ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME, AND ELECTRONIC APPARATUS INCLUDING THE ORGANIC LIGHT-EMITTING DEVICE
20230217805 · 2023-07-06
Inventors
- Bumwoo Park (Yongin-si, KR)
- Jeoungin Yi (Seoul, KR)
- Ohyun Kwon (Seoul, KR)
- Virendra Kumar Rai (Hwaseong-si, KR)
- Juhee Moon (Hwaseong-si, KR)
- Byoungki Choi (Hwaseong-si, KR)
Cpc classification
C09K2211/185
CHEMISTRY; METALLURGY
C09K2211/1044
CHEMISTRY; METALLURGY
C09K11/025
CHEMISTRY; METALLURGY
International classification
Abstract
An organometallic compound represented by Formula 1:
##STR00001##
wherein M.sub.1 is a transition metal, Ln.sub.1 is a ligand represented by Formula 1A, Ln.sub.2 is a ligand represented by Formula 1B, n1 is 1 or 2, and n2 is 1 or 2:
##STR00002##
##STR00003##
wherein ring CY.sub.3 is: a 5-membered N-containing heterocyclic group; or a 5-membered N-containing heterocyclic group condensed with a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group, ring CY.sub.4 is: a 6-membered carbocyclic group; a 6-membered heterocyclic group; a 6-membered carbocyclic group condensed with a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group; or a 6-membered heterocyclic group condensed with a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group, Y.sub.1 is O, S, Se, or C(R.sub.1)(R.sub.2), Y.sub.2 is O or S, and b30, b40, R.sub.1, R.sub.2, R.sub.11 to R.sub.14, R.sub.21 to R.sub.26, R.sub.30, and R.sub.40 are as defined herein.
Claims
1. An organometallic compound, represented by Formula 1: ##STR00578## wherein, in Formula 1, M.sub.1 is a transition metal, Ln.sub.1 is a ligand represented by Formula 1A, Ln.sub.2 is a ligand represented by Formula 1B, n1 is 1 or 2, and n2 is 1 or 2, Formula 1A Formula 1B ##STR00579## ##STR00580## wherein, in Formulae 1A and 1B, ring CY.sub.3 is: a 5-membered N-containing heterocyclic group; or a 5-membered N-containing heterocyclic group condensed with a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group, ring CY.sub.4 is: a 6-membered carbocyclic group; a 6-membered heterocyclic group; a 6-membered carbocyclic group condensed with a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group; or a 6-membered heterocyclic group condensed with a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group, Y.sub.1 is O, S, Se, or C(R.sub.1)(R.sub.2), Y.sub.2 is O or S, R.sub.1, R.sub.2, R.sub.11 to R.sub.14, R.sub.21 to R.sub.26, R.sub.30, and R.sub.40 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.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), provided that at least one of R.sub.1, R.sub.2, R.sub.11 to R.sub.14, R.sub.21 to R.sub.26, R.sub.30, or R.sub.40 is —Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), neighboring two or more of a plurality of R.sub.30 are optionally linked together 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 a plurality of R.sub.40 are optionally linked together 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.1, R.sub.2, R.sub.11 to R.sub.14, R.sub.21 to R.sub.26, R.sub.30, and R.sub.40 are optionally linked together 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, b30 is 1, 2, 3, 4, 5, or 6, b40 is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, * and *′ each indicate a binding site to M.sub.1, 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.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, and the substituted monovalent non-aromatic condensed heteropolycyclic 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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, —CI, —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.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, —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.29), or —P(═O)(Q.sub.38)(Q.sub.39), and 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), osmium (Os), 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 a sum of n1 and n2 is 3.
4. The organometallic compound of claim 1, wherein ring CY.sub.3 is a 1H-pyrrole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, a benzimidazole group, an imidazopyridine group, an imidazopyrimidine group, or an imidazopyrazine group, and ring CY.sub.4 is a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phenanthroline group, a quinoxaline group, or a quinazoline group.
5. The organometallic compound of claim 1, wherein Y.sub.1 is O or S, and Y.sub.2 is O.
6. The organometallic compound of claim 1, wherein Ln.sub.1 includes —Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3).
7. The organometallic compound of claim 1, wherein at least one of R.sub.11 to R.sub.14 and R.sub.21 to R.sub.26 is Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or-Ge(Q1)(Q2)(Q3).
8. The organometallic compound of claim 1, wherein at least one of R.sub.11 and R.sub.21 to R.sub.24 is Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3).
9. The organometallic compound of claim 1, wherein Ln.sub.2 is represented by Formula 1B-1 or 1B-2: ##STR00581## ##STR00582## wherein, in Formulae 1B-1 and 1B-2, X.sub.31 is C(R.sub.31) or N and X.sub.32 is C(R.sub.32) or N, X.sub.33 is C(R.sub.33)(R.sub.34) or N(R.sub.33), X.sub.35 is C(R.sub.35) or N, X.sub.36 is C(R.sub.36) or N, X.sub.37 is C(R.sub.37) or N, and X.sub.38 is C(R.sub.38) or N, X.sub.41 is C(R.sub.41) or N, X.sub.42 is C(R.sub.42) or N, X.sub.43 is C(R.sub.43) or N, and X.sub.44 is C(R.sub.44) or N, R.sub.31 to R.sub.38 are each independently as described in connection with R.sub.30 in claim 1, R.sub.41 to R.sub.44 are each independently as described in connection with R.sub.40 in claim 1, and * and *′ each indicate a binding site to M.sub.1.
10. The organometallic compound of claim 1, wherein a moiety represented by ##STR00583## in Formula 1B is represented by one of Formulae 3-1 to 3-12: ##STR00584## ##STR00585## ##STR00586## ##STR00587## ##STR00588## ##STR00589## ##STR00590## ##STR00591## ##STR00592## ##STR00593## ##STR00594## ##STR00595## wherein, in Formulae 3-1 to 3-12, R.sub.31 to R.sub.33 and R.sub.35 to R.sub.38 are each independently as described in connection with R.sub.30 in claim 1, * indicates a binding site to M.sub.1, and *″ indicates a binding site to a neighboring atom.
