, and 503 and ii) R.sub.10a may each independently be:
[0263] hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, or a C.sub.1-C.sub.20 alkoxy group;
[0264] a C.sub.1-C.sub.20 alkyl group or a C.sub.1-C.sub.20 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;
[0265] a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzosilolyl group, or a group represented by Formula 91, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —O(Q.sub.31), —S(Q.sub.31), —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —P(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), —P(═O)(Q.sub.31)(Q.sub.32), or any combination thereof; or
[0266] —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2), and
[0267] Q.sub.1 to Q.sub.3 and Q.sub.31 to Q.sub.33 may each independently be:
[0268] —CH.sub.3, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CH.sub.2CH.sub.3, —CH.sub.2CD.sub.3, —CH.sub.2CD.sub.2H, —CH.sub.2CDH.sub.2, —CHDCH.sub.3, —CHDCD.sub.2H, —CHDCDH.sub.2, —CHDCD.sub.3, —CD.sub.2CD.sub.3, —CD.sub.2CD.sub.2H, or —CD.sub.2CDH.sub.2; or
[0269] an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each unsubstituted or substituted with deuterium, a C.sub.1-C.sub.10 alkyl 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:
##STR00090##
[0270] wherein in Formula 91,
[0271] ring CY.sub.91 and ring CY.sub.92 may each independently be a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0272] X.sub.91 may be a single bond, O, S, N(R.sub.91), B(R.sub.91), C(R.sub.91a)(R.sub.91b), or Si(R.sub.91a)(R.sub.91b),
[0273] R.sub.91, R.sub.91a, and R.sub.91b are respectively the same as described in connection with R.sub.82, R.sub.82a, and R.sub.82b,
[0274] R.sub.10a is the same as described in the disclosure, and
[0275] * indicates a binding site to a neighboring atom.
[0276] For example, in Formula 91,
[0277] ring CY.sub.91 and ring CY.sub.92 may each independently be a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group, each unsubstituted or substituted with at least one R.sub.10a, and
[0278] R.sub.91, R.sub.91a, and R.sub.91b may each independently be:
[0279] hydrogen or a C.sub.1-C.sub.10 alkyl group; or
[0280] a phenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each unsubstituted or substituted with deuterium, a C.sub.1-C.sub.10 alkyl 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.
[0281] In one or more embodiments, i) R.sub.61 to R.sub.66, R.sub.71 to R.sub.74, R.sub.81 to R.sub.85, R.sub.82a, R.sub.82b, R.sub.83a, R.sub.83b, R.sub.84a, R.sub.84b, R.sub.500a, R.sub.500b, R.sub.501 to R.sub.508, R.sub.505a, R.sub.505b, R.sub.506a, R.sub.506b, R.sub.507a, R.sub.507b, R.sub.508a, and R.sub.508b in Formulae 2, 3-1 to 3-5, 502, and 503 and ii) R.sub.10a may each independently be:
[0282] hydrogen, deuterium, —F, a cyano group, a nitro group, —CH.sub.3, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a group represented by one of Formulae 9-1 to 9-19, a group represented by one of Formulae 10-1 to 10-249, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), or —P(═O)(Q.sub.1)(Q.sub.2) (wherein Q.sub.1 to Q.sub.3 are the same as described in the disclosure):
##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100##
[0283] wherein in Formulae 9-1 to 9-19 and 10-1 to 10-249, * indicates a binding site to a neighboring atom, “Ph” represents a phenyl group, and “TMS” represents a trimethylsilyl group.
[0284] a71 to a74 and a501 to a504 in Formulae 3-1 to 3-5, 502, and 503 respectively indicate numbers of R.sub.71 to R.sub.74 and R.sub.501 to R.sub.504, and may each independently be an integer from 0 to 20. When a71 is 2 or more, two or more of R.sub.71(s) may be identical to or different from each other, when a72 is 2 or more, two or more of R.sub.72(s) may be identical to or different from each other, when a73 is 2 or more, two or more of R.sub.73(s) may be identical to or different from each other, when a74 is 2 or more, two or more of R.sub.74(s) may be identical to or different from each other, when a501 is 2 or more, two or more of R.sub.501(s) may be identical to or different from each other, when a502 is 2 or more, two or more of R.sub.502(s) may be identical to or different from each other, when a503 is 2 or more, two or more of R.sub.503(s) may be identical to or different from each other, and when a504 is 2 or more, two or more of R.sub.504(s) may be identical to or different from each other. a71 to a74 and a501 to a504 may each independently be an integer from 0 to 8.
[0285] In an embodiment, in Formula 2, a group represented by *-(L.sub.61).sub.b61-R.sub.61 and a group represented by *-(L.sub.62).sub.b62-R.sub.62 may each not be a phenyl group.
[0286] In an embodiment, in Formula 2, a group represented by *-(L.sub.61).sub.b61-R.sub.61 may be identical to a group represented by *-(L.sub.62).sub.b62-R.sub.62.
[0287] In one or more embodiments, in Formula 2, a group represented by *-(L.sub.61).sub.b61-R.sub.61 and a group represented by *-(L.sub.62).sub.b62-R.sub.62 may be different from each other.
[0288] In one or more embodiments, in Formula 2, b61 and b62 may each be 1, 2, or 3, and L.sub.61 and L.sub.62 may each independently be a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, each unsubstituted or substituted with at least one R.sub.10a.
[0289] For example, R.sub.61 and R.sub.62 in Formula 2 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), or —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), and
[0290] Q.sub.1 to Q.sub.3 may each independently be a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C.sub.1-C.sub.60 alkyl group, a C.sub.1-C.sub.60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
[0291] In an embodiment,
[0292] a group represented by *-(L.sub.61).sub.b61-R.sub.61 in Formula 2 may be a group represented by one of Formulae CY51-1 to CY51-26, and/or
[0293] a group represented by *-(L.sub.62).sub.b62-R.sub.62 in Formula 2 may be a group represented by one of Formulae CY52-1 to CY52-26, and/or
[0294] a group represented by *-(L.sub.63).sub.b63-R.sub.63 in Formula 2 may be a group represented by one of Formulae CY53-1 to CY53-27, —C(Q.sub.1)(Q.sub.2)(Q.sub.3), or —Si(Q.sub.1)(Q.sub.2)(Q.sub.3):
##STR00101## ##STR00102## ##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111##
[0295] wherein in Formulae CY51-1 to CY51-26, CY52-1 to CY52-26, and CY53-1 to CY53-27,
[0296] Y.sub.63 may be a single bond, O, S, N(R.sub.63), B(R.sub.63), C(R.sub.63a)(R.sub.63b), or Si(R.sub.63a)(R.sub.63b),
[0297] Y.sub.64 may be a single bond, O, S, N(R.sub.64), B(R.sub.64), C(R.sub.64a)(R.sub.64b), or Si(R.sub.64a)(R.sub.64b),
[0298] Y.sub.67 may be a single bond, O, S, N(R.sub.67), B(R.sub.67), C(R.sub.67a)(R.sub.67b), or Si(R.sub.67a)(R.sub.67b),
[0299] Y.sub.68 may be a single bond, O, S, N(R.sub.68), B(R.sub.68), C(R.sub.68a)(R.sub.68b), or Si(R.sub.68a)(R.sub.68b),
[0300] Y.sub.63 and Y.sub.64 in Formulae CY51-16 and CY51-17 may not both simultaneously be a single bond,
[0301] Y.sub.67 and Y.sub.68 in Formulae CY52-16 and CY52-17 may not both simultaneously be a single bond,
[0302] R.sub.51a to R.sub.51e, R.sub.61 to R.sub.64, R.sub.63a, R.sub.63b, R.sub.64a, and R.sub.64b are each the same as described in connection with R.sub.61, wherein each of R.sub.51a to R.sub.51e may not be hydrogen,
[0303] R.sub.52a to R.sub.52e, R.sub.65 to R.sub.68, R.sub.67a, R.sub.67b, R.sub.68a, and R.sub.68b are each the same as described in connection with R.sub.62, wherein each of R.sub.52a to R.sub.52e may not be hydrogen,
[0304] R.sub.53a to R.sub.53e, R.sub.69a, and R.sub.69b are each the same as described in connection with R.sub.63, wherein each of R.sub.53a to R.sub.53e may not be hydrogen, and
[0305] * indicates a binding site to a neighboring atom.
[0306] For example,
[0307] R.sub.51a to R.sub.51e and R.sub.52a to R.sub.52e in Formulae CY51-1 to CY51-26 and CY52-1 to 52-26 may each independently be:
[0308] a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzosilolyl group, or a group represented by Formula 91, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, or any combination thereof; or
[0309] —C(Q.sub.1)(Q.sub.2)(Q.sub.3) or —Si(Q.sub.1)(Q.sub.2)(Q.sub.3),
[0310] Q.sub.1 to Q.sub.3 may each independently be a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each unsubstituted or substituted with deuterium, a C.sub.1-C.sub.10 alkyl 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,
[0311] in Formulae CY51-16 and CY51-17, i) Y.sub.63 may be O or S, and Y.sub.64 may be Si(R.sub.64a)(R.sub.64b), or ii) Y.sub.63 may be Si(R.sub.63a)(R.sub.63b), and Y.sub.64 may be O or S, and
[0312] in Formulae CY52-16 and CY52-17, i) Y.sub.67 may be O or S, and Y.sub.68 may be Si(R.sub.68a)(R.sub.68b), or ii) Y.sub.67 may be Si(R.sub.67a)(R.sub.67b), and Y.sub.68 may be O or S.
[0313] In an embodiment, L.sub.81 to L.sub.85 in Formulae 3-1 to 3-5 may each independently be:
[0314] a single bond;
[0315] *—C(Q.sub.4)(Q.sub.5)-*′ or *—Si(Q.sub.4)(Q.sub.5)-*′; or
[0316] a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, 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, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, or a benzothiadiazole group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a dimethyldibenzosilolyl group, a diphenyldibenzosilolyl group, —O(Q.sub.31), —S(Q.sub.31), —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —P(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), —P(═O)(Q.sub.31)(Q.sub.32), or any combination thereof, and
[0317] Q.sub.4, Q.sub.5, and Q.sub.31 to Q.sub.33 may each independently be hydrogen, deuterium, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group.
[0318] In one or more embodiments, a group represented by
##STR00112##
in Formulae 3-1 and 3-2 may be a group represented by one of Formulae CY71-1(1) to CY71-1(8), and/or
[0319] a group represented by
##STR00113##
in Formulae 3-1 and 3-3 may be a group represented by one of Formulae CY71-2(1) to CY71-2(8), and/or
[0320] a group represented by
##STR00114##
in Formulae 3-2 and 3-4 may be a group represented by one of Formulae CY71-3(1) to CY71-3(32), and/or
[0321] a group represented by
##STR00115##
in Formulae 3-3 to 3-5 may be a group represented by one of Formulae CY71-4(1) to CY71-4(32), and/or
[0322] a group represented by
##STR00116##
in Formula 3-5 may be a group represented by one of Formulae CY71-5(1) to CY71-5(8):
##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127##
[0323] wherein in Formulae CY71-1(1) to CY71-1(8), CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), CY71-4(1) to CY71-4(32), and CY71-5(1) to CY71-5(8),
[0324] X.sub.81 to X.sub.85, L.sub.81, b.sub.81, R.sub.81, and R.sub.85 are the same as described in the disclosure,
[0325] X.sub.86 may be a single bond, O, S, N(R.sub.86), B(R.sub.86), C(R.sub.86a)(R.sub.86b), or Si(R.sub.86a)(R.sub.86b),
[0326] X.sub.87 may be a single bond, O, S, N(R.sub.87), B(R.sub.87), C(R.sub.87a)(R.sub.87b), or Si(R.sub.87a)(R.sub.87b),
[0327] X.sub.86 and X.sub.87 in Formulae CY71-1(1) to CY71-1(8) and CY71-4(1) to CY71-4(32) may not both simultaneously be a single bond,
[0328] X.sub.88 may be a single bond, O, S, N(R.sub.88), B(R.sub.88), C(R.sub.88a)(R.sub.88b), or Si(R.sub.88a)(R.sub.88b),
[0329] X.sub.89 may be a single bond, O, S, N(R.sub.89), B(R.sub.89), C(R.sub.89a)(R.sub.89b), or Si(R.sub.89a)(R.sub.89b),
[0330] X.sub.88 and X.sub.89 in Formulae CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), and CY71-5(1) to CY71-5(8) may not both simultaneously be a single bond, and
[0331] R.sub.86 to R.sub.89, R.sub.86a, R.sub.86b, R.sub.87a, R.sub.87b, R.sub.88a, R.sub.88b, R.sub.89a, and R.sub.89b are the same as described in connection with R.sub.81.
