ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME, AND ELECTRONIC APPARATUS INCLUDING ORGANIC LIGHT-EMITTING DEVICE

Abstract

An organometallic compound, represented by Formula 1:

M.sub.1(L.sub.1).sub.n1(Ln.sub.2).sub.n2 Formula 1

wherein M.sub.1 is a transition metal, Ln.sub.1 is a ligand represented by Formula 1-1, Ln.sub.2 is a ligand represented by Formula 2-1 or Formula 2-2, n1 is 1 or 2, and n2 is 1 or 2:

##STR00001##

wherein CY.sub.11, CY.sub.12, X.sub.31, X.sub.32, R.sub.10A, R.sub.10B, R.sub.21 to R.sub.28, R.sub.31 to R.sub.37, R.sub.41 to R.sub.44, b11, and b12 are as defined herein, and * and *′ each indicate a binding site to M.sub.1.

Claims

1. An organometallic, compound represented by Formula 1:
M.sub.1(Ln.sub.1).sub.n1(Ln.sub.2).sub.n2 Formula 1 wherein, in Formula 1, M.sub.1 is a transition metal, Ln.sub.1 is a ligand represented by Formula 1-1, Ln.sub.2 is a ligand represented by Formula 2-1 or Formula 2-2, n1 is 1 or 2, and n2 is 1 or 2, ##STR00106## wherein, in Formulae 1-1, 2-1, and 2-2, CY.sub.11 is a 5-membered carbocyclic group or a 5-membered heterocyclic group, CY.sub.12 is a 6-membered heterocyclic group, X.sub.31 and X.sub.32 are each independently O or S, R.sub.10A, R.sub.10B, R.sub.21 to R.sub.28, R.sub.31 to R.sub.37, and R.sub.41 to R.sub.44 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.1-C.sub.60 alkylthio group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.2-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 alkyl aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 aryl alkyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkyl heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 heteroaryl alkyl group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryloxy group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —Ge(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.4)(Q.sub.5), —B(Q.sub.6)(Q.sub.7), —P(Q.sub.8)(Q.sub.9), or —P(═O)(Q.sub.8)(Q.sub.9), two or more of R.sub.10A are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group, two or more of R.sub.10B are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group, two or more of R.sub.21 to R.sub.28 are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group, two or more of R.sub.31 to R.sub.37 are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group, two or more of R.sub.41 to R.sub.44 are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group, neighboring two or more of R.sub.10A, R.sub.10B, R.sub.21 to R.sub.28, R.sub.31 to R.sub.37, and R.sub.41 to R.sub.44 are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group, b11 is 1, 2, 3, or 4, b12 is 1, 2, 3, or 4, and *′ each indicate a binding site to M.sub.1, and at least one substituent of the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.1-C.sub.60 alkylthio group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.1-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.1-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted C.sub.7-C.sub.60 alkyl aryl group, the substituted C.sub.7-C.sub.60 aryl alkyl group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted C.sub.1-C.sub.60 heteroaryl group, the substituted C.sub.2-C.sub.60 alkyl heteroaryl group, the substituted C.sub.2-C.sub.60 heteroaryl alkyl group, the substituted C.sub.1-C.sub.60 heteroaryloxy group, the substituted C.sub.1-C.sub.60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, the substituted monovalent non-aromatic condensed heteropolycyclic group, the substituted C.sub.5-C.sub.30 carbocyclic group, and the substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group is: deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —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, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.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.1-C.sub.60 alkylthio 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.1-C.sub.60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —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, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.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.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —Ge(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.14)(Q.sub.15), —B(Q.sub.16)(Q.sub.17), —P(Q.sub.18)(Q.sub.19), —P(═O)(Q.sub.18)(Q.sub.19), or a combination thereof; 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.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group; 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.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —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, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.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.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.7-C.sub.60 alkyl aryl group, a C.sub.7-C.sub.60 aryl alkyl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.2-C.sub.60 heteroaryl alkyl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q.sub.21)(Q.sub.22)(Q.sub.23), —Ge(Q.sub.21)(Q.sub.22)(Q.sub.23), —N(Q.sub.24)(Q.sub.25), —B(Q.sub.26)(Q.sub.27), —P(Q.sub.28)(Q.sub.29), —P(═O)(Q.sub.28)(Q.sub.29), or a combination thereof; or —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —Ge(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.34)(Q.sub.35), —B(Q.sub.36)(Q.sub.37), —P(Q.sub.38)(Q.sub.39), or —P(═O)(Q.sub.38)(Q.sub.39), wherein Q.sub.1 to Q.sub.9, Q.sub.11 to Q.sub.19, Q.sub.21 to Q.sub.29, and Q.sub.31 to Q.sub.39 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.1-C.sub.60 alkylthio group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 alkyl aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 aryl alkyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkyl heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 heteroaryl alkyl group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryloxy group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

2. The organometallic compound of claim 1, wherein M.sub.1 is iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

3. The organometallic compound of claim 1, wherein M.sub.1 is Ir, and the sum of n1 and n2 is 3.

4. The organometallic compound of claim 1, wherein CY.sub.11 is a cyclopentadiene group, a furan group, a thiophene group, a selenophene, a 1H-pyrrole 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, or a thiadiazole group, and CY.sub.12 is a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

5. The organometallic compound of claim 1, wherein each Ln.sub.1 is independently represented by Formula 1A or 11B: ##STR00107## wherein, in Formulae 1A and 1B, CY.sub.11, and R.sub.21 to R.sub.28 are as defined in claim 1, X.sub.11 is C(R.sub.11) or N, X.sub.12 is C(R.sub.12) or N, R.sub.11 and R.sub.12 are each as defined in connection with R.sub.10A in claim 1, and and *′ each indicate a binding site to M.sub.1.

6. The organometallic compound of claim 1, wherein each Ln.sub.1 is independently represented by Formula 1A-1, 1A-2, 1B-1, or 11B-2: ##STR00108## wherein, in Formulae 1A-1, 1A-2, 1B3-1, and 1B3-2, R.sub.21 to R.sub.28 are as defined in claim 1, X.sub.11 is C(R.sub.11) or N, X.sub.12 is C(R.sub.12) or N, X.sub.13 is C(R.sub.13) or N, and X.sub.14 is C(R.sub.14) or N, X.sub.1 is O, S, Se, N(R.sub.15), or C(R.sub.15)(R.sub.16), R.sub.11 to R.sub.16 are each independently as defined in connection with R.sub.10A in claim 1, and and *′ each indicate a binding site to M.sub.1.