11. The organometallic compound of claim 1, wherein R.sub.1, R.sub.2, R.sub.11 to R.sub.14, R.sub.21 to R.sub.26, R.sub.30, and R.sub.40 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: ##STR00596## ##STR00597## ##STR00598## ##STR00599## ##STR00600## ##STR00601## ##STR00602## ##STR00603## ##STR00604## ##STR00605## ##STR00606## ##STR00607## ##STR00608## ##STR00609## ##STR00610## ##STR00611## ##STR00612## ##STR00613## ##STR00614## ##STR00615## ##STR00616## ##STR00617## ##STR00618## ##STR00619## ##STR00620## ##STR00621## ##STR00622## ##STR00623## ##STR00624## ##STR00625## ##STR00626## ##STR00627## ##STR00628## ##STR00629## ##STR00630## ##STR00631## ##STR00632## ##STR00633## ##STR00634## ##STR00635## ##STR00636## ##STR00637## ##STR00638## ##STR00639## ##STR00640## ##STR00641## ##STR00642## ##STR00643## ##STR00644## ##STR00645## ##STR00646## ##STR00647## ##STR00648## ##STR00649## ##STR00650## ##STR00651## ##STR00652## ##STR00653## ##STR00654## ##STR00655## ##STR00656## ##STR00657## ##STR00658## ##STR00659## ##STR00660## ##STR00661## ##STR00662## ##STR00663## ##STR00664## ##STR00665## ##STR00666## ##STR00667## ##STR00668## ##STR00669## ##STR00670## ##STR00671## ##STR00672## ##STR00673## ##STR00674## ##STR00675## ##STR00676## ##STR00677## ##STR00678## ##STR00679## ##STR00680## ##STR00681## ##STR00682## ##STR00683## ##STR00684## ##STR00685## ##STR00686## ##STR00687## ##STR00688## ##STR00689## ##STR00690## ##STR00691## ##STR00692## ##STR00693## ##STR00694## ##STR00695## ##STR00696## ##STR00697## ##STR00698## ##STR00699## ##STR00700## ##STR00701## ##STR00702## ##STR00703## ##STR00704## ##STR00705## ##STR00706## ##STR00707## ##STR00708## ##STR00709## ##STR00710## ##STR00711## ##STR00712## ##STR00713## ##STR00714## ##STR00715## ##STR00716## ##STR00717## ##STR00718## ##STR00719## ##STR00720## ##STR00721## ##STR00722## ##STR00723## ##STR00724## ##STR00725## ##STR00726## ##STR00727## ##STR00728## ##STR00729## ##STR00730## ##STR00731## ##STR00732## ##STR00733## ##STR00734## ##STR00735## ##STR00736## ##STR00737## ##STR00738## ##STR00739## ##STR00740## ##STR00741## ##STR00742## ##STR00743## ##STR00744## ##STR00745## ##STR00746## ##STR00747## ##STR00748## ##STR00749## ##STR00750## ##STR00751## ##STR00752## ##STR00753## ##STR00754## ##STR00755## ##STR00756## ##STR00757## ##STR00758## ##STR00759## ##STR00760## ##STR00761## ##STR00762## ##STR00763## ##STR00764## ##STR00765## ##STR00766## ##STR00767## ##STR00768## ##STR00769## ##STR00770## ##STR00771## ##STR00772## ##STR00773## ##STR00774## ##STR00775## ##STR00776## ##STR00777## ##STR00778## ##STR00779## ##STR00780## ##STR00781## ##STR00782## ##STR00783## ##STR00784## ##STR00785## ##STR00786## ##STR00787## ##STR00788## ##STR00789## ##STR00790## ##STR00791## ##STR00792## ##STR00793## ##STR00794## ##STR00795## ##STR00796## ##STR00797## ##STR00798## ##STR00799## ##STR00800## ##STR00801## ##STR00802## ##STR00803## ##STR00804## ##STR00805## ##STR00806## ##STR00807## ##STR00808## ##STR00809## ##STR00810## ##STR00811## ##STR00812## ##STR00813## ##STR00814## ##STR00815## ##STR00816## ##STR00817## ##STR00818## ##STR00819## ##STR00820## ##STR00821## ##STR00822## ##STR00823## ##STR00824## ##STR00825## ##STR00826## ##STR00827## ##STR00828## ##STR00829## ##STR00830## ##STR00831## ##STR00832## ##STR00833## ##STR00834## ##STR00835## ##STR00836## ##STR00837## ##STR00838## ##STR00839## ##STR00840## ##STR00841## ##STR00842## ##STR00843## ##STR00844## ##STR00845## ##STR00846## ##STR00847## ##STR00848## ##STR00849## ##STR00850## ##STR00851## ##STR00852## ##STR00853## ##STR00854## ##STR00855## ##STR00856## ##STR00857## ##STR00858## ##STR00859## ##STR00860## ##STR00861## ##STR00862## ##STR00863## ##STR00864## ##STR00865## ##STR00866## ##STR00867## ##STR00868## ##STR00869## ##STR00870## ##STR00871## ##STR00872## ##STR00873## ##STR00874## ##STR00875## ##STR00876## ##STR00877## ##STR00878## ##STR00879## ##STR00880## ##STR00881## ##STR00882## ##STR00883## ##STR00884## ##STR00885## ##STR00886## ##STR00887## ##STR00888## ##STR00889## ##STR00890## ##STR00891## ##STR00892## ##STR00893## ##STR00894## ##STR00895## ##STR00896## ##STR00897## ##STR00898## ##STR00899## ##STR00900## ##STR00901## ##STR00902## ##STR00903## ##STR00904## ##STR00905## ##STR00906## ##STR00907## ##STR00908## ##STR00909## ##STR00910## ##STR00911## ##STR00912## ##STR00913## ##STR00914## ##STR00915## ##STR00916## ##STR00917## ##STR00918## ##STR00919## ##STR00920## ##STR00921## ##STR00922## ##STR00923## ##STR00924## ##STR00925## ##STR00926## ##STR00927## ##STR00928## ##STR00929## ##STR00930## ##STR00931## ##STR00932## ##STR00933## ##STR00934## ##STR00935## ##STR00936## ##STR00937## ##STR00938## ##STR00939## ##STR00940## ##STR00941## ##STR00942## ##STR00943## ##STR00944## ##STR00945## ##STR00946## ##STR00947## ##STR00948## ##STR00949## ##STR00950## ##STR00951## ##STR00952## ##STR00953## ##STR00954## ##STR00955## ##STR00956## ##STR00957## ##STR00958## ##STR00959## ##STR00960## ##STR00961## ##STR00962## ##STR00963## ##STR00964## ##STR00965## ##STR00966## ##STR00967## ##STR00968## ##STR00969## ##STR00970## ##STR00971## ##STR00972## ##STR00973## ##STR00974## ##STR00975## ##STR00976## ##STR00977## ##STR00978## ##STR00979## ##STR00980## ##STR00981## ##STR00982## ##STR00983## ##STR00984## ##STR00985## ##STR00986## ##STR00987## ##STR00988## ##STR00989## ##STR00990## ##STR00991## ##STR00992## ##STR00993## ##STR00994## ##STR00995## ##STR00996## ##STR00997## ##STR00998## ##STR00999## ##STR01000## ##STR01001## ##STR01002## ##STR01003## ##STR01004## ##STR01005## ##STR01006## ##STR01007## ##STR01008## ##STR01009## ##STR01010## 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.