[0332] Detailed Examples of Second Compound to Fourth Compound
[0333] In an embodiment, the second compound may include at least one of Compounds ETH1 to ETH84:
##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149##
[0334] In one or more embodiments, the third compound may include at least one of Compounds HTH1 to HTH52:
##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160##
[0335] In one or more embodiments, the fourth compound may include at least one of Compounds DFD1 to DFD12:
##STR00161## ##STR00162## ##STR00163##
[0336] In the compounds above, “Ph” represents a phenyl group, “D.sub.5” represents substitution with five deuterium atoms, and “D.sub.4” represents substitution with four deuterium atoms. For example, a group represented by
##STR00164##
may be identical to a group represented by
##STR00165##
[0337] In an embodiment, the light-emitting device may satisfy at least one of Conditions 1 to 4:
[0338] Condition 1
[0339] lowest unoccupied molecular orbital (LUMO) energy level (eV) of the third compound >LUMO energy level (eV) of the first compound;
[0340] Condition 2
[0341] LUMO energy level (eV) of the first compound >LUMO energy level (eV) of the second compound;
[0342] Condition 3
[0343] highest occupied molecular orbital (HOMO) energy level (eV) of the first compound >HOMO energy level (eV) of the third compound; and
[0344] Condition 4
[0345] HOMO energy level (eV) of the third compound >HOMO energy level (eV) of the second compound.
[0346] Each of the HOMO energy level and LUMO energy level of each of the first compound, the second compound, and the third compound may be a negative value, and may be measured according to a known method.
[0347] In one or more embodiments, an absolute value of a difference between the LUMO energy level of the first compound and the LUMO energy level of the second compound may be about 0.1 eV or more and about 1.0 eV or less, an absolute value of a difference between the LUMO energy level of the first compound and the LUMO energy level of the third compound may be about 0.1 eV more and about 1.0 eV or less, an absolute value of a difference between the HOMO energy level of the first compound and the HOMO energy level of the second compound may be about 1.25 eV or less (for example, about 1.25 eV or less and about 0.2 eV or more), and an absolute value of a difference between the HOMO energy level of the first compound and the HOMO energy level of the third compound may be about 1.25 eV or less (for example, about 1.25 eV or less and about 0.2 eV or more).
[0348] When the relationships between LUMO energy level and HOMO energy level satisfy the conditions as described above, the balance between holes and electrons injected into the emission layer may be achieved.
[0349] The light-emitting device may have a structure of a first embodiment or a second embodiment.
Description of First Embodiment
[0350] According to the first embodiment, the first compound may be included in the emission layer of the interlayer in the light-emitting device, wherein the emission layer may further include a host, the first compound may be different from the host, and the emission layer may emit phosphorescence or fluorescence emitted from the first compound. That is, in the first embodiment, the first compound may be a dopant or an emitter. For example, the first compound may be a phosphorescent dopant or a phosphorescence emitter.
[0351] The phosphorescence or the fluorescence emitted from the first compound may be blue light.
[0352] The emission layer may further include an auxiliary dopant. The auxiliary dopant may serve to improve luminescence efficiency from the first compound by effectively transferring energy to the first compound which is a dopant or an emitter.
[0353] The auxiliary dopant may be different from each of the first compound and the host.
[0354] For example, the auxiliary dopant may be a delayed fluorescence-emitting compound.
[0355] In one or more embodiments, the auxiliary dopant may be a compound including at least one cyclic group including B and N as ring-forming atoms.
Description of Second Embodiment
[0356] According to the second embodiment, the first compound may be included in the emission layer of the interlayer in the light-emitting device, wherein the emission layer may further include a host and a dopant, the first compound may be different from each of the host and the dopant, and the emission layer may emit phosphorescence or fluorescence (for example, delayed fluorescence) emitted from the dopant.
[0357] For example, the first compound in the second embodiment may serve as an auxiliary dopant that transfers energy to a dopant (or an emitter), not as a dopant.
[0358] In one or more embodiments, the first compound in the second embodiment may serve as an emitter, and may additionally serve as an auxiliary dopant that transfers energy to a dopant (or an emitter).
[0359] For example, the phosphorescence or the fluorescence emitted from the dopant (or the emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (for example, blue delayed fluorescence).
[0360] The dopant (or the emitter) in the second embodiment may be a phosphorescent dopant material (for example, the organometallic compound represented by Formula 1, an organometallic compound represented by Formula 401, or any combination thereof) or any fluorescent dopant material (for example, the compound represented by Formula 501, the compound represented by Formula 502, the compound represented by Formula 503, or any combination thereof).
[0361] The blue light of the first embodiment and the second embodiment may have a maximum emission wavelength in a range of about 430 nm to about 480 nm, about 430 nm to about 475 nm, about 440 nm to about 475 nm, or about 450 nm to about 470 nm.
[0362] The auxiliary dopant in the first embodiment may include, for example, the fourth compound represented by Formula 502 or 503.
[0363] The host in the first embodiment and the second embodiment may be any host material (for example, the compound represented by Formula 301, the compound represented by 301-1, the compound represented by Formula 301-2, or any combination thereof).
[0364] In one or more embodiments, the host in the first embodiment and the second embodiment may be the second compound, the third compound, or any combination thereof.
[0365] According to another aspect, provided is an electronic apparatus including the light-emitting device. The electronic apparatus may further include a thin-film transistor. For example, the electronic apparatus may further include a thin-film transistor including a source electrode and a drain electrode, and the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. In an embodiment, the electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. More details for the electronic apparatus are the same as described in the disclosure.
[0366] According to another aspect, provided is the organometallic compound represented by Formula 1. Details for Formula 1 are the same as described in the disclosure.
[0367] [Description of
[0368]
[0369] Hereinafter, a structure of the light-emitting device 10 according to an embodiment and a method of manufacturing the light-emitting device 10 will be described with reference to
[0370] [First Electrode 110]
[0371] In
[0372] The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high work function material that facilitates injection of holes.
[0373] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO.sub.2), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof.
[0374] The first electrode 110 may have a single-layered structure consisting of a single layer or a multi-layered structure including a plurality of layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
[0375] [Interlayer 130]
[0376] The interlayer 130 may be located on the first electrode 110. The interlayer 130 may include an emission layer.
[0377] The interlayer 130 may further include a hole transport region located between the first electrode 110 and the emission layer and an electron transport region located between the emission layer and the second electrode 150.
[0378] The interlayer 130 may further include metal-containing compounds such as organometallic compounds, inorganic materials such as quantum dots, and the like, in addition to various organic materials.
[0379] In one or more embodiments, the interlayer 130 may include, i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer located between the two or more emitting units. When the interlayer 130 includes the emitting units and the charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.
[0380] [Hole Transport Region in Interlayer 130]
[0381] The hole transport region may have i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer consisting of a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
[0382] The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.
[0383] For example, the hole transport region may have a multi-layered structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein, in each structure, layers are stacked sequentially from the first electrode 110.
[0384] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
##STR00166##
[0385] wherein in Formulae 201 and 202,
[0386] L.sub.201 to L.sub.204 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0387] L.sub.205 may be *—O—*′, *—S—*′, *—N(Q.sub.201)-*′, a C.sub.1-C.sub.20 alkylene group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.20 alkenylene group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0388] xa1 to xa4 may each independently be an integer from 0 to 5,
[0389] xa5 may be an integer from 1 to 10,
[0390] R.sub.201 to R.sub.204 and Q.sub.201 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0391] R.sub.201 and R.sub.202 may optionally be linked to each other via a single bond, a C.sub.1-C.sub.5 alkylene group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.2-C.sub.5 alkenylene group unsubstituted or substituted with at least one R.sub.10a to form a C.sub.8-C.sub.60 polycyclic group (for example, a carbazole group or the like) unsubstituted or substituted with at least one R.sub.10a (for example, see Compound HT16),
[0392] R.sub.203 and R.sub.204 may optionally be linked to each other via a single bond, a C.sub.1-C.sub.5 alkylene group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.2-C.sub.5 alkenylene group unsubstituted or substituted with at least one R.sub.10a to form a C.sub.8-C.sub.60 polycyclic group unsubstituted or substituted with at least one R.sub.10a, and
[0393] na1 may be an integer from 1 to 4.
[0394] For example, each of Formulae 201 and 202 may include at least one of groups represented by Formulae CY201 to CY217:
##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173##
[0395] wherein in Formulae CY201 to CY217, R.sub.10b and R.sub.10c are the same as described in connection with R.sub.10a, ring CY.sub.201 to ring CY.sub.2O.sub.4 may each independently be a C.sub.3-C.sub.20 carbocyclic group or a C.sub.1-C.sub.20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with at least one R.sub.10a as described herein.
[0396] In an embodiment, ring CY.sub.201 to ring CY.sub.204 in Formulae CY201 to CY217 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
[0397] In one or more embodiments, each of Formulae 201 and 202 may include at least one of groups represented by Formulae CY201 to CY203.
[0398] In one or more embodiments, Formula 201 may include at least one of the groups represented by Formulae CY201 to CY203 and at least one of the groups represented by Formulae CY204 to CY217.
[0399] In one or more embodiments, in Formula 201, xa1 may be 1, R.sub.201 may be a group represented by one of Formulae CY201 to CY203, xa2 may be 0, and R.sub.202 may be a group represented by one of Formulae CY204 to CY207.
[0400] In one or more embodiments, each of Formulae 201 and 202 may not include a group represented by one of Formulae CY201 to CY203.
[0401] In one or more embodiments, each of Formulae 201 and 202 may not include a group represented by one of Formulae CY201 to CY203, and may include at least one of the groups represented by Formulae CY204 to CY217.
[0402] In one or more embodiments, each of Formulae 201 and 202 may not include a group represented by one of Formulae CY201 to CY217.
[0403] For example, the hole transport region may include one of Compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), or any combination thereof:
##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190##
[0404] A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole-transporting characteristics may be obtained without a substantial increase in driving voltage.
[0405] The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer, and the electron blocking layer may block the leakage of electrons from an emission layer to a hole transport region. Materials that may be included in the hole transport region may be included in the emission auxiliary layer and the electron blocking layer.
[0406] [p-Dopant]
[0407] The hole transport region may further include, in addition to the materials as described above, a charge-generation material for improving conductive properties. The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer consisting of a charge-generation material).
[0408] The charge-generation material may be, for example, a p-dopant.
[0409] In an embodiment, a LUMO energy level of the p-dopant may be about −3.5 eV or less.
[0410] In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound containing element EL1 and element EL2, or any combination thereof.
[0411] Examples of the quinone derivative may include TCNQ, F4-TCNQ, and the like.
[0412] Examples of the cyano group-containing compound may include HAT-CN, a compound represented by Formula 221, and the like:
##STR00191##
[0413] wherein in Formula 221,
[0414] R.sub.221 to R.sub.223 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, and
[0415] at least one of R.sub.221 to R.sub.223 may each independently be a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group, each substituted with: a cyano group; —F; —Cl; —Br; —I; a C.sub.1-C.sub.20 alkyl group substituted with a cyano group, —F, —Cl, —Br, —I, or any combination thereof; or any combination thereof.
[0416] In the compound containing element EL1 and element EL2, element EL1 may be metal, metalloid, or a combination thereof, and element EL2 may be non-metal, metalloid, or a combination thereof.
[0417] Examples of the metal may include: an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (for example, titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); a post-transition metal (for example, zinc (Zn), indium (In), tin (Sn), etc.); and a lanthanide metal (for example, lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).
[0418] Examples of the metalloid may include silicon (Si), antimony (Sb), and tellurium (Te).
[0419] Examples of the non-metal may include oxygen (O) and halogen (for example, F, Cl, Br, I, etc.).