7. The organometallic compound of claim 1, wherein each Ln.sub.1 is independently represented by Formula 11-1, 11-2, 11-3, or 11-4: ##STR00109## wherein, in Formulae 11-1 to 11-4, R.sub.21 to R.sub.28 are as defined in claim 1, X.sub.1 is O, S, Se, N(R.sub.15), or C(R.sub.15)(R.sub.16), R.sub.11 to R.sub.16 are each independently as defined in connection with R.sub.10A in claim 1, and and *′ each indicate a binding site to M.sub.1.

8. The organometallic compound of claim 1, wherein each Ln.sub.2 is independently represented by Formula 21-1, 21-2, 21-3, or 21-4: ##STR00110## wherein, in Formulae 21-1 to 21-4, R.sub.31 to R.sub.37 are as defined in claim 1, and and *′ each indicate a binding site to M.sub.1.

9. The organometallic compound of claim 1, wherein each Ln.sub.2 is represented by one of Formulae 22-1 to 22-16: ##STR00111## ##STR00112## ##STR00113## wherein, in Formulae 22-1 to 22-16, R.sub.41 to R.sub.44 are as defined in claim 1, provided that none of R.sub.41 to R.sub.44 is hydrogen, and and *′ each indicate a binding site to M.sub.1.

10. The organometallic compound of claim 1, wherein R.sub.10A, R.sub.10B, R.sub.21 to R.sub.28, R.sub.31 to R.sub.37, and R.sub.41 to R.sub.44 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, 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.1-C.sub.60 alkylthio group, —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), or —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), or a group represented by one of Formulae 9-1 to 9-67, 9-201 to 9-244, 10-1 to 10-154, or 10-201 to 10-350: ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## wherein, in Formulae 9-1 to 9-67, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350, * indicates a binding site to a neighboring atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group.

11. The organometallic compound of claim 1, wherein R.sub.31 to R.sub.37 are each independently hydrogen, deuterium, a methyl group, an ethyl group, 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 2-methylbutyl group, a sec-pentyl group, a tert-pentyl group, a neo-pentyl group, a 3-pentyl group, or a 3-methyl-2-butyl group.

12. The organometallic compound of claim 1, wherein R.sub.41 to R.sub.44 are each independently hydrogen, deuterium, a methyl group, an ethyl group, 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, an isopentyl group, a 2-methylbutyl group, a sec-pentyl group, a tert-pentyl group, a neo-pentyl group, a 3-pentyl group, a 3-methyl-2-butyl group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.20 alkylphenyl group, or a naphthyl group.

13. The organometallic compound of claim 1, wherein the organometallic compound is a compound represented by one of Formulae 31-1 to 31-8: ##STR00159## ##STR00160## ##STR00161## wherein, in Formulae 31-1 to 31-8, M.sub.1, n1, n2, R.sub.21 to R.sub.28, R.sub.31 to R.sub.37, and R.sub.41 to R.sub.44 are as defined in claim 1, X.sub.1 is O, S, Se, N(R.sub.15), or C(R.sub.15)(R.sub.16), and R.sub.11 to R.sub.16 are each independently as defined in connection with R.sub.10 in claim 1.

14. The organometallic compound of claim 1, wherein the organometallic compound is electrically neutral.

15. The organometallic compound of claim 1, wherein the organometallic compound is one or more of Compounds 1 to 32: ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169##

16. An organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, and wherein the organic layer further comprises at least one of the organometallic compound of claim 1.

17. The light-emitting device of claim 16, wherein the emission layer comprises the at least one organometallic compound.

18. The organic light-emitting device of claim 17, wherein the emission layer further comprises a host, and an amount of the host in the emission layer is greater than an amount of the organometallic compound in the emission layer.

19. The light-emitting device of claim 16, wherein the first electrode is an anode, the second electrode is a cathode, the organic layer 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 electron blocking layer, a buffer 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.

20. An electronic apparatus, comprising the organic light-emitting device of claim 16.

Description

DETAILED DESCRIPTION

[0035] Reference will now be made in further detail to exemplary embodiments, examples of which are illustrated in the accompanying drawing, wherein like reference numerals refer to like elements throughout the specification. In this regard, the present exemplary embodiments may have different forms and should not be construed as being limited to the detailed descriptions set forth herein. Accordingly, the exemplary embodiments are merely described in further detail below, by referring to the FIGURE, to explain one or more aspects. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

[0036] The terminology used herein is for the purpose of describing one or more exemplary embodiments only and is not intended to be limiting. As used herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. The term “or” means “and/or.” It will be further understood that the terms “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.

[0037] It will be understood that, although the terms first, second, third etc. may be used herein to describe various elements, components, regions, layers, and/or sections, these elements, components, regions, layers, and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer, or section from another element, component, region, layer, or section. Thus, a first element, component, region, layer, or section discussed below could be termed a second element, component, region, layer, or section without departing from the teachings of the present embodiments.

[0038] Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.

[0039] It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.

[0040] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

[0041] “About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

[0042] An aspect of the present disclosure provides an organometallic compound represented by Formula 1:

M.sub.1(Ln.sub.1).sub.n1(Ln.sub.2).sub.n2 Formula 1

wherein M.sub.1 in Formula 1 is a transition metal.

[0043] In one or more embodiments, M.sub.1 in Formula 1 may be a fourth-row transition metal of the Periodic Table of Elements, a fifth-row transition metal of the Periodic Table of Elements, or a sixth-row transition metal of the Periodic Table of Elements.

[0044] In one or more embodiments, M.sub.1 may be iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0045] For example, M.sub.1 may be Ir, Os, Pt, Pd, or Au.

[0046] In one or more embodiments, M.sub.1 may be Ir.

[0047] In Formula 1, n1 is 1 or 2.

[0048] In Formula 1, n2 is 1 or 2.

[0049] In one or more embodiments, M.sub.1 may be Ir, and the sum of n1 and n2 may be 3.

[0050] Ln.sub.1 in Formula 1 is a ligand represented by Formula 1-1:

##STR00003##

wherein * and *′ each indicate a binding site to M.sub.1.

[0051] A bond between *—N moiety in Formula 1-1 and M.sub.1 in Formula 1 is a coordinate bond.

[0052] A bond between *′-C in Formula 1 and M.sub.1 in Formula is a covalent bond.

[0053] CY.sub.11 in Formula 1-1 is a 5-membered carbocyclic group or a 5-membered heterocyclic group.

[0054] In one or more embodiments, CY.sub.11 may be a cyclopentadiene group, a furan group, a thiophene group, a selenophene, a 1H-pyrrole 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, or a thiadiazole group.

[0055] CY.sub.12 in Formula 1-1 is a 6-membered heterocyclic group.

[0056] In one or more embodiments, CY.sub.12 may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0057] In Formula 1-1, two or more of R.sub.10A are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group; two or more of R.sub.10B are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group; and two or more of R.sub.21 to R.sub.28 are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group.