12. The organometallic compound of claim 1, wherein at least one of R.sub.11 to R.sub.14 is 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 neopentyl group, a 3-pentyl group, a 3-methyl-2-butyl group, a cyclopentyl group, or a cyclohexyl group.
13. The organometallic compound of claim 1, wherein the organometallic compound is a compound represented by Formula 30-1 or 30-2: ##STR01011## ##STR01012## wherein, in Formulae 30-1 and 30-2, M.sub.1, n1, n2, Y.sub.1, Y.sub.2, R.sub.11 to R.sub.14, and R.sub.21 to R.sub.26 are respectively as described in claim 1, R.sub.31 to R.sub.33 and R.sub.35 to R.sub.38 are each independently as described in connection with R.sub.30 in claim 1, and R.sub.41 to R.sub.44 are independently as described in connection with R.sub.40 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 of Compounds 1 to 56: ##STR01013## ##STR01014## ##STR01015## ##STR01016## ##STR01017## ##STR01018## ##STR01019## ##STR01020## ##STR01021## ##STR01022## ##STR01023## ##STR01024## ##STR01025## ##STR01026## ##STR01027## ##STR01028## ##STR01029## ##STR01030## ##STR01031## ##STR01032## ##STR01033## ##STR01034## ##STR01035## ##STR01036## ##STR01037## ##STR01038## ##STR01039## ##STR01040## ##STR01041## ##STR01042## ##STR01043## ##STR01044## ##STR01045## ##STR01046## ##STR01047## ##STR01048## ##STR01049## ##STR01050## ##STR01051## ##STR01052## ##STR01053## ##STR01054## ##STR01055## ##STR01056## ##STR01057## ##STR01058## ##STR01059## ##STR01060## ##STR01061## ##STR01062## ##STR01063## ##STR01064## ##STR01065## ##STR01066## ##STR01067## ##STR01068## .
16. An organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer arranged 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 organic light-emitting device of claim 16, wherein the emission layer comprises the at least one of the 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 at least one organometallic compound in the emission layer.
19. The organic 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 arranged between the first electrode and the emission layer, and an electron transport region arranged 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
BRIEF DESCRIPTION OF THE DRAWING
[0030] The above and other aspects, features, and advantages of certain exemplary embodiments of the disclosure will be more apparent from the following detailed description taken in conjunction with the
DETAILED DESCRIPTION
[0031] Reference will now be made in detail to one or more 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 descriptions set forth herein. Accordingly, the exemplary embodiments are merely described in further detail below, by referring to the
[0032] 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.” As used herein, the term “and/or” includes any and all combinations of one or more of the same 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. 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.
[0033] 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.
[0034] 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.
[0035] 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.
[0036] 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.
[0037] “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.
[0038] Hereinafter, a work function or a highest occupied molecular orbital (HOMO) energy level is expressed as an absolute value from a vacuum level. In addition, when the work function or the HOMO energy level is referred to be “deep,” “high” or “large,” the work function or the HOMO energy level has a large absolute value based on “0 eV” of the vacuum level, while when the work function or the HOMO energy level is referred to be “shallow,” “low,” or “small,” the work function or HOMO energy level has a small absolute value based on “0 eV” of the vacuum level.
[0039] An aspect of the present disclosure provides an organometallic compound represented by Formula 1:
##STR00007##
wherein, n Formula 1, M.sub.1 is a transition metal.
[0040] For example, M.sub.1 may be a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, or a third-row transition metal of the Periodic Table of Elements.
[0041] In one or more embodiments, M.sub.1 may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
[0042] In one or more embodiments, M.sub.1 may be Ir, Pt, Os, or Rh.
[0043] In one or more embodiments, M.sub.1 may be Ir.
[0044] In Formula 1, n1 is 1 or 2, and n2 is 1, 2, or 3.
[0045] In one or more embodiments, a sum of n1 and n2 may be 2 or 3.
[0046] In one or more embodiments, M.sub.1 may be Ir, and the sum of n1 and n2 may be 3.
[0047] In one or more embodiments, M.sub.1 may be Pt, and the sum of n1 and n2 may be 2.
[0048] In Formula 1, Ln.sub.1 is a ligand represented by Formula 1A:
##STR00008##
[0049] In Formula 1A, Y.sub.1 may be O, S, Se, or C(R.sub.1)(R.sub.2).
[0050] In one or more embodiments, Y.sub.1 may be O or S.
[0051] In one or more embodiments, Ln.sub.1 may include —Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3).
[0052] In Formula 1, Ln.sub.2 is a ligand represented by Formula 1B:
##STR00009##
[0053] In Formula 1B, ring CY.sub.3 is: (i) a 5-membered N-containing heterocyclic group; or (ii) a 5-membered N-containing heterocyclic group condensed with a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group.
[0054] In one or more embodiments, ring CY.sub.3 may be a 1 H-pyrrole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, a benzimidazole group, an imidazopyridine group, an imidazopyrimidine group, or an imidazopyrazine group.
[0055] In Formula 1B, ring CY.sub.4 is: (i) a 6-membered carbocyclic group; (ii) a 6-membered heterocyclic group; (iii) a 6-membered carbocyclic group condensed with a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group; or (iv) a 6-membered heterocyclic group condensed with a C.sub.5-C.sub.30 carbocyclic group or a C.sub.1-C.sub.30 heterocyclic group.
[0056] In one or more embodiments, ring CY.sub.4 may be a phenyl group, a naphthalene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phenanthroline group, a quinoxaline group, or a quinazoline group.
[0057] In Formula 1B, Y.sub.2 is O or S.
[0058] In one or more embodiments, Y.sub.2 may be O.