[0420] Examples of the compound containing element EL1 and element EL2 may include metal oxide, metal halide (for example, metal fluoride, metal chloride, metal bromide, or metal iodide), metalloid halide (for example, metalloid fluoride, metalloid chloride, metalloid bromide, or metalloid iodide), metal telluride, or any combination thereof.
[0421] Examples of the metal oxide may include tungsten oxide (for example, WO, W.sub.2O.sub.3, WO.sub.2, WO.sub.3, W.sub.2O.sub.5, etc.), vanadium oxide (for example, VO, V.sub.2O.sub.3, VO.sub.2, V.sub.2O.sub.5, etc.), molybdenum oxide (MoO, Mo.sub.2O.sub.3, MoO.sub.2, MoO.sub.3, Mo.sub.2O.sub.5, etc.), and rhenium oxide (for example, ReO.sub.3, etc.).
[0422] Examples of the metal halide may include alkali metal halide, alkaline earth metal halide, transition metal halide, post-transition metal halide, and lanthanide metal halide.
[0423] Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.
[0424] Examples of the alkaline earth metal halide may include BeF.sub.2, MgF.sub.2, CaF.sub.2, SrF.sub.2, BaF.sub.2, BeCl.sub.2, MgCl.sub.2, CaCl.sub.2, SrCl.sub.2, BaCl.sub.2, BeBr.sub.2, MgBr.sub.2, CaBr.sub.2, SrBr.sub.2, BaBr.sub.2, BeI.sub.2, Mgl.sub.2, Cal.sub.2, SrI.sub.2, and BaI.sub.2.
[0425] Examples of the transition metal halide may include titanium halide (for example, TiF.sub.4, TiCl.sub.4, TiBr.sub.4, TiI.sub.4, etc.), zirconium halide (for example, ZrF.sub.4, ZrCl.sub.4, ZrBr.sub.4, ZrI.sub.4, etc.), hafnium halide (for example, HfF.sub.4, HfCl.sub.4, HfBr.sub.4, HfI.sub.4, etc.), vanadium halide (for example, VF.sub.3, VCl.sub.3, VBr.sub.3, VI.sub.3, etc.), niobium halide (for example, NbF.sub.3, NbCl.sub.3, NbBr.sub.3, NbI.sub.3, etc.), tantalum halide (for example, TaF.sub.3, TaCl.sub.3, TaBr.sub.3, TaI.sub.3, etc.), chromium halide (for example, CrF.sub.3, CrCl.sub.3, CrBr.sub.3, CrI.sub.3, etc.), molybdenum halide (for example, MoF.sub.3, MoCl.sub.3, MoBr.sub.3, MoI.sub.3, etc.), tungsten halide (for example, WF.sub.3, WCl.sub.3, WBr.sub.3, WI.sub.3, etc.), manganese halide (for example, MnF.sub.2, MnCl.sub.2, MnBr.sub.2, MnI.sub.2, etc.), technetium halide (for example, TcF.sub.2, TcCl.sub.2, TcBr.sub.2, TcI.sub.2, etc.), rhenium halide (for example, ReF.sub.2, ReCl.sub.2, ReBr.sub.2, ReI.sub.2, etc.), iron halide (for example, FeF.sub.2, FeCl.sub.2, FeBr.sub.2, FeI.sub.2, etc.), ruthenium halide (for example, RuF.sub.2, RuCl.sub.2, RuBr.sub.2, RuI.sub.2, etc.), osmium halide (for example, OsF.sub.2, OsCl.sub.2, OsBr.sub.2, OsI.sub.2, etc.), cobalt halide (for example, CoF.sub.2, CoCl.sub.2, CoBr.sub.2, CoI.sub.2, etc.), rhodium halide (for example, RhF.sub.2, RhCl.sub.2, RhBr.sub.2, RhI.sub.2, etc.), iridium halide (for example, IrF.sub.2, IrCl.sub.2, IrBr.sub.2, IrI.sub.2, etc.), nickel halide (for example, NiF.sub.2, NiCl.sub.2, NiBr.sub.2, NiI.sub.2, etc.), palladium halide (for example, PdF.sub.2, PdCl.sub.2, PdBr.sub.2, PdI.sub.2, etc.), platinum halide (for example, PtF.sub.2, PtCl.sub.2, PtBr.sub.2, PtI.sub.2, etc.), copper halide (for example, CuF, CuCl, CuBr, CuI, etc.), silver halide (for example, AgF, AgCl, AgBr, AgI, etc.), and gold halide (for example, AuF, AuCl, AuBr, AuI, etc.).
[0426] Examples of the post-transition metal halide may include zinc halide (for example, ZnF.sub.2, ZnCl.sub.2, ZnBr.sub.2, ZnI.sub.2, etc.), indium halide (for example, InI.sub.3, etc.), and tin halide (for example, SnI.sub.2, etc.).
[0427] Examples of the lanthanide metal halide may include YbF, YbF.sub.2, YbF.sub.3, SmF.sub.3, YbCl, YbCl.sub.2, YbCl.sub.3 SmCl.sub.3, YbBr, YbBr.sub.2, YbBr.sub.3, SmBr.sub.3, YbI, YbI.sub.2, YbI.sub.3, and SmI.sub.3.
[0428] Examples of the metalloid halide may include antimony halide (for example, SbCl.sub.5, etc.).
[0429] Examples of the metal telluride may include alkali metal telluride (for example, Li.sub.2Te, Na.sub.2Te, K.sub.2Te, Rb.sub.2Te, Cs.sub.2Te, etc.), alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal telluride (for example, TiTe.sub.2, ZrTe.sub.2, HfTe.sub.2, V.sub.2Te.sub.3, Nb.sub.2Te.sub.3, Ta.sub.2Te.sub.3, Cr.sub.2Te.sub.3, Mo.sub.2Te.sub.3, W.sub.2Te.sub.3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu.sub.2Te, CuTe, Ag.sub.2Te, AgTe, Au.sub.2Te, etc.), post-transition metal telluride (for example, ZnTe, etc.), and lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
[0430] [Emission Layer in Interlayer 130]
[0431] When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other to emit white light. In one or more embodiments, the emission layer may have a structure in which two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material are mixed with each other in a single layer, and thus emit white light.
[0432] The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0433] An amount of the dopant in the emission layer may be from about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
[0434] In an embodiment, the emission layer may include a quantum dot.
[0435] The emission layer may include a delayed fluorescence material. The delayed fluorescence material may serve as a host or a dopant in the emission layer.
[0436] A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within these ranges, desirable light-emission characteristics may be obtained without a substantial increase in driving voltage.
[0437] [Host]
[0438] The host in the emission layer may include the second compound or the third compound described in the disclosure, or any combination thereof.
[0439] The host may include a compound represented by Formula 301:
[Ar.sub.301].sub.xb11-[(L.sub.301).sub.xb1-R.sub.301].sub.xb21 Formula 301
[0440] wherein in Formula 301,
[0441] Ar.sub.301 and L.sub.301 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0442] xb11 may be 1, 2, or 3,
[0443] xb1 may be an integer from 0 to 5,
[0444] R.sub.301 may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, —Si(Q.sub.301)(Q.sub.302)(Q.sub.303), —N(Q.sub.301)(Q.sub.302), —B(Q.sub.301)(Q.sub.302), —C(═O)(Q.sub.301), —S(═O).sub.2(Q.sub.301), or —P(═O)(Q.sub.301)(Q.sub.302),
[0445] xb21 may be an integer from 1 to 5, and
[0446] Q.sub.301 to Q.sub.303 are the same as described in connection with Q.sub.1.
[0447] For example, when xb11 in Formula 301 is 2 or more, two or more of Ar.sub.301(s) may be linked to each other via a single bond.
[0448] In one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
##STR00192##
[0449] wherein in Formulae 301-1 and 301-2,
[0450] ring A.sub.301 to ring A.sub.304 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0451] X.sub.301 may be O, S, N-[(L.sub.304).sub.xb4-R.sub.304], C(R.sub.304)(R.sub.305), or Si(R.sub.304)(R.sub.305),
[0452] xb22 and xb23 may each independently be 0, 1, or 2,
[0453] L.sub.301, xb1, and R.sub.301 are the same as described in the disclosure,
[0454] L.sub.302 to L.sub.304 are each independently the same as described in connection with L.sub.301,
[0455] xb2 to xb4 are each independently the same as described in connection with xb1, and
[0456] R.sub.302 to R.sub.305 and R.sub.321 to R.sub.324 are the same as described in connection with R.sub.301.
[0457] In one or more embodiments, the host may include an alkali earth metal complex, a post-transition metal complex, or any combination thereof. For example, the host may include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or any combination thereof.
[0458] In one or more embodiments, the host may include one of Compounds H1 to H124, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combination thereof:
##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210##
[0459] In one or more embodiments, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
[0460] The host may have various modifications. For example, the host may include only one kind of compound, or may include two or more kinds of different compounds.
[0461] [Phosphorescent Dopant]
[0462] The emission layer may include, as a phosphorescent dopant, the first compound as described herein.
[0463] In one or more embodiments, when the emission layer includes the first compound as described herein and the first compound serves as an auxiliary dopant, the emission layer may include a phosphorescent dopant.
[0464] The phosphorescent dopant may include at least one transition metal as a central metal.
[0465] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
[0466] The phosphorescent dopant may be electrically neutral.
[0467] For example, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
##STR00211##
[0468] wherein in Formulae 401 and 402,
[0469] M may be a transition metal (for example, iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
[0470] L.sub.401 may be a ligand represented by Formula 402, and xc1 may be 1, 2, or 3, wherein, when xc1 is 2 or more, two or more of L.sub.401(s) may be identical to or different from each other,
[0471] L.sub.402 may be an organic ligand, and xc2 may be 0, 1, 2, 3, or 4, wherein, when xc2 is 2 or more, two or more of L.sub.402(s) may be identical to or different from each other,
[0472] X.sub.401 and X.sub.402 may each independently be nitrogen or carbon,
[0473] ring A.sub.401 and ring A.sub.402 may each independently be a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group,
[0474] T.sub.401 may be a single bond, *—O—*′, *—S*′, *—C(═O)—*′, *—N(Q.sub.411)-*′, *—C(Q.sub.411)(Q.sub.412)-*′, *—C(Q.sub.411)═C(Q.sub.412)-*′, *—C(Q.sub.411)=*′, or *=C═*′,
[0475] X.sub.403 and X.sub.404 may each independently be a chemical bond (for example, a covalent bond or a coordinate bond), O, S, N(Q.sub.413), B(Q.sub.413), P(Q.sub.413), C(Q.sub.413)(Q.sub.414), or Si(Q.sub.413)(Q.sub.414),
[0476] Q.sub.411 to Q.sub.414 are the same as described in connection with Q.sub.1,
[0477] R.sub.401 and R.sub.402 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.20 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, —Si(Q.sub.401)(Q.sub.402)(Q.sub.403), —N(Q.sub.401)(Q.sub.402), —B(Q.sub.401)(Q.sub.402), —C(═O)(Q.sub.401), —S(═O).sub.2(Q.sub.401), or —P(═O)(Q.sub.401)(Q.sub.402),
[0478] Q.sub.401 to Q.sub.403 are the same as described in connection with Q.sub.1,
[0479] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0480] * and *′ in Formula 402 each indicate a binding site to M in Formula 401.
[0481] For example, in Formula 402, i) X.sub.401 may be nitrogen, and X.sub.402 may be carbon, or ii) each of X.sub.401 and X.sub.402 may be nitrogen.
[0482] In one or more embodiments, when xc1 in Formula 401 is 2 or more, two ring A.sub.401(s) in two or more of L.sub.401(s) may be optionally linked to each other via T.sub.402, which is a linking group, and two ring A.sub.402(s) may be optionally linked to each other via T.sub.403, which is a linking group (see Compounds PD1 to PD4 and PD7). T.sub.402 and T.sub.403 are the same as described in connection with T.sub.401.
[0483] L.sub.402 in Formula 401 may be an organic ligand. For example, L.sub.402 may include a halogen group, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, a —CN group, a phosphorus group (for example, a phosphine group, a phosphite group, etc.), or any combination thereof.