[0058] In one or more embodiments, each Ln.sub.1 may independently be represented by Formula 1A or 11B:

##STR00004##

[0059] wherein, in Formulae 1A and 1B,

[0060] CY.sub.11, R.sub.21 to R.sub.28 are as described above,

[0061] X.sub.11 may be C(R.sub.11) or N, X.sub.12 may be C(R.sub.12) or N,

[0062] R.sub.11 and R.sub.12 may each independently be as described in connection with R.sub.10, and

[0063] * and *′ each indicate a binding site to M.sub.1.

[0064] In one or more embodiments, each Ln.sub.1 may independently be represented by Formula 1A-1, 1A-2, 1B-1, or 1B-2:

##STR00005##

wherein, in Formulae 1A-1, 1A-2, 1B-1, and 1B-2,

[0065] R.sub.21 to R.sub.28 are as described above,

[0066] X.sub.11 may be C(R.sub.11) or N, X.sub.12 may be C(R.sub.12) or N, X.sub.13 may be C(R.sub.13) or N, and X.sub.14 may be C(R.sub.14) or N,

[0067] X.sub.1 may be O, S, Se, N(R.sub.15), or C(R.sub.15)(R.sub.16),

[0068] R.sub.11 to R.sub.16 may respectively be as described in connection with R.sub.10, and

[0069] * and *′ each indicate a binding site to M.sub.1.

[0070] In one or more embodiments, each Ln.sub.1 may independently be represented by Formula 11-1, 11-2, 11-3, or 11-4:

##STR00006##

wherein, in Formulae 11-1 to 11-4,

[0071] R.sub.21 to R.sub.28 are as described herein,

[0072] X.sub.1 may be O, S, Se, N(R.sub.15), or C(R.sub.15)(R.sub.16),

[0073] R.sub.11 to R.sub.16 may respectively be as described in connection with R.sub.10, and

[0074] * and *′ each indicate a binding site to M.sub.1.

[0075] Ln.sub.2 is a ligand represented by Formula 2-1 or 2-2:

##STR00007##

wherein * and *′ each indicate a binding site to M.sub.1.

[0076] A bond between *—X.sub.31 moiety in Formula 2-1 and M.sub.1 in Formula 1 is a coordinate bond.

[0077] A bond between *—X.sub.32 moiety in Formula 2-1 and M.sub.1 in Formula 1 is a covalent bond.

[0078] A bond between *—O moiety in Formula 2-2 and M.sub.1 in Formula 1 is a covalent bond.

[0079] A bond between *—N moiety in Formula 2-2 and M.sub.1 in Formula 1 is a coordinate bond.

[0080] X.sub.31 and X.sub.32 in Formula 2-1 are each independently O or S.

[0081] In Formulae 2-1, two or more of R.sub.31 to R.sub.37 are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group. In Formula 2-2, two or more of R.sub.41 to R.sub.44 are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group.

[0082] In one or more embodiments, each Ln.sub.2 may independently be represented by one of Formulae 21-1 to 21-4:

##STR00008##

wherein, in Formulae 21-1 to 21-4,

[0083] R.sub.31 to R.sub.37 are as described herein, and

[0084] * and *′ each indicate a binding site to M.sub.1.

[0085] In one or more embodiments, each Ln.sub.2 may independently be represented by one of Formulae 22-1 to 22-16:

##STR00009## ##STR00010## ##STR00011##

wherein, in Formulae 22-1 to 22-16,

[0086] R.sub.41 to R.sub.44 are as described herein, provided that none of R.sub.41 to R.sub.44 may be hydrogen, and

[0087] * and *′ each indicate a binding site to M.sub.1.

[0088] In one or more embodiments, in Formulae 1-1, 2-1, and 2-2, R.sub.10A, R.sub.10B, R.sub.21 to R.sub.28, R.sub.31 to R.sub.37, and R.sub.41 to R.sub.44 are each independently

[0089] hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.1-C.sub.60 alkylthio group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.2-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 alkyl aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 aryl alkyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkyl heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 heteroaryl alkyl group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryloxy group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.4)(Q.sub.5), —B(Q.sub.6)(Q.sub.7), —P(Q.sub.8)(Q.sub.9), or —P(═O)(Q.sub.8)(Q.sub.9).

[0090] In one or more embodiments, R.sub.10A, R.sub.10B, R.sub.21 to R.sub.28, R.sub.31 to R.sub.37, and R.sub.41 to R.sub.44 may each independently be

[0091] hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.2-C.sub.20 alkenyl group, a C.sub.1-C.sub.20 alkoxy group, or a C.sub.1-C.sub.20 alkylthio group;

[0092] a C.sub.1-C.sub.20 alkyl group, a C.sub.2-C.sub.20 alkenyl group, a C.sub.1-C.sub.20 alkoxy group, or a C.sub.1-C.sub.20 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —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, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.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 bicyclo[2.2.1]heptyl group), a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C.sub.1-C.sub.20 alkyl)cyclopentyl group, a (C.sub.1-C.sub.20 alkyl)cyclohexyl group, a (C.sub.1-C.sub.20 alkyl)cycloheptyl group, a (C.sub.1-C.sub.20 alkyl)cyclooctyl group, a (C.sub.1-C.sub.20 alkyl)adamantanyl group, a (C.sub.1-C.sub.20 alkyl)norbornanyl group, a (C.sub.1-C.sub.20 alkyl)norbornenyl group, a (C.sub.1-C.sub.20 alkyl)cyclopentenyl group, a (C.sub.1-C.sub.20 alkyl)cyclohexenyl group, a (C.sub.1-C.sub.20 alkyl)cycloheptenyl group, a (C.sub.1-C.sub.20 alkyl)bicyclo[1.1.1]pentyl group, a (C.sub.1-C.sub.20 alkyl)bicyclo[2.1.1]hexyl group, a (C.sub.1-C.sub.20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C.sub.1-C.sub.20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or a combination thereof,

[0093] 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 bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C.sub.1-C.sub.20 alkyl)phenyl group, a biphenyl group, a terphenyl 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 or azadibenzothiophenyl group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —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, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.20 alkyl group, a deuterated C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20alkoxy group, a C.sub.1-C.sub.20 alkylthio 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 bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C.sub.1-C.sub.20 alkyl)cyclopentyl group, a (C.sub.1-C.sub.20 alkyl)cyclohexyl group, a (C.sub.1-C.sub.20 alkyl)cycloheptyl group, a (C.sub.1-C.sub.20 alkyl)cyclooctyl group, a (C.sub.1-C.sub.20 alkyl)adamantanyl group, a (C.sub.1-C.sub.20 alkyl)norbornanyl group, a (C.sub.1-C.sub.20 alkyl)norbornenyl group, a (C.sub.1-C.sub.20 alkyl)cyclopentenyl group, a (C.sub.1-C.sub.20 alkyl)cyclohexenyl group, a (C.sub.1-C.sub.20 alkyl)cycloheptenyl group, a (C.sub.1-C.sub.20 alkyl)bicyclo[1.1.1]pentyl group, a (C.sub.1-C.sub.20 alkyl)bicyclo[2.1.1]hexyl group, a (C.sub.1-C.sub.20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C.sub.1-C.sub.20 alkyl)phenyl group, a biphenyl group, a terphenyl 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, or a combination thereof; or