[0059] In one or more embodiments, Ln.sub.2 may be represented by Formula 1B-1 or 1B-2:
##STR00010##
##STR00011##
[0060] In Formulae 1B-1 and 1B-2, [0061] X.sub.31 may be C(R.sub.31) or N, and X.sub.32 may be C(R.sub.32) or N, [0062] X.sub.33 may be C(R.sub.33)(R.sub.34) or N(R.sub.33), [0063] X.sub.35 may be C(R.sub.35) or N, X.sub.36 may be C(R.sub.36) or N, X.sub.37 may be C(R.sub.37) or N, and X.sub.38 may be C(R.sub.38) or N, [0064] X.sub.41 may be C(R.sub.41) or N, X.sub.42 may be C(R.sub.42) or N, X.sub.43 may be C(R.sub.43) or N, and X.sub.44 may be C(R.sub.44) or N, [0065] R.sub.31 to R.sub.38 may each independently be as described in connection with R.sub.30, [0066] R.sub.41 to R.sub.44 may each independently be as described in connection with R.sub.40, and [0067] * and *′ each indicate a binding site to a neighboring atom.
[0068] In one or more embodiments, a moiety represented by
##STR00012##
in Formula 1B may be represented by one of Formulae 3-1 to 3-12:
##STR00013##
##STR00014##
##STR00015##
##STR00016##
##STR00017##
##STR00018##
##STR00019##
##STR00020##
##STR00021##
##STR00022##
##STR00023##
##STR00024##
[0069] In Formulae 3-1 to 3-12, [0070] R.sub.31 to R.sub.33 and R.sub.35 to R.sub.38 may each independently be as described in connection with R.sub.30, [0071] * indicates a binding site to M.sub.1, and [0072] *″ indicates a binding site to a neighboring atom.
[0073] In Formula 1, R.sub.1 to R.sub.6, R.sub.10, R.sub.20, R.sub.30, and R.sub.40 to R.sub.42 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.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).
[0074] In Formula 1B, b30 is 1, 2, 3, 4, 5, or 6.
[0075] In one or more embodiments, b30 may be 1, 2, 3, 4, or 5.
[0076] In one or more embodiments, b30 may be 1, 2, or 3.
[0077] In Formula 1B, b40 is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
[0078] In one or more embodiments, b40 may be 1, 2, 3, 4, 5, 6, 7, or 8.
[0079] In one or more embodiments, b40 may be 1, 2, 3, 4, 5, or 6.
[0080] In one or more embodiments, b40 may be 1, 2, 3, or 4.
[0081] In one or more embodiments, b40 may be 1 or 2.
[0082] In one or more embodiments, R.sub.10, R.sub.20, R.sub.30, and R.sub.40 to R.sub.42 may each independently be: [0083] 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 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, —SF.sub.5, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, or a C.sub.1-C.sub.20 alkylthio group; [0084] a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, or a C.sub.1-C.sub.30 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 norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or a combination thereof; [0085] a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a 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, or an imidazopyrimidinyl group; [0086] a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a 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, or an imidazopyrimidinyl 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.20 alkyl group, a C.sub.1-C.sub.20 alkoxy 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 phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, or a combination thereof; or [0087] —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).
[0088] In one or more embodiments, R.sub.10, R.sub.20, R.sub.30, and R.sub.40 to R.sub.42 may each independently be: [0089] 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 [0090] a group represented by one of Formulae 9-1 to 9-61, 9-201 to 9-237, 10-1 to 10-129, or 10-201 to 10-350:
[0091] In Formulae 9-1 to 9-61, 9-201 to 9-237, 10-1 to 10-129, 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.
[0092] In Formulae 1A and 1B, two or more of a plurality of R.sub.30; two or more of a plurality of R.sub.40; or neighboring two or more of R.sub.1, R.sub.2, R.sub.11 to R.sub.14, R.sub.21 to R.sub.26, R.sub.30, and R.sub.40 are optionally linked together 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.
[0093] In one or more embodiments, two or more of a plurality of R.sub.30; two or more of a plurality of R.sub.40; or neighboring two or more of R.sub.1, R.sub.2, R.sub.11 to R.sub.14, R.sub.21 to R.sub.26, R.sub.30, and R.sub.40 may optionally be linked together via a single bond, a double bond, or a first linking group to form a C.sub.5-C.sub.30 carbocyclic group that is unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.30 heterocyclic group that is unsubstituted or substituted with at least one R.sub.10a (for example, a fluorene group, a xanthene group, an acridine group, or the like, each unsubstituted or substituted with at least one R.sub.10a). R.sub.10a may be as described in connection with R.sub.11.
[0094] The first linking group may be selected from *—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)—*′, and .sub.*—C≡C—.sub.*′, R.sub.8 and R.sub.9 may each independently be as described in connection with R.sub.11, and * and *′ each indicate a binding site to a neighboring atom.
[0095] In one or more embodiments, Q.sub.1 to Q9, Q.sub.11 to Q19, Q21 to Q29, and Q31 to Q39 may each independently be: [0096] deuterium, —CH.sub.3, -CD.sub.3, -CD.sub.2H, -CDH.sub.2, —CH.sub.2CH.sub.3, —CH.sub.2CD.sub.3, —CH.sub.2CD.sub.2H, —CH.sub.2CDH.sub.2, —CHDCH.sub.3, —CHDCD.sub.2H, —CHDCDH.sub.2, —CHDCD.sub.3, —CD.sub.2CD.sub.3, —CD.sub.2CD.sub.2H, or —CD.sub.2CDH.sub.2; [0097] an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, or a naphthyl group; or [0098] an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, or a naphthyl group, each substituted with at least one of deuterium, a C.sub.1-C.sub.10 alkyl group, a phenyl group, or a combination thereof.
[0099] In one or more embodiments, the organometallic compound may be represented by Formula 30-1 to 30-2:
##STR00420##
##STR00421##
[0100] In Formulae 30-1 and 30-2, [0101] M.sub.1, n1, n2, Y.sub.1, Y.sub.2, R.sub.11 to R.sub.14, R.sub.21 to R.sub.26, R.sub.31 to R.sub.33, and R.sub.41 to R.sub.48 may respectively be as described herein, [0102] R.sub.11 to R.sub.14 may each independently be as described in connection with R.sub.10, [0103] R.sub.21 to R.sub.24 may each independently be as described in connection with R.sub.20, [0104] R.sub.31 to R.sub.34 are each independently as described in connection with R.sub.30, and [0105] R.sub.41 to R.sub.48 may each independently be as described in connection with R.sub.40.