[0484] The phosphorescent dopant may include, for example, one of Compounds PD1 to PD39 or any combination thereof:
##STR00212## ##STR00213## ##STR00214## ##STR00215## ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220##
[0485] [Fluorescent Dopant]
[0486] When the emission layer includes the first compound as described herein and the first compound serves as an auxiliary dopant, the emission layer may further include a fluorescent dopant.
[0487] In one or more embodiments, when the emission layer includes the first compound as described herein and the first compound serves as a phosphorescent dopant, the emission layer may further include an auxiliary dopant.
[0488] The fluorescent dopant and the auxiliary dopant may each independently include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
[0489] For example, the fluorescent dopant and the auxiliary dopant may each independently include a compound represented by Formula 501:
##STR00221##
[0490] wherein in Formula 501,
[0491] Ar.sub.501, L.sub.501 to L.sub.503, R.sub.501, and R.sub.502 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0492] xd1 to xd3 may each independently be 0, 1, 2, or 3, and
[0493] xd4 may be 1, 2, 3, 4, 5, or 6.
[0494] For example, Ar.sub.501 in Formula 501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, or a pyrene group) in which three or more monocyclic groups are condensed together.
[0495] In one or more embodiments, xd4 in Formula 501 may be 2.
[0496] For example, the fluorescent dopant and the auxiliary dopant may each independently include one of Compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:
##STR00222## ##STR00223## ##STR00224## ##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231##
[0497] In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include the fourth compound represented by Formula 502 or 503 as described herein.
[0498] [Delayed Fluorescence Material]
[0499] The emission layer may include, as a delayed fluorescence material, the fourth compound as described herein.
[0500] In one or more embodiments, the emission layer may include the fourth compound, and may further include a delayed fluorescence material.
[0501] In the disclosure, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
[0502] The delayed fluorescence material included in the emission layer may act as a host or a dopant, depending on the type of other materials included in the emission layer.
[0503] In an embodiment, the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material may be greater than or equal to 0 eV and less than or equal to 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material satisfies the above-described range, up-conversion from the triplet state to the singlet state of the delayed fluorescence materials may effectively occur, and thus, the luminescence efficiency of the light-emitting device 10 may be improved.
[0504] For example, the delayed fluorescence material may include i) a material including at least one electron donor (for example, a π electron-rich C.sub.3-C.sub.60 cyclic group, such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, or a π electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group), and ii) a material including a C.sub.8-C.sub.60 polycyclic group in which two or more cyclic groups are condensed while sharing boron (B).
[0505] Examples of the delayed fluorescence material may include at least one of Compounds DF1 to DF9:
##STR00232##
[0506] [Quantum Dot]
[0507] The emission layer may include a quantum dot.
[0508] The term “quantum dot” as used herein refers to a crystal of a semiconductor compound, and may include any material capable of emitting light of various emission wavelengths according to the size of the crystal.
[0509] A diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.
[0510] The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
[0511] The wet chemical process is a method including mixing a precursor material with an organic solvent and then growing a quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles can be controlled through a process which costs lower, and is easier than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
[0512] The quantum dot may include: a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; a Group IV element or compound; or any combination thereof.
[0513] Examples of the Group II-VI semiconductor compound may include: a binary compound, such as CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe; or any combination thereof.
[0514] Examples of the Group III-V semiconductor compound may include: a binary compound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb; or any combination thereof. The Group III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including the Group II element may include InZnP, InGaZnP, InAlZnP, and the like.
[0515] Examples of the Group III-VI semiconductor compound may include: a binary compound, such as GaS, GaSe, Ga.sub.2Se.sub.3, GaTe, InS, InSe, In.sub.2S.sub.3, In.sub.2Se.sub.3, or InTe; a ternary compound, such as InGaS.sub.3, or InGaSe.sub.3; or any combination thereof.
[0516] Examples of the Group I-III-VI semiconductor compound may include: a ternary compound, such as AgInS, AgInS.sub.2, CuInS, CuInS.sub.2, CuGaO.sub.2, AgGaO.sub.2, or AgAlO.sub.2; or any combination thereof.
[0517] Examples of the Group IV-VI semiconductor compound may include: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe; a quaternary compound, such as SnPbSSe, SnPbSeTe, or SnPbSTe; or any combination thereof.
[0518] The Group IV element or compound may include: a single element compound, such as Si or Ge; a binary compound, such as SiC or SiGe; or any combination thereof.
[0519] Each element included in a multi-element compound such as the binary compound, the ternary compound, and the quaternary compound may be present at a uniform concentration or non-uniform concentration in a particle.
[0520] The quantum dot may have a single structure in which the concentration of each element in the quantum dot is uniform, or a core-shell dual structure. For example, the material included in the core and the material included in the shell may be different from each other.
[0521] The shell of the quantum dot may act as a protective layer that prevents chemical degeneration of the core to maintain semiconductor characteristics, and/or as a charging layer that imparts electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multi-layer. The interface between the core and the shell may have a concentration gradient in which the concentration of an element existing in the shell decreases toward the center of the core.
[0522] Examples of the shell of the quantum dot may be an oxide of metal, metalloid, or non-metal, a semiconductor compound, or a combination thereof. Examples of the oxide of metal, metalloid, or non-metal may include: a binary compound, such as SiO.sub.2, Al.sub.2O.sub.3, TiO.sub.2, ZnO, MnO, Mn.sub.2O.sub.3, Mn.sub.3O.sub.4, CuO, FeO, Fe.sub.2O.sub.3, Fe.sub.3O.sub.4, CoO, Co.sub.3O.sub.4, or NiO; a ternary compound, such as MgAl.sub.2O.sub.4, CoFe.sub.2O.sub.4, NiFe.sub.2O.sub.4, or CoMn.sub.2O.sub.4; or any combination thereof. Examples of the semiconductor compound may include, as described herein, a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; or any combination thereof. For example, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0523] A full width at half maximum (FWHM) of an emission wavelength spectrum of the quantum dot may be about 45 nm or less, for example, about 40 nm or less, for example, about 30 nm or less, and within these ranges, color purity or color reproducibility may be increased. In addition, since the light emitted through the quantum dot is emitted in all directions, the viewing angle of light may be improved.
[0524] In addition, the quantum dot may be in the form of spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplate particles.
[0525] Since the energy band gap may be adjusted by controlling the size of the quantum dot, light having various wavelength bands may be obtained from the emission layer including the quantum dot. Accordingly, by using quantum dots of different sizes, a light-emitting device that emits light of various wavelengths may be implemented. In detail, the size of the quantum dot may be selected to emit red, green and/or blue light. In addition, the size of the quantum dot may be configured to emit white light by combining light of various colors.
[0526] [Electron Transport Region in Interlayer 130]
[0527] The electron transport region may have i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer consisting of a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
[0528] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0529] For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein, for each structure, constituting layers are sequentially stacked from the emission layer.
[0530] The electron transport region (for example, the buffer layer, the hole blocking layer, the electron control layer, or the electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group.
[0531] For example, the electron transport region may include a compound represented by Formula 601:
[Ar.sub.601].sub.xe11-[(L.sub.601).sub.xe1-R.sub.601].sub.xe21 Formula 601
[0532] wherein in Formula 601,
[0533] Ar.sub.601 and L.sub.601 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0534] xe11 may be 1, 2, or 3,
[0535] xe1 may be 0, 1, 2, 3, 4, or 5,
[0536] R.sub.601 may be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, —Si(Q.sub.601)(Q.sub.602)(Q.sub.603), —C(═O)(Q.sub.601), —S(═O).sub.2(Q.sub.601), or —P(═O)(Q.sub.601)(Q.sub.602),
[0537] Q.sub.601 to Q.sub.603 are the same as described in connection with Q.sub.1,
[0538] xe21 may be 1, 2, 3, 4, or 5, and
[0539] at least one of Ar.sub.601, L.sub.601, and R.sub.601 may each independently be a π electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group unsubstituted or substituted with at least one R.sub.10a.
[0540] For example, when xe11 in Formula 601 is 2 or more, two or more of Ar.sub.601(s) may be linked to each other via a single bond.
[0541] In one or more embodiments, Ar.sub.601 in Formula 601 may be a substituted or unsubstituted anthracene group.
[0542] In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:
##STR00233##
[0543] wherein in Formula 601-1,
[0544] X.sub.614 may be N or C(R.sub.614), X.sub.615 may be N or C(R.sub.615), X.sub.616 may be N or C(R.sub.616), and at least one of X.sub.614 to X.sub.616 may be N,
[0545] L.sub.611 to L.sub.613 are the same as described in connection with L.sub.601,
[0546] xe611 to xe613 are the same as described in connection with xe1,
[0547] R.sub.611 to R.sub.613 are the same as described in connection with R.sub.601, and
[0548] R.sub.614 to R.sub.616 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a.
[0549] For example, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
[0550] The electron transport region may include one of Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1, 10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq.sub.3, BAlq, TAZ, NTAZ, or any combination thereof:
##STR00234## ##STR00235## ##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240## ##STR00241## ##STR00242## ##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247##
[0551] A thickness of the electron transport region may be in a range of about 100 Å to about 5,000 Å, for example, about 160 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, a thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be from about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, and a thickness of the electron transport layer may be from about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thicknesses of the buffer layer, hole blocking layer, electron control layer, electron transport layer and/or electron transport layer are within these ranges, satisfactory electron-transporting characteristics may be obtained without a substantial increase in driving voltage.
[0552] The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
[0553] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0554] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or ET-D2:
##STR00248##
[0555] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.
[0556] The electron injection layer may have i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer consisting of a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
[0557] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0558] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0559] The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may include oxides, halides (for example, fluorides, chlorides, bromides, or iodides), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
[0560] The alkali metal-containing compound may include alkali metal oxides, such as Li.sub.2O, Cs.sub.2O, or K.sub.2O, alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI, or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, BaxSr.sub.1-xO (wherein x is a real number satisfying the condition of 0<x<1), Ba.sub.xCa.sub.1-xO (wherein x is a real number satisfying the condition of 0<x<1), and the like. The rare earth metal-containing compound may include YbF.sub.3, ScF.sub.3, Sc.sub.2O.sub.3, Y.sub.2O.sub.3, Ce.sub.2O.sub.3, GdF.sub.3, TbF.sub.3, YbI.sub.3, ScI.sub.3, TbI.sub.3, or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include lanthanide metal telluride. Examples of the lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La.sub.2Te.sub.3, Ce.sub.2Te.sub.3, Pr.sub.2Te.sub.3, Nd.sub.2Te.sub.3, Pm.sub.2Te.sub.3, Sm.sub.2Te.sub.3, Eu.sub.2Te.sub.3, Gd.sub.2Te.sub.3, Tb.sub.2Te.sub.3, Dy.sub.2Te.sub.3, Ho.sub.2Te.sub.3, Er.sub.2Te.sub.3, Tm.sub.2Te.sub.3, Yb.sub.2Te.sub.3, and Lu.sub.2Te.sub.3.
[0561] The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include i) one of ions of the alkali metal, the alkaline earth metal, and the rare earth metal and ii), as a ligand bonded to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenyl benzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0562] The electron injection layer may consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material (for example, a compound represented by Formula 601).
[0563] In an embodiment, the electron injection layer may consist of i) an alkali metal-containing compound (for example, alkali metal halide), ii) a) an alkali metal-containing compound (for example, alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, a LiF:Yb co-deposited layer, or the like.
[0564] When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
[0565] A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
[0566] [Second Electrode 150]
[0567] The second electrode 150 may be located on the interlayer 130 as described above. The second electrode 150 may be a cathode, which is an electron injection electrode, and as a material for the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low-work function, may be used.
[0568] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0569] The second electrode 150 may have a single-layered structure or a multi-layered structure including a plurality of layers.
[0570] [Capping Layer]
[0571] A first capping layer may be located outside the first electrode 110, and/or a second capping layer may be located outside the second electrode 150. In detail, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in this stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in this stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in this stated order.
[0572] Light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer or light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.
[0573] The first capping layer and the second capping layer may increase external luminescence efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 may be increased, so that the luminescence efficiency of the light-emitting device 10 may be improved.
[0574] Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or more (at 589 nm).
[0575] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
[0576] At least one of the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may be optionally substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one of the first capping layer and the second capping layer may each independently include an amine group-containing compound.