[0094] —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.4)(Q.sub.5), —B(Q.sub.6)(Q.sub.7), —P(Q.sub.8)(Q.sub.9), or —P(═O)(Q.sub.8)(Q.sub.9),

[0095] wherein Q.sub.1 to Q.sub.9 may each independently be:

[0096] deuterium, —F, —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, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, —CH.sub.2CF.sub.3, —CH.sub.2CF.sub.2H, —CH.sub.2CFH.sub.2, —CHFCH.sub.3, —CHFCF.sub.2H, —CHFCFH.sub.2, —CHFCF.sub.3, —CF.sub.2CF.sub.3, —CF.sub.2CF.sub.2H, or —CF.sub.2CFH.sub.2; or

[0097] 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, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with at least one of deuterium, —F, a C.sub.1-C.sub.10 alkyl group, a phenyl group, or a combination thereof.

[0098] In one or more embodiments, R.sub.10A, R.sub.10B, R.sub.21 to R.sub.28, R.sub.31 to R.sub.37, and R.sub.41 to R.sub.44 may each independently be

[0099] hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —CD.sub.3, —CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, 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.1-C.sub.60 alkylthio group; or

[0100] a group represented by one of Formulae 9-1 to 9-67, 9-201 to 9-244, 10-1 to 10-154, or 10-201 to 10-350:

##STR00012## ##STR00013## ##STR00014## ##STR00015## ##STR00016## ##STR00017## ##STR00018## ##STR00019## ##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037##

##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058##

[0101] wherein, in Formulae 9-1 to 9-67, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350, * indicates a binding site to a neighboring atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group.

[0102] In one or more embodiments, R.sub.10A, R.sub.10B, R.sub.21 to R.sub.28, R.sub.31 to R.sub.37, and R.sub.41 to R.sub.44 may each independently be hydrogen, deuterium, a methyl group, an ethyl group, 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 2-methylbutyl group, a sec-pentyl group, a tert-pentyl group, a neo-pentyl group, a 3-pentyl group, a 3-methyl-2-butyl group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.20 alkylphenyl group, or a naphthyl group.

[0103] In one or more embodiments, R.sub.10A, R.sub.10B, and R.sub.21 to R.sub.28 may each independently be hydrogen, a C.sub.1-C.sub.60 alkyl group, a C.sub.1-C.sub.60 aryl group, —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), or —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3).

[0104] In one or more embodiments, R.sub.31 to R.sub.37 may each independently be hydrogen, deuterium, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a 2-methylbutyl group, a sec-pentyl group, a tert-pentyl group, a neo-pentyl group, a 3-pentyl group, or a 3-methyl-2-butyl group.

[0105] In one or more embodiments, R.sub.41 to R.sub.44 may each independently be hydrogen, deuterium, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a 2-methylbutyl group, a sec-pentyl group, a tert-pentyl group, a neo-pentyl group, a 3-pentyl group, a 3-methyl-2-butyl group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.20 alkylphenyl group, or a naphthyl group.

[0106] When b11 is 2 or greater, each R.sub.10A may be identical to or different from each other, when b12 is 2 or greater, each R.sub.10B may be identical to or different from each other, and when b20 is 2 or greater, each R.sub.20 may be identical to or different from each other.

[0107] Regarding Formula 1-1, two or more of R.sub.10A are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group; two or more of R.sub.10B are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group; and neighboring two or more of R.sub.10A, R.sub.10B, R.sub.21 to R.sub.28, R.sub.31 to R.sub.37, and R.sub.41 to R.sub.44 are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group.

[0108] Regarding Formula 2-1 and 2-2, two or more of R.sub.21 to R.sub.28 are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group; two or more of R.sub.31 to R.sub.37 are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group, two or more of R.sub.41 to R.sub.44 are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group, and neighboring two or more of R.sub.10A, R.sub.10B, R.sub.21 to R.sub.28, R.sub.31 to R.sub.37, and R.sub.41 to R.sub.44 are optionally bonded to each other to form a substituted or unsubstituted C.sub.5-C.sub.30 carbocyclic group or a substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group

[0109] In one or more embodiments, two or more of a plurality of R.sub.10A; two or more of a plurality of R.sub.10B; or neighboring two or more of R.sub.10A, R.sub.10B, R.sub.21 to R.sub.28, R.sub.31 to R.sub.37, and R.sub.41 to R.sub.44 may optionally be bonded to each other via a single bond, a double bond, or a first linking group to form a C.sub.5-C.sub.30 carbocyclic group unsubstituted or substituted with at least one R.sub.10C, or a C.sub.1-C.sub.30 heterocyclic group unsubstituted or substituted with at least one R.sub.10C (for example, a fluorene group, a xanthene group, or an acridine group, unsubstituted or substituted with at least one R.sub.10C). R.sub.10C may be as described in connection with R.sub.10A.

[0110] The first linking group may be one or more of *—N(R.sub.8)—*′, *—B(R.sub.8)—*′, *—P(R.sub.8)—*′, *—C(R.sub.8)(R.sub.9)—*′, *—Si(R.sub.8)(R.sub.9)—*′, *—Ge(R.sub.8)(R.sub.9)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O).sub.2—*′, *—C(R.sub.8)=*′, *═C(R.sub.8)—*′, *—C(R.sub.8)═C(R.sub.9)—*′, *—C(═S)—*′, *—C≡C—*′, or a combination thereof, R.sub.8 and R.sub.9 are as described in connection with R.sub.10, and each of * and *′ indicates a binding site to a neighboring atom.

[0111] In one or more embodiments, the organometallic compound may be a compound represented by one or more of Formulae 31-1 to 31-8:

##STR00059## ##STR00060## ##STR00061##

wherein, in Formulae 31-1 to 31-8,

[0112] M.sub.1, n1, n2, R.sub.21 to R.sub.28, R.sub.31 to R.sub.37, and R.sub.41 to R.sub.44 are as described herein,

[0113] X.sub.1 is O, S, Se, N(R.sub.15), or C(R.sub.15)(R.sub.16),

[0114] R.sub.11 to R.sub.16 are respectively be as described in connection with R.sub.10A.

[0115] In one or more embodiments, the organometallic compound may be electrically neutral.