[0106] In one or more embodiments, examples of the “C.sub.5-C.sub.30 carbocyclic group that is unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.30 heterocyclic group that is unsubstituted or substituted with at least one R.sub.10a” include a phenyl (benzene) group, a naphthalene group, a cyclopentane group, a cyclopentadiene group, a cyclohexane group, a cycloheptane group, a bicyclo[2.2.1]heptane group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, or a benzosilole group, each unsubstituted or substituted with at least one R.sub.10a. R.sub.10a may be as described in connection with R.sub.11. The C.sub.5-C.sub.30 carbocyclic group and the C.sub.1-C.sub.30 heterocyclic group may respectively be as described herein.
[0107] In one or more embodiments, at least one of R.sub.10(s) in the number of b10, R.sub.20(.sub.S) in the number of b20, R.sub.30(S) in the number of b30, R.sub.40(S) in the number of b40, R.sub.41, and R.sub.42 may be 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, a 2-methylbutyl group, a sec-pentyl, a tert-pentyl, a neo-pentyl, a 3-pentyl, a 3-methyl-2-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a phenyl group, a biphenyl group, a C.sub.1-C.sub.20 alkylphenyl group, a naphthyl group, —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), or —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3), each unsubstituted or substituted with at least one deuterium.
[0108] In one or more embodiments, at least one of R.sub.11 to R.sub.14 may be 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 cyclopentyl group, or a cyclohexyl group.
[0109] In one or more embodiments, at least one of R.sub.30(S) in the number of b30 may be 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, or a naphthyl group.
[0110] In one or more embodiments, in Formulae 1B-1, 1B-2, 3-1 to 3-12, 30-1, or 30-2, at least one of R.sub.30(s) in the number of b30 may be 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, an neo-pentyl group, a 3-pentyl group, a 3-methyl-2-butyl group, a phenyl group, or a naphthyl group.
[0111] In one or more embodiments, in Formula 1A, at least one of R.sub.11 to R.sub.14 may be Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3).
[0112] In one or more embodiments, in Formula 1A, at least one of R.sub.21 to R.sub.26 may be Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or —Ge(Q.sub.1)(Q.sub.2)(Q.sub.3).
[0113] In one or more embodiments, in Formula 1A, at least one of R.sub.11 and R.sub.21 to R.sub.24 may be Si(Q.sub.1)(Q.sub.2)(Q.sub.3) or-Ge(Q.sub.1)(Q.sub.2)(Q.sub.3).
[0114] In one or more embodiments, the organometallic compound may include one to four silyl groups (-Si(Q.sub.1)(Q.sub.2)(Q.sub.3)) and/or one or four germyl groups (-Ge(Q.sub.1)(Q.sub.2)(Q.sub.3)).
[0115] In one or more embodiments, the organometallic compound may include one or two silyl groups (-Si(Q.sub.1)(Q.sub.2)(Q.sub.3)) and/or one or two germyl groups (-Ge(Q.sub.1)(Q.sub.2)(Q.sub.3)).
[0116] In one or more embodiments, the organometallic compound may include one silyl group (-Si(Q.sub.1)(Q.sub.2)(Q.sub.3)) or one germyl group (-Ge(Q.sub.1)(Q.sub.2)(Q.sub.3)).
[0117] In one or more embodiments, the organometallic compound may be one of Compounds 1 to 56:
##STR00422##
##STR00423##
##STR00424##
##STR00425##
##STR00426##
##STR00427##
##STR00428##
##STR00429##
##STR00430##
##STR00431##
##STR00432##
##STR00433##
##STR00434##
##STR00435##
##STR00436##
##STR00437##
##STR00438##
##STR00439##
##STR00440##
##STR00441##
##STR00442##
##STR00443##
##STR00444##
##STR00445##
##STR00446##
##STR00447##
##STR00448##
##STR00449##
##STR00450##
##STR00451##
##STR00452##
##STR00453##
##STR00454##
##STR00455##
##STR00456##
##STR00457##
##STR00458##
##STR00459##
##STR00460##
##STR00461##
##STR00462##
##STR00463##
##STR00464##
##STR00465##
##STR00466##
##STR00467##
##STR00468##
##STR00469##
##STR00470##
##STR00471##
##STR00472##
##STR00473##
##STR00474##
##STR00475##
##STR00476##
##STR00477##
[0118] In one or more embodiments, the organometallic compound may be electrically neutral.
[0119] The organometallic compound represented by Formula may satisfy the structure of Formula 1, include the ligands represented by Formulae 1A and 1B, and may be substituted with at least one silyl group or at least one germyl group. Due to this structure, the organometallic compound represented by Formula 1 has excellent luminescence characteristics, and in particular, may have such characteristics suitable for use as a luminescent material with high color purity by controlling the emission wavelength range.
[0120] In addition, the organometallic compound represented by Formula 1 has excellent electrical mobility, and thus, electronic devices including the organometallic compound, for example, organic light-emitting devices including the organometallic compound may show low driving voltage, high efficiency, a long lifespan, and reduced roll-off phenomenon.
[0121] In addition, the photochemical stability of the organometallic compound represented by Formula 1 is improved, and thus, electronic devices including the organometallic compound, for example, organic light-emitting devices including the organometallic compound may show high emission efficiency, long lifespan, and high color purity.
[0122] The highest occupied molecular orbital (HOMO) energy level, lowest unoccupied molecular orbital (LUMO) energy level, energy gap, triple (T.sub.1) energy level, single (S.sub.1) energy level, of organometallic compounds 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 basis level , and results thereof are shown in Table 1 with energy levels reported as electron Volts (eV).
TABLE-US-00001 Compound HOMO (eV) LUMO (eV) S.sub.1 (eV) T.sub.1 (eV) Compound 1 -4.580 -1.282 2.647 2.388 Compound 2 -4.566 -1.266 2.645 2.389
##STR00478##
##STR00479##
[0123] Referring to Table 1, it was confirmed that the organometallic compound represented by Formula 1 has suitable electrical characteristics for use as a dopant in an electric device, for example, an organic light-emitting device.