[0577] For example, at least one of the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0578] In one or more embodiments, at least one of the first capping layer and the second capping layer may each independently include one of Compounds HT28 to HT33, one of Compounds CP1 to CP6, β-NPB, or any combination thereof:
##STR00249##
[0579] [Film]
[0580] The organometallic compound represented by Formula 1 may be included in various films. Accordingly, another aspect provides a film including the organometallic compound represented by Formula 1. The film may be, for example, an optical member (or a light control means) (for example, a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorbing layer, a polarizing layer, a quantum dot-containing layer, or the like), a light-blocking member (for example, a light reflective layer, a light absorbing layer, or the like), a protective member (for example, an insulating layer, a dielectric layer, or the like).
[0581] [Electronic Apparatus]
[0582] The light-emitting device may be included in various electronic apparatuses. For example, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, or the like.
[0583] The electronic apparatus (for example, a light-emitting apparatus) may further include, in addition to the light-emitting device, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or the color conversion layer may be located in at least one traveling direction of light emitted from the light-emitting device. For example, light emitted from the light-emitting device may be blue light or white light. Details for the light-emitting device are the same as described above. In an embodiment, the color conversion layer may include a quantum dot. The quantum dot may be, for example, a quantum dot as described herein.
[0584] The electronic apparatus may include a first substrate. The first substrate may include a plurality of subpixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the subpixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the subpixel areas.
[0585] A pixel-defining film may be located among the subpixel areas to define each of the subpixel areas.
[0586] The color filter may further include a plurality of color filter areas and light-shielding patterns located among the color filter areas, and the color conversion layer may further include a plurality of color conversion areas and light-shielding patterns located among the color conversion areas.
[0587] The color filter areas (or the color conversion areas) may include a first area emitting first color light, a second area emitting second color light, and/or a third area emitting third color light, and the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths from one another. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the color filter areas (or the color conversion areas) may include quantum dots. In detail, the first area may include red quantum dots, the second area may include green quantum dots, and the third area may not include quantum dots. Details for the quantum dots are the same as described in the disclosure. The first area, the second area, and/or the third area may each further include a scatterer.
[0588] For example, the light-emitting device may emit first light, the first area may absorb the first light to emit first-first color light, the second area may absorb the first light to emit second-first color light, and the third area may absorb the first light to emit third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. In detail, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
[0589] The electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device as described above. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light-emitting device.
[0590] The thin-film transistor may further include a gate electrode, a gate insulating film, or the like.
[0591] The activation layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.
[0592] The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be located between the color filter and/or color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and simultaneously prevents ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic apparatus may be flexible.
[0593] Various functional layers may be additionally located on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the use of the electronic apparatus. Examples of the functional layers may include a touch screen layer, a polarizing layer, and the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by using biometric information of a living body (for example, fingertips, pupils, etc.).
[0594] The authentication apparatus may further include, in addition to the light-emitting device as described above, a biometric information collector.
[0595] The electronic apparatus may be applied to various displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various measuring instruments, meters (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and the like.
[0596] [Description of
[0597]
[0598] The light-emitting apparatus of
[0599] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be located on the substrate 100. The buffer layer 210 may prevent penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
[0600] A TFT may be located on the buffer layer 210. The TFT may include an activation layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0601] The activation layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0602] A gate insulating film 230 for insulating the activation layer 220 from the gate electrode 240 may be located on the activation layer 220, and the gate electrode 240 may be located on the gate insulating film 230.
[0603] An interlayer insulating film 250 may be located on the gate electrode 240. The interlayer insulating film 250 may be located between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
[0604] The source electrode 260 and the drain electrode 270 may be located on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the activation layer 220, and the source electrode 260 and the drain electrode 270 may be located in contact with the exposed portions of the source region and the drain region of the activation layer 220.
[0605] The TFT is electrically connected to a light-emitting device to drive the light-emitting device, and is covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. A light-emitting device is provided on the passivation layer 280. The light-emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.
[0606] The first electrode 110 may be located on the passivation layer 280. The passivation layer 280 may be located to expose a portion of the drain electrode 270 without fully covering the drain electrode 270, and the first electrode 110 may be located to be connected to the exposed portion of the drain electrode 270.
[0607] A pixel defining layer 290 including an insulating material may be located on the first electrode 110. The pixel defining layer 290 may expose a portion of the first electrode 110, and an interlayer 130 may be formed in the exposed portion of the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic organic film. Although not shown in
[0608] The second electrode 150 may be located on the interlayer 130, and a capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
[0609] The encapsulation portion 300 may be located on the capping layer 170. The encapsulation portion 300 may be located on a light-emitting device to protect the light-emitting device from moisture or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), or the like), or any combination thereof; or any combination of the inorganic films and the organic films.
[0610]
[0611] The light-emitting apparatus of
[0612] [Manufacture Method]
[0613] Respective layers included in the hole transport region, the emission layer, and respective layers included in the electron transport region may be formed in a region (or a predetermined region) by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, laser-induced thermal imaging, and the like.
[0614] When layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10.sup.−8 torr to about 10.sup.−3 torr, and a deposition speed of about 0.01 Å/sec to about 100 Å/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed.
Definition of Terms
[0615] The term “C.sub.3-C.sub.60 carbocyclic group” as used herein refers to a cyclic group consisting of carbon only as a ring-forming atom and having 3 to 60 carbon atoms, and the term “C.sub.1-C.sub.60 heterocyclic group” as used herein refers to a cyclic group that has 1 to 60 carbon atoms and further has, in addition to carbon, a heteroatom as a ring-forming atom. The C.sub.3-C.sub.60 carbocyclic group and the C.sub.1-C.sub.60 heterocyclic group may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. For example, the C.sub.1-C.sub.60 heterocyclic group has 3 to 61 ring-forming atoms.
[0616] The “cyclic group” as used herein may include the C.sub.3-C.sub.60 carbocyclic group and the C.sub.1-C.sub.60 heterocyclic group.
[0617] The term “π electron-rich C.sub.3-C.sub.60 cyclic group” as used herein refers to a cyclic group that has 3 to 60 carbon atoms and does not include *—N═*′ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group” as used herein refers to a heterocyclic group that has 1 to 60 carbon atoms and includes *—N═*′ as a ring-forming moiety.
[0618] For example,
[0619] the C.sub.3-C.sub.60 carbocyclic group may be i) group T1 or ii) a condensed cyclic group in which two or more groups T1 are condensed with each other (for example, a cyclopentadiene group, an adamantane group, a norbornane group, a benzene group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a perylene group, a pentaphene group, a heptalene group, a naphthacene group, a picene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indenophenanthrene group, or an indenoanthracene group),
[0620] the C.sub.1-C.sub.60 heterocyclic group may be i) group T2, ii) a condensed cyclic group in which two or more groups T2 are condensed with each other, or iii) a condensed cyclic group in which at least one group T2 and at least one group T1 are condensed with each other (for example, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, etc.),
[0621] the π electron-rich C.sub.3-C.sub.60 cyclic group may be i) group T1, ii) a condensed cyclic group in which two or more groups T1 are condensed with each other, iii) group T3, iv) a condensed cyclic group in which two or more groups T3 are condensed with each other, or v) a condensed cyclic group in which at least one group T3 and at least one group T1 are condensed with each other (for example, the C.sub.3-C.sub.60 carbocyclic group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, etc.),
[0622] the π electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group may be i) group T4, ii) a condensed cyclic group in which two or more groups T4 are condensed with each other, iii) a condensed cyclic group in which at least one group T4 and at least one group T1 are condensed with each other, iv) a condensed cyclic group in which at least one group T4 and at least one group T3 are condensed with each other, or v) a condensed cyclic group in which at least one group T4, at least one group T1, and at least one group T3 are condensed with one another (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, etc.),
[0623] the group T1 may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or a bicyclo[2.2.1]heptane) group, a norbornene 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,
[0624] the group T2 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidine group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group, or a dihydropyridazine group,
[0625] the group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group, and
[0626] the group T4 may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.
[0627] The terms “the cyclic group, the C.sub.3-C.sub.60 carbocyclic group, the C.sub.1-C.sub.60 heterocyclic group, the π electron-rich C.sub.3-C.sub.60 cyclic group, or the π electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group” as used herein refer to a group condensed to any cyclic group, a monovalent group, or a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of a formula for which the corresponding term is used. For example, the “benzene group” may be a benzo group, a phenyl group, a phenylene group, or the like, which may be easily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”
[0628] Examples of the monovalent C.sub.3-C.sub.60 carbocyclic group and the monovalent C.sub.1-C.sub.60 heterocyclic group may include a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and examples of the divalent C.sub.3-C.sub.60 carbocyclic group and the monovalent C.sub.1-C.sub.60 heterocyclic group may include a C.sub.3-C.sub.10 cycloalkylene group, a C.sub.1-C.sub.10 heterocycloalkylene group, a C.sub.3-C.sub.10 cycloalkenylene group, a C.sub.1-C.sub.10 heterocycloalkenylene group, a C.sub.6-C.sub.60 arylene group, a C.sub.1-C.sub.60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.
[0629] The term “C.sub.1-C.sub.60 alkyl group” as used herein refers to a linear or branched aliphatic hydrocarbon monovalent group that has one to sixty carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group. The term “C.sub.1-C.sub.60 alkylene group” as used herein refers to a divalent group having the same structure as the C.sub.1-C.sub.60 alkyl group.
[0630] The term “C.sub.2-C.sub.60 alkenyl group” as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of the C.sub.2-C.sub.60 alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C.sub.2-C.sub.60 alkenylene group” as used herein refers to a divalent group having the same structure as the C.sub.2-C.sub.60 alkenyl group.
[0631] The term “C.sub.2-C.sub.60 alkynyl group” as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C.sub.2-C.sub.60 alkyl group, and examples thereof include an ethynyl group and a propynyl group. The term “C.sub.2-C.sub.60 alkynylene group” as used herein refers to a divalent group having the same structure as the C.sub.2-C.sub.60 alkynyl group.
[0632] The term “C.sub.1-C.sub.60 alkoxy group” as used herein refers to a monovalent group represented by —OA.sub.101 (wherein A.sub.101 is the C.sub.1-C.sub.60 alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
[0633] The term “C.sub.3-C.sub.10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. The term “C.sub.3-C.sub.10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C.sub.3-C.sub.10 cycloalkyl group.
[0634] The term “C.sub.1-C.sub.10 heterocycloalkyl group” as used herein refers to a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and examples are a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C.sub.1-C.sub.10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C.sub.1-C.sub.10 heterocycloalkyl group.
[0635] The term “C.sub.3-C.sub.10 cycloalkenyl group” as used herein refers to a monovalent cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C.sub.3-C.sub.10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C.sub.3-C.sub.10 cycloalkenyl group.
[0636] The term “C.sub.1-C.sub.10 heterocycloalkenyl group” as used herein refers to a monovalent cyclic group that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in the cyclic structure thereof. Examples of the C.sub.1-C.sub.10 heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C.sub.1-C.sub.10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C.sub.1-C.sub.10 heterocycloalkenyl group.
[0637] The term “C.sub.6-C.sub.60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms, and the term “C.sub.6-C.sub.60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. Examples of the C.sub.6-C.sub.60 aryl group include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group. When the C.sub.6-C.sub.60 aryl group and the C.sub.6-C.sub.60 arylene group each include two or more rings, the rings may be condensed with each other.
[0638] The term “C.sub.1-C.sub.60 heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms. The term “C.sub.1-C.sub.60 heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms. Examples of the C.sub.1-C.sub.60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and a naphthyridinyl group. When the C.sub.1-C.sub.60 heteroaryl group and the C.sub.1-C.sub.60 heteroarylene group each include two or more rings, the rings may be condensed with each other.
[0639] The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, and an indeno anthracenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group described above.
[0640] The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having non-aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphtho indolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group described above.
[0641] The term “C.sub.6-C.sub.60 aryloxy group” as used herein indicates —OA.sub.102 (wherein A.sub.102 is a C.sub.6-C.sub.60 aryl group), and the term “C.sub.6-C.sub.60 arylthio group” as used herein indicates —SA.sub.103 (wherein A.sub.103 is a C.sub.6-C.sub.60 aryl group).