[0116] In one or more embodiments, the organometallic compound may be one or more of Compounds 1 to 32:

##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068## ##STR00069##

[0117] The organometallic compound represented by Formula 1 may satisfy the structure of Formula 1. In one or more embodiments, the ligand represented by Formula 1-1 has a lowest unoccupied molecular orbital (LUMO) ring having a structure in which a 5-membered ring represented by CY.sub.11 is condensed with a 6-membered ring represented by CY.sub.12, and a highest occupied molecular orbital (HOMO) ring having a phenanthrene structure, resulting in a long conjugation structure. Accordingly, the stability of the molecule and the optical alignment thereof can be improved. In one or more embodiments, the organometallic compound may include a ligand represented by Formula 2-1 or 2-2. Without wishing to be bound to theory, because of this structure, an electronic device, for example, an organic light-emitting device, including the organometallic compound represented by Formula 1 may exhibit low driving voltage, high efficiency, and long lifespan, and narrower full width at half maximum (FWHM).

[0118] The HOMO energy level, LUMO energy level, lowest singlet (S.sub.1) energy level, and lowest triplet (T.sub.1) energy level of organometallic compound represented by Formula 1 were evaluated by density functional theory (DFT) using the Gaussian 09 program with the molecular structure optimization obtained at the B3LYP level, and results thereof are shown in Table 1 (where energies are provided in electron Volts (eV).

TABLE-US-00001 TABLE 1 Compound HOMO LUMO S.sub.1 T.sub.1 structure (eV) (eV) (eV) (eV) Compound 1 −4.582 −1.582 2.370 1.968 Compound 11 −4.647 −1.750 2.380 1.947 Compound 12 −4.695 −1.759 2.384 1.954 Compound 2 −4.550 −1.575 2.350 1.959

##STR00070##

[0119] From Table 1, it was confirmed that the organometallic compound represented by Formula 1 has such electric characteristics that are suitable for use as a dopant for an electronic device, for example, an organic light-emitting device.

[0120] In one or more embodiments, the FWHM of the emission peak of the emission spectrum or the electroluminescence spectrum of the organometallic compound may be about 75 nanometers (nm) or less, such as 75 nm or less. For example, the FWHM of the emission peak of the emission spectrum or the electroluminescence (EL) spectrum of the organometallic compound may be from about 30 nm to about 75 nm, from about 40 nm to about 70 nm, or from about 45 nm to about 68 nm.

[0121] In one or more embodiments, a maximum emission wavelength (also referred to as an emission peak wavelength maximum, Amax) of an emission peak of an emission spectrum or an EL spectrum of the organometallic compound may be in a range of about 600 nm to about 750 nm.

[0122] Synthesis methods of the organometallic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples provided herein.

[0123] The organometallic compound represented by Formula 1 is suitable for use in an organic layer of an organic light-emitting device, for example, for use as a dopant in an emission layer of the organic layer. Thus, another aspect provides an organic light-emitting device that includes: a first electrode; a second electrode; and an organic layer that is located between the first electrode and the second electrode and includes an organic layer including an emission layer and at least one of the organometallic compounds represented by Formula 1.

[0124] Since the organic light-emitting device has an organic layer containing the organometallic compound represented by Formula 1 as described above, excellent characteristics may be obtained with respect to driving voltage, current efficiency, external quantum efficiency, a roll-off ratio, and lifespan, and the FWHM of the emission peak of the EL spectrum is relatively narrow.

[0125] The organometallic compound of Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by Formula 1 may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the organometallic compound represented by Formula 1 in the emission layer is smaller than an amount of the host).

[0126] In one embodiment, the emission layer may emit red light. For example, the emission layer may emit red light having a maximum emission wavelength in a range of about 600 nm to about 750 nm.

[0127] The expression “(an organic layer) includes at least one of the organometallic compounds” used herein may include a case in which “(an organic layer) includes identical organometallic compounds represented by Formula 1” and a case in which “(an organic layer) includes two or more different organometallic compounds represented by Formula 1.”

[0128] For example, the organic layer may include, as the organometallic compound, only Compound 1. In this embodiment, Compound 1 may be included in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include, as the organometallic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may exist in an identical layer (for example, Compound 1 and Compound 2 all may exist in an emission layer).

[0129] The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.

[0130] In one or more embodiments, in the organic light-emitting device, the first electrode is an anode, and the second electrode is a cathode, and the organic layer 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, and the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0131] The term “organic layer” used herein refers to a single layer and/or a plurality of layers located between the first electrode and the second electrode of the organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including a metal.

[0132] The FIGURE is a schematic cross-sectional view showing one or more aspects of an organic light-emitting device 10 according to one or more embodiments. Hereinafter, the structure and manufacturing method of the organic light-emitting device 10 according to one or more embodiments of the present disclosure will be described in connection with FIGURE. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.

[0133] A substrate may be additionally located under (or beneath) the first electrode 11 or above (or on top of) the second electrode 19. For use as the substrate, any suitable substrate that is used in organic light-emitting devices available in the art may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and/or water resistance.

[0134] In one or more embodiments, the first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO.sub.2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be metal, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).

[0135] The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 11 is not limited thereto.

[0136] The organic layer 15 may be located on the first electrode 11.

[0137] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

[0138] The hole transport region may be located between the first electrode 11 and the emission layer 15.

[0139] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.

[0140] The hole transport region may include only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, wherein, for each structure, respective layers are sequentially stacked in this stated order from the first electrode 11.

[0141] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (L-B) deposition.

[0142] When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature in a range of about 100° C. to about 500° C., a vacuum pressure in a range of about 10.sup.−8 torr to about 10.sup.−3 torr, and a deposition rate in a range of about 0.01 angstroms per second (Å/sec) to about 100 Å/sec. However, the deposition conditions are not limited thereto.

[0143] When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

[0144] The conditions for forming the hole transport layer and the electron blocking layer may be similar to (for example, the same as) the conditions for forming the hole injection layer.

[0145] The hole transport region may include at least one selected from m-MTDATA (4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N′-di(naphthalene-1-yl)-N,N′-diphenyl-benzidine (NPB), β-NPB, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (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), a compound represented by Formula 201 below, or a compound represented by Formula 202:

##STR00071## ##STR00072## ##STR00073## ##STR00074##

[0146] Ar.sub.101 and Ar.sub.102 in Formula 201 may each independently be:

[0147] a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group; or

[0148] a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.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.1-C.sub.60 alkylthio group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.7-C.sub.60 alkyl aryl group, a C.sub.7-C.sub.60 aryl alkyl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.2-C.sub.60 heteroaryl alkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof.

[0149] xa and xb in Formula 201 may each independently be an integer from 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.