[0124] In one or more embodiments, the full width at half maximum (FWHM) of the emission peak of the emission spectrum or the electroluminescence spectrum of the organometallic compound may be 70 nanometers (nm) or less. For example, the FWHM of the emission peak of the emission spectrum or the electroluminescence spectrum of the organometallic compound may be from about 30 nm to about 65 nm, from about 40 nm to about 63 nm, or from about 45 nm to about 62 nm.
[0125] In one or more embodiments, the maximum emission wavelength (emission peak wavelength, λ.sub.max) of the emission peak of the emission spectrum or electroluminescence spectrum of the organometallic compound may be from about 490 nm to about 550 nm.
[0126] 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 described below.
[0127] Accordingly, the organometallic compound represented by Formula 1 may be suitable for use as a dopant in an organic layer, for example, an emission layer, of an organic light-emitting device. Thus, another aspect of the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode; and an organic layer that is located between the first electrode and the second electrode and includes an emission layer, wherein the organic layer includes at least one organometallic compound represented by Formula 1.
[0128] As described above, due to the inclusion of the organic layer including the organometallic compound represented by Formula 1, the organic light-emitting device may have excellent characteristics in terms of driving voltage, current efficiency, power efficiency, external quantum efficiency, lifespan, and/or color purity. Also, such an organic light-emitting device may have a reduced roll-off phenomenon and a relatively narrow electroluminescent (EL) spectrum emission peak FWHM.
[0129] The organometallic compound represented by Formula 1 may be used between a pair of electrodes of the 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 included in the emission layer).
[0130] In one or more embodiments, the emission layer may emit green light. For example, the emission layer may emit red light having a maximum emission wavelength in a range of about 490 nm to about 550 nm.
[0131] The expression “(an organic layer) includes at least one organometallic compound represented by Formula 1” as 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”.
[0132] In one or more embodiments, 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 embodiment, Compound 1 and Compound 2 may exist in an identical layer (for example, Compound 1 and Compound 2 may all exist in the emission layer).
[0133] 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.
[0134] In one or more embodiments, in the organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region arranged between the first electrode, and the emission layer and an electron transport region arranged between the emission layer and the second electrode, wherein 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.
[0135] The term “organic layer” as 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 metal.
[0136] The
[0137] A substrate may be additionally arranged under the first electrode 11 or above the second electrode 19. For use as the substrate, any 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.
[0138] The first electrode 11 may be, for example, 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. In one or more embodiments, 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).
[0139] 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.
[0140] The organic layer 15 is located on the first electrode 11.
[0141] The organic layer 15 may include: the hole transport region; the emission layer; and the electron transport region.
[0142] The hole transport region may be located between the first electrode 11 and the emission layer.
[0143] 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.
[0144] The hole transport region may include only either a hole injection layer or a hole transport layer. 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 constituting layers for each structure are sequentially stacked in this stated order from the first electrode 11.
[0145] 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 such as vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.
[0146] 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.
[0147] When the hole injection layer is formed by spin coating, the coating conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, the coating conditions may include a coating speed in a range of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and a heat treatment temperature for removing a solvent after coating in a range of about 80° C. to about 200° C. However, the coating conditions are not limited thereto.
[0148] Conditions for forming the hole transport layer and the electron blocking layer may be as the conditions for forming the hole injection layer.
[0149] The hole transport region may include at least one of 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4′,4″-tris(N, N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), p-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, or a compound represented by Formula 202:
##STR00480##
##STR00481##
##STR00482##
##STR00483##
##STR00484##
##STR00485##
##STR00486##
##STR00487##
##STR00488##
##STR00489##
##STR00490##
##STR00491##
##STR00492##
wherein, in Formula 201, Ar.sub.101 and Ar.sub.102 may each independently be: [0150] 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; or [0151] 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 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, or a combination thereof.
[0152] In Formula 201, xa and xb may each independently be an integer from 0 to 5, or may each independently be 0, 1, or 2. For example, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.
[0153] In Formulae 201 and 202, R.sub.101 to R.sub.108, R.sub.111 to R.sub.119, and R.sub.121 to R.sub.124 may each independently be: [0154] 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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, 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), or a C.sub.1-C.sub.10 alkylthio group; [0155] 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, or a combination thereof; [0156] a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group; or [0157] 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a C.sub.1-C.sub.10 alkylthio group, or a combination thereof, but embodiments of the present disclosure are not limited thereto.
[0158] In Formula 201, R.sub.109 may be: [0159] a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group; or [0160] a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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, a pyridinyl group, or a combination thereof.
[0161] In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments of the present disclosure are not limited thereto:
##STR00493##
wherein, in Formula 201A, R.sub.101, R.sub.111, R.sub.112, and R.sub.109 may each independently be as described herein.
[0162] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include one or more of Compounds HT1 to HT20, but embodiments of the present disclosure are not limited thereto:
##STR00494##
##STR00495##
##STR00496##
##STR00497##
##STR00498##
##STR00499##
##STR00500##
##STR00501##
##STR00502##
##STR00503##
##STR00504##
##STR00505##
##STR00506##
##STR00507##
##STR00508##
##STR00509##
##STR00510##
##STR00511##
##STR00512##
##STR00513##
[0163] A thickness of the hole transport region may be in a 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.
[0164] 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.
[0165] The charge-generation material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto. Nonlimiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenum oxide; or a cyano group-containing compound, such as Compound HT-D1 or F12, but are not limited thereto:
##STR00514##
##STR00515##
##STR00516##
[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, the emission layer may be formed on the hole transport region by using one or more suitable methods such as vacuum deposition, spin coating, casting, and/or LB deposition. 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 forming the electron blocking layer may be selected from materials for the hole transport region described above and host materials to be explained later. However, the material for forming the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, the material for forming the electron blocking layer may be mCP, which will be described below.
[0170] The emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1.
[0171] In one or more embodiments, the host may include at least one of 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′-dimethylbiphenyl (CDBP), N,N,′N″-1,3,5-tricarbazoloylbenzene (TCP), 1,3-bis(carbazol-9-yl)benzene (mCP), Compound H50, or Compound H51:
##STR00517##
##STR00518##
##STR00519##
##STR00520##
##STR00521##
##STR00522##
##STR00523##
##STR00524##
##STR00525##
[0172] In one or more embodiments, the host may further include a compound represented by Formula 301:
##STR00526##
wherein, in Formula 301, Ar.sub.111 and Ar.sub.112 may each independently be: [0173] a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group; or [0174] 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.
[0175] In Formula 301, Ar.sub.113 to Ar.sub.116 may each independently be: [0176] a C.sub.1-C.sub.10 alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, or a pyrenyl group; or [0177] 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.