[0642] The term “C.sub.7-C.sub.60 aryl alkyl group” as used herein refers to -A.sub.104A.sub.105 (where A.sub.104 may be a C.sub.1-C.sub.54 alkylene group, and A.sub.105 may be a C.sub.6-C.sub.59 aryl group), and the term “C.sub.2-C.sub.60 heteroaryl alkyl group” as used herein refers to -A.sub.106A.sub.107 (where A.sub.106 may be a C.sub.1-C.sub.59 alkylene group, and A.sub.107 may be a C.sub.1-C.sub.59 heteroaryl group).
[0643] The term “R.sub.10a” as used herein refers to:
[0644] deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
[0645] a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, or a C.sub.1-C.sub.60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.7-C.sub.60 arylalkyl group, a C.sub.2-C.sub.60 heteroarylalkyl group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.11)(Q.sub.12), —B(Q.sub.11)(Q.sub.12), —C(═O)(Q.sub.11), —S(═O).sub.2(Q.sub.11), —P(═O)(Q.sub.11)(Q.sub.12), or any combination thereof;
[0646] a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.7-C.sub.60 arylalkyl group, or a C.sub.2-C.sub.60 heteroarylalkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.7-C.sub.60 arylalkyl group, a C.sub.2-C.sub.60 heteroarylalkyl group, —Si(Q.sub.21)(Q.sub.22)(Q.sub.23), —N(Q.sub.21)(Q.sub.22), —B(Q.sub.21)(Q.sub.22), —C(═O)(Q.sub.21), —S(═O).sub.2(Q.sub.21), —P(═O)(Q.sub.21)(Q.sub.22), or any combination thereof; or
[0647] —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), or —P(═O)(Q.sub.31)(Q.sub.32).
[0648] Q.sub.1 to Q.sub.3, Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23, and Q.sub.31 to Q.sub.33 used herein may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxy group; a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C.sub.1-C.sub.60 alkyl group, a C.sub.1-C.sub.60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C.sub.7-C.sub.60 aryl alkyl group; or a C.sub.2-C.sub.60 heteroaryl alkyl group.
[0649] The term “heteroatom” as used herein refers to any atom other than a carbon atom. Examples of the heteroatom include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0650] The term “third-row transition metal” used herein includes hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and the like.
[0651] “Ph” as used herein refers to a phenyl group, “Me” as used herein refers to a methyl group, “Et” as used herein refers to an ethyl group, “tert-Bu” or “Bu.sup.t” as used herein refers to a tert-butyl group, and “OMe” as used herein refers to a methoxy group.
[0652] The term “biphenyl group” as used herein refers to “a phenyl group substituted with a phenyl group.” In other words, the “biphenyl group” is a substituted phenyl group having a C.sub.6-C.sub.60 aryl group as a substituent.
[0653] The term “terphenyl group” as used herein refers to “a phenyl group substituted with a biphenyl group”. In other words, the “terphenyl group” is a substituted phenyl group having, as a substituent, a C.sub.6-C.sub.60 aryl group substituted with a C.sub.6-C.sub.60 aryl group.
[0654] * and *′ as used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula or moiety.
[0655] Hereinafter, compounds according to embodiments and light-emitting devices according to embodiments will be described in detail with reference to the following synthesis examples and examples. The wording “B was used instead of A” used in describing Synthesis Examples means that an identical molar equivalent of B was used in place of A.
EXAMPLES
Synthesis Example 1: Synthesis of Compound 3
[0656] ##STR00250## ##STR00251##
[0657] (Synthesis of Intermediate 3-1)
[0658] 5.6 g (20 mmol) of 2-iodobiphenyl, 6.1 g (30 mmol) of 2-bromo-5-methoxyaniline, 0.022 g (0.1 mmol) of palladium acetate, 0.061 g (0.2 mmol) of P(o-tol).sub.3, and 13 g (40 mmol) of cesium carbonate were placed in a reaction vessel, and suspended in 100 ml of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 120° C., and stirred for 36 hours. After completion of the reaction, the reaction result was cooled at room temperature, 300 mL of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 4.9 g (18 mmol) of Intermediate [3-1].
[0659] (Synthesis of Intermediate 3-2)
[0660] 4.9 g (18 mmol) of Intermediate [3-1], 5.8 g (27 mmol) of 2-bromo-4(tert-butyl)pyridine, 8.3 g (36 mmol) of potassium triphosphate, 0.66 g (3.6 mmol) of CuI, and 0.4 g (3.6 mmol) of picolinic acid were placed in a reaction vessel, and suspended in 60 ml of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160° C., and stirred for 24 hours. After completion of the reaction, the reaction result was cooled at room temperature, 100 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 6.1 g (15 mmol) of Intermediate [3-2].
[0661] (Synthesis of Intermediate 3-3)
[0662] 6.1 g (15 mmol) of Intermediate [3-2] was suspended in an excess of bromic acid solution. The reaction mixture was heated to a temperature of 110° C., and stirred for 24 hours. After completion of the reaction, the reaction product was cooled at room temperature, and an appropriate amount of sodium hydrogen carbonate was added thereto to perform neutralization. 100 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 5.1 g (13 mmol) of Intermediate [3-3].
[0663] (Synthesis of Intermediate 3-4)
[0664] 5.1 g (13 mmol) of Intermediate [3-3], 4.3 g (19.5 mmol) of 1-(3-bromophenyl)-1H-imidazole, 6.0 g (26 mmol) of potassium triphosphate, 0.47 g (0.26 mmol) of CuI, and 0.03 g (0.26 mmol) of picolinic acid were placed in a reaction vessel, and suspended in 50 ml of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160° C., and stirred for 36 hours. After completion of the reaction, the reaction result was cooled at room temperature, 100 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 5.3 g (10 mmol) of Intermediate [3-4].
[0665] (Synthesis of Intermediate 3-5)
[0666] 5.3 g (10 mmol) of Intermediate [3-4] and 15 mmol of diphenyliodonium were suspended in toluene. The reaction mixture was heated to a temperature of 110° C., and stirred for 24 hours. After completion of the reaction, the reaction result was cooled at room temperature, 100 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 6.1 g (8.2 mmol) of Intermediate [3-5].
[0667] (Synthesis of Intermediate 3-6)
[0668] 6.1 g (8.2 mmol) of Intermediate [3-5] and 5.31 g (32 mmol) of ammonium hexafluorophosphate were placed in a reaction vessel, and suspended in a mixed solution including 100 ml of methyl alcohol and 25 ml of water. The reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, the resulting solid was filtered and washed with ether. The washed solid was dried to obtain 5.8 g (7.7 mmol) of Intermediate [3-6].
[0669] (Synthesis of Compound 3)
[0670] 5.8 g (7.7 mmol) of Intermediate [3-6], 2.96 g (8.08 mmol) of dichloro(1,5-cyclooctadiene)platinum, and 1.26 g (15.4 mmol) of sodium acetate were suspended in 80 ml of dioxane. The reaction mixture was heated, and stirred at 110° C. for 72 hours. After completion of the reaction, the reaction result was cooled at room temperature, 100 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 2.17 g (2.7 mmol) of Compound 3.
Synthesis Example 2: Synthesis of Compound 26
[0671] ##STR00252## ##STR00253## ##STR00254##
[0672] (Synthesis of Intermediate 26-1)
[0673] 4.9 g (18 mmol) of Intermediate [3-1], 5.8 g (27 mmol) of 2-fluoro-4-methyl-5-phenylpyridine, and 8.3 g (36 mmol) of potassium triphosphate were placed in a reaction vessel, and suspended in 60 ml of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160° C., and stirred for 12 hours. After completion of the reaction, the reaction result was cooled at room temperature, 100 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 7.0 g (16 mmol) of Intermediate [26-1].
[0674] (Synthesis of Intermediate 26-2)
[0675] 7.0 g (16 mmol) of Intermediate [26-1] was suspended in an excess of bromic acid solution. The reaction mixture was heated to a temperature of 110° C., and stirred for 24 hours. After completion of the reaction, the reaction product was cooled at room temperature, and an appropriate amount of sodium hydrogen carbonate was added thereto to perform neutralization. 100 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 6.0 g (14 mmol) of Intermediate [26-2].
[0676] (Synthesis of Intermediate 26-3)
[0677] 6.0 g (14 mmol) of Intermediate [26-2], 3.7 g (21 mmol) of 1-bromo-3-fluorobenzene, and 6.5 g (28 mmol) of potassium triphosphate were placed in a reaction vessel, and suspended in 50 ml of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160° C., and stirred for 12 hours. After completion of the reaction, the reaction result was cooled at room temperature, 100 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 6.4 g (11 mmol) of Intermediate [26-3].
[0678] (Synthesis of Intermediate 26-4)
[0679] 6.4 g (11 mmol) of Intermediate [26-3], 2.64 g (11 mmol) of N.sup.1-(4-(t-butyl)phenyl)benzene-1,2-diamine, SPhos (0.83 mmol), Pd.sub.2(dba).sub.3 (0.55 mmol), and sodium t-butoxide (22 mmol) were suspended in 100 ml of a toluene solvent, heated to a temperature of 100° C., and stirred for 5 hours. After completion of the reaction, the solvent was removed therefrom under reduced pressure, and an extraction process was performed thereon by using methylene chloride and distilled water. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 7.0 g (9.4 mmol) of Intermediate [26-4].
[0680] (Synthesis of Intermediate 26-5)
[0681] 7.0 g (9.4 mmol) of Intermediate [26-4] was dissolved in 470 mmol of triethyl orthoformate, and then, 11.3 mmol of HCl was added dropwise thereto. The reaction mixture was heated to a temperature of 80° C., and stirred for 20 hours. After completion of the reaction, the solvent was removed therefrom under reduced pressure, and an extraction process was performed thereon by using methylene chloride and distilled water. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 5.3 g (6.7 mmol) of Intermediate [26-5].
[0682] (Synthesis of Intermediate 26-6)
[0683] 5.3 g (6.7 mmol) of Intermediate [26-5] and 3.3 g (20.1 mmol) of ammonium hexafluorophosphate were placed in a reaction vessel, and suspended in a mixed solution including 100 ml of methyl alcohol and 25 ml of water. The reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, the resulting solid was filtered and washed with ether. The washed solid was dried to obtain 5.7 g (6.3 mmol) of Intermediate [26-6].
[0684] (Synthesis of Compound 26)
[0685] 5.7 g (6.3 mmol) of Intermediate [26-6], 2.54 g (6.93 mmol) of dichloro(1,5-cyclooctadiene)platinum, and 1.03 g (12.6 mmol) of sodium acetate were suspended in 80 ml of dioxane. The reaction mixture was heated, and stirred at 110° C. for 72 hours. After completion of the reaction, the reaction result was cooled at room temperature, 100 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 1.79 g (1.9 mmol) of Compound 26.
Synthesis Example 3: Synthesis of Compound 33
[0686] ##STR00255## ##STR00256##
[0687] (Synthesis of Intermediate 33-1)
[0688] 4.9 g (18 mmol) of Intermediate [3-1], 2.6 g (27 mmol) of 2-fluoropyridine, and 8.3 g (36 mmol) of potassium triphosphate were placed in a reaction vessel, and suspended in 60 ml of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160° C., and stirred for 12 hours. After completion of the reaction, the reaction result was cooled at room temperature, 100 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 5.8 g (16.5 mmol) of Intermediate [33-1].
[0689] (Synthesis of Intermediate 33-2)
[0690] 5.8 g (16.5 mmol) of Intermediate [33-1] was suspended in an excess of bromic acid solution. The reaction mixture was heated to a temperature of 110° C., and stirred for 24 hours. After completion of the reaction, the reaction product was cooled at room temperature, and an appropriate amount of sodium hydrogen carbonate was added thereto to perform neutralization. 100 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 5.0 g (15 mmol) of Intermediate [33-2].
[0691] (Synthesis of Intermediate 33-3)
[0692] 5.0 g (15 mmol) of Intermediate [33-2], 4.0 g (22.5 mmol) of 1-bromo-3-fluorobenzene, and 7.0 g (30 mmol) of potassium triphosphate were placed in a reaction vessel, and suspended in 60 ml of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160° C., and stirred for 12 hours. After completion of the reaction, the reaction result was cooled at room temperature, 100 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 6.4 g (13 mmol) of Intermediate [33-3].