[0150] R.sub.101 to R.sub.108, R.sub.111 to R.sub.119 and R.sub.121 to R.sub.124 in Formulae 201 and 202 may each independently be:

[0151] hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.10 alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, or the like), a C.sub.1-C.sub.10 alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, or the like), a C.sub.1-C.sub.10 alkylthio group;

[0152] a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, or a C.sub.1-C.sub.10 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a phosphoric acid group or a salt thereof;

[0153] a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group; or

[0154] a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, or a C.sub.1-C.sub.10 alkylthio group,

[0155] but embodiments of the present disclosure are not limited thereto.

[0156] R.sub.109 in Formula 201 may be:

[0157] a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group; and

[0158] a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a C.sub.1-C.sub.20 alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group.

[0159] According to one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A below, but embodiments of the present disclosure are not limited thereto:

##STR00075##

[0160] R.sub.101, R.sub.111, R.sub.112, and R.sub.109 in Formula 201A are each as described in the present specification.

[0161] For example, the compound represented by Formula 201, and the compound represented by Formula 202 may include one of compounds HT1 to HT20 illustrated below, but are not limited thereto:

##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082##

[0162] A thickness of the hole transport region may be in the range of about 100 angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, a thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 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.

[0163] The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.

[0164] The charge-generation material may be, for example, a p-dopant. The p-dopant may be one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto.

[0165] For example, non-limiting examples of the p-dopant are: a quinone derivative, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), and F6-TCNQ; a metal oxide, such as a tungsten oxide or a molybdenum oxide; or a cyano group-containing compound, such as Compounds HT-D1 or F12, but embodiments are not limited thereto:

##STR00083##

[0166] The hole transport region may include a buffer layer.

[0167] Also, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of a formed organic light-emitting device may be improved.

[0168] Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, L-B deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer although the deposition or coating conditions may vary according to a material that is used to form the hole transport layer.

[0169] Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be selected from materials for the hole transport region described above and materials for a host to be explained later. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be mCP, which will be explained later.

[0170] The emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1.

[0171] The host may include at least one selected from 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi), 3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), 9,10-di(naphthalene-2-yl)anthracene (ADN, also referred to as “DNA”), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP), TCP, mCP, Compound H50, OR Compound H51:

##STR00084##

[0172] In one or more embodiments, the host may include a compound represented by Formula 301:

##STR00085##

[0173] Ar.sub.111 and Ar.sub.112 in Formula 301 may each independently be:

[0174] a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group; or

[0175] a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group, each substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof.

[0176] Ar.sub.113 to Ar.sub.116 in Formula 301 may each independently be:

[0177] a C.sub.1-C.sub.10 alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, or a pyrenyl group; or

[0178] a phenyl group, a naphthyl group, a phenanthrenyl group, or a pyrenyl group, each substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof.

[0179] g, h, i, and j in Formula 301 may each independently be an integer from 0 to 4, and may be, for example, 0, 1, or 2.

[0180] Ar.sub.113 and Ar.sub.116 in Formula 301 may each independently be:

[0181] a C.sub.1-C.sub.10 alkyl group, substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof;

[0182] a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl, a phenanthrenyl group, or a fluorenyl group;

[0183] a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, or a fluorenyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.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.1-C.sub.60 alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, or a combination thereof, or

##STR00086##

[0184] but embodiments of the present disclosure are not limited thereto.

[0185] In one or more embodiments, the host may include a compound represented by Formula 302:

##STR00087##

[0186] Ar.sub.122 to Ar.sub.125 in Formula 302 are as described in detail in connection with Ar.sub.113 in Formula 301.

[0187] Ar.sub.126 and Ar.sub.127 in Formula 302 may each independently be a C.sub.1-C.sub.10 alkyl group (for example, a methyl group, an ethyl group, or a propyl group).

[0188] k and I in Formula 302 may each independently be an integer from 0 to 4. For example, k and I may be 0, 1, or 2.

[0189] When the organic light-emitting device 10 is a full-color organic light-emitting device 10, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit white light.

[0190] When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.

[0191] 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, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.

[0192] An electron transport region may be located on the emission layer.

[0193] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0194] For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, and the structure of the electron transport region is not limited thereto. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.

[0195] Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.

[0196] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), or bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (BAlq), but embodiments of the present disclosure are not limited thereto:

##STR00088##

[0197] A thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.

[0198] The electron transport layer may further include at least one selected from BCP, Bphen, tris(8-hydroxyquinolinato)aluminum (Alq.sub.3), BAIq, 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), and 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ):

##STR00089##

[0199] In one or more embodiments, the electron transport layer may include at least one of ET1 to ET25, but are not limited thereto:

##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098##

[0200] A thickness of the electron transport layer may be in the range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transporting characteristics without a substantial increase in driving voltage.

[0201] The electron transport layer may include a metal-containing material in addition to the material as described above.

[0202] The metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate, LiQ) or ET-D2:

##STR00099##

[0203] The electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode 19 thereinto.

[0204] The electron injection layer may include at least of LiF, NaCl, CsF, Li.sub.2O, or BaO.

[0205] A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the ranges described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.

[0206] The second electrode 19 is located on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the second electrode 19. In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0207] Hereinbefore, the organic light-emitting device has been described with reference to the FIGURE, but exemplary embodiments of the present disclosure are not limited thereto.

[0208] Another aspect provides a diagnostic composition including at least one organometallic compound represented by Formula 1.

[0209] The organometallic compound represented by Formula 1 provides high luminescent efficiency. Accordingly, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.

[0210] The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.

[0211] The term “C.sub.1-C.sub.60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, and a hexyl group. The term “C.sub.1-C.sub.6 alkylene group” as used herein refers to a divalent group having the same structure as the C.sub.1-C.sub.60 alkyl group.

[0212] The term “C.sub.1-C.sub.60 alkoxy group” 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.

[0213] The term “C.sub.1-C.sub.6 alkylthio group” used herein refers to a monovalent group represented by —SA.sub.101 (wherein A.sub.101 is the C.sub.1-C.sub.60 alkyl group).

[0214] The term “C.sub.2-C.sub.60 alkenyl group” as used herein refers to a hydrocarbon group formed by substituting 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.

[0215] The term “C.sub.2-C.sub.60 alkynyl group” as used herein refers to a hydrocarbon group formed by substituting 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.

[0216] The term “C.sub.3-C.sub.10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl 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.

[0217] The term “C.sub.1-C.sub.10 heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si, Se, Ge, and S as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof include 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.

[0218] The term “C.sub.3-C.sub.10 cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting 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.

[0219] The term “C.sub.1-C.sub.10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, P, Si, Se, Ge, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C.sub.1-C.sub.10 heterocycloalkenyl group are 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.

[0220] The term “C.sub.6-C.sub.60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 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 having 6 to 60 carbon atoms. Examples of the C.sub.6-C.sub.60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl 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 fused to each other.