[0178] In Formula 301, g, h, i, and j may each independently be an integer from 0 to 4, and for example, may each independently be 0, 1, or 2.
[0179] In Formula 301, Ar.sub.113 to Ar.sub.116 may each independently be: [0180] a C.sub.1-C.sub.10 alkyl group which is substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or a combination thereof; [0181] a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, or a fluorenyl group; [0182] 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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
##STR00527##
[0183] In one or more embodiments, the host may include a compound represented by Formula 302:
##STR00528##
wherein, in Formula 302, Ar.sub.122 to Ar.sub.125 may each independently be as described in connection with Ar.sub.113 in Formula 301.
[0184] In Formula 302, Ar.sub.126 and Ar.sub.127 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).
[0185] In Formula 302, k and I may each independently be an integer from 0 to 4. For example, k and I may each independently be 0, 1, or 2.
[0186] 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, based on 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, and various modifications are possible.
[0187] 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.
[0188] 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 luminescence characteristics may be obtained without a substantial increase in driving voltage.
[0189] Next, the electron transport region is located on the emission layer.
[0190] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
[0191] 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, but 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.
[0192] Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be as the conditions for forming the hole injection layer.
[0193] 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(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), but embodiments of the present disclosure are not limited thereto:
##STR00529##
##STR00530##
[0194] 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.
[0195] The electron transport layer may further include at least one of BCP, Bphen, Alq.sub.3, BAlq, 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ):
##STR00531##
##STR00532##
##STR00533##
##STR00534##
[0196] In one or more embodiments, the electron transport layer may include at least one of Compounds ET1 to ET25, but embodiments of the present disclosure are not limited thereto:
##STR00535##
##STR00536##
##STR00537##
##STR00538##
##STR00539##
##STR00540##
##STR00541##
##STR00542##
##STR00543##
##STR00544##
##STR00545##
##STR00546##
##STR00547##
##STR00548##
##STR00549##
##STR00550##
##STR00551##
##STR00552##
##STR00553##
##STR00554##
##STR00555##
##STR00556##
##STR00557##
##STR00558##
##STR00559##
[0197] A thickness of the electron transport layer may be in a 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 these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
[0198] The electron transport layer may include a metal-containing material in addition to the material as described above.
[0199] 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:
##STR00560##
##STR00561##
[0200] The electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode 19 thereinto.
[0201] The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or a combination thereof.
[0202] 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 162 is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
[0203] 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 has a relatively low work function. For example, the material for forming the second electrode 19 may be lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag). 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.
[0204] Hereinbefore, the organic light-emitting device has been described with reference to the
[0205] Another aspect of the present disclosure provides a diagnostic composition including at least one organometallic compound represented by Formula 1.
[0206] The organometallic compound represented by Formula 1 provides high luminescence efficiency, and accordingly, the diagnostic composition including the at least one organometallic compound may have high diagnostic efficiency.
[0207] The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.
[0208] 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 examples thereof are 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, a hexyl group, and the like. The term “C.sub.1-C.sub.60 alkylene group” as used herein refers to a divalent group having the same structure as the C.sub.1-C.sub.60 alkyl group.
[0209] 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 are a methoxy group, an ethoxy group, an isopropyloxy group, and the like.
[0210] The term “C.sub.1-C.sub.60 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).
[0211] 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 are an ethenyl group, a propenyl group, a butenyl group, and the like. 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.
[0212] 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 are an ethynyl group, a propynyl group, and the like. 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.
[0213] The term “C.sub.3-C.sub.10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like. 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.
[0214] 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, Ge, Se, and S as a ring-forming atom and 1 to 10 carbon atoms, and examples thereof are a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. 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.
[0215] 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 examples thereof are a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. 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.
[0216] The term “C.sub.2-C.sub.10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one hetero atom selected from N, O, P, Si, Ge, Se, and S as a ring-forming atom, 2 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, a 2,3-dihydrothiophenyl group, and the like. The term “C.sub.2-C.sub.10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C.sub.2-C.sub.10 heterocycloalkenyl group.
[0217] 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 are a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, and the like. 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 two or more rings may be fused to each other.
[0218] The term “C.sub.7-C.sub.60 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.
[0219] The term “C.sub.1-C.sub.60 heteroaryl group” as used herein refers to a monovalent group having a cyclic aromatic system that has at least one heteroatom selected from N, O, P, Si, Ge, Se, and S as a ring-forming atom, and 1 to 60 carbon atoms. The term “C.sub.1-C.sub.60 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, Ge, Se, 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, an isoquinolinyl group, and the like. 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 two or more rings may be fused to each other.
[0220] 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.
[0221] The term “C.sub.6-C.sub.60 aryloxy group” as used herein indicates -OA.sub.102 (wherein A.sub.102 is the 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 the C.sub.6-C.sub.60 aryl group).
[0222] The term “C.sub.1-C.sub.60 heteroaryloxy group” used herein indicates -OA.sub.104 (wherein A.sub.104 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.105 (wherein A.sub.105 is the C.sub.1-C.sub.60 heteroaryl group).
[0223] 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 are a fluorenyl group and the like. 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.
[0224] 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, Ge, Se, 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 are a carbazolyl group and the like. 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.
[0225] 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.
[0226] 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, Ge, Se, 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.
[0227] In the present specification, TMS represents * —Si(CH.sub.3).sub.3, and TMG represents * —Ge(CH.sub.3).sub.3.
[0228] 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.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 hetero arylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be: [0229] 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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; [0230] a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, or a C.sub.1-C.sub.60 alkoxy group, each 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.1-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(═O)(Q.sub.18)(Q.sub.19), or a combination thereof; [0231] 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; [0232] 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.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, —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(═O)(Q.sub.28)(Q.sub.29), or a combination thereof; or [0233] —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), or —P(═O)(Q.sub.38)(Q.sub.39), and [0234] Q.sub.1 to Q.sub.9, Q.sub.11 to Q19, Q.sub.21 to Q29, and Q.sub.31 to Q39 may each independently be 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 C.sub.1-C.sub.60 heteroaryloxy group, a 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.