[0693] (Synthesis of Intermediate 33-4)
[0694] 6.4 g (13 mmol) of Intermediate [33-3], 4.5 g (13 mmol) of N1-([1,1′:3′,1″-terphenyl]-2′-yl-2,2″,3,3″,4,4″,5,5″,6,6″-d.sub.10)benzene-d.sub.4-1,2-diamine, SPhos (0.98 mmol), Pd.sub.2(dba).sub.3 (0.65 mmol), and sodium t-butoxide (26 mmol) were suspended in 100 ml of a toluene solvent, heated to a temperature of 100° C., and stirred for 5 hours. After completion of the reaction, the solvent was removed therefrom under reduced pressure, and an extraction process was performed thereon by using methylene chloride and distilled water. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 8.5 g (11 mmol) of Intermediate [33-4].
[0695] (Synthesis of Intermediate 33-5)
[0696] 8.5 g (11 mmol) of Intermediate [33-4] was dissolved in 550 mmol of triethyl orthoformate, and then, 13 mmol of HCl was added dropwise thereto. The reaction mixture was heated to a temperature of 80° C., and stirred for 20 hours. After completion of the reaction, the solvent was removed therefrom under reduced pressure, and an extraction process was performed thereon by using methylene chloride and distilled water. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 8.2 g (10 mmol) of Intermediate [33-5].
[0697] (Synthesis of Intermediate 33-6)
[0698] 8.2 g (10 mmol) of Intermediate [33-5] and 4.9 g (30 mmol) of ammonium hexafluorophosphate were placed in a reaction vessel, and suspended in a mixed solution including 200 ml of methyl alcohol and 50 ml of water. The reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, the resulting solid was filtered and washed with ether. The washed solid was dried to obtain 8.5 g (9.2 mmol) of Intermediate [33-6].
[0699] (Synthesis of Compound 33)
[0700] 8.5 g (9.2 mmol) of Intermediate [33-6], 3.37 g (10.1 mmol) of dichloro(1,5-cyclooctadiene)platinum, and 1.5 g (18.4 mmol) of sodium acetate were suspended in 100 ml of dioxane. The reaction mixture was heated to a temperature of 110° C., and stirred for 72 hours. After completion of the reaction, the reaction result was cooled at room temperature, 200 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 2.59 g (2.7 mmol) of Compound 33.
Synthesis Example 4: Synthesis of Compound 73
[0701] ##STR00257##
[0702] (Synthesis of Intermediate 73-2)
[0703] Intermediate [73-2] was obtained in the same manner as used to prepare Intermediate [3-2] in Synthesis Example 1, except that Intermediate [73-1] was used instead of Intermediate [3-1], and 2-bromopyridine was used instead of 2-bromo-4(tert-butyl)pyridine.
[0704] (Synthesis of Intermediate 73-3)
[0705] Intermediate [73-3] was obtained in the same manner as used to prepare Intermediate [3-4] in Synthesis Example 1, except that Intermediate [73-2] was used instead of Intermediate [3-3], and 3-(1H-benzo[d]imidazole-1-nyl)benzenethiol was used instead of 1-(3-bromophenyl)-1H-imidazole.
[0706] (Synthesis of Intermediate 73-4)
[0707] 6.2 g (10 mmol) of Intermediate [73-3], 8.8 g (15 mmol) of Intermediate [A-1], and 0.18 g (1.0 mmol) of Cu(OAc).sub.2 were added to dimethyl sulfoxide, and the reaction mixture was heated to a temperature of 150° C. and stirred for 12 hours. After completion of the reaction, the reaction result was cooled at room temperature, 100 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 6.2 g (6.5 mmol) of Intermediate [73-4].
[0708] (Synthesis of Compound 73)
[0709] 2.6 g (2.6 mmol) of Compound 73 was obtained in the same manner as used to prepare Compound 3 in Synthesis Example 1, except that Intermediate [73-4] was used instead of Intermediate [3-6].
Synthesis Example 5: Synthesis of Compound 87
[0710] ##STR00258## ##STR00259##
[0711] (Synthesis of Intermediate 87-1)
[0712] Intermediate [87-1] was obtained in the same manner as used to prepare Intermediate [3-1] in Synthesis Example 1, except that 4″-(t-butyl)-2′-iodo-1,1′:4′,1″-terphenyl was used instead of 2-iodobiphenyl, and 2,5-dibromoaniline was used instead of 2-bromo-5-methoxyaniline.
[0713] (Synthesis of Intermediate 87-2)
[0714] Intermediate [87-2] was obtained in the same manner as used to prepare Intermediate [3-2] in Synthesis Example 1, except that Intermediate [87-1] was used instead of Intermediate [3-1], and 2-bromopyridine was used instead of 2-bromo-4(tert-butyl)pyridine.
[0715] (Synthesis of Intermediate 87-3)
[0716] Intermediate [87-3] was obtained in the same manner as used to prepare Intermediate [3-4] in Synthesis Example 1, except that Intermediate [87-2] was used instead of Intermediate [3-3], and 3-(1H-benzo[d]imidazole-1-nyl)benzenethiol was used instead of 1-(3-bromophenyl)-1H-imidazole.
[0717] (Synthesis of Intermediate 87-4)
[0718] Intermediate [87-4] was obtained in the same manner as used to prepare Intermediate [73-4] in Synthesis Example 4, except that Intermediate [87-3] was used instead of Intermediate [73-3], and Intermediate [A-2] was used instead of Intermediate [A-1].
[0719] (Synthesis of Compound 87)
[0720] 1.8 g (1.8 mmol) of Compound 87 was obtained in the same manner as used to prepare Compound 3 in Synthesis Example 1, except that Intermediate [87-4] was used instead of Intermediate [3-6].
Synthesis Example 6: Synthesis of Compound 100
[0721] ##STR00260## ##STR00261##
[0722] (Synthesis of Intermediate 100-2)
[0723] Intermediate [100-2] was obtained in the same manner as used to prepare Intermediate [3-2] in Synthesis Example 1, except that Intermediate [100-1] was used instead of Intermediate [3-1].
[0724] (Synthesis of Intermediate 100-3)
[0725] Intermediate [100-3] was obtained in the same manner as used to prepare Intermediate [3-3] in Synthesis Example 1, except that Intermediate [100-2] was used instead of Intermediate [3-2].
[0726] (Synthesis of Intermediate 100-4)
[0727] Intermediate [100-4] was obtained in the same manner as used to prepare Intermediate [3-4] in Synthesis Example 1, except that Intermediate [100-3] was used instead of Intermediate [3-3].
[0728] (Synthesis of Intermediate 100-5)
[0729] Intermediate [100-5] was obtained in the same manner as used to prepare Intermediate [73-4] in Synthesis Example 4, except that Intermediate [100-4] was used instead of Intermediate [73-3], and Intermediate [A-3] was used instead of Intermediate [A-1].
[0730] (Synthesis of Compound 100)
[0731] 8.3 g (10 mmol) of Intermediate [100-5], 2.5 g (11 mmol) of Pd(OAc).sub.2, and 0.25 g (30 mmol) of sodium acetate were suspended in 100 ml of dioxane. The reaction mixture was heated to a temperature of 120° C., and stirred for 24 hours. After completion of the reaction, the reaction result was cooled at room temperature, 200 ml of distilled water was added thereto, and an extraction process was performed thereon by using ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried using sodium sulfate. A residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 1.97 g (2.5 mmol) of Compound 100.
Synthesis Example 7: Synthesis of Compound 122
[0732] ##STR00262## ##STR00263##
[0733] (Synthesis of Intermediate 122-1)
[0734] Intermediate [122-1] was obtained in the same manner as used to prepare Intermediate [3-2] in Synthesis Example 1, except that 4-iodo-3-phenylpyridine was used instead of 2-iodobiphenyl.
[0735] (Synthesis of Intermediate 122-2)
[0736] Intermediate [122-2] was obtained in the same manner as used to prepare Intermediate [3-2] in Synthesis Example 1, except that Intermediate [122-1] was used instead of Intermediate [3-1].
[0737] (Synthesis of Intermediate 122-3)
[0738] Intermediate [122-3] was obtained in the same manner as used to prepare Intermediate [33-3] in Synthesis Example 3, except that Intermediate [122-2] was used instead of Intermediate [33-2].
[0739] (Synthesis of Intermediate 122-4)
[0740] Intermediate [122-4] was obtained in the same manner as used to prepare Intermediate [33-4] in Synthesis Example 3, except that Intermediate [122-3] was used instead of Intermediate [33-3].
[0741] (Synthesis of Intermediate 122-5)
[0742] Intermediate [122-5] was obtained in the same manner as used to prepare Intermediate [33-5] in Synthesis Example 3, except that Intermediate [122-4] was used instead of Intermediate [33-4].
[0743] (Synthesis of Intermediate 122-6)
[0744] Intermediate [122-6] was obtained in the same manner as used to prepare Intermediate [33-6] in Synthesis Example 3, except that Intermediate [122-5] was used instead of Intermediate [33-5].
[0745] (Synthesis of Compound 122)
[0746] 1.4 g (1.5 mmol) of Compound 122 was obtained in the same manner as used to prepare Compound 100 in Synthesis Example 6, except that Intermediate [122-6] was used instead of Intermediate [100-5].
Synthesis Example 8: Synthesis of Compound 138
[0747] ##STR00264##
[0748] (Synthesis of Intermediate 138-2)
[0749] Intermediate [138-2] was obtained in the same manner as used to prepare Intermediate [3-2] in Synthesis Example 1, except that Intermediate [138-1] was used instead of Intermediate [3-1], and 2-bromopyridine was used instead of 2-bromo-4(tert-butyl)pyridine.
[0750] (Synthesis of Intermediate 138-3)
[0751] Intermediate [138-3] was obtained in the same manner as used to prepare Intermediate [3-4] in Synthesis Example 1, except that Intermediate [138-2] was used instead of Intermediate [3-3], and 3-(1H-benzo[d]imidazole-1-nyl)benzenethiol was used instead of 1-(3-bromophenyl)-1H-imidazole.
[0752] (Synthesis of Intermediate 138-4)
[0753] Intermediate [138-4] was obtained in the same manner as used to prepare Intermediate [73-4] in Synthesis Example 4, except that Intermediate [138-3] was used instead of Intermediate [73-3], and Intermediate [A-4] was used instead of Intermediate [A-1].
[0754] (Synthesis of Compound 138)
[0755] 1.2 g (1.6 mmol) of Compound 138 was obtained in the same manner as used to prepare Compound 100 in Synthesis Example 6, except that Intermediate [138-4] was used instead of Intermediate [100-5].
Synthesis Example 9: Synthesis of Compound 176
[0756] ##STR00265## ##STR00266##
[0757] (Synthesis of Intermediate 176-1)
[0758] Intermediate [176-1] was obtained in the same manner as used to prepare Intermediate [3-1] in Synthesis Example 1, except that 4(t-butyl)2-iodo-1,1′-biphenyl was used instead of 2-iodobiphenyl, and 2,5-dibromoaniline was used instead of 2-bromo-5-methoxyaniline.
[0759] (Synthesis of Intermediate 176-2)
[0760] Intermediate [176-2] was obtained in the same manner as used to prepare Intermediate [3-2] in Synthesis Example 1, except that Intermediate [176-1] was used instead of Intermediate [3-1], and 2-bromopyridine was used instead of 2-bromo-4(tert-butyl)pyridine.
[0761] (Synthesis of Intermediate 176-3)
[0762] Intermediate [176-3] was obtained in the same manner as used to prepare Intermediate [3-4] in Synthesis Example 1, except that Intermediate [176-2] was used instead of Intermediate [3-3], and 3-bromobenzenethiol was used instead of 1-(3-bromophenyl)-1H-imidazole.
[0763] (Synthesis of Intermediate 176-4)
[0764] Intermediate [176-4] was obtained in the same manner as used to prepare Intermediate [33-4] in Synthesis Example 3, except that Intermediate [176-3] was used instead of Intermediate [33-3], and Intermediate [A-5] was used instead of N1-([1,1′:3′,1″-terphenyl]-2′-nyl-2,2″,3,3″,4,4″,5,5″,6,6″-d.sub.10)benzene-d.sub.4-1,2-diamine.