[0221] The term “C.sub.7-C.sub.6 alkyl aryl group” as used herein refers to a C.sub.6-C.sub.60 aryl group substituted with at least one C.sub.1-C.sub.60 alkyl group. The term “C.sub.7-C.sub.60 aryl alkyl group” as used herein refers to a C.sub.1-C.sub.60 alkyl group substituted with at least one C.sub.6-C.sub.60 aryl group.

[0222] The term “C.sub.1-C.sub.6 heteroaryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and 1 to 60 carbon atoms. The term “C.sub.1-C.sub.6 heteroarylene group” as used herein refers to a divalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and 1 to 60 carbon 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, and an isoquinolinyl group. When the C.sub.6-C.sub.60 heteroaryl group and the C.sub.6-C.sub.60 heteroarylene group each include two or more rings, the rings may be fused to each other.

[0223] The term “C.sub.2-C.sub.60 alkyl heteroaryl group” as used herein refers to a C.sub.1-C.sub.60 heteroaryl group substituted with at least one C.sub.1-C.sub.60 alkyl group. The term “C.sub.2-C.sub.60 heteroaryl alkyl group” as used herein refers to a C.sub.1-C.sub.60 alkyl group substituted with at least one C.sub.1-C.sub.60 heteroaryl group.

[0224] 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).

[0225] The term “C.sub.1-C.sub.60 heteroaryloxy group” as used herein indicates —OA.sub.102, (wherein A.sub.102, is a C.sub.1-C.sub.60 heteroaryl group), and the term “C.sub.1-C.sub.60 heteroarylthio group” as used herein indicates —SA.sub.103 (wherein A.sub.103 is a C.sub.1-C.sub.60 heteroaryl group).

[0226] 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 a fluorenyl 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.

[0227] The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 2 to 60 carbon atoms) having two or more rings condensed with each other, a heteroatom selected from N, O, P, Si, Se, Ge, and S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl 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.

[0228] The term “C.sub.5-C.sub.30 carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C.sub.5-C.sub.30 carbocyclic group may be a monocyclic group or a polycyclic group.

[0229] The term “C.sub.1-C.sub.30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, Se, Ge, and S other than 1 to 30 carbon atoms. The C.sub.1-C.sub.30 heterocyclic group may be a monocyclic group or a polycyclic group.

[0230] At least one substituent of the substituted C.sub.5-C.sub.30 carbocyclic group, the substituted C.sub.1-C.sub.30 heterocyclic group, the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.1-C.sub.60 alkylthio group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.1-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.1-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted C.sub.7-C.sub.60 alkyl aryl group, the substituted C.sub.7-C.sub.60 aryl alkyl group, the substituted C.sub.7-C.sub.60 alkylaryl group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted C.sub.1-C.sub.60 heteroaryl group, the substituted C.sub.2-C.sub.60 alkyl heteroaryl group, the substituted C.sub.2-C.sub.60 heteroaryl alkyl group, the substituted C.sub.2-C.sub.60 alkyl heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, the substituted monovalent non-aromatic condensed heteropolycyclic group, the substituted C.sub.5-C.sub.30 carbocyclic group, and the substituted or unsubstituted C.sub.1-C.sub.30 heterocyclic group is:

[0231] deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —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, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.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.1-C.sub.60 alkylthio group;

[0232] 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.1-C.sub.60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —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, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.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.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q.sub.11)(Q.sub.12), —Si(Q.sub.13)(Q.sub.14)(Q.sub.15), —B(Q.sub.16)(Q.sub.17), —P(Q.sub.18)(Q.sub.19), or —P(═O)(Q.sub.18)(Q.sub.19);

[0233] 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.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;

[0234] 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.7-C.sub.60 alkyl aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF.sub.5, —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, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C.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.1-C.sub.60 alkylthio group, 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.7-C.sub.60 alkyl aryl group, a C.sub.7-C.sub.60 aryl alkyl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a C.sub.2-C.sub.60 alkyl heteroaryl group, a C.sub.2-C.sub.60 heteroaryl alkyl group, a C.sub.1-C.sub.60 heteroaryloxy group, a C.sub.1-C.sub.60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q.sub.21)(Q.sub.22), —Si(Q.sub.23)(Q.sub.24)(Q.sub.25), —B(Q.sub.26)(Q.sub.27), —P(Q.sub.28)(Q.sub.29), or —P(═O)(Q.sub.28)(Q.sub.29); and

[0235] —N(Q.sub.31)(Q.sub.32), —Si(Q.sub.33)(Q.sub.34)(Q.sub.35), —B(Q.sub.36)(Q.sub.37), —P(═O)(Q.sub.38)(Q.sub.39), or —P(═O)(Q.sub.38)(Q.sub.39),

[0236] wherein Q.sub.1 to Q.sub.9, Q.sub.11 to Q.sub.19, Q.sub.21 to Q.sub.29, and Q.sub.31 to Q.sub.39 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.1-C.sub.60 alkylthio group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 alkyl aryl group, a substituted or unsubstituted C.sub.7-C.sub.60 aryl alkyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkyl heteroaryl group, a substituted or unsubstituted C.sub.2-C.sub.60 heteroaryl alkyl group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryloxy group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0237] Hereinafter, compounds and organic light-emitting devices according to one or more exemplary embodiments are described in further detail with reference to Synthesis Example and Examples. However, the organic light-emitting device is not limited thereto. The wording “‘B’ was used instead of ‘A’” used in describing Synthesis Examples means that an amount of ‘A’ used was identical to an amount of ‘B’ used, in terms of a molar equivalent.

EXAMPLES

Synthesis Example 1: Synthesis of Compound 1

[0238] ##STR00100## ##STR00101##

(1) Synthesis of Compound 1A

[0239] In a nitrogen environment, 7-bromo-2-methylthieno[2,3-c]pyridine (1.0 gram (g), 4.4 millimole (mmol)) and phenanthren-9-yl boronic acid (1.1 g, 4.8 mmol) were dissolved in 90 milliliters (mL) of 1,4-dioxane, and then, potassium carbonate (K.sub.2CO.sub.3) (1.4 g, 13.1 mmol) was dissolved in 35 mL of deionized (DI) water, and this mixed solution was added to the reaction mixture. Next, a palladium catalyst (tetrakis(triphenylphosphine)palladium (0), Pd(PPh.sub.3).sub.4) (0.25 g, 0.22 mmol) was added thereto. Afterwards, the resultant reaction mixture was stirred under reflux at a temperature of 110° C. After being allowed to cool to room temperature and subsequent extraction, the obtained solid was subjected to column chromatography (eluent: methylene chloride (MC) and hexanes) to obtain 1.3 g (yield of 88%) of compound 2-methyl-7-(phenanthren-9-yl)thieno[2,3-c]pyridine. The obtained compound was identified by high resolution mass spectrometry (HRMS) using matrix assisted laser desorption ionization (MALDI) and high performance liquid chromatography (HPLC) analysis.