[0235] Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Examples and Examples. However, the compound and the organic light-emitting device are 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
[0236] Synthesis Example 1: Synthesis of Compound 1
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Synthesis of Compound 1A
[0237] Under a nitrogen environment, 2-chloro-4-isopropylpyridine (1.5 grams (g), 9.6 millimoles (mmol)) and (7-(trimethylsilyl)dibenzo[b,d]furan-4-yl)boronic acid (3.3 g, 11.6 mmol) were dissolved in 180 milliliters (mL) of 1,4-dioxane. Next, a solution containing potassium carbonate (K.sub.2CO.sub.3) (3.1 g, 22.4 mmol) dissolved in 60 mL of deionized (DI) water was added thereto, and then a palladium catalyst (tetrakis(triphenylphosphine)palladium(0), Pd(PPh.sub.3).sub.4) (0.25 g, 0.22 mmol) was also added thereto. Afterwards, the resultant reaction mixture was stirred and heated under reflux at a temperature of 110° C. After allowing it to cool to room temperature, an extraction process was performed thereon, a solid thus obtained was subjected to column chromatography (eluent: ethyl acetate (EA) and hexanes) to obtain (4-isopropyl-2-(7-(trimethylsilyl)dibenzo[b,d]furan-4-yl)pyridine (Compound 1A(1)) 2.9 g (yield of 84%). The obtained compound was identified by high resolution mass spectrometry (HRMS using matrix assisted laser desorption ionization (MALDI)) and HPLC analysis.
[0238] HRMS (MALDI) calcd for C.sub.23H.sub.25NOSi: m/z: 359.54 Found: 360.14.
Synthesis of Compound 1A
[0239] Compound 1A(1) (8.6 g, 23.8 mmol) and iridium chloride (4.0 g, 13.4 mmol) were mixed with 120 mL of 2-ethoxyethanol and 40 mL of DI water, and stirred and heated under reflux for 24 hours. Then, the reaction temperature was allowed to lower to room temperature. The resulting solid was separated by filtration, washed sufficiently with DI water, methanol, and hexanes, in this stated order, and then dried in a vacuum oven to obtain 9.2 g (yield of 87%) of Compound 1A. Compound 1A obtained was used in the next reaction without an additional purification process.
Synthesis of Compound 1
[0240] Compound 1A (1.5 g, 0.79 mmol), 2-(1-methyl-1H-benzo[d]imidazol-2-yl)phenol (0.4 g, 1.78 mmol), and sodium carbonate (Na.sub.2CO.sub.3) (0.3 g, 2.83 mmol) were added and mixed with 20 mL of 2-ethoxyethanol. The mixed solution was then stirred and heated under reflux for 3 hours, and then the reaction temperature was lowered to room temperature. The resulting solid was filtered and washed with DI water, methanol, and n-hexane, in this stated order, and then dried in a vacuum oven. The obtained solid was subjected to column chromatography (eluent: methylene chloride (MC) and hexanes) to obtain 0.72 g (yield of 80%) of Compound 1. The obtained compound was identified by HRMS and HPLC analysis.
[0241] HRMS (MALDI) calcd for C.sub.60H.sub.59IrN.sub.4O.sub.3Si.sub.2 : m/z: 1132.54 Found: 1133.52.
[0242] Synthesis Example 2: Synthesis of Compound 2
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[0243] Compound 2 was obtained in a similar manner as in synthesis of Compound 1, except that (7-(trimethylgermyl)dibenzo[b,d]furan-4-yl)boronic acid was used instead of (7-(trimethylsilyl)dibenzo[b,d]furan-4-yl)boronic acid . The obtained compound was identified by HRMS and HPLC analysis.
[0244] HRMS (MALDI) calcd for C.sub.60H.sub.59Ge.sub.2IrN.sub.4O.sub.3 : m/z: 1221.63 Found: 1222.59.
Example 1
[0245] As an anode, an ITO-patterned glass substrate was cut to a size of 50 millimeters (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 ITO-patterned glass substrate was loaded onto a vacuum deposition apparatus.
[0246] Compound HT3 and Compound F12 (p-dopant) were vacuum-co-deposited on the anode at a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 angstroms (Å), and Compound HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,650 Å.
[0247] Subsequently, Compound GH3 (host) and Compound 1 (dopant) were co-deposited at a weight ratio of 92:8 on the hole transport layer to form an emission layer having a thickness of 400 Å.
[0248] 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.
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##STR00572##
Example 2 and Comparative Examples 1 to 3
[0249] Organic light-emitting devices were manufactured in a similar manner as in Example 1, except that compounds shown in Table 2 were respectively used instead of Compound 1 as a dopant in forming an emission layer.
[0250] The driving voltage (volts, V), maximum emission wavelength (λ.sub.max, nm) in emission spectra, maximum external quantum efficiency (Max EQE, %), and roll-off ratio (%) of each of the organic light-emitting devices of Examples 1 and 2 and Comparative Examples 1 to 3 were evaluated, 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 roll-off ratio was calculated according to Equation 20.
Equation 20
[0251] Roll-off ratio = {1- (efficiency / maximum luminescence efficiency)} X 100 %
TABLE-US-00002 No. Dopant in emission layer Driving voltage (V) Amax(EL) (nm) Max EQE (%) Roll-off ratio (%) Example 1 Compound 1 4.5 532 22 12 Example 2 Compound 2 4.5 532 22 12 Comparative Example 1 Compound A 4.7 528 20 15 Comparative Example 2 Compound B 4.8 538 21 14 Comparative Example 3 Compound C 4.7 530 21 15
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[0252] Referring to Table 2, it was confirmed that the organic light-emitting devices of Examples 1 and 2 had low driving voltage and low roll-off ratio and high EQE. In detail, it was confirmed that the organic light-emitting devices of Examples 1 and 2 had lower driving voltage and lower roll-off ratio and higher EQE than those of the organic light-emitting devices of Comparative Examples 1 to 3.
[0253] As described above, according to the one or more embodiments, an organometallic compound may have excellent electrical characteristics and thermal stability. In particular, the organometallic compound has a high glass transition temperature so that crystallization thereof may be prevented, and electric mobility thereof may be improved. Accordingly, an electronic device, such as an organic light-emitting device, using the organometallic compound may have low driving voltage, high efficiency, a long lifespan, a reduced roll-off ratio, and a relatively narrow FWHM of an emission peak in an electroluminescence spectrum.
[0254] Thus, due to the use of the organometallic compound, a high-quality organic light-emitting device may be implemented. In addition, an electronic apparatus including the organic light-emitting device may be provided.
[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 one or more other exemplary embodiments. While one or more embodiments have been described with reference to the