[0765] (Synthesis of Intermediate 176-5)
[0766] Intermediate [176-5] was obtained in the same manner as used to prepare Intermediate [33-5] in Synthesis Example 3, except that Intermediate [176-4] was used instead of Intermediate [33-4].
[0767] (Synthesis of Intermediate 176-6)
[0768] Intermediate [176-6] was obtained in the same manner as used to prepare Intermediate [33-6] in Synthesis Example 3, except that Intermediate [176-5] was used instead of Intermediate [33-5].
[0769] (Synthesis of Compound 176)
[0770] 1.2 g (1.3 mmol) of Compound 176 was obtained in the same manner as used to prepare Compound 100 in Synthesis Example 6, except that Intermediate [176-6] was used instead of Intermediate [100-5].
[0771] .sup.1H NMR and MS/FAB of the compounds synthesized according to Synthesis Examples are shown in Table 1.
[0772] Synthesis methods for other compounds than the compounds shown in Table 1 may be easily recognized by those skilled in the technical field by referring to the synthesis paths and source materials described above.
TABLE-US-00001 TABLE 1 Compound MS/FAB No. .sup.1H NMR (CDCI.sub.3, 400 MHz) found calc. 3 δ 8.14-8.12(m, 2H), 7.96-7.94(m, 2H), 7.69(d, 803.2221 803.2224 1H), 7.60-7.58(m, 2H), 7.41-7.35(m, 4H), 7.20- 7.05(m, 3H), 6.85(d, 1H), 6.70(d, 1H), 6.60- 6.51 (m, 5H), 5.43(s, 2H), 1.32(s, 9H) 26 δ 8.46(s, 1H), 8.11(d, 1H), 7.97-7.95(m, 2H), 943.2847 943.2850 7.69(d, 1H), 7.61-7.59(m, 2H), 7.46-7.39(m, 7H), 7.18-7.10(m, 8H), 6.95-6.85(m, 4H), 6.71 (s, 1H), 6.66(d, 1H), 2.68(s, 3H), 1.33(s, 9H) 33 δ 8.22-8.20(m, 2H), 8.11-8.10(m, 2H), 7.97- 959.3309 959.3308 7.95(m, 2H), 7.69(d, 1H), 7.60-7.56(m, 3H), 7.40-7.38(m, 3H), 7.18-7.14(m, 4H), 6.95- 6.85(m, 4H), 6.66-6.58(m, 3H) 73 δ 8.12(d, 1H), 7.96-7.92(m, 3H), 7.76(d, 2H), 1001.3090 1001.3091 7.61-7.42(m, 8H), 7.23-7.20(m, 4H), 7.14- 7.11(m, 3H), 7.06(d, 1H), 6.95-6.91(m, 4H), 6.63-6.57(m, 2H), 1.42(s, 18H) 87 δ 8.12(d, 1H), 7.96-7.93(m, 3H), 7.60-7.55(m, 1001.3089 1001.3091 4H), 7.38-7.37(m, 2H), 7.29-7.11(m, 11H), 6.95- 6.91 (m, 4H), 6.63-6.57(m, 2H), 1.38(s, 9H), 1.33(s, 9H) 100 δ 8.11(d, 1H), 7.96(d, 2H), 7.71-7.69(m, 2H), 788.2145 788.2143 7.60(d, 2H), 7.47(m, 1H), 7.05-6.99(m, 4H), 6.85(d, 1H), 6.67(d, 1H), 6.52-6.47(m, 3H), 6.38(d, 2H), 5.43(s, 2H), 1.35(s, 9H), 1.32(s, 9H) 122 δ 9.05(s, 1H), 8.26-8.22(m, 3H), 8.12(d, 1H), 927.2976 927.2974 7.96(d, 2H), 7.69(d, 1H), 7.60(d, 2H), 7.39(m, 1H), 7.15-7.06(m, 4H), 6.94-6.85(m, 4H), 6.67- 6.65(m, 2H), 6.52(d, 1H), 1.32(s, 9H) 138 δ 8.11(d, 1H), 7.96(d, 2H), 7.90(s, 1H), 7.75(d, 755.1381 755.1383 2H), 7.60-7.43(m, 9H), 7.24(d, 1H), 7.12- 7.11(m, 1H), 6.84(d, 1H), 6.62-6.57(m, 3H), 5.43(s, 2H) 176 δ 8.11(d, 1H), 7.96(d, 2H), 7.90(d, 1H), 7.63- 912.2476 912.2478 7.55(m, 6H), 7.43-7.41 (m, 3H), 7.30(d, 1H), 7.23-7.06(m, 9H), 6.95-9.92(m, 3H), 6.63- 6.58(m, 2H), 1.37(s, 9H), 1.26(s, 9H)
Example 1
[0773] As an anode, a glass substrate (product of Corning Inc.) with a 15 Ω/cm.sup.2 (1,200 Å) ITO formed thereon was cut to a size of 50 mm×50 mm×0.7 mm, sonicated using isopropyl alcohol and pure water each for 5 minutes, and then washed by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes. Then, the glass substrate was mounted on a vacuum deposition apparatus.
[0774] 2-TNATA, which is a known compound in the art, was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 600 Å, and then, 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred to as NPB) as a hole transport compound was vacuum-deposited thereon to form a hole transport layer having a thickness of 300 Å.
[0775] Compound 3, Compound ETH2, and Compound HTH29 were co-deposited on the hole transport layer to form an emission layer having a thickness of 400 Å. In this regard, an amount of Compound 1 was 10 wt % based on a total weight (100 wt %) of the emission layer, and a weight ratio of Compound ETH2 to Compound HTH29 was 3:7.
[0776] Next, Compound ETH2 was vacuum-deposited to form a hole blocking layer having a thickness of 50 Å, Alq.sub.3 was deposited on the emission layer to form an electron transport layer having a thickness of 300 Å, and then, LiF, which is a halogenated alkali metal, was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited to form a cathode having a thickness of 3,000 Å to form an LiF/Al electrode, thereby completing the manufacture of an organic light-emitting device.
##STR00267## ##STR00268##
Example 2
[0777] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound ETH68 and Compound HTH41 were used instead of Compound ETH2 and Compound HTH29.
Example 3
[0778] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound 26 was used instead of Compound 3, and Compound ETH2 and Compound HTH41 were used instead of Compound ETH2 and Compound HTH29.
Example 4
[0779] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound 33 was used instead of Compound 3, and Compound ETH68 and Compound HTH29 were used instead of Compound ETH2 and Compound HTH29.
Example 5
[0780] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound 73 was used instead of Compound 3, and Compound ETH68 and Compound HTH29 were used instead of Compound ETH2 and Compound HTH29.
Example 6
[0781] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound 87 was used instead of Compound 3, and Compound ETH68 and Compound HTH29 were used instead of Compound ETH2 and Compound HTH29.
Example 7
[0782] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound 100 was used instead of Compound 3, and Compound ETH2 and Compound HTH41 were used instead of Compound ETH2 and Compound HTH29.
Example 8
[0783] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound 122 was used instead of Compound 3, and Compound ETH68 and Compound HTH29 were used instead of Compound ETH2 and Compound HTH29.
Example 9
[0784] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound 138 was used instead of Compound 3, and Compound ETH68 and Compound HTH29 were used instead of Compound ETH2 and Compound HTH29.
Example 10
[0785] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound 176 was used instead of Compound 3, and Compound ETH2 and Compound HTH41 were used instead of Compound ETH2 and Compound HTH29.
Example 11
[0786] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound 33 was used instead of Compound 3, Compound ETH2 and Compound HTH41 were used instead of Compound ETH2 and Compound HTH29, and Compound DFD1 was additionally used to form an emission layer.
Example 12
[0787] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound 73 was used instead of Compound 3, Compound ETH68 and Compound HTH29 were used instead of Compound ETH2 and Compound HTH29, and Compound DFD2 was additionally used to form an emission layer.
Comparative Example 1
[0788] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound CE1 was used instead of Compound 3, and Compound ETH2 alone was used instead of Compound ETH2 and Compound HTH29 to form an emission layer having a thickness of 300 Å.
Comparative Example 2
[0789] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound CE2 was used instead of Compound 3, and Compound ETH2 alone was used instead of Compound ETH2 and Compound HTH29 to form an emission layer having a thickness of 300 Å.
Comparative Example 3
[0790] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound CE3 was used instead of Compound 3, and Compound ETH2 alone was used instead of Compound ETH2 and Compound HTH29 to form an emission layer having a thickness of 300 Å.
Comparative Example 4
[0791] An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, Compound CE4 was used instead of Compound 3, and Compound ETH2 alone was used instead of Compound ETH2 and Compound HTH29 to form an emission layer having a thickness of 300 Å.
Evaluation Example 1
[0792] The driving voltage (V) at 1,000 cd/n.sup.2, color purity (CIEx,y), luminescence efficiency (cd/A), color conversion efficiency (cd/Ay), maximum emission wavelength (nm), and lifespan (T.sub.95) of the organic light-emitting devices manufactured according to Examples 1 to 12 and Comparative Examples 1 to 4 were each measured by using a Keithley MU 236 and a luminance meter PR650, and results thereof are shown in Table 2. In Table 2, the lifespan (T.sub.95) is a measure of the time taken when the luminance reaches 95% of the initial luminance.
TABLE-US-00002 TABLE 2 Color Maximum Driving conversion emission Lifespan Dopant Host Luminance Voltage Efficiency efficiency wavelength of device compound compound (cd/m.sup.2) (V) CIE.sub.(x, y) (cd/A) (cd/A/y) (nm) (T.sub.95, h) Example 1 3 ETH2/HTH29 1000 4.3 (0.14, 0.16) 16.2 105.5 461 35.3 Example 2 3 ETH68/HTH41 1000 4.2 (0.14, 0.16) 16.5 107.1 461 34.6 Example 3 26 ETH2/HTH41 1000 4.4 (0.14, 0.17) 16.4 97.7 464 79.3 Example 4 33 ETH68/HTH29 1000 4.6 (0.14, 0.16) 20.4 128.4 463 102.7 Example 5 73 ETH68/HTH29 1000 4.5 (0.14, 0.17) 19.8 120.3 465 85.2 Example 6 87 ETH68/HTH29 1000 4.4 (0.14, 0.16) 19.2 120.5 464 76.3 Example 7 100 ETH2/HTH41 1000 4.2 (0.14, 0.13) 13.5 129.4 454 15.6 Example 8 122 ETH68/HTH29 1000 4.3 (0.14, 0.14) 18.4 132.1 457 40.4 Example 9 138 ETH68/HTH29 1000 4.3 (0.14, 0.14) 13.2 95.3 458 18.1 Example 10 176 ETH2/HTH41 1000 4.2 (0.14, 0.13) 18.1 139.8 456 38.8 Example 11 33/DFD1 ETH2/HTH41 1000 4.2 (0.14, 0.15) 22.3 149.5 461 92.3 Example 12 73/DFD2 ETH68/HTH29 1000 4.1 (0.14, 0.15) 19.8 133.1 462 88.5 Comparative CE1 ETH2 1000 4.4 (0.14, 0.19) 9.6 51.6 454 2.5 Example 1 Comparative CE2 ETH2 1000 5.1 (0.35, 0.60) 38.5 64.3 543 10 Example 2 Comparative CE3 ETH2 1000 5.3 (0.36, 0.58) 33.8 58.6 548 8.4 Example 3 Comparative CE4 ETH2 1000 4.5 (0.15, 0.18) 10.1 56.1 460 4.5 Example 4
##STR00269## ##STR00270## ##STR00271##
[0793] From Table 2, it was confirmed that the organic light-emitting devices according to Examples 1 to 12 had superior driving voltage, luminescence efficiency, color conversion efficiency, and lifespan characteristics to those of the organic light-emitting devices according to Comparative Examples 1 to 4.
[0794] According to the one or more embodiments, the use of the organometallic compound may enable the manufacture of a light-emitting device having high efficiency and a long lifespan and a high-quality electronic apparatus including the light-emitting device.
[0795] It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.