[0240] HRMS (MALDI) calcd for C.sub.22H.sub.15NS: m/z: 325.43 Found: 326.14.

(2) Synthesis of Compound 1B

[0241] Compound 1A (1.3 g, 3.83 mmol) and iridium chloride (0.6 g, 1.70 mmol) were mixed with 30 mL of 2-ethoxyethanol and 10 mL of DI water, and the mixture was stirred under reflux for 24 hours, and then, the temperature was allowed to reach ambient temperature. The solid thus obtained was separated by filtration, washed sufficiently with water, methanol, and hexanes, in this stated order, and then, dried in a vacuum oven, so as to obtain 1.1 g (yield of 67%) of Compound 1B. Compound 1B obtained was used in the next reaction without an additional purification process.

(3) Synthesis of Compound 1

[0242] Pentane-2,4-dione (0.16 g, 1.60 mmol) and potassium carbonate (K.sub.2CO.sub.3) (0.22 g, 1.6 mmol) were added to Compound 1B (1.10 g, 0.64 mmol), and mixed with 15 mL of 2-ethoxyethanol, and stirred for 18 hours at a temperature of 90° C. Then, the temperature was allowed to cool to ambient temperature. After extraction, the obtained solid was subjected to column chromatography (eluent: MC and hexanes) to obtain 0.60 g (yield of 45%) of Compound 1. The obtained compound was identified by HRMS and HPLC analysis.

[0243] HRMS (MALDI) calcd for C.sub.41H.sub.31IrN.sub.2O.sub.2S.sub.2: m/z: 840.05 Found: 841.06.

Synthesis Example 2: Synthesis of Compound 2

[0244] ##STR00102## ##STR00103##

[0245] 0.66 g (43% yield) of Compound 2 was obtained in a similar manner as used to prepare Compound 1 of Synthesis Example 1, except that in synthesizing Compound 2A, 7-bromo-2-phenylthieno[2,3-c]pyridine (1.8 g, 6.2 mmol) was used instead of 7-bromo-2-methylthieno[2,3-c]pyridine. The obtained compound was identified by HRMS and HPLC analysis.

[0246] HRMS (MALDI) calcd for C.sub.51H.sub.35IrN.sub.2O.sub.2S.sub.2: m/z: 964.19 Found: 965.18.

Example 1

[0247] As an anode, an ITO-patterned glass substrate was cut to a size of 50 millimeter (mm)×50 mm×0.5 mm, sonicated with isopropyl alcohol and DI water, each for 5 minutes, and then cleaned by exposure to Ultraviolet (UV) rays and ozone for 30 minutes. The resultant glass substrate was loaded onto a vacuum deposition apparatus.

[0248] Compounds HT3 and F12(p-dopant) were co-deposited by vacuum on the anode at the weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and Compound HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,600 Å.

[0249] Then, RH3 (host) and Compound 1 (dopant) were co-deposited at a weight ratio of 97:3 on the hole transport layer to form an emission layer having a thickness of 400 Å.

[0250] Then, Compound ET3 and LiQ (n-dopant) were co-deposited on the emission layer at the volume ratio of 50:50 to form an electron transport layer having a thickness of 350 Å, LiQ was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 1,000 Å, thereby completing the manufacture of an organic light-emitting device.

##STR00104##

Example 2 and Comparative Examples 1 to 7

[0251] Organic light-emitting devices were manufactured in a similar manner as in Example 1, except that Compounds shown in Table 2 were each used instead of Compound 1 as a dopant in forming an emission layer.

[0252] The driving voltage (Volt, V), roll-off ratio (%), maximum emission wavelength (λ.sub.max, nm), and lifespan (LT.sub.97, relative %) of each of the organic light-emitting devices manufactured according to Examples 1 and 2 and Comparative Examples 1 to 7, and results thereof are shown in Table 2. As evaluation apparatuses, a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used. The lifespan is reported as a relative value based on Comparative Example 1 (100%). The roll-off ratio was calculated according to Equation 1:

Roll-off ratio={1−(efficiency/maximum luminescence efficiency)}×100% Equation 1

TABLE-US-00002 TABLE 2 Driving Roll-off Lifespan Molecular voltage ratio λ.sub.max (Relative No. structure (V) (%) (nm) value, %) Example 1 Compound 1 5.0 12 660 120 Example 2 Compound 11 4.8 11 667 130 Comparative Compound A 4.9 13 624 100 Example 1 Comparative Compound B 5.4 16 666 40 Example 2 Comparative Compound C 5.0 14 580 40 Example 3 Comparative Compound D 5.1 14 595 40 Example 4 Comparative Compound E 5.2 15 590 20 Example 5 Comparative Compound F 5.4 16 585 15 Example 6 Comparative Compound G 4.5 15 535 10 Example 7

##STR00105##

[0253] From Table 2, it can be seen that the organic light-emitting devices of Examples 1 and 2 had low driving voltage and roll-off ratio, and excellent lifespan characteristics. In addition, it can be seen that the organic light-emitting devices of Examples 1 and 2 had lower or equivalent driving voltages, lower roll-off ratios, and longer lifespans compared to the organic light-emitting devices of Comparative Examples 1 to 7. Also, it can be seen that the organic light-emitting devices of Examples 1 and 2 were suitable for red light emission, unlike the organic light-emitting devices of Comparative Example 7.

[0254] The organometallic compound has excellent electrical characteristics and stability. Accordingly, an electronic device, for example, an organic light-emitting device, using the organometallic compound may have a low driving voltage, high efficiency, long lifespan, reduced roll-off ratio and relative narrow FWHM of the emission peak of the electroluminescence (EL) spectrum. Thus, due to the use of the organometallic compounds, a high-quality organic light-emitting device may be embodied.

[0255] It should be understood that the exemplary embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each exemplary embodiment should typically be considered as available for other similar features or aspects in other exemplary embodiments. While one or more exemplary embodiments have been described with reference to the FIGURE, 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.

ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME, AND ELECTRONIC APPARATUS INCLUDING ORGANIC LIGHT-EMITTING DEVICE

Inventors

Cpc classification

Classification Explorer

H10K2101/30

ELECTRICITY

Classification Explorer

H10K50/11

ELECTRICITY

Classification Explorer

C07F15/0033

CHEMISTRY; METALLURGY

Classification Explorer

H10K85/342

ELECTRICITY

Classification Explorer

H10K2101/40

ELECTRICITY

Classification Explorer

H10K2101/10

ELECTRICITY

International classification

Classification Explorer

C07F15/00

CHEMISTRY; METALLURGY

Classification Explorer

H10K85/30

ELECTRICITY

Abstract

Claims

